CHEMISTOY
LIBRARY
DYES CLASSIFIED
BY INTERMEDIATES
Dyes tabularly arranged under each
intermediate, with statistical and other
data for both dyes and intermediates.
Glossary of Dye and Intermediate
names alphabetically arranged.
BY
R. NORRIS SHREVE
Consulting Chemist
EN COLLABORATION WITH
WARREN N. WATSON
AND
A. R. WILLIS
Chemists, U. S. Tariff Commission
BOOK DEPARTMENT
The CHEMICAL CATALOG COMPANY, Inc.
ONE MADISON AVENUE, NEW YORK, U. S. A.
COPYRIGHT, 1922, BY
The CHEMICAL CATALOG COMPANY, Inc.
All Rights Reserved
Press of
J. J. Little & Ives Company
New York, U. S. A.
TABLE OF CONTENTS
PAGE
PREFACE 3
ABBREVIATIONS 5
'INTRODUCTION 7
PART I. INTERMEDIATES AND DYE TABLES ... 17
KEY TO PART I 18
INTERMEDIATES WITH DYE TABLES. THE ARRANGEMENT OF INTER-
MEDIATE NAMES is ALPHABETICAL AND INCLUDES CHEMICAL AND
COMMON OR TRIVIAL NAMES 19
FORMULA INDEX OF INTERMEDIATES . 581
PART II. DYE NAMES 587
GLOSSARY OF DYE NAMES 589
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 625
472415
PREFACE
Experience in the manufacture of dyes indicates that the proper
viewpoint for a correct technical program is from the intermediate side.
This is a direct corollary of the fact that the intermediates are the
materials out of which dyes are fabricated. Furthermore, the tremen-
dous complexity of the dye industry, the interrelationship of one dye to
another or of one intermediate to another, as well as the relationship of
dyes and intermediates to the whole organic chemical industry, all
require that there be available tables showing the commercial dyes
derived from each important intermediate. To give this is the prime
object of this work.
It is believed that this book will be of service not only to manufac-
turers in looking for uses of any intermediate, but to research chemists
and to students. Since the tables give the various outlets and the
poundage imported and manufactured, the book will aid the merchant
in the buying or selling of dyes and intermediates. The very com-
plete glossary of names, both of dyes and intermediates, will help in
many directions, especially as the intermediate part includes the
so-called common or trivial names. This feature will be of great
service in reading the older literature and patents.
The intermediate names are alphabetically arranged. Under each
principal name is given the synonyms, which are also cross-indexed in
their alphabetical order. A special feature is the giving of the name
used by Chemical Abstracts; this, together with the listing of the prin-
cipal formulas, will aid in the use of the Chemical Abstracts by the Dye .
Chemist.
A Formula Index to the names of the intermediates and to the pages
is given following the main part of this book containing the alphabetical
treatment of the intermediates. Here the formulas of the intermediates
are listed in an alphabetical order as in a dictionary, except that CH
comes first; and in this way a 5-atom formula may precede a 3-atom
one. This is similar to the excellent formula index of the 1920 Chemical
Abstracts.
After the writer had been engaged for some time in the preparation
of this book, he was informed of a somewhat similar classification
undertaken by Messrs. Warren N. Watson and A. R. Willis of the
Tariff Commission, Washington, D.C. It was deemed fair to cooper-
3
4 PREFACE
ate and to associate the two works by the mutual use of the other names
as " collaborators." Messrs. Watson and Willis have published a part
of their work, comprising about a third of the Schultz dyes, in the
Color Trade Journal serially from May to September during 1921.
This serial publication by Messrs. Watson and Willis and this book by
the writer are separate and independent productions. The writer,
however, takes this occasion to express his appreciation for advice and
help to Messrs. Watson and Willis.
It is a pleasure to acknowledge help from Dr. Austin M. Patterson
on the Chemical Abstracts nomenclature. Aid has also been rendered
by J. R. Minevitch, M. N. Conklin and Oscar Newman. The statistical
data are taken from the yearly Census of Dyes and Coal Tar Chemicals
compiled by the U. S. Tariff Commission, and from Artificial Dyestuffs
Used in the United States by Thomas H. Norton.
R. NORRIS SHBEVE.
NEW YORK CITY
December, 1921.
ABBREVIATIONS
Dye Application Column
A Acid dye
ACr Acid chrome dye
B Basic dye
CL Color lake
D Direct dye
MF Color made on fiber
M Mordant dye
S Sulfur dye
ss Spirit soluble dye
V Vat dye
Statistics Column
I '14 Imports, Fiscal Year 1914 (year ending
June 30, 1914)
I '20 Imports, Calendar Year 1920
M'17 .
M'18
M'19
Manufactured in Calendar Year
1917, 1918, 1919, or 1920
M'20 .....
Literature References
BARNETT, ANTHRACENE AND ANTHRAQUINONE
E. de Barry Barnett, Anthracene and Anthraquinone, 1921.
D. Van Nostrand & Co.
BEIL.
Beilstein, Handbuch der organischen Chemie (3rd Ed.).
BER.
Berichte der Deutschen Chemischen Gesellschaft.
CAIN, INTERMEDIATE PRODUCTS
J. C. Cain, The Manufacture of Intermediate Products for Dyes,
Second Edition 1919, Macmillan & Co.
FRDL.
P. Friedlaender, Fortschritte der Teerfarbenfabrikation, 1877-1916,
12 vols., Julius Springer.
6 ABBREVIATIONS
GREEN, ORGANIC COLORING MATTERS
A. G. Green, A Systematic Survey of the Organic Colouring Matters,
1908 Edition, Macmillan & Co.
GEORGIEVICS AND GRANDMOUGIN, DYE CHEMISTRY
G. von Georgievics and E. Grandmougin, translated by F. A.
Mason. A Textbook of Dye Chemistry, 1920. Scott Green-
wood & Son.
HEUMANN, ANILINFARBEN
K. Heumann (Fourth part edited by G. Schultz), Die Anilinfarben
und ihre Fabrikation, Four Parts, 1888-1906, Friedrich Viewig.
LANGE, SCHWEFELFARBSTOFFE
Otto Lange, Die Schwefelfarbstoffe, ihre Herstellung und Verwen-
dung, 1912, Otto Spamer.
LANGE, ZWISCHENPRODUKTE
Otto Lange, Die Zwischenprodukte der Teerfarbenfabrikation,
* 1920, Otto Spamer.
THORPE, Die. CHEMISTRY
Edw. Thorpe, A Dictionary of Applied Chemistry, First Edition,
Longmans Green & Co.
ULLMANN, ENZY. TECH. CHEMIE
Enzyklopaedie der technischen Chemie, Edited by Dr. Fritz Ull-
mann, 1914. Urban & Schwarzenberg.
Miscellaneous
o ortho
m meta
p para
a alpha
j8 beta
N Nitrogen (signifies nitrogen attachment
of radical)
C. A. nomen. . . Chemical Abstracts nomenclature
(mols) Molecules
Schultz Number . Number for dye as given in Schultz,
Farbstofftabellen, 1914 Edition.
INTRODUCTION
The contents of this book fall into two parts: first, an alphabetical
list of intermediates with their data and dye tables, and second, an
aphabetical list of dye names referring to their Schultz numbers when
known, by which any dye here classified can be found in the tables by
looking in the "Page Index of Schultz Numbers" at the end of the book
for the appropriate pages.
Often an intermediate is known by as many as half a dozen names,
and each one is listed in its alphabetical order, but the synonyms all
refer to one name under which are arranged the tables and other data.
Thus the book is a glossary of intermediate names. In selecting the
name given at the head of the data for a certain intermediate, the
writer was influenced first by considerations of clearness and then
of custom and usage. For a full discussion of this important nomen-
clature question, reference is made to the nomenclature section of this
introduction.
Following the synonyms, is given the structural formula, the empirical
formula, and the molecular weight. It is the emphatic opinion of the
writer that the indexing of organic compounds by their formulas is the
simplest, the most universal, and the clearest. Chemical Abstracts,
starting with 1920, has inserted a formula index, and it is believed that
chemists can find a given intermediate quicker and more surely in
Chemical Abstracts by the use of this formula index than by the ordinary
subject index. The formulas given here will be an aid in this direction.
Furthermore a formula index is included in this book.
Under each intermediate there is listed a short description of methods
of Formation followed by Literature References. These are not exhaustive
in any sense, but the aim has been to give the usual commercial prepa-
ration together with several references to the literature for any one who
desires more details. The references to Lange, Zwischenprodukte,
cover the German patents.
In order to give some basis for judging the extent to which a dye or
an intermediate is used, the statistical data for importation and manu-
facture in the United States is given under Statistics. These data are
taken from the following government reports : Census of Dyes and Coal-
Tar Chemicals, by U. S. Tariff Commission; Artificial Dyestuffs Used in
the U. S., by Thomas H. Norton, and Chemicals and Allied Products
7
8 INTRODUCTION
Used in the U. S. by E. R. Pickrell. The Imports 1914 both under inter-
mediates and under dyes refer to the imports for the fiscal year ending
June 30, 1914. Otherwise the imports, and always the amounts manu-
factured, refer to the calendar year marked. It is believed that the
addition of these statistical data to the tables will be of much service in
pointing out forcibly the relative commercial importance of the dyes
and intermediates, and will help to complete development of the dye
industry in America. In considering these statistics, it must be borne
in mind that since 1914 the United States has been endeavoring to
fully supply her own needs, and proceeded naturally along the lines of
least resistance, so that often a dye was manufactured because of its
comparative simplicity, to be later superseded by a more suitable dye
of more complexity. The Imports for 1914 (fiscal year ending June
30, 1914) are "normal" except that Vat Dyes were not imported as
heavily that year as had been the usual case.
The statistics of import of a dye, especially for the fiscal year ending
June 30, 1914, often include a number of very similar though not
identical dyes. These statistics were obtained by adding together the
individual dye weights as listed by Norton under a given Schultz
number.
Where F14, M'19, Manufactured 1919, etc., are given followed by a
question mark, it indicates that the dye or intermediate was imported
or manufactured for the year marked but in amounts that have not
been disclosed by the U. S. Government.
When a figure is given for imports or manufactures of dyes or inter-
mediates, this figure always refers to pounds.
The tables proper give for any intermediate all the dyes listed in
Schultz, Farbstofftabellen, 1914 Edition, that are derived from this
intermediate. This includes practically all of the important dyes
except a few of the newer ones of undisclosed constitution. Thus a
given dye is separately arranged under each of its intermediates. As
there is named in a special column the Other Intermediates constituting
a dye besides the one at the head of each table, the intermediate rela-
tionship is clearly stated.
The following dyes listed in Schultz, Farbstofftabellen (1914), are
not classified, on account of lack of information as to their composition-
30 Radial Yellow G 706 Cachou de Laval
87 Peri Wool Blue 707 Sulfine Brown
608 Euchrysine 708 Sulfaniline Brown
609 Homophosphine G 744 Sulfo Black B, 2B
INTRODUCTION 9
751 Krygene Brown RB 756 Kryogene Black TGO
752 Kryogene Direct Blue GO 757 Sulfogene Brown G, D
753 Kryogene Direct Blue B 863 Anthraquinone Blue Green B XO
754 Kryogene Direct Blue 3B 871 Indanthrene Violet RN Extra
755 Kryogene Black BNX
In very many cases, the writer has supplemented the information
in Schultz, Farbstofftabellen, as to composition of dyes, and hence has
been able to classify many dyes whose composition is indefinite in this
book. In a number of instances when Schultz refers the dyes to com-
plex intermediates, these have been split into simpler components, and
the components as well as the complex parent compound have all been
indexed. Also certain obvious errors in Schultz, Farbstofftabellen, have
been corrected, as for example, where in #182, reference is made to
l-amino-4-naphthol-sulf onic acids which the patent refers to ai : a 4 -
sulfonic acids (l-amino-8-naphthol-sulfonic acids) and specifically names
H acid in the example given.
When the patents describing a dye list a number of intermediates,
then those listed under Example I of the patent are chosen for classifica-
tion unless, of course, Schultz, Farbstofftabellen, gives definite composi-
tion to the dye. Quite often intermediates are indexed even though
not a component part of the final dye, provided they were necessary
to its manufacture, e.g. benzoic acid in the manufacture of certain of
the Triphenyl-methane Dyes as Diphenylamine Blue and Aniline Blue.
All possible intermediates for any given dye are not indexed, but it
is hoped to extend the present classification at a later date. Previous
tables resembling those given here, but along much less extensive lines,
are to be found in Heumann, Die Anilinfarben und ihre Fabrikation
IV, II, 2, pages 1943-2013, and Lefevre, Traite des Matieres Colorantes
(1896), pages 140-407.
In the column in the tables headed Other Intermediates Used and
Notes, there is given first the intermediates other than the one 'at the
head of the table, which compose the dye in question. Unless other-
wise marked, it is to be understood that one molecule of an intermediate
is used. When more than one molecule is employed, of the intermediate
heading the table, then the name of this intermediate is also given in
the Other Intermediates column followed by the number of molecules
(mols) that are used in the dye.
The notes are in brackets, and are mostly self-explanatory, and refer
chiefly to constituents, such as sulfur (S), sodium sulfide (Na 2 S), and
the like, which enter into the formation of the dye. Such steps as
10 INTRODUCTION
Sulfonation, Bromination, and Chlorination are given, but Coupling
by Diazotization and Condensation are to be understood.
Under notes is generally listed the name of a given dye if it is a step
in the preparation of the dye classified in the table, but this component
dye is not used as the index or heading for any of the dye classification
tables, and this fact is indicated by placing the name of the component
dye in a bracket.
Indigo is an exception, and the dyes based on it are tabulated there-
under as well as under the various component intermediates.
The last column in the tables classifies the dyes by their usual method
of application as indicated by the following abbreviations.
A Acid dye
ACr Acid chrome dye
B Basic dye
CL Color lake
D ........ Direct dye
MF Color made on fiber
M Mordant dye
S Sulfur dye
ss Spirit soluble dye
V Vat dye
A classification of this kind is not very exact in certain cases where
a dye is susceptible of several different methods of application. The
aim has been to give the mode of application most generally employed.
Regarding the naming of the dyes, there is used in the tables that
name first given in Schultz, Farbstofftabellen (1914), followed by a
second name in those cases where the second name is more generally
used in the United States than the first Schultz name.
A glossary of the ordinary German and Swiss names, together with
many of the American and English names, is given in the back of the
book. It would have been very helpful to have added to this list all
the current American and English marks, but in the present develop-
ment stage of the American dye industry, this turned out to be im-
practical. The list as given includes those listed and classified by
Norton in Artificial Dyestuffs Used in U. S., with various corrections
and a considerable number of additions. These names refer to "Schultz' '
numbers where known, and as the last few pages of the book give a list
of the pages on which occur references to any "Schultz" number, the
place of any dye of known constitution can be readily found, together
with the data,regarding that dye.
INTRODUCTION 11
In the tables, the dyes are classified under the usual constitutional
headings, which are here grouped in the following list:
Nitroso Dyes
Nitro Dyes
Stilbene Dyes
Pyrazolone Dyes
Monoazo Dyes
Disazo Dyes
Trisazo Dyes
Tetrakisazo Dyes
- Auramines
^.Triphenyl-methane Dyes
Diphenyl-naphthyl-methane Dyes
Xanthone Dyes
- Acridine Dyes
Quinoline Dyes
Thiobenzenyl Dyes
Indophenol
Oxazine Dyes
Thiazine Dyes
Azine Dyes
Sulfur Dyes
Anthraquinone and Allied Dyes
Indigo Group Dyes
Aniline Black Group
NOMENCLATURE
The scientific naming of intermediates has indeed been confused,
and in many instances a number of names have been used for the same
compound, or the same name for several different compounds. It has
been the aim of this book to give the various names met with in the
literature for the intermediates, and to cross-index these names in the
alphabetical arrangement, thus giving a glossary of intermediate
names for all those common intermediates here considered. Further-
more the common or trivial names are listed in a very complete manner
and include the trivial names for many intermediates not specially
considered here. As mentioned before, there has been chosen for the
principal name from among the various synonyms that name which is
clear and which is sanctioned by custom. In so choosing, the tendency
has been to adopt a few of the well-known trivial or common names,
12 INTRODUCTION
such as H Acid and Nevile-Winther's Acid, in place of the strictly
chemical names; for the writer's experience is that dye men, whether
in the research laboratory, the factory, or the office, speak of H Acid for
example, and not l-amino-8-naphthol-3 : 6-disulfonic acid.
The most scientific nomenclature is that used by Chemical Abstracts
of the American Chemical Society. This is fully explained in the
Introduction to Decennial Index of Chemical Abstracts, as well as in
the Journal of the American Chemical Society. 1
It, however, offers the disadvantage of requiring considerable study
to master its principles, which often vary from the practice of the dye
industry, and furthermore there is comparatively little literature per-
taining to dyes and intermediates in the years covered by Chemical
Abstracts.
On the other hand, organic chemistry is now so complex that more
attention must be paid to scientific naming of organic compounds,
and also the amount of dye literature contained in Chemical Abstracts
is increasing yearly, so that it is to the advantage of the dye chemist
to familiarize himself with the procedure of Chemical Abstracts, and it
cannot be too strongly recommended that every one make a study
of the principles of Chemical Abstracts nomenclature as disclosed in
the references given above.
This book aims to give the Chemical Abstracts name for each inter-
mediate; and in the many cases where this name differs from the one
in common use, this Chemical Abstracts name is so designated by
being marked C. A. nomen., as an abbreviation for Chemical Abstracts
Nomenclature. If only one name is listed, it is to be understood that
this is the one sanctioned by Chemical Abstracts.
Beginning with the 1920 volumes of Chemical Abstracts, a Formula
Index is included, which offers the easiest way to find reference to a
chemical compound or its nomenclature.
In case of many benzene derivatives, the writer has adopted the
Chemical Abstracts nomenclature, as there is considerable confusion
in the literature regarding these names, and as the Chemical Abstracts
procedure does not vary greatly as a rule from well-recognized practice.
However, in case of many of the naphthalene derivatives the Chemical
Abstracts practice is so far from what is commonly used that the Chem-
ical Abstracts names are only given as synonyms. The men responsible
for Chemical Abstracts are showing a great willingness to bring their
1 Patterson and Curran, J. Amer. Chem. Soc. 39, 1623-38 (1917).
INTRODUCTION 13
system as near to that used in practice as possible, and in all probability
the near future will show closer accord.
The very common use of more than one of the terms ortho, meta, and
para, to indicate position of substituents, is very confusing and should
be dropped in preference either to the procedure of Chemical Abstracts
where one such term is used in connection with numbers, or to the
use of numbers alone. For example, m-nitro-p-toluidine (CH 3 = 1) and
o-amino-phenol-p-sulfonic acid should be replaced by 2-nitro-p-toluidine
(NH 2 =1) and 2-amino-l-phenol-4-sulfonic add, the present Chemical
Abstracts usage. In the former case the writer much prefers the name
l-amino-2-nitro-4-toluene.
Chemical Abstracts uses p-toluidine (NH 2 = 1) and p-phenylene-dia-
mine and the like as "index compounds" with the various substituents
as modifiers, arranged in an inverted order in their indices. In this
book the practice of Chemical Abstracts in this regard is followed,
except for the inversion for the principal name of the intermediate.
The other names are given as synonyms and cross-indexed. However,
in the body of the tables, such terms as o-amino-phenol-p-sulfonic acid
are used in a few cases because of their very common usage, and conse-
quent quick recognition.
Treating the matter broadly, the gist of the Chemical Abstracts
nomenclature practice is that the " chief function" of a compound is
expressed in the main part of the name, which with "its functional
ending, if any, is placed first in the index, the names of the substituents
following." The numbering starts from the "chief function" and is
not varied by the addition of substituents, for instance, 2: 7-naphtha-
lene-sulfonic acid is an "index compound," as is likewise 1 naphthalene-
sulfonic acid; and their amino, halogen, and nitro derivatives are
indexed thereunder. For instance, Laurent's Acid or what is ordinarily
called l-naphthylamine-5-sulfonic acid is indexed by Chemical Abstracts
under 1-naphthalene-sulfonic acid, and called 5-amino-l -naphthalene-
sulfonic acid. In the decennial index, hydroxy was also considered as
a substituent.
However, naphthol-sulfonic acids and phenol-sulfonic acids are now
recognized by Chemical Abstracts as exceptions to their rule of assigning
the chief function to acids, and of allowing only one functional ending
in the index name. So that while in the decennial index these -ol-
sulfonic acids had their numbering start with the sulfonic group, now
the numbering begins with the hydroxyl. For example, l-naphthol-4-
sulfonic acid and l-naphthol-8: 6-disulfonic acid. In case of amino- nitro-
14 INTRODUCTION
chloro- derivatives and the like, the positions are referred to the set
numbering of the index compound. Take H Acid, this is viewed as a
derivative of index compound l-naphthol-3: 6-disulfonic acid by Chemical
Abstracts, and is named in their index as 8-amino-l-naphthol-3: 6-
disulfonic add, or in their inverted form as l-naphthol-3: 6-disulfonic
acid, 8-amino-.
This numbering is quite different from the ordinary numbering of
l-amino-8-naphthol-3: 6-disulfonic acid for H Acid. The giving in this
book of both nomenclatures will help in the using of Chemical Ab-
stracts, and as a further aid in this direction the first letter of the
index compound as employed in Chemical Abstracts is italicized.
The rule of Chemical Abstracts regarding arrangement of substituents,
reads as follows: "The names of substituent radicals in the name of a
compound are arranged in alphabetical order." This is an excellent
practice and should be universally adopted. In conformance with this,
benzyl-ethyl-aniline is recommended, and not ethyl-benzyl-aniline.
In the naming of toluene derivatives, the usual custom has been to
start numbering from the CH 3 group irrespective of other substituents.
In Chemical Abstracts, the numbering starts from the chief function,
and the order of the chief function is: "onium compounds, acid (car-
boxylic first), acid halide, amide, imide, aldehyde, nitrile, ketone, alcohol,
phenol, mercaptan, amine, imine, ether, sulfide (and sulfoxide and sul-
fone)." So whenever sulfonic acid is present, the start of the numbering
is with this group, except that the carboxylic group, being an acid radical,
is of same order as sulfonic, and has been given precedence over the
sulfonic radical. Instead of toluidine-sulfonic acid with the numbering
based on the CHs, Chemical Abstracts uses amino-o- (or m- or p-)
toluene-sulfonic acid and starts the numbering with the sulfonic acid
group. Toluidines start their numbering from the NH 2 group, as it has
precedence over CH 3 . Another divergence of the Chemical Abstracts
practice from the ordinary numbering is the place of the numbers
or letters in such terms as the following:
Ordinary Practice Chemical Abstracts Practice
Naphthalene-2: 7-disulfonic Acid 2: 7-Naphthalenedisulfonic Acid
Toluene-p-sulf onic Acid p-Toluenesulfonic Acid
The custom of using hyphens to set off radicals and substituents from
each other and from the parent compound is extensively used in this
book for the sake of clearness, and as an aid to the eye and the mind.
No one thinks of a complex organic chemical as a whole, but as a com-
INTRODUCTION 15
plex of various substituents around a central body; therefore the
writing of a long name like tetramethyldiaminodiphenymethane as one
word is very reprehensible and should be early abandoned. Otherwise
the careless practice of writing as two or more separate words the
name of one chemical individual is bound to increase; already this
latter practice is gaining too much headway, as can be seen by an
inspection of our trade or semi-technical journals.
The rule about hyphens as used here is to insert them between
all radicals, and between the radicals and the parent body, except
in the case of compound radicals, such as melhylamino- (CH 3 NH-),
tetraethyl-, disulfonic- and the like. Methylamino should not be written
methyl-amino. While Chemical Abstracts does not employ hyphens
in this broad way, yet the use of hyphens has been extended to the
names otherwise following Chemical Abstracts procedure.
It is clearly recognized that the nomenclature here used is not always
consistent as between the scientific and common usage. For example
while ^-amino-l-phenol-4-sulfonic add is listed as the principal name
of this intermediate, yet in the body of the tables the ordinarily used
synonym o-amino-phenol-p-sulfonic acid is given because of its quick
recognition. However, the movement to a more scientific nomen-
clature such as used by Chemical Abstracts should be encouraged as
much as possible, and such terms as o-amino-phenol-p-sulfonic add
should be dropped gradually.
PART I
INTERMEDIATES
KEY TO PART I INTERMEDIATES AND DYE TABLES
The arrangement is alphabetical not only by chemical but by trivial
or common names. Many trivial names are listed for intermediates
which are not further considered. Dye tables and other data ac-
company those intermediates which enter directly into the formation
of the commonly used dyes.
Synonyms and trivial names are given for the intermediates, and
these synonyms and trivial names are listed not only under the ap-
propriate intermediate but also separately in the alphabetical arrange-
ment.
That chemical name called for by the Chemical Abstracts nomen-
clature is to be found either as the principal name of each intermediate
or among its synonyms. This is distinguished by being followed by
the abbreviation C. A. nomen., except when only one name is used for
an intermediate, in which case this name is the one in common usage
and is also that one sanctioned by Chemical Abstracts. In the indices
of Chemical Abstracts the names are alphabetically arranged under a
number of " parent compounds" which in ordinary usage are preceded
by the modifying radicals. As this book follows the ordinary usage,
it was thought that it would be helpful to designate the Chemical Ab-
stracts " parent compound," which is done by italicizing the first
letter of these "parent compounds" in those names following Chemical
Abstracts nomenclature.
The prefixes m-, o-, p-, a-, j8- and the like are not considered in the
main alphabetical arrangement. Hence /3-naphthol (beta-naphthol) is
to be found under N.
The import statistics are not for each strictly individual dye mark,
but represent a group identical to or closely resembling a given Schultz
dye. These figures are arrived at by adding the total poundage of these
dyes arranged by Norton under each Schultz number in his book,
Artificial Dyestuffs Used in U. S.
Unless otherwise marked, it is to be understood that only one mole-
cule of each intermediate is a part of a dye. Furthermore, when more
than one molecule is employed of the intermediate heading a dye table,
the name of this intermediate is entered under the Other Intermediates
column followed by the number of molecules involved.
A fuller consideration of these principles is to be found in the Intro-
duction. See also abbreviations on page 5.
18
INTERMEDIATES
The intermediates are arranged alphabetically by their chemical
names and by their trivial or common names, and they are accompanied
by the dye tables and other data. See Introduction, or page 18, for
explanation of this arrangement.
A Acid
l:7-Dihydroxy-naphthalene-3:6-disulfonic
herein)
Acenaphthenequinone (C. A. nomen.)
7: 8-Diketo-acenaphthene
CO-CO
Acid (not considered
FORMATION. From acenaphthene by oxidation
LITERATURE. Cain, Intermediate Products (2d Ed.), 242
Dyes Derived from Acenaphthenequinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
907
Ciba Scarlet G
1 J 14: 22,265
2-Hydroxy-thio-
V
I '20: 25,578
naphthene
908
Ciba Red R
I '14: 1,001
2-Hydroxy-thionaph-
V
thene [Bromination]
911
Ciba Orange G
I' 14: 222
5-Amino-2-hydroxy-
V
thionaphthene
3-Acenaphthenol (C. A. nomen.)
See, 3-Hydroxy-acenaphthene
8- Acetamido - 5 - amino - 2> naphthalene - sulfonic Acid (C. A,
nomen.)
See, Acetyl-l:4-riaphthylene-diamine-6-sulfonic Acid
19
- \: : .DYES CLASSIFIED BY INTERMEDIATES
1-Acetamido-anthraquinone
NH . CO . CH 3
= Ci6H u NO,:=265
FORMATION. From 1-amino-anthraquinone by action of acetic an-
hydride on solution in oleum
LITERATURE. Lange, Zwischenprodukte, #3124
Dyes Derived from 1-Acetamido-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
813
Indanthrene
I '14: 1,268
1:6- (or 1:7-) Diacet-
V
Copper R
amido-anthraquinonc
2-Acetamido-anthraquinone
3^265
FORMATION. From 2-amino-anthraquinone by action of acetic an-
hydride on oleum solution
LITERATURE. Lange, Zwischenprodukte, #3124
Dyes Derived from 2-Acetamido-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
812
Indanthrene
I '14: 2,103
1:6- (or 1:7-) Diacet-
V
Orange R T
I '20: 381
amido-anthraquinone
8-Acetamido-l-naphthol-3 : 6-disulf onic Acid
See, Acetyl-H Acid
DYES CLASSIFIED BY INTERMEDIATES
Acetanilide
NH.COCH 3
21
STATISTICS. Manufactured 1917: 1,897,703 Ibs.
Manufactured 1918: 2,085,088 Ibs.
Manufactured 1919: 1,934,125 Ibs.
Manufactured 1920: 2,667,252 Ibs.
FORMATION. By heating aniline with glacial acetic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 52
Lange, Zwischenprodukte, #117
USES. For preparation of p-nitro-acetanilide, and for p-nitro-aniline
Aceto-acetic Ethyl Ester
CH 3 . CO . CH 2 . CO . OC 2 H 5 = C 6 H 10 O 3 = 130
FORMATION. By the reaction of dry sodium ethylate and dry ethyl
acetate
Dyes Derived from Aceto-acetic Ethyl Ester
Schult-
Number
for Dye
Ordinary Name and I
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYES
19
Flavazine L
I '14: 38,908
Aniline
A
Fast Light Yellow
I '20: 9,327
Phenyl-hydrazine-p-
sulfonic Acid
22
Xylene Yellow 3 G
I '14: 23,074
2: 5-Dichloro-phenyl-
A
I '20: 77,782
hydrazine-4-sulfonic
Acid
25
Dianil Yellow 3 G
Primuline-sulfonic Acid
!D
27
Dianil Yellow 2 R
Primuline-sulfonic Acid
D
Phenyl-hydrazine-p-sul-
fonic Acid
ANTHRAQUINONE AND
ALLIED DYES
773
Anthracene Yellow
I '14: 4,046
Pyrogallol
M
N-Acetyl-l-amino-8-naphthol-3 : 6-disulf onic Acid
See, Acetyl-H Acid
22
DYES CLASSIFIED BY INTERMEDIATES
Acetyl-H Acid
JV-Acetyl-l-amino-8-naphthol-3: 6-disulfonic Acid
8-Acetamido-l-naphthol-3:6-disulfonic Acid (C. A. nomen.)
HO NH.CO.CH 3
H0 3 S
S0 3 H
STATISTICS. Manufactured '20: ?
FORMATION. From H acid by acetylation
Dyes Derived from Acetyl-H Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
42
Amido Naphthol
RedG
I '14: 3,500
M '17: ?
Aniline
A
M '18: ?
M'19: ?
M '20: 132,637
I '20: 2,028
66
Amido Naphthol
Red6B
I '14: 45,697
M'18: ?
p-Amino-acetanilide
A
M'19: ?
M '20: 142,567
I '20: 1,299
Acetyl-1: 4-naphthylene-diamine-6-sulfonic Acid
8-Acetamido-5-amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
NH 2
H0 3 S
NH.CO.CHs
FORMATION. From mixture of l-naphthylamine-6-and-7-sulfonic acids
(Cleve's Acids) by acetylation with glacial acetic acid, nitration
with mixed acid, and reduction with iron.
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 152
DYES CLASSIFIED BY INTERMEDIATES
23
Dyes Derived from Acetyl-1 : 4-naphthylene-diamine-6-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
273
Diaminogen Blue BB
I '14: 8,308
a-Naphthylamine
D
M'17: ?
Schaeffer's Acid
I '20: 5,936
[Saponification]
274
Diaminogen B
I '14: 313,629
a-Naphthylamine
D
I '20: 18,120
Gamma Acid
[Saponification]
Acetyl-p-phenylenediamine
See, p-Amino-acetanilide (C. A. nomen.)
o-Acid (of Glaus and Voltz)
See, Croceine Acid
1:2:4 Acid
See, l-Amino-2-naphthol-4-sulfonic Acid
(3 Acid or Beta Acid
See, Anthraquinone-2-sulfonic Acid
d Acid or Delta Acid
See, l-Naphthylamine-4: 8-disulfonic Acid and 2-Naphthyl-
amine-7-sulf onic Acid
e Acid or Epsilon Acid
See, l-Naphthol-3: 8-disulfonic Acid
See, l-Naphthylamine-3 : 8-disulfonic Acid
and 1 : 8-Dihydroxy-naphthalene-3-sulf onic Acid (not con-
sidered herein)
r Acid or Zeta Acid
Naphthasultone-3-sulfonic Acid (not considered herein)
24 DYES CLASSIFIED BY INTERMEDIATES
X Acid or Lambda Acid
See, l-Naphthylamine-2-sulfonic Acid
M Acid or Mu Acid
See, l-Naphthylamine-6-sulfonic Acid
p Acid or Rho Acid
See, Anthraquinone-1 : 5-disulf onic Acid
X Acid or Chi Acid
See, Anthraquinone-1 : 8-disulf onic Acid
Alen's a or Alen's Alpha Acid. (This is generally followed by the class
of the compound, e.g., Alen's a Naphthylamine-disulfonic Acid)
See, Freund's Acid (l-Naphthylamine-3: 6-disulfonic Acid)
l-Nitro-naphthalene-3: 6-disulfonic Acid (not considered
herein)
Alen's |8 or Alen's Beta Acid. (Generally followed by the class of the
compound, e.g., Alen's Naphthylamine-disulfonic Acid)
l-Naphthylamine-3 : 7-disulf onic Acid (not considered herein)
l-Nitro-naphthalene-3 : 7-disulf onic Acid (not considered herein)
Alizarin
1 : 2-Dihydroxy-anthraquinone
a : /3-Dihydroxy-anthraquinone
XXX OH
XX X /~VTT
=:Ci 4 H 8 O 4 = 240
STATISTICS. See #778 in following table
FORMATION. From sodium 2-anthraquinone-sulfonate by fusion with
caustic oda for 2-3 days at 200 C., in autoclave, and in presence of
potassium chlorate
LITERATURE. Schultz, Farbstofftabellen (1914 Ed.), #778
DYES CLASSIFIED BY INTERMEDIATES
25
Dyes Derived from Alizarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
778
Alizarin
I '14: 202,392
M
M'17: ?
M'18: ?
M'19: ?
M'20: ?
I '20: 8,575
779
Alizarin Orange
I '14: 14,239
[Nitration]
M
M'19: ?
M '20: ?
I '20: 500
780
Alizarin Red
I '14: 81,919
[Sulfonation]
M
M'17: ?
I '20: 12,628
781
Erweco Alizarin Acid
[Sulfonation]
M
RedBS
783
Purpurin
[Oxidation]
M
787
Alizarin Bordeaux B
I '20: 20
[Oxidation]
M
788
Alizarin Cyanine R
I '20: 16,781
[Alizarin Bordeaux B,
M
Oxidation]
797
Alizarin Garnet R
I '14: 720
[1-Nitro-alizarin, Re-
M
duction]
798
Alizarin Maroon W
I '20: 2,014
[Crude Nitro-alizarin,
M
Reduction]
799
Alizarin Cyanine G
I '20: 339
[Alizarin Cyanine R,
M
Amidation]
854
Alizarin Viridine DG
I '20: 11,397
[Alizarin Bordeaux B]
M
p-Toluidine (2 mols)
[Sulfonation]
862
Alizarin Blue
I '14: 54,706
[Purpurin]
M
Black B
I '20: 28,802
Aniline
[Sulfonation]
Alpha = a
Note. This is not considered in the alphabetical arrangement,
e.g. alpha-Naphthol is indexed as a-Naphthol under "N."
However (3-Naphthol is placed after a-Naphthol
Alpha-Naphthol
See, a-Naphthol under N.
26 DYES CLASSIFIED BY INTERMEDIATES
p-Amino-acetanilide (C. A. nomen.)
Acetyl-p-phenylene-diamine
NH.CO.CH 3
NH 2
STATISTICS. Imported '14: 6,261 Ibs.
Manufactured '17: ?
Manufactured '18: 177,990 Ibs.
Manufactured '19: 62,567 Ibs.
Manufactured '20: 97,275 Ibs.
FORMATION. From p-nitro-acetanilide by reduction with iron and
acetic acid at not higher than 60 C.
LITERATURE. Cain, Intermediate Products (2d Ed.), 89
Lange, Zwischenprodukte, #558
Dyes Derived from p-Amino-acetanilide
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
61
Victoria Violet
I '14: 52,365
Chromotropic Acid
A
M'17: ?
[Saponification]
M'18: ?
M '19: 105,086
I '20: 2,082
M'20: ?
64
Azo Acid Red B
I '14: 78,305
l-Naphthol-3:6-disul-
A
Lanafuchsine
M'17: ?
fonic Acid
M'18: ?
M'19: 15,272
I '20: 674
M'20: ?
65
Azo Coralline L
M'17: ?
RAcid
A
M'18: ?
M'19: ?
I '20: 249
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
27
Dyes Derived from p-Amino-acetanilide (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
66
Amino Naphthol
I '14: 45,697
Acetyl-H Acid
A
Red6B
M'18: ?
M'19: ?
I '20: 1,299
M '20: 142,567
67
Chromotrope 6B
I '14: 2,818
Chromotropic Acid
A
M'17: ?
M'18: ?
M'19: 77,481
M'20: ?
DISAZO DYES
239
Azotol C
ra-Phenylene-diamine
MF
[Amino-chrysoidine]
/3-Naphthol
243
Coomassie Wool
a-Naphthylamine
A
Black R
Schaeffer's Salt
244
Coomassie Wool
M'18: ?
a-Naphthylamine
A
Black S
M'19: ?
RSalt
290
Violet Black
Nevile-Winther Acid
D
a-Naphthylamine
296
Cotton Yellow G
I '14: 31,472
Salicylic Acid (2 mols)
D
I '20: 4,651
p-Amino-acetanilide (2
mols)
Phosgene
SULFUR DYES
714
Thiophor Yellow
p-Phenylene-diamine
S
Bronze G
Benzidine
[Sulfur]
715
Thiocatechine
[Sulfur]
S
3-Amino-alizarin (C. A. nomen.)
/3-Amino-alizarin
CO OH
FORMATION. From 3-nitro-alizarin by reduction.
28
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3-Ammo-alizarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
803
Alizarin Blue WX
I '14: 319,394
3-Nitro-alizarin
M
M'19: ?
[Glycerol]
I '20: 5,585
804
Alizarin Blue S
I '14: 117,850
3-Nitro-alizarin
M
I '20: 43,679
[Glycerol]
808
Alizarin Green X
I '14: 135,191
3-Nitro-alizarin
M
I '20: 4,254
[Glycerol; Oxidation]
809
Alizarin Indigo
3-Nitro-alizarin
M
BlueS
[Glycerol; Oxidation]
4-Amino-alizarin (C. A. nomen.)
a-Amino-alizarin
OH
lOH
r=C 14 H 9 NO 4 =
STATISTICS. See #797 in following table
FORMATION. From 4-nitro-alizarin by reduction with alkaline sulfides
LITERATURE. Schultz, Farbstofftabellen (1914 Ed.), #797
Dyes Derived from 4-Amino-alizarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
797
Alizarin Garnet R
I '14: 720
[This is 4-Amino-ali-
M
zarin]
805
Alizarin Green S x
I '14: 15,885
[Glycerol]
M
a-Amino-alizarin
See, 4-Amino-alizarin (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
29
/3-Amino-alizarin
See, 3-Amino-alizarin (C. A. nomen.)
2-Amino-5-(p-amino-phenyl)-6enzene-sulfonic Acid (C. A. nomen.
SO S H=1)
See, Benzidine-sulfonic Acid
P-(P-Amino-anilino) -phenol (C. A. nomen.)
See, 4-Amino-4'-hydroxy-diphenylamine
1-Amino-anthraquinone (C. A. nomen.)
a-Amino-anthraquinone
CO
NH 2
FORMATION. (1) From 1-nitro-anthraquinone by reduction with sodium
sulfide
(2) From anthraquinone-1-sulfonic acid (potassium salt) by
heating with 10 per cent ammonia in an autoclave to 180-190
LITERATURE. Ullmann, Enzy. tech. Chemie. 1, 474
Lange, Zwischenprodukte, #3066, 3109, 3158
Dyes Derived from 1-Amino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
814
Algol YeUow W G
I '14: 5,185
Benzoyl chloride
V
I '20: 4
824
Algol Orange R
I '14: 51
2-Chloro-anthraquinone
V
I '20: 406
826
Indanthrene Red G
2 : 6-Dichloro-anthraqui-
none
1 - Amino-ant hraquinone
(2 mols)
830
Indanthrene Red R
I '14: 2,099
2 : 7-Dichloro-anthra-
V
I '20: 6,595
quinone
1-Amino-anthraqui-
none (2 mols)
834
Algol Gray B
I '14: 1,192
1-Chloro-anthraquinone
V
I '20: 840
[Nitration, Reduction]
870
Algol Corinth R
I '20: 134
2-Chloro-anthraquinone
V
[Nitration, Reduction]
Benzoyl chloride
30
DYES CLASSIFIED BY INTERMEDIATES
2-Amino-anthraquinone (C. A. nomen.)
/3-Amino-anthraquinone
STATISTICS. Manufactured '19: ?
Manufactured '20:?
FORMATION. From sodium anthraquinone-2-sulfonate by heating with
ammonia water in an autoclave at 200 C., preferably in the presence
of an oxidizing substance
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 476
Lange, Zwischenprodukte, #3107
Cain, Intermediate Products (2d Ed.), 254
Dyes Derived from 2-Amino-anthraquinone
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQITINONE AND
ALLIED DYES
810
Helidone
I '14: 20,744
2-Amino-anthraquinone
Yellow 3 G N
I '20: 2,515
(2 mols)
V
Phosgene
811
Algol Yellow 3G
I '14: 1,604
2-Amino-anthraquinone
I '20: 570
(2 mols)
V
*
[Succinic acid]
825
Algol Red B
I '14: 2,399
4-Bromo-N-methyl-
V
I '20: 4,151
anthrapyridone
837
Indanthrene Blue R
I '14: 500
2-Amino-anthraquinone
V
(2 mols)
838
Indanthrene Blue
I '14: 187,379
2-Amino-anthraquinone
V
RS
M'17: ?
(2 mols)
I '20: 16,385
[Alkaline Reduction]
M'20: ?
[or Indanthrene Blue
R reduced]
846
Indanthrene Dark
2-Amino-anthraqui-
V
Blue BT
none (2 mols)
[Glycerol (4 mols)]
[or Benzanthrone-quin-
oline (2 mols)]
DYES CLASSIFIED BY INTERMEDIATES
31
Dyes Derived from 2-Amino-anthraquinone (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
(continued)
849
Indanthrene Yellow
I '14: 75,192
2-Amino-anthraquinone
V
G
M'19: ?
(2 mols)
I '20: 75,665
M'20: ?
867
Indanthrene Brown
I '14: 6,175
2-Amino-anthraquinone
V
B
I '20: 3,511
(2 mols)
1 : 5- and 1 : 8-Amino-anthraquinone-sulf onic Acids
5-and 8-Amino-l-emthraquinone-sulfonic Acids (C. A. nomeri)
(H0 3 S) co NH 2
303
H0 3 S
FORMATION. Anthraquinone is sulfonated to a mixture of 1 : 5-and
1 : 8-disulfonic acids, which are then partly amidated by treatment
with ammonia
LITERATURE. Cain, Intermediate Products (2d Ed.), 252
Ullmann, Enzy. tech. Chemie, 1, 475
Lange, Zwischenprodukte, #3265
Dye Derived from 1: 5- and 1: 8-Amino-anthraquinone-sulf onic Acids
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
851
Alizarin Direct
1 '14: 10,201
[Dibromination]
A
BlueB
I '20: 2,982
Aniline
[Sulfonation]
32
DYES CLASSIFIED BY INTERMEDIATES
Amino-azo-benzene
Phenyl-azo-aniline (C. A. nomen.)
N
STATISTICS. Imported '14: very small
Manufactured '17: 141,888 Ibs.
Manufactured '18: 171,594 Ibs.
Manufactured '19: 82,755 Ibs.
Manufactured '20: 152,310 Ibs.
FORMATION. The amino-azo-benzene is prepared from aniline, by
molecular rearrangement of diazo-amino-benzene, which in turn is
made from aniline and diazo-benzene chloride (diazotized aniline)
LITERATURE. Cain, Intermediate Products (2d Ed.), 81
Dyes Derived from Amino-azo-benzene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
31
Amino-azo-benzene
M'17: ?
S3
Spirit Yellow
M'18: 52,283
M'19: ?
M'20: ?
137
Fast Yellow
I '14: 37,378
[Oleum]
A
Acid Yellow
M'17: ?
M'18: ?
I '20: 7,848
M'20: ?
DISAZO DYES
223
Sudan III
I '14: 2,409
0-Naphthol
S3
M '17: ?
MF
M'18: ?
M'19: ?
M'20: ?
224
Cloth Red G
I '14: 401
Nevile-Winther Acid
A
M'19: ?
M'20: ?
225
Croceine AZ
I '14: 500
l-Naphthol-3: 6-disul-
A
'20: 100
fonic Acid
226
Croceine B
l-Naphthol-4: 8-disul-
A
fonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-azo-benzene (continued)
33
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
227
Brilliant
I '14: 125,137
GAcid
A
Croceine M
M'17: ?
M'18: 84,643
M '19: 157,509
I '20: 49
M '20: 129,124
228 '
Ponceau 5R
I '14: 2,880
2-Naphthol-3:6:8-
A
Erythrine P
M'17: ?
trisulfonic Acid
M'19: ?
229
Azo Acid Violet
I '14: 150
1 : 8-Dihydroxy-naph-
A
I '20: 11
thalene-4-sulfonic
M'20: ?
Acid
279
Benzo Fast Scarlet
I '14: 36,674
J Acid
D
M'19: ?
Phosgene
I '20: 24,153
AZINE DYES
696
Indamine Blue
Aniline (excess)
B
697
Induline (Spirit
I '14: 25,342
Aniline (excess)
S3
Soluble)
M'17: ?
M'18: 8,589
M'19: 436,201
M '20: 140,400
699
Induline (Water
I '14: 29,177
Aniline (excess)
A
Soluble)
M'17: 183,739
[Sulfonation]
M'18: 91,724
M'19: 130,704
I '20: 500
M '20: 168,048
701
Paraphenylene
p-Phenylene-diamine
B
BlueR
Amino-azo-benzene-disulfonic Acid
6-Amino-3 : 4'-azo-bis6enzene-sulf onic Acid (C. A. nomen.)
S0 3 H
Ci 2 HiiN 3 O 6 S 2 357
OBMATION. From amino-azo-benzene by sulfonation with oleum
34 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-azo-benzene-disulfonic Acid
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
247
Double Scarlet
I '14: 39,522
/3-Naphthol
A
Scarlet EC
M'17: ?
M'18: 74,203
M'19: ?
M'20: ?
251
Croceine Scarlet
I '20: 100
Croceine Acid
A
Amino-azo-benzene-sulfonic Acid
p-(p-Amino-phenyl-azo)-6enzene-sulfonic Acid (C. A. nomen.)
= 277
FORMATION. From amino-azo-benzene by sulfonation at low tempera-
ture by means of oleum
Dyes Derived from Amino-azo-benzene-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
246
Cloth Scarlet G
I '14: 9
I '17: ?
/3-Naphthol
A
I '18: ?
I '19: ?
I '20: ?
248
249
250
Fast Scarlet B
Croceine Scarlet 3B
Milling Orange
I '14: 1,755
I '14: 9,613
I '14: 4,370
Schaeffer's Acid
Croceine Acid
Salicylic Acid
A
A
M
6-Amino-3: 4'-azo-bis6enzene-sulfonic Acid (C. A. nomen.}
See, Amino-azo-benzene-disulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
a-Amino-azo-naphthalene
4-(Naphthyl-azo)-l-naphthylamine (C. A. nomen.)
35
\-N:N-?
= C 2 oH 15 N 3 =:297
H 2 N
FORMATION. From a-naphthylamine, this compound is prepared by
mixing equal molecules of a-diazo-naphthalene chloride (from
a-naphthylamine) and a-naphthylamine hydrochloride in cold
aqueous solution.
Dyes Derived from a-Amino-azo-naphthalene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
694
Rose Magdala
I '14: 597
a-Naphthylamine
A
Fast Pink for Silk
695
Paraphenylene Violet
I '20: 337
p-Phenylene-diamine
B
o-Amino-azo-toluene
p-(o-Tolyl-azo)-o-foluidine (C. A. nomen.)
CH 3 CH 3
=C 14 H 15 N 3 = 225
STATISTICS. Manufactured 1917: 14,355 Ibs.
Manufactured 1918- ?
Manufactured 1919: 4,836
Manufactured 1920: ?
FORMATION. From o-toluidine, by molecular rearrangement of diazo-
amino-toluene, which in turn is made by the reaction of equal
molecules of o-toluidine and diazo-toluene chloride (diazotized
o-toluidine)
LITERATURE. Cain, Intermediate Products (2d Ed.), 82.
36
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Amino-azo-toluene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
68
Spirit Yellow R
[This is amino-azo-
ss
Yellow Fat Color
toluene]
149
Fast YeUow R
[Oleum]
A
DISAZO DYES
230
Cloth Red 3 GA
I '14: 251
Bronner's Acid
M
231
Cloth Red 3B Extra
I '14: 15
Ethyl-2-naphthjd-
M
I '20: 84
amine-7-sulfonic Acid
232
Sudan IV
I '14: 51
/3-Naphthol
ss
M'17: 13,334
MF
M'18: 14,904
M'19: ?
M'20: ?
233
Cloth Red B
I '14: 1,962
Nevile-Winther Acid
M
t
M'18: ?
M'19: ?
M '20: ?
234
Cloth Red G
I '14: 554
Schaeffer's Acid
M
235
Croceine 3B
M'19: ?
l-Naphthol-4: 8-disul-
A
M'20: ?
fonic Acid
236
Cloth Red B
I '14: 14,293
RAcid
A
Wool Red B
M'17: ?
M'18: ?
M'19: ?
M'20: ?
o-Amino-azo-toluene-sulfonic Acid
4-(4-Amino-ra-tolyl-azo)-w-foluene-sulfomc Acid (C. A. nomen.)
CH
CH
FORMATION. o-Amino-azo-toluene is sulfonated with oleum
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Amino-azo-toluene-sulfonic Acid
37
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
252
253
Cloth Scarlet R
Orseilline BB
/3-Naphthol
Nevile-Winther's Acid
M
A
254
Bordeaux G
Schaeffer's Acid
A
255
Croceine Scarlet 8B
Ponceau 6RB
I '14: 2,379
I '20: 154
Croceine Acid
A
Amino-azo-xylene
4-(2: 4-Xylyl-azo)-2: 5-zylidine (C. A. nomen.)
H 3 C
FORMATION. From xylidine, and by action of diazo-ra-xylidine (2:4-
xylidine) on p-xylidine (2: 5-xylidine)
LITERATURE. Nolting and Forel, Ber. 18, 2668 (1885)
Nietzki, Ber. 13, 471 (1880)
Schultz, Chemie Steinkohlenteers 1, 137
Dyes Derived from Amin6-azo-xylene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
237
Bordeaux BX
Schaeffer's Acid
A
238
Union Fast Claret
R Acid
A
m- Ammo -6enz aldehyde
HCO
NH 2 =
38
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Benzaldehyde is nitrated, resulting in a mixture of o- and
w-nitro-benzaldehyde (20 and 80 per cent). The reduction is
effected and the o-derivative is removed by treating the crude
nitration mixture with sodium hydrosulfite and hydrochloric acid,
whereupon the o-derivative crystallizes out as the anhydro-
derivative of o-amino-benzaldehyole. The solution contains the
m-amino-benzaldehyde, and it is used directly
LITERATURE. Cain, Intermediate Products (2d Ed.), 144, 145
Lange, Zwischenprodukte, #316-318
USES. For preparation of m-Hydroxy-benzaldehyde
P-Amino-6enz aldehyde
HCO
NH 2
FORMATION. p-Nitro-toluene, in alcoholic solution, is run into a solu-
tion of sulfu in caustic soda; and the mixture is heated under a
reflux condenser for 1J hours, and then separated
LITERATURE. Lange, Zwischenprodukte, #319-327
Ullmann, Enzy. tech. Chemie, 2, 307
Dyes Derived from p-Amino-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
129
Chromazone Red A
T14: 243
Chromotropic Acid
M
130
Chromazone Blue R
Chromotropic Acid
M
Ethyl-phenyl-hydrazine
p-Amino-6enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)
See, p-Amino-benzylidine-ethyl-phenyl-hydrazone
l-Amino-4-benzamido-anthraquinone (C. A. nomen.)
See, l-Amino-4-benzoylamino-anthraquinone
DYES CLASSIFIED BY INTERMEDIATES
39
2-Amino-p-6enzene-disulfonic Acid (C. A. nomen.}
Aniline-2 : 5-disulf onic Acid
S0 3 H
/\NH 2 = c H NO S =: 253
\/
S0 3 H
FORMATION. The sodium salt of 4-chloro-3-nitro-benzene-sulfonate is
boiled with sodium sulfite, resulting in formation of sodium 2-nitro-
benzene-disulfonate, which is reduced with iron and acetic acid to
aniline-2: 5-disulf onic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 49
Lange, Zwischenprodukte, #957
USES. For preparation of ethyl-w-amino-phenol
4-Amino-/n-6enzene-disulfonic Acid (C. A. nomen.}
Aniline-2 : 4-disulf onic Acid
S0 3 H
S0 3 H
' 253
NH 2
FORMATION. By heating sulfanilic acid (p-aniline-sulfonic acid) with
oleum at 170-180 C.
LITERATURE. Ann. 198, 17
Beilstein, Organische Chemie (3 auf.) II, 571
Dye Derived from 4-Amino-/n-6enzene-disulfomc Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
263
Jet Black R
a-Naphthylamine
Phenyl-a-naphthyl-
A
amine
m-Amino-benzene-sulfonic Acid
See, Metanilic Acid
40 DYES CLASSIFIED BY INTERMEDIATES
p-Amino-benzene-sulfonic Acid
See, Sulfanilic Acid
Amino-benzenyl-o-amino-thio-cresol
See, Dehydro-thio-p-toluidine
m-Amino-6enzoic Acid
COOH
137
FORMATION. m-Nitrobenzoic acid is reduced with iron and acetic acid
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 333
Dyes Derived from /n-Amino-benzoic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
203
Yellow Fast-to-soap
Diphenylamine
M
204
Diamond Yellow G
Salicylic Acid
M
TETRAKISAZO DYE
486
Direct Brown J
I '14: 3,640
w-Phenylene-diamine
D
(3 mols)
m-Amino-benzoic Acid
(2 mols)
o-Amino-benzoic Acid
See, Anthranilic Acid
l-Amino-4-benzoylamino-anthraquinone
l-Amino-4-benzamido-anthraquinone (C. A. nomen.)
CO NH2
r=C 21 H 14 N 2 3 =:342
NH . COC 6 H 6
DYES CLASSIFIED BY INTERMEDIATES
41
FORMATION. By heating 1 : 4-Diaminoanthraquinone in a toluene or
nitro-benzene solution with benzoyl chloride
LITERATURE. Cf. UUmann, Enzy. tech. Chemie, 1, 164
Dye Derived from l-Amino-4-berLzoylamino-anthraquinone
Schultz
X umber
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
c/itton
Class
AXTHRAQUINONE AND
ALLIED DYES
833
Algol Olive R
1 '14: 13,334
l-Benzoylamino-4-
V
I '20: 461
chloro-anthraquinone
[Chloro-sulfonic Acid]
p-Amino-benzyl-diethylamine
p-Amino-A r : A r -diethyl-l>enzylamine (C. A. nomen.)
FORMATION. p-Nitro-benzyl chloride is treated with 2 mols of diethyl-
amine in alcoholic solution at 100 C.; and the resulting p-nitro-
benzyl-diethylamine is reduced with SnCk and HC1 to the p-amino-
benzyl-diethylamine
LiTEBATUBE. ^Ber. 28, 1141
Cf. Lange, Zwischenprodukte, #255
Dye Derived from p-Amino-benzyl-diethylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Appli-
rsjtifjn
Class
TRISAZO DYE
435
Janus Brown B
a-Xaphthylamine
B
Resorcinol or jw-phenyl-
ene-diamine
[or Chrysoidine]
42
DYES CLASSIFIED BY INTERMEDIATES
o-Amino-benzyl-dimethylamine
o-Amino-A r :N-dimethyl-&enzylamine (C. A. nomen.)
CH 2 .N(CH 3 ) 2
NH ' =
150
FORMATION. o-Nitro-benzyl chloride is treated with 2 mols of dimethyl-
amine in alcoholic solution at 100 C., and the resulting o-nitro-
benzyl-dimethylamine is reduced with SnCl 2 and HC1 to the
o-amino-benzyl-dimethylamine
LITERATURE. Cf. Ber. 28, 1141
Cf. Lange, Zwischenprodukte, #250, 255
Dyes Derived from o-Amino-benzyl-dimethylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
74
MONOAZO DYES
Tannin Orange
I '14: 2,202
I '20: 349
p-Amino-benzyl-di-
methylamine
/3-Naphthol (2 mols)
B
75
New Phosphine G
I '14: 500
p-Amino-benzyl-di-
m'ethylamine
Resorcinol (2 mols)
B
p-Amino-benzyl-dimethylamine
p-Ammo-N: N-dimethyl-frenzylaimne (C. A. nomen.)
CH 2 . N(CH 3 ) 2
NH 2
FORMATION. p-Nitro-benzyl chloride is treated with 2 mols of dimethyl -
amine in alcoholic solution at 100 C.; and the resulting p-nitro-
benzyl-dimethylamine is reduced with SnCl 2 and HC1 to the p-
amino-benzyl-dimethylamine
LITERATURE. Ber. 28, 1141
Lange, Zwischenprodukte, #255
DYES CLASSIFIED BY INTERMEDIATES
43
Dyes Derived from p-Amino-benzyl-dimethylamine
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
74
MONOAZO DYES
Tannin Orange R
I '14: 2,202
I '20: 249
o-Amino-benzyl-di-
methylamine
!(3-Naphthol (2 mols)
B
75
New Phosphine G
I '14: 500
o-Amino-benzyl-di-
methylamine
Resorcinol (2 mols)
B
p-Amino-benzyl-ethyl-aniline-sulfonic Acid
See, Ethyl-sulfobenzyl-p-phenylene-diamine
p-Amino-benzylidene-ethyl-phenyl-hydrazone
Ethyl-phenyl-hydrazone of p-Amino-benzaldehyde
p-Amino-6enzaldehyde Ethyl-phenyl-hydrazone (C. A. nomen.)
/C2H5
HC:N.N<
X C 6 H 5
NH 2
FORMATION. By condensation of ethyl-phenyl-hydrazine and p-amino-
benzaldehyde
Dye Derived from p-Amino-benzylidene-ethyl-phenyl-hydrazone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
130
MONOAZO DYE
Chromazone Blue R
Chromotropic Acid
M
44 DYES CLASSIFIED BY INTERMEDIATES
l-Amino-2-bromo-4-hydroxy-anthraquinone
4-Amino-3-bromo-l-hydroxy-anthraquinone (C. A nomen.)
rr c V>
^coA; H
Ci4H 8 BrN0 3 318
FORMATION. From l-amino-2 : 4-dibromo-anthraquinone by heating
with monohydrate at 100-110
LITERATURE. Lange, Zwischenprodukte, #3314
Dye Derived from l-Amino-2-bromo-4-hydroxy-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
844
Algol Blue 3G
I '14: 9,191
l-Amino-2-bromo-4-
V
I '20: 3,896
hydroxy-anthraqui-
none (2 mols)
4-Amino-3-bromo-l-hydroxy-anthraquinone (C. A. nomen.)
See, l-Amino-2-bromo-4-hydroxy-anthraquinone
l-Amino-4-bromo-2-methyl-anthraquinone
= Ci 5 H 10 BrN0 2 = 316
Br
FORMATION. 2-methyl-anthraquinone (which is obtained by the con-
densation of toluene with phthalic anhydride) is nitrated and
reduced. The resulting l-amino-2-methyl-anthraquinone is bromi-
nated in a glacial acetic acid solution and the l-amino-4-bromo-
2-methyl-anthraquinone is formed
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 486
Barnett, Anthracene and Anthraquinone, 80, 192, 229
Cain, Intermediate Products (2d Ed.), 260
DYES CLASSIFIED BY INTERMEDIATES 45
Dyes Derived from l-Amino-4-bromo-2-methyl-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Uied and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
859
Cyananthrol R
I '14: 18,792
p-Toluidine
A
I '20: 2,416
[Sulfonation]
860
Cyananthrol G
I '20: 5,127
p-Toluidine
A
[Sulfonation]
l-Amino-6-chloro-anthraquinone
,ca
ci
Dye Derived from l-Amino-6-chloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
V
827
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
Bordeaux B extra
I '14: 28,728
I '20: 4,056
l-Amino-6-chloro-an-
thraquinone (2 mols)
2: 7-Dichloro- anthra-
qumone
2-Amino-6-chloro-6enzene-sulfonic Acid (C. A. nomen.)
3-Chloro-aniline-2-sulfonic Acid
m-Chloro-aniline-o-sulfonic Acid
S0 3 H
Cl, |NH 2 _.
207.5
FORMATION. By the reduction of m-chloro-nitro-benzene-o-sulfonic
acid in the usual way.
46 DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Beil. II, 571
Dye Derived from 2-Amino-6-chloro-benzene-sulfonic Acid
Schultz
Number
JOT Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
131
MONOAZO DYE
Permanent Orange R
/3-Naphthol
CL
l-Amino-4-chloro-3-methyl-benzene-6-sulfonic Acid
, 2-Amino-5-chloro-p-foluene-sulfonic Acid (C. A. nomen.
2-Amino-5-chloro-p-toluene-sulfonic Acid (C. A. nomen.
2-Chloro-5-toluidine-4-sulfonic Acid (CH$ = 1)
l-Amino-4-chloro-3-methyl-benzene-6-sulfonic Acid
S0 3 H
NH2 = C 7 H 8 C1N0 3 S = 221.5
STATISTICS. Manufactured '20: 22,753 Ibs
FORMATION. From o-chloro-toluene-p-sulfonic acid (CH 3 = 1) by nitra-
tion and subsequent reduction
LITERATURE. Lange, Zwischenprodukte, #1022
Dye Derived from2-Amino-5-chloro-p-toluene-sulfonic Acid (S0 3 H=1)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
153
Lake Red C
I '14: 306,607
/3-Naphthol
CL
M'19: ?
I '20: 4,105
DYES CLASSIFIED BY INTERMEDIATES 47
4-Amino-chrysoidine (C.A. nomen.)
2:4: 4'-Triamino-azo-benzene
H 2 N
" = Ci 2 Hi 3 N 5 = 227
FORMATION. (1) p-Amino-acetanilide (acetyl-p-phenylene-diamine) is
diazotized and combined with m-phenylene-diamine, and then the
acetyl group removed
(2) p-Nitro-aniline is diazotized and combined with w-phenylene-
diamine, and the product reduced with sodium sulfide
LITERATURE. Lange, Zwischenprodukte, #1765
Dye Derived from 4-Amino-chrysoidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
239
DISAZO DYE
Azotol C
jS-Naphthol
MF
2-Amino-p-cresol (OH=1, C.A.nomen.)
w-Amino-p-cresol (CHz=l)
3-Amino-p-cresol (Eng. and Germ, nomen.
C 7 H 9 NO=:123
FORMATION. (1) p-Cresol is nitrated and then reduced with SnCl 2 and
HC1. (2) p-Toluidine is treated with nitric and nitrous acids so as
to form 2-nitro-p-cresol (OH = 1), which is then reduced to the
amino compound
LITERATURE. Ber. 22, 348; 24, 1960
Beil. II, 752
48 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2-Amino-p-cresol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
260
Eric-Chrome
I '14: 882
Sulfanilic acid
ACr
Verdon
jS-Naphthol
3-Amino-p-cresol (Eng. andGer. nomen. CH 3 = 1)
See, 2-Amino-p-cresol (OH =1, C. A. nomen.)
3-Amino-p-cresol (OH=1, C. A. nomen.)
6-Amino-p-cresol (CH 3 =1)
o-Amino-p-cresol (CH 3 = 1 , Ger. and English nomen.}
OH
FORMATION. p-Toluidine is nitrated, and the 3-nitro-p-toluidine
sulfate (NH 2 = 1) therefrom is treated with NaN0 2 in the cold
and then boiled with dilute sulfuric acid, thus forming 3-nitro-p-
cresol, which latter on reduction with SnCl 2 and HC1 gives 3-amino-
p-cresol
LITERATURE. Beil. II, 751, 753
Dye Derived from 3-Amino-p-cresol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
576
Rhodamine 3G
I '14: 19,568
Dimetliylamino - hy-
B
I '20: 855
droxy - benzoyl- ben-
zoic acid
[Ethyl esterification]
6- Amino-p-cresol (CH 3 =1)
See 3-Amino-p-cresol (OH =1, C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
m-Amino-p-cresol (CH 3 = 1)
See, 2-Amino-p-cresol (OH = 1, C. A. nomen.)
o-Amino-p-cresol (CH Z =1)
See, 3-Amino-p-cresol (OH = 1 , C. A . nomen.)
2-Amino-/>-cresol Methyl Ether (OCH 3 =1)
6-Methoxy-ra-toluidine (C. A. nomen. NH Z =1)
m-Amino-p-cresol Methyl Ether (CH S =1)
3-Amino-4-cresol Methyl Ether (CN 3 =1)
OCH 3
49
CH 3
FORMATION. 2-Nitro-p-cresol (OH = 1), obtained by action of nitrous
and excess nitric acids upon p-toluidine, is methylated and reduced
LITERATURE. Ber. 22, 348; 24, 960
Dyes Derived from 2-Amino-/>-cresol Methyl Ether (OCH Z =1)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
96
MONOAZO DYES
Chrome Fast
Yellow GG
I '14: 150
I '20: 500
Salicylic Acid
M
100
Eosamine B
I '14: 1,914
I '20: 1,600
l-Naphthol-3:8-disul-
fonic Acid
A
101
Goccinine B
RAcid
A
439
TRISAZO DYES
Direct Indigo Blue A
M'18: ?
Benzidine
H Acid (2 mols)
D
440
Direct Indigo
Blue BK
Benzidine
Gamma Acid (2 mols)
D
50
DYES CLASSIFIED BY INTERMEDIATES
m-Amino-/>-cresol Methyl Ether (CH S =1)
See, 2-Amino-p-cresol Methyl Ether (OCH Z =
l-Amino-2: 4-dibromo-snthraquinone
CO
CO
2
Br
Br
FORMATION. 1-Amino-anthraquinone is treated in nitro-benzene solu-
tion and at about 120-130 with an excess of bromine
LITERATURE. Ullmann, Enzy. tech Chemie, 1, 475
Ger. Pat., 160,169
Dye Derived from l-Amino-2: 4-dibromo-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
855
Alizarin Pure Blue B
p-Toluidine
ACr
[Sulfonation]
2-Amino-4: 6- dichloro -phenol
OH
1 | | NH2 = C 6 H 5 C1 2 NO 178
1
FORMATION. 4: 6-Dichloro-2-nitro-phenol is reduced with tin and
hydrochloric acid
LITERATURE. Beil. II, 727
Dye Derived from 2-Amino-4: 6-dichloro-phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
86
MONOAZO DYE
Azarine S
0-Naphthol
M
DYES CLASSIFIED BY INTERMEDIATES 51
4-Amino-l-diethylamino-benzene-3-thiosulfonic Acid
See, Diethyl-p-phenylene-diamine4hiosulfonic Acid
p -Ami no - die thyl - aniline
See, N: AT-Diethyl-p-phenylene-diamine (C A. nomen.)
/>-Amino-diethyl-aniline-thiosulfonic Acid
See, Diethyl-p-phenylene-diamine-thiosulfonic Acid
p-Ammo-N: AT-diethyl-benzylamine (C. A. nomen.)
See, p-Amino-benzyl-diethylamine
2-Amino-5-dimethylamino-6enzene-thiosulfonic Acid (C. A.
nomen.)
See, Dimethyl-p-phenylene-diam'ne-thiosulfonic Acid
m-Amino-dimethyl-aniline
See N: N Dimethyl-w-phenylene-diamine C. A. nomen.)
/>-Amino-dimethyl-aniline
See, N: AT-Dimethyl-p-phenylene-diamine (C. A. nomen.)
j)-Amino-dimethyl-aniline-thiosulfonic Acid
See, D!methyl-p-phenylene-diamine-thiosulfonic Acid
o-Amino-AT: AT-dimethyl-ftenzylainine (C. A. nomen.)
See, o-Amino-benzyl-dimethylamine
p-A.min.o-N: ^V-dimethyl-feenzylamine (C. A. nomen.)
See, p-Amino-benzyl-dimethylamine
4'-Amino-2 : 4-dinitro-diphenylamine
N- 2: 4-Dinitro-phenyl)-p-phenylene-diamine (C. A. nomen.)
N0 2
2N ~ NH ~ NH 2 Ci2Hi Q N 4 04 = 274
52
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. l-Ch'oro-2: 4-dinitro-benzene is condensed with p-phenyl-
ene-diamine
LITERATURE. Lange, Zwischenprodukte, #1666
Dye Derived from 4'-Amino-2 : 4-dinitro-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
727
SULFUR DYE
Auronal Black B
[Glycerol; S+Na.S]
S
o-Amino-diphenylamine
JV-Phenyl-o-phenylene-diamine (C. A. nomen.)
NH 2
<^\=rC 12 H 12 N 2 = 184
FORMATION. By reducing o-nitro-diphenylamine (from o-bromo-nitro-
benzene and aniline) by heating with ammonium sulfide
LITERATURE. Lange, Zwischenprodukte, #1611
Chem. Zeitung, 18, 1095
Ber. 23, 1843
Dye Derived from o-Amino-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
668
AZINE DYE
Flavinduline O
'14: 660
Phenanthrene-quinone
B
^-Amino-diphenylamine
JV-Phenyl-p-ph nylene-diamine (C. A. nomen.)
= Ci 2 H 12 N 2 = 184
DYES CLASSIFIED BY INTERMEDIATES
53
FORMATION. This intermediate can be prepared by reducing Orange
IV, by means of sodium sulfide and sulfur. The Orange IV
results from the coupling of diazotized sulfanilic acid with di
phenylamine
LITERATURE. Lange, Zwischenprodukte, #1611
Cain, Intermediate Products (2d Ed.), 74
Dyes Derived from />-Amino-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
687
Rosolan
I '20: 1,083
Aniline
o-Toluidine
B
ANILINE BLACK
[Oxidation]
GROUP
922
Diphenyl Black
I '14: 1,470
M'19: ?
M'20: ?
p-Amino-diphenyl-
amine (x mols)
[Oxidation]
Special
/>-Amino-diphenylamine-2-sulonic Acid
2-Anilino-5-amino-6enzene-sulfonic Acid (C. A. nomen.)
H 2 N
S0 8 H
NH
FORMATION.- p-Chloro-nitro-benzene is sulfonated to 2-chloro-5-nitro-
benzene-sulfonate, which latter in presence of glycerol and sodium
carbonate is condensed with aniline to form p-nitro-diphenylamine-
2-sulfonic acid. This is reduced by iron and hydrochloric acid,
resulting in p-amino-diphenylamine-2-sulfonic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 75
Cf. Lange, Zwischenprodukte, #1646, 1647
USES. For preparation of the Nerol Dyes
54 DYES CLASSIFIED BY INTERMEDIATES
a- (-Amino-W-ethyl-aniIino)-/>- toluene -sulfonic Acid (C. A.
rumen.)
See, Ethyl-sulfobenzyl-p-phenylene-diamine
a-(4-Amino-^-ethyl-3-sulfomercapto-anilino)-j)-toluene-sulfonic
Acid (C. A. nomen.)
See, Ethyl-sulfobenzyl -p-phenylene-diamine-thiosulf onic Acid
/>-Amino-ethyl-o-toluidine
See, Af 3 -Ethyl-4-ra-tolyene-diamine (C. A. nomen.
^-Amino-ethyl-o-toluidine
See, JV^Ethyl-p-tolylene-diamine
Amino-G Acid 1
2-Naphthylamine-6: 8-disulfonic Acid
7-Amino-l : 3-naphthalene-disulf onic Acid (C. A . nomen.)
/3-Naphthylamine-7-disulfonic Acid
/3-Naphthylamine-disulfonic Acid G
H0 3 S
STATISTICS. Manufactured 1918: ?
Manufactured 1919: ?
Manufactured 1920: 894,624 Ibs.
FORMATION. From G acid, by heating the sodium salt with ammonia
and sodium bisulfite solution, in an autoclave under pressure
LITERATURE. Lange, Zwischenprodukte, #2599
Cain, Intermediate Products (2d Ed.), 209
1 Occasionally in the older literature, this 2-naphthylamine-6 : 8-disulfonic Acid
has been called G Acid.
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-G Acid
55
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
178
MONOAZO DYE
Crumpsall Yellow
Salicylic Acid
A
270
DISAZO DYES
Brilliant Croceine 9B
Aniline
G and R Acids
A
271
Diamine Blue 6G
1 - Amino-2-naphthol
ethyl ether
/3-Naphthol
D
272
Naphthol Black B
Brilliant Black B
I '14: 103,598
M'19: ? .
I '20: 50
a-Naphthylamine
R Acid
A
l-Amino-4-hydroxy-anthraquinone
4-Amino-l-hydroxy-anthraquinone (C. A. nomen.)
NH 2
OH
FORMATION. (1) From quinazarin by heating with ammonia. (2) From
1-amino-anthraquinone by heating with sulfuric acid (66 Be.) and
boric acid to 180-200 C. "
LITERATURE. Lange, Zwischenprodukte, #3253-3255
Dye Derived from l-Amino-4-hydroxy-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
818
Algol Pink R
I '14: 126
Benzoyl chlqride
V
I '20: 1,368
56
DYES CLASSIFIED BY INTERMEDIATES
4-Amino-l-hydroxy-anthraquinone (C. A. nomen.)
See, l-Amino-4-hydroxy-anthraquinone
4-Amino-4 / -hydroxy-diphenylainine
p-(p-Amino-anilino) -phenol (C. A. nomen.)
H 2 N
NH
FORMATION. From phenol and p-phenylene-diamine by oxidation at
low temperature
LITERATURE. Lange, Zwischenprodukte, #1639-1643
Dye Derived from 4-Amino-4'-hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
732
Autogene Black
I '14: 7,495
Phenol
s
[S 2 C1 2 ; S + NasS]
2-Amino-7-hydroxy-diphenylenazine
See, 2-Amino-8-hydroxy-phenazine
2-Amino-4'-hydroxy-4-nitro-diphenylamine
4-Nitro-2-amino-4'-hydroxy-diphenylamine
p-(2-Amino-4-nitro-anilino) -phenol -(C. A. nomen.)
NH 2
NH ^"^OH Ci 2 HiiN 3 3 = 245
FORMATION. Chloro-dinitro-benzene is condensed with p-amino-
phenol in presence of an acetate to 2: 4-dinitro-4'-hydroxy-di-
phenylamine, which by partial reduction furnishes the above de-
rivative.
LITERATURE. Beil II, spl, 399; IV, spl, 397
Lange, Zwischenprodukte, #1670
Thorpe, Die. Chemistry, 2, 245
DYES CLASSIFIED BY INTERMEDIATES 57
Dyes Derived from 2-Amino-4'-hydroxy-4-nitro-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
726
SULFUR DYES
Pyrogene Direct Blue
Pyrogene Blue
I '14: 10,934
I '20: 2,498
[Alcohol; S+NasS]
S
730
Pyrogene Black G
I '14: 8,725
[S+Na^S; It is not cer-
tain that the amino-hy-
droxy - nitro - diphenyl-
amine referred to is
the one with the posi-
tions given above]
S
736
Thion Blue B
I '14: 7,353
I '20: 11,855
[CSa; S+NasS]
S
2-Amino-8-hydroxy-phenazine
2-Amino-7-hydroxy-diphenylenazine
8-Amino-2-phenazinol (C. A. nomen.)
HO
N-
N
NH 2
C 12 H 9 N 3 211
FORMATION. l-Chloro-2 : 4-dinitro-benzene condensed with p-amino-
phenol, the product reduced, and the resulting diamino-hydroxy-
diphenylamine oxidized in alkaline solution with manganese dioxide
LITERATURE. Lange, Zwischenprodukte, #1969
Cain, Intermediate Products (2d Ed.), 83
Dye Derived from 2-Amino-8-hydroxy-phenazine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
739
Immedial
I '14: 15,496
[S+NasS]
S
Bordeaux G
Immedial Maroon B
58 DYES CLASSIFIED BY INTERMEDIATES
5-Amino-2-hydroxy-^hionaphthene (C.A. numbering}
6-Amino-3-hydroxy-thionaphthene (German numbering)
\
H or
CH 2 =C 8 H 7 NOS 165
H 2 N
FORMATION. 4-Acetamido-2-amino-benzoic acid is diazotized, reacted
first with potassium xanthate (C2H 5 O . CS . SK) and then with
chloro-acetic acid, forming 4-acetamido-2-thioglycolic-benzoic acid,
which by melting forms the desired 5-amino-2-hydroxy-thio-
naphthene
LITERATURE. Lange, Zwischenprodukte, #2166
Ullmann, Enz. tech. Chemie, 3, 568
Dyes Derived from 5-Amino-2-hydroxy-thionaphthene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
902
INDIGO GROUP DYES
Helindone Brown 2R
I ; 14: 876
I '20: 1,778
2-Isatin-anilide
[Bromination; ? classi-
fication]
V
903
Helindone Brown 5R
2-Isatin-anilide
[Bromination]
V
904
Helindone Brown G
I '14: 13,086
I '20: 2,200
Isatin
[Bromination]
V
911
Ciba Orange G
I '14: 222
Acenaphthenequinone
[Bromination]
V
914
Helindone Orange D
I '20: 17
5-Amino-2-hydroxy-
thionaphthene (2 mols)
[Bromination]
V
6-Amino-3-hydroxy-thionaphthene (German numbering)
See, 5-Amino-2-hydroxy-thionaphthene (C. A. numbering)
DYES CLASSIFIED BY INTERMEDIATES
l-Amino-4-methoxy-anthraquinone
NH,
59
CH 3
FORMATION. Probably by the nitration and subsequent reduction of
1-methoxy-anthraquinone. The 1-methoxy-anthraquinone is ob-
tained from 1-nitro-anthraquinone by heating with an alcoholic
solution of potassium methylate with exclusion of water
LITERATURE. Cf. Barnett, Anthracene and Anthraquinone, 169, 279,
280, 287
Dyes Derived from l-Amino-4-methoxy-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
815
ANTHRAQUINONE AND
ALLIED DYES
Algol Scarlet G
I '20: 959
Benzoyl chloride
V
829
Algol Bordeaux 3B
I '20: 61
l-Amino-4-methoxy-an-
thraquinone (2 mols)
2: 6-Dichloro-anthra-
V
quinone
l-Amino-2-methyl-anthraquinone
TVTTT
,co v
CHg
FORMATION. 2-Methyl-anthraquinone is dissolved in sulfuric acid
solution and nitrated with sodium nitrate. The nitro compound
is then separated and reduced with sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 260
Lange, Zwischenprodukte, #3209
60 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from l-Amino-2-methyl-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
^Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
868
Cibanone Brown B
I '14: 399
[Sulfur]
V
3-Amino-4-methyl-diphenylamine
See, A^-PhenyM-ra-tolylene-diamine
IV-Amino-5-methyl-2-phenyl-thiazol-sulfonic Acid
See, Dehydro-thio-p-toluidine-sulfonic Acid
N- (3-Amino-4-methyl-phenyl) -/>-toluene-sulf amide
3'-Amino~(p-foluene-sulfo)-p-toluide (C. A. nomen.)
(Example of m-amino-aryl-sulfamide)
= Ci 4 H 16 N 2 2 S = 276
CH 3
FORMATION. 3-Nitro-p-toluidine (NH2 =1) is suspended in water,
p-toluene-sulfochloride and soda added. The reaction product
is purified by solution in dilute caustic soda and precipitation with
hydrochloric acid. This nitro body is now reduced with zinc dust
and hydrochloric acid to the amino-sulfamide
LITERATURE. Lange, Zwischenprodukte, #1801
Schultz-Heumann, Anilinfarben, 4, 2103
Ger. Pat. 135,016
Dyes Derived from W-(3-Amino-4-methyl-phenyl)--toluene-sulf amide
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
92
Metachrome
Picramic Acid
M
Bordeaux R
DYES CLASSIFIED BY INTERMEDIATES 61
a-Amino-naphthalene
See, a-Naphthylamine
/3-Amino-naphthalene
See, |8-Naphthylamine
3-Amino-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)
See, Amino-R Acid
4-Amino-l: 5-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: 8-disulfonic Acid
4-Amino-l : 6-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: Q-and-A: 7-disulfonic Acids
4-Amino-l: 7-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-4: Q-andA: 7-disulfonic Acids
4-Amino-2:-7-naphthalene-disulfonic Acid (C. A. nomen.)
See, Freund's Acid
5-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-5 : 7-disulfonic Acid
6-Amino-l : 3-naphthalene-disulfonic Acid (C. A. nomen.)
See, 2-Naphthylamine-5 : 7-disulfonic Acid
7-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
See, Amino-G Acid
8-Amino-l : 6-napthalene-disulfonic Acid (C. A. nomen.)
See, l-Naphthylamine-3 : 8-disulfonic Acid
l-Amino-naphthalene-4-sulfonic Acid
See, Naphthionic Acid
J-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
ISee, l-Naphthylamine-2-sulfonic Acid
62 DYES CLASSIFIED BY INTERMEDIATES
2-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 2-Naphthylamine-l-sulfonic Acid
4-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Naphthionic Acid
5-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Laurent's Acid
6-Amino-2-naphthalene-sulfonic Acid (C. A. nomen )
See, l-Naphthylamine-6-sulfonic Acid
6-a7w^8-Amino-2-naphthalene-sulfonic Acids (C. A. nomen.)
See, l-Naphthylamine-G-cwd-T-sulfonic Acids
6-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, Broenner's Acid
6-and-7-Amino-l-naphthalene-sulfonic Acids (C. A. nomen.)
See, 2-Naphthylamine-5-an-cresol (OH=1)
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
85
Omega Chrome
Phenyl- 1 -naphthyl-
ACr
Black PV
amine-8-sulfonic Acid
l-Amino-8-nitro-2-naphthol-4-sulfonic Acid
Nitro-l:2:4 Acid
2 N NH 2
tOH
FORMATION. From l-amino-2-naphthol-4-sulfonic Acid by nitration
LITERATURE. Lange, Zwischenprodukte, #2688
Dyes Derived from l-Amino-8-nitro-2-naphthol-4-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONAZO DYES
183
Eriochrome Black T
I '14: 129,550
a-Naphthol
ACr
M'18: ?
M'19: ?
I '20: 2,624
M'20: ?
184
Eriochrome Black A
I '14: 96,570
/3-Naphthol
ACr
M'17: ?
M'18: ?
M'19: 686,710
I '20: 14,262
M'20: ?
2-Amino-6-nitro-l- J phenol-4-sulfonic Acid (C. A. nomen. OH=1)
6-Nitro-2-amino-phenol-4-sulfonic Acid
2-Nitro-6-amino-phenol-4-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
OH
77
FORMATION. From phenol by sulfonation, dinitration and partial
reduction with sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 129
Lange, Zwischenprodukte, #1130
Dye Derived from 2-Arnino-6-nitro-phenol-4-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
159
Acid Alizarin
I '14: 16,800
jS-Naphthol
M
Black R
M'19: ?
I '20: 439
M'20: ?
6-Amino-5-nitroso-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, l-Nitroso-2-naphthylamine-6-sulfonic Acid
m-Amino-phenol
OH
>NH 2
C 6 H 7 NO=:109
FORMATION. By the fusion of Metanilic Acid (3-amino-benzene-
sulfonic acid) with caustic soda at about 280-290
LITERATURE. Ber. 32, 2112-2124
Lange, Zwischenprodukte, #582-584
78 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Amino-phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
90
Chrome Brown P
Picramic Acid
M
ANILINE BLACK
GROUP
923
Fuscamine
I '14: 54,005
m-Amino-phenol
Fur
M '19: ?
(x mols)
I '20: 1,600
[Oxidation on hair]
(M '20: 168,459)
/>-Amino-phenol
OH
NH 2
STATISTICS. Imported '14: 10,631 Ibs.
Manufactured '17: ?
Manufactured '18: 113,428 Ibs.
Manufactured '19: 128,627 Ibs.
Manufactured '20: 41,474 Ibs.
FORMATION. Phenol is treated with sodium nitrite in the cold and the
resulting p-nitroso-phenol is reduced with sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 117
Lange, Zwischenprodukte, #585-589
Dyes Derived from ^-Amino-phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
14
84
STILBENE DYE
Diphenyl Chrysoine
MONOAZO DYE
Azo Chromine
I '14: 9,898
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
Pyrogallol
D
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Amino-phenol (continued)
79
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
709
SULFUR DYES
Italian Green
I '14: 298
M'18: ?
I '20: 2,603
[Sulfur, etc.]
S
717
Vidal Black I
I '14: 7,495
[Na 2 S+S]
S
724
Immedial Black
I '14: 54,696
M'18: ?
l-Chloro-2: 4-dinitro-
benzene
[S+Na,S]
S
725
Immedial Dark
Brown A
Immedial Brown B
I '14: 23,887
M'18: ?
l-Chloro-2: 4-dinitro-
benzene
[NaOH; S+Na 8 S]
S
726
Pyrogene Direct Blue
Pyrogene Blue
I '14: 10,934
I '20: 2,498
l-Chloro-2: 4-dinitro-
benzene
[Alcohol; S+Na*S]
S
733
Immedial Indone
I '14: 4,236
o-Toluidine
[S+Na 2 S]
S
734
Pyrogene Yellow
I '14: 18,515
I '20: 2,701
p-Nitro-benzyl chloride
3
923
ANILINE BLACK
GROUP
Ursol P
I '14: 54,005
M'19: ?
I '20: 1,600
M '20: 168,459
p-Amino-phenol
(x mols)
[Oxidation]
Fur
4-Amino-l-phenol-2: 6-disulfonic Acid (OH=1) (C. A. nomen.)
p-Amino-phenol-a-disulfonic Acid
OH
H0 3 S| /N |S0 3 H _ C6H7N07S2 = 269
Note. Position of the sulfonic groups not fully established.
80
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Nitroso-dimethyl-aniline hydrochloride or nitroso-phenol
is introduced into a solution of sodium bisulfite, and warmed to
effect solution. Then concentrated hydrochloric is added and the
liquor boiled for two hours, using direct steam
LITERATURE. Ger. Pat. 65,236
Beil. spl. II, 492
Lange, Zwischenprodukte, #1154
Dye Derived from 4- Amino-l-pheno!-2 : 6-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Ot}ier Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
158
Chrome Brown
RR
I '14: 7,241
M'17: ?
Pyrogallol
M
I '20: 2,183
/>- Ammo-phenol Ethyl Ether
See, p-Phenetidine
2-Amino-l-phenol-4-sulfonic Acid (C. A. nomen. OH=1)
o-Amino-phenol-p-sulfonic Acid
OH
NHa r=
S0 3 H
STATISTICS. Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. Chloro-benzene is sulfonated and nitrated. The chloro-
body is then hydrolyzed to the phenol by boiling with caustic soda,
and finally reduced to 2-amino-phenol-4-sulfonic acid by means of
sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 129
DYES CLASSIFIED BY INTERMEDIATES
81
Dyes Derived from 2-Amino-l-phenol-4-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
154
Acid Alizarin
Brown B
I '14: 18,264
M'17: ?
m-Phenylene-diamine
M
Palatine Chrome
M'18: ?
Brown W
M'19: ?
I '20: 845
M'20: ?
155
Acid Alizarin
I '20: 201
Resorcinol
M
Garnet R
M'20: ?
156
Acid Alizarin
Violet N
I '14: 1,199
M'19: ?
/3-Naphthol
ACr
Palatine Chrome
M'20: ?
Violet
157
Diamond Black PV
I '14: 285,074
M '20: ?
1 : 5-Dihydroxy-naph-
thalene
M
3-Amino-l-phenol-4-sulfonic Acid (C. A. nomen. OH=1.)
Amino-phenol-sulfonic Acid III
INK,
r=C 6 H 7 NO 4 S:=189
S0 3 H
FORMATION. By fusion with caustic soda of the aniline-disulfonic acid
prepared by sulfonation of metanilic acid.
Note. Amino-phenol-sulfonic acid III is not 5-amino-phenol-2-
sulfonic acid
LITERATURE. Ber. 39, 3345
Lange, Zwischenprodukte, #942
82 DYES CLASSIFIED BY INTERMEDIATES .
Dyes Derived from 3-Amino-l-phenol-4-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
339
Brilliant Orange G
I '14: 6,321
Benzidine
D
M'17: ?
Salicylic Acid
TRISAZO DYE
481
Azo Corinth
Tolidine
D
Naphthionic Acid
Resorcinol
o-Amino-phenol-/>-sulfonic Acid
See, 2-Amino-l-phenol-4-sulfonic Acid
Amino-phenol-sulfonic Acid III
See, 3-Amino-l-phenol-4-sulfonic Acid (OH = 1)
Amino-phenol-sulfonic Acid IV
3-Amino-l-phenol-6-sulfonic Acid (not considered herein)
Amino-phenol-sulfonic Acid V
3-Amino-l-phenol-5-sulfonic Acid (not considered herein)
p- (-Amino-phenyl-azo) -&enzene-sulf onic Acid
See, Amino-azo-benzene-sulfonic Acid
l-(/>-Amino-phenyl)-5-methyl-benzothiazole (C. A. nomen.)
See, Dehydro-thio-p-toluidine
IV-Amino-2-phenyl-5-methyl-thiazol
See, Dehydro-thio-p-toluidine
^-Amino-phenyl-toluthiazole
See, Dehydrothio-p-toluidine
(m-Amino-phenyl)-trimethyl-ammonium Chloride
Trimethyl-w-amino-phenyl-ammonium chloride
C1N(CH 3 ) 3
^ 186.5
DYES CLASSIFIED BY INTERMEDIATES
83
FORMATION. m-Nitro-aniline by heating in methanol (methyl alcohol)
solution with hydrochloric acid is transformed into w-nitro-phenyl-
trimethyl-ammonium chloride (and m-nitro-dimethyl-aniline) . The
m-nitro-phenyl-trimethyl-ammonium chloride is dissolved in water
and reduced with zinc dust and hydrochloric acid
LITERATURE. Lange, Zwischenprodukte, #549,564
Green, Organic Coloring Matters (1908), 12
Dyes Derived from (m-Amino-phenyl)-trimethyl-ammonium Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
60
Azo Phosphine GO
I '14: 50
Resorcinol
B
DISAZO DYES
222
Janus Yellow G
I '14: 2,250
Resorcinol
B
I '20: 758
m-Nitro-aniline
240
Janus Red B
I '14: 250
m-Toluidine
B
I '20: 176
0-Naphthol
TKISAZO DYE
435
Janus Brown B
a-Naphthylamine
B
or m-Toluidine
Aniline
m-Phenylene-diamine
Amino-R Acid
2-Naphthylamine-3 : 6-disulf onic Acid
jfr-Naphthylamine-disulfonic Acid R
j3-Naphthylamine-a-disulfonic Acid
3-Amino-2 : 7-naphthalene-disulf onic Acid (C. A nomen.)
H0 3 S
NH 2
S0 3 H
Ci H 9 N0 6 S 2 =:303
FORMATION. By heating R salt with ammonia in an autoclave, in
presence of ammonium bisulfite
LITERATURE. Cain, Intermediate Products (2d Ed.), 207
Lange, Zwischenprodukte, #2594
Thorpe, Die. Chemistry, 3, 604
84 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Amino-R Acid
Schulte
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
120
MONOAZO DYE
Salmon Red
M'20: ?
Dehydro-thio-m-xyli-
dine
D
314
DISAZO DYES
Pyramine Orange 2R
I '14: 2,789
Benzidine
Nitro-m-phenylene-
diamine
D
315
Congo Orange R
I '14: 1,623
I '20: 75
Benzidine
Phenol
[Ethylation]
D
316
Brilliant Congo G
Benzidine
Broenner's Acid
D
332
Dianil Garnet B
Benzo Fast Red
I '14: 5,985
I '20: 3,799
Benzidine
Gamma Acid
D
358
Brilliant Dianol
RedR
Diphenyl Red
I '14: 14,305
I '20: 3,704
Dichloro-benzidine
Amino-R Acid (2 mols)
D
359
Trypan Red
Benzidine-sulfonic Acid
Amino-R Acid (2 mols)
Medi-
cinal
369
Brilliant Purpurin R
I '14: 8,051
Tolidine
Naphthionic Acid
D
370
Brilliant Congo R
I '14: 19,133
I '20: 11,129
Tolidine
Broenner's Acid
D
373
Congo Orange R
I '14: 7,027
I '20: 254
Tolidine
Phenol
[Ethylation]
D
5-Amino-salicylic Acid
COOH
lOH
H 2 N
DYES CLASSIFIED BY INTERMEDIATES
85
STATISTICS. Imported '14: 9,188 Ibs.
Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: 37,769 Ibs.
Manufactured '20: ?
FORMATION. (1) From the corresponding nitro-salicylic acid by re-
duction. (2) By reducing the azo-dye, benzene-azo-salicylic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 150
Dyes Derived from 5-Amino-salicylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
275
Diamond Black F
I '14: 462,306
a-Naphthylamine
ACr
M'17: ?
Nevile-Winther Acid or
M '18: ?
l-naphthol-5-sulfonic
M '19: 222,938
Acid
I '20: 2,226
M '20: ?
276
Diamond Green B
I '14: 8,622
a-Naphthylamine
ACr
M'18: ?
1 : 8-Dihydroxy-naph-
I '20: 4,016
thalene- 4- sulfonic
Acid
277
Anthracene Acid
I '14: 17,793
l-Naphthylamine-6-
M
Black DSF
and 7-sulfonic Acids,
etc.
TETRAKTSAZO DYE
492
Anthracene Acid
l-Naphthylamine-6-sul-
M
Brown B
fonic Acid (2 mols)
ACr
m-Phenylene-diamine
Ammo-salicylic Acid
(2 mols)
TRIPHENYL-METHANE
DYE
550
Chrome Bordeaux
Hydrol
M
[Oxidation]
Amino-Schaeffer's Acid
See, Broenner's Acid
86
DYES CLASSIFIED BY INTERMEDIATES
l-(4-Amino-?-sulfo-phenyl)-5-methyl-&enzothiazole(C. A. nomen.)
See, Dehydro-thio-p-toluidine-sulfonic Acid
4-Amino-4: 5-sultam-l: 3: 5-naphthalene-trisulfonic Acid (C. A.
nomen.)
See t 1 : 8-Naphthasultam-2 : 4-disulf onic Acid
m-Amino-tetramethyl-' : ^''-diamino-triphenyl-methane
N': N': N": JV"-Tetramethyl-w: p': p"-methenyl-trisaniline (C.
A. women.)
(CH 3 ) 2 N
N(CH 3 ) 2 = C 23 H 27 N 3 345
NH 2
FORMATION. m-Nitro-benzaldehyde and dimethyl-aniline are con-
densed in the presence of acids or zinc chloride to m-nitro-tetra-
methyl-p : p-diamino-triphenyl-methane, which by reduction gives
the w-amino-derivative
LITERATURE. Schultz, Chemie Steinkohlenteers (3 aufl.), 1, 115, 116.
Dye Derived from m-Amino-tetramethyl-/>':/>' / -diamino-triphenyl-
methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
510
Azo Green
Salicylic Acid
M
4-Amino-m-foluene-sulfonic Acid (C. A. nomen.
o-Toluidine-m-sulfonic Acid (CH 3 = 1)
S0 3 H
ICH,
NH 2
C 7 H 9 NO 3 S 187
DYES CLASSIFIED BY INTERMEDIATES
87
FORMATION. From o-toluidine acid sulfate by heating in an oven
LITERATURE. Cain, Intermediate Products (2d Ed.), 57
Dyes Derived from 4-Amino-m-toluene-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYE
24
Pigment Fast
Yellow R
3-Methyl-l-phenyl-5-
pyrazolone
CL
MONOAZO DYE
151
Orange HO, T
I '14: 90,747
M'17: ?
/3-Naphthol
A
M'19: ?
I '20: 20
M'20: ?
6-Amino-o-toluene-sulfonic Acid (C. A. nomen. S0 3 H=1)
p-Toluidine-o-sulfonic Acid (CH 3 = 1)
S0 3 H
H 2 N
STATISTICS. Manufactured '20: ?
FORMATION. From p-toluidine sulfate by heating in oven (baking
process)
LITERATURE. Green, Organic Coloring Matters (1908), 22
Lange, Zwischenprodukte, #839,237
Dyes Derived from 5-Amino-o-toluene-sulfonic
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
A
150
MONOAZO DYES
Fast Yellow N
Diphenylamine
152
Lithol Rubine B
Permanent Red 4B
I '14: 101,395
M'19: ?
I '20: 2,983
M'20: ?
3-Hydroxy-2-naphthoic
Acid
CL
88 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 5-Amino-o-toluene-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
852
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Direct
Violet R
I '20: 251
Quinizarin
A
865
Alizarin Direct
Green G
I '14: 2,000
I '20: 31,851
M'20: ?
Quinizarin
p-Toluidme-3-sulfonic
Acid (2 mols)
ACr
3'-Amino-(/Htoluene-sulfo)-/>-toluide (C. A. nomen.)
See, JV-(3-Amino-4-methyl-phenyl) -p-toluene-sulf amide
4- (4-Amino-m-tolyl-azo)-m -toluene -sulfonic Acid (C. A. nomen.)
See, o-Amino-azo-toluene-sulfonic Acid
l-(4-Amino-m-tolyl)-3: 5-dimethyl-&enzothiazole (C. A. nomen.)
See, Dehydro-thio-m-xylidine
l-(6-Amino-m-tolyl)-3:5-dimethyl-benzothiazole (C. A. nomen.)
See, tso-Dehydro-thio-m-xylidine
l-Amino-4: 5: 8-trihydroxy-anthraquinone
8-Amino-l: 4: 5-trihydroxy-anthraquinone (C. A. nomen.)
HO
CO
OH
FORMATION. 4: 8-Dinitro-anthramfin (p-dinitro-anthrarufin) is heated
with sulfuric and boric acids at temperature of water bath, forming
l-nitro-4: 5: 8-trihydroxy-anthraquinone. (At higher tempera-
tures the 1:4:5: 8-tetrahydroxy-anthraquinone is formed.) By
reduction of the 1-nitro-derivative, the desired amino-derivative
results.
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Ger. Pat. 125,579; Frdl. 6, 335; Chem. Zen. 1901, II,
1189
Dye Derived from l-Amino-4: 5: 8-trihydroxy-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
823
ANTHRAQUINONE AND
ALLIED DYES
Algol Violet B
I '20: 69
Benzoyl chloride
V
Andre sen's Acid
See, l-Naphthol-3 : 8-disulf onic Acid
This trivial name also applied to:
2-Naphthylamine-4 : 7-disulfonic Acid
Anhydro-formaldehyde-aniline
1:3: 5-Triphenyl-hexahydro-s-riazine (C. A. nomen.)
Formaniline
| | =:C 21 H 21 N 3 =:315
H 6 C 6 .N N.C 6 H 5
\C/
H 2
Note. Some of the older books give the formula as C^H^N:
STATISTICS. Manufactured 1920, but in an undisclosed amount.
FORMATION. By condensation of aniline and formaldehyde
LITERATURE. Beilstein, Organische Chemie (3d auf.), 2, spl. 233
Cain and Thorpe, Synthetic Dyestuffs, 90
Dye Derived from Anhydro-formaldehyde-aniline
Schultz
Number
for Dye
511
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
Parafuchsine
Paramagenta
M '14: 65,026
M'18: ?
M'19: ?
M'20: ?
Aniline
Aniline hydrochloride
[Nitro-benzene and
ferric chloride]
B
90 DYES CLASSIFIED BY INTERMEDIATES
Anhydro-formaldehyde-o-toluidine
FORMATION. By condensation of o-toluidine and formaldehyde
Dyes Derived from Anhydro-formaldehyde-o-toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
513
New Fuchsine
I '14: 300
o-Toluidine
B
M'18: ?
o-Toluidine
M'19: ?
hydrochloride
M'20: ?
[o-Nitro-toluene and
ferrous chloride]
93
STATISTICS. Imported '14: 4,553,028 Ibs.
Manufactured '17: 30,149,397 Ibs.
Manufactured '18: 25,867,488 Ibs.
Manufactured '19: 25,792,695 Ibs.
Manufactured '20:-^ 1,259, 142 Ibs.
FORMATION. Benzene is nitrated to nitro-benzene with mixed nitric
and sulfuric acid. The nitro-benzene is reduced to aniline with
iron turnings and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 40
Lange, Zwischenprodukte, #69-82
DYES CLASSIFIED BY INTERMEDIATES
91
Dyes Derived from Aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
STILBENE DYE
12
Diphenyl
Aniline (2 mols)
D
Citronine G
Dinitro-dibenzyl-
disulfonic Acid
or
Dinitro-distilbene-
disulfonic Acid
or
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
PYRAZOLONE DYES
19
Flavazine L
I '14: 38,908
3-Methyl-l-p-sulfo-
A
Fast Light Yellow
I '20: 9,327
phenyl-5-pyrazolone
or
Phenyl-hydrazine-p-
sulfonic Acid
Aceto-acetic Ethyl
Ester
20
Flavazine S
I '14: 81,375
l-p-Sulfophenyl-5-
A
I '20: 1,500
pyrazolone-3-car-
boxylic Acid
or
Phenyl-hydrazine-p-
sulfonic Acid
Oxal-acetic Ester
MONOAZO DYES
31
Amino-azo-benzene
M'17: ?
Aniline (2 mols)
S3
Spirit Yellow
M'18: 52,283
M'19: ?
M '20: ?
32
Butter Yellow
I '14: 4,062
Dimethyl-aniline
S3
Oil Yellow
M'17: 33,180
M'18: 27,669
M'19: 31,156
M'20: 74,182
33
Chrysoidine
I '14: 63,303
w-Phenylene-diamine
B
M'17: 195,756
M'18: 376,495
M'19: 314,581
M '20: 585,648
92
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued) '
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
34
Chrysoidine R
I '14: 111,006
m-Tolylene-diamine
B
M'17: 58,115
M '18: 137,035
^
M '19: 220,542
M '20: 186,793
I '20: 1,102
35
Sudan G
I '14: 798
Resorcinol
ss
36
Sudan I
I '14: 4,554
/3-Naphthol
88
Oil Orange
M'17: 32,455
M'18: 29,670
M'19: 75,868
M '20: 116,624
37
Ponceau 4 GB
I '14: 13,046
Schaeffer's Acid
A
Croceine Orange
M'17: ?
*
M'18: 30,824
M'19: 17,274
M '20: 96,573
38
Orange G
I '14: 48,456
GAcid
A
M'17: ?
M'18: ?
M'19: ?
M '20: 120,874
I '20: 100
39
Ponceau G
M'17: ?
RAcid
A
M'19: ?
40
Chromotrope 2R
I '14: 5,000
Chromotropic Acid
A
M'17: ?
M'18: ?
M'19: ?
M '20: ?
41
Fast Acid
M'18: ?
HAcid
A
Fuchsine B
M'19: 26,699
M'20: 30,678
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
42
Amido Naphthol
I '14: 3,500
Acetyl-H Acid
A
RedG
M'17: ?
M'18: ?
M'19: ?
I '20: 2,028
M '20: 132,637
43
Tolane Red B, G
KAcid
A
44
Azo Archil R
,
2 R Acid
A
45
Brilliant Lake Red R
I '14: 31,674
3-Hydroxy-2-naphthoic
CL
I '20: 1,071
Acid
58
Alizarin Yellow R
I '14: 97,057
Salicylic Acid
M
M '17: 215,468
[Nitration]
M '18: 385,910
M '19: 130,424
I '20: 860
M'20: 83,334
124
Diazine Green S
I '14: 1,340
o-Toluidine
B
p-Tolylene-diamine
[or Safranine]
Dimethyl-aniline
125
Diazine Black
I '14: 2,630
o-Toluidine
B
I '20: 701
p-Tolylene-diamine
[or Safranine]
Phenol
126
Indoine Blue R
I '14: 15,353
o-Toluidine
B
Union Blue R
M'17: ?
p-Tolylene-diamine
M'18: ?
[or Safranine]
/3-Naphthol
127
Methyl Indone B
M'17: ?
o-Toluidine
B
p-Tolylene-diamine
[or Safranine]
[' ' Amino-naphthols ' ']
94 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
128
Janus Gray B
o-Toluidine
B
p-Tolylene-diamine
[or Safranine], etc.
182
Fast Sulf on
I '14: 4,871
HAcid
A
Violet 5BS
I '20: 4,740
Benzene- (or Toluene-)
Brilliant Sulfon
sulfonyl Chloride
RedB
DISAZO DYES
215
Blue Black N
I '14: 2,653
KAcid
A
p-Nitro-aniline
216
Domingo Blue
l-Amino-8-naphthol-
A
Black B
3 : 5-disulf onic Acid
p-Nitro-aniline
217
Naphthol Blue Black
I '14: 431,027
HAcid
A
M '17: 620,218
p-Nitro-aniline
M'18:
1,158,309
M'19:
1,877,860
I '20: 340
M'20:
2,608,864
219
Chrome Patent
KAcid
ACr
Green N
Picramic Acid
241
Neutral Gray G
I '14: 2,546
a-Naphthylamine
D
M'19: ?
Gamma Acid
I '20: 3,472
M'20: ?
242
Sulfone Black G
l-Naphthylamine-6-anrf
A
7-sulfonic Acid
1 : 8-Dihydroxy-naphth-
alene-4-sulfonic Acid
270
Brilliant Croceine 9B
Amino-G Acid
A
R and G Acids
DYES CLASSIFIED BY INTERMEDIATES
95
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
Benzo Fast Scarlet
TRISAZO DYES
Janus Brown B
Crumpsall Direct
Fast Brown B
Crumpsall Direct
Fast Brown
Erie Direct
Black GX
Direct Deep
Black E, EW
Erie Direct
Black RX
Cotton Black E
Erie Direct
Green ET
Columbia Black
Green D
I '14: 36,674
M'19: ?
I '20: 24,153
I '14:
1,246,536
M'17: ?
M'18: ?
M'19:
7,250,007
M'20:
7,736,994
I '14: 248,567
M'19: ?
M'20:
2,050,741
M'17: ?
M'18: ?
M'19: 69,700
M'20: ?
JAcid
Phosgene
Trimethyl-m-amino-
phenyl-ammonium
chloride or p-Amino-
benzyl-diethylamine
a-Naphthylamine or
ra-Toluidine
m-Phenylene-diamine
Benzidine
Salicylic Acid
Gamma Acid
Benzidine
Salicylic Acid
Phenyl-gamma Acid
Benzidine
HAcid
w-Phenylene-diamine
Benzidine
HAcid
m-Tolylene-diamine
Benzidine
HAcid
Phenol
Benzidine
Salicylic Acid
l-Amino-8-Naphthol-
4-sulf onic Acid
B
D
D
D
D
D
D
96
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schult
Numbe
forDy
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
(continued)
482
Alizarin Yellow FS
o-Toluidine and
M
p-Toluidine
[or Fuchsine]
Salicylic Acid (3 mols)
TRIPHENYL-METHANE
DYES
511
Parafuchsine
I '14: 65,02
p-Toluidine
B
Paramagenta
M'18: ?
Aniline (2 mols)
M '19: ?
[Iron and nitro-benzene
M'20: ?
or arsenic Acid]
or
p-Nitro-benzaldehyde
Aniline sulfate (2 mols
[Zinc chloride; ferrous
chloride]
or
p: p'Diamino-diphenyl-
methane or anhydro-
formaldehyde-aniline
[Nitro-benzene and fer-
ric chloride]
512
Fuchsine
I '14: 87,102
p-Toluidine
B
Magenta
M'17: 17,739
o-Toluidine
M '18: 71,675
[Nitro-benzene, iron
M '19: 155,830
and zinc chloride or
I '20: 189
arsenic acid]
M '20: 284,285
514
Red Violet 5R
I '14: 331
[Magenta methylated
B
I '20: 750
or ethylated]
or
o-Toluidine
p-Toluidine
Nitro-benzene, iron
and zinc chloride or
arsenic acid]
Methylation or ethyl-
ation]
DYES CLASSIFIED BY INTERMEDIATES
97
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
j>D YES (continued)
520
Light Blue Superfine
1 '14: 2,149
[Para-rosaniline tri-
ss
Spirit Soluble
phenylated]
Diphenylamine Blue
or
Aniline (5 mols)
p-Toluidine
[Benzoic Acid]
521
Spirit Blue
I '14: 50,563
[Magenta phenylated]
S3
Aniline Blue
M'17: ?
or
M'18: ?
Aniline (2-4 mols)
M'19: ?
o-Toluidine
I '20: 723
p-Toluidine
M'20: ?
[Benzoic Acid]
524
Fuchsine S
I '14: 19,098
[Magenta sulfonated]
A
Acid Magenta
I '20: 524
or
M'20: ?
o-Toluidine
p-Toluidine
[sulfonation]
525
Red Violet'SRS
[Magenta ethylated and
A
sulfonated]
or
o-Toluidine
p-Toluidine
[Ethylation and
sulfonation]
526
Acid]Violet 4RS
[Magenta dimethylated,
A
trisulfonated]
or
o-Toluidine
p-Toluidine
[Dimethylation, Tri-
sulfonation]
535
Methyl Alkali Blue
I '14: 273
[Triphenyl-p-rosaniline
A
M'18: ?
sulfonated]
M'19: ?
or
I '20: 29
p-Toluidine
Aniline (5 mols)
[Sulfonation]
98
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRJPHENYL-METHANE
DYES
(continued)
536
Alkali Blue
I '14: 286,751
[Spirit BlueorTriphenyl-
A
M '17: ?
p-rosaniline-j- di-
1
M'18: 43,184
phenyl-rosaniline
M'19: 77,796
sulfonated]
I '20: 6,778
or
M'20: 74,253
o-Toluidine
p-Toluidine
Aniline (3-5 mols)
[Sulfonation]
537
Methyl Blue for Silk
I '14: 34,867
[Triphenyl-p-rosaniline
A
Marine Blue B
M '18: ?
mono- and di-sulfo-
M'19: ?
nated]
I '20: 2,395
or
M'20: ?
o-Toluidine
p-Toluidine
Aniline (4 mols)
[Sulfonation]
538
Methyl Blue
I '14: 50,255
[Triphenyl-p-rosaniline
B
Cotton Blue
di- and tri-sulf onated]
or
o-Toluidine
p-Toluidine
Aniline (4 mols)
[Di-and Tri-sulf onation]
539
Water Blue
I '14: 91,152
[Spirit Blue or Tri-
A
Soluble Blue
M '18: ?
phenyl-p-rosaniline+
M'19: 16,315
diphenyl-rosaniline
I '20: 1,387
di- and tri-sulf onated]
M'20: 98,770
or
o-Toluidine
p-Toluidine
Aniline (3-5 mols)
[Di- and tri-sulf onation]
DYES CLASSIFIED BY INTERMEDIATES
99
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-ME THANE
DYES (continued)
540
Pacific Blue
p-Rosaniline-}- diamino-
D
diphenyl-methane
and sulfonation]
or
o-Toluidine
p-Toluidine
Diamino-diphenyl-
- methane
[Sulfonation]
541
Brilliant Dianil
[/3-Naphthyl-rosaniline
B
Blue 6G
sulfonated]
or
/3-Naphthylamine
(3 mols)
o-Toluidine
p-Toluidine
[Disulfonation]
XANTHONE DYES
572
Rhodamine G
I '14: 2,648
[Rhodamine B heated
B
I '20: 517
with aniline to re-
move one QjHs group
or
Phthalic anhydride
Diethyl-m-amino-
phenol (2 mols)
580
Fast Acid Violet B
I '14: 20,688
[Dichloro-fluoresceine
A
M '19: ?
and aniline or p-tol-
I '20: 2,907
uidine; sulfonation]
or
Aniline (2 mols)
Phthalic Anhydride
Resorcinol
[PC1 6 ; Sulfonation]
ACRIDINE DYE
606
Phosphine
I '14: 168,175
[Magenta by-product]
B
M'17: ?
or
M'18: ?
p-Toluidine
M '19: 14,648
o-Toluidine
I '20: 19,259
M '20: ?
100
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
622
Delphine Blue B
M'17: ?
Nitroso-dimethyl-
M
M '18: ?
aniline
M'19: 43,827
Gallic Acid
I '20: 29,643
[Sulfonation]
M'20: 76,719
or
[Gallocyanine treated
with aniline; Sulfo-
nation]
630
Cyanazurine
Nitroso-dimethyl-
M
aniline
Gallamide
[Reduction]
640
Modern Azurine DH
Gallic Acid Methyl
M
Ester
Nitroso-dimethyl-
aniline
646
Coreine AR
Gallamide
M
Nitroso-diethyl-aniline
or Diethyl-amino-
azo- benzene
[Sulfonation]
or
[Coreine RR; Sulfona-
tion]
AZINE DYES
672
Azo Carmine G
I '14: 17,500
Aniline (3 mols)
A
M'17: ?
a-Naphthylamine
M'18: ?
[Disulfonation]
M'19: ?
--
I '20: 196
.
M'20: ?
673
Azo Carmine B
I '20: 549
Aniline (3 mols)
A
a-Naphthylamine
[Trisulfonation]
DYES CLASSIFIED BY INTERMEDIATES 101
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
674
AZINE DYES
(continued)
Rosinduline 2G
I '20: 201
Aniline (3 mols)
a-Naphthylamine
[Trisulfonation; heated
to 160]
A
675
Rosinduline G
I '20: 40
Aniline (2 mols)
l-Nitroso-2-naphthyl-
amine-6-sulf onic Acic
A
679
Safranine
I '14: 59,921
M'17: ?
M '18: 106,591
M '19: 131,042
I '20: 386
M '20: 149,629
p-Tolylene-diamine
o-Toluidine
B
680
Methylene
Violet BN
I '14: 1,521
M'17: ?
I '20: 33
Aniline (2 mols)
Dimethyl-p-phenylene-
diamine
[Oxidation]
B
682
Nigramine
Nitroso-dimethyl-
aniline
B
683
Safranine MN
I '14: 198
M'18: ?
M'19: ?
M '20: ?
Dimethyl-p-phenylene-
diamine
o- or p-Toluidine
[Oxidation]
B
684
Brilliant Rhoduline
Red
N 3 -Ethyl-4-m-tolylene-
diamine
Methyl-o-toluidine
B
686
Amethyst Violet
Diethyl-p-phenylene-
diamine
Diethyl-aniline
^Oxidation]
A
"c c * ? , J>
102 DYES CLASSIFIED BY INTERMEDIATES
H4 v''' 1 :'*' 1 -' ''
rixroo Tiorivorl frrvm Anilino (ffi/nt^vtiia^
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
(continued)
687
Rosolane O
I '20: 1,083
p-Amino-diphenyl-
B
amine
o-Toluidine
[Oxidation]
688
Rosolane
I '14: 796
Toluidines (3 mols)
B
Mauve
I '20: 3
[Oxidation]
693
Milling Blue
I '14: 3,082
Aniline (3 mols)
M
a-Naphthylamine
(2 mols)
[Sulfonation]
or
Aniline (2 mols)
Phenyl-a-naphthyl-
amine (2 mols)
Phenol
[Sulfonation]
696
Indamine Blue
Aniline (excess)
B
Amino-azo-benzene
697
Induline, Spirit
I '14: 25,342
Aniline (excess)
ss
Soluble
M'17: ?
Amino-azo-benzene
M'18: 8,589
M'19:-436,201
M '20: 140,400
698
Nigrosine, Spirit
I '14: 186,595
Aniline (excess)
S3
Soluble
M '17: 302,706
Nitro-benzene
M '18: 314,151
[Iron]
M '19: 346,167
or
M '20: 919,242
Aniline (excess)
Nitro-phenol
699
Induline, Water
I '14: 29,177
Aniline (excess)
A
Soluble
M '17: 183,739
Amino-azo-benzene
M'18: 91,724
[Sulfonation]
M '19: 130,704
I '20: 500
M '20: 168,048
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
103
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
(continued)
700
Nigrosine, Water
I '14: 398,112
Aniline (excess)
A
Soluble
M'17:
Nitro-benzene
1,968,458
[Iron; Sulfonation]
M'18:
or
1,191,343
Aniline (excess)
M'19:
Nitro-phenol
1,660,149
[Sulfonation]
I '20: 501
M'20:
2,743,021
702
Para Blue
Aniline (3-4 mols)
B
o-Toluidine
p-Toluidine
p-Phenylene-diamine
or
'
[Spirit Blue and p-
Phenylene-diamine]
SULFUR DYES
719
Thional Black
I '14: 16,865
p- (o- or ra-)Nitro-ani-
S
line
o-Nitro-phenol (2 mols)
[NasS+S]
729
Kryogene Pure
Aniline (2 mols)
S
BlueR
Dimethyl-p-phenylene-
diamine
[NasS+S]
*
or
[Methylene Violet;
S, NaaS]
ANTHRAQUINONE AND
ALLIED DYES
851
Alizarin Direct
I '14: 10,201
1 : 5- (and 1 : 8-) Amino-
A
BlueB
I '20: 2,982
anthraquinone-sul-
fonic Acid
[Dibromination, Sulfo-
nation]
857
Erweco Alizarin
Dinitro-anthraflavin-
ACr
Acid Blue R
disulfonic Acid
Aniline (2 mols)
[Sulfonation]
104
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
(continued)
861
Anthraquinone
I '20: 917
Aniline (2 mols)
ACr
Blue SR
Tetrabromo-1 : 5-di-
amino-anthraquinone
[Sulfonation]
862
Alizarin Blue
I '14: 54,706
Purpurin [or through
M
Black B
I '20: 28,802
Alizarin, or 2-Anthra-
quinone-sulfonic acid
[Sulfonation]
864
Anthraquinone
I '14: 1,709
1 -Nitr o-anthraquinone-
ACr
Green GX
I '20: 2,531
6-sulfonic Acid
[Halogenation]
p-Toluidine
INDIGO GROUP
DYES
874
Indigo
I '14:
Aniline (2 mols)
V
8,507,359
[Chloro-acetic, Soda-
M '17: 274,771
mide]
M'18:
[or CSz, KCN, etc.]
3,083,888
M'19:
8,863,824
I '20: 520,347
M'20:
18,178,231
876
Indigo MLB
Aniline (2 mols)
V
Indigo White
[Chloro-acetic, Soda-
mide, Reduction]
[or CSs, KCN, etc.,
Reduction]
[or Indigo, Reduction]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
105
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Manufacture
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
Indigotine
Indigotine P
Brom Indigo
Rath jen
Indigo MLB/RR
Helindone Blue BB
Indigo RB
Dianthrene Blue 2B
Bromo Indigo
Ciba Blue 2B
Indigo MLB/5B
Ciba Blue G
Indigo MLB/6B
Indigo KG
Brilliant Indigo
BASF/2B
Brilliant Indigo
BASF/B
I '14: 19,329 Aniline (2 mols) etc.
M '17: | [or Indigo, Sulfonation]
1,876,787
M'18:
1,434,703
M'19:-
1,699,670
I '20: 5,512
M'20:
1,395,000
Aniline (2 mols), etc.
[or Indigo, Sulfonation]
I '14: 53,610| Aniline (2 mols), etc.
M '20: ? [or Indigo, Bromination]
I '14: 6,856 Aniline (2 mols), etc.
M '17: 14,100 [or Indigo, Bromination
M'20: ?
I '14: 16,880| Aniline (2 mols), etc.
M '19: ? | [or Indigo, Bromination
I '20: 35,857
I '14: 1,356| Aniline (2 mols), etc.
I '20: 1,008 [or Indigo, Bromination
I '14: 3,191 Aniline (2 mols), etc.
I '20: 4,130| [or Indigo, Bromination
M'20:
I '14: 4,518| Aniline (2 mols), etc.
[or Indigo, Chlorination,
Bromination]
I '14: 8,175| Aniline (2 mols), etc.
I '20: 3,503) ror Indigo, Chlorination]
106 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
886
Brilliant Indigo
I '14: 12,057
Aniline (2 mols), etc.
V
BASF/G
[or Indigo, Chlorination,
Bromination]
889
Indigo Yellow 3G
Aniline (2 mols), etc.
V
Benzoyl chloride
1
[or Indigo, Benzoyl
chloride]
890
Ciba Yellow G
I '14: 48
Aniline (2 mols), etc.
V
Benzoyl Chloride
[Bromination]
[or Indigo Yellow 3G,
ANILINE BLACK
Bromination]
GROUP
922
Aniline Black
I '14: 1,470
Aniline (x mols)
MF
M'19: ?
[Oxidation on fiber]
M'20: ?
Aniline-2: 4-disulfonic Acid
See, 4-Amino-m-benzene-disulfonic Acid
Aniline-2: 5-disuIfonic Acid
See, 2-Amino-p-benzene-disulfonic Acid
Aniline-^-sulfonic Acid
See, Sulfanilic Acid
2-Anilino-6-amino-6enzene-sulfonic Acid (C. A. nomen.)
See, p-Amino-diphenylamine-2-sulfonic Acid
4-(-Anilino-anilino)-o-cresol (C. A. nomen.)
See, 4-Phenylamino-4 '-hydroxy- (phenyl-3 '-tolylamine)
-(-Anilino-anilino) -phenol (C. A. nomen.)
See, 4-Phenylamino-4'-hydroxy-diphenylamine
DYES CLASSIFIED BY INTERMEDIATES 107
Anilino-benzene-sulfonic Acid (C. A. nomen.)
See, Diphenylamine-sulfonic Acid
8- Anilino-5- (^-hydroxy-anilino) -1-naphthalene-sulf onic Acid
(C. A. nomen.)
See, 4-(p-Hydroxy-phenyl-amino)-l-phenylamino-naphtha-
lene-8-sulfonic Acid
8-Anilino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, Phenyl-l-naphthylamine-8-sulfonic Acid
7-Anilino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, Phenyl-gamma Acid
m- Aniline-phenol (C. A. nomen.)
See, w-Hydroxy-diphenylamine
2-Anilino-3-/>seudoindolone (C. A. nomen.)
See, 2-Isatin Anilide
Aniline Salt
Note. This is Aniline Hydrochloride.
See, Aniline
o-Anisidine (NH*=1)
NH 2
= 123
STATISTICS. Imported 7 14: 1,411 Ibs.
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. o-Nitro-anisole is reduced at 100-110 by means of iron
and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 71
108 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Anisidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
93
Pigment Purple A
I '14: 99
0-Naphthol
CL
Sudan R
94
Azo Eosine
I '14: 1,001
Nevile Winther Acid
A
M'18: ?
M'19: ?
95
Azo Cochineal
I '14: 952
l-Naphthol-4: 8-
A
Cochineal Scarlet B
disulfonic Acid
96
Chrome Fast
I '14: 150
Salicylic Acid
M
Yellow GG
I '20: 500
DISAZO DYE
259
Ponceau 10 RB
I '14: 201
Sulfanilic Acid
A
Croceine Acid
Anthracene
= Ci4Hio=178
STATISTICS. Imported '14: $37,240 in value
Manufactured '17: ?
Manufactured '18: 225,552 Ibs.
Manufactured '19: 1,381,944 Ibs.
Imported '19: 51,895 Ibs.
Manufactured '20: 711,258 Ibs.
Imported '20: 648,095 Ibs.
FORMATION. From coal-tar by extraction and purification
LITERATURE. Cain, Intermediate Products (2d Ed.), 244
USES. For manufacture of anthraquinone and anthraquinone deriva-
tives
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Anthracene
109
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
791
Indanthrene
I '20: 11
[Sulfur]
V
Olive G
M'18: ?
Anthrachrysone
1:3:5: 7-Tetrahydroxy-anthraquinone
OH
CC
HO
FORMATION. From 3: 5-Dihydroxy-benzoic acid by heating with con-
centrated sulfuric acid
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 483
Beil. Ill, 436; III spl. 312
Dyes Derived from Anthrachrysone
Schultz
Number
for Dyes
Ordinary Name and
Class of Dye
Statistics of.
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
790
ANTHRAQUINONE AND
ALLIED DYES
Acid Alizarin
Blue BB
I '14: 26,642
I '20: 3,539
[Sulfonation, Nitration,
Reduction, etc.]
ACr
796
Acid Alizarin
Green G
I '20: 1,334
[Sulfonation, Nitration,
Sodium sulfide reduc-
tion]
ACr
1: 9-Anthradiol (C. A. nomen.)
See, 1-Hydroxy-anthranol
110
DYES CLASSIFIED BY INTERMEDIATES
Anthraflavic Acid
2: 6-Dihydroxy-anthraquinone (not considered herein)
Anthranilic Acid (C. A. nomen. COOH=1)
o-Amino-benzoic Acid
COOH
|NH2
137
STATISTICS. Imported '14: 106 Ibs.
Manufactured '17: ?
Manufactured '18: 11,826 Ibs.
Manufactured '19: 22,976 Ibs.
Manufactured '20: ?
FORMATION. Phthalic anhydride is melted and heated to 240, where-
upon ammonia gas is introduced, forming phthalimide. This
latter is treated with sodium hypochlorite, forming anthranilic
acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 147
Lange, Zwischenprodukte, #357-367, 1619
Dyes Derived from Anthranilic Acid
Schultz
Number
JOT Dye
Ordi ary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
200
Lake Red D
I '14: 2,428
/3-Naphthol
CL
M'17: ?
M'18: ?
M'19: ?
M'20: ?
201
Pigment Scarlet G
M'17: ?
Schaeffer's Acid
CL
M'18: ?
.
M'19: ?
202
Acid Alizarin Red B
I '14: 7,374
R-Acid
ACr
Palatine Chrome
M '18: ?
CL
RedB
M'19: 28,081
I '20: 1,342
M '20: 67,817
DYES CLASSIFIED BY INTERMEDIATES
111
Dyes Derived from Anthranilic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
832
Indanthrene
I '14: 11,667
Anthranilic Acid
V
Violet RN
I '20: 49
(2 mols)
1 :5-Dichloro-anthraqui-
none
Anthrano'
See, 9-Anthrol
Anth aquinone
,C(X
208
STATISTICS. Imported '14: 29,850 Ibs.
Manufactured '18: ?
Manufactured '19: 294,260 Ibs.
Manufactured '20: 539,619 Ibs.
FORMATION. (1) From anthracene by appropriate oxidation means;
for example, chromic acid. (2) From o-benzoyl-benzoic acid by
action of sulfuric acid. The o-benzoyl-benzoic acid is prepared
by reacting together phthalic anhydride, benzene and aluminum
chloride
LITERATURE. Cain, Intermediate Products (2d Ed.), 244
Lange, Zwischenprodukte, #23, 648, 3065-3080
112 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Anthraquinone
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import an' I
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
863
Anthraquinone
Blue Green BXO
I '14: 6,552
I '20: 849
[?]
A
Note. Most of the dyes listed in the class " Anthraquinone and Allied
Dyes" (Schultz, #758-873) are derived indirectly from anthraquinone.
These dyes are, however, not tabulated under anthraquinone, but under that
intermediate from which directly derived.
Anthraquinone-1 : 5-and-l : 8-disulf onic Acids
Rho Acid is trivial name for the 1 : 5-disulfonic Add
Chi Acid is trivial name for the 1: 8-disulfonic Acid
S0 3 H H0 3 S S0 3 H
and
368
STATISTICS. The anthraquinone-1 : 5-disulf onate was manufactured in
1918, 1919, 1920 by one company. Amount was not disclosed
FORMATION. Anthraquinone is sulfonated with strong oleum in the
presence of mercury or mercuric oxide to a mixture of the 1 : 5- and
1 : 8-disulfonic acids, which are separated by crystallization
LITERATURE. Cain, Intermediate Products (2d Ed.), 252
Lange, Zwischenprodukte, #3290-3293
USES. The 1 : 5-acid is employed for making anthrarufin, 1 :5-dichloro-
anthraquinone, etc.
Anthraquinone-2: C-disulfonic Acid
a-Anthraquinone-disulf onic Acid
H0 3 S
Of
\Ac
S0 3 H
DYES CLASSIFIED BY INTERMEDIATES
113
FORMATION. From anthraquinone by heating with 45 per cent oleum
to 160-170 C., dilution with water, neutralization with caustic
soda and evaporation until the 2 : 6 acid crystallizes out (2 : 7 acid
in mother liquor)
LITERATURE. Cain, Intermediate Products (2d Ed.), 253
Lange, Zwischenprodukte, #3290
Dyes Derived from Anthraquinone-2 : 6-disulfonic Acid
TIT 7 ) Ordinary Name and
forDe\ Class f Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
785
ANTHRAQUINONE AND
ALLIED DYES
Alizarin GI
Flavopurpurin
I '14: 49,021
[Alkaline Fusion]
M
786
Alizarine Red 3WS
[Alkaline fusion,
sulfonation]
M
Anthraquinone-2: 7-disulfonic Acid
/3-Anthraquinone-disulfonic Acid
HOS| / \ /
\A
S0 3 H
STATISTICS . Manufactured '19:-
Manufactured '20:-
== 368
FORMATION. From anthraquinone by heating with 45 per cent Oleum,
dilution with water, neutralization with caustic soda, and evapora-
tion until the 2: 6 disulfonic acid crystallizes out. The 2: 7 disul-
fonic acid is then obtained (as sodium salt) by evaporating this
mother liquor to dryness
LITERATURE. Cain, Intermediate Products (2d Ed.), 253
Lange, Zwischenprodukte, #3290
114
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Anthraquinone-2 : 7-disulf onic Acid
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
784
ANTHRAQUINONE AND
ALLIED DYES
Alizarin SX
Isopurpurin
I '14: 14,273
M'19: ?
I '20: 49
M'20: ?
[Alkaline fusion]
M
a-Anthraquinone-disulfonic Acid
See, Anthraquinone-2 : 6-disulfonic Acid
/3-Anthraquinone-disulf onic Acid
See, Anthraquinone-2: 7-disulf onic Acid
Anthraquinone-2-sulf onic Acid
Anthraquinone-/3-sulfonic Acid
Acid or Beta Acid
Silver salt (Sodium derivative)
0-Sulfonic Acid
S0 3 H
STATISTICS. Manufactured 1918: ?
Manufactured 1919: ?
Manufactured 1920: ?
FORMATION. From anthraquinone by sulfonating with an equal
weight of 45-50 per cent oleum and heating up to 160 C., diluting,
neutralizing with caustic soda, and evaporating to crystallization
of the sodium salt ("Silver salt")
LITERATURE. Cain, Intermediate Products (2d Ed.), 251
Lange, Zwischenprodukte, #3156-3163
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Anthraquinone-2-sulfonic Acid
115
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
778
Alizarin
I '14: 202,392
[Oxidation]
M
M'17: ?
M'18: ?
M'19: ?
I '20: 8,575
M'20: ?
779
Alizarin Orange
I '14: 14,239
[Alizarin, Nitration]
M
M'19: ?
I '20: 500
M'20: ?
780
Alizarin Red
I '14: 81,919
[Alizarin, Sulfonation]
M
M'17: ?
I '20: 12,628
781
Erweco Alizarin
[Alizarin, Sulfonation]
M
Acid Red BS
783
Purpurin
[Alizarin, Oxidation]
M
787
Alizarin Bordeaux B
I '20: 20
[Alizarin, Oxidation]
M
788
Alizarin Cyanine R
I '20: 16,781
[Alizarin Bordeaux B,
M
Oxidation]
797
Alizarin Garnet R
I '14: 720
[4-Nitro-alizarin, Re-
M
duction]
798
Alizarin Maroon W
I '20: 2,014
[Crude Nitro-alizarin,
M
Reduction]
799
Alizarin Cyanine G
I '20: 339
[Alizarin Cyanine R,
M
Amidation]
854
Alizarin Viridine DG
I '20: 11,397
[Alizarin Bordeaux B]
M
p-Toluidine (2 mols)
[Sulfonation]
862
Alizarin Blue
I '14: 54,706
[Purpurin]
M
Black B
I '20: 28 ; 802
Aniline
[Sulfonation]
116
DYES CLASSIFIED BY INTERMEDIATES
Anthraquinone-3-sulfonic Acid
See, Anthraquinone-2-sulfonic Acid
2-Anthraquinone-urea Chloride
See, 2-Anthraquinonyl-urea Chloride
2-Anthraquinonyl-urea Chloride
2-Anthraquinone-urea Chloride
CO
FORMATION. From 2-Amino-anthraquinone in nitro-benzene solution
by action of phosgene at 50
LITERATURE. Lange, Zwischenprodukte, #3123
Dyes Derived from 2-Anthraquinonyl-urea Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
835
ANTHRAQUINONE AND
ALLIED DYES
Helindone
Orange GRN
I '20: 74
2-Anthraquinonyl-urea
chloride (2 mols)
V
836
Helindone
Brown 2GN
I '20: 15,238
2-An thraquinon yl-urea
chloride (2 mols)
Diamino-anthraqui-
nones, [various]
V
Anthrarufin
1 : 5-Dihydroxy-anthraquinone
TO OH
HO
DYES CLASSIFIED BY INTERMEDIATES
117
STATISTICS. Manufactured 1918: ?
Manufactured 1919: ?
Manufactured 1920: ?
FORMATION. 'This compound is obtained by the action of milk of lime
on either anthraquinone-1 : 5-disulf onic acid or on 1 : 5-dinitro-
anthraquinone
LITERATURE. Cain, Intermediate Products (2d Ed.), 257
Ullmann, Enzy. tech. Chemie, 1, 481
Lange, Zwischenprodukte, #3269, 3272, 3287
Dye Derived from Anthrarufin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
858
Alizarin Saphirol B
M'18: ?
[Sulfonation, Nitration,
ACr
M'19: ?
Reduction]
I '20: 28,210
M'20: ?
1-Anthrol (C. A. nomen.)
a-Anthrol
1-Hydroxy-anthracene
OH
FORMATION. From 1-anthracene-sulfonic acid by fusion with 5 parts
of caustic soda at about 250
LITERATURE. Schmidt, Ber. 37, 66 (1904)
Thorpe, Die. Chemistry, 1, 274; (1921 Ed.), 1, 352
Dye Derived from 1-Anthrol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
893
INDIGO GROUP DYE
Alizarin Indigo G
I J 20: 1,596
Dibromo-isatin chloride
V
118
DYES CLASSIFIED BY INTERMEDIATES
9-Anthrol (C. A. women.)
9-Hydroxy-anthracene
Anthranol
OH
FORMATION. Anthraquinone is reduced with tin in boiling glacial
acetic acid solution, or with iron and ferrous chloride solution
LITERATURE. Cain, Intermediate Products (2d Ed.), 262
Thorpe, Die. Chemistry, 1, 272; (1921 Ed.), 1, 349
Lange, Zwischenprodukte, #3038-3040
Dyes Derived from 9-Anthrol
Schultz
Number
for Dye
763
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
Dark Blue BO
I '14: 11,096
I '20: 13,917
M'20: ?
9-Anthrol (2 mols)
[Glycerol (2 mols)]
V
764
Indanthrene
Violet RT
9-Anthrol (2 mols)
[Glycerol (2 mols),
Halogenation]
or
[Indanthrene Dark Blue
BO and Halogenation]
V
765
Indanthrene
Green B
I '14: 72,251
M'19: ?
I '20: 6,765
M'20: ?
9-Anthrol (2 mols)
[Glycerol (2 mols),
Nitration]
or
[Indanthrene Dark Blue
BO and Nitration]
V
872
Leucol Brown B
I '20: 22
V
Armstrong's Acid
See, Naphthalene-1 : 5-disulfonic Acids
DYES CLASSIFIED BY INTERMEDIATES 119
Armstrong's 5 Acid
See, Naphthalene-1 : 5-disulfonic Acid
Armstrong and Wynne's Acid
l-Naphthol-3-sulfonic Acid (not considered herein)
Armstrong and Wynne's Acid II
See, 2-Naphthylamine-5: 7-disulfonic Acid
5: 5' -A oxy-bis-o-toluidine (C. A. nomen.)
See, Diamino-azoxy-toluene
jfr-Azoxy-o-toluidine
See, Diamino-azoxy-toluene
BAcid
See, l-Amino-8-naphthol-3: 5-disulfonic Acid
This trivial name also applied to
l-Amino-7-naphthol-3-sulfonic Acid
2: 3-Dihydroxy-naphthalene-6 : 8-disulfonic Acid
Badische Acid
See, 2-Naphthylamine-8-sulfonic Acid
Baum s Acid
l-Naphthol-2-sulfonic Acid (not considered herein)
Bayer's Acid
See, Croceine Acid
See, 2-Naphthylamine-7-sulfonic Acid
Benzal-bisxylidine (C. A. nomen.)
See, Diamino-dixylyl-phenyl-methane
120 DYES CLASSIFIED BY INTERMEDIATES
Benz aldehyde
HCO
STATISTICS. Imported '14: 20,475 Ibs.
Manufactured '17: 132,336 Ibs.
Manufactured '18: 360,591 Ibs.
Manufactured '19: 518,634 Ibs.
Manufactured '20: 702,543 Ibs.
FORMATION. (1) From toluene by chlorination to benzylidine chloride,
CeHsCHC^, and by heating this with milk of lime under pressure.
(2) From toluene by oxidation with manganese dioxide and
sulfuric acid
LITEBATURE. Cain, Intermediate Products (2d Ed.), 138
Lange, Zwischenprodukte, #20-41
Dyes Derived from Benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-
METHANE DYES
495
Malachite Green
I '14: 183,852
Dimethyl-aniline
B
M '17: 130,229
(2 mols)
M '18: 290,416
[Oxidation]
M '19: 560,301
I '20: 100
M '20: 654,237
499
Brilliant Green
I '14: 73,904
Diethyl-aniline (2 mols)
B
M'18: ?
[Oxidation]
M'19: ?
I '20: 25
M '20: ?
502
Guinea Green B
I '14: 49,971
Ethyl-sulfobenzyl-
A
Acid Green 3BG
M'17: ?
aniline (2 mols)
M'18: ?
[Oxidation]
M'19: ?
I '20: 278
M '20: ?
DYES CLASSIFIED BY INTERMEDIATES
121
Dyes Derived from Benzaldehyde (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
504
TRIPHENYL-METHANE
DYES (continued)
Light Green SF
Bluish
1 '14: 6,693
M'17: ?
M'18: ?
Benzyl-methyl-
aniline (2 mols)
[Sulfonation and
Oxidation]
A
505
Light Green SF
Yellowish
I '14: 71,462
M'19: ?
I '20: 7,490
M'20: ?
Benzyl-ethyl-
aniline (2 mols)
[Sulfonation and
Oxidation]
A
604
ACRIDINE DYES
Acridine Orange R
Dimethyl-w-phenylene-
diamine (2 mols)
[Ammonia removal;
Oxidation]
B
605
Benzoflavine
I '14: 600
w-Tolylene-diamine
(2 mols)
[Ammonia removal,
Oxidation]
B
Benzaldehyde-disulfonic Acid
4-Formyl-w-6enzene-disulfonic Acid (C. A. nomen.)
HCO
I J SO * H = C 7 H 6 7 S 2 = 266
S0 3 H
FORMATION. Toluene is sulf onated with oleum to the 2 : 4-disulf onic
acid, which is then oxidized with manganese dioxide
LITERATURE. Lange, Zwischenprodukte, #899
122 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Benzaldehyde-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
579
Sulf o Rhodamine B
I '14: 1,698
Diethyl-m-amino-
A
Xylene Red B
phenol (2 mols)
[Oxidation]
Benzaldehyde-o-sulfonic Acid
o-Formyl-&enzene-sulfonic Acid (C. A. nomen.)
HCO
r /""I TT /~\ Q1 -| O^*
FORMATION. By heating o-chloro-benzaldehyde with Na 2 S0 3 at around
170-180 under pressure
LITERATURE. Cain, Intermediate Products (2d Ed.), 146
Lange, Zwischenprodukte, #504-506
Dyes Derived from Benzaldehyde-o-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-
METHANE DYES
506
Erioglaucine
I '14: 66,526
Ethyl-sulfobenzyl-
A
M'19: ?
aniline
I '20: 6,160
or
M '20: ?
Benzyl-ethyl-aniline
(2 mols) [and sulfona-
tion]
[Oxidation]
553
Eriochrome
I '14: 2,249
o-Cresotic Acid (2 mols)
ACr
Cyanine R
I '20: 2,205
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES 123
Benzamido- (C. A. nomen. for C 6 H 5 CO . N H)
See, Benzoylamino-
Note. The C. A. name for this radical is the scientific one, and it is listed
as an alternate, but in view of the widespread use of benzoylamino-, the
latter is given precedence at the present time.
l-Benzamido-4-chloro-anthraquinone (C. A. nomen.)
See, l-Benzoylamino-4-chloro-anthraquinone
7-meso-Benzanthren-7-one (C. A. nomen.)
See, Benzanthrone
Benzanthrone
7-weso-Benzanthren-7-one (C. A. nomen.)
Ci 7 Hi<>0~230
STATISTICS. Manufactured '19: ?
Manufactured '20: ?
FORMATION. (1) From anthranol and glycerol by condensation by
means of sulfuric acid. (Anthranol is made from anthraquinone.)
(2) From anthracene in sulfuric acid solution, by addition of glycerol
and heating to 100-110 C. until the anthracene disappears. The
reaction mass is then diluted with water, salted out and purified
LITERATURE. Cain, Intermediate Products (2d Ed.), 262
Lange, Zwischenprodukte, #3584
124
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzanthrone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
763
Indanthrene
I '14: 11,096
Benzanthrone (2 mols)
V
Dark Blue BO
I '20: 13,917
764
Indanthrene
Benzanthrone (2 mols)
V
Violet RT
[Halogenation]
[or Indanthrene Dark
Blue BO and halo-
genation]
765
Indanthrene
I '14: 72,251
Benzanthrone (2 mols)
V
Green B
M'19: ?
[Nitration]
I '20: 6,765
[or Indanthrene Dark
M '20: ?
Blue BO and Nitra-
tion]
Benzanthrone-quinoline
Phenanthroquinolinone (C. A. nomen.)
FORMATION. From 2-amino-anthraquinone and glycerol by warming
with condensing agents, for example, sulfuric acid
LITERATURE. Lange, Zwischenprodukte, #3596
Ullmann, Enzy. tech. Chemie, 3, 314
Dye Derived from Benzanthrone-quinoline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
846
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene Dark
Blue BT
Benzanthrone-quino-
line (2 mols)
V
DYES CLASSIFIED BY INTERMEDIATES
Benzene-azo-diethylaniline
See, p-Diethylamino-azo-benzene
Benzene-sulfonyl Chloride
S0 2 C1
= 176.5
125
FORMATION. From benzene-sulfonic acid by treatment with phos-
phorus pentachloride
LITERATURE. Bucherer, Farbenchemie, 78, 150
Dye Derived from Benzene-sulfonyl Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
182
Fast Sulfon Violet
I '14: 4,871
H Acid
A
Brilliant Sulfon
I '20: 4,740
Aniline
RedB
Benzidine
H 2 N
NH 2 Ci 2 H 12 N 2 =:184
STATISTICS. Imported '14: 55,245 Ibs.
Manufactured '17: 1,766,582 Ibs.
Manufactured '18: 2,501,887 Ibs.
Manufactured '19: 1,319,629 Ibs.
Manufactured '20: 2,183,583 Ibs.
FORMATION. Nitro-benzene is reduced to hydrazo-benzene with zinc
or iron in presence of caustic soda; the hydrazo-benzene is re-
arranged to benzidine by treatment with acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 89
Lange, Zwischenprodukte, #1204
126 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine
SchuUz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
15
Chicago Orange G
p-Nitro-toluene-o-
D
sulfonic Acid
102
Diamond Flavine G
I '14: 23,089
Salicylic Acid
M
M'17: ?
M'18: ?
M'19: ?
M '20: ?
103
Dutch Yellow
Salicylic Acid
M
[Sodium sulfite]
DISAZO DYES
306
Pyramine Orange 3G
I '14: 7,863
Nitro-m-phenylene-
D
I '20: 396
diamine
m-Phenylene-diamine-
disulfonic Acid
307
Congo Red
I '14: 20,629
Naphthionic Acid
D
M'17: ?
(2 mols)
M '18: 587,153
M '19 .873,734
M'20:
1,502,630
308
Diazo Black B
I '14: 62,854
Laurent's Acid (2 mols)
D
309
Glycine Red
a-Naphthyl-glycine
D
Naphthionic Acid
310
Glycine Corinth
. ..
a-Naphthyl-glycine
D
(2 mols)
311
Orange TA
I '14: 602
Naphthionic Acid
D
M'17: ?
Cresol
M'18: ?
M'19: ?
M'20: ?
312
Congo Corinth G
I '14: 44,157
Nevile Winther's Acid
D
M'17: ?
Naphthionic Acid
M'18: ?
M'19: 137,704
M'20: 242,503
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
127
Schultz
Number
forDy
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
313
Congo Rubine
I '14: 46,213
Croceine Acid
D
M'17: ?
Naphthionic Acid
M'18: ?
I '20: 2,601
314
Pyramine
I '14: 2,789
Nitro-ra-phenylene-
D
Orange RR
diamine
Amino-R Acid
315
Congo Orange G
I '14: 1,623
Phenol
D
I '20: 75
Amino-R Acid
[Ethylation]
316
Brilliant Congo G
Amino-R Acid
D
Broenner's Acid
317
Pyramidol
Resorcinol (2 mols)
D
Brown BG
318
Benzidine Puce
0-Naphthol
MF
319
Diamine Scarlet
I '14: 41,175
Phenol
D
I '20: 11,340
GAcid
[Ethylation]
320
Bordeaux
I '14: 1,335
Croceine Acid (2 mols)
D
M'18: ?
M'19: ?
M'20: ?
321
Heliotrope 2B
I '14: 1,473
Croceine Acid
D
I '20: 60
l-Naphthol-4:8-
disulfonic Acid
322
Trisulfon
I '14: 1,124
/3-Naphthol
D
Violet B
M'17: ?
l-Naphthol-3:6:8-tri-
M'18: ?
sulfonic Acid
M'19: ?
I '20: 7,927
M'20: ?
128 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued')
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
323
(continued)
Dianil Blue R
M '20: ?
Chromotropic Acid
(2 mols)
D
324
Chicago Blue 4R
I '14: 1,199
Croceine Acid
1 -Amino-8-naphthol-4-
sulfonic Acid
D
325
Columbia Blue R
I '14: 3,071
l-Naphthol-3: 8-disul-
fonic Acid
D
1 -Amino-8-naphthol-4-
sulfonic Acid
326
Oxamine Violet
Oxydiamine Violet BF
I '14: 23,981
I '20: 732
J Acid (2 mols)
D
327
Diamine Violet N
I '14: 18,263
M'19: ?
Gamma Acid (2 mols)
D
M'20: 92,503
328
Diamine Black RO
Dianol Black RW
I '14: 8,253
Gamma Acid (2 mols)
D
329
Diamine Brown V
M'19: ?
w-Phenylene-diamine
Gamma Acid
D
330
Zambesi Brown G
I '14: 4,028
I '20: 1,104
Gamma Acid
2: 7-Naphthylene-
diamine-sulfonic Acid
D
331
Alkali Dark
Brown GV
Nitroso-/3-naphthol
Gamma Acid
D
332
Dianil Garnet B
Benzo Fast Red
I '14: 5,985
I '20: 3,799
Gamma Acid
Amino-R Acid
D
333
Diamine Black BH
Oxamine Black BHN
I '14: 619,430
M'17: ?
Gamma Acid
HAcid
D
M'18: ?
M'19: 485,046
I '20: 5,512
M '20: 803,501
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
129
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
334
Diphenyl Blue
I '14: 26,240
Ethyl-gamma Acid
D
Black
HAcid
335
Naphthamine
I '14: 49,016
Gamma Acid
D
Black RE
KAcid
336
Benzo Cyanine R
I '14: 201
HAcid
D
l-Amino-8-naphthol-4-
sulfonic Acid
337
Diamine Blue BB
I '14: 19,035
H Acid (2 mols)
D
Benzo Blue BB
M'17:
1,445,059
M'18:
1,523,985
M'19:
1,380,335
M'20:
1,789,774
338
Naphthamine Blue
I '14: 11,707
K Acid (2 mols)
D
2B
I '20: 400
339
Brilliant Orange G
I '14: 6,321
Salicylic Acid
D
M'17: ?
3-Amino-phenol-4-
sulfonic Acid
340
Benzo Orange R
I '14: 1,073
Salicylic Acid
D
M'17: ?
Naphthionic Acid
M'18: 50,422
M'19: 42,807
I '20: 220
M'20: 86,210
340 (1)
Chlorazol
Salicylic Acid
D
Orange 2R
2-Naphthylamine-7-
sulfonic Acid
341
Crumpsall Direct
M'17: ?
Salicylic Acid
D
Fast Red R
M'18: ?
R Salt
M'19: ?
M'20: ?
130
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
342
DISAZO DYES
(continued)
Chrysamine G
I '14: 608
M'17: 26,061
M'18: 28,846
M'19: 54,279
I '20: 9,810
M'20: 49,342
Salicylic Acid
(2 mols)
D
343
Diamine Fast
RedF
I '14: 50,479
M'19: 56,864
I '20: 4,040
M '20: 115,865
Gamma Acid
Salicylic Acid
D
344
345
Diamine Brown M
Oxamine Maroon
I '14: 65,396
M'18: ?
M'19: 15,957
M '20: 257,872
Salicylic Acid
Gamma Acid
Salicylic Acid
l-Amino-5-naphthol-7-
sulfonic Acid
D
D
346
Oxamine Red
I '14: 11,636
I '20: 848
JAcid
Salicylic Acid
D
347
Diphenyl Brown RN
Salicylic Acid
Methyl-gamma Acid
D
348
Diphenyl Brown BN
I '14: 13,471
Salicylic Acid
Dimethyl-gamma Acid
D
349
Diamine Brown B
I '20: 24
Salicylic Acid
Phenyl-gamma Acid
D
350
Alkali Yellow R
Salicylic Acid
Dehydrothio-p-tolui-
dine-sulfonic Acid
D
351
Cresotine Yellow G
I '14: 1,748
M'17. ?
M'18: ?
M'19: ?
M '20: ?
o-Cresotic Acid
(2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
131
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
352
Direct Violet R
I '14: 661
w-Tolylene-diamine
D
M'19: ?
I: 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
353
Direct Indigo
I '14: 6,000
1 : 7-Dihydroxy-6-naph-
D
Blue BN
thoic-3-sulfonic Acid
HAcid
354
Direct Gray R
I '20: 4,927
1: 7-Dihydroxy-6-naph-
D
thoic-3-sulfonic Acid
(2 mols)
TRISAZO DYES
438
Melogene Blue BH
M'17: ?
H Acid (2 mols)
D
M'18: ?
p-Xylidine
439
Direct Indigo
M'18: ?
H Acid (2 mols)
D
Blue A
ra-Amino-p-cresol
Methyl Ether
440
Direct Indigo
Gamma Acid (2 mols)
D
Blue BK
w-Amino-p-cresol
Methyl Ether
441
Diazo Blue
M'19: ?
H Acid (2 mols)
D
Black RS
M'20: ?
a-Naphthylamine
442
Direct Black V
I '14: 145,738
Gamma Acid
D
a-Naphthylamine
2 R Acid
443
Direct Indone
a-Naphthylamine
D
BlueR
HAcid
2 R Acid
444
Crumpsall Direct
Salicylic Acid
D
Fast Brown B
Aniline
Gamma Acid
445
Crumpsall Direct
Salicylic Acid
D
Fast Brown
Aniline
Phenyl-gamma Acid
132
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
446
TRISAZO DYES
(continued)
Benzo Olive
I '14: 1,149
Salicylic Acid
a-Naphthylamine
HAcid
D
447
Benzo Gray S Extra
I 7 14: 802
Salicylic Acid
a-Naphthylamine
Nevile Winther's Acid
D
448
Diamine Bronze G
I '14: 4,495
Salicylic Acid
HAcid
w-Phenylene-diamine
D
449
Trisulfon
Brown B
I '14: 16,781
I '20: 38,616
2 R Acid
Salicylic Acid
ra-Phenylene-diamine
D
462
Erie Direct
Black GX
Direct Deep
Black EW
I '14:
1,246,536
M'17: ?
M'18: ?
M'19:
7,250,007
M'20:
7,736,994
Aniline
HAcid
m-Phenylene-diamine
D
463
Erie Direct
Black RX
Cotton Black E
I '14: 248,567
M'19: ?
M'20:
2,050,741
Aniline
HAcid
m-Tolylene-diamine
D
464
Erie Direct
Green E T
M'17: ?
M'18: ?
M'19: 69,700
M'20: ?
Aniline
HAcid
Phenol
D
465
Columbia Black
Green D
Salicylic Acid
Aniline
1: 8-Amino-naphthol-4-
sulfonic Acid
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
133
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
466
TEISAZO DYES
(continued)
Eboli Green
l-Amino-8-naphthol-
3 : 5-disulf onic Acid
Salicylic Acid
Sulfanilic Acid
D
467
Diphenyl Green G
I '20: 2,205
Phenol
H Acid
o-Chloro-p-nitro-
aniline
D
468
Diphenyl Green 3G
Salicylic Acid
H Acid
o-Chloro-p-nitro-
aniline
D
469
Chloramine Black N
I '14: 39,600
M'19: ?
I '20: 1,763
M'20: ?
w-Phenylene-diamine
HAcid
2: 5-Dichloro-aniline
D
470
Chloramine
Green B
I '14: 1,675
M'19: ?
Phenol
HAcid
2 : 5-Dichloro-aniline
D
471
472
Chloramine Blue 3G
Chloramine
Blue HW
I '14: 286
M'19: ?
I '20: 882
H Acid (2 mols)
2 :5-Dichloro-aniline
Gamma Acid
HAcid
2: 5-Dichloro-aniline
D
D
473
Diamine Black HW
I '20: 342
Gamma Acid
HAcid
p-Nitro-aniline
D
474
Diamine Green B
Oxamine Green B
I '14: 77,100
M'17: ?
M '18: 295,147
M'19: 305,854
I '20: 2,460
M '20: 420,138
Phenol
HAcid
7?-Nitro-aniline
D
134
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzidine (continued)
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
(continued)
475
Diamine Green G
I '14: 7,329
Salicylic Acid
D
Oxamine Green G
M'17: ?
HAcid
M'18: 29,118
p-Nitro-aniline
M '19: 136,638
I '20: 1,332
M'20: 53,292
476
Benzamine
I '14: 16,988
Sulfanilic Acid
D
Brown 3GO
M'17: ?
w-Phenylene-diamine
M'18: ?
Salicylic Acid
M'19: ?
M '20: 623,757
477
Congo Brown G
I '14: 52,141
Sulfanilic Acid
D
Naphthamine Brown
M'17: ?
Resorcinol
4G
M'18: ?
Salicylic Acid
M'19: ?
I '20: 443
M '20: 229,489
478
Columbia Green
I '14: 45,162
Salicylic Acid
D
M'18: ?
Sulfanilic Acid
I '20: 7,555
l-Amino-8-naphthol-4-
sulfonic Acid
479
Dianil Black R
Chromotropic Acid
D
Naphthionic Acid
m-Phenylene-diamine
480
Congo Brown R
I '14: 3,045
Resorcinol
D
Salicylic Acid
Laurent's Acid
TETRAKISAZO DYES
489
Hessian Brown BBN
Sulfanilic Acid (2 mols)
D
Resorcinol (2 mols)
490
Cotton Brown A
I '14: 29,074
Naphthionic Acid
D
(2 mols)
m-Phenylene-diamine
(2 mols)
DYES CLASSIFIED BY INTERMEDIATES
135
Dyes Derived from Benzidine (continued]
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYES
712
Kyrogene Yellow G
I '14: 1,126
I '20: 1,543
w-Tolylene-dithio-urea
[Sulfur]
s
714
Thiophor Yellow
Bronze G
p-Phenylene-diamine
p-Amino-acetanilide
[Sulfur]
s
Benzidine-disulfonic Acid
6: 6'-Diaminora: m'-bi(&enzene-sulfonic) Acid (C. A. nomen.)
4: 4 / -Diamino-diphenyl-3: 3'-disulfonic Acid
= Ci 2 H 12 N 2 6 S 2 = 344
H0 3 S ' S0 3 H
FORMATION. From benzidine sulfate by heating with 2 parts of sulfuric
acid at about 210 for forty-eight hours
LITERATURE. Cain, Intermediate Products (2d Ed.), 94
Griess and Duisberg, Ber, 22, 2464 (1889)
Cf. Griess, Ber., 14, 300 (1881)
Cf. Farbenfabriken, Ger. Pat. 27954
Dyes Derived from Benzidine-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
360
Pyramine Orange R
I '14: 21,329
Nitro-m-phenylene-
D
I '20: 7,821
diamine
TRISAZO DYES
459
Benzo Black Blue G
Nevile-Winther's Acid
D
(2 mols)
a-Naphthylamine
460
Benzo Black Blue 5G
I '14: 602
1 : 8-Dihydroxy-naph-
D
thalene-4-sulfonic
Acid (2 mols)
a-Naphthylamine
136 DYES CLASSIFIED BY INTERMEDIATES
Benzidine-sulfon-disulfonic Acid
4 : 4 / -Diamino-diphenyl-2 : 2'-sulf on-disulf onic Acid
2 : 7-Diamino-9-dioxide-? :?-dibenzothiophene-disulfonic Acid (C
A. nomen.)
2(S0 3 H)
H 2 N
NH 2 = Ci 2 HioN2O 8 S3 = 406
FOKMATION. Benzidine sulfate is heated with 40 per cent oleum for
1 hour at 100 in an autoclave, and then at 150 until a sample
dissolves in hot water and does not give a yellow precipitate with
alkali
LITERATURE. Lange, Zwischenprodukte, #1275
Dyes Derived from Benzidine-sulfon-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
361
Sulfonazurine
I '14: 300
Phenyl-a-naphthyl-
D
amine (2 mols)
Benzidine-sulfonic Acid
2-Amino-5-(p-amino-phenyl)-6enzene-sulfonic Acid (C. A. nomen
SO S H=1)
H 2 N
H0 3 S
NH 2 = Ci 2 Hi 2 N 2 O 3 S = 264
DYES CLASSIFIED BY INTERMEDIATES
137
FORMATION. From benzidine sulfate by evaporating to dryness with
dilute sulfuric acid (1J/2 mols), and then heating in air bath at
about 170 for 24 hours
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 318
Dyes Derived from Benzidine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
359
Trypan Red
Amino-R Acid (2 mols)
Medi-
cinal
TETRAKISAZO DYE
491
Dianil Black PR
Gamma Acid (2 mols)
D
m-Phenylene-diamine
(2 mols)
Benzoic Acid
COOH
STATISTICS. Imported '14: 352,201 Ibs.
Manufactured '17: 219,210 Ibs.
Manufactured '18: 282,212 Ibs.
Manufactured '19: 720,320 Ibs.
Manufactured '20: 743,113 Ibs.
FORMATION. (!) From toluene by chlorination to benzo-trichloride,
and hydrolysis with milk of lime. (2) From toluene by direct
oxidation with nitric acid
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 325
kange, Zwischenprodukte, #24, 59
138
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzole Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-
METHANE DYES
509
Chrome Green
Hydrol
M
[Oxidation]
520
Light Blue Superfine
I '14: 2,149
Aniline (5 mols)
ss
Spirit Soluble
p-Toluidine
Diphenylamine Blue
or
[p-Rosaniline tripheny-
lated]
521
Spirit Blue
I '14: 50,563
Aniline (2-4 mols)
ss
Aniline Blue
M'17: ?
o-Toluidine
M'18: ?
p-Toluidine
M'19: ?
or
I '20. 723
[Fuchsine or Rosaniline
M'20: ?
base phenylated]
ANTHRAQUINONE AND
ALLIED DYES
770
Alizarin Yellow A
Pyrogallol
M
782
Anthracene Brown
I '14: 115,586
Gallic Acid
M
Alizarin Brown
M'17: ?
M'18: ?
M'19: 40,426
I '20: 2,728
M'20: 42,840
Benzo-trichloride
a-Trichloro-foluene (C. A. nomen.)
CC1 3
= C 7 H 5 Cl 3 r= 195.5
STATISTICS. Imported '14< very small
Manufactured ' 18 : ?
Manufactured '20; ?
DYES CLASSIFIED BY INTERMEDIATES
139
FORMATION. From toluene by treatment with chlorine, preferably in
presence of catalyst
LITERATURE. Cain, Intermediate Products (2d Ed.), 19
Dyes Derived from Benzo-trichloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
QUINOLINE DYE
610
Quinoline Red
Quinaldine
B
Isoquinoline
ANTHRAQUINONE AND
ALLIED DYES
770
Alizarin Yellow A
Pyrogallol
M
l-Benzoylamino-4-chloro-anthraquinone
l-Benzamido-4-chloro-anthraquinone (C. A. nomen.)
NH.COC 6 H 5
, 361.5
FORMATION. By heating l-Amino-4-chloro-anthraquinone with ben-
zoyl chloride
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 164
Dye Derived from l-Benzoylamino-4-chloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
833
Algol Olive R
I J 14: 13,334
I '20: 481
l-Benzoylammo-4-
amino-anthraquinone
[Chloro-sulfonic acid]
V
140
DYES CLASSIFIED BY INTERMEDIATES
o-Benzoyl-fcenzoic Acid
COOH
I CO < > = Ci 4 Hio0 3 226
STATISTICS. Manufactured 1920: ?
FORMATION. By condensation of phthalic anhydride and benzene in
presence of aluminum chloride
LITERATURE. Heller, Zeit. angew. Chem., 19, 669 (1906)
HeUer, Ber., 41, 3631 (1908)
Cain, Intermediate Products (2d Ed.), 249
USES. For synthesis of anthraquinone
Benzoyi Chloride
COC1
STATISTICS. Manufactured '17: 20,621 Ibs.
Manufactured '18: 6,585 Ibs.
Manufactured '19: ?
Manufactured '20: 14,277 Ibs.
FORMATION. From benzoic acid by action of sulfuryl chloride
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 329
Lange, Zwischenprodukte, #42
Dyes Derived from Benzoyi Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
814
ANTHRAQUINONE AND
ALLIED DYES
Algol Yellow WG
I '14: 5,185
I '20: 4
1-Amino-anthraqui-
none
V
815
Algol Scarlet G
I '20: 959
l-Amino-4-methoxy-
anthraquinone
V
DYES CLASSIFIED BY INTERMEDIATES
141
Dyes Derived from Benzoyl Chloride (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
(continued)
816
Algol Red 5G
I '14: 1,338
1 : 4-Diamino-anthra-
V
I '20: 51
quinone
Benzoyl chloride
(2 mols)
817
Algol Yellow R
I '14: 4,887
1 : 5-Diamino-anthra-
V
I '20: 2,299
quinone
M'20: ?
Benzoyl chloride
(2 mols)
818
Algol Pink R
I '14: 126
l-Amino-4-hydroxy-
V
I '20: 1,368
anthraquinone
819
Algol Red R
I '14: 2,322
1 : 5-Diamino-anthra-
V
I '20: 7,335
quinone
Benzoyl chloride
(2 mols)
[Oxidation]
821
Algol Brilliant
I '14: 3,893
Diamino-anthramfm
V
Violet 2B
I '20: 827
Benzoyl chloride
(2 mols)
822
Algol Brilliant
I '14: 6,195
1:2: 4-Triamino-an-
V
Orange FR
I '20: 482
thraquinone (?)
823
Algol Violet B
I '20: 69
l-Amino-4: 5: 8-tri-
V
hydroxy-anthraqui-
none
870
Algol Corinth R
I '20: 134
1-Amino-anthraquinone
V
2-Chloro-anthraquinone
[Nitration, Reduction]
142 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Benzoyl Chloride (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GKOUP
DYES
889
Indigo Yellow 3G
Indigo or Phenyl-gly-
cine or Phenyl-gly-
cine-o-carboxylic acid
or Thiocarbanilide or
'
Aniline or Phthalic
Anhydride
890
Ciba Yellow G
I '14: 48
Indigo or Phenyl-gly-
cine or Phenyl-gly-
cine-o-carboxylic acid
or Thiocarbanilide or
Aniline or Phthalic
Anhydride
[Bromination]
N-Benzoyl-o-tolidine
H 3 C
CH a
. NH/~~\- <^~^>NH 2 C 2 iH 20 N 2 O = 316
STATISTICS. Manufactured 1919: ?
FORMATION. Tolidine is heated in toluene solution with benzoyl
chloride under a reflux condenser
LITERATURE. Lange, Zwischenprodukte, #1281
Dyes Derived from AT-Benzoyl-o-tolidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
104
MONOAZO DYE
Benzoyl Pink
Nevile-Winther's Acid
D
DYES CLASSIFIED BY INTERMEDIATES 143
[(W-Benzyl-anilino) -methyl] -benzene-sulfonic Acid (C. A. nomen.)
See Dibenzyl-aniline-sulfonic Acid
Benzyl Chloride
a-Chloro-foluene (C. A. nomen.)
CH 2 C1
^ 126.5
STATISTICS. Imported '14: 4,589 Ibs.
Manufactured '17: 136,179 Ibs.
Manufactured '18: 690,930 Ibs.
Manufactured '19: 720,953 Ibs.
Manufactured '20: 1,246,412 Ibs.
FORMATION. From boiling toluene by passing in chlorine until the
theoretical amount (37.5%) has been absorbed
LITERATURE. Cam, Intermediate Products (2d Ed.), 15
Lange, Zwischenprodukte, #5
Dyes Derived from Benzyl Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TEIPHENYL-
METHANE DYES
517
Methyl Violet 5B
I '14: 22,387
[Benzylation of Methyl
B
Benzyl Violet
M'17: ?
Violet]
I '20: 3,313
or
Dimethyl-aniline
(3 mols)
Phenol
523
Fast Green
I '14: 14,347
m-Nitro-benzaldehyde
A
I '20: 3,612
Dimethyl-aniline
(2 mols)
Benzyl chloride (2 mols)
[Sulfonation, Oxidation]
XANTHONE DYE
586
Chrysoline
I '20: 1,402
Phthalic Anhydride
A
Resorcinol (2 mols)
144 DYES CLASSIFIED BY INTERMEDIATES
Benzyl-ethyl-aniline
Ethyl-benzyl-aniline
JV-Ethyl-7V-phenyl-&enzylamine (C. A. nomen.)
C 2 H 5 . N . CH
STATISTICS. Imports 1914: small amount
Manufactured 1917: ?
Manufactured 1918: ?
Manufactured 1919: ?
Manufactured 1920: 159,636 Ibs.
FOKMATION. From one part of ethyl-aniline and two parts of benzyl
chloride, by boiling under a reflux condenser for four hours
LITERATURE. Cain, Intermediate Products (2d Ed.), 69
Dyes Derived from Benzyl-ethyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
505
Light Green SF
I '14: 71,462
Benzyl-ethyl-aniline
A
Yellowish
M'19: ?
(2 mols)
I '20: 7,490
Benzaldehyde
M'20: ?
[Sulfonation; Oxidation]
506
Erioglaucine
I '14: 66,526
Benzyl-ethyl-aniline
A
M'19: ?
(2 mols)
I '20: 6,160
Benzaldehyde-o-sul-
M'20: ?
fonic acid
[Sulfonation; Oxidation]
508
Xylene Blue AS
I '14: 8,238
Benzyl-ethyl-aniline
A
I '20: 5,573
(2 mols)
3-Methyl-benzalde-
hyde-4: 6-disulfonic
Acid
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES
145
Dyes Derived from Benzyl-ethyl-aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
(continued)
545
Patent Blue A
I '14: 63,744
Benzyl-ethyl-aniline
A
M'18: ?
(2 mols)
I '20: 44,801
ra-Nitro-benzaldehyde
or m-Hydroxy-benzal-
dehyde
[Sulfonation; Oxidation
Benzyl-ethyl-aniline-disulfonic Acid
A^-Ethyl-A7"-(p-sulfo-beDzyl)-metanilic Acid (C. A. nomen.)
C 2 H 5 N CH
3 H
Note. Position of sulfonic group in the benzyl radical is not fully de-
termined
STATISTICS. Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION. Benzyl-ethyl-aniline is dissolved with cooling in two parts
of 20 per cent oleum, and is then treated with two and a half parts
of 80 per cent oleum, and the mixture warmed at 60 until the
sulfonation is complete
LITERATURE. Cain, Intermediate Products (2d Ed.), 70
Lange, Zwischenprodukte, #1500
146
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Benzyl-ethyl-aniline-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TREPHENYL-
METHANE DYES
528
Fast Acid
Violet 10B
I '14: 12,919
M'17: ?
M'18: ?
Hydrol
[Oxidation]
A
M'19: ?
I '20: 10,086
M'20: ?
Benzyl-ethyl-aniline-sulfonic Acid 1
See, Ethyl-sulfobenzyl-aniline
Benzyl-ethyl-^-phenylene-diamine-sulfonic Acid
See t Ethyl-sulfobenzyl-p-phenylene-diamine
3-Benzylimino-4-methyl-diphenylamine
See, ATM3eiizyl-Ar^)henyl-4-w-torylene-diarmne
Benzyl-methyl-aniline
Methyl-benzyl-aniline
]V-Methyl-]V-phenyl-6enzylamme (C. A. nomen.)
FORMATION. From methyl-aniline and benzyl chloride by heating
together on a water bath for a few hours
LITERATURE. Cain, Intermediate Products (2d Ed.), 69
1 The data and the dye table should have been placed here rather than under ethyl-
sulfobenzyl-aniline. The Author.
DYES CLASSIFIED BY INTERMEDIATES
147
Dyes Derived from Benzyl-methyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-
METHANE DYES
504
Light Green SF
Bluish
I '14: 6,693
M'17: ?
M'18: ?
Benzyl-methyl-aniline
(2 mols)
Benzaldehyde
[Sulfonation; Oxidation]
527
Acid Violet 4BN
I '14: 29,184
I '20: 23,335
M'20: ?
Ketone
[Sulfonation]
A
Benzyl-a-naphthylamine
N-Benzyl-1-naphthylamine (C. A. nomen.)
HN . CE
FORMATION. a-Naphthylamine is heated in an autoclave with benzyl
chloride in the presence of a catalyst
LITERATURE. Lange, Zwischenprodukte, #1363
Dye Derived from Benzyl-a-naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
654
Nile Blue 2B
5-Diethylamino-2-
B
nitroso-phenol
148 DYES CLASSIFIED BY INTERMEDIATES
W 3 -Benzyl-W-phenyl-4-m-folylene-diamine (C. A. nomen
Phenyl-p-amino-benzyl-o-toluidine (CH 3 = 1)
3-Benzylimino-4-methyl-diphenylamine
NH
= C 20 H 2 oN 2 288
FORMATION. -1-Tn-Tolylene-diamine hydrochloride is melted with ani-
line at 220-270, forming AP-phenyl-l-m-tolylene-diamine. This
latter body upon being warmed with benzyl chloride with or with-
out a diluent such as alcohol forms the benzyl-derivative desired
LITERATURE. Lange, Zwischenprodukte, #1621, 1622, 1734
Dyes Derived from W'-Benzyl-A^-phenyM-m-tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
684
Rhoduline Violet
I '14: 2,751
I '20: 35
Nitroso-dimethyl-
aniline
B
684
Rhoduline Red B
Nitroso-ethyl-aniline
B
684
Rhoduline Red G
Nitroso-ethyl-o-
toluidirie
B
Beta=j3
Note. This is not considered in the alphabetical arrangement, e.g.
beta-Naphthol is indexed as (3-Naphthol under "N". However /3-
Naphthol is placed after a-Naphthol
Beta Acid
See, Anthraquinone-2-sulfonic Acid
Beta-Naphthol
See, /3-Naphthol under N
DYES CLASSIFIED BY INTERMEDIATES
149
Bi-compounds
See, Di-compounds, e.g., for binitro-benzol (or -benzene), see
dinitro-benzene
/>:/>'-Bis(diethylamino)-&enzohydrol (C. A. nomen.)
See, p : p'-Tetraethyl-diamino-benzohydrol
^:/>'-Bis(diethylamino)-&enzophencne (C. A. nomen.)
See, p : p'-Tetraethyl-diamino-benzophenone
/>:/>'-Bis(dimethylamino)-&enzohydrol (C. A. nomen.)
See, Hydrol
/>:/>'-Bis(dimethylamino)-&enzophenone (C. A. nomen.)
See, Ketone
3:5-Bis[/5-(5-hydroxy-7-sulfo-2-naphthyl)-carbamido]-/>-^oluene-
sulfonic Acid (C. A. nomen.)
See, Sulf o-w-tolylene-diamine-bis (carbonyl-amino-naphthol-
sulfonic Acid)
Broenner's Acid
See, page 152
1 -Bromo-anthr aqulnone
Br
CO^/
FORMATION. From potassium salt of anthraquinone-1-sulfonic acid,
by treatment with bromine and acid
LITERATURE. Lange, Zwischenprodukte, #3083
Dye Derived from l-Bromo- nthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
873
ANTHRAQUINONE AND
ALLIED DYES
Helindone
Brown AN
I '14: 2,831
I '20: 16,290
1-Bromo- anthraquinone
(2 mols)
1 : 4-Diamino-anthra-
V
qumone
150
DYES CLASSIFIED BY INTERMEDIATES
6-Bromo-2-hydroxyl-3-methy--fhionaphthene (C. A. and English
numbering)
6-Bromo-3-hydroxyl-4-methyl-(l)-thionaphthene (German num-
bering)
Br
\
CH
C 9 H 7 BrOS =
CH 3
FORMATION. 4-Bromo-6-nitro-2-methyl-benzoic acid is reduced with
NaA; the ammo-compound diazotized, and then treated with
potassium xanthogenate (potassium ethyl xanthate). The xantho-
genate compound upon being treated with chloro-acetic acid forms
bromo-methyl-phenyl-thioglycol-o-carboxylic acid
Br/\S.CH 2 .COOH
X/COOH
CH 3
This compound upon being fused with caustic alkali, forms the
carboxylic acid of 5-bromo-2-hydroxy-3-methyl-thionaphthene.
The carboxylic acid decomposes, evolving C02, when its solution
is acidified and warmed
LITERATURE. Lange, Zwischenprodukte, #2169
Georgievics and Grandmougin, Dye Chemistry, 433, 437
Cf. Cain, Intermediate Products (2d Ed.), 158, 159
Dye Derived from 5-Bromo-2-hydroxyl-3-methyl-thiDnaphthene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
910
Helindone Pink BN
I '14: 41,699
5-Bromo-2-hydroxyl-3-
V
I '20: 17,162
methyl-thionaphthene
(2 mols)
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES
I-Bromo-4-methylamino-anthraquinone
C(
151
NH . CH 3
FORMATION. From 1-methylamino-anthraquinone by treating its
pyridine solution with bromine and warming on the water bath
LITERATURE. Lange, Zwischenprodukte, #3190
Dye Derived from l-Bromo-4-methylamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
856
Alizarin Astrol B
I '14: 10,907
p-Toluidine
ACr
I '20: 15,518
[Sulfonation]
[? Classification]
2-Bromo-l-methylammo-anthraquinone
m NH.CHa
>
Br
FORMATION. From l-amino-2-bromo-anthraquinone by methylation
with dimethyl-sulfate
LITERATURE. Lange, Zwischenprodukte, #3191
Dye Derived from 2-Bromo-l-methylammo-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
839
Algol Blue K
I '14: 150
2-Bromo-l-methyl-
V
I '20: 218
amino-anthraqui-
none (2 mols)
152
DYES CLASSIFIED BY INTERMEDIATES
4-Bromo-W-methyl-anthrapyridone
6-Bromo-3-methyl-3: 7-pm'-naphthoquinoline-2(3) : 7-dione (C.A,
nomen.)
/ co \
HC N . CH 3
H
J V\
I =C 17 H,
)BrN0 2 =
co/Y
FORMATION. (1) From 1-methylamino-anthraquinone, by acetylation
of amino group, and condensation to the JV-methyl-anthra-
pyridone. Bromination of this latter compound in the 4 position
results in 4-bromo-A^-methyl-anthrapyridone. (2) From 4-bromo-
1-methylamino-anthraquinone by acetylation and closing the ring
LITERATURE. Lange, Zwischenprodukte, #3609
Georgievics and Grandmougin, Dye Chemistry, 464-465
Ullmann, Enzy. tech. Chemie, 1, 192
Dye Derived from 4-Bromo-W-methyl-anthrapyridone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
825
Algol Red B
I '14: 2,399
2-Amino-anthraq ui-
V
I '20: 4,151
none
6-Bromo-3-methyl-3 : 7-/>eri-naphthoquinoline-2(3) : 7-dione (C. A 1
nomen.)
See, 4-Bromo-Af-methyl-anthrapyridone
Broenner's Acid
2-Naphthylamine-6-sulfonic Acid
6-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
Naphthylamine-sulfonic Acid Br.
j8-Naphthylamine-/3-sulfonic Acid
Amino-Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES
153
H0 3 S
STATISTICS. Imported '14: 2,316 Ibs.
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. By heating the sodium salt of Schaeffer's Acid with con-
centrated ammonia in an autoclave at 180
LITERATURE. Cain, Intermediate Products (2d Ed.), 206
Lange, Zwischenprodukte, #2371-2376
Thorpe, Die. Chemistry, 3, 601
Dyes Derived from Broenner's Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
172
MONOAZO DYES
Fast Brown 3B
I '14: 1,477
a-Naphthol
A
174
Double Brilliant
Scarlet G
I '14: 210,429
M'17: ?
M'20: ?
/3-Naphthol
A
176
Double Scarlet
Extra S
Scarlet 2R
I '14: 10,182
M'17: ?
I '20: 1,653
Nevile-Winther's Acid
A
177
230
Chrome Yellow D
Mordant Yellow
DISAZO DYES
Cloth Red 3G, 3GA
I '14: 129,651
M'17. ?
M'18: 32,011
M'19: ?
I '20: 1,389
M'20: ?
I '14: 251
Salicylic Acid
or
o-Cresotic Acid
o-Amino-azo-toluene
M
M
302
Hessian Brilliant
Purple
Diamino-stilbene-
disulfonic Acid
Broenner's Acid
(2 mols)
D
154 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Broenner's Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
316
DISAZO DYES
(continued)
Brilliant Congo G
Benzidine
Amino-R Acid f
D
357
Dianol Red B
Dichloro-benzidine
Broenner's Acid
(2 mols)
D
365
Benzo Purpurin B
I '14: 21,090
M'17: ?
M'18: ?
M'19: ?
Tolidine
Broenner's Acid
(2 mols)
D
366
Diamine Red B
Delta Purpurin 5B
I '14: 21,058
M'17: ?
M'18: ?
I '20: 1,896
Tolidine
2-Naphthylamine-7-
sulfonic Acid
D
368
Brilliant Purpurin
4B
I '14: 6,634
Tolidine
Naphthionic Acid
D
370
Brilliant Congo R
I '14: 19,133
I '20: 11,129
Tolidine
Amino-R Acid
D
CAcid
1 : 5-Dihydroxy-naphthalene-2-sulfonic Acid
2-Naphthol-4: 8-disulfonic Acid
2-Naphthylamine-4 : 8-disulfonic Acid
(These intermediates not considered herein)
Carbazole
Dibenzo-pyrrole
Diphenylene-imide
H
DYES CLASSIFIED BY INTERMEDIATES
155
STATISTICS. Imported '14: very small
Manufactured ' 18 : ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. By extraction from coal-tar or crude anthracene
LITERATURE. Ullmann, Enzy. tech. Chemie, 3, 274
Lange, Zwischenprodukte, page 308
Dyes Derived from Carbazole
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
748
SULFUR DYE
Hydron Blue
I '14: 296,723
I '20: 19,210
M'20: ?
p-Nitroso-phenol
[S+NaaS]
V
Carbolic Acid
See, Phenol
Carbonyl Chloride
See, Phosgene
2-Carboxy-5-chloro-phenyl-thioglycolic Acid
See, 5-Chloro-phenyl-thioglycol-o-carboxylic Acid
^-(Carboxy-methyl)-anthranilic Acid (C. A. nomen.)
See, Phenyl-glycine-o-carboxylic Acid
2-(Carboxy-methyl-mercapto)-4-chloro-benzoic Acid (C. A. nomen.)
See, 5-Chloro-phenyl-thioglycol-o-carboxylic Acid
Cassella's Acid
See, 2-Naphthol-7-sulfonic Acid
Cassella's Acid F
See, 2-Naphthylamine-7-sulfonic Acid
156
DYES CLASSIFIED BY INTERMEDIATES
Chi Acid
See, Anthraquinone-1 : 8-disulfonic Acid
Chicago Acid
See, l-Amino-8-naphthol-2 : 4-disulf onic Acid
3-Chloro-aniline-2-sulfonic Acid
See, 2-Amino-6-chloro-benzene-sulfonic Acid
5-Chloro-o-anisidine (NH* = 1 )
NH 2
tOCHa ___ C7 H 8C1NO -_ 157>5
FORMATION. 1 : 4-Dichloro-3-nitro-benzene is boiled with caustic potash
and methyl alcohol and the resulting chloro-nitro-anisol is reduced
with iron and acetic acid
LITERATURE. J. Soc. Chem. Ind. 21, 610 (1902)
U. S. Pat. 695,812
Laaige, Zwischenprodukte, #1034
Dye Derived from 5-Chloro-o-anisidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
A ppli-
cation
Class
MONOAZO DYE
97
Chloranisidine
/3-Naphthol
MF
Scarlet
I-Chloro-anthraquinone (C. A. nomen.)
a-Chloro-anthraquinone
CO 0,
= 242.5
FORMATION. From potassium anthraquinone-1-sulfonate by treatment
at 100-with chlorine and dilute hydrochloric acid
LITERATURE. Lange, Zwischenprodukte, #3081, 3083, 3086
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1-Chloro-anthraquinone
157
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
834
Algol Gray B
I '14: 4,192
1 - Amino-anthr aquinone
V
I '20: 890
[Nitration, Reduction]
2-Chloro-anthraquinone (C. A. nomen.)
/3-Chloro-anthraquinone
aCOv xv
\X \pi
I =C 14 H 7 C10 2 := 242.5
FORMATION. (1) From sodium anthraquinone-2-sulfonate in aqueous
solution, by adding hydrochloric acid, and by passing in chlorine
until all the 2-chloro-anthraquinone is precipitated out. (2) From
phthalic anhydride and chloro-benzcne by first condensing in pres-
ence of A1C1 3 to chloro-benzoyl-benzoic acid, and then by warming
with sulfuric acid to 2-chloro-anthraquinone
LITERATURE. Lange, Zwischenprodukte, 3082, 3083
Ullmann, Enzy. tech. Chemie, 1, 472
Dyes Derived from 2-Chloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
V
824
ANTHRAQUINONE AND
ALLIED DYES
Algol Orange R
I '14: 51
I '20: 406
1-Amino-anthraquinone
828
Indanthrene
Bordeaux B
I '20: 2,741
2-Chloro-anthraquinone
(2 mols)
1 : 5-Diamino-anthra-
V
quinone
870
Algol Corinth R
1*29: 134
1-Amino-anthraquinone
[Nitration, Reduction]
Benzoyl chloride
V
158 DYES CLASSIFIED BY INTERMEDIATES
l-Chloro-anthraquinone-2-carboxylic Acid
/~\i
,co x
COOH
286.5
FORMATION. 2-Methyl-l-nitro-anthraquinone is treated with chlorine
in nitre-benzene solution, whereby the nitro group is substituted
by chlorine and the methyl group oxidized, thus forming 1-chloro-
anthraquinone-2-carboxylic acid
LITERATURE. Lange, Zwischenprodukte, #3171
Ullmann, Enzy tech. Chemie, 1, 484
Dye Derived from l-Chloro-anthraquinone-2-carboxylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
831
Indanthrene
I '14: 6,056
/3-Naphthylamiue
V
RedBN
I '20: 4,766
o-Chloro- frenzaldehyde
HCO
:1 rzzC 7 H 6 C10 140.5
STATISTICS. Manufactured '20: ?
FORMATION. From o-chloro-benzyl alcohol by oxidation with nitric
acid in a sulphuric acid solution at about 40 C,
LITERATURE. J. Soc. Chem. Ind. 18, 576 (1899)
Lange, Zwischenprodukte, #179-184
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Chloro-benzaldehyde
159
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
496
TRIPHENYL-
METHANE-DYES
Setoglaucine
I '20: 1,102
Dimethyl-aniline
(2 mols)
[Oxidation]
B
500
Setocyanine O
I '14: 923
I '20: 1,102
Ethyl-o-toluidine
(2 mols)
[Oxidation]
B
503
Night Green A
Neptune Green
Brilliant Milling
Green B
I '14: 40,868
M'19: ?
I '20: 10,940
M'20: ?
Ethyl-sulfobenzyl-ani-
line (2 mols)
[Oxidation]
A
551
Eriochrome
Azurol B
I '14: 21,060
I '20: 7,275
o-Cresotic acid (2 mols)
[Oxidation]
ACr
2-Chloro-benzaldehyde-6-sulfonic Acid
3-Chloro-2-formyl-6enzene-sulfonic Acid (C. A. nomen.)
HCO
xiwsOi 1^1 o TT oi fi Q oon PI
v^/7JtJ-5^>'-'-Vy4*^ ^j\Jt-nitro- toluene (C. A. nomen.)
See, p-Nitro-benzyl Chloride
(m-Chloro-phenyl-mercapto) -acetic Acid (C. A. nomen.)
See, m-Chloro-phenyl-thioglycolic Acid
m-Chloro-phenyl-thioglycolic Acid
(m-Chloro-phenyl-mercapto)-acetic Acid (C. A. nomen.)
S.CH 2 .COOH
C 8 H 7 C10 2 S=: 202.5
FORMATION. m-Chloro-aniline is diazotized, coupled with potassium
xanthate (C 2 H 5 . CS . SK), hydrolyzed to the mercapto-derivative,
and condensed with chloro-acetic acid
LITERATURE. Cf. Lange, Zwischenprodukte, #688
Dye Derived from m-Chloro-phenyl-thioglycolic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
917
Helindone Red B
I '14: 100
m-Chloro-phenyl-thio-
V
I '20: 200
glycolic Acid (2 mols)
[Oleum Condensation]
5-Chloro-phenyl-thioglycol-o-carboxylic Acid
2-Carboxy-5-chloro-phenyl-thioglycolic Acid
2-(Carboxy-methyl-mercapto)-4-chloro-6enzoic Acid (C. A.
nomen.)
Clf /Ns |S.CH 2 .COOH
i^COOH
FORMATION. 4-Chloro-anthranilic acid is diazotized, and reacted with
potassium ethyl xanthate, and then with chloro-acetic acid,
resulting in the formation of the chloro-phenyl-thioglycol-o-carboxy
acid
LITERATURE. Lange, Zwischenprodukte, #2170; cf. #518
172
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 5-Chloro-phenyl-thioglycol-o-carboxylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
909
Ciba Red B
5-Chloro-phenyl-thio-
V
glycol-o-carboxylic
acid (2 mols)
a-Chloro-toluene (C. A. nomen.)
See, Benzyl Chloride
2-Chloro-5-toluidine-4-sulfonic Acid (CH3=1)
See, 2-Amino-5-chloro-p-foluene-sulfonic Acid (C. A. nomen
(4-Chloro-o-tolyl-mercapto) -acetic Acid (C. A. nomen.}
See, 4-Chloro-2-tolyl-thioglycolic Acid
4-Chloro-2-tolyl-thioglyeolic Acid
(4-Chloro-o-tolyl-mercapto)-acetic Acid (C. A. nomen.)
S.CH 2 COOH
nrC 9 H 9 C10 2 S=: 216.5
FORMATION. 4-Chloro-o-toluidine (NH 2 =1) is diazotized, coupled
with potassium xanthate (C 2 H 6 O . CS . SK), hydrolyzed to the
mercapto-derivative, and condensed with chloro-acetic acid
LITERATURE. Lange, Zwischenprodukte, #688
Cf. Geogievics and Grandmougin, Dye Chemistry, 437
DYES CLASSIFIED BY INTERMEDIATES
173
Dye Derived from 4-Chloro-2-tolyl-thioglycolic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
918
Helindone Red 3B
I '14: 27,874
4-Chloro-2-tolyl-thio-
V
I '20: 4,385
glycolic Acid (2 mols)
[Oleum Condensation]
[There is some question
as to the Cl- and
CH 3 - positions of that
chloro-tolyl-thiogly-
colic acid used]
Chromogen I
See, Chromotropic Acid
Chromotrope Acid
See, Chromotropic Acid
Chromotropic Acid
1 : 8-Dihydroxy-naphthalene-3 : 6-disulfonic Acid
4: 5-Dihydroxy-2 : 7-naphthalene-disulfonic Acid (C. A. nomen.)
Chromotrope Acid
Chromogen I
HO OH
H0 3 S
S0 3 H
STATISTICS. Manufactured '18: ?
Manufactured ' 19: 164,654 Ibs.
Manufactured '20: 152,352 Ibs.
FOKMATION. (1) From l-Naphthol-3 : 6 : 8-trisulf onic acid by fusion
of the sodium salt of this acid with caustic soda at 170-220.
(2) From H acid by heating with a dilute caustic soda solution
in an autoclave at about 265
LITERATURE. Cain, Intermediate Products (2d Ed.), 232
Lange, Zwischenprodukte, #2775, 2670
174 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Chromotropic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
40
Chromotrope 2R
I 4 '14: ^5,000
Aniline
A
d * 1
M/19: "%?
57
Chromotrope 2B
I '14: 7,970
M'18: ?
p-Nitro-aniline
ACr
M'19: ?
M'20: ?
61
Victoria Violet
I '14: 52,365
M'17: ?
M'18: ?
M'19: 105,086
I '20: 2,182
M '20: ?
p-Phenylene-diamine
actually from
p-Nitro-aniline and
Reduction
or
p-Amino-acetanilide
and Saponification
A
67
Chromotrope 6B
I '14: 2,818
M'17: ?
p-Amino-acetanilide
A
M'18: ?
M'19: 77,481
M '20: ?
114
Chromotrope 10B
M'19: ?
a-Napiithylamine
A
129
Chromazone Red A
I '14: 243
p-Amino-benzaldehyde
M
130
Chromazone Blue R
p-Amino-benzaldehyde
Ethyl-phenyl-hydra-
M
zine
or
p-Amino-benzylidine-
ethyl-phenyl-hydra-
zone
171
Chromotrope 8B
M'18: ?
Naphthionic Acid
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Chromotropic Acid (continued)
175
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
292
Acid Alizarine
p-Phenylene-diamine
M
Black I
Salicylic Acid
323
Dianil Blue R
M '20: ?
Benzidine
D
Chromotropic Acid
(2 mols)
379
Dianil Blue 2R
I '14: 14,434
Tolidine
D
Benzo New Blue 2B
Nevile-Winther's Acid
380
Dianil Blue B
Tolidine
D
Chromotropic Acid
(2 mols)
415
Dianil Blue G
M'19: ?
Dianisidine
D
M'20: ?
Chromotropic Acid
(2 mols)
TRISAZO DYE
479
Dianil Black R
Benzidine
D
Naphthionic Acid
m-Phenylene-diamme
ANTHRAQUINONE AND
ALLIED DYES
777
Chromogen I
[Oxidation on fiber]
ACr
Chrysazin
1 : 8-Dihydroxy-anthraquinone (not considered herein)
Chryseic Acid
4-Nitro-l-naphthol (not considered herein)
Cincholepidine
See, Lepidine
Cleve's Acid
See, l-Naphthol-5-sulfonic Acid
See, l-Naphthylamine-6-sulfonic Acid
See, l-Naphthylamine-7-sulfonic Acid
176 DYES CLASSIFIED BY INTERMEDIATES
Cleves a Acid
See, Laurent's Acid (l-Naphthylamine-5-sulfonic Acid)
Cleve's p Acid
See, l-Naphthylamine-6-sulfonic Acid
Also applied to l-Nitro-naphthalene-6-sulfonic acid
Cleve's 7 Acid
l-Naphthylamine-3-sulfonic Acid (not considered herein)
Cleve's 5 Acid
See, l-Naphthylamine-7-sulfonic Acid
This trivial name also applied to
l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)
Cleve's B Acid
See, l-Naphthylamine-7-sulfonic Acid
This trivial name also applied to
l-Nitro-naphthalene-6-sulfonic Acid (not considered herein)
l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)
Cleve's Acids
See, l-Naphthylamine-6-and-7-sulfonic Acids
Cleve's a-Nitro-naphthalene-sulfonic Acid
l-Nitro-napthalene-5-sulfonic Acid (not considered herein)
Cleve's 7-Nitro-naphthalene-sulfonic Acid
l-Nitro-naphthalene-3-sulfonic Acid (not considered herein)
Cleve's 5-Nitro-naphthalene-sulfonic Acid
l-Nitro-naphthalene-8-sulfonic Acid (not considered herein)
Cleve's 0-Nitro-naphthalene-sulfonic Acid
l-Nitro-naphthalene-6-sulfonic Acid (not considered herein)
l-Nitro-naphthalene-7-sulfonic Acid (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES
Cresol
177
Note. C. A. practice is to start the numbering of cresols from the OH
group unless there is present a substituent of (< higher order" as SO^H.
European practice is generally to start numbering with
OH
= C 7 H 9 O=:108
STATISTICS. Imported '14: 245,835 Ibs.
Manufactured '19: ?
Manufactured '20: ?
FORMATION. Extracted from coal tar
LITERATURE. Lange, Zwischenprodukte, #438-452
Dye Derived from Cresol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation ^
Class
DISAZO DYE
311
Orange TA
I '14: 602
Benzidine
D
M'17: ?
Naphthionic Acid
M'18: ?
M'19: ?
M'20: ?
2: 3-Cresotic Acid (C. A. nomen.)
See, o-Cresotic Acid
o-Cresotic Acid
o-Cresotinic Acid
2: 3-Cresotic Acid (C. A. nomen.)
o-Homo-salicylic Acid
COOH
r=C 8 H 8 3 152
178
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Imported '14: very small
Manufactured '20: ?
FORMATION. By dissolving o-cresol in caustic soda, evaporating to a
dry powder; then by treating this powder with carbon dioxide
under pressure
LITERATURE. Cain, Intermediate Products (2d Ed.), 153
Lange, Zwischenprodukte, #775
Dyes Derived from o-Cresotic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
177
Chrome Yellow D
Broenner's Acid
M
DISAZO DYES
351
Cresotine Yellow G
I '14: 1,748
Benzidine
D
M'17: ?
o-Cresotic Acid (2 mols)
M'18: ?
M'19: ?
,
M'20: ?
392
Toluylene
I '14: 67,022
Tolidine
D
Orange G
M'18: ?
4: 6-Diamino-ra-
M '19: ?
toluene-sulfonic Acid
I '20: 273
M'20: ?
395
Cresotine Yellow R
Tolidine
D
o-Cresotic acid (2 mols)
TRIPHENYL-
METHANE DYES
551
Eriochrome
I '14: 21,060
o- Chloro-benzaldehyde
ACr
Azurol B
I '20: 7,275
[or other halogen]
o-Cresotic Acid (2 mols)
[Oxidation]
552
Chromal Blue G
I '14: 1,335
2-Chloro-5-nitro-ben-
M
zaldehyde
o-Cresotic Acid (2 mols)
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Cresotic Acid (continued)
179
Schultz
Number
or Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES (continued)
553
Eriochrome
1 '14: 2,249
Benzaldehyde-o-sulfonic
ACr
Cyanine R
I '20: 2,205
Acid
o-Cresotic Acid (2 mols)
[Oxidation]
554
Chrome Azurol S
I '14: 2,469
2-Chloro-benzaldehyde-
ACr
I '20: 551
6-sulfonic Acid
o-Cresotic Acid (2 mols)
[Oxidation]
o-Cresotinic Acid
See, o-Cresotic Acid
Croceine Acid
2-Naphthol-8-sulfonic Acid (C. A. nomen.)
Bayer's Acid
0-Naphthol-sulfonic Acid B (of Schultz)
0-Naphthol-a-sulfonic Acid (of Bayer & Co.'s Patents)
Croceine Sulfonic Acid
o-Acid (of Claus and Voltz) l
Rumpff Acid
H0 3 S
. /\
iOH
STATISTICS. Manufactured 1919:
Manufactured 1920:
FORMATION. /3-Naphthol is sulfonated at a low temperature, forming
mostly croceine acid, but accompanied by some Schaeffer's acid.
They are generally separated by crystallization of their salts
LITERATURE. Cain, Intermediate Products (2d Ed.), 225
Lange, Zwischenprodukte, #2435-2439
Thorpe, Die. Chemistry, 3, 625
1 Glaus and Voltz incorrectly assigned to this aci4 the constitution, 2-naphthol-3-
sulfonic aciclr
180 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Croceine Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
167
Croceine Scarlet
I '14: 3,101
Naphthionic Acid
A
3BX
M'17: ?
M'18: ?
M'19: ?
I '20: 650
M'20: ?
DISAZO DYES
249
Croceine Scarlet 3B
I '14: 9,613
Amino-azo-benzene-
A
sulfonic Acid
251
Croceine Scarlet
I '20: 100
Amino-azo-benzene-
A
disulfonic Acid
255
Croceine Scarlet 8B
I '14: 2,379
Amino-azo-toluene-
A
Ponceau 6 RB
I '20: 154
sulfonic Acid
259
Ponceau 10 RB
I '14: 201
Sulfanilic Acid
A
o-Anisidine
313
Congo Rubine
I '14: 46,213
Benzidine
D
M'17: ?
Naphthionic Acid
M'18: ?
I '20: 2,601
320
Bordeaux
I '14: l,33f
Bonzidine
D
M'18: ?
Croceine Acid (2 mols)
M'19: ?
M '20: ?
321
Heliotrope 2B
I '14: 1,473
Benzidine
D
I '20: 60
l-Naphthol-4:8-
disulfonic Acid
324
Chicago Blue 4R
I '14: 1,199
Benzidine
D
1 - Amino-8-naphthol-4-
sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Croceine Acid (continued)
181
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
384
Chicago Blue 2R
I '14: 23,877
Tolidine
D
Diamine Blue C2R
l-Amino-8-naphthol-4-
sulfoDic Acid
420
Azidine Wool
Dianisidine
D
BlueB
l-Ammo-8-naphthol-4-
sulfonic Acid
Croceine-sulfonic Acid
See, Croceine Acid
\l/ Cumidine
See, Pseudocumidine (C. A. nomen.)
Dahl's Acid
See, 2-Naphthylamine-5-sulfomc Acid
Dahl's Acid II
See, l-Naphthylamine-4 :6-disulf onic Acid
Dahl's Acid III
See, l-Naphthylamine-4 :7-disulf onic Acid
Dahl's Acids
l-Naphthol-4 :6-and-4 :7-disulf onic Acids (not considered herein)
Dehydro-thio-/>-toluidine
IV-Amino-5-methyl-2-phenyl-thiazol
Amino-benzenyl-0-amino-thio-cresol
p-Amino-phenyl-toluthiazole
l-(p-Amino-phenyl)-5-methyl-6enzothiazole (C. A. nomen.)
=Ci 4 H 12 N 2 S =
182
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Bjy heating together 3J^ parts of p-toluidine with 1 part
of sulfur, gradually raising the temperature to the boiling point, and
finally fractionally distilling off the dehydro-thio-p-toluidine in a
vacuum
LITERATURE. Cain, Intermediates (2d Ed.), 77
Lange, Zwischenprodukte, #2219-2223
Dyes Derived from Dehydro-thio-/>-toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
117
MONOAZO DYES
Erica 2GN
I '14: 1,171
M'19: ?
I '20: 337
l-Naphthol-3:8-
disulfonic Acid
D
118
Geranine
Brilliant Geranine
I '14: 18,917
M'19: ?
I '20: 527
l-Naphthol-4:8-disul-
fonic Acid or 1-Naph-
thol-3-sulfonic Acid
or 1 : 8-Dihydroxy-
naphthalene-4-sul-
fonic Acid
D
119
Diamine Rose
I '14: 5,269
M'18: ?
M'19: ?
M'20: ?
l-Chloro-8-naphthol-
3 : 6-disulfonic Acid
D
614
THIOBENZENYL DYES
Chromine G
I '14: 1,001
[Sulfur, Methylation,
Sulfonation]
D
618
Thioflavine T
I '14: 35,224
I '20: 5,807
[Methylation]
B
Dehydro-thio-/>-toluidine-sulfonic Acid
IV-Amino-5-methyl-2-phenyl- i thiazol-sulfonic Acid
DTS (abbreviation for above in compounds, less NH^)
l-(4-Amino-?-sulfo-phenyl)-5-methyl-6enzothiazole (C. A. nomen.)
8
CH-
C . C 6 H 3 (S0 3 H) . NH 2 = Ci 4 Hi 2 N 2 3 S2 = 320
\ H X
DYES CLASSIFIED BY INTERMEDIATES
183
STATISTICS. Manufactured '19: ?
Manufactured '20: 51,961 Ibs.
FORMATION. By sulfonation of the "primuline melt" (from p-toluidine
and sulfur), and purification from the primuline-sulfonic acid also
formed
LITERATURE. Cain, Intermediate Products (2d Ed.), 78
Lange, Zwischenprodukte, #2237
Ullmann, Enzy. tech. Chemie, 3, 677
Dyes Derived from Dehydro-thio-/>-toluidine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
STILBENE DYES
16
Curcuphenine
Dehydro-thio-p-tolui-
D
dine-sulfonic Acid
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
17
Chlorophenine
Dehydro-thio-p-tolui-
D
dine-sulfonic Acid
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
[Reduction]
18
Diphenyl Fast
I '14: 10,229
Dehydro-thio-p-tolui-
D
Yellow
I '20: 1,102
dine-sulfonic Acid
(2 mols)
Dinitro-dibenzyl-disul-
fonic Acid or
Dinitro-stilbene- .
disulfonic Acid
MONOAZO DYES
51
Nitrophenine
I '14: 423
p-Nitro-aniline
D
Thiazol Ye low R
M'20: ?
190
Alkali Brown
M'19: ?
m-Phenylene-diamine
D
Benzo Brown 5R
M'20: 2,987
193
Clayton Cloth Red
I '14: 100
j8-Naphthol
A
Stanley Red
M'18: ?
M'19: ?
M'20: ?
184
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dehydro-thio-/>-toluidine-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
194
Rosophenine 10B
I '14: 3,077
Nevile-Winther's Acid
D
Thiazine Red R
M'19: ?
M'20: ?
196
Titan Red
I '14: 886
Schaeffer's Acid
D
M'19: ?
M'20: ?
198
Clayton Yellow
I '14: 29,879
Dehydro-thio-p-tolui-
D
Thiazol Yellow
M'18: ?
dine-sulfonic Acid
Mimosa C
M'19: ?
(2 mols)
I '20: 11,182
M'20: ?
199
Oriol Yellow
I '14: 13,416
Salicylic Acid
D
Cotton YeUow R
I '20: 125
M'20: ?
DISAZO DYE
209
Terracotta FC
I '14: 551
Naphthionic Acid
D
m-Phenylene-diamine
350
Alkali Yellow R
Benzidine
D
Salicylic Acid
THIOBENZENYL DYE
617
Chloramine Yellow
I '14: 180,497
[Oxidation]
D
Diamine Fast Yellow
M'17: ?
Columbia Yellow
M '18: 123,816
M'19: 54,077
I '20: 4,810
M'20: 100,248
Dehydro-thio-m-xylidine
IV-Amino-2-phenyl-5 : 7 : III-trimethyl-thiazol
l-(4-Amino-m-tolyl-)-3:5-dimethyl-6enzothiazole (C. A. nomen.)
H 3 C
268
DYES CLASSIFIED BY INTERMEDIATES
185
STATISTICS. Manufactured '19: ?
Manufactured '20: ?
FORMATION. From w-xylidine and sulfur by heating to the boiling
point until there is no further evolution of hydrogen sulfide; and by
separating by distillation from the excess m-xylidine, and by solution
in 30% hydrochloric acid from the tso-dehydro-thio-m-xylidine
LITERATURE. Lange, Zwischenprodukte, #2232
Cain, Intermediate Products (2d Ed.), 80
Anschiitz and Schultz, Ber., 22, 582 (1889)
Paul, Zeitsch. angew. Chem., 9, 679 (1896)
Dyes Derived from Dehydro-thio-m-xylidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
120
MONOAZO DYES
Salmon Red
M'20: ?
Amino-R Acid
D
121
Erica B
I '14: 5,349
I '20: 2,393
M'19: ?
l-Naphthol-3:8-
disulfonic Acid
D
122
Erica G
I '14: 2,370
I '20: 1,142
M'18: ?
G Acid
D
z'so-Dehydro-thio-m-xylidine
l-(6-Amino-w-tolyl)-3: 5-dimethyl-6enzothiazole (<7. A. nomen.)
H 3 C
FORMATION. As a by-product in the manufacture of dehydro-thio-w
xylidine (see dehydro-thio-m-xylidine)
LITERATURE. See dehydro-thio-w-xylidine
Heumann, Anilinefarben, 4, 752
186 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from zso-Dehydro-thio-m-xylidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
123
Emine Red
Schaeffer's Acid
A
Delta Acid
See, l-Naphthylamine-4 : 8-disulfonic Acid
and 2-Naphthylamine-7-sulf onic Acid
1: 6- (or 1: 7-)Diacetamido-anthraquinone
/\/ C
H 3 C.OC.NH j f T
\Ac
NH . CO . CH 3
FORMATION. The above intermediate is obtained by reduction and
acetylation of the easily soluble dinitro-anthraquinone, prepared
from the crude dinitration product of anthraquinone.
LITERATURE. Ger. Pat. 72,685, 198,048
Lange, Zwischenprodukte, #3218
Dyes Derived from 1:6- (or l:7-)Diacetamido-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
812
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
Orange RT
I '14: 2,103
I '20: 382
2-Acetamido-
anthraquinone
V
813
Indanthrene
Copper R
I '14: 1,268
1-Acetamido-
anthraquinone
V
DYES CLASSIFIED BY INTERMEDIATES 187
Diacetyl-o : o'-dinitro-benzidine
Diacetyl-3 : 3'-dinitro-benzidine (numbering from point of attach-
ment)
2:2'-Dimtro-p:p'-biacetanilide (C. A. nomen. with numbering from
" chief function" or the acetamido groups)
2 N NO 2
H 3 COC . HN/"" / ~\NH . COCH 3 == Ci 6 H 14 N 4 6 = 358
FORMATION. Benzidine is acetylated by boiling with acetic acid under
a reflux, and the resulting diacetyl-compound is nitrated by dissolv-
ing in 10 parts of nitric acid (sp. gr. 1.48) with cooling
LITERATURE. Beil, IV, 964
Brunner and Witt, Ber. 20, 1024 (1887)
Dye Derived from Diacetyl-o : o'-dinitro-benzidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
715
SULFUR DYE
Thiocatechine
[Sulfur and NajjS]
S
p-(2: 4-Diamino-anilino) -phenol (C. A. nomen.)
See, 2: 4-Diamino-4'-hydroxy-diphenylamine
1 : 4-Diamino-anthraquinone
= Ci 4 Hi N 2 O 2 =:238
FORMATION. From l-nitro-4-amino-anthraquinone (derived from 1-
amino-anthraquinone) by reduction with alkaline sodium sulfide
LITERATURE. Lange, Zwischenprodukte, #3221, 3232, 3233
Ullmann, Enzy. tech. Chemie, 1, 477
188 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 1 : 4-Diamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and .
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
816
ANTHRAQUINONE AND
ALLIED DYES
Algol Red 5G
I '14. 1,338
I '20: 51
Benzoyl chloride
(2 mols)
V
873
Helindone
Brown AN
I '14: 2,831
I '20: 16,290
1-Bromo-anthraquinone
(2 mols)
V
1 : 5-Diamino-anthraquinone
CO
NIL
FORMATION. (1) From 1 : 5-dinitro-anthraquinone by reduction.
(2) From 1 : 5-anthraquinone-disulfonic acid by treatment with
ammonia
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 477
Lange, Zwischenprodukte, #3109, 3115, 3222, 3265
Dyes Derived from 1 : 5-Diamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
817
Algol Yellow R
I '14: 4,887
Benzoyl chloride
V
I '20: 2,299
(2 mols)
M'20: ?
819
Algol Red R
I '14: 2,322
Benzoyl chloride
V
I '20: 7,335
(2 mols)
[Oxidation]
828
Indanthrene
I '20: 2,741
2-Chloro-anthraquinone
V
Bordeaux B
(2 mols)
DYES CLASSIFIED BY INTERMEDIATES 189
Dyes Derived from 1 : 5-Diamino-anthraquinone (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
845
ANTHRAQUINONE AND
ALLIED DYES
(continued)
Indanthrene
Maroon R
I '20: 46
1 : 5-Diamino-anthra-
quinone (2 mols)
V
848
Indanthrene
GrayB
I '14: 401
I '20: 2,639
1 : 5-Diamino-anthra-
quinone (2 mols ?)
V
Diamino-anthraquinones
(Probably a mixture of the 1: 4, ! 5 and 1: 8)
o
JNH 2
Dyes Derived from Diamino-anthraquinones
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
836
Helindone
I '20: 15,238
2-Anthraquinonyl-urea
V
Brown 3GN
chloride (2 mols)
4: 8-Diamino-anthrarufin
H 2 N OH
4 270
HO NH 2
FORMATION. 1 : 5-Dinitro-anthraquinone is partly reduced, giving 1 : 5-
dihydroxyamino-anthraquinone, which is then transformed into
diamino-anthrarufin
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 275
190 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 4:8-Diamino-anthrarufin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHBAQTJINONE AND
ALLIED DYES
820
Algol Brilliant
I '14: 12,784
Diamino-anthrarufin
V
Violet R
I '20: 7,856
(2 mols)
[Succinic Acid]
821
Algol Brilliant
I '14: 3,893
Benzoyl chloride
V
Violet 2B
I '20: 827
(2 mols)
Diamino-azoxy-toluene
p-Azoxy-o-toluidine
5:5'-Azoxy-bis-o-foluidine (C. A. nomen.)
H 2 N
C 14 H 16 N 4 = 256
O
NH 2
FORMATION. From 5-nitro-o-toluidine (NH 2 = 1) by reduction, using
zinc dust and caustic soda
LITERATURE. Cain, Intermediate Products (2d Ed.), 99
Lange, Zwischenprodukte, #1792
Dyes Derived from Diamino-azoxy-toluene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
483
TRISAZO DYES
St. Denis Red
Rosophenine 4B
I '14: 1,496
I '20: 550
Nevile-Winther's Acid
(2 mols)
D
484
Milling Scarlet B,S
Nevile-Winther's Acid
RAcid
A
DYES CLASSIFIED BY INTERMEDIATES 191
4: 6-Diamino-m-benzene-disulfonic Acid (C. A. nomen.)
See, w-Phenylene-diamine-disulfonic Acid
2: 6-Diamino-benzene-sulfonic Acid (C. A. women.)
See, p-Phenylene-diamine-sulfonic Acid
6: 6'-Diamino-m: m'-bi(benzene-sulfonic) Acid (C. A. nomen.)
See, Benzidine-disulfonic Acid
2: 2'-Diamino-5: 5'-bi-m-toluene-sulfonic Acid (C. A. nomen.)
See, o-Tolidine-disulfonic Acid
1 : 4-Diamino-2 : 3-dibromo-anthraquinone
NIL
Ci4H 8 Br 2 N 2 2 =r396
FORMATION. By brominating 1 : 4-diamino-anthraquinone, probably in
nitro-benzene solution. (The corresponding chloro-compound is
made by action of sulfuryl chloride)
LITERATURE. Cf. Lange, Zwischenprodukte, #3334
Barnett, Anthracene and Anthraquinone, 170-175, 190-
231
Dyes Derived from l:4-Diamino-2: 3-dibromo-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYE
847
Algol Green B
I '14: 2,796
l:4-Diamino-2: 3-di-
V
I '20: 527
bromo-anthraqui-
none (2 mols)
192
DYES CLASSIFIED BY INTERMEDIATES
2 : 7-Diamino-9-dioxide-? : ?-c?ibenzothiophene-disulfonic Acid
(C. A. nomen.)
See, Benzidine-sulfon-disulfonic Acid
p : ^'-Diamino-diphenylarnine
p:p'-Imino-bisaniline (C. A. nomen.)
199
STATISTICS. Imported '14: very small amount
FORMATION. Equal molecules of aniline and p-phenylene-diamine are
oxidized at by means of potassium permanganate to a blue in-
damine, which is then reduced with zinc dust and hydrochloric acid
LITERATURE. Nietzke, Ber., 16, 474
Lange, Zwischenprodukte, #1636, 1753
Dye Derived from />:/>'-Diamino-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANILINE BLACK
GROUP
923
Furreine DB
I '14: 54,005
p: p'-Diamino-diphenyl-
Fur
M'19: ?
amine (x mols) (?)
I '20: 1,600
[Oxidation on hair]
M '20: 168,459
4: 4 / -Diamino-diphenyl-3: 3'-disulfonic Acid
See, Benzidine-disulfonic Acid
p: /j'-Diamino-diphenylethylene-o: o'-disulfonic Acid
See 9 Diamino-stilbene-disulfonic Acid
p: ^'-Diamino-diphenyl-methane
p: p'-Methylene-bisaniline (C. A. nomen.)
H 2 N
H
NIL
DYES CLASSIFIED BY INTERMEDIATES
193
STATISTICS. Manufactured '20: ?
FORMATION. 50 parts of anhydro-formaldehyde-aniline (from equal
parts of aniline and 40 per cent formaldehyde), 100 parts of aniline
and 70 parts of aniline salt are heated together on a water bath,
condensing to the p: p'-diamino-diphenyl-methane
LITERATURE. Schultz, Farbstofftabellen (1914), #511
Lange, Zwischenprodukte, #1297
Dyes Derived from p : />'-Diamino-diphenyl-inethane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
298
Milling Red R
R Acid (2 mols)
A
TRIPHENYL-METHANE
DYES
511
Parafuchsine
Paramagenta
I '14 65,026
M'18: ?
M'19: ?
Aniline
Nitro-benzene
B
M'20: ?
540
Pacific Blue
Aniline
D
o-Toluidine
p-Toluidine
[Sulfonation]
;
or
[p-Rosaniline-fBenzoie
acid and sulf onation]
p : ^'-Diamino-diphenyl-sulfide
See, Thioaniline
4: 4'-Diamino-diphenyl-2: 2'-sulfon-disulfonic Acid
See, Benzidine-sulfon-disulfonic Acid
Diamino-diphenyl-urea-disulfonic Acid
5. 5'-Ureido-bis(2-amino-&enzene-sulfonic Acid) (C. A. nomen.)
3 Sv /S0 3 H
NH CO NH <^>NH 2 = CiaHi^O 7 S 2 402
194
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. 24 Parts of 4-nitro-amino-benzene-3-sulfonic acid is dis-
solved in water containing 5.5 parts of soda ash, and phosgene
conducted in until the reaction is completed, as indicated by test
not diazotizing. The dinitro-body is now reduced with iron
LITERATURE. Lange, Zwischenprodukte, #1823.
Dye Derived from Diamino-diphenyl-urea-disulfonic acid
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
297
Benzo Fast
I '14: 3,252
Gamma acid (2 mols)
D
Pink 2BL
I '14: 1,226
p : ^ -Diamino-ditolyl-amine
4:4'-Imino-bis-o-toluidine (C A. nomen. NH 2 =1)
H 3 C CH 3
~ Cl4Hl7N2 == 227
FORMATION. By semidine rearrangement of amino-azo-o-toluene
whereby the hydrochloride of amino-azo-o-toluene is dissolved in
sulfurous acid solution and reduced with zinc dust, the product
poured into 50 per cent sulfuric acid, boiled and crystallized
LITERATURE. Barber and Sisley, Sur un noveau mode de formation de
la p-diamino-diphenylamine
Bull. Soc. Chim. [3] 33, 1232-34 (1905)
Chem. Centr. 1906 [1], 232
Dye Derived from p : ^'-Diamino-ditolyl-amine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
295
Diphenyl Fast Black
I '14: 882
Gamma Acid
D
m-Tolylene-diamine
DYES CLASSIFIED BY INTERMEDIATES
p : /-Diamino-ditolyl-methane
4: 4'-Methylene-bis-o-foluidine (C. A. nomen.)
195
H 3 C
CH 3
H 2 N
NH 2 = Ci 5 Hi 8 N 2 = 226
FORMATION. 100 parts of anhydro-formaldehyde-aniline + 250 parts of
o-toluidine hydrochloride + 500 parts of o-toluidine are warmed
together on a water bath; and after 12 hours the mass is made al-
kaline and the aniline is distilled off with the aid of steam. (The
anhydro-formaldehyde-aniline is only used as a carrier for the for-
maldehyde)
LITERATURE. Lange, Zwischenprodukte, #1315, 1316
Dye Derived from />:/-Diamino-ditolyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
'**
DYE
513
New Fuchsine O
I 14: 300
o-Toluidine
B
M'18: ?
o-Nitro-toluene
M'19: ?
M'20: ?
Diamino-dixylyl-methane
Methylene-biszylidine (C. A. nomen)
NH 2 NH 2
CH 3 CH 3
CH 3 CH 3
= 254
FORMATION. From formaldehyde and xylidine in the presence of a
condensing agent
196 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Diamino-dixylyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
299
DISAZO DYE
Cinnabar Scarlet BF
R Acid (2 mols)
CL
Diamino-dixylyl-phenyl-methane
Benzal-biszylidine (C. A. nomen.)
NH
CH
CH
FOEMATION. From benzaldehyde and xylidine in the presence of a
condensing agent
LITERATURE. Lange, Zwischenprodukte, #1434
Dye Derived from Diamino-dixylyl-phenyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
300
Cotton Ponceau
R Acid (2 mols)
CL
Cinnabar Scarlet G
Di-^-amino-ethoxy-diphenyl
See, Ethoxy-benzidine
1: 3-Diamino-2-hydroxy-benzene-6-sulfonic Acid
See, 2: 6-Diamino-l-phenol-4-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
197
2 : 4-Diamino-4 / -hydroxy-diphenylamine
p-(2:4-Diamino-anilino)-phenol (C. A. nomen.)
H 2 N/~ /
NH
FOBMATION. Molecular proportions of 4-chloro-l : 3-dinitro-benzene
and p-amino-phenol are heated to boiling in aqueous suspension with
somewhat more than theoretical amount of limestone. The heat-
ing is done by direct steam in a vessel provided with a reflux con-
denser. After all the chloro-nitro-benzene has disappeared, the
liquid is cooled and the crystalline 2 : 4-dinitro-4'-hydroxy-diphenyl-
amine is separated and washed. This is then reduced to the de-
sired 2 : 4-diamino-4'-hydroxy-diphenylamine
LITERATURE. Cain, Intermediate Products (2d Ed.), 74
Lange, Zwischenprodukte, #1670
Dye Derived from 2 : 4-Diamino-4 / -hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
A ppli~
cation
Class
732
SULFUR DYE
Autogene Black
I '14: 7,495
Phenol
S
a-Diamino-naphthalene
1 : 5-Diamino-naphthalene (not considered herein)
/3-Diamino-naphthalene
1 : 8-Diamino-naphthalene (not considered herein)
4: 5-Diamino-2 : 7-naphthalene-disulfonic Acid (C. A. nomen.)
See, 1 : 8-Naphthylene-diamine-3 : 6-disulfonic Acid
4 : 8-Diamino-2 : 6-naphthalene-disulfonic Acid (C. A. nomen.)
See, 1 : 5-Naphthylene-diamine-3 : 7-disulfonic Acid
1 : 4-Diamino-2-naphthalene-sulf onic Acid (C. A. nomen.)
See, 1 : 4-Naphthylene-diamine-2-sulf onic Acid
198
DYES CLASSIFIED BY INTERMEDIATES
2: 7-Diamino-naphthalene-sulfonic Acid (C. A. nomen.)
See, 2 : 7-Naphthylene-diamine-sulf onic Acid
5: 7-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1 : 3-Naphthylene-diamine-6-sulf onic Acid
6: 8-Diammo-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1 : 4-Naphthylene-diamine-6-sulf onic Acid
2: 6-Diamino-l-phenol-4-sulfonic Acid (C. A. nomen. OH=1)
1 : 3-Diamino-2-hydroxy-benzene-5-sulfonic Acid
OH
H 2 N, 1NH 2 C 6 H 8 N 2 4 S =
S0 3 H
FORMATION. Phenol is sulfonated by dissolving in hot sulfuric acid,
cooled, diluted, and then dinitrated, using nitric acid and heating
to boiling. The dinitro-phenol-sulfonate is then isolated, dissolved
in water, and reduced with ammonium sulfide, and the diamine
precipitated by acidification
LITERATURE. Lange, Zwischenprodukte, #1137
Cain, Intermediate Products (2d Ed.), 129, 130
Dyes Derived from 2 : G-Diamino-l-phenol-4-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
288
DISAZO DYES
Acid Alizarin
Black SE
Palatine Chrome
Black F
I '14: 19,185
I '20: 34,302
j3-Naphthol (2 mols)
ACr
289
Acid Alizarin
Black SN
Palatine Chrome
Black S
M'17: ?
M'18: ?
M 19: ?
/3-Naphthol
Schaeffer's Acid
ACr
DYES CLASSIFIED BY INTERMEDIATES 199
Diamino-stilbene-disulfonic Acid
p: p'-Diamino-diphenylethylene-o: o'-disulfonic Acid
DS (abbreviation for above in compounds, less 2-NH^)
4: 4'-Diamino-2 : 2'-stilbene-disulfonic Acid (C. A. nomen.)
S0 3 H H0 3 S_
STATISTICS. Manufactured '17: ?
Manufactured ' 18 : ?
Manufactured '19: 5,021 Ibs.
Manufactured '20: 142,227 Ibs.
FORMATION. From sodium salt of p-nitro-toluene-o-sulfonate by dis-
solving in water and boiling with caustic soda until the color be-
comes deep red. Then reduction is effected by adding zinc dust
until the liquid is decolorized
LITERATURE. Cain, Intermediate Products (2d Ed.), 98
Lange, Zwischenprodukte, #1454
Dyes Derived from Diamino-stilbene-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
301
Hessian Purple N
I '14: 465
/3-Naphthylamine
D
(2 mols)
302
Brilliant Hessian
Broenner's Acid
D
Purple
(2 mols)
303
Brilliant Yellow
I '14: 278,000
Phenol (2 mols)
D
Paper Yellow
M'17: ?
*
A
M'18: 1,664
M'19: 48,723
I '20: 126
M'20: 91,218
304
Chrysophenine G
I '14: 157,799
Phenol (2 mols)
D
M'17: ?
[Ethylation]
M'18: 41,663
M'19: 86,795
I '20: 3,661
M '20: 247,202
305
Hessian Yellow
Salicylic Acid (2 mols)
D
200
DYES CLASSIFIED BY INTERMEDIATES
3: 5-Diamino-/>-foluene-sulfonic Acid (C. A. nomen. S0 3 H = 1)
l-Tolylene-2 : 6-diamine-4-sulf onic Acid
Toluylene-diamine-sulfonic Acid
l-Methyl-2 : 6-diammo-benzene-4-sulf onic Acid
SO 3 H
H 2 N0NH 2 = C 7 H 10 N 2 3 S = 202
CH 3
FORMATION. From o-nitro-toluene by sulfonation, nitration and re-
duction
LITERATURE. Lange, Zwischenprodukte, #1096
Dyes Derived from 3 : 5-Diamino-p-toluene-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
D
285
DISAZO DYES
Toluylene Brown G
m-Phenylene-diamine
286
Toluylene Yellow
I '14: 5,485
Nitro-m-phenylene-
diamine (2 mols)
D
287
Toluylene
Orange RR
I '14: 500
/3-Naphthylamine
(2 mols)
D
488
TETRAKISAZO DYE
Toluylene Brown R
I '14: 201
Naphthionic Acid
(2 mols)
w-Phenylene-diamine
(2 mols)
D
4: 6-Diamino-m-toluene-sulfonic Acid (C. A. nomen. SOaH=l)
m-Tolylene-diamine-sulfonic Acid
ra-Toluylene-diamine-sulfonic Acid
l-Methyl-2 : 4-diamino-benzene-5-sulfonic Acid
S0 3 H
H 2 N( / N
U
NH 2
C 7 HioN 2 3 S 202
DYES CLASSIFIED BY INTERMEDIATES
201
STATISTICS. Manufactured in 1918, 1919, 1920, but in undisclosed
quantities
FORMATION. By addition of w-tolylene-diamine sulfate to oleum, and
heating the mixture for three hours on a water bath.
LITERATURE. Cain, Intermediate Products (2d Ed.), 87
Lange, Zwischenprodukte, #1096
Dyes Derived from 4: 6-Diamino-m-toluene-sulfonic Acid (SO Z H = 1)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
362
Toluylene Orange R
I '14: 25,908
Tolidine
D
Oxydiamine
M'19: ?
4: 6-Diamino-m-
Orange R
I '20: 1,653
toluene-sulfonic
Acid (2 mols)
392
Toluylene Orange G
I '14: 67,022
Tolidine
D
M'18: ?
o-Cresotic Acid
M'19: ?
M'20: ?
I '20: 273
Dianisidine
o-Dianisidine
D (abbreviation for Dianisidine in compounds, without the 2-
groups)
O.CH 3
= 244
STATISTICS. Imported '14: 10,656 Ibs.
Manufactured '17: 11,702 Ibs.
Manufactured ' 18 : ?
Manufactured '19: 107,441 Ibs.
Manufactured '20: ?
FORMATION. o-Nitro-anisole is reduced by zinc dust in presence of
caustic soda and alcohol to hydrazo-anisole, which is rearranged to
dianisidine by being warmed with dilute sulfuric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 96
, Zwischenprodukte, #1204
202 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dianisidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
405
406
DISAZO DYES
Benzopurpurin 10B
Diazurine B
I '14: 47,768
M'18: ?
M'19: ?
M'20: 41,265
I '20: 2,205
Naphthionic Acid
(2 mols)
l-Naphthylamine-6-
sulf onic Acid (2 mols)
0-Naphthol (2 mols)
D
D
407
Azo Violet
Naphthionic Acid
Nevile-Winther's Acid
D
408
Dianisidine Blue
/3-Naphthol (2 mols)
D
408(1)
Azophor Blue D
[Stable tetrazo-dianisole
used with p-nitro-
aniline]
MF
408(2)
Azophor Black S
I '14: 140
[Stable tetrazo-dianisole
mixed with diazo ra-
nitro-aniline, etc.]
MF
409
Trisulfon Blue B
I '14: 813
l-Naphthol-3:6:8-
trisulfonic Acid
/3-Naphthol
D
410
Benzoazurine G
I '14: 78.699
M'18: ?
M '19: 150,589
I '20: 287
M '20: 237,328
Nevile-Winther's Acid
(2 mols)
D
411
Benzoazurine 3G
I '20: 201
l-Naphthol-5-sulfonic
(2 mols)
D
412
Congo Blue 2B
RAcid
Nevile-Winther's Acid
D
413
Direct Violet BB
I '14: 4,396
1 : 7-Dihydroxy-naph-
thalene-4-sulfonic
Acid
m-Tolylene-diamine
D
DYES CLASSIFIED BY INTERMEDIATES
203
Dyes Derived from Dianisidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
414
(continued)
Indazurine B
1 : 7-Dihydroxy-naph-
thalene-4-sulf onic Acid
RAcid
D
415
Dianil Blue G
M'19: ?
M'20: ?
Chromotropic Acid
(2 mols)
D
416
Brilliant Azurine 5G
I '14: 22,324
I '20: 1,563
1 : 8-Dihydroxy-naph-
thalene-4-sulf onic Acid
(2 mols)
D
417
Chlorazol Blue
3GorR
I '14: 10,151
l-Chloro-8-naphthol-5-
sulfonic Acid (2 mols)
or
l-Chloro-8-naphthol-4-
sulf onic Acid (2 mols)
D
418
Diamine Brilliant
BlueG
I '14: 11,592
I '20: 51
l-Chloro-8-naphthol-
3 : 6-disulf onic Acid
(2 mols)
D
419
Chicago Blue RW
I '14: 15,176
M'19: ?
I '20: 351
M'20: ?
l-Amino-8-naphthol-
2: 4-disulfonic Acid
/3-Naphthol
D
420
Azidine Wool Blue B
Croceine Acid
l-Amino-8-naphthol-
4-sulfonic Acid
D
421
Oxamine Blue B
I '14: 35,891
I '20: 13
l-Amino-5-naphthol-7-
sulf onic Acid
Nevile-Winther's Acid
D
422
Chicago Blue 4B
I '14: 8,269
l-Amino-8-naphthol-
2: 4-disulfonic Acid
l-Amino-8-naphthol-4-
sulfonic Acid
D
204 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dianisidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
423
DISAZO DYES
(continued)
Chicago Blue B
M'18: ?
l-Amino-8-naphthol-4-
sulfonic Acid (2 mols)
D
424
Chicago Blue 6B
I '14: 118,542
M '19: ?
I '20: 7,480
M'20: ?
l-Amino-8-naphthol-
2: 4-disulfonic Acid
(2 mols)
D
425
Benzo Cyanine 3B
I '14: 1,001
HAcid
l-Amino-8-naphthol-4-
sulfonic Acid
D
426
Diamine Pure Blue
Benzamine Pure
Blue
I '14: 12,881
M'17: ?
M'18: ?
M' 19: 192,350
'20: 652
M '20: 223,100
H Acid (2 mols)
D
427
Indazurine GM
1: 7-Dihydroxy-2-mph-
thoic-4-sulfonic Acid
Nevile-Winther's Acid
D
428
Direct Blue B
I '14: 21,421
M'17: 14,823
M'18: ?
I '20: 7,055
1 : 7-Dihydroxy-6-naph-
thoic-3-sulf onic Acid
Nevile-Winther's Acid
D
429
Indazurine BB
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
RAcid
D
430
Indazurine 5GM
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
HAcid
D
455
TRISAZO DYES
Columbia Black B
I '14: 165,727
2 R Acid
w-Tolylene-diamine
(2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES
205
Dyes Derived from Dianisidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture '
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
D
456
TBISAZO DYES
(continued}
Congo Fast Blue B
Benzo Fast Blue B
I '14: 100,495
I '20: 1,821
a-Naphthylamine
l-Naphthol-3: 8-disul-
fonic Acid
457
Trisulfon
Brown GG
I '14: 7,562
I '20: 38,411
2 R Acid
Salicylic Acid
m-Phenylene-diamine
D
Dibenzo-pyrrole
See, Carbazole
Dibenzyl-aniline-sulfonic (disulfonic) Acid
[(N-Benzyl-anilino)-methyl]-frenzene-sulfonic Acid (C. A. nomen.)
C 6 H 5 . CH 2 N CH 2 . C 6 H 4 . S0 3 H
FORMATION. Aniline, benzyl chloride and sodamide are mixed together
and then heated up on water bath until ammonia is all off, resulting
in the formation of dibenzyl-aniline. This latter is then sulfonated
LITERATURE. Lange, Zwischenprodukte, #1561
Dye Derived from Dibenzyl-aniline-sulfonic (disulfonic) Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
531
Eriocyanine A
I '14: 25,091
Tetramethyl-p: p'-dia-
A
I '20: 8,223
mino-benzohydrol-
sulf onic Acid
[Oxidation]
206 DYES CLASSIFIED BY INTERMEDIATES
6:7-Dibromo-2-chloro-3-pseudoindolone (C. A. nomen.)
See, 5: 7-Dibromo-isatin Chloride
5: 7-Dibromo-isatin Chloride
5: 7-Dibromo-2-chloro3-pfeeudoindolone (C. A. nomen.)
Br
N
\
C . Cl = C 8 H 2 Br 2 ClNO = 323.5
Br
FORMATION. Isatin is gently warmed with bromine in concentrated
sulfuric acid, giving 5 : 7-dibromo-isatin, which is then warmed
with phosphorus pentachloride and benzene
LITERATURE. Ullmann, Enzy. tech. Chemie, 6, 526
Lange, Zwischenprodukte, #2122
Dyes Derived from 5 : 7-Dibromo-isatin Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
893
INDIGO GROUP DYES
Alizarin Indigo G
I '20: 1,596
1-Anthrol
V
895
Alizarin Indigo 3R
I '20: 3,514
a-Naphthol
V
2: 5-Dichloro-aniline
NH 2
0,^
FORMATION. From 2: 5-dichloro-nitro-benzene by reduction with iron
and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 50
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2 : 5-Dichloro-aniline
207
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
218
Nigrophor BASF
l-Amino-8-naphthol-5-
MF
sulfonic Acid
p-Nitro-aniline
TRISAZO DYES
469
Chloramine
I '14: 39,600
Benzidine
D
Black N
M'19: ?
m-Phenylene-diamine
I '20: 1,763
HAcid
M '20: ?
470
Chloramine
I '14: 1,675
Benzidine
D
Green B
M'19: ?
Phenol
M'20: ?
H Acid
471
Chloramine
I '14: 286
Benzidine
D
Blue 3G
M'19: ?
H Acid (2 mols)
I '20: 882
472
Chloramine
Benzidine
D
Blue HW
Gamma Acid
HAcid
1 : 5-Dichloro-anthraquinone
277
FORMATION. Sodium 1 : 5-anthraquinone-disulf onate in dilute hydro-
chloric acid is heated to boiling and treated with a solution of
sodium chlorate
LITERATURE. Cain, Intermediate Products (2d Ed.), 250
Lange, Zwischenprodukte, #3083, 3086
Ullmann, Enzy. tech. Chemie, 1, 472
208
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1 : 5-Dichloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
832
Indanthrene
I '14: 11,667
Anthranilic Acid
V
Violet RN
I '20: 49
(2 mols)
2 : 6-Dichloro-anthraquinone
x\ /c<
/V \/ \ci
C1 \A
xxx co
FORMATION. 2: 6-Anthraquinone-disulfonic acid is treated with
chlorine
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 472
Cf. Ber., 37, 4706
Lange, Zwischenprodukte, #3164, 3165
Dyes Derived from 2 : 6-Dichloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
826
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene Red G
1-Amino-anthraquinone
(2 mols)
V
829
Algol Bordeaux 3B
I '20: 61
l-Amino-4-methoxy-
anthraquinone (2 mols)
V
2: 7-Dichloro-anthraquinone
'CO
Cl
CO
Cl
DYES CLASSIFIED BY INTERMEDIATES
209
FORMATION. From anthraquinone-2: 7-disulfonic acid by treatment
with hydrochloric acid and sodium chlorate; or better from 9: 10-
dichloro-anthracene-2 : 7-disulfonic acid by treatment with the same
reagents
LITERATURE. Ullmann, Enzy. tech. Chemie, 1, 472
Lange, Zwischenprodukte, #3165
Dyes Derived from 2:7-Dichloro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
827
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
Bordeaux B extra
I '14: 28,728
I '20: 4,056
l-Amino-6-chloro-an-
thraquinone (2 mols)
V
830
Indanthrene Red R
I '14: 2,099
I '20: 6,595
1-Amino-anthraquinone
(2 mols)
V
2: 5-Dichloro-benzaldehyde
HCO
FORMATION. From 2-chlor-5-nitro-benzaldehyde by the substitution
of the nitro group by chlorine
LITERATURE. Lange, Zwischenprodukte, #669
Beil, III, 13
Dyes Derived from 2 :5-Dichloro-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
497
TRIPHENYL-METHANE
DYES
New Fast Green 2B
Victoria Green 3B
I '14: 44,595
Dimethyl-aniline
(2 mols)
[Oxidationl
B
501
Glacier Blue
Brilliant Glacier
Blue
I '14: 2,495
Methyl-o-toluidine
(2 mols)
[Oxidation]
B
210
DYES CLASSIFIED BY INTERMEDIATES
o : o'-Dichloro-benzidine
2: 2'-Dichloro-benzidine (C. A. nomen. NH%=1)
3: 3'-Dichloro-benzidine (Usual numbering, point oj 'attachment = 1 )
Cl Cl
H 2 N< / ~~V-< / ~~ X >NH 2 = C 12 H 10 C1 2 N 2 = 253
FORMATION. (1) By chlorinating of diacetyl-benzidine, and hydrolyz-
ing product. (2) By reducing o-chloro-nitro-benzene in alkaline
solution with zinc, and rearranging with acid the o: o'-dichloro-
hydrazo-benzene formed (similar to benzidine formation from nitro-
benzene)
LITERATURE. Cain, Intermediates (2d Ed.), 94
Lange, Zwischenprodukte, #1229, 1230
Dyes Derived from o : o' Dichloro-benzidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
356
DISAZO DYES
Dianol Red 2B
I '14: 4,422
I '20: 17,632
Naphthionic Acid
(2 mols)
D
357
Dianol Red B
Broenner's Acid
(2 mols)
D
358
Brilliant Dianol Red
R extra
Diphenyl Red
I '14: 14,305
I '20: 3,704
Amino-R Acid
(2 mols)
D
2: 6-Dichloro-4-(4: 5-dihydro-5-keto-3-methyl-l-pyrazolyl)-&en-
zene-sulfonic Acid (C. A. nomen.)
See, l-(2': 5'-Dichloro^'-sulfo-phenyl)-3-methyl-5-pyrazolone
2: 5-Dichloro-nitro-benzene
N0 2
01 =C 6 H 3 Cl 2 N0 2 =rl92
DYES CLASSIFIED BY INTERMEDIATES
211
FORMATION. By nitration of p-dichloro-benzene with mixed acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 14
Lange, Zwischenprodukte, #674
USES. For preparing 2: 5-dichloro-aniline
3: 6-Dichloro-^hthalic Acid
COOH
C1/\COOH
STATISTICS. Imported '14: very small
Manufactured '18: ?
FORMATION. (1) From dichloro-naphthalene tetrachloride, by oxida-
tion with nitric acid. (2) From phthalic anhydride dissolved in
oleum by chlorination in presence of iodine, and by separation from
the isomers formed at the same time
LITERATURE. Lange, Zwischenprodukte, #992
Cain, Intermediate Products (2d Ed.), 165
Dyes Derived from 3 : 6-Dichloro-phthalic Acid
tSchuttz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
584
Fast Acid
I '14: 3,022
Resorcinol (2 mols)
A
BlueR
I '20: 130
p-Phenetidine (2 mols)
[PC1 5 ; Sulfonationl
or
[Tetrachloro-fluores-
ceine and p-phene-
tidine; Sulfonation]
593
Phloxine P
I '14: 2,244
Resorcinol (2 mols)
A
M'17: ?
[Bromination]
M'18: ?
or
M'19: ?
[Dichloro-fluoresceine
M'20: ?
brominated]
212
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3 : 6-Dichloro-phthalic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
(continued)
594
Cyanosine, Spirit
Resorcinol (2 mols)
A
Soluble
[Bromination, methyla-
tion]
or "s .
[Phloxine P methyl
ester]
595
Rose Bengal
I '14: 2,277
Resorcinol (2 mols)
A
M'20: ?
[lodation]
or
[Dichloro-fluoresceine
iodated]
l-(2 : 5-Dichloro-4-sulfo-phenyl)-3-methyl-5-pyrazolone
2 : 5-Dichloro-4-(4 :5-dihydro-5-keto-3-methyl-l-pyrazolyl) -&en-
zene-sulfonic Acid (C. A. nomen.)
Cl
N-
/\ C1
OC N
S0 3 H = C 10 H 8 C1 2 N 2 4 S = 323
H.U.
CH 3
FORMATION. 2: 5-Dichloro-aniline-4-sulfonic acid is diazotized and re-
duced to 2: 5-dichloro-phenyl-hydrazine-4-sulfonic acid, which latter
body by condensation with ethyl acetoacetate forms the above
pyrazolone derivative
LITERATURE. Cain, Intermediate Products (2d Ed.), 170
Cf. Lange, Zwischenprodukte, #138
DYES CLASSIFIED BY INTERMEDIATES
213
Dye Derived from l-(2: 5-Dichloro-4-sulfo-phenyl)-3-methyl-5-
pyrazolone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYE
22
Xylene Yellow 3G
I '14: 23,074
Sulfanilic Acid
A
I '20: 77,782
^-Diethylamino-azo-benzene
Benzene-azodiethylaniline
N: JV-Diethyl-p-phenylazo-aniline (C. A. nomen.)
= Ci 6 Hi 9 N 3 = 253
FORMATION. By coupling diazo-benzene chloride (diazotized aniline)
with diethyl-aniline
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 80
Dyes Derived from ^-Diethylamino-azo-benzene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class 1
OXAZINE DYES
641
Coreine RR
I '14: 1,320
Gallamide
M
Ccelestine Blue B
I '20: 44
*v.:. ti
646
Coreine AR
Gallamide
M
Aniline
[Sulfonation]
or
[Coreine RR, Aniline,
Sulfonation]
/>-Diethylamino-benzoyl Chloride
COC1
= CnHi 4 ClNO = 211.5
N(C 2 H 5 ) 2
214
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. (1) p-Amino-benzoic acid is ethylated, and then treated
with phosphorus pentachloride to form the desired acid chloride.
(2) Diethyl-aniline is subjected to the action of phosgene first at
ordinary temperatures until no more gas is absorbed, and then after
melting the crystalline mass first obtained. The product is mixed
with water and the excess of diethyl-aniline removed by acetic acid.
The acid chloride is formed by treatment with phosphorus penta-
chloride
LITERATURE. Cain, Intermediate Products (2d Ed.), 148
Dye Derived from />-Diethylamino-benzoyl Chloride
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
534
TRIPHENYL-METHANE
DYE
Acid Violet 7B
I '14: 21,665
I '20: 51
N-Methyl-diphenyl-
amine (2 mols)
A
3-Diethylamino-^-cresol (C. A. nomen. OH=1)
Diethyl-w-amino-p-cresol (OH=1)
OH
N(C 2 H 5 ) 5
FORMATION. From diethyl-o-toluidine by sulfonation in the cold with
oleum and caustic soda fusion of the sulfonic acid
LITERATURE. Mohlau, Klimmer and Kahl, Zeit. Farb. Chem., 1902
316
Lange, Zwischenprodukte, #815
Dye Derived from 3-Diethylamino-/>-cresol (OH=1)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
620
Capri Blue GON
T 14: 128
Nitroso-dimethyl-ani-
B
line
DYES CLASSIFIED BY INTERMEDIATES 215
Diethyl-m-amino-^-cresol (OH=1)
See, 3-Diethylamino-p-cresol (C. A. nomen. OH=1)
5-Diethylamino-2-nitroso-^henol (C. A. nomen.)
Ni troso-diethyl-m-amino-ph enol
OH
ONO _ n XTrk
v^lO-H-14lN 2 v_/ 2 = ly4
FORMATION. Diethyl-m-amino-phenol (which can be prepared by sul-
fonating diethyl-aniline and then fusing the sulfonic acid to pro-
duce the diethyl-m-amino-phenol) is dissolved in hydrochloric acid,
cooled with ice to C., and sodium nitrite solution introduced
LITERATURE. Lange, Zwischenprodukte, #906
Dyes Derived from 5-Diethylamino-2-nitroso-phenol
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
653
Nile Blue A
I '14: 1,518
I '20: 1,241
a-Naphthylamine
B
654
Nile Blue 2B
Benzyl-a-naphthyl-
B
amine
m-Diethylamino-/>henol (C. A. nomen.)
Diethyl-m-amino-phenol
OH
lN(C 2 H 5 ) s
165
STATISTICS. Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. Diethyl-aniline is sulfonated with oleum, and ' the re-
sulting diethyl-aniline-m-sulfonic acid fused with caustic soda
LITERATURE. Cain, Intermediate Products (2d Ed.), 122
Lange, Zwischenprodukte, #603-606, 2263
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Diethylamino-phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
570
Rhodamine S
I '14: 600
Diethyl-ra-amino-
A
I '20: 273
phenol (2 mols)
[Succinic Anhydride]
572
Rhodamine G
I '14: 2,648
Phthalic Anhydride
B
I '20: 517
Diethyl-m-amino-
phenol (2 mols)
Aniline [Removes one
QjEU group]
or
[Rhodamine B heated
with Aniline Salt]
573
Rhodamine B
I '14: 59,354
Phthalic Anhydride
B
M'17: ?
Diethyl-m-amino-
M'18: ?
phenol (2 mols)
M'19: ?
M'20: ?
I '20: 24,709
574
Rhodamine 3B
Phthalic Anhydride
B
Diethyl-m-amino-
phenol (2 mols)
[Ethyl esterification]
or
[Rhodamine B
ethylated]
579
Sulf o Rhodamine B
I '14: 1,698
Benzaldehyde-di-
A
Xylene Red B
sulf onic Acid
Diethyl-w-amino-
phenol (2 mols)
[Oxidation]
581
Fast Acid Eosine G
I '14: 650
Phthalic Anhydride
A
Fast Acid
I '20: 5,234
Diethyl-m-amino-
PhloxineA
phenol (2 mols)
or
[Rhodamine B, sulfo-
nated]
DYES CLASSIFIED BY INTERMEDIATES
21?
Diethyl-aniline
N:iV-Diethyl-aniline (C. A. nomen.)
N(C 2 H 5 ) 2
STATISTICS. Imported '14: very small quantity
Manufactured '17: 3,955 Ibs.
Manufactured '18: 48,048 Ibs.
Manufactured '19: 30,000 Ibs.
Manufactured '20: 180,542 Ibs.
FORMATION. Aniline is heated in an autoclave with ethyl alcohol in
the presence of a catalyst, for example, hydrochloric acid, hydro-
bromic acid, or iodine
LITERATURE. Cain, Intermediate Products (2d Ed.), 68
Lange, Zwischenprodukte, #128
Dyes Derived from Diethyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
499
Brilliant Green
I '14: 73,904
M'18: ?
M'19: ?
I '20: 25
Diethyl-aniline (2 mols)
Benzaldehyde
[Oxidation]
B
M '20: ?
507
Xylene Blue VS
I '14: 2,130
I '20: 27,254
Diethyl-aniline (2 mols)
3-Methyl-benzalde-
hyde-4 :6-disulfonic
Acid
A
[Oxidation]
518
Ethyl Violet
Ethyl Purple
I '14: 51,933
Tetraethyl-diamino-
benzophenone
B
or
Diethyl-aniline (3 mols)
Phosgene
or
Tetraethyl-diamino-
diphenyl-methane
218
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diethyl-aniline (continued)
Schullz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES (continued)
530
Acid Violet 6B
I '14: 161,624
Ethyt-sulfobenzyl-
A
Formyl Violet
M'17: ?
aniline (2 mols)
Guinea Violet
M'18: ?
[Formaldehyde, Oxida-
M'19: ?
tion]
I '20: 3,925
M '20: 144,207
543
Patent Blue V
I '14: 196,228
Diethyl-aniline (2 mols)
A
M'17: ?
m-Nitro-benzaldehyde
M'18: ?
or m-Hydroxy-
I '20: 36,420
benzaldehyde
[Sulfonation, Oxidation]
544
Cyanine B
I '14: 8,398
Diethyl-aniline (2 mols)
A
I '20: 24
m-Nitro-benzaldehyde
or m-Hydroxy-
benzaldehyde
[Sulfonation, Oxidation]
or
[Patent Blue Oxidized]
AZINE DYE
686
Amethyst Violet
Diethyl-p-phenylene-
A
diamine
Aniline or p-Toluidine
[Oxidation]
Diethyl-aniline-m-sulfonic Acid
N: -AT-Diethyl-raetanilic Acid (C. A. nomen.)
FORMATION. From diethyl-aniline by sulfonation with oleum
LITERATURE. Cain, Intermediate Products (2d Ed.), 122
Lange, Zwischenprodukte, #631
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diethyl-aniline-m-sulfonic Acid
219
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
59
Wool Violet S
I '14: 308
2 : 4-Dinitro-aniline
A
M'18: ?
M'19: ?
N: W-Diethyl-metanilic Acid (C. A. nomen.)
See, Diethyl-aniline-m-sulfonic Acid
N: W-Diethyl-/>-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-diethyl-aniline
N: Ar-Diethyl-/>-phenylazo-aniline (C. A. nomen.)
See, p-Diethylamino-azo-benzene
N: W'-Diethyl-m-phenylene-diamine (C. A. nomen.)
s-Diethyl-ra-phenj' lene-diamine
HNC 2 H 5
lNH.C 2 H 5 ^C 10 H 16 N 2
FORMATION. Probably by heating resorcinol with ethylamine in the
presence of a dehydrating agent
LITERATURE. Cf. Green, Organic Coloring Matters (1908), 37.
Cf. Calm, Ber., 16, 2792 (1883)
Dye Derived from N: W'-Diethyl-m-phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
678
Fast Neutral
M'17: ?
Nitroso-dimethyl-
B
Violet B
aniline
220
DYES CLASSIFIED BY INTERMEDIATES
N: JV-Diethyl-p-phenylene-diamine (C. A. nomen.)
p- Amino-diethy 1-an iline
N(C 2 H 6 ) 2
NIL
FORMATION. Diethyl-aniline is converted into p-nitroso-diethyl-aniline
by nitrous acid, which by reduction with zinc dust and hydrochloric
acid yields the p-amino-diethyl-aniline
LITERATURE. Cf. Lange, Zwischenprodukte, #561-563
Dye Derived from N: #-Diethyl-/>-phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
686
Amethyst Violet
Diethyl-aniline
A
Aniline or p-Toluidine
[Oxidation]
s-Diethyl-m-phenylene-diamine
See, N : N'-Diethyl-w-phenylene-diamine
Diethyl-/>-phenylene-diamine-thiosulfonic Acid
p-Amino-diethyl-aniline-thiosulfonic Acid
4-Amino-l-diethylamino-benzene-3-thiosulfonic Acid
2-Amino-5-diethylamino-6enzene-thiosulfonic Acid (C. A. nomen.)
N(C 2 H 6 ) 2
S.S0 3 H
276
FORMATION. 12 parts of the zinc chloride double salt of diethyl-p-
phenylene-diamine are dissolved in 90 parts of water, treated with
a solution of 25 parts of aluminum sulfate and 20 parts of sodium
thiosulfate in 70 parts of water, and finally oxidized with 3 parts of
potassium bichromate dissolved in 30 parts of water
LITERATURE. Lange, Zwischenprodukte, #931, 932
DYES CLASSIFIED BY INTERMEDIATES 221
Dye Derived from Diethyl-/>-phenylene-diamine-thiosulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
THIAZINE DYE
666
Indochromogen S
1 : 2-Naphthoquinone-
M
4: 6-disulfonic Acid
3: 4-Dihydro-3: 4-diketo-l : 7-naphthalene-disulf onic Acid (C. A.
nomen.)
See, 1 : 2-Naphthoquinone-4 : 6-disulfonic Acid
3:4-Dihydro-3:4-diketo-l-naphthalene-sulfonic Acid (C. A.
nomen.)
See, 1 : 2-Naphthoquinone-4-sulfonic Acid
/>-(4:5-Dihydro-5-keto-3-methyl-l-pyrozolyl)-benzene-sulfonic
Acid (C. A. nomen.)
See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone
1 : 2-Dihydroxy-anthraquinone
See, Alizarin
1 : 5-Dihydroxy-anthraquinone
See, Anthrarufin
2 : 4-Dihydroxy-benzoic Acid
See, j8-Resorcylic Acid (C. A. nomen.)
3: 5-Dihydroxy-benzoic Acid
See, a-Resorcylic Acid (C. A. nomen)
m-Dihydroxy-benzoic Acid
See, a-Resorcylic Acid (C. A. nomen.)
1: 7-Dihydroxy-2-carboxy-naphthalene-4-sulfonic Acid
See, 1 : 7-Dihydroxy-2-naphthoic-4-sulfonic Acid
222
DYES CLASSIFIED BY INTERMEDIATES
1 : 7-Dihydroxy-6-carboxy-naphthalene-3-sulf onic Acid
See, 1 : 7-Dihydroxy-6-naphthoic-3-sulf onic Acid
Dihydroxy-/3-methyl-coumarin
See, 7 : 8-Dihydroxy-4-methyl-coumarin (C. A. nomen.)
7:8-Dihydroxy-4-methyl-coumarin (C. A. nomen.)
Dihydroxy-/?-methyl-coumarin
HO
FORMATION. From pyrogallol and acetoacetic ethyl ester
LITERATURE. J. pr. Ch. (2) 26, 68
Ber., 16, 2127 (1883)
Dye Derived from 7: 8-Dihydroxy-4-methyl-coumarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYE
773
Anthracene Yellow
I '14: 4,046
[Brominationl
M
1: 6-Dihydroxy-naphthalene
1: 5-Naphthalenediol (C. A. nomen.)
OH
HO
STATISTICS. Manufactured '19:
Manufactured '20:
DYES CLASSIFIED BY INTERMEDIATES
223
FORMATION. By caustic soda fusion of sodium naphthalene-1 : 5-disul-
fonate or of sodium l-naphthol-5-sulfonate
LITERATURE. Cain, Intermediate Products (2d Ed.), 230
Lange, Zwischenprodukte, #2392
Thorpe, Die. Chemistry, 3, 646
Dye Derived from 1 : 5-Dihydroxy-naphthalene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
157
Diamond Black PV
I '14: 285,074
o-Amino-phenol-p-
M
sulfonic Acid
2 : 7-Dihydroxy-naphthalene
2: 7-Naphthalenediol (C. A. nomen.)
FORMATION. By caustic soda fusion of F acid (2-naphthol-7-sulfonic
acid)
LITERATURE. Lange, Zwischenprodukte, #2401
Green, Organic Coloring Matters (1908), 54
Thorpe, Die. Chemistry, 3, 647
Dyes Derived from 2: 7-Dihydroxy-naphthalene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITROSO DYE
3
Dioxine
[Nitrous Acid]
M
OXAZINE DYE
655
Muscarine
Nitroso-dimethyl-
B
aniline
224 DYES CLASSIFIED BY INTERMEDIATES
1: 7-Dihydroxy-naphthalene-2-carboxylic-4-sulfonic Acid
See, 1 : 7-Dihydroxy-2-naphthoic-4-sulf onic Acid
1: 7-Dihydroxy-naphthalene-6-carboxylic-3-sulfonic Acid
See, 1 : 7-Dihydroxy-6-naphthoic-3-sulf onic Acid
1 : 8-Dihydroxy-naphthalene-3 : 6-disulf onic Acid
See, Chromotropic Acid
4: 6-Dihydroxy-2: 7-naphthalene-disulfonic Acid (C. A. nomen.}
See, Chromotropic Acid
1 : 7-Dihydroxy-naphthalene-4-sulf onic Acid
4: 6-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
OH
HO/V^ = C HO S = 240
\A/
S0 3 H
FORMATION. From 1 hydroxy-naphthalene-2-carboxylic-4 : 7-disulf onic
acid by fusion with alkalis, whereby first a sulfonic group is replaced
by hydroxyl and then at a higher temperature carbon dioxide is
split out
LITERATURE. Lange, Zwischenprodukte, #2617, 2618
Thorpe, Die. Chemistry, 3, 650
Dyes Derived from l:7-Dihydroxy-naphthalene-4-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
413
DISAZO DYES
Direct Violet BB
I '14: 4,396
Dianisidine
m-Tolylene-diamine
D
414
Indazurine B
Dianisidine
R Acid
D
DYES CLASSIFIED BY INTERMEDIATES
1 : 8-Dihydroxy-naphthalene-4-sulf onic Acid
Dihydroxy-naphthalene-sulfonic Acid S
S Acid
4: 5-Dihydroxy-l-naphthalene-sulfomc Acid (C. A. nomen.)
HO OH
225
S0 3 H
STATISTICS. Imports '14: 2,178 Ibs.
FORMATION. (1) From l-naphthol-4 : 8-disulfonic acid by fusion with
caustic soda, preferably in an autoclave. (2) From 1-naphthyl-
amine-4 : 8-disulfonic acid by fusion with caustic soda, in an auto-
clave. (3) From l-amino-8-naphthol-4-sulfonic acid by heating
with sodium sulfite
LITERATURE. Cain, Intermediate Products (2d Ed.), 230
Lange, Zwischenprodukte, #2621, 2622
Dyes Derived from 1 : 8-Dihydroxy-naphthalene-4-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Impoit and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
63
MONOAZO DYES
Azo Acid Blue
I '14: 45,098
I '20: 9,222
Dimethyl-p-phenylene-
diamine
or
p-Nitro-aniline [Reduc-
tion and alkylation]
A
71
Azo Fuchsine B
Toluidine
A
118
Brilliant Geranine
I '14: 18,917
M'19: ?
I '20: 527
Dehydro-thio-p-
toluidine
D
146
Azo Fuchsine G
I '14: 17,819
I' 20: 3,694
Sulfanilic Acid
A
147
Azo Fuchsine 6B
I '14: 13,206
M'17: ?
M'18: ?
Sulfanilic Acid (?)
A
226 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 1 : 8-Dihydroxy-naphthalene-4-sulfonic
(continued)
Acid
Schultz
Number
for Dye
Ordinary Nome and
Class oj Dye
Statistics of
Impott and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
229
Azo Acid Violet
I '14: 150
Amino-azo-benzene
A
I '20: 11
M'20: ?
242
Sulfon Black G
Aniline
A
l-Naphthylamine-6-
and 7-sulfonic Acids
j$
[Cleve's Acids]
262
Victoria Black B
I '14: 557
Sulfanilic Acid
A
a-Naphthylamine
276
Diamond Green B
I '14: 8,622
Amino-salicylic
ACr
M'18: ?
a-Naphthylamine
I '20: 4,061
416
Brilliant
I '14: 22,324
Dianisidine
D
Azurine 5G
I '20: 1,563
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid (2 mols)
TRISAZO DYES
452
Benzo Indigo Blue
Tolidine
D
a-Naphthylamine
1 : 8-Dihydroxy-naph-
thalene-4-s ulf onic
Acid (2 mols)
460
Benzo Black
I '14: 602
Benzidine-disulfonic-
D
Blue 5G
Acid
a-Naphthylamine
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid (2 mols)
4: 5-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1 : 8-Dihydroxy-naphthalene-4-sulf onic Acid
4:6-Dihydroxy-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, 1 : 7-Dihydroxy-naphthalene-4-sulf onic Acid
DYES CLASSIFIED BY INTERMEDIATES 227
Dihydroxy-naphthalene-sulfonic Acid S
See, 1 : 8-Dihydroxy-naphthalene-4-sulfonic Acid
Dihydroxy-naphthoic Acid L
2 : 6-Dihydroxy-3-naphthoic Acid (not considered herein)
Dihydroxy-naphthoic Acid S
1 : 7-Dihydroxy-6-naphthoic Acid (not considered herein)
1 : 7-Dihydroxy-2-naphthoic-4-sulfonic Acid
1 : 7-Dihydroxy-naphthalene-2-carboxylic-4-sulf onic Acid
1 : 7-Dihydroxy-2-earboxy-naphthalene-4-sulf onic Acid
1: 7-Dihydroxy-4-sulfo-2-naphthoic Acid (C. A. nomen.)
OH
HOf / \ / NcOOH -
\/\/
SO 3 H
FORMATION. l-Hydroxy-2-naphthoic acid is disulfonated with 4 parts
of 20 per cent oleum, the product isolated and fused with caustic
soda at 190-200
LITERATURE. Cain, Intermediate Products (2d Ed.), 242
Lange, Zwischenprodukte, 2677
Dyes Derived from 1 : 7-Dihydroxy-2-naphthoic-4-sulfonic Acid
9*4.
284
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
396
DISAZO DYES
Indazurine RM
Tolidine
Nevile-Winther's Acid
D
399
Indazurine TS
Tolidine
Gamma Acid
D
427
Indazurine GM
Dianisidine
Nevile-Winther's Acid
D
429
Indazurine BB
Dianisidine
R Acid
D
430
Indazurine 5GM
Dianisidine
HAcid
D
228 DYES CLASSIFIED BY INTERMEDIATES
1 : 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
1 : 7-Dihydroxy-naphthalene-6-carboxylic-3-sulf onic Acid
1: 7-Dihydroxy-6-carboxy-naphthalene-3-sulfonic Acid
Nigrotic Acid
Nigrotinic Acid
3: 5-Dihydroxy-7-sulfo-2-naphthoic Acid (C. A. nomen.)
OH
HO
HOOC
S0 3 H
FORMATION. 2-Hydroxy-3-naphthoic acid is disulfonated with 4 parts
of 24 per cent oleum at 125-150 for from two to three hours, the
product isolated, and fused with 2 parts of caustic soda at about
210-220 and then at 230-240
LITERATURE. Cain, Intermediate Products (2d Ed.), 241
Lange, Z\vischenprodukte, #2678
Dyes Derived from 1 : 7-Dihy droxy-6-naphthoic-3-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
352
DISAZO DYES
Direct Violet R
I J 14: 661
M'19: ?
Benzidine
w-Tolylene-diamine
D
353
Direct Indigo
Blue BN
I '14: 6,000
Benzidine
HAcid
D
354
Direct Gray R
I '20: 4,927
Benzidine
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
(2 mols)
D
397
Direct Blue R
M'17: ?
Tolidine
Nevile-Winther's Acid
D
DYES CLASSIFIED BY INTERMEDIATES
229
Dyes Derived from 1 : 7-Dihydroxy-6-naphthoic-3-sulf onic Acid
(continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
398
Direct Gray B
Tolidine
D
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfomc Acid
(2 mols)
428
Direct Blue B
I '14: 21,421
Dianisidine
D
M'17: 14,823
Nevile-Winther's Acid
M'18: ?
I '20: 7,055
1 : 2-Dihy droxy-naphthoquinone
See, Naphthazarin
5 : 6-Dihydroxy-l : 4-naphthoquinone
See, Naphthazarin
5: 6-Dihydroxy-a-naphthoquinone
See, Naphthazarin
1: 7-Dihydroxy-4-sulfo-2-naphthoic Acid (C. A. nomen.)
See, 1 : 7-Dihydroxy-2-naphthoic-4-sulfonic Acid
3: 5-Dihydroxy-7-sulfo-2-naphthoic Acid (C. A. nomen.)
See, 1 : 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
Dihydroxy-tartaric Acid
Dioxy-tartaric Acid
C:(OH) 2 .COOH
C:(OH) 2 .COOH
C 4 H 6 O 8 =
230
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By oxidation of tartaric acid with strong nitric acid in
presence of oleum
LITERATURE. Cain, Intermediate Products (2d Ed.), 168 '
Dyes Derived from Dihydroxy-tartaric Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYE
23
Tartrazine
I '14: 272,477
Phenyl-hydrazine-p-
A
M'17: ?
sulfonic Acid (2 mols)
M'18: ?
M'19: ?
I '20: 47,877
M '20: 701,722
3:6-Dihydroxy-9-xanthene-proprionic Acid, 7-Lactone (C. A.
nomen.)
See, Resorcinol-succinein
-(0-Dimethylamino-anilino) -phenol (C. A. nomen.)
See, 4J3imethylamino^'-hydroxy-diphenylamine
Dimethylamino-azo-benzene-disulfonic Acids
5-Dimethylammo-o : p'-azo-bis(6enzene-sulfonic Acid) (C. A.
nomen. for 7)
6-Dimethylamino-w : p / -azo-bis(6enzene-sulfonic Acid) (C. A.
nomen. for II)
H0 3 S
and
(I)
(II)
S0 3 H
= 385
DYES CLASSIFIED BY INTERMEDIATES
231
FORMATION. The compound represented by " Formula I" is prepared
by coupling diazotized sulfanilic acid with dime thy 1-aniline-w-
sulfonic acid (prepared by sulfonating dimethyl-aniline). The iso-
meric compound represented in all probability by "Formula II,"
is made by direct sulfonation of dimethylamino-azo-benzene by
means of oleum
LITERATURE. Ger. Pat. 80434, Methods (b) and (a). Frdl. 4, 490
Cf. Ullmann, Enzy. tech. Chemie, 2, 81
Dye Derived from Dimethylamino-azo-benzene-disulfonic Acids
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
628
OXAZINE DYE
Gallocyanine MS
I '20: 22
Gallic Acid
M
^-Dimethylamino-benzaldehyde
HCO
:
N(CH 3 ) 2
FORMATION. -Dimethyl-aniline is changed into dimethylamino-benzyl
alcohol by treatment with hydrochloric acid and formaldehyde.
This is then oxidized by adding nitroso-dimethyl-aniline directly
to the crude alcohol, resulting in the formation of dimethylamino-
benzylidene-amino-dimethyl-aniline, (CH 3 ) 2 N.C 6 H 4 .CH: N.C 6 H 4 .-
N(CH 3 ) 2 . This latter by treatment with nitrous acid or formalde-
hyde forms pure p-dimethylamino-benzaldehyde
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 307
Lange, Zwischenprodukte, #333-335
232 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Dimethylamino-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TEIPHENYL-METHANE
DYE
529
Acid Violet 6B
Ethyl-sulfobenzyl-
aniline (2 mols)
[Oxidation]
A
564
Naphthalene Green
V
I >14: 22,144
I '20: 9,291
Dimethyl-aniline
m-Xylene
A
/>-Dimethylamino-benzoyl Chloride
OCC1
r=C 9 Hi ClNO = 183.5
'(CH 3 ) 2
FORMATION. From dimethyl-aniline by action of phosgene
LITERATURE. Beil., 2, 1271
Dye Derived from />-Dimethylamino-benzoyl Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
533 .
Acid Violet 7BN
Methyl-diphenylamine-
A
sulf onic Acid (2 mols)
Dimethylamino-benzoyl-methyl-aniline
Dime thy lamino-benzo-methyl-aniline (Schultz nomen.)
p-Dimethylamino-Af-methyl-frenzanilide (C. A, nomen.)
CH 3
(CH 3 ) 2 N
\
O.N
nrCi 6 Hi 8 N 2 0=^254
DYES CLASSIFIED BY INTERMEDIATES
233
FORMATION. Dimethyl-aniline reacting with phosgene forms p-di
methylamino-benzoyl chloride, which latter unites with methyl
aniline to form the p-dimethylamino-benzoyl-methyl-aniline
LITERATURE. Cf. Ger. Pat. 41751, 44077
Cf. Georgievics and Grandmougin, Dye Chemistry, 174
Dye Derived from Dimethylamino-benzoyl-methyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYL-METHANE
DYE
493
Auramine
I '14: 449,276
M'17: ?
Dimethyl-aniline
B
M'18: 45,634
M '19 :127,567
M J 20: ?
I } 20: 74,414
6-(/>-Dimethylamino-benzyl)-W: JV-dimethyl-metanilic Acid (C. A.
nomen.)
See, p: p'-Tetramethyl-diamino-diphenylmethane-sulfonic
Acid
5- Dimethylamino- a- (p- dimethylamino- phenyl)- a- hydroxy- o-
foluene-sulfonic Acid (C. A. nomen.)
See, p: p'-Tetramethyl-diamino-benzohydrol-sulfonic Acid
(Dimethylamino-hydroxy-benzoyl) -benzoic Acid
o-(4-Dimethylamino-2-hydroxy-benzoyl)-6enzoic Acid (C. A. no-
men.)
OH
FORMATION. By condensing phthalic anhydride and w-dimethylamino-
phenol
234
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 232
Lange, Zwischenprodukte, #1394, 1395 (Note Lange's
formula is at variance with structure given above, which,
however, corresponds to the generally accepted formula)
Dyes Derived from (Dimethylamino-hydroxy-benzoyl) benzole Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
575
XANTHONE DYES
Rhodine 12GM
Resorcinol Methyl
Ether
[Ethyl esterification]
B
576
Rhodamine 3G
I '14: 19,568
I '20: 855
3-Amino-p-cresol
[Ethyl esterificationj
B
577
Rhodine 2G
Ethyl-w-amino-phenol
[Ethyl esterification]
B
578
Rhodamine 12GF
Resorcinol
[Formaldehyde;
esterification]
B
4-Dimethylamino-4'-hydroxy-diphenylamine
p-(p-Dimethylammo-anilino) -phenol (C. A. nomen.)
(CH 3 ) 2 N
NH
H
FORMATION. (1) Dimethyl-p-phenylene-diamine is heated with the
hydrochloride of p-amino-phenol. (2) Dimethyl-p-phenylene-
diamine and phenol are simultaneously oxidized and the product
carefully reduced
LITERATURE. Lange, Zwischenprodukte, #1644
Lange, Swefelfarbstoffe, 145 ; 157
DYES CLASSIFIED BY INTERMEDIATES 235
Dye Derived from 4-Dimethylamino-4 / -hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
728
SULFUR DYE
Immedial Sky Blue
M'17: ?
[S+NasS]
S
4-Dimethylamino-3 / -methoxy-benzophenone (C. A. nomen.)
Me thoxy -dimethy lamino-benzophenone
N(CH 3 ) :
FORMATION. 10 parts of ra-methoxy-benzanilide, 14 parts of dimethyl-
aniline and 7 parts of phosphorus oxychloride are heated together
carefully on the water bath at 90. The melt is treated with 50
parts of water and 5 parts of hydrochloric acid, and the yellow brown
solution warmed to 70-80 until the color has disappeared, which
indicates the completion of the splitting off of the aniline. More
water is now added, the precipitate filtered, washed, dried, and
crystallized from two parts of alcohol. From the filtrate aniline
and dimethyl-aniline can be recovered
LITERATURE. Lange, Zwischenprodukte, #1383
Dye Derived from 4-Dimethylamino-3'-methoxy-benzophenone
Schultz
Number
for Dye
Ordinary Nome and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
547
Ketone Blue 4BN
Methyl-diphenylamine
[Sulfonation]
A
-Dimethylamino-W-methyl-&enzanilide (C. A. nomen.)
See, Dimethylamino-benzoyl-methyl-aniline
236 DYES CLASSIFIED BY INTERMEDIATES
2-Dimethylamino-8-naphthol-6-sulfonic Acid
See, Dimethyl-gamma Acid
7-Dimethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, Dimethyl-gamma Acid
5-Dimethylammo-2-nitroso-/>-cresol (OH=l t C. A. nomen.)
Nitroso-dimethyl-m-amino-p-cresol (OH = 1)
OH
NO
180
CH 3
FORMATION. 3-Dimethylamino-p-cresol (OH = 1) [which can be ob-
tained by decomposing diazo-dimethyl-o-toluidine in an acid solu-
tion] is dissolved in hydrochloric acid, cooled to C., and nitrosified
with aqueous solution of sodium nitrite
LITERATURE. Lange, Zwischenprodukte, #1089
Dye Derived from 5-Dimethylamino-2-nitroso--cresol
Schultz
Numbei
jar Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Uesd and Notes
Dye
Appli-
cation
Class
621
OXAZINE DYE
Cresyl Blue 2BS
p-Phenylene-diamine
B
m-Dimethylamino-^henol (C. A. nomen.)
m-Hydroxy-dimethyl-aniline
Dimethyl-m-amino-phenol
*OH
lN(CH 3 ) 2
FORMATION. By caustic soda fusion of dime thy 1-aniline-m-sulfonic
acid, prepared by sulfonating dimethyl-aniline with oleum
LITERATURE. Lange, Zwischenprodukte, #603-606, 2263
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Dimethylamino-phenol
237
Schult:
Numbei
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
568
XANTHONE DYES
Pyronine G
m-Dimethylamino-
phenol (2 mols)
[Oxidation]
B
569
Acridine Red B
m-Dimethylamino-
phenol (2 mols)
[Oxidation]
or
[Oxidation of Pyronine
G with KMnO 4 ]
B
570
Rhodamine S
I '14: 600
I '20: 273
m-Dimethylamino-
phenol (2 mols)
[Succinic Anhydride]
A
Dimethyl-aniline
N: JV-Dimethyl-aniline (C. A. nomen.)
N(CH 3 ) 2
STATISTICS. Imported '14: 48,642 Ibs.
Manufactured '17: 2,847,093 Ibs.
Manufactured '18: 4,263,458 Ibs.
Manufactured '19: 3,559,654 Ibs.
Manufactured '20: 5,447,107 Ibs.
FORMATION. By heating aniline and methanol (methyl alcohol) in an
autoclave in the presence of sulfuric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 62
Lange, Zwischenprodukte, #129
238
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dimethyl-aniline
Schult?
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
32
Butter Yellow
I '14: 4,062
Aniline
ss
OH Yellow
M'17: 33,180
M'18: 27,669
M'19: 31,156
M'20: 74,182
124
Diazine Green S
I '14: 1,340
p-Tolylene-diamine
B
o-Toluidine
Aniline or o-Toluidine
or
Safranine
138
Helianthine
I '14: 500
Sulfanilic Acid
A
Methyl Orange
M'18: ?
M'19: ?
M'20: ?
AURAMINES
493
Auramine
I '14: 449,276
Dimethylamino-benzo-
B
M'17: ?
methylaniline
M'18: 45,634
M'19: 127,567
I '20: 74,414
M'20: ?
TRIPHENYL-METHANE
DYES
495
Malachite Green
I '14: 183,852
Dimethyl-aniline
B
M'17: 130,229
(2 mols)
M'18: 290,416
Benzaldehyde
,
M'19: 560,301
[Oxidation]
I '20: 100
M'20: 654,237
496
Setoglaucine
I '20: 1,102
Dimethyl-aniline
B
(2 mols)
o-Chloro-benzaldehyde
[Oxidation]
497
New Fast Green 2B
I '14: 44,595
Dimethyl-aniline
B
Victoria Green 3B
(2 mols)
2: 5-Dichloro-benzalde-
hyde -
[Oxidation]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dimethyl-aniline (continued)
239
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TBIPHENYL-METHANE
DYES (continued)
510
Azo Green
Dimethyl-aniline
M
(2 mols)
w-Nitro-benzaldehyde
Salicylic Acid
[Oxidation]
515
Methyl Violet
I '14 :255,063
Dimethyl-aniline
B
M'17: 375,107
(3 mols)
M '18: 632,196
[Phenol]
M'19: 574,436
[Oxidation]
I '20: 3,312
M '20: 600,873
516
Crystal Violet
I '14: 51,872
Ketone
B
M'17: ?
or
M'18: ?
Dimethyl-aniline
M'19: ?
(3 mols)
I '20: 2,919
Phosgene
M'20: ?
or
Hydrol
[Oxidation]
517
Methyl Violet 5B
I '14: 22,387
[Benzylation of Methyl
B
Benzyl Violet
I '20: 3,313
Violet]
M'17: ?
or
.
Benzyl-chloride
Dimethyl-aniline
(3 mols)
[Phenol]
519
Methyl Green
[Methyl Chloride of
B
Methyl Violet]
or
Dimethyl-aniline
(3 mols)
[Phenol and Methyl
'
Chloride]
240
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Dimethyl-aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufactuie
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL- METHANE
DYES (continued)
523
Fast Green
I '14: 14,347
m-Nitrobenzaldehyde
A
I '20: 10,461
Dimethyl-aniline
(2mols)
Benzyl-chloride
(2 mols)
[Sulfonation, Oxidation]
564
Naphthalene
I '14: 22,144
p-Dimethylamino-
A
Green V
I '20: 9,291
benzaldehyde
w-Xylene
THIAZINE DYES
659
Methylene Blue
I '14: 185,958
Dimethyl-aniline
B
M '17: 268,435
(2 mols)
M '18 :312,572
[Naa&Os, etc.]
M'19:-HL65,992
or
I '20: 2,053
Nitroso-dimethyl-
M '20: 577,264
aniline
[NasSaOs, etc.]
or
Dimethyl-p-phenylene
diamine
[NaaSaOs, etc.]
660
Methylene Green
I' 14: 30,812
Dimethyl-aniline
B
M'18: ?
(2 mols)
M'19: 2,435
[Na^Oa, Nitration]
I '20: 1,049
or
Nitroso-dimethyl-
aniline
[NaaS-A, etc.; Nitra-
tion]
or
Dimethyl-p-phenylene-
diamine
[Naa&Os, etc.; Nitra-
tion]
or
[Methylene Blue
nitrated]
661
Thionine Blue^G
I '14: 18,618
Ethyl-methyl-aniline
B
I '20: 330
[Nas&Os, etc.]
DYES CLASSIFIED BY INTERMEDIATES 241
N:N-Dimethyl-p: />'-azo-bisaniline (C. A. nomen.)
See, Dimethyl-p : p'-diamino-azo-benzene
2: 2 / -Dimethyl-l : I'-bianthraquinone (C. A. nomen.)
2: 2'-Dimethyl-l : I'-dianthraquinonyl
==C 30 Hi 8 04 442
FORMATION. l-Amino-2-methyl-anthraquinone is dissolved in sulfuric
acid and sodium nitrite added. The isolated and dried diazonium
sulfate is stirred into acetic anhydride, and copper powder added.
Nitrogen is evolved and the combination takes place, forming the
bianthraquinone derivative
LITERATURE. Lange, Zwischenprodukte, #3491-3493
Cain, Intermediate Products (2d Ed.), 261
Dyes Derived from 2 : 2 / -Dimethyl-l : I'-bianthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
760
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
Gold Orange G
Pyranthrone
I '14: 20,092
I '20: 7,617
[2 mols E^O removed]
V
761
Indanthrene
Gold Orange R
I '14: 50,496
I '20: 35,338
[2 mols EfeO removed,
Chlorination]
[or Pyranthrone 760,
chlorinated]
V
762
Indanthrene
Scarlet G
I '14: 99
I '20: 399
[2 mols H^O removed,
Bromination]
[or Pyranthrone 760,
brominated]
V
242
DYES CLASSIFIED BY INTERMEDIATES
Dimethyl-/> : />'-diamino-azo-benzene
N: AT-Dimethyl-p : p'-azo-bisaniline (C. A. nomen.)
(CH 3 ) 2 N
= Ci 4 H 16 N 4 = 240
FORMATION. (1) By coupling of diazotized p-nitro-aniline with di'
methyl-aniline and subsequent reduction with sodium sulfide.
(2) By coupling of diazotized p-amino-acetanilide with dimethyl-
aniline and splitting off of acetyl group
LITERATURE. Heumann, Anilinfarben, 3, 1467; 4, 1026
Cf. Lange, Zwischenprodukte, #1760
Dye Derived from Dimethyl-^ : j^-diamino-azo-benzene
Schullz
Number
lor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
239
DISAZO DYE
AzotolC
/3-Naphthol
MF
4: 4 / -Dimethyl-diamino-3: 3'-ditolyl-methane
Dimethyl-diamino-di-o-tolyl-methane
4:4'-Methylene-bis(A r -methyl-o-foluidine) (C. A. nomen.)
/NNH.CHS _ n ^ _
OUT OTT 017X1 22lN 2 -
V^H2 \ >v>>Jl3
FORMATION. By condensing formaldehyde and two molecules of
methyl-o-toluidine
LITERATURE. Cain, Intermediate Products (2d Ed.), 104
Lange, Zwischenprodukte, #1318
Dye Derived from 4:4 / -Dimethyl-diamino-3:3 / -ditolyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AURAMINES
494
Auramine G
I '14: 1,902
[Sulfur, Ammonium
B
chloride, etc.]
DYES CLASSIFIED BY INTERMEDIATES
243
Dimethyl-diamino-di-o-tolyl-methane
See, 4: 4'-Dimethyl-diamino-3 : 3'-ditolyl-methane
2: 2-Dimethyl-l : I'-dianthraquinonyl
See, 2: 2'-Dimothyl-l : l'-6ianthraquinone (C. A. nomen.)
Dimethyl-gamma Acid
2-Dimethylamino-8-naphthol-6-sulfonic Acid
7-Dimethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
HO
H0 3 Sl
FORMATION. G acid is heated with dimethylamine in an autoclave
around 200, the dimethylamino-G acid thus obtained is fused with
caustic soda at 210-220, and the dimethyl-gamma acid isolated
LITERATURE. Lange, Zwischenprodukte, #2550
Dyes Derived from Dimethyl-gamma Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
206
Diphenyl
I '14: 8,642
p-Nitro-toluene-o-
D
Catechine G
sulfonic Acid
p-Phenylene-diamine
[Diphenyl Orange RR]
DISAZO DYES
348
Diphenyl
I '14: 13,471
Salicylic Acid
D
Brown BN
Benzidine
393
Diphenyl
M'20: ?
Salicylic Acid
D
Brown 3GN
Tolidine
N: AT-Dimethyl-^-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-dimethyl-aniline
244 DYES CLASSIFIED BY INTERMEDIATES
N: W-Dimethyl-m-/>henylene-diamine (C. A. nomen.)
w-Amino-dimethyl-aniline
N(CH 3 ) 2
FORMATION. Dimethyl-aniline is nitrated with mixed acid, and the
w-nitro-dimethyl-aniline separated from the para isomer. The
w-derivative is now reduced to dimethyl-ra-phenylene-diamine
LITERATURE. Green, Organic Coloring Matter (1908), 32
Dyes Derived from N: ^-Dimethyl-m-phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
603
ACRIDINE DYES
Acridine Orange NO
I '14: 2,336
I '20: 1,925
Dimethyl-m-phenylene-
diamine (2 mols)
[Formaldehyde, Oxida-
tion, etc.]
B
604
Acridine Orange R
Dimethyl-w-phenylene-
diamine (2 mols)
Benzaldehyde
[Ammonia removal;
Oxidation]
B
W:#-Dimethyl-^-phenylene-diamine (C. A. nomen.)
p-Amino-dimethyl-aniline
N(CH 3 ) 2
STATISTICS. Imported ' 14 : very small
Manufactured '17: ?
Manufactured '18: ?
Manufactured '20: 314,931
DYES CLASSIFIED BY INTERMEDIATES
245
FORMATION. Dimethyl-aniline by action of nitrous acid forms nitroso-
dimethyl-aniline, which by reduction with zinc dust and hydro-
chloric acid furnishes dimethyl-p-phenylene-diamine
LITERATURE. Lange, Zwischenprodukte, #561-563
Dyes Derived from AT: W-Dimethyl-/>-phenylene-diamine
Schultz
Number
lor Dye
Ordinary Name and
Calss of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
62
MONOAZO DYES
Azogalleine
Pyrogallol
M
63
Azo Acid Blue
I '14: 45,098
I '20: 4,485
1 : 8-Dihydroxy-naph-
thalene-4-sulf onic Acid
M
619
INDOPHENOL
Indophenol
M'17: ?
M'18: ?
M '19: 126,611
M'20: ?
a-Naphthol
[Oxidation]
V
627
OXAZINE AND
THIAZINE DYES
Modern Cyanine
Nitroso-dimethyl-
aniline
Gallamide
M
659
Methylene Blue
I '14: 185,958
M '17: 268,435
M'18: 312,572
Dimethyl-aniline
[Naa&Os, etc.]
B
I '20: 2,053
M '20: 577,264
660
Methylene Green
I '14: 30,812
M'18: ?
M'19: 2,435
I '20: 1,047
Dimethyl-aniline
[Na2S20a, etc.]
[Nitration]
or
[Methylene Blue
nitrated]
B
661
Thionine Blue G
I '14: 18,618
I '20: 2,030
Ethyl-methyl-aniline
[Nas&Os, etc.]
B
246 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from N: W-Dimethyl-/>-phenylene-diamme (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
669
Neutral Violet
Dimethyl-p-phenylene-
B
diamine (2 mols)
w-Phenylene-diamine
670
Neutral Red
M'18: ?
m-Tolylene-diamine
B
680
Methylene
I '14: 1,521
Aniline (2 mols)
B
Violet BN
M'17: ?
[Oxidation]
I '20: 33
681
Methylene Gray
I '14: 29,507
Dimethyl-p-phenylene-
B
New Fast Gray
M'17: ?
diamine (2+ mols)
M'18: 16,746
[Oxidation]
M'19: 28,458
I '20: 509
M'20: 31,620
683
Safranine MN
I '14: 198
Aniline
B
M'18: ?
o- or p-Toluidine
M'19: ?
[Oxidation]
M'20: ?
690
Diphene Blue R
I '20: 3,124
s?/w-Di-p-tolyl-w-
B
Metaphenylene
phenylene-diamine
BlueR
[Oxidation]
SULFUR DYES
729
Kryogene Pure
Aniline (2 mols)
S
BlueR
[S+NaaS]
or
[Methylene Violet;
S+Na^S]
731
Thiophor Indigo C J
a-Naphthol
3
[S+NaaS]
N: ^-Dimethyl-/>-phenylene-diamine-thiosulfonic Acid
p-Amino-dimethyl-aniline-thiosulfonic Acid
l-Amino-4-dimethylamino-benzene-2-thiosulfonic Acid
2-Amino-5-dimethylamino-6enzene-thiosulfonic Acid (C.
nomen.)
A.
DYES CLASSIFIED BY INTERMEDIATES
N(CH 3 ) 2
247
NH
FORMATION. 10 parts of dimethyl-p-phenylene-diamine sulfate are dis-
solved in 100 parts of water and cooled to 0, and a cold solution of
5.5 parts of potassium bichromate in 60 parts of water and 18 parts
by volume of 50 per cent acetic acid, is introduced quickly during
agitation. To the crystal mass is now added at once a solution of
22 parts of sodium thiosulfate and 27 parts of aluminum sulfate
in 70 parts of water, and the mixture agitated at 10-20. Upon
cooling to the desired product separates out
LITERATURE. Lange, Zwischenprodukte, #931
Dyes Derived from N: W-Dimethyl-^phenylene-diamine-thiosulfonic
Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
661
THIAZINE DYES
Thionine Blue G O
I '14: 18,618
I '20: 2,030
Ethyl-methyl-aniline
B
664
Lenco-gallo
Thionine DH
Gallic Acid
M
665
Urania Blue
I '14: 132
m-phenylene-diamine
A
667
Brilliant Alizarin
BlueG
Indochromine T
I '14: 19,481
M'19: ?
I '20: 3,214
M'20: ?
1 : 2-Naphthoquinone-
4: 6-disulfonic Acid
M
#:#'-Di-2-naphthyl-m-phenylene-diamine
t NH /N NH
248
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. 108 parts of ra-phenylene-diamine, 432 parts of /3-naphthol
and 2-3 parts of iodine are heated together at 200 and finally
at 260. The melt is powdered, and washed successively with
dilute caustic soda, hydrochloric acid, water, alcohol, and ether.
The residue is crystallized from aniline. Yield good
LITERATURE. Lange, Zwischenprodukte, #2875, 2876
Dyes Derived from W:W'-Di-2-naphthyl-m-phenylene-diamine
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import, and
Manufacture
Other Intermediates
sed and Notes
Dye
Appli-
cation
Class
THIAZINE DYE
665
Urania Blue
I '14: 132
Dimethyl-p-phenylene-
A
diamine- thiosulfonic
Acid
AZINE DYE
692
Naphthazine Blue
I '14: 6,261
Nitroso-dimethyl-
A
I '20: 2,249
aniline
2: 4-Dinitro-aniline (C. A. women.)
w-Din itro-aniline
NH 2
= C 6 H5N 3 04=183
N0 2
FORMATION. Aniline is condensed with phthalic acid, and the phthal-
anil dinitrated. Upon heating the latter product with aniline
under pressure the 2 : 4-dinitro-aniline is split off
LITERATURE. Lange, Zwischenprodukte, #539
Dyes Derived from 2 : 4-Dinitro-aniline
ScKultz
Number
jor Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufactwe
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
59
Wool Violet S
I '14: 308
Diethyl-anilme-w-
A
M'18: ?
sulfonic Acid
M'19: ?
DYES CLASSIFIED BY INTERMEDIATES
m-Dinitro-aniline
See, 2: 4-Dinitro-cmiline (C. A. nomen.)
p-(2: 4-Dinitro-anilino) -phenol (C. A. nomen.)
See, 2: 4-Dinitro-4'-hydroxy-diphenylamine
4: 8-Dinitro-anthrachrysone-2: 6-disulfonic Acid
240
2 N
C(
OH
_ p N q __
H0 3 s X OH -C 14 H 6 N 2 16 S 2 -522
\/ \co/ \/
HO N0 2
FORMATION. Anthrachrysone is sulfonated and nitrated
LITERATURE. Green, Organic Coloring Matters (1908), #554 and #557
Dye Derived from 4: 8-Dinitro-anthrachrysone-2 : 6-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONB AND
ALLIED DYE
796
Acid Alizarin
I '20: 1,334
[Sodium sulfide
ACr
Green G
reduction]
1: 5-Dinitro-anthraflavic-3: 7-disulfonic Acid
HOsS/N/
HO \A
N0 2
CO
N
S0 3 H
Ci 4 H 6 N 2 Oi 4 S 2 =:490
FORMATION. By the sulfonation and nitration of anthraflavic acid
(which is prepared by heating m-hydroxy-benzoic acid with sul-
furic acid at 190 C.)
LITERATURE. Thorpe, Die. Chemistry, 1, 84
Cf. Bucherer, Lehrbuch des Farbenchemie, 339 (1914)
250 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1 : 6-Dinitro-anthraflavic-3 : 7-disulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
857
Erweco Alizarin
Aniline (2 mols)
ACr
Acid Blue R
[Sulfonation]
Dinitro-anthraquinone
(1 : 5-and 1 : 8-Dinitro-anthraquinones)
00
O,N
238
STATISTICS. Manufactured '19: ?
FORMATION. The mixed compounds are obtained from anthraquinone,
by nitration in sulfuric acid solution, and by pouring the nitration
product into water
LITERATURE. Cain, Intermediate Products (2d Ed.), 253
Dyes Derived from Dinitro-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Othei I mer mediates
Used and Notes
Dye
Appli-
cation
Class
749
SULFUR DYE
Anthraquinone Black
[S+NaaS]
S
790
ANTHRAQUINONE AND
ALLIED DYES
Anthracene
Blue
I '14: 26,642
I '20: 3,539
[Sulfonation, Oxidation
ACr
801
Anthracene
Blue WGG
I '20: 1,500
[Oxidation]
M
802
Anthracene
Blue WG new
[Oxidation]
M
DYES CLASSIFIED BY INTERMEDIATES
1 : 5-Dinitro-anthraquinone
6 238
251
O 2 N
STATISTICS. Manufactured '20: ?
FORMATION. From anthraquinone in sulfuric acid solution by nitra-
tion with HN0 3 or NaN0 3 . The mixed 1 : 5 and 1 : 8 dinitro-
, anthraquinones are recovered by pouring the nitration mixture into
water. By extraction of the mixed dinitro-compounds with ace-
tone or alcohol, the 1 : 5-dinitro-anthraquinone is left behind
LITERATURE. Cain, Intermediate Products (2d Ed.), 253
Lange, Zwischenprodukte, #3218
Dyes Derived from 1 : 5-Dinitro-anthraquinone
Schuitz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
749
SULFUR DYE
Anthraquinone Black
[S+NasS]
S
800
ANTHRAQUINONE AND
ALLIED DYES
Anthracene
Blue WG
I '14: 54,812
I '20: 2,049
[Oxidationl
M
853
Anthraquinone
Violet
I '14: 1,202
I '20: 1,649
p-Toluidine (2 mols)
[SulfonationJ
ACr
m-Dinitro-fcenzene
N0 2
STATISTICS. Imported '14: 164,650 Ibs.
Manufactured '17: 2,333,192 Ibs.
Manufactured '18: 4,115,269 Ibs.
Manufactured '19: 2,280,282 Ibs.
Manufactured '20: 3,380,112 Ibs.
252
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By nitration of nitro-benzene or of benzene, using mixed
acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 32
Cf. Lange, Zwischenprodukte, #543
USES. For the manufacture of w-nitro-aniline and w-phenylene-
diamine
2 : 2'-Dinitro-/> : ^'-biacetanilide
See, Diacetyl-o: o'-dinitro-benzidine
2: 4-Dinitro-chloro-benzene
See, l-Chloro-2 : 4-dinitro-benzene (C. A. nomen.)
Dinitro-/>-cresol
OH
N0 2
N0 2
FORMATION. Probably by the dinitration of p-cresol
LITERATURE. Cf. Thorpe, 2, 165
Cf. Lange, Schwefelfarbstoffe, 132, 381
Dye Derived from Dinitro-/>-cresol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
725
Immedial Dark
I '14: 23,887
[S+NasS]
S
Brown A
M'18: ?
Immedial Brown B
Dinitro-dibenzyl-disulfonic Acid
2: 2'-Ethylene-bis(5-nitro-6enzene-sulfonic Acid) (C. A. nomen.)
SO 3 H HO 3 S
" ~ 432
DYES CLASSIFIED BY INTERMEDIATES
253
FORMATION. 12 parts of sodium p-nitro-toluene-sulfonate are dissolved
in 50 parts of hot water, and treated with 100 parts of sodium
hypochlorite solution (2 per cent HOC1) and 50 parts of caustic
soda solution (40) at 70. At end of reaction, cooled with ice to
40 and after crystallizing several hours, the product is filtered off.
LITERATURE. Lange, Zwischenprodukte, #1460
Dyes Derived from Dinitro-dibenzyl-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
STILBENE DYES
10
Mikado Yellow
I '14: 85,795
Dinitro-dibenzyl-disul-
D
Stilbene Yellow
M'18: ?
fonic Acid (2 mols)
M'20: ?
12
Diphenyl
Aniline
D
Citronine G
18
Diphenyl Fast
I '14: 10,229
Dehydrothio-toluidine-
D
Yellow
sulf onic Acid (2 mols)
I '20: 1,102
or Primuline-sulfonic
Acid (2 mols)
2: 5-Dmitro-diphenylamine-3': 4-disulfonic Acid
3: 5-Dinitro-3': 4-imino-bis(6enzene-sulfonic Acid) (C. A. nomen.)
NO,
S0 3 H
HO
NH
NO,
FORMATION. By reaction of l-chloro-2: 6-dinitro-benzene-4-sulfonic
acid and metanilic acid in presence of sodium acetate
LITERATURE. Lange, Zwischenprodukte, #1712
Cf. Schultz, Farbstofftabellen, #542
254 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2 : 5-Dinitro-diphenylamine-3' : 4-disulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
542
Agalma Green B
I '14: 2,294
Hydrol
A
2: 4-Dinitro-diphenylamine-3'-sulfonic Acid
JV-(2: 4-Dinitro-phenyl)-metanilic Acid (C. A. nomen.)
N0 2
S0 3 H
NH
= 339
FORMATION. From chloro-dinitro-benzene and metanilic acid
LITERATURE. Lange, Zwischenprodukte, #1673
Cf. Schultz, Farbstofftabellen (1914), #738
Dye Derived from 2:4-Dinitro-diphenylamine-3'-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Clcss of Dye
Statistics of
Impoit and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
738
SULFUR DYE
Cotton Black
[S+NaaS]
S
2: 4-Dinitro-diphenylamine-4'-sulfonic Acid
N-(2: 4-Dinitro-phenyl)-sulfanilic Acid (C. A. nomen.)
N0 2
~" = 339
FORMATION. From chloro-dinitro-benzene and sulfanilic Acid
LITERATURE. Lange, Zwischenprodukte, #1673
Cf. Schultz, Farbstofftabellen, #738
DYES CLASSIFIED BY INTERMEDIATES 255
Dye Derived from 2 : 4-Dinitro-diphenylamine-4'-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Impoit end
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
738
SULFUR DYE
Cotton Black
[S+NasS]
S
2: 4-Dinitro-4'-hydroxy-diphenylamine
p-(2:4-Dinitro-anilino)-phenol (C. A. nomen.)
N0 2
NH
= Ci 2 H 9 N 3 05 =- 275
STATISTICS. Manufactured 1919 but amount not disclosed
FORMATION. From chloro-dinitro-benzene and p-amino-phenol by
boiling molecular proportions in an aqueous suspension with
slightly more than the theoretical amount of limestone
LITERATURE. Cain, Intermediate Products (2d Ed.), 73
Lange, Zwischenprodukte, #1670
Dyes Derived from 2: 4-Dinitro-4'-hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
S
724
SULFUR DYES
Immedial Black
I '14: 54,696
M'18: ?
[S+NaaS]
*
725
Immedial Dark
Brown A
Immedial Brown B
I '14: 23,887
M'18: ?
[NaOH; S+Na^S]
3
726
Pyrogene Direct Blue
Pyrogene Blue
I '14: 10,934
I '20: 2,498
[Alcohol; S+ NasS]
S
3: S-Dinitro-S': 4-imino-bis(&enzene-sulfonic Acid) (C. A. nomen.)
See, 2: 5-Dinitro-diphenylamine-3': 4-disulfonic Acid
256 DYES CLASSIFIED BY INTERMEDIATES
1 : 5-and 1 : 8-Dinitro-naphthalenes
NO 2 2 N NO 2
/VN
and I = Ci H 6 N 2 4 =:218
_-\/ \A/
2 N
STATISTICS. Imported '14: very small amount
Manufactured '18: ?
Manufactured '19: ?
FORMATION. From a-nitro-naphthalene by nitration
LITERATURE. Cain, Intermediate Products (2d Ed.), 170
Dyes Derived from 1 : 5- and 1 : 8-Dinitro-naphthalenes
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
774
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Black
I '14: 205,439
I '20: 17,421
[Oxidationl
M
775
Alizarin Dark
Green W
Phenol
[Oxidationl
M
776
Printing Black for
Wool
[Reduction!
A
1: 5-Dinitro-naphthalene
a-Dinitro-naphthalene
NO 2
218
O 2 N
FORMATION. a-Nitro-naphthalene is nitrated, resulting in formation
of 1 : 5 and 1 ; 8-dinitro-naphthalenes in the proportion of about
DYES CLASSIFIED BY INTERMEDIATES
257
1 : 2. This crude product is washed with water and dried, and
then extracted first with carbon disulfide to remove nitro-naph-
thalene, and second with acetone to remove the 1 : 8 isomer,
leaving behind the 1 : 5 isomer. (See 1 : 8-dinitro-naphthalene)
LITERATURE. Cain, Intermediate Products (2d Ed.), 170
Lange, Zwischenprodukte, #2315
Dyes Derived from 1 : 5-Dinitro-naphthalene
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
745
Melanogene Blue
[S+NaaS]
s
ANTHRAQUINONE AND
ALLIED DYES
789
Anthracene
I '14: 107,778
[Oxidation]
M
Blue WR
I '20: 103,913
M'20: ?
1 : 8-Dinitro-naphthalene
0-Dinitro-naphthalene
O 2 N N0 2
FORMATION. a-Nitro-naphthalene is nitrated, resulting in the formation
1 : 5 and 1 : 8-dinitro-naphthalenes in the proportion of about 1 : 2.
The nitration mass upon cooling deposits most of the 1 : 5-isomer,
and upon pouring this filtrate into water the 1 : 8-isomer is pre-
cipitated, which can be purified by crystallization from benzene.
(See 1 : 5-dinitro-benzene)
LITERATURE. Cain, Intermediate Products (2d Ed.), 170
Lange, Zwischenprodukte, #2315
258 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 1 : 8-Dinitro-naphthalene
Schidtz
Numbei
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermedic tes
Used and Notes
Dye
Appli-
cation
Class
740
SULFUR DYES
Fast Black B
[NasS]
S
741
Fast Black BS
[NaaS; Alkalies]
or
[Fast Black B; Alkalies;
S
742
Printing Blue for
Wool
[Na2S,NaHS0 3 ,NaOH]
S
743
Kryogene Brown A
[Na2S,NaHS0 3 ,NaOH
S+NaaS]
S
750
Kryogene Brown A, G
I '14: 10,313
[NaHS0 8 ; S+NaaS]
S
a-Dinitro-naphthalene
See, 1 : 5-Dinitro-naphthalene
0-Dinitro-naphthalene
See, 1 : 8-Dinitro-naphthalene
7-Dinitro-naphthalene
1 : 3-Dinitro-naphthalene (not considered herein)
5-Dinitro-naphthalene
1 : 6-Dinitro-naphthalene (not considered herein)
2: 4-Dinitro-phenol
OH
L> W2 f^ TT T\T f\ ~t Q A
OeiluN 2^5 Io4
NO 2
STATISTICS. Manufactured '20: ?
DYES CLASSIFIED BY INTERMEDIATES
259
FORMATION. From chloro-dinitro-benzene by boiling with sodium
carbonate solution
LITERATURE. Cain, Intermediate Products (2d Ed.), 113
Lange, Zwischenprodukte, #577, 1121
Dyes Derived from 2:4-Dinitro-phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYES
720
Sulfur Black
I '14:
[S+NaaS]
S
4,923,981 (?)
M'17:
9,298,631
M'18:
12,385,130
M'19:
14,504,770
I '20: 662
M'20:
16,305,037
721
Sulfur Black
[p-Amino-phenol-
S
Thio Cotton Black
sulfonic Acid]
[S+Na*S]
722
Auronal Black
I '14: 50,879
[S+Na 2 Sl
3
723
Autogene Black EEB
[S+NaaS]
S
N-(2: 4-Dinitro-phenyl)-metanilic Acid (C. A. women.)
See, 2: 4-Dinitro-diphenylamine-3'-sulfonic Acid
N-(2: 4-Dmitro-phenyl)-^henylene-diamine (C. A. women.)
See 4 / -Amino-2: 4-dinitro-diphenylamine
N-(2: 4-Dinitro-phenyl)-sulfanilic Acid (C. A. women.)
See 2: 4-Dinitro-diphenylamine-4 / -sulfonic Acid
260 DYES CLASSIFIED BY INTERMEDIATES
Dinitro-stilbene-disulfonic Acid
4: 4'-Dinitro-stilbene-2 : 2'-disulfonic Acid (C. A. nomen.)
S0 3 H H0 3 S
2 N/~\ CH : CH
= Ci4H 10 N 2 OioS 2 = 430
STATISTICS. Manufactured '19:
FORMATION. p-Nitro-toluene-sulfonic acid is dissolved in weak caustic
soda solution and oxidized with sodium hypochlorite solution. If
the product contains dinitro-dibenzyl-disulfonic acid, it is again
oxidized with sodium hypochlorite in caustic soda solution.
LITERATURE. Cain, Intermediate Products (2d Ed.), 39
Lange, Zwischenprodukte, #1453
Dyes Derived from Dinitro-stilbene-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Othei Intermediates
Used and Notes
Dye
Appli-
cation
Class
10
STILBENE DYES
Mikado Yellow
Stilbene Yellow
I '14: 85,795
M'18: ?
M'20: ?
Dinitro-stilbene-disul-
fonic Acid (2 mols)
D
11
Mikado Orange
Chloramine
Orange G
I '14: 26,010
M'17: ?
M'18: ?
M'19: ?
M'20: 38,287
Dinitro-stilbene-disul-
fonic Acid (2 mols)
[Reduction]
D
12
Diphenyl
Citronine G
Aniline (2 mols)
D
13
Polychromine B
Diphenyl Orange RR
I '14: 16,113
M'18: ?
p-Phenylene-diamine
(2 mols)
D
18
Diphenyl Fast
YeUow
I '14: 10,229
I '20: 1,102
Dehydrothio-toluidine-
sulf onic Acid (2 mols)
or Primuline-sulfonic
Acid (2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES 261
2: 4-Dinitro-foluene (C. A. nomen.)
w-Dinitro-toluene
CH 3
STATISTICS. Imported '14 : 547,701
Manufactured '18: ?
Manufactured 7 19: 746,266
Manufactured '20: 1,847,191
FORMATION. From toluene by nitration with mixed acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 34
Lange, Zwischenprodukte, #789
USES. For manufacture of w-tolylene-diamine
Diphenylamine
NH /" =CiuN = 169
STATISTICS. Imported '14: 81,137
Manufactured '17: ?
Manufactured ' 18 : ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. By heating aniline and aniline hydrochloride together
in an autoclave, provided with a replaceable acid-proof enamelled
lining
LITERATURE. Cain, Intermediate Products (2d Ed.), 72
Lange, Zwischenprodukte, #1598-1600
262
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Diphenylamine
SckuUz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediated
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
134
Metanil Yellow
I '14: 284,606
M'17: ?
Metanilic Acid
A
M'18: ?
M'19: 477,143
I '20: 8,456
M '20: 629,437
135
Metanil Yellow,
Brominated
Metanilic Acid
[Bromination]
A
136
Acid Yellow
Metanilic Acid
A
MGS, GG
[Sulfonation]
139
Orange IV
I '14: 19,020
M'19: ?
Sulfanilic Acid
A
I '20: 608
140
Azoflavine RS
Curcumeine
I '14: 39,869
I '20: 5,225
Sulfanilic Acid
[Nitration]
A
141
Azo Yellow 3G
I '14: 114,689
M'17: ?
M'18: ?
Sulfanilic Acid
[Nitration]
A
M'19: ?
I '20: 4,818
M'20: ?
142
Brilliant Yellow S
Curcuniine
I '14: 9,934
Sulfanilic Acid
[Sulfonation]
A
150
Fast Yellow N
p-Toluidine-o-sulfonic
Acid
A
203
Yellow Fast To Soap
m-Amino-benzoic Acid
M
Diphenylamine-sulfonic Acid
Anilino-6enzene-sulfonic Acid (C. A. nomen.)
H0 3 S
NH
DYES CLASSIFIED BY INTERMEDIATES
263
FORMATION. By sulfonation of diphenylamine, and purification from
the disulfonate formed simultaneously
LITERATURE. Schultz, Die Chemie des Steinkohlentheers (3 aufl.), 1,
181
Lange, Zwischenprodukte, #1615-1617
Dyes Derived from Diphenylamine-sulfonic Acid
Schuliz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
538
Methyl Blue
I '14: 50,255
Diphenylamine-sulfonic
B
Cotton Blue
Acid (3 mols)
Diphenylene-imide
See, Carbazole
Diphenyl-methyl-amine
See, N-Methyl-diphenylamine (C. A. nomen.)
Diphenyl-naphthyl-methane
1-Naphthyl-diphenyl-raethane (C. A. nomen.)
(~^ TT on/i
v/"23JLli8 ^lr
FORMATION. From benzo-hydrol by heating with naphthalene and
P 2 5 at 140-145 for some hours
LITERATURE. A. Lehne, Ueber die Condensation von Benzhydrol und
Naphthalin, Ber, 13, 358 (1880)
Richter, Lex. d. Kohlenstoff Verbindungen, 4193
264
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Diphenyl-naphthyl-methane
Schultz
Number
jor Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
ca.ion
Class
DIPHENYL-NAPHTHYL-
METHANE DYE
565
Acid Blue B
I '14: 180,423
[Sulfonation]
A
Wool Blue G
I '20: 1,852
M'20: ?
N: W'-Diphenyl-m-^henylene-diamine (C. A. nomen.)
s-Dipheny 1-m-phenylene-diamin e
HN /N NH
FORMATION. From resorcinol and aniline by heating together in presence
of calcium chloride and a little zinc chloride at 210
LITERATURE. Green, Organic Coloring Matters (1908), 37
Cf. Schultz, Farbstofftabellen, #689
Dyes Derived from N: #'-Diphenyl-m-phenylene-diamine
Schultz
Number
Jor Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
267
DISAZO DYES
Phenylene Black
l-Naphthylamine-4: 7-
disulfonic Acid
a-Naphthylamine
A
267
Anthracite Black
I '14: 99
M'17: ?
I '20: 220
Freund's Acid
a-Naphthylamine
A
689
AZINE DYE
Indazine M
Nitroso-dimethylaniline
(1 and 2 mols)
B
DYES CLASSIFIED BY INTERMEDIATES
Diphenyl-thiourea
See, Thio-carbanilide (C. A. nomen.)
Disulfo Acid C
2-Naphthylamine-4: 8-disulfonic Acid (not con&idered herein)
Disulfo Acid E
See, l-Naphthol-3: 8-disulfonic Acid
Disulfo Acid F
2-Naphthylamine-3: 7-disulfonic Acid (not considered herein)
Disulfo Acid S
See, l-Naphthylamine-4: 8-disulfonic Acid
265
N: #'-(/> :/>'-Ditolyl)-2: 7-naphthylene-diamine
H
= C 24 H 22 N 2 = 338
FORMATION. By heating 2: 7-dihydroxy-naphthalene with p-toluidine
and p-toluidine hydrochloride
LITERATURE. Green, Organic Coloring Matters (1908), 38
Lange, Zwischenprodukte, #2886
Dye Derived from N:N'-(p:p'-"Ditolyi)-2: 7-naphthylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
677
Basle Blue R
Nitroso-dimethyl-
B
aniline
266 DYES CLASSIFIED BY INTERMEDIATES
N: N'-(o: o'-Ditolyl)-m-phenylene-diamine (C. A. nomen.)
Di-0-tolyl-w-phenylene-diamine
CH 3 H 3 C
HN /N NH
FORMATION. Presumably by heating resorcinol with o-toluidine in
presence of condensing agent. Cf. Di-p-tolyl-w-phenylene-diamine
LITERATURE. Ullmann, Enzy. tech. Chemie, 9, 63
Dye Derived from #: AT-(o:o'-Ditolyl)-m-phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
691
AZINE DYE
Metaphenylene
BlueB
I '14: 50
Nitroso-dimethyl-
aniline
B
N: W'-(:'-Ditolyl)-m-phenylene-diamine (C. A. nomen.)
Di-p-tolyl-w-phenylene-diamine
NH
FORMATION. From resorcinol, p-toluidine, and p-toluidine hydro-
chloride by heating together in presence of calcium chloride and a
little zinc chloride
LITERATURE. Ullmann, Enzy. tech. Chemie, 9, 63
Green, Organic Coloring Matters (1908), 37
DYES CLASSIFIED BY INTERMEDIATES 267
Dye Derived from W: W'-(^:^'-Ditolyl)-m-phenylene-diamine
Schultz
Number
jor Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cc lion
Class
AZINE DYE
690
Diphene Blue R
I '20: 3,124
Dimethyl-p-phenylene-
B
Metaphenylene
diamine
BlueR
D S
DT
See, Diamino-stilbene-disulfonic Acid
See, Dehydro-thio-p-toluidine-sulfonic Acid
Ebert and Merz a Acid
See, Naphthalene-2: 7-disulfonic Acid
Ebert and Merz Acid
Naphthalene-2: 6-disulfonic Acid (not considered here)
Epsilon Acid
See, l-Naphthol-3: 8-disulfonic Acid
See, l-Naphthylamine-3 : 8-disulfonic Acid
and 1 : 8-Dihydroxy-naphthalene-3-sulfonic Acid (not con-
sidered herein)
Erdmann's M Acid
See, l-Naphthylamine-6-sulfonic Acid
Ethoxy-benzidine
Di-p-aminoethoxy-diphenyl
2-Ethoxy-6enzidine (C. A. nomen. NH 2 =1)
H 6 C 2
"~ = Cl4Hl6N2 = 228
268
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Aniline is diazotized and coupled with phenol-p-sulfonic
acid and the product ethylated with ethyl bromide, thus forming,
benzene-azo-phenetole-sulfonic acid. This is then reduced in an
aqueous solution with zinc dust and caustic soda followed by
acidification with hydrochloric acid, resulting in preparation of
ethoxy-benzidine-sulfonic acid which is heated in an autoclave with
water (at 170) to split out the sulfonic acid group
LITERATURE. Weinberg, Ber. 20, 3171
Lange, Zwischenprodukte, #1224, 1249
Heumann, Anilinfarben 4, 380
Dyes Derived from Ethoxy-benzidine
Schulti
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
401
DISAZO DYES
Diamine Blue 3R
Nevile-Winther's Acid
(2 mols)
D
402
Diamine Blue Black
E
2-Naphthol-3:7-disul-
fonic Acid
Gamma Acid
D
403
Diamine Black BO
Gamma Acid (2 mols)
D
404
Diamine Yellow N
M'17: ?
I '20: 313
Salicylic Acid
Phenol
[Ethylation]
D
5-Ethoxy-2-hydroxy-fhionaphthene-l-carboxylic Acid (C. A.
nomen.)
6-Ethoxy-3-hydroxy-l-thionaphthene-2-carboxylic Acid (German
numbering)
c.COOH or
c * H *f [ CH.COOH
\/V
l^
DYES CLASSIFIED BY INTERMEDIATES
269
FORMATION. 5-Hydroxy-o-toluidine (amino-p-cresol) is acetylated to
protect the amino group, and then ethylated with diethyl-sulfate
for example. The resulting 2-acetamido-4-ethoxy-toluene is
oxidized with potassium permanganate to 2-acetamido-4-ethoxy-
benzoic acid. The acetyl group is split off by boiling with caustic
soda, acid added, and the amino group diazotized with sodium
nitrite, and reacted with potassium xanthate. This xanthate
compound, upon being treated with sodium chloro-acetate and
caustic soda, yields 5-ethoxy-phenyl-thioglycol-o-carboxylic acid.
This latter heated with caustic soda condenses to 5-ethoxy-2-
hydroxy-thionaphthene-1-carboxylic acid. The successive reaction
steps are as follows:
HO/NNH . COCH,
C 2 H 5 Or / \NH . COCH 3 " C.HsOf^NH . COCH,
CH 3 I JCOOH
. CzaOi/Ns . CS . OC 2 H 5 _^ (XH*0/Ns . CH 2 . COOH
tycoon l^ycooH
* C2H5 | / | ^CH . COOH
\/\co/
LITERATURE. Lange, Zwischenprodukte, #2167, 2168
Georgievics and Grandmougin, Dye Chemistry, 437
Dyes Derived from 5-Ethoxy-2-hydroxy-thionaphthene-l-carboxylic
Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used rind Notes
Dye
Appli-
cation
Class
913
INDIGO GROUP DYES
Helindone Orange R
I '14: 14,511
I '20: 3,155
5-Ethoxy-2-h y d r o x y-
thionaphthene-1-car-
boxylic Acid (2 mols)
V
915
Helindone Fast
Scarlet R
I '14: 4,302
I '20: 3,748
5-Ethoxy-2-h y d r o x y-
thionaphthene- 1 -car-
boxylic Acid (2 mols)
r [Bromination]
V
270 DYES CLASSIFIED BY INTERMEDIATES
3-Ethoxy-4'-methyl-diphenylamine (C. A. nomen.)
3-Ethoxy-phenyl-4'-toly 1-amine
C 2 H 5
^Ci 5 H 17 NO = 227
FORMATION. 100 parts of w-hydroxy-phenyl-p-tolyl-amine, 20.5 parts
of caustic soda solution (40 ?), 200 parts of alcohol, and 75 parts of
ethyl chloride are heated together in an autoclave at 110-120 for
7-8 hours
LITERATURE. Lange, Zwischenprodukte, #1624, 1625
Dye Derived from 3-Ethoxy-4'-methyl-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Impoit and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
548
Acid Violet 6BN
I '14: 6,861
Ketone
A
I '20: 5,582
[Sulfonation]
2-Ethoxy-l-naphthylamine (C. A. nomen.)
See, l-Amino-2-naphthol Ethyl Ether
3-Ethylamino-4-methyl-diphenylamine
See, ^-Ethyl-^-phenyW-m-tolylene-diamine
7-Ethylamino-2-naphthalene-sulfonic Acid (C. A. nomen.)
See, Ethyl-2-naphthylamine-7-sulfonic Acid
2-Ethylamino-8-naphthol-6-sulfonic Acid
See, Ethyl-gamma Acid
7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
See, Ethyl-gamma Acid
DYES CLASSIFIED BY INTERMEDIATES 271
Ethyl-amino-naphthol-sulfonic Acid y
See, Ethyl-gamma Acid
m-Ethylamino-phenol (C. A. nomen.)
Ethyl-w-amino-phenol
OH
INH . c 2 H 5
FORMATION. Ethyl-aniline is sulfonated with 23 per cent oleum, the
sodium ethyl-aniline-m-sulfonate isolated and fused with caustic
potash for ten hours at 200-220
LITERATURE. Cain, Intermediate Products (2d Ed.), 120
Lange, Zwischenprodukte, #593-595
Dyes Derived from m-Ethylamino-phenol
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import a'nd
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
571
Rhodamine 6G
I '14: 37,515
I '20: 8,574
m-Ethylamino-phenol
(2 mols)
Phthalic anhydride
[Ethyl esterificationj
B
577
Rhodine 2G
Dimethylamino - hy-
droxy - benzoyl - ben-
zoic Acid
B
[Ethyl esterification]
//-Ethyl-aniline (C. A. nomen.)
Ethyl-aniline
NH . C 2 H 5
272 DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: 195,161
Manufactured '20: ?
FORMATION. By heating aniline hydrochloride and ethyl alcohol
together in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 67
Lange, Zwischenprodukte, #93
USES. For preparation of ethyl-methyl-aniline and benzyl-ethyl-
aniline
a-(#-ethyl-anilino)-j!>-toluene-sulfonic Acid (C. A. nomen.)
See, Ethyl-sulfobenzyl-aniline
Ethyl-benzyl-aniline
See, Benzyl-ethyl-aniline
Ethyl-benzyl-aniline-sulfonic Acid
See, Ethyl-sulfobenzyl-aniline
2: 2 / -Ethylene-bis (5-nitro-&enzene-sulfonic Acid) (C. A. nomen.)
See, Dinitro-dibenzyl-disulfonic Acid
Ethyl-F Acid
See, Ethyl-2-naphthylamine-7-sulfonic Acid
Ethyl-gamma Acid
2-Ethylamino-8-naphthol-6-sulfonic Acid
Ethylamino-naphthol-sulfonic Acid 7
7-Ethylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
IHO
/X ,NH.C 2 H 5
H0 3 Sl
DYES CLASSIFIED BY INTERMEDIATES
273
FORMATION. G acid (2-naphthol-6 : 8-disulfonic acid) is heated with
ethylamine in an autoclave at about 200. The ethylamino-G acid
thus obtained is fused with caustic soda at 210-220, and the ethyl-
gamma acid isolated
LITERATURE. Lange, Zwischenprodukte, #2550
Dye Derived from Ethyl-gamma Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
334
Diphenyl Blue Black
I '14: 26,240
HAcid
D
Benzidine
6-Ethylmercapto-2-hydroxy-rhionaphthene-l-carboxylic Acid (C
A. nomen.)
5-Ethylthio-2-hydroxy-thionaphthene-l-carboxylic Acid
6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-
man numbering)
C 2 H 5 S
C.COOH or
C 2 H 5 S
S
CH.COOH
CO/
FORMATION. 4-Acetamido-anthranilic acid is diazotized and treated
with potassium xanthate. This xanthate compound is reacted
with chloro-acetic acid and then hydrolyzed to split the acetyl
group from the 4-amino radical. This amino group is now diazo-
tized and reacted with potassium xanthate. This second xanthate
compound is treated with ethyl-sulfate, resulting in the formation of
5-ethylmercapto-phenyl-thioglycol-o-carboxylic acid. This latter,
upon being heated with caustic soda, condenses to 5-ethylmercapto-
274
DYES CLASSIFIED BY INTERMEDIATES
2-hydroxy-thionaphthene-l-carboxylic acid. The successive re-
action steps are as follows:
CH 3 CO .
CH 3 CO .
C 2 H 6 . SC .
CH 3 CO . HNs . CS . OC 2 H 5
. CH 2 . COOH
. CH 2 . COOH
. CH 2 . COOH _ C 2 H 5 S s . CH 2 . COOH
"sJCOOH
V
cH .
COOH
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 436-437
Lange, Zwischenprodukte, #2175
Dye Derived from 5-Ethylmercapto-2-hydroxy-thionaphthene-l-
carboxylic Acid
SchuLtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
sed and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
916
Helindone Scarlet S
I '14: 5,515
I '20: 56
5-Ethylmercapto-2-hy-
droxy-thionaphthene
1-carboxylic Acid (2
mols)
JV-Ethyl-W-methyl-anUine (C. A. nomen.)
Ethyl-methyl-aniline
Methyl-ethyl-aniline
FORMATION. From ethyl-aniline by methylation, or from methyl-
aniline by ethylation
LITERATURE. Beil. II, 334
DYES CLASSIFIED BY INTERMEDIATES
275
Dye Derived from Ethyl-methyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufactwe
Other Intermediates
Used and Notes
Dye
Appli-
cation
Gloss
THIAZINE DYE
661
Thionine Blue GO
1 '14: 18,618
Dimethyl-p-phenylene-
B
I '20: 2,030
diamine - thiosulf onic
Acid
[Oxidation, etc.]
or
Nitroso-dimethyl-
aniline
[Reduction, Oxidation,
NaaSaOs, etc.]
or
Dimethyl-p-phenylene-
diamine
[Naa&Os, Oxidation,
etc.]
or
Dimethyl-aniline
[Na2S20 3 , etc.]
Ethyl-a-naphthylamine
JV-Ethyl-1-naphthylamine (C. A. nomen.)
NH .
STATISTICS. Imported '14: 1,102 Ibs.
FORMATION. By treating a-naphthylamine with ethyl bromide
LITERATURE. Limpricht, Ann. 99, 117 (1856)
Friedlaender and Welmans, Ber. 21, 3124 (1888)
Bamberger and Helwig, Ber. 22, 1315 (1889)
Thorpe, Die. Chemistry, 3, 587
276 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Ethyl-a-naphthyl-amine
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
sed and Notes
Dye
Appli-
cation
Class
186
MONOAZO DYE
Lanacyl Violet B
1 '14: 3,628
M'17: ?
M'18: ?
HAcid
A
DlPHENYL-NAPHTHYL-
558
METHANE-DYE
Victoria Blue R
I '14: 4171
I '20: 97
Hydrol or Ketone
B
Ethyl-2-naphthylamine-7-sulfonic Acid
Ethyl-F Acid
Ethyl-j8-naphthylamine-5-sulfonic Acid
7-Ethylamino-2-naphthalene-sulfonic Acid (C. A. nomen.)
H0 3 S
NH . C 2 H 5
C 12 H 13 N0 3 S =
FORMATION. By ethylation of 2-naphthylamine-7-sulfonic acid by
means of an ethyl halide or sodium ethyl sulfate, in an autoclave
at 100-110 C. for several hours
LITERATURE. Lange, Zwischenprodukte, #2385
Dyes Derived from Ethyl-2-naphthylamine-7-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
231
DISAZO DYES
Cloth Red 3B
Extra
I '14: 15
I '20: 84
o-Amino-azo-toluene
M
371
Roseazurine G
Tolidine
2-Naphthylamine-7-
sulfonic Acid
D
372
Rosazurine B
Tolidine
Ethyl-2-naphthyl-
amine-7-sulf onic Acid
(2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES
277
Ethyl-0-naphthylamine-d-sulfonic Acid
See, Ethyl-2-naphthylamine-7-sulfonic Acid
#-Ethyl-/>-nitroso-aniline (C. A. nomen.)
See, p-Nitroso-ethyl-aniline
W-Ethyl-4-nitroso-o-*oluidine (C. A. nomen. NHR =1)
See, Nitroso-ethyl-o-toluidine
W-Ethyl-W-phenyl-fcenzylamine (C. A. nomen.)
See, Benzyl-ethyl-aniline
Ethyl-phenyl-hydrazine
a-Ethyl-a-phenyl-Aydrazine (C. A. nomen.)
N.NH 2 =C 8 Hi 2 N 2 =:136
FORMATION. Phenyl-hydrazine is treated with metallic sodium to
form the sodium compound, from which by means of ethyl iodide
the ethyl-phenyl-hydrazine is prepared
LITERATURE. Thorpe, Die. Chemistry, 3, 53
Dye Derived from Ethyl-phenyl-hydrazine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Othei Intermediates
Used and Notes
Dye
Appfa
cation
Class
MONOAZO DYE
130
Chromazone Blue R
p-Amino-benzaldehyde
Chromotropic Acid
M
^-Ethyl-^-phenyl-l-m-^olylene-diamine (NH 2 ,=1,C. A. nomen.)
Phenyl-p-amino-ethyl-o-toluidine (CH 3 =1)
3-Ethylamino-4-methyl-diphenylamine
NH
278
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. A^-PhenyW-w-tolylene-diamine (q.v.) is heated for ten
hours with ethyl bromide at 150-175
LITERATURE. Ger. Pat. 87,667, Frdl. IV, 85
Beilstein, Organische Chemie (3 auf.), IV spl. 400
Lange, Zwischenprodukte, #1750, 1755, referring to the
same patent, gives a different formula
Dye Derived from ^-Ethyl-^-phenyl-l-m-tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
sed and Notes
Dye
Appli-
cation
Class
AZINE DYE
684
Brilliant Rhoduline
Nitroso-ethyl-o-
B
Red
toluidine
Ethyl-sulfobenzyl-aniline
Benzyl-ethyl-aniline-sulfonic Acid
Ethyl-benzyl-aniline-sulfonic Acid
a-(AT-Ethyl-anilino)-p-foluene-sulfonic Acid (C. A. nomen.)
C 2 H 5 . N .
= Ci 5 Hi 7 NO 3 S 291
STATISTICS. Manufactured 1919 and 1920, but in undisclosed quantities
FORMATION. By sulfonation of benz>l-ethyl-aniline with 20 per cent
oleum at 40-50
LITERATURE. Cain, Intermediate Products (2d Ed.), 69
Cf. Lange, Zwischenprodukte, #1500
DYES CLASSIFIED BY INTERMEDIATES
279
Dyes Derived from Ethyl-sulfobenzyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
50
MONOAZO DYE
Azo Cardinal G
M'14: ?
p-Nitro-aniline
A
502
TRIPHENYL-METHANE
DYES
Guinea Green
Acid Green 2BG
I '14: 49,971
M'17: ?
M'18: ?
M'19: ?
I '20: 278
M'20: ?
Ethyl-sulfobenzyl-
aniline (2 mols)
Benzaldehyde
[Oxidation]
A
503
Night Green A
Neptune Green
Brilliant Milling
Green B
I '14: 40,868
M'19: ?
I '20: 10,940
M'20: ?
Ethyl-sulfobenzyl-
aniline (2 mols)
o-Chloro-benzaldehyde
[Oxidation]
A
506
Erioglaucine
I '14: 66,526
M'19: ?
I '20: 6,160
M'20: ?
Ethyl-sulfobenzyl-
aniline (2 mols)
Benzaldehyde-o-
sulfonic Acid
[Oxidation]
A
529
Acid Violet 6B
Ethyl-sulfobenzyl-
aniline (2 mols)
Dimethyl-p-amino-
benzaldehyde
[Oxidation]
A
530
Acid Violet 6B
Formyl Violet
Guinea Violet
I '14: 161,624
M'17: ?
M'18: ?
M '19: ?
I '20: 3,925
M'20: 144,207
Diethyl-aniline
Ethyl-sulfobenzyl-
aniline (2 mols)
[Oxidation]
A
662
THIAZINE DYE
Thiocarmine R
I '14: 1,399
Ethyl-sulfobenzyl-p-
phenylene-diamine
[Nas&Os, etc.]
A
280
DYES CLASSIFIED BY INTERMEDIATES
#-Ethyl-W-(p-sulfo-benzyl)-metanilic Acid (C. A. nomen.)
See, Benzyl-ethyl-aniline-disulfonic Acid
Ethyl-sulfobenzyl-/)-phenylene-diamine
Benzyl-ethyl-p-phenylene-diamine-sulfonic Acid
p-Amino-benzyl-ethyl-aniline-sulfonic Acid
a-(p-Amino-Af-ethyl-anilino)-p-foluene-sulfonic Acid (C. A.
nomen.)
C 2 H 5 N CH
= 306
NH 2
FORMATION. Benzyl-ethyl-aniline-sulfonic acid is changed into the
nitroso-derivative with nitrous acid, and this latter is reduced with
sulfite
LITERATURE. Lange, Zwischenprodukte, #1499, 929
Cf. Cain, Intermediate Products (2d Ed.), 69
Dye Derived from Ethyl-sulfobenzyl-^-phenylene-diamine
SchuLtz
Number
Jor Dye
Ordinal y Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
THIAZINE DYE
662
Thocarmine R
I '14: 1,399
Ethyl-sulfobenzyl-
A
aniline
[NasSaOs, etc.]
Ethyl-sulfobenzyl-^-phenylene-diamine-thiosulfonic Acid
a-(4-Amino-JV-ethyl-3-sulf omercapto-anilino)-p-Zo 1 u e n e - s ul f o n i c
Acid (C. A. nomen.)
C 2 H 5 N CH 2
s.so 3 H
NH 2
= Ci 5 Hi 8 N 2 6 S 3 =
DYES CLASSIFIED BY INTERMEDIATES
281
FORMATION. Ethyl-sulfobenzyl-p-phenylene-diamine is dissolved in
dilute hydrochloric acid, zinc chloride solution and sodium thio-
sulfate solution added; and then oxidized quickly with solution of
sodium bichromate
LITERATURE. Lange, Zwischenprodukte, #1501
Dye Derived from Ethyl-sulfobenzyl-^-phenylene-diamine-thiosulfonic
Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
THIAZINE DYE
667
Brilliant Alizarin
I '14: 19,481
1 : 2-Naphthoquinone
M
Blue
M'19: ?
Indochromine T
I '20: 3,214
M'20: ?
6-Ethylthio-2-hydroxy-thionaphthene-l-carboxylic Acid
See, 5-Ethylmercapto-2-hydroxy-thionaphthene-l-carboxylic
Acid (C. A. nomen.)
6-Ethylthio-3-hydroxy-l-thionaphthene-2-carboxylic Acid (Ger-
man numbering)
See, 5-Ethylmercapto-2-hydroxy-thionaphthene-l-carboxylic
Acid (C. A. nomen.)
W-Ethyl-o-foluidine (C. A. nomen.)
Ethy 1-o-toluidine
HNC 2 H 5
QCH, =
FORMATION. From o-toluidine hydrochloride and ethyl alcohol by
heating together in an autoclave at about 200. The crude product
contains considerable o-toluidine, which can be removed as sulfate
by adding just sufficient sulfuric acid to' combine with it, allowing
to cool, and centrifugating
LITERATURE. Cain, Intermediate Products (2d Ed.), 71
Lange, Zwischenprodukte, #128
282 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from W-Ethyl-o-toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermedictes
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
500
Setocyanine
I '14: 923
Ethyl-o-toluidine
B
I '20: 1,102
(2 mols)
o-Chloro-benzaldehyde
[Oxidation]
546
Cyanol
I '14: 40,015
Ethyl-o-toluidine
A
I '20: 7,954
(2 mols)
m-Hydroxy-benzalde-
hyde
[Sulfonation, Oxidation]
THIAZINE DYE
x
663
New Methylene Blue
I '14: 30,392
Ethyl-o-toluidine
B
N
I '20: 513
(2 mols)
[Nitroso-derivative,
NasSaOs, etc.]
or
p-Amino-ethyl-o-
toluidine
[NaaSaOs, etc.]
#-Ethyl-p-foluidine (C. A. nomen.)
Ethyl-p-toluidine
HNC 2 H 5
FORMATION. From p-toluidine hydrochloride and ethyl alcohol by
heating together in an autoclave and purification of resulting
product
LITERATURE. Cf. Cain, Intermediate Products (2d Ed.), 71
Lange, Zwischenprodukte, #128
Ger. Pat. 21,241, Frdl. 1, 21
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from W-Ethyl-/>-toluidine
283
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufactw e
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
671
AZINE DYE
Induline Scarlet
I '14: 198
I '20: 154
a-Naphthylamine
AP-Ethyl-4-m-folylene-diamine (C. A. nomen. NH 2 =1)
p-Amino-ethyl-o-toluidine (CH S =1)
NH 2
INH.CA
CH 3
FORMATION. From 5-nitro-ethyl-o-toluidine (NH 2 = 1) [4-nitro-ethyl-o-
toluidine (CH 3 = 1)] by reduction with zinc dust and hydro-
chloric acid
LITERATURE. Beilstein, Organische Chemie (3 auf,) ; IV, 601
J. Chem. Soc., 67, 247
Dye Derived from // 3 -Ethyl-4-m-tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manujactu. e
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
684
Brilliant Rhoduline
Methyl-o-toluidine
B
Red
Aniline
^-Ethyl-^-tolylene-diamine (C. A. nomen.)
p-Amino-ethyl-o-toluidine
NH.C 2 H 5
C 9 Hi 4 N 2 150
NH 2
284
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. From 4-nitroso-ethyl-o-toluidine (NHR= 1) by reduction
with SnCl 2 +HCl
LITERATURE. -Beil. II, 609
Dye Derived from W-Ethyl-^-tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
663
THIAZINE DYE
New Methylene Blue
N
I '14: 30,392
I '20: 513
Ethyl-o-toluidine
[Nas&Os]
B
Ewer and Pick's Acid
See, Naphthalene- 1 : 6-disulfonic Acid
F Acid 1
See, 2-Naphthol-7-sulfonic Acid
See, 2-Naphthylamine-7-sulfonic Acid
2-Naphthylamine-3 : 7-disulf onic Acid (not considered herein)
2-Amino-7-naphthol-3-sulfonic Acid (not considered herein)
2: 7-Dihydroxy-naphthalene-3-sulfonic Acid (not considered herein)
Formaniline
See, Anhydro-formaldehyde-aniline
4-Formyl-m-&enzene-disulfonic Acid (C. A. nomen.)
See, Benzaldehyde-disulfonic Acid
o-Formyl-fcenzene-sulfonic Acid (C. A. nomen.)
See, Benzaldehyde-o-sulfonic Acid
4-Formyl-6-methyl-m-benzene-disulfonic Acid
See, 3-methyl-benzaldehyde-4: 6-disulfonic Acid
Forsling's Acid I
See, 2-Naphthylamine-8-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Forsling's Acid II
See, 2-Naphthylamine-5-sulfonic Acid
Freund's Acid
l-Naphthylamine-3 : 6-disulfonic Acid
4-Amino-2: 7-naphthalene-disulfonic Acid (C. A. nomen.)
a-Naphthylamine-a-disulfonic Acid
Alan's a Acid
NH 2
285
H0 3 S
S0 3 H
= Ci H 9 NO 6 S 2 =:303
STATISTICS. Imported '14: 5,246 Ibs.
Manufactured '18: ?
Manufactured '19: ?
FORMATION. Naphthalene is heated with five parts of concentrated
sulfuric acid for about 8 hours at 160-200, the mixture is cooled
and two parts of 50 per cent nitric add are added. After reacting
for some time the nitration mass is diluted and reduced with iron
LITERATURE. Cain, Intermediate Products (2d Ed.),
Thorpe, Die. Chemistry, 3, 592
Lange, Zwischenprodukte, #2591
Dyes Derived from Freund's Acid
195
Schultz
Numbei
Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermedictes
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
266
Naphthylamine
I '14: 152,141
a-Naphthylamine
A
Black D
M'17: ?
(2 mols)
M'18: 29,724
M'19: ?
I '20: 1,687
M'20: ?
267
Anthracite Black
I '14: 99
a-Naphthylamine
A
M'17: ?
Diphenyl-m-phenylene-
I '20: 220
diamine
286 DYES CLASSIFIED BY INTERMEDIATES
G Acid *
2-Naphthol-6 : 8-disulfonic Acid (C. A. nomen.)
/3-Naphthol-/3-disulfonic Acid
0-Naphthol-7-disulfonic Acid
/3-Naphthol-disulfonic Acid G
/3-Naphthol-disulfonic Acid 7
YAcid
H0 3 S
H0 3 S
OH
STATISTICS. Imported 14' : 11,624 Ibs.
Manufactured '18: ?
Manufactured '19: 732,192 Ibs.
Manufactured '20: 1,446,605 Ibs.
FORMATION. Sulfonation of /3-naphthol and separation from the R
acid simultaneously formed
LITERATURE. Cain, Intermediate Products (2d Ed.), 227
Thorpe, Die. Chemistry, 3, 627
Lange, Zwischenprodukte, #2659-2661
Dyes Derived from G Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
38
Orange G
I '14: 48,456
Aniline
A
M'17: ?
M'18: ?
M'19: ?
I '20: 100
M '20: 120,874
1 Occasionally in the old literature G acid is used to mean Gamma acid (or
2-Amino-8-naphthol-6-sulfonic acid), or 2-Naphthylamine-6: 8-disulfonic acid, or
1 : 7-Dihydroxy-naphthalene-3-sulf onic acid.
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from G Acid (continued)
287
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
113
Crystal Ponceau
I '14: 628
a-Naphthylamine
A
122
Erica G
I '14: 2,370
Dehydro-thio-w-xyli-
D
M'18: ?
dine
I '20: 1,142
169
Cochineal Red A
I '14: 32,645
Naphthionic Acid
A
M'17: ?
M'18: ?
M '19: 231,519
M '20: 288,945
DISAZO DYES
227
Brilliant Croceine M
I '14: 125,137
Amino-azo-benzene
A
M'17: ?
M'18: 84,643
M '19: 157,509
I '20: 49
M '20: 129,124
270
Brilliant Croceine 9B
Amino-G Acid
A
Aniline
RAcid
319
Diamine Scarlet B
I '14: 41,175
Benzidine
D
I '20: 10,565
Phenol
[Ethylation]
DlPHENYL-NAPHTHYL-
METHANE DYE
566
Wool Green S
I '14: 60,073
Hydrol
A
M'17: ?
M'19: ?
I '20: 127,764
M '20: 212,362
Gallamic Acid
See, Gallamide (C. A. nomen.)
Gallamide (C. A. nomen.)
Gallamic Acid
Gallic Acid Amide
288
DYES CLASSIFIED BY INTERMEDIATES
CO.NH 2
FORMATION. From tannin by boiling with strong solution of am-
monium sulfite and aqueous ammonia until the excess of ammonia
has been driven off. The amide crystallizes out upon cooling
LITERATURE. Green, Organic Coloring Matters (1908), 46
Lange, Zwischenprodukte, #1546
Dyes Derived from Gallamide
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
627
OXAZINE DYES
Modern Cyanine
Nitroso-dimethyl-aniline
Dimethyl-p-phenylene-
diamine
[Reduction]
M
630
Cyanazurine
Nitroso-dimethyl-aniline
Aniline
[Reduction]
M
637
Gallamine Blue
I '14: 2,756
I '20: 16,446
Nitroso-dimethyl-aniline
M
638
Amido Gallamine
Blue
Nitroso-dimethyl-aniline
[Ammonia, Reduction]
M
641
Coreine RR
Coelestine Blue B
I '14: 1,320
I '20: 44
N itroso-diethyl-aniline
or Diethylamino-azo-
benzene
M
646
Coreine AR
Nitroso-diethyl-aniline
or Diethylamino-azo-
benzene
Aniline
[Sulfonation]
or
[Coreine RR; Aniline;
Sulfonation]
M
DYES CLASSIFIED BY INTERMEDIATES
Gallanilic Acid
See, Gallanilide (C. A. nomen.)
Gallanilide (C. A. nomen.)
Gallanilic Acid
Gallic Acid Anilide
289
CO NH
4 245
H
STATISTICS. Manufactured '19: ?
. a Manufactured '20 : ?
FORMATION. From tannin by heating with aniline
LITERATURE. Green, Organic Coloring Matters (1908), 46
C/. Lange, Zwischenprodukte, #1546
Dye Derived from Gallanilide
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
639
Gallanilic Violet R, B
Ni tr oso-dimethy 1- (or
M
diethyl-) aniline
Gallic Acid
3:4: 5-Trihydroxy-benzoic Acid
COOH
STATISTICS. Imported '14: 61,644 Ibs.
Manufactured regularly, but in amounts that are not
yearly disclosed
290
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. From nut galls (Chinese or Aleppo) by action of ferments
or acids, and subsequent extraction and crystallization
LITERATURE. Green, Organic Coloring Matters (1908), 46
Lange, Zwischenprodukte, #1112
Dyes Derived from Gallic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
599
Galleine
I '14: 15,404
Phthalic Anhydride
M
M'19: ?
Gallic Acid (2 mols)
I '20: 5,075
M'20: ?
601
Coeruleine S
I '14: 3,404
Phthalic Anhydride
M
M'19: ?
Gallic Acid (2 mols)
I '20: 9,392
[Dehydration]
or
[Galleine dehydrated]
OXAZINE DYES
622
Delphine Blue B
M'17: ?
Nitroso-dimethylaniline
M
M'18: ?
Aniline
M'19: 43,827
[Sulfonation]
I '20: 29,643
or
M '20: 76,719
[Gallocyanine, Aniline,
Sulfonation]
624
Modern Violet N
I '20: 5,688
Nitroso-dimethylaniline
M
[C0 2 split off]
or
*
[Gallocyanine heated]
625
Chrome Heliotrope
Nitroso-methyl-aniline
M
[Reduction]
626
Gallocyanine
I '14: 78,253
Nitroso-dimethylaniline
M
M'17: ?
M '18: 435,460
M'19: 365,243
I '20: 12,414
M'20: 70,169
DYES CLASSIFIED BY INTERMEDIATES
291
Dyes Derived from Gallic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
(continued)
628
Gallocyanine MS .
I '20: 22
Dimethylamino-azo-
M
benzene-disulfonic
Acid
or
Nitroso-dimethyl-
aniline
[Sulfonation; Oxidation
629
Gallogreen DH
Nitroso-dimethyl-
M
Modern Blue
aniline
[Formaldehyde, Reduc-
tion]
or
[Gallocyanine, Formal-
dehyde, Reduction]
631
Chromocyanine V
M'18: ?
Nitroso-dimethyl-
M
M'19: ?
aniline
I '20: 1,287
[Sulfonation]
M'20: ?
or
[Gallocyanine, Sulfites]
632
Ultra Violet LGP
I '14: 4,368
Nitroso-dimethyl-
M
aniline (2 mols)
Gallic Acid (2 mols)
633
Indalizarine R
I '20: 551
Nitroso-dimethyl-
M
aniline
[Sulfonation]
634
Indalizarine Green
Nitroso-dimethyl-
M
aniline
[Sulfonation; Nitration]
or
[Indalizarine nitrated]
635
Blue 1900 TC
I '20: 1,933
Nitroso-dimethyl-
M
Modern Violet
aniline
[Reduction]
292 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gallic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
(continued)
642
Phenocyanine TC
I '20: 4,740
Nitroso-dimethyl-
M
aniline
Resorcinol
or
[Gallocyanine, Resorci-
nol]
643
Phenocyanine TV
M'17: ?
Nitroso-dimethyl-
M
I '20: 1,543
aniline
Resorcinol
[Sulfonation]
or
*
[Phenocyanine sulfo-
nated]
644
Ultracyanine B
Nitroso-dimethyl-
M
aniline
Resorcinol [Alkaline
Condensation]
or
[Gallocyanine; Resorci-
nol; Alkaline Con-
densation]
645
Gallazine A
Nitroso-dimethyl-
M
aniline
Schaeffer's Acid
[Oxidation]
or
[Gallocyanine,
Schaeffer's Acid
Oxidation]
THIAZINE DTE
664
Leuco-gallo
Dimethyl-p-phenylene-
M
Thionine DH
diamine-thiosulfonic
Acid
DYES CLASSIFIED BY INTERMEDIATES
293
Dyes Derived from Gallic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
*
ALLIED DYES
772
Galloflavine W
I '14: [838
Gallic Acid (2 mols)
M
I '20: 24
782
Anthracene Brown
I '14: 115,586
Benzoic Acid
M
Alizarin Brown
M'17: ?
or Phthalic Anhydride
M'18: ?
M'19: 40,426
I '20: 2,728
M'20: 42,840
Gallic Acid Amide
See, Gallamide (C. A. nomen.)
Gallic Acid Anilide
See, Gallanilide (C. A. nomen.)
Gallic Acid Methyl Ester
CO.OCHs
( JOH =
H
FORMATION. From gallic acid by heating with methanol (methyl
alcohol) and hydrochloric acid
LITERATURE. Green, Organic Coloring Matters (1908), 40
294 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gallic Acid Methyl Ester
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
636
Prune
I '14: 3,197
Nitroso-dimethyl-aniline
M
I '20: 4,418
640
Modern Azurine DH
Nitroso-dimethyl-aniline
M
Aniline
Gamma Acid
2-Amino-8-naphthol-6-sulfonic Acid
Amino-naphthol-sulfonic Acid 7
Amino-naphthol-sulfonic Acid G
G Acid (occasionally in old literature)
7-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
HO
HO a
H 3S
= CioH 9 N0 4 S == 239
STATISTICS. Manufactured '18: ?
Manufactured '19: 155,025 Ibs.
Manufactured '20: 418,456 Ibs.
FORMATION. /3-Naphthol is sulfonated to R and G acids, and these
two /3-naphthol-disulfonic acids are separated. The sodium salt
of G acid is heated in an autoclave with ammonia and sodium
bisulfite solution to form amino-G acid (2-naphthylamine-6: 8-
disulfonic acid). This latter is fused in an autoclave with caustic
soda, thus forming gamma acid.
LITERATURE. Cain, Intermediate Products (2d Ed.), 236
Lange, Zwischenprodukte, #2546
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gamma Acid
295
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
241
245
DISAZO DYES
Neutral Gray G
Nyanza Black B
I '14: 2,546
M'19: ?
I '20: 3,472
M'20: ?
Aniline
a-Naphthylamin
p-Nitro-aniline
a-Naphthylamine
[p-Nitro-aniline reduced
after coupling]
D
D
274
Diaminogene BB
I '14: 313,629
I '20: 18,120
Acetyl-1 : 4-naphthy-
lene-diamine-6-sul-
f onic Acid
a-Naphthylamin
D
295
Diphenyl Fast Black
I '14: 882
p: p'-Diamino-ditolyl-
amine
w-Tolylene-diamine
D
297
Benzo Fast
Pink 2BL
I '14: 3,252
I '20: 1,226
Diamino-diphenyl-urea-
disulfonic Acid
Gamma Acid (2 mols)
D
327
Diamine Violet N
I '14: 18,263
M'19: ?
M'20: 92,503
Benzidine
Gamma Acid (2 mols)
D
328
Diamine Black RO
Dianol Black RW
I '14: 8,253
Benzidine
Gamma Acid (2 mols)
D
329
Diamine Brown V
M'19: ?
Benzidine
w-Phenylene-diamine
D
330
Zambesi Brown G
I '14: 4,028
I '20: 1,104
Benzidine
2: 7-Naphthylene-dia-
mine-sulfonic Acid
D
331
Alkali Dark
Brown GV
Benzidine
Nitroso-/3-naphthol
D
332
Dianil Garnet B
Benzo Fast Red
I '14: 5,985
I '20: 3,799
Benzidine
Amino-R Acid
D
296
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Gamma Acid (continued)
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
333
Diamine Black BH
I '14: 619,430
Benzidine
D
Oxamine Black BHN
M'17: ?
HAcid
M'18: ?
M'19:-485,046
I '20: 5,512
M '20: 803,501
335
Naphthamine
I '14: 49,016
Benzidine
D
Black RE
KAcid
343
Diamine Fast Red F
I '14: 50,479
Benzidine
D
M'19: 56,864
Salicylic Acid
I '20: 4,040
M '20: 115,865
344
Diamine Brown M
I '14: 65,396
Benzidine
D
M'18: ?
Salicylic Acid
M'19: 15,959
M '20: 257,872
399
Indazurine TS
Tolidin
D
1 : 7-Dihydroxy-2-naph-
thoic-4-sulf onic Acid
402
Diamine Blue
Ethoxy-benzidine
D
Black E
2-Naphthol-3: 7-disul-
fonic Acid
403
Diamine Black BO
Ethoxy-benzidine
D
Gamma Acid (2 mols)
TRISAZO DYES
436
Columbia Black FF
I '14:--402,997
l-Naphthylamine-6-
D
M '18: ?
and 7-sulfonic Acids
M'19: ?
ra-Phenylene-diamine
I '20: 23,350
p-Phenylene-diamine
M'20: ?
437
Iso-Diphenyl
Resorcinol
D
Black R
p-Phenylene-diamine
w-Phenylene-diamine
DYES CLASSIFIED BY INTERMEDIATES
297
Dyes Derived from Gamma Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
440
TRISAZO DYES
(continued)
Direct Indigo
Blue BK
Benzidine
w-Amino-p-cresol
Methyl Ether
Gamma Acid (2 mols)
D
442
Direct Black V
I '14: 145,738
Benzidine
2R Acid
a-Naphthylamine
D
444
Cr.irnpsall Direct
Fast Brown B
Benzidine
Salicylic Acid
Aniline
D
461
Coomassie Union
Blacks
1 : 4-Naphthylene-dia-
mine-2-sulfonic Acid
w-Phenylene-(or Toly-
lene-) diamine or
Resorcinol (2 mols)
D
472
ChloramineBlueHW
Benzidine
2: 5-Dichloro-aniline
HAcid
D
473
491
Diamine Black HW
TETRAKISAZO DYE
Dianil Black PR
I '20: 342
Benzidine
p-Nitro-aniline
HAcid
Benzidine sulf onic Acid
Gamma Acid (2 mols)
w-Phenylene-diamine
(2 mols)
D
D
G R Acid
See, l-Naphthol-3: 6-disulfonic Acid
298 DYES CLASSIFIED BY INTERMEDIATES
H Acid
l-Amino-8-naphthol-3 : 6-disulf onic Acid
Amino-naphthol-disulfonic Acid H
8-Amino-l-naphthol-3 : 6-disulf onic Acid (C. A. nomen.)
HO NH 2
H0 3 S
S0 3 H
STATISTICS. Imported '14: 96,296 Ibs.
Manufactured '17: 3,089,273 Ibs.
Manufactured '18: 3,837,534 Ibs.
Manufactured ' 19: 2,883,228 Ibs.
Manufactured '20: 5,180,993 Ibs.
FORMATION. Naphthalene is trisulfonated with oleum, and then nitrated
and reduced with iron, resulting in the formation of Koch acid or
1-naphthy lamine-3 : 6 : 8-trisulf onic acid. This latter is now fused in
an autoclave with caustic soda, forming H acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 237
Lange, Zwischenprodukte, #2720-2724
Thorpe, Die. Chemistry, 3, 641
Dyes Derived from H Acid
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
41
MONOAZO DYES
Fast Acid
Fuchsine B
M'18: ?
M'19: 26,699
M'20: 30,678
Aniline
A
182
Fast Sulf on
Violet 5BS
Brilliant Sulf on
RedB
I '14: 4,871
I '20: 4,740
Aniline
Benzene- (or Toluene-)
sulfo chloride
A
186
Lanacyl Violet B
I '14: 3,628
M'17: ?
M'18: ?
Ethyl-a-naphthylamine
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
187
Lanacyi Blue BB
I '14: 4,200
5-Amino-l-naphthol
A
188
Tolyl Blue SR
I '14: 45,038
Phenyl-1-naphthyl-
A
Sulfon Acid Blue R
M'17: ?
amine-8-sulf onic Acid
M'18: ?
M'19: ?
M '20: 454,185
189
Sulf on Acid Blue B
I '14: 35,560
Tolyl-1-naphthylamine-
A
M'17: ?
8-sulfonic Acid
M'19: ?
M'20: ?
DISAZO DYES
217
Naphthol Blue Black
I '14:-431,027
p-Nitro-aniline
A
Agalma Black 10B
M'17: 620,218
Aniline
M'18:
^__
1,158,309
M'19:
1,877,860
I '20: 840
M'20:
2,608,864
261
Buffalo Black 10B
M'17: ?
Sulfanilic Acid
A
M'18: ?
a-Naphthylamine
M'19: ?
M'20: ?
264
Fast Sulfon
M'19: ?
Naphthionic Acid
A
Black F
I '20: 2,204
/3-Naphthol
M'20: ?
333
Diamine Black BH
I '14: 619,430
Benzidine
D
Oxamine Black BHN
M'17: ?
Gamma Acid
M'18: ?
M'19:-485,046
I '20: 5,512
M'20: 803,501
300 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
334
Diphenyl Blue Black
I '14: 26,240
Benzidine
D
Ethyl-gamma Acid
336
Benzo Cyanine R
I '14: 201
Benzidine
D
l-Amino-8-naphthol-4-
sulfonic Acid
337
Diamine Blue 2B
I '14: 19,035
Benzidine
D
Benzo Blue 2B
M'17:
H Acid (2 mols)
1,445,059
M'18:
1,523,985
M'19:
1,380,335
M'20:
1,789,774
353
Direct Indigo
I '14: 6,000
Benzidine
D
Blue BN
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
381
Azo Black Blue B, R
Tolidine
D
w-Hydroxy-diphenyl-
amine
382
Azo Mauve B
M'17: ?
a-Naphthylamine
D
*
M'20: ?
Tolidiue
383
Naphthazurine B
I '14: 4,782
Tolidine
D
/3-Naphthylamine
386
Diamine Blue BX
I '14: 1,740
Tolidine
D
Benzo Blue BX
M'17: ?
Nevile-Winther's Acid
M'18: ?
M'19: 92,214
I '20: 4,520
M '20: 90,147
390
Benzo Cyanine B
I '14: 201
Tolidine
D
l-Amino-8-naphthol-4-
sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
301
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
391
Diamine Blue 3B
I '14: 1,365
Tolidine
D
Benzo Blue 3B
M'17: 14,533
H Acid (2 mols)
M'18: 99,645
M '19: 182,946
I '20: 1,124
M '20: 136,891
425
Benzo Cyanine 3B
I '14: 1,001
Dianisidine
D
1 - Amino-8-naphthol-4-
sulfonic Acid
426
Diamine Pure Blue
I '14: 12,881
Dianisidine
D
Benzamine Pure
M'17: ?
H Acid (2 mols)
Blue
M'18: ?
M' 19: 192,350
I '20: 662
M '20: 223,100
430
Indazurine 5 GM
Dianisidiae
D
1 : 7-Dihydroxy-2-naph-
thoic-4-sulf onic Acid
TRISAZO DYES
438
Melogene Blue BH
M'17: ?
Benzidine
D
M'18: ?
p-Xylidine
H Acid (2 mols)
439
Direct Indigo Blue A
M'18: ?
H Acid (2 mols)
D
Benzidine
m-Amino-p-cresol
Methyl Ether
441
Diazo Blue Black RS
M'19: ?
Benzidine
D
M'20:~ ?
a-Naphthylamine
H Acid (2 mols)
443
Direct Indone
Benzidine
D
BlueR
a-Naphthylamine
2 R Acid
446
Benzo Olive
I '14: 1,149
Benzidine
D
Salicylic Acid
a-Naphthylamine
302 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
448
TRISAZO DYES
(continued)
Diamine Bronze G
I '14: 4,495
Benzidine
Salicylic Acid
m-Phenylene-diamine
D
462
Erie Direct
Black GX
Direct Deep
Black EW
I '14:
1,246,536
M'17: ?
M'18: ?
M'19:
7,250,007
M'20:
7,736,994
Benzidine
Aniline
m-Phenylene-diamine
D
463
Erie Direct
Black RX
Cotton Black E
I '14: 248,567
M'19: ?
M '20:
2,050,741
Benzidine
Aniline
m-Tolylene-diamine
D
464
Erie Direct
Green ET
M'17: ?
M'18: ?
M'19: 69,700
M'20: ?
Benzidine
Aniline
Phenol
D
467
Diphenyl Green G
I '20: 2,205
Benzidine
o-Chloro-p-nitro-aniline
Phenol
D
468
Diphenyl Green 3G
Benzidine
0-Chloro-p-nitro-aniline
Salicylic Acid
D
469
Chloramine Black N
I '14: 39,600
M'19: ?
I '20: 1,763
Benzidine
2: 5-Dichloro-aniline
m-Phenylene-diamine
D
470
Chloramine Green B
I '14: 1,675
M'19: ?
M'20: ?
Benzidine
2: 5-Dichloro-aniline
Phenol
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from H Acid (continued)
303
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Impoit and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
(continued)
471
Chloramine Blue 3G
I '14: 286
Benzidine
D
M'19: ?
2: 5-Dichloro-aniline
I '20: 882
H Acid (2 mols)
472
Chloramine
Benzidine
D
Blue HW
2: 5-Dichloro-aniline
Gamma Acid
473
Diamine Black HW
I '20: 342
Benzidine
D
p-Nitro-aniline
Gamma Acid
474
Diamine Green B
I '14: 77,100
Benzidine
D
Oxamine Green B
M'17: ?
p-Nitro-aniline
M '18: 295,147
Phenol
M '19: 305,854
I '20: 2,460
M '20: 420,138
~__
475
Diamine Green G
I '14: 7,329
Benzidine
D
Oxamine Green G
M'17: ?
p-Nitro-aniline
M'18: 29,118
Salicylic Acid
M '19: 136,638
I '20: 1,332
M'20: 53,292
Histazarin
2 : 3-Dihydroxy-anthraquinone (not considered herein)
o-Homo-salicylic Acid
See, o-Cresotic Acid
^-Hydrazine-benzene-sulfonic Acid (C. A. nomen.)
See, Phenyl-hydrazine-p-sulfonic Acid
a-Hydro-juglone
1:4: 5-Trihydroxy-naphthalene (not considered herein)
304
DYES CLASSIFIED BY INTERMEDIATES
Hydrol
Tetramethyl-diamino-benzohydrol
p: p / -Bis(dimethylamino)-6enzohydrol (C. A. nomen.)
Michler's Hydrol
H
(CH 3 ) 2 N
N (CH 3 ) 2 s= C 17 H 22 N 2 == 270
H
STATISTICS. Manufactured '20: 88,583 Ibs.
FORMATION. Dimethyl-aniline is condensed with formaldehyde in
presence of hydrochloric acid, and the resulting product is oxidized
with lead peroxide; or the corresponding ketone (tetramethyl-
diamino-benzophenone) is reduced with zinc
LITERATURE. Cain, Intermediate Products (2d Ed.), 102-3
Lange, Zwischenprodukte, #1358
Dyes Derived from Hydrol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
498
Turquoise Blue
I '14: 1,541
p-Nitro-toluene
B
I '20: 1,407
[Oxidation]
509
Chrome Green
Benzoic Acid
M
[Oxidation]
516
Crystal Violet
I '14: 51,872
Dimethyl-aniline
B
M'17: ?
[Oxidation]
M'18: ?
M'19: ?
I '20: 2,919
M'20: ?
528
Fast Acid Violet 10B
I '14: 12,919
Benzyl-ethyl(methyl)-
A
M'17: ?
aniline-disulf onic Acid
M'18: ?
[Oxidation]
M'19: ?
I '20: 10,086
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Hydrol (continued)
305
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
542
(continued)
Agalma Green B
I '14: 2,294
4-Chloro-3 : 5-dinitro-
benzene-sulfonic Acid
A
Metanilic Acid
or
Dinitro-diphenylamine-
disulfonic Acid
549
Chrome Violet
I '14: 51
Salicylic Acid
[Oxidation]
M
550
Chrome Bordeaux
Amino-salicylic Acid
[Oxidation]
M
DlPHENYL-NAPHTHYL-
METHANE DYES
558
Victoria Blue R
I '14: 4,171
I '20: ' 97
Ethyl-a-naphthylamine
[Oxidation]
B
559
Victoria Blue B
I '14: 127,769
M'17: ?
Phenyl-a-naphthyl-
amine
B
M'18: ?
M'19: ?
[Oxidation]
I '20: 4,171
M'20: ?
562
Fast Acid Blue B
I '14: 33,251
I '20: 6,478
l-Naphththylamine-2-
sulfonic Acid
[Oxidation]
A
563
New Patent Blue B
I '14: 595
I '20: 1,814
Naphthionic Acid
or
Laurent's Acid
A
[Substitution of -NH^
by -S0 3 Na and Oxida-
tion]
564
Naphthalene Green V
I '14: 22,144
I '20: 9,291
Naphthalene
or
Naphthalene-2: 7-disul-
fonic Acid
A
306 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Hydrol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYL-NAPHTHYL-
METHANE DYES
(continued)
566
Wool Green S
I '14: 60,073
G Acid
A
M'17: ?
M'19: ?
I '20: 127,764
M '20: 212,362
567
Chrome Blue
l-Hydroxy-2-naphthoic
M
Acid
[Oxidation]
OXAZINE DYE
652
New Fast Blue F
I '14: 2,502
Nitroso-dimethyl-
B
aniline
/3-Naphthol
or
[Meldola's Blue]
3-Hydroxy-acenaphthene
4-Hydroxy-acenaphthene (German numbering)
3-Acenaphthenol (C. A. nomen.)
CH 2 -CH 2
FORMATION. From 3-amino-acenaphthene by diazotizing and then
boiling to hydrolyze the diazo group
LITERATURE. Lange, Zwischenprodukte, #2957
Frdl. 10, 544
Dye Derived from 3-Hydroxy-acenaphthene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
894
INDIGO GROUP DYES
Alizarin Indigo B
I '14: 402
I '20: 291
2-Isatin Anilide
V
DYES CLASSIFIED BY INTERMEDIATES
4-Hydroxy-acenaphthene (German numbering)
See, 3-Hydroxy-acenaphthene
1-Hydroxy-anthracene
See, 1-Anthrol (C. A. nomen.)
9-Hydroxy-anthracene
See, 9-Anthrol (C. A. nomen.)
1-Hydroxy-anthranol
l-Hydroxy-9-anthrol
a-Hydroxy-anthranol
1: 9-Anthradiol (C. A. nomen.)
OH
'
307
H
FORMATION. 1-Hydroxy-anthraquinone is reduced with hydrosulfite
and alkali or with stannous chloride and hydrochloric acid
LITERATURE. Ger. Pat. 242,053; Frdl. 10, 532
Barnett, Anthracene and Anthraquinone
Dye Derived from 1-Hydroxy-anthranol
SchuUz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
896
INDIGO GROUP DYES
Helindone Blue 3GN
I '14: 622
I '20: 2,527
2-Isatin Anilide
V
a-Hydroxy-anthranol
See, 1-Hydroxy-anthranol
l-Hydroxy-9-anthrol
See, 1-Hydroxy-anthranol
308 DYES CLASSIFIED BY INTERMEDIATES
m-Hydroxy- benzaldehyde
CHO
IOH
-C 7 H 6 2 =122
FORMATION. From w-amino-benzaldehyde by diazotizing the amino-
group and then boiling until the nitrogen evolution ceases
LITERATURE. Cain, Intermediate Products (2d Ed.), 145
Lange, Zwischenprodukte, #461
Dyes Derived from m-Hydroxy-benzaldehyde
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
543
TRIPHENYL-METHANE
DYES
Patent Blue V
I '14: 196,228
M'17: ?
M'18: ?
I '20: 36,420
Diethyl-aniline (2 mols)
[Sulfonation, Oxidation]
A
544
Cyanine B
I '14: 8,398
I '20: 24
Diethyl-aniline (2 mols)
[Sulfonation, Oxidation]
or
[Oxidation of Patent
Blue]
A
545
Patent Blue A
I '14: 63,744
M'18: ?
I '20: 44,801
Benzyl-ethyl-aniline
(2 mols)
[Sulfonation, Oxidation]
JE*
546
Cyanol
I '14: 40,015
I '20: 7,954
Ethyl-o-toluidine
(2 mols)
[Sulfonation, Oxidation.
A
m-Hydroxy-dimethyl-aniline
See, w-Dimethylamino-phenol (C. A. nomen.]
DYES CLASSIFIED BY INTERMEDIATES
m-Hydroxy-diphenylamine
Phenyl-w-amino-phenol
m-Anilino-phenol (C. A. nomen.)
309
NH
= 185
FORMATION. (1) From resorcinol by heating with aniline and zinc
chloride at 280-290. (2) From ra-amino-phenol by heating with
aniline hydrochloride in an autoclave at 210-215
LITERATURE. Cain, Intermediate Products (2d Ed.), 55
Lange, Zwischenprodukte, #1613
Dyes Derived from m-Hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
381
Azo Black Blue B, R
Tolidine
D
H Acid
OXAZINE DYE
658
Fast Black
I '14: 1,960
Nitroso-dimethyl-
B
I '20: 2,883
aniline
^-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A.
nomen.)
See, /3-Hydroxy-naphthoquinonyl-aniline-p-sulfonic Acid
l-Hydroxy-naphthalene-2-carboxylic Acid
See, l-Hydroxy-2-naphthoic Acid (C. A. nomen.)
2-Hydroxy-naphthalene-3-carboxylic Acid
See, 3-Hydroxy-2-naphthoic Acid (C. A. nomen.)
Hydroxy-naphthalene-sulfonic Acids
See, Naphthol-sulfonic Acids
310 DYES CLASSIFIED BY INTERMEDIATES
l-Hydroxy-2-naphthoic Acid (C. A. nomen.)
l-Hydroxy-naphthalene-2-carboxylic Acid
o-Oxy-naphthoic Acid
o-Naphthol-carboxylic Acid
OH
/ NV/' X. /"-sulonic Acid
AT-(3-Hydroxy-4-keto-l(4)-naphthylidene)-sulfanilic Acid (C. A,
nomen.)
312
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. The potassium salt of 1 : 2-naphthoquinone-4-sulfonic
acid is condensed with the sodium salt of sulfanilic acid, splitting
off a sulfonic group and furnishing the /3-hydroxy-naphthoquinonyl-
aniline-p-sulfonic acid
LITERATURE. Lange, Schwefelfarbstoffe, 393,139
Lange, Zwischenprodukte, #2870, 2871
Schultz, Farbstoiftabellen, #747
Dye Derived from /3-Hydroxy-naphthoquinonyl-aniline--sulfonic
Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUE DYE
747
Thional Brown G
I '14: 110
[S+Na2S]
S
I '20: 43,219
4- (^-Hydroxy-phenyl-amino) -l-phenylamino-naphthalene-8-
sulfonic Acid
8-Anilino-5-(p-hydroxy-anilino)-l-naphthalene-sulfonic Acid (C.
A. nomen.)
H0 3 S NH
NH
OH
FORMATION. By condensation of phenyl-l-naphthylamine-8-sulfonic
acid and p-amino-phenol
LITERATURE. Lange, Schwefelfarbstoffe, 425
DYES CLASSIFIED BY INTERMEDIATES
313
Dye Derived from 4-(^-Hydroxy-phenyl-amino)-l-phenylamino-naph-
thalene-8-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
746
SULFUR DYE
Thional Green B
Katigene Green
I '14: 63,929
I '20: 14,370
[NaaS+S]
S
2-Hydroxy-fhionaphthene (C. A. and English women.)
3-Hydroxy-l-thionaphthene (German numbering)
Thioindoxyl
CH 2 or | I
/ \A
3,
C4)H
FORMATION. Thiosalicylic acid with chloro-acetic acid gives phenyl
thioglycolic-o-carboxylic acid:
.CH 2 .COOH
COOH
This body, by heating with a little water and caustic soda, closes
up the second ring and forms 2-hydroxy-thionaphthene-l-carboxylic
acid, which in warm acid solution decomposes, losing C02 and form-
ing 2-hydroxy-thionaphthene
LITERATURE. -Lange, Zwischenprodukte, #2148-2163
Georgievics and Grandmougin, Dye Chemistry, 432-434
Schultz, Farbstofftabellen (5 auf.), #912
Cain, Intermediate Products (2d Ed.), 159
314
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Hydroxy-thionaphthene
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
899
INDIGO GEOUP DYES
Ciba Gray G
I '14: 675
2-Isatin anilide
[Bromination]
V
900
Ciba Violet 3B
I '14: 2,667
2-Isatin anilide
[Bromination]
V
900
Thio Indigo Violet K
2-Isatin anilide
[Bromination]
V
901
Ciba Violet B
I '14: 20,836
I '20: 18,287
2-Isatin anilide
[Bromination]
V
905
Thio Indigo
Scarlet R
I '20: 270
Isatin
V
906
Thio Indigo
Scarlet G
I '20: 1,291
Isatin
[Bromination]
V
907
Ciba Scarlet G
I '14: 22,265
I '20: 25,578
Acenaphthenequinone
V
908
Ciba Red R
I '14: 1,001
Acenaphthenequinone
[Bromination]
V
912
Thio Indigo Red B
I '14: 1,102
I '20: 275
2-Hydroxy-thionaph-
thene (2 mols)
V
919
Ciba Bordeaux B
I '14: 899
I '20: 1,786
2-Hydroxy-thionaph-
thene (2 mols)
[Bromination]
or
[Bromination of Thio
Indigo Red R]
V
3-Hydroxy-thionaphthene
See, 2-Hydroxy-thionaphthene
DYES CLASSIFIED BY INTERMEDIATES 315
2-Hydroxy-fhionaphthene-l-carboxylic Acid (C. A. nomen.)
3-Hydroxy-(l)-thionaphthene-2-carboxylic Acid (German num-
bering)
Thioindoxyl-carboxylic Acid
s \
C.COOH =C 9 H 6 3 S =
FORMATION. From phenyl-thioglycol-o-carboxylic acid through closing
of the side chain upon fusion with caustic soda. (The carboxylic
group is very easily split off with the formation of 2-hydroxy-
thionaphthene.) Cf. 2-hydroxy-thionaphthene
LITERATURE. Cain, Intermediate Products (2d Ed.), 159
Lange, Zwischenprodukte, #2148-2163
USES. See 2-hydroxy-thionaphthene
/
I Acid
See, J Acid
p: ^'-Imino-bissniline (C. A. nomen.)
See, p: p'-Diamino-diphenylamine
4:4'-Imino-bis-o-foluidine (C. A. nomen. NHz=l)
See, p : p'-Diamino-ditoly 1-amine
Indanthrene
See, Indanthrone
Indanthrene -sulfonic Acid
See, Indanthrone-sulfonic Acid
316 DYES CLASSIFIED BY INTERMEDIATES
Indanthrone
Dianthraquinone-dihydroazine
Indanthrene (C. A. nomen.)
-CO
Y N ,
J NIL
FORMATION. Anthraquinone is sulfonated with oleum to 2-anthraqui-
none-sulfonic acid, which upon being heated in an autoclave with
ammonia forms 2-amino-anthraquinone. This latter by the action
of alkali at 200-300 is converted to indanthrone
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 449-450
Barnett, Anthracene and Anthraquinone, 342
Schultz, Farbstofftabellen (1914 Ed.), #837
Dyes Derived from Indanthrone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
837
ANTHRAQUINONE AND
ALLIED DYES
Indanthrene
BlueR
I '14: 500
[This is indanthrone]
V
838
Indanthrene
Blue RS
I '14: 187,379
M'17: ?
I '20: 16,385
M'20: ?
[Reduction]
V
840
Indanthrene
Blue
I '14: 6,120
I '20: 551
[Oxidation]
V
841
Indanthrene
Blue 2GS
I '14: 10,163
I '20: 500
m
V
842
Indanthrene
Blue GCD
I '14: 478,980
M'19: ?
I '20: 147,620
[Dichlorination]
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Indanthrone (continued}
317
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
V
843
ANTHRAQUINONE AND
ALLIED DYES
(continued)
Indanthrene
Blue GC
I '14: 1,499
I '20: 4,700
[Dibromination]
850
Indanthrene
Blue WB
I '14: 32,957
I '20: 2,998
[?]
V
Indanthrone-sulfonic Acid
Indanthrene-sulfonic Acid (C. A. nomen.)
=C 2 8Hi4N 2 7 S 522
FORMATION. (1) From 2-amino-anthraquinone-sulfonic acid by fusion
with caustic alkali at 200-300 C. (2) By sulfonating indan-
throne (obtained by alkaline fusion of 2-amino-anthraquinone)
LITERATURE. Barnett, Anthracene and Anthraquinone, 352
Thorpe, Die. Chemistry, 3, 101 et seq.
Dye Derived from Indanthrone-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
840
Indanthrene
I '14: 6,120
V
Blue
I '20: 1,702
318
DYES CLASSIFIED BY INTERMEDIATES
Indigo "
Note. Indigo is of course a dye and not an intermediate. However
because of their close mutual connection, it was considered worth while to
list together the dyes derived directly from indigo. All of these dyes are
also classified by the various intermediates that are used for the manufacture
of indigo , namely :
1. Phenyl-glycine (2 mols)
2. Phenyl-glycine-o-carboxylic Acid (2 mols)
8. Thiocarbanilide (2 mols)
4. Aniline (2 mols)
5. Phthalic anhydride (2 mols)
Dyes Derived from Indigo
Schultz
Number
jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
874
Indigo
I '14:
V
8,507,359
M '17 :274,771
M '18:
3,083,888
M'19:
8,863,824
I '20: 520,347
M '20:
18,178,231
876
Indigo MLB
[Reduction]
V
Indigo White
877
Indigotine
I '14: 19,329
[Sulfonation]
A
M'17:
1,876,787
M '18:
1,434,703
M'19:
1,699,670
I '20: 5,512
M'20:
1,395,000
878
Indigotine P
[Sulfonation]
A
DYES CLASSIFIED BY INTERMEDIATES
319
Dyes Derived from Indigo (continued)
Schulta
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
879
INDIGO GROUP DYES
(continued)
Brom Indigo
Rath jen
Indigo MLB/RR
I '14: 53,610
M'20: ?
[Bromination]
V
880
Helindone Blue BB
Indigo RB
I '14: 6,856
M'17: 14,100
I '20: 3,691
M'20: ?
[Bromination]
V
881'
Dianthrene
Blue 2B
Bromo Indigo FB
Ciba Blue 2B
I '14: 16,880
M'19: ?
I '20: 35,857
[Bromination]
V
882
Indigo MLB/5B
Ciba Blue G
I '14: 1,356
I '20: 1,008
[Bromination]
V
883
Indigo MLB/6B
Indigo KG
I '14: 3,191
I '20: 4,130
M '20: ?
[Bromination]
V
884
Brilliant Indigo
BASF/2B
I '14: 4,518
[Chlorination, Bromina-
tion]
V
885
Brilliant Indigo
BASF/B
I '14: 8,175
I '20: 3,503
[Chlorination]
V
886
Brilliant Indigo
BASF/G
I '14: 12,057
[Chlorination, Bromina-
tion]
V
889
Indigo Yellow 3G
Benzoyl Chloride
V
890
Ciba Yellow G
I '14: 48
Benzoyl Chloride
[Bromination]
V
Indigo Red
See, Indirubin
320
DYES CLASSIFIED BY INTERMEDIATES
Indirubin (C. A. nomen.}
Oxindole- [A 3>2/ ]-pseudoindoxy 1
Indigo Red
H
C 16 Hi N 2 O 2 262
/
00
FORMATION. By reaction of indoxyl on isatin in the " indoxyl melt "
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 410
Ger. Pat. 192,682; Frdl. 9, 533
Dye Derived from Indirubin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
897
INDIGO GROUP DYES
Ciba Heliotrope B
[Brommation]
V
Indoxyl (C. A. nomen.)
3-Hydroxy-indole
NH
CH 2 or
FORMATION. From phenyl-glycine by fusion with sodamide
LITERATURE. Lange, Zwischenprodukte, #2057-2084
Dye Derived from Indoxyl
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
897
Ciba Heliotrope B
Isatin
V
[Bromination]
DYES CLASSIFIED BY INTERMEDIATES
321
Isatin (C. A. nomen.)
2-Hydroxy-3-pseudoindolone
\ /\/ N \
CO or | | C.OH
^co/ N ^ //NX CO/
STATISTICS. Imported ; 14: very small
Manufactured '20: ?
FORMATION. From indoxyl by oxidation
LITERATURE. Lange, Zwischenprodukte, #1815, 2023, 2110-2116
Dyes Derived from Isatin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
897
INDIGO GROUP DYES
Ciba Heliotrope B
Indoxyl
[Bromination]
V
898
Helindone Violet D
.
7-Methyl-indoxyl
[Bromination]
V
904
Helindone Brown G
I '14: 13,086
I '20: 2,200
5-Amino-2-hydroxy-
thionaphthene
[Bromination]
V
905
Thio Indigo
Scarlet R
I '20: 370
2-Hydroxy-thionaph-
thene
V
906
Thio Indigo
Scarlet G
I '20: 1,291
2-Hydroxy-thionaph-
thene
[Bromination]
V
2-Isatin Anilide
a-Isatin Anilide
Isatin-2-phenylimide
2-Anilino-3-pseudoindolone (C. A. nomen.)
N
C NH
CO/
= 222
322
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Aniline is condensed with carbon disulfide to thiocarbani-
lide (CeH6 . NH)2 CS, which is treated in solution with potassium
cyanide and lead carbonate, resulting in the formation of the
corresponding cyanide. This cyanide is reacted with yellow am-
monium sulfide (containing NH4.S. S.NH^), and a thioamide is
formed:
C 6 H 5 .N, / NH *
C 6 H 5 .NH
This compound upon being heated with sulfuric acid gives a good
yield of 2-isatin anilide
LITERATURE. Lange, Zwischenprodukte, #2132-2134
Georgievics and Grandmougin, Dye Chemistry, 413
Dyes Derived from 2-Isatin Anilide
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
894
INDIGO GROUP DYES
Alizarin Indigo B
I '14: 402
I '20: 291
3-Hydroxy-acenaph-
thene
V
896
Helindone Blue 3GN
I '14: 622
I '20: 2,527
1-Hydroxy-anthranol
V
899
Ciba Gray G
I '14: 675
2-Hydroxy-thionaph-
thene
[Bromination]
V
900
Ciba Violet 3B
I '14: 2,667
2-Hydroxy-thionaph-
thene
[Bromination]
V
900
Thioindigo Violet K
2-Hydroxy-thionaph-
thene
[Bromination]
V
901
Ciba Violet B
I '14: 20,836
I '20: 18,287
2-Hydroxy-thionaph-
thene
[Bromination]
V
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Isatin Anilide (continued)
323
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics aj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
902
INDIGO GROUP DYES
(continued)
Helindone Brown 2R
I '14: 876
I '20: 1,778
5-Amino-l-hydroxy-
thionaphthene
[Bromination]
V
903
Helindone Brown 5R
5-Amino-l-hydroxy-
thionaphthene
[Bromination]
V
a-Isatin Anilide
See, 2-Isatin Anilide
Isatin-2-phenylimide
See, 2-Isatin Anilide
Isoanthraflavic Acid
2 : 7-Dihydroxy-anthraquinone (not considered herein)
Iso-7 Acid
See, J Acid
Iso-naphthazarin
2: 3-Dihydroxy-l : 4-naphthoquinone (not considered herein)
Isoquinoline
z=C 9 H 7 N 129
STATISTICS. Imported '14: very small
324
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Isoquinoline is extracted from coal-tar or prepared by
synthetical means
LITERATURE. Lange, Zwischenprodukte, #1997
Dye Derived from Isoquinoline
Schultz
Number
Jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
QUINOLINE DYE
610
Quinoline Red
Benzo-trichloride
B
Quinaldine
J Acid
2-Amino-5-naphthol-7-sulfonic Acid
Amino-naphthol-sulfonic Acid J
6-Amino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
I Acid
Iso-7 Acid
H03S 00 NHt = c N ' No *= 239 i
no
STATISTICS. Imports '14: 1,153 Ibs.
Manufactured '20: ?
FORMATION. /3-Naphthylamine is disulfonated to a mixture of 2-
naphthylamine-5 : 7-disulf onic acid and 2-naphthylamine-6 : 8-
disulfonic acid. The latter is amino-G acid and is a step in the
preparation of gamma acid. The former is fused with caustic soda
in an autoclave to form J acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 235
Lange, Zwischenprodukte, #2542
Thorpe, Die. Chemistry, 3, 640
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from J Acid
325
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics o)
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cotion
Class
DISAZO DYES
279
Benzo Fast Scarlet
I '14: 36,674
M'19: ?
I '20: 24,153
J Acid (2 mols)
Phosgene
Aniline or
Toluidine or
D
Xylidine or
/3-Naphthylamine or
Amino-azo-benzene
(2 mols)
326
Oxamine Violet
Oxy Diamine Violet
BF
I '14: 23,981
I '20: 732
Benzidine
J Acid (2 mols)
D
346
Oxamine Red
I '14: 11,636
I '20: 848
Benzidine
Salicylic Acid
D
385
Oxamine Blue 4R
I '14: 573
Tolidine
D
M'20: ?
Nevile-Winther's Acid
Juglone
5-Hydroxy-l : 4-naphthoquinone (not considered herein)
K Acidi
l-Amino-8-naphthol-4 : 6-disulf onic Acid
Amino-naphthol-disulfonic Acid K
8-Amin.o-l-naphthol-3 : 5-disulfonic Acid (C. A. nomen.)
HO NH 2
H0 3 S
S0 3 H
1 K acid is also occasionally used as trivial name for 1:1- Dihydroxy-naphthalcnc-
3: 5-disulfonic acid.
326
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Naphthalene is disulfonated to the 1 : 5 acid, and then
further sulfonated to the 1 : 3 : 5-trisulf onic acid. This trisulfonic
acid while still in the sulfonation mixture is diluted with a little ice,
and cooled, and it is then nitrated cold with the theoretical amount
of mixed acid. It is reduced with iron, forming 1-naphthylamine-
4:6: 8-trisulfonic acid, which upon being fused with caustic soda
in an autoclave yields the K acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 239
Lange, Zwischenprodukte, #2728
Thorpe, Die. Chemistry, 3, 642
Dyes Derived from K Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Impart and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
43
MONOAZO DYE
Tolane Red B, G
Aniline
A
215
DISAZO DYES
Blue Black N
I '14: 2,653
Aniline
p-Nitro-aniline
A
219
Chrome Patent
Green N
Aniline
Picramic Acid
ACr
335
Naphthamine Black
RE
I '14: 49,016
Benzidine
Gamma Acid
D
338
Naphthamine Blue
2Bor3B
I '14: 11,707
I '20: 400
Benzidine or
Tolidine
K Acid (2 mols)
D
Kalle's Acid
l-Naphthylamine-2: 7-disulfonic Acid (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES
Ketone
Tetramethyl-diamino-benzophenone
p: p'-Bis(dimethylamino)-6enzophenone (C. A. nomen.)
Michler's Ketone
Ketone Base
=3268
STATISTICS. Imported '14: small amount
Manufactured ' 17 : ?
Manufactured '18: 73,208 Ibs.
Manufactured '19: 281,057 Ibs.
Manufactured '20: 90,664 Ibs.
FORMATION. From dimethyl-aniline by reaction with phosgene
LITERATURE. Cain, Intermediate Products (2d Ed.), 103
Lange, Zwischenprodukte, #1382
Dyes Derived from Ketone
327
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AURAMINES
493
Auramine
I '14: 449,276
[Ammonium chloride
B
M'17: ?
and Zinc chloride]
M'18: 45,634
M J 19: 127,567
I '20: 74,414
M'20: ?
TRIPHBNYL-METHANE
DYES
516
Crystal Violet
I '14: 51,872
Dimethyl-aniline
B
M'17: ?
M'18: ?
M'19: ?
I '20: 2,919
M'20: ?
*
522
Victoria Blue 4R
I '14: 9,599
Methyl-phenyl-a-
B
I '20: 152
naphthylamine
328 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Ketone (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
527
(continued)
Acid Violet 4BN
I '14: 29,184
I '20: 23,335
B enzyl-methyl-aniline
A
548
Acid Violet 6BN
I '14: 6,861
I '20: 5,582
3-Ethoxy-4'-methyl-
diphenylamine
[Sulfonation]
A
DlPHENYL-NAPTHYL-
METHANE DYES
558
Victoria Blue R
I '14: 4,171
I '20: 97
Ethyl-a-naphthylamine
B
559
Victoria Blue B
I '14: 127,769
M'17: ?
Phenyl-a-napthyl-
amine
B
M'18: ?
M'19: ?
I '20: 11,782
M'20: ?
561
Acid Violet 5BNS
I '14: 1,896
Methyl-(Ethyl-) phenyl-
j8-naphthylamine
A
566
Wool Green S
I '14: 60,073
M'17: ?
M'19: ?
/3-Naphthol
[Sulfonation]
A
I '20: 127,764
M '20: 212,362
ACRIDINE DYE
607
Rheonine
I '14: 19,704
m-Phenylene-diamine
B
6-Keto-l-(^-sulfo-phenyl)-3-A2-y/>razoline-carboxylic Acid (C. A
nomen.)
See, l-(p-Sulfo-phenyl)-5-pyrazolone-3-carboxylic Acid
Koch's Acid
See, l-Naphthylamine-3: 6: 8-trisulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES 329
L Acid
See, l-Naphthol-5-sulfonic Acid (C. A. nomen.)
See Laurent's Acid
2: 6-Dihydroxy-naphthalene-3-carboxylic Acid (not con-
sidered herein)
Lambda Acid or \ Acid
See, l-Naphthylamine-2-sulfonic Acid
Landschoff and Meyer's Acid
l-Naphthylamine-2 : 5-disulf onic Acid (not considered here)
Laurent's a Acid
l-Nitro-naphthalene-5-sulfonic Acid (not considered herein)
Laurent's Acid
l-Naphthylamine-5-sulfonic Acid
a-Naphthylamine-sulfonic Acid L
5-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
Naphthalidine-sulfonic Acid
Naphthalidinic Acid
Cleve's a Acid
L Acid
Laurent's Naphthalidinic Acid
NH 2
H0 3 S
STATISTICS. Imported '14: 2,832
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: 294,352
FORMATION. (1) From a-naphthylamine by sulfonation with oleum.
(2) From a-naphthalene-sulfonic acid by nitration reduction and
separation from the l-naphthylamine-8-sulfonic acid also formed
LITERATURE. Cain, Intermediate Products (2d Ed.), 190
Lange, Zwischenprodukte, #2360-2
Thorpe, Die, Chemistry, 3, 590
330
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Laurent's Acid
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
53
MONOAZO DYE
Archil Substitute
3VN
p-Nitro-aniline
A
162
Brilliant Fast
RedG
/3-Naphthol
A
265
DISAZO DYES
Sulfoncyanine
Black B
I '14: 69,590
M'17: ?
M'18: ?
M'19: ?
M '20: ?
a-Naphthylamine or
1-Naphthylamine-
6- and 7-sulf onic
Acids
Phenyl-1-naphthyl-
amine-8-sulfonic Acid
A
308
Diazo Black B
I '14: 62,854
Laurent's Acid (2 mols)
Benzidine
D
364
Benzopurpurin 6B
I '14: 9,171
I '20: 4,743
Laurent's Acid (2 mols)
Tolidine
D
480
TRISAZO DYE
Congo Brown R
I '14: 3,045
Benzidine
Resorcinol
Salicylic Acid
D
563
DlPHENYL NAPHTHYL-
METHANE DYE
New Patent Blue B
I '14: 595
I '20: 1,814
Hydrol
[Substitution of NH 2 by
S0 3 H; Oxidation]
A
Laurent's Naphthalidinic Acid
See, Laurent's Acid (l-Naphthylamine-5-sulfonic Acid)
DYES CLASSIFIED BY INTERMEDIATES 331
Lepidine (C. A. nomen.)
4-Methyl-quinoline (N=l)
7-Methyl-quinoline
Cincholepidine
143
FORMATION. (1) From cinchonine by distillation with caustic potash.
(2) By saturating a mixture of methylal [CH 2 (OCH 3 )2] and acetone
with gaseous hydrochloric acid, and then heating this with aniline
and concentrated hydrochloric acid
LITERATURE. Thorpe, Die. Chemistry, 4, 478
Dye Derived from Lepidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
QUINOLINB DYE
611
Quinoline Blue
Quinoline
Photo-
[Amyl-iodidel
graphy
^-Leucaniline
See, Triamino-triphenyl-methane
Leuco-zso-naphthazarin
1: 2: 3: 4-Tetrahydroxy-naphthalene (not considered herein)
Leuco-naphthazarin
1: 2: 5: 8-Tetrahydroxy-naphthalene (not considered herein)
Leucotrope
Benzyl-dimethyl-phenyl-ammonium Chloride (not considered
herein)
332 DYES CLASSIFIED BY INTERMEDIATES
Liebman and Studer's Acid
l-Naphthol-7-sulfonic Acid (not considered herein)
MAcid
See, l-Amino-5-naphthol-7-sulfonic Acid
l-(or 2-)Mercapto-anthraquinone
SH
FORMATION. By forming mercapto-benzoyl-benzoic acid and then
closing the ring
LITERATURE. Barnett, Anthracene and Anthraquinone, 183, 184
Lange, Zwischenproduckte, #3143-3147, 3527
Dye Derived from l-(or 2-)Mercapto-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
869
Algol Brown B
I '14: 1,596
'V
I '20: 4,727
o-Mercapto-benzoic Acid (C. A. nomen.)
See, Thio-salicylic Acid
Mesidine (C. A. nomen.)
2:4: 6-Trimethyl-aniline
NH 2
3 < ,CH 3 ^
H:
DYES CLASSIFIED BY INTERMEDIATES
333
FORMATION. By the nuclear methylation of aniline, whereby aniline
hydrochloride is heated with methanol (methyl alcohol) under
pressure at 300-350. There is formed, in addition to mesidine,
p- and o-toluidine, m-xylidine, etc.
LITERATURE. Ullmann, Enzy. tech. Chemie, 8, 30
Dye Derived from Mesidine
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
583
Acid Rosamine A
I '14: 50
Mesidine (2 mols)
A
I '20: 141
Resorcinol (2 mols)
Phthalic Anhydride
[PC1 5 ; Sulfonation]
or
[Dichloro-fluoresceine ;
Mesidine (2 mols);
Sulfonation]
Meta=m
Note. This is not considered in the alphabetical arrangement, e.g.
meta-Phenylene-diamine is indexed as m-Phenylene-diamine under "P."
However m-Phenylene-diamine precedes p-Phenylene-diamine
Metanilic Acid (C. A. nomen.)
w-Amino-benzene-sulfonic Acid
m-Sulfanilic Acid
S0 3 H
iNHi
STATISTICS. Manufactured '17: ?
Manufactured '18: 249,922 Ibs.
Manufactured '19: 453,137 Ibs.
Manufactured '20: 499,304 Ibs.
FORMATION. By sulfonating nitro-benzene with oleum, and reduction
with iron
334
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Cain, Intermediate Products (2d Ed.), 47
Lange, Zwischenprodukte, #619, 620
Dyes Derived from Metanilic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
134
MONOAZO DYES
Metanil Yellow
I '14: 284,606
M'17: ?
M'18: ?
M '19 :477,143
I '20: 8,456
M '20: 629,437
Diphenylamine
A
135
Metanil Yellow
Brominated
Diphenylamine
[Bromination]
A
136
Acid Yellow
MGS, GG
Diphenylamine
[Sulfonation]
A
210
DISAZO DYES
Cotton Orange R
I '14: 16,459
I '20: 51
Primuline-sulfomc Acid
w-Phenylene-diamine-
disulfonic Acid
D
256
Sulf on Black 3B
a-Naphthylamine
Phenyl-1-naphthyl-
amine-8-sulf onic Acid
A
257
Sulfoncyanine
I '14: 145,694
M'17: ?
M '18: ?
M'19: ?
I '20: 18,327
M'20: ?
a-Naphthylamine or
l-Naphthylamine-6-
and 7-sulf onic Acids
Phenyl- or Tolyl-
1-naphthylamine-
8-sulfonic Acid
A
258
Naphthalene Acid
Black 4B
I '14: 7,994
l-Naphthylamine-6-
and 7-sulf onic Acids
a-Naphthylamine
A
542
TMPHENYL-METHANE
DYE
Agalma Green B
I '14: 2,294
4-Chloro-3 : 5-dinitro-
benzene-sulfonic Acid
Hydrol
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from MetanilicTAcid (continued)
335
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
IDye
Appli-
cation
Class
SULFUR DYE
738
Cotton Black
l-Chloro-2: 4-dinitro-
S
benzene
[S+NaaS]
Methoxy-dimethylamino-benzophenone
See, 4-Dimethylamino-3-methoxy-benzophenone (C. A,
nomen.)
6-Methoxy-m-toluidine (C. A. nomen. NHz=l)
See, 2-Amino-p-cresol Methyl Ether
1-Methylamino-anthraquinone
NH . CH 3
= Ci5H n N02 =
FORMATION. 1-Chloro-anthraquinone is reacted with p-toluene-sulfon-
methyl-amide (CH 3 . C 6 H 4 . S0 2 . NH . CH 3 ), splitting off HC1 and
forming l-(p-toluene-sulfon-methyl-amino)-anthraquinone. This
latter readily decomposes in presence of sulfuric acid, fprming
1-methylarnino-anthraquinone
LITERATURE. Lange, Zwischenprodukte, #3113, 3115, 3117, 3118,3476
Barnett, Anthracene and Anthraquinone, 197, etc.
Dye Derived from 1-Methylamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYE
866
Leucol Dark
I '20: 120
V
Green B
336 DYES CLASSIFIED BY INTERMEDIATES
2-Methylamino-8-naphthol-6-sulfonic Acid
See, Methyl-gamma Acid
7-Methylamino-l-naphthol-3-sulfonic Acid (C. A. nomen.}
See, Methyl-gamma Acid
jV-Methyl-aniline
Methyl-aniline
HNCH 3
C 7 H 9 N=107
FORMATION. By heating aniline and methanol (methyl alcohol) in the
presence of sulfuric acid in an autoclave; or by heating aniline
hydrochloride and methanol in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 61
Lange, Zwischenprodukte, #92
USES. For preparation of ethyl-methyl-aniline and for benzyl-methyl-
aoiline
2-Methyl-anthraquinone (C. A. nomen.)
/3-Methyl-anthraquinone
FORMATION. Phthalic anhydride is dissolved in toluene, and heated
with Aids whereby p-toluyl-o-benzoic acid is formed, which latter,
upon being dissolved in oleum and heated, forms the 2-methyl-
anthraquinone
LITERATURE. Cain, Intermediate Products (2d Ed.), 259
Heller and Schiilke, Ber. 41, 3632 (1908)
C/. Elbs, J. pr. Chem. [II] 33, 318 (1886)
Cf. Limpricht and Wiegand, Ann. 311, 178 (1900)
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Methyl-anthraquinone
337
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
759
Anthraflavone G
I '14: 7,143
2-Methyl-anthraqui-
V
I '20: 2,354
none (2 mols)
792
Cibanone Orange R
I '20: 6,125
[Sulfur]
V
795
Cibanone Yellow R
I '14: 298
[Sulfur]
V
I '20: 14,032
/3-Methyl-anthraquinone
See, 2-Methyl-anthraquinone
3-Methyl-benzaldehyde-4 : 6-disulf onic Acid
4-Formyl-6-methyl-m-6enzene-disulfonic Acid (C. A. nomen.)
CHO
S0 3 H
FORMATION. Probably by oleum sulfonation of m-tolualdehyde
(m-tolualdehyde can be made by oxidation of m-xylene)
LITERATURE. Thorpe, Die Chemistry, 5, 516
Cf. Lange, Zwischenprodukte, #784
Dyes Derived from 3-Methyl-benzaldehyde-4:6-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
'Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
507
TRIPHENYL-METHANE
DYES
Xylene Blue VS
I '14: 2,130
I '20: 27,254
Diethyl-aniline (2 mols)
[Oxidation]
A
508
Xylene Blue AS
I '14: 8,238
I '20: 5,573
Benzyl-ethyl-aniline
(2 mols)
[Oxidation]
A
338
DYES CLASSIFIED BY INTERMEDIATES
Methyl-benzanthrone
9-Methyl-7-weso-6enzanthrenone (C. A. nomen.)
H 3 C
FORMATION. By condensation of 2-methyl-anthrone with glycerol and
sulfuric acid at about 120 C.
LITERATURE. Barnett, Anthracene and Anthraquinone, 324
Fr. Pat. 407,593
C/. Ger. Pat. 209,351. Frdl. 9, 836
Dyes Derived from Methyl-benzanthrone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
793
ANTHRAQUINONE AND
ALLIED DYES
Cibanone Blue 3G
[Sulfur]
V
794
Cibanone Black B
I 14: 2,802
[Sulfur]
V
l-Methyl-2 : 4-diamino-benzene-5-sulf onic Acid
See, 4 : 6-Diamino-m-toluene-sulfonic Acid (C. A. nomen.
SO,H=1)
l-Methyl-2 : 6-diamino-benzene-4-sulf onic Acid
See t 3 : 5-Diamino-p-foluene-sulfonic Acid (C. A. nomen.
#-Methyl-diphenylamine (C. A. nomen.)
Diphenyl-methyl-amine
DYES CLASSIFIED BY INTERMEDIATES
339
FORMATION. From diphenylamine by heating with hydrochloric acid
and methanol (methyl alcohol) in an autoclave at 250
LITERATURE. Cain, Intermediate Products (2d Ed.), 73
Dyes Derived from W-Methyl-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
532
Alkali Violet 6B
I '14: 3,020
Tetraethyl-diamino-
benzophenone
[Sulfonation]
A
534
Acid Violet 7B
I '14: 21,665
I '20: 51
Diethyl-p-amino-
benzoyl Chloride
N-Methyl-diphenyl-
amine (2 mols)
A
547
Ketone Blue 4BN
Methoxy-dimethyl-
amino-benzophenone
[Sulfonation]
A
JV-Methyl-diphenylamine-sulfonic Acid
<^~\ N / "N} S0 3 H = Ci 3 H 13 N0 3 S = 263
CH 3
FORMATION. By Sulfonation of methyl-diphenylamine
LITERATURE. Beilstein, Organische Chemie (3 auf.), II spl., 324
Dye Derived from W-Methyl-diphenylamine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
533
Acid Violet 7BN
p-Dimethylamino-
A
benzoyl chloride
AT-Methyl-d i p h e n y 1-
amine-sulfonic Acid
(2 mols)
340 DYES CLASSIFIED BY INTERMEDIATES
p : ^'-Methylene-bisaniline (C. A. nomen.)
See, p : p'-Diamino-diphenyl-methane
^:/-Methylene-bis(AT: AT-diethyl-aniline) (C. A. nomen.)
See, p: p'-Tetraethyl-diamino-diphenyl-methane
:^'-Methylene-bis(W: AT-dimethyl-aniline) (C. A. nomen.)
See, p : p'-Tetramethyl-diarnino-diphenyl-methane
4:4'-Methylene-bis(W-methyl-o-toluidine) (C. A. nomen.)
See, 4 : 4'-Dimethyl-diamino-3 : 3'-ditolyl-methane
4: 4'-Methylene-bis-o-toluidine (C. A. nomen.)
See, p : p'-Diamino-ditolyl-methane
Methylene-bisxylidine (C. A. nomen.)
See, Diamino-dixylyl-methane
Methyl-ethyl-aniline
See, Ethyl-methyl-aniline
Methyl-gamma Acid
2-Methylamino-8-naphthol-6-sulfonic Acid
7-Methylamino-l-?iaphthol-3-sulfonic Acid (C. A. nomen.)
HO
HO Si Y J NH ' CH3 - Ci^uNO^ = 253
3 \y\x
FORMATION. G salt (Sodium salt of 2-naphthol-6 : 8-disulf onic acid)
is heated in an autoclave with methylamine; and the resulting
2-methylamino-naphthalene-6 : 8-disulf onic acid is fused with caustic
soda in an autoclave, forming methyl-gamma acid. (See Gamma
acid)
LITERATURE, Lange, Zwischenprodukte, #2550
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Methyl-gamma Acid
341
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
347
Diphenyl Brown RN
Benzidine
D
Salicylic Acid
7-Methyl-indoxyl
, TTT
\
CH >
C 9 H 9 NO =
FORMATION. o-Toluidine is reacted with chloro-acetic acid, forming
o-tolyl-glycine. This body upon fusion with sodamide will in all
probability form 7-methyl-indoxy. (There is no direct reference
in the literature to 7-methyl-indoxyl)
LITERATURE. Lange, Zwischenprodukte, #241
Dye Derived from 7-Methyl-indoxyl
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
898
Helindone Violet D
Isatin
V
[Bromination]
9-Methyl-7-meso-benzanthrenone (C. A. nomen.)
See, Methyl-benzanthrone
W-Methyl-^-nitroso-aniline (C. A. nomen.}
See, p-Nitroso-methyl-aniline
342 DYES CLASSIFIED BY INTERMEDIATES
Methyl-phenyl-a-naphthylamine
JV-Methyl-N-phenyl-1-naphthylamine (C. A. nomen.)
H 3 C N
FORMATION. Phenyl-a-naphthylamine is methylated by heating with
methanol (methyl alcohol) and hydrochloric acid under pressure
LITERATURE. Schultz, Chemie des Steinkohlentheers (3 aufl. 1900)
1,117
Dye Derived from Methyl-phenyl-a-naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TEIPHENYL-METHANE
DYE
522
Victoria Blue 4R
I '14: 9,599
Ketone
B
I '20: 152
Methyl-(Ethyl-)phenyl-j3-naphthylamine
JV-Methyl-(Ethyl-)JV-phenyl-2-naphthylamine (C. A. nomen.)
CH 3
N
233
FORMATION. Phenyl-/3-naphthylamine is methylated by heating in
an autoclave with methanol (methyl alcohol) and hydrochloric
acid
LITERATURE. Lange, Zwischenprodukte, #2897
DYES CLASSIFIED BY INTERMEDIATES 343
Dye Derived from Methyl- (Ethyl-) phenyl-/3-naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and,
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYL-NAPHTHYL-
METHANE DYE
561
Acid Violet 5BNS
I '14: 1,896
Ketone
A
[Sulfonation]
3-Methyl-l-phenyl-5-^yrazolone (C. A. nomen.)
l-Phenyl-3-methyl-5-pyrazolone
N
OC N
CioHi N 2 0=:174
H 2 C C . CH 3
STATISTICS. Imported '14: 449 Ibs.
FORMATION. By heating the reaction product of phenyl-hydrazine
and aceto-acetic ethyl ester
LITERATURE. Lange, Zwischenprodukte. #138
Dyes Derived from 3-Methyl-l-phenyl-5-pyrazolone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
21
PYRAZOLONE DYES
Pigment Chrome
Yellow L
Toluidine
CL
24
Pigment Fast
Yellow R
0-Toluidine-ra-sulfonic
Acid
CL
26
28
Dianil Yellow R
Pigment Fast
Yellow G
M'19: ?
I '20: 170
Primuline-sulfonic
Acid
p-Sulfo-anthranilic
Acid
D
CL
29
Eriochrome Red B
I '14: 5,491
l-Amino-2-naphthol-4-
sulfonic Acid
CL
344 DYES CLASSIFIED BY INTERMEDIATES
2-Methyl-quinoline
See, Quinaldine (C. A. women.)
4-Methyl-quinoline (N=l)
See, Lepidine (C. A. nomen.)
a-Methyl-quinoline
See, Quinaldine (C. A. nomen.)
7-Methyl-quinoline
See, Lepidine (C. A. nomen.)
Methyl Resorcinol
See, Resorcinol Methyl Ether
3-Methyl-l- (p-zuU o-phenyl) -5-pyrazolone
l-(p-Sulfophenyl)-3-methyl-5-pyrazolone
: 5-Dihydro-5-keto-3-methyl-l-pyrazolyl)-&enzene-sulf onic
Acid (C. A. nomen.)
OC N =Ci HioN 2 4 S 254
i2C C .
FORMATION. (1) By sulfonating 3-methyl-l-phenyl-5-pyrazolone by
heating with 4 parts of 30 per cent oleum. (2) By heating phenyl-
hydrazine-p-sulfonic acid with aceto-acetic ethyl ester in 50 per
cent acelic acid solution for few hours
.-
LITERATURE. Cain, Intermediate Products (2d Ed.), 169
Lange, Zwischenprodukte, #138
DYES CLASSIFIED BY INTERMEDIATES 345
Dyes Derived from 3-Methyl-l-(-sulfo-phenyl)-5-pyrazolone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYES
19
Flavazine L
I '14: 38,908
Aniline
A
Fast Light Yellow
I '20: 9,327
27
Dianil Yellow 2R
Primuline-sulfonic Acid
D
JV-Methyl-o-foluidine (C. A. nomen. NHR =1}
Methyl-0-toluidine
HN CH 3
STATISTICS. Manufactured '19: ?
FORMATION. (1) By heating o-toluidine, methanol (methyl alcohol)
and hydrochloric acid in an autoclave. (2) By condensing o-
toluidine and formaldehyde, and reducing to methyl-o-toluidine
LITERATURE. Cain, Intermediate Products (2d Ed.), 60, 70
Cf. Lange, Zwischenprodukte, #128
Dyes Derived from W-Methyl-o-toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AURAMINE DYE
494
Auramine G
I '14: 1,902
Methyl-o-toluidine (2
B
mols)
[Formaldehyde, sulfur,
ammonium chloride,
TRIPHENYL-METHANE
etc.]
DYE
501
Glacier Blue
I '14: 2,495
Methyl-o-toluidine (2
B
Brilliant Glacier
mols)
Blue
2: 5-Dichloro-benzalde-
hyde
[Oxidation]
AZINE DYE
684
Brilliant Rhoduline
JV 3 -Ethyl-4-ra-tolylene-
B
Red
diamine
Aniline
346 DYES CLASSIFIED BY INTERMEDIATES
Michler's Hydrol
See, Hydrol
Michler's Ketone or Base
See, Ketone
Monochloro-benzene 1
See, Chloro-benzene
Monoethyl-aniline 1
See, Ethyl-aniline
Monomethyl-aniline 1
See, Methyl-aniline
Mononitro-chloro-benzene 1
See, Chloro-nitro-benzene
Monosulfonic Acid F
See, 2-Naphthol-7-sulfonic Acid
Monosulf o Acid H
l-Amino-8-naphthol-3-sulfonic Acid (not considered herein)
Mu Acid
See, l-Naphthylamine-6-sulfonic Acid
Myrbane Oil
See, Nitro-benzene
Naphtha-
See also, Naphtho-
a-Naphthahydroquinone
1 : 4-Dihydroxy-naphthalene (not considered herein)
/3-Naphthahydroquinone
1 : 2-Dihydroxy-naphthalene (not considered herein)
1 " Mono " is superfluous and is consequently not recommended.
DYB8 CLASSIFIED BY INTERMEDIATES 347
Naphthalene (C. A. nomen.)
Naphthalin
Note. Naphthalene is a crude and not an intermediate as a rule
STATISTICS.
Refined Naphthalene
Manufactured Imported
Calendar Year 1917: 35,342,911 Ibs. 267,057 Ibs.
" " 1918: 33,701,779 Ibs. 2,795 Ibs.
" 1919: 17,625,235 Ibs. 7,650 Ibs.
" 1920: 30,230,734 Ibs. 3,697,562 Ibs.
FORMATION. From coal tar by extraction and purification
LITERATURE. Thorpe, Die. Chemistry, 3, 560
Dyes Derived from Naphthalene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
564
DlPHENYL-NAPHTHYL-
METHANE DYE
Naphthalene
Green V
I '14: 22,144
I '20: 9,291
Hydrol
A
758
ANTHRAQUINONE AND
ALLIED DYES
Sirius Yellow G
Phthalic anhydride
CL
1: 6-Naphthalenediol (C. A. nomen.)
See, 1 : 5-Dihydroxy-naphthalene
2: 7-Naphthalenediol (C. A. nomen.)
See, 2: 7-Dihydroxy-naphthalene
348 DYES CLASSIFIED BY INTERMEDIATES
Naphthalene-1 : 5- and 1 : 6-disulf onic Acids
The 1 : 5 acid is also called:
Armstrong's Acid
Armstrong's 6 Acid
Naphthalene-7-disulfonic Acid of Armstrong and Wynne
Naphthalene-S-disulfonic Acid of Beilstein and Schultz
The 1 : 6-acid is also catted:
Ewer and Pick's Acid
Naphthalene-? : /3-disulfonic Acid of Armstrong and Wynne
Naphthalene-7-disulfonic Acid of Beilstein and Schultz
SO 3 H S0 3 H
/VN
and urkQ1 | Ci H 8 6 S 2 288
,^\X
H0 3 S
FORMATION. The above acids are prepared by sulfonation of naphtha-
lene with five parts of 23 per cent oleum at 60; or with five parts
of ordinary sulfuric acid (66) using first one part at 180 to form the
/3-sulfonic acid and then four parts at 95-100 for 20-24 hours
If the 1 : 5-acid alone is wanted the conditions of sulfonation are
varied slightly, generally starting with the a-sulfonic acid. The
separation is effected by crystallizing out the 1 : 5 acid or its sodium
salt from the diluted sulfonation product
LITERATURE. Cain, Intermediate Products (2d Ed.), 176, 177
Thorpe, Die. Chemistry, 3, 575
USES. The mixed acids are used for the preparation of 1-naphthyl-
amine-3: 8- and 4: 8-disulfonic acids, and the separation then made
The 1: 5-acid is used for making naphthalene-1 : 3 : 5-trisulf onic
acid
Naphthalene-2: 7-disulfonic Acid
a-Naphthalene-disulfonic Acid (of Ebert and Merz)
Ebert and Merz a Acid
DYES CLASSIFIED BY INTERMEDIATES
349
STATISTICS. Manufactured 1918, 1919, 1920 in undisclosed quantities
FORMATION. Sodium 2-naphthalene-sulfonate is further sulfonated by
dissolving in about two parts of monohydrate or a larger amount
of 66 sulfuric acid, and heating to 180 for 6-8 hours. There is
formed principally naphthalene-2: 6- and 2:7-sulfonic acids, and
the separation is effected through the calcium salts, the 2:6 salt
being less soluble
LITERATURE. Lange, Zwischenprodukte, #2442
Ger. Pat. 61,730
Thorpe, Die. Chemistry, 3, 577 >
Dyes Derived from Naphthalene-2 : 7-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Impart and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYL-NAPHTHYL-
METHANE DYE
564
Naphthalene
I '14: 22,144
Hydrol
A
Green V
I '20: 9,291
[Oxidation]
Naphthalene-? : 0-disulfonic Acid of Armstrong and Wynne
See, Naphthalene-1 : 6-disulf onic Acid
Naphthalene-7-disulfonic Acid of Armstrong and Wynne
See, Naphthalene-1 : 5-disulf onic Acid
Naphthalene-5-disulfonic Acid of Beilstein and Schultz
See, Naphthalene-1 : 5-disulfonic Acid
Naphthalene-7-disulfonic Acid of Beilstein and Schultz
See, Naphthalene-1 : 6-disulfonic Acid
a-Naphthalene-disulfonic Acid of Ebert and Merz
See, Naphthalene-2: 7-disulfonic Acid
Naphthalene-1: 3: 5-trisulfonic Acid
S0 3 H
f^ TT f\ QJ -- OCO
ri/~v TT v>'10'--*-8^-'9'^3 ~~~" "Oo
bUsli
HO/ ^
350 DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By sulfonation of naphthalene-1 : 5-disulfonic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 179
Thorpe, Die. Chemistry, 3, 578
USES. For preparation of l-naphthylamine-4: 6: 8-trisulfonic acid
Naphthalene-1 : 3 : 6-trisulf onic Acid
Trisulfonic Acid
S0 3 H
368
FORMATION. By sulfonating naphthalene for some hours at 180 with
24 per cent oleum, or preferably by sulfonating sodium naphtha-
Iene-j8-sulfonate at a low temperature with forty per cent oleum
LITERATURE. Cain, Intermediate Products (2d Ed.), 181
Lange, Zwischenprodukte, #2662
Thorpe, Die. Chemistry, 3, 578
USES. For preparation of l-naphthol-3 :6-disulf onic acid and 1-naph-
thylamine-3 : 6 : 8-trisulfonic acid. The latter acid is the last step
prior to the manufacture of H acid (l-amino-8-naphthol-3: 6-di-
sulfonic Acid)
Naphthalic Acid
Naphthalene-1 : 8-dicarboxylic Acid (not considered herein)
Naphthalidam
See t a-Naphthylamine
Naphthalidine
/See, a-Naphthylamine
Naphthalidine-sulfonic Acid
See, Laurent's Acid
DYES CLASSIFIED BY INTERMEDIATES 351
Naphthalidinic Acid
See, Laurent's Acid
Naphthalin
See, Naphthalene
Naphthapyrogallol
1:2: 3-Trihydroxy-naphthalene (not considered herein)
a-Naphthaquinol
1 : 4-Dihydroxy-naphthalene (not considered herein)
/3-Naphthaquinol
1 : 2-Dihydroxy-naphthalene (not considered herein)
1 : 2-Naphthaquinone
See, 1: 2-Naphthoquinone (C. A. nomen.)
a-Naphthaquinone
1 : 4-Naphthoquinone (not considered herein)
/3-Naphthaquinone
See, 1 : 2-Naphthoquinone
1 : 8-Naphthasultam-2 : 4-disulf onic Acid
4-Amino-4 : 5-sultam-l : 3 : 5-naphthalene-trisulfonic Acid (C. A.
nomen.)
S0 2 -NH
S0 3 H _ = 365
3 H
FORMATION. The acid sodium l-naphthylamine-4: 8-disulfonate is sul-
f onated with two parts of 40 per cent oleum, and warmed to 80-90.
This warming is continued until a sample no longer diazotizes and
does not form a dye with diazotized sulfanilic acid
352
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Cain, Intermediate Products (2d Ed.), 201
USES. For preparation of l-amino-8-naphthol-2 : 4-disulfonic Acid
Naphthazarin (C. A. nomen.)
5 : 6-Dihy droxy-1 : 4-naphthoquinone
5 : 6-Dihydroxy-a-naphthoquinone
1 : 2-Dihydroxy-naphthoquinone
Oxy-juglone
HO
FORMATION. Crude dinitro-naphthalene (a mixture of 1:5- and 1 : 8-
dinitro-naphthalene) is treated with oleum and sulfur
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 333
Cf. Lange, Zwischenprodukte, #2759
Schultz, Farbstofftabellen (1914), #774
Thorpe, Die. Chemistry, 3, 656, 569
Dyes Derived from Naphthazarin
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
774
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Black
I '14: 205,439
I '20: 17,421
[NaHS0 3 ]
M
775
Alizarin Dark
Green W
Phenol
M
1: 2-j3-Naphthazoledione (C. A. nomen.)
See, /3-Naphthisatin
DYES CLASSIFIED BY INTERMEDIATES
o-Naphthionic Acid
See, l-Naphthylamine-2-sulfonic Acid
353
Naphthionic Acid
Naphtholic Acid
Piria's Acid
l-Naphthylamine-4-sulfonic Acid
l-Amino-naphthalene-4-sulfonic Acid
4-Amino-l-naphthalene-sulfonic Acid (C. A. numbering)
Note.C. A. nomenclature is Naphthionic Acid, but C. A. numbers
from the -SO S H group, instead of from -NH 2 group, as is the usual procedure
NH 2
S0 3 H
STATISTICS. Manufactured '17: ?
Manufactured '18: 1,462,216 Ibs.
Manufactured '19: 2,008,189 Ibs.
Manufactured '20: 3,773,191 Ibs.
FORMATION. By " baking" a-naphthylamine and sulfuric acid plus a
little oxalic acid in pans in an oven
LITERATURE. Cain, Intermediate Products (2d Ed.), 189
Lange, Zwischenprodukte, #2359
Thorpe, Die. Chemistry, 3, 590
Dyes Derived from Naphthionic Acid
Schultz
Number
for Dye
52
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Closs
A
MONOAZO DYES
Archil Substitute V
p-Nitro-aniline
91
Anthracyl Chrome
Green AD
I '14: 4,596
M'18: ?
I '20: 3,316
Picramic Acid
ACr
354
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
160
Naphthylamine
I '14: 68,281
a-Naphthol
ACr
Brown
M'17: ?
Fast Brown N
M'18: ?
M'19: ?
M'20: ?
161
Fast Red A
I '14: 46,359
/3-Naphthol
A
M '17: 191,424
M '18: 242,215
M '19: 267,582
I '20: 948
M '20: 433,989
163
Azo Rubine
I '14: 230,763
Nevile-Winther's Acid
A
M '17: 197,621
M'18: 79,779
M '19: 187,264
I '20: 1,102
M '20: 470,949
164
Fast Red VR
I '14: 20,714
l-Naphthol-5-sulfonic
ACr
M'17: ?
Acid
M'18: ?
M'19: ?
I '20: 6,290
M'20: ?
165
Azo Red A
l-Naphthol-3: 6-disul-
A
fonic Acid
166
Fast Red E
I '14: 2,473
Schaeffer's Acid
A
M'17: ?
M'18: ?
M'19: ?
M'20: ?
167
Croceine Scarlet 3BX
I '14: 13,101
Croceine Acid
A
M'17: ?
M'18: ?
M'19: ?
I '20: 651
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
355
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
168
Amaranth
I '14: 86,067
R Acid
A
M'17: 66,069
M'18: 73,539
M '19: 294,416
I '20: 110
M '20: 204,958
169
Cochineal
I '14: 32,645
G Acid
A
Red A
M'17: ?
M'18: ?
M '19: 231,519
M '20: 288,945
170
Ponceau 6R
2-Naphthol-3:6:8-
A
trisulfonic Acid
171
Chromotrope 8B
M'18: ?
Chromotropic Acid
A
DISAZO DYES
209
Terra Cotta FC
I '14: 551
Primuline or
D
Dehydro-thio-
toluidine-sulfonic
Acid
m-Phenylene-diamine
213
Fast Brown
I '14: 3,206
Resorcinol
A
M'17: ?
Naphthionic Acid
M'18: ?
(2 mols)
M'19: ?
-
M'20: ?
264
Fast Sulf on
M'19: ?
HAcid
A
Black F
I '20: 2,204
/3-Naphthol
M'20: ?
307
Congo Red
I '14: 20,629
Benzidine
D
.
M'17: ?
Naphthionic Acid
M'18: 587,153
(2 mols)
M'19: 873,734
M'20:
1,502,630
356
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
309
Glycine Red
Benzidine
D
a-Naphthyl-glycine
311
Orange TA
I '14: 602
Benzidine
D
M'17: ?
Cresol
M'18: ?
M'19: ?
M'20: ?
312
Congo Corinth G
I '14: 44,157
Benzidine
D
M'17: ?
Nevile-Winther's Acid
M'18: ?
M '19: 137,704
M '20: 242,503
313
Congo Rubine
I '14: 46,213
Benzidine
D
M'17: ?
Croceine Acid
M'18: ?
I '20: 2,601
340
Benzo Orange R
I '14: 1,073
Benzidine
D
M'17: ?
Salicylic Acid
M'18: 50,422
M'19: 42,807
I '20: 220
M'20: 86,210
356
Dianol Red 2B
I '14: 4,422
Dichloro-benzidine
D
I '20: 17,632
Naphthionic Acid
(2 mols)
363
Benzo Purpurin 4B
I '14: 351,712
Tolidine
D
M'17: ?
Naphthionic Acid
M'18: 356,522
(2 mols)
M'19: 288,021
I '20: 3,492
.
M'20: 617,629
368
Brilliant
I '14: 6,634
Tolidine
D
Purpurin 4B
Broenner's Acid
DYES CLASSIFIED BY INTERMEDIATES
357
Dyes Derived from Naphthionic Acid (continued)
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
369
Brilliant Purpurin R
I '14: 8,051
Tolidine
D
Amino-R Acid
374
Congo 4R
M'18: ?
Tolidine
D
Congo Red 4R
Resorcinol
375
Congo Corinth B
I '14: 2,196
Tolidine
D
M'19: ?
Nevile-Winther's Acid
405
Benzopurpurin 10B
I '14: 47,768
Dianisidine
. D
M'18: ?
Naphthionic Acid
M'19: ?
(2 mols)
I '20: 2,205
M'20: 41,265
407
Azo Violet
Dianisidine
D
Nevile-Winther's Acid
TRISAZO DYES
479
Dianil Black R
Benzidine
D
Chromotropic Acid
ra-Phenylene-diamine
481
Azo Corinth
Tolidine
D
Resorcinol
3- Amino- 1 - phenol-4-
sulfonic Acid
TETRAKISAZO DYES
487
Benzo Brown B
I '14: 438
m-Phenylene-diamine
D
M'20: ?
(3 mols)
Naphthionic Acid
(2 mols)
488
Toluylene Brown R
I '14: 201
3 : 5-Diamino-p-toluene-
D
sulfonic Acid
m-Phenylene-diamine
(2 mols)
Naphthionic Acid
(2 mols)
358 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Naphthionic Acid (continued)
Schultz
Number
Jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TETRAKISAZO DYES
(continued)
490
Cotton Brown A
I '14: 29,074
Benzidine
D
w-Phenylene-diamine
(2 mols)
Naphthionic Acid
(2 mols)
DlPHENYL-NAPHTHYL-
-METHANE DYE
563
New Patent Blue B
I '14: 595
Hydrol
A
I '20: 1,814
[Substitution of NH 2 by
S0 3 H; Oxidation]
/3-Naphthisatin
2-Naphthisatin
1 : 2-/3-Naphthazoledione (C. A. nomen.for ketoform)
1: 2-Diketo-l: 2-dihydro-/3-naphthindole
CO CO CO C.OH
NH
or
N
FORMATION. 0-Naphthylamine is reacted with glyoxal sodium bisul-
fite compound forming /3-naphthindol-sulfonate
. S0 3 Na
By adding acetic acid and sodium nitrite to a solution of this latter
body in warm water, there results isonitroso-naphthoxindole
/CrN.OH
Ci H<< >CO , which upon being boiled with sulfuric acid
\NH
forms the /3-naphthisatin
LITERATURE. Beilstein, Organische Chemie (2 auf.) II, 624; II spl.342
Cf. Lange, Zwischenprodukte, #2965
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthisatin
359
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
891
INDIGO GROUP DYES
Ciba Green G
I '14: 119
/3-Naphisatin (2 mols)
[Bromination]
V
892
Helindone Green G
I '20: 1,248
/3-Naphthisatin (2 mols)
[Bromination]
V
2-Naphthisatin
j 0-Naphthisatin
1-Naphthol
See, a-Naphthol
2-Naphthol
See, /3-Naphthol
a-Naphthol
1-Naphthol (C. A. nomen.)
OH
STATISTICS. Imported '14: 405,578 Ibs.
Manufactured '17: 72,329 Ibs.
Manufactured '18: 136,723 Ibs.
Manufactured '19: 135,025 Ibs.
Manufactured '20: ?
FOKMATION. (l)Naphthalene is sulfonated cold to a-naphthalene-
sulfonic acid, which is then fused with caustic soda to form the
a-naphthol. (2) a-Naphthylamine hydrochloride or sulfate is
hydrolyzed to a-Naphthol by heating with water in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 212
Lange, Zwischenprodukte, #2269-2271
Thorpe, Die. Chemistry, 3, 614
360 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITRO DYES
6
Martius Yellow
I '14: 3,295
[Dinitration]
A
I '20: 26
7
Naphthol Yellow S
I '14: 251,222
[Dinitration, Sulfona-
A
M'17: ?
tion]
M'18: ?
M'19: ?
M'20: ?
MONOAZO DYES
105
Sudan Brown
M'17: ?
a-Naphthylamine
ss
M '18: ?
M'19: ?
144
Orange I
I '14: 8,305
Sulfanilic Acid
A
M'17: ?
M'18: ?
M'19: ?
I '20: 1,323
M'20: 14,684
160
Naphthylamine
I '14: 68,281
Naphthionic Acid
ACr
Brown
M'17: ?
Fast Brown N
M'18: ?
M'19: ?
M'20: ?
172
Fast Brown 3B
I '14: 1,477
Broenner's Acid
A
180
Erio Chrome Blue
I '14: 57,000
l-Amino-2-naphthol-4-
ACr
Black B
M'17: 9,326
sulfonic Acid
M'18: ?
M'19: ?
I '20: 20,371
M'20: 29,255
183
Erio Chrome Black T
I '14: 129,550
Nitro-1 -amino-2-naph-
ACr
M'18: ?
thol-4-sulfonic Acid
M'19: ?
I '20: 2,624
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthol (continued)
361
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
212
Fast Brown G
I '14: 17,407
Sulf anilic Acid (2 mols)
A
Acid Brown G
I '20: 485
214
Fast Brown
I '14: 2,000
Xylidine-sulfonic Acid
A
(2 mols)
INDOPHENOL DYE
619
Indophenol
M'17: ?
Nitroso-dimethyl-
V
M'18: ?
aniline or
M 19: 126,611
Dimethyl-p-
M'20: ?
phenylene-diamine
SULFUR DYE
731
Thiophor Indigo CJ
Dimethyl-p-phenylene-
S
diamine
[S+NasS]
895
INDIGO GROUP DYE
Alizarin Indigo 3R
I '20: 3,514
Dibromo-isatin
V
Chloride
0-Naphthol
2-Naphthol (C. A. nomen.)
STATISTICS. Imported '14: 1,264,525 Ibs.
Manufactured '17: 5,952,772 Ibs.
Manufactured '18: 5,254,637 Ibs.
Manufactured '19: 4,916,416 Ibs.
Manufactured '20: 11,920,714 Ibs.
FORMATION. Naphthalene is sulfonated to jS-naphthalene-sulfonic acid;
this is fused with caustic soda, and the resulting /3-naphthol is
isolated and purified
LITERATURE. Cain, Intermediate Products (2d Ed.), 212
Thorpe, Die, Chemistry, 3, 614, 622
362
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 0-Naphthol
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITROSO DYE
2
Gambine Y
[Nitroso-derivative]
M
Fast Printing Green
MONOAZO DYES
36
Sudan I
I '14: 4,554
Aniline
S3
Oil Orange
M'17: 32,455
M'18: 29,670
M'19: 75,868
M '20: 116,624
46
m-Nitraniline
m-Nitro-aniline
MF
Orange
56
Paranitraniline Red
I '14: 49,847
p-Nitro-aniline
MF
M'17: ?
M'18: ?
M'19: ?
M'20: ?
72
Pigment Orange R
p-Nitro-o-toluidine
CL
MF
73
Pigment Fast
I '14: 49,708
m-Nitro-p-toluidine
CL
Red HL
M'17: ?
Lithol Fast
M'18: ?
Scarlet R
M'19: ?
Helio Fast Red RL
I '20: 1,001
M'20: ?
74
Tannin Orange R
I '14: 2,202
o- and p-Amino-benzyl-
B
I '20: 347
dimethyl-amine
76
Sudan II
I '14: 501
Xylidine
ss
M'17: 27,595
M'18: 23,692
M'19: ?
I
M'20: 170,658
86
Azarine S
2-Amino-4: 6-dichloro-
M
phenol
93
Pigment Purple A
I '14: 99
o-Anisidine
CL
Sudan R
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued)
363
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
97
Chloranisidine
Chloro-anisidine
MF
Scarlet
98
Naphthol Pink
I '14: 99
p-Nitro-o-anisidine
MF
Nitrosamine
PinkBX
99
Tuscaline Orange G
ra-Nitro-o-anisidine
CL
*
MF
106
Carmine Naphth
I '14: 6,565
a-Naphthylamine
CL
Garnet
M'17: ?
Autol Red RL
M'18: ?
M'19: ?
M'20: ?
115
Azo Turkish Red
/3-Naphthylamine
MF
126
Indoin Blue R
I '14: 15,353
Safranine
B
Union Blue R
M'17: ?
or
M'18: ?
ra-Tolylene-diamine
o-Toluidine
Aniline
131
Permanent Orange R
2-Amino-6-chloro-ben-
CL
zene-sulfonic Acid
132
Lake Red P
I '14: 60,345
p-iNitro-aniline-a-sul-
CL
M '17: ?
fonic Acid
M'18: ?
M'19: ?
I '20: 1,750
145
Orange II
I '14: 128,877
Sulfanilic Acid
A
M'17: 712,586
M'18: 916,890
M'19:
1,133,925
I '20: 2,265
M'20:
1,850,341
364
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued)
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
148
MONOAZO DYES
(continued)
Fast Orange
I '14: 1,250
M'17: ?
o-Nitro-aniline-p-
sulfonic Acid
CL
151
Orange T and HO
I '14: 90,747
M'17: ?
M'19: ?
I '20: 20
M'20: ?
o-Toluidine-m-sulfonic
Acid
A
153
Lake Red C
I '14: 306,607
M'19: ?
I '20: 4,105
M'20: ?
2-Chloro-5-toluidine-
4-sulfonic Acid
CL
156
Acid Alizarin
Violet N
Palatine Chrome
Violet
I '14: 1,199
M'19: ?
M'20: ?
o-Amino-phenol-p-sul-
fonic Acid
ACr
159
Acid Alizarin
Black R
I '14: 16,800
M'19: ?
I '20: 439
M'20: ?
2-Amino-6-nitro-l-
phenol-4-sulfonic
Acid
M
161
Fast Red A
I '14: 46,359
M'17: 191,424
M '18: 242,215
M'19: 267,582
I '20: 948
M'20: 433,989
Naphthionic Ac'd
A
162
Brilliant Fast Red G
Laurent's Acid
A
"~173 "
Lithol Red R
I '14: 281,963
M 17: ?
M '18: 353,104
M'19: 269,169
M'20: ?
2-Naphthylamine-l-
sulfonic Acid
CL
DYES CLASSIFIED BY INTERMEDIATES
365
Dyes Derived from /3-Naphthol (continued)
Schultz
Number
jo? Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
174
Double Brilliant
I '14: 210,429
Broenner's Acid
A
Scarlet
M'17: ?
M'20: ?
175
Ponceau for Silk
I '14: 727
2-Naphthylamine-8-
A
and 5-sulf onic Acids
181
Palatine Chrome
I '14: 248,721
1 - Amino-2-naphthol-4-
ACr
Black 6B
M'17: ?
sulfonic Acid
Salicine Black U
M '18: 469,159
M '19: 739,372
M'20: 2,001
M'20:
1,074,248
184
Erio Chrome
I '14: 96.570
Nitro-l-amino-2-naph-
ACr
Black A
M'17: ?
thol-4-sulfonic Acid
M'18: ?
M '19: 686,700
' '**" '
I '20: 14,262
M'20: ?
185
Anthracene Chrome
I '14: 51,577
2-Amino-3-"naphthol-6-
M
Black
I '20: 2,339
sulfonic Acid
193
Clayton Cloth Red
I '14: 100
Dehydro-thio-p-
A
Stanley Red
M'18: ?
toluidine-sulfonic
M'19: ?
Acid
M'20: ?
200
Lake Red D
I '14: 2,428
Anthranilic Acid
CL
M'17: ?
M'18: ?
M'19: ?
M'20: ?
DISAZO DYES
223
Sudan III
I '14: 2,409
Amino-azo-benzene
S3
M'17: ?
MF
M'18: ?
M'19: ?
M'20: ?
366
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
232
(continued)
Sudan IV
I '14: 51
o-Amino-azo-toluene
ss
M'17: 13,334
M'18: 14,904
M'19: ?
MF
M'20: ?
239
Azotol C
Amino-chrysoidine
MF
or
p-Amino-acetanuide and
jw-phenylene-diamine
or
.AT-Dimethyl-p: p'-dia-
mino-azo-benzene
240
Janus Red B
I '14: 250
I '20: 176
m-Amino-phenyl-tri-
methyl-ammonium
Chloride
B
w-Toluidine
246
Cloth Scarlet G
I '14: 9
Amino-azo-benzene-
A
M'17: ?
sulfonic Acid
M'18: ?
M'19: ?
M'20: ?
247
Double Scarlet
Scarlet EC
I '14: 39,522
M'17: ?
Amino-azo-benzene-
disulfonic Acid
A
M'18: 74,203
M'19: ?
M'20: ?
252
Cloth Scarlet R
o-Amino-azo-toluene-
M
sulfonic Acid
260
Erio Chrome
I '14: 882
Sulfanilic Acid
ACr
Verdon A
m-Amino-2>-cresol
264
Fast Sulf on Black F
M'19: ?
I '20: 2,204
M'20: ?
Naphthionic Acid
HAcid
A
DYES CLASSIFIED BY INTERMEDIATES
367
Dyes Derived from |3-Naphthol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
271
DISAZO DYES
{continued}
Diamine Blue 6G
Amino-G Acid
l-Amino-2-naphthol
Ethyl Ether
D
288
Acid Alizarine
Black SE
Palatine Chrome
Black F
I 14: 19,185
I '20: 34,302
2: 6-Diamino-phenol-
4-sulfonic Acid
/S-Naphthol (2 mols)
ACr
289
Acid Alizarine
Black SN
Palatine Chrome
Black S
M'17: ?
M'18: ?
M'19: ?
2 : 6-Diamino-phenol-4-
sulf onic Acid
Schaeffer's Acid
ACr
318
Benzidine Puce
Benzidine
j8-Naphthol (2 mols)
MF
322
Trisulfon Violet B
I 14: 1,124
M'17: ?
M'18: ?
M'19: ?
I '20: 7,927
M'20: ?
Benzidine
l-Naphthol-3:6:8-tri-
sulfonic Acid
D
378
Trisulfon Blue R
I '14: 911
M'19: ?
M'20: ?
l-Naphthol-3:6:8-tri-
sulfonic Acid
Tolidine
D
400
Milling Scarlet 4R
Acid Anthracene
Red3B
I '14: 18,330
I '20: 2,336
o-Tolidine-disulfonic
Acid
0-Naphthol (2 mols)
A
406
Diazurine B
Dianisidine
l-Naphthylamine-6-
sulfonic Acid (2 mols)
/3-Naphthol (2 mols on
fiber)
D
368
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued)
Schullz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
408
Dianisidine Blue
I '14: 240
Dianisidine
D
iS-Naphthol (2 mols)
409
Trisulfon Blue C
I '14: 813
Dianisidine
D
l-Naphthol-3:6:8-
trisulfonic Acid
419
Chicago Blue RW
I '14: 15,176
Dianisidine
D
M'19: ?
1 -Amino-8-naphthol-
I '20: 351
2 : 4-disulf onic Acid
M'20: ?
434
Coomassie Navy
I '20: 42,357
1 : 4-Naphthylene-dia-
A
Blue
mine-2-suLfonic Acid
RAcid
DlPHENYL-NAPHTHYL-
METHANE DYE
566
Wool Green S
I '14: 60,073
Ketone
A
M'17: ?
[Sulfonation]
M'19: ?
I '20: 127,764
M '20: 212,362
OXAZINE DYES
649
New Blue R
I '14: 32,509
Nitroso-dimethyl-
B
Meldola's Blue
M'17: ?
aniline
Cotton Blue
M'18: 22,613
M'19: ?
I '20: 5,240
M'20: ?
650
New Blue B
Nitroso-dimethyl-
B
aniline (2 mols)
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthol (continued)
369
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
(continued)
651
New Methylene
Nitroso-dimethyl-
B
Blue GG
aniline
[Dimethyl-amine,
Oxidation]
or
[Meldola's Blue, Di-
methyl-amine, Oxi-
dation]
652
New Fast Blue F
I '14. 2,502
Nitroso-dimethyl-
B
aniline
Hydrol
or
[Meldola's Blue;
Hydrol]
a-Naphthol-carboxylic Acid
See, l-Hydroxy-2-naphthoic Acid
/3-Naphthol-carboxylic Acid
See, 3-Hydroxy-2-naphthoic Acid
l-Naphthol-3 : 6-disulf onic Acid (C. A. nomen.)
R G Acid
G R Acid
a-Naphthol-disulfonic Acid R G
OH
H0 3 S
S0 3 H
STATISTICS. Manufactured '19: ?
Manufactured '20: ?
370
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. (1) By fusing sodium naphthalene-l:3: 6-trisulfonate
with half its weight of caustic soda and half its weight of water in
an autoclave. (2) By diazotizing l-naphthylamine-3 : 6-disulfonic
acid and adding to boiling dilute sulfuric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 218
Lange, Zwischenprodukte, #2636
Thorpe, Die. Chemistry, 3, 619
Dyes Derived from l-Naphthol-3: 6-disulfonic Acid
Schullz
Number
Jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
64
Azo Acid Red B
1 '14: 78,305
p-Amino-acetanilide
A
Lanafuchsine
M'17: ?
t - '
M'18: ?
M'19: 15,272
I '20: 674
M'20: ?
81
Palatine Scarlet A
I '14: 7,510
m-Xylidine
A
Brilliant Cochineal
2R
109
Palatine Red A
I '14: 300
a-Naphthylamine
A
M'18: ?
M'19t ?
165
Azo Red A
Naphthionic Acid
A
DISAZO DYES
225
Croceine AZ
I '14: 500
Amino-azo-benzene
A
I '20: 100
l-Naphthol-3: 8- disulfonic Acid (C. A. nomen.)
Andresen's Acid
e-Acid or Epsilon Acid
a-Naphthol--disulfonic Acid
Disulfo Acid E
H0 3 S OH
S0 3 H
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Manufactured '20: ?
371
FORMATION. Heat a solution of the acid sodium salt of 1-naphthyl-
amine-3: 8-disulfonic acid in an autoclave for 5 hours at 180
LITERATURE. Cain, Intermediate Products (2d Ed.), 219
Lange, Zwischenprodukte, #2638, 2639
Thorpe, Die. Chemistry, 3, 619
Dyes Derived from l-Naphthol-3 : 8-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
100
Eosamine B
I '14: 1,914
ra-Amino-p-cresol-
A
I '20: 1,600
methyl ether
117
Erica 2 GN
I '14: 1,171
Dehydro-thio-p-tolui-
D
M'19: ?
dine
I '20: 337
121
Erica B
I 14: 5,349
Dehydro-thio-m-
D
M'19: ?
xylidine
I '20: 2,393
DISAZO DYES
325
Columbia Blue R
I '14: 3,071
Benzidine
D
l-Amino-8-naphthol-4-
sulfonic Acid
387
Columbia Blue G
I '14: 7,094
Tolidine
D
l-Amino-8-naphthol-4-
sulfonic Acid
TEISAZO DYES
451
Congo Fast Blue R
I '14: 4,449
Tolidine
D
M'18: ?
a-Naphthylamine
I '20: 723
l-Naphthol-3: 8-disul-
fonic Acid (2 mols)
456
Congo Fast Blue B
I '14: 100,495
Dianisidine
D
Benzo Fast Blue B
I '20: 1,821
a-Naphthylamine
l-Naphthol-3: 8-disul-
fonic Acid (2 mols
372
DYES CLASSIFIED BY INTERMEDIATES
l-Naphthol-4: 8-disulfonic Acid (C. A. nomen.)
Schoellkopf s Acid
a-Naphthol-disulfonic Acid Sch
a-Naphthol-5-disulfonic Acid
a-Naphthol-disulfonic Acid S
S Acid
H0 3 S OH
SO 3 H
STATISTICS. Manufactured '19: ?
FORMATION. From l-naphthylamine-4 : 8-disulfonic acid by diazotizing
and running this diazo solution, into dilute sulfuric acid. This
latter is now boiled to complete the decomposition
LITERATURE. Cain, Intermediate Products (2d Ed.), 219
Lange, Zwischenprodukte, #2647
Thorpe, Die. Chemistry, 3, 620
Dyes Derived from l-Naphthol-4: 8-disulfonic Acid
Schultz
Number
jar Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
80
MONOAZO DYES
Wool Scarlet R
I '14: 39,888
Xylidine
A
95
110
Azo Cochineal
Cochineal Scarlet B
Buffalo Rubine
I '14: 952
o-Anisidine
a-Naphthylamine
A
A
118
226
Geranine
DISAZO DYES
Croceine B
I '14: 18,917
M'19: ?
I '20: 527
Dehydro-thio-p-
toluidine
Amino-azo-benzene
D
A
235
i
Croceine 3B
M'19: ?
M'20: ?
Amino-azo-toluene
A
321
Heliotrope 2B
I '14: 1,473
I '20: 60
Benzidine
Croceine Acid
D
DYES CLASSIFIED BY INTERMEDIATES 373
2-Naphthol-3 : 6-disulf onic Acid
See, R Acid
2-Naphthol-3 : 7-disulf onic Acid (C. A. nomen.)
j3-Naphthol-5-disulfonic Acid
/3-Naphthol-disulfonic Acid F
_ p H _
CioH 8 7 S 2 -
FORMATION. 2-Naphthol-7-sulfonic acid is heated with 66 sulfuric
acid for a considerable time at 120
LITERATURE. Lange, Zwischenprodukte, #2653, 2654
Thorpe, Die. Chemistry, 3, 627
Dye Derived from 2-Naphthol-3 : 7-disulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
402
Diamine Blue
Ethoxy-bcnzidine
D
Black E
Gamma Acid
2-Naphthol-6: 8-disulfonic Acid
See, G Acid
a-Naphthol-6-disulfonic Acid
See, l-Naphthol-4 : 8-disulfonic Acid
a-Naphthol-e-disulfonic Acid
See, l-Naphthol-3 : 8-disulfonic Acid
a-Naphthol-disulfonic Acid GR
See, l-Naphthol-3 : 6-disulf onic Acid
a-Naphthol-disulfonic Acid RG
See, l-Naphthol-3 : 6-disulf onic Acid
374 DYES CLASSIFIED BY INTERMEDIATES
a-Naphthol-disulfonic Acid S
See, l-Naphthol-4 : 8-disulf onic Acid
a-Naphthol-disulfonic Acid Sch
See, l-Naphthol-4: 8-disulf onic Acid
0-Naphthol-a-disulfonic Acid
See, R Acid
/3-Naphthol-/3-disulf onic Acid
See, G Acid
/3-Naphthol-7-disulf onic Acid
See, G Acid
j8-Naphthol-5-disulfonic Acid
See, 2-Naphthol-3: 7-disulfonic Acid
/3-Naphthol-disulf onic Acid C
2-Naphthol-4: 8-disulf onic Acid (not considered herein)
0-Naphthol-disulf onic Acid P
See, 2-Naphthol-3: 7-disulfonic Acid
0-Naphthol-disulfonic Acid G
See, G Acid
0-Naphthol-disulf onic Acid R
See, R Acid
Naphtholic Acid
See, Naphthionic Acid
l-Naphthol-4-sulf onic Acid
See, Nevile-Winther's Acid
DYES CLASSIFIED BY INTERMEDIATES 375
l-Naphthol-5-sulfonic Acid (C. A. nomen.)
LAcid
Cleve's Acid
a-Naphthol-sulfonic Acid C
a-Naphthol-sulfonic Acid L
224
STATISTICS. Imported '14: 25,126 Ibs.
Manufactured ' 18 : ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. (1) From naphthalene-1 : 5-disulfonic acid by fusion with
caustic soda. (2) From l-naphthylamine-5-sulfonic acid by diazo-
tizing, and boiling the diazo solution with dilute sulfuric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 218
Lange, Zwischenprodukte, #2422-2424
Thorpe, Die. Chemistry, 3, 617
Dyes Derived from l-Naphthol-5-sulfonic Acid
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manujacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
78
Cochineal Scarlet 4R
Xylidine
A
108
Double Ponceau R
a-Naphthylamine
A
164
Fast Red VR
I '14: 20,714
Naphthionic Acid
ACr
M'17: ?
M'18: ?
M'19: ?
I '20: 6,290
M'20: ?
376
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from l-Naphthol-5-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
275
Diamond Black F
I '14:-462,306
Amino-salicylic Acid
ACr
M'17: ?
a-Naphthylamine
M'18: ?
M' 19: 222,938
I '20: 2,226
M'20: ?
411
Benzoazurine 3G
I '20: 201
Dianisidine
D
l-Naphthol-5-sulfonic
Acid (2 mols)
2-Naphthol-l-sulfonic Acid
Tobias Acid
(Falsely called /3-naphthyl-sulfuric Acid)
S0 3 H
C0 OH
= C 10 H 8 4 S =
STATISTICS. Manufactured in 1918, 1919, 1920 in indeterminate
amounts
FORMATION. By sulfonating /3-naphthol with 2-2J^ parts of 90-92
per cent sulfuric acid at about 40
LITERATURE. Cain, Intermediate Products (2d Ed.), 222
Lange, Zwischenprodukte, #2427
Thorpe, Die. Chemistry, 3, 624
USES. For preparation of 2-naphthylamine-l-sulfonic acid
2-Naphthol-6-sulf onic Acid
See, Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES
2-Naphthol-7-sulfonic Acid (C. A. nomen.)
/3-Naphthol-5-sulfonic Acid
jft-Naphthol-sulfonic Acid F
FAcid
Monosulfonic Acid F
Cassella's Acid
377
H0 3 S/\/\OH _ r H0 ,_
I I | OioM 8 (J 4 o
224
STATISTICS. Imported '14: 1,996 Ibs.
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. By fusing sodium naphthalene-2 : 7-disulfonate with
caustic soda solution in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 224
Lange, Zwischenprodukte, #2434
Thorpe, Die. Chemistry, 3, 625
Dyes Derived from 2-Naphthol-7-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class aj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
56
Paranitraniline Red
I '14: 49,847
p-Nitro-aniline
MF
M'17: ?
[0-Naphthol]
M'18: ?
M'19: ?
2-Naphthol-8-sulfonic Acid
See, Croceine Acid
a-Naphthol-sulfonic Acid 5
l-Naphthol-8-sulfonic Acid (not considered herein)
378 DYES CLASSIFIED BY INTERMEDIATES
a-NaphthoI-sulf onic Acid C
See, l-Naphthol-5-sulfonic Acid
a-Naphthol-sulfonic Acid L
/See, l-Naphthol-5-sulfonic Acid
a-Naphthol-sulfonic Acid NW
See, Nevile-Winther's Acid
a-Naphthol-sulfonic Acid S
l-Naphthol-8-sulfonic Acid (not considered herein)
/3-Naphthol-a-sulfonic Acid of Armstrong and Schultz
See, Schaeffer's Acid
0-Naphthol-a-sulfonic Acid (of Bayer & Go's patents)
See, Croceine Acid
/3-Naphthol-/3-sulf onic Acid
See, Schaeffer's Acid
j8-Naphthol-7-sulfonic Acid
2-Naphthol-5-sulfonic Acid (not considered herein)
/3-Naphthol-6-sulfonic Acid
See, 2-Naphthol-7-sulfonic Acid
/3-Naphthol-sulf onic Acid B
See, Croceine Acid
/3-Naphthol-sulf onic Acid F
See, 2-Naphthol-7-sulfonic Acid
/3-Naphthol-sulf onic Acid S
See, Schaeffer's Acid
DYES CLASSIFIED BY INTERMEDIATES
/3-Naphthol-sulfonic Acid Schaeffer
See, Schaeffer's Acid
379
l-Naphthol-3: 6: 8-trisulfonic Acid (C. A. nomen.)
H0 3 S OH
H0 3 S
S0 3 H
^ 384
STATISTICS. Imported '14: 6,443 Ibs.
Manufactured 'IS: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. From l-naphthylamine-3: 6: 8-trisulfonic acid by diazo-
tizing in the presence of a large excess of sulfuric acid and then
boiling and purifying
LITERATURE. Cain, Intermediate Products (2d Ed.), 221
Lange, Zwischenprodukte, #2785, 2786
Thorpe, Die. Chemistry, 3, 621
Dyes Derived from l-Naphthol-3: 6: 8-trisulfonic Acid
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
322
Trisulfon Violet B
I '14: 1,124
Benzidine
D
M'17: ?
/3-Naphthol
M'18: ?
M'19: ?
I '20: 7,927
.
M'20: ?
378
Trisulfon Blue R
I '14: 911
Tolidine
D
M'19: ?
j8-Naphthol
M'20: ?
409
Trisulfon Blue B
I '14: 813
Dianisidine
D
jS-Naphthol
380 DYES CLASSIFIED BY INTERMEDIATES
2-Naphthol-3 : 6: 8-trisulfonic Acid (C. A. nomen.)
0-Naphthol-trisulfonic Acid
H0 3 S
H0 3 S
OH
S0 3 H
STATISTICS. Manufactured '19: ?
FORMATION. From /3-naphthol by sulfonation with 2 parts of con-
centrated sulfuric acid at 70-80, then with 2 more parts of concen-
trated sulfuric acid at 120, and finally with 2 parts of 40 per cent
oleum at 150
LITERATURE. Cain, Intermediate Products (2d Ed.), 229
Lange, Zwischenprodukte, #2792
Thorpe, Die. Chemistry, 3, 628
Ullmann, Enzy. tech. Chemie, 8, 351
Dyes Derived from 2-Naphthol-3 : 6 : 8-trisulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
170
Ponceau 6R
Naphthionic Acid
A
DISAZO DYE
228
Ponceau 5R
I '14: 2,880
Amino-az o-benzene
A
Erythrine P
M'17: ?
M'18: ?
jS-Naphthol-trisulfonic Acid
See, 2-Naphthol-3: 6: 8-trisulfonic Acid
a-Naphthol-trisulfonic Acid S
l-Naphthol-2: 4: 8-trisulfonic Acid (not considered herein)
Naphtho-picric Acid
2:4: 5-Trinitro-l-naphthol (not considered herein)
DYES CLASSIFIED BY INTERMEDIATES 381
1 : 2-Naphthoquinone ((7. A. nomen.)
0-Naphthaquinone
1 : 2-Naphthaquinone
O
=rO
FORMATION. From Orange II as follows: Sulfanilic acid is diazotized
and coupled with /3-naphthol to form Orange II. This azo dye is
reduced with stannous chloride to l-amino-2-naphthol, which is
oxidized with sodium bichromate and sulfuric acid to jS-naphtho-
quinone
LITERATURE. Thorpe, Die. Chemistry, 3, 654
Lange, Zwischenprodukte, #23, 648, 2408
Dye Derived from 1 : 2-Naphthoquinone
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
THIAZINE DYE
667
Brilliant Alizarin
I '14: 19,481
Ethyl-sulfobenzyl-p-
M
BlueG
M'19: ?
phenylene-diamine-
Indochromine T
I '20: 3,214
thiosulfonic Acid
M'20: ?
1: 2-Naphthoquinone-4: 6-disulfonic Acid
/3-Naphthoquinone-4 : 6-disulfonic Acid
3:4-Dihydro-3:4-diketo-l: 7-naphthalene-disulfonic Acid (C. A
nomen.)
H0 3 S
=0
382
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. l-Nitroso-2-naphthol-6-sulfonic acid is treated with bi-
sulfite forming l-amino-2-naphthol-4: 6-disulfonic acid. This latter
body is now oxidized with nitric acid under 15, resulting in 1:2-
naphthoquinone-4: 6-disulfonic acid
LITERATURE. Ullmann, Enzy. tech. Chemie, 8, 358
Cf. Lange, Zwischenprodukte, #2408
Thorpe, Die. Chemistry, 3, 657
Dyes Derived from l:2-Naphthoquinone-4: 6-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
THIAZINE DYES
666
Indochromogen S
Diethyl - p - phenylene-
diamine-thiosulfonic-
M
Acid
667
Brilliant Alizarin
BlueG
I '14: 19,481
M'19: ?
Dimethyl-p-phenylene-
diamine-thiosulfonic
M
Indochromine T
I '19: 3,214
M'20: ?
Acid
/3-Naphthoquinone-4 : 6-disulfonic Acid
See, 1: 2-Naphthoquinone-4: 6-disulfonic Acid
1 : 2-Naphthoquinone -4-sulf onic Acid
/3-Naphthoquinone-4-sulfonic Acid
3:4-Dmydro-3:4-diketo-l-naphthalene-sulfonic Acid (C. A
DYES CLASSIFIED BY INTERMEDIATES
383
FORMATION. 2-Amino-l-naphthol-4-sulfonic acid or l-amino-2-naph-
thol-4-sulfonic acid is oxidized with nitric acid
LITERATURE. Ullmann, Enzy. tech. Chemie, 8, 358
Thorpe, Die. Chemistry, 3, 657
Cf. Lange, Zwischenprodukte, #2631
Dyes Derived from 1 : 2-Naphthoquinone-4-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
656
OXAZINE DYES
Alizarin Green G
M'19: ?
l-Amino-2-naphthol-6-
sulfonic Acid
M
657
Alizarin Green B
I 14: 551
2-Ammo-l-naphthol-4-
sulfonic Acid
M
fi-Naphthoquinone-4-sulf onic Acid
See, 1 : 2-Naphthoquinone-4-sulfonic Acid
Naphtho-resorcin
1 : 3-Dihydroxy-naphthalene (not considered herein)
Naphthoyl-benzoic Acid
o-1-Naphthoyl-frenzoic Acid (C. A. nomen.)
CO. OH _
\
FORMATION. From phthalic anhydride and naphthalene by heating
together in the presence of benzene and aluminium chloride
LITERATURE. Lange, Zwischenprodukte, #2812
Schultz, Farbstofftabellen (1914), #758
384 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Naphthoyl-benzoic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
758
Sirius Yellow G
CL
Naphthsultam-disulfonic Acid S
l-Naphthylamine-2 : 4 : 8-trisulf onic Acid (not considered herein)
1-Naphthylamine
See, a-Naphthylamine
2-Naphthylamine
See, /3-Naphthylamine
a-Naphthylamine
1-Naphthylamine (C. A. nomen.)
a-Amino-naphthalene
Naphthalidam
Naphthalidine
NH 2
STATISTICS. Imported '14: 112,226 Ibs.
Manufactured '17: 3,516,686 Ibs.
Manufactured '18: 2,671,601 Ibs.
Manufactured '19: 1,552,828 Ibs.
Manufactured '20: 5,177,547 Ibs.
FORMATION. Naphthalene is mononitrated, using mixed acid, and the
resulting a-nitro-naphthalene is reduced with iron and hydrochloric
acid to a-naphthylamine
LITERATURE. Cain, Intermediate Products (2d Ed.), 181
Lange, Zwischenprodukte, #2262
Thorpe, Die. Chemistry, 3, 586
DYES CLASSIFIED BY INTERMEDIATES
385
Dyes Derived from a-Naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
105
Sudan Brown
M'17: ?
a-Naphthol
ss
M'18: ?
M'19: ?
106
Carmine Naphth
I '14: 6,565
0-Naphthol
CL
Garnet
M'17: ?
Autol Red RL
M.'IS: ?
M'19: ?
M'20: ?
107
Sulfamine Brown A
I '14: 132
Nitroso-/3-naphthol
M
M'18: ?
M'19: ?
I '20: 2,630
M'20: ?
108
Double Ponceau R
l-Naphthol-5-sulfonic
A
Acid
109
Palatine Red A
I '14: 300
l-Naphthol-3: 6-disul-
A
M'18: ?
fonic Acid
M'19: ?
110
Buffalo Rubine
l-Naphthol-4:6-disul-
A
fonic Acid
111
Fast Red BT
M'17: ?
Schaeffer's Acid
A
M'18: ?
M'19: ?
112
Fast Red B
I '14: 25,821
RAcid
A
Bordeaux B
M'17: 120,595
M'18: 200,415
M'19: 161,862
I '20: 7,882
M'20: 217,406
113
Crystal Ponceau
I '14: 628
GAcid
A
114
Chromotrope 10B
M'19: ?
Chromotropic Acid
A
386 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
218
NigrophorBASF
l-Amino-8-naphthol-5-
sulfonic Acid
MF
2: 5-Dichloro-aniline
220
Palatine Black A
I '14: 299,274
I '20: 200
l-Amino-8-naphthol-4-
sulfonic Acid
A
Sulfanilic Acid
241
Neutral Gray G
I '14: 2,546
M'19: ?
Aniline
Gamma Acid
D
I '20: 3,472
M'20: ?
243
Coomassie Wool
Black R
Acetyl-p-phenylene-
diamine
A
Schaeffer?s Acid
244
Coomassie Wool
Black S
M'18: ?
M'19: ?
Acetyl-p-phenylene-
diamine
A
R Acid
245
Nyanza Black B
p-Nitro-aniline
[Reduced]
Gamma Acid
D
256
Sulfon Black 3B
Metanilic Acid
A
Phenyl-1-naphthyl-
amine-8-sulf onic Acid
257
Sulfoncyanine
I '14: 145,694
M'17: ?
M'18: ?
M'19: ?
Metanilic Acid
Phenyl- or Tolyl-
1-naphthylamine-
8-suif onic Acid
A
I '20: 18,327
M'20: ?
258
Naphthalene Acid
Black 4B
I '14: 7,994
Metanilic Acid
l-Naphthylamine-6-
and 7-sulfonic Acids
A
261
Buffalo Black 10B
M'17: ?
SuKanilic Acid
A
M'18: ?
HAcid
M'19: ?
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
387
Dyes Derived from a-Naphthylamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
262
Victoria Black B
I '14: 557
Sulfanilic Acid
A
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid
263
Jet Black R
Aniline-2 : 4-disulf onic
A
Acid
Phenyl-a-naphthyl-
amine
265
Sulfoncyanine
I '14: 69,590
Laurent's Acid
A
Black B
M'17: ?
Phenyl-1-naphthyl-
M'18: ?
amine-8-sulfonic Acid
M'19: ?
M'20: ?
266
Naphthylamine
I '14: 152,141
Freund's Acid
A
Black D
M'17: ?
a-Naphthylamine
M'18: 29,724
(2 mols)
M'19: ?
I '20: 1,687
M'20: ?
267
Anthracite Black
I '14: 99
Freund's Acid
A
M'17: ?
Diphenyl-w-phenylene-
I '20: 220
diamine
267
Phenylene Black
l-Naphthylamine-4: 7-
A
disulf onic Acid
Diphenyl-m-phenylene-
diamine
268
Naphthyl Blue
Black N
l-Naphthylamine-4: 6-
and 4 : 7-disulf onic
A
Acids
1 -Amino-2-naphthol
Ethyl Ether
269
Naphthol Black 6B
I '14: 120,512
I '20: 1,500
l-Naphthylamine-4: 6-
and 4: 7-disulf onic
A
M'20: ?
Acids
RAcid
388
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
Schuliz
Number
Jor Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
272
(continued)
Naphthol Black B
Brilliant Black B
I '14: 103,598
M'19: ?
Amino-G Acid
R Acid
A
I '20: 50
273
Diaminogen Blue BB
I '14: 8,308
M'17: ?
I '20: 5,936
Acetyl-1 : 4-diamino-
naphthalene-6-sul-
fonic Acid
SchaefFer's Acid
D
274
Diaminogen B
I '14: 313,629
I '20: 18,120
Acetyl-1 : 4-diamino-
naphthalene-6-sul-
fonic Acid
D
Gamma Acid
275
Diamond Black F
I '14:-^62,306
M'17: ?
Amino-salicylic Acid
Nevile-Winther's Acid
ACr
M '18: ?
M'19: 222,938
I '20: 2,226
M'20: ?
or l-Naphthol-5-
sulfonic Acid
276
Diamond Green B
I '14: 8,622
M'18: ?
I '20: 4,061
Amino-salicylic Acid
1 : 8-Dihydroxy-naph-
thalene-4-s u 1 f o n i c
Acid
ACr
278
Biebrich Patent
Black
l-Naphthylamine-6-
and 7-sulf onic Acids
A
etc.
290
Violet Black
Nevile-Winther's Acid
D
p-Phenylene-diamine or
Amino-acetanilide
382
Azo Mauve B
M'17: ?
Tolidine
D
M'20: ?
HAcid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
389
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cclion
Gloss
DISAZO DYES
(continued}
432
Diamine Cutch
1 : 5-Naphthylene-dia-
D
Naphthylene Violet
mine-3 : 7-disulf onic
Acid
a-Naphthylamine
(2 mols)
TRISAZO DYES
435
Janus Brown B
Trimethyl-m-amino-
B
phenyl-ammonium
Chloride
Aniline
m-Phenylene-diamine
or
p-Amino-benzyl-
diethyl-amine
Resorcinol
m-Phenylene-diamine
441
Diazo Blue
M'19: ?
Benzidine
D
Black RS
M'20: ?
H Acid (2 mols)
442
Direct Black V
I '14: 145,738
Benzidine
D
2R Acid
Gamma Acid
443
Direct Indone
Benzidine
D
Blue R
2R Acid
H Acid
446
Benzo Olive
I '14: 1,149
Benzidine
D
Salicylic Acid
HAcid
447
Benzo Gray S
I '14: 802
Benzidine
D
Salicylic Acid
Nevile-Winther's Acid
450
Benzo Black Blue R
Tolidine
D
Nevile-Winther's Acid
(2 mols)
390 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
451
TRISAZO DYES
(continued)
Congo Fast Blue R
I '14: 4,449
M'19: ?
I '20: 723
Tolidine
l-Naphthol-3: 8-disul-
fonic Acid (2 mols)
D
452
Benzo Indigo Blue
Tolidine
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid (2 mols)
D
456
Congo Fast Blue B
Benzo Fast Blue B
I '14: 100,495
I '20: 1821
Dianisidine
l-Naphthol-3 : 8-disul-
fonic Acid
D
459
Benzo Black Blue G
Benzidine-disulfonic
Acid
Nevile-Winther's Acid
(2 mols)
D
460
653
Benzo Black Blue 5G
OXAZINE DYE
Nile Blue A
I '14: 602
I '14: 1,518
I '20: 1,241
B enzidine-disulf onic
Acid
1 : 8-Dihydroxy-naph-
thalene-4-s u 1 f o n i c
Acid (2 mols)
5-Diethylamino-2-
nitroso-phenol
D
B
671
AZINE DYES
Induline Scarlet
I '14: 198
I '20: 154
Ethyl-p-toluidine
B
672
Azo Carmine G
I '14: 17,500
M'17: ?
M'18: ?
M'19: ?
I '20: 196
M'20: ?
Aniline (3 mols)
[Disulfonation]
A
673
Azo Carmine B
I '20: 549
Aniline (3 mols)
[Trisulfonation]
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthylamine (continued)
391
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
(continued)
674
Rosinduline 2G
I '20: 201
Aniline (3 mols)
A
[Trisulfonation, heated
to 160]
or
[Azo Carmine B heated
to 160]
693
Milling Blue
I '14: 3,082
Aniline (3 mols)
M
a-Naphthylamine
(2 mols)
[Sulfonation]
694
Rose Magdala
I '14: 597
a-Amino-azo-naph-
A
Fast Pink for Silk
thalene
/3-Naphthylamine
2-Naphthylamine (C. A. nomen.)
/3-Amino-naphthalene
__-M Q
= 143
STATISTICS. Imported '14: 11,204 Ibs.
Manufactured '17: ?
Manufactured '18: 31,317 Ibs.
Manufactured '19: 99,597 Ibs.
Manufactured '20: ?
FORMATION. From 0-naphthol by heating in an autoclave with am-
monium sulfite and ammonia.
LITERATURE. Cain, Intermediate Products (2d Ed.), 187
Lange, Zwischenprodukte, #2262
Thorpe, Die. Chemistry, 3, 598
392 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from /3-Naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
115
MONOAZO DYES
Azo Turkish Red
/3-Naphthol
MF
116
281
Sul famine Brown B
DISAZO DYES
Azidine Fast
Scarlet 4BS
Nitroso-/3-naphthol
[Sodium bisulfite]
o-Toluidine
Sulfo-m-tolylene-dia-
mine-bis (carbonyl-
amino-naphthol-
sulfonic Acid)
M
D
282
Azidine Fast
Scarlet 7BS
/3-Naphthylamine
(2 mols)
Sulfo-m-tolylene-dia-
mine-bis (carbonyl-
amino-n a p h t h o 1-
sulfonic Acid)
D
287
Toluylene Orange
RR
I '14: 500
/3-Naphthylamine
(2 mols)
3 : 5-Diamino-p-toluene-
sulfonic Acid
D
301
Hessian Purple N
I '14: 465
/3-Naphthylamine
(2 mols)
Diamino-stilbene-disul-
fonic Acid
D
383
Naphthazurine B
I '14: 4,782
Tolidine
HAcid
D
433
Coomassie Black B
1 : 4-Naphthylene-dia-
mine-2-suKonic Acid
R Acid
A
DYES CLASSIFIED BY INTERMEDIATES
393
Dyes Derived from 0-Naphthylamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
541
Brilliant Dianil
/3-Naphthylamine
B
Blue 6G
(3 mob)
Aniline
o-Toluidine
p-Toluidine
[Disulfonation]
or
/3-Naphthylamine
(3 mols)
[Rosaniline; Disulf ema-
nation]
ANTHEAQUINONE DYE
831
Indanthrene Red BN
I '14: 6,056
1-Chloro-anthraqui-
V
I '20: 4,766
none-2-carboxylic
Acid
l-Naphthylamine-3: 6-disulfonic Acid
See, Freund's Acid
l-Naphthylamine-3: 8-disulfonic Acid
a-Naphthylamine--disulfonic Acid
e Acid or Epsilon Acid
8-Aminol: 6-raaphthalene-disulfonic Acid (C. A. nomen.)
H0 3 S NH 2
CioH 9 NO 6 S 2 =303
STATISTICS. Manufactured in 1919 and 1920 but in undisclosed quanti-
ties
FORMATION. Naphthalene-1 : 5- and 1 : 6-disulfonic acids are nitrated
and reduced, resulting in l-naphthylamine-3 : 8- and 4: 8-disulfonic
acids. The separation is effected by crystallizing out the acid
sodium salt of l-naphthylamine-3 ; 8-disulfonic acid
394
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Cain, Intermediate Products (2d Ed.), 196
Lange, Zwischenprodukte, #2575, 2576
Thorpe, Die. Chemistry, 3, 592
l-Naphthylamine-4: 6- and 4: 7-disulfonic Acids
a-Naphthylamine-disulfonic Acids D
Dahl's Acids II and III (respectively)
4-Amino-l : 6-naphthalene-disulf onic Acid (C. A . nomen.)
4-Amino-l: 7-naphthalene-disulfonic Acid (C. A. nomeri)
NH 2 NH 2
and
H0 3 S xx
S0 3 H
(Acid II) (Acid III)
STATISTICS. Manufactured '20: ?
FORMATION. From naphthionic acid by sulfonation with 25 per cent
oleum
LITERATURE. Cain, Intermediate Products (2d Ed.), 198
Thorpe, Die. Chemistry, 3, 593, 594
Lange, Zwischenprodukte, #2577-2582
Dyes Derived from l-Naphthylamine-4: 6- and 4: 7-disulfonic Acids
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
54
Apollo Red B
I '14: 904
p-Nitro-aniline
A
DISAZO DYES
267
Phenylene Black
I '14: 99
a-Naphthylamine
A
M'17: ?
Dipheny-m-phenylene-
I '20: 220
diamine
[4: 7 Acid onlyl
268
Naphthyl Blue
a-Naphthylamine
A
Black N
l-Amino-2-naphthol
Ethyl Ether
269
Naphthol Black 6B
I '14: 120,512
a-Naphthylamine
A
I '20: 1,500
R Acid
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES 395
l-Naphthylamine-4: 8-disulfonic Acid
d Acid or Delta Acid
Schoellkopf s Acid
Disulfo-acid S
4-Amino-l: 5-naphthalene-disulfonic Acid (C. A. nomen.)
a-Naphthylamine-5-disulfonic Acid
a-Naphthylamine-disulfonic Acid S
S Acid
H0 3 S
STATISTICS. Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION. When naphthalene-1 : 5- and 1 : 6-disulfonic acids are
nitrated and reduced, there is formed a mixture of 1-naphthylamine-
3:8- and 4: 8-disulfonic acids. See under l-naphthylamine-3 : 8-
disulfonic acid. The 4: 8-acid is also made by sulfonating 1-
naphthylamine-8-sulfonic acid with three parts of 10 per cent
oleum.
LITERATURE. Cain, Intermediate Products (2d Ed.), 200
Lange, Zwischenprodukte, #2575, 2583-2585
Thorpe, Die. Chemistry, 3, 594
USES. For making l-amino-8-naphthol-4-sulf onic acid, 1 : 8-dihydroxy-
naphthalene-4-sulfonic acid, and 1: 8-naphthasultam-2: 4-disulfonic
acid
l-Naphthylamine-5: 7-disulfonic Acid
5-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
NH,
303
396 DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By sulfonation of the acetyl derivative of 1-naphthyl-
amine-5-sulfonic acid or of a-naphthylamine
LITERATURE Cain, Intermediate Products (2d Ed ), 200
Lange, Zwischenprodukte, #2586
Thorpe, Die. Chemistry, 3, 594
USES. For preparation of l-amino-5-naphthol-7-sulfonic acid
2-Naphthylamine-3: 6-disulfonic Acid
See, Amino-R Acid
2-Naphthylamine-5 : 7-disulf onic Acid
6-Amino-l: 3-naphthalene-disulfonic Acid (C. A. nomen.)
/3-Naphthylamine-disulfonic Acid II of Armstrong and Wynne
Armstrong and Wynne's Acid II
H03 S| /Y\
xA/
H0 3 S
STATISTICS. Manufactured in 1919 and 1920 in undisclosed amounts
FORMATION. By sulfonation of either 2-naphthylamine-5-sulfonic acid,
or j8-naphthylamine, or 2-naphthylamine-7-sulfonic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 208
Lange, Zwischenprodukte, #2598
Thorpe, Die. Chemistry, 3, 605
USES. For preparation of J acid (2-amino-5-naphthol-7-sulfonic acid)
2-Naphthylamine-6 : 8-disulf onic Acid
/See, Amino-G Acid
a-Naphthylamine-a-disulfonic Acid
/See, Freund's Acid
DYES CLASSIFIED BY INTERMEDIATES 397
a-Naphthylamine-/3-disulfonic Acid
l-Naphthylamine-3 : 7-disulf onic Acid (not considered herein)
a-Naphthylamine-6-disulfonic Acid
See, l-Naphthylamine-4: 8-disulfonic Acid
a-Naphthylamine-e-disulfonic Acid
See, l-Naphthylamine-3 : 8-disulfonic Acid
a-Naphthylamine-disulfonic Acids D
See, l-Naphthylamine-4: 6- and 4: 7-disulf onic Acids
a-Naphthylamine-disulfonic Acid S
See, l-Naphthylamine-4: 8-disulfonic Acid
0-Naphthylamine-a-disulfonic Acid
See, Ammo-R Acid
0-Naphthylamine-7-disulfonic Acid
See, Amino-G Acid
/3 -Naphthylamine -5 - disulf onic Acid
2-Naphthylamine-2 : 7-disulf onic Acid (not considered herein)
/3-Naphthylamine-disulfonic Acid II of Armstrong and Wynne
See, 2-Naphthylamine-5 : 7-disulf onic Acid
/3-Naphthylamine-disulfonic Acid C
2-Naphthylamine-4: 8-disulfonic Acid (not considered herein)
0-Naphthylamine-disulfonic Acid P
2-Naphthylamine-3: 7-disulf onic Acid (not considered herein)
/3-Naphthylamine-disulfonic Acid G
See, Amino-G Acid
398
DYES CLASSIFIED BY INTERMEDIATES
/3-Naphthylamine-disulfonic Acid R
See, Amino-R Acid
Naphthylamine Ether
See, l-Amino-2-naphthol Ethyl Ether
l-Naphthylamine-2-sulfonic Acid
X Acid
o-Naphthionic Acid
l-Amino-2-7iaphthalene-sulf onic Acid (C. A . nomen.)
NH S
STATISTICS. Manufactured '18: ?
Manufactured ' 19 : ?
FORMATION. By heating naphthionic acid and naphthalene in a pan
fitted with a stirrer and reflux condenser, at the boiling point of
naphthalene (217) for few hours
LITERATURE. Cain, Intermediate Products (2d Ed.), 189
Thorpe, Die. Chemistry, 3, 589
Lange, Zwischenprodukte, #2352-2355
Dye Derived from l-Naphthylamine-2-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYLr
562
NAPHTHYL-METHANE
DYE
Fast Acid Blue B
I '14: 33,251
I '20: 6,478
Hydrol
[Oxidation]
A
l-Naphthylamine-4-sulfonic Acid
See, Naphthionic Acid
DYES CLASSIFIED BY INTERMEDIATES
399
l-Naphthylamine-5-sulfonic Acid
See, Laurent's Acid
l-Naphthylamine-6-sulfonic Acid l
a-Naphthylamine-/3-sulfonic Acid
d-Naphthylamine-/3-sulfonic Acid Cl
Cleve's /3 Acid
Cleve's Acid
Erdmann's M Acid or ju Acid
5-Amino-2-naphthalene-sulfonic Acid (C. A. women.)
NH 2
H0 3 S
STATISTICS. Imported '14: 5,493 Ibs.
Manufactured ' 18 : ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. From napththionic acid by heating with sulfuric acid at
120-130
LITERATURE. Lange, Zwischenprodukte, 2363
Thorpe, Die. Chemistry, 3, 591
Cf. Cain, Intermediate Products (2d Ed.), 192
Dyes Derived from l-Naphthylamine-6-sulfonic Acid
Sehultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
406
Diazurine B
l-Naphthylamine-6-
D
sulf onic Acid (2 mols)
Dianisidine
/3-Naphthol (2 mols on
-,r
fiber)
TETRAKISAZO DYE
492
Anthracene Acid
l-Naphthylamine-6-
M
Brown B
sulfonic Acid (2 mols)
ACr
Ammo-salicylic Acid
(2 mols)
!
w-Phenylene-diamine
See l-Naphthylamine-6- and 7-sulfonic Acids, page 400
400 DYES CLASSIFIED BY INTERMEDIATES
l-Naphthylamine-6- and 7-sulfonic Acids
Cleve's Acids
Naphthylamine-sulfonic Acids Cleve
a-Naphthylamine-sulfonic Acids Cl
5-and 8-Amino-2-naphthalene-sulfonic Acids (C. A. nomen.)
NH,
NH 2
H0 3 S
and
=C M H 9 N0 8 S =
FORMATION. Naphthalene is sulfonated hot to /3-naphthalene-sul-
fonic acid, this latter in sulfuric acid solution is nitrated cold with
mixed acid. The excess acidity is removed with ground limestone
(CaCOs), and the nitre-compounds reduced with iron borings and
a little acetic acid to a mixture of l-naphthylamine-6-and-7-sulfonic
acids
LITERATURE. Cain, Intermediate Products (2d Ed.), 192
Lange, Zwischenprodukte, #2363, 2364
Thorpe, Die. Chemistry, 3, 591
Dyes Derived from l-Naphthylamine-6- and 7-sulfonic Acids
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
242
Sulf on Black G
Aniline
A
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid
257
Sulfoncyanine
I '14: 145,694
M'17: ?
M'18: ?
M'19: ?
Metanilic Acid
Phenyl- or Tolyl-
1-naphthylamine-
8-sulfonic Acid
A
I '20: 18,325
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES 401
Dyes Derived from l-Naphthylamine-6- and 7-sulfonic Acid (continued)
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
258
Naphthalene Acid
I '14: 7,794
Metanilic Acid
A
Black 4B
a-Naphthylamine
265
Sulfoncyanine
I '14: 69,590
Laurent's Acid
A
Black B
M'17: ?
Phenyl-1-naphthyl-
M'18: ?
amine-8-sulf onic Acid
M'19: ?
M'20: ?
277
Anthracene
I '14: 17,793
Amino-salicylic Acid,
M
Acid Black
etc.
278
Biebrich Patent
a-Naphthylamine, etc.
A
Black
TRISAZO DYES
436
Columbia Black
I '14: 402,997
p-Phenylene-diamine
D
FF
M'18: ?
Gamma Acid
*
M'19: , ?
w-Phenylene-diamine
I '20: 23,350
M'20: ?
458
Carbon Black
p-Phenylene-diamine-
D
sulfonic Acid from
p-nitro-aniline-o-sul-
fonic Acid
ra-Phenylene-(or Toly-
lene-)-diamine or
1 : 3-naphthylene-dia-
mine-6-sulfonic Acid
(2 mols)
1-Naphthylamine -7-sulfonic Acid
a-Naphthylamine-0-sulfonic Acid
Cleve's Acid
Cleve's d Acid
Cleve's Acid
See, l-Naphthylamine-6- and 7-sulfonic Acids
402 DYES CLASSIFIED BY INTERMEDIATES
l-Naphthylamine-8-sulfonic Acid
8-Arnino-l-naphthalene-sulfonic Acid (C. A. nomen.)
a-Naphthylamine-sulfonic Acid S
S Acid
Peri Acid
Schoellkopf 's Acid
H0 3 S NH 2
STATISTICS. Manufactured '19: ?
Manufactured '201562,939 Ibs.
FORMATION. Naphthalene is sulfonated at 60 to a-naphthalene-
sulfonic acid and then nitrated below 40 to l-nitro-naphthalene-8-
sulfonic acid, which latter upon reduction with iron furnishes the
l-naphthylamine-8-sulfonic acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 193
Lange, Zwischenprodukte, #2365
Thorpe, Die. Chemistry, 3, 591
USES. For manufacture of l-naphthylamine-4: 8-disulfonic acid
2-Naphthylamine-l-sulfonic Acid
Tobias Acid
2-Amino-l-naphthalene-sulfonic Acid (C. A. nomen.)
S0 3 H
= Ci H 9 N0 3 S = 223
STATISTICS. Manufactured '18: ?
Manufactured '19: 84,260 Ibs.
Manufactured '20: 325,036 Ibs.
DYES CLASSIFIED BY INTERMEDIATES
403
FORMATION. Sodium 2-naphthol-l-sulfonate (from /3-naphthol and
sulfuric acid at 40) is heated with ammonium hydrogen sulfite
and ammonia in an autoclave at from 100 to 150
LITERATURE. Cain, Intermediate Products (2d Ed.), 205
Lange, Zwischenprodukte, #2367
Thorpe, Die. Chemistry, 3, 601
Dyes Derived from 2-Naphthylamine-l-sulfonic Acid
Schultz
Numbei
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufactwe
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
173
Lithol Red R
I '14: 281,963
/3-Naphthol
CL
M'17: ?
i
M'18: 353,104
M '19: 269,169
M'20: ?
179
Lake Bordeaux B
3-Hydroxy-2-naph-
CL
thoic Acid
2-Naphthylamine-5-sulfonic Acid
/S-Naphthylamine-Y-sulfonic Acid
/3-Naphthylamine-sulf onic Acid D
Dahl's Acid
Forsling's Acid II
See, 2-Naphthylamine-5- and 8-sulfonic Acids
2-Naphthylamine-5- and 8-sulfonic Acids 1
6- and 7-Amino-l-naphthalene-sulfonic Acids (C. A. nomen.)
H0 3 S
and
=C 10 H 9 N0 3 S-223
STATISTICS. Imported '14: 23,265 Ibs. for the 2-naphthylamine-8-
sulfonic Acid
1 See 2-Naphthylamine-5-sulfonic Acid and 2-Naphthylamine-8-sulfonic Acid,
404 DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By sulfonation of /3-naphthylamine
LITERATURE. Cain, Intermediate Products (2d Ed.), 205
Lange, Zwischenprodukte, #2368-2370, 2380-2383
Thorpe, Die. Chemistry, 3, 601, 603
Dye Derived from 2-Naphthylamine-5- and 8-sulfonic Acids
Schultz
Number
Jor Dye
Ordinal y Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
175
MONOAZO DYE
Ponceau for Silk
I '14: 727
/3-Naphthol
A
2-Naphthylamine-6-sulfonic Acid
See, Broenner's Acid
2-Naphthylamine-7-sulfonic Acid
/3-Naphthylamine-5-sulfonic Acid
jS-Naphthylamine-sulfonic Acid F
FAcid
Delta Acid
Bayer's Acid
Cassella's Acid F
7-Amino-2-naphthalene-sulfonic Acid (C. A. nomen.)
FORMATION. Sodium 2-naphthol-7-sulfonic acid (from caustic soda
fusion of naphthalene-2: 7-disulfonic acid) is heated with am-
monium acid sulfite solution and ammonia water in an autoclave
at 100 to 150
LITERATURE. Cain, Intermediate Products (2d Ed.), 207
Lange, Zwischenprodukte, #2377-2379
Thorpe, Die. Chemistry, 3, 602
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2-Naphthylamine-7-sulfonic Acid
405
Schuttz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
340
Chlorazol Orange 2R
Benzidine
Salicylic Acid
D
366
Diamine Red B
Deltapurpurin 5B
I J 14: 21,058
M'17: ?
M'18: ?
Tolidine
Broenner's Acid
D
I '20: 1,896
367
Diamine Red 3B
Tolidine
D
Deltapurpurin 7B
2 -Naphthylamine-7-sul-
sulfonic Acid (2 mols)
371
Rosazurine G
Tolidine
D
Ethyl-2-naphthyl-
amine-7-sulfonic Acid
2-Naphthylamine-8-sulfomc Acid
/3-Naphthylamine-a-sulfonic Acid
Badische Acid
Forsling's Acid I
See, 2-Naphthylamine-5 and -8-sulfonic Acids
a-Naphthylamine-j6-sulfonic Acid
See, l-Naphthylamine-6-sulfonic Acid
a-Naphthylamine-o-sulfonic Acid
See, l-Naphthylamine-7-sulfonic Acid
Naphthylamine-sulfonic Acid Br
See, Broenner's Acid
a-Naphthylamine-/3-sulfonic Acid 01
See, l-Naphthylamine-6-sulfonic Acid
406 DYES CLASSIFIED BY INTERMEDIATES
a-Naphthylamine-sulfonic Acids Cl
See, l-Naphthylamine-6-cwd 7-sulfonic Acids
Naphthylamine-sulf onic Acids Cleve
See, l-Naphthylamine-6-and 7-sulfonic Acids
a-Naphthylamine-sulfonic Acid L
See, Laurent's Acid
a-Naphthylamine-sulfonic Acid S
See, l-Naphthylamine-8-sulfonic Acid
/3-Naphthylamine-a-sulfonic Acid
See, 2-Naphthylamine-8-sulfonic Acid
j8-Naphthylamine-/3-sulfonic Acid
See, Broenner's Acid
/3-Naphthylamine-7-sulfonic Acid
See, 2-Naphthylamine-5-sulfonic Acid
/3-Naphthylamine-S-sulfonic Acid
See, 2-Naphthylamine-7-sulfonic Acid
/3-Naphthylamine-sulfonic Acid D
See, 2-Naphthylamine-5-sulfonic Acid
0-Naphthylamine-sulfonic Acid F
See, 2-Naphthylamine-7-sulfonic Acid
l-Naphthylamine-3 : 6 : 8-trisulf onic Acid
Koch's Acid
8-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C. A. nomen.)
H0 3 S NH 2
Ci H 9 NO 9 S 3 ==383
DYES CLASSIFIED BY INTERMEDIATES 407
STATISTICS. Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: 1,418,560 Ibs.
Manufactured '20: 3,921,950 Ibs.
FORMATION. Naphthalene is sulfonated to naphthalene-1 : 3 : 6-trisul-
fonic acid, using oleum; and this trisulfonic acid is nitrated cold,
and then reduced with iron
LITERATURE. Cain, Intermediate Products (2d Ed.), 202
Lange, Zwischenprodukte,, #2747, 2748
Thorpe, Die. Chemistry, 3, 595
USES. For preparation of H acid (l-Amino-8-naphthol-3:6-disulfonic
acid)
l-Naphthylamine-4: 6: 8-trisulfonic Acid
8-Amino-l: 3: 5-naphthalene-trisulfonic Acid (C. A. nomen.)
H0 3 S NH 2
= Ci H 9 N0 9 S 3 = 383
S0 3 H
FORMATION. Sodium naphthalene-1 : 5-disulfonate is sulfonated to
naphthalene-1 : 3 : 5-trisulfonic acid, and this is nitrated cold, and
then reduced with iron
LITERATURE. Cain, Intermediate Products (2d Ed.), 202
Lange, Zwischenprodukte, #2750
Thorpe, Die. Chemistry, 3, 596
USES. For preparation of K acid (l-amino-8-naphthol-4 : 6-disulfoni c
acid)
2-Naphthylamine-3: 6: 8-trisulfonic Acid
7-Amino-l: 3: 6-naphthalene-trisulfonic Acid (C. A. nomen.)
H0 3 S
. /\
)NH 2
408
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By sulfonation of amino-G acid (as potassium or sodium
salt of 2-naphthylamine-6 : 8-disulf onic acid) with 40 per cent
oleum at 80-90 and finally at 120-130. The amino-G acid is
made by amidation of G salt or by sulf onating j(5-naphthylamine
LITERATURE. Cain, Intermediate Products (2d Ed.), 210
Lange, Zwischenprodukte, #2757
Thorpe, Die. Chemistry, 3, 606
USES. For making 2R acid (2-Amino-8~naphthol-3 : 6-disulf onic Acid)
4-(Naphthyl-azo)-l-naphthylamine (C. A. nomen.)
See, o-Amino-azo-naphthalene
1-Naphthyl-diphenyl-methane (C. A. nomen.)
See, Diphenyl-naphthyl-methane
1 : 5-Naphthylene-diamine-3 : 7-disulf onic Acid
4 : 8-Diamino-2 : 6-naphthalene-disulf onic Acid (C. A . nomen.)
NH 2
= 318
FORMATION. Naphthalene-2 : 6-disulf onic acid (from sulfonation of
naphthalene) is dissolved in sulf uric acid and nitrated at 20-30.
The resulting 1 : 5-dinitro-naphthalene-3 : 7-disulf onic acid is salted
out and reduced
LITERATURE. Cain, Intermediate Products (2d Ed.), 178
Lange, Zwischenprodukte, #2700
Thorpe, Die. Chemistry, 3, 613
Dyes Derived from 1: 5-Naphthylene-diamine-3 : 7-disulf onic Acid
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
431
Diamine Golden
Phenol (2 mols)
D
Yellow
[Ethylation]
432
Diamine Cutch
I '14: 300
a-Naphthylamine
D
Naphthylene Violet
I '20: 49
(2 mols)
DYES CLASSIFIED BY INTERMEDIATES 409
1 : 8-Naphthylene-diamine-3 : 6-disulf onic Acid
4: 5-Diamino-2 : 7-naphthalene-disulfonic Acid (C. A. nomen.)
H 2 N NH 2
CioHioN 2 6 S 2 318
FORMATION. Naphthalene-2 : 7-disulf onic acid (from sulfonation of
naphthalene) is dissolved in strong sulfuric acid and is then di-
nitrated warm with strong nitric acid and sodium nitrate. The
dinitro-acid is reduced
LITERATURE. Lange, Zwischenprodukte, #2704
Cf. Cain, Intermediate Products (2d Ed.), 178
Thorpe, Die. Chemistry, 3, 613
Dyes Derived from 1 : 8-Naphthylene-diamine-3 : 6-disulfonic Acid
Schultz
Number
jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
55
MONOAZO DYE
Brilliant Archil C
I '14: 401
p-Nitro-aniline
A
1: 3-Naphthylene-diamine-6-sulfonic Acid
5: 7-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)
NH 2
H0 3 S -C 10 H 10 N 2 3 S-238
FORMATION. l-Naphthylamine-3 : 6-disulf onic acid (by nitration and
reduction of naphthalene-2 : 7-disulf onic acid) is heated with
ammonia in an autoclave at 160-180
LITERATURE. Lange, Zwischenprodukte, #2483
Thorpe, Die. Chemistry, 3, 612
Cf. Cain, Intermediate Products (2d Ed.), 195
410 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 1 : 3-Naphthylene-diamine-6-sulfonic Acid
Schultz
Number
for Dye
Oidinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYE
458
Carbon Black
1 : 3-Naphthylene-dia-
D
mine-6-sulfonic Acid
(2 mols)
p-Nitroa niline-o-sul-
fonic Acid
l-Naphthylamine-6- or
7-sulfonic Acid
1: 4-Naphthylene-diamine-2-sulfonic Acid
1: 4-Diamino-2-naphthalene-sulfonic Acid (C. A. nomen.)
NH 2
I I J S 3H =C 10 H 10 N 2 3 S = 238
\A/
NH 2
FORMATION. By reduction of the azo derivatives of l-naphthylamine-2-
sulfonic acid
LITERATURE. Cf. Thorpe, Die. Chemistry, 3, 611, 612
Dyes Derived from 1 : 4-Naphthylene-diamine-2-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
433
DISAZO DYES
Coomassie Black B
RAcid
/3-Naphthylamine
A
434
Coomassie Navy
Blue
I '20: 42,357
RAcid
jS-Naphthol
A
461
TRISAZO DYE
Coomassie Union
Black
<
Gamma Acid
m-Phenylene- (or Toly-
lene-)diamine or
Resorcinol (2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES 411
1 : 4-Naphthylene-diamine-6-sulfonic Acid
5: 8-Diamino-2-riaphthalene-sulfonic Acid (C. A. nomen.)
(Acetyl-compound used)
NH 2
JJQ gi i i == CioHio^OsS = 238
FORMATION. A mixture of l-naphthylamine-6-(and 7-)sulfonic acids
(Cleve's Acids) is acetylated with glacial acetic acid, the excess of
acetic acid distilled off, and the acetylated acids dissolved in 5 parts
of sulfuric acid. These acids are nitrated with mixed acid contain-
ing 43 per cent nitric acid, cooled, diluted with ice and water, and
salted out with about 2 parts of salt. The sodium l-acetamido-4-
nitro-6-(and 7-)sulfonates are now reduced hot with iron and some
acetic acid. The acetyl-compound is isolated and used as such,
the acetyl-group being split off after coupling
LITERATURE. Cain, Intermediate Products (2d Ed.), 210
Lange, Zwischenprodukte, #2486
Thorpe, Die. Chemistry, 3, 612
Dyes Derived from 1 : 4-Naphthylene-diamine-6-sulf onic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
273
Diaminogen Blue BB
I 14: 8,308
M'17: ?
a-Naphthylamine
Schaeffer's Acid
D
I '20: 5,936
274
Diaminogen B
I '14: 313,629
I '20: 18,120
a-Naphthylamine
Gamma Acid
D
2 : 7-Naphthylene-diamine-sulf onic Acid
2: 7-Diamino-naphthalene-sulfonic Acid (C. A. nomen.)
=C M H t oNiOiS=238
412
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. Probably by first sulfonating the 2: 7-dihydroxy-naphtha-
lene and then by action of ammonia on the 2: 7-dihydroxy-naphtha-
lene-sulfonic acid
LITERATURE. Ger. Pat. 79780, 80070; Frdl. 4, 948, 949
Cf. Thorpe, Die. Chemistry, 3, 610, 611, 650
Dye Derived from 2 : 7-Naphthylene-diamine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
330
DISAZO DYE
Zambesi Brown G
I '14: 4,028
I '20: 1,104
Benzidine
Gamma acid
D
o-Naphthylene-diamine-j3-sulfonic Acid
1 : 2-Naphthylene-diamine-6-sulf onic Acid (not considered
herein)
o-Napthylene-diamine-T-sulfonic Acid
1 : 2-Naphthylene-diamine-5-sulf onic Acid (not considered
herein)
o-Naphthylene-diamine-5-sulfonic Acid
1 : 2-Naphthylene-diamine-7-sulf onic Acid (not considered
herein)
o-Naphthyl-glycine
7V-(l-Naphthyl)-01ycine (C. A. nomen.)
NH.CH ? COOH
FORMATION. From a-naphthylamine by reaction with chloro-acetic
acid
LITERATURE. Lange, Zwischenprodukte, #2264
Ger. Pat. 79861 of 1893
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from a-Naphthyl-glycine
413
Schultz
Numbe
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
309
DISAZO DYES
Glycine Red
Benzidine
Naphthionic Acid
D
310
Glycine Corinth
Benzidene
a-Naphthyl-glycine
(2 mols)
D
0-Naphthyl-sulfuric Acid
See, 2-Naphthol-l-sulfonic Acid
Nevile-Winther's Acid
l-Naphthol-4-sulfonic Acid (C. A. nomen.)
NWAcid
a-Naphthol-sulfonic Acid NW
= C 10 H 8 4 S=:224
STATISTICS. Manufactured '18: 340,074 Ibs.
Manufactured '19: 344,449 Ibs.
Manufactured '20: 561,929 Ibs.
FORMATION. From the sodium salt of naphthionic acid by hydrolyzing
the amino group
LITERATURE. Cain, Intermediate Products (2d Ed.), 217
Thorpe, Die. Chemistry, 3, 617
Lange, Zwischenprodukte, #2415-2421
414 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
77
MONOAZO DYES
Azo Coccine 2R
Xylidine
A
94
Azo Eosine
I '14: 1,001
M'18: ?
M'19: ?
o-Anisidine
A
\
104
Benzoyl Pink
Benzoyl-o-tolidine
D
163
Azo Rubine
I '14: 230,763
M '17: 197,621
M'18: 79,779
M '19: 187,264
I '20: 1,102
M'20:-470,949
Naphthionic Acid
A
176
Double Scarlet S
Scarlet 2R
I '14: 10,182
M'17: ?
I '20: 1,653
Broenner's Acid
A
194
Rosophenine 10B
Thiazine Red R
I' 14: 3,077
M'19: ?
M'20: ?
Dehydrothio-p-tolui-
dine-sulfonic Acid
D
195
Rosophenine SG
M'18: ?
M'19: ?
M'20: 19,639
Primuline
D
224
DISAZO DYES
Cloth Red G
I '14: 401
M'19: ?
M'20: ?
Amino-azo-benzene
A
233
Cloth Red B
I '14: 1,962
M'18: ?
M'19: ?
M'20: ?
Amino-azo-toluene
M
253
Orseilline BB
Amino-azo-toluene-sul-
fonic Acid
A
DYES CLASSIFIED BY INTERMEDIATES
415
Dyes Derived from Nevile Winther's Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued}
275
Diamond Black F
I '14: 462,306
a-Naphthylamine
ACr
M'17: ?
Amino-salicylic Acid
M'18: ?
M '19: 222,938
I '20: 2,226
M'20: ?
290
Violet Black
a-Naphthylamine
D
p-Phenylene-diamine
or Amino-acet-
anilide
291
Azo Alizarin
Salicylic Acid
M
Bordeaux W
p-Phenylene-diamine
312
Congo Corinth
I '14: 44,157
Benzidine
D
M'17: ?
Naphthionic Acid
M'18: ?
M '19: 137,704
M '20: 242,503
355
Anthracene Red
I '14: 3,873
o-Nitro-benzidine
ACr
M'19: ?
Salicylic Acid
I '20: 104
M'20: ?
375
Congo Corinth B
I '14: 2,196
Tolidine
D
M'19: ?
Naphthionic Acid
377
Azo Blue
I '14: 498
Tolidine
D
M'19: ?
Nevile- Winther's Acid
M'20: ?
(2 mols)
379
Dianil Blue 2R
I '14: 14,434
Tolidine
D
Benzo New Blue 2B
Chromotropic Acid
385
Oxamine Blue 4R
I '14: 573
Tolidine
D
M'20: ?
J Acid
-
416
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid (continued)
Schultz
Number
for Dye
Ordinary Name, and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
386
Diamine Blue BX
I '14: 1,740
Tolidine
D
Benzo Blue BX
M '17: ?
H Acid
M '18: ?
M '19: 92,214
I '20: 4,520
M '20: 90,147
396
Indazurine RM
Tolidine
D
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
397
Direct Blue R
M'17: ?
Tolidine
D
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
401
Diamine Blue 3R
Ethoxy-benzidine
D
Nevile-Winther's Acid
(2 mols)
407
Azo Violet
Dianisidine
D
Naphthionic Acid
410
Benzoazurine G
I '14: 78,699
Dianisidine
D
M'18: ?
Nevile-Winther's Acid
M '19: 150,589
(2 mote)
I '20: 287
M '20: 237,328
412
Congo Blue 2B
Dianisidine
D
RAcid
421
Oxamine Blue B
I '14: 35,891
Dianisidine
D
I '20: 13
l-Amino-5-naphthol-7-
sulfonic Acid
427
Indazurine GM
Dianisidine
D
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
428
Direct Blue B
I '14: 21,421
Dianisidine
D
M'17: 14,823
1 : 7-Dihydroxy-6-naph-
M'18: ?
thoic-3-sulfonic Acid
I '20: 7,055
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nevile-Winther's Acid (continued)
417
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
447
TRISAZO DYES
Benzo Gray S
I '14: 802
Benzidine
Salicylic Acid
a-Naphthylamine
D
450
Benzo Black Blue R
Tolidine
a-Naphthylamine
Nevile-Winther's Acid
(2 mols)
D
459
Benzo Black Blue G
Benzidine-disulfonic
Acid
a-Naphthylamine
Nevile-Winther's Acid
(2 mols)
D
483
St. Denis Red
Rosophenine 4B
I '14: 1,496
I '20: 550
Diamino-azoxy-toluene
Nevile-Winther's Acid
(2 mols)
D
484
Milling Scarlet B
Diamino-azoxy-toluene
RAcid
A
Nigrotic Acid
See, 1 : 7-Dihydroxy-6-naphthoic-3-sulfonic Acid
Nigrotinic Acid
See, 1 : 7-Dihydroxy-6-naphthoic-3-sulf onic Acid
Nitro-l:2:4Acid
See, l-Amino-8-nitro-2-naphthol-4-sulfonic Acid
^-Nitro-acetanilide
NH.COCHs
418
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Manufactured '17: ?
Manufactured '18: 541,552 Ibs.
Manufactured '19: 669,658 Ibs.
Manufactured '20: 569,728 Ibs.
FORMATION. Aniline is acetylated to acetanilide, which is dissolved in
sulfuric acid and then nitrated with mixed acid in the cold
LITERATURE. Cain, Intermediate Products (2d Ed.), 53
USES. For the manufacture of p-nitro-aniline and acetyl-p-phenylene-
diamine (p-amino-acetanilide)
Nitro-alizarin, crude
Ci 4 H 7 N0 6 = 285
FORMATION. Alizarin is dissolved in sulfuric acid and nitrated
Dye Derived from Nitro-alizarin, crude
SchuUz
Number
jor Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHBAQUINONE AND
ALLIED DYES
798
Alizarin Maroon W
I '20: 2,014
[Reduction]
M
3-Nitro-alizarin (C. A. nomen.)
0-Nitro-alizarin
1 : 2-Dihydroxy-3-nitro-anthraquinone
OH
,co>
STATISTICS. Refer to the dye, Alizarin Orange, which is 3-nitro-alizarin
FORMATION. From alizarin by nitration of its boric ester
LITERATURE. Schultz, Farbstofftabellen (1914), #779
Lange, Zwischenprodukte, #3341
Georgievics and Grandmougin, Dye Chemistry, 268
DYES CLASSIFIED BY INTERMEDIATES
419
Dyes Derived from 3-Nitro-alizarin
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
779
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Orange
I '14: 14,239
M'19: ?
I '20: 500
M'20: ?
[This is 3-nitro-alizarin]
M
803
Alizarin Blue WX
I '14: 319,394
M'19: ?
I ; 20: 5,585
3-Amino-alizarin
[Glycerol]
M
804
Alizarin Blue S
I '14: 117,850
I '20: 43,679
3-Amino-alizarin
[Glyceroll
M
808
Alizarin Green X
I '14: 135,191
I '20: 4,254
3-Amino-alizarin
[Glycerol; Oxidation]
M
809
Alizarin Indigo
BlueS
3-Amino-alizarin
[Glycerol; Oxidation]
M
4-Nitro-alizarin (C. A. nomen.)
a-Nitro-alizarin
,CCX
OH
OH
NO 2
FORMATION. This compound is made by nitration of alizarin in weak
oleum solution, or by nitration of the methyl, benzoyl, or arsenic
ester of alizarin
LITERATURE. Georgievics and Grandmougin, Dye Chemistry, 268
Schultz, Farbstofftabellen (1914), #779
420 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 4-Nitro-alizarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
797
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Garnet R
I '14: 720
[Reduction]
M
805
Alizarin Green S
I '14: 15,885
Nitro-benzene
[Reduction; Glycerol]
M
a-Nitro-alizarin
See, 4-Nitro-alizarin
/3-Nitro-alizarin
See, 3-Nitro-alizarin
6-Nitro-m-amino-benzene-sulfonic Acid
See, 6-Nitro-metanilic Acid (C. A. nomen.)
o-Nitro-o-amino-^-cresol
See, 2-Amino-6-nitro-p-cresol (C. A. nomen. OH = 1)
2-Nitro-6-amino-l-phenol-4-sulfonic Acid
See, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid
6-Nitro-2-amino-l-phenol-4-sulfonic Acid
See, 2-Amino-6-nitro-l-phenol-4-sulfonic Acid
m-Nitro-aniline
NH 2
= C 6 H 6 N 2 2 =
STATISTICS. Imported 7 14: 3,527 Ibs.
Manufactured '17: 228,279 Ibs.
Manufactured '18: 630,802 Ibs.
Manufactured '19: 68,600 Ibs.
Manufactured '20: ?
DYES CLASSIFIED BY INTERMEDIATES
421
FORMATION. Benzene is nitrated with mixed acid to dinitro-benzene,
and this body is reduced with sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 51
Lange, Zwischenprodukte, #537, 542
Dyes Derived from m-Nitro-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
46
w-Nitraniline Orange
/3-Naphthol
MF
47
Orange III
M'18: ?
RAcid
A
48
Alizarin Yellow GG
I '14: 144,761
Salicylic Acid
M
M'17:
1,452,622
M'18:
2,233,208
M '19: 163,170
M '20: 211,580
49
Prague Alizarin
/3-Resorcylic Acid
M
Yellow G
DISAZO DYES
222
Janus Yellow G
I '14: 2,250
Resorcinol
B
I '20: 758
w-Amino-phenyl-tri-
methyl-ammonium
Chloride
408
Azophor Black S
m-Nitro-aniline (? mols)
D
Dianisidine
^-Nitro-aniline
NH 2
N0 2
422
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Imported '14: 771,682 Ibs.
Manufactured '17: 1,724,008 Ibs.
Manufactured ' 18: 1,320,064 Ibs.
Manufactured '19: 1,310,658 Ibs.
Manufactured '20: 2,138,492 Ibs.
FORMATION. (1) Aniline is acetylated to acetanilide, which is then
nitrated with mixed acid to p-nitro-acetanilide. The latter com-
pound is hydrolyzed by boiling with caustic soda to p-nitro-aniline.
(2) p-Chloro-nitro-benzene is heated with ammonia under pressure
LITERATURE. Cain, Intermediate Products (2d Ed.), 51
Lange, Zwischenprodukte, #533, 538-541
Dyes Derived from />-Nitro-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
50
Azo Cardinal G
M'18: ?
Ethyl-sulfobenzyl-
aniline
A
51
Nitrophenine
Thiazol Yellow R
I '14: 423
M'20: ?
Dehydrothio-toluidine-
sulfonic Acid
D
52
Archil Substitute V
Naphthionic Acid
A
53
Archil Substitute
Laurent's Acid
A
3VN
54
Apollo Red B
I '14: 904
l-Naphthylamine-4: 6-
and -4 : 7-disulf onic
A
Acids
55
Brilliant Archil C
I '14: 401
I '20: 100
1 : 8-Naphthylene-dia-
mine-3 : 6-disulf onic
A
Acid
56
Paranitraniline Red
I '14: 49,847
M'17: ?
/3-Naphthol
MF
M'18: ?
M'19: ?
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Nitro-aniline (continued)
423
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
57
Chromotrope 2B
I '14: 7,970
Chromotropic Acid
ACr
M'18: ?
M'19: ?
M'20: ?
58
Alizarin Yellow R
I '14: 97,059
Salicylic Acid
M
M '17: 215,468
M '18: 385,910
M '19: 130,424
I '20: 860
M'20: 83,334
61
Victoria Violet
I '14: 52,365
Chromotropic Acid
A
M'17: ?
[Reduction]
M'18: ?
M' 19: 105,086
I '20: 2,162
M'20: ?
63
Azo Acid Blue B
I '14: 45,098
1 : 8-Dihydroxy-naph-
A
I '20: 4,485
thalene-4-sulfonic
Acid
[Methylation]
DISAZO DYES
215
Blue Black N
I '14: 2,653
Aniline
A
l-Amino-8-naphthol-
4:6-disulfonicAcid
216
Domingo Blue
Black B
Aniline
l-Amino-8-naphthol-
A
3 : 5-disulf onic Acid
217
Naphthol Blue Black
I '14: 431,027
Aniline
A
Agalma Black 10B
M '17: 620,218
HAcid
M'18:
1,158,309
M'19:
1,877,860
I '20: 84
M'20:
2,608,86
424 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitro-aniline (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued}
218
NigrophorBASF
2 : 5-Dichloro-aniline
MF
l-Amino-8-naphthol-5-
sulfonic Acid
221
Anthracene Acid
M'17: ?
Sulfanilic Acid
ACr
Brown G
M'18: ?
Salicylic Acid
I '20: 225
245
Nyanza Black B
a-Naphthylamine
D
Gamma Acid
[p-Nitro-aniline reducec
after coupling]
408
Azophor Blue D
Dianisidine
D
Azophor Black S
TRISAZO DYES
473
Diamine Black HW
I '20: 342
Benzidine
D
Gamma Acid
HAcid
474
Diamine Green B
I '14: 77,100
Benzidine
D
Oxamine Green B
M'17: ?
Phenol
M'18: 295,147
HAcid
M '19: 305,854
I '20: 2,460
M '20: 420,138
475
Diamine Green G
I '14: 7,329
Benzidine
D
Oxamine Green G
M'17: ?
Salicylic Acid
M'18: 29,118
HAcid
M '19: 136,638
I '20: 1,332
M'20: 53,292
SULFUR DYE
719
Thional Black
I '14: 16,865
o-Nitro-phenol
S
[NaaS plus S]
or
o-Nitro-phenol (2 mols)
Aniline
[NazS plus S]
DYES CLASSIFIED BY INTERMEDIATES 425
2-Nitro-aniline-4-sulfonic Acid (NH 2 =1)
See, 4-Amino-3-nitro-benzene-sulfonic Acid (C. A. nomen.)
4-Nitro-aniline-2-sulfonic Acid (NH 2 =1)
See, 2-Amino-5-nitro-benzene-sulfonic Acid (C. A. nomen
S0 3 H = 1)
4-Nitro-aniline-3-sulfonic Acid
See, 6-Nitro-metanilic Acid (C. A. nomen.)
o-Nitro-aniline-^-sulfonic Acid (NH 2 =1)
See, 4-Amino-3-nitro-benzene-sulfonie Acid (C. A. nomen.)
^-Nitro-aniline-o-sulfonic Acid (NH 2 =1)
See, 2-Amino-5-nitro-benzene-sulfonic Acid (C. A. nomen
4-Nitro-o-anisidine (C. A. nomen. NH 2 =1)
p-Nitro-o-anisidine (NH 2 -1)
NH 2
|OCH 3
N0 2
FORMATION. o-Anisidine is acetylated, then nitrated, and saponified
by heating with 70 per cent sulfuric acid. The resulting mixture
of 4- and 5-nitro-o-anisidines, is separated by crystallization from
40 per cent sulfuric acid
LITERATURE. Lange, Zwischenprodukte, #911
Dye Derived from 4-Nitro-o-anisidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
98
Naphthol Pink
Nitrosamine
I '14: 99
/3-Naphthol
MF
PinkBX
426 DYES CLASSIFIED BY INTERMEDIATES
5-Nitro-o-anisidine (C. A. nomen. NH 2 =1)
m-Nitro-o-anisidine (NH2=1)
NH 2
OOCH 3 r=CHNO=168
7823
FORMATION. o-Anisidine is acetylated, then nitrated, and saponified
by heating with 70 per cent sulfuric acid. The resulting mixture
of 4- and 5-nitro-o-anisidines is separated by crystallization from
40 per cent sulfuric acid
LITERATURE. Lange, Zwischenprodukte, #911
Dye Derived from 5-Nitro-o-anisidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
99
Tuscaline Orange G
/3-Naphthol
CL
MF
m-Nitro-o-anisidine
See, 5-Nitro-o-anisidine (C. A. nomen.
/>-Nitro-o-anisidine (NH 2 =1)
See, 4-Nitro-o-anisidine (C. A. nomen.
o-Nitro-anisole
OCH 3
=:C 7 H 7 N0 3 =
STATISTICS. Manufactured '18: ?
Manufactured ' 19 : ?
Manufactured '20: 273,327 Ibs.
FORMATION. (1) From o-nitro-phenol by methylation. (2) From
o-chloro-nitro-benzene by action of methanol (methyl alcohol) and
caustic soda
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Cain, Intermediate Products (2d Ed.), 96
Cf. Lange, Zwischenprodukte, #578
USES. For preparation of dianisidine
l-Nitro-anthraquinone-6-sulfonic Acid
5-Nitro-2-anthraquinone-sulfonic Acid (C. A. nomen.)
N0 2
427
FORMATION. When anthraquinone-2-sulfonate of sodium is nitrated
with a mixture of equal parts of " fuming" nitric acid and sulfuric
acid (66) there arises a mixture of the a-nitro and /3-nitro-an-
thraquinone-sulfonic acid which can be separated by dilution,
whereupon the a-acid is precipitated. The a-acid is undoubtedly
l-nitro-anthraquinone-6-sulfonic acid
LITERATURE. Glaus, Ber. 15, 1515 (1882)
Cf. Lange, Zwischenprodnkte, #3160, 3263
Dye Derived from l-Nitro-anthraquinone-6-sulfonic Acid
Schuttz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
864
Anthraquinone
I '14: 1,709
Aniline
ACr
Green GX
I '20. 2,531
[Halogenation]
p-Toluidine
5-Nitro-2-anthraquinone-sulfonic Acid (C. A. nomen.)
See, l-Nitro-anthraquinone-6-sulfonic Acid
m-Nitro-&enzaldehyde
CHO
=C 7 H 5 N0 3 =151
428
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Imported '14: very small
Manufactured '17: ?
Manufactured '18: ?
Manufactured '20: ?
FORMATION. From benzaldehyde by nitration at not above 30-35.
(Twenty per cent o-nitro-derivative also formed)
LITERATURE. Cain, Intermediate Products (2d Ed.), 144
Lange, Zwischenprodukte, #296
Dyes Derived from m-Nitro-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENTL-METHANE
DYES
510
Azo Green
Dimethyl-aniline
(2 mols)
Salicylic Acid
[Oxidation]
M
523
Fast Green
I '14: 14,347
I '20: 10,461
Dimethyl-aniline
(2 mols)
Benzyl Chloride (2 mols)
[Sulfonation, Oxidation
A
543
Patent Blue V
I '14: 196,228
M'17: ?
M'18: ?
Diethyl-aniline (2 mols]
[Sulfonation, Oxidation
A
I '20: 36,420
544
Cyanine B
I '14: 8,398
I '20: 24
Diethyl-aniline (2 mols]
[Sulfouation, Oxidation
A
545
Patent Blue A
I '14: 63,744
M'18: ?
I '20: 44,801
Benzyl-ethyl-aniline
(2 mols)
[Sulfonation, Oxidation'
A
o-Nitro-benzaldehyde
HCO
DYES CLASSIFIED BY INTERMEDIATES 429
STATISTICS. Manufactured '18: ?
FORMATION. When benzaldehyde is nitrated, there results about 20
per cent of the o-nitro- and about 80 per cent of the m-nitro-
derivative. The nitration product is poured into water, and the
oily o-derivative is separated from the solid w-compound by
pressing
LITERATURE. Cain, Intermediate Products (2d Ed.), 143
Lange, Zwischenprodukte, 22, 37, 38, 40, 181, 254, 275,
278, 289-302
Dye Derived from o-Nitro-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
875
Indigo Salt T
[Acetone; NaOH]
Print-
ing
^-Nitro-6enzaldehyde
CHO
STATISTICS. Imported '14: very small
FORMATION. From p-nitro-toluene by oxidation
LITERATURE. Lange, Zwischenprodukte, #275, 303-312
Dye Derived from ^-Nitro-benzaldehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
511
Parafuchsine
I '14: 65,026
Aniline (Sulfate)
B
Paramagenta
M'18: ?
(2 mols)
M'19: ?
[Zinc chloride; ferrous
M'20: ?
chloride]
430 DYES CLASSIFIED BY INTERMEDIATES
Nitro-benzene
Myrbane Oil
N0 2
STATISTICS. Imported '14: 1,502,205 Ibs.
Manufactured 17: 42,975,655 Ibs.
Manufactured ' 18: 38,250,332 Ibs.
Manufactured '19:-42,544,017 Ibs.
Manufactured '20: 53,244,008 Ibs.
FORMATION. From benzene by nitration with mixed acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 20
Lange, Zwischenprodukte, #264-268
Dyes Derived from Nitro-benzene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
511
Parafuchsine
I '14: 65,026
Aniline (2 mols)
B
Paramagenta
M'18: ?
p-Toluidine
M'19: ?
or
M'20: ?
p : p'-Diamino-diphenyl-
methane or
Anhydro-formalde-
hyde-aniline
Aniline and aniline hy-
drochloride
[Ferric chloride]
512
Magenta
I '14: 87,102
Aniline
B
Fuchsine
M'17: 17,739
o-Toluidine
M'18: 71,675
p-Toluidine
M' 19: 155,830
[Iron and zinc chloride]
I '20: 189
M '20: 284,285
-
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nitro-benzene (continued)
431
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
698
Nigrosine, Spirit
I '14: 186,595
Aniline (excess)
88
Soluble
M '17: 302,706
[Iron]
M 18: 314,151
M '19: 346,167
M '20: 919,242
700
Nigrosine, Water
I '14: 398,112
Aniline (excess)
A
Soluble
M'17:
[Iron, Sulfonation]
1,968,458
M'18:
1,191,343
M'19:
1,660,149
I '20: 501
M'20:
2,743,021
SULFUR DYE
718
St. Denis Black
p-Phenylene-diamine
S
Phenol
[S2C1 2 , S, NaaS]
ANTHRAQUINONE AND
ALLIED DYES
805
Alizarin Green S
I '14: 15,885
4-Amino-alizarin
M
[Reduction; glycerol]
3-Nitro-benzidine (C. A. nomen.
See, o-Nitro-frenzidine
o-Nitro-benzidine
3-Nitro-6enzidine (C. A. nomen.
N0 2
H 2 N '
STATISTICS. Manufactured '19: ?
FORMATION. By nitration of benzidine in sulfuric acid solution
432
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Green, Organic Coloring Matters (1908), 41
Eng. Pat. 13475 of 1892
Lange, Zwischenprodukte, #1220
Dye Derived from o-Nitro-benzidine
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
355
Anthracene Red
I '14: 3,873
Salicylic Acid
ACr
M'19: ?
Nevile-Winther's Acid
I '20: 104
M'20: ?
^-Nitro-benzyl Chloride
a-Chloro-p-nitro-toluene (C. A. nomen.)
CH 2 C1
N0 2
= 171.5
FORMATION. (1) By passing chlorine into p-nitro-toluene heated to
185-190. (2) By dropping benzyl chloride into fuming nitric
acid cooled to -15 C.
LITERATURE. Ann. 185, 271
Ber. 6, 1056
C/. Lange, Zwischenprodukte, #250
Dye Derived from />-Nitro-benzyl Chloride
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
S
734
SULFUR DYE
Pyrogene Yellow
I '14: 18,515
I '20: 2,701
p- Ammo-phenol
[S+NasSj
DYES CLASSIFIED BY INTERMEDIATES
o- and />-Nitro-chloro-benzenes
See, o- and p-Chloro-nitro-benzenes (C. A. nomen.)
Nitro-diphenylamine-sulf onic Acid
433
FORMATION. Diphenylamine in sulfuric acid solution is heated with
20 per cent oleum at 80-100, and is then nitrated with nitric
acid at 50-80, resulting in formation of "nitrated diphenylamine-
sulfonic acid "
LITERATURE. Lange, Die Schwefel-farbstoffe, 145
Dye Derived from Nitro-diphenylamine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
737
Cotton Brown
I '14: 2,206
[S+NasS]
S
Sulfine Brown
3-Nitro-flavopurpurin (C. A. nomen.)
0-Nitro-flavopurpurin
3-Nitro-l : 2: 6-trihydroxy-anthraquinone
o
OH
Y> H
A>'
FORMATION. By nitration of flavopurpurin
LITERATURE. Ger. Pat. 54,624, Frdl. 2, 122
434 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 3-Nitro-flavopurpurin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
M
806
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Black P
I '14: 229,500
[Glycerol]
807
Alizarin Black S
I '14: 259,991
[Glycerol]
M
/3-Nitro-flavopurpurin
See, 3-Nitro-flavopurpurin
6-Nitro-metanilic Acid (C. A. nomen.)
4-Nitro-aniline-3-sulfonic Acid
6 -Nitro-m-amino-benzene-sulf onic Acid
S0 3 H
2 N(
JNH 2
C 6 H 6 N 2 O 5 S=:218
FORMATION. Sodium metanilate is acetylated, dissolved in sulfuric acid
and nitrated with mixed acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 56
USES. For preparation of nitro-m-phenylene-diamine
Nitro-phenol crude
OH OH
NO *
and
N0 2
STATISTICS. Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: ?
FORMATION. From phenol by nitration with nitric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), Ill
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Nitro-phenol crude
435
Schullz
Number
for Dye
Ordinary Name and
Class o] Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
698
Nigrosine, Spirit
I '14: 186,595
Aniline (excess)
S3
Soluble
M' 17: 362,706
M '18: 314,151
M '19: 346,167
M '20: 919,242
700
Nigrosine, Water
I '14: 398,112
Aniline (excess)
A
Soluble
M'17:
[Sulfonation]
1,968,458
M'18:
. .
1,191,343
M'19:
1,660,149
I '20: 501
M'20:
2,743,021
o-Nitro-/>henol
OH
STATISTICS. Imported '14: very small
Manufactured 17: 58,128 Ibs.
Manufactured '18: 143,277 Ibs.
Manufactured '19: 18,373 Ibs.
Manufactured '20: ?
FORMATION. (1) Phenol is nitrated with nitric acid, resulting in an
oily mixture of o- and p-nitro-phenol. The o-derivative is separated
by distillation and purified by steam distillation. (2) o-Chloro-
nitro-benzene is hydrolyzed to the o-nitro-phenol by boiling with
caustic soda
LITERATURE. Cain, Intermediate Products (2d Ed.), Ill
Lange, Zwischenprodukte, #574-577
436 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from o-Nitro-phenol
Schullz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
719
Thional Black
I '14: 16,865
p-(o- or m-)Nitro-
aniline
S
[Na^S+S]
or
p-(o- or ?n-)Nitro-
aniline
Aniline
o-Nitro-phenol (2 mols)
[NasS+S]
STATISTICS. Imported '14: 4,780 Ibs.
Manufactured '17: 413,216 Ibs.
Manufactured '18: 192,259 Ibs.
Manufactured '19* 76,191 Ibs.
Manufactured '20* 125,693 Ibs.
FORMATION. (1) Phenol is nitrated with nitric acid to an oily mixture
of o- and p-nitro phenol, from which the o-isomer is removed by
distillation. The residue upon being extracted with hot water
yields the p-isomer, which crystallizes out from the aqueous extract
upon cooling. (2) p-Chloro-nitro-benzene is hydrolyzed to the
p-nitro-phenol by boiling with caustic soda
LITERATURE. Cain, Intermediate Products (2d Ed.j, 111
Lange, Zwischenprodukte, #574-576
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from ^-Nitro-phenol
437
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
709
SULFUR DYE
Italian Green
[Sulfur, etc.]
S
4-Nitro-m-phenylene-diamine
NH 2
>NH 2
N0 2
FORMATION. 5-Amino-2-nitro-benzene-sulfonic Acid (4-nitro-aniline-3-
sulfonic acid) is heated in an autoclave with 25 per cent ammonia
water for three hours at 170-180
LITERATURE. Cain, Intermediate Products (2d Ed.), 86
Dyes Derived from 4-Nitro-m-phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
191
Pyramine Yellow R j I '14: 5,727
Primuline-sulfonic Acic
D
I '20: 100
DISAZO DYES
286
Toluylene Yellow
I '14: 5,485
3: 5-Diamino-p-toluene-
D
sulfonic Acid
Nitro-m-phenylene-
diamine (2 mols)
306
Pyramine Orange 3G
I '14: 7,863
I '20: 396
Benzidine
ra-Phenylene-diamine-
D
disulfonic Acid
314
Pyramine Orange 2R
I '14: 2,789
Benzidine
D
Amino-R Acid
360
Pyramine Orange R
I '14: 21,329
Benzidine-disulfonic
D
I '20: 7,821
Acid
Nitro-w-phenylene-
diamine (2 mols)
438 DYES CLASSIFIED BY INTERMEDIATES
(o-Nitro-phenyl-mercapto) -acetic Acid (C. A. nomen.}
See, o-Nitro-phenyl-thioglycolic Acid
o-Nitro-phenyl-thioglycolic Acid
(o-Nitro-phenyl-mercapto)-acetic Acid (C. A. nomen.)
S.CH 2 .COOH
0"' =
= 213
FORMATION. o-Chloro-nitro-benzene in hot alcoholic solution is treated
with thiogly colic acid and caustic soda solution, and then boiled
for two hours under a reflux condenser
LITERATURE. Lange, Zwischenprodukte, #611
Dye Derived from o-Nitro-phenyl-thioglycolic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
921
Helindone Gray 2B
o-Nitro-phenyl-thio-
V
glycolic Acid (2 mols)
[Chloro-sulfonic Acid;
Reduction]
Nitroso-diethyl-m-amino-phenol
See, 5-Diethylamino-2-nitroso-phenol (C. A. nomen.)
^-Nitroso-diethyl-aniline
N : N-Diethyl-p-nitroso-aniline (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Imported '14: very small
FORMATION. From diethyl-aniline by action of nitrous acid
LITERATURE. Lange, Zwischenprodukte, #531
Dyes Derived from ^-Nitroso-diethyl-aniline
439
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
639
Gallanilic Violet R,B
I '20: 100
Gallanilide
M
641
Coreine RR
I '14: 1,320
Gallamide
M
Coelestine Blue B
I '20: 44
646
Coreine AR
Gallamide
M
Aniline
[Sulfonation]
or
[Coreine RR, Aniline,
Sulfonation]
Nitroso-dimethyl-m-amino-^-cresol
See, 5-Dimethylamino-2-nitroso-p-cresol (C. A. nomen.)
jfr-Nitroso-dimethyl-aniline
N: AT-Dimethyl-p-nitroso-aniline (C. A. nomen.)
N(CH 3 ),
NO
=:C 8 H 10 N 2 =
STATISTICS. Manufactured '17: 96,166 Ibs.
Manufactured '18: 851,821 Ibs.
Manufactured '19: 592,663 Ibs.
Manufactured '20: 155,986 Ibs.
FORMATION. From dimethyl-aniline by action of nitrous acid upon a
cold solution of the hydrochloride
LITERATURE. Lange, Zwischenprodukte, #531
440
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
.Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDOPHENOL
619
Indophenol
M'17: ?
a-Naphthol
V
M'18: ?
M '19: 126,611
M'20: ?
OXAZINE AND
THIAZINE DYES
620
Capri Blue GON
I '14: 128
3-Diethylamino-p-
B
cresol(0#=.0
622
Delphine Blue B
M'17: ?
Gallic Acid
M
M'18: ?
Aniline
M'19: 43,827
[Sulfonation]
M'20: 76,719
or
I '20: 29,643
[Aniline on Gallocya-
nine, Sulfonation]
623
Pyrogallol-Cyanine-
Pyrogallol-5-sulfonic
M
Sulfonic Acids
Acid
624
Modern Violet N
I '20: 5,688
Gallic Acid
M
[C02 removed by heat]
or
[Gallocyanine heated]
626
Gallocyanine
I '14: 78,253
Gallic Acid
M
M'17: ?
M '18:^35,460
M '19: 365,243
I '20: 12,414
M'20: 70,169
627
Modern Cyanine
Gallamide
M
Dimethyl-p-phenylene-
diamine
[Reduction]
or
[Gallocyanine; Di-
methyl-p-phenylene-
diamine; Reduction]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continwd)
441
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediate
Used and Notes
Dye
Appli-
cation
Class
M
628
OXAZINE AND
THIAZINE DYES
(continued)
Gallocyanine MS
Gallic Acid
[Sulfonation]
or
[Leuco-gallocyanine sul-
fonated; oxidized]
629
Gallogreen DH
Modern Blue
Gallic Acid
[Formaldehyde]
or
[Formaldehyde on
Gallocyanine]
M
630
Cyanazurine
Gallamide
Aniline
[Reduction]
M
631
Chromocyanine V
M'18: ?
M'19: ?
I '20: 1,289
M '20: ?
Gallic Acid
[Sulfonation]
or
[Sulfite on Gallo-
cyanine]
M
632
Ultraviolet LGP
I '14: 4,368
Gallic Acid (2 mols)
Nitroso-dimethyl-ani-
line (2 mols)
M
633
Indalizarine R
I '20: 551
Gallic Acid
[Sulfonation]
M
634
Indalizarine Green
Gallic Acid
[Sulfonation; Nitration
or
[Nitration of Indaliza-
rine]
M
635
Blue 1900 TC
Modern Violet
I '20: 1,933
Gallic Acid
[Reduction]
M
636
Prune
I '14: 3,197
I '20: 4,418
Gallic Acid Methyl
Ester
M
442 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Nitroso-dimethyl-aniline (continued)
Schultz
Number
far Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
637
OXAZINE AND
THIAZINE DYES
(continued)
Gallamine Blue
I '14: 2,756
I '20: 16,446
Gallamide
M
638
Amido Gallamine
Blue
Gallamide
[Ammonia; Reduction]
M
639
Gallanilic Violet R,B
I '20: 100
Gallanilide
M
640
Modern Azurine DH
Gallic Acid Methyl
Ester
Aniline
M
642
Phenocyanine TC
I '20: 4,740
Gallic Acid
Resorcinol
M
643
Phenocyanine TV
M'17: ?
I '20: 1,543
Gallic Acid
Resorcinol
[Sulfonation]
or
[Phenocyanine sulfo-
nated]
M
644
Ultracyanine B
Gallic Acid
Resorcinol
or
[Gallocyanine;
Resorcinol]
M
645
Gallazine A
Gallic Acid
Schaeffer's Acid
[Oxidation]
or
[Gallocyanine,
Schaeffer's, Oxidation]
M
647
Nitroso Blue MR
Resorcine Blue
Resorcinol
MF
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
443
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dyo
Appli-
cation
Class
OXAZINE AND
THIAZINE DYES
(continued)
649
New Blue R
I '14: 32,509
/3-Naphthol
B
Meldola's Blue
M'17: ?
Cotton Blue
M'18: 22,613
M'19: ?
I '20: 5,240
M'20: ?
650
New Blue B
0-Naphthol
B
Nitroso-dimethyl-
aniline (2 mols)
651
New Methylene
j8-Naphthol
B
Blue GG
[Dimethyl-amine,
Oxidation]
or
[Meldola's Blue, Di-
methyl-amine, Oxida-
tion]
652
New Fast Blue F
I '14: 2,502
j8-Naphthol
B
Hydrol
or
[Meldola's Blue, Hydrol
655
Muscarine
2: 7-Dihydroxy-naph-
B
thalene
658
Fast Black
I '14: 1,960
m-Hydroxy-diphenyl-
B
I '20: 2,883
amine
659
Methylene Blue
I '14: 185,958
Dimethyl-aniline
B
M'17: 268,435
[Naa&Os, etc.]
M'18: 312,572
M'19: 465,992
I '20: 2,053
M '20: 577,264
660
Methylene Green
I '14: 30,812
M'18: ?
Dimethyl-aniline
[NagSgOs etc.; Nitration
B
M'19: 2,435
or
I '20: 1,047
[Methylene Blue
nitrated]
444
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Nitroso-dimethyl-aniline (continued)
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
661
OXAZINE AND
THIAZINE DYES
(continued)
Thionine Blue GO
I '14: 18,618
I '20: 2,030
Ethyl-methyl-aniline
[Na-j&Os, etc.l
B
670
AZINE DYES
Neutral Red
M'18: ?
m-Tolylene-diamine
[Oxidation]
B
676
Neutral Blue
I '14: 615
JV-Phenyl-jff-naphthyl-
amine
B
677
X
Basle Blue R
#:#'-Ditolyl-2:7-
naphthylene-diamine
B
^678
Fast Neutral
Violet B
M'17: ?
N: AT'-Diethyl-m-
phenylene-diamine
B
681
Methylene Gray
New Fast Gray
I '14: 29,507
M'17: ?
M'18: 16,746
M'19: 28,458
I '20: 9
M'20: 31,620
[Boiling with alcohol]
B
682
Nigramine
Aniline
B
684
Rhoduline Violet
I '14: 2,751
I '20: 35
A^-PhenyW-m-toly-
lene-diamine
or
W-Benzyl-A^-phenyW-
m-tolylene-diamine
B
685
Tannin Heliotrope
I '14: 1,398
I '20: 249
Xylidine
B
689
Indazine M
Nitroso-dimethyl-ani-
line (1 and 2 mols)
Diphenyl-ra-phenylene-
diamine
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Nitroso-dimethyl-aniline (continued)
445
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
691
AZINE DYES
(continued)
Metaphenylene
BlueB
I '14: 50
N: #'-Di-o-tolyl-m-
phenylene-diamine
B
692
Naphthazine Blue
I '14: 6,261
I '20: 2,249
AW-Di-2-naphthyl-
m-phenylene-diamine
[Sulfonation]
A
703
Rubramine
o-Toluidine
p-Toluidine
B
704
Indamine 3R
o-Toluidine
B
705
Indamine 6R
I '14: 66,170
I '20: 9,681
o-Toluidine
p-Toluidine
B
^-Nitroso-ethyl-aniline
JV-Ethyl-p-nitroso-aniline (C. A. nomen.)
NH.C 2 H 5
= C 8 H 10 N 2 =
FORMATION. From ethyl-aniline by action of nitrous acid on the solu-
tion in strong alcoholic hydrochloric acid
LITERATURE. Cf. Lange, Zwischenprodukte, #529
Dye Derived from ^-Nitroso-ethyl-aniline
Sctiultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
684
Rhoduline Red B
JV 1 -Phenyl-4-m-
B
tolylene-diamine
or
iWBenzyl-A^-phenyl-
4-m-tolylene-diamine
446 DYES CLASSIFIED BY INTERMEDIATES
^-Nitroso-ethyl-o-toluidine
AT-Ethyl-4-nitroso-o-foluidine (C. A. nomen. NHR=1)
NH . C 2 H 5
|CH 3
FORMATION. From ethyl-o-toluidine in an alcoholic solution of hydro-
chloric acid, by action of NaNO 2 solution in the cold
LITERATURE. Beilstein, Organische Chemie (3d aufL), II, spl., 248
C/. Lange, Zwischenprodukte, #529
Dyes Derived from Nitroso-ethyl-o-toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYES
684
Rhoduline Red G
JY^Phenyl^-w-
B
tolylene-diamine
or
A^-Benzyl-JV'-phenyl-
4-m-tolylene-diamine
684
Brilliant Rhoduline
#3-Ethyl-JVM>henyl-4-
B
Red
m-tolylene-diamine
^-Nitroso-methyl-aniline
JV-Methyl-p-nitroso-aniline (C. A. nomen.)
NH.CH 3
FORMATION. From methyl-aniline by action of nitrous acid on the
solution in strong alcoholic hydrochloric acid
LITERATURE. Lange, Zwischenprodukte, #529
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from />-Nitroso-methyl-aniline
447
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
625
Chrome Heliotrope
Gallic Acid
M
[Reduction]
l-Nitroso-2-naphthol (C. A. nomen.}
a-Nitroso-/3-naphthol
N.OH
NO
vy
STATISTICS. Manufactured in 1918 and 1919, but in undisclosed
quantities
FORMATION. From /3-naphthol by action of nitrous acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 216
Lange, Zwischenprodukte, #2330
Dyes Derived from l-Nitroso-2-naphthol
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITROSO DYE
2
Gambine Y
[This is l-Nitroso-2-
M
naphthol]
MONOAZO DYES
107
Sulfamine Brown A
I '14: 132
a-Naphthylamine
M
M'18: ?
M'19: ?
I '20: 2,630
M ; 20: ?
116
Sulfamine Brown B
/3-Naphthylamine
M
DISAZO DYES
331
Alkali Dark
Benzidine
D
Brown GV
Gamma Acid
448 DYES CLASSIFIED BY INTERMEDIATES
l-Nitroso-2-naphthylamine-G-sulfonic Acid
6-Amino-5-nitroso-2-naphthalene-sulfonic Acid (C. A. nomen.}
NO
HO 3 S
NH 5
FORMATION. One part of l-nitroso-2-naphthol-6-sulfonic acid (nitroso-
Schaeffer's Acid) is heated with one part of 25 per cent ammonia
for three hours at 60
LITERATURE. Lange, Zwischenprodukte, #2479
Dye Derived from l-Nitroso-2-naphthylamine-6-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
675
AZINE DYE
Rosinduline G
Aniline (2 mols)
A
/>-Nitroso-^henol
OH
NO
:=C 6 H 6 N0 2 =123
STATISTICS. Imported '14: very small amount
Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: 155,273
Manufactured '20: 167,855
FORMATION. From phenol by action of nitrous acid in the cold
LITERATURE. Cain, Intermediate Products (2d Ed.) 111
Lange, Zwischenprodukte, 573
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from />-Nitroso-phenol
449
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYE
748
Hydron Blue
I '14: 296,723
Carbazole
V
I '20: 19,210
[S+NasS]
M'20: ?
4-Nitroso-resorcinol
OH
| QH = C 6 H 5 N0 3 =139
NO
FORMATION. Resorcinol is dissolved in alcohol, one molecule of caustic
soda added, and then gradually one molecule of isoamyl nitrite is
introduced with cooling
LITERATURE. Beilstein, Organische Chemie (3d Ed.), II, 923
Dye Derived from 4-Nitroso-resorcinol
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
648
Iris Blue
Resorcinol
A
[Bromination]
2-Nitro-m-folualdehyde (C. A. women.)
o-Nitro-tolylaldehyde
HCO
)N0 2
450
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. w-Tolylaldehyde is nitrated, and then the two isomerie
nitro-compounds separated by distillation under reduced pressure
LITERATURE. Lange, Zwischenprodukte, #758, 759
Ger. Pat. 113,604 Frdl. 6, 128
Dye Derived from 2-Nitro-m-tolualdehyde
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
888
Indigo MLB/T
I '14: 10,730
2-Nitro-m-tolualdehyde
V
I '20: 827
(2 mols)
[Acetone, NaOH]
o-Nitro- toluene (C. A. nomen.}
o-Nitro-toluol
C 7 H 7 NO 2 =
STATISTICS. Imported '14: 42,482 Ibs.
Manufactured '17: 1,002,822 Ibs.
Manufactured ' 18: 1,240,499 Ibs.
Manufactured '19: 1,366,599 Ibs.
Manufactured '20: 2,173,279 Ibs.
FORMATION. Toluene is nitrated with mixed nitric and sulfuric acids
to a mixture of o- and p-nitro-toluenes. The separation is effected
by means of fractional distillation and freezing the o-isomer being
distilled off and the p-body separated as a solid by cooling the
still residue
LITERATURE. Cain, Intermediate Products (2d Ed.), 32
Lange, Zwischenprodukte, #230-233
DYES CLASSIFIED BY INTERMEDIATES
451
Dyes Derived from o-Nitro-toluene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
513
New Fuchsine O
1 '14: 300
Anhydro-formaldehyde-
B
M '18: ?
o-toluidine or
M'19: ?
Diamino-o-di-
M'20: ?
tolyl-methane
o-Toluidine
p-Nitxo- toluene (C. A. nomen.)
p-Nitro-toluol
NO 2
STATISTICS. Imported '14: very small
Manufactured '17: 567,314 Ibs.
Manufactured '18: 670,645 Ibs.
Manufactured '19: 1,263,056 Ibs.
Manufactured '20: 2,004,089 Ibs.
FORMATION. Toluene is nitrated with mixed nitric and sulfuric acids
to a mixture of o- and p-nitro-toluene. The separation is effected
by means of fractional distillation and freezing, the o-isomer
being distilled off and the p-body separated as a solid by cooling
the still residue
LITERATURE . Cain, Intermediate Products (2d Ed.), 32
Lange, Zwischenprodukte, #230-233
452 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from />-Nitro-toluene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
498
Turquoise Blue
I '14: 1,541
I '20: 1,407
Hydrol or
4: 4'-Tetraethyl-
diamino-benzohydrol
B
6-Nitro-o-toluene-sulfonic Acid (C. A. nomen. SOsH=l)
p-Nitro-toluene-o-sulfonic Acid (CHz=l)
S0 3 H
= C 7 H 7 N0 5 S=r217
2 N
STATISTICS. Manufactured '20: ?
FORMATION. From p-nitro -toluene by sulfonation with oleum
LITERATURE. Cain, Intermediate Products (2d Ed.), 34
Lange, Zwischenprodukte, #837
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
STILBENE DYES
9
Sun Yellow
I '14: 232,688
p-Nitro-toluene-o-sul-
D
Direct Yellow R
M '17: 420,685
fonic Acid (4 mols)
M '18: 307,702
[Alkalies]
M' 19: 440,924
I '20: 1,404
M '20: 348,849
10
Mikado Yellow
I '14: 85,795
p-Nitro-toluene-o-sul-
D
Stilbene Yellow
M'18: ?
fonic Acid (4 mols)
M'19: ?
[Alkalies; Oxidation]
DYES CLASSIFIED BY INTERMEDIATES
453
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
11
STILBENE DYES
(continued)
Mikado Orange
Chloramine
Orange G
I '14: 26,010
M'17: ?
M'18: ?
M'19: ?
M'20: 38,287
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
[Alkalies; Oxidation]
D
12
Diphenyl Citronine G
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
Aniline (2 mols)
D
13
Polychromine B
Diphenyl Orange RR
I '14: 16,113
M'18: ?
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
p-Phenylene-diamine
(2 mols)
D
14
Diphenyl Chrysoine
I '14: 9,898
p-Ni tro-tol uene-0-sul-
fonic Acid (2 mols)
p-Amino-phenol
(2 mols)
[Ethylation]
D
15
Chicago Orange G
Benzidine
D
16
Curcuphenine
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
Dehydro-thio-p-tolui-
dine-sulfonic Acid
(2 mols)
D
17
Chlorophenine
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
Dehydro-thio-p-tolui-
dine-sulfonic Acid
(2 mols)
[Reduction]
D
454
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 5-Nitro-o-toluene-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
205
Diphenyl Chrysoine
p-Nitro-toluene-o-sul-
D
RR
fonic Acid (2 mols)
p-Phenylene-diamine
(2 mols)
Phenol
[Ethylation]
206
Diphenyl Catechine
I '14: 8,642
p-Nitro-toluen e-o-sul-
D
G
fonic Acid (2 mols)
p-Phenylene-diamine
(2 mols)
Dimethyl-gamma Acid
207
Diphenyl Fast
I '14: 992
p-Nitro-toluene-o-sul-
D
Brown G
fonic Acid (2 mols)
p-Phenylene-diamine
(2 mols)
Phenyl-gamma Acid
^-Nitro-toluene-o-sulfonic Acid (CHz=l)
See, 5-Nitro-o-toluene-sulfonic Acid (C. A. nomen. SO^H = 1)
2-Nitro-/>-foluidine (C. A. nomen. NH 2 =1)
m-Nitro-p-toluidine (CH 3 = 1)
NH 2
= C 7 H 8 N 2 O2 = 152
CH 3
STATISTICS. Imported '14: 10,513 Ibs.
Manufactured '17: ?
Manufactured '18: 24,415 Ibs.
Manufactured '19: 58,454 Ibs.
Manufactured '20: 71,197 Ibs.
DYES CLASSIFIED BY INTERMEDIATES
455
FORMATION. From acetyl-p-toluidine by nitration
LITERATURE. Cain, Intermediate Products (2d Ed.), 58
Lange, Zwischenprodukte, #790
Dye Derived from 2-Nitro-/>-toluidine (NH 2 =1)
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
73
Pigment Fast
I '14: 49,708
jS-Naphthol
CL
RedHL
M J 17: ?
Lithol Fast Red RL
M'18: ?
Lithol Fast Scarlet
M'19: ?
I '20: 1,001
M'20: ?
3-Nitro-/>-toluidine (C. A. nomen. NH 2 =1)
o-Nitro-p-toluidine (CH 3 1)
NH 2
STATISTICS. 20,737 Ibs. imported in fiscal year 1914
FORMATION. From dinitro-toluene by partial reduction, using iron and
sulfur dioxide
LITERATURE. Lange, Zwischenprodukte, #536, 539, 790, 791
5-Nitro-o-*oluidine (C. A. nomen. NH 2 =1)
p-Nitro-o-toluidine (CH 3 = 1)
NH 2
CHs r*TTTvjn 1 e;9
f\ A.TI i \^/7jn.8iN 2vy 2 ~ J.i>^
U 2 JN
STATISTICS. Imported '14: 30,642 Ibs.
Manufactured '20: ?
456 DYES CLASSIFIED BY INTERMEDIATES
FORMATION. From o-toluidine by nitration
LITERATURE. Cain, Intermediate Products (2d Ed.), 58
Lange, Zwischenprodukte, #790
Dyes Derived from 5-Nitro-o-toluidine (NH 2 =1)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITRO DYE
8
Pigment Chlorine
M'19: ?
5-Nitro -o-toluidine
CL
M'20: ?
(2 mols)
MONOAZO DYE
72
Pigment Orange R
/3-Naphthol
CL
MF
m-Nitro-/>-toluidine
See, 2-Nitro-p-toluidine (C. A. nomen.
o-Nitro-/>-toluidine (CH S =1)
See, 3-Nitro-p-toluidine (C. A. nomen. NH Z = 1)
^-Nitro-o-toluidine (CH S =1)
See, 5-Nitro-o-toluidine (C. A. nomen. NH Z =1)
o-Nitro-toluol
See, o-Nitro-toluene (C. A. nomen.)
/>-Nitro-toluol
See, p-Nitro-toluene (C. A. nomen.)
o-Nitro-tolylaldehyde
See, 2-Nitro-w-tolualdehyde (C. A. nomen.)
3-Nitro-l: 2: 6-trihydroxy-anthraquinone
See, 3-Nitro-flavopurpurin (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES 457
NW Acid
See, Nevile-Winther's Acid
Ortho=o
Note. This is not considered in the alphabetical arrangement, e.g.,
orlho-Toluidine is indexed as o-Toluidine under "T." However, o-
Toluidine precedes p-Toluidine
Oxy-compounds
See, Hydroxy-compounds
Oxy-juglone
See, Naphthazarin
%
a-Oxy-naphthoic Acid
See, l-Hydroxy-2-naphthoic Acid
0-Oxy-naphthoic Acid
See, 3-Hydroxy-2-naphthoic Acid
a-Oxy-naphthoic-sulfonic Acid
l-Hydroxy-2-naphthoic-4-sulfonic Acid (not considered herein)
/3-Oxy-naphthoic-sulf onic Acid L
2-Hydroxy-3-naphthoic-6-sulfonic Acid (not considered herein)
/3-Oxy-naphthoic-sulfonic Acid S
2-Hydroxy-3-naphthoic-8-sulfonic Acid (not considered herein)
Note. This is not considered in the alphabetical arrangement, e.g., para-
Nitro-aniline is indexed as p-Nitro-aniline under "N." However, p-Nitro-
aniline follows m-Nitro-aniline
458
DYES CLASSIFIED BY INTERMEDIATES
Peri Acid
See, l-Naphthylamine-8-sulfonic Acid
Peri-naphthylene-diamine
1 : 8-Naphthylene-diamine (not considered herein)
Phenanthraquinone
See, Phenanthrene-quinone
Phenanthrene-quinone (C. A. nomen.)
9: 10-Dihydro-9 : 10-diketo-phenanthrene
Phenanthraquinone
O O
FORMATION. From phenanthrene by oxidation with sodium bichromate
and sulfuric acid
LITERATURE. Lange, Zwischenprodukte, #648
Green, Organic Coloring Matters (1908), 65
Dye Derived from Phenanthrene-quinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
668
Flavinduline O
I '14: 660
o-Amino-diphenyl-
B
amine
Phenanthroquinolinone (C. A. nomen.)
See, Benzanthrone-quinoline
/>-Phenetidine (C. A. nomen.)
p-Amino-phenol Ethyl Ether
NH 2
DYES CLASSIFIED BY INTERMEDIATES
459
STATISTICS. Imported '14: 125,524 Ibs.
Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: ?
FOKMATION. From p-amino-phenol by ethylation of the hydroxyl.
Before ethylation the amino group is protected; for example, by
forming the benzylidine compound by treatment of the p-amino-
phenol with benzaldehyde
LITERATURE. Lange, Zwischenprodukte, #590
Dye Derived from ^-Phenetidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
584
Fast Acid Blue R
I '14: 4,022
p-Phenetidine (2 mols)
A
I '20: 130
3 : 6-Dichloro-phthalic
Anhydride
Resorcinol (2 mols)
[PC1 5 ; Sulfonation]
Phenol (C. A. nomen.)
Carbolic Acid
STATISTICS. Imported '14: 10,108,781 Ibs.
Manufactured '17: 64,146 499 Ibs.
Manufactured '18: 106,794,277 Ibs.
Manufactured '19: 1,543,659 Ibs.
Manufactured '20: ?
FORMATION. (1) By distillation from coal tar. (2) By synthesis from
benzene, in which case the benzene is sulfonated to benzene-sulfonic
acid, which is then fused with caustic soda
LITERATURE. Cain, Intermediate Products, 104
Lange, Zwischenprodukte, #142-145
460 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
NITRO DYE
5
Picric Acid
M'19: ?
B
M'20: ?
MONOAZO DYES
125
Diazine Black
I '14: 2,630
p-Tolylene-diamine
B
I '20: 701
o-Toluidine
Aniline or
o-Toluidine .
or
[Safranine]
205
Diphenyl
p-Nitro-toluene-o-sul-
D
Chrysoine RR
fonic Acid
p-Phenylene-diamine
DISAZO DYES
303
Brilliant Yellow
I '14: 278,000
Diamino-stilbene-
D
Paper Yellow
M'17: ?
disulfonic Acid
A
M'18: 1,664
Phenol (2 mols)
M'19: 48,723
I '20: 126
M'20: 91,218
304
Chrysophenine G
I '14: 157,799
Diamino-stilbene-disul-
D
M'17: ?
fonic Acid
M'18: 41,663
Phenol (2 mols)
M'19: 86,795
[Ethylation]
I '20: 3,661
M'20: 247,202
315
Congo Orange G
I '14: 1,623
Benzidine
D
I '20: 75
Amino-R Acid
[Ethylation]
319
Diamine Scarlet B
I '14: 41,175
Benzidine
D
I '20: 10,565
GAcid
373
Congo Orange R
I '14: 7,027
Tolidine
D
I '20: 254
Amino-R Acid
[Ethylation]
DYES CLASSIFIED BY INTERMEDIATES
461
Dyes Derived from Phenol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
404
Diamine Yellow N
M'17: ?
Ethoxy-benzidine
D
I '20: 313
Salicylic Acid
[Ethylation]
431
Diamine Golden
1 : 5-Naphthylene-dia-
D
Yellow
mine-3 : 7Klisulf onic .
Acid
Phenol (2 mols)
[Ethylation]
TRISAZO DYES
464
Erie Direct
M'17: ?
Benzidine
D
Green ET
M'18: ?
HAcid
M'19: 69,700
Aniline
M'20: ?
467
Diphenyl Green G
I '20: 2,205
Benzidine
D
HAcid
o-Chloro-p-nitro-
aniline
470
Chloramine Green B
I '14: 1,675
Benzidine
D
M'19: ?
HAcid
M'20: ?
2 : 5-Dichloro-aniline
474
Diamine Green B
I '14: 77,100
Benzidine
D
Oxamine Green B
M'17: ?
HAcid
M '18: 295,147
p-Nitro-aniline
M'19: 305,854
I '20: 2,460
M'20:-^20,138
TRIPHENYL-METHANE
DYES
515
Methyl Violet
I '14: 255,063
Dimethyl-aniline
B
M'17: 375,107
(3 mols)
M '18: 632,196
M'19: 574,436
I '20: 3,312
M'20: 600,873
462
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
(continued}
517
Methyl Violet 5B
I '14: 22,387
[Benzylation of Methyl
B
Benzyl Violet
M'17: ?
Violet]
I '20: 3,313
or
Dimethyl-aniline
(3 mols)
Benzyl Chloride
519
Methyl Green
[Methyl Chloride of
B
Methyl Violet]
or
Dimethyl-aniline
(3 mols)
[Methyl Chloride]
555
Aurine
I '14: 784
Phenol (3 mols)
S3
M'18: ?
[Heated with oxalic and
CL
I '20: 336
sulfuric acids]
556
Red Coralline
[Aurine treated with
CL
ammonia]
or
Phenol (3 mols)
[Heated with oxalic and
sulfuric acid; treated
with ammonia]
AZINE DYE
693
Milling Blue
I '14: 3,082
Aniline (2 mols)
M
Phenyl-a-naphthyl-
amine (2 mols)
[Sulfonation]
SULFUR DYES
718
St. Denis Black B
p-Phenylene-diamine
S
Nitro-benzene
[SjClj, S, NasS]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenol (continued)
463
tichultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
SULFUR DYES
(continued)
732
Autogene Black
I '14: 7,495
4-Amino-4'-hydroxy-
S
diphenylamine
or
2 : 4-Diamino-4 / -hy-
droxy-diphenylamine
[SaCla; S+NaaS]
ANTHRAQUINONE AND
ALLIED DYES
775
Alizarin Dark
Naphthazarin
M
Green W
or
Dinitro-naphthalene
Phenyl-^-amino-benzyl-o-toluidine (CHs =1)
See, ^-Benzyl-AT^phenyW-m-tolylene-diamine (NH 2 =1)
Phenyl-^-amino-ethyl-o-toluidine (CHa =1)
See, N^Ethyl-N^phenyM-w-tolylene-diamine (NHz=l)
4-Phenylamino-4'-hydroxy-diphenylamine
p-(p-Anilino-anilino)-phenol (C. A. nomen.)
=
= 276
FORMATION. (1) From p-amino-diphenylamine and phenol by oxida-
tion in acid solution and then reduction of the indophenol.
(2) From diphenylamine and p-amino-phenol (p-nitroso-phenol)
by oxidation and then reduction of the indophenol
LITERATURE. Cain, Intermediate Products (2d Ed.), 76
Lange, Zwischenprodukte, #1721
Lange, Schwefelfarbstoffe, 161
464 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 4-Phenylamino-4'-hydroxy-diphenylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
735
SULFUR DYE
Pyrogene Indigo
I '14: 22,661
[S+Na*S]
s
4-Phenylainino-4'-hydroxy-(phenyl-3 / -tolylamine)
4-(p-Anilino-anilino)-o-cresol (C. A. nomen. OH =1)
NH
/CH 3
NH <;> OH = Ci 9 H 18 N 2 = 290
\-/
FORMATION. From p-amino-diphenylamine and o-cresol by oxidation
and subsequent reduction of the indophenol formed
LITERATURE. Lange, Zwischenprodukte, #1721
Dye Derived from 4-Phenylamino-4'-hydroxy-(phenyl-3'-tolylamine)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
735
SULFUR DYE
Pyrogene Indigo
I '14: 22,661
[S+NaaS]
S
2-Phenylamino-8-naphthol-6-sulfonic Acid
See, Phenyl-gamma Acid
Phenyl-m-amino-phenol
See, m-Hydroxy-diphenylamine
Phenyl-^-amino-o-toluidine
See, AH-Phenyl^-w-tolylene-diamine
DYES CLASSIFIED BY INTERMEDIATES
Phenyl-azo-aniline (<7. A. nomen.)
See, Amino-azo-benzene
465
m-Phenylene-diamine
STATISTICS. Manufactured '17: 220,956 Ibs.
Manufactured '18: 641,299 Ibs.
Manufactured '19: 609,789 Ibs.
Manufactured '20: 658,313 Ibs.
FORMATION. From m-dinitro-benzene by reduction with iron and
hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 85
Lange, Zwischenprodukte, #550
Dyes Derived from m-Phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
33
Chrysoidine Y
1 '14: 63,303
Aniline
B
M' 17: 195,756
M '18: 376,495
M '19: 314,581
M '20: 585,648
88
Acid Anthracene
I '14: 33,053
Picramic Acid
ACr
Brown R
M'17: ?
[Substituted phenylene-
M'19: ?
diamine-sulf onic Acids
F 20: 1,400
M'20: ?
89
Metachrome
I '14: 1,001
Picramic Acid
M
Brown B
M'17: ?
M '18: 349,961
M'19: ?
M '20: 192,914
466
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
154
Acid Alizarine
I '14: 18,264
o-Amino-phenol-p-
M
Brown B
M'17: ?
sulfonic Acid
Palatine Chrome
M'18: ?
Brown W
M'19: ?
I '20: 845
M'20: ?
190
Alkali Brown
M'19: ?
Dehydro-thio-p-tolui-
D
Benzo Brown 5R
M'20: 2,987
dine-sulfonic Acid
or
Primuline
DISAZO DYES
208
Leather Brown
I '14: 500
p-Phenylene-diamine
B
M'19: ?
(2 mols)
M'20: ?
209
Terracotta FC
I '14: 551
Primuline or Dehydro-
D
thio-p-toluidine-
sulfonic Acid
Naphthionic Acid
239
Azotol C
p-Amino-acetanilide
MF
/3-Naphthol
283
Bismarck Brown
I '14: 35,020
m-Phenylene-diamine
B
M '17: 309,857
(3 mols)
M '18: 378,208
M'19: 412,574
M'20: 514,218
285
Toluylene Brown G
3: 5-Diamino-p-toluene-
D
sulfonic Acid
329
Diamine Brown V
M'19: ?
Benzidine
D
Gamma Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine (continued)
467
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
B
435
TRISAZO DYES
Janus Brown B
Trimethyl-m-amino-
phenyl-ammonium
Chloride or
p Amino-benzyl-di-
ethylamine
a-Naphthylamine or
w-Toluidine
Aniline
436
Columbia Black FF
I '14: 402,997
M'18: ?
M'19: ?
I '20: 23,350
M'20: ?
l-Naphthylamine-6-and
7-sulfonic Acids
p-Phenylene-diamine
Gamma Acid
D
437
Isodiphenyl Black R
p-Phenylene-diamine
Gamma Acid
Resorcinol
D
448
Diamine Bronze G
I '14: 4,449
Benzidine
Salicylic Acid
HAcid
D
449
Trisulfon Brown B
I '14: 16,781
I '20: 38,616
Benzidine
Salicylic Acid
2R Acid
D
454
Trisulf on Brown G
I '14: 1,323
Tolidine
Salicylic Acid
2R Acid
D
457
Trisulfon Brown GG
I '14 7,562
I '20: 38,411
Dianisidine
Salicylic Acid
2R Acid
D
468 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine (continued}
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
(continued)
458
Carbon Black
p-Phenylene-diamine-
D
sulfonic Acid (from p-
nitro-aniline-o-sul-
fonic Acid)
l-Naphthylamine-6(7)-
sulfonic Acid
m-Phenylene-diamine
(2 mols)
461
Coomassie Union
1 : 4-Naphthylene-dia-
D
Black
mine-2-sulfonic Acid
Gamma Acid
m-Phenylene-diamine
(2 mols)
462
Erie Direct Black GX
1 '14:
Benzidine
D
Direct Deep
1,246,536
Aniline
Black EW
M'17: ?
HAcid
M'18: ?
M'19:
7,250,007
M'20:
7,736,994
469
Chloramine Black N
I '14: 39,600
Benzidine
D
M'19: ?
HAcid
I '20: 1,763
2 : 5-Dichloro-aniline
M'20: ?
476
Benzamine Brown
I '14: 16,988
Benzidine
D
3GO
M'17: ?
Sulfanilic Acid
M'18: ?
Salicylic Acid
M'19: ?
M'20: 623,757
479
Dianil Black R
Benzidine
D
Naphthionic Acid
Chromotropic Acid
DYES CLASSIFIED BY INTERMEDIATES 469
Dyes Derived from m-Phenylene-diamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
485
TETRAKISAZO DYES
Benzo Brown G
I '14: 41,905
M'17: ?
M'18: ?
M'19: 83,506
I '20: 2,286
M '20: 109,648
SulfaniUc Acid (2 mols
m-Phenylene-diamine
(3 mols)
D
486
Direct Brown J
I '14: 3,640
m-Amino-benzoic Acid
(2 mols)
m-Phenylene-diamine
(3 mols)
D
487
Benzo Brown B
I '14: 438
M'20: ?
Naphthionic Acid
(2 mols)
m-Phenylene-diamine
(3 mols)
D
488
Toluylene Brown R
I '14: 201
Naphthionic Acid
(2 mols)
3 : 5-Diamino-p-toluene-
sulfonic Acid
m-Phenylene-diamine
(2 mols)
D
490
Cotton Brown A
I '14: 29,074
Benzidine
Naphthionic Acid
(2 mols)
m-Phenylene-diamine
(2 mols)
D
491
Dianil Black PR
Benzidine-sulfonic Acid
Gamma Acid (2 mols)
m-Phenylene-diamine
(2 mols)
D
492
Anthracene Acid
Brown B
Ammo-salicylic Acid
(2 mols)
l-Naphthylamine-6-sul-
fonic Acid (2 mols)
M
ACr
470
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Phenylene-diamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ACRIDINE DYE
607
Rheonine
I '14: 19,704
Ketone
B
AZINE DYE
669
Neutral Violet
Dimethyl-p-phenylene-
diamine (2 mols)
[Oxidation]
/>-Phenylene-diamine
Note. In a number of cases where p-phenylene-diamine was apparently
used, actually its acetyl-derivative p-amino-acetanilide, or even p-nitro-
aniline, was employed', and after the first coupling, the second amino group
was then freed and diazotized. Here both compounds are generally
indexed.
NH S
C 6 H 8 N 2 =
STATISTICS. Imported '14: 11,088 Ibs.
Manufactured '17: 272,056 Ibs.
Manufactured '18: 215,148 Ibs.
Manufactured '19: 234,332 Ibs.
Manufactured '20: ?
FORMATION. (1) From amino-azo-benzene by reduction. (2) From p-
nitro-aniline by reduction
LITERATURE. Cain, Intermediate Products (2d Ed.), 87
Lange, Zwischenprodukte, #552-555
DYES CLASSIFIED BY INTERMEDIATES
471
Dyes Derived from ^-Phenylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
D
13
STILBENE DYE
Polychromine B
Diphenyl Orange RR
I '14: 16,113
M'18: ?
p-Phenylene-diamine
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
61
MONOAZO DYES
Victoria Violet
I '14: 52,365
M'17: ?
M'18: ?
M '19: 105,086
I '20: 2,182
M'20: ?
Chromotropic Acid
[The p-Phenylene-dia-
mine from p-Nitro-
aniline or p-Amino-
acetanilide]
A
205
Diphenyl Chrysoine
RR
p-Phenylene-diamine
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
Phenol
[Ethylation]
D
206
Diphenyl Catechine
G
I '14: 8,642
p-Phenylene-diamine
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
Dimethyl-gamma Acid
D
207
Diphenyl Fast
Brown G
I '14: 992
p-Phenylene-diamine
(2 mols)
p-Nitro-toluene-o-sul-
fonic Acid (2 mols)
Phenyl-gamma Acid
D
208
DISAZO DYES
Leather Brown
I '14: 500
M'19: ?
M'20: ?
p-Phenylene-diamine
(2 mols)
m-Phenylene-diamine
B
290
Violet Black
Nevile-Winther's Acid
a-Naphthylamine
D
291
Azo Alizarin
Bordeaux W
Salicylic Acid
Nevile-Winther's Acid
M
472 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Phenylene-diamine (continued)
Schultz
Number
or Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
292
Azo Alizarin
Salicylic Acid
M
Black I
Chromotropic Acid
TRISAZO DYES
436
Columbia Black FF
I '14: 402,997
1 -Naphthylamine-6-
D
M'18: ?
and-7-sulfonic Acids
M'19: ?
Gamma Acid
I '20: 23,350
ra-Phenylene-diamme
M'20: ?
437
Isodiphenyl Black R
Gamma Acid
D
Resorcinol
m-Phenylene-diamine
OXAZINE DYE
621
Cresyl Blue 2BS
5-Dimethylamino-2-
B
nitroso-p-cresol
AZINE DYES
695
Paraphenylene
I '20: 337
a-Amino-azo-naph-
B
Violet
thalene
701
Paraphenylene
Amino-azo-benzene
B
BlueR
702
Para Blue
Aniline (3-4 mols)
B
o-Toluidine
p-Toluidine
or
[Spirit Blue]
SULFUR DYES
713
Thiophor Bronze 5G
M'19: ?
[p-Amino-acet-black]
S
[Sulfur]
714
Thiophor Yellow
p-Amino-acetanilide
S
Bronze C
Benzidine
[Sulfur]
718
St. Denis Black B
Phenol
S
Nitro-benzene
[SaCla, S, Na,S]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Phenylene-diamine (continued)
472
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
727
Auronal Black B
l-Chloro-2:4-dinitro-
S
benzene
[Glycerol; S+Na^S]
ANILINE BLACK
GROUP
923
Ursol D, DB
[Oxidation on hair]
Fur
m-Phenylene-diamine-disulfonic Acid
4: 6-Diamino-m-6enzene-disulfonic Acid (C. A. nomen. SO^H = 1)
NH 2
HO 3 S|/\ _ q
s. JNHa
S0 3 H
FORMATION. From m-phenylene-diamine hydrochloride by treating it
with five parts of 40 per cent oleum, heating at 100 for several
hours, then at 120 for 6-10 hours
LITERATURE. Lange, Zwischenprodukte, #1146, 1147
Green, Organic Coloring Matters (1908), 36
Dyes Derived from m-Phenylene-diamine-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
192
MONOAZO DYES
Cotton Orange G
I '14: 1,877
Primuline
D
210
DISAZO DYES
Cotton Orange R
I '14: 16,459
I '20: 51
Primuline-sulfonic Acid
Metanilic Acid
D
306
Pyramine Orange 3G
I '14: 7,863
I '20: 396
Benzidine
Nitro-m-phenylene-
diamine
D
474 DYES CLASSIFIED BY INTERMEDIATES
^-Phenylene-diamine-sulfonic Acid
2: 5-Diamino-frenzene-sulfonic Acid (C. A. nomen.)
Note. As a rule this compound is not used as such, being formed as the
azo derivative in the dye molecule from the reduction of the azo derivative of
p-nitro-aniline-o-sulfonic acid
NH 2
/\S0 3 H =
FORMATION. From p-nitro-aniline-o-sulfonic acid by reduction
LITERATURE. Lange, Zwischenprodukte, #920-924
Dye Derived from />-Phenylene-diamine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYE
458
Carbon Black
l-Naphthylamine-6(7)-
D
sulfonic Acid
m-Phenylene-(Toly-
lene-)diamine or
l:3-Naphthylene-
diamine-6-sulfonic
Acid (2 mols)
Phenyl-gamma Acid
2-Phenylamino-8-naphthol-6-sulfonic Acid
7-Anilino-l-naphthol-3-sulfonic Acid (C. A. nomen.)
HO
H0 3 S
NH
DYES CLASSIFIED BY INTERMEDIATES
475
FORMATION. From gamma acid (2-amino-8-naphthol-6-sulfonic acid)
by heating with aniline and aniline hydrochloride at 160
LITERATURE. Lange, Zwischenprodukte, #2846-2847
Dyes Derived from Phenyl-gamma Acid
Schultz
Number
JOT Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
207
Diphenyl Fast
I '14: 992
p-Nitro-toluene-o-sul-
D
Brown G
fonic Acid
p-Phenylene-diamine
DISAZO DYES
349
Diamine Brown B
I '20: 24
Benzidine
D
Salicylic Acid
TBISAZO DYE
445
Crumpsall Direct
Benzidine
D
Fast Brown O
Salicylic Acid
Aniline
Phenyl-glycine
JV-Phenyl-gflycine (C. A. nomen.)
NH.CH 2 .COOH
STATISTICS. Manufactured '17: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. By action of chloro-acetic acid on aniline
LITERATURE. Cain, Intermediate Products (2d Ed.), 153
Lange, Zwischenprodukte, #96-109, 111
476
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
874
Indigo
I '14:
Phenyl-glycine (2 mols)
V
8,507,359
[Sodamide]
M'17: 274,771
M'18:
3,083,888
M'19:
8,863,824
I '20: 520,347
M'20:
18,178,231
876
Indigo MLB
Phenyl-glycine (2 mols)
V
Indigo White
f [Sodamide, Reduction]
or
[Indigo, Reduction]
877
Indigotine
I '14: 19,329
Phenyl-glycine (2 mols),
A
M'17:
etc.
1,876,787
or
M'18:
[Indigo, Sulfonation]
1,434,703
M'19:
1,699,670
I '20: 5,512
M'20:
1,395,000
878
Indigotine P
Phenyl-glycine
A
(2 mols), etc.
or
[Indigo, Sulfonation]
879
Brom Indigo
I '14: 53,640
Phenyl-glycine
V
Rath jen
M'20: ?
(2 mols), etc.
Indigo MLB/RR
or
[Indigo, Bromination]
880
Helindone Blue BB
I '14: 6,856
Phenyl-glycine
V
Indigo RB
M'17: 14,100
(2 mols), etc.
I '20: 3,691
or
M'20: ?
[Indigo, Bromination]
DYES CLASSIFIED BY INTERMEDIATES
477
Dyes Derived from Phenyl-glycine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
881
Dianthrene Blue 2B
I '14: 16,880
Phenyl-glycine
V
Bromo Indigo FB
M'19: ?
(2 mols), etc.
Ciba Blue 2B
I '20: 35,857
or
[Indigo, Bromination]
882
Indigo MLB/5B
I '14: 1,356
Phenyl-glycine
V
Ciba Blue G
I '20: 1,008
(2 mols), etc.
or
[Indigo, Bromination]
883
Indigo MLB/6B
I '14: 3,191
Phenyl-glycine
V
Indigo KG
I '20: 4,130
(2 mols), etc.
M'20: ?
or
[Indigo, Bromination]
884
Brilliant Indigo
I '14: 4,518
Phenyl-glycine
V
BASF/2B
(2 mols), etc.
or
[Indigo, Chlorination,
Bromination]
885
Brilliant Indigo
I '14: 8,117
Phenyl-glycine
V
BASF/B
I '20: 3,503
(2 mols), -etc.
or
[Indigo, Chlorination]
886
Brilliant Indigo
I '14: 12,057
Phenyl-glycine
V
BASF/G
(2 mols), etc.
or
[Indigo, Chlorination,
Bromination]
889
Indigo Yellow 3G
Phenyl-glycine
(2 mols), etc.
V
Benzoyl chloride
or
[Indigo, Benzoyl
chloride]
478 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine (continued)
Schultz
Numebr
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYE
(continued)
890
Ciba Yellow G
I '14: 48
Phenyl-glycine
V
(2 mols), etc.
Benzoyl chloride
or
[Indigo, Benzoyl
chloride, Bromina-
tion]
Phenyl-glycine-o-carboxylic Acid
N-(Carboxy-methyl)-anthranilic Acid (C. A. nomen.)
COOH
ONH.CH 2 .COOH
:C 9 H 9 N0 4 =195
FORMATION. Phthalic anhydride is converted through phthalimide
into anthranilic acid. This latter by reaction with chloro-acetic
acid forms the phenyl-glycine-o-carboxy acid
LITERATURE. Lange, Zwischenprodukte, #379, 383-393
Dyes Derived from Phenyl-glycine-o-carboxylic Acid
SchuUz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
874
Indigo
I '14:
Phenyl-glycine-o-car-
V
8,507,359
boxylic Acid (2 mols)
M '17: 274,771
[Sodamide]
M'18:
3,083,888
M'19:
8,863,824
I '20: 520,347
M '20:
18,178,23 1
DYES CLASSIFIED BY INTERMEDIATES 479
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dy,
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
876
Indigo MLB
Phenyl-glycine-o-car-
V
Indigo White
boxylic Acid (2 mols)
[Sodamide, Reduction]
or
[Indigo, Reduction]
877
Indigotine
I '14: 19,329
Phenyl-glycine-o-car-
A
M'17:
boxylic Acid (2 mols),
1,876,787
etc.
M'18:
or
1,434,703
[Indigo, Sulfonation]
M'19:
1,699,670
I '20: 5,512
M'20:
1,395,000
878
Indigo tine P
Phenyl-glycine-o-car-
A
boxylic Acid (2 mols),
etc.
or
[Indigo, Sulfonation]
879
Bromo Indigo
I '14: 53,610
Phenyl - glycine - o - car-
V
Rathjen
M'20: ?
boxylic Acid (2 mols)
Indigo MLB/RR
etc.
or
[Indigo, Bromination]
880
Helindone Blue BB
Indigo RB
I '14: 6,856
M'17: 14,100
Phenyl - glycine - o - car-
boxylic Acid (2 mols),
V
I '20: 3,691
etc.
M'20: ?
or
[Indigo, Bromination]
881
Dianthrene Blue 2B
Bromo Indigo FB
I '14: 16,880
M'19: ?
Phenyl - glycine - o - car-
boxylicAcid(2mols),
V
Ciba Blue 2B
I '20: 35,857
etc.
or
[Indigo, Bromination]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
882
Indigo MLB/5B
I '14: 4,356
Phenyl - glycine - o - car-
V
Ciba Blue G
I '20: 1,002
boxylic Acid (2 mols),
etc.
or
[Indigo, Bromination]
883
Indigo MLB/6B
I '14: 3,191
Phenyl - glycine - o - car-
V
Indigo KG
I '20: 4,130
boxylic Acid (2 mols),
M'20: ?
etc.
or
[Indigo, Bromination]
884
Brilliant Indigo
I '14: 4,518
Phenyl - glycine - o - car-
V
BASF/2B
boxy lie Acid (2 mols),
etc.
or
[Indigo, Chlorination,
Bromination]
885
Brilliant Indigo
I '14: 8,175
Phenyl - glycine - o - car-
V
BASF/B
I '20: 3,503
boxylic Acid (2 mols),
etc.
or
[Indigo, Chlorination]
886
Brilliant Indigo
I '14: 12,057
Phenyl - glycine - o - car-
V
BASF/G
boxylic Acid (2 mols),
etc.
or
[Indigo, Bromination,
Chlorination]
889
Indigo Yellow 3G
Phenyl - glycine - o - car-
V
boxylic Acid (2 mols),
etc.
Benzoyl chloride
or
[Indigo, Benzoyl
chloride^
DYES CLASSIFIED BY INTERMEDIATES 481
Dyes Derived from Phenyl-glycine-o-carboxylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
890
Ciba Yellow G
F 14: 48
Phenyl - glycine - o - car-
V
boxylic Acid (2 mols),
etc.
Benzoyl chloride
[Bromination]
or
[Indigo Yellow 3G,
Bromination]
Phenyl-hydrazine-^-sulfonic Acid
p-Hydrazino-frenzene-sulfonic Acid (C. A. nomen.)
NH.NH 2
S0 3 H
STATISTICS. Manufactured '20: 441,117 Ibs.
FORMATION. (1) Sulfanilic acid is diazotized and then reduced with
sodium bisulfite. (2) Aniline is diazotized and reduced with
sodium bisulfite, forming phenyl-hydrazine, which is then sulfonated
with 66 sulfuric acid at 100
LITERATURE. Cain, Intermediate Products (2d Ed.), 49
Lange, Zwischenprodukte, #629
Dyes Derived from Phenyl-hydrazine-^-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
A
19
PYRAZOLONE DYES
Flavazine L
Fast Light Yellow
I '14: 38,908
I '20: 9,327
Aniline
[Ethyl Aceto-acetate]
20
Flavazine S
I '14: 81,375
I '20: 1,500
Aniline
[Ethyl Oxal-acetate]
A
482
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-hydrazine-/>-sulfonic Acid (continued)
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYKAZOLONE DYES
23
(continued)
Tartrazine
I '14: 272,477
M'17: ?
M'18: ?
M'19: ?
Phenyl-hydrazine-p-
sulfonic Acid (2 mols)
Dihydroxy-tartaric
Acid
A
I '20: 47,877
M '20: 701,722
or
Sulfanilic Acid
[Ethyl Oxal-acetate]
27
Dianil Yellow 2R
Primuline-sulfonic Acid
D
[Ethyl Aceto-acetate]
l-Phenyl-3-methyl-5-pyrazolone
See, 3-Methyl-l-phenyl-5-pyrazolone
Phenyl-a-naphthylamine
JV-Phenyl-1-naphthylamine (C. A. nomen.)
NH
STATISTICS. Manufactured '17: ?
Manufactured '18: ?
Manufactured ' 19 : ?
Manufactured '20: ?
FORMATION. From a-naphthylamine hydrochloride and aniline by
heating together
LITERATURE. Cain, Intermediate Products (2d Ed.), 187
C/. Lange, Zwischenprodukte, #2827
Thorpe, Die. Chemistry, 3, 587
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phenyl-a-naphthylamine
483
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
263
Jet Black R
Aniline-2: 4-disulfonic
A
Acid
a-Naphthylamine
361
Sulfonazurine
I '14: 300
Benzidine-sulfon-disul-
D
fonic Acid
Phenyl-a-naphthyl-
amine (2 mols)
DlPHENYL-NAPHTHYL-
METHANE DYE
559
Victoria Blue B
I '14: 127,769
Ketone
B
M'17: ?
or
M'18: ?
Hydrol
M'19: ?
I '20: 11,782
M'20: ?
AZINE DYE
-
693
Milling Blue
I '14: 3,082
Aniline (2 mols)
M
Phenyl-a-naphthyl-
amine (2 mols)
Phenol
[Sulfonation]
Phenyl-/3-naphthylamine
7V-Phenyl-2-naphthylamine (C. A. nomen.)
-NH
FORMATION. From /3-naphthol and aniline (or hydrochloride) by
heating together in an open vessel to around 200
LITERATURE. Lange, Zwischenprodukte, #2827
Thorpe, Die. Chemistry, 3, 599
484 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Phenyl-j3-naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AZINE DYE
676
Neutral Blue
1 '14: 615
Nitroso-dimethyl-
B
aniline
Phenyl-l-naphthylamine-8-sulfonic Acid
8-Anilino-l-naphthalene-sulfonic Acid (C. A. nomen.)
Phenyl-peri Acid
HO 3 S NH
STATISTICS. Imported '14: 9,139 Ibs.
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. l-Naphthylamine-8-sulfonic acid, aniline, and aniline
hydrochloride are heated together in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 194
Dyes Derived from Phenyl-l-naphthylamine-8-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
85
Omega Chrome
Black PV
2-Amino-6-nitro-p-
cresol
ACr
188
Tolyl Blue SR
Sulfon Acid Blue R
I '14: 45,038
M'17: ?
HAcid
A
M'18: ?
M'19: ?
M '20: 454,185
DYES CLASSIFIED BY INTERMEDIATES
485
Dyes Derived from Phenyl-l-naphthylamine-8-sulfonic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
256
Sulfon Black 3B
Metanilic Acid
A
a-Naphthylamine
257
Sulfoncyanine
I '14: 145,649
Metanilic Acid
A
M'17: ?
a-Naphthylamine
M'18: ?
M'19: ?
I '20: 18,327
M'20: ?
265
Sulfoncyanine
I '14: 69,590
Laurent's Acid
A
Black B
M'17: ?
a-Naphthylamine or
M'18: ?
l-Naphthylamine-6-
M'19: ?
and 7-sulf onic Acids
M'20: ?
W-Phenyl-o-phenylene-diamine (C. A. nomen.)
See, o-Aminodiphenylamine
W-Phenyl--phenylene-diamine (C. A. nomen.)
See, p-Amino-diphenylamine
Wi-Phenyl-4-m-tolylene-diamine (C. A. nomen. NH 2 =1)
Phenyl-p-amino-o-toluidine (CH S =1)
3- Amino-4-methy 1-diph eny lamine
NH
FORMATION. From m-tolylene-diamine hydrochloride by melting with
aniline at 220-270
LITERATURE. Lange, Zwischenprodukte, #1621, 1622
486 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from ^-Phenyl-4-m-tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
684
AZINE DYES
Rhoduline Violet
I '14: 2,751
I '20: 35
Nitroso-dimethyl-
aniline
B
684
Rhoduline Red B
Nitroso-ethyl-aniline
B
684
Rhoduline Red G
Nitroso-ethyl-o-
toluidine
B
Phosgene (C. A. nomen.)
Carbonyl Chloride
\C1
STATISTICS. Imported '14: very small
Manufactured in recent years in undisclosed quantities
FORMATION. From chlorine and carbon monoxide, in presence of a
catalyst, for example, a suitable charcoal
LITERATURE. Ullmann, Enzy. tech. Chemie, 3, 498
Dyes Derived from Phosgene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
279
DISAZO DYES
Benzo Fast Scarlet
I '14: 36,674
M'19: ?
I '20: 24,153
J Acid (2 mols)
Aniline
Amino-azo-benzene
D
296
Cotton Yellow G
I '14: 31,472
I '20: 4,651
Acetyl-p-phenylene-
diamine (2 mols)
Salicylic Acid (2 mols)
D
DYES CLASSIFIED BY INTERMEDIATES
487
Dyes Derived from Phosgene (continued)
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
516
Crystal Violet
I '14: 51,872
Dimethyl-aniline
B
M'17: ?
(3 mols)
M'18: ?
M'19: ?
I '20: 2,919
M'20: ?
518
Ethyl Violet
I '14: 51,933
Diethyl-aniline (3 mols)
B
Ethyl Purple
ANTHRAQUINONE AND
ALLIED DYES
810
Helidone Yellow
I '14: 20,744
2-Amino-anthraqui-
V
3GN
I '20: 2,515
none (2 mols)
Phthalic Anhydride
,co,
/v \
I I
N/Nx/
STATISTICS. Imported '14: 63,574 Ibs.
Manufactured '17: 138,857 Ibs.
Manufactured '18: 227,414 Ibs.
Manufactured '19: 290,677 Ibs.
Manufactured '20: 796,210 Ibs.
FORMATION. (1) Naphthalene is oxidized with air in presence of a
catalyst. (2) Naphthalene is oxidized by means of sulfur trioxide
in presence of mercury.
LITERATURE. Cain, Intermediate Products (2d Ed.), 162
488
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride
Schvltz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
571
Rhodamine 6G
I '14: 37,515
Ethyl-m-amino-phenol
B
I '20: 8,574
(2 mols)
[Ethylation]
572
Rhodamine G
I '14: 2,648
Diethyl-m-amino-
B
I '20: 217
phenol (2 mols)
Aniline [removes one
C2H 5 group]
or
[Heating of Rhodamine
B with aniline salt]
i
573
Rhodamine B
I '14: 59,354
Diethyl-m-amino-
B
M'17: ?
phenol (2 mols)
M'18: ?
or
M'19: ?
Resorcinol (2 mols)
I '20: 24,709
[PC1 5 ; diethyl-amine]
M'20: ?
574
Rhodamine 3B
Diethyl-w-amino-
B
phenol (2 mols)
[Ethyl esterification]
or
[Ethyl ester of Rhoda-
mine B]
580
Fast Acid Violet B
I '14: 20,688
Resorcinol (2 mols)
A
I '20: 2,907
Aniline or
M'19: ?
p-Toluidine (2 mols)
[PC1 5 ; sulfonation]
or
[Dichloro-fluoresceine
and Aniline or
p-Toluidine; sul-
fonation]
DYES CLASSIFIED BY INTERMEDIATES
489
Dyes Derived from Phthalic Anhydride (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
(continued)
581
Fast Acid Eosine G
I '14: 650
Diethyl-wi-amino-
A
Fast Acid Phloxine A
I '20: 5,234
phenol (2 mols)
[Sulfonation]
or
[Rhodamine B, suljo-
nated]
582
Fast Acid
I '14: 875
Resorcinol (2 mols)
A
Violet A2R
I '20: 2,679
o-Toluidine (2 mols)
M'20: ?
[PC1 5 , Sulfonation]
or
[Dichloro-fluoresceine
and o-toluidine,
Sulfonation]
583
Acid Rosamine A
I '14: 50
Resorcinol (2 mols)
A
I '20: 141
Mesidine (2 mols)
[PC1 5 , Sulfonation]
or
[Dichloro-fluoresceine
and mesidine, sulf o-
nation]
585
Uranine
I '14: 2,273
Resorcinol (2 mols)
A
Fluoresceine
M'17: ?
M'19: ?
I '20: 10
586
Chrysoline
I '20: 1,402
Resorcinol (2 mols)
A
Benzyl Chloride
587
Eosine
I '14: 94,528
Resorcinol (2 mols)
A
M'17: 68,496
[Bromine]
M '18: 161,153
or
M '19: 121,303
[Tetrabromo-flupre-
I '20: 296
sceine]
M'20: 85,489
490 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
588
XANTHONE DYES
(continued)
Eosine Spirit Solubl.
Methyl Eosine
Resorcinol (2 mols)
[Bromine; Methyl
esterificjation]
or
Eosine methyl ester]
ss
589
Eosine S
I '14: 2,315
M'20: ?
M'20: ?
Resorcinol (2 mols)
[Bromine; Ethyl
esterification]
or
[Eosine ethyl ester]
ss
590
Eosine BN
Acid Eosine
I '14: 20,143
I '20: 1,132
M'20: ?
Resorcinol (2 mols)
[Bromination, Nitra-
tion]
or
[Dibromo-fluoresceine
nitrated]
A
591
Erythrosine G
I '14: 99
Resorcinol (2 mols)
[lodation]
or
[Diiodo-fluoresceine]
A
592
Erythrosine B
I '14: 4,350
M'17: 505
M'18: 1,636
M'19: ?
I '20: 9
M'20: 6,874
Resorcinol (2 mols)
[lodation]
or
[Tetraiodo-fluoresceine]
A
599
Galleine
I '14: 15,404
M'19: ?
I '20: 7,469
M'20: ?
Gallic Acid (2 mols)
or
Pyrogallol (2 mols)
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
491
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
(continued)
600
Coeruleine B
M'19: ?
Resorcinol (2 mols)
M
M'20: ?
[Dehydration]
or
[Fluoresceine
dehydrated]
601
Coeruleine S
I '14: 3,404
Gallic Acid (2 mols)
M
M'19: ?
of
I '20: 9,392
Pyrogallol (2 mols)
[Dehydration]
or
[Galleine dehydrated]
QUINOLINE DYES
612
Quinoline Yellow
I '14: 79,553
Quinaldine
S3
Spirit Soluble
I '20: 205
613
Quinoline Yellow
I '14: 15,354
Quinaldine
A
Water Soluble
I '20: 34,440
[Sulfonation]
ANTHRAQUINONE AND
ALLIED DYES
758
Sirius Yellow G
Naphthalene
CL
782
Anthracene Brown
I '14: 115,586
Gallic Acid
M
Alizarin Brown
M'17: ?
M'18: ?
M'19: 40,426
I '20: 2,728
M'20: 42,840
INDIGO GROUP DYES
874
Indigo
I '14:
Phthalic Anhydride
V
8,507,359
(2 mols)
M '17: 274,771
M'18:
3,083,888
M'19:
8,863,824
M'20:
18,178,231
I '20: 520,347
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
Schultz
Number
for Dye
Ordinary Name and
Class o] Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
876
Indigo MLB
Phthalic Anhydride
V
Indigo White
(2 mols)
[Reduction]
877
Indigotine
I '14: 19,329
Phthalic Anhydride
A
M'17:
(2 mols)
1,876,787
[Sulfonation]
M'18:
1,434,703
M'19:
1,699,670
M'20:
1,395,000
I '20: 5,512
878
Indigotine P
Phthalic Anhydride
A
(2 mols)
[Sulfonation]
879
Brom Indigo
I '14: 53,610
Phthalic Anhydride
V
Rath jen
M '20: ?
(2 mols)
[Bromination]
880
Helindone Blue BB
I '14: 6,856
Phthalic Anhydride
V
Indigo RB
M'17: 14,100
(2 mols)
I '20: 3,691
[Bromination]
M'20: ?
881
Dianthrene Blue 2B
I '14: 16,880
Phthalic Anhydride
V
Bromo Indigo FB
M'19: ?
(2 mols)
Ciba Blue 2B
I '20: 35,857
[Bromination]
882
Indigo MLB/5B
I '14: 1,356
Phthalic Anhydride
V
Ciba Blue G
I '20: 1,008
(2 mols)
[Bromination]
883
Indigo MLB/6B
I '14: 3,191
Phthalic Anhydride
V
Indigo KG
I '20: 4,130
(2 mols)
M'20: ?
[Bromination]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Phthalic Anhydride (continued)
493
Schultz
Number
for Dye
884
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
(continued)
Brilliant Indigo
BASF/2B
I '14: 4,518
Phthalic Anhydride
(2 mols)
[Chlorination, Bromina-
tion]
V
885
Brilliant Indigo
BASF/B
I '14: 8,175
I '20: 3,503
Phthalic Anhydride
(2 mols)
[Chlorination]
V
886
889
Brilliant Indigo
BASF/G
Indigo Yellow 3G
I '14: 12,057
Phthalic Anhydride
(2 mols)
[Chlorination, Bromina-
tion]
Phthalic Anhydride
(2 mols)
Benzoyl Chloride
V
V
890
Ciba Yellow G
I '14: 48
Phthalic Anhydride
(2 mols)
Benzoyl Chloride
[Bromination]
V
Phthalimide
CO
NH = C 8 H 5 NO 2 147
O'
STATISTICS. Manufactured in 1920 in undisclosed amount
FORMATION. By treatment of molten phthalic anhydride with gaseous
ammonia
LITERATURE. Cain, Intermediate Products (2d Ed.), 147
USES. For preparation of anthranilic acid
Piria's Acid
See, Naphthionic Acid
494
DYES CLASSIFIED BY INTERMEDIATES
Picramic Acid
OH
02N/NNH2 ;_,
N0 2
STATISTICS. Manufactured '17: ?
Manufactured '18: 235,652 Ibs.
Manufactured '19: 150,458 Ibs.
Manufactured '20: 138,350 Ibs.
FORMATION. From picric acid by reduction, using sodium hydrogen
sulfide or sodium sulfide
LITERATURE. Cain, Intermediate Products (2d Ed.), 117
Dyes Derived from Picramic Acid
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli
cation-
Class
MONOAZO DYES
88
Acid Anthracene
I '14: 33,053
m-Phenylene-diamine-
ACr
Brown R
M'17: ?
[sulfonic Acids]
M'19: ?
I '20: 1,400
M '20: ?
89
Metachrome
I '14: 1,001
m-Phenylene-diamine
M
Brown B
M'17: ?
or
M '18: 349,961
m-Tolylene-diamine
M'19: ?
or
M '20: 192,914
Chloro-w-phenylene-
diamine
90 s
Chrome Brown P
m-Amino-phenol
M
91
Anthracyl Chrome
I '14: 4,596
Naphthionic Acid
ACr
Green D
M'18: ?
I '20: 3,316
92
Metachrome
3-Amino-4-methyl-
M
Bordeaux R
phenyl-p-tolyl-sul-
famide
DISAZO DYE
219
Chrome Patent
Aniline
ACr
Green N
KAcid
DYES CLASSIFIED BY INTERMEDIATES 495
Picric Acid
2 N/\
OH
N0 2
NO 2
STATISTICS. Manufactured in 1919 and 1920 in an indeterminate
amount for dyeing purposes. Prior to 1919 it was made in very
large quantities for explosive uses
FORMATION. Phenol is sulfonated and then trinitrated
LITERATURE. Cain, Intermediate Products (2d Ed.), 114
Lange, Zwischenprodukte, #1116-1121
Schultz, Farbstofftabellen (1914), #5
USES. For the manufacture of picramic acid. It is also a dye, Schultz #5
Primuline-sulfonic Acid (Sodium Salt)
(This is the " =.
v\coA^
DYES CLASSIFIED BY INTERMEDIATES
499
FORMATION. From alizarin by oxidation with manganese dioxide and
sulfuric acid
LITERATURE. Lange, Zwischenprodukte, #3129, 3271
Barnett, Anthracene and Anthraquinone
Dyes Derived from Purpurin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
783
ANTHRAQUINONE AND
ALLIED DYES
Purpurin
M
862
Alizarin Blue
Black B
I '14: 54,706
I '20: 28,802
Aniline
[Sulfonation]
M
Pyrogallic Acid
See, Pyrogallol
Pyrogallol (C. A. nomen.)
1:2: 3-Trihydroxy-benzene
Pyrogallic Acid
OH
!OH
OH
STATISTICS. Imported '14: 24,964 Ibs.
Manufactured regularly, but amounts not disclosed
FORMATION. From gallic acid by heating in an autoclave in presence of
water
LITERATURE. Lange, Zwischenprodukte, #958
Green, Organic Coloring Matters (1908), 45
500 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Pyrogallol
Schidtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
62
Azo Galleine
Dimethyl-p-phenylene-
diamine
M
84
Azo Chromine
p-Amino-phenol
M
158
Chrome Brown RR
I '14: 7,241
M'17: ?
4-Amino-l-phenol-2: 6-
disulfonic Acid
M
I '20: 2,183
XANTHONE DYES
599
Galleine
I '14: 15,404
M'19: ?
I '20: 5,075
M'20: ?
Phthalic Anhydride
Pyrogallol (2 mols)
M
601
Coeruleine S
I '14: 3,404
M'19: ?
I '20: 9,392
Phthalic Anhydride
Pyrogallol (2 mols)
[Dehydration]
M
or
[Galleine dehydrated]
ANTHRAQUINONE AND
ALLIED DYES
769
Alizarin Yellow C
[Acetic Acid]
M
770
Alizarin Yellow A
Benzoic Acid
M
or
Benzo trichloride
773
Anthracene Yellow
I '14: 4,046
[Aceto-acetic Ethyl
Ester; Bromination]
M
Pyrogallol-5-sulfonic Acid
3:4: 5-Trihydroxy-6enzene-sulfonic Acid (C. A. nomen.)
OH
H0 3 S
DYES CLASSIFIED BY INTERMEDIATES
501
FORMATION. 1 : 3-Dichloro-2-hydroxy-benzene-5-sulfonic acid (as po-
tassium salt) is fused with concentrated caustic potash solution at
150-160
LITERATURE. Lange, Zwischenprodukte, #959
Ger. Pat., 203,145; Frdl. 9, 247
Dyes Derived from Pyrogallol-5-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
623
Pyrogallol-cyanine-
Nitroso-dimethyl-
M
sulfonic Acid
aniline
Quinaldine (C. A. nomen.)
2-Methyl-quinoline
a-Methyl-quinoline
STATISTICS. Manufactured '19: ?
Manufactured '20: ?
FORMATION. By condensing aniline and p&racetaldehyde either cold,
or hot, in the latter case using hydrochloric acid and aluminum or
zinc chloride to catalyze the reaction
LITERATURE. Cain, Intermediate Products (2d Ed.), 84
Lange, Zwischenprodukte, #2000-2002
502 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Quinaldine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
610
QUINOLINE DYES
Quinoline Red
Benzo-trichloride
Isoquinoline
B
612
Quinoline Yellow
Spirit Soluble
I '14: 79,553
I '20: 205
Phthalic Anhydride
ss
613
Quinoline Yellow
Water Soluble
I '14: 15,354
I '20: 34,440
Phthalic Anhydride
[Sulfonation]
A
Quinizarin (C. A. nomen.}
1 : 4-Dihydroxy-anthraquinOne
CO
CO
OH
OH
FORMATION. From anthraquinone by oxidation with sulfuric acid in
presence of boric acid
LITERATURE. Lange, Zwischenprodukte, #3233, 3260, 3268, 3270,
3274,3276,3314,3351
Cain, Intermediate Products (2d Ed,), 255
Dyes Derived from Quinizarin
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
852
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Irisol D
p-Toluidine
[Sulfonation]
A
852
Alizarin Direct
Violet R
4-Toluidine-3-sulfonic
Acid
A
DYES CLASSIFIED BY INTERMEDIATES
503
Dyes Derived from Quinizarin (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
865
ANTHRAQUINONE AND
ALLIED DYES
(continued)
Alizarin Cyanine
Green E
p-Toluidine (2 mols)
[Sulfonation]
ACr
865
Alizarin Direct
Green G
I '14: 2,000
I '20: 31,851
M'20: ?
4-Toluidine-3-sulfomc
Acid (2 mols)
ACr
Quinoline
STATISTICS. Imported '14: very small
Manufactured '19: ?
FORMATION. (1) By extraction from coal-tar. (2) By synthesis
through the heating together of aniline, nitro-benzene, glycerol and
sulfuric acid for some time, first at 125 and then at 180
LITERATURE. Lange, Zwischenprodujrte, #1995
Thorpe, Die. Chemistry, 4, 468
Dye Derived from Quinoline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
611
QUINOLINE DYE
Quinoline Blue
Lepidine
[Amyl iodide]
Photo-
graphy
504 DYES CLASSIFIED BY INTERMEDIATES
RAcid
2-Naphthol-3: 6-disulfonic Acid (C. A. nomen.)
/3-Naphthol-disulfonic Acid R
/3-Naphthol-a-disulfonic Acid
Note. R Add is occasionally applied to other naphthalene derivatives,
e.g., 2-amino-3-naphthol-6-sulfonic acid, 2-naphthylamine-3 : 6-disulfonic
acid, 2: 3-dihydroxy-naphthalene-6-sulfonic Add
H0 3 S
OH
SO 3 H
STATISTICS. Imported '14: 46,267 Ibs.
Manufactured '18: 712,033 Ibs.
Manufactured ' 19: 1,008,007 Ibs.
Manufactured '20: 1,250,674 Ibs.
FOKMATION. From /3-naphthol by disulfonation, and separation from
the G acid simultaneously formed
LITERATURE. Cain, Intermediate Products (2d Ed.), 226
Lange, Zwischenprodukte, #2651, 2652
Thorpe, Die. Chemistry, 3, 626
Dyes Derived from R Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
39
MONOAZO DYES
Ponceau G
M'17: ?
M'19: ?
Aniline
A
47
Orange III
M'18: ?
0-Naphthol
A
65
Azo Coralline L
M'17: ?
M'18: ?
M'19: ?
I '20: 249
M'20: ?
p-Amino-acetanilide
A
DYES CLASSIFIED BY INTERMEDIATES
505
Dyes Derived from R Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
82
Ponceau R, 2R
I '14: 35,259
Xylidine
A
Scarlet R, 2R
M'17: 633,429
M'18:
1,189,054
M'19: 552,680
M'20:
ILJ-
1,286,002
83
Ponceau 4R
I '14: 3,557
Pseudocumidine
A
M'17: ?
M'18: ?
M'19: 24,152
M'20: ?
101
Coccinine B
w-Amino-p-cresol
A
Methyl Ether
112
Fast Red B
I '14: 25,821
a-Naphthylamine
A
Bordeaux B
M'17: 120,595
-,
M'18: 200,415
M'19: 161,862
I '20: 7,882
M'20: 217,406
168
Amaranth
I '14: 86,067
Naphthionic Acid
A
M'17: 66,069
M'18: 73,539
M'19: 294,416
I '20: 110
M'20: 204,958
202
Acid Alizarin Red B
I '14: 7,374
Anthranilic Acid
ACr
Palatine Chrome
M'18: ?
CL
RedB
M'19: 28,081
I '20: 1,342
M'20: 67,817
DISAZO DYES
236
Cloth Red B
I '14: 14,293
o-Amino-azo-toluene
A
Wool Red B
M'17: ?
M'18: ?
M'19: ?
M'20: ?
506 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from R Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Ustd and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
238
Union Fast Claret
Amino-azo-xylene
A
244
Coomassie Wool
M'18: ?
Acetyl-p-phenylene-
A
Black S
M'19: ?
diamine
a-Naphthylamine
269
Naphthol Black 6B
I '14: 120,512
l-Naphthylamine-4: 6-
A
I '20: 1,500
and -4: 7-disulfonic
M'20: ?
Acids
a-Naphthylamine
270
Brilliant Croceine 9B
Amino-G Acid
A
Aniline
G Acid or R Acid
272
Naphthol Black B
I '14: 103,598
Amino-G Acid
A
Brilliant Black B
M'19: ?
a-Naphthylamine
I '20: 50
298
Milling Red R
Diamino-diphenyl-
A
methane
R Acid (2 mols)
299
Cinnabar Scarlet BF
Diamino-dixylyl-
CL
mrthane
R Acid (2 mols)
300
Cinnabar Scarlet G
Diamino-dixylyl-
CL
Cotton Ponceau
phenyl-methane
R Acid (2 mols)
341
Crumpsall Direct
M'17: ?
Benzidine
D
Fast Red R
M'18: ?
Salicylic Acid
M'19: ?
M'20: ?
412
Congo Blue 2B
Dianisidine
D
Nevile-Winther's Acid
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from R Acid (continued)
507
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
414
Indazurine B
Dianisidine
D
1 : 7-Dihydroxy-naph-
thalene-4-s u 1 f o n i c
Acid
429
Indazurine BB
Dianigidine
D
1 : 7-Dihydroxy-2-naph-
thoic-4 sulfonic Acid
433
Coomassie Blaok B
1 : 4 -Naphthylene-dia-
A
mine-2-sulfonic Acid
0-Naphthylamine
434
Coomassie Navy
I '20: 42,357
1 : 4-Naphthylene-dia-
A
Blue
mine-2-sulfonic Acid
/3-Naphthol
TRISAZO DYE
484
Milling Scarlet B
Diamino-azoxy-toluene
A
Nevile-Winther's Acid
2R Acid
2-Amino-8-naphthol-3 : 6-disulf onic Acid
Amino-naphthol-disulfonic Acid RR or 2R
7-Amino-l-naphthol-3: 6-disulf onic Acid (C. A. nomen.)
HO
H0 3 S
NH 2
S0 3 H
FORMATION. From sodium 2-naphthylamine-3 : 6 : 8-trisulf onate by
fusion with caustic soda at 220-260
LITERATURE. Cain, Intermediate Products (2d Ed.), 239
Lange, Zwischenprodukte, #2734
508 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2R Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
44
MONOAZO DYE
Azo Archil R
Aniline
A
442
TRISAZO DYES
Direct Black V
I '14: 145,738
Benzidine
a-Naphthylamine
Gamma Acid
D
443
Direct Indone
BlueR
Benzidine
a-Naphthylamine
HAcid
D
449
Trisulfon Brown B
I '14: 16,781
I '20: 38,616
Benzidine
Salicylic Acid
w-Phenylene-diamine
D
453
Columbia Black R
I '14: 1,307
Tolidine
m-Tolylene-diamine
(2 mols)
D
454
Trisulfon Brown G
I '14: 1,323
Tolidine
Salicylic Acid
w-Phenylene-diamine
D
455
Columbia Black B
I '14: 165,727
Dianisidine
m-Tolylene-diamine
(2 mols)
D
457
Trisulfon
Brown GG
I '14: 7,562
I '20: 38,411
Dianisidine
Salicylic Acid
m-Phenylene-diamine
D
Red Acid
l:5-Dihydroxy-naphthalene-3:7-disulfonic Acid (not considered
herein)
Resorcine
See, Resorcinol (C. A. nomen.)
DYES CLASSIFIED BY INTERMEDIATES
Resorcinol (C. A. nomen.)
509
STATISTICS. Imported '14: 61,624 Ibs.
Manufactured ' 17 : ?
Manufactured '18 : 2,087 Ibs.
Manufactured '19: 96,397 Ibs.
Manufactured '20: 139,315 Ibs.
FORMATION. Benzene is disulfonated with oleum, and the resulting
benzene-ra-disulfonic acid is fused with a large excess of caustic
soda
LITERATURE. Cain, Intermediate Products (2d Ed.), 130
Dyes Derived from Resorcinol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
1
NITROSO DYE
Solid Green O
[Dinitroso Derivative]
M
11
STILBENE DYE
Mikado Orange
Chloramine
Orange G
1 ; 14: 26,010
M'17: ?
M'18: ?
M'19: ?
M '20: 38,287
p-Nitro-toluene-o-sul-
fonic Acid (4 mols)
[Resorcinol as reducing
agent]
D
35
MONOAZO DYES
Sudan G
I '14: 798
Aniline
88
60
Azo Phosphine GO
I '14: 50
ra-Amino-phenyl-tri-
methyl-ammomum
Chloride
B
75
New Phosphine G
I '14: 500
Amino-benzyl-
dimethyl-amine
B
510 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
143
Chrysoine
I '14: 6,252
Sulfanilic Acid
A
Tropaeoline
M'17: ?
M'18: ?
M'19: ?
M'20: ?
155
Acid Alizarin
I '20: 201
o-Amino-phenol-p-
M
Garnet R
M'20: ?
sulfonic Acid
DISAZO DYES
211
Resorcine Brown
I '14: 13,189
m-Xylidine
A
M'17: ?
Sulfanilic Acid
M'18: ?
M'19: ?
I '20: 2,484
M'20: ?
213
Fast Brown
I '14: 3,206
Naphthionic Acid
A
M'17: ?
(2 mols)
M'18: ?
M'19: ?
M'20: ?
222
Janus Yellow G
I '14: 2,250
ra-Nitro-aniline
B
I '20: 758
w-Amino-phenyl-tri-
methyl-ammonium
Chloride
317
Pyramidol
Benzidine
D
Brown BG
Resorcinol (2 mols)
374
Congo 4R
M'18: ?
Tolidine
D
Congo Red 4R
Naphthionic Acid
376
Pyramidol Brown T
Tolidine
D
Resorcinol (2 mols)
TRISAZO DYES
435
Janus Brown B
p-Amino-benzyl-
B
diethyl-amine
a-Naphthylamine
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
511
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
(continued)
437
Isodiphenyl Black R
p-Phenylene-diamine
D
(2 mols)
Gamma Acid
461
Coomassie Union
1 : 4-Naphthylene-dia-
D
Blacks
mine-2-sulfonic Acid
Gamma Acid
Resorcinol (2 mols)
477
Congo Brown G
I '14: 52,141
Benzidine
D
Naphthamine
M'17: ?
Sulfanilic Acid
Brown 4G
M'18: ?
Salicylic Acid
M'19: ?
I '20: 443
M '20: 229,489
480
Congo Brown R
I '14: 3,045
Benzidine
D
Laurent's Acid
Salicylic Acid
481
Azo Corinth
Tolidine
D
Naphthionic Acid
3-Amino-phenol-4-sul-
f onic Acid
TETRAKISAZO DYE
489
Hessian Brown BBN
Benzidine
D
Sulfanilic Acid (2 mols)
Resorcinol (2 mols)
XANTHONE DYES
573
Rhodamine B
I '14: 59,354
Phthalic Anhydride
B
M'17: ?
Resorcinol (2 mols)
M'18: ?
[Phosphorus penta-
M'19: ?
chloride; diethyl-
I '20: 24,709
amine]
M'20: ?
578
Rhodamine 12 GF
Dimethylamino-hy-
B
droxy-b e n z o y 1-
benzoic Acid
[Formaldehyde;
esterification]
512
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
580
XANTHONE DYES
(continued}
Fast Acid Violet B
I '14: 20,688
M'19: ?
I '20: 2,907
Phthalic Anhydride
Resorcinol (2 mols)
Aniline or p-io\-
uidine (2 mols)
[PC1 5 ; sulfonation]
A
582
Fast Acid VioletA2R
I '14: 875
I '20: 2,679
M'20: ?
Phthalic Anhydride
Resorcinol (2 mols)
o-Toluidine (2 mols)
[PC1 5 ; sulfonation]
A
583
Acid Rosamine A
I '14: 50
I '20: 141
Phthalic Anhydride
Resorcinol (2 mols)
Mesidine (2 mols)
[PC1 5 ; Sulfonation]
A
584
Fast Acid Blue R
I '14: 4,022
I '20: 130
3: 6-Dichloro-phthalic
Acid
Resorcinol (2 mols)
p-Phenetidine (2 mols)
[PC1 5 ; Sulfonation]
A
585
Uranine
Fluoresceine
I '14: 2,273
M'17: ?
M'19: ?
I '20: 10
Phthalic Anhydride
Resorcinol (2 mols)
A
586
Chrysoline
I '20: 1,402
Phthalic Anhydride
Resorcinol (2 mols)
Benzyl Chloride
A
587
Eosine
I '14: 94,528
M'17: 68,496
M '18: 161,153
M'19: 121,303
I '20: 296
M'20: 85,489
Phthalic Anhydride
Resorcinol (2 mols)
[Bromination]
or
[Fluoresceine
brominated]
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
513
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
(continued)
588
Eosine Spirit Soluble
Phthalic anhydride
88
Methyl Eosine
Resorcinol (2 mols)
[Bromination, methyla-
tion]
or
[Eosine methyl ester]
589
Eosine SP
I '14: 2,315
Phthalic Anhydride
88
M'20: ?
Resorcinol (2 mols)
[Bromination, ethyla-
tion]
or
Eosine ethyl ester]
590
Eosine BN
I '14: 20,143
Phthalic Anhydride
A
Acid Eosine
I '20: 1,132
Resorcinol (2 mols)
M'20: ?
[Bromination, nitration
or
[Dibromo-fluoresceine
dinitrated]
591
Erythrosine G
I '14: 99
Phthalic Anhydride
A
Resorcinol (2 mols)
[lodation]
or
[Fluoresceine iodated]
592
Erythrosine B
I '14: 4,350
Phthalic Anhydride
A
M'17: 505
Resorcinol (2 mols)
M'18: 1,636
[lodation]
M'19: ?
or
I '20: 9
[Fluoresceine iodated]
M'20: 6,874
593
Phloxine P
I '14: 2,244
3 : 6-Dichloro-phthalic
M'17: ?
Acid
M'18: ?
Resorcinol (2 mols)
M'19: ?
[Bromination]
M'20: ?
514 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Resorcinol (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
(continued)
594
Cyanosine Spirit
3 : 6-Dichloro-phthalic
A
Soluble
Acid
Resorcinol (2 mols)
[Bromination, methyla-
tion]
or
[Phloxine methyl ester]
595
Rose Bengal
I '14: 2,277
3 : 6-Dichloro-phthalic
A
M'20: ?
Acid
Resorcinol (2 mols)
[lodation]
596
Phloxine
I '14: 1,020
Tetrachloro-phthalic
A
Acid
Resorcinol (2 mols)
[Bromination]
597
Rose Bengal B
I '14: 1,354
Tetrachloro-phthalic
A
M'17: ?
Acid
M'18: ?
Resorcinol (2 mols)
M'19: ?
[lodation]
598
Cyanosine B
Tetrachloro-phthalic
ss
Acid
Resorcinol (2 mols)
[Ethylation]
or
[Phloxine ethylated]
600
Coeruleine B
M'19: ?
Phthalic Anhydride
M
M '20: ?
Resorcinol (2 mols)
[Dehydration]
[Fluoresceine
dehydrated]
OXAZINE DYES
642
Phenocyanine TC
I '20: 4,740
Nitroso-dimethyl-
M
aniline
Gallic Acid
or
[Gallocyanine]
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Eesorcinol (continued)
515
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYES
(continued)
643
Phenocyanine T V
M 17 -
Nitroso-dimethyl-
M
I '20: 1,543
aniline
Gallic Acid
[Sulfonation]
or
[Gallocyanine;
Sulfonation]
644
Ultracyanine B
Nitroso-dimethyl-
M
aniline
Gallic Acid
[Alkaline Condensation]
or
[Gallocyanine alkaline
condensation with
resorcinol]
647
Nitroso Blue MR
Nitroso-dimethyl-
MF
Resorcine Blue
aniline
648
Iris Blue
Nitroso-resorcinol
A
[Bromination]
Resorcinol Methyl Ether
Methyl-resorcinol
m-Methoxy-phenol (C. A. nomen.)
IOCH 3
FORMATION. From resorcinol by methylation
LITERATURE. Ullmann, Enzy. tech. Chemie, 9, 490
516
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Resorcinol Methyl Ether
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
575
Rhodine 12 GM
Dimethylamino-hy-
B
droxy-b e n z o y 1 -
benzole Acid
[Ethyl esterification]
Resorcinol-succinein
3 : 6-Dihydroxy-9-zanthene-propionic Acid; 7-Lactone (C. A
nomen.)
CH 2 O
CH 2 .CO
FORMATION. From resorcinol and succinic acid (or its anhydride) by
Seating together at about 200 C.
LITERATURE. Cohen, Theoretical Organic Chemistry (1918 Ed.), 461
Dye Derived from Resorcinol-succinein
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
570
Rhodamine S
I '14: 600
[Dimethyl-amine
A
I '20: 273
2mols]
a-Resorcylic Acid (C. A. nomen.)
3: 5-Dihydroxy-benzoic Acid
m-Dihydroxy-benzoic Acid
COOH
= C 7 H 6 O 4 =154
DYES CLASSIFIED BY INTERMEDIATES 517
FORMATION. From 3: 5-disulfo-benzoic acid by caustic soda fusion
LITERATURE. Lange, Zwischenprodukte, #881
Ullmann, Enzy. tech. Chemie, 2, 345
Dye Derived from a-Resorcylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
771
Resoflavine W
a-Resorcylic Acid
M
(2 mols)
[Oxidation]
j3-Resorcylic Acid (C. A. nomen.)
2 : 4-Dihydroxy-benzoic Acid
FORMATION. By heating resorcinol with a solution of potassium bi-
carbonate under reflux
LITERATURE. Ullmann, Enzy. tech. Chemie, 2, 345
Bistrzycki and Kostanecki, Ber. 18, 1984 (1885)
Dye Derived from 0-Resorcylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
49
Prague Alizarin
w-Nitro-aniline
M
Yellow G
RG Acid
See, l-Naphthol-3 : 6-disulfonic Acid
518 DYES CLASSIFIED BY INTERMEDIATES
Rho Acid
See, Anthraquinone-1 : 5-disulfonic Acid
Rumpff Acid
See, Croceine Acid
S Acid
See, l-Amino-8-naphthol-4-sulfonic Acid
See, 1 : 8-Dihydroxy-naphthalene-4-sulfonic Acid
See, l-Naphthylamine-8-sulfonic Acid
See, l-Naphthylamine-4 : 8-disulf onic Acid
l-Naphthol-8-sulfonic Acid (not considered herein)
1 : 8-Dihydroxy-naphthalene-2 : 4-disulf onic Acid (not
considered herein)
1 : 7-Dihydroxy-naphthalene-6-carboxylic Acid (not con-
sidered herein)
Note. The use of S as a trivial name is very confusing and should be
avoided
2S Acid
See, l-Amino-8-naphthol-2: 4-disulf onic Acid
Salicylic Acid
o-Hydroxy-benzoic Acid
COOH
= C 7 H 6 3 =:138
Technical U. S. P.
Ibs. Ibs.
STATISTICS. Manufactured '17: 960,339 2,495,285
Manufactured '18: 1,395,630 3,270,462
Manufactured ' 19 : 3,467,055 2,619,726
Manufactured '20: 3,914,163 2,663,494
FORMATION. Phenol is treated with caustic soda, dried and powdered;
and then subjected to action of carbon dioxide under pressure and
at 100-145
DYES CLASSIFIED BY INTERMEDIATES
519
LITERATURE. Cain, Intermediate Products (2d Ed.), 149
Lange, Zwischenprodukte, #145, 471-475, 479
Dyes Derived from Salicylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
48
Alizarin Yellow GG
I '14: 144,761
m-Nitro-aniline
M
M'17:
1,452,622
M'18:
2,233,208
M'19: 163,170
M '20: 211,580
58
Alizarin Yellow R
I '14: 97,059
p-Nitro-aniline
M
M '17: 215,468
or
M '18: 385,910
Aniline [with nitration
M '19: 130,424
after coupling]
I '20: 860
M'20: 83,334
96
Chrome Fast
I '14: 150
o-Anisidine
M
Yellow GG
I '20: 500
or
m-Amino-p-cresol
Methyl Ether
102
Diamond Flavine G
I '14: 23,089
Benzidine
M
M'17: ?
M'18: ?
M'19: ?
M'20: ?
103
Dutch Yellow
Benzidine
M
[Sodium sulfite]
133
Eriochrome
I '14: 1,433
p-Nitro-aniline-o-
ACr
Phosphine R
sulf onic Acid
177
Chrome Yellow D
I '14: 129,651
Broenner's Acid
M
Mordant Yellow O
M'17: ?
M'18: 32,011
M'19: ?
I '20: 1,389
M'20: ?
520 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
178
MONOAZO DYES
(continued)
Crumpsall Yellow
Amino-G Acid
A
199
Oriol Yellow
Cotton Yellow R
I '14: 13,416
I '20: 125
M'20: ?
D ehydrothio-p-t olui-
dine-sulfonic Acid
or
Primuline
D
204
Diamond Yellow G
m- or p-Amino-benzoic
Acid
M
221
DISAZO DYES
Anthracene Acid
Brown G
M'17: ?
M'18: ?
I '20: 225
Sulfanilic Acid
p-Nitro-aniline
ACr
250
Milling Orange
I '14: 4,370
Amino-azo-benzene-
sulfonic Acid
M
291
Azo Alizarin
Bordeaux W
p-Phenylene-diamine
Nevile-Winther's Acid
M
292
Azo Alizarin
Black I
p-Phenylene-diamine
Chromotropic Acid
M
294
Anthracene Yellow C
Fast Mordant
Yellow
I '14: 3,678
I '20: 887
Thio -aniline
Salicylic Acid (2 mols)
A
ACr
296
Cotton Yellow G
I '14: 31,472
I ; 20: 4,651
p-Amino-acetanilide
(2 mols)
Salicylic Acid (2 mols)
Phosgene
D
305
Hessian Yellow
Diamino-stilbene-disul-
fonic Acid
Salicylic Acid (2 mols)
D
339
Brilliant Orange G
I '14: 6,321
M'17: ?
Benzidine
3 -Amino-phenol-4-
sulfonic Acid
D
DYES CLASSIFIED BY INTERMEDIATES
521
Dyes Derived from Salicylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
340
DISAZO DYES
(continued)
Benzo Orange R
I '14: 1,073
M'17: ?
M'18: 50,422
M'19: 42,807
I '20: 220
M'20: 86,210
Benzidine
Naphthionic Acid
D
340
Chlorazol Orange 2R
1
Benzidine
2-Naphthylamine-7-
sulf onic Acid
D
341
Crumpsall Direct
Fast Red R
M'17: ?
M'18: ?
M'19: ?
M'20: ?
Benzidine
RSalt
D
342
Chrysamine G
I '14: 608
M'17: 26,061
M'18: 28,846
M'19: 54,279
I '20: 9,810
M'20: 49,342
Benzidine
Salicylic Acid
(2 mols)
D
343
Diamine Fast
RedF
I '14: 50,479
M'19: 56,864
I '20: 4,040
M'20: 115,865
Benzidine
Gamma Acid
[Acid coupling]
D
344
Diamine Brown M
I '14: 65,396
M'18: ?
M'19: 15,959
M'20: 257,872
Benzidine
Gamma Acid
[Alkaline coupling]
D
345
Oxamine Maroon
Benzidine
l-Amino-5-naphthol-7-
sulfonic Acid
D
346
Oxamine Red
I '14: 11,636
I '20: 848
Benzidine
J Acid
D
522 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
347
DISAZO DYES
(continued)
Diphenyl Brown RN
Benzidine
Methyl-gamma Acid
D
348
Diphenyl Brown BN
I '14: 13,471
Benzidine
Dimethyl-gamma Acid
D
349
Diamine Brown B
I '20: 24
Benzidine
Phenyl-gamma Acid
D
350
Alkali Yellow R
Benzidine
Dehydrothio-p-tolui-
dine-sulfonic Acid
D
355
Anthracene Red
I '14: 3,873
M'19: ?
I '20: 104
M'20: ?
o-Nitro-benzidine
Nevile-Winther's Acid
ACr
393
Diphenyl Brown
3GN
M'20: ?
Tolidine
Dimethyl-gamma Acid
D
394
Chrysamine R
I '14: 6,261
M'20: ?
Tolidine
Salicylic Acid (2 mols)
D
404
Diamine Yellow N
M'17: ?
I '20: 313
Ethoxy-benzidine
rhenol
[Ethylation]
D
444
TRISAZO DYES
Crumpsall Direct
Fast Brown B
Benzidine
Aniline
Gamma Acid
D
445
Crumpsall Direct
Fast Brown
Benzidine
Aniline
Phenyl-gamma Acid
D
446
Benzo Olive
I '14: 1,149
Benzidine
a-Naphthylamine
HAcid
D
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
523
Schultz
Number
jor Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
447
TRISAZO DYES
(continued)
Benzo Gray S
I '14: 802
Benzidine
a-Naphthylamine
Nevile-Winther's Acid
D
448
Diamine Bronze G
I '14: 4,495
Benzidine
w-Phenylene-diamine
HAcid
D
449
Trisulfon
Brown B
I '14: 16,781
I '20: 38,616
Benzidine
w-Phenylene-diamine
2R Acid
D
454
Trisulfon
Brown G
I '14: 1,323
Tolidine
m-Phenylene-diamine
2R Acid
D
457
Trisulfon
Brown GG
I '14: 7,562
I '20: 38,411
Dianisidine
m-Phenylene-diamine
2R Acid
D
465
Columbia Black
Green D
Benzidine
l-Amino-8-naphthol-4-
sulf onic Acid
Aniline
D
466
Eboli Green
Benzidine
Sulfanilic Acid
l-Amino-8-naphthol-
3: 5-disulfonic Acid
D
468
Diphenyl Green 3G
Benzidine
HAcid
o-Chloro-p-nitro-
aniline
D
475
Diamine Green G
Oxamine Green G
I '14: 7,329
M'17: ?
M'18: 29,118
M '19: 136,638
I '20: 1,332
M'20: 52,292
Benzidine
HAcid
p-Nitro-aniline
D
524
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYES
476
(continued}
Benzamine Brown
3GO
I '14: 16,988
M'17: ?
Benzidine
Sulfanilic Acid
D
M'18: ?
M'19: ?
. w-Phenylene-diamine
M '20: 623,757
477
Congo Brown G
Naphthamine
Brown 4G
I '14: 52,141
M'17: ?
M'18: ?
Benzidine
Sulfanilic Acid
Resorcinol
D
M'19: ?
I '20: 443
M '20: 229,489
478
Columbia Green
I '14: 45,162
M'18: ?
Benzidine
Sulfanilic Acid
D
I '20: 7,555
l-Amino-8-naphthol-4-
sulfonic Acid
480
Congo Brown R
I '14: 3,045
Benzidine
Laurent's Acid
D
Resorcinol
482
Alizarin Yellow FS
Aniline and
M
o-Toluidine
p-Toluidine
Salicylic Acid (3 mols)
or
[Fuchsine and
Salicylic Acid]
TRIPHENYL-METHANE
DYES
510
Azo Green
m-Amino-tetramethyl-
p: p'-diamino-tri-
phenyl-methane
or from
m-Nitro-benzaldehyde
and dimethyl-aniline
(2 mols)
[Oxidation]
M
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Salicylic Acid (continued)
525
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRI PHEN YL-METHANE
DYES
(continued)
549
Chrome Violet
I '14: 51
Hydrol
M
[Oxidation]
557
Chrome Violet
I '14: 220
Salicylic Acid (3 mols)
M
M'18: ?
[Formaldehyde and
sulfuric Acid]
Schaeffer's a Acid
l-Naphthol-2-sulfonic Acid (not considered herein)
Schaeffer's Acid*
Schaeffer's Acid
2-Naphthol-6-sulfonic Acid (C. A. nomen.)
/3-Naphthol-sulfonic Acid S
/3-Naphthol-sulfonic Acid Schaeffer
/3-Naphthol-a-sulfonic Acid of Armstrong and Schultz
/3-Naphthol-/3-sulfonic Acid
H0 3 S
OH
STATISTICS. Manufactured '17: 1,108,049 Ibs. 2
Manufactured '18: 169,383 Ibs.
Manufactured '19: 146,111 Ibs.
Manufactured '20: 475,243 Ibs.
FORMATION. By sulfonation of /3-naphthol, and separation from the
Croceine acid formed simultaneously j
1 Schaeffer's Acid is very occasionally used when referring to l-Naphthol-2-sulfonic
acid, but this is more properly known as Schaeffer's a acid.
2 Includes Croceine Acid.
526
DYES CLASSIFIED BY INTERMEDIATES
LITERATURE. Cain, Intermediate Products (2d Ed.), 223
Lange, Zwischenprodukte, #2430-2432
Thorpe, Die. Chemistry, 3, 624
Dyes Derived from Schaeffer's Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
4
Naphthol Green
1 '14: 19,146
[Nitroso-Derivative]
A
M'17: 75,850
M'18: 22,465
M'19: 34,646
I '20: 100
M'20: ?
37
Ponceau 4GB
I '14: 13,046
Aniline
A
Croceine Orange
M'17: ?
M '18: 30,824
M'19: 17,274
M'20: 96,573
70
Brilliant Orange
I '14: 21,480
Toluidine
A
M'17: ?
M'18: ?
M'19: ?
M'20: ?
79
Brilliant Orange R
I '14: 4,204
Xylidine
A
Xylidine Orange RR
M'17: ?
M'18: 18,909
M'19: ?
M'20: ?
111
Fast Red BT
M'17: ?
a-Naphthylamine
A
M'18: ?
M'19:- ?
123
Emine Red
Isodehydro-thio-w-
A
xylidine
166
Fast Red E
I '14: 2,473
Naphthionic Acid
A
M'17: ?
M'18: ?
M'19: ?
M'20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Schaeffer's Acid (continued)
527
Schultz
Number
JOT Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
196
Titian Red
I '14: 886
Dehydro-thio-p-tolui-
D
M'19: ?
dine-sulfonic Acid
M'20: ?
i
197
Thiazine Red G
I '14: 4,861
Primuline
D
M'18: ?
.
M'19: 11,886
M '20: 13,988
201
Pigment Scarlet G
M '17: ?
Anthranilic Acid
CL
M'18: ?
M'19: ?
DISAZO DYES
234
Cloth Red G
I '14: 554
0-Amino-azo-toluene
M
237
Bordeaux BX
Amino-azo-xylene
A
243
Coomassie Wool
Acetyl-p-phenylene-
A
Black R
diamine
a-Naphthylamine
248
Fast Scarlet B
I '14: 1,755
Amino-azo-benzene-
A
sulf onic Acid
254
Bordeaux G
Amino-azo-toluene-
A
sulf onic Acid
273
Diaminogene
I '14: 8,308
Aeetyl-1 : 4-naphthyl-
D
Blue BB
M'17: ?
ene-diamine-6-sul-
I '20: 5,936
fonic Acid
a-Naphthylamine
289
Acid Alizarin
M'17: ?
2: 6-Diamino-l-phenol-
ACr
Black SN
M'18: ?
4-sulfonic Acid
Palatine Chrome
M'19: ?
0-Naphthol
Black S
293
Milling Red G
I '14: 699
Thioaniline
A
I '20: 200
Schaeffer's Acid
(2 mols)
528 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Schaeffer's Acid (continued)
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
OXAZINE DYE
645
Gallazine A
.
Nitroso-dimeth yl-
M
aniline
Gallic Acid
[Oxidation]
Schoellkopf's Acid
See, l-Naphthol-4 : 8-disulf onic Acid
l-Naphthylamine-4 : 8-disulf onic Acid
l-Naphthylamine-8-sulfonic Acid
Also used for l-Naphthol-8-sulfonic Acid, which is not
here indexed, but the intermediate generally referred to
is that one listed first above
Semi-naphthalidam
1 : 5-Diamino-naphthalene (not considered herein)
Siver Salt (Sodium derivative)
See, Anthraqumone-2-sulfonic Acid
SS Acid or 2S Acid
See, l-Amirio-8-naphthol-2 : 4-disulf onic Acid
m-Sulfanilic Acid
See, Metanilic Acid
Sulfanilic Acid (C. A. nomen.
p-Amino-benzene-sUlfonic acid
Aniline-p-sulfonic acid
S0 3 H
NH S
DYES CLASSIFIED BY INTERMEDIATES
529
STATISTICS. Imported '14: 4,477 Ibs.
Manufactured '17: 1,184,412 Ibs.
Manufactured '18: 1,247,478 Ibs.
Manufactured '19: 1,023,861 Ibs.
Manufactured '20: 1,796,838 Ibs.
FORMATION. From aniline by heating with sulfuric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 47
Lange, Zwischenprodukte, #615-620
Dyes Derived from Sulfanilic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYES
22
Xylene Yellow 3G
I '14: 23,074
l-(2: 5-Dichloro-4-sulfo-
A
I '20: 77,782
phenyl) -3-methyl-5-
pyrazolone
23
Tartrazine
I '14: 272,477
p-Phenyl-hydrazine-
A
M'17: ?
sulfonic Acid
M'18: ?
M'19: ?
I '20: 47,877
M '20: 701,722
MONOAZO DYES
138
Helianthine
I '14: 500
Dimethyl-aniline
A
Methyl Orange
M'18: ?
M'19: ?
M'20: ?
139
Orange IV
I '14: 19,020
Diphenylamine
A
M'19: ?
I '20: 608
140
Azoflavine RS
I '14: 39,869
Diphenylamine
A
Curcumeine
I ; 20: 5,225
[Nitration]
141
Azo Yellow 3G
I '14: 114,689
Diphenylamine
A
M'17: ?
[Strong nitration]
M'18: ?
.
M'19: ?
I '20: 4,818
M'20: ?
530
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
142
Brilliant Yellow S
I '14: 9,934
Diphenylamine
A
Curcumine
[Sulfonation]
143
Chrysoine
I '14: 6,252
Resorcinol
A
Tropoeoline
M'17: ?
M'18: ?
M'19: ?
M'20: ?
144
Orange I
I '14: 8,305
a-Naphthol
A
M'17: ?
M'18: ?
M'19: ?
I '20: 1,323
M'20: 14,684
145
Orange II
I 1 14: 128,877
/3-Naphthol
A
M'17: 712,586
M'18: 916,890
M'19:
1,133,925
I '20: 2,265
-
M'20:
1,850,341
146
Azo Fuchsine G
I '14: 17,819
1 : 8-Dihydroxy-naph-
A
I '20: 3,694
thalene-4-sulfonic
Acid
147
Azo Fuchsine 6B
I '14: 13,206
1 : 8-Dihydroxy-naph-
A
M'17: ?
thalene-4-sulfomc
M'18: ?
Acid
[? Classification]
DISAZO DYES
211
Resorcine Brown
I '14: 13,189
w-Xylidine
A
M'17: ?
Resorcinol
M'18: ?
M'19: ?
I '20: 2,484
M '20: ?
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
531
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
212
MONOAZO DYES
(continued]
Fast Brown G
Acid Brown G
I '14: 17,407
I '20: 485
a-Naphthol
Sulfanilic Acid (2 mols)
A
220
Palatine Black A
Buffalo Black PY
I '14: 299,274
I '20: 200
l-Amino-8-naphthol-4-
sulfonic Acid
a-Naphthylamine
A
221
Anthracene Acid
Brown G
M'17: ?
M'18: ?
I '20: 225
p-Nitro-aniline
Salicylic Acid
ACr
259
Ponceau 10 RB
I '14: 201
o-Anisidine
Croceine Acid
A
260
Eriochrome
Verdone A
I '14: 882
w-Amino-p-cresol
0-Naphthol
ACr
261
Buffalo Black 10B
M'17: ?
M'18: ?
M'19: ?
M'20: ?
a-Naphthylamine
HAcid
A
262
Victoria Black B
I '14: 557
a-Naphthylamine
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic Acid
A
466
TRISAZO DYES
Eboli Green
Benzidine
Salicylic Acid
l-Amino-8-naphthol-
3 : 5-disulf onic Acid
D
476
Benzamine Brown
3 GO
I '14: 16,988
M'17: ?
M'18: ?
M'19: ?
M '20: 623,757
Benzidine
m-Phenylene-diamine
Salicylic Acid
D
532
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Sulfanilic Acid (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
477
Congo Brown G
I '14: 52,141
Benzidine
D
Naphthamine Brown
M'17: ?
Resorcinol
4G
M'18: ?
Salicylic Acid
M'19: ?
I '20: 443
M '20: 229,489
478
Columbia Green
I '14: 45,162
Benzidine
D
M'18: ?
Salicylic Acid
I '20: 7,555
l-Amino-8-naphthol-4-
sulfonic Acid
TETRAKISAZO DYES
485
Benzo Brown G
I '14: 41,905
m-Phenylene-diamine
D
M'17: ?
(3 mols)
M'18: ?
Sulfanilic Acid (2 mols)
M'19: 83,506
I '20: 2,286
M '20: 109,648
489
Hessian Brown BBN
Benzidine
D
Resorcinol (2 mols)
Sulfanilic Acid (2 mols)
SULFUR DYE
738
Cotton Black
l-Chloro-2:4-dinitro-
S
tenzene
[S plus Na^S]
jfr-Sulfo-anthranilic Acid (<7. A. nomen.)
2-Amino-4-sulfo-benzoic Acid
o-Amino-p-sulfo-benzoic Acid
COOH
NHi -
S0 3 H
C 7 H 7 N0 6 S =
DYES CLASSIFIED BY INTERMEDIATES
533
FORMATION. o-Nitro-toluene is sulphonated with oleum. The resulting
o~nitro-toluene-p-sulfonic acid is converted into the sodium salt
and heated with a 40 per cent caustic soda solution at 90-95
LITERATURE. Lange, Zwischenprodukte, #855
Dye Derived from ^-Sulfo-anthranilic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
28
PYRAZOLONE DYE
Pigment Fast
Yellow G
M'19: ?
I '20: 170
3-Methyl-l-phenyl-5-
pyrazolone
CL
Sulfo-naphthalic Acid
Naphthalene-1-sulfonic Acid (not considered herein)
/3-Sulfonic Acid
See, Anthraguinone-2-sulfonic Acid
l-(^-Sulfo-phenyl)-3-methyl-5-pyrazolone
See, 3-Methyl-l-(p-sulfo-phenyl)-5-pyrazolone
-phenyl) -5-pyrazolone-3-carboxylic Acid
Tartrazinogen-sulfonic Acid
5-Keto-l-(p-sulfo-phenyl)-3-A 2 -pyrazoline-carboxylic Acid (C. A.
nomen.)
/ N \O S 3H
OC N
H 2 C C.COOH
534
DYES CLASSIFIED BY INTERMEDIATES
FORMATION. By condensation of phenyl-hydrazine-p-sulfonic acid and
ethyl oxalacetate
LITERATURE. Cain, Intermediate Products (2d Ed.), 168
Lange, Zwischenprodukte, #138
Dye Derived from l-(/>-Sulfo-phenyl)-5-pyrazolone-3-carboxylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
20
PYRAZOLONE DYE
Flavazine S
I '14: 81,375
I '20: 1,500
Aniline
A
Sulfo-m-tolylene-diamine-bis-(carbonyl-amino-naphthol-sul-
f onic Acid)
Sulfo-w-tolylene-diamine-dicarbonyl-dihydroxy-dinaphthylamine-
disulfonic Acid
3 : 5-Bis [0-(5-hydroxy-7-sulf o-2-naphthyl) -carbamide ]-p-tolu ene-
sulfonic Acid (C. A. nomen.)
CH 3
. CO . HNj // \NH . CO .
HO
S0 3 H
732
FORMATION. ^By condensation of tolylene-diamine-sulfonic acid
(CH3:NH 2 :NH 2 :S03H = 1:2:6:4) with two molecules of J acid
(2-amino-5-naphthol-7-sulfonic acid), by means of phosgene
(COC1 2 )
LITERATURE. Ger. Pat. 236,594, Frdl. 10, 904
Lange, Zwischenprodukte, #2912
DYES CLASSIFIED BY INTERMEDIATES 535
Dyes Derived from Sulfo-m-tolylene-diamine-bis-(carbonyl-amino-
naphthol-sulf onic Acid)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
280
DISAZO DYES
Azidine Fast
Scarlet GGS
o-Toluidine (2 mols)
D
281
Azidine Fast
Scarlet 4BS
o-Toluidine
/3-Naphthylamine
D
282
Azidine Fast
Scarlet 7BS
/3-Naphthylamine
(2 mols)
D
Tartrazinogen-sulfonic Acid
See, l-(p-Sulfo-phenyl)-5-pyrazolone-3-carboxylic Acid
2:4: 6 : 8-Tetrabromo-l : 5-diamino-anthraquinone
Br
H 2 N
X
C
Br
Br
FORMATION. By bromination of 1 : 5-diamino-anthraquinone
LITERATURE. Scholl and Berblinger, Ber. 37, 4180 (1904)
Barnett, Anthracene and Anthraquinone, 229
Cf. Lange, Zwischenprodukte, #3231, 3404, 3405
Dye Derived from 2: 4: 6: 8-Tetrabromo-l: 5-diamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
861
Anthraquinone
I '20: 917
Aniline (2 mols)
ACr
Blue SR
[Sulfonation]
536 DYES CLASSIFIED BY INTERMEDIATES
Tetrachloro-phthalic Acid
Cl
Cl/NcOOH
Gil JCOOH
Cl
STATISTICS. Imported '14: 1,102 Ibs.
FORMATION. Phthalic anhydride is warmed for some hours at 200 with
6 parts of antimony pentachloride, and chlorine is conducted
through the molten mass for from 8 to 12 hours
LITERATURE. Lange, Zwischenprodukte, #1184
Dyes Derived from Tetrachloro-phthalic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manujacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYES
596
Phloxine
I '14: 1,020
Resorcinol (2 mote)
A
[Bromination]
597
Rose Bengal B
I '14: 1,354
Resorcinol (2 mols)
A
M'17: ?
[lodation]
M'18: ?
M'19: ?
598
Cyanosine B
Resorcinol (2 mols)
ss
[Bromination;
Ethylation]
or
[Phloxine ethylated]
p : ^'-Tetraethyl-diamino-benzohydrol
p : p ; -Tetraethyl-diamino-diphenyl-carbinol
p: p'-Bis(diethylamino)-&enzohydrol (C. A. nomen.)
(C 2 H 5 )2N
H
O
H
N(C 2 H 5 ) 2 =C 2 iH 30 N 2 == 326
DYES CLASSIFIED BY INTERMEDIATES
537
FORMATION. Diethyl-aniline is condensed with formaldehyde in the
presence of hydrochloric acid to tetraethyl-diamino-diphenyl-
methane. This body is now oxidized to the hydrol with lead
peroxide
LITERATURE. Lange, Zwischenprodukte, #1354
Dye Derived from p: ^'-Tetraethyl-diamino-benzohydrol
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
498
DYE
Turquoise Blue
I '14: 1,541
I '20: 1,407
p-Nitro-toluene
[Oxidation]
B
p : j&'-Tetraethyl-diamino-benzophenone
p: p'-Bis(diethylamino)-frenzophenone (C. A. nomen.)
(C 2 H 5 ) 2 N/~"\ CO /~"\N(CtH B )2 = C 2 iH 28 N 2 = 324
FORMATION. By condensation of diethyl-aniline (2 mols) and phosgene
(carbonyl chloride)
LITERATURE. Lange, Zwischenprodukte, #1382
Dyes Derived from p : ^-Tetraethyl-diamino-benzophenone
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYI^-METHANE
DYES
518
Ethyl Violet
I '14: 51,933
Diethyl-aniline
B
Ethyl Purple
532
Alkali Violet 6B
I '14: 3,020
Methyl-diphenyl-
A
amine
[Sulfonation]
DlPHENYL-NAPHTHYL-
METHANE DYE
560
Night Blue
I '14: 361
p-Tolyl-a-naphthyl-
B
M'19: ?
amine
I '20: 11
538 DYES CLASSIFIED BY INTERMEDIATES
p : ^'-Tetraethyl-diamino-diphenyl-carbinol
See, p: p'-Tetraethyl-diamino-benzohydrol
p : ^'-Tetraethyl-diamino-diphenyl-methane
p: p'-Methylene-bis-[JV : JV-diethyl-aniline] (C. A. nomen.)
= C 21 H 30 N 2 = 310
FORMATION. By condensation of diethyl-aniline with formaldehyde
in the presence of hydrochloric acid
LITERATURE. Cf. Cain, Intermediate Products (2d Ed.), 102
Cf. Lange, Zwischenprodukte, #1301
Dye Derived from p : y-Tetraethyl-diamino-diphenyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
518
Ethyl Violet
I '14: 51,933
Diethyl-aniline
B
Ethyl Purple
1:3:5: 7-Tetrahydroxy-anthraquinone
See, Anthrachrysofle
Tetramethyl-diamino-benzohydrol
See, Hydrol
p : ^'-Tetramethyl-diamino-benzohydrol-sulf onic Acid
5-Dimethylamino-a-(p-dunethylamino-phenyl)-a-hydroxy-o-tolu-
ene-sulfonic Acid (C. A. nomen.)
H
S0 3 H
Ci 7 H 22 N 2 4 S = 350
DYES CLASSIFIED BY INTERMEDIATES
539
FORMATION. Tetramethyl-diamino-diphenyl-methane (from condensa-
tion of dimethyl-aniline and formaldehyde) is dissolved in mono-
hydrate and sulfonated with 25 per cent oleum at 110. This
methane-sulfonic acid is now oxidized with lead peroxide to the
hydrol derivative
LITERATURE. Ger. Pat. 88085; Frdl. 4, 219
Cain, Intermediate Products (2d Ed.), 102
Lange, Zwischenprodukte, #1312
Georgievics and Grandmougin, Dye Chemistry, 208
Dye Derived from Tetramethyl-diamino-benzohydrol-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
531
Eriocyanine A
I '14: 25,001
I '20: 8,223
M'20: ?
Dibenzyl-aniline-sul-
fonic [or disulf onic]
Acid
A
[Oxidation]
Tetramethyl-diamino-benzophenone
See, Ketone
p : ^'-Tetramethyl-diamino-diphenyl-methane
p: p'-Methylene-bis-[JV: JV-dimethyl-aniline] (C. A. nomen.)
= 254
STATISTICS. Manufactured '20: ?
FORMATION. From dimethyl-aniline (2 mols) by condensing with
formaldehyde in the presence of hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 102
Lange, Zwischenprodukte, #1301
540
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from p : />'-Tetramethyl-diamino-diphenyl-methane
Schvltz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
AURAMINES
493
Auramine
I '14: 449,276
[Sulfur and ammonia]
B
M'17: ?
M'18: 45,634
/
M '19: 127,567
I '20: 74,414
M'20: ?
ACRIDINE DYE
603
Acridine Orange NO
I '14: 2,336
[Dinitration, Reduc-
B
I '20: 1,925
tion]
[Ammonia Removal,
Oxidation]
p : ^'-Tetramethyl -diamino-diphenylmethane-sulf onic Acid
6-(p-Dimethylamino-benzyl)-N: JV-dimethyl-wetanilic Acid (C.A
nomen.)
H0 3 S
= Ci 7 H 2 2N 2 3 S = 334
FORMATION. By sulfonation of tetramethyl-diamino-diphenylmethane;
or by condensation of dimethyl-metanilic acid and dimethyl-aniline
with formaldehyde
LITERATURE. Lange, Zwischenprodukte, #1312
Cain, Intermediate Products (2d Ed.), 102
Georgievics and Grandmougin, Dye Chemistry, 208
USES. For preparation of p: p'-tetramethyl-diamino-benzohydrol-sul-
fonic acid
N': N':N": tf"-Tetramethyl-m : p' : />"-methenyl-trisaniline (C.A.
nomen.)
See, w-Amino-tetramethyl-p': p^-diamino-triphenyl-methane
DYES CLASSIFIED BY INTERMEDIATES 541
a-Tetranitro-naphthalene
From 1 : 5-Dinitro-naphthalene
/3-Tetranitro-naphthalene
1:3:6: 8-Tetranitro-naphthalene (not considered herein)
7-Tetranitro-naphthalene
1:3:5: 8-Tetranitro-naphthalene (not considered herein)
6 -Tetranitro -naphthalene
1:2:5: 8-Tetramtro-naphthalene (not considered herein)
Thioaniline
p: p'-Thio-bisaniline (C. A. nomen.)
p: p'-Diamino-diphenyl-sulfide
H 2 N
NIL
FORMATION. From aniline by heating with sulfur in presence of lead
oxide
LITERATURE. Meyer-Jacobson, Organische Chemie (1902), II, 1, 476
Dyes Derived from Thioaniline
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
293
DISAZO DYES
Milling Red G
I '14: 699
I '20: 200
Schaeffer's Acid
(2 mols)
A
294
Anthracene Yellow C
Fast Mordant
Yellow
I '14: 3,678
I '20: 887
Salicylic Acid (2 mols)
A
ACr
p: y-Thio-bisaniline (C. A. nomen.)
See, Thioaniline
542
DYES CLASSIFIED BY INTERMEDIATES
Thio-carbanilide (C. A. nomen.)
Diphenyl-thiourea
NH.CS.NH
STATISTICS. Manufactured '17: ?
Manufactured '18: 1,326,236 Ibs.
Manufactured '19: 2,268,375 Ibs.
Manufactured '20: 2,226,807 Ibs.
FORMATION. From aniline by action of carbon disulfide
LITERATURE. Ullmann, Enzy. tech. Chemie, 6, 304
Dyes Derived from Thio-carbanilide
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
874
Indigo
I '14:
Thio-carbanilide
V
8,507,359
(2 mols)
M '17: 274,771
[KCN, etc.]
M '18:
3,083,888
M'19:
8,863,824
I '20: 520,347
M'20:
18,178,231
876
Indigo MLB
Thio-carbanilide
V
Indigo White
(2 mols)
[KCN, etc.; Reduction]
or
[Indigo Reduced]
877
Indigotine
I '14: 19,329
Thio-carbanilide
A
M'17:
(2 mols), etc.
1,876,787
or
M'18:
[Indigo Sulf onated]
1,434,703
M'19:
1,699,670
I '20: 5,512
M'20:
1,395,000
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Thio-carbanilide (continued)
543
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
878
INDIGO GROUP DYES
(continued)
Indigotine P
Thio-carbanilide
(2 mols), etc.
or
[Indigo Sulfonated]
A
879
Brom Indigo
Rath jen
I '14: 53,610
M'20: ?
Thio-carbanilide
(2 mols), etc.
or
[Indigo Brominated]
V
880
Helindone Blue BB
Indigo RB
I '14: 6,856
M'17: 14,100
I '20: 3,691
M'20: ?
Thio-carbanilide
(2 mols), etc.
or
[Indigo, Brominated]
V
881
Dianthrene Blue 2B
Bromo Indigo FB
Ciba Blue 2B
I '14: 16,880
M'19: ?
I '20: 35,857
Thio-carbanilide
(2 mols), etc.
or
[Indigo, Brominated]
V
882
Indigo MLB/5B
Ciba Blue G
I '14: 1,356
I '20: 1,008
Thio-carbanilide
(2 mols), etc.
or
[Indigo, Brominated]
V
883
Indigo MLB/6B
Indigo KG
I '14: 3,191
I '20: 4,130
M'20: ?
Thio-carbanilide
(2 mols), etc.
or
[Indigo, Brominated]
V
884
Brilliant Indigo
BASF/2B
I '14: 4,518
Thio-carbanilide
(2 mols), etc.
or
[Indigo, Chlorinated
Brominated]
V
885
Brilliant Indigo
BASF/B
I '14: 8,175
I '20: 3,503
Thio-carbanilide
(2 mols), etc.
or
[Indigo Chlorinated]
V
544 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Thio-carbanilide (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli
cation
Class
INDIGO GROUP DYES
(continued}
886
Brilliant Indigo
I '14: 12,057
Thio-carbanilide
V
BASF/G
(2 mols), etc.
or
[Indigo Chlorinated,
Brominated]
889
Indigo Yellow 3G
Thio-carbanilide
V
(2 mols), etc.
Benzoyl Chloride
or
[Indigo, Benzoyl
^Chloride]
890
Ciba Yellow G
I 14: 48
Thio-carbanilide
V
(2 mols), etc.
Benzoyl Chloride
- v '
[Bromination]
or
[Indigo Yellow 3G,
Brominated]
Thio-indoxyl
See, 2-Hydroxy-thionaphthene
Thio-indoxyl-carboxylic Acid
See, 2-Hydroxy-thionaphthene-l-carboxylic Acid
o-Thiol-benzoic Acid
See, Thio-salicylic Acid
Thio-salicylic Acid
o-Mercapto-6enzoic Acid (C. A. nomen.)
o-Thiol-benzoic Acid
Thiophenol-o-carboxylic Acid
COOH
DYES CLASSIFIED BY INTERMEDIATES
545
FORMATION. (1) From o-chloro-benzoic acid by reaction with potas-
sium hydrogen sulfide. (2) From anthranilic acid by diazotizing
and then running into a solution of sodium polysulfide and sodium
hydroxide
LITERATURE. Cain, Intermediate Products (2d Ed.), 151
Lange, Zwischenprodukte, #507-510
Dyes Derived from Thio-salicylic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
INDIGO GROUP DYES
912
Thio Indigo Red B
I '14: 1,102
Thio-salicylic Acid
V
I '20: 275
(2 mols)
[Chloro-acetic Acid
2 mols; etc.]
919
Ciba Bordeaux B
I '14: 899
Thio-salicylic Acid
V
I '20: 1,786
(2 mols)
[Chloro-acetic Acid
2 mols; etc.; Bromi-
nation]
or
[Thio Indigo Red,
brominated]
Tobias Acid
See, 2-Naphthylamine-l-sulfonic Acid
Also applied to, 2-Naphthol-l-sulfonic Acid
Tolidine
See, o-Tolidine
o-Tolidine (C. A. nomen.)
Tolidine
H 3 C
H 2 N
CH 3
NH 2
546
DYES CLASSIFIED BY INTERMEDIATES
STATISTICS. Imported '14: 5,874 Ibs.
Manufactured '17: ?
Manufactured '18: ?
Manufactured '19: 143,012 Ibs.
Manufactured '20: 375,905 Ibs.
FORMATION. From o-nitro-toluene by reduction with zinc dust and
hydrochloric acid, and conversion of the hydrazo-toluene into
tolidine by boiling with hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 95
Lange, Zwischenprodukte, #1204, 1216
Dyes Derived from o-Tolidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
338
Naphthamine
I '14: 11,707
K Acid (2 mols)
D
Blue 3B
I '20: 400
362
Toluylene Orange R
I '14: 25,908
4: 6-Diamino-w-tolu-
D
Oxy Diamine Orange
M'19: ?
ene-sulfonic Acid
I '20: 1,653
(2 mols)
363
Benzopurpurin 4B
I '14: 351,712
Naphthionic Acid
D
M'17: ?
(2 mols)
M '18: 356,522
M '19: 288,021
I '20: 3,492
M '20: 617,629
364
Benzo Purpurin 6B
I '14: 9,171
Laurent's Acid (2 mols)
D
I '20: 4,743
365
Benzopurpurin B
I '14: 21,090
Broenner's Acid
D
M'17: ?
(2 mols)
M'18: ?
M'19: ?
366
Diamine Red B
I '14: 21,058
2-Naphthylamine-7-
D
Deltapurpurin 5B
M'17: ?
sulfonic Acid
M'18: ?
Broenner's Acid
I '20: 1,896
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued}
547
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
367
(continued)
Diamine Red 3B
Deltapurpurin 7B
2-Naphthylamine-7-
sulfonic Acid (2 mols)
D
368
Brilliant Purpurin
4B
T 14: 6,634
Naphthionic Acid
Broenner's Acid
D
369
^Brilliant Purpurin R
I '14: 8,051
Amino-R Acid
Naphthionic Acid
D
370
Brilliant Congo R
I '14: 19,133
I '20: 11,129
Amino-R Acid
Broenner's Acid
D
371
Rosazurine G
Ethyl-2-naphthyl-
amine-7-sulf onic Acid
D
2-Naphthylamine-7-
sulfonic Acid
372
Rosazurine B
Ethyl-2-naphthylamine-
7-sulfonic Acid
D
(2 mols)
373
Congo Orange R
I 14: 7,027
I '20: 254
Amino-R Acid
Phenol
D
[Ethylation]
374
Congo 4R
Congo Red 4R
M'18: ?
Naphthionic Acid
Resorcinol
D
375
Congo Corinth B
I '14: 2,196
M'19: ?
Naphthionic Acid
Nevile-Winther's Acid
D
376
Pyramidol Brown T
Resorcinol (2 mols)
D
377
Azo Blue
I '14: 198
Nevile-Winther's Acid
D
M'19: ?
M'20: ?
(2 mols)
378
Trisulfon Blue R
I '14: 911
M'19: ?
l-Naphthol-3:6:8-
trisulfonic Acid
D
M'20: ?
/3-Naphthol
548 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
Schultz
Number
Jar Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
(continued)
379
Dianil Blue 2R
I '14: 14,434
Chromotropic Acid
D
Benzo New Blue 2B
Nevile-Winther's Acid
380
Dianil Blue B
Chromotropic Acid
D
(2 mols)
381
Azo Black Blue B, R
HAcid
D
m-Hydroxy-diphenyl-
amine
382
Azo Mauve B
M'17: ?
HAcid
D
M'20: ?
a-Naphthylamine
383
Naphthazurine B
I '14: 4,782
HAcid
D
/3-Naphthylamine
384
Chicago Blue 2R
I '14: 23,877
Croceine Acid
D
Diamine Blue C2R
l-Amino-8-naphthol-4-
sulfonic Acid
385
Oxamine Blue 4R
I '14: 573
JAcid
D
M'20: ?
Nevile-Winther's Acid
386
Diamine Blue BX
I '14: 1,740
Nevile-Winther's Acid
D
Benzo Blue BX
M'17: ?
HAcid
M'18: ?
M'19: 92,214
I '20: 4,520
M'20: 90,147
387
Columbia Blue G
I '14: 7,094
l-Naphthol-3:8-
D
disulfonic Acid
l-Amino-8-naphthol-4-
sulf onic Acid
388
Chicago Blue R
l-Amino-8-naphthol-4-
D
sulf onic Acid (2 mols
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
549
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
389
DISAZO DYES
(continued)
Eboli Blue B
l-Amino-8-naphthol-
3 : 5-disulf onic Acid
(2 mols)
D
390
Benzo Cyanine B
I '14: 201
HAcid
l-Amino-8-naphthol-4-
sulfonic Acid
D
391
Diamine Blue 3B
Benzo Blue 3B
I '14: 1,365
M'17: 14,533
M'18: 99,645
M '19: 182,946
I '20: 1,120
M '20: 136,891
H Acid (2 mols)
D
392
Toluylene Orange G
I '14: 67,022
M'18: ?
M'19: ?
I '20: 273
M'20: ?
4: 6-Diamino-77i-tolu-
ene-sulf onic Acid
o-Cresotic Acid
D
393
Diphenyl Brown
3GN
M'20: ?
Salicylic Acid
Dimethyl-gamma Acid
D
394
395
Chrysamine R
Cresotine Yellow R
I '14: 6,261
M'20: ?
Salicylic Acid (2 mols)
o-Cresotic Acid
(2 mols)
D
D
396
Indazurine RM
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
Nevile-Winther's Acid
D
397
Direct Blue R
M'17: ?
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
Nevile-Winther's Acid
D
398
Direct Gray B
1 : 7-Dihydroxy-6-naph-
thoic-3-sulfonic Acid
(2 mols)
D
550 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Tolidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
399
DISAZO DYES
(continued)
Indazurine GS
1 : 7-Dihydroxy-2-naph-
thoic-4-sulfonic Acid
Gamma Acid
D
450
TRISAZO DYES
Benzo Black Blue R
a-Naphthylamine
Nevile-Winther's Acid
(2 mols)
D
451
Congo Fast Blue R
I '14: 4,449
M'19: ?
I '20: 723
a-Naphthylamine
l-Naphthol-3:8-disul-
fonic Acid (2 mols)
D
452
Benzo Indigo Blue
a-Naphthylamine
1 : 8-Dihydroxy-naph-
thalene-4-sulfonic
Acid (2 mols)
D
453
Columbia Black R
I '14: 1,307
2 R Acid
m-Tolylene-diamine
(2 mols)
D
454
Trisulfon Brown G
I '14: 1,323
2 R Acid
Salicylic Acid
m-Phenylene-diamine
D
481
Azo Corinth
Naphthionic Acid
Resorcinol
3-Amino-l-phenol-4-
sulfonic Acid
D
o-Tolidine-disulfonic Acid
2: 2 / -Diamino-5: S'-bi-m-toluene-sulfonic Acid (C. A. nomen.)
H 3 C CH 3
I 2 N<^^-<(^\NH 2 == C 14 H 16 N 2 6 S 2 = 372
HO 3 S ' SO 3 H
DYES CLASSIFIED BY INTERMEDIATES
551
FORMATION. From tolidine sulfate by heating with 2 parts of sulfuric
acid at 210 from 36 to 48 hours
LITERATURE. Cain, Intermediate Products (2d Ed.), 96
Lange, Zwischenprodukte, #1269-1271
Dye Derived from o-Tolidine-disulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
400
Milling Scarlet 4R
I '14: 18,330
0-Naphthol (2 mols)
A
Acid Anthracene
I '20: 2,336
RedSB
/>-Toluene-sulfochloride
See, p-Toluene-sulfonyl Chloride (C. A. nomen.)
/>-Toluene-sulfonyl Chloride (C. A. nomen.)
p-Toluene-sulfochloride
S0 2 C1
07x1701020 190.5
CH 3
STATISTICS. Imports '14: small amount
Manufactured ' 17 : ?
Manufactured ' 18 : ?
Manufactured '19: 58,932 Ibs.
Manufactured '20: ?
FORMATION. Toluene is sulfonated with oleum giving a mixture of
o- and p-toluene-sulfonic acids, which are converted to sodium
salts and dried, and then treated with PCl 3 -fCl, resulting in o- and
p-toluene-sulfonyl chlorides. The POC1 3 formed is first distilled
off and then the mass cooled, whereupon the p-toluene-sulfonyl
chloride crystallizes out
LITERATURE. Thorpe, Die. Chemistry, 4, 606
Biel., II, 132
552 DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from />-Toluene-sulfonyl Chloride
Schuitz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
182
Fast Sulfon Violet
I '14: 4,871
HAcid
A
Brilliant Sulfon
I '20: 4,740
Aniline
RedB
Toluidines, mixed
Mixed Toluidines
NH 2
CH3 and
Q
NIL
STATISTICS. Imported '14: 108,835 Ibs.
Manufactured '17: 1,366,321 Ibs.
Manufactured '18: 308,667 Ibs.
Manufactured '19: 806,210 Ibs.
Manufactured '20: 1,145,361 Ibs.
FORMATION. Toluene is nitrated using mixed acid, and the mixture of
o- and p-nitro-toluenes is reduced with iron and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 57
Lange, Zwischenprodukte, #234-240
Dyes Derived from Toluidines, mixed
Schuitz
Number
for Dye
Ordinary Name artid
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
PYRAZOLONE DYE
21
Pigment Chrome
3-Methyl-l-phenyl-5-
CL
Yellow L
pyrazolone
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Toluidines, mixed (continued)
553
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
70
Brilliant Orange
I '14: 21,480
M'17: ?
Schaeffer's Acid
A
M'18: ?
M'19: ?
M'20: ?
71
Azo Fuchsine B
1 : 8-Dihydroxy-naph-
thalene-4-sulf onic Acid
A
AZINE DYE
688
Rosolane
I '14: 796
Aniline
B
Mauve
I '20: 3
Toluidines (3 mols)
m-Toluidine
Note. C. A. numbering begins with NH Z) while German and English
numbering generally start from CH Z
NH 2
>CH 3
STATISTICS. Imported '14: 945 Ibs.
Manufactured '20: ?
FORMATION. w-Nitro-benzaldehyde is chlorinated to w-nitro-benzyli-
dine chloride (CeH^ . N(>2 . CHCy, which by reduction with zinc
at low temperatures, forms m-toluidine
LITERATURE. Ber. 13, 677; 15, 2011; 18, 3398
Dyes Derived from m-Toluidine
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Vsed and Notes
Dye
Appli-
cation
Class
DISAZO DYE
240
Janus Red B
I '14: 250
w-Amino-phenyl-tri-
B
I '20: 176
methyl-ammonium
Chloride
/3-Naphthol
554 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRISAZO DYE
435
Janus Brown B
w-Amino-phenyl-tri-
B
methy 1-ammoniu m
Chloride
Aniline
m-Phenylene-diamine
o-Toluidine
Note. C. A. numbering begins with NH 2) while German and English
numbering generally starts from GHz
STATISTICS. Imported '14: 656,320 Ibs.
Manufactured '17: 336,985 Ibs.
Manufactured '18: 638,874 Ibs.
Manufactured '19: 1,002,982 Ibs.
Manufactured '20: 1,302,097 Ibs.
FORMATION. Toluene is nitrated to a mixture of o- and p-nitro-toluenes,
which are separated. The o-nitro-toluene is reduced with iron
and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 57
Lange, Zwischenprodukte, #234-240
Dyes Derived from o-Toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
68
Spirit Yellow R
M'19: ?
o-Toluidine (2 mols)
ss
M'20: ?
69
Chrysoidine R
m^Tolylene-diamine
B
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
555
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
124
Diazine Green S
I '14: 1,340
p-Tolylene-diamine
B
Aniline or
2d mol o-Toluidine
[Preceding used as
Safranine]
with
Dimethyl-aniline
125
Diazine Black
I '14: 2,630
p-Tolylene-diamine
B
I '20: 701
Aniline or
2d mol o-Toluidine
[Preceding used as
Safranine]
with
Phenol
126
Indoine Blue R
I '14: 15,353
p-Tolylene-diamine
B
Union Blue R
M'17: ?
Aniline or
M'18: ?
2d mol o-Toluidine
[Preceding used as
Safranine]
with
.
/3-Naphthol
127
Methyl Indoine B
M'17: ?
p-Tolylene-diamine
B
Aniline or
2d mol o-Toluidine
[Preceding used as
Safranine]
with
' ' Amino-naphthols ' '
128
Janus Gray B
p-Tolylene-diamine
B
Aniline or
2d mol o-Toluidine
[Preceding used as
Safranine]
[Other intermediate
unknown]
556
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYES
280
Azidine Fast
o-Toluidine (2 mols)
D
Scarlet GGS
Sulfo-m-tolylene-dia-
mine-bis(carbonyl-
amino-naphthol-sul-
fonic Acid)
281
Azidine Fast
/3-Naphthylamine
D
Scarlet 4BS
Sulfo-m-tolylene-dia-
mine-bis(carbonyl-
amino-naphthol-sul-
fonic acid)
TEISAZO DYE
482
Alizarin Yellow
Aniline and
M
FS
p-Toluidine [as
Fuchsine]
Salicylic Acid (3 mols)
TRIPHENYL-METHANE
DYES
512
Magenta
I '14: 87,102
Aniline
B
Fuchsine
M'17: 17,739
p-Toluidine
M '18: 71,675
[Arsenic Acid or
M' 19: 155,830
Nitro-benzene]
I '20: 189
M '20: 284,285
513
New Fuchsine O
I '14: 300
Anhydro-formalde-
B
M'18: ?
hyde-o-toluidine or
M'19: ?
Diamino-o-ditolyl-
M '20: ?
methane
[o-Nitro-toluene, etc.]
514
Red Violet 5R
I '14: 331
Aniline
B
I '20: 750
p-Toluidine
[Nitro-benzene, etc., or
Arsenic Acid]
[Methylation or ethyl-
ation]
or
[Magenta methylated
or ethylated]
DYES CLASSIFIED BY INTERMEDIATES
557
Dyes Derived from o-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics oj
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
(continued)
521
Spirit Blue
I '14: 50,563
Aniline (3-4 mols)
S3
Aniline Blue
M'17: ?
p-Toluidine
M'18: ?
[Benzoic Acid]
M'19: ?
or
I '20: 723
[Magenta phenylated]
M'20: ?
524
Fuchsine S
I '14: 19,098
Aniline
A
Acid Magenta
I '20: 524
p-Toluidine
M'20: ?
[Sulfonation]
or
[Magenta sulf onated]
525
Red Violet 5RS
Aniline
A
p-Toluidine, etc.
[Ethylation Sulfona-
tion]
or
[Red Violet 5R,
sulfonated]
526
Acid Violet 4RS
Aniline
A
p-Toluidine
[Dimethylation,
Trisulfonation]
or
[Magenta dimethylated,
trisulfonated]
536
Alkali Blue
I '14: 286,751
p-Toluidine
A
M'17: ?
Aniline (3-4 mols)
M'18: 43,184
[Sulfonation]
M'19: 77,796
or
I '20: 6,778
[Spirit Blue sulfonated]
M'20: 74,253
558
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
537
DYES (continued)
Methyl Blue for Silk
Marine Blue
I '14: 34,867
M'18: ?
M'19: ?
I '20: 2,395
M'20: ?
Aniline (4 mols)
p-Toluidine
[Sulfonation]
A
538
Methyl Blue
Cotton Blue
I '14: 50,255
Aniline (4 mols)
p-Toluidine
[Di- and trisulfonation]
B
539
Water Blue
Soluble Blue
I '14: 91,152
M'18: ?
M'19: 16,315
I '20: 1,387
M'20: 98,770
p-Toluidine
Aniline (3-4 mols)
[Di- and tri-sulf onation]
or
[Spirit Blue di- and tri-
sulfonated]
A
540
Pacific Blue
Aniline
D
p-Toluidine
Diamino-diphenyl-
methane
[Sulfonation]
541
Brilliant Dianil
Blue 6G
/3-Naphthylamine
(3 mols)
Aniline
B
XANTHONE DYE
p-Toluidine
[Disulfonation]
582
Fast Acid Violet
A2R
ACRIDTNE DYE
I '14: 875
I '20: 2,679
M'20: ?
Phthalic Anhydride
Resorcinol (2 mols)
o-Toluidine (2 mols)
[PC1 5 , Sulfonation]
A
606
Phosphine
I '14: 168,175
M'17: ?
p-Toluidine
Aniline
B
M'18: ?
M'19: 14,648
I '20: 19,259
M'20: ?
[Magenta by-product]
ji
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from o-Toluidine (continued)
559
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
679
AZINE DYES
Safranine
I '14: 59,921
M'17: ?
M '18: 106,591
M '19: 131,042
I '20: 386
M '20: 149,629
p-Tolylene-diamine
Aniline or
o-Toluidine (extra
mol)
B
683
Salfranine MN
I '14: 198
M'18: ?
M'19: ?
M'20: ?
Dimethyl-p-phenylene-
diamine
Aniline
[Oxidation]
B
687
Rosolane O
I '20: 1,083
o-Amino-diphenylamine
Aniline
[Oxidation]
B
702
Para Blue
Aniline (3-4 mols)
p-Toluidine
p-Phenylene-diamine
or
[Spirit Blue, p-Pheny-
lene-diamine]
B
703
Rubramine
Nitroso-dimethyl-
aniline
p-Toluidine
B
704
Indamine 3R
Nitroso-dimethyl-
aniline
B
705
Indamine 6R
I '14: 66,170
I '20: 9,681
Nitroso-dimethyl-
aniline
p-Toluidine
B
733
SULFUR DYE
Immedial Indone
I '14: 4,236
p-Amino-phenol
[S+NaaS]
S
888
INDIGO GROUP DYE
Indigo MLB/T
I '14: 10,730
I '20: 827
o-Toluidine (2 mols)
[Chloro-acetic, soda-
mide, etc.]
V
560
DYES CLASSIFIED BY INTERMEDIATES
^-Toluidine
Note. C. A. numbering begins with NH^, while German and English
numbering generally starts from CH S
STATISTICS. Imported '14: 24,686 Ibs.
Manufactured '17: 223,778 Ibs.
Manufactured '18: 205,852 Ibs.
Manufactured '19: 575,841 Ibs.
Manufactured '20: 894,169 Ibs.
FORMATION. Toluene is nitrated to a mixture of o- and p-nitro-toluenes,
which are separated. The p-nitro-toluene is reduced with iron
and hydrochloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 58
Lange, Zwischenprodukte, #234^240, 261
Dyes Derived from ^-Toluidine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRTSAZO DYES
482
Alizarin Yellow FS
Aniline and
M
o-Toluidine [or
Magenta]
Salicylic Acid (3 mols)
TRIPHENYL-METHANE
DYES
511
Parafuchsine
I '14: 65,026
Aniline (2 mols)
B
Paramagenta
M'18: ?
[Nitro-benzene and iron
M'19: ?
or Arsenic Acid]
M'20: ?
512
Magenta
I '14: 87,102
Aniline
B
Fuchsine
M'17: 17,739
o-Toluidine
M'18: 71,675
[Nitro-benzene, etc.; or
M'19: 155,830
Arsenic Acid]
I '20: 189
M'20: 284,285
DYES CLASSIFIED BY INTERMEDIATES
561
Dyes Derived from ^-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES (continued)
514
Red Violet 5R
I '14: 331
Aniline
B
I '20: 750
o-Toluidine
[Nitro-benzene, etc.;
or Arsenic Acid]
[Methylation or ethyla-
tion]
or
[Magenta methylated
or ethylated]
520
Light Blue Superfine
I '14: 2,149
Aniline (5 mols)
ss
Spirit Soluble
[Benzoic Acid]
Diphenylamine Blue
521
Spirit Blue
I '14: 50,563
Aniline (3-4 mols)
S3
Aniline Blue
M'17: ?
o-Toluidine
M'18: ?
[Benzoic Acid]
M'19: ?
or
I '20: 723
[Magenta phenylated]
M'20: ?
524
Fuchsine S
I '14: 19,098
Aniline
A
Acid Magenta
I '20: 524
o-Toluidine
M'20: ?
[Sulfonation]
or
[Magenta sulfonated]
525
Red Violet 5RS
Aniline
o-Toluidine
A
[Ethylation, Sulfona-
tion]
or
[Red Violet 5R
sulfonated]
526
Acid Violet 4RS
Aniline
A
o-Toluidine
[Dimethylation, Tri-
sulfonation]
or
[Magenta methylated,
sulfonated]
562
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYES
(continued)
535
Methyl Alkali Blue
I '14: 273
Aniline (5 mols)
A
M'18: ?
[Sulfonation]
M'19: ?
I '20: 29
536
Alkali Blue
I '14: 286,751
o-Toluidine
A
M'17: ?
Aniline (3-4 mols)
M'18: 43,184
[Sulfonation]
M'19: 77,796
I '20: 6,778
M'20: 74,253
537
Methyl Blue for Silk
I '14: 34,867
o-Toluidine
A
Marine Blue
M'18: ?
Aniline (4 mols)
M'19: ?
[Sulfonation]
I '20: 2,395
M'20: ?
538
Methyl Blue
I '14: 50,255
o-Toluidine
Cotton Blue
Aniline (4 mols)
B
[Di- and tri-sulf onation]
539
Water Blue
I '14: 91,152
o-Toluidine
A
Soluble Blue
M'18: ? .
Aniline (3-5 mols)
M '19: 16,315
[Di- and tri-sulf onation]
I '20: 1,387
or
M '20: 98,770
[Spirit Blue Sulfonated]
540
Pacific Blue
Aniline
D
o-Toluidine
Diamino-diphenyl-
methane
[Sulfonation]
541
Brilliant Dianil
/3-Naphthylamine
B
Blue 6G
(3 mols)
Aniline
o-Toluidine
[Disulfonation]
DYES CLASSIFIED BY INTERMEDIATES
563
Dyes Derived from ^-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
XANTHONE DYE
580
Fast Acid Violet B
I '14: 20,688
Phthalic anhydride
A
' ;' t
M'19: ?
Resorcinol (2 mols)
I '20: 2,907
p-Toluidine (2 mols) or
Aniline (2 mols)
[PC1 5 , Sulfonation]
ACRIDINE DYE
606
Phosphine
I '14: 168,175
Aniline
B
M'17: ?
o-Toluidine or
M'18: ?
2d mol Aniline
M'19: 14,648
[Magenta by-product]
I '20: 19,259
M'20: ?
THIOBENZENYL DYE
616
Primuline
I '14: 67,976
p-Toluidine (4 mols)
D
M'17: 72,461
[Sulfur, Sulfonation]
M '18: 72,778
M'19: 271,338
I '20: 441
M '20: 183,179
^
AZINE DYES
683
Safranine MN
I '14: 198
Dimethyl-p-phenylene-
B
M'18: ?
diamine
M'19: ?
Aniline
M'20: ?
[Oxidation]
686
Amethyst Violet
Diethyl-p-phenylene-
D
diamine
Diethyl-aniline
[Oxidation]
702
Para Blue
Aniline (3-4 mols)
B
o-Toluidine
p-Phenylene-diamine
or
[Spirit Blue and p-
Phenylene-diamine]
703
Rubramine
Nitroso-dimethyl-
B
aniline
o-Toluidine
564 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Toluidine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
705
AZINE DYE
(continued)
Indamine 6R
1 '14: 66,170
I '20: 9,681
Nitroso-dimethyl-
aniline
o-Toluidine
B
852
ANTHRAQUINONE AND
ALLIED DYES
Alizarin Irisol D, R
I '20: 401
Quinizarin
[Sulfonation]
A
853
Anthraquinone
Violet
I '14: 1,202
I '20: 1,649
1 : 5-Dinitro-anthraqui-
none
[Sulfonation]
ACr
854
Alizarin Viridine
DG, FF
I '20: 11,397
Anthraquinone-2-sul-
fonic Acid
[Sulfonation]
[Or through Alizarin
Bordeaux from Aliz-
arin]
M
855
Alizarin Pure
BlueB
l-Amino-2: 4-dibromo-
anthraquinone
[Sulfonation]
ACr
856
Alizarin Astrol B
I '14: 10,907
I '20: 15,518
1 -Bromo-4-methyl-
amino-anthraquinone
[Sulfonation]
ACr
859
Cyananthrol R
I '14: 18,792
I '20: 2,416
1 - Amino-4-bromo-2-
methyl-anthraquinone
[Sulfonation]
A
860
Cyananthrol G
1 -Amino-4-b r omc -
(chloro) -2-methyl-an-
thraquinone, etc.
[Sulfonation]
A
864
Anthraquinone
Green GX
I '14: 1,709
I '20: 2,531
1-Nitro-anthraquinone-
6-sulfonic Acid
Aniline
ACr
DYES CLASSIFIED BY INTERMEDIATES
565
Dyes Derived from ^-Toluidine (continued)
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONE AND
ALLIED DYES
(continued)
865
Alizarin Cyanine
Quinizarin
ACr
Green E
p-Toluidine (2 mols)
[Sulfonation]
o-Toluidine-m-sulfonic Acid
See, 4-Amino-ra-toluene-sulfonic Acid (C. A. nomen.)
/>-Toluidme-o-sulfonic Acid
See, 5-Amino-o-toluene-sulfonic Acid (C. A. nomen.)
8-^-Toluino-l-naphthalene-sulfonic Acid (C. A. nomen.)
See, p-Tolyl-l-naphthylamine-8-sulfonic Acid
m-Toluylene-diamine
See, w-Tolylene-diamine
o: ^-Toluylene-diamine
See, w-Tolylene-diamine
Toluylene-diamine-sulfonic Acid
See, 3: 5-Diamino-p-toluene-sulfonic Acid (C. A. nomen.)
m-Toluylene-diamine-sulfonic Acid
See, 4: 6-Diamino-w-toluene-sulfonic Acid (C. A. nomen.)
^-(o-Tolyl-azo-)-o-toluidine (C. A. nomen.)
See, 0-Amino-azotoluene
566 DYES CLASSIFIED BY INTERMEDIATES
4-m-Tolylene-bis(thiourea) (C. A. nomen.}
See t ra-Tolylene-dithiourea
4-m-Tolylene-diamine (C. A. nomen.)
See, w-Tolylene-diamine
m-Tolylene-diamine
4-w-Tolylene-diamine (C. A. nomen. NH%=1)
ra-Toluylene-diamine
o: p-Toluylene-diamine
Note. English and Germans often start numbering from
NH 2
NIL
STATISTICS. Imported ' 14 : 135,383 Ibs.
Manufactured '17: 302,596 Ibs.
Manufactured '18: 612,163 Ibs.
Manufactured '19:-^39,544 Ibs.
Manufactured '20: 689,036 Ibs.
FORMATION. From m-dinitro-toluene by reduction with iron and hydro-
chloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 86
Dyes Derived from m-Tolylene-diamine
Schu h
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
34
Chrysoidine R
I '14: 111,006
Aniline
B
M'17: 58,115
M '18: 137,035
M '19: 220,542
,
I '20: 1,102
M '20: 186,793
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Tolylene-diamine (continued)
567
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
.
(continued)
69
Chrysoidine R
o-Toluidine
B
DISAZO DYES
284
Vesuvine B
I '14: 171,133
m-Tolylene-diamine
B
Bismarck Brown R
M'17: 262,600
(3 mols)
M '18: 295,080
M '19: 631,308
M '20: 484,929
295
Diphenyl Fast
I '14: 882
Gamma Acid
D
Black
p: p'-diamino-ditolyl-
amine
352
Direct Violet R
I '14: 661
Benzidine
M'19: ?
1 : 7-Dihydroxy-6-naph-
D
thoic-3-sulfonic Acid
413
Direct Violet BB
I '14: 4,396
Dianisidine
D
1 : 7-Dihydroxy-naph-
thalene-4-sulfonic
Acid
TRISAZO DYES
453
Columbia Black R
I '14: 1,307
Tolidine
D
2R Acid
m-Tolylene-diamine
(2 mols)
455
Columbia Black B
I '14: 165,727
Dianisidine
D
2R Acid
m-Tolylene-diamine
(2 mols)
458
Carbon Black
p-Phenylene-diamine-
D
sulfonic Acid
[from p-Nitro-aniline-
o-sulfonic Acidj
l-Naph1Jiylamine-6(7)-
sulfonic Acid
m-Tolylene-diamine
(2 mols)
568
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from m-Tolylene-diamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
461
TRISAZO DYES
(continued)
Coomassie Union
Black
[ : 4-Naphthylene-dia-
mine-2-sulfonic Acid
Gamma Acid
m-Tolylene-diamine
(2 mols)
D
463
Erie Direct
Black RX
Cotton Black E
I '14: 248,567
M'19: ?
M'20:
2,050,741
Benzidine
Aniline
H Acid
D
602
ACBIDINE DYES
Acridine Yellow
I '14: 1,913
M'19: ?
m-Tolylene-diamine
(2 mols)
[Formaldehyde, Am-
monia removal,
Oxidation]
B
605
Benzoflavine
I '14: 600
m-Tolylene-diamine
(2 mols)
Benzaldehyde
[Ammonia removal,
Oxidation]
B
670
AZINE DYE
Neutral Red
M'18: ?
Nitroso-dimethyl-
aniline or
Dimethyl-p-phenylene-
diamine
[Oxidation]
B
710
SULFUR DYE
Immedial Yellow D
I '14: 13,400
[Sulfur]
8
711
Immedial Orange N
I '14: 500
[Sulfur]
8
DYES CLASSIFIED BY INTERMEDIATES
^-Tolylene-diamine (C. A. nomen. NH 2 =1)
p-Toluylene-diamine
Note. English and Germans often start numbering with CH$
569
NH 2
122
STATISTICS. Manufactured '20: ?
FORMATION. By reduction of amino-azo-toluene (from o-toluidine)
with zinc dust and hydrochloric acid
LITERATURE. Nietzki, Ber. 10, 1158
Green, Organic Coloring Matters (1908), 37
Dyes Derived from ^-Tolylene-diamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
124
MONOAZO DYES
Diazine Green S
I '14: 1,340
o-Toluidine*
Aniline or o-Toluidine
[or Safranine]
Dimethyl-aniline
B
125
Diazine Black
I '14: 2,630
I '20: 701
o-Toluidine
Aniline or o-Toluidine
[or Safranine]
Phenol
B
126
Indoine Blue R
I '14: 15,353
M'17: ?
M'18: ?
o-Toluidine
Aniline or o-Toluidine
[or Safranine]
j8-Naphthol
B
570 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from />-Tolylene-diamine (continued)
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
127
Methyl Indone B
M'17: ?
o-Toluidine
B
Aniline or o-Toluidine
[or Safranine]
[" Amino-naphthols "]
128
Janus Gray B
o-Toluidine
B
Aniline or o-Toluidine
[or Safranine]
etc.
AZINE DYE
679
Safranine
I '14: 59,920
o-Toluidine
B
M'17: ?
Aniline or
M '18: 106,591
2d mol o-Toluidine
M '19: 131,042
I '20: 386
M '20: 149,629
l-Tolylene-2 : 6-diamine-4-sulf onic Acid
See, 3: 5-Diamino-p-toluene-sulfonic Acid (C. A. nomen.)
m-Tolylene-diamine-sulfonic Acid
See, 4: 6-Diamino-ra-toluene-sulfonic Acid (C. A. nomen.)
m-Tolylene-dithiourea
4-w-Tolylene-bis[thicmrea] (C. A. nomen.)
NH.CS.NH 2
INH.CS.NH,
DYES CLASSIFIED BY INTERMEDIATES
571
FORMATION. By heating w-tolylene-diamine thiocyanate several hours
on a water bath
LITERATURE. Lange, Zwischenprodukte, #801
Dyes Derived from m-Tolylene-dithiourea
Schultz
Number
jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
712
SULFUR DYES
Kryogene Yellow G
I '14: 1,126
I '20: 1,543
Benzidine
[Sulfur!
S
716
Kryogene Yellow R
I '14: 4,804
[Sulfur]
S
^-Tolyl-a-naphthylamine
N-p-Tolyl-1-raiphthylamine (C. A. nomen.)
FORMATION. From a-naphthylamine hydrochloride and p-toluidine
by heating together to about 280
LITERATURE. Cain, Intermediate Products (2d Ed.), 186
Dye Derived from />-Tolyl-a-naphthylamine
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DlPHENYL-NAPHTHYL-
METHANE DYE
560
Night Blue
I '14: 361
Tetraethyl-diamino-
B
M'19: ?
benzophenone
I '20: 11
572 DYES CLASSIFIED BY INTERMEDIATES
^-Tolyl-l-naphthylamine-8-sulfonic Acid
8-p-Toluino-l-naphthalene-sulfonic Acid (C. A. nomen.)
Tolyl-peri Acid
H0 3 S NH
STATISTICS. Imports '14: 1,097 Ibs.
Manufactured '18: ?
Manufactured '19: ?
Manufactured '20: ?
FORMATION. From l-naphthylamine-8-sulfonic acid and p-toluidine
by heating together in an autoclave
LITERATURE. Cain, Intermediate Products (2d Ed.), 195
Lange, Zwischenprodukte, #2859
Dyes Derived from ^-Tolyl-l-naphthylamine-8-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYE
189
Sulfon Acid Blue B
I '14: 35,560
HAcid
A
M'17: ?
-
M'19: ?
M'20: ?
DISAZO DYE
257
Sulfoncyanine
I '14: 145,694
Metanilic Acid
A
M'17: ?
a-Naphthylamine
M'18: ?
M'19: ?
I '20: 18,327
M'20: ?
Tolyl-peri Acid
See, p-Tolyl-l-naphthylamine-8-sulfonic Acid
DYES CLASSIFIED BY INTERMEDIATES 573
1:2: 4-Triarnino-anthraquinone
CO
CO
FORMATION. 1 : 4-j3iamino-anthraquinone is diacetylated, and then
nitrated with nitric acid of sp. gr. 1.5. By reduction of the nitrated
product the 1:2: 4-triamino-anthraquinone is prepared
LITERATURE. Lange, Zwischenprodukte, #3333
Dye Derived from 1 : 2 : 4-Triamino-anthraquinone
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
ANTHRAQUINONB AND
ALLIED DYES
822
Algol Brilliant
I '14: 6,195
Benzoyl Chloride
V
Orange FR
I '20: 482
Triamino-triphenyl-methane
Tris(p-amino-phenyl) -methane (C. A. nomen.}
p-Leucaniline
H 2 N
NH 2
FORMATION. (1) From para-rosaniline by reduction with zinc. (2) From
corresponding nitro-compounds by reduction
LITERATURE. Beilstein, Organische Chemie (3d Ed.), 4, 1194
574
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from Triamino-triphenyl-methane
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE
511
Parafuchsine
I '14: 65,026
(Oxidation)
B
Paramagenta
M'18: ?
M '19: ?
M'20: ?
a-Trichloro-toluene
See, Benzo-trichloride
3:4:5-Trihydroxy-benzoic Acid
See, Gallic Acid
Trimethyl-m-amino-phenyl-ammonium Chloride
See, (w-Amino-phenyl)-trimethyl-ammonium Chloride
a-Trinitro-naphthalene
1:3: 5-Trinitro-naphthalene (not considered herein)
/3-Trinitro-naphthalene
1:3: 8-Trinitro-naphthalene (not considered herein)
7-Trinitro-naphthalene
1:4: 5-Trinitro-naphthalene (not considered herein)
5-Trinitro-naphthalene
1:2: 5-Trinitro-naphthalene (not considered herein)
1:3: 5-Triphenyl-hexahydro-s-triazine (C. A. nomen.)
See, Anhydro-formaldehyde-aniline
DYES CLASSIFIED BY INTERMEDIATES
Tris(^-amino-phenyl) -methane (C. A. nomen.)
See, Triamino-triphenyl-methane
575
Trisulfonic Acid
See, Naphthalene-1: 3: 6-trisulfonic Acid
5: 5'-Ureido-bis(2-amino-benzene-sulfonic Acid) (C. A. nomen.)
See, Diamino-diphenyl-urea-disulfonic Acid
m-Xylene (C. A. nomen.)
w-Xylol
CsHio 106
CH 3
FORMATION. This occurs in commercial crude xylol as the most abun-
dant constituent, and is separated from its isomers by treating the
crude xylol with a limited quantity of sulfuric acid, and by hydroly-
sis of the sulfonate formed
LITERATURE. Green, Organic Coloring Matters (1908 Ed.), 5
Dye Derived from m-Xylene
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
TRIPHENYL-METHANE
DYE(?)
564
Naphthalene Green
I '14: 22,144
p-Dimethylamino-
A
V
I '20: 9,291
benzaldehyde
Dimethyl-aniline
576
DYES CLASSIFIED BY INTERMEDIATES
Xylidine
The crude mixture contains the following isomers:
NH 3 NH 2 NH 2
H 3 C/\CH 3
TT
3
2:4-xylidine
(m-4-xylidine)
2: 5-xylidine
(p-xyfidine)
2:6-xylidine
(m-2-xylidine)
NH 2
NH 2
CH,
CH,
CH,
2:3-xylidine
(o-3-xylidine)
r
-3
3:4-xylidine
(o-3-xylidine)
(C. A. nomen. NHz
(C. A. nomen.
STATISTICS. Imported '14: 21,836 Ibs.
Manufactured '17:-^25,873 Ibs.
Manufactured '18: 534,834 Ibs.
Manufactured '19: 386,635 Ibs.
Manufactured '20: 1,054,476 Ibs.
FORMATION. Xylene is nitrated with mixed acid, preferably cold.
The mixed nitro-xylenes are then reduced with iron and hydro-
chloric acid
LITERATURE. Cain, Intermediate Products (2d Ed.), 58
Lange, Zwischenprodukte, #742-747
Dyes Derived from Xylidine
SchuLtz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
76
MONOAZO DYES
Sudan II
I '14: 501
M'17: 27,595
M'18: 23,692
M'19: ?
M '20: 170,658
0-Naphthol
S3
77
Azo Coccine 2R
Nevile-Winther's Acid
A
78
Cochineal Scarlet 4R
l-Naphthol-5-sulfonic
Acid
A
DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from Xylidine (continued)
577
Schultz
Number
for Dye
Ordinary Name and
Clus* of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
(continued)
79
Brilliant Orange R
I '14: 4,204
Schaeffer's Acid
A
Xylidine Orange 2R
M'17: ?
M'18: 18,909
M'19: ?
M'20: ?
80
Wool Scarlet R
I '14: 39,888
l-Naphthol-4:8-disul-
A
f onic Acid
82
Ponceau R
I '14: 35,259
RAcid
A
M '17: 633,429
M'18:
1,189,054
M '19: 552,680
M'20:
1,286,002
AZINE DYE
685
Tannin Heliotrope
I '14: 1,398
Nitroso-dimethyl-
B
I '20: 249
aniline
2:4-Xylidine (C. A. nomen. NH 2 =1)
m4-Xylidine(C# 3 =-0
m-Xylidine
NH 2
STATISTICS. Manufactured '20: but amount not disclosed
FORMATION. By separation from commercial xylidine as acetate
LITERATURE. Cain, Intermediate Products (2d Ed.), 59
578 DYES CLASSIFIED BY INTERMEDIATES
Dyes Derived from 2 : 4-Xylidine
Schultz
Number
Jor Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
MONOAZO DYES
81
Palatine Scarlet A
Brilliant Cochineal
I '14: 7,510
l-Naphthol-3:6-disul-
fonic Acid
A
82
Ponceau 2R
Scarlet 2R
I '14: 35,259
M '17: 633,429
M '18:
1,189,054
M '19: 552,680
M'20:
RAcid
[Only small part of total
production from m-
xylidine]
A
1,286,002
DISAZO DYE
211
Resorcine Brown
I '14: 13,189
M'17: ?
Sulfanilic Acid
Resorcinol
A
M'18: ?
M'19: ?
I '20: 2,484
M'20: ?
2: 5-Xylidine (C. A. nomen. NH 2 =1)
p-Xylidine(C# 3 =.0
NH 2
FORMATION. Crude xylidine is treated with sufficient glacial acetic
acid to cause the ra-xylidine acetate to crystallize out. The mother
liquor is mixed with hydrochloric acid, and after a few days the
p-xylidine hydrochloride is separated
LITERATURE. Cain, Intermediate Products (2d Ed.), 59
Lange, Zwischenprodukte, #742-747
DYES CLASSIFIED BY INTERMEDIATES
Dye Derived from 2 : 5-Xylidine
579
Schultz
Number
for Dye
Ordinary Name and
Class oj Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
438
TRISAZO DYE
Melogene Blue BH
M'17: ?
M J 18: ?
Benzidine
H Acid (2 mols)
D
m-Xylidine
See, 2: 4-Xylidine (C. A. nomen.)
m-4-Xylidine
See, 2: 4-Xylidine (C. A. nomen.)
/>-Xylidine
See, 2: 5-Xylidine (C. A. nomen.)
Xylidine-sulfonic Acid
C 6 H 2 . NH 2 . (CH 3 ) 2 . S0 3 H C 8 HnN0 3 S = 201
FORMATION. Probably by sulfonation of either crude or purified
xylidine with sulfuric acid in a vacuum or in a current of an indiffer-
ent gas
LITERATURE. Thorpe, Die. Chemistry, 5, 797, 798
Junghahn, Ber. 35, 3747-3767 (1902)
Dye Derived from Xylidine-sulfonic Acid
Schultz
Number
for Dye
Ordinary Name and
Class of Dye
Statistics of
Import and
Manufacture
Other Intermediates
Used and Notes
Dye
Appli-
cation
Class
DISAZO DYE
214
Fast Brown O
I '14: 2,000
Xylidine-sulfonic Acid
A
(2 mols)
a-Naphthol
580 DYES CLASSIFIED BY INTERMEDIATES
4-(2: 4-Xylyl-azo)-2: 5-xylidine (C. A. nomen.)
See, Amino-azo-xylene
Y Acid
See, G Acid
Yellow Acid
1 : 3-Dihydroxy-naphthalene-5 : 7-disulf onic Acid (not considered
herein)
Zeta Acid
Naphthasultone-3-sulfonic Acid (not considered herein)
FORMULA INDEX OF INTERMEDIATES
The formulas are indexed here for the 487 intermediates for which
data and tables are listed. Only one chemical name is given, but on
the pages referred to there are enumerated the various trivial names and
synonyms.
The arrangement of the formulas follows that of the 1920 Chemical
Abstracts (C. A. 14, 4557) where "The arrangement of symbols in
formulas is alphabetical except that in carbon compounds C always
comes first, followed immediately by H." "The arrangement of the
formulas is also alphabetical except that the number of atoms of any
specific kind influences the order of compounds," e.g., all compounds
with CG come before those with Cy, thus CeHsCl precedes C 7 H6C1NO 2 .
This is likewise true for all the other atoms, and consequently we find
C 7 H 6 C1NO 2 before C 7 H 9 N, and C 8 H 2 Br 2 ClNO before C 8 H 2 C1 4 O 4 .
It is believed that a formula index affords the easiest and surest way
to find an organic compound, and it is for this reason that this index
is given. This is particularly true of intermediates where often many
names are used for the same chemical individual.
CChO
CiHsOs
CgHsClN2O4
CsHsChNOz
CeHsNsO?
CH4C1NO2
CeHsCl
C6H 5 C1O2S
CeH&ChN
CeHsChNO
CiHsNOa
CeH 6 NOs
CH 6 NsO4
CeHsNjOs
CeHeClNOsS
PAGE
Phosgene 486
Dihydroxy-tartaric Acid 229
l-Chloro-2: 4-dinitro-benzene 161
4-Chlon>-3: 5-dinitro-benzene-
sulfonic Acid 162
2: 5-Dichloro-nitro-benzene 210
Picric Acid 495
o-and ^-Chloro-nitro-benzenes 169
2-Chloro-5-nitro-benzene-sul-
fonic Acid 169
4-Chloro-3-nitro-benzene-sul-
fonic Acid 170
m-Dinitro-benzene 251
2:4-Dinitro-phenol 258
Chloro-benzene 161
2-Chloro-4-nitro-aniline 167
Benzene-sulfonyl Chloride 125
2: 5-Dichloro-aniline 206
2-Amino-4: 6-dichloro-phenol 50
Nitro-benzene 430
p-Nitroso-phenol 448
Nitro-phenol, crude 434
o-Nitro-phenol 435
p-Nitro-phenol 436
4-Nitroso-resorcinol 449
2: 4-Dinitro-aniline 248
Picramic Acid 494
2-Amino-6^chloro-benzene-sul-
fonic Acid 45
m-Nitro-aniline 420
p-Nitro-aniline 421
2-Amino-5-nitro-benzene-sul-
fonic Acid 74
4-Amino-3-nitro-benzene-sul-
fonic Acid 75
6-Nitro-metamlic Acid 434
PAGE
C6H 6 N 2 O 6 S
CeHeO
CeHsOs
CeHeOeS
C 6 H 7 N
CeHvNO
C 6 H 7 N0 3 S
C 6 H 7 NO4S
CeHioOa
C 7 H4ClNOs
C 7 H 4 Cl2O
2-Amino r 6-nitro-phenol-4-
sulfonic Acid
Phenol
Resorcinoi
Pyrogallol
Pyrogallol-5-sulfonic Acid
Aniline
TO-Amino-phenol
&A.mino-phenol
etanilic Acid
Sulfanilic Acid
2-Amino-phenol-4-sulfonic
Acid ou
3-Amino-phenol-4-sulfonic
Acid 81
2-Amino-p-benzene-disulfonic
Acid 39
4-Amino-7ra-benzene-disul-
fonic Acid
4-Amino-phenol-2: 6-disul-
fonic Acid 79
4-Nitro-m-phenylene-diamine 437
m-Phenylene-diamine
p-Phenylene-diamine _ 470
p-Pheriylene-diamine-sulfonic
Acid 474
Pheny 1-hy drazine-p-sulf onic
Acid
2: 6-Diamino-l-phenol-4-sui
fonic Acid
m-Phenylene-diamine-disul-
fonic Acid
Aceto-acetic Ethyl Ester
2-Chloro-5-nitro-benzaldehyde 168
2-Chloro-6-nitro-benzaldehyde 168
2: 5-Dichloro-benzaldehyde 209
77
459
509
499
500
90
77
78
333
528
481
198
473
581
582
FORMULA INDEX OF INTERMEDIATES
C 7 H S C10
PAGE
Benzoyl Chloride 140
C 8 H 7 NOj
o-Chloro-benzaldehyde 158
C 8 H 7 N04S
C 7 HsClO4S
2-Chloro-benzaldehyde-6-sul-
fonic Acid 15S
C 8 H 8 N 2 Os
C7H6Clj
Benzo-trichloride
C 8 H 8 O 3
C7H 8 NOa
m-Nitro-benzaldehyde 427
C 8 H 8 O B
o-Nitro-benzaldehyde 428
CsH 8 O 7 S 2
C7H 6 C1NO 2
p-Nitro-benzaldehyde 429
p-Nitro-benzyl Chloride 432
C 8 HN
C?H6N*2O4
2: 4-Dinitro-toluene 261
C 7 H 6 N 2 O S
Dinitro-p-cresol 252
CsH.NO
C 7 H 6 O
Benzaldehyde 120
C 8 H 9 NO 2
C7HeO 2
Benzoic Acid 137
CsHio
C 7 H 6 O 2 S
m-Hydroxy-benzaldehyde 308
Thio-salicylic Acid 544
C 8 HioN 2 O
Salicylic Acid 518
c 7 nJo!
a-Resorcylic Acid 516
/3-Resorcylic Acid 517
CsHnN
C 7 HeO4S
Benzaldehyde-o-sulfonic Acid 122
C 7 H 6 6
Gallic Acid 289
C 7 H 6 O 7 S 2
Benzaldehyde-disulfonic Acid 121
C 7 H 7 C1
Benzyl Chloride 143
p-Toluene-sulfonyl Chloride 551
CgHnNO
CrHrNO
m-Amino-benzaldehyde 37
C 7 H 7 N0 2
p-Amino-benzaldehyde 38
m-Amino-benzoic Acid 40
Anthranilic Acid 110
o-Nitro-toluene 450
CgHnNOsS
C 7 H 7 NO,
p-Nitro-toluene 451
5-Amino-salicylic Acid 84
C 8 Hi 2 N 2
o-Nitro-anisole 426
C 7 H 7 NO4
Gallamide 287
C 7 H 7 NO t S
5-Nitro-o-toluene-sulfonic
Acid 452
C TTi^NoO^^
p-Sulfo-anthramlic Acid 532-
C 7 H 8 C1NO
5-Chloro-o-anisidine 156
C HsOaS
C 7 H 8 C1N0 3 S
2-Amino-5-chloro-p-toluene-
sulfonic Acid 46
C 9 H7BrOS
Si.'*?*),
p-Nitroso-methyl-aniline 446
2-Nitro-p-toluidine 454
C 9 H 7 C1O 4 S
3-Nitro-p-toluidine 455
5-Nitro-o-toluidine 455
C 9 H 7 N
C 7 H 8 N 2 O 3
2-Amino-6-nitro-p-cresol 75
4-Nitro-o-anisidine 425
C 9 H 9 C1O 2 S
5-Nitro-o-anisidine 426
C 7 H 8 O
Cresol 177
C 9 H 9 NO
C 7 H 8 2
Resorcinol Methyl Ether 515
CH 9 NO4
C 7 H 9 N
AT-Methyl-aniline 336
Toluidines (mixed) 552
C 9 HioClNO
m-Toluidine 553
o-Toluidine 554
CoHnNO
p-Toluidine 560
C 7 HNO .
2-Amino-p-cresol 47
C 9 Hi 2 N 2
3-Amino-p-cresol 48
C 9 Hi 2 N 2 O 2
o-Anisidine 107
C 7 H 9 NOsS
4-Amino-m-toluene-sulf oni c
C 9 Hi 2 N 4 S2
Acid 86
CHuN
5-Amino-o-toluene-sulfonic
Acid 87
C7HioN 2
m-Tolylene-diamine 566
p-Tolylene-diamine 569
C 7 HioN 2 O 3 S
3 : 5-Diamino-p-toluene-sul-
CHi 4 N 2
fonic Acid 200
4 : 6-Diamino-m-toluene-sul-
f onic Acid 200
C 8 H 2 Br 2 ClNO
5: 7-Dibromo-isatin Chloride 206
C 8 H 2 CU04
Tetrachloro-phthalic Acid 536
C 8 H 4 C1 2 O4
C 8 H 4 3
3 : 6-Dichloro-phthalic A cid 211
Phthalic Anhydride 487
C 9 HiBClN!
C 8 H 5 NO 2
Isatin 321
CioH 6 N 2 O4
Phthalimide 493
C 8 H 6 C1NO4S
4-Chloro-2-nitro-phenyl-
thiogly colic Acid 170
CsHeOS
2-Hydroxy-thionaphthene 313
CioH 6 O 2
C 8 H 7 C10 2 S
m-Chloro-pheny 1-thiogly colic
CioH 6 O 4
Acid 171
CioHeOsS
C 8 H 7 NO
Indoxyl 320
C 8 H 7 NOS
5-Amino-2-hydroxy-thionaph-
CioH 6 8 S 2
thene 58
PAGE
449
438
417
177
293
337
90
21
475
575
26
439
445
237
271
345
576
577
578
2-Nitro-m-tolualdehyde
o-Nitro-phenyl-thioglycolic
Acid
p-Nitro-acetanilide
o-Cresotic Acid
Gallic Acid Methyl Ester
3-Methyl-benzaldehyde-4: 6-
distilfomc Acid
Anhy dro-f orm aldehy de-o-
toluidine
Acetanilide
Phenyl-glycine
m-Xylene
p-Amino-acetanilide
p-Nitroso-dimethyl-aniline
p-Nitroso-ethyl-aniline
Dimethyl-aniline
N-Ethyl-aniline
JV-Methyl-o-toluidine
Xylidine
2: 4-Xylidine (NH 2 = 1)
2:5-Xylidine (NH 2 = 1)
2-Amino-p-cresol Methyl
Ether 49
m Dimethylamino-phenol 236
TO-Ethylamino-phenol 271
p--Phenetidine 458
Xylidine-sulfonic Acid 579
N: A'-Dimethyl-m-phenylene-
diamine 244
AT: JV-Dimethyl-p-phenylene-
diamine 244
Ethyl-phenyl-hydrazine 277
N: JV-pimcthyl-p-phenylene-
diamine-thipsulfonic Acid 246
2-H ydroxy-thionaphthene-1-
carboxylic Acid 315
5rBrpmo-2-hydroxyl-3-methyl-
thiooaphthene 150
5-Chloro-phenyl-thioglycol-
o-carboxylic Acid 171
Isoquinoline 323
Quinoline 503
4-ChloTo-2-Tolyl-thioglycolic
Acid 172
7-Methyl-indoxyl 341
Phenyl-glycine-o-carboxylic
Acid ' 478
p-Dimethylamino-benzoyl
Chloride 232
p-Dimethylamino-benzalde-
hyde 231
p-Nitroso-ethyl-o-toluidine 446
5-Dimethylamino-2-nitroso-
p-cresol 236
m-Tolylene-dithiourea 570
JV-E thy 1- .TV-methyl-aniline 274
TyT-Ethyl-o-toluidine 281
A r -Ethyl-p-toluidine 282
Mesidine 332
Pseudocumidine 497
o-Amino-benzyl-dimethylamine 42
p-Amino-benzyl-dimethyl-
amine 42
JV-Ethyl-4-m-tolylene-dia-
mine 283
A^-Ethyl-p-tolylene-diamine 283
(m-Amino-phenyl)-trimethyl-
ammonium Chloride 82
1 : 5-Dinitro-naphthalene 256
1 : 5-and 1 : 8-Dinitro-naphtha-
lenes 256
1 : 8-Dinitro-naphthalene 257
1 : 2-Naphthoquinone 381
Naphthazarin 352
1 : 2-Naphthoquinone-4-sul-
fonic Acid 382
1: 2-Naphthoquinone-4: 6-
disulfonic Acid 381
FORMULA INDEX OF INTERMEDIATES
583
PAGE
CioH 7 ClO 48 l-Chloro-8-naphthol-4-sulf onic
Acid
l-Chloro-8-naphthol-5-suifonic
Acid 16
CioH 7 ClO 7 S 2 l-Chloro-8-naphthol-3: 6-
disulfonic Acid
CioH 7 NO 2 l-Nitroso-2-naphthol 447
CioH 7 NO 8 S3 1 : 8-Naphthasultam-2 : 4-di-
sulfonic Acid 351
CioHs Naphthalene 347
CioH 8 Cl 2 N 2 O4S l-(2: 5-Dichloro-4-sulfo-phen-
yl)-3-methyl-5-pyrazolone
CioH 8 N 2 O4S l-Nitroso-2-naphthylamine-
6-sulfonic Acid
CioHsNisOeS l-Ammo-8-nitro-2-naphthol-
4-sulfomc Acid
l-(p-Sulfo-phenyl)-5-pyrazo-
lone-3-carboxylic Acid
CioHsO a-Naphthol
0-Naphthol
CioH 8 O2 1: 5-Dihydroxy-naphthalene
2: 7-Dihydroxy-naphthalene
CioH 8 O4 7: 8-Dihydroxy-4-methyl-
coumarin
CioH 8 O4S Croceine Acid
l-Naphthol-5-sulfonic Acid
2-Naphthol-l-sulfonic Acid
2-Naphthol-7-sulfonic Acid
Nevile-Winther's Acid
Schaeffer's Acid
CioHsOsS 1: 7-Dihydroxy-naphthalene-
4-sulfonic Acid
1 : 8-Dihydroxy-naphthalene-
4-sulfonic Acid
CioH 8 O6S2 Naphthalene-1: 5-disulfonic
Acid
Naphthalene-1 : 6-disulfonic
Acid
Naphthalene-2 : 7-disulf onic
Acid
CioHsO 7 S 2 G Acid
l-Naphthol-3: 6-disulfonic
Acid
l-Naphthol-3: 8-disulfonic
Acid
l-Naphthol-4: 8-disulfonic
Acid
2-Naphthol-3: 7-disulf onic
Acid
R Acid
CioH 8 OsS 2 Chromotropic Acid
CioHsOgSs Naphthalene-1 : 3: 5-trisul-
fonic Acid
Naphthalene-1: 3: 6-trisul-
fonic Acid
doHsOioSa l-Naphthol-3: 6: 8-trisulfonic
Acid 379
2-Naphthol-3: 6: 8-trisulfonic
Acid
CioH.N Lepidine
a-Naphthylamine
/3-N aphthy lamine
Quinaldine
CioHgNO 5-Amino-l-naphthol
GioEUNOsS Broenner's Acid
Laurent's Acid
Naphthionic Acid
1 -Naphthy lamine-2-sulf onic
Acid
1 -N aphthy lamine-6-sulf onic
Acid 399, 400
l-Naphthylamine-7-sulfonic
Acid 400, 401
l-Naphthylamine-8-sulfonic
Acid ' 402
2-Naphthylamine-l-sulfonic
Acid ' 402
2-Naphthylamine-5-sulfonic
Acid 403
448
76
533
359
361
222
223
222
179
375
376
377
413
525
224
225
348
348
348
369
370
372
373
504
173
349
350
380
331
384
391
501
62
152
329
353
398
CioH.NOiS
CioH 9 NOS 2
CioH.NOvSz
CioH,NO 9 S3
7ioHi 5 NO
IioHisNOsS
!ioHiN 2
PAGE
2-Naphthylamine-7-sulfonic
Acid
2-Naphthylamine-8-sulfonic
Acid 403, 405
l-Amino-2-naphthol-4-sulfonic
Acid 67
l-Amino-2-naphthol-6-sulfonic
Acid 68
1 -Amino-5-naphthol-7-sulf onic
Acid 69
l-Amino-8-naph thol-4-sulf onic
Acid 69
l-Amino-8-naphthol-5-sulfonic
Acid
2- Amino- 1-naph thol-4-sulf onic
Acid 72
2-Amino-3-naphthol-6-sulfonic
Acid
Gamma Acid
J Acid
Amino-G Acid
Amino-R Acid
Freund's Acid
l-Naphthylamine-3: 8-disul-
fonic Acid
1-Naphthy lamine-4: 6-disul-
fonic Acid
1-Naphthy lamine-4: 7-disul-
fonic Acid
1-Naphthy lamine-4: 8-disul-
fonic Acid
1-Naphthy lamine-5: 7-disul-
fonic Acid
2-Naphthylamine-5: 7-disul-
fonic Acid
l-Amino : -8-naphthol-2: 4-di-
sulfonic Acid
l-Aminc^S-naphthol-S: 5-di-
sulfonic Acid
H Acid
K Acid
2 R Acid
l-Naphthylamine-3: 6: 8-
trisulfonic Acid
1-Naphthy lamine-4: 6: 8-
trisulfonic Acid
2-Naphthylamine-3: 6: 8-
trisulfonic Acid
3-Methy 1- 1-pheny 1-5-py ra-
zolone
1 : 3-Naphthylene-diamine-6-
sulfonic Acid 409
1 : 4-Naphthylene-diamine-2-
sulfonio Acid
1 : 4-Naphthylene-diamine-6-
sulfonic Acid
2: 7-Naphthylene-diamine-
sulfonic Acid
3-Methyl-l-(p-sulfophenyl)-
5-pyrazolone
1: 5-N aphthy lene-diamine-
3 : 7-disulf onic Acid
1 : 8-Naphthylene-diamine-
3: 6-disulfonic Acid
4-Chloro-6-methoxy-3-methyl-
fihenyl-thioglycolic Acid 163
itroso-diethyl-aniline
5-Diethylamino-2-nitroso-
phenol
Diethyl-aniline
m-Diethylamino-phenol
Diethyl-aniline-m-sulfonic
Acid
N: AT'-Diethyl-ro-phenylene-
diamine
N: JV'-Diethyl-p-phenylene-
diamine
404
71
72
294
324
64
83
285
393
394
394
395
395
396
63
64
298
325
507
406
407
407
343
410
411
411
408
409
438
215
217
215
218
219
220
Diethyl-p-phenylene-diamine-
thiosulfonic Acid 220
584
FORMULA INDEX OF INTERMEDIATES
PAGE
CuHsOs
l-Hydroxy-2-naphthoic Acid 310
3-Hydroxy-2-naphthoic Acid 310
CnH 8 O 7 S
1: 7-Dihydroxy-2-naphthoic-
C13H14N407S2
4-sulfonic Acid 227
1 : 7-Dihydroxy-6-naphthoic-
Ci4HeBr4N 2 O 2
3-sulfonic Acid 228
CuHioO 3 S 2
5-Ethylmercapto-2-hydroxy-
thionaphthene-1-carboxylic
CuHeCbOi!
Acid 273
CnHioO4S
5-Ethoxy-2-hydroxy-thionaph-
Ci4H 6 N 2 O 6
thene-1-carboxyhc Acid 268
CnHuNO4S
CuHuClNO
Methyl-gamma Acid 340
p-Diethylamino-benzoyl
Chloride 213
Ci 4 H 6 N 2 Oi4S 2
CuH 6 N 2 Oi6S 2
CuHnNO
3-Diethylamino-p-cresol ' 214
CnHigNj
Ci 2 H0 2
p-Amino-benzyl-diethylamine 41
Acenaphthenequinone IS
Ci4H 7 Br0 2
Ci 2 H 7 NO 2
/3-Naphthisatin 358
Ci 2 HN
Carbazole 154
Ci4H 7 ClO 2
C 12 H,N 3
CuH.NaOs
2-Amino-8-hydroxy-phenazine 57
2: 4-Dinitro-4'-hydroxy-
Ci4H 7 NOe
diphenylamine 255
Ci 2 H,N 3 O 7 S
2 : 4-Dinitro-diphenylamine-
3'-sulfonic Acid 254
Ci 4 H 7 NO 7
2: 4-Dinitro-dipheny lamine-
Ci 4 H 7 NO 7 S
4'-sulfonic Acid 254
ClzH.NsOloSz
2 : 5-Dinitro-diphenylamine-
3: 4-disulfonic Acid 253
CuHsBrNOj
CuHioClsNs
o: o'-Dichloro-benzidine 210
Ci4H 8 Br 2 N 2 O 2
Ci 2 HioN 2 OsS
Nitro-diphenylamine-sulfonic
Acid 433
Ci 4 H 8 ClNO 2
CizHjoNzOgSs
Benzidine-sulfon-disulfonic
Acid 136
Ci 4 H 8 O 2
CHioN4O4
4'-Amino-2: 4-dinitro-di-
CijHioO
phenylamine 51
3-Hydroxy-acenaphthene 306
Ci4H 8 2 S
Ci 2 HnN
CizHnNO
Diphenylamine 261
m-Hydroxy-diphenylamine 309
Cl4H 8 04
Ci 2 H n NO 2
Ci 2 HiiNOsS
a-Naphthyl-glycine 412
Diphenylamine-sulfonic Acid 262
Ci4H 8 O 5
Ci 2 HnNO 8 S 2
Acetyl-H Acid 22
C 1 4H 8 O 5 S
Amino-azo-benzene 32
CuHsOs
c! 2 HnN 3 O 2
o-Nitro-benzidine 431
Ci4H 8 O 8 S 2
Ci 2 HuN 3 O 3
2-Amino-4'-hydroxy-4-nitro-
diphenylamine 56
CuHuNjOsS
Amino-azo-benzene-sulfonic
Acid 34
CwHuNaOeSz
Amino-azo-benzene-disulfonic
Acid 33
Ci4H 9 NO 2
C 12 H, 2 N,
o-Amino-diphenylamine 52
p-Amino-diphenylamine 52
CuHsNOs
Benzidine 125
Ci 2 Hi 2 N 2 O
4-Amino-4'-hydroxy-diphenyl-
Ci 4 HNO4
amine 56
CizHuN^aS
p-Amino-diphenylamine-2-
sulfonic Acid 53
Ci4HNOt
Benzidine-sulfonic Acid 136
CuH.NOsS
Ci 2 Hi 2 N 2 O4S
Acetyl-1: 4-naphthylene-dia-
mine-6-sulfonic Acid 22
CuHio
Ci 2 H 12 N 2 O 6 S 2
Benzidine-disulfonic Acid 135
CuHioNstO
Ci 2 Hi 2 N 2 S
Thioaniline 541
Ci 4 HioN 2 O2
Ethyl-o-naphthylamine 275
CwH^NO
l-Amino-2-naphthol Ethyl
Ether 66
Ci 4 HioN 2 O4
Ci 2 HiNO 3 S
Ethyl-2-naphthylamine-7-sul-
Ci4HioN 2 OioS 2
fonic Acid 276
Ci 2 Hi 3 N04S
Dimethyl-gamma Acid 243
CuHioO
Ci 2 Hi 3 N 3
Ethyl-gamma Acid 272
p: p'-Diamino-diphenylamine 192
2: 4-Diamino-4'-hydroxy-di-
Ci 4 HioO 2
CuHioOs
phenylamine 197
CitHuNiOi
Ci 2 HuN6
4-Amino-chrysoidine 47
CitHuNO*
Gallanilide 289
Ci 4 Hi 2 N 2 OsS 2
CisHuNiS
Thio-carbanilide 542
Ci 3 HnN
Ci 3 Hi 3 NO 3 S
JV-Methyl-diphenylamine 338
JV-Methyl-diphenylamine-
Ci 4 Hi 2 N 2 OioS 2
sulfonic Acid 339
"i TT "Ma
Ci 3 Hi 4 N 2
p: p'-Diamino-diphenyl-
^ 14 JJ 14 >sJ 2 Q 6 g 2
methane 192
PAGE
A^-PhenyW-m-tolylene-
diamine 485
Diamino-diphenyl-urea-disul-
' ' " 193
fonic Acid
2:4:6: 8-Tetrabromo-l: 5-
diamino-anthraquinone
1 : 5-Dichloro-anthraquinone
2 : 6-Dichloro-anthraquinone
2 : 7-Dichloro-anthraquinone
Dinitro-anthraquinones
1 : 5-Dinitro-anthraquinone
1: 5-Dinitro-anthraflavic-3: 7-
disulfonic Acid
4: 8-Dinitro-anthrachrysone-
2: 6-disulfonic Acid 249
1-Bromo-anthraquinone 149
l-Amino-2 : 4-dibromo-anthra-
quinone 50
1-Chloro-anthraquinone 156
2-Chloro-anthraquinone
Nitro-alizarin (crude)
3-Nitrc-alizarin
4-Nitro-alizarin
3-Nitro-flavopurpurin
l-Nitro-anthraquinone-6-
sulfonic Acid
l-Amino-2-bromo-4-hydroxy-
anthraquinone
1: 4-Diamino-2: 3-dibromo-
anthraqui none
l-Amino-6-chloro-anthra-
quinone
Anthraquinone
Phenanthrene-quinone
l-(or 2-)Mercapto-anthra-
quinone
Alizarin
Anthrarufin
Quinizarin
Purpurin
Anthraquinone-2-sulf onic Acidl 14
Anthrachrysone 109
Anthraquinone- 1: 5-and 1: 8-
disulfonic Acids
Anthraquinone-2: 6-disulfonic
Acid 112
Anthraquinone-2: 7-disulfonic
Acid
1-Amino-anthraquinone
2-Amino-anthraqiunone
l-Amino-4-hydroxy-anthra-
quinone
3-Amino-alizaiin
4-Amino-alizarin
l-Amino-4: 5: 8-trihydroxy-
anthraquinone
1: 5-and 1: 8-Amino-anthia-
quinone-sulfonic Acids
Anthracene
2-Isatin Anilide
Diamino-anthraquinones
1 : 4-Diamino-anthraquinone
1 : 5-Diamino-anthraquinone
4: 8-Diamino-anthrarufin
Dinitro-stilbene-disulfonic
Acid
1-Anthrol
9-Anthrol
1-Hydroxy-anthranol
o-Benzoyl-benzoic Acid
1:2: 4-Triamino-anthra-
535
207
208
208
250
251
249
157
418
418
419
433
427
44
191
45
111
458
332
24
116
502
498
112
113
29
30
55
27
28
88
31
108
321
189
187
188
189
117
118
307
140
quinone 573
Dehy dr o-thio-p- toluidine-
sulfonic Acid 182
Dimt ro-dibenzy 1-disulf onic
Acid 252
Dehydro-thio-p-toluidine 181
Diamino-stilbene-disulfonic
Acid 199
FORMULA INDEX OF INTERMEDIATES
585
CuHisN Benzyl-methyl-amline
CuHuNs o-Amino-azo-toluene
CuHuN 3 O 3 S o-Amino-azo-toluene-sulfonic
Acid
Ci 4Hi sN 3 O tSz Dime thy lami nq-azo-benzene-
disulfonic Acids
Ci4Hi6N 2 o-Tolidine
Ci4HisN 2 O 4-Dimethylamino-4'-hydroxy-
diphenylamine
Ethoxy-benzidine
Ci4Hi 6 N 2 O 2 Dianisidine
Ci4Hi6N 2 O 2 S A 7 -(3-Amino-4-methyl-phenyl)
p-toluene-sulf amide
CuHiN 2 O6S 2 o-Tolidine-disulfonic Acid
Ci4HiN4 Dimethyl-p: p'-diamino-azo-
benzene
Ci4Hi6N 4 O Diamino-azoxy-toluene
CnHnNs p: p -Diamino-ditolyl-amine
CuH 7 ClO4 l-Chloro-anthraquinone-2-
carboxylic Acid
CuHsClNOs 2-Anthraquinonyl-urea
Chloride
CisHioBrNO 2 l-Amino-4-bromo-2-methyl-
anthraquinone
l-Bromo-4-methylamino-
anthraquinone
2-Bromo-l-methylamino-
anthraquinone
Ci5HioO 2 2-Methyl-anthraquinone
CisHiiNO 2 l-Amino-2-meth>l-anthra-
quinone
1-Methylamino-anthraquinone 335
CisHnNOs l-Amino-4-methoxy-anthra-
quinone
Ci5Hi7N Benzyl-ethyl-aniline
CuHnNO 3-Ethoxy-4'-methyl-diphenyl-
amine
CisHnNOsS Ethyl-sulfobenzyl-aniline
Ci5Hi7NOeS 2 Benzyl-ethyl-aniline-disul-
fonic Acid
CisHnNa p-Amino-benzylidene-ethyl-
phenyl-hydrazone
Ci5HisN2 p: p'-Diammo-ditolyl-methane"195
A rs -Ethyl-A ri -phenyl-4-wi-
toly lene-d iamine
Ci5HisN 2 O 3 S Ethyl-sulfobenzyl-p-pheny-
lene-diamine
CisHi 8 N 2 O6S 3 Ethyl-sulfobenzyl-p-phenyl-
ene-diamine-thiosulfonic
Acid
Ci6HioN 2 O2 Indirubin
CisHnNOs 1-Acetamido-anthraquinone
2-Acetamido-anthraquinone
0-Hy droxy -naphthoquinony 1-
aniline-p-sulf onic A cid
Resorcinol-surcinein
Phenyl-a-naphthylamine
Phenyl-^-naphthylamine
Pheny 1- 1-naphthy lamine-S-
sulfonic Acid
Pheriyl-gamma Acid
DiacetVl-o: o'-dinitro-benzi-
dine
(Dimethylamino-hydrqxy-
benzoyl)-benzoic Acid
Dehydro-thio-m-xylidine
tso-Dehydro-thio-m-xylidine
4-Dimethylamino-3'-methoxy-
benzophenone
Ci6HisN 2 O Dimethylamino-benzoyl-
methyl-aniline
CieHnNj Amino-azo-xylene
p-Diethylamino-azo-benzene
Ci7H 9 ClO Chloro-benzanthrone
Ci 7 Hi BrNO2 4-Bromo-A r -methyl-anthra-
pyridope
CieHisN
Ci sHi 3 NO 3 S
Ci6Hi 3 NO4S
Ci6HuN4O
Ci6HisNO4
CieHiBN 2 S
PAGE
146
CnHioO
PAGB
Benzanthrone 123
35
CnHiiN
Benzyl-a-naphthylamine 147
Methyl-phenyl-a-naphthyl-
36
amine 342
Methyl-phenyl-0-naphthyl-
230
amine 342
545
234
CnHuNOaS
p-Tolyl-a-naphthylamine 571
p-Tolyl-l-naphthylamine-8-
sulfonic Acid 572
267
CnH 2 oN 2 O
Ketone 327
201
CnH 22 N2
Diamino-dixylyl-methane 195
)-
4: 4'-Dimethyl-diamino-3: 3'-
60
ditolyl-methane 242
550
p: p'-Tetramethyl-diamino-
diphenyl-methane 539
242
Ci7H~2 2 N 2 O
Hydrol 304
190
194
Ci7H 22 N 2 O 3 S
p: p'-Tetramethyl-diamino-
diphenyl-methane-sulfonic
Acid 540
158
CnHnNiOiS
p: p'-Tetramethyl-diamino-
benzohydrol-sulfonic Acid 538
116
44
C 18 Hi 2 O
CisHi 2 O 3
Methyl-benzanthrone
Naphthoyl-benzoic Acid 383
1: 6- (or 1: 7-)Diacetamido-
anthraquinone 186
151
Ci8HiN 2
N: JV'-Diphenyl-m-phenylene-
diamine 264
151
CigHieNzO
4- Pheny lamino-4 '-hy droxy-
336
diphenylamine 463
59
ie335
Ci,HisN 2
C,,Hi,N 3
C 20 HnNO
4-Pheny lamino-4 '-hydroxy-
(phenyl-3'-tolylamine)
Triamino-triphenyl-methane 573
Benzanthrone-quinoline
59
144
270
C 20 H 16 N 3
C 20 Hi,NO 3 S
C 20 H 20 N 2
a-Ammo-azo-naphthalene 35
Dibenzyl-aniline-sulf onic Acid 205
A^-Benzyl-A^-phenyl^-m-
tolylene-diamine 148
278
N: N'-(o: o'-Ditolyl)-m-
phenylene-diamine 266
145
N: N'(p: p'-Ditolyl)-w-
phenylene-diamine 266
43
C 2 iHi 2 ClNO a
l-Benzoylamino-4-chloro-an-
e!95
thraquinone 139
C 2 iH 34 N 2 Oi
l-Amino-4-benzoylamino-
277
anthraquinorie
280
C 2 iH 20 N 2 O
C 2 iH 2 iN 3
C 2 iH 28 N 2 O
JV-Benzoy 1-o-tolidine
Anhydro-formaldehy de-aniline 89
p: p'-Tetraethyl-diamino-ben-
zophenone 537
280
C 2 iH 30 N 2
p: p'-Tetraethyl-diamino-di-
320
20
C 2 iH 30 N 2
phenyl-methane 538
p: p'-TetraeMiyl-diamino-ben-
20
zohydrol 536
311
C 22 Hi 8 N 2 04S
4- (p-Hy droxy-pheny 1-amino) -
1-phenylamino-naphthalene-
516
8-sulfomc Acid
482
483
C 23 H, 8
C 23 H 26 N 2
Diphenyl-naphthyl-methane 263
Diamino-dixyiyl-phenyl-me-
thane 19 6
484
474
C 23 H 27 N 3
m-Amino-tetramethyl-p': p"-
diamino-triphenyl-methane 86
187
233
C 2 4H 22 N 2
C 26 H2oN,
JV: ^'-(p:p'-Ditolyl)-2:7-
naphthyiene-diamme 265
N: Ar'-Di-2-naphthyl-m-
phenylene-diamine
184
C* TT TV Oj
Indan throne
185
c3S?aOS
Indanthrone-sulfpnic Acid 317
4 Primuline-sulfonic Acid (So-
235
dium Salt)
232
37
213
Primuline-sulfonic Acid 495
Sulfo-m-tolylene-diamine-bis-
(carbonyl-amino-naphthol-
sulfonic Acid) 534
160
C 30 Hi 8 O4
2: 2'-Dimethyl-l: I'-bianthra-
quinone
152
PART II
GLOSSARY OF DYE NAMES
AND
PAGE INDEX OF SCHULTZ NUMBERS
GLOSSARY OF DYE NAMES
The number of dye names in use is very large. Norton, in Artificial
Dyestuffs Used in U. S., lists almost six thousand in his index where
often a number of individual marks are grouped together under the
abbreviation V.M. (Various Marks).
The list of dyes in stock in the German dye factories on August 15,
1919, the so-called Reparation Dyes, embrace over seven thousand
marks.
Throughout Germany, Switzerland, United States, France and Eng-
land, there are probably twelve thousand different dye marks in use,
many of these being for the same chemical compound of the same or
of different degrees of purity.
This glossary is based largely upon the list given in the index of Dr.
Thomas H. Norton's Artificial Dyestuffs Used in the U. S., which is
used by permission. A number of corrections have been made to this
list, and a great number of additions. These additions comprise all
the names first given in Schultz's Farbstofftabellen, and many more from
various sources. However, a number of the separate marks for a
given name are often here listed on the same line to save space.
The new American and English names that have arisen during the
past few years have not been included, due to difficulty of adequately
treating them.
This glossary copies Norton in assigning Schultz numbers followed by
letters to dyes closely related to a given Schultz Dye. Norton's prac-
tice regarding dyes of unknown composition is also used, the numbers
here employed being the same as given in Norton. Hence ready refer-
ence can be made to Norton's book for statistical information con-
cerning these dyes of unknown composition, which could not be classi-
fied in these tables. Some of Norton's dyes of unknown composition
have been identified and the proper Schultz number assigned.
Under Serial Number Column those numbers without any letter
prefixed refer to Schultz Numbers; those with a prefix of A, S, or U
refer to Azo, Sulfur or unclassified dyes of unknown composition.
V.M. is used for Various Marks as applied to dye names, and Var.
means various manufacturers and is employed rather than list a con-
siderable number of manufacturers for a given dye.
589
590 GLOSSARY OF DYE NAMES
The following abbreviations are used for manufacturers.
A Actien-Gesellschaft f iir Anilin-Fabrikation, Berlin
AW A. Wiescher & Co., Successors, Haeren, Belgium
B Badische Anilin- und Soda-Fabrik, Ludwigshaf en
BrAlizCo. British Alizarin Co.
BD British Dyes, Ltd., Huddersfield
BK Leipziger Anilinfabrik Beyer & Kegel, Furstenberg
By Farbenfabriken vorm. F. Bayer & Co., Leverkusen
ByCo Bayer & Co., Rensselaer, N. Y.
C Leopold Cassella & Co., Frankfort on the Main
CICo .... Clayton Aniline Co., Clayton near Manchester
CDCo . . .Central Dyestuff Co., Newark, N. J.
CG Chemikalienwerk Griesheim, Griesheim on the Main
CJ ' Carl Jager Anilinfarbenf abrik, Diisseldorf
CR Clauss & Co. (formerly Claus & R6e), Clayton near Manchester
CV Colne Vale Chemical Co., Milnsbridge near Huddersfield
DH Farbwerke vorm. L. Durand, Huguenin & Co., Germany and
France
FA Parbwerk Ammersfoort, Ammersfoort, Netherlands
G Geigy, Basel
GrE Chemische Fabrik Griesheim-Elektron, Offenbach on the Main
H Read Holliday & Sons, Huddersfield
H&M .... Heller & Merz Co., Newark, N. J.
I Gesellschaft fur chemische Industrie, Basel
K Kalle & Co., Biebrich on the Rhine
Ki Kinzlberger & Co., in Prague
L Farbwerk Miilheim vorm. A. Leonhardt & Co., Mulheim
Lev Levenstein, Ltd., Crumpsall Vale
M Farbwerke vorm. Meister Lucius & Bnining, Hochst
NF Niederlandesche Farben-und Chemikalienf abrik Delft, Delft.
P Socie*t6 Anonyme des Matieres colorantes et produits chimiques
St. Denis (formerly A. Poirrer), St. Denis
Q Imports of Unknown Source
S Chemische Fabrik vorm. Sandoz & Co. Basel
Sch Schoellkopf Aniline & Chemical Works, Buffalo, now National
Aniline & Chemical Co.
tM Chemische Fabriken vorm. Weiler-ter-Meer, Uerdinger
WB W. Beckers Aniline and Chemical Works, Brooklyn
WD Wiilfing Dahl & Co., Barmen
Note. Within the past few years many of these companies have consolida .ed or
changed names.
GLOSSARY OF DYE NAMES
591
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Acetyl Red GX
B
U90
tM BK
212
Acetylene Bl ic 3 B
G
U648
K
2i2a
Acetylene Blue 6 B ....
G
U649
Acid Brown RN
G
212a
M
159
Acid Brown SR
K
2i2a
Acid Alizarin Black R ....
M
159
I
212a
Acid Alizarin Black SE . . . .
Acid Alizarin Black SN . . . .
M
M
288
289
Acid Brown Y
A.cid Chrome Black G ....
P
I
212
Al47a
Acid Alizarin Black SR
Acid Alizarin Brown B
Acid Alizarin Blue
Acid Alizarin Blue BB, GR.
Acid Alizarin Garnet
Acid Alizarin Garnet R . . . .
Acid Alizarin Green B, G .
Acid Alizarin Green 3 G
CV
B
M'
M'
M
I
M
288a
154
790
790
155
155
796
796a
202
Acid Chrome Black LG
Acid Chrome Black RH. . . .
Acid Chrome Black RH
Acid Chrome Black RHN . .
Acid Chrome Black WS
Acid Chrome Black 1551 . . .
Acid Chrome Blue
Acid Chiome Blue (reddish)
By
y
BK
By
CV
K
AW
Bv
A147
A148
A610
A148a
A149
A723
U302
A532
U209
Acid Alizarin Violet N .
M
294
CV
A724
Acid Alizarin Yellow GGW.
M
Bv
156
88
Acid Chrome Blue 3 G
Acid Chrome Red N
By
CV
U206
A725
Acid Anthracene Brown M, P
Acid Anthracene Brown PG
Acid Anthracene Brown R. .
Acid Anthracene Brown
RH, W
By
By
By
By
88a
88a
88
88a
Acid Chrome Blue 2 R
Acid Chrome Blue 5 R
Acid Chrome Violet R
Acid Corinth
A.cid Corinth 240 S
By
By
By
tM
G
U207
U208
U210
U522
U602
Acid Anthracene Brown
WSG
Bv
88a
Acid Cresol Black 4196
GrE
g
U501
166a
B?
400
O
166a
AcidAnthracene Red 5 BL, G
Acid Black
&
400a
217e
Acid Cyanine BF
A.cid Dark Green
A
705b
505b
I
217e
590
Acid Black AS
Q
269c
Acid Eosine CA G ....
B
590a
Acid Black 10 B
WB
217
Acid Eosine 3 G
CJ
590a
Acid Black 6 BA
Acid Black 4 BD
CG
I
217e
217e
Acid Eosine L new, LB ....
Acid Eosine L 27314, SP . . .
B
B
590a
590a
Acid Black BR
G
269c
A.cid Eosine 1632
K
590a
Acid Blark "RTf
tM
269
Acid Eosine 13389 ....
CJ
590a
Acid Black D
I
217e
A-cid Fast Blue SB
WB
189
Acid Black F
Bv
A144
A.cid Fast Blue SR . . .
WB
188
Arid "Rim-* - TTW
Q
269c
AW
A533
Acid Black G HA HAS . .
I
217e
A,cid Fast Violet
AW
U551
Acid Black H* '
S
217e
524
Acid Black KB ....
269c
I
504
Acid Black M
A145
tM
502a
Acid Black M
BK
217e
A.cid Green
WD
505
Acid Black M . . .
jj
269 c
A.cid Green (V M )
c
505a
Acid Black ^O
s
217e
Acid Green 2 A B, 2 BA. . .
tM
502a
Acid Black 32
jj
269 c
Acid Green 2 B
p
502
Acid Rlcipk 90^4
J
217e
Acid Green 6B BW ....
504
Acid Black 2195
Acid Blue
BK
AW
217e
543c
Acid Green 2 BG
tM
K
502
505
Acid Blue ....
H&M
539
Acid Green GG
By
505
Acid Blue
|
U301
877
I
U301
B
U91
Acid Blue B
s
565
Acid Magenta
Bv.C
524
g
565b
H.Sch
524
Arirl "RliiA "RA ' C*' T~)RS'
Q
543c
CV
524
Acid Blue E
AW
543c
Acid Magenta B, F
G
524
Acid Blue EX
s
565b
Acid Magenta FCNS
GrE
524
j
U301
Acid Magenta G
G
524
Acid Blue AG
K
U301
M
524
Acid Blue PN
O
543c
A,B
524
Acid Blue R '
AW
543c
Acid Magenta S
GrE
524
Acid Blue R
g
565b
CV
524
Acid Blue 5 R ....
Q
543c
Acid Magenta Crystals I ...
CV
524
Acid Blue RBF
562
Acid Milling Black B
265
Acid Blue V ......
AW
543
Acid Milling Red G
293
Acid Blue Y
AW
543c
Acid Milling Scarlet
c'lCo
AW
484
A53
M
609c
tM
722
(V.M.)
Anthiacene Brown
C
B
Bv
181a
782
782a
Auronal Black 3 A, 4 A
Auronal Black 4 A, 4 G, 5 G
\uroral Black B
G
tM
tM
722a
722a
727
Antniacene orow :'
H
782
Auronal Black N 2 R
tiki
722
Bv
782a
Auronal Black 3
tM
722a
Anthracene Brown SW. . . .
B
782
Auronal Blue D
tM
tM
S137
S138
(V M )
C
A318
Auional Orange R
tM
S140
tM
S139
FF
C
865
Aurophosphine G, 4 G
A
606a
Q
A322
Q
U785
AntnraceneL/nroma ^e i
p
732
(V.lVi.)
Anthracene Chrome Black
(V M )
C
c
A3 13
185
Autogene Black EEB
Autol Red BL
Autol Red RL, RLP
P
B
B
723
56
106
Anthracene Chrome Black
FF ex
C
185
Azarine S
Azidine Blue B, BALG
M
CJ
86
410
c
A323
Azidine Blue 3 B
CJ
391
Anthra.fnnp Chrome Green
c
A325
Azidine Blue BAN
CJ
410
596
GLOSSARY OF DYE NAMES
Name
Man u-
fao-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
' Azidine Blue BX
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
M
M
M
M
M
K, M
S
By
& y
M
M
M
WD
K
Var.
By
By
A
DH
DH
f
M
GrE
By, etc
Sch
M
A
B
Var
B
B
B
B
K
k"
G
A
By
WD
WD
GrE
By
By, etc.
C
C
B
B
B
tM
B
B
B
B
By
By
By
386
410
313
A454
A455
281
282
A456
280
392
424
304
420
A418
A419
A420
A421
63
63
63
63a
A151
64b
64
64a
64
163
163
168
229
229
141
292
291
A 152
44
A422
381
377
112
160a
50
673
672
673
673
672
672
A389
164
163b
84
77
95
65
65
481
65
A153
94
A329
A332
141a
141a
141a
140
141a
140
141
141a
71
147
146
"
Bv
AW
AW
K
B
CV
B
GrE
C
GrE
CV
CV
CV
I
C
A
FA
M
M
M
M
C,A
S
Sch
C, etc.
tM
GrE
S
A
WB
C
GrE
g y
C
C
K
K,M
Var.
Sch
tM
Sch
tM
tM
K
K
I
K
K
AW
DH
Q
B"
Q
WD
WD
WD
WD
WD
M
C
C
WD
K
A, etc.
Bv.CG
S, etc.
147
62
510
A537
A538
A390
A 67
146
A68
382
A333
A457
A727
A728
A729
U786
U787
A423
A334
44
312a
408
408
46
60
165
A711
163
163
163
163
168
163
163
239
115
407
A335
61
A336
A391
141
141
141
141c
141
141
141
141c
U306
U306
520a
U306
U307
U552
677
IT788
499
U100
U789
337
476a
476
426
326
318
U275
U276
A526
410
410
410
410
Azidine Blue 24574
Azo Galleine
Azidine Bordeaux G
Azo Green
Azo Indigine 6 B
Azidine Dark Brown
Azidine Fast Orange ES. . .
Azidine Fast Scarlet 4 BS .
Azidine Fast Sacrlet 7 BS .
Azidine Fast Scarlet E 4 B
Azidine Fast Scarlet GGS .
Azo Indigine S
Azo Indigine 419, 420
Azo Magenta 6 BX
Azo Magenta G
Azo Magenta RS
Azo Mauve B
Azo Merino Black
Azo Milling Yellow 5 G
Azomine Black FF
Azidine Sky Blue FF
Azidine Yellow CP
Azidine Wool Blue B
Azo Acid Black B 15
Azo Acid Black 3 BL
A zomine Fast Yellow AL . . .
Azomine Milling Black N . .
Azo Acid Black R
Azo Acid Black TL II
Azomine Yellow R
Azo Orange Rubine
Azo Orseille 2 B
Azo Acid Blue B ....
Azo Acid Blue B
Azo Acid Blue 2 G
Azo Acid Brown 26049
Azo Acid Magenta G
Azo Acid Red B
Azo Orseille R
Azo Orseilline
Azophor Black S
Azophor Orange MN
Azo Phosphine GO
\ zo R^ A
Azo Acid Red 5 B
Azo Acid Red BA
^.zo Rhodine 2 B
Azo Acid Rubine (V.M.) . .
Azo Acid Rubine 2 B
Azo Acid Violet
\zo Rubine (V M.)
Azo Acid Violet A 2 B, AL
Azo Rubine S
^.zo Rubine SG
Azo Alizarin Black I
Azo Alizarin Bordeaux W .
Azo Alizarin Brown I
Azo Archil R
Azo Black O
\zo Rubine WB
\zotol C
\zo Turkish Red
^.zo Violet
Azo Black Blue B, R
Azo Blue
Azo Wool Black (V.M.)....
Azo Wool Blue (V.M.)
Azo W ool Violet (V.M.) ....
\./o Wool Violet 415
Azo Bordeaux
Azo Cardinal G
\.zo Yellow
Azo Carmine
Azo Carmine B
\ zo Yellow
Azo Yellow 3 A, 3 AN
V/o Yellow A 5 W
Azo Carmine BX
Azo Carmine G
Azo Yellow 3 G
Azo Carmine GX
Azo Cerise M, 1618
Azo Chrome Blue B
Azo Chrome Blue R
Azo Chromine
Azo Coccine 2 R ...
Azure Blue
^.zure Blue A ASI . . .
Azure Blue O, VS
"Rnsif R1nr>k TFS
Azo Cochineal
Azo Coralline
Azo Corinth ....'....
Sasic Gray
Jasic Green Z
iasic Kraft Brown Y 2
Azo Crimson S
Azo Eosine . . ,
Azo Fast Blue (V.M.)
Azo Fast Violet
Jenzamine Azo Blue G . . . .
ienzamine Brown 3 G
ienzamine Brown 3 GO
tenzamine Pure Blue
ienzamine Violet G
Benzidine Pure
Azo Flavine CX
Azo Flavine FF, 3 G
Azo Flavine GX, 3 R
Azo Flavine 3 R
Azo Flavine 2 RNH, RX. . .
Azo Flavine RS
Azo Flavine S
enzine Blue
Azo Flavine SGR
enzoazurine (V.M.)
enzoazurine G
Azo Fuchsine B
Azo Fuchsine 6 B
Azo Fuchsine G, 4 G
epzoazurjne G , . . .
GLOSSARY OF DYE NAMES
597
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Benzoazurine 3 G
By etc
411
GrF
605
Benzoazurine R
By
GrE
410
385
Benzof orm Blue B
By
Bv
A196
A197
WB
410
A
U71
Benzo Black Blue G
Bv
459
Benzoform Orange G
Bv
A198
Benzo Black Blue 5 G
Benzo Black Blue R
By
Bv
460
450
Benzof orm Red G
A y
Bv
U72
A199
Benzo Blue 2 B
Bv
337
Benzoform Red 2 GF
Bv
A200
Benzo Blue 3 B ....
Bv
391
Bv
A201
Benzo Blue BX
Bv
386
Bv
A202
Benzo Blue RW
By
419
Bv
447
Benzo Bordeaux 6 B
By
A 154
Benzo Green BB . .
By
A184
Benzo Brilliant Blue 2 GDN
BK
A442
Bv
A185
Benzo Bronze E
By
A155
Benzo Green FF
Bv
A186
By
A156
Benzo Green FFG
By
A187
Bv
487
Bv
A188
Benzo Brown BX
Benzo Brown D 3 G
Benzo Brown G
By
By
Bv
490
485a
485
Benzoin Blue 5 GN, RH . . .
ienzoin Brilliant Blue GDN
Benzoin Brown C
BK
BK
BK
410
410
477
Benzo Brown 5 G, 2 GC, 3 GC
Benzo Brown MC, NBX. . .
i
485a
485a
ienzoin Fast Red AE
Benzo Indigo Blue
BK
By
194
452
Benzo Brown 5 R
Benzo Brown RC, TR
By
By
190
485a
Senzo New Blue 2 B
Benzo New Blue 5 B
By
Bv
379
379
Benzo Chrome Black Blue B
Benzo Chrome Biown B . . . .
Benzo Chrome Brown BS . . .
|
By
A157
A158
A159
ienzo New Red 4 B
Jenzo Olive
Benzo Orange R
Bj
B?
A189
446
340
Benzo Chrome Brown G . . . .
Benzo Chrome Brown 5 G . .
By
Bv
A160
A161
Jenzo Pure Yellow FF
4
A190
365a
Benzo Chrome Brown R
By
A162
Benzopurpurin
H
365
Benzo Copper Blue B ....
Bv
A163
I
365a
Benzo Copper Blue 2 B ....
By
Bv
A164
390
Jenzopu'purin AM
By
A etc
365a
365
Bv
425
r, ^ P A T3
A* etc
363
Bv
336
By etc
364
Bv
A165
A etc
405
Benzo Dark Green B
Bv
A166
A
363
Benzo Dark Green GG
Bv
A167
BK
363
Benzo Deep Black SS
Bv
A168
zopurpu i 4
GrE
363
Benzo Fast Black
G
A611
Benzopurpurin 4 &r. ....
363
Benzo Fast Black L
By
A169
Benzo Red 10 B
y
A191
Benzo Fast Blue B, BN ....
By
456
Benzo Red 12 B ....
By
A192
Benzo Fast Blue FRL, 2 GL
Benzo Fast Blue 4 GL, 2 L.
Benzo Fast Blue R
By
? y
456a
456a
451
Jenzo Rhoduline Red B. . .
3enzo Rhoduline Red 3 B. .
By
By
Bv
A203
A204
A193
Benzo Fast Bordeaux 6 BL.
Benzo Fast Brown 3 GL . . .
By
A170
A171
rJenzo Rubine SC
B
By
A194
319
Benzo Fast Brown RL
By
A172
Benzo Scarlet BC
By
A195
Benzo Fast Eosine BL
By
A173
Benzo Sky Blue
By
426
Benzo Fast Gray
By
A174
CR
517
Benzo Fast Gray BL
By
A175
Benzo Violet O
By
326
Benzo Fast Heliotrope BL. .
Benzo Fast Heliotrope 4 BL
By
By
A176
A177
Jenzo Violet R
Benzoyl Pink
? y
326a
104
Benzo Fast Heliotrope 5 RH
Benzo Fast Heliotrope 2 RL
By
Bv
A178
A179
Benzyl Black B
A661
U651
Benzo Fast Orange 2 RL. . .
Benzo Fast Orange S
By
Bv
A180
A181
Jenzyl Bordeaux B, 17619. .
Benzyl Green B
U652
503
Benzo Fast Orange WS
By
340a
A662
Benzo Fast Pink 2 BL . ...
Benzo Fast Red .
By
Bv
297
332
Benzyl Violet
Benzyl Violet 4 B, 6 B, 10 B
517
517
BenzoFastRedSBL 9BL D
Bv
332
Benzyl Violet 5 BN
I
517
Benzo Fast Red FC
Bv
343
Betamine Blue 8 B
541
Benzo Fast Red GL, L. ...
Benzo Fast Rubine BL. . . .
Benzo Fast Scarlet (V.M.). .
BenzoFast Scarlet 4BS, 5BS
Benzo Fast Scarlet 8 BS,
8BSN
fe
ly y
By
332
A183
279
279
279
Biebrich Acid Blue G
Biebrich Acid Blue V
Biebrich Acid Violet R
iiebrich Patent Black
iismarck Acid Brown
Bismarck Brown . .
K
K
K
K
By
A, etc.
U308
U309
A392
278
A205
283
Benzo Fast Scarlet GS. . . .
Benzo Fast Violet NC
By '
By
Bv
279
327
327a
iismarck Brown (V.M.) . . .
Bismarck Brown EL
C
A
I
283
283
283
Benzo Fast Yellow 4 GL
Bv
29 6a
CV.etc.
284
Benzo Fast Yellow 5 GL . .
Benzn Fast Yellow RL. .
By
Bv
296
296a
Bismarck Brown 2 R, 2 RV
Bismarck Brown Y . .
tM
Sch
284
283
598
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Bismarck Brown YS
tM
283
Brilliant Acid Blue A
A, By
545
Bismarck Brown 53
Bismarck Brown 1568
Sch
CV
284
283
Brilliant Acid Blue B, FF, L
Brilliant Acid Blue V
By
By
545c
543
Black (V.M.)
Black (V.M )
CJ
H
U494
U749
Brilliant Acid Blue 25601 . . .
Brilliant Acid Carmine B,
S
545c
Black AJ
p
700a
BOO
GrE
66b
Black BH
AW
U553
Brilliant Acid Green 6 B
Bv
503
Black CBR
p
698
Brilliant Acid Red G
K
U312
Black CE
H
U749
Brilliant Alizarin Blue
Var
667
Black C 2 N
p
698
Brilliant Alizarin Blue D 3 G
M
667
Black DX
H
U749
Brilliant Alizarin Blue D 6 G
M
667
Black E
B
U101
Brilliant Alizarin Blue DRI
M
667
Black HB
AW
U554
Brilliant Alizarin Blue R. &
Black M
H
U749
(V M )
Bv
667
Black N
H
U749
Brilliant Alizarin Blue R. .. .
CR
667
Black NSA
p
700a
Brilliant Alizarin Blue 3 R
By
667
Black RW, X
H
U749
Brilliant Alizarin Green ....
WD
657a
Black soluble in fats
G
U605
Brilliant Anthrazurol
B
U105
Q
U277
Brilliant Archil C
C
55
Black Base BB
B
U102
Brilliant Azo Acid Blue 3 G
s
63b
Black Base S
B
U103
Brilliant Azure Blue VS
j
U313
Black Black O . . ,
Blue (V M )
M
H
U428
U750
Brilliant Azurine B, R, 5 R.
By
By A L
416a
416
Blue AS
s
U695
Brilliant Benzo Blue 6 B
Bv'
424
Blue 3 BB
GrE
U502
Bv
A207
Blue BS . .
p
539
Brilliant Benzo Violet B . . .
By
A208
Blue 5 BS
tM
U524
Brilliant Benzo Violet 2 R
Bv
A209
Blue BS 3 BB
GrE
U503
Brilliant Benzo Fast Violet
BlueBSJ
GrE
U504
2 RL
By
A206
Blue BSR
GrE
U505
Brilliant Benzo Fast Violet
Blue CA
I
U653
BL
By
A206a
Blue CV
AW
U555
Brilliant Black ....
Var
272
Blue DB
U790
Brilliant Black B
B etc
272
Blue DR
Q
U791
Brilliant Black 3 B, G ....
B
272
Blue DS
H
U750
Brilliant Blue A
CV
U725
Blue JB
c
U278
Brilliant Blue G
g
U699
Blue N
8
U696
Brilliant Blue GG
CV
U726
Blue PCN
DH
697
Brilliant Blue 217
O
U793
Blue PCV
G
U606
Brilliant Blue 286
Q
U794
Blue RR
GrE
U506
Brilliant Bordeaux SD
A
Al
BlueS R
Blue RS .
tM
p
U525
537b
Brilliant Brown 205
Q
B
U795
U106
Blue 25
s
U697
Brilliant Carmine GG
B
U107
Blue 26
8
U698
B
U108
Blue 214
B
U104
8
626
Blue 1900 TC
Blue 16519
DH
L
635
U514
Brilliant Chrome Violet BD
Brilliant Cloth Blue
l y
549a
189a
Blue 27071
Blue for silk RN .
? y
U217
537b
Brilliant Cochineal 2 R ....
C
A L
81
316
Blue (greenish) spirit soluble
M
521
Brilliant Congo R
A, L
370
Blue Black B
M
269b
Bv
370
Blue Black N. .
K
215
Brilliant Congo R
S
370
Blue Black O
Blue Black for Half Wool G
Blue Crystals 3035
M
By
K
269b
U218
U309
Brilliant Congo Blue B
Brilliant Congo Blue 5 R. . .
Brilliant Congo Violet R
A
A
A
U73
U74
U75
Blue Residue BW 6 M
K
U310
Brilliant Copper Blue BW
A
U76
Boma Black BH . .
AW
U556
Brilliant Copper Blue GW
A
U77
Boma Black BHX
AW
U557
Bv
538
Boma Pink
AW
U558
C
227
Boma Yellow BBF
Bordeaux
AW
AW
U559
168
Brilliant Croceine 3 B, MOO
c y
227
270
Bordeaux extra
Bordeaux B
Sch
Var
320
112
Brilliant Croceine 3 BA
By
GrE
227
227
Bordeaux BLA
Bordeaux BR
tM
BK
320
112
Brilliant Croceine NZ
M
M
227
163
Bordeaux BX
Bv
237
1V & t P * n '-vr'
M
163
Bordeaux COV
A
320
Brilliant Delphine Blue B
j
U314
Bordeaux G
By M
254
Brilliant Delphine Blue BS
Bordeaux G
BK
112
VS
8
622
Bordeaux R
BK K
112
Brilliant Dianil Blue 6 G
M
541
Bordeaux S
Bordeaux 5005. . .
A
BK
168
112
Brilliant Dianol Red R
Brilliant Diazine Blue 1230
LW
K
358
U315
Bordeaux Black. .
Q
U792
Brilliant Double Scarlet. . .
BK
176b
GLOSSARY OF DYE NAMES
399
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Brilliant Fast Black
I
U654
Brilliant Yellow S
B etc
142
Brilliant Fast Blue
Brilliant Fast Blue B
Brilliant Fast Blue 3 BX. . .
AW
By
By
A539
A210
A211
Bromofluoresceic Acid A 3 G
Bromofluoresceic Acid BA
BL
M
M
587b
587b
Brilliant Fast Blue 2 G
Brilliant Fast Blue 4 G ....
By
Bv
A212
A213
Bromofluoresceic Acid Crys-
tals
M
587b
Brilliant Fast Red G
B
162
Bv
881
Brilliant Fast Red P
Brilliant Geranine B
By
Bv
A214
118
Bromo Indigo Rathjen
P
879
135
Brilliant Glacier Blue
I
501
Brown . . .
BK
U479
Brilliant Green
Var
499
Brown A 1678
B
Ulll
Brilliant Green B
tM
495
Brown GC
G
U607
Brilliant Green 6 B . . .
499
Brown PCC
DH
U596
Brilliant Green BN
tM
499
Brown Y
H
283
Brilliant Green D
c
499
Brown PCC
G
U607
Brilliant Green PND
GrE
499
Brown 43
s
U700
Brilliant Green S
CJ
499
Brown 359
Lev
283b
Brilliant Hessian Purple. . . .
L
302
Brown 37104
H
283
Brilliant Indigo B
B
885
Buffalo Black AD . "...
Sch
266
Brilliant Indigo BD
B
885
Buffalo Black 2 B
Sch
272
Brilliant Indigo 2 B, BED.
Brilliant Indigo 4 G
B
B
884
887
Buffalo Black 4 B
Buffalo Black 8 B 10 B
Sch
Sch
269
261
Brilliant Indigo G, GD,
Buffalo Black EA
Sch
268
4 GD
B
886
Buffalo Black NB
Sch
217
Brilliant Lake Red R
M
45
Buffalo Black PY
Sch
220
Brilliant Lanafuchsine
(V.M.)
Brilliant Milling Blue(V.M.)
Brilliant Milling Blue B
Brilliant Milling Green B . . .
Brilliant Naphthol Blue
Brilliant Orange G
C
C
K
C
C
A, By
M '
U280
U281
U316
503
U282
339
70
Buffalo Black R
Buffalo Chrome Black BWN
Buffalo Cyanine R, 3 R
Buffalo Direct Blue G
Buffalo Direct Cardinal 7 B
Buffalo Direct Crimson B . .
Buffalo Direct Garnet R . . .
Sch
Sch
Sch
Sch
Sch
Sch
Sch
Sch
261
275
257
410
405
313
312
362
Brilliant Orange R ...
M.etc.
79
Buffalo Direct Orange Y . . .
Sch
392
Brilliant Orseille
C
55
Buffalo Direct Red 4 B ....
Sch
363
Brilliant Orseille C
Brilliant Patent Blue A ....
Brilliant Patent Blue A ....
Brilliant Phosphine
C
K
M
I
55
U317
545
606b
Buffalo Direct Violet 4 R. ..
Buffalo Direct Yellow CG . .
Buffalo Direct Yellow CRR
Buffalo Fast Blue B ....
Sch
Sch
Sch
Sch
375
342
394
189
Brilliant Phosphine G, 5 G .
I
606
Buffalo Fast Blue R
Sch
188
Brilliant Pink
s
57 la
Buffalo Fast Crimson G . . . .
Sch
64
Brilliant Ponceau 5 R
Brilliant Pure Yellow 6 G . .
Brilliant Purpurin 4 B
Brilliant Purpurin 10 B ....
Brilliant Purpurin R
Brilliant Red R paste
By
By
A, By
A
A, etc.
169
U219
368
368a
369
45
Buffalo Fast Crimson R
Buffalo Fast Fuchsine B
Buffalo Flamine B
Buffalo Flamine G
Buffalo Rubine
Butter Yellow
Sch
Sch
Sch
Sch
Sch
A, etc.
66
147
94
95
110
32
Brilliant Rhodulin Red B
By
684b
Cachou (V M )
Lev
U731
Brilliant Rhodulin Violet
By
684a
P
706
Brilliant Safranine G
A
679
Calcutta Black D
H
U751
Sch
684
S
626
Brilliant Scarlet (V M )
c
U283
Calcutta Blue 2
s
U701
Brilliant Scarlet AL
M
A424
842
Brilliant Scarlet NY 47
B
U109
765
Brilliant Scarlet R
BK
A443
763
Brilliant Scarlet 2 R
tM
A515
766
Brilliant Scarlet 3 R
Sch
169
Candle Blue
K
U318
Brilliant Scarlet 4 R 4 RSP
tM
A516
K
U319
Brilliant Scarlet 141113
B
U110
B
606
Brilliant Sky Blue 5 B
Bv
U220
Capri Blue GON
By, L
620
Brilliant Sky Blue 6 B
424
L
620a
Brilliant Sky Blue G
By
U221
Carbazole Wool Green ... .
C
U284
Brilliant Sky Blue 5 G
By
541
Carbide Black
I
462f
Brilliant Sky Blue 8 G
By
U223
Carbide Black E, EX, SX .
I
462f
Brilliant Sulfonazurine R . .
Brilliant Sulfon Red B 5 B
By
361a
Carbide Fast Black GF . . .
Carbide Violet V
I
I
462f
462g
10 B
S
182
Carbindol Blue R
748
Brilliant Victoria Blue RB . .
BrilliantWool Blue B FFR G
I
Bv
559b
562a
Carbon Black (V. M.)
Carbon Black 4 B
K
M
458
272
Brilliant Yellow
By
U224
Cardinal 3 B
H
512
Brilliant Yellow
Var
303
Cardinal Red J
H
161
Brilliant Yellow
tM
142
Carmine Blue A
AW
U560
Brilliant Yellow C
Sch
303
Carmine special
P
U592
600
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Carmine Blue V ....
K
U320
Chloramine Yellow GG
Carmine Brilliant Blue. . . .
AW
U561
HW M
Bv
617
Carmine Naphth Garnet . .
Carmoisine
DH
A, S
106
163
Chloramine Yellow M
Chloramine Yellow RC ....
S
By
617
617
Carmoisine B
Bv
163
M
97
Carmoisine 3 B
By
163a
Chloranthrene Yellow G ...
849
Carmoisine 6 B R
H
163a
Chlorantine Blue BB
A663
Carmoisine L WS
163
A664
Carpet Red B, BT, R
Carthamine 6 A B
K
tM
U321
570-
Chlorantine Brown R
A665
A666
Cashmere Black 3 BN . . . .
Cashmere Black MCS
Cashmere. Black V
Cashmere Blue TG
y
g
A215
A733
A216
A217
Chlorantine Brown 15895. .
Chlorantine Fast Blue RL .
Ohlorantine Lilac B
A667
451
A668
A669
Celestial Blue
WD
U541
A670
Celestine Blue B ....
Bv
641
A671
Cerasine Brown AN
Cerasine Dark Red I, II. ...
c y
c
U285
223a
Chlorantine Pure Blue ... .
A672
358
c
oe
A673
Cerasine Red 56 I, 56 II ...
Ceres Blue 4
c
Bv
223
U225
Chlorantine Yellow JJ
Chlorazol Blue GBDS
H
617
417
Ceres Brown 3
By
U226
Chlorazol Blue 3 G
H
417
Ceres Brown 4
By
U227
H
417
Ceres Orange 3
By
U228
Ph1nrn7nl Rrilliant Blue 3 B,
Ceres Red 3
By
U229
10 B
H
417a
Ceres Red 6
Cerise DN DIV
?
U230
512
Chlorazol Brilliant Blue 14B,
F ...
H
417a
Cerise M
tM
C1 n
Cerise N
c
512
RH
H
A734
Ceroflavine
B
U112
Chlorazol Brilliant Green G
H
A738
Cerotine Scarlet G
CJ
34b
H
A735
Chicago Blue B
A
42 V
II
A740
Chicago Blue 2 R
Chicago Blue 4 R
Chicago Blue RW
A
A
384
324
Chlorazol Fast Blue RH. . . .
Chlorazol Fast Bordeaux B.
H
H
A741
A742
A 740
Chicago Blue new
A
G.
422a
Chlorazol Fast Scarlet RH . .
H
H'
A744
A 74C
Chicago Red 111.
China Blue
G
A
A612
Chlorazol Fast Yellow AF. .
H
H 1
A746
A 747
Chinaldine Yellow
Chloramine Black BH
Chloramine Black BH
Chloramine Black EXD, FF
Chloramine Black HW
Chloramine Black N
1 'GCCCCCODC/
613
469
333
469a
473
469
Chlorazol Fast Yellow BS . .
Chlorazol Fast Yellow R . . .
Chlorazol Green B
Chlorazol Green G
Chlorazol Orange 2 R
Phlnrarnl "Rprl A
H
H
H
H
H
u
A748
A749
474
A750
340
A751
Chloramine Blue 2 B
Chloramine Blue 3 B ...
s
g
337
471 a
Chlorazol Sky Blue FF. . . . .
H
A752
Chloramine Blue 3 G
s
471
H
A754
Chloramine Blue BXR
S
386
Chlorazol Violet 3 B
H
A755
Chloramine Brilliant Red 8 B
S
472
358
Chlorazol Violet R
Chlorophenine
H
CICo
A756
17
Chloramine Brown G
By
A218
AW
U568
Chloramine Dark Green B . .
S
470a
B
U113
Chloramine Fast Red F, FF
S
343
U114
Chloramine Fast Yellow B.
By
617
Chromal Blue G, GC
G
552
Chloramine Green B
Chloramine Green G
S
y
470
475
Dhromal Dark Blue K .....
G
552a
TTfiOS
Chloramine Orange
g
Chloramine Orange G
Chloramine Pure Blue
Chloramine Red B, 3 B
S
11
471b
319
Chromanil Black BF
Chromanil Black FF
Chromanil Blue R
A
A
A.
A2
A3
A4
Chloramine Red 8 B, 8 BS .
Chloramine Sky Blue Aconc
I"
358
426
Chromanil Brown 2 G
Chromazine Blue G
A
M
A5
U429
Chloramine Sky Blue 6 B, FF
Chloramine Violet
Chloramine Violet N
Chloramine Violet R . .
S
t y
Bv
424
A220
327
A221
yhromazone Blue R
yhromazone Red (new) , A . .
Chrome Acid Black
G
G
I
130
129
U655
TTQCC
Chloramine Yellow
By etc
617
CC4
Chloramine Yellow DB, FF
By
617
Chrome Black
WD
275a
Chloramine Yellow G
S
617
Chrome Black BA. .
O
A765
GLOSSARY OF DYE NAMES
601
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Chrome Black A
CG
275a
Chrome Fast Yellow R, 2 R
A
177
Chrome Black DF
Chrome Black DF
AW
M
275a
A425
Chrome Gallus Brown RR. .
G
Bv
158a
509
Chrome Black FPP, G . .
AW
275 a
Chrome Green (V. M.)
K
U324
Chrome Black I
H
275a
Chrome Green C
K
U324
Chrome Black LV
K
U322
L
U515
Chrome Black M Z
H
275 a
DH
625
Chrome Black 2841
Chrome Black 57006
K
H
U322
275 a
Chrome Leather Black E. . .
Chrome Leather Black E . . .
B
By
U116
U233
Chrome Blue
Chrome Blue ATX
^
567
163b
Chrome Leather Black E. . .
Chrome Leather Black EA..
w
B
U702
U117
Chrome Blue B
WB
626
Chrome Leather Black I . .
WD
U542
Chrome Blue 2 B, FBX
Chrome Blue G
BK
Q
163b
163b
Chrome Leather Black M . .
Chrome Leather Brown R. .
U234
U703
Chrome Blue R
AW
163
Chrome Orange GR
By
U235
Chrome Blue R
WB
599
Chrome Patent Green N . . .
K
219
Chrome Blue RX
Chrome Blue Black B
B
K
163b
U323
Chrome Red 2593
K
Bv
U325
549
By
550
G
557
Chrome Brown .
AW
158a
Chrome Violet Brown 9457 .
K
U326
Chrome Brown CS
K
158a
Chrome Violet S for print-
Chrome Brown P
p
90
G
557
Chrome Brown RR
G
158
Bv
177
Chrome Brown RVV
Q
158
Chrome Yellow
I
177e
Chrome Brown 414
Lev
158a
Chrome Yellow D, DF
By
177
Chrome Brown 2813
K
158a
Chrome Yellow G, GG
s
177e
Chrome Deep Black A
G
275b
Chrome Yellow R
AW
177e
tM
275
Chrome Yellow R
Bv
177
Chrome Deep Black G
G
275b
Chrome Yellow SM, 2501...
K
A393
Chrome Deep Black G
Chrome Fast Black
tM
G
275
275
Chromine G
K
s
614
614a
Chrome Fast Black A
CG
181c
275c
Chromine Blue.
A
AW
U562
U563
Chrome Fast Black F
A.
A6
AW
U564
275
AW
U565
Chrome Fast Black FW
Chrome Fast Black P4B . . .
Chrome Fast Black PF
Chrome Fast Black PON
I
A
A
CG
275c
A7
A8
181c
Chromine Fast Blue S
Chromine Violet 2 R
Chromocitronine R
AW
AW
DH
DH
U566
U567
140a
631
Chrome Fast Black PT
A
A9
M
777
Chrome Fast Black PV
157
M
U430
Chrome Fast Black PWBL
181
DH
U597
Chrome Fast Black PWRR
181
M
57
Chrome Fast Black 12172
CG
18lc
M
67
Chrome Fast Blue B
B
U115
Chromotrope 8 B
M
171
Chrome Fast Blue 4 B . .
Chrome Fast Blue R
A
U78
U657
Chromotrope 10 B
Chromotrope DW ... .
M
M
114
57a
Chrome Fast Blue 13366
U658
M
164
Chrome Fast Brown A. .
A674
A675
Chromotrope 2 R
M
M
40
57a
Chrome Fast Brown G . .
Chrome Fast Brown R. .
Chrome Fast Brown TP
A
Bv
A676
A10
U231
Chromoxane Blue R
Chromoxane Violet 5 B ....
By
By
By.etc.
U236
U237
342
Chrome Fast Brown TV
A677
S
342
Chrome Fast Brown V
A679
By, I
394
Chrome Fast Brown 12684
A678
tM
304c
Chrome Fast Brown 15823
A680
tM
304c
Chrome Fast Cyanine G
A681
Chrysoidine
Var
33
Chrome Fast Garnet BL
A
U79
B
33
A682
Chrysoidine AR
tM
34
A683
Chrysoidine C 2 E
p
33
Chrome Fast Green 16394
A684
B
33
Chrome Fast Orange R . . . .
Chrome Fast Orange RD . . .
Chrome Fast Pure Blue BX
I
By
A685
U232
551
Chrysoidine GS
Chrysoidine 3 N
Chrysoidine R
tM
Var
33
33
34
Chrome Fast Red G
A
All
Chrysoidine R
C.DH
69
I
A686
Sch
34
Chrome Fast Yellow BN. . .
CG
177d
96a
Chrysoidine RD
Chrysoidine RE
CV
P
33
34
Chrome Fast Yellow 2 G. . .
Chrome Fast Yellow GG,
5 G .
A
I
96
96a
Chrysoidine RG
Chrysoidine RL, RLE .
Chrysoidine T base
B"
B
34
34
34a
Chrome Fast Yellow GA. O.
I
96a
Chrysoidine Y
Var
33
602
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Chrysoidine 2 Y
tM
33
Cloth Scarlet 2584
K
U327a
Chrysoidine 46803
Chrysoidine Base
A
K
33
33
Cloth Yellow R
Cocceine Orange
GrE
p
A458
227a
Chrysoidine crystals
Sch
33
Coccine 2 BG, 3 BG
A
167
Var
143
M
101
Chrysolarine A
tM
U526
Cochineal
p
81b
Chrysoline
G, S, P
586
Cochineal Red A
B
169
Chrysophenine
I S
304
Cochineal Scarlet B
WD
95
Chrysophenine G
Var
304
Cochineal Scarlet 4 R
Pch
78
Chrysophenine GOO
L
304
Coerulein B
M
600
Chrysophenine R, W
By
304a
Ccerulein I
B
601
Chrysophenine III
AW
304
Ccerulein MS powder
DH
601
Chrysophenine 190
K
304
Ccerulein S
B etc
601
Ciba Blue B
880
Coerulein SL powder
BD
601
Ciba Blue 2 B 2 BD
881
Ccerulein SW'
B Bv
601
Ciba Blue G, G 2 B
882
Columbia Black
A *
436
Ciba Bordeaux B
Ciba Gray B, G
9ir
899
Columbia Black B
Columbia Black EA
A
A
455
455 a
Ciba Green G
Ciba Heliotrope B
Cibanone Black B, BG, 2 G
Cibanone Blue 3 G
Cibanone Brown B, V
Cibanone Green G
891
897
794
793
868
792a
Columbia Black FF, FB , F 2 B
Columbia Black R
Columbia Black WA
Columbia Black Green D . . .
Columbia Blue G, GM
A
A
A
A
A
A
436
453
455a
465
387
325
Cibanone Olive B, G
Cibanone Orange R
792b
792
Columbia Bordeaux B
A
A
U80
A12
Cibanone Yellow R
Ciba Orange G
795
911
Columbia Brown R
Columbia Catechine 3 B . .
A
A
A13
U81
Ciba Pink R
Ciba Red R
910a
908
Columbia Catechine G
Columbia Catechine O
A
A
U82
U83
Ciba Red B
909
Columbia Catechine R
A
U84
Ciba Red G . .
906
Columbia Fast Black D. . . .
A
U86
Ciba Scarlet G
907
Columbia Fast Black FF. . .
A
U87
Ciba Violet B
901
Columbia Fast Black G . . . .
A
U88
Ciba Violet 3 B
900
Columbia Fast Black V ....
A
U89
Ciba Violet R
901
Columbia Fast Blue 2 G . . .
A
A16
Ciba Yellow G
890
Columbia Fast Blue R
A
A17
Cinnabar Scarlet BF
Cinnabar Scarlet G, R
Citronine GOO
BK
BK
L
299
300
141
Columbia Fast Red F. . . .
Columbia Fast Scarlet 4 B . .
A
A
A
343
279
478
Citronine GOOO, 2 ROOOO
Claret NY Z 1413
GrE
B
140
U118
Columbia Green B, 3 B, G .
Columbia Orange R
A
A
478
A14
Claret Lake BL
By
U238
Columbia Violet R ....
A
A15
Claret Red
B
U119
A
617
Claret Red
H
A757
I
U663
Claret Red B, BO
Claret Red SS
Claret Red X
M
B
M
112a
U120
112a
/oomassie Acid Blue R. . . .
Coomassie Black B
BD
lev
Lev
188
433
217
Clayton Cloth Red
CICo
193
Lev
434
Clayton Yellow
CICo
198
BD
252
Cloth Blue 1769, 1770
Cloth Fast Black B
K
U327
U659
Coomassie Union Blacks-. . .
Coomassie Wool Black D
Lev
Lev
461
266
Cloth Fast Blue B. . .
Cloth Fast Blue GTB
Cloth Fast Blue R
Cloth Fast Red R
Cloth Red B
By
693
U661
257
484
233
Coomassie Wool Black S . . .
Coomassie Wool Black R. . .
Concentrated Blue BB
Concentrated Cotton Blue
B 2
Lev
Lev
H
M
244
243
U752
539
Cloth Red B...
GiE, K
236
A
307
Cloth Red BB
K
A394
Congo 4 R
A
374
Cloth Red B, 2 B
WD
236
Congo Blue 2 B
Bv
412
Cloth Red 3 B
Cloth Red BA
? y
231
236
Dongo Blue 3 B
A
Var
391
477
Cloth Red BC . .
By
223a
A Lev
477
Cloth Red BO
GrE
236
Congo Brown R
A, Lev
490
Cloth Red G
By
224
Var
375
Cloth RedG...
By.GrE
234
Var
312
Cloth Red GA
234
A
456
Cloth Red 3 GA
Cloth Red GFL, GL
Cloth Red O
A
A
M
230
234
236
}ongo Fast Blue R
/ongo Magenta
Congo Magenta 3616. .
A
K
K
451
A395
A395
Cloth Red 1769, 2586
K
A394
Congo Orange G
Var
315
Cloth Scarlet C, G
K
246
Congo Orange R
A, L
373
Cloth Scarlet R . .
K
252
oneo Orange R. RG. . .
Bv
373
GLOSSARY OF DYE NAMES
603
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Congo Red
Var
Sch
By
Var
S
BK
CG
DH
DH
GrE
l y
B
B
S
WD
K
B
B
B
&v
K
B
K
S
B
B
K
Lev
B
WD
307
307
374
313
313
313
313
646
641
609e
606e
A69
A70
U121
462c
738
A396
A71
A72
A73
462c
462c
A396
463
A396
462c
A75
462h
A396
462 C
A74
538
649
538a
U328
U490
538a
U328
538a
U328
539
649
538a
649
538a
539
737
490
U329
490a
U122
490a
490a
U329
490a
U329
490a
U123
490a
U329
490a
312
A732
U330
U732
363
U331
U733
A714
U516
U332
U124
Lev
K
1
Lev
K
B, S
B
K
I
Lev
B
BK
A
B
B
tM
C
Lev
S
B
GrE
CG
B
Lev
B
K
Lev
Lev
?
B
B
B
GrE
GrE.M
GrE
GrE
L
L
By
AW
C
Sch
Sch
Var
Var
Sch
C
Sch
K
By, etc.
By
l y
By
By.K
WD
Sch
WD
K
K
H
H
H
H
H
H
U734
U333
210c
34d
210a
U333
192
210
U333
34c
210b
U125
300
Ul
366
363
307
307a
307a
365
363
307
307a
313
313a
227
U334
227b
227
U735
U796
U797
U798
U735
199b
304
296
296
199
U510
351
351
395
621
U517
163a
U569
225
226
235
37
37
70
37
37
169a
249
255
249a
255
167
167
A527
227
A528
251
251
720IE
S174
S175
S176
S177
S181
Congo Red 4 B
Congo Red 4 R
Congo Rubine
Cotton Orange
Cotton Orange
Cotton Orange
Cotton Orange (V. M.)
Cotton Orange FB, GK. . .
Congo Rubine G
Congo Rubine Z
Congo Rubine 8714
Coreine AR AB
Cotton Orange R
Cotton Orange RR, R 2 O .
Cotton Orange W&?
Cotton Orange Brown ( V . M .
Cotton Pink B
Coieine 2 R
Corioflavine G,GG,GOOO,R
Coriphosphine OS, OX
Corvan Black BG
Corvafi Black T
Corvoline BT
Cotton Pure Blue B
Cotton Black
Cotton Black
Cotton Black (V. M.)
Cotton Black 3 B
Cotton Black BGX
Cotton Black BNX
Cotton Red 65 A, 201 A. ..
Cotton Red B
Cotton Black BT ....
Cotton Red 4 B <
Cotton Red 4 B
Cotton Black CC, CT
Cotton Black CK
Cotton Black E
Uotton Red 8 BN
Cotton Black GB
Cotton Black GS, RS
Cotton Black PF
Cotton Scarlet
Cotton Scarlet
Cotton Black RW
Cotton Scarlet
Cotton Scarlet NP, NPX. ..
Cotton Violet 43 A
Cotton \ iolet 2 B
Cotton Black UG
Cotton Black V Y ...
Cotton Black 4 '
Cotton Blue
Cotton Violet 5 B
Cotton Blue
Cotton Violet R
Cotton Violet X
Cotton Blue (V. M.)
Cotton Blue B
Lev
K
CG
GrE
K
M
B
BK
wb
C
K
Lev
B
ev
K
S
K
Lev
B
I, S
K
Lev
B.GrE
Lev
K
Lev
B
K
Lev
S
L
K
B
Cotton Yellow
Cotton Blue BCB
Cotton Blue BCB
Cotton Yellow CH
Cotton Yellow G ...
Cotton Blue BR
Cotton Yellow GI, GX. ...
Cotton Yellow R
Cotton Blue BSJ
Cotton Blue CC
Cotton Blue G
Cresol Black (V. M.)
Cresotine Yellow G
Cresotine Yellow GOO . . .
Cresotine Yellow R
Cotton Blue N
Cotton Blue OOO
Cotton Blue R RN
Cresyl Blue BBS, RRN . . .
Cresyl Fast Violet 2 B . ...
Crimson BBT
Cotton Blue 5190
Cotton Blue Double cone. . .
Cotton Brown
>imson Benine G
Cotton Brown (V. M.)
Cotton Brown B
Cotton Brown B
Croceine B
Cotton Brown CNP
Cotton Brown CR
Croceine Orange
Cotton Brown FS
Cotton Brown 4 G
Cotton Brown O, 2 R
Cotton Brown 3 R
Uroceine Scarlet (V. M.) . . .
Croceine Scarlet 3 B
Cotton Brown RN
Croceine Scarlet 7 B, 8 B. . .
Croceine Scarlet 10 B
Croceine Scarlet 8 BL
Croceine Scarlet 2 BX
Croceine Scarlet 3 BX
Cotton Brown T
Cotton Brown V
Cotton Brown 100, 137, 153
Cotton Corinth G
Cotton Cutch 21 A
Cotton Dark Green B, N . . .
Cotton Dark Green 138 ....
Cotton Fast Red 4 BSP, 4 BX
Croceine Scarlet MOO
Croceine Scarlet MOO
Croceine Scarlet O
>oceine Scarlet OO
Cross Dye Black (V. M.). . .
Cross Dye Blue FR
Cotton Green A, 88 A,
105 A B
Cotton Green D
Cotton Green 2 G
>oss Dye Brown 2 D
>ross Dye Brown 4 R
Cotton Milling Black . .
Cross Dye Green G
604
GLOSSARY OF DYE NAMES
Name
Mami-
fac-
turer
Serial
No.
Name
Manu-
fac-
tuier
Serial
No.
Cross Dye Yellow D
H
H
H
Lev
Lev
Lev
..Lev
S178
S179
S180
444
445
341
178
38
38
113
113
U543
U286
516
516
516
516
516
83
A689
A687
A688
A690
A690
A690
140
140
140
142
142
9
16
A540
A426
A715
A691
U727
U728
U729
860
859
859
859
630
544
544
544a
U527
U664
546
566b
566
598
594
A19
537a
U736
U528
U2
622
366
366a
366
367
333d
333d
U570
333
U571
U572
U573
Developed Blue GG
AW
AW
AW
C
C
C
C
C
C
C
C
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
s
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
c
A
A
c
c
c
c
c
U574
U575
U576
A338
A339
A340
A341
A342
333b
333
403
473
328
402
384a
337
391
386
384
271
401
419
418
319a
A343
A344
A345
448
344
349
344
329
A346
A7J6
432
A347
A348
A349
A351
A352
A353
A354
A355
343
A357
A358
61 7a
296
431
431
241
474a
474
475
A360
A361
A362
A363
A364
A365
A366
A367
426
A371
A372
363a
366
367
119
121
319
319
424
Developed Brown M
Cross Dye Yellow Y
Crumpsall Direct Fast
Diamine Aldehyde Blue. . .
Diamine Aldehyde Scarlet.
Diamine Azo Blue
Diamine Azo Bordeaux B. .
Diamine Azo Scarlet (V.M.
Diamine Black (V. M.) . . .
Crumpsall Direct Fast
Crumpsall Direct Fast Red R
Crystal Orange 2 G
Var
B, etc.
A.BK
WD
C
Var
A"
B
I
Sch
I
I
I
I
I
I
A, BK
BK
A
tM.G
G
L
CICo
AW
M
S
CV
cv
cv
B
B
B
B
DH
A, M
A
CV
tM
I
C
C
c
I
M,K,S
A
Lev
Lev
tM
A
S, By
AW
Var
Lev
WD
2w
AW
AW
AW
AW
Diamine Black HW
Diamine Black RO . . .
Diamine Blue Black E. . . .
Diamine Blue (V. M.) ....
Diamine Blue 2 B
Crystal Violet 5 BO
Diamine Blue BX
rVvatnl Violet CV
Crystal Violet 484
Diamine Blue 3 R
Cupranil Brown R
Diamine Brilliant Blue G. . .
DiamineBrilliantBordeauxR
Diamine Brilliant Rubine. . .
Diamine Brilliant Scarlet. . .
Diamine Brilliant Violet
Diamine Bronze G
Diamine Brown (V. M.)
Cupranil Brown 12366 ....
Cupranil Brown 15596 ... .
Cupranil Brown 15903 ....
c/urcum* ne. . .
Diamine Brown V
Diamine Catechine (V.M.) .
Diamine Catechine G
i^urcupne i e. .
Diamine Dark Blue B
Diamine Dark Green N ... .
Diamine Fast Black (V.M.)
Diamine Fast Blue (V. M.).
Diamine Fast Bordeaux. . . .
Diamine Fast Brown (V.M.)
Cutch Brown R
Cyanthracene Blue 3 B ....
Cy anthracene Blue 2 BL. . .
Cyanthracene Yellow S . . . .
Cyanthrol EGA, G, 3 GO
Diamine Fast Orange (V.M.,
Diamine Fast Red F & , (V . M )
Diamine Fast Scarlet(V.M.)
Diamine Fast Violet (V.M.
Diamine Fast Yellow (V.M.
Diamine Fast Yellow 3 G .
Diamine Gold
Diamine Golden Yellow. . .
Cyananthrol RBA, RBX. . .
Cyananthrol RXO, RBY. . .
PvnnntrPTi RlilP 13623
Cyanol (V M )
Diamine Green (V. M.)
Pvnnnl Prppn (V M. )
a me oreen D . .
Diamine Heliotrope (V. M.)
Diamine Jet Black (V. M.) .
)iamine Neron (V.M.)
Cyanosine spirit soluble
Dark Navy Blue 2035
Dark Purple (printing paste)
Deep Black D
Deep Fat Black Color
Diamine Nitrazol Brown G .
)iamine Nitrazol Green
Mamine Nitrazol Orange. . .
)iamine Orange (V. M.) . . .
Deltapurpurin 3 B
)iamineral Blue (V. M.) . . .
Deltapurpurin 7 B
Diamine Red (V.M.)
Develop Black
Develop Black NZ
Developed Black B ...
Diamine Rose (V. M.)
Diamine Rose FFB
Diamine Scarlet (V. M.)... .
Diamine Scarlet HS ....
Developed Black BH
Developed Black N
Developed Black R
Developed Black W . .
Diamine Sky Blue FF . .
GLOSSARY OF DYE NAMES
605
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Diamine Sky Blue (V M.) . .
c
A368
Diazine Black 1401
K
IOK
Diarnine Violet N
c
327
Diazine Green S
K
Diamine Violet Red B
Diamine Yellow (V M )
C
c
A369
A370
Diazo Black B, OB, OT
Diazo Black R
By
Bv
308
OQO
Diamine Yellow CP
c
304
Diazo Black 10020
BK
QQQ
c
404
Diazo Black BHAD
S
000
c
274
Diazo Black BHN
By
000
Diaminogen Blue (V.M.) . . .
Diaminogen Blue BB, NA. .
c
c
273
273
Diazo Black BHN
Diazo Blue X
WB
Bv
333
A236
Diaminogen Sky Blue N . . .
c
A373
Diazo Blue Black RS
By
441
Diamond Black
Var
275
Diazo Bordeaux 7 B
By
A225
Diamond Black AF, CY,
Diazo Brilliant Black
364
EA ET
By
275
Diazo Brilliant Black B . . . .
By
364
Diamond Black F
B, L. Bv
275
Diazo Brilliant Orange GR .
Bv
A226
Diamond Black FB ....
B By
275
Diazo Brilliant Scarlet B . . .
By
A227
Bv
275
Diazo Brilliant Scarlet 3 B .
Bv
A228
Diamond Black GAF . . .
B
275
Diazo Brilliant Scarlet 6 B .
Bv
A232
Diamond Black P 2 B, PV,
PVT
By
157
Diazo Brilliant Scarlet 2 BL
Diazo Brilliant Scarlet 5 BL
By
Bv
A230
A231
Diamond Blue R
Diamond Blue Black EB . . .
By
By
Bv
164a
181
A222
Diazo Brilliant Scarlet BG .
Diazo Brilliant Scarlet G. . .
Diazo Brilliant Scarlet PR.
By
By
By
A229
A233
A234
Diamond Flavine G
By
102
276
Diazo Brilliant Scarlet PR. .
Diazo Brilliant Scarlet S 4 B
WD
Bv
A529
A235
jJiamona Lreen. . .
B
495
Bv
A237
Bv
276
By
A238
iJiamo id. Lireen . ..
B
495
By
A239
Diamond Green G GF, GN
B
499
Diazo Brown NR
By
A240
Bv
276
Diazo Brown 3 RB
By
A241
jJiamona ijreen o o
Bv
276
Bv
A242
Diamond Green special ....
"
276
U128
Diazo Fast Black BHX
Diazo Fast Black G
By
By
A243
A244
iJiamona iviage
B
U129
Diazo Fast Black MG
By
A245
Diamond Phosphine (V.M.)
Diamond Red BH
C
By
609b
A223
Diazo Fast Black SD
Diazo Fast Black V
By
By
A246
A247
By
A224
Diazo Fast Bordeaux BL. . .
By
A248
Diamond Violet BB .
AW
U577
Diazo Fast Green GE
By
A249
Diamond Yellow G
Bv
204
Diazo Fast Red 7 BL
By
A250
Dianil Black PR
M
491
Diazo Fast Violet BL
By
A251
M
479
Diazo Fast Violet 3 RL . . .
By
A252
M
380
Diazo Fast Yellow G
By
A253
Dianil Blue G
M
415
Diazo Fast Yellow 2 G
By
A254
M
323
Diazogene Black
AW
A541
Dianil Blue 2 R
M
379
Diazogene Black AB
AW
A542
M
A427
Diazogene Black AD
AW
A543
Dianil Garnet B
M
332
AW
A545
Dinnil Vpllnw 1 G
M
25
AW
A546
Diani] Yellow R
M
26
Diazogene Blue 2 R, 4585 . .
K
A397
Dinnil Ypllnw 2 R
M
27
AW
A547
M
408
AW
A548
Dinnol Rlark (V M )
Lev
436a
AW
A549
Dianol Black BH
436a
Diazo Indigo Blue BR
By
274a
Dianol Black E
Lev
436a
Diazo Indigo Blue 2 RL, 3 RL
By
274a
Diannl TVIar>V T?X
Lev
436a
CV
U730
Dianol Black RO RW
Lev
328
Diazo Olive G
By
A255
Dianol Blue 402
Lev
424a
Diazophenyl Black L
G
A613
Lev
424b
Diazophenyl Blue BC
G
A614
Lev
356a
Diazo Pure Blue 3 GL
By
A255a
Lev
356a
By
A256
Dianol Fast Red K
BD
279
Diazo Skv Blue 3 GL
By
A258
BD
343
Diazo Sky Blue B
By
A257
Lev
474
Diazurine B
By
406
L v
356b
Q
U799
Lev
356c
M
U431
BD
356
M
888
Dianol Red B
Lev
357
Dioxine
L
3
Lev
356
Diphene Blue B
A
695a
I
881
Diofapne Blue R
A
690
Diazanil BB
M
273
Diphenylamine Blue
DH
520
M
A428
Diphenyl Black
M
922
A429
Diphenvl Black L
G
A615
125
Diphenyl Black RC
G
A616
Diazine Black H . .
Sch
333
Diphenyl Blue 3 BC
G
A617
606
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Diphenyl Blue BEG
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
G
H
H
AW
A\V
K
g
I
By
CG
K
S
K
t y
K
P
l y
CV
K
I
S
H
K
K
A618
A620
A619
A621
334
348
348
393
348
347
449
206
617
18a
14
14
205
12
A633
A622
A623
A624
A625
A626
295
207
A627
343
A628
18
18
A629
467
468
A629
467
13a
13
358
358
A634
A635
U753
442a
A550
A551
U335
442a
U335
A692
A259
333a
U335
442a
U335
A260
442a
U335
442
A261
U335
442a
U335
A693
442a
428a
U336
U336
Direct Blue AB
Direct Blue B
?
1
BK
Q
K
AW
S
CG
K
I
I
WB
K
I
CV
I
H
By
Lev
I
L
K
K
L
428a
428
428a
379b
428a
U336
428a
428a
428a
428a
U336
397
428a
337
U336
428a
428a
428a
428a
455
455b
428b
A502
U337
U337
A503
457
A636
A504
486
344
A505
344a
U337
A717
A718
A694
A552
U338
U340
U339
A695
344
U341
478b
U342
A20
462a
462
U343
463
A696
A553
U344
U345
A262
U346
392c
343
343a
A698
U704
U347
279
U348
617c
617c
398
681
354
Dipbenyl Blue BTC
Diphenyl Blue BBFC
Diiect Blue 3 B
Direct Blue 5 B
Diphenyl Blue 2 R ....
Diphenyl Blue Black
Diphenyl Brown BBNC,
BGN
Direct Biue 5 B . .
Direct Blue 7 B, 12 B, BK,
FF
Dipbenyl Brown BN, BVCN
Diphenyl Brown 3 GN.
3 QNC
Direct Blue BX
Direct Blue C, G
Direct Blue 3 G
Diphenyl Brown GS
Direct Blue GN
'Direct Blue GRC, N 2 B, R,
5 R
Diiect Blue R ...
Diphenyl Brown TB . . .
Diphenyl Catechine G
Diphenyl Chlorine Yellow FF
Diphenyl Chlorine Yellow G,
Direct Blue RW
Direct Blue WBB
Direct Blue X 2 B
Diphenyl Chrysoine G, GC.
Dipbenyl Chrysoine 3 GN,
Direct Blue 30
Direct Blue 7079
Direct Blue 13108, 13503. . .
Direct Blue 51096
Diphenyl Chrysoine RR
Direct Blue Black B
Diphenyl Dark Green BC . .
Diphenyl Deep Black GC . .
Diphenyl Deep Black GN . .
Diphenyl Deep Black GWC
Diphenyl Deep Black VN . .
Diphenvl Deep Black VP...
Diphenyl Fast Black
Direct Blue Black 313
Direct Brilliant Blue 8 B . . .
Direct Brown
Direct Brown (V. M.)
Direct Brown B, H
Direct Brown 2 G ...
Diphenyl Fast Brown G,
Direct Brown 3 GNC
Direct Brown HB ....
G
L
I
I
L
I
S
S
AW
K
K
K
I
L
K
I
K
A
By
r
? y
AW
K
K
i
i
i
s
K
I
K
tM
GrE
I
P
I
Diphenyl Fast Gray BC. . . .
Diphenyl Fast Red
Direct Brown J, JJB, JP. . .
Diphenyl Fast Violet BC. . .
Diphenyl Fast Yellow extra
Diphenyl Fast Yellow G . . .
Diphenyl Green BC
Direct Brown N
Direct Brown RW
Direct Brown TB
Direct Catechine G
Diphenyl Green G
Direct Catechine 30
Diphenyl Green 3 G
Direct Chrome Black 14722
Direct Chrome Brown
Direct Cotton Blue GS, RDB
Direct Cotton Gray
Diphenyl Green 3 GC, 3 GF
Diphenyl Green KGW
Diphenyl Orange GG
Diphenyl Orange RR
Direct Cotton G.een 2 B. . .
Direct Cutch GG ....
DiphenylRedSB.SC...
Diphenyl Red 184, 340. . .
Diphenyl Scarlet 3 B
Diphenyl Violet BVC. . . .
Disulphine Blue 47073 DS
Direct Black (V. M.)
Direct Blac. ABC
Direct Black C
Direct Dark Brown M
Direct Dark Green
Direct Dark Green S
Direct Dark Violet BE
Direct Deep Black E
Direct Deep Black E
Direct Deep Black EW
Direct Deep Black NTS
Direct Deep Black RW
Direct Fast Black B
Direct Black D
Direct Black D
Direct Black DB ...
Direct Black E
Direct Black FBS ....
Direct Fast Blue FFB
Direct Fast Brown C, GB. .
Direct Fast Brown GG
Direct Fast Gray RN
Direct Fast Orange 16710. .
Direct Fast Red F
Direct Fast Red 17727, 25420
Direct Fast Scarlet (V. M.) .
Direct Fast Scarlet 4 BS . . .
Direct Fast Scarlet 4 BS,
8 BS
Direct Black FBS
Direct Black G
Direct Black '} G
Diiect Black 3 R
Direct Black RC
Direct Black RO
Direct Black T
Direct Black V
Direct Black VT
DirectBlack WC, 3899, 3919
Direct Black 7565
Direct Black 8535
Direct Black 14714
Direct Fast Scarlet SE
Direct Fast Violet 3654
Direct Fast Yellow
Direct Black 33336
Direct Fast Yellow OO, R. .
Direct Gray B
Direct Bme. .
Direct Blue (V. M.)
Direct Blue A
Direct Gray B J
Direct Gray R..
GLOSSARY OF DYE NAMES
607
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
I
CG
1,8
CG
CG
S
I
CG
8r
OU
b
I
I
I
B
K
K
S
I
G
I
K
L
BK
CG
K
i.s
DH
S
K
I
I
S
BK
I
WB
S
S
I
H"
I
CG
?
s
K
CG
I
K
A
K
S
H
I
GrE
Sch
K
L
K
GrE
G
K
By.GrE
GrE
Sch
AW
478a
A444
478a
A445
A446
475
478a
A447
478a
A448
478a
439
440
353
443
U349
U349
392b
392
lib
362
lla
A506
392b
392b
U491
U350
307b
307b
307b
U351
307b
A699
U800
U705
U706
U480
A700
426
A719
A720
A700
424
413a
413
A449
352
352
413a
A398
A450
413a
9b
9g
9b
9e
9h
304b
A459
9
9b
304b
9b
9f
A460
9d
9h
9b
9
A461
9
617b
9o
Direct Yellow WH
WB
CICo
L
L
L
L
L
L
L
tM.etc.
%
1
A,Lev
AW
AW
AW
AW
AW
AW
K
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
AW
M
AW
AW
342
9h
9
304b
A507
A508
A509
A509a
A510
216
61
174
108
A263
A264
247
176
A554
A555
A556
A557
A558
A559
U352
A560
A562
A563
A561
A564
A565
A566
A567
A568
A569
A570
A571
A572
A573
A574
A575
A576
A577
A578
A579
A580
A581
A582
A583
A584
A585
A586
A587
A589
A590
A591
A592
A593
A594
A595
A596
A597
U433
A599
A598
842
838
849
881
882
883
912
917
Direct Green B
Direct Yellow Z
Direct Yellow 242
Direct Green C
Direct Yellow 19305
Domingo Alizarin Black EF
Domingo Alizarin Black G. .
Domingo Alizarin Blue R. . .
Domingo Alizarin Bordeaux
Domingo Black 46216
Domingo Blue Black B
Domingo Violet A
Double Brilliant Scarlet G. .
Direct Green G
Direct Green G
Direct Green 3 GG Y ...
Direct Green KGD
Direct Green U
Direct Green 10865 .
Direct Green 9753, 34267.. .
Direct Indigo Blue BK
Direct Indigo Blue BN
Direct Indone Blue R
Direct Navy Blue
Double Ponceau 2 R
Double Ponceau 4 R
Double Scarlet
Direct Navy Blue B
Double Scarlet extra S
Drazaline Alizarin
Drazaline Black BH
Direct Orange BR, G
Drazaline Blue 10 B ...
Direct Orange R
Drazaline Blue 2 BFL
Drazaline Blue CV
Drazaline Blue F
Direct Orange 1901
Drazaline Blue FF
Drazaline Blue FS
Direct Pure Blu?
Drazaline Blue RFL
Direct Purple N
Direct Red
Drazaline Blue VVV
Drazaline Blue Black HWF
Drazaline Bordeaux 6 B
Drazaline Brilliant Yellow. .
Drazaline Brown C 3 B . . . .
Direct Red B
Direct Red 3 B
Direct Red N
Direct Red 215 1725
Drazaline Brown G
Drazaline Brown 3 GL
Drazaline Brown 4 J
Drazaline Brown R
Direct Scarlet B
Direct Scarlet FB
Drazaline Chlorine Yellow G
Drazaline Diamond Violet
BB
Direct Sky Blue
Direct mcv "Rlno R
Direct Sky Blue FF
Drazaline Fast Blue 4 GFL.
Drazaline Fast Gray
Direct Skv Blue 22
Drazaline Fast Red
Direct Sky Blue, greenish . .
Direct Violet B
Drazaline Fast Red F
Drazaline Fast Yellow B . . .
Drazaline Garnet BB
Drazaline Garnet FL
Direct Violet R
Direct Violet R
Direct Violet R
Drazaline Indigo Blue
Direct Violet RR
Direct Violet 3653, 4561. . . .
Drazaline New Red 10 B. . .
Drazaline Orange FL
Direct Violet, 12932, 18510.
Direct Yellow (V M ^
Drazaline Orange G
Dirpct Vpllnw "R
Drazaline Red F
Direct Yellow BK
Drazaline Red FL
Direct Yellow C
Drazaline Red FV
Direct Yellow CR
Drazaline Sky Blue FF
Drazaline Violet D ....
Direct Yellow EGOO
Direct Yellow F
Direct Yellow G, GBE, GR
Direct Yellow G
Drazaline Violet NFL
Drazaline Violet VB
Drazaline Yellow R
Direct Ypllrvw 2 fl
Drazaline Yellow R
Direct Yellow 6 G
Drazaline Yellow S
Drazaiine Yellow T
Direct Yellow GOO
Direct Yellow MC
Duranthrene Blue CC
Duranthrene Blue RS
Direct Yellow PC
Direct Yellow PI
Duranthrene Yellow
BD
BD
BD
BD
BD
Direct Yellow R
Direct Yellow 2 RF
Direct Yellow TO
Durindone Blue 6 B
Durindone Red B
Direct Yellow V
Durindone Red N
608
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Durindone Scarlet R
Dutch Yellow
BD
FA
905
103
Eriochrome Green H
G
G
U615
U616
Eboli Blue B ...
L
389
G
U617
Eboli Green
L
466
G
U618
Eclipse Black C
G
720G
Eriochrome Olive G
G
U619
Eclipse Brown B
G
S141
G
133
Eclipse Brown GC . ...
G
S142
Eriochrome Red AW B
G
29
Eclipse Brown R
Eclipse Fast Brown BC . . .
G
G
S143
S144
Eriochrome Verdon A, S . .
G
G
260
A643
Eclipse Fast Brown GC . . .
Eclipse Fast Brown 3 GC .
Eclipse Fast Brown 4 R. . .
Eclipse Fast Dark Brown BC
Eclipse Fast Red Brown . .
Eclipse Fast Red Brown E
Eclipse Phosphine GGC. . .
Eclipse Phosphine RRC. . .
G
G
G
G
G
G
G
G
S145
S146
S147
S148
S149
S150
S151
S152
Eriochrome Violet 2 BL. . .
Eriochrome Yellow 2 G
Eriochrome Yellow 3 G . .
Eriochrome Yellow GR ...
Eriochrome Yellow S . .
Eriocyanine A, AC, R. .
Erio Fast Blue SWR
Erioflavine SX
G
G
G
G
G
G
G
G
A644
A645
A646
A647
A648
531
A637
19
Eclipse Yellow G
G
S153
Eriofloxine 6 B
G
66
Eclipse Yellow 3 G
G
S154
Eriofloxine 2 G
G
42
A
123
G
506
A
100
Erioglaucine A AP EP X
G
CLOfi
Var
587
H
506
Eosine (V M)
Var
587
G
564
B Bv
587a
G
564
Eosine AG
B
587n
G
K4
Eosine AG A 3 G, BB. . . .
M
587
G
A649
Eosine BN BNL ....
B
590
Erio Violet BC
G
U610
Eosine CA W
B
587a
Erio Violet RLC
G
U611
Eosine S SP
B
589
G
503
Eosine Spirit Soluble
tM
588
Erweco Alizarin Acid Blue R
RWCo
857
Eosine (yellowish) 701
Era Black J
G
Lev
587
275
Erweco Alizarin Acid Red BS
Erythrine 7 B
RWCo
B
781
255
Ergane Yellow G
B
U130
Q
A3 74
Ergane Yellow R
B
U131
B
228
Ergane Yellow W
B
U132
B
249
B
U133
M
592
B
U134
M
592
B
U135
M etc
592
B
U136
B L
591
Erica B
A, etc
121
Ethyl Acid Blue RR
B
63
Erica BB
S
121
Ethyl Acid Violet S 4 BXX.
B
61
Erica BN
A
121
Ethyl Blue B
B
A 76
A Lev
122
B etc
518
Erica G
s
122a
Ethyl Violet
B G
518
Erica GN
A
122
Ethyl Violet
M I
518
Erica 2 GN
A
117
Ethyl Violet 8682
I
518
Erie Direct Black G, GX. . .
Sch
462
Euchrysine (V M )
B
608
Erie Direct Black R
Erie Direct Black RX
Sch
Sch
463
463
Euchrysine RR, GG, GNX,
GRNT
B
608
Erie Direct Brown GB
Erie Direct Brown GR
Erie Direct Brown 3 RB. . .
Sch
Sch
Sch
477a
477
344
Euchrysine NX, RT, RRD.
Euchrysine 3R, 3 RX
B
B
AW
608
603
A600
Erie Direct Brown RF, 2 RF
Erie Direct Green ET
Erie Direct Green MT
Sch
Sch
Sch
488
464
474
Excelsior Lake Scarlet (V.M.)
Excelsior Scarlet G
Excelsior Scarlet 3 R
C
M
M
A375
U434
U435
Erie Direct Green WT
Sch
464
Export Blue 1504 . . .
B
U137
Erie Orange 2 R
Sch
311
562
Erioazurine BC
G
A638
Fast Acid Blue B
Bv
562
Eriocarmine 2 BC
G
A639
Fast Acid Blue 3 B
562d
Eriochromal Brown EB ....
G
U612
Fast Acid Blue R
M
584
Eriochromal Gray 5 G
G
U613
Fast Acid Blue RH . ...
H
584a
Eriocbrome Azurol B, BC . .
G
G
551
554
? ast Acid Eosine G
M
Bv
581
41
Eriocbrome Black A
G
184
Fast Acid Green RH
H
503a
Eriochrome Black T
G
183
Fast Acid Magenta G
M
581a
Eriochrome Blue BlackB.BC
Eriochrome Blue Black G .
G
G
180
180a
Fast Acid Marine Blue
HBBX
B
U138
Eriochrome Blue Black R . .
Eriochrome Brown RC
G
G
G
181
A640
A641
Fast Acid Navy Blue GRI. .
?ast Acid Phloxine A
Fast Acid Red A
I
M
M
U665
581
581b
Eriochrome Brown V
G
G
A642
553
Fast Acid Red EB, EGG. . .
Fast Acid Red RH
L
H
67a
67a
Eriochrome Geranol R . .
G
U614
Fast Acid Violet , ,
AW.C
580a
GLOSSARY OF DYE NAMES
609
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Fast Acid Violet
582
Fast Mordant Yellow
Var
2Q4.
Fast Acid Violet A 2 R
Fast Acid Violet B ....
M
By
582
562
Fast Mordant Yellow G
Fast Navy Blue
B
K
294
fi4Q
Fast Acid Violet B
M
580
Fast Navy Blue A
GrE
649
Fast Acid Violet 3 B
K
U353
Fast Navy Blue BNNOO,
Fast Acid Violet 10 B
Bv
528
RZOO . .
GrF
64Q
Fast Acid Violet ERR
Fast Acid Violet R ...
B
K
U139
U353
Fast Neutral Violet B
c
I
678
35
Fast Acid Violet R RBE
M
580a
M
148
Fast Acid Violet RGE ....
M
582
Fast Paper Yellow G
CG
U492
Fast Acid Violet RX
H
580a
Fast Parme
AW
U580
Fast Acid Violet 416
K
U353
Fast Pink BN GN
I
604.
Fast Acid Yellow (V M ) .
c
23a
Fast Pink for silk
DH
694
Fast Acid Yellow RBE
M
U436
Bv
A265
Fast Acid Yellow RH
H
137a
Fast Printing Green
K
2
Fast Black
G
U622
Fast Printing Yellow R . . . .
Bv
U240
Fast Black ....
L
658
Fast Red A
Var
161
Fast Black B
B
740
Fast Red A
B
A77
Fast Black BS ....
B
741
Fast Red
Var
168
Fast Black N
B
160
Fast Red
Var
161
Fast Blue
tM
699
Fast Red A
WB
166
Fast Blue AOOOO
GrE
699b
Fast Red ANSX
B
A78
Fast Blue B
A.
697
Fast Red AV
B By
161
Fast Blue B
AW
699
Fast Red B
B etc
112
Fast Blue BB
G
U623
Fast Red BN
B
112
Fast Blue 3 BB ....
GrE
699b
Fast Red BT
Bv etc
111
Fast Blue O
M
699
Fast Red CJ
B
163
Fast Blue R
B K
699
Fast Red E
Var
166
Fast Blue RD
A
649
B
A79
Fast Blue Z
G
U624
Fast Red NS
By
168
Fast Blue 62105
A
649
Fast Red G
M
161
BK
236a
Fast Red S
Sch
161
Fast Bordeaux G
BK
236a
Fast Red VR
WD
164
U545
6B
GrE
66c
Fast Sailor Blue A, R
AW
649
Fast Biiliiant Black 12349
j
U666
B
U141
j^
172
Fast Scarlet B
K
248
Bv
213
Fast Scarlet BX
B
U142
j^
172
Fast Scarlet BXG
B
U143
Fast Brown G
A
212
Fast Straw Yellow V
AW
A601
Fast Brown GS
Fast Brown N
G
B
U625
160
Fast Sulf on Black
Fast Sulf on Black F
B"
264
264
Fast Brown O
M
214
Fast Sulf on Violet 5 BS. .
S
182
Fast Chrome Black.
Fast Chrome Black
AW
jj
U578
275a
Fast Sulf on Violet 4 R . . .
Fast Toluylene Red
S
GrE
182
358a
Fast Chrome Black K
BK
U481
Fast Victoria Violet S 4 B .
GrE
61d
O
U801
Fast Violet R
AW
A602
L
U518
AW
U581
wn
TT ^4.4.
Fast Wool ^carlet 4 R
BK
U482
Fast Direct Yellow 22090
g
304b
Fast Yellow
Var
137
B
590b
Fast Yellow FY
Lev
137
AW
U579
Fast Yellow GR
tM
137
GrE
681
Fast Yellow N
p
150
"Fflqt Prav PPR
PG
681
K.BK
149
tM
U529
C
137
Rv
523
Fast Yellow Y
B
149
Fast Green bluish . . S
%
523
U582
Fast Yellow 95
Fast Violet
Q
137
626
AW
TJ583
Flavazine E 3 GL
M
20a
AW
U584
M
19
AW
U585
M
20
AW
U586
M
20a
D-.
TTOQQ
B
668
Fast I ight Green ....
lv
523a
Flavophosphine G, 4 G, R. .
M
609d
TW
38
785
"Ffl.<*t Ticrht Vpllnw O 2 O
rsy
Var
585
3G, GGN
B y
19
U140
Formyl Violet (V.M.)
C
P
53C
U595
B V
19a
Q
U802
Fast Mordant Black FH . .
M
T PV
275
U737
French Red
P, etc.
Var
U593
512
M
A430
P
512
Paat A/Trvrrlont TUl1< "R
M
A431
Fuchsine B
tM
512
610
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
GrE
tM
Sch
B
Sch
I
By
By
512
512
513
524
512
250 a
U241
U242
923
923
637
639
645
U626
599
599
599
626
626
626
626
628
772
629
6f>8a
U243
U244
641
2
118
512
U4
659b
501
U245
310
309
288
145
698a
U357
495a
U5S7
U354
495a
U144
U707
U803
495a
U356
495
495
495
U356
495
U356
U355
U355
U507
539
U5
U6
U7
U8
U9
U10
A22
A 23
Ull
U12
U13
503
Guinea Fast Green 3 B . . .
Guinea Fast Green 2 G . . .
Guinea Fast Red BL
A
A
A
A
A
A
A
Var
A
A
A
Var
A
A
I'
L
M
M
M
M
M
M
C
GrE
A
GrE
C
B
G
G
G
G
G
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
M
Iff
M
M
M
M
By
By
By
By
By
By
U15
U16
U17
U18
U19
U20
U21
502
502
505
A24
530
530o
530
U246
U519
U520
U437
U438
U439
28
U441
U442
A376
U508
U23
U508
U287
138
141
436
436
424
A453
921
880
896
896ft
904a
873
904*
904
836
902
903
907
915
921
892
921*
914
835
913
910
910
917
91S
916
920
920
898
920
810a
810
810
810a
A266
858
73
73
A268
A269
Fuchsine NB
Fuchsine S
Guinea Fast Red 4 BL. . . .
Fuchsine TR
Fulling Orange 16700
Guinea Fast Violet AL. . . .
Guinea Fast Violet 10 B. . .
Fur Black DM
Fur Gray 27953
H By
DH
G
By,etc.
B
Var
B
I
B
DH
B
DH
By
Iy
Gallanilic Violet R, B
Guinea Violet 4 B. 6 B
Guinea Violet S 4 B
Gallazol Blue 4 G
Galleine .
Half "W ool Blue 3 R
Half Wool Green 63816 . . .
Half Wool Green 63816 N
Galleine SR, SW, W
Gallocyanine D
Hansa Rubine G
Galloflavine W
Gailo Green DH
Hat Blank (V TVT ">
Hat Black A 4 AN
Gallo Violet D
Hat Black B*
Gallo Violet DF
lat Black L S
H
^ y
A
G
By
Ki
Ki
A
f y
K
H
AW
K
H
B
B
S
8
K
tM
H
tM
K
H
K
K
K
GrE
M
A
A
A
A
A
A
A
A
A
A
A
A
Helianthine G, GG, GFF, R
Heligoland Black BH
Heligoland Black FFNX . . .
(Gloria "Rlnrk N
Helindone Black RRG
lelindone Blue 3 GN
Helindone Blu6 3 R
Golden Brown
Gray NO
lelindone Brown AN
Gray Blue 0095
lelindone Brown G
lelindone Brown 3 GN ....
lelindone Brown 2 R
lelindone Brown 5 R
Helindone Fast Scarlet C. . .
Helindone Fast Scarlet R, RC
lelindone Gray 2 B, BR. . .
Green BX
Green HD
Green PLX
Green VGW
Green 21
Orppn 241
Green 15825
Helindone Printing Black
2 RQ
[elindone Orange D
[elindone Orange GRN. . . .
Helindone Pink AN, BN . . .
Helindone Red 3 B
Green residue D
Grela Red R
Guernsey Blue O
Helindone Violet B, BB
Guinea Bordeaux B
Guinea Bordeaux 6 B
Helindone Violet R
Helindone Yellow CG
Helindone Yellow GG vat . .
Helindone Yellow 3 GN
elindone Yellow RN
elio Bordeaux BL
elio Fast Blue BL
Helio Fast Red
Guinea Brown R
Guinea Brown 2 R
Guinea Carmine B
Guinea Carmine D
Guinea Cyanine LB
Guinea Cyanine LG
Guinea Cyanine LR
Guinea Fast Green B . .
elio Fast Red RL, TRL . .
elio Fast Ruberine RL
elio Fast Violet AL . .
GLOSSARY OF DYE NAMES
611
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Helio Fast Yellow 8 GL ,
Bv
A270
Indanthrene NN ....
B
873a
Helio Red RM
By
A271
B
768a
Helio Red RMT
By
A272
Indanthrene Black B, BB. .
B
768a
Heliotrope 2 B
A L By
321
Indanthrene Blue 3 G
B
840
Hessian Brilliant Purple ....
Hessian Brown BBN
L
L
302
489
Indanthrene Blue GC
Indanthrene Blue GCD
B
B
843
842
Hessian Fast Red F
L
343
Indanthrene Blue GGS
Hessian Purple N ...
By L
301
GGSL
B
841
305
Indanthrene Blue GG SP
B
841
Hoffmans Violet
p
514
Indanthrene Blue 3 GP ....
B
840
L
609
Indanthrene Blue R ...
B
837
L
609
Indanthrene Blue RS
B
838
Hydranthrene Brilliant Cop-
per D
813
Indanthrene Blue WB
Indanthrene Blue WR
B
B
850
850a
Hydranthrene Dark Blue. . .
Hydranthrene Olive R .
Hydranthrene Yellow AG,
AR
'.'.'.
763
791
849
Indanthrene Blue Green B. .
Indanthrene Bordeaux B. . .
Indanthrene Bordeaux B
B
B
B
765a
828
827
Hydrazine Yellow OO
GrE
A462
B
867
Hydrazine Yellow SO
Hydrazol Black
GrE
AW
A463
AG03
Indanthrene Brown B
Indanthrene Claret B
B
B
867
828
Hydrazol Black R
Hydrazol Chrome Black CB
Hydrazol Chrome Black DB
Hydron Blue (V. M.)
Hydron Blue G R
AW
AW
AW
C
A604
A 605
A606
748
748
Indanthrene Claret B extra.
Indanthrene Copper R
Indanthrene Dark Blue BD
Indanthrene Dark Blue BO
Indanthrene Dark Blue BT
B
B
B
B
B
827
813
763
763
846
Hydron Brown (V. M.)
Hydron Olive G
C
c
748a
748b
Indanthrene Fast Blue RR.
Indanthrene Gold Orange G
B
B
837a
760
Hydron Violet
Hydron Yellow G
c
c
748c
748d
Indanthrene Gold Orange B
Indanthrere Gold Orange RS
B
B
761
761
Hylidine Ponceau 2 R
G
tM
U627
U532
Indanthrene Gold Orange
2 RT
B
761
Immedial Black (V. M.) . . . .
Immedial Blue (V. M.)
Immedial Bordeaux G
C
C
C
724
724a
739
720
Indanthrene Gray B, BP . . .
Indanthrene Green B
Indanthiene Maroon R. . . .
B
B
B
B
848
765
845
791
Immedial Brilliant Carbon
F FG
(2
720
Indanthrene Orange RT
B
B
812
873b
p
S69
Indanthrene Red BN
B
831
Immedial Brown (V. M.) . . .
Immprliil rVrhnn (V M 1
c
/-
725
720
Indanthrene Red G
Indanthrene Red R
B
B
826
830
c
S70
Indanthrene Red Brown R.
B
873c
Immedial Cutch (V. M.) . . .
Immedial Dark Brown
(V. M )
c
c
S71
725
Indanthrene Red Violet RRN
Indanthrene Scarlet G, GS .
Indanthrene Violet B
B
B
B
873d
762
768
Immedial Dark Green B . . .
Immedial Deep Green G . . .
Immedial Direct Blue(V.M.)
Immedial Green (V. M.) . . .
Immedial Green Blue
c
c
c
c
c
c
S73
S74
S75
746
746
S76
Indanthrene Violet R
Indanthrene Violet RN . . .
Indanthrene Violet RR. . .
Indanthrene Violet RT . . .
Indanthiene Violet Yellow
G P
B
B
B
B
B
766
832
767
764
849a
Immedial Indone (V. M.)...
c
c
733
733a
Indanthrene Yellow G, GP.
B
C
849
689
Q
S77
414
immeaiai JxnaKi
c
739
429
S78
427
S7Q
430
p
711
396
S80
Indazurine TS
399
Q
728
India Rose 17285
U667
S81
Indian Red
G
U628
Immedial Yellow (V. M.). . .
c
710
Indian Yellow (V.M.)
Indian Yellow G GN
C
By
141b
141
(V. M.)
c
S82
Indian Yellow R
By
140
Imperial Green GI
By
A273
247
Indigene R
Indigene Blue BB
w
I
A701
Bv
7b
I
A702
DH
633
Var
874
DH
634
Var
874
CG
704
Indigo powder
Var
874
Indamine 6 R
CG
M
705
696
ndigo solution
Indigo FBP
M
y
874
874
B
837
Ind go G
B
888
612
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Indigo 7 G
Bv
874
Janus Yellow
\a
Indigo KB paste
K
881
Janus Yellow G
M
222
Indigo KG
K
883
Japan Black
B
U145
Indigo MLB
M
874
Japan Black B
B
U146
Indigo MLB 2 B
M
880
B
U148
Indigo MLB 4 B ....
M
881
Japan Black MBG
B
U149
Indigo MLB 5 B
M
882
Japan Black MF
B
U150
Indigo MLB 6 B
M
883
Jasmine
G
U629
Indigo MLBR, MLBRR. . .
M
879
Jasmine high cone
G
140
Indigo MLBT
M
888
Jaune M6tanile Brom6
p
135
Indigo MLB Vat I
M
876
Jet Black APX
B
U151
Indigo NC
Bv
874
Jet Black R
Bv
262
Indigo RB
B
880
Jet Black RR
B
U152
Indigo T
888
Jute Black B
By
U153
Indigo Acid Blue A
545
Jute Black I
tM
U533
Indigo Blue N
874
Jute Black RNT
B
U153
Indigo Blue 275
CJ
874
Jute Coal Black S
Bv
U154
Indigo Carmine Blue BG. . .
Indigo Extract A, AN 4
Indigo Salt T
A
B
K
U23
877
875
Katigene Black (V. M.) . . . .
Katigene Black Brown BW.
Katigene Black Brown GN.
1
Bv
720
S39
S40
Indigo Yellow 3 G
Indigo White
I
B
889
876
Katigene Black Brown R. . .
Katigene Blue Black 4 BPA
By
Bv
S41
720
Indigotine ....
Var
877
Katieene Brilliant Black B,
Indigotine P
B
878
FG
Bv
720
Indigotine 500 ....
A
877
Katigene Brilliant Green 3 G
By
843
Indo Carbon
c
748
Katigene Brown 2 R
By
S45
667
By
S46
Indochromine RR, T
Indochromine Black EXD . .
s
g
667
667a
Katigene Chrome Blue 5 G .
U
S47
S48
666
Katigene Deep Black B
Bv
720
Indocyanine B, 2 RF
A
G
705a
699 c
Katigene Direct Blue B . . . .
Katigene Direct Blue RF
By
Bv
S49
S50
Indoine
WD
126
Bv
746
Sch
126
Katigene Green 2 B 4 B,
Indoine Blue R
B
126
2 G MK
Bv
746
DH
619
Bv
S51
Indo Violet BF
A
U24
By
S52
Induline
Var
699
Bv
S53
Induline
Var
697
Katigene Indigo 3 GT ....
By
S54
Induline B
Bv
699
Katigene Khaki G
Bv
S55
Induline 2 B
CJ
699
Katigene Olive GN ....
By
S56
Induline BA ....
p
697
Bv
S57
Induline DB N
tM
699
Katigene Red Brown R . . . .
B
S58
Induline NN
B
699
Katigene Red Brown 3 R. .
Bv
S59
Induline NBL
Bv
699
Katigene Violet B
By
S60
Induline RN
K
699
Katigene Violet 3 R ...
By
S61
Induline S
j
697
Kati<*ene Yellow G
Bv
S62
Induline WLX
B
699
Katigene Yellow GG ....
By
S63
Induline 1768, 1778
K
699
Katigene bellow GR
By
S64
Induline 10350 ....
I
697
Katigene Yellow Brown GG
By
S65
Induline 38724 38725
jj
699
Katigene Yellow Brown GR
Bv
S66
Induline Black'base 5789 . . .
Induline Red (V M )
K
j
700
699 a
Katigene Yellow Brown 9 R
Katigene Yellow Brown RL
&
S67
S68
Induline Scarlet (Iris Blue)
B
671
Ketone Blue 4 BN ....
M
547
Induline Spirit Soluble
Var
697
Ketone Fast Violet 10 B
I
528
Induline Water Soluble ....
Var
699
Kiton Blue N
I
U668
Ingrain Black
H
A759
Kiton Blue V ...
I
543
Ingrain Black 4 B
H
A758
Kiton Fast Green V
I
564
Ink Blue BJTBNOO
GrE
U509
Kiton Fast Orange G ...
I
U669
Ink Blue BJTNO
GrE
U509
Kiton Red 6 B
I
U672
Ink Blue BNOO
GrE
U509
Kiton Red G
I
U673
Intensive Blue B
Iris Blue
? y
562
648
Kiton Fast Violet 10 B
Kiton Violet 12 B
I
I
528
U674
Irisamine
c
576
Kiton Fast Yellow 3 G
I
U670
Irisamine G
c
576
Kiton Fast Yellow R
I
U671
Irisamine G ex ...
g
576
Kiton Yellow G
I
U675
Isamine Blue (V. M.)
c
U288
Kiton Yellow GG
I
U676
Isodiphenyl Black R
G
437
Kraft Brown L
B
U155
Isopurpurin
784
Kraft Brown basic YZ
B
U155
Italian Green
709
Kryogene Black BNX
B
755
Janus Brown B
M
435
Kryogene Black TBO TG
B
720
Janus Gray B
M
128
Kryogene Black TGE, TGO
B
720
Janus Red B...
M
240
Krvoeene Black TGO. . .
B
756
GLOSSARY OF DYE NAMES
613
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Kryogene Blue BNO
B
753
Lemon Yellow R
J
Tjocrj
Kryogene Brown A
Kryogene Brown A, G . . . .
B
B
743
750
Leuco-Gallo Thionine DH . .
Leucol Dark Green B. .
DH
Bv
664
86fi
Kryogene Brown GX
B
750
Leucol Brown B
B?
872
Kryogene Brown R B
Light Blue
tM
KOI
RBNXX
B
751
Light Blue G
tM
KOQ
Kryogene Brown RXX . . .
Kryogene Direct Blue B .
B
B
75la
753
I ight Blue Superfine Spirit
Soluble . .
M
520
Kryogene Direct Blue 3 B. .
Kryogene Direct Blue
BNAGX
B
B
754
753
Light Green A ex cone
Light Green 2 A
Light Green 2 G cone
tM
tM
B
503
518
505
Kryogene Direct Blue G, GO
B
752
Light Green SF
B
504
Kryogene Green GX
B
754a
Lio'ht Green SF . ...
B
505
Kryogene Pure Blue R
B
729
Light Green SF Bluish
B
504
Kryogene Red Brown GRXX
Kryogene Violet 3 RX . . .
B
B
751b
754b
Light Green SF Yellowish. .
Light Green SF Yellowish
B
505
505
Kryogene Yellow
712
Light Green SL
505
Kryogene Yellow G GG . . .
B
712
Light Green Yellowish . .
505
Kryogene Yellow R
B
716
Lilac PC
DH
U599
Lacquer Black R
A.
U25
Lilac PC
G
U631
Lake Black C
C
U289
Liquid Oil Black N
tM
U536
Lake Black P
G
U630
H
566
Lake Blue ABII
M
U443
Lithol Claret B ...
B
A80
Lake Blue ABOII
M
U444
Lithol Fast Orange R
B
A82
Lake Blue AV
M
U445
Lithol Fast Scarlet B, G, RN
B
73a
Lake Blue AVO
M
U446
Lithol Fast Scarlet R
B
73
Lake Blue I
B
U156
Lithol Red 3 B, GG, 3 G. . .
B
173a
Lake Blue RT
BK
U483
Lithol Red R
B
173
Lake Bordeaux B
M
179
Lithol Red RG RS
B
173a
Lake Purple 3 P
B
U157
Lithol Rubiua B, BN, G, RG
B
152
Lake Red
Var
153
Var
512
Lake Red C
M
153
B
512
Lake Red D
M
200
Magenta AB
B
512
Lake Red P
M
132
c
512
C
A377
Magenta FABS
jj
512
Lake Scarlet Red D
M
A435
B
512
Lake Yellow 2827
Bv
U247
Magenta TP
tM
512
C
187
B
512
Lanacyl Violet B, BF
Lanafuchsine (V. M.)
Leather Black (V. M.)
Leather Black BO
Leather Black CR
Leather Black I
C
C
C
B
B
I
J
186
64
U290
UI58
U159
U677
TJ358
Magenta crystals
Magenta crystals 3
Magenta crystals II
Malachite Green
Malachite Green (V. M.) . . .
Malachite Green Base
Marine Blue B
Var
tM
tM
Var
Var
Var
I
512
512
512
495
495
495
537
Leather Black R
tM
U535
Marine Blue RR
tM
U537
Leather Black T
M
U447
Aia oo . . . . .
Bv
512
GrE
U511
512
GrE
208
Mars Red AX GX
B
163
J
U359
A BK
6
Leather Brown GG
Bv
U248
Martius Yellow 741
G
6
T
Lev
283 a
Martius Yellow 6749
BK
6
I
283a
P etc
688
Leather Flavine 9118
j
G0fiV.
TTOfiO
Silver Gray N
700
Sudan G, 2 G.. . .
A y
35
Silver Gray P
A
700
Sudan R
A
93
Sirius Yellow G
B
758
Sudan I
A
36
Sitara Fast Red RL
tM
56
Sudan II
A
76
Sitara Orange I
tM
A523
Sudan III
A etc
223
Sky Blue FFO . ...
s
424
Sudan IV
232
Solamine Blue B
A
A44
Sudan Brown
A
105
Solamine Red
A
A44a
Sch
105
Solfigene Blue Green B
Solfigene Blue Green 16444.
I
I
U684
U683
Sulfamine Brown A
Sulfamine L-rown B
WD
WD
107
116
I
U685
J
708
Solfigene Cyanine
I
U686
Sulfine Blue B '.......
CG
S125
Solfigene Deep Black (V.M.)
I
U688
Sulfine Blue RR
CG
S126
Solfigene Deep Black 14717.
I
U687
Sulfine Brown
707
Solfigene Gieen GG
Solid Blue (V. M.)
I
C
U689
U296
Sulfine Brown
Sulfine Brown B, G . . .
CG
CG
737
737
Solid Blue 3 R
S
699
Sulfo Blacks B, 2 B
H
744
Solid Blue RX
G99
Sulfo Green B, C
NF
U550
Solid Blue SBAOOOO
Solid Blue SBSOOO
GrE
GrE
699
699
lulf o Rhodamine B
Sulfo Rosazeine B
M
M
579
U475
Solid Blue Base SBXBX . .
GrE
699
Sulfo Rosazeine G. ...
M
U476
Q
U812
Sulfogene Brown G D
I
757
Solid Brown KF
Q
U813
AW
U589
Solid Brown O
M
U474
Sulfoline G . .
K
U387
Solid Green (V M )
c
495
AW
U590
Solid Green 3 G
O
499
Sulfon Acid Black N 2 B
Bv
U261
Solid Green O
M
1
Sulfon Acid Blue B
By
189
Solid Red B
U814
fcmlfon Acid Blue R
By
188
Solid Yellow G
O
137
ulf on Acid Green B
By
U262
Soluble Blue
ByCo
537
ulfon Black 3 B
By
256
Soluble Blue
Var
539
ulfon Black G
By
242
Soluble Blue
H&M
537
ulfon Blue R
By
188
Soluble Blue (V M )
Var
539 -
ulfon Orange G 5 G
Bv
A297
Soluble Blue AOOOO
GrE
539
ulfon Violet R
By
A298
Soluble Blue B BCBII . . .
CG
539
ulfon Yellow 5 G, R
By
A299
Soluble Blue BLSE 3 BS
p
539
By
361
Soluble Blue BS 3B B, BSJ
GrE
539
ulf oncy anine
Var
257
Soluble Blue C 2, C 3, C 5,
CX
K
539
ulfoncyanine BB, GR, 5 R,
SR
B
257a
Soluble Blue ELOOO
Soluble Blue HA IN 4 R
GrE
539
ulfoncyanine G, GR, 5 R,
5 RT .
By
257
TB TL . ...
B
539
ulfoncyanine Black B, 2 B
By
265
Soluble Blue 5 R
tM
539
ulfoncyanine Black BB,
Soluble Blue RM
M
539
GR
B
265a
Soluble Blue base SBXR
GrE
539
ulfur Black
Var
720
tM
539
WD
721
tM
539
ulfur Black
A
720
Soluble Navy Blue
G
539c
ulfur Black A, AW, AWL .
A
720
Sorbin Red
B
64
ulfur Black B, 2 B, 4 B . . .
A
720
Sorbin Red X . .
B
64
ulfur Black 2 B, BR, BRH,
B
U190
GF
K
720
Special Phosphine G
S
606
ulfur Black FAG, FT
A
720
Spirit Black
G
U645
ulfur Black H, JBL
A
720
622
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Sulfur Black KCB, MA . .
K
720
Tannin Heliotrope
c
685
Sulfur Black T, TFA, TG .
A
720
Tannin Orange R
c
74
Sulfur Black TR
Lev
720
Tannin Orange R
s
606
Sulfur Black TS, 5274, 5276
j
720
Tartrazine
Var
23
Sulfur Black 5285, 5289
Sulfur Black 108583
K
A
720
720
Tartrazine G, X, XX
Terra Cotta FC
B
G
23
209
Sulfur Black Brown N
A
SI
Terra Cotta 2 RN RGN
G
58
Sulfur Black Brown NR
A
S2
Tetracyanol A ...
c
545
Sulfur Blue B
A
S3
Tetracyanol SFV
C
543
Sulfur Blue BE
BK
Si 23
Thiazine Blue
G
A659
Sulfur Blue BG CHL
J
S83
Thiazine Brown R
B
U192
Sulfur Blue D
A
S4
Thiazine Red G
B
197
Sulfur Blue G
K
S83
Thiazine Red R
B
194
Sulfur Blue L
A
S6
Thiazine Yellow G, 3 G, GL
Bv
198
Sulfur Blue PR
A
7
Thiazol Yellow G
S
198
Sulfur Blue R
A
S8
Thiazol Yellow GR
BD
198
Sulfur Blue 2 R
A
S9
Thiazol Yellow R, RH
Bv
51
Sulfur Blue 4 R
A
S10
Thiocarbone NNG
C
720
Sulfur Blue RR
BK
S124
Thiocannine R . .
c
662
Sulfur Blue U
J
S83
Thio Catechine
p
715
Sulfur Brilliant Green GK. .
Sulfur Bronze 136
A
Lev
Sll
S168
Thio Cotton Black
Thioflavine (V M )
WD
C
721
618
Sulfur Bronze 158
Lev
S169
Thioflavine OIO
K
615
Sulfur Brown CI 4 R ...
A
S12
Thioflavine S
S C
615
Sulfur Brown G
A
S13
Thioflavine T
c
618
Sulfur Brown 2 G ....
A
S14
Thioflavine 654
K
615
Sulfur Brown 6 G
Sulfur Brown M ....
A
I
S15
S165
Thiogene Black BB, 5 B . . .
Thiogene Black M, MA,
M
720
Sulfur Brown O
A
S16
MM
M
720
Sulfur Brown OB
A
S17
Thiogene Black ML, MZ .
M
720
Sulfur Brown 527
Lev
S170
Thiogene Blue RL
M
S99
Sulfur Brown 731 ....
Lev
S171
Thiogene Blue R
M
S97
Sulfur Brown (bluish)
J
S84
Thiogene Blue 2 R
M
S98
Sulfur Brown (reddish)
J
S84
Thiogene Cyanine B
M
S107
Sulfur Catechu G
A
S18
Thiogene Cyanine G
M
S108
Sulfur Catechu R
A
S19
Thiogene Dark Red G ....
M
S109
Sulfur Corinth B
Sulfur Corinth CLB
A
A
S20
S21
Thiogene Deep Blue BR . . .
Thiogene Deep Blue
M
M
Sill
S110
Sulfur Green 2 BK
A
S22
Thiogene Green BL
M
S112
Sulfur Green 4 BK
A
S23
Thiogene Green G
M
S113
Sulfur Green G
A
S24
Thiogene Green GG ....
M
S114
Sulfur Green 4 GK
A
S25
Thiogene Green GL
M
S115
Sulfur Green 309
Lev
S172
Thiogppp Khaki N ....
M
S116
Sulfur Green 330
Lev
S173
Thiogene New Blue JL
M
S117
Sulfur Indigo BA ....
A
S26
Thiogene Olive Green GGN
M
S118
Sulfur Indigo CL
A
S28
Thiogene Orange R
M
S119
Sulfur Indigo CLGG
A
S29
Thiogene Violet V
M
S120
Sulfur Indigo Blue RCL
Sulfur Indigo Blue 827
K
K
S85
S85
Thiogene Yellow GG
Thiogene Yellow 5 G
M
M
S121
S122
Sulfur Olive
g
S167
Thiogene Brown G
M
S100
Sulfur Olive B
A
S30
Thiogene Brown GG
M
S102
Sulfur Red Brown 2 RK
A
S31
Thiogene Brown GC
M
S101
Sulfur Red Brown 6 RK
A
S32
Thiogene Brown GR
M
S103
Sulfur Violet R
A
S33
Thiogene Brown G 2 R . . . .
M
S104
Sulfur Violet Y
A
S34
Thiogene Brown R
M
S105
Sulfur Yellow ES
K
U388
Thiogene Brown S
M
S106
Sulfur Yellow G
Sulfur Yellow G
Sulfur Yellow G
S
A
K
712
S35
U388
Thio Indigo Brown G
Thio Indigo Brown 2 R ....
K
K
K
904
902
913
Sulfur Yellow 4 G
A
S36
Thio Indigo Pink 247, 2475.
K
910
Sulfur Yellow I
A
S37
Thio Indigo Pink Rose BW .
K
910
Sulfur Yellow R
A
S38
Thio Indigo Red B
K
912
Sulfur Yellow R
I
S166
Thio Indigo Red 3 B
K
918
Sultan 5 B
H
363
Thio Indigo Rose AN, BN
X
910
Sultan 10 B
H
405
Thio Indigo Scarlet G
K
906
Sultan Orange DS
Sultan Yellow H
H
H
304d
304
Thio Indigo Scarlet R
Thio Indigo Scarlet S, 6086.
K
K
905
916
Sun Yellow
Var
9
Thio Indigo Violet 2 B
K
920
Sun Yellow G, GS, RR
Sun Yellow 3 GC
Supramine Brown R
S
G
Bv
9
9
U263
Thio Indigo Violet K
Thio Indigo Yellow 3 GN . .
Thional Black G .
k K
s
900
913a
719
By
U264
Thional Brilliant Green 29
s
746
Tabora Black X. . ,
A
A45
Thional Brown. . .
S
747
GLOSSARY OF DYE NAMES
623
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Thional Brown G
S
S
8
S
S
K
K
K
K
K
A, M
A
K
K
K
Lev
Lev
Lev
K
K
K
K
K
K
K
I
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
CJ
GrE
GrE
GrE
GrE
GrE
GrE
H
H
H
H
H
H
H.BD
K
B, M
GrE
GrE
GrE
&
fc
Var
GrE.S
M
GrE
GrE
GrE
GrE
M
M
M
M
747
746
746
746
747
720
736
S86
S87
736a
661
661
S88
889
890
719
720
198
891
S92
S93
720
896
S94
895
720
720
8127
713
8128
8129
731
8130
8131
8132
714
Sl32a
U815
720
720
720
720
8133
S134
A761
A762
A763
A764
196
196
198
U690
43
659a
A477
285
488
U266
U265
392d
392
392
392
287
287
358
286
286
265
257
189
188
Tolyl Blue ST 7656
M
I
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
GrE
S
8
S
S
8
S
8
8
C, etc.
H
M
M
I*
B
B
B
B
B
B
B
8
S
S
K
S
S
K
8
H
C
S
A
S
M
K
C
Lev
K
257b
U691
A478
A479
A480
A481
A482
A483
A484
A485
A486
A487
A488
A490
A491
A492
A489
A493
A494
343
617
474
A495
A496
A497
A498
319
A499
A500
304
409
409a
378
449
449
454
457
322
143
139
391
359
U692
498
498
99
U193
U195
U194
U196
U197
U198
U199
U714
58
632a
632a
632
635
632a
644
462e
462d
462d
462d
126a
126
126a
126a
238
A412a
Thional Dark Green GN . .
Thional Green
Tonka Brown GS
Triazol Blue B
Thional Green GG
Thional Red Brown
Triazol Blue BOO
Triazol Blue BBOO
Thion Black (V. M.)
Triazol Blue 4 BOO
Thion Blue B
Triazol Blue R
Triazol Blue 3242
Triazol Bordeaux B
Thion Brown (V. M.) . . .
Thion Dark Blue BO
Thion Direct Blue
Thionine Blue GO
Thionine Blue OO, 3 O
Thion Green 2G
Thion Green 829
Thion Navy Blue (V. M.) . .
Thionol Black ....
Triazol Brown GOOA
Triazol Brown GOOO
Triazol Brown HRO
Triazol Brown SOOO
Triazol Dark Blue BHOOO
Triazol Dark Blue
BHPOOOO
Thionol Black S, XX
Thionol Yellow GR
Triazol Dark Blue BHTOOO
Triazol Dark Blue BOO. . . .
Triazol Dark Blue 3 G
Triazol Dark Blue ROO. . . .
Triazol Fast Red L
Thion Orange (V. M.)
Thion Purple O
Thion Violet
Thion Violet Black
Triazol Fast Yellow 2
GOOOO
Thion Yellow (V M )
Thion Yellow 2 G
Triazol Green B
Thion Yellow 5 G
Triazol Green BPOO
Triazol Green GPOO
Thiophenol Black T
Thiophor Black WLN
Thiophor Blue B
Triazol Pure Blue 3 B ....
Triazol Pure Blue R
Thiophor Bronze 5 G
Triazol Red B
Thiophor Dark Brown B. . .
Thiophor Deep Green CG . .
Thiophor Indigo CJ
Triazol v iolet R
Triazol Violet RR
Triazol Yellow NBPOO. . . .
Trisulfon Blue B
Trisulfon Blue 3 G .....
Thiophor Khaki
Thiophor Orange O ....
Thiophor Yellow R
Thiophor Yellow Bronze G .
Thiophor Yellow Olive
Thio Vesuvine BB
Trisulfon Brown
Msulfon Brown A, B, MB.
Trisulfon Brown G
Thioxine Black ABOOOO . .
Thioxine Black ABBOOOO.
Thioxine Black 3 BOOO. . .
Thioxine Black GB, 1151,
3705. .
Msulfon Brown GG
Trisulfon Violet B
Tropseoline (V. M.)
Trypan Blue
Thioxine Brown 5 G
Thioxine Brown 2 GR
Titan Como 2 B
Turmeric Yellow OOO
Titan Como R
'urquoise Blue B, BB, G. . .
Titan Fast Black B
Titan Orange
Typophor Black FB
Titan Red
Typophor Brown FR
'ypophor Black F 3 R
Typophor Brown FB
Titan Scarlet Y
Titan Yellow G, Y
Tolamine Violet ....
Tolane Red B G
Typophor Yellow FR
Toluidine Blue
Typophor Yellow F 3 R. . . .
Ultra Flavine SD ....
Toluylene Black GOO
Toluylene Brown G
Toluylene Brown R .
Ultra Orange R
Ultra Violet B
Toluylene Fast Brown 2 R .
Toluylene Fast Brown 3 G .
Toluylene Fast Orange GL.
Toluylene Orange
Toluylene Orange G ....
Ultra Violet FKN
Ultra Violet LGP
Ultra Violet MO
Ultra Violet 943
Ultracyanine B
Union Acid Black BH, GH .
Union Black
Union Black BRN
Union Black SOJ
Toluylene Orange GOO
Toluylene Orange R
Toluylene Orange RR . .
Toluylene Red OO, RT
Union Blue H
Toluylene Yellow 6'6
Tolyl Black B, BB, BG
Tolyl Blue 5 R
Union Blue R
Union Blue (V. M.)
Tolyl Blue SB
Union Fast Claret
Tolvl Blue SR . .
Union Red B . .
624
GLOSSARY OF DYE NAMES
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Union Red BS
K
A412b
Water Blue S 2 K
A
539
Universal Black B
By
U267
Wood Red 40 F
Sch
168
Urania Blue
WD
665
Wool Black (V M )
K
U390
Uranine
A, etc
585
Wool Black (V M )
Lev
220b
Uranine A
B
585
Wool Black (V M )
O
220b
Uranine N
M
585
Wool Black 6 A, 6 AN
tM
217g
Ursol . .
923
Wool Black B, 2 B . .
A
220b
Ursol A
A
923
Wool Black B ..
K
U390
Ursol ADF
A
923
Wool Black BB
AW
272c
Ursol D
A
923
Wool Black 3 B.
Lev
220b
Ursol DB
A
923
Wool Black 4 B 6 B 4 BC
A
220
Ursol DF
A
923
Wool Black 4 B
I
272c
Ursol GG
A
923
Wool Black 10 B
tM
217g
Ursol P
A
923
Wool Black 4 BFL, 6 BS,
Ursol PP
A
923
4BX
A
220
Ursol Gray AL
A
923
Wool Black CD, CL
K
U390
Varnish Black
WD
U548
Wool Black DW
BK
269
Varnish Black 5 R
O
U816
Wool Black G GR GRF
A
220b
Vesuvine (V. M.)
B
284
Wool Black 6 G
G
U646
G
169
Wool Black GG
tM
217
Victoria Black B
Bv
262
Wool Black HN
tM
217g
Victoria Blue B
Var
559
Wool Black LR
K
U390
Victoria Blue B base
Var
559
Wool Black MX
Q
220b
Victoria Blue BE, BS, BSS .
B
559
Wool Black N . .
M
A441
Victoria Blue R
Var
558
Wool Black NN .
I
272c
Victoria Blue 4 R
Victoria Blue Base
Var
s
522
559a
WoolBlackN4B
Wool Black NC.
By
K
A301
U390
Victoria Blue Base 61272. .
H
559a
Wool Black NP...
By
A302
Victoria Brilliant Blue B . .
Victoria Fast Violet B . . . .
Victoria Fast Violet 2 R
M
By
By
559b
U268
U269
Wool Black NP
Wool Black NR
Wool Black SG
CG
K
GrE
272c
U390
272c
Victoria Green
Var
497a
Wool Black V
K
U390
Victoria Green BF
B
497a
Wool Black 9904
BK
269
Victoria Green 4833, 4834 . .
Victoria Green Base
By
B, tM
497a
497a
Wool Black (greenish)
Wool Blue
K
c
U390
U300
Victoria Navy Blue L
Bv
U270
Wool Blue
Q
538b
Victoria Pure Blue B
B
559
Wool Blue (V. M.)
K
U391
Victoria Scarlet R ....
M
A439
Wool Blue (V M ) ...
Lev
565a
Victoria Scarlet 2 R, 4 R. . .
tM
169
Wool Blue B
AW
565
Victoria Scarlet 3 R
Victoria Violet (V M )
M
Var
A440
61
Wool Blue 2 B, 5 B, G
Wool Blue 2 BX
A
A
565
565a
Victoria Yellow
M
134
Wool Blue G, 2 G, G 446 N
K
U391
Vidal Black I
p
717
Wool Blue M
AW
562b
Vigoureux Brown I
M
U477
Wool Blue N
By
562
Vigoureux Fast Black T. . . .
Vigoureux Green B
M
c
159a
U299
Wool Blue R, RX
Wool Blue R
A
By
565a
562b
Violamine B ....
M
580
Wool Blue 5 R ...
H
538
Violamine 3 B
M
584
Wool Blue S
K
U391
Violamine R
M
582
Wool Blue S ...
538b
Violet 2 B
K, tM
516a
Wool Blue 2 S
U391
Violet 6 B
Q
517
Wool Blue SB
AW
562b
Violet DV
Q
516a
Wool Blue SDOO SLOO .
B
530d
Violet NX
AW
516a
Wool Blue SR
By
562
Violet 9 O 300 XE
p
516a
Wool Blue TB
K
U391
Violet 55396
H
516a
Wool Blue 1092
A
565a
Violet Base 2 B
51 6a
Wool Blue Black 2019
K
U392
Violet Base 5747
K
516a
Wool Brown MC, P, SVR,
Violet Black
B
290
UB, 2808
K
U393
Violet Crystals
s
516
Wool Canary OD
H
U765
Violet Crystals . .
K
516
Wool Cerise SR
K
U394
Violet Crystals 5 BO 6 BO
I
516
Wool Claret 21 B
Lev
U742
Violet Crystals O
M
516
Wool Claret Red 87 B, 211,
Violet Crystals 142 S
K
516
357
Lev
U743
Violet Direct VR
G
A660
Wool Fast Black B
B
U200
Violet Modern N
DH
624
Wool Fast Blue BL
B
U201
Violet Neutral O
M
516a
Wool Fast Blue BL
By
U271
Violettine 3 R
AW
U591
Wool Fast Blue GL
By
U272
Viridanthrene B
B
765
Wool Fast Blue L
I
U693
Vitoline Yellow 5 G, R. . .
Vulcan Blue BO
tM
Lev
606
U740
Wool Fast Orange G
Wool Fast Yellow G
B
B
U202
U203
Vulcan Blue G
Lev
U741
Wool Fast Yellow 5 GX. . . .
B
U204
Water Blue
C, etc.
539
Wool Fast Yellow WG
B
U205
Water Blue MX..
Q
539
Wool Green (V. M.) . .
K
U395
GLOSSARY OF DYE NAMES
625
Name
Manu-
fac-
turer
Serial
No.
Name
Manu-
fac-
turer
Serial
No.
Wool Green
tM
566a
Xylene Light Yellow R
J
00
Wool Green B ....
566
Xylene Light Yellow R
oo
Wool Green BS
Bv BK
566
Xylene Red B
g
K7Q
Wool Green S
Var
566
Xylene Yellow
22
Wool Green SAK, 16437 . . .
I
566a
Xylene Yellow 3 G
K
22
Wool Green SC
G
566
BK tM
7Q
WoolJet Black 3 B
A
220c
Xylidine Scarlet
Sch
82
Wool Red
Wool Red (V. M.)
K
c
168b
236
Yellow (V. M.)
Yellow (V M )
CJ
I
U500
141d
Wool Red C
g
236b
Yellow CP
Lev
142a
Wool Red CS
Wool Red G
K
B
168b
A 140
Yellow FY
Yellow NF
H
BK
U773
U487
Wool Red K 10 BX
B
A141
Yellow NF
O
U817
Wool Red L, MC, SOC
K
168b
Yellow PC
DH
U601
Wool Red SB
CG
64
Yellow R
W
141d
Wool Red 7742
BK
168b
Yellow 2 S
p
137
Wool Scarlet
K
U396
Yellow (for feathers)
WD
U549
Wool Scarlet (V. M.)
Wool Scarlet 5 B
Lev
H
80b
80c
Yellow Black M
Yellow Fast-To-Soap
BK
p
U488
203
Wool Scarlet R
Sch
80
Yellow Fat Color
B
68
Wool Scarlet RR
B
A142
Yellow Green 6 B
BK
U489
Wool Scarlet 4 R
Wool Scarlet 3 RB
BK
B
80a
A143
Zambesi Black B
Zambesi Black 2 BA
A
A
A46
A47
Wool Violet B ...
O
59a
Zambesi Black BH
A
A48
Wool Violet R
K
U397
Zambesi Black BR
A
A49
Wool Violet S
B
59
Zambesi Black OTA
A
A53
Wool Violet SL
K
U398
A
A50
Wool Yellow
Sch
23
Zambesi Black F
A
A51
Wool Yellow AT, D, G
Wool Yellow LDV, R
Wool Yellow S
K
K
G
U399
U399
143
Zambesi Black OBA
Zambesi Black R
Zambesi Black V
A
A
A
A54
A52
A55
Wool Yellow T
G
23
Zambesi Black VM
A
A56
Wool Yellow 1501
K
U399
Zambesi Bordeaux 7 B
A
A57
Xanthine CJB
I
606
Zambesi Brown
330
Xanthine I . .
p
606
Zambesi Brown G, 2 G
A
330
XL Acid Eosine5 B
H
590a
A
330a
XL Blue
H
U770
Zambesi Pure Blue 4 B ....
A
274b
XL Blue GR
H
U770
Zambesi Red B
A
A58
XL Brown RH
H
284a
Zambesi Red 4 B
A
A59
XL Green Y
H
U771
Zambesi Red 6 B
A
A60
H
U772
Zambesi Red 8 B
A
A61
Xylene Blue AS ASL BS
g
508
A
A62
Xylene Blue VS
s
507
Zambesi Scarlet 6 B
A
A63
s
564
Zambesi Scarlet 2 BL
A
A64
Xylene Light Yellow
Var
22
Zambesi Scarlet FR
A
A65
Xvlene Lnrht Yellow 2 G. .
K. S
22
Zambesi Scarlet PR . .
A
A66
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES
As the Glossary of Dye Names refers only to Schultz numbers, by look-
ing in this index for the Schultz number, there can be found the pages
on which any dye is tabulated.
This procedure was adopted for the reason that a Driven dye, charac-
terized by a Schultz number, will be known under very many names.
Such names are listed in the Glossary but could not all be placed in the
tables without unnecessarily enlarging this book.
Sehulta
Schultz
Schultz
Number Page
Number Page
Number Page
509
54 394, 422
107 385, 447
362, 447
55 409, 422
108 375, 385
223
56 362, 377, 422
109 370, 385
526
57 174, 423
110 372, 385
460
58 93, 423, 519
111 385, 526
360
59 219, 248
112 385, 505
360
60 83, 509
113 287, 385
456
61 26, 174, 423, 471
114 174, 385
452
62 245, 500
115 363, 392
10 253, 260, 452
63 225, 245, 423
116 392, 447
11 260, 453, 509
64 26, 370
117 182, 371
12 91, 253, 260, 453
65 26, 504
118 182, 225, 372
13 260, 453, 471
66 22, 27
119 165, 182
14 78, 453
67 27, 174
120 84, 185
15 126, 453
68 36, 554
121 185, 371
16 183, 453
69 554, 567
122 185, 287
17 183, 453
70 526, 553
123 186, 526
18 183, 253, 260, 496
71 225, 553
124 93, 238, 555, 569
19 21,91,345,481
72 362, 456
125 93, 460, 555, 569
20 91, 481, 534
73 362, 455
126 93, 363, 555, 569
21 343, 552
74 42, 43, 362
127 93, 555, 570
22 21, 213, 529
2S 230, 482, 529
75 42, 43, 509
76 362, 576
128 94, 555, 570
129 38, 174
24 87, 343
77 414, 576
130 38, 43, 174, 277
25 21, 496
78 375, 576
131 46, 363
26 343, 496
79 526, 577
132 74, 363
27 21, 345. 482, 496
80 372, 577
133 74, 519
28 343, 533
81 370, 578
134 262, 334
29 67, 343
82 505, 577, 578
135 262, 334
30 Not classified
83 498, 505
136 262, 334
31 32, 91
84 78, 500
137 32
32 91, 238
85 76, 484
138 238, 529
33 91, 465
86 50, 362
139 262, 529
34 92, 566
87 Not classified
140 262, 529
35 92, 509
88 465, 494
141 262, 529
36 92, 362
89 465, 494
142 262, 530
37 92, 526
90 78, 494
143 510, 630
38 92, 286
91 353, 494
144 360, 530
39 92, 504
92 60, 494
145 363, 530
40 92, 174
93 108, 362
146 225, 530
41 92, 298
94 108, 414
147 225, 530
42 22, 93
95 108, 372
148 75, 364
43 93, 326
44 93, 508
96 49, 108, 519
97 156, 363
149 36
150 87, 262
45 93, 311
98 363, 425
151 87, 364
46 362, 421
99 363, 426
152 87, 311
47 421, 504
100 49, 371
153 46, 364
48 421, 519
101 49, 505
154 81, 466
49 421, 517
102 126, 519
155 81, 510
50 279, 422
103 126, 519
156 81, 364
51 183, 422
104 142, 414
157 81, 223
52 353, 422
105 360, 385
158 80, 500
53 330, 422
106 363, 385
159 77, 364
627
628 PAGE INDEX OF SCHULTZ NUMBERS FOR DYES
Schullz
Number Page
160 354, 360
161 354, 364
162 330, 364
163 354, 414
164 354, 375
165 354, 370
166 354, 526
167 180, 354
168 355, 505
169 287, 355
170 355, 380
171 174, 355
172 153, 360
173 364, 403
174 153, 365
175 365, 404
176 153, 414
177 153, 178, 519
178 55, 520
179 311, 403
180 68, 360
181 68, 365
182 94, 125, 298, 552
183 76, 360
184 76, 365
185 72,365
186 276, 298
187 63, 299
188 299, 484
189 299, 572
190 183, 466, 496
191 437, 496
192 473, 496
193 183, 365
194 184, 414
195 414, 496
196 184, 527
197 496, 527
198 184, 497
199 184, 497, 520
200 110, 365
201 110, 527
202 110, 505
203 40, 262
204 40, 520
205 454, 460, 471
206 243, 454, 471
207 454, 471, 475
208 466, 471
209 184, 355, 466, 497
210 334, 473, 497
211 510, 530, 578
212 361, 531
213 355, 510
214 361, 579
215 94, 326, 423
216 65, 94, 423
217 94, 299, 423
218 71, 207, 386, 424
219 94, 326, 494
220 70, 386, 531
221 424, 520, 531
222 83, 421, 510
223 32, 365
224 32, 414
225 32, 370
226 32, 372
227 33, 287
228 33, 380
229 33, 226
230 36, 153
231 36. 276
232 36, 366
233 36, 414
234 36, 527
235 36, 372
236 36, 505
237 37, 527
Schultz
Schultz
Number Page
Number Page
238
37, 506
315 84, 127, 460
239
27, 47, 242, 366, 466
316 84, 127, 154
240
83, 366, 553
317 127, 510
241
94, 295, 386
318 127, 367
242
94,226,400
319 127, 287, 460
243
27, 386, 527
320 127, 180
244
27, 386, 506
321 127, 180, 372
245
295, 386, 424
322 84, 127, 367, 379
246
34, 366
323 128, 175
247
34, 366
324 70, 128, 180
248
34, 527
325 70, 128, 371
249
34, 180
326 128, 325
250
34, 520
327 128, 295
251
34, 180
328 128, 295
252
37, 366
329 128, 295, 466
253
37, 414
330 128, 295, 412
254
37, 527
331 128, 295, 447
255
37, 180
332 84, 128, 295
256
334, 386, 485
333 128, 296, 299
257
334, 386, 400, 485, 572
334 129, 273, 300
258
334, 386, 401
335 129, 296, 326
259
108, 180, 531
336 70, 129, 300
260
48, 366, 531
337 129, 300
261
299, 386, 531
338 129, 326, 546
262
226, 387, 531
339 82, 129, 520
263
39, 387, 483
340 129, 129, 356, 405,
264
299, 355, 366
521, 521
265
330, 387, 401, 485
341 129, 506, 521
266
285, 387
342 130, 521
267
264, 264, 285, 387, 387,
343 130, 296, 521
394
344 130, 296, 521
268
67, 387, 394
345 69, 130, 521
269
387, 394, 506
346 130, 325, 521
270
55, 94, 287, 506
347 130, 341, 522
271
55, 67, 367
348 130, 243, 522
272
55, 388, 506
349 130, 475, 522
273
23, 388, 411, 527
350 130, 184, 522
274
23, 295, 388, 411
351 130, 178
275
85, 376, 388, 415
352 131, 228, 567
276
85, 226, 388
353 131, 228, 300
277
85, 401
354 131, 228
278
388, 401
355 415, 432, 522
279
33, 95, 325, 486
356 210, 356
280
535, 556
357 154, 210
281
392, 535, 556
358 84, 210
282
392, 535
359 84, 137
283
466
360 135, 437
284
567
361 136, 483
285
200, 466
362 201, 546
286
200, 437
363 356, 546
287
200, 392
364 330, 546
288
198, 367
365 154, 546
289
198, 367, 527
366 154, 405, 546
290
27, 388, 415, 471
367 405, 547
291
415, 471, 520
368 154, 356, 547
292
175, 472, 520
369 84, 357, 547
293
527, 541
370 84, 154, 547
294
520, 541
371 276, 405, 547
295
194, 295, 567
372 276, 547
296
27, 486, 520
373 84, 460, 547
297
194, 295
374 357, 510, 547
298
193, 506
375 357, 415, 547
299
196, 506
376 510, 547
300
196, 506
377 415, 547
301
199, 392
378 367, 379, 547
302
153, 199
379 175, 415, 548
303
199, 460
380 175, 548
304
199, 460
381 300, 309, 548
305
199, 520
382 300, 388, 548
306
126, 437, 473
383 300, 392, 548
307
126, 355
384 70, 181, 548
308
126, 330
385 325, 415, 548
309
126, 356, 413
386 300, 416, 548
310
126, 413
387 70, 371, 548
311
126, 177, 356
388 70, 548
312
126, 356, 415
389 65, 549
313
127, 180, 356
390 70, 300, 549
114
84, 127, 437
391 301, 549
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 629
Schultz
Schultz
Schultz
Number Page
Number Page
Number Page
392 178, 201, 549
467 133, 167, 302, 461
544 218, 308, 428
393 243, 522, 549
468 133, 167, 302, 523
545 145, 308, 428
394 522, 549
469 133, 207, 302, 468
546 282, 308
395 178, 549
470 133, 207, 302, 461
547 235, 339
396 227, 416, 549
471 133, 207, 303
548 270, 328
397 228, 416, 549
472 133, 207, 297, 303
549 305, 525
398 229, 549
473 133, 297, 303, 424
550 85, 305
399 227, 296, 550
474 133, 303, 424, 461
551 159, 178
400 367, 551
475 134, 303, 424, 523
552 168, 178
401 268, 416
476 134, 468, 524, 531
553 122, 179
402 268, 296, 373
477 134, 511, 524, 532
554 159, 179
403 268, 296
478 71, 134, 524 532
555 462
404 268, 461, 522
479 134, 175, 357, 468
556 462
405 202, 357
480 134, 330, 511, 524
557 525
406 202, 367, 399
481 82, 357, 511, 550
558 276, 305, 328
407 202, 357, 416
482 96, 524, 556, 560
559 305, 328, 483
408 202, 202, 202, 368, 42 1,
483 190, 417
560 537, 571
424
484 190, 417, 507
561 328, 343
409 202, 368, 379
485 469, 532
562 305, 398
410 202, 416
486 40, 469
563 305. 33C, 358
411 202, 376
487 357, 469
564 232, 240, 305, 347,
412 202, 416, 506
488 200, 357, 469
349, 575
413 202, 224, 567
489 134, 511, 532
565 264
414 203, 224, 507
490 134, 358, 469
566 287, 306, 328, 368
415 175, 203
491 137, 297, 469
567 306, 310
416 203, 226
492 85, 399, 469
568 237
417 166, 166, 203
493 233, 238, 327, 540
569 237
418 165, 203
494 242, 345
570 216, 237, 516
419 64, 203, 368
495 120, 238
- 571 271, 488
420 70, 181, 203
496 159, 238
572 99, 216, 488
421 69, 203, 416
497 209, 238
573 216, 488, 511
422 64, 70, 203
498 304, 452, 537
574 216, 488
423 71, 204
499 120, 217
575 234, 516
424 64, 204
500 159, 282
576 48, 234
425 71, 204, 301
501 209, 345
577 234, 271
426 204, 301
502 120, 279
578 234, 511
427 204, 227, 416
503 159, 279
579 122, 216
428 204, 229, 416
504 121, 147
580 99, 488, 512, 563
429 204, 227, 507
505 121, 144
581 216, 489
430 204, 227, 301
506 122, 144, 279
582 489, 512, 558
431 408, 461
507 217, 337
583 333, 489, 512
432 389, 408
508 144, 337
584 211, 459, 512
433 392, 410, 507
509 138, 304
585 489, 512
434 368, 410, 507
510 86, 239, 428, 524
586 143, 489, 512
435 41, 83, 95, 389, 467, 510,
511 89, 96, 193, 429, 430,
587 489, 512
554
560, 574
588 490, 513
436 296, 401, 467, 472
512 96, 430, 556, 560
589 490, 513
437 296, 467, 472, 511
513 90, 195, 451, 556
590 490, 513
438 131, 301, 479
514 96, 556, 561
591 490, 513
439 49, 131, 301
515 239, 461
592 490, 513
440 49, 131, 297
516 239, 304, 327, 487
593 211, 513
441 131, 301, 389
517 143, 239, 462
594 212, 514
442 131, 297, 389, 508
518 217, 487, 537, 538
595 212, 514
443 131, 301, 389, 508
519 239, 462
596 514, 536
444 95, 131, 297, 522
520 97, 138, 561
597 514, 536
445 95, 131, 475, 522
521 97, 138, 557, 561
598 514, 536
446 132, 301, 389, 522
522 327, 342
599 290, 490, 500
447 132, 389, 417, 523
523 143, 240, 428
600 491, 514
448 132, 302, 467, 523
524 97, 557, 561
601 290, 491, 500
449 132, 467, 508, 523
525 97, 557, 561
602 568
450 389, 417, 550
526 97, 557, 561
603 244, 540
451 371, 390, 550
527 147, 328
604 121, 244
452 226, 390, 550
528 146, 304
605 121, 568
453 508, 550, 567
529 232, 279
606 99, 558, 563
454 467, 508, 523, 550
530 218, 279
607 328, 470
455 204, 508, 567
531 205, 539
608 Not classified
456 205, 371, 390
532 339, 537
609 Not classified
457 205, 467, 508, 523
533 232, 339
610 139, 324, 502
458 74, 401, 410, 468, 474,
534 214, 339
611 331, 503
567
535 97, 562
612 491, 502
459 135, 390, 417
536 98, 557, 562
613 491, 502
460 135, 226, 390
537 98, 558, 562
614 182
461 297, 410, 468, 511, 568
538 98, 263, 558, 562
615 497
462 95, 132, 302, 468
539 98, 558, 562
616 497, 563
463 95, 132, 302, 568
540 99; 193, 558, 562
617 184
464 95, 132, 302, 461
541 99, 393, 558, 562
618 182
465 71, 95, 132, 523
542 163, 254, 305, 334
619 245, 361, 440
466 65, 133, 523, 531
543 218, 308, 428
620 214, 440
630 PAGE INDEX OF SCHULTZ NUMBERS FOR DYES
Schultz
Schultz
Schultz
Number
Page
Number
Page
Number
Page
621
236, 472
697
33, 102
775
256, 352, 463
622
100, 290, 440
698
102, 431. 435
776
256
623
440, 501
699
33, 102
777
175
624
290, 440
700
103, 431, 435
778
25, 115
625
290, 447
701
33, 472
779
25, 115,v419
626
290, 440
702
103, 472, 559, 563
780
25, 115
627
245, 288, 440
703
445, 559, 563
781
25, 115
628
231, 291, 441
704
445, 559
782
138, 293, 491
629
291, 441
705
445, 559, 564
783
25, 115, 499
630
100, 288, 441
706
Not classified
784
114
631
291, 441
707
Not classified
785
113
632
291, 441
708
Not classified
786
113
633
291, 441
709
79, 437
787
25, 115
634
291, 441
710
568
788
25, 115
635
291, 441
711
568
789
257
636
294, 441
712
135, 571
790
109, 250
637
288, 442
713
472
791
109
638
288, 442
714
27, 135, 472
792
337
639
289, 439, 442
715
27, 187
793
338
640
100,291,442
716
571
794
338
641
213, 288, 439
717
79
795
337
642
292, 442, 514
718
431, 462, 472
796
109, 249
643
292, 442, 515
719
103, 424, 436
797
25, 28, 115, 420
644
292, 442, 515
720
259
798
25, 115, 418
645
292, 442, 528
721
259
799
25, 115
646
100, 213, 288, 439
722
259
800
251
647
442, 515
723
259
801
250
648
449, 515
724
79, 162, 255
802
250
649
368, 443
725
79, 162, 252, 255
803
28, 419
650
368, 443
726
57, 79, 162, 255
804
28, 419
651
369, 443
727
52, 162, 473
805
28, 420, 431
652
306, 369, 443
728
235
806
434
653
215, 390
729
103, 246
807
434
654
147, 215
730
57
808
28, 419
655
223, 443
731
246, 361
809
28, 419
656
68, 383
732
56, 197, 463
810
30, 487
657
72, 383
733
79, 559
811
30
658
309, 443
734
79, 432
812
20, 186
659
240, 245, 443
735
464, 464
813
20, 186
660
240, 245, 443
736
57
814
29, 140
661
240, 245, 247. 275, 444
737
433
815
59, 140
662
279, 280
738
162, 254, 255, 335, 532
816
141, 188
663
282, 284
739
57
817
141, 188
664
247, 292
740
258
818
55, 141
665
247, 248
741
258
819
141, 188
666
221, 382
742
258
820
190
667
247,281,381,382
743
258
821
141, 190
668
52, 458
744
Not classified
822
141, 573
669
246, 470
745
257
823
89, 141
670
246, 444, 568
746
313
824
29, 157
671
283, 390
747
312
825
30, 152
672
100, 390
748
155, 449
826
29, 208
673
100, 390
749
250, 251
827
45, 209
674
101, 391
750
258-
828
157, 188
675
101, 448
751
Not classified
829
59, 208
676
444, 484
752
Not classified
830
29, 209
677
265, 444
753
Not classified
831
158, 393
678
219, 444
754
Not classified
832
111, 208
679
101, 559, 570
755
Not classified
833
41, 139
680
101, 246
756
Not classified
834
29, 157
681
246, 444
757
Not classified
835
116
682
101, 444
758
347, 384, 491
836
116, 189
683
101, 246. 333, 559, 563
759
337
837
30, 316
684
101, 148, 278, 283, 345
760
241
838
30, 316
444, 445, 446, 446,
761
241
839
151
486, 486, 486
762
241
840
316, 317
685
444, 577
763
118, 124
841
316
686
101, 218, 220, 563
764
118, 124
842
316
687
53, 102, 559
765
118, 124
843
317
688
102, 553
766
160
844
44
689
264, 444
767
160
845
189
690
246, 267
768
160
846
30, 124
691
266, 445
769
500
847
191
692
248, 445
770
138, 139, 500
848
189
693
102, 391, 462, 483
771
517
849
31
694
35, 391
772
293
850
317
695
35, 472
773
21, 222, 500
851
31, 103
696
33, 102
774
256, 352
852
88, 502, 502, 564
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 631
Schultz
Schultz
Schultz
Number
Page
Number
Page
Number
Page
853
251, 564
878
105, 318,
476,
479, 492,
896
307, 322
854
25, 115, 564
543
897
320, 320,
321
855
50, 564
879
105, 319,
476,
479, 492,
898
321, 341
856
151, 564
543
899
314, 322
857
103, 250
880
105, 319,
476, 479, 492,
900
314, 322,
322
858
117
543
901
314, 322
859
45, 564
881
105, 319,
477,
479, 492,
902
58, 323
860
45, 564
543
903
58, 323
861
104, 535
882
105, 319,
477,
480, 492,
904
58, 321
862
25, 104, 115, 499
543
905
314, 321
863
112
883
105, 319,
477,
480,492,
906
314, 321
864
104, 427, 564
543
907
19, 314
865
88, 503, 503, 565
884
105, 319,
477,
480, 493,
908
19, 314
866
335
543
909
172
867
31
885
105, 319,
477,
480, 493,
910
150
868
60
543
911
19, 58
869
332
886
106, 319,
477,
480, 493,
912
314, 545
870
29, 141, 157
544
913
269
871
Not classified
887
168
914
58
872
118
888
450, 559
915
269
873
149, 188
889
106, 142,
319,
477, 480,
916
274
874
104, 318, 476, 478, 491,
493, 54
4
917
171
542
890
106, 142,
319,
478, 481,
918
173
875
429
493, 54
4
919
314, 545
876
104, 318, 476, 479, 492,
891
359
920
164
542
892
359
921
170, 438
877
105, 318, 476, 479, 492,
893
117, 206
922
53, 106
542
894
306, 322
923
78, 79, 192, 473
895
206, 361
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