The Manufacture or Production of Colouring Matters, and Materials therefor.
Year: 1894

page_text: [Communicated from abroad by THE FARRENFABriken, vormals FRIEDRICH
BAYER & Co., of Elberfeld, Germany.]
The Manufacture or Production of Colouring Matters, and Materials
therefor.
1 HENRY EDWARD NEWTON of The Office for Patents, 6 Bream's Buildings,
Chancery Lane in the County of London, Patent Agent, do hereby declare the
nature of this invention to be as follows:-
It has been described in the Annalen der Chemie, volume 265, page 87, that
paranitrochlorobenzene is, by sulphonation, converted into orthochloro metanitro
benzene sulphonic acid, having the formula:
My foreign correspondents have now found, that this chloronitrobenzene sulphonic
acid is transformed into the new paranitro paramido diphenylamine orthosulphonic
acid, if, for instance, a salt of the said chloronitro-sulphonic acid, in hot watery
solution, and in the presence of alkaline salts which are decomposed by hydro
chloric acid, is allowed to act on the free paraphenylenediamine. The alkaline salts
of the resulting para nitro paramido diphenylamine-ortho-sulphonic acid dissolve
readily in water, affording a slightly yellowish brown coloured solution, and the
said parauitro paramido diphenylamine ortho sulphonic acid separates in small
greyish-brown crystals (soluble with difficulty in water), on adding mineral acids
to the solution of its alkaline salts in water.
The researches of my foreign correspondents have further shewn, that the para-
nitro paramido diphenylamine ortho-sulphonic acid is, by reduction, converted into

page_text: This diamido diphenylamine mono sulphonic acid is insoluble in dilute acetic acid,
but dissolves readily in dilute mineral acids, ammonia, alkaline hydroxides and
alkaline carbonates. The hydrochloride of the new diamido acid separates in a
crystalline state from its concentrated solutions in water, and forms with stannous
chloride a double salt, which dissolves with difficulty in concentrated muriatic acid.
The reduction can be effected in alkaline, or, more profitably, in acid solution, by
means of methods known and in use for analogous purposes.
In order to illustrate the production of the two new acids hereinbefore referred
to, viz., paranitro paramido diphenylamine ortho sulphonic acid, and para-diamido
diphenylamine ortho sulphonic acid, the following examples are given. The parts
are by weight.
PRODUCTION OF PARANITRO PARAMIDO DIPHENYLAMINE ORTHO SULPHONIC
ACID FROM ORTHO CHLORO NETA NITRO BENZENE SULPHONIC ACID AND
PARA PHENYLENE DIAMINE.
6.6 parts of calcium salt of the ortho chloro meta nitro benzene sulphonic acid,
together with 2.2 parts of para phenylene diamine, are dissolved in about 500 parts
of hot water.
2:8 parts of crystallized sodium acetate are then added, while
stirring.
The resulting liquid is heated for some time, until it reaches boiling point.
It assumes a yellowish-brown colour. A concentrated solution, in water, of
5-8 parts of sodium carbonate in crystals is added, under continued stirring. After
boiling for about hour, the separated calcium carbonate is filtered off, and the
new acid thus formed is precipitated by adding muriatic acid to the resulting
filtrate. The paranitro paramido diphenylamine sulphonic acid, after standing for
several hours at a low temperature, is filtered off, washed with water and dried at
100 degrees Centigrade.
CONVERSION OF
PARANITRO PARAMIDO DIPHENYLAMINE SULPHONIC ACID
INTO PARA DIAMIDO-DIPHENYLAMINE SULPHONIC ACID.
3.1 parts of the para nitro paramido diphenylamine ortho sulphonic acid are gradually
introduced into a solution prepared by dissolving 113 parts of stannous chloride in

page_text: 35 parts of concentrated hydrochloric acid. The mixture is heated to about
40 degrees Centigrade, and continuously stirred. The sulphonic acid dissolves.
On cooling, the double salt of the diamido acid with stannous chloride separates.
It is filtered off and pressed, and re-dissolved in water. The resulting solution is
treated with zinc (in order to remove the tin), and filtered. The free paradiamido
diphenylamine ortho sulphonic acid is separated by an addition of sodium acetate
to the filtrate concentrated. It forms white Hakes, which become crystalline after
a short time, and it is purified, if necessary, by crystallization from water.
exhibits considerable stability against the oxidising action of the air.
It
The reduction, as a matter of course, can also be effected by means of iron or
zinc dust in acetic acid, or dilute mineral acid solutions, or in any other suitable
manner.
According to the researches of my foreign correspondents, the paratiamitlo
diphenylamine, ortho-sulphonic acid yields, by diazotisation, a tetrazo compound
which can be used for producing valuable dye-stuffs.
It is known that the meta position of the sulphonic group relatively to the one
amido group contained in the benzidine nucleus, exerts an influence, inasmuch as
the dye-stuffs obtained by diazotising benzidine meta sulphonic acid, and coupling
the tetrazo compound with amines or phenols, no longer shew the property of
striking on unmordanted cotton. Owing to this fact, it might have been naturally
expected that the before mentioned diamido diphenylamine sulphonic acid, when
diazotised and coupled with known dye-stuff components, would yield such azo
colouring matters as have no affinity to unmordanted vegetable fibre, which would
also be in accordance with the fact, that the non-sulphonated diamido diphenylamine,
by diazotisation and combination with the usual dye-stuff components, produces
colouring-matters possessing but slight affinity for cotton fibre.
The researches of my foreign correspondents have also shewn, that almost all
colouring matters obtained by combining the tetrazo derivative of paradiamido
diphenylamine, ortho monosulphonic acid with phenols, amines, sulphonic or
carboxylic acids thereof, do not possess the properties of the so-called benzidine
dye-stufts, inasmuch as they give but weak and valueless shades. Even the
colouring matter which is analogous to the dye-stuff known in commerce as
diamine black," and which results from the combination of two molecular propor-
tions of amidonaphthol mono sulphonic acid G. with one molecular proportion of the
tetrazo compound of para diamitlo diphenylamine sulphonic acid, is entirely valueless,
as it yields only slightly bluish grey shades.
According to the researches of my foreign correspondents, valuable dye stuff's,
distinguished for their great affinity to vegetable fibre, are, however, obtained from
the said diamido diphenylamine sulphonic acid, if its tetrazo compound is combined
with such components as contain basic groups, for instance, metaphenylene diamine,
metatoluylendiamine, chrysoidines, the so-called Bismarck browns, or the like.
My foreign correspondents have found, that not only the symmetrical disazo
dyestuffs containing two molecular proportions of a metadiamine, chrysoidine,
Bismarck-brown, or the like, but also the mixed disazo dyestuff's produced from
equal molecular proportions of tetrazotised paradiamido-diphenylamine-ortho-mono-
sulphonic acid, and metadiamines, or the like, and any other dyestuff components,
possess great techuical value, and the researches have further shewn, that those
colouring-matters are also very valuable which can be produced by combining the
tetrazo derivative of paradiamidodiphenylamine-ortho-sulphonic acid with one or two
molecular proportions of amines capable of further diazotisation, or (in any order)
with one molecular proportion of such an amine and one molecular proportion of
another component, by further dinzotising the intermediate products so formed, and
coupling the resulting diazo or tetrazo compounds with one or two molecular
proportions of a diamine, chrysoidine, or a dyestuff of the Bismarck brown series,
or with one molecular proportion of a diamine, chrysoidine, or a dyestuff of the
Bismarck-brown series, and one molecular proportion of any other dyestuff
component.

page_text: DYESTUFF
OBTAINED
FROM ONE MOLECULAR PROPORTION OF DIAMIDO-
DIPHENYLAMINEMONOSULPHONIC ACID AND TWO MOLECULAR PROPOR-
TIONS OF METAPHENYLENEDIAMINE.
28 parts of paradiamidodiphenylamine-ortho-monosulphonic acid, are stirred
into 300 parts of water, and subsequently dissolved by an addition of 3 parts of
muriatic acid (20 degrees Baumé). A concentrated solution in water of 14 parts
of sodium nitrite is added, in order to prepare the tetrazo compound. When the
formation of the latter is complete, a concentrated watery solution of 3-8 parts of
metaphenylenediamine hydrochloride is allowed to flow into the resulting liquid
mixture, and the complete formation of the dye-stuff is finally caused by an addition
of sodium acetate. The colouring-matter, which is, by a suitable treatment,
converted into the sodium salt, is isolated in the usual manner. It possesses the
following formula:-
It produces intense red shades on unmordanted cotton, and when fixed on the
fibre, can be diazotised and combined with known developers, such as betanaphthol,
metaphenylenediamine, or the like, very deep shades being thus obtained, which
withstand washing.
Similar dyestuff's result, if the metaphenylenediamine used in the above third
example, is replaced by equivalent quantities of other meta diamines, such as
metatoluylenediamine or the like, or chrysoidines, or the so called dyestuffs of the
Bismarck-brown series; or if the tetrazodiphenylaminemonosulphonic acid is
combined with one molecular proportion of the one metadiamine chrysoidine, or
dyestuff of the Bismarck brown series, or the like, and one molecular proportion
of another of these components; or if the said tetrazo compound is coupled (in
any order) with one molecular proportion of a meta diamine, chrysoidine, dyestuff
of the Bismarck-brown series, or the like, and one molecular proportion of another
dyestuff' component.
66
"
According to the researches of my foreign correspondents, the so called
chrysoidines" and "dyestuffs of the Bismarck-brown series can be used in place
of metadiamines for producing the dyestuffs herein before and hereinafter defined.
My foreign correspondents mean by the above expression "chrysoidines," generally
those products which can be obtained by coupling one molecular proportion of a
diazo compound with one molecular proportion of a metadiamine, or one molecular
proportion of a tetrazo compound, either with two molecular proportions of a
metadiamine, or (in any order) with one molecular proportion of a metadiamine
and one molecular proportion of another dyestuff component, and the sulphonic
or other derivatives of these azo compounds; and my foreign correspondents

page_text: understand by the above expression "dyestuffs of the Bismarck-brown series,"
generally those colouring matters which can be produced by coupling diazo or
tetrazo derivatives of metadiamido-compounds with inetadiamines, and the sulphonic
and other derivatives of these azo compounds.
COLOURING-MATTER
PRODUCED FROM ONE MOLECULAR PROPORTION OF
DIAMIDODIPHENYLAMINEMONOSULPHONIC ACID, ONE MOLECULAR PRO-
PORTION OF AMIDONAPHTHOL MONOSULPHONIC ACID G, AND TWO
MOLECULAR PROPORTIONS OF METAPHENYLENEDIAMINE.
The tetrazo compound obtained from 2-8 parts of paradiamidodiphenylamine mone
sulphonic acid, in the manner described in the preceding third example, is allowed
to How quickly into a solution containing 24 parts of beta-amido-a-naphthol-beta3-
monosulphonic acid, and rendered alkaline. The resulting intermediate product,
the formation of which is complete within a short time, is diazotised by acidulating
the mixture by means of muriatic acid, and subsequently adding a concentrated
watery solution of 0.7 parts of sodium nitrite. A solution prepared from 3.8 parts
of metaphenylenediaminehydrochloride is added to the resulting tetrazo solution,
and the dye-stuff, which is obtained after adding sodium acetate, is isolated in a
suitable manner. It produces black shades on unmordanted cotton, and the resulting
shades exhibit more than double the intensity which results from the use of the
black cotton-dyes hitherto known. The shades are also distinguished for their
fastness against acids and alkalies. It possesses the following formula :—
SONa
Valuable colouring-matters are also obtained, if the beta-amido-a-naphthol-
beta-monosulphonic acid used in the last example, is replaced by other amido-
naphtholsulphonic acids, or, in general, by an amine capable of further diazotisation,
or if the metaphenylenediamine used as last component in the said example, is
replaced by two molecular proportions of another metadiamine, or a chrysoidine,
or a "dye-stuff of the Bismarck-brown series (employing the same or two different
ones), or by one molecular proportion of a metadiamine, chrysoidine, or dyestuff
of the Bismarck-brown series, and one molecular proportion of another dyestuff
component.
Analogous dye stuffs result, if the tetrazodiphenylaminemonosulphonic acid is
combined with two molecular proportions of an amido product capable of further
diazotisation (employing either the same or two different ones, in particular amido-
naphtholsulphonic acids), or, in any order, with one molecular proportion of such
an amido product, and one molecular proportion of a phenol or the like, and if the
intermediate products are diazotised and combined with metadiamines, chrysoidines,
or dyestuff's of the Bismarck-brown series, or, in case two molecular proportions are

page_text: to be coupled (in any order) with one molecular proportion of a metadiamine,
chrysoidine, or dyestuff of the Bismarck-brown series, and one molecular proportion
of another dyestuff component.
The colouring matters thus obtained are in general distinguished for their great
dyeing power and fasiness, and by their capability of being diazotisable (when
fixed on the fibre), and of combining with the usual developers.
According to the researches of my foreign correspondents, the dye-stuffs
herein before defined also possess value, inasmuch as they, when fixed on the fibre,
and diazotised, likewise on the fibre, yield, by a subsequent treatment with dilute
alkalies or acids, or by a treatment in oxidising baths, for instance, such as are
prepared from potassiumdichroinate, shades which are distinguished for a still
greater intensity and fastness.
Dated this 4th day of December 1894.
NEWTON & SON,
Agents for the Applicant.
The Manufacture or Production of Colouring Matters, and Materials
therefor.
I HENRY EDWARD NEWTON of The Office for Patents, 6 Bream's Buildings,
Chancery Lane in the County of London, Patent Agent, do hereby declare the
nature of this invention and in what manner the same is to be performed, to be
particularly described and ascertained in and by the following statement :-
It is stated in the Annalen der Chemie, volume 265, page 87, that paranitro-
chlorobenzene is converted by sulphonation into the orthochlorometanitrobenzene
sulphonic acid of the formula—
My foreign correspondents have now found that this chloronitrobenzene
sulphonic acid is transformed into a new paranitroparamidodiphenylamineortho-
sulphonic acid, if, for instance, a salt of the said chlorouitro sulphonic acid,
dissolved in hot water, together with sodium acetate or some other alkaline salt,
decomposable by hydrochloric acid, is allowed to act on paraphenylenediamine.
The alkaline salts of this paranitroparamidodiphenylamineorthosulphonic
readily dissolve in water, affording a slightly yellowish brown-colored solution, and
the acid separates in small greyish-brown crystals (soluble with difficulty in water),
on adding mineral acids to the solution of its alkaline salts.
acid
The researches of my foreign correspondents have further shown, that the said
paranitroparamidodiphenylamine orthosulphonic acid is converted by reduction

page_text: into the corresponding paradiamidodiphenylamineorthosulphonic acid, having the
formula-
This diamido-diphenylaminemonosulphonic acid dissolves with difficulty in water
and dilute acetic acid, but readily in dilute solutions of mineral acids, ammonia,
alkaline hydroxides, and alkaline carbonates. The hydrochloride of the new
diamido acid separates in a crystalline state from its concentrated solutions in
water, and forms with stannous chloride a double salt which dissolves with difficulty
in concentrated muriatic acid.
The reduction can be effected in alkaline, or, more profitably, in acid solution,
by means of the known methods in use for analogous purposes.
To illustrate the production of the two new acids hereinbefore referred
to, ciz.paranitroparamidodiphenylamine orthosulphonic acid and paradiamido-
diphenylamine ortho sulphonic acid, the following examples are given. The parts
are by weight.
PRODUCTION OF
ACID FROM
DIPHENYLAMINE ORTHOSULPHONIC
BENZENESULPHONIC ACID AND
PARANITROPARAMIDO
ORTHOCHLOROMETANITRO
PARA PHENYLENEDIAMINE.
6-6 parts of the calcium salt of orthochlorometauitro benzene sulphonic acid and
22 parts of paraphenylene diamine are dissolved in about 500 parts of hot water,
together with 2-8 parts of crystallised sodium acetate. On boiling the liquid, it
gradually assumes a yellowish-brown color. After boiling for about 2 hours, the
new acid which has been formed is precipitated by adding muriatic acid. The
liquid is then allowed to cool, and after several hours the acid is filtered off, washed
with water, and dried at 100 degrees Centigrade.
CONVERSION OF PARANITROPARAMIDODIPHENYLAMINE SULPHONIC ACID INTO
PARADIAMIDO DIPHENYLAMINE SULPHONIC ACID.
3.1 parts of the paranitroparamido diphenylamine orthosulphonic acid are

page_text: gradually stirred into a solution of 11.3 parts of staunous chloride in 35 parts of
concentrated muriatic acid heated to about 40 degrees Centigrade. The sulphonic
acid dissolves, but as the liquid cools, the double salt of the new diamido acid and
stannous chloride separates out. This salt is filtered off, pressed, and redissolved
in water, and the solution is treated with zinc, in order to remove the tin. The
liquid is subsequently concentrated, and the free paradiamido diphenylamine ortho
sulphonic acid is then separated by adding sodium acetate to the concentrated
filtrate. It forms white flakes, which become crystalline after a short time. It is
purified, if necessary, by crystallization from water. Its stability on exposure to
the oxidising action of the air, is not inconsiderable.
As a matter of course, the reduction can also be effected by means of iron, or of
zinc dust, in acetic acid, or dilute mineral acid solutions, or in any other suitable
manner.
The researches of my foreign correspondents show, that paradiamido diphenyl-
amine orthosulphonic acid yields, on diazotisation, a tetrazo compound which can
be used for producing valuable dye-stuffs.
It is known that the meta position of the sulphonic group relatively to the one
amido group contained in the benzidine nucleus, exerts an influence, inasmuch as
the dye-stuffs obtained by diazotising benzidine meta sulphonic acid, and coupling
its tetrazo derivative with amines or phenols, have not the property of striking on
unmordanted cotton. Owing to this fact, it might naturally have been expected
that when the herein described diamido diphenylamine sulphonic acid was diazotised
and coupled with the known dye-stuff components, it would yield azo coloring
matters having no affinity to unmordanted vegetable fibres, a behaviour which
would also be in accordance with the fact, that when nonsulphonated diamido
diphenylamine is diazotised, and combined with the usual dye-stuff components, it
produces coloring matters possessing but slight affinity for cotton fibre.
The researches of my foreign correspondents have, indeed, shown that almost
all coloring matters obtained by combining the tetrazo derivative of paradiamido
diphenylamine orthomonosulphonic acid with phenols, amines, sulphonic or
carboxylic acids thereof, are destitute of the properties of the so-called benzidine
dye-stuffs, inasmuch as they give but weak and valueless shades. Even the
coloring matter which is analogous to the dye-stuff known in commerce as
"diamine black," and which is formed by the combination of two molecular
proportions of amidonaphtholmonosulphonic acid G with a molecular proportion of
the tetrazo derivative of paradiamido diphenylamine sulphonic acid, is entirely
valueless, as it yields only slightly bluish grey shades.
According to the researches of my foreign correspondents, valuable dye-stuffs,
distinguished for their great affinity for vegetable fibre, are, however, obtained
from the said diamido diphenylamine sulphonic acid, if its tetrazo derivative is
combined with components containing basic groups, for, instance metaphenylene
diamine, metatoluylenediamine, or the like.
My foreign correspondents have found that not only the symmetrical disazo
dye-stuffs containing two molecular proportions of a metadiamine, or the like, but
also the mixed disazo dye stuff's produced from molecular proportions of tetrazo-
tised paradiamido diphenylamineortho monosulphonic acid, metadiamines, or the
like, and any other dye-stuff components, possess great technical value; and their
researches have further shown that the coloring matters are also very valuable
which can be produced by combining the tetrazo derivative of paradiamido
diphenylamine orthosulphonic acid, with one or two molecular proportions of
amines which, when coupled, are capable of being further diazotised, or (in any
order) with a molecular proportion of such an amine, and a molecular proportion
of another component, by further diazotising the intermediate products so formed,
and coupling the diazo or tetrazo derivatives, as the case may be, with either one
or two molecular proportions of a meta diamine, or with a molecular proportion of
a meta diamine and a molecular proportion of any other dye-stuff' component.

page_text: DYE-STUFF OBTAINED FROM ONE MOLECULAR PROPORTION OF DIAMIDODI-
PHENYLAMINEMONOSULPHONIC ACID AND TWO MOLECULAR PROPORTIONS
OF META PHENYLENE DIAMINE.
28 parts of paradiamido diphenylamine-ortho-monosulphonic acid are stirred into
300 parts of water, and subsequently dissolved by adding 3 parts of muriatic acid
(20 degrees Baumé). A concentrated solution of 14 parts of sodium nitrite is then
added, in order to prepare the tetrazo compound. When the formation of the
latter is complete, a concentrated solution, in water, of 3:8 parts of metaphenelene
diamine hydrochloride is allowed to flow into the liquid mixture, and the formation
of the dye-stuff is finally completed by adding sodium acetate. The coloring
matter is converted into the sodium salt by suitable treatment, and isolated in the
usual manner. It possesses the following formula :-
produces intense red shades on unmordanted cotton, and, when fixed on the
fibre, can be diazotised and combined with the known developers, such as beta
naphthol, metaphenylene diamine, or the like,-very deep shades being thus obtained,
which withstand washing.
Similar dye-stuffs are formed by using, instead of the metaphenelene diamine of
the above third example, equivalent quantities of other meta diamines, such as
metatoluylenediamine, or the like, or if the tetrazo diphenylamine monosulphonic
acid is combined with a molecular proportion of one metadiamine, and a molecular
proportion of another of these components, or if the said tetrazo compound is
coupled (in any order) with a molecular proportion of a metadiamine and a
molecular proportion of another dye-stuff component..
COLORING MATTER
OF
MOLECULAR
PRODUCED FROM ONE MOLECULAR PROPORTION
DIAMIDO DIPHENYLAMINE MONO SULPHONIC ACID, ONE
PROPORTION OF
AMIDONAPHTHOLMONOSULPHONIC ACID G, AND TWO
MOLECULAR PROPORTIONS OF METAPHENYLENE DIAMINE.
The tetrazo compound obtained from 2.8 parts of paradiamido diphenylamine
monosulphonic acid in the manner described in the preceding third example, is
allowed to flow quickly into an alkaline solution containing 2-4 parts of beta, amido
alpha, naphthol beta, monosulphonic acid. The intermediate product, the formation
of which is complete within a short time, is diazotised by acidulating the mixture
by means of muriatic acid, and subsequently adding a concentrated solution
of 0-7 parts of sodium nitrite. A solution of 3-8 parts of meta phenylenediamine
hydrochloride is then added to the tetrazo solution. The formation of the dye-stuff
is hastened by adding sodium acetate. The coloring matter is isolated in a suitable
B

page_text: manner.
It produces black shades on unmordanted cotton of more than double the
intensity of those afforded by the black cotton dyes hitherto known, and also
distinguished for their fastness in presence of acids and alkalies. It is represented
by the following formula :—
SO,Na
NH,
Valuable coloring matters are also obtained, if, instead of the beta, amido alpha
naphtholbeta, monosulphonic acid of the last example, equivalent quantities are
used of other amidonaphtholsulphonic acids, or, in general, of amines which, when
coupled, may be further diazotised, or by substituting for the metaphenylenediamine
used as last component in the said example, either two molecular proportions of
another meta diamine, or molecular proportions of each of two different amines, or
a molecular proportion of a meta diamine and a molecular proportion of another
dye-stuff component, using these in any order.
Analogous dye-stuffs are formed if the tetrazo diphenylaminemonosulphonic
acid is combined with two molecular proportions of an amido compound capable of
being further diazotised (using either one or two different compounds, especially in
the case of the amidonaphtholsulphonic acids), or, in any order, with a molecular
proportion of such an amido compound and a molecular proportion of a phenol or
the like, and if the intermediate products are rediazotised, and combined with
metadiamines, or in case two molecular proportions are to be coupled (in any
order) with a molecular proportion of a meta diamine and a molecular proportion
of another dye-stuff component.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed, as communicated to
me from abroad, I declare that what I claim is :-
1. The production of paranitro paramidodiphenylamine ortho sulphonic acid of
the formula-

page_text: 1
from orthochlorometanitro benzene sulphonic acid (CI: SO₂H NQ₂ = 1:2:4) and
paraphenylenediamine.
2. The conversion of paranitro paramidodiphenylamine orthosulphonic acid by
reduction into the paradiamidodiphenylamine ortho sulphonic acid of the formula-
3. The process for producing paradiamidodiphenylamine ortho sulphonic acid,
which process consists in allowing orthochlorometanitro benzene sulphonic acid, or
salts thereof, to act on paraphenylene diamine, and subsequently reducing the
so-formed paranitro parainido diphenylamine ortho sulphonic acid, or salts thereof.
4. The production of azo dye-stuffs by means of the tetrazo derivative of para-
diamidodiphenylamine orthosulphonic acid.
5. The process for producing symmetrical and mixed disazo dye-stuffs, which
process consists in combining a molecular proportion of the tetrazo derivative of
paradiamidodiphenylamine ortho sulphonic acid, either with two molecular pro-
portions of meta-diamine (using. either one or two different amines), or (in any
order) with a molecular proportion of a metadiamine and a molecular proportion
of another dye-stuff' component.
6. The production of trisazo and tetrakisazo coloring matters by combining a
molecular proportion of the tetrazo derivative of paradiamido diphenylamine ortho
sulphonic acid with a molecular proportion of an amido compound which, when
coupled, may be further diazotised, or with two molecular proportions of such au
amido compound (using either one or two different amido compounds), or, in any
order, with a molecular proportion of such an amido compound and a molecular
proportion of another dye-stuff component, rediazotising the so-formed intermediate
products, and subsequently combining, in the one case, the diazo compound with a
single molecular proportion of a meta diamine, and, in the other case, the tetrazo
compound with two molecular proportions of a meta diamine (using either the same
or two different metadiamines), or, in any order, with a molecular proportion of a
meta diamine and a molecular proportion of another dye-stuff component.
7. As new products of manufacture
a) paranitro paramidodiphenylamine ortho sulphonic acid;
haundiamid dishonelaming orthosulphonia raid. and
same result.
Dated this 3rd day of September 1895.
NEWTON & SON,
Agents for the Applicant.
NEWTON & SON,
Agents for the Applicant.