The Manufacture and Production of New Brown Colouring Matter.
Year: 1899

page_text: PROVISIONAL SPECIFICATION.
The Manufacture and Production of New Brown Colouring Matter.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields, in the County of London,
Gentleman, do hereby declare the nature of this invention (which has been
communicated to me from abroad by the Badische Anilin & Soda Fabrik of
Ludwigshafen-on-Rhine, in the German Empire) to be as follows:-
It is known that on nitrating para-amido-phenol-ortho-sulphoacid, a nitro-
amido-phenol-sulphoacid is obtained, which is regarded as the ortho-sulphoacid
of para-amido-ortho-nitro-phenol. My foreign correspondents have discovered
that if this body be treated with dinitro-chlor-benzene in the presence of suit-
able substances for binding hydrochloric acid, such, for instance, as soda, or
sodium acetate, then, in a short time, an almost complete reaction takes place
between the two bodies forming a tri-nitro-hydroxy-di-phenylamine-sulphoacid.
My foreign correspondents have found that this di-phenylamine derivative, on
heating with sulphur and sodium sulphide yields a colouring-matter which
possesses an excellent affinity for vegetable fibres, dyeing them brown-maroon
shades. If the goods so dyed be treated with sulphate of copper in a bath
acidified with acetic acid the shade changes towards dark-brown. The colour of
the goods, both before and after this treatment, is characterised by an excellent
degree of fastness.
The following examples will serve to further illustrate the nature of the inven-
tion, but the invention is not confined to these examples. The parts are by
weight.
EXAMPLE 1.
CONDENSATION OF ORTHO-NITRO-PARA-AMIDO-PHENOL-ORTHO-SULPHOACID WITH DI-
NITRO-CHLOR-BENZENE.
Dissolve about fifty-eight parts of ortho-nitro-para-amido-phenol-ortho-sulpho-
acid in about one hundred and eighty parts of water, containing about twenty
parts of calcined soda, then add thirteen parts of calcined soda and
Boil the mixture
fifty parts of dinitro-chlor-benzene to the solution.
in
a
an
inverted
for
vessel, fitted with
condenser,
about four
hours, or until the di-nitro-chlor-benzene has practically disappeared. Allow
the solution to cool. A paste of crystalline flakes of the diphenylamine derivative
forms. Collect by filtering, wash with a little common salt solution, press and
dry. If desired the reaction product can be purified by re-dissolving in water,
filtering to get rid of insoluble impurities, precipitating with common salt, and
again collecting.
TE

page_text: with sixty parts of sulphur and one hundred and fifty parts of crystalline sodium
sulphide. Heat the mixture in an iron pot slowly to a temperature of about
140° Centigrade. Maintain at this temperature and stir until the mass becomes
so solid that it can be pulverised, then reduce to powder. This powder can be
directly used in dyeing. It is soluble in water, the solutions being red-brown
and it dyes unmordanted cotton reddish-brown shades, which become dark-brown
on treatment with copper sulphate in a bath acidified with acetic acid. The
colouring-matter can be precipitated from its aqueous solution by common salt.
It can also be precipitated (by ammonium chloride, or hydro-chloric acid,) in the
form of brown flocks which, in either case, can be dissolved in a solution con-
taining an excess of sulphide of soda the solution being violet.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.
'
The Manufacture and Production of New Brown Colouring Matter.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields, in the County of London,
Gentleman, do hereby declare the nature of this invention (which has been
communicated to me from abroad by the Badische Anilin & Soda Fabrik of
Ludwigshafen-on-Rhine, in the German Empire) and in what manner the same
is to be performed to be particularly described and ascertained in and by the
following statement:-
It is known that on nitrating para-amido-phenol-ortho-sulphoacid, a nitro-
amido-phenol-sulphoacid is obtained, which is regarded as the ortho-sulphoacid
of para-amido-ortho-nitro-phenol. My foreign correspondents have discovered
that if this body be treated with dinitro-chlor-benzene in the presence of suit-
able substances for binding hydrochloric acid, such, for instance, as soda, or
sodium acetate, then, in a short time, an almost complete reaction takes place
between the two bodies forming a tri-nitro-hydroxy-di-phenylamine-sulphoacid.
My foreign correspondents have found that this di-phenylamine derivative on
heating with sulphur and sodium sulphide yields a colouring matter which
possesses an excellent affinity for vegetable fibres, dyeing them brown-maroon
shades. If the goods so dyed be treated with sulphate of copper in a bath
acidified with acetic acid the shade changes towards dark brown. The colour of
the goods, both before and after this treatment, is characterised by an excellent
degree of fastness.
The following examples will serve to further illustrate the nature of the inven-
tion and the manner in which it can be carried into practice, but the invention
is not confined to these examples.
The parts are by weight.
EXAMPLE 1.
CONDENSATION OF ORTHO-NITRO-PARA-AMIDO-PHENOL-ORTHO-SULPHOACID WITH DI-
NITRO-CHLOR-BENZENE.
Dissolve about fifty-eight parts of ortho-nitro-para-amido-phenol-ortho-sulpho-
acid in about one hundred and eighty parts of water, containing about twenty
parts of calcined soda, then add thirteen parts of calcined. soda and
fifty parts of dinitro-chlor-benzene to the solution. Boil the mixture
in a vessel, fitted with an inverted condenser, for about four

page_text: hours, or until the di-nitro-chlor-benzene has practically disappeared: Allow
the solution to cool: A paste of crystalline flakes of the diphenylamine derivative
forms. Collect by filtering, wash with a little common salt solution, press and
dry. If desired the reaction product can be purified by re-dissolving in water,
filtering to get rid of insoluble impurities, precipitating with common salt, and
again collecting.
EXAMPLE 2.
CONVERSION OF THE DIPHENYL-AMINE DERIVATIVE OBTAINED ACCORDING TO
EXAMPLE 1 INTO THE NEW BROWN COLOURING MATTER.
Mix together thirty parts of the dry product, obtained according to Example 1,
with sixty parts of sulphur and one hundred and fifty parts of crystalline sodium
sulphide. Heat the mixture in an iron pot slowly to a temperature of about
140 degrees Centigrade. Maintain at this temperature. and stir, until the mass be-
comes so solid that it can be pulverized, then reduce to powder. This powder can
be directly used in dyeing. It is soluble in water, the solutions being red-brown,
and it dyes unmordanted cotton reddish-brown shades, which become dark-brown
on treatment with copper sulphate in a bath acidified with acetic acid. The
colouring matter can be precipitated from its aqueous solution by common salt.
It can also be precipitated (by ammonium chloride, or hydro-chloric acid,) in the
form of brown flocks which, in either case, can be dissolved, in a solution con-
taining an excess of sulphide of soda the solution being violet.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what
I claim is:-
1. In the manufacture of new brown colouring matter condensing the herein-
before defined nitro-amido-phenol sulpho-acid with di-nitro-chlor-benzene sub-
stantially as herein before described.
2. In the manufacture of new brown colouring matter the condensation of
ortho-nitro-para-amido-phenol-ortho-sulphoacid with di-nitro-chlor-benzene as
hereinbefore described under Example 1.
3. The manufacture of new brown colouring matter by treating the condensa-
tion product of di-nitro-chlor-benzene and the herein defined nitro-amido-phenol-
sulphoacid with sulphur and an alkaline sulphide, substantially as hereinbefore
described.
4. The manufacture of new brown colouring matter substantially as described
under Example 2.
5. As a new product of manufacture brown colouring matter such as can be
obtained by heating the condensation product of dinitro-chlor-benzene and the
herein defined nitro-amido-phenol-sulpho acid with sulphur and an alkaline
sulphide, substantially as hereinbefore described.
Dated this 6th day of July 1900.
JOHNSONS & WILLCOX.
47, Lincoln's Inn Fields, London, W.C., Agents.