The Production of a Substituted Meta Diamine and of Colouring Matters Derived therefrom.
Year: 1889

page_text: Date of Application, 17th Dec., 1889
Complete Specification Left, 13th Sept., 1890-Accepted, 18th Oct., 1890
PROVISIONAL SPECIFICATION.
[Communicated from abroad by LA SOCIÉTÉ ANONYME DES MATIÈRES COLORANTES
ET PRODUITS CHIMIQUES DE ST. DENIS, of 105, Rue Lafayette, Paris, France.]
The Production of a Substituted Meta Diamine and of Colouring
Matters Derived therefrom.
I, JOHN IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Consulting Engineer and Patent Agent, do hereby declare
the nature of this invention to be as follows:-
This invention relates to the preparation of a substituted dinitrated and dis-
symetric meta diamine, and of coloring matters derived therefrom.
For this purpose there is taken as point of departure dinitrochloro-benzol Cl. NO³
- 2 4, and the process is as follows:
NO 1
1
a. By either simply mixing (or in alcoholic solution or otherwise) 10 kilos. of
dinitrochloro-benzol with 7 kilos. of meta-mido dimethylaniline and then heating for
some time in a water bath, there is obtained the product of condensation dinitro-
metamido dimethyl diphenylamine. The reaction product dried and treated with
benzine or hot alcohol, gives on cooling very fine laminated crystals of an orange
color of the fusing point of 136°.
This substituted meta diamine is soluble in mineral acids and in acetic acid, and
insoluble in water. The solutions in mineral acids give up the base on dilution.
b. By heating 14 kilos. of hydrochlorate of nitroso dimethyl-aniline together with
15 kilos. of substituted meta base (dinitro metamido-dimethyldiphenylamine) in acetic
or alcoholic solution, there is soon produced a blue colorination of slightly violet hue
of the whole mass, which is readily precipitated by the addition of sea salt.
The precipitate is again dissolved in water and precipitated in a medium slightly
acidulated with hydrochloric acid, by means of an additional quantity of salt, when
it gives a brilliant and crystalline brownish-red mass having considerable coloring
power.
If the 14 kilos. of hydro-chlorate of nitroso-dimethylaniline be replaced by an
equivalent quantity of hydro-chlorate of nitroso-diethylaniline, there is obtained a
coloring matter somewhat similar to the preceding one.
The aqueous solutions of these coloring matters are characterised by a strong red
fluorescence, which remains after dyeing on silk or cotton, being visible with the latter
in artificial light.
c. These dinitrated coloring matters when treated with ordinary reducing agents,
such as iron and hydrochloric acid; tin or zinc and hydrochloric acid, give reaction
products which are also coloring matters.
The coloring matters obtained by the process described under (b) dye wool a blue
violet color, cotton mordanted with tannin a blue violet color which is fluorescent in
artificial light, and silk a violet color.
The coloring matters obtained by the process (c) dye wool and cotton a violet-red
color, and silk a red-violet color.
Dated this 17th day of December 1889.
זזדי
D TACT AXZ
ТАГТ А X
Agents for the Applicant.

page_text: COMPLETE SPECIFICATION.
The Production of a Substituted Meta Diamine and of Colouring
Matters Derived therefrom.
I, JOHN IMRAY of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Consulting Engineer and 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 :-
This invention relates to the preparation of a substituted dinitrated and dis-symetric
meta diamine, and of coloring matters derived therefrom.
For this purpose there is taken as point of departure dinitrochloro-benzol Cl. NO²
- NO2-1-2 4 and the process is as follows:
a. By either simply mixing (or in alcoholic solution or otherwise) 10 kilos. of
dinitrochloro-benzol with 7 kilos. of metamido dimethylaniline and then heating for
some time in a water bath, there is obtained the product of condensation dinitro-
metamido dimethyl diphenylamine.
The reaction product dried and treated with benzine or hot alcohol, gives on cooling
very fine laminated crystals of an orange color of the fusing point of 136°.
This substituted meta-diamine is soluble in mineral acids and in acetic acid, and
insoluble in water. The solutions in mineral acids give up the base on dilution.
b. By heating 14 kilos. of hydrochlorate of nitroso-dimethylaniline together with
15 kilos. of substituted meta base (dinitro metamido-dimethyl-diphenylamine) in acetic
or alcoholic solution, there is soon produced a blue colorination, of slightly violet hue
of the whole mass, which is readily precipitated by the addition of sea salt.
The precipitate is again dissolved in water and precipitated in a medium slightly
acidulated with hydrochloric acid, by means of an additional quantity of salt, when it
gives a brilliant and crystalline brownish red mass having considerable coloring
power.
If the 14 kilos. of hydrochlorate of nitroso-dimethylaniline be replaced by an
equivalent quantity of hydrochlorate of nitroso-diethylaniline, there is obtained a
coloring matter somewhat similar to the preceding one.
The aqueous solutions of these coloring matters are characterised by a strong red
fluorescence, which remains after dyeing on silk or cotton, being visible with the latter
in artificial light.
c. These dinitrated colouring matters when treated with ordinary reducing agents,
such as iron and hydrochloric acid tin or zinc and hydrochloric acid, give reaction
products which are also coloring matters.
The coloring matters obtained by the process described under (b) dye wool a blue.
violet color, cotton mordanted with tannin a blue violet color, which is fluorescent in
artificial light, and silk a violet color.
The coloring matters obtained by the process (c) dye wool and cotton a violet-red
color, and silk a red-violet color.
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 1
claim is :
1. The production of dinitro metadimethylamido diphenylamine by condensation of
iinitrochlorobenzol (CI. NO2 - NO2-1-2-4) with metamido-dimethylaniline.
2. The condensation of dinitrometadimethyl-amido-diphenylamine with nitroso-
dimethyl-aniline.
Dated this 13th day of September 1890.
ABEL & IMRAY,
Agents for the Applicant.