Production of Azo Coloring Matters from Dioxynaphthalinmono- sulphonates.
Year: 1889

page_text: Date of Application, 30th Aug., 1889
Complete Specification Left, 20th May, 1890-Accepted, 21st June, 1890
[Communicated from abroad by THE FARBWERKE VOrmals Meister LUCIUS AND
BRUNING, of Hoechst /Main, in the Empire of Germany, Chemical Manu-
facturers.]
Production of Azo Coloring Matters from Dioxynaphthalinmono-
sulphonates.
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the County
of London, Fellow of the Institute of Patent Agents, do hereby declare the nature of
this invention to be as follows:-
In the Provisional Specification No. 9642 of 1889 is described a new method for
producing dioxynaphthalinmonosulphonates.
These sulphonates (2 mol.) combine quite easily in slightly acid, neutral or alkaline
solution with tetrazo compounds (1 mol.) forming thereby substantive coloring matters.
For example, 55 parts by weight of dioxynaphthalinmonosulphonate of sodium R
(prepared from the beta-naphthol disulphonic acid R) are dissolved in 1000 parts
by weight of water and to this solution are added 70 parts by weight of carbonate
of soda. 184 parts by weight of benzidine are then diazotated in the well known
manner, and the tetrazo compound thus formed is added slowly at ordinary temperature
and under constant agitation to the above solution of the dioxynaphthalinesulphonate
of sodium. The action is completed in about 6 hours. The whole coloring matter
formed can be separated and obtained in the usual way.
The reaction seems to take place in 2 phases: first there are formed intermediary
products, which for one molecule of the tetrazo compound contain only one molecule
of dioxynaphthalinsulphonate of sodium.
For example: 12.2 parts by weight of dimethoxybenzidine are diazoiated in the
usual way. To the tetrazo compound thus formed, is added a solution of 13.1 parts
by weight of dioxynaphthalinsulphonate of sodium Y (prepared from the beta-
naphtholdisulphonic acid Y) in 200 parts by weight of water and afterwards a solution
of 32 parts by weight of acetate of soda in 200 parts by weight of water.
A short time after admixture the intermediary product separates in form of lumps.
The intermediary products thus formed are colored, but they do not possess the
qualities of coloring matters. They are insoluble in water and soda solutions and
contain still a diazo group apt to be coupled with a second molecule of the same or of
another combinable body, for example, a molecule of a phenol, a base or a sulphonic
acid of the bodies mentioned.
When to the intermediary product above mentioned are added for example 12.3 parts
by weight of naphthionate of sodium dissolved in 100 parts by weight of water, the
action is completed in about 12 hours and there is thus formed a coloring matter
having the constitution

page_text: COMPLETE SPECIFICATION.
Production of Azo Coloring Matters from Dioxynaphthalinmono-
sulphonates.
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the County
of London, Fellow of the Institute of Patent Agents, 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:-
In the Specification No. 9642 of 1889 is described a new method for producing
dioxynaphthalinmonosulphonates.
These sulphonates (2 mol.) combine quite easily in slightly acid, neutral or alkaline
solution with tetrazo compounds (1 mol.) forming thereby substantive coloring matters.
For example, 55 parts by weight of dioxynaphthalinmon osulphonate of sodium R
(prepared from the beta-naphtholdisulphonic acid R) are dissolved in 1000 parts by
weight of water and to this solution are added 70 parts by weight of carbonate of
soda. 184 parts by weight of benzidine are then diazotated in the well known
manner and the tetrazo compound thus formed is added slowly at ordinary temperature
and under constant agitation to the above solution of the dioxynaphthalinesulphonate
of sodium. The action is completed in about 6 hours. The whole coloring matter
formed can be separated and obtained in the usual way.
The reaction seems to take place in 2 phases: first there are formed intermediary
products which for one molecule of the tetrazo compound contain only one molecule
of dioxynaphthalinsulphonate of sodium.
For example: 12-2 parts by weight of dimethoxybenzidin are diazotated in the
ustat way. To the tetrazo compound thus formed, is added a solution of 13.1 parts
by weight of dioxynaphthalinsulphonate of sodium Y (prepared from the beta-
naphtholdisulphonic acid Y) in 200 parts by weight of water, and afterwards a
solution of 32 parts by weight of soda in 200 parts by weight of water.
A short time after admixture the intermediary product separates in form of lumps.
The intermediary products thus formed are colored, but they do not possess the
qualities of coloring matters. They are insoluble in water and soda solutions, and
contain still a diazo group apt to be coupled with a second molecule of the same or of
another combinable body, for example, a molecule of a phenol, a base or a sulphonic
acid of the bodies mentioned.
When to the intermediary product above mentioned are added for example 12-3 parts
by weight of naphthionate of sodium dissolved in 100 parts by weight of water, the
action is completed in about 12 hours and there is thus formed a coloring matter
having the constitution :
Having now particularly described and ascertained the nature of this inven- 4
tion and in what manner the same is to be performed, I declare that what I
claim is :-
1. The production of coloring matters by combining, substantially as herein
described, the dioxynaphthalinmonosulphonates described in the Specification No. 9642
of 1889 with tetrazo compounds, such as: Tetrazodiphenyl, Tetrazoditolyl, Tetrazo- 4
dimethoxydiphenyl, Tetrazo-diethoxydiphenyl, Tetrazostilben, Tetrazostilbendisul-
phonic acid.
2. The coloring matters produced by the combination above referred to.