A Process for the Manufacture of Black Colouring Matters.
Year: 1890

page_text: Date of Application, 24th Sept., 1890
Complete Specification Left, 29th May, 1891-Accepted, 4th July, 1891
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE SOCIETY OF CHEMICAL INDUSTRY
IN BASLE, of Basle, Switzerland.]
A Process for the Manufacture of Black Colouring Matters.
1, 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:-
This invention relates to the production of new black colouring matters derived
from the monoalkylised derivatives of betanaphthylamine, particularly from mono-
(ß) H
ethyl-beta-naphthylamine of the formula C₁H, N- C₂H,-described by
Henriques (see Berichte der Deutschen Chem. Gesellschaft tome 17. page 2668).
The following is the process :-
_
First, diazo compounds of naphthylamine disulphonic acids are allowed to react
in the well known manner upon alpha-naphthylamine.
The azo dye thus produced is diazotated and then combined with mono-ethyl-
beta-naphthylamine.
EXAMPLE I :
35 kilos of alpha-naphthylamine disulphonate of soda, obtained by sulphonation
of alpha-naphthylamine or alpha-naphthylamine-monosulphonic acid in the known
manner, and 7 kilos of nitrite of sodium are dissolved in 600 kilos of water and the
solution is allowed to run slowly into 35 kilos of muriatic acid, then a solution of
18 kilos of hydrochlorate of alpha-naphthylamine is added. The well known
intermediate compound is immediately formed.
To a solution of this azo compound there are added 11 kilos of hydrochloric acid
and 7 kilos of nitrite of sodium.
The brownish diazo-azo compound thus produced is introduced into a cooled
solution of 17.5 kilos of mono-ethyl-beta-naphthylamine in 15 kilos of muriatic
acid.
After addition of an equivalent quantity of acetate of sodium, the formation of
the dye stuff begins and the reaction is completed in twelve hours.
The dye stuff is precipitated by common salt in the shape of a black mass, which
is filtered pressed and dried.
The colouring matter thus obtained forms a splendid black colour, easily soluble
in water with a blue black colour. By addition of soda lye or ammonia, the
solution is not changed; with concentrated sulphuric acid it changes into a pure
green colour.
The dye stuff dyes wool and silk from grey to blue black, according to its
strength; the dye resists the action of soap, of the atmosphere and of light, and
has the following formula :-
DXAMPLE 11:
For the production of a grey black colouring matter from mono-amyl-beta-
naphthylamine, the diazo compound of the amido-azo-naphthaline disulphonic acid,
obtained as described in Example I, is precipitated with common salt, filtered and
D1

page_text: introduced into the alcoholic solution of 21.5 kilos of mono-amylbetanaphthyl-
amine.
After 24 hours' repose the formation of the colouring matter is completed. It is
then neutralized with soda, the alcohol is evaporated, the remaining colouring
matter is extracted with water, precipitated with common salt, filtered, pressed and
dried.
By this process the colouring matter is obtained in the form of a black powder,
which is easily soluble in water.
In a bath acidulated with acetic acid it dyes wool grey black with a greenish
shade.
The process may be conducted in a similar manner substituting for the mono-
ethyl-betanaphthylamine, 16 kilos of monomethylbetanaphthylamine, or instead of
the alphanaphthylamine disulphonic acid, a sulphonic acid of beta-naphthylamine
or the disulphonic acids of aniline, toluidine and xylidine may be employed.
Dated this 24th day of September 1890.
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
A Process for the Manufacture of Black Colouring Matters.
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:
This invention relates to the production of new black colouring matters derived
from the monoalkylised derivatives of betanaphthylamine, particularly from mono-
(ẞ) H
ethyl-beta-naphthylamine of the formula C₁H, N C,H,-described by
Henriques (see Berichte der Deutschen Chem. Gesellschaft tome 17. page 2668).
The following is the process :-
10
First, diazo compounds of naphthylamine disulphonic acids are allowed to react
in the well known manner upon alpha-naphthylamine.
The azo dye thus produced is diazotated and then combined with mono-ethyl-
beta-naphthylamine.
EXAMPLE I.
35 kilos of alpha-naphthylamine disulphonate of soda, obtained by sulphonation
of alpha-naphthylamine or alpha-naphthylanine-monosulphonic acid in the known
manner, and 7 kilos of nitrite of sodium are dissolved in 600 kilos of water and the
solution is allowed to run slowly into 35 kilos of muriatic acid, then a solution of
18 kilos of hydrochlorate of alpha-naphthylamine is added. The well known
intermediate compound is immediately formed.
To a solution of this azo compound there are added 11 kilos of hydrochloric acid
and 7 kilos of nitrite of sodium.
The brownish diazo-azo compound thus produced is introduced into a cooled
solution of 17.5 kilos of mono-ethyl-beta-naphthylamine in 15 kilos of muriatic
acid.
After addition of an equivalent quantity of acetate of sodium, the formation of
the dye stuff begins and the reaction is completed in twelve hours.
The dye stuff is precipitated by common salt in the shape of a black mass, which
is filtered, pressed and dried.
The colouring matter thus obtained forms a splendid black powder easily soluble
in water with a blue black colour. By addition of soda lye or ammonia, the

page_text: solution is not changed; with concentrated sulphuric acid it changes into a pure
green colour.
The dye stuff dyes wool and silk from grey to blue black, according to its
strength; the dye resists the action of soap, of the atmosphere and of light, and has
the following formula:-
EXAMPLE II.
For the production of a grey black colouring matter from mono-amyl-beta-
naphthylamine, the diazo compound of the amido-azo-naphthaline disulphonic acid,
obtained as described in Example I, is precipitated with common salt, filtered and
introduced into the alcoholic solution of 21.5 kilos of mono-amylbetanaphthyl-
amine.
After 24 hours repose the formation of the colouring matter is completed. It is
then neutralized with soda, the alcohol is evaporated, the remaining colouring
matter is extracted with water, precipitated with common salt, filtered pressed and
dried.
By this process the colouring matter is obtained in the form of a black powder,
which is easily soluble in water.
In a bath acidulated with acetic acid it dyes wool grey black with a greenish
shade.
The process may be conducted in a similar manner substituting for the mono-
ethyl-betanaphthylamine, 16 kilos of monomethylbetanaphthylamine, or instead of
the alphanaphthylamine disulphonic acid, a sulphonic acid of beta-naphthylamine
or the disulphonic acids of aniline, toluidine and xylidine may be employed.
Having now particularly described and ascertained the nature of my said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
1. The process of producing black colouring matters from the mono alkylised
derivatives of beta-naphtylamine by their combination with the diazo compounds of
the intermediate azo-dyes, resulting from naphtylamine disulphonic acids or from
disulphonic acids of aniline, toluidine or xylidine with alpha-naphtylamine sub-
stantially as described.
2. The black colouring matters produced as above set forth.
ABEL & IMRAY,
Agents for the Applicant.