Manufacture of New Colouring Matters Derived from Muscarine.
Year: 1894

page_text: Date of Application (in United Kingdom), 4th Aug., 1894
Complete Specification Left, 22nd Apr., 1895-Accepted, 24th May, 1895.
Manufacture of New Colouring Matters Derived from Muscarine.
We, JEAN CLAUDE LOUIS DURAND, DANIEL EDOUARD HUGUENIN and.
ADOLPHE JEAN JAMES D'ANDIRAN, constituting the Firm of L. Duraul
Huguenin & Co., Manufacturers, of St. Fons (Rhone) France, do hereby declare
the nature of this invention to be as follows:-
According to this invention, muscarine, obtained by the action of nitrosodi-
methylaniline on dioxynaphthaline 2-7, is treated with ammonia, fatty or aromatic
or sulphoconjugate aromatic amines for the production of new colouring matters.
For example, 1 part muscarine is heated on the water bath with 3 parts aniline,
after reaction, alcohol is added, and after cooling, filtering and washing with alcohol,
the resulting green colouring matter is pressed and dried.
The mother liquor acidulated with muriatic acid produces another colouring
matter of blue gray colour. The two colouring matters thus produced give variou°
colours with various solvents, these colours depending upon the proportions of the
ingredients and the time and temperature of the initial reaction. Both sets of
colouring matters are applicable for printing fabrics.
Dated this 4th day of August 1894.
ABEL & IMKAY,
Agents for the Applicants..
COMPLETE SPECIFICATION.
Manufacture of New Colouring Matters Derived from Muscarine. .
We, JEAN CLAUDE LOUIS DURAND, DANIEL EDOUARD HUGUENIN. and
ADOLPHE JEAN JAMES D'ANDIRAN, constituting the Firm of L. Durand
Huguenin & Co., Manufacturers, of St. Fons (Rhone) France, do hereby declaro
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 :-
Our invention relates to the manufacture of new colouring matters by the action
of ammonia, fatty or aromatic amines or sulphoconjugate aromatic amines on
muscarine which is obtained by the action of nitrosodimethylaniline on dioxy-
naphthaline 2-7.
By way of example we shall describe more particularly the colouring matters
obtained by the action of aniline on muscarine, the mode of operation being almost
the same in the various cases.

page_text: We cause 1 part muscarine to act at the temperature of the water bath on
3 parts aniline; the mass, at first liquid, becomes somewhat thickened towards the
end of the operation. When a sample taken from the mass and dissolved in alcohol
and acetic acid no longer manifests the presence of muscarine, the heating is
stopped, an equal volume of alcohol is added to the mass, and the whole is well
stirred and left to cool. After cooling, it is filtered, washed with alcohol to remove
thoroughly all traces of aniline; it is then pressed and dried.
The dried product thus obtained constitutes a green colouring matter which
dissolves very readily in acetic acid.
In the mother liquor there is a blue gray colouring matter which can be easily
obtained by acidulating the liquor with muriatic acid, filtering and drying.
This second colouring matter also dissolves very readily in acetic acid. These
colouring matters have the following characteristics.
Both of them are insoluble in pure water and benzene; both are soluble in
alcohol but in different degrees. With sulphuric acid they can produce sulpho-
conjugate derivatives.
The green colouring matter dissolves in aniline producing a violet colour,
whereas the gray blue colouring matter dissolves in aniline producing a blue gray
colour.
In acetic acid alone or with alcohol added, the green colouring matter dissolves
colouring the solvent green blue, whereas the gray blue colouring matter dissolves
in the same solvents colouring them blue violet gray.
The solution of the green colouring matter in alcohol having caustic soda added
to it presents a red tint, whereas the gray blue colouring matter dissolves in alcohol
and caustic soda producing a red violet colour.
In concentrated sulphuric acid the green colouring matter dissolves producing a
brown violet solution; the blue gray colouring matter gives with the same solvent
a dirty green solution.
Both colouring matters dissolve in sulphuric acid having nitric acid added to it,
producing a dirty red solution.
By adding a little water to the solution of the green colouring matter in sulphuric
acid, the solution becomes orange coloured, but, under like conditions, the solution
of the gray blue colouring matter in sulphuric acid becomes violet in colour. Au
addition of much water to the solution of the green colouring matter in sulphuric
acid gives this solution a violet colour, and precipitates the colouring matter again;
whereas an addition of much water to the solution of the gray blue colouring
matter in sulphuric acid gives this solution a violet tint.
The gray blue colouring matter is as insoluble in concentrated as in dilute
muriatic acid; as for the green colouring matter, it is insoluble in dilute muriatic
acid, whilst it slightly dissolves in concentrated muriatic acid producing a brown
coloured solution, which gives a violet precipitate on addition of water.
In nitric acid of 40° Bé. the green colouring matter dissolves producing a green
solution; under like conditions the gray blue colouring matter gives a brown violet
solution. An addition of caustic soda to a solution of the green colouring matter
produces a violet precipitate, whereas an addition of caustic soda to a solution of
the blue gray colouring matter produces a gray precipitate. Both the colouring
matters can be used in paste form.
They are especially applicable to the printing of fabrics, they resist soap and
light. They print on taunin, with subsequent treatment with tartar emetic.
According to the proportions of aniline employed, the temperature at which the
reaction takes place, and the duration of the heating, there may be obtained a
series of colouring matters varying from violet blue to strong green, passing through
indigo blue; we therefore do not limit ourselves to the proportions of aniline, the
temperature or the time of heating above indicated.

page_text: Having now particularly described and ascertained the nature of this invention
and in what manner the same is to be performed, we declare that what we
claim is :-
1. The herein described manufacture of new colouring matters by the action
of ammonia, fatty or aromatic amines or of sulphoconjugate aromatic amines, on
muscarine.
2. The manufacture of colouring matters by heating on the water bath muscarine
with addition of aniline, substantially as described.
3. The manufacture of a green and of a blue gray colouring matter by treating
with alcohol the product resulting from the reaction of aniline on muscarine at
the temperature of the water bath, and by separating by filtration the green
colouring matter less easily soluble in alcohol, and by precipitating the blue gray
colouring matter from the mother liquor by addition of muriatic acid, substantially
as described.
4. The colouring matters manufactured as above set forth.
ABEL & IMRAY,
Agents for the Applicants.