Manufacture of New Derivates of Tannin and Catechine and of Colouring Matters Obtained therefrom.
Year: 1889

page_text: Date of Application, 30th Sept., 1889-Accepted, 2nd Nov., 1889
COMPLETE SPECIFICATION.
Manufacture of New Derivates of Tannin and Catechine and of
Colouring Matters Obtained therefrom.
We, JEAN CLAUDE LOUIS DURAND, DANIEL EDOUARD HUGUENIN, and ADOLPHE
JEAN JAMES D'ANDIRAN; of the Société I. Durand, Huguenin & Cie., Manufacturers,
of Bâle, Switzerland, 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 :-
According to the Specification No. 4899 of 1881, colouring matters bearing the
generic name "Gallocyanines" were produced by the reaction of nitrous derivates of
tertiary aromatic amines on various tannins, catechine and gallic acid. The object of
the present invention is the production of new gallocyanines by the reaction of the
same nitrous derivates of tertiary aromatic amines on a set of new substances derived
from tannin and catechine. These substances are amides obtained by the condensation
of tannin or catechine with primary aromatic amines.
In order that our invention may be more clearly understood, we shall describe,
in the way of example, the preparation of gallonaphthylamides, that is to say,
products of condensation of tannin with the naphthylamines.
They are obtained simply by heating tannin with alpha- or beta naphthylamine.
The product of condensation is the alpha or the beta gallonaphthylamide, according as
alpha or beta naphthylamine is employed in the operation. We introduce one part of
tannin into about three parts of melted naphthylamine; when the whole is dissolved
we heat gradually to 150°-180° C. At first there is great evolution of water
vapour, and the completion of the reaction is indicated by cessation of all but very
slight ebullition. On cooling, the new substance crystallises before the naphthylamine,
the excess of which is separated by running the hot mass into benzine or other solveni
which can remove excess of untransformed amine without dissolving the gallonaph-
thylamide.
This process is described by way of example only, as various proportions and
temperatures may be employed for obtaining the desired result.
A similar reaction takes place with catechine which we have condensed with aniline,
the toluidines, xylidines, &c., as well as with the a and ẞ naphthylamines.
All these bodies react on the hydrochlorate of nitrosodimethylaniline and the
nitrous derivates of the tertiary aromatic amines generally, producing colouring
matters in a manner quite analogous to that described in the Specification No. 4899
of 1881 above referred to. These colours are scarcely soluble in the ordinary solvents,
they give products of reduction with alkaline bisulphites and dye mordanted fibres
red violet to very blue violet.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, we declare that what we
claim is :-
1. The process of manufacturing products of condensation of tannin with the a
and ẞ napththylamine, and products of condensation of catechine with the primary
aromatic amines hereinbefore mentioned.
2. The products obtained by the process referred to in the preceding claim.
3. The process of manufacturing colouring matters by the action of the condensation
products above referred to on the salts of nitrous derivates of tertiary aromatic
amines, and of manufacturing their products of reduction or combination.with
bisulphites.

page_text: 4. The new colouring matters and bisulphite combinations referred to in the
preceding claim.
5. The use of the new colouring matters for dyeing or printing, either alone or in
admixture with other suitable substances.
Dated this 30th day of September 1889.
ABEL & IMRAY,
Agents for the Applicants.