Improvements in the Manufacture of Colouring Matters of the Rosinduline Series.
Year: 1896

page_text: Date of Application, 27th Apr., 1896
Complete Specification Left, 13th Jan., 1897-Accepted, 13th Mar., 1897
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE ACTIEN-GESELLSCHAFT FÜR ANILIN-
FABRIKATION, of Berlin, in the Empire of Germany, Chemical Manu-
facturers.]
Improvements in the Manufacture of Colouring Matters of the
Rosinduline Series.
1, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery Lane,
in the County of London, Consulting Engineer and Chartered Patent Agent, do
hereby declare the nature of this invention to be as follows:-
It has been proposed to produce rosinduline dorivatives by treating with oxidising
agents equimolecular proportions of a-naphthylamine or its derivatives and o-amido-
diphenylamine-sulphonic acid or its homologues.
My foreign correspondents have now discovered that the aforementioned
roainduline derivatives inay be converted by phenylation and subsequent sulphona-
tion into valuable more highly sulphonated derivatives of phenylated rosindulines.
The following is an illustration of the invention, which is not limited to the
substances and methods of operating mentioned as these may be varied without
departing from the character of this invention.
10 kilos. of the rosinduline sulphonic acid obtained as indicated in Example I of
the Specification No. 16217 of 1895, 30 kilos. of aniline and 5 kilos. of bydro-
chloric aniline are heated to from 165° to 170° C. for about 2 hours. The
phenylated rosinduline sulphonic acid separates as a green crystalline powder of
metallic lustre. The excess of aniline is removed in the usual way by means of
steam or of diluted acids.
The phenylrosinduline-sulphonic acid obtained is scarcely soluble in water. Its
soda salt sparingly dissolves in cold water more readily in hot water.
The phenylrosinduline-sulphonic acid dyes wool in au acidulated bath blue-red
tints.
It is converted into trisulphonic acid in the following manner.
10 kilos. of the above described compound are introduced whilst stirring into
about 30 kilos. of fuming sulphuric acid of 32% of anhydride at from 30° to 35° C.
Then, the mixture is heated to from 65° to 70° C. for about 4 hours. After cooling,
the mixture is allowed to flow upon ice, about two or three times the quantity of
the sulphuric acid.
The precipitated sulphonic acid is separated by filtration and converted into.its
soda salt, from the solution of which the dyestuff is isolated by means of common
salt.
It dyes wool clear blue-red tints of a remarkable fastness to light and alkalies
and is distinguished by its great equalisating power.
The trisulphonic acid is readily soluble in water and forms well characterised
Balts.
The di-soda salt is sparingly soluble in cold water, but dissolves easily on heating.
It crystallises in beautiful brown lamellæ. By means of common salt it is entirely
precipitated. It is insoluble in alcohol.
The acid barium and calcium salts are nearly insoluble in water.

page_text: By these properties, the above described acid is distinguished from the phenyl-
rosinduline trisulphonic acids mentioned in the English Patent No. 19167 of 1890.
and the German Patent No. 67198.
Dated this 27th day of Antil 1908
ABEL & IMRAY,
Agents for the Applicant.
Improvements in the Manufacture of Colouring Matters of the
Rosinduline Series.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery Lane,
in the County of London, Consulting Engineer and Chartered 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:-
It has been proposed to produce rosinduline derivatives by treating with oxidising
agents equimolecular proportions of a-naphthylamine or its derivatives and o-amido-
diphenylamine-sulphonic acid or its homologues.
My foreign correspondents have uow discovered that the aforementioned
rosinduline derivatives may be converted by phenylation and subsequent sulphona-
tion into valuable more highly sulphonated derivatives of phenylated rosindulines.
The following is an illustration of the invention, which is not limited to the
substances and methods of operating mentioned, as those may be varied without
departing from the character of this invention.
10 kilos. of the rosinduline sulphonic acid obtained as indicated in Example I of
the Specification No. 16217 of 1895, 30 kilos. of aniline and 5 kilos. of hydro-
chloric aniline are heated to from 165° to 170° C. for about 2 hours. The
phenylated rosinduline sulphonic acid separates as a green crystalline powder of
metallic lustre. The excess of aniline is removed in the usual way by means of
steam or of diluted acids.
The phenyl rosinduline sulphonic acid obtained is scarcely soluble in water.
Boda salt sparingly dissolves in cold water, more readily in hot water.
Its
The phenyl rosinduline sulphonic acid dyes wool in an acidulated bath blue red
tints. It is converted into trisulphonic acid in the following manner.
10 kilos. of the above described compound are introduced whilst stirring into
about 30 kilos. of fuming sulphuric acid of 32 per cent. of anhydride at from 30°
to 35° C. Then, the mixture is heated to from 65° to 70° C. for about 4 hours.
After cooling, the mixture is allowed to flow upon ice, about two or three times the
quantity of the sulphuric acid. The precipitated sulphonic acid is separated by
filtration and converted into its soda salt, from the solution of which the dyestuff
is isolated by means of common salt. It dyes wool clear blue-red tints of a
remarkable fastness to light and alkalies and is distinguished by its great
equalisating power.
The trisulphonic acid is readily soluble in water and forms well characterised
salts.
The di-soda salt is sparingly soluble in cold water, but dissolves easily on
heating.
It crystallises in beautiful brown lamellæ.
By means of common salt it is entirely precipitated. It is insoluble in alcohol.
The acid barium and calcium salts are uearly insoluble in water.
By these properties, the above described acid is distinguished from the phenyl

page_text: rosinduline trisulphonic acids mentioned in the English Patent No. 19167 of 1890
and the German Patent No. 67198.
In the above example instead of aniline ortho- or para-toluidine may be used.
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
I claim is :-
1. The herein described manufacture of phenyl- or tolyl-rosinduline sulphonic
acid by the action of aniline or ortho- or para-toluidine upon the rosinduline-
derivatives described in the Specification No. 16217 of 1895.
2. The manufacturo of phenyl-or tolyl-rosinduline trisulphonic acid by the
action of fuming sulphuric acid upon the compounds manufactured as set forth in.
Claim 1.
3. The dyestuffs manufactured as above set forth.
ABEL & IMRAY,
Agents for the Applicant..