Production of Black Colouring Matters from Amidoflavopurpurine and Amidoanthrapurpurine.
Year: 1890

page_text: Date of Application, 16th Apr., 1890
Complete Specification Left, 23rd Dec., 1890-Accepted, 24th Jan., 1891
PROVISIONAL SIMULETUATION.
[Communicated from abroad by THE FARBWERKE VORMALS MEISTER LUCIUS AND
BRUNING, of Hoechst-am-Maine, in the Empire of Germany.]
Production of Black Colouring Matters from
Amidoflavopurpurine
and Amidoanthrapurpurine.
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:-
From flavopurpurine can be prepared, by nitration and suitable treatment of the
betanitro flavopurpurine obtained, with reducing agents, an amidodavopurpurine C14
H, O. NH, from which by treatment with glycerine, sulphuric acid and an oxidizing
agent, is obtained the corresponding quinoline compound.
In order to produce the quinoline compound, 1 part of amidoflavopurpurine in
powder is dissolved in 7 parts of sulphuric acid of 66° and thereto is added part
of glycerine and part of nitro-benzol. The whole is heated slowly to 110° C.
and kept at this temperature for 8 hours. The melt is pressed into cold water and
the sulphate, which will separate is decomposed into the free base by filtration and
washing with water. In order to obtain from this raw material the quinoline in
a pure state, use is made of the property possessed by it of forming with bisulphite of
soda a compound that is easily soluble in water. The bisulphite solution is liberated
from the impurities it may contain, by filtration and the quinoline is precipitated by
sursaturation with common salt or sulphuric acid. It is filtered off, washed, and may
he used as coloring matter by itself or in admixture with bisulphite, in solution, for
dyeing wool and printing on cotton.
The novel coloring matter can be distinguished already by its appearance from
alizarine-blue, its colour varying, from violet-brown to black (in paste) whereas the
latter is blue. Dyed on wool or printed on cotton, it furnishes grey to black shades
according to the larger or smaller quantity used.
It dissolves in bisulphite more readily than the alizarine blue and it is not possible
to separate it from its moderately concentrated bisulphite solutions by the addition of
soda lye in the form of a soda salt soluble with difficulty, as is the case with alizarine-
blue, and this by reason that the coloring matter is of easy solubility in soda lye,
showing violet-red coloration.
With acids the coloring matter forms salts, but they are soluble in water with
greater difficulty than those of alizarine blue.
By continued washing with water they are also decomposed into the base and the
acid. In the solvents generally used for anthraquinone derivatives it is of difficult
solubility.
From its hot solution in naptha, alcohol, amylalcohol acetylacetic ether or
carbolic acid it precipitates in the form of greenish-black flakes which however do
not disclose crystalline form even when greatly magnified.
Heated carefully, the body melts and afterwards sublimates in form of microscopic
small needles with greenish lustre. Heated in alkaline solution with zinc dust, it
furnishes, like alizarine blue a "dye-vat." Heated quickly in a tube with the
twenty fold quantity of zinc-dust, it is converted into the anthraquinoline described
by Graebe. In exactly the same way as is produced from beta nitro flavopurpurine,
beta amidoflavopurpurine and from this the quinoline, amido anthrapurpurine and its
quinoline are produced from beta nitroanthrapurpurine.
The anthrapurpurine-quinoline is as regards its chemical and physical qualities very

page_text: similar to the flavopurpurine-quinoline described hereinbefore, only it gives blueish
shades on being dyed on wool or printed on cotton.
Dated this 10th 11000
ABEL & IMRAY.
Agents for the Applicants.
Production of Black Colouring Matters from Amidoflavopurpurine
and Amidoanthra purpurine.
I, OLIVER [MRAY, 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 :--
From flavopurpurine can be prepared by nitration and suitable treatment of the beta
nitroflavopurpurine obtaine!, with reducing agents, an amidoflavopurpurine C₁,H,O,.
NH2, from which by treatment with glycerine, sulphuric acid and an oxidizing agent,
is obtained the corresponding quinoline compound.
In order to produce the quinoline compound, 1 part of amidoflavopurpurine in
powder is dissolved in 7 parts of sulphuric acid of 66° and thereto is added part of
glycerine and part of nitro-benzol. The whole is heated slowly to 110° C. and kept
at this temperature for 8 hours. The melt is pressed into cold water and the
sulphate which will separate is decomposed into the free base by filtration and washing
with water. In order to obtain from this raw material the quinoline in a pure state,
use is made of the property possessed by it of forming with bisulphite of soda a
compound that is easily soluble in water.
The bisulphite solution is liberated from the impurities it may contain, by
filtration and the quinoline is precipitated by sursaturation with common salt or
sulphuric acid. It is filtered off, washed, and may be used as coloring matter by
itself or in admixture with bisulphite, in solution for dyeing wool and printing on
cotton.
The novel coloring matter can be distinguished already by its appearance from
alizarine-blue, its colour varying, from violet-brown to black (in paste) whereas the
latter is blue. Dyed on wool or printed on cotton, it furnishes grey to black shades
according to the larger or smaller quantity used.
It dissolves in bisulphite more readily than the alizarine blue and it is not possible
to separate it from its moderately concentrated bisulphite solutions by the addition of
soda lye in the form of a soda salt soluble with difficulty as is the case with alizarine-
blue, and this by reason that the coloring matter is of easy solubility in soda lye
showing violet-red coloration.
With acids the coloring matter forms salts, but they are soluble in water with greater
difficulty than those of alizarine blue.
By continued washing with water they are also decomposed into the base and
the acid. In the solvents generally used for anthraquinone derivatives it is of
difficult solubility.
From its hot solution in naptha, a'cohol, amylalcohol acetylacetic etlier or carbolic
acid it precipitates in the form of greenish-black flakes which however do not disclose
crystalline form even when greatly magnified.
Heated carefully, the body melts and afterwards sublimates in form of microscopic
small needles with greenish lustre. Heated in alkaline solution with zinc dust it
furnishes like alizarine blue a "dye-vat." Heated quickly in a tube with the twenty
fold quantity of zinc-dust, it is converted into the anthraquinoline described by
Graebe. In exactly the saine way as is produced from beta nitro flavopurpurine, beta
amido flavopurpurine and from this the quinoline, amido anthrapurpurine and its
quinoline are produced from beta nitro-anthrapurpurine.
The anthrapurpurine-quinoline is as regards its chemical and physical qualities very

page_text: similar to the flavopurpurine-quinoline described hereinbefore, only it gives blueish
shades on being dyed on wool or printed on cotton.
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 production of black coloring matters by heating amidoflavopurpurine or
amidoanthrapurpurine together with glycerine, sulphuric acid and an oxidating agent,
such as nitrobenzol, substantially as described.
2. The black colouring matters produced as above set forth.
ABEL & IMRAY,
Agents for the Applicant.