The Manufacture and Production of New Colouring-matters of the Anthracene Series.
Year: 1899

page_text: Date of Application, 18th Dec., 1899
Complete Specification Left, 24th Aug., 1900-Accepted, 20th Oct., 1900
PROVISIONAL SPECIFICATION.
The Manufacture and Production of New Colouring-matters of the
Anthracene Series.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields, in the County of
London, Gentleman, do hereby declare the nature of this invention (which has
been communicated to me by the Badische Anilin & Soda Fabrik of Ludwig-
shafen-on-Rhine, in the German Empire) to be as follows:--
It is known that upon nitrating anthraquinone mono-sulphoacid, by treatment
with a mixture of sulphuric and nitric acids, two isomeric mono-nitro-anthra-
quinone-sulphoacids are obtained. These bodies are distinguished from one
another by their different solubility in water, the less soluble one being termed
the "alpha "acid, and the more soluble one the "beta" acid (see Claus. Berichte,
Vol. 15, p. 1514).
The present invention consists in the manufacture of new colouring-matters
from these two mono-nitro-anthraquinone-sulphoacids. The said new colouring-
matters are obtained by heating the said nitro-sulphoacids, or either of them,
with aromatic amines. The said new colouring-matters are sulphoacids
which are soluble in water and which dye unmordanted and chrome mordanted
wool, red, violet, and brown shades. Speaking generally the process for the
production of the said new colouring-matters consists in heating one
or both
of the said nitro-sulphoacids with an aromatic amine, usually at the boiling
point of the amine. The formation of the colouring-matters can be recognised
from the colour of the melt obtained.
The following example will serve to further illustrate the nature of the inven-
tion, but the invention is not confined to the example. The parts are by
weight.
EXAMPLE.
COLOURING-MATTER FROM BETA-NITRO-ANTHRAQUINONE-MONO-SULPHOACID AND
PARA-TOLLIDINE.
A pre-
Melt about one hundred parts of para-toluidine in a vessel provided with a
stirrer, and add about ten parts of the said beta nitro-sulphoacid. Heat the
mixture till it boils, and continue heating until the melt has assumed a cherry-
red colour which no longer increases in intensity. To isolate the new colouring-
matter allow the melt to cool to about eighty degrees Centigrade and then add
about one hundred and fifty parts of alcohol and allow to further cool.
cipitate forms which consists of any unchanged nitro-sulphoacid and some
colouring-matter. Filter this off from the alcoholic mother liquid and precipi-
tate the pure colouring-matter by adding twice its volume of ether. The colour-
ing-matter obtained in this way is a brown-violet crystalline powder. Separate
the colouring-matter from the mother-liquor by decanting and filtration. The

page_text: new colouring-matter so obtained yields bluish bordeaux-red shades when dyed
on unmordanted, or on chrome mordanted, wool.
In a similar manner new colouring-matters can be obtained from the "alpha"
nitro-anthraquinone-sulphoacids and also from both the said nitro-sulphoacids.
Other aromatic amines can be used instead of para-toluidine. If desired the
conditions of the reaction can be varied; diluents such as naphthalene can be
used and the colouring-matter can be isolated from the melt in other ways.
Dated this 18th day of December 1899.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.
The Manufacture and Production of New Colouring-matters of the
Anthracene Series.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields, in the County of
London, Gentleman, do hereby declare the nature of this invention (which has
been communicated to me from abroad by the Badische Anilin & Soda Fabrik,
of Ludwigshafen-on-Rhine, in the German Empire), and in what manner the
same is to be performed to be particularly described and ascertained in and by
the following statement:-
It is known that upon nitrating anthraquinone-mono-sulphoacid, by treatment
with a mixture of sulphuric and nitric acids, two isomeric mono-nitro-anthra-
quinone-sulphoacids are obtained. These bodies are distinguished from one
another by their different solubility in water, the less soluble one being termed
the alpha "acid, and the more soluble one the beta acid (see Claus. Bericlite,
Volume 15, page 1514).
"
"
The present invention consists in the manufacture of new colouring matters
from these two mono-nitro-anthraquinone-sulphoacids. The said new colouring
matters are obtained by heating the said nitro-sulphoacids, or either of them,
with primary aromatic amines. The said new colouring matters are sulphoacids
which are soluble in water, and which dye unmordanted and chrome mordanted
wool, red, violet, and brown shades. Speaking generally the process for the
production of the said new colouring matters consists in heating one, or both,
of the said nitro sulphoacids with a primary aromatic amine, usually at the
boiling point of the amine. The formation of the colouring matters can be
recognised from the colour of the melt obtained.
The following example will serve to further illustrate the nature of the inven-
tion and the manner in which it may be carried into practical effect but it is
not confined to this example. The parts are by weight.
EXAMPLE.
COLOURING MATTER FROM BETA-NITRO-ANTHRAQUINONE-MONO-SULPHOACID AND
PARA-TOLUIDINE.
Melt about one hundred parts of para-toluidine in a vessel provided with a
stirrer, and add about ten parts of the said beta-nitro-sulphoacid. Heat the
mixture till it boils, and continue heating until the melt has assumed a cherry-
red colour which no longer increases in intensity. To isolate the new colouring
matter allow the melt to cool to about eighty degrees Centigrade, and then add
about one hundred and fifty parts of alcohol and allow to further cool.
A pre-

page_text: cipitate forms which consists of any unchanged nitro-sulphoacid and some
colouring matter. Filter this off from the alcoholic mother liquid and precipi-
tate the pure colouring matter by adding twice its volume of ether. The colour-
ing matter obtained in this way is a brown-violet crystalline powder. Separate
the colouring matter from the mother-liquor by decanting and filtration. The
new colouring matter so obtained yields bluish bordeaux-red shades when dyed
on unmordanted, or on chrome mordanted, wool.
"
"
In a similar manner new colouring matters can be obtained from the alpha
nitro-anthraquinone-sulphoacid and also from the mixture of both the said
beta" and "alpha" nitro-sulphoacids. Other primary aromatic amines such
as aniline, ortho-toluidine, and alpha-naphthylamine, can be used instead of
para-toluidine. If desired the conditions of the reaction can be varied. Diluents
such as naphthalene can be used and the colouring matter can be isolated from
the melt in other ways.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed I declare that what
I claim is―
1. The manufacture of new colouring matters of the anthracene series by
heating a mono-nitro-anthraquinone-sulphoacid or a mixture of mono-nitro-
anthraquinone-sulphoacids with a primary aromatic amine substantially as
herein before described.
2. The manufacture of a colouring matter from beta-nitro-anthraquinone-
mono-sulphoacid and para-toluidine substantially as described in the foregoing
example.
3. As a new article of manufacture the new colouring matters of the anthra-
cene series such as can be obtained as hereinbefore described and claimed.
Dated this 24th day of August 1900.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.