The Manufacture or Production of New Anthraquinone Derivatives
Year: 1899

page_text: Date of Application, 26th Jan., 1899
Complete Specification Left, 23rd Oct., 1899-Accepted, 25th Nov.,
1809
[Communicated from abroad by the FARBENFABRIKEN VORMALS FRIEDRICH BAYER AND
Co., of Elberfeld, Germany.]
The Manufacture or Production of New Anthraquinone Derivatives
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the
nature of this invention to be as follows:-
In the Specification of Letters Patent No. 1201107, my foreign correspondents
shewed that very valuable dyestuffs, consisting of diamidodioxyanthraquinone
disulphonic acids, can be obtained by first sulphonating 15 dioxyanthraquinone
(authrarufine), or 1.8 dioxyanthraquinone (crysazine); secondly nitrating the
resulting disulphonic acids; and finally, reducing the dinitro-disulphonic acids thus
obtained.
My foreign correspondents have now found that another valuable dye-stuff of this
class can be obtained by using 1.7 dioxyanthraquinone, having the formula-
20 parts of 1-7 dioxyanthraquinone are dissolved in 80 parts of fuming sulphuric
acid containing 20 per cent. of SO. This solution is heated at from 90 to 100 degrees
Centigrade, until a test portion, when mixed with water, yields a clear liquid. The
solution is then allowed to cool, and is mixed with 120 parts of a sulphuric acid of
66 degrees Baumé. To the resulting mixture, 25.5 parts of a mixture concentrated
sulphuric and nitric acid (containing 0.2 kilo's. by weight of nitric acid in each litre)
are gradually added, keeping the temperature of the liquid at about 25 degrees
Centigrade. When the nitration is finished, which will be the case after about from
4 to 5 hours, the liquid is poured on ice. To the resulting mixture, potassium
chloride is added, in order to precipitate the potassium salt of the dinitro-17 dioxy-
anthraquinone disulphonic acid, which is thus obtained in the shape of a yellow
017

page_text: powder that is soluble in water, and in concentrated sulphuric acid with a yellow
color.
By treating this dinitrodisulphonic acid with suitable reducing agents, the new
dye-stuff is obtained, which, as above mentioned, is a diamido disulphonic acid of
17 dioxyanthraquinone. In order to obtain this body, my foreign correspondents
may proceed as follows:-
A solution of 5 parts of the above described potassium salt in 200 parts of water is
mixed with a solution prepared from 13 parts of stannous chloride, 30 parts of water,
and 30 litres (in case the parts are kilos. by weight) of concentrated hydrochloric
acid (containing 33 per cent. of HCl). The reduction takes place immediately, and
is finished by heating to from 50 to 80 degrees Centigrade. The so-produced
coloring matter separates for the most part during the reaction.
When filtered off and dried, it represents a dark powder soluble in water with a red
color. By dilute alkalies it is dissolved with a pure blue color.
My foreign correspondents do not confine theniseives to the particulars given in
the above example, as this is merely typical, and can be altered within wide
limits.
Dated this 26th day of January 1899.
NEWTON & SON,
Agents for the Applicant.
COMPLETE SPECIFICATION.
The Manufacture or Production of New Anthraquinone Derivatives.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, 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 :-
In the Specification of Letters Patent No. 12011% my foreign correspondents
shewed that very valuable dyestuffs, consisting of diamidodioxyanthraquinone
disulphonic acids can be obtained by first sulphonating 1.5-dioxyanthraquinone
(anthrarufine), or 1, 8-dioxyanthraquinone (chrysazine); secondly, nitrating the
resulting disulphonic acids; and finally reducing the dinitrodisulphonic acids thus
obtained.
My foreign correspondents have now found that another valuable dye-stuff
of this class can be obtained by using 1.7-dioxyanthraquinone, having the
formula
instead of 1.5 or 1.8-dioxyanthraquinone in the above mentioned process.
The new diamidodioxyanthraquinone disulphonic acid obtained from 1,7 dioxy-
anthraquinone, dyes wool, in acid baths, even violet shades, and yields, on chrome-
mordanted wool, blue shades.
In order to illustrate the production of this dye-stuff, the following example is 40
given, the parts being by weight.

page_text: EXAMPLE.
20 parts of 1.7-dioxyanthraquinone are dissolved in 80 parts of fuming sulphuric
acid, containing 20 per cent. of SO. This solution is heated at from 90 to 100
degrees Centigrade, until a test-portion, when mixed with water, yields a clear
liquid. The solution is then allowed to cool, and is mixed with 120 parts of a
sulphuric acid of 66 degrees Baumé. To the resulting mixture, 25.5 litres (in case
the parts are kilos. by weight) of a mixture of concentrated sulphuric and nitric
acids (containing 0.2 kilos. by weight of nitric acid in each litre) are gradually
added, keeping the temperature of the liquid at about 25 degrees Centigrade. When
the nitration is finished, which will be the case after about from 4 to 5 hours, the liquid
is poured on ice. To the resulting mixture, potassium chloride is added, in order
to precipitate the potassium salt of the dinitro 1.7 dioxyanthraquinone disulphonic
acid, which is thus obtained in the shape of a yellow powder that is soluble in water,
and in concentrated sulphuric acid, with a yellow color. It dyes wool, in acid baths,
yellowish shades.
By treating this dinitrodisulphonic acid with suitable reducing agents, the new
dye-stuff is obtained, which, as above mentioned, is a diamidodisulphonic acid of
1.7 dioxyanthraquinone. In order to obtain this body, my foreign correspondents
may proceed as follows:-
A solution of 5 parts of the above described potassium salt in 200 parts of water, is
mixed with a solution prepared from 13 parts of stannous chloride, 30 parts of water,
and 30 litres (in case the parts are kilos. by weight) of concentrated hydrochloric acid
(containing 33 per cent. of HCl). The reduction takes place immediately, and is
finished by heating to from 50 to 80 degrees Centigrade. The coloring matter so
produced separates for the most part during the reaction. When filtered off and
dried, it represents a dark powder soluble in water with a red color. By dilute
alkalies, it is dissolved with a pure blue color.
My foreign correspondents do not confine themselves to the particulars given in
the above example, as this is merely typical, and can be altered within wide limits.
Thus, the reduction of the dinitro-compound can also be effected direct on the fibre,
for instance, by dyeing wool in acid baths with the dinitrodisulphonic acid of 1.7-dioxy-
anthraquinone, and treating the fibres thus impregnated with solutions of suitable
reducing agents.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed, as communicated to
ine from abroad, I declare that what I claim is :-
1.) The process for producing a disulphonic acid of 1-7-dioxyanthraquinone by
treating the latter with sulphonating agents, substantially as herein before described.
2.) The production of a dinitrodioxyanthraquinone disulphonic acid, by nitrating
the disulphonic acid referred to in the foregoing Claim 1, substantially as herein-
before described.
3.) Producing a diamidodioxyanthraquinone disulphonic acid by treating, with
suitable reducing agents, the dinitro compound referred to in Claim 2, either in bulk,
or when on the fibre, substantially as herein before described.
4.) The manufacture of a new diamidodisulphonic acid of 1.7-dioxyanthraquinone,
by first sulphonating 1.7-dioxyanthraquinone, secondly, nitrating the disulphonic
acid thus obtained, and, finally, reducing the resulting dinitro compound, substantially
as bereinbefore described.
5.) As new articles of manufacture, the new compounds obtainable according to
the processes herein before described and claimed.