The Manufacture or Production of Anthraquinone Dye-stuffs.
Year: 1897

page_text: Date of Application, 25th Aug., 1897
Complete Specification Left, 23rd May, 1898-Accepted, 2nd July, 1898
[Communicated from abroad by THE FARBENFABRIKEN vorinals FRIEDERICH BAYER &
Co., of Elberfeld, Germany.]
The Manufacture or Production of Anthraquinone Dye-stuffs.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Paten Agent, do hereby declare the
nature of this invention to be as follows:-
My foreign correspondents discovered some time since, that new anthraquinone
derivatives could be obtained, by sulphonation, nitration, and reduction, from
anthrarufine and chrysazine, disulphonic acids of diamido-antlirarufine and diamido-
chrysazine being thus produced, which latter compounds have the respective
formulae-
According to the researches of my foreign correspondents, the said disulphonic
acids represent very valuable blue coloring matters.
My foreign correspondents have now found another process for producing the
above-mentioned diamido disulphonic acids, which process (in general terms)
consists in treating with sulphurous anhydride, alkaline sulphites, bisulphites, or the
like, paradinitro-anthrarufine (described by R. E. Schmidt and Gattermann, see
Berichte der Deutschen Chemischen Gesellschaft," 29. p. 2940) and paradinitro-
chrysazine, which, according to the researches of my foreign correspondents, can be
obtained by nitrating chrysazive.
The new process proceeds most probably in the following manner.-By the action
of the sulphites or bisulphites on the said dinitro compound, intermediate products
are first produced, which dissolve in water with a brown color. By further acting
ou these intermediate products with sulphites or bisulphites, they are transformed
into the finished dye-stuffs. This transformation can be performed more rapidly if
the intermediate products are treated with caustic alkalies. The dye-stuffs produced
in this manner exhibit the properties of the paradiamido anthrarufine and para-
diamidochrysazine disulphonic acids discovered by my foreign correspondents.
C31

page_text: In order to illustrate the new process, the following example is given, which
merely typical.
The parts are by weight:-
EXAMPLE.
IS
A mixture containing 10 parts of a 20 per cent. paste of para-dinitro
anthrarufine and 100 parts of a sodium bisulphite solution of 40 degrees Baumé,
is heated on a water bath. By this operation, the dinitro anthrarufine is gradually
dissolved, with a brown color, the above-mentioned intermediate product being
formed. If the most part of the dinitro anthrarufine has dissolved, the resulting
solution, which exhibits a violet color, owing to the formation of a small quantity
of the finished dye-stuff, is diluted with warm water, and filtered, in order to remove
a small quantity of unchanged dinitro anthrarufine. Subsequently soda-lye is
added to this violet solution, until the color has turned into greenish-blue. Finally
the sodium salt of the diamido anthrarufine disulfonic acid thus produced is
precipitated by the addition of common salt to the said greenish-blue solution.
In an analogous manner, paradiamido chrysazine disulphonic acid can be obtained
from paradinitro-chrysazine.
My foreign correspondents do not intend to confine themselves to the particulars
given in the foregoing example, as these can be varied within wide limits. Thus,
for instance, instead of soda-lye, other caustic alkalies can be used for the purpose
of transforming the intermediate products into the finished dye-stuffs, or this
transformation can be performed, as above mentioned, by further heating the
intermediate products with alkaline sulphites or bisulphites.
Dated this 25th day of August 1897.
COMI DUIN
The Manufacture or Production of Anthraquinone Dye-stuffs.
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 :-
My foreign correspondents discovered some time since that new anthraquinone
derivatives could be obtained by sulphonation, nitration, and reduction, from
anthrarufine and chrysazine, disulphonic acids of diamidoanthrarufine and diamido
chrysazine being thus produced, which latter compounds have the respective
formulae

page_text: According to the researches of ny foreign correspondents, the said disul phonic
acids represent very valuable blue colouring matters.
My foreign correspondents have now found another process for producing the
above mentioned diamidodisulphonic acids, which process (in general terms)
consists in treating with alkaline sulphites, bisulphites, or the like, paradinitro-
anthrarufine (described by R. E. Schmidt and Gattermann, see Berichte der
Deutschen Chemischen Gesellschaft, 29, p. 2910) and paradinitrochrysazine,
which, according to the researches of my foreign correspondents, can be obtained
by nitrating chrysazine.
The new process proceeds in the following manner :-By the action of the
sulphites or bisulphites on the said dinitro compounds, intermediate products
are first produced, which dissolve in water with a brown colour. By further
acting ou these intermediate products with sulphites or bisulphites, they
are transformed into the finished dyestuffs. This transformation can be
performed more rapidly if the intermediate products are treated with caustic
alkalies. The dye-stuffs produced in this manner exhibit the properties of the
para-diamidoanthrarufine and para-diamidochrysazine disulphonic acids discovered
by my foreign correspondents.
In order to illustrate the new process, the following example is given, which is
A mixture containing 10 parts of a 20 per cent. paste of paradinitroanthrarufine
and 100 parts of a sodium bisulphite solution, of 40 degrees Baumé, is heated on
a water-bath. By this operation the dinitroanthrarufine is gradually dissolved,
developing a brown colour, the above mentioned intermediate product being thus
formed. If the most part of the dinitroanthrarufine has dissolved, the resulting
solution, which exhibits a violet colour, owing to the formation of a small quantity
of the finished dyestuff, is diluted with warm water, and filtered, in order to
remove a small quantity of unchanged dinitroanthrarufine. Subsequently soda
lye is added to this violet solution, until the colour has turned into greenish blue.
Finally the sodium salt of the diamido anthrarufinedisulphonic acid thus produced
is precipitated by the addition of common salt to the said greenish blue
solution.
In an analogous manner paradiamido chrysazin edisulphonic acid can be obtained
from paradinitrochrysazine.
My foreign correspondents do not intend to confine themselves to the particulars
given in the foregoing example, as these can be varied within wide limits. Thus,
for instance, instead of soda lye, other caustic alkalies can be used for the purpose
of transforming the intermediate products into the finished dye-stuffs, or this
transformation can be performed, as above mentioned, by further beating the
intermediate products with alkaline sulphites or bisulphites.
Having now particularly described and ascertained the nature of the said inven-
tion, and in what manner the same is to be performed (as communicated to me
from abroad), I declare that what I claim is :-
1. The process for producing paradiamidoanthrarufine disulphonic acid and
paradiamido chrysazine disulphonic acid, which process consists in heating para-
dinitroanthrarufine and paradinitrochryṣazine with alkaline sulphites or bisulphites,
substantially as hereinbefore described.
2. The production of new intermediate products by heating paradinitroanthrarufine
and paradinitrochrysazine with alkaline sulphites or bisulphites, substantially as
hereinbefore described.
3. The transformation of the intermediate products mentioned in the foregoing
Claim 2 into paradiamido anthrarufine disulphonic acid and paradiamidochrysazine

page_text: disulphonic acid, by heating the said intermediate products with caustic alkalies, or
with other substances yielding the same result, substantially as hereinbefore
described.
4. As new articles of manufacture, the new intermediate products hereinbefore
defined.
1000