Improvements in the Manufacture of Dyes of the Rosaniline Series and of Leuco Compounds thereof.
Year: 1892

page_text: Date of Application, 14th Jan., 1892
Complete Specification Left, 12th Oct., 1892-Accepted, 26th Nov., 1892
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Dyes of the Rosaniline Series
and of Leuco Compounds thereof.
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of
Middlesex Gentleman do hereby declare the nature of this invention which
has been communicated to me from abroad, by The Badische Anilin and
Soda Fabrik of Ludwigshafen-on-Rhine in the Empire of Germany to be as
follows
-
In the Provisional Specification No. 11275 of 1891 there is described the manu-
facture of new dyes of the rosaniline series by the condensation of tetra alkyl-
diamido-benzo-phenone with meta-methoxy-phenyl-para-tolylamine and other
analogous alkyl ethers of meta-hydroxy-amido compounds.
It is known that in many cases dyes resulting from condensations of tetra-alkyl-
diamido-benzophenones, can also be obtained indirectly from the corresponding
benzhydrols. The present invention relates to the modification of the process
described in the above named Specification which consists in condensing meta-
methoxy-phenyl-para-tolylamine and other analogous alkyl ethers of meta-hydroxy-
amido-compounds with tetra-alkyl-diamido benzhydrols, whereby leuko compounds
of the above mentioned dyestuffs are obtained. On oxidizing these leuko com-
pounds these basic rosanilin dyes themselves result and on sulphonation as described
in that application yield the acid violet dyes further the leuco compounds can
themselves be sulphonated when leuco-sulpho-acids are obtained and these on
oxidation give acid dyes which are substantially if not absolutely identical with
those obtainable as described in the aforesaid Provisional Specification No. 11275
of 1891.
and the following alkyl-ethers or meta-hydroxy-amido-compounds are instances or
those giving good results
Meta-methoxy-phenyl-para-tolylamine
Meta-ethoxy-phenyl-para-tolylamine
Meta-methoxy-phenyl-ortho-tolylamine
Meta-ethoxy-phenyl-ortho-tolylamine
Meta-methoxy-phenyl-meta-xylylamine
Meta-ethoxy-phenyl-meta-xylylamine.
The condensation of tetra-alkyl-diamido-benzhydrols with the above mentioned
alkyl-ethers of meta-oxy-amido compounds proceeds very readily the presence of
an acid is sufficient to bring it about and a solvent such as alcohol assists. the
progress of the reaction.
The leuco bases can be oxidized in the usual way by treatment with a superoxide
in acid solution.
The sulphonation of the leuco bases can be readily effected by fuming sulphuric
acid containing say about 23 to 30 per cent. free anhydride (SO,) and the leuco
acids can be oxidized in a manner similar to that above described.
Dated this 14th day of January 1892.

page_text: Improvements in the Manufacture of Dyes of the Rosaniline Series
and of Leuco Compounds thereof.
I, JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of
Middlesex, Gentleman do hereby declare the nature of this invention which bas
been communicated to me from abroad by The Badische Anilin and Soda Fabrik
of Ludwigshafen-on-Rhine in the Empire of Germany 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. 11,27 of 1891 granted to me there
is described the manufacture of new dyes of the rosaniline series by the con-
densation of tetra-alkyl-diamido-benzophenone with meta-methoxy-phenyl-para-
tolylamine and other analogous alkylethers of meta-hydroxy-amido compounds.
It is known that in many cases dyes resulting from condensations of tetra-alkyl-
diamido-benzophenones, can also be obtained indirectly from the corresponding
benzhydrols.
The present invention relates to the modification of the process described in the
above named Specification, which consists in condensing meta-methoxy-phenyl-
-para-tolylamine or other analogous alkyl-ethers of meta-hydroxy-amido compounds
with tetra-alkyl-diamido-benzhydrols, whereby leuco-compounds related to the
above mentioned dyestuffs are obtained. On oxidizing these lecuo-compounds,
basic rosaniline dyes are formed, and on sulphonation in the manner described in
the aforementioned Specification of Letters Patent No. 11275" yield acid violet
dyes which are of a chemical nature the same as that of those described in 'the
said Specification. Prepared in the manner herein described the dyes obtained
yield duller shades than when prepared as described in the said Specification
No. 11275 of 1891.
The benzhydrols to be used in carrying out this invention are tetra-methyl-
diamido-benzhydrol and tetra-ethyl-diamido-benzhydrol and the following alkyl-
ethers of meta-hydroxy-amido-compounds are instances of those giving good
results.
Meta-methoxy-phenyl-para-tolylamine
Meta-ethoxy-phenyl-para-tolylamine
Meta-methoxy-phenyl-ortho-tolylamine
Meta-ethoxy-phenyl-ortho-tolylamine
Meta-methoxy-phenyl-meta-xylylamine and
Meta-ethoxy-phenyl-meta-xylylamine.
The condensation of tetra-alkyl-diamido-benzhydrols 'with 'the above mentioned
alkyl ethers of meta-hydroxy-amido compounds proceeds very readily, the presence
of an acid being sufficient to bring it about and a solvent (such for instance as
alcohol) assists the progress of the reaction.
The leuco-bases 'obtained 'can be oxidized in the usual way by treatment with
superoxide in acid solution.
a
The sulphonation of the said leuco bases 'can be readily effected by fuming
sulphuric acid containing say about 23 to 30 per cent. free anhydride (SO3) and the
leuco-acids can be oxidized in a manner similar to' that above described.
The following examples will serve to illustrate the nature of the invention and
the manner in which it can be carried into practical effect, but the details may be
conveniently varied without essentially altering the nature of the product obtained..
The parts are by weight.

page_text: (2.) As new articles of manufacture the leuco-bases such as can be obtained by
the process hereinbefore described and claimed by the first claiming clause.
(3.) The process for the manufacture of basic dyes of the rosaniline series which
consists in first preparing a leuco-base as hereinbefore described and claimed by
the first claiming clause and then oxidizing it all substantially as described.
(4.) The process for the manufacture of acid dyes of the rosaniline series which
consists in preparing a basic dye as hereinbefore described and claimed by the
preceding third claiming clause and then sulphonating it in the manner described
in the Specification No. 11275 all substantially as hereinbefore described.
(5.) The process for the manufacture of acid dyes of the rosaniline series which
consists in first preparing a leuco-base as herein before described and claimed by
the preceding first claiming clause, then sulphonating it and finally oxidizing the
leuco-sulpho acid obtained all substantially as hereinbefore described.
Dated this 12th day of October 1892.
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, Agents.