Manufacture of Derivatives of the Triphenylmethane Series.
Year: 1895

page_text: Date of Application, 2nd Dec., 1895
Complete Specification Left, 24th Aug., 1896-Accepted, 3rd Oct., 1896
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE ACTIEN GESELLSCHAFT FÜR ANILIN
FABRIKATION, of Berlin, in the Empire of Germany, Chemical Manu-
facturers.]
Manufacture of Derivatives of the Triphenylmethane Series.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Consulting Engineer and Chartered Patent
Agent, do hereby declare the nature of this invention to be as follows:-
The manufacture of violet colouring matters belonging to the triphenylmethane
series by condensation of aromatic aldehydes, preferably dimethyle-para-amido-
benzaldehyde with sulphonic acids of aromatic amines and subsequent oxidation
has been described in the Specification No. 7550 of 1889, and in the German
Patent No. 73126 of 1893.
In pursuance of their researches, my foreign correspondents have found that
ortho-chloro-dimethyle para-amidobenzaldehyde is a very suitable compound for
the manufacture of triphenylemethane colouring matters distinguished by the
brightness of their tints."
The ortho-chloro-dimethyle-para-amidobenzaldehyde may be obtained by the
method used for the production of dimethyle-amidobenzaldehyde. The ortho-
chloro-dimethyle-para-amidobenzaldehyde is readily soluble in alcohol and ether,
sparingly volatile with steam, and crystallises from an aqueous solution in small
crystalline needles having their melting point 82° C.
According to the condensation of this aldehyde being effected with amines or
sulphonic acids of amines, basic or acid colouring matters may be obtained
respectively.
If one molecule of ortho-chloro-dimethyle-para-amidobenzaldehyde is allowed to
act upon two molecules of au amine in presence of or without any condensing agent
the corresponding leuco compound is formed, which, on oxidation, is transformed
into a basic colouring matter.
9 kilos. of ortho-chloro-dimethyle-para-amidobenzaldehyde and 15 kilos. of
dimethyle aniline are dissolved in dilute sulphuric acid and heated for 24 hours.
The condensation product is precipitated by means of caustic soda and the excess.
of dimethyle aniline is removed with steam.
The leuco compound thus formed is filtered off and transformed, by oxidising it
with a suitable oxidising agent, as for instance lead dioxide, into the corresponding
dye stuff; it dyes tannin mordanted cotton a violet blue tint and may also be fixed
on wool from an acid or neutral bath with the same tint.
Acid colouring matters may be obtained in a similar way by condensing
one molecule of ortho-chloro-dimethyle-para-amido benzaldehyde with
a) two molecules of the sulphonic acid of an amine, or
b) with one molecule of an amine and one molecule of the sulphonic acid of an
amine and by subsequently oxidizing the leuco compounds thus obtained.
Price 811

page_text: EXAMPLE.
9 kilos. of ortho-chloro-dimethyle-para-amidobenzaldehyde and 29.1 kilos. of
ethyl-benzyle aniline sulphonic acid are dissolved in dilute sulphuric acid. The
condensation being completed, the solution is neutralised by means of caustic
soda and the leuco compound is precipitated therefrom by addition of common
salt.
The oxidation being effected in the well known manner, a colouring matter is
obtained which dyes wool blue tints from an acid bath.
If in the foregoing example a mixture of 15 kilos. of ethylbenzyle aniline sulphonic
acid and 61 kilos. of dimethyle aniline be substituted for the 29.1 kilos. of ethyl-
benzyle aniline sulphonic acid, a colouring matter is obtained dyeing wool blue violet
tints from an acid bath.
For the dimethyle aniline and ethylbenzyle-aniline-sulphonic acid used in the
above examples the corresponding equivalents of amines or sulphonic acids thereof
may be substituted yielding various triphenylemethane colouring matters of a basic
or acid nature.
Dated this 2nd dar of December 1895
ABEL & IMRAY,
Agents for the Applicant.
CUAILLETE SEMIFICATION.
Manufacture of Derivatives of the Triphenylmethane Series.
1, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery Lane,
in the County of London, Consulting Engineer and Chartered 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:-
The manufacture of violet colouring matters belonging to the triphenylmethane
series by condensation of aromatic aldehydes, preferably dimethyle-para-amido-
benzaldehyde with sulphonic acids of aromatic amines and subsequent oxidation
bas been described in the Specification No. 7550 of 1889, and in the German
Patent No. 73126 of 1893.
In pursuance of their researches, my foreign correspondents have found that
ortho-chloro-dimethyle para-amidobenzaldehyde is a very suitable compound for the
manufacture of triphenylemethane colouring matters distinguished by the brightness
of their tints.
The ortho-chloro-dimethyle-para-amido-benzaldehyde may be obtained by the
method used for the production of dimethyle-amido-benzaldehyde. The ortho-
chloro-dimethyle-para-amidobenzaldehyde is readily soluble in alcohol and ether,
sparingly volatile with steam, and crystallises from an aqueous solution in small
crystalline needles having their melting point 82° C.
According to the condensation of this aldehyde being effected with amines
or sulphonic acids of amines, basic or acid colouring matters may be obtained
respectively.
If one molecule of ortho-chloro-dimethyle-para-amidobenzaldehyde is allowed to
act upon two molecules of an amine in presence of or without any condensing
agent the corresponding leuco compound is formed, which, on oxidation, is
transformed into a basic colouring matter.

page_text: The condensation product is precipitated by means of caustic soda and the excess
of dimethyle aniline is removed with steam. The leuco compound thus formed
is filtered off and transformed, by oxidising it with a suitable oxidising agent, as for
instance lead dioxide, into the corresponding dye stuff; it dyes tannin mordanted
cotton a violet blue tint and may also be fixed on wool from an acid or neutral bath
with the same tint.
Acid colouring matters may be obtained in a similar way by condensing
one molecule of ortho-chloro-dimethyle-para-amido benzaldehyde with
a) two molecules of the sulphonic acid of an amine, or
b) with one molecule of an amine and one molecule of the sulphonic acid of
an amine and by subsequently oxidising the leuco compounds thus obtained.
EXAMPLE.
9 kilos. of ortho-chloro-dimethyle-para-amidobenzaldehyde and 29.1 kilos. of
ethyl-benzyle aniline sulphonic acid are dissolved in dilute sulphuric acid. The
condensation being completed, the solution is neutralised by means of caustic soda
and the leuco compound is precipitated therefrom by addition of common salt.
The oxidation being effected in the well known manner, a colouring matter is
obtained which dyes wool blue tints from an acid bath.
If in the foregoing example a mixture of 15 kilos. of ethylbenzyle aniline sulphonic
acid and 6.1 kilos. of dimethyle aniline be substituted for the 29.1 kilos. of ethyl-
benzyle aniline sulphonic acid, a colouring matter is obtained dyeing wool blue violet
tints from an acid bath.
For the dimethyle aniline and ethylbenzyle-aniline-sulphonic acid used in the
above examples the corresponding equivalents of amines or sulphonic acids or other
substitution products thereof may be substituted yielding various triphenylemethane
colouring matters of a basic or acid nature.
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 manufacture of new leuco-compounds of the triphenylemethane series by
condensing one molecular proportion of ortho-chloro-dimethyle-para-amidobenzal-
dehyde with two molecular proportions of amines, sulphonic acids or other sub-
stitution products thereof equal to or different from each other, substantially as
described.
2. The conversion of the leuco-compounds, referred to in Claim 1, by oxidation
into colouring matters, substantially as described.
3. The new leuco-compounds and colouring matters manufactured as above set
forth.
Dated this 24th day of August 1896.
ABEL & IMRAY,
Agents for the Applicant.