Manufacture of Colouring Matters Derived from Paratoluidine, Metaxylidine, Pseudo-cumidine, and Mesidine, with Tetra- Methyldiamido Benzhydrol.
Year: 1889

page_text: Date of Application, 13th Aug., 1839
Complete Specification Left, 6th May, 1890-Accepted, 13th Aug., 1890
PROVISIONAL SPECIFICATION.
[Communicated from abroad by LA SOCIÉTÉ ANONYME DES MATIÈRES COLORANTES ET
PRODUITS CHIMIQUES DE ST. DENIS, of 105, Rue Lafayette, Paris, France.]
Manufacture of Colouring Matters Derived from Paratoluidine,
Metaxylidine, Pseudo-cumidine, and Mesidine, with Tetra-
Methyldiamido Benzhydrol.
<I
I. OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the County
of London, Fellow of the Institute of Patent Agents, do hereby declare the nature of
this invention to be as follows:-
My correspondents have discovered that paratoluidine, a metasylidine, pseudo-
cumidine, and amido trimethylbenzole, or mesidine, can be condensed on tetra-
methyldiamido benzhydrol, and thus produce new leuco-bases which are capable of
producing colouring matters ranging from bluish green to greenish blue.
As an example of the mode of operating I will describe the process as applied to
paratoluidine; the others are in every respect similar. The condensing agents employed
are hydrochloric acid and sulphuric acids, and the leuco bases obtained vary.
If one molecule of tetramethyldiamido benzhydrol be heated in a water bath during
24 hours with two molecules of hydrochloric acid and one molecule and a half of
hydrochlorate of paratoluidine until the complete transformation of the hydrol is
obtained, there is obtained, after purification, a leuco-base of a certain constitution and
having a point of fusion of 180° C.
If there be heated to 30° C. only, during one or two days, 27 kilos. of tetramethyl-
diamido benzhydrol, 12 kilos. of paratoluidine and 320 kilos. of concentrated sulphuric
acid of 66° Beaume, there will be obtained after purification a leuco-base of different
constitution from the preceding, the point of fusion of which is 160° ().
These two leuco bases give, by direct oxidation, triamidotetramethyltriphenyl-
carbinol, which is a green colouring matter which will dye wool in a neutral bath and
cotton with a tannin mordant.
These two oxidized leuco bases can be diazotized with one molecule of nitrite of
soda, or they may be first hydroxylised and afterwards oxidized, when, on boiling in
a very acid aqueous medium, they will give the corresponding monohydroxylised
derivative, forming green colouring matters having special properties.
These two
leuco-bases benzylized, sulpho conjugated, and oxidized, give also very fine greenish-
blue colouring matters. They are obtained in the following manner.
36 kilos. of one of the leuco-bases are treated with 26 kilos. of chloride of benzyle,
22 kilos. carbonate of soda and 200 litres of water, and heated for some hours in a
reflux apparatus.
After reaction, the excess of chloride of benzyle is eliminated, and the benzylic
base, transformed into sulphate, is dried and subjected to sulpho-conjugation. 50 kilos.
of this substance are treated hot with 250 kilos. of fuming sulphuric acid until a
sample is completely soluble in boiling water.
The sulphuric acid in excess is then saturated, the leuco-base, sulpho conjugated,
solidified and very soluble, is filtered, and the liquors obtained are transformned into
colouring matters by oxidation.
The colouring matters obtained possess a great affinity for wool fibre, owing to
their great solubility in water and their acid character, and they dye the same in an
acid bath with the greatest facility.
Dated this 12th day of Amont 1000
ABEL & IMRAY,
Agents for the Applicant.

page_text: Manufacture of Colouring Matters Derived from Paratoluidine,
Metaxylidine, Pseudo Cumidine, and Mesidine, with Tetra-
methyldiamido Benzhydrol.
a
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Fellow of the Institute of Patent Agents, do hereby declare
the nature of this invention and in what manner the same is to he performed,
to be particularly described and ascertained in and by the following statement :-
My correspondents have discovered that paratoluidine, a metaxylidine, pseudo
cumidine, and amido trimethylbenzole or mesidine, can be condensed on tetramethyl-
diamido benzhydrol, and thus produce new leuco bases capable of giving colouring
matters ranging from bluish green to greenish blue.
As an example of the mode of operating I will describe the process as applied to
paratoluidine the others are in every respect similar.
The condensing agents employed aro hydrochloric acid and sulphuric acids, and the
leuco bases obtained vary.
If one molecule of tetramethyldiamido benzhydrol be heated in a water bath during
24 hours with two molecules of hydrochloric acid and one molecule and a half of
hydrochlorate of paratoluidine until the complete transformation of the hydrol is
effected, there is obtained, after purification, a leuco base of a certain constitution
having a point of fusion of 180° C.
If there be heated to 30° C. only, during one or two days, 27 kilos. of tetramethyl-
diamido-benzlıydrol, 12 kilos. of paratoluidine and 320 kilos of concentrated sulphuric
acid of 66° Beaumé, there will be obtained after purification a leuco base of different
constitution from the preceding, the point of fusion of which is 160° C.
These two leuco bases give colouring matters by oxidation effected as follows.
10 kilo. of the leuco base is dissolved in 10 kilo. of hydrochloric acid at 21° Bé., and
150 litres of water.
The mixture is agitated, cooled to 10° C. and has added to it by small doses 8.5 kilo.
of binoxide of lead. Thus is obtained triamidotetramethyltriphenylcarbinol, which is
a green colouring matter which will dye wool in a neutral bath and cotton with a
tannin mordant.
These two oxidized leuco bases can be diazotized with one molecule of nitrate of soda
and transformed into their hydroxylised derivatives or they may be first diazotised,
transformed into hydroxylised derivative and afterwards oxidized in the usual way,
in order to obtain the corresponding carbinol.
These two leuco bases benzylised, sulpho conjugated, and oxidized, give also
very fine greenish blue colouring matters. They are obtained in the following
manner.
36 kilos. of one of the leuco bases are treated with 26 kilos. of chloride of benzyle,
22 kilos. carbonate of soda and 200 litres of water, and heated for some hours in a
reflux apparatus.
After reaction, the excess of chloride of benzyle is oliminated,
and
the benzylic base, transformed into sulphate, is dried and subjected to sulpho con-
jugation. 50 kilos. of this substance are treated hot with 250 kilos. of fuming
sulphuric acid until a sample is completely soluble in boiling water.
The sulphuric acid in excess is then saturated, the sulpho conjugated leuco base
which is very soluble, is filtered and the liquors obtained are transformed into
colouring matters by oxidation effected as above described by means of binoxide
of lead.
The colouring matters obtained possess a great affinity for wool fibre, owing to
their great solubility in water and their acid character, and they dye the same in an
acid bath with the greatest facility.

page_text: 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 :-
The manufacture of basic or acid blue green to green blue colouring matters by
condensing paratoluidine, metaxylidine, pseudo cumidine, amidotrimethylbenzol or
mesidine on tetramethyldiamidobenzhydrol, oxidising and hydroxylising these leuco
bases, or benzylising, sulphonising and then oxidising them.
Dated this 6th day of May 1890.
ABEL & IMRAY,
Agents for the Applicant