Manufacture of Colouring Matters Dyeing Yellow with Mordants.
Year: 1895

page_text: Date of Application, 24th June, 1895
Complete Specification Left, 2nd Mar., 1896-Accepted, 4th Apr.,
1896
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE ACTIEN GESELLSCHAFT FÜR ANILIN
FABRIKATION, of Berlin, in the Empire of Germany, Chemical
Manufacturers.]
Manufacture of Colouring Matters Dyeing Yellow with Mordants.
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 dye stuffs dyeing yellow with chromium mordants obtained by the action of
aniline or its homologues upon salicylic acid are of no technical value on account
of the feeble tinctorial power of their chromium lakes.
By employing the nitroderivatives of amines (para and meta nitraniline for
instance) the dyeing affinity of the colouring matter thus obtained has been
increased to such an extent that the latter can technically be used with good results
(see Specification No. 17583 of 1887); the entrance of the nitro group however
considerably reduces their solubility.
Colouring matters of greater solubility may be produced by substituting for the
nitro group certain other acid groups as, for instance, the sulpho group, but without
obtaining the same effect as regards intensity of the shade. Amido sulphonic acids
of the naphthaline series and salicylic acid also form dye stuffs not particularly
distinguished by their dyeing properties.
The present invention is based upon the striking observation, that a neutral
group viz. the oxy-alkyl-group, produces an effect similar to that obtained by groups
bearing an acid character as pronounced as the nitro group.
The entrance of an oxy-alkyl-group into the nucleus of aniline or its homologues
has been found to bring about a considerable increase in the dyeing affinity of the
azo colouring matters derived therefrom and distinguishes them from the dye stuffs
of the Specification No. 17583 of 1887 by a greenish tint and by greater solubility
which for dyeing and printing purposes is of considerable importance.
The following is the typical formula of the colouring matters manufactured
according to the present invention.

page_text: The following example is given in order to illustrate the process for the
production of the new colouring matters.
:
The solution of the diazo derivative of 42 kilos. of meta-amido-para-cresol
methylether (CH, OCH₁: NH₂ = 1:4:3) is allowed to flow into a cooled solution
of 50 kilos. of salicylic acid, kept alkaline throughout the reaction. As soon as
the combination is completed the mixture is heated to boiling, the excess of alkali
is removed by neutralizing with acid, and the colouring matter is precipitated by
means of common salt in the shape of yellow crystalline needles. It dyes chromium
mordanted wool a bright yellow.
If, in the above example, for the meta-amido-para-cresol ether the equivalent
quantity of ortho-amidophenol-methyl ether be substituted, a similar colouring
matter is obtained. A product dyeing with a more greenish tint may be produced
by employing para-amidophenol ether or meta-amido-phenol ether. Similar results
may be obtained if in the above examples, instead of the methyl ethers the ethyl
ethers are used.
Dated this 24th dow of June 1805
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Manufacture of Colouring Matters Dyeing Yellow with Mordants.
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 and in what manner the same is to
be performed to be particularly described and ascertained in and by the following
statement:
The dye stuffs dyeing yellow with chromium mordants obtained by the action of
ariline or its homologues upon salicylic acid are of no technical value on account of
the feeble tinctorial power of their chromium lakes.
By employing the nitroderivatives of amines (para- and meta-nitraniline for
instance) the dyeing affinity of the colouring matter thus obtained has been
increased to such an extent that the latter can technically be used with good results
(see Specification No. 17583 of 1887); the entrance of the nitro group however
considerably reduces their solubility.
Colouring matters of greater solubility may be produced by substituting for
the nitro group certain other acid groups as, for instance, the sulpho group, but
without obtaining the same effect as regards intensity of the shade.
Amido sulphonic acids of the naphthalene series and salicylic acid also form
dye stuffs not particularly distinguished by their dyeing properties.
The present invention is based upon the striking observation, that a neutral
group, viz. the oxy-alkyl-group, produces an effect similar to that obtained by
groups bearing an acid character as pronounced as the the nitro group.
The entrance of an oxy-alkyl-group into the nucleus of aniline or its homologues
has been found to bring about a considerable increase in the dyeing affinity of the
azo colouring matters derived therefrom and distinguishes them from the dye stuffs
of the Specification No. 17583 of 1887 by a greenish tint and by greater solubility,
which for dyeing and printing purposes is of considerable importance.
The following is the typical formula of the colouring matters manufactured
according to the present invention.

page_text: where R represents an oxy carbonic acid such as salicylic or cresotinic acid and
the like, X an alkyl radical and Y, if present, any other group, substituting a.
hydrogen atom of the benzene ring. The oxy-alkyl-group may occupy the ortho-
meta or para-position, respectively to the azo group and it has been found that the
tints obtained from the para and meta derivatives resemble each other, both
shewing a strongly greenish hue, whilst the ortho derivatives have a less.
greenish hue.
The following example is given in order to illustrate the process for the
production of the new colouring matters.
The solution of the diazo derivative of 42 kilos. of meta-amido-para-cresol
methyl ether (CH2: OCH, NH, 1:4:3) is allowed to flow into a cooled solution
of 50 kilos. of salicylic acid, kept alkaline throughout the reaction. As soon as
the combination is completed the mixture is heated to boiling, the excess of alkali
is removed by neutralizing with acid, and the colouring matter is precipitated by
means of common salt in the shape of yellow crystalline needles. It dyes chromium,
mordanted wool a bright yellow.
If in the above example, for the meta-amido-para-cresol ether the equivalent.
quantity of ortho-amidophenol-methyl ether be substituted, a similar colouring
matter is obtained. A product dyeing with a more greenish tint may be produced
by employing para-amidophenol ether or meta-amido-phenol ether. Similar results.
may be obtained if in the above examples, instead of the methyl ethers the ethyl
ethers are used.
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 herein described manufacture of colouring matters dyeing yellow with
mordants by combining the diazo-derivatives of aromatic amines containing the.
oxy-alkyl-group with phenol-carbo-acids.
2. The colouring matters manufactured as above set forth.
A
1 1
T
1 1000
ABEL & IMRAY,
Agents for the Applicant..