Improvements in the Manufacture of Colouring Matters.
Year: 1893

page_text: Date of Application, 5th Aug., 1893
Complete Specification Left, 2nd May, 1894-Accepted, 2nd June,
1894*
PROVISIONAL SPECIFICATION.
[Communicated from abroad by Messrs. WIRTH & Co., of Frankfort-on-the-Main,
in the Empire of Germany, acting as Agents of A. Leonhardt & Co., of
Muhlheim, near Frankfort-on-the-Main, in the Empire of Germany, Aniline
Colour Manufacturers.]
Improvements in the Manufacture of Colouring Matters.
i
I, HENRY HARRIS LAKE, of the Firm of Haseltine Lake & Co., Patent Agents,
45 Southampton Buildings, in the County of Middlesex, do hereby declare the
nature of this invention to be as follows:-
This invention relates to the production of greenish to reddish blue basic
colouring matters derived from metaamidocresol or monoalkylmetaamidocresol
(CH, NH, OH = 1:2:4).
:
These colouring matters can be produced according to the following methods:
1st. Paranitroso derivatives of aromatic amines or chlorimides are condensed with
the amidocresols.
2nd. Instead of the paranitroso derivatives or chlorimides, the corresponding
aromatic paradiamines (such as paraphenylenediamine, paraamidodimethylaniline)
can be employed in which case these latter are subjected to an oxidation, together
with the amidocresols.
3rd. Amidoazo compounds which by reduction yield aromatic paradiamines
(such as benzol-azo-dimethylaniline, amidoazobenzol, benzol-azo-a-naphthylamine)
are condensed with the amidocresols.
4th. Amidoazo compounds derived from the amidocresols (such as benzol-azo-
amidocresol) are condensed with aromatic amines (such as a-naphthylamine or
aromatic diamines) or with the amidocresols.
:
5th. Amidoazo compounds derived from dialkylmetaamidophenols or dialkyl-
metaamidocresols are condensed with the amidocresols.
6th. Instead of the amidoazo compounds mentioned under the 5th method,
the corresponding nitroso compounds (such as nitrosodimethylmetaamidophenol) may
be employed.
'
The above mentioned condensations are effected by heating the two components
in a suitable dissolving or distributing agent, such as spirit or acetic acid, by
preference in the presence of some mineralic acid; and the oxidation according to
the 2nd method is effected by heating the solution of the two components (a
paradiamine and the amidocresols) with an oxidizing agent, such as ferric chloride.
Dated this 5th day of August 1893.
'
HASELTINE, LAKE & Co.,
45, Southampton Buildings, London, W.C.,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Improvements in the Manufacture of Colouring Matters.
I, HENRY HARRIS LAKE, of the Firm of Haseltine, Lake & Co., Patent Agents,
45 Southampton Buildings, in the County of Middlesex, 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:―
0 This invention relates to the production of greenish to reddish blue basic

page_text: colouring matters deriving from metaamiuocresoL
or its monoalkylated derivatives (monomethyl or monoethylmetaamidocresol being
especially employed).
:
Such colouring matters may be obtained, first, by reacting with the mononitroso
derivatives or azo derivatives of dialkylmetaamidophenol or dialkylmetaamidocresol
(CH, NR, OH = 1:2:4) on the amidocresols; second, by transforming the
amidocresols into azo compounds and combining the latter with the amidocresöls or
with aromatic amines; third, by condensing the amidocresols with paranitroso
derivatives of aromatic amines or dichlorimides or aromatic paradiamines or
aromatic paraamido azo compounds.
The following directions will show .in what manner this invention is to be carried
out practically.
First. Preparation of the azo derivatives employed for the purpose, of this
invention. In the Specification 21154" I have shown how azo derivatives of
dialkylmetaamidophenols or cresols can be produced. In a similar way the azo
compounds deriving from metaamidocresol or its monoalkylated derivatives are
obtained, for instance, benzolazoamidocresol is produced by diazotizing one
molecular proportion of aniline and pouring the solution of diazobenzene into an
alkaline solution of one molecular proportion of metaamidocresol, whereby an orange
precipitate is formed, which is pressed and dried.
Second. Production of colouring matters deriving from the nitrosoderivatives
of dialkylamidophenols or cresols or the corresponding azo compounds, and amido-
cresol or monoalkylamidocresol. The production is effected by heating the two
relative compounds (preferably about three molecular proportions of the nitroso
or azo compound to two molecular proportions of the amidocresol) in suitable
dissolving or distributing agent such as spirit or acetic acid or the like.
EXAMPLES.
a
"L
1st. A mixture of 6 kilos. of amidocresol, 16 kilos. of chlorhydrate of
nitrosodimethylmetaamidocresol and 40 litres of spirit is heated at the reflux
cooler until the reaction is finished and the nitroso compound has disappeared. The
mass is then diluted with about 200 litres of hot water, any impurities are removed
from the solution by adding about 7 kilos. of acetate of sodium and the colouring
matter is precipitated from the cooled and filtered liquid by common salt and
chloride of zinc. It dyes mordanted cotton in blue shades.
2nd. 6 kilos. of ethylmetaamidocresol, 15 kos. of benzola zodimethylmeta-
amidophenol, 10 litres of hydrochloric acid of 30% and 40 litres of spirit are
heated at the reflux cooler until (after several hours) the mass has assumed a green
tint. It is then diluted with about 200 litres of boiling water and about 10 kilos.
of acetate of sodium are added to the solution which by this addition assumes a
clear blue colour. After cooling down and filtering the colouring matter is
precipitated with common salt and chloride of zinc. It dyes in blue shades on
mordanted cotton.
Third. Production of colouring matters deriving from azo derivatives of amido-
cresol or monoalkylated amidocresol and aromatic amines. Amongst aromatic
amines the following have been especially tried: alphanaphthylamine or its
alkylated derivatives, metaamidomethyl or metaamidoethylorthotoluidin, meta-
amidodimethylparatoluidine benzlymetaamidodimethylparatoluidine, tetramethyl-
metaphenylenediamine.
'
The production of the colouring matters is effected in an analogous way to that
pointed out under second.
EXAMPLES.

page_text: "
diluted with hot water the solution is purified with 5 kos. of carbonate of sodium
and the colouring matter is precipitated in the usual way. It dyes mordanted
cotton in blue shades.
2nd. 15 kilos. of chlorhydrate of benzolazoalphanaphthylamine, 6 kilos. of
ethylmetaamidocresol, 10 litres of muriatic acid of 30% and 50 litres of spirit are
heated at the reflux cooler until the solution is coloured bluish violet. After
cooling down the dyestuff is crystallized. It dyes mordanted cotton in reddish
blue shades.
Seventh. Production of colouring matters deriving from aromatic paradiamines
and amidocresol or monoalkylamidocresol. By operating in this way, the two
relative components are to be subjected to an oxidation in a suitable manuer.
Example: dissolve 6 kilos. of amidocresol, 20 kilos. of acetate of sodium,
10 kilos. of chlorhydrate of paratoluylenediamine in about 500 litres of boiling
water and gradually add to the boiling liquid about 140 litres of a solution of
ferric chloride of 15%. After cooling, the liquid is filtered and the colouring
matter is precipitated from the solution by chloride of zinc and common salt. It
dyes mordanted cotton in violet blue shades.
Having now particularly described and ascertained the nature of the said
invention, and in what manner the same is to be performed, as communicated to
me.by my foreign correspondents, I declare that what I claim is :-
1. The production of reddish to greenish blue basic colouring matters deriving
from metaamidocresol (CH, NH,: OH = 1:2:4) or its monomethylated or
monoethylated derivative by the hereinbefore described process which consists in
(a) Reacting with the said metaamidocresol or monoalkylmetaamidocresol on
the nitroso derivatives or azo derivatives of dialkylmetuamidophenol or
dialkylmetaamidocresol (CH, : NR,: OH = 1:2:4) substantially as herein-
before described.
(b) Reacting with the azo compounds of the said metaamidocresol or monoalkyl-
metaamidocresol on alphanaphthylamine or its alkylated derivatives, meta-
amidomethyl- or metaamidoethylorthotoluidine, metaamidodimethylpara
toluidine, benzylmetanmidodimethylparatoluidine, tetramethylmetaphenylenė-
diamine substantially as hereinbefore described.
(c) Reacting with the azo compounds of the said metaamidocresol or monoalkyl-
metaamidocresol on the said metaamidocresol or monoalkylmetaamidocresol
substantially as hereinbefore described.
(d) Reacting with the said metaamidocresol or monoalkylmetaamidocresol on
aromatic paranitroso derivatives or dichlorimides or paraamidoazo derivatives
especially on those pointed out in the Specification substantially as herein-
before described.
(e) Reacting with the said metaamidocresol or monoalkylmetaamidocresol on
aromatic paradiamines and especially on paratoluylenediamine in the
presence of a suitable oxidizing agent substantially as herein before
described.
2. The greenish to reddish blue basic colouring matters produced substantially
as herein before described.
032
HASELTINE, LAKE & Co.,
45, Southampton Buildings, London, W.C.,
Agents for the Applicant.