Year: 1899

page_text: Date of Application, 26th June, 1899
Complete Specification Left, 7th Mar., 1900--Accepted, 21st Apr., 1900
R
NH.CH,COOH
NH.CH,.COOH,
and which can be obtained in the manner described in the Berichte der Deutschen
Chemischen Gesellschaft, vol. 16, p. 514-516, or by the action of two molecules of
monochloracetic acid on a watery solution of one molecule of a meta diamine of the
benzene series in the presence of sodium acetate, the sulphonic acids of these
diglycines, and the alkyl derivatives of the meta-diamidosulphonic acids of the
benzene series, such as the methyl, ethyl, benzyl derivatives, or the like.
The coloring matters thus obtained dye unmordanted wool, in acid baths, in
general, from reddish-brown to brown shades, which, by a subsequent treatment
with chromium compounds, such as potassium bichromate er the like, are changed
into fast and deep brown shades.

page_text: It may be remarked that, of the above mentioned dye-stuff components, the
sulphonic acids of the glycines and of the diglycines, and the alkyl derivatives of the
metadiamido sulphonic acids, are unknown up to the present time. My foreign
correspondents prepare the sulphonic acids of the glycines and of the diglycines by
acting either with one or with two molecules of monochloracetic acid on one mole-
cule of the corresponding metadiamido sulphonic acids, preferably in the presence of
sodium acetate, or of other condensing agents acting in the same or in a similar
Inanner. The alkyl derivatives of the metadiamidosulphonic acids can be obtained
(according to the researches of my foreign correspondents) by the action of alkyl
haloids (such as methyl chloride, methyl bromide, ethyl iodide, benzyl chloride, or
the like), or of the salts of alkyl-sulphuric acids (such as the sodium salt of methyl-
sulphuric acids or the like) on the metadiamidosulphonic acids of the benzene
series.
In order to illustrate the production of the new coloring matters, my foreign
correspondents give the following examples, the parts being by weight :-
EXAMPLE A.
The diazo
19.9 parts of picramic acid are diazotised in the known manner.
derivative thus obtained is isolated by filtration, and then stirred into a solution
which has been obtained by dissolving 16-6 parts of amidophenylglycine in 200 parts
of water, with the addition of a sufficient quantity of sodium carbonate.
The resulting mixture is stirred for about 12 hours. Subsequently it is heated
to about 80 degrees Centigrade, and then mixed with common salt. The dye-stuff
which precipitates is isolated by filtration, pressed, and dried. It dyes wool, in acid
baths, reddish-brown shades, which, by a subsequent treatment, with potassium
bichromate, are changed into fast deep brown shades.
EXAMPLE B.
(which has been prepared by heating a watery solution of one molecule of the sodium
salt of metaphenylenediaminemonosulphonic acid with one molecule of mono-
chloracetic acid in the presence of sodium acetate), are dissolved in a solution
prepared from 200 parts of water and 6 parts of sodium carbonate. To the resulting
liquid the diazo derivative obtained from 19.9 parts of picramic acid in the manner
described in the foregoing example, is added with continuous stirring. The mixture
thus obtained is further stirred for about 12 hours. Subsequently it is heated to
about 80 degrees Centigrade, and then mixed with a suitable quantity of common
salt. Finally the finished dye-stuff is filtered off, pressed, and dried. It dyes
unmordanted wool in acid baths reddish-brown shades, which, by a subsequent
treatment with potassium bichromatic, are changed into deep brown shades, which
are fast to milling and to light.

page_text: parts of pieramic acid is stirred into a solution prepared from 200 parts of water,
6 parts of sodium carbonate, and 18-8 parts of the neutral sodium salt of the
diglycine of metaphenylenediamine, which body has the formula:-
The resulting mixture is stirred for about 12 hours. Subsequently it is heated
to about 80 degrees Centigrade, and the finished dye-stuff is completely separated
therefrom with the aid of common salt. Finally, the coloring matter is filtered off,
pressed, and dried. It dyes wool, in acid baths, reddish brown shades, which, when
treated with sodium bichromate, are changed into deep brown shades, fast to milling
and to light.
water.
EXAMPLE D.
22.4 parts of the sodium salt of monomethylmetaphenylenediamine sulphonic acid
(which has been prepared by the action of one molecule of methyliodide on one
molecule of metaphenylene diaminesulphonic acid), are dissolved in 100 litres of
The resulting solution is mixed first with 13.6 parts of sodium acetate, and
then (while continuously stirring) with the diazo derivative prepared in the manner
herein before described from 19.9 parts of picramic acid. After being further stirred
for about 12 hours, the mixture is heated to about 80 degrees Centigrade, and then
a sufficient quantity of common salt is added thereto. The dye-stuff which separates
is isolated by filtration, pressed, and dried.
It dyes wool in acid baths reddish-brown shades, which can be changed into deep
brown shades fast to milling and to light by a subsequent treatment with potassium
bichromate.
Similar results are obtained if, instead of the bodies used in examples, other of the
hereinbefore mentioned dye-stuff components are combined with the diazo derivatives
of pieramic acid.
It may be remarked that my foreign correspondents do not intend to confine them-
selves to the above specification, as the details therein given can be varied or
modified within wide limits, without altering thereby the nature of the present
invention.
Dotad this 4th day of 1000
NEWTON & SON,
Agents for the Applicant.
The Manufacture or Production of New Azo Coloring Matters and
of New Intermediate Products for the Production of such
Coloring Matters.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the
0 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 :-

page_text: My foreign correspondents have found that new valuable mono-azo dye-stuffs
obtained by combining the diazo-derivatives of picramic acid-
are
and which can be obtained in the manner described in the "Berichte der Deutschen
chemischen Gesellschaft," Vol. 16, pp. 514-516, or by the action of two molecules of
mono-chloracetic acid on a watery solution of one molecule of a metadiamine of the
benzene series, in the presence of sodium acetate, and the alkyl derivatives of the
metadiamidosulphonic acids of the benzene series, such as the methyl, ethyl, benzyl
.derivatives, or the like.
The coloring matters thus obtained dye unmordanted wool, in acid baths, in general,
from reddish-brown to brown shades, which, by a subsequent treatment with chromium
compounds, such as potassium bichromate or the like, are changed into fast and
deep-brown shades.
It may be remarked that, of the above mentioned dye-stuff components, the
sulphonic acids of the glycines, and the alkyl derivatives of the metadiamidosulphonic
acids, are unknown up to the present.time. My foreign correspondents prepare the
sulphonic acids of the glycines by acting with one molecule of monochloroacetic acid
on one molecule of the corresponding metadiamido sulphonic acids, preferably in the
presence of sodium acetate, or of other condensing agents, acting in the same or in a
similar manner. The alkyl derivatives of the metadiamido sulphonic acids can be
obtained (according to the researches of my foreign correspondents) by the action of
alkylizing agents, such as alkyl haloids (for instance, methyl chloride, methyl
bromide, ethyl iodide, benzyl chloride, or the like), or of the salts of alkyl sulphurie
acids, (such as the sodium salt of methyl sulphuric acid or the like) on the meta-
diamidosulphonic acids of the benzene series.
In order to illustrate the production of the new coloring matters, my foreign
correspondents give the following examples, the parts being by weight:

page_text: about 80 degrees Centigrade, and then mixed with common salt. The dye-stuu
It dyes wool, in acid
which precipitates is isolated by filtration, pressed, and dried.
baths, reddish-brown shades, which, by a subsequent treatment with potassium
bichromate, are changed into fast deep-brown shades.
(which has been prepared by heating a watery solution of one molecule of the sodium
salt of metaphenylene diamine monosulphonic acid with one molecule of mono-
chloracetic acid in the presence of sodium acetate) are dissolved in a solution pre-
pared from 200 parts of water and 6 parts of sodium carbonate. To the resulting
liquid, the diazo derivative obtained from 19.9 parts of picramic acid, in the manner
described in the foregoing example, is added with continuous stirring. The mixture
thus obtained is further stirred for about 12 hours. Subsequently, it is heated to
about 80 degrees Centigrade, and then mixed with a suitable quantity of common
salt. Finally, the finished dye stuff is filtered off, pressed, and dried. It dyes
unmordantel wool, in acid baths, reddish-brown shades, which, by a subsequent
treatment with potassium bichromate, are changed into deep-brown shades, which
are fast to milling and to light.
'
EXAMPLE C.
The diazo derivative which has been obtained in the known manner from 19.9 parts
of picramic acid is stirred into a solution prepared from 200 parts of water, 6 parts of
sodium carbonate and 18.8 parts of the neutral sodiuin salt of the diglycine of meta-
phenylene diamine, which body has the formula-
The resulting mixture is stirred for about 12 hours. Subsequently, it is heated to
about 80 degrees Centigrade, and the finished dye-stuff is completely separated there-
from with the aid of common salt. Finally, the coloring matter is filtered off, pressed,
O and dried. It dyes wool, in acid baths, reddish-brown shades, which, when treated
with sodium bichromate, are changed into deep brown shades fast, to milling and to

page_text: water. The resulting solution is mixed, first, with 13.6 parts of sodium acetate, and
then (while continuously stirring) with the diazo derivatives prepared in the manner
herein before described from 19.9 parts of picramic acid. After being further stirred
for about 12 hours, the mixture is heated to about 80 degrees Centigrade, and then
a sufficient quantity of common salt is added thereto. The dye-stuff which separates
is isolated by filtration, pressed, and dried.
It dyes wool, in acid baths, reddish-brown shades, which can be changed into deep-
brown shades, fast to milling and to light, by a subsequent treatment with potassium
bichromate.
Similar results are obtained if, instead of the bodies used in the examples, other of
the herein before mentioned dye-stuff components are combined with diazo derivatives
of picramic acid.
It may be remarked that my foreign correspondents do not intend to confine them-
selves to the above Specification, as the details therein given can be varied or
modified within wide limits, without altering thereby the nature of the present
invention.
. 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 from abroad, I declare that what I claim is :-
1. The process for the production of amidophenylglycine sulphonic acids, and
homologues thereof, which process consists in causing one molecule of mono chloro
acetic acid to act on one molecule of a metadiamidobenzene sulphonic acid, or homo-
logues thereof, substantially as herein before described.
2. The process for the production of alkyl derivatives of metadiamidobenzene
sulphonic acids, by the action of alkylizing agents on the metadiamido sulphonic
acids of the benzene series, substantially as herein before described.
3. The process for the production of new azo coloring matters, which process con-
sists in combining the diazo derivative of picramic acid with amidophenylglycine, or
its homologues, with amidophenylglycine sulphonic acids or their homologues, or
with the diglycine derivatives of ineta-diamines of the benzene series, or with
alkylized metadiamido benzene sulphonic acids, or the homologues thereof, substan-
tially as hereinbefore described.
4. As new articles of manufacture, the sulphonic acids of the glycines and the
alkylderivatives of the meta-diamido sulphonic acids obtainable by the processes
herein before described and claimed.
5. As new articles of manufacture, the new dye-stuffs obtainable by the processes
herein before described and claimed.
Dated th: Mah
1
1000