Manufacture of Brown Dyestuffs for Wool.
Year: 1899

page_text: Date of Application, 4th Jan., 1899
Complete Specification Left, 20th Sept., 1899-Accepted, 21st Oct., 1899
PROVISIONAL SPECIFICATION.
Manufacture of Brown Dyestuffs for Wool.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention (as communicated to me from abroad by The Farbwerke vormals: Meister
Lucius and Brüning, of Hoechst a/Main, in the Empire of Germany, Chemical
Manufacturers) to be as follows:-
My foreign correspondents have found that by the action of diazotised 1:2:3 : 5-
and 1:25: 3-nitroamidophenolsulphonic acids, picramic acid, or amidophenol-
sulphonic acid upon metaphenylenediamine or metatoluylenediamine or their
sulphonic acids, new brown dyestuffs may be obtained which are valuable for
properties superior to those of other dyestuffs.
If wool be dyed with these colouring matters and subsequently treated with
bichromate, then the intensity of shade increases and the dye is characterized at the
same time by superior fastness. The existence and position of the hydroxyl in these
dyestuffs appears to be of great influence, as similarly formed dyestuffs, not
containing this group or containing it in a different position, cannot be obtained
in the same manner in equally fast shades.
The process is illustrated by the following examples :-
23.4 kilos. of nitroamidophenolsulphonic acid are diazotised by means of 32 kilos.
of hydrochloric acid and 6.9 kilos. of sodium nitrite, and the product is introduced
into a solution of 10.8 kilos. of metaphenylenediamine and 26 kilos. of sodium
acetate.
The dyestuff is formed at once and after being allowed to stand for a short time
it is salted out; it is in the form of a greenish brown powder, soluble in water with
5 a brown red and with a somewhat more yellow colour in water made alkaline. The
solution in concentrated sulphuric acid is yellow-red.
EXAMPLE II.
19.9 kilos. of picramic acid are diazotised in the usual manner and introduced into
an aqueous solution of 18.8 kilos. of metaphenylenediaminesulphonic acid, and
26 kilos. of sodium acetate. After standing for 12 hours the dyestuff is salted out.
It is in the form of a brown powder, soluble in water with a red brown colour, which
on addition of alkalies becomes more yellow. The solution in concentrated sulphuric
acid is carmine red.

page_text: into an aqueous solution. of 12.2 kilos. of metatoluylenediamine and 26 kilos. of
sodium acetate and allowed to stand for from 2 to 3 days while being well stirred, the
forination of the dyestuff proceeding slowly.
The dyestuff, on being salted out and dried in the usual manner, is in the form of
a brown powder, soluble in water with a brown colour; its tint does not change on
.addition of alkali. The solution in concentrated sulphuric acid in brown.
EXAMPLE IV.
19.9 kilos. of pioramic acid are diazotised and the diazo compound is introduced
into a solution of 21 kilos. of metatoluylenediamine sulphonic acid and 26 kilos. of
sodium acetate. After standing about 12 hours the dyestuff is salted out and 1
filtered.
When in a dry state, the dyestuff is in the form of a brown powder, soluble in
water with a reddish brown colour and in sulphuric acid with a brownish yellow
colour.
Addition of alkalies only slightly changes the tint of the aqueous solution, which 1
becomes a pale yellow.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention (as communicated to me from abroad by The Farbwerke vormals Meister
Lucius and Brüning, of Hoechst a/Main, in the Empire of Germany, Chemical
Manufacturers) and in what manner the saine is to be performed, to be particularly
described and ascertained in and by the following statement:-
My foreign correspondents have found that by the action of diazotised
1:2:3:5- and 1:25:3- nitroamidophenolsulphonic acids, picramic acid, or
amidophenolsulphonic acid upon metaphenylenediamine or metatoluylenediamine or
their sulphonic acids, new brown dyestuffs may be obtained which are valuable for
properties superior to those of other dyestuffs.
If woul be dyed with these colouring matters and subsequently treated with
bichromute, then the intensity of shade increases and the dye is characterised at the
same time by superior fastness. The existence and position of the hydroxyl in these
dyestuffs appears to be of great influence, as similarly formed dyestuffs, not contain-
ing his group or containing it in a different position, cannot be obtained in the same
manner in equally fast shades.
The process is illustrated by the following examples :—
EXAMPLE 1.
23.4 kilos. of nitroamidophenolsulphonic acid (NH,: OH: NO, :80,H = 1:2:3:5)
are diazotised by means of 32 kilos. of hydrochloric acid and 6.9 kilos. of sodium
nitrite, and the product is introduced into a solution of 10.8 kilos. of metaphenylene-
diamine and 26 kilos. of sodium acetate:-
40
The dyestuff is formed at once and after being allowed to stand for a short time it 46
is salted out; it is in the form of a greenish brown powder, soluble in water with a

page_text: 19.9 kilos. of pioramic acid are diazotised in the usual manner and introduced into
5 an aqueous solution of 18.8 kilos. of metaphenylenediaminesulphonic acid, and
26 kilos. of sodium acetate. After standing for 12 hours the dyestuff is salted out. It
is in the form of a brown powder, soluble in water with a red brown colour, which on
addition of alkalies becomes more yellow. The solution in concentrated sulphuric
is carmine red.
19.9 kilos. of picramic acid are diazotised and the diazo-compound is introduced into
a solution of 21 kilos. of metatoluylene-diamine-sulphonic acid and 26 kilos. of
sodium acetate. After standing about 12 hours the dyestuff is salted out and
filtered.
When in a dry state, the dyestuff is in the form of a brown powder, soluble in
water to a reddish brown solution and in sulphuric acid to a brownish yellow
solution.
Addition of alkalies only slightly changes the tint of the aqueous solution, which
becomes a pale yellow.
:
:
H
:
:
Other valuable brown dyestuffs are obtained in a corresponding manner by com-
bining nitroamidophenolsulphonic acid (NH, OH NO, : SOH = 1:2:5: 3) with
1 3 4 meta-phenylenediaminesulphonic acid, meta-toluylene-diaminesulphonic
acid obtained by sulphonating meta-toluylenediamine, meta-toluylenediamine-
sulphonic acid (CH, NH, NH, 80,H=1:2: 6:4) 1:2:4-meta-toluylene-
diamine, or meta-phenylenediamine; by combining nitroamidophenolsulphonic acid
(NH, OH NO, 80 H = 1:2:8:5) with meta-toluylenediamine, meta-pheny-
lenediaminesulphonic acid, or meta-toluylenediaminesulphonic acids; by combining
amidophenolsulphonic acid (NH, OH: SO₂H=1:2:4) with meta-phenylene-
diaminesulphonic acid, or meta-toluylenediaminesulphonic acid; by combining
amidophenolsulphonic acid (NH, OH: SO,H=1:2: 5) with meta-toluylene-
diamine, meta-phenylenediaminesulphonic acid or meta-toluylenediaminesulphonic
acid; and by combining picramic acid with meta-toluylenediaminesulphonic acid
(CH:NH:NH:SOH=1:2:6:4)
:
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is be performed, I declare that what I
claim is
1. The herein described manufacture of brown dyestuffs for wool, by combining
diazotised nitroamidophenolsulphonic acids (NH, OH: NO₂: 80₂H=1:2:5:3
and 1 : 2 : 3 : 5) with meta-phenylenediamine, meta-toluylenediamine, meta-pheny-
lenediaminesulphonic acid or meta-toluylenediaminesulphonic acid; diazotised ortho-

page_text: amidophenolsulphonic acids (NH, OH: 80,H=1:2:4 and 1: 2: 5) with meta-
toluylenediamine, meta-phenylenediaminesulphonic acid or meta-toluylenediamine-
sulphonic acid; diazotised picramic acid with meta-phenylenediaminesulphonic acid
or meta-toluylenediaminesulphonic acids.
2. The dyestuffs manufactured as above set forth.