Azo dyestuffs derived from nitraniline sulphonic acids
Year: 1895

page_text: Date of Application, 28th Oct., 1895
Complete Specification Left. 27th July, 1896-Accepted, 5th Sept., 1896
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention to be as follows:-
Azo dyestuffs derived from nitraniline sulphonic acids have hitherto not been
employed for dyeing.
Before the invention by my foreign correspondents of the m-nitraniline sulphonic
acid obtained from m-dinitrobenzene, the sulphonic acid of ortho-nitraniline was the
only nitraniline sulphonic acid available for industrial purposes; the method of
formation of the known m-nitraniline sulphonic acid (Ann. 205, p. 102) not
admitting of practical application.
By employing the m-nitraniline sulphonic acid obtained from m-dinitrobenzene
by their new method, my foreign correspondents have succeeded in producing azo
dyestuffs which possess important advantages over the known dyestuffs obtained
not only from o-nitraniline sulphonic acid but also from m-nitraniline. Thus, for
example, both the dyestuffs obtained from the diazodised new m-nitraniline sulphonic
acid and amidonaphthol sulphouic acid G and dimethylaniline respectively surpass the
corresponding dyestuffs derived from o-nitraniline sulphonic acid, not only in greater
purity of the tints but also by greater fastness to alkalies; thus also the dyestuff
from meta-nitraniline sulphonic acid and chromotrop acid is faster to alkali than
the corresponding dyestuff derived from o-nitraniline sulphonic acid, and its tint
is considerably more vivid.
If the dyestuff of commerce obtained from m-nitrodiazobenzene and salicylic acid
is compared with the corresponding dyestuff made from diazotised m-nitraniline
sulphonic acid the latter exhibits advantages consisting in considerably greater
tinctorial power and in greater fastness to water; the latter quality is practically
perfect in the case of the dyestuff containing the sulpho group.
The manufacture of the new dyestuffs is effected by acting upon oxy- and amido-
derivatives of benzene and naphthalene or their sulphonic and carboxylic acids with
the difficultly soluble diazo compound of the above mentioned m-nitraniline
sulphonic acid, either in acid or in alkaline solution according to the component
chosen.
EXAMPLE:
2.18 kilos. m-nitraniline sulphonic acid are stirred up with 1-2 kilos. hydrochloric
acid and sufficient water to form a thin paste, and a solution of 0.69 kiles. sodium
nitrite is run in gradually at the ordinary temperature. The diazo compound thus
formed is run into a solution of 2.39 kilos. of amidonaphtholsulphonic acid G, which
is stirred up with water to form a thin paste. The liquid at once assumes an
intensely red colour. After stirring for a considerable time the dyestuff is
converted into the sodium salt by neutralising the solution with soda, and precipitated
[Price xd I

page_text: in the usual way with salt.
In the dry state, the dyestuff is a brown powder easily
soluble in water with a fine red colour. It dyes wool a bluish-red, dyes woven
goods evenly, and the dyes are very fast to alkali.
Dated this 28th day of October 1895.
ABEL & IMRAY,
Agents for the Applicant.
Manufacture of Azo Dyestuffs from New M-Nitraniline Sulphonic
Acid.
1, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in
the County of London, 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 :-
Azo dyestuffs derived from nitraniline sulphonic acids have hitherto not been
employed for dyeing.
Before the invention by my foreign correspondents of the m-nitraniline sulphonic
acid obtained from m-dinitrobenzene, the sulphonic acid of ortho-nitraniline was the
only nitraniline sulphonic acid available for industrial purposes; the method of
formation of the known m-nitraniline sulphonic acid (Ann. 205, p. 102) not
admitting of practical application.
By employing the m-nitraniline sulphonic acid obtained from m-dinitrobenzene by
their new method, my foreign correspondents have succeeded in producing azo
dyestuffs which possess important advantages over the known dyestuffs obtained
not only from o-nitraniline sulphonic acid but also from m-nitraniline. Thus, for
example, both the dyestuffs obtained from the diazotised new m-nitraniline
sulphonic acid and amidonaphthol sulphonic acid G and dimethylaniline respectively
surpass the corresponding dyestuffs derived from o-nitraniline sulphonic acid, not
only in greater purity of the tints but also by greater fastness to alkalies; thu-
also the dyestuff from meta-nitraniline sulphonic acid and chromotropic acid is
faster to alkali than the corresponding dyestuff derived from o-nitraniline sulphonic
acid, ant is considerably more vivid.
If the dyestuff of commerce obtained from m-nitrodiazobenzene and salicylic
acid is compared with the corresponding dyestuff made from diazotised m-nitraniline
sulphonic acid the latter exhibits advantages consisting in considerably greater
tinctorial power and in greater fastness to water; the latter quality is practically
perfect in the case of the dyestuff containing the sulpho group.
The manufacture of the new dyestuffs is effected by acting upon oxy- and amido-
derivatives of benzene and naphthalene or their sulphonic and carboxylic acids
with the difficultly soluble diazo compound of the above mentioned m-nitraniline
sulphonic acid, either in acid or in alkaline solution, according to the component
chosen.
EXAMPLE.
2.18 kilos. m-nitraniline sulphonic acid are stirred up with 1-2 kilos. hydrochloric
acid and sufficient water to form a thin paste, and a solution of 0.69 kilo. sodium
nitrite is run in gradually at the ordinary temperature. The diazo compound thus
formed is run into a solution of 2.39 kilos. of amidonaphtholsulphonic acid G,
which is stirred up with water to form a thin paste. The liquid at once assumes
an intensely red colour. After stirring for a considerable time, the dyestuff is
converted into the sodium salt by neutralising the solution with sode, and precipi-
tated in the usual way with salt. In the dry state, the dyestuff is a brown powder

page_text: easily soluble in water with a fine red colour. It dyes wool a blueish-red, dyes
woman goods evenly, and the dyes are very fast to alkali
In like manner azo dyestuffs, varying in tint from yellow to red, can be obtained
by combining the diazo compound of the m-nitranilinesulphonic acid described in
the Specification No. 14383 of 1895 with oxy- or amido-derivatives of benzene or
naphthalene or with the sulpho- or carboxyl-acids of such compounds as for
example:
In like manner azo dyestuffs, varying in tint from yellow to red, can be obtained
by combining the diazo compound of the m-nitranilinesulphonic acid described in
the Specification No. 14383 of 1895 with oxy- or amido-derivatives of benzene or
naphthalene or with the sulpho- or carboxyl-acids of such compounds as for
example:
m-nitraniline sulphonic acid (diazotised) with
Amidonaphtholmonosulphonic acid G.
Amidonaphtholdisulphonic acid of the German Patent No. 53023.
Chromotropic acid.
Dioxynaphthalinemonosulphonic acid S.
Naphthionic acid.
B-naphtholsulphonic acid F.
8-
a-
B-
"
"
"
Salicylic acid.
B-oxynaphthoic acid.
Dimethylaniline.
Diethylaniline.
Diphenylamine.
Methyldiphenylamine.
Methylbenzylaniline.
m-phenylenediamine.
m-toluylenediamine.
2.6.
"
"
Neville and Winther.
2.8.
"
Phenyl-3-naphthylamine.
Having now particularly described and ascertained the nature of my said 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 azo dyestuffs varying in tint from yellow
to red by combining the diazo compound of the m-nitranilinesulphonic acid described
in the Specification No. 14383 of 1895 with oxy- or amido-derivatives of benzene
or naphthalene or with the sulpho- or carboxyl-acids of such compounds.
2. The azo-colouring matters manufactured as set forth.
Dated this 10th day of July 100€.
11
Having now particularly described and ascertained the nature of my said 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 azo dyestuffs varying in tint from yellow
to red by combining the diazo compound of the m-nitranilinesulphonic acid described
in the Specification No. 14383 of 1895 with oxy- or amido-derivatives of benzene
or naphthalene or with the sulpho- or carboxyl-acids of such compounds.
2. The azo-colouring matters manufactured as set forth.
Dated this 10th dow of T... 100
ABEL & IMRAY,
Agents for the Applicant.