Manufacture of New Colouring Matters derived from Para- phenylenediamine for Dyeing Wool.
Year: 1899

page_text: Date of Application, 16th Jan., 1899
Complete Specification Left, 7th Oct., 1899-Accepted, 11th Nov., 1899
PROVISIONAL S
Manufacture of New Colouring Matters derived from Para-
phenylenediamine for Dyeing Wool.
I, JOHN IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the
County of London, Consulting Engineer and Chartered Patent Agent, do hereby
declare the nature of this invention (as communicated to me from abroad by La
Societé L. Durand Huguenin & Cie., of St. Fons, Rhone, France, Manufacturers.) to
be as follows:-
According to the publications up to the present time (see German Patent N° 70885
and "Fortschritte der Theer farben fabrikation und verwandter Industriezweige" by
Friedlander 1877 to 1887 page 523) the diazo colouring matters containing the
tetrazo derivative of paraphenylenediamine cannot be applied to the dyeing of wool
on account of their weak resistance to light, and there exists in effect, no such disazo-
colouring matter for wool in commerce.
My correspondents have however found that, contrary to the above facts disazo-
colouring matters can be obtained containing the tetrazo-derivative of paraphenylene-
diamine which resist light and fulling and which are therefore of considerable
industrial value, if one of the components coupled with the said tetrazo-derivative is
formed by an orthocarboxylised phenol of the benzene series or of the naphthalene
series, such as salicylic acid and its homologues, or the a- or the B-oxynaphthoic acid
(melting point 216° C.), while the other component coupled with the said tetrazo-
derivative is constituted by a sulphonic acid of a-naphthol, ß-naphthol, or dioxy-
naphthalenes such as aa dioxynaphthalene, B-a-dioxynaphthalene &c.,
amidonaphthols, such as a₁-u, amidonaphthol, B₁-a-amidonaphthol &c.
or
The colouring matters thus obtained produce upon wool which is chromed either
before or after dyeing, tints which are exceedingly resisting to light and fulling.
They constitute the first colouring matters for wool applicable to industry which
contain the tetrazo derivative of paraphenylenediamine.
EXAMPLE.
27 kilos. of para-amidobenzenelazosalicylic acid (obtained either by combination
muitrodiazobenzene with salicylic acid, and the subsequent reduction of the

page_text: the other known mono- and disulphonic acid of a-naphthol, ẞ-naphthol, of dioxynaph-
thalenes such as a-a dioxynaphthalene, B₁-a, dioxynaphthalene &c., of amidonaph-
thols, such as a₁-a, amido-naphthol, B,-a, amidonaphthol &c.
The salicylic acid can be replaced by cresotinic acid (ortho-oxy-toluic acid)
a-oxynaphthoic acid or ẞ-oxynaphthoic acid (fusing point 216º C.).
1000
ABEL & IMRAY,
Agents for the Applicant.
Manufacture of New Colouring Matters derived from Para-
phenylenediamine for Dyeing Wool.
I, JOHN IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the County
of London, Consulting Engineer and Chartered Patent Agent, do hereby declare the
nature of this invention (as communicated to me from abroad by La Societé
L. Durand Huguenin & Cie, of St. Fous, Rhone, France, Manufacturers) and in what
manner the same is to be performed, to be particularly described and ascertained
in and by the following statement :-
According to published statements (German Patent No. 70885; "Fortschritte
der Theerfarbenindustrie und verwandter Industriezweige" by Friedlander, Vol. I
page 523) the disazo-dyestuffs which have the tetrazo-derivatives of paraphenylene-
diamine in the middle position are not applicable to dyeing wool because of their
feeble degree of fastness to light.
My foreign correspondents have found that dyestuffs for wool which are fast to
light and milling and are derived from paraphenylenediamine may be obtained if
salicylic acid or one of its homologues be used as one of the components and a
sulphonic acid of a- or B-naphthol or of a-dioxynaphthalene as the other. The
dyestuffs thus produced dye chromium-mordanted wool, the tints being fast to light
and milling.
The best parent material for these new dyestuffs is para-amidobenzeneazosalicylic
acid; this is diazotised and combined with another component. This process is con-
trary to Meldola's statement (Journal of the Chemical Society, 1885 I. p. 668) that
the diazo-derivative of para-amidobenzeneazosalicylic acid does not combine with
naphtholsulphonic acids.
EXAMPLE 1.
27 kilos. of para-amido-benzeneazosalicylic acid are diazotised in the usual manner
and the product is added to a solution of 30 kilos. of sodium a₁-, a₂-naphthol-sulpho-
nate (Neville & Winther's acid), made alkaline with sodium carbonate, in such a
manner that the mixture remains alkaline all the time. After 24 hours the mixture
is heated to 70° C. and the dyestuff is salted out, pressed and dried; it dyes chromium
mordanted wool bluish red tints; its solution in water is red and that in strong
sulphuric acid is blue.
EXAMPLE 2.
The diazo-compound from 27 kilos. of amidobenzeneazosalicylic acid is added to a
solution of 26 kilos. of sodium a₁-a-dioxynaphthalene-a-sulphonate in such a manner
that the mixture remains alkaline with sodium carbonate all the time and that
there is always an excess of sodium a₁-u-dioxynaphthalene-ag-sulphonate. After
24 hours the mixture is warmed and the dyestuff is salted out, pressed and dried; it
dyes chromium mordanted wool black,

page_text: The process is the same as that described under Example 2 save that 36 kilos. of
sodium a-a-dioxynaphthalene-ß-B-disulphonate (chromotrope acid) are substituted
for the sodium a₁-a-dioxynaphthalene-a-sulphonate. The dyestuff obtained dyes
chromium mordanted wool black shades.
Similarly there may be used a₁-a-naphtholsulphonic acid, B₁-a,-naphtholsulphonic
acid, or B-B-naphtholsulphonic acid as the component to be combined with diazotised
para-amidobenzene-azosalicylic acid.
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 mordant dyestuffs for wool by combining
diazotised para-amido-benzeneazosalicylic acid with one of the following compo-
ments-a-naphtholsulphonic acid, a-a-naphtholsulphonic acid, B₁-a-naphthol-
sulphonic acid, B-B-naphtholsulphonic acid, a-a-dioxynaphthalene-a-sulphonie
acid, a-a-dioxynaphthalene-ß-B-disulphonic acid (chromotrope acid).
2. The dyestuffs manufactured as above set forth.
ABEL & IMRAY,
Agents for the Applicant.
Dated this 7th day of October 1899.
ABEL & IMRAY,
Agents for the Applicant.