Manufacture of a New Naphthylen-diamine Mono Sulpho Acid, and of Colouring Matters Derived therefrom.
Year: 1894

page_text: Date of Application, 27th Apr., 1894
Complete Specification Left, 16th Jan., 1895-Accepted, 16th Feb., 1895
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE ACTIEN GESELLSCHAFT FÜR ANILIN
FABRIKATION. of Berlin, in the
Empire of Germany, Chemical
Manufacturers.]
Manufacture of a New Naphthylen-diamine Mono Sulpho Acid, and
of Colouring Matters Derived therefrom.
I, CHARLES DENTON ABEL of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Consulting Engineer and Chartered Patent
Agent, do hereby declare the nature of this invention to be as follows:-
This invention relates to the manufacture of a new diamido-naphthalene mono
sulpho acid and colouring matters derived therefrom.
For this purpose the B 3, dihydroxy-naphthalene ẞs mono sulpho acid is con-
verted by the action of ammonia into the new ẞ, ß, naphthylen-diamine ẞ, mono
sulpho acid.
The following is an example illustrating one way in which this invention can be
practically carried out.
100 kilos. of the sodium salt of the ẞ, ẞ, dihydroxynaphthalene ẞ, mono sulpho
acid are heated with 200 kilos. of ammonia solution containing about 22 per cent.
ammonia at a temperature of about 160° to 170° C. After 10 hours of thus heating,
the temperature is raised to 200° to 220° C. and the heating is continued for
10 hours more.
The mixture is then dissolved in water, the excess of ammonia is
removed by boiling, and the new acid is precipitated by means of hydrochloric
acid.
The new ẞ, B, naphthylen-diamine ẞ, mono sulpho acid is sparingly soluble in
water, its sodium salt is more soluble in water, showing a little blue fluorescence.
With chloride of iron it produces a blue solution, it yields no diazo compound but
an azimido compound.
Instead of the B, ẞ, dihydroxy-naphthalene ẞ, mono sulpho acid, the amido
naphthol sulpho acid R may be treated in an analogous manner, with the like
result.
The new acid produces valuable dye stuffs with the diazo compounds of amines,
para-diamines, amido-azo-bodies and their sulpho- and carbo-acids. These colouring
matters, especially those derived from the tetrazo-compounds of para-diamines,
directly dye unmordanted cotton in an alkaline or salt bath. Generally, the brown
tint prevails in the colours thus obtained.
The manufacture of these colouring matters may be carried out in the manner
generally adopted for the production of azo-dyes.
Dated this 27th day of April 1894.
ABEL & IMKAI,
Agents for the Applicant.

page_text: Manufacture of a New Naphthylen-diamine Mono Sulpho Acid, and.
of Colouring Matters Derived therefrom.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Consulting Engineer and 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::-
:
This invention relates to the manufacture of a new diamido-naphthalene mono
sulpho acid and colouring matters derived therefrom.
For this purpose the B₁ ẞ, dihydroxynaphthalene ẞ, mono sulpho acid is con-
verted by the action of ammonia into the new ẞ₁ ẞ: naphthylen diamine ẞ, mono
sulpho acid.
The following is an example illustrating one way in which this invention can be
practically carried out.
100 kilos. of the sodium salt of the ẞ, ẞ, dihydroxynaphthalene ẞ, mono sulpho
acid are heated with 200 kilos. of ammonia solution (containing about 22 per cent.
ammonia) at a temperature of about 160° to 170° C. After 10 hours of thus
heating, the temperature is raised to 200° to 220° C. and the heating is continued
for 10 hours more.
The mixture is then dissolved in water, the excess of ammonia
is removed by boiling, and the new acid is precipitated by means of hydrochloric
.acid.
The new Bi B, naphthylen-diamine ẞ, mono sulpho acid is sparingly soluble in
water, its sodium salt is more soluble in water, shewing a little blue fluorescence.
With chloride of iron it produces a blue solution, it yields no diazo compound but
an azimido compound.
Instead of the ẞ₁ ẞ, dihydroxy-naphthalene ẞ, mono sulpho acid, the amido
naphthol sulpho acid R may be treated in an analogous mauner, with the like
result.
My foreign correspondents have found that the said ß, ß,-naphthylendiamine
B, sulphonic acid is capable of combining with tetrazotised paradiamines such as
benzidine, tolidine, dianisidine and their homologues and analogues. There may
be thus produced dyestuffs termed "symmetrical" and "mixed" which dye on
unmordanted cotton tints varying from orange to brown.
"
The following example illustrates the process for producing the so called
symmetrical" dyestuffs derived from tetrazotised paradiamines and the new
naphthylendiamine sulphonic acid.
One molecular proportion of benzidine is tetrazotised in the well known manner
and combined in alkaline solution with two molecular proportions of the sodium
salt of the Biẞ,-naphthylendiamin-3-sulphonic acid. The formation of the
new colouring matter begins at once and is completed after about 24 hours. It
dyes unmordanted cotton from an alkaline or salt bath brown red.
In the mixed dyestuffs above referred to only one of the diazo groups in the
tetrazotised paradiamine is combined with the BB-naphthylenediamine-ß,-sulphonic
acid the other diazo group being united with an amine, diamine, phenol, amido-
phenol of the benzene or naphthalene series and their sulpho and carbo acids.
The following example illustrates the process for producing the so called
"mixed" dyestuffs.
One molecular proportion of benzidine is tetrazotised in the well known manner
and combined in alkaline solution with one molecular proportion of the sodium
salt of the new naphthylendiamine sulphonic acid. After the combination of the
intermediate product is complete-one molecular proportion of an alkaline solution
of salicylic acid is added. The formation of the new dyestuff is completed after

page_text: about 24 hours. The colouring matter is separated by means of salt; it dyes
unmordanted cotton yellowish brown. The combination may also be carried out in
the inverse way, that is to say, by combining the tetrazo compound first with
salicylic acid and then with the naphthylendiamin sulphonic acid.
My foreign correspondents have further found that the ß ß-naphthylendiamin-
B-sulphonic acid is capable of combining with one or two molecules of diazotised
amines or amidonzo bodies of the benzene and naphthalene series, their sulphonic
and carbonic acids or other convenient substitution derivatives thereof.
The colouring matters thus obtained are valuable dyestuffs, which dye on cotton
and wool tints varying from orange to brown.
The following is an example.
One molecular proportion of aniline is diazotised in the usual way and added to
a neutral solution of one molecular proportion of the sodium salt of the (31 ẞr-
naphthylendiamine-ß-sulphonic acid. After the formation of the new dyestuff is
complete, the whole is rendered alkaline by boiling with carbonate of soda, and the
new colouring matter is separated by salt. It dyes wool in an acidulated bath
yellowish orange.
The colouring matter resulting from the combination of two molecular propor-
tions of diazobenzene and the new acid is not so easily soluble: it dyes wool
yellowish red.
Other azo dyestuffs derived from the new acid may be produced in a similar
manner and according to the methods known to chemists who are familiar with the
preparation of azo dyes.
Having now particularly described and ascertained the nature of my said
invention and in what manner the same is to be performed, I declare that what I
claim is :-
:-
1. The herein described manufacture of a new ẞ1 B,-naphthylendiamine-ẞ-
sulphonic acid by heating the sodium salt of the dioxynaphthaline sulphonic acid R
with ammonia in a closed vessel.
2. The herein described manufacture of azo-dyestuffs derived from the ẞ₁ Br
naphthylene-diamine-ß,-sulphonic acid above referred to.
3 The BB-naphthylenediamine-ẞ,-sulphonic acid manufactured
described.
as herein
4. The azo dyestuffs derived from the ẞ₁ß,-naphthylendiamine-ßs-sulphonic acid
above referred to and manufactured as herein described.
Dated this 14th day of January 1895.
ABEL & IMRAT,
Agents for the Applicant.