The Manufacture of New Sulphonic Acids and of Colouring Matters and other Products therefrom.
Year: 1899

page_text: Date of Application, 26th June, 1899
Complete Specification Left, 24th Mar., 1900-Accepted, 23rd June, 1900
The Manufacture of New Sulphonic Acids and of Colouring Matters
and other Products therefrom.
We, IVAN LEVINSTEIN, Managing Director, FRITZ POLLAK, Ph.D., Chemist,
and LEVINSTEIN LIMITED, Chemical Manufacturers, all of Minshull Street, Man-
chester, in the County of Lancaster, do hereby declare the nature of this inven-
tion to be as follows:
We have discovered that if alpha,naphthylamine alpha, sulphonic acid be
suitably treated, as for example at a temperature of from 0° to 50° C., with nitric
acid in presence of sulphuric acid, it is converted into a new body to which we
attribute the constitution of an alpha,amido-alpha,nitro alpha,sulphonic acid.
This new product is a colouring matter which dyes wool in a neutral or acid
bath, greenish-yellow shades.
We have further discovered that this new substance, when diazotised and com-
bined with amines, diamines, phenols, amidophenols, oxyphenols both of the
benzene and of the naphthalene series, as well as with their sulphonic or car-
boxylic acids, forms yellow to black colouring matters somewhat resembling
those obtained from paranitraniline, but generally bluer in shade.
We have also found that these new colouring matters may be reduced by
means of sodium sulphide or similar reducing agents, whereby the nitro group
is transformed into the amido group.
The further new colouring matters thus obtained may be rediazotised and com-
bined with the well known azo colour components.
These disazo colouring matters produce shades varying from red to black and
are of great technical value on account of their affinity for animal and vegetable
fibres.
We have yet further discovered that our new alpha amido-alpha,nitro-alpha-
sulphonic acid may be easily reduced, whereby a new diamidonaphthalene sul-
phonic acid is formed to which we attribute the constitution of an alpha,alpha-
naphthylenediamine alpha,(alpha)-monosulphonic acid.
Amongst other valuable properties which this last described new sulphonic
acid possesses; we have found that it is valuable as a photographic developer. It
developes very slowly and is thus of peculiar advantage for use in the develope-
ment of overexposed plates.
Dated this Twenty-third day of June A.D 1900
W. E. HEYS & SON,
Agents for the Applicants.

page_text: The Manufacture of New Sulphonic Acids and of Colouring Matters
and other Products therefrom.
We, IVAN LEVINSTEIN, Managing Director, FRITZ POLLAK, Ph.D., Chemist,
and LEVINSTEIN LIMITED, Chemical Manufacturers, all of Minshull Street, Man-
chester, in the County of Lancaster, do hereby declare the nature of this inven-
tion, and in what manner the same is to be performed, to be particularly described
and ascertained in and by the following statement:–
We have discovered that if alpha,naphthylamine alpha, tulphonic acid be
suitably treated, as for example at a temperature of from 0° to 100 C., with nitric
acid in presence of sulphuric acid, it is converted into a new body to which we
attribute the constitution of an alpha,amido-alpha,nitro-alphagsulphonic acid.
This new product is a colouring matter which dyes wool in a neutral or acid
bath, greenish yellow shades.
We have further discovered that this new substance, when diazotised and com-
bined with amines, diamines, phenols, amidophenols or oxyphenols, either of the
benzene cr of the naphthalene series, as well as with their respective sulphonic
or carboxylic acids, forms yellow to black colouring matters somewhat resembling
those obtained from paranitraniline, but generally bluer in shade.
We have also found that our new alpha,amido-alpha, nitro-alpha,sulphonic
acid may be easily reduced, whereby a new diamidonaphthalene sulphonic acid
is formed, to which we attribute the constitution of an alpha,alpha, naphthylene-
diamine-alpha (alpha) monosulphonic acid.
The following examples illustrate in what manner we may carry our inven-
tion into practical effect.
EXAMPLE I.
Production of the new (alphajamido-alpha-nitro-alpha,)-sulphonic acid.
22.3 kilos. of alpha,naphthylamine-alpha,sulphonic acid is dissolved in 150 kilos.
of sulphuric acid (660 Bé.) and nitrated with a mixture of nitric and sulphuric
acids containing 6.3 kilos. of nitric acid, the temperature being kept, during the
operation, between about 0° and 10° C. After some hours, the mixture is run
into 500 litres of water, whereupon the new alpha,amido-alpha,nitro-alpha, sul-
phonic acid separates out in the form of yellow flakes. It, and its diazo compound,
are moderately soluble in water. Instead of the mixed acids, nitric acid alone
may be employed for the nitration.
EXAMPLE IF.
Production of diazo colouring matters from the new (alpha,amido-alpha,nitro-
alpha) sulphonic acid.
26.8 kilos. of alpha,amido-alpha,nitro-alpha, sulphonic acid is diazotised in
the usual way with 7 kilos. of sodium nitrite and hydrochloric acid. The diazo
body so obtained is combined, in an alkaline solution, with 32 kilos. of alpha,-
alpha dioxynaphthalene beta,beta disulphonic acid and stirred for several hours.
The mixture is then heated to about 80° C. and the colour is afterwards salted
out and filtered off. It is a greenish black powder producing a bright red solu-
tion in acid, which changes by the addition of alkali, to violet-red. It dyes wool,
in a slightly acid bath, a blue-red shade. Analogous dye-stuffs are produced in
carrying out the process described under this example, if, in place of the dioxy-
naphthalene disulphonic acid 1.8.3.6., amines, phenols, or amidophenols, of the
benzene or naphthalene series, or their sulphonic or carboxylic acids are used.

page_text: EXAMPLE III.
Production of a new diamido naphthalene sulphonic acid from the new (alpha,-
amido-alpha,nitro-alpha) sulphonic acid.
The nitronaphthylamine monosulphonic acid is suspended in water to which
there is then added an equivalent proportion of an alkali. The resulting solution
is then run into a reducing mixture of iron and acetic acid, and heated for some
hours. After the reaction is finished, the dissolved iron is precipitated with
magnesia, and alpha,alpha,naphthylenediamine-alpha,(alpha) sulphonic acid is
obtained from the filtrate by precipitation with hydrochloric acid.
greyish needles and oxidises easily in alkaline solution.
It forms
Having now particularly described and ascertained the nature of our said
invention and in what manner the same is to be performed, we declare that what
we claim is:-
-
1. As a new article of manufacture, the new (alpha,amido-alpha,nitro-alpha,)
sulphonic acid, produced substantially as herein before described.
2. As new articies of manufacture, the new diazo colouring matters produced
from the new (alpha,amido-alpha,nitro-alpha) sulphonic acid, substantially as
hereinbefore described.
3. As a new article of manufacture, the new diamido-naphthalene sulphonic
acid produced from the new (alpha,amido-alpha,nitro-alpha) sulphonic acid, and
to which we have attributed the constitution of an alpha,alpha,naphthy-
lenediamine alpha,(alpha) monosulphonic acid, substantially as herein before
described.
4. The manufacture or production of a new sulphonic acid to which we have
attributed the constitution of an alpha,amido-alpha,nitro-alpha, sulphonic acid,
substantially as herein before described.
5. The manufacture or production of new diazo colouring matters from the new
sulphonic acid described in the 4th claim, substantially as hereinbefore described.
6. The manufacture or production of the new diamido-naphthalene sulphonic
acid from the new sulphonic acid described in the 4th claim, substantially as
herein before described.
013 1
1
T
1000