Improvements in the Manufacture of Sulpho Acids of the Naphthalene Series, and of Colouring Matters derived therefrom.
Year: 1897

page_text: Date of Application, 19th Mar., 1897
Complete Specification Left, 11th Dec., 1897-Accepted, 22nd Jan., 1898
[Communicated from abroad by FARBWERK MUHLHEIM vormals A. LEONHARDT & Co.,
Muhlheim-on-the-Main, in the Empire of Germany.]
Improvements in the Manufacture of Sulpho Acids of the Naphthalene
Series, and of Colouring Matters derived therefrom.
I, HENRY HARRIS LAKE, of the Firm of Haseltine, Lake & Co., Patent Agents,
45, Southampton Buildings, in the County of Middlesex, do hereby declare the nature
of this invention to be as follows:-
In the Specification of former Patent No. 19253 95 it is stated that by introducing
into the 1.8 amidonaphthol-3-sulphoacid one further sulphogroup in the position 5, a
disulphoacid is obtained, which may be very advantageously employed for the
production of azocolouring matters.
Now I have found that azocolouring matters of even more beautiful and deeper
shades are produced, when after the introduction of the 5 sulphogroup, the
amidogroup is subjected to an alkylation.
For the production of this alkylamidonaphthaldisulphoacid I make use of the
methods generally known for the alkylation of amidophenols taking care however,
that the 5. sulphogroup is not eliminated by too elevated a temperature. The
alkylamidonaphthol disulphoacid thus produced is more easily soluble in water than
the non alkylated acid. When heated with diluted sulphuric acid up to about 130° C.,
alkylamidonaphthol monosulphonic acid is obtained, which can be equally employed
for the production of azocolouring matters.
This production of azocolouring matters is effected in the generally well known
manner, best in alkaline solutions."
The alkylated acids may also be combined with
several molecules of a diazocompound.
For instance, ethylamidonaphtholdisulphoacid, when combined with
diazobenzene yields a dark claret dye
a-diazonaphthalene yields a deep blue dye
tetrazodiphenyl yields a blue dye
2 mol. of paranitrodiazobenzene yields a deep green dye
dianisidine-azo-salicylic acid yields a green dye.

page_text: Improvements in the Manufacture of Sulpho Acids of the Naphthalene
Series, and of Colouring Matters derived therefrom.
I, HENRY HARRIS LAKE, of the Firm of Haseltine, Lake & Co., Patent Agents,
45, Southampton Buildings, in the County of Middlesex, 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 :-
In the Specification of former Patent No. 1925305 it is stated that by introducing
into the 1.8.amidonaphthol-3-sulphoacid one furthersu lphogroup in the position 5,
a disulphoacid is obtained which may be very advantageously employed for the
production of azocolouring matters.
Now I have found that azocolouring matters of even more beautiful and deeper
shades are produced when after the introduction of the 5-sulphogroup the
amidogroup is subject to an alkylation.
For the production of this alkylamidonaphtholdisulphoacid I make use of the
methods generally known for the alkylation of amidophenols taking care however
that the 5-sulphogroup is not eliminated by too elevated a temperature. For
instance, in order to produce ethylamidonaphthol disulphoacid, I proceed as follows:
3 kilos of amidonaphtholdisulphoacid obtained as described in the above
mentioned prior Specification No. 1925305 are dissolved in 15 litres of water and
0.5 kilos of carbonate of soda and the solution is heated together with 10 litres of
spirit and 1-5 litres of ethylbromide in a closed vessel during about 12 hours up to
about 90° C. After cooling, the mass is acidulated with hydrochloric acid and spirit
and ethylbromide is distilled over. The alkylated acid crystallizes from the
concentrated solution; it is more easily soluble in water than the non-alkylated acid
and is only with difficulty precipitated by common salt. The watery solution when
treated with nitrous acid yields a yellow solution which does not turn to violet by the
addition of carbonate of soda. By heating the alkylated acid with dilute sulphuric
acid up to 130° C., the 5-sulphogroup is split off.
The production of azocolouring matters from this alkylated disulphoacid is effected
in a way quite analogous to that described in the said former specification. The
most valuable products are obtained by the action of one molecular quantity of a
diazo (diazoazo) compound or of one half molecular quantity of a tetrazocompound.
The combination is best effected in a watery solution made alkaline by carbonate of
soda. However the alkylated disulphoacid is also capable of combining with
diazobodies in weakly acidulated solutions or with several molecular quantities of
diazobodies.
For instance, by combining the alkylated disulphoacid with the following diazo-
bodies, the following corresponding shades are obtained:
diazobenzene
a-diazonaphthalene
diazoazobenzene
a-diazoazonaphthalenesulphoacid
tetrazodinhonal
deep claret
dark blue
greenish black
greenish black

page_text: Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed, as communicated to
me by my foreign correspondent, I declare that what I claim is
:-
1. The process of producing 1.8-alkylamidonaphthol-3-5-disulphoacid which
process consists in alkylating 1.8 amidonaphthol-3-5-disulphoacid substantially as
hereinbefore described.
2. The process of producing azocolouring matters by the action of diazo- or
tetrazocompounds on 1.8-alkylamidonaphthol-3-5-disulphoacid, substantially as
hereinbefore described.
3. The 1.8 alkylainidonaphthol-3-5-disulphoacid produced as claimed under the
HASELTINE, LAKE & Co.,
45, Southampton Buildings, London, W.C., Agents for the Applicant.