Re-action of Aromatic Hydrazin Sulphonic Acids on Retenchinon.
Year: 1888

page_text: Re-action of Aromatic Hydrazin Sulphonic Acids on Retenchinon.
A communication from abroad by THE ACTIENGESELLSCHAFT FÜR CHEMISCHE
INDUSTRIE RHEINAU, Baden, in the Empire of Germany.
1, WILLIAM PHILLIPS THOMPSON F.C.S. M.I.M.E. of the Agency for Foreign
Patent Solicitors 6, Lord Street Liverpool and 6 Bank Street Manchester both in
the County of Lancaster and 323 High Holborn in the County of Middlesex Civil
Engineer do hereby declare the nature of this invention to be as follows:-
Hitherto unsuccessful attempts have been made to condense retenchinon with the
aromatic hydrazins as also shown by the recent researches of Bamberger and Hooker
(Annalen der Chemie und Pharmacie, Pages 124, 229).
By this invention, however, this has been effected and it has been found by
exhaustive experiments that the process is possible, when instead of the free hydrazins,
the sulphonic acids of the latter are used, to act on the retenchinon.
The hydrazin sulphonic acids to be employed are themselves easily prepared as is
known, by the reduction of the diazosulphonic acid through sulphide or chloride of
tin. The hydrazin sulphonic acids which come into use amongst others in the process,
are those which are obtained from the following compounds in the aforesaid manner,
namely,
Sulphanilic acid, meta-amido benzo sulphonic acid, orthotoluidine-parasulphonic
acid, paratoluidine orthosulphonic acid, xyloidine sulphonic acid (from the com-
inercial metaxyloidine); cumidin sulphonic acid (from pseudo cumidin): a-naphtly-
amine sulphonic acid, B-naphtylamine sulphonic acid (German Patent No. 22547),
B-naphtylamine-6-sulphonic acid benzidin disulphonic acid and benzidinsulphondi-
sulphonic acid. The extraction of the colouring substances is effected in the following
manner.
.
The necessary. quantities of retenchinon and hydrazin sulphonic acid for example
26.4 kilogrammes (1 molecule) retenchinon and 37.6 kilogrammes (2 molecules)

page_text: phenyl hydrazin sulphonic acid, are introduced into the water needed for the solution
of the resulting colouring substances; the liquor is heated gradually to the boiling
point, and the boiling is continued until both sulphonic acid and chinone have
dissolved themselves and give a completely clear red coloured liquor. Then neutrali-
sation is effected with soda and the colouring substance precipitated with commion
salt.
4
The tinge of the colours obtained hitherto by the reaction of the aromatic hydrazin
sulphonic acid on retenchinon lies between orange red or bluish red. These colours
are characterised by their great fastness. For instance it is not possible to succeed in
removing these colours from wool dyed with them by leaving them for 24 hours in a
solution of soap at 1 per cent. Some are so well fixed on the wool that they cannot
be removed, either by a cold or by a boiling solution of soda. They colour together
wool and silk in the acid bath and are withdrawn completely from the dyeing bath
both by wool and silk.
Dated this 17th day of

page_text: UHC
corouring рuрstances by CEC
Re-action of Aromatic Hydrazin Sulphonic Acids on Retenchinon.
A communication from abroad by THE ACTIENGESELLSCHAFT FÜR CHEMISCHE
INDUSTRIE RHEINAU, Baden, in the Empire of Germany.
•
I, WILLIAM PHILLIPS THOMPSON, F.C.S. M.I.M.E. of the Agency for Foreign
Patent Solicitors, 6, Lord Street, Liverpool and 6, Bank Street, Manchester, both in
the County of Lancaster, and 323, High Holborn, in the County of Middlesex, Civil
Engineer, 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 :-
Hitherto unsuccessful attempts have been made to condense retenchinon with the.
aromatic hydrazins, as also shown by the recent researches of Bamberger and Hooker,
(Annalen der Chemie und Pharmacie, Pages 124, 229).
By this invention, however, this has been effected, and it has been found by
exhaustive experiments that the process is possible, when, instead of the free
hydrazins, the sulphonic acids of the latter are used, to act on the retenchinon.
The hydrazin sulphonic acids to be employed are themselves easily prepared as is
known by the reduction of the diazosulphonic acid, through sulphide or chloride of
tin. The hydrazin sulphonic acids which come into use amongst others in the
process, are those which are obtained from the following compounds in the aforesaid
manner, namely
Sulphanilic acid, meta-amido benzol sulphonic acid, orthotoluidine-parasulphonic
acid, paratoluidine orthosulphonic acid, xyloidine sulphonic acid (from the commercial
metaxyloidine); cumidin sulphonic acid (from pseudo cumidin; a-naphtylamine
sulphonic acid, -naphtylamine sulphonic acid (German Patent No. 22547) B-naphtyl-
amine -sulphonic acid benzidin disulphonic acid and benzidin-sulphondisulphonic
acid. The extraction of the coloring substances is effected in the following
manner :-
The necessary quantities of retenchinon and hydrazin sulphonic acid, for example,
26.4 kilogrammes (1 molecule) retenchinon and 37.6 kilogrammes (2 molecules)
phenyl hydrazin sulphonic acid are introduced into the quantity of water needed for
the solution of the resulting coloring substances; the liquor is heated gradually
to the boiling point, and the boiling is continued until both sulphonic acid and
chinone have dissolved themselves completely and give a clear and red colored
liquor. Then neutralisation is effected with soda and the coloring substance pre-
cipitated with common salt.
The tinge of the colors obtained hitherto by the reaction of the aromatic hydrazin
sulphonic acid on retenchinon lies between orange red and bluish red. These
colors are characterised by their great fastness. For instance, it is not possible to

page_text: succeed in removing these colors from wool dyed with them by leaving them for
24 hours in a solution of soap at 1 per cent. Some are so well fixed on the wool that
they cannot be removed either by a cold or by a boiling solution of soda. They
color together wool and silk in the acid bath, and are withdrawn completely from the
dyeing bath both by wool and silk.
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 correspondents, I declare that what I claim is :-
1. The process of manufacturing coloring substances by condensing aromatic
hydrazin sulphonic acid with retenchinon.
2. The red coloring matter produced by the condensation of an aromatic hydrazin
sulphonic acid with retenchinon, and having the characteristics above described.
Dated this 17th dox of Donember 188e
WM. P. THOMPSON & Co.,
Agents for the Applicant.