The Manufacture of Basic Dyestuffs from Alpha-naphtho-quinone- dichlorimide.
Year: 1891

page_text: Date of Application, 29th June, 1891
Complete Specification Left, 15th Mar., 1892-Accepted. 7th May. 1892
PROVISIONAL SPECIFICATION.
The Manufacture of Basic Dyestuffs from Alpha-naphtho-quinone-
dichlorimide.
1. JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of
Middlesex, Gentleman, do hereby declare the nature of this invention which has
been communicated to me from abroad by the Badische Anilin and Soda-Fabrik
of Ludwigshafen on Rhine in the Empire of Germany to be as follows :--
In the Specification of Letters Patent No. 4476 of 1888 granted to me there is
described the preparation of blue basic dyestuff's (eg. Nile blue) by the condensation
of nitroso-derivatives of alkylated metamido-phenol with alpha-naphthylamine and
certain analogous compounds.
The present invention is based upon the discovery that dyes of this class can be
obtained by the condensation of dialkylated metamido-phenol with alpha-naphtho-
quinone-dichlorimide.
The said dichlorimide results from the action of hypochlorites on 1-4 naphthylene
diamine in the presence of a mineral acid and can be used in a variety of ways
for the manufacture of dyestuffs.
The condensation of the dichlorimide with the dialkylated metamidophenol
compounds can be readily effected by gently heating the bodies together in the
presence of a suitable solvent such as wood-spirit, alcohol, acetic acid, water or
certain salt solutions.
The following directions for the preparation of Nile-blue will serve as an example
to illustrate this invention.
Mix together about eight parts of diethyl-metamido-phenol and about eleven
parts of alpha-naphthoquinone-dichlorimide with about thirty parts of wood-spirit,
and warm the mixture carefully to a temperature of about fifty to sixty degrees
centigrade. A rapid reaction takes place, and in a short time the solution becomes
a semi solid mass of shining green crystals of the colouring matter.
When no
further increase in the quantity is observed cool the mixture filter off the mother
liquor wash with wood-spirit till the wash is of a pure blue colour, and then dry.
The colouring matter is thus obtained in the form of its hydrochlorate and can be
converted into its commercial form of sulphate as described in the aforesaid
Specification of Letters Patent No. 4476 of 1888.
Analogues of diethyl-metamidophenol can replace this body in the above
example when a similar reaction takes place and analogous dyes are obtained, such
analogues are for instance dimethyl-metamidophenol, dimethylortho amido-para-
cresol, metahydroxy-di-phenylamine and meta hydroxy phenyl naphthylamine.
Dated this 29th day of June 1891.
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, W.C., Agents.
COMPLETE SPECIFICATION.
The Manufacture of Basic Dyestuffs from Alpha-naphtho-quinone-
dichlorimide.
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of
Middlesex Gentleman do hereby declare the nature of this invention (which has
been communicated to me from abroad by the Badische Anilin & Soda Fabrik of
Ludwigshafen on Rhine in the Empire of Germany) and in what manner the
Price 8d.1

page_text: same is to be performed to be particularly described and ascertained in and by the
following statement. :-
In the Specification of Letters Patent No. 4476 of 1888 granted to me, there is
described the preparation of blue basic dyestuff (e.g. Nile blue) by the condensation
of nitroso-derivatives of alkylated metamido-phenol with alpha-naphthylamine and
certain analogous compounds.
The present invention is based on the discovery of my foreign correspondents
that dyes of this class can be obtained by the condensation of dialkylated meta-
amido-phenol or analogous compounds with alpha-naphtho-quinone-dichlorimide.
The said dichlorimide results from the action of hypochlorites on
naphthylene diamine in the presence of a mineral acid (see Beilstein Vol. 111.
p. 1022).
1.4
The condensation of the dichlorimide with the dialkylated metamidophenol
compounds can be readily effected by gently heating the bodies together in the
presence of a suitable solvent such as wood-spirit, alcohol, acetic acid, water or
certain salt solutions.
The following directions for the preparation of Nile blue will serve as an
example to illustrate the invention and the manner in which it can be carried into
practical effect. Mix together about eight parts by weight of diethyl-metamido-
phenol and about eleven parts by weight of alpha-naphthoquinone-dichlorimide
with about thirty parts by weight of wood spirit, and warm the mixture carefully
to a temperature of about fifty to sixty degrees centigrade. A rapid reaction
takes place, and in a short time the solution becomes a semi-solid mass of shining
green crystals of the colouring matter. When no further increase in the quantity
is observed, cool the mixture, filter off the mother liquor, wash with wood-spirit
till the wash is of a pure blue colour and then dry. The colouring matter is thus
obtained in the form of its hydrochlorate, and can be converted into its commercial
form of sulphate as described in the aforesaid Specification of Letters Patent
No. 4476 of 1888.
Analogues of diethyl-metamidophenol can replace this body in the above
example when a similar reaction takes place and analogous dyes are obtained; such
analogues are dimethyl-metamidophenol, dimethyl-ortho-amido-para-cresol, meta-
hydroxy-diphenylamine and metahydroxy-phenyl-naphthylamine.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
1. The manufacture of basic dyestuffs-namely Nile blue and analogues thereof
by condensing alpha-naphthoquinone-dichlorimide with a dialkylated meta-amido-
phenol or analogous compounds hereinbefore mentioned, all substantially as
bereinbefore described.
2. The manufacture of the basic dyestuff known as Nile blue by the condensa-
tion of alpha-naphthoquinone-dichlorimide with diethyl-meta-amido-phenol sub-
stantially as hereinbefore described in the example.
th: 15th dare at March 1800
J. H. JOHNSON & Co.,
Agents.