The Manufacture and Production of New Basic Dyestuffs.
Year: 1891

page_text: Date of Application, 22nd June, 1891
Complete Specification Left, 10th Mar., 1892-Accepted, 16th Apr., 1892
PROVISIONAL SPECIFICATION.
The Manufacture and Production of New Basic Dyestuffs.
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 and Soda Fabrik
of Ludwigshafen on Rhine in the Empire of Germany) to be as follows:-
In the Specification to Letters Patent No. 4476 of 1888 granted to me there is
described the manufacture of the mono-nitroso-compounds of di-methyl and diethyl-
metamido-phenol and the production of blue basic dyestuffs (e.g. Nile blue)
by the condensation of these nitroso-compounds with alpha-naphthylamine and
its alkyl derivatives, such as ethyl-alpha-naphthylamine and dimethyl-alpha-
naphthylamine.
My foreign correspondents have now discovered that new and valuable basic
dyes can be obtained by condensing the hereinbefore mentioned nitroso-compounds
with other derivatives of alpha-naphthylamine instead of with alpha-naphthylamine
itself or those alkyl compounds mentioned in the aforesaid Specification of Letters
Patent No. 4476 of 1888.
Such a compound is for instance benzyl-alpha-naphthylamine. This body appears
to have been prepared by the action of alpha-naphthylamine on benzyl-amine but
can be more advantageously obtained by the interaction of two molecular proportions
of alpha-naphthylamine and one molecular proportion of benzyl-chloride in the
presence of a suitable solvent such as toluene at the temperature of the water bath.
By the action of hydrochloric acid gas in an ethereal solution of benzyl-alpha-
naphthylamine it can be converted into its hydrochlorate.
Instead of benzyl-alpha-naphthylamine other analogous compounds can be
employed.
To more clearly illustrate the nature of this invention 1 give by way of example
the following directions for the production of a new greenish-blue dye from
nitroso-diethyl-metamido-phenol and benzyl-alpha-naphthylamine the parts being
by weight.
Mix about sixty-nine parts of the hydrochlorate of nitroso-diethyl-metamido-
phenol and about fifty four parts of hydrochlorate of benzyl-alpha-naphthylamine
with about one hundred parts of spirits of wine and gradually heat the mixture on
the water bath in a vessel fitted with a reflux condenser. The reaction usually
sets in below sixty degrees centigrade and sufficient heat is evolved to cause
the mixture to boil. Maintain the temperature so that it boils for from three to
four hours. The mixture may then be allowed to cool and the crystalline
precipitate obtained be separated from the mother liquor and directly used for
dyeing or printing or it may be dissolved in water and reprecipitated by means
of hydrochloric acid, and isolated in the usual way by filtering, pressing and
drying.
Instead of the hydrochlorates of the nitroso-compound ani of the benzyl-alpha-
naphthylamine other salts may be used or the free bases themselves.
The dyestuff obtained as above described is in the form of its hydrochlorate
readily soluble in water and can therefore be used in this form for dyeing purposes.
If instead of the nitroso-diethyl-metamido-phenol, the dimethyl-compound be taken
the dye obtained is of a redder shade of blue and is in the form of hydrochlorate
less soluble in water so that it is preferably converted into its more readily soluble
sulphate.
The process for the preparation of the dyestuff from the dimethyl-

page_text: compound is in other respects precisely the same, as that hereinbefore described in
the example.
Dated this on d
£ 1001
J. H. JOHNSON & Co.,.
47, Lincoln's Inn Fields, Agents.
COMPLETE SPECIFICATION.
The Manufacture and Production of New Basic Dyestuffs.
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 & Soda Fabrik
of Ludwigshafen on Rhine in the Empire of Germany) 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 to Letters Patent No. 4476 of 1888 granted to me there is
described the manufacture of the mono-nitroso-compounds of di-methyl and di-ethyl-
metamido-phenol and the production of blue basic dyestuffs (e.g. Nile blue) by
the condensation of these nitroso-compounds with the alpha-naphthylamine and
its alkyl derivatives, such as ethyl-alpha-naphthylamine and di-methyl-alpha-
naphthylamine.
My foreign correspondents have discovered that new and valuable basic dyestuffs
can be obtained by condensing the hereinbefore mentioned nitroso-compounds with
benzyl alpha-naphthylamine instead of with alphanaphthylamine itself or those
alkyl-compounds mentioned in the aforesaid Specification of Letters Patent
No. 4476 of 18SS.
Benzyl-alpha-naphthylamine appears to have been prepared by the action of
alpha-naphthylamine on benzyl-amine but can be more advantageously obtained by
the interaction of two molecular proportions of alpha-naphthylamine and onc
molecular proportion of benzyl-chloride in the presence of a suitable solvent such
as toluene at the temperature of the water bath. By the action of hydrochloric
acid gas on an ethereal solution of benzyl-alpha-naphthylamine it can be converted
into its hydrochlorate.
To more clearly illustrate this invention and the manner in which it can be
carried into practical effect I give by way of example the following directions for
the production of a new greenish-blue dye from. nitroso-di-ethyl-metamido-phenol
and benzyl-alpha-naphthylamine the parts being by weight. Mix about sixty-nine
parts of the hydrochlorate of nitroso-diethyl-metamido-phenol and about fifty four
parts of hydrochlorate of benzyl-alpha-naphthylamine with abont one hundred parts
of spirits of wine and gradually heat the mixture on the water bath in a vessel
fitted with a reflux condenser. The reaction usually sets in below sixty degrees
centigrade and sufficient heat is evolved to cause the mixture to boil. Maintain
the temperature so that it boils for from three to four hours.
The mixture may
then be allowed to cool and the crystalline precipitate obtained be separated from
the mother liquor and directly used for dyeing and printing or it may be dissolved
in water and reprecipitated by means of hydrochloric acid and isolated in the usual
way by filtering pressing and drying.
Instead of the hydrochlorates of the nitroso compound and of the benzyl-alpha-
naphthylamine other salts of these compounds may be used or one of the compounds.
may be in the free or uncombined form. In the last case it is advisable to use
glacial acetic acid as the diluent.
The dyestuff obtained as above described is in the form of its hydrochlorate
readily soluble in water and can therefore be used in this form for dyeing. If
instead of the nitroso-di-ethyl-metamido-phenol, the di-methyl-compound be taken,
the dye obtained is of a redder shade of blue and is in the form of a hydrochlorate

page_text: less soluble in water so that it is preferably converted into its more readily soluble
sulphate. The process for the preparation of the dyestuff from the di-methyl-
compound is in other respects precisely the same, as that hereinbefore described in
the example.
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
claim is :-
:-
1. The manufacture of basic dyestuff's by condensing the nitroso-compound of
dimethyl-meta-amido-phenol, or of di-ethyl-meta-amido-phenol with benzyl-alpha-
naphthylamine substantially as herein before described.
2. The manufacture of basic dyestuffs by the condensation of the nitroso-di-alkyl-
meta-amido-phenols, hereinbefore mentioned, with benzyl-alpha-naphthylamine
substantially as herein described in the example.
3. As new articles of manufacture, the new dyestuffs such as can be obtained
as herein before described.
Dated this 10th day of Maal 100
J. H. JOHNSON & Co.,
Agents.