Production of an Imide Compound of Fluorescöine Chloride and of Coloring Matters therefrom.
Year: 1889

page_text: Date of Application, 15th Apr., 1889
Complete Specification Left, 28th Dec., 1889-Accepted, 1st Mar., 1890
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE FARBWERKE VORMALS MEISTER LUCIUS AND
BRUNING, of Hoexhst-am-Maine, in the Empire of Germany, a Company carrying
on business as Chemical Manufacturers.]
Production of an Imide Compound of Fluorescöine Chloride and of
Coloring Matters therefrom.
1, OLIVER IMRAY of No. 28 Southampton Buildings Chancery Lane in the County
of London, Fellow of the Institute of Patent Agents, do hereby declare the nature
of this invention to be as follows:-
By the action of ammonia upon fluorescëine chloride water is liberated and there
is obtained, an imide compound of the fluoresceinechloride Co H₁₁ CI, NO,.
This compound is readily obtained by heating fluorescëinechloride with concentrated
aqueous ammonia for 6 to 8 hours to 190°-200° C. The same compound is obtained
by heating fluoresceinechloride with salmiac in presence of lime and chlorzine to 240°
or 260° C.; but by this treatment coloured basic products are formed simultaneously
by interchange of chloro-atoms with residues of ammonia.
The imide compound of the fluoresceinechloride is colorless, melting at 235° C. It
is insoluble in water, or in aqueous acids and alkalies, but is easily soluble in warm
alcohol, in chloroform and benzol. From the latter it crystallises in strong brilliant
prisms which contain crystalbenzol and decay when exposed to air at ordinary
temperature. Concentrated hydrochloric acid or sulphuric acid does not react upon
it, and it remains unchanged when boiled with zinc powder in alkaline alcoholio
solution.
When it is melted with the fatty and aromatic bases or their hydrochlorates in
presence of chlorzine at 250° to 270° C. the imide compound of the fluorescëine-
chloride furnishes red to blue violet coloring matters soluble in alcohol, which by
sulphonation can be rendered soluble in water.

page_text: COMPLETE SPECIFICATION.
Production of an Imide Compound of Fluoresceine Chloride and of
Coloring Matters therefrom.
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the County
of London, Fellow of the Institute of Patent Agents, 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 :-
--
By the action of ammonia upon fluoresceine chloride, water is liberated and there
is obtained an imide compound of fluoresceine chloride C, H₁₁ Cl, NO,.
This compound is readily obtained by heating fluoresceine chloride with concentrated
aqueous ammonia for 6 to 8 hours to 190°-200° C.
The same compound is obtained by heating fluoresceine chloride with salammoniac
in presence of lime and chlorzine to 240° or 260° C.; but by this treatment coloured
basic products are formed simultaneously by interchange of chloro-atoms with residues
of ammonia.
The imide compound of the fluoresceine chloride is colourless, melting at 235° C.
It is insoluble in water, or in aqueous acids and alkalies, but is easily soluble in warm
alcohol, in chloroform and benzol.
From the latter it crystallises in strong brilliant prisms which contain crystal benzol
and decay when exposed to air at ordinary temperature. Concentrated hydrochloric
acid or sulphuric acid does not react upon it, and it remains unchanged when boiled
with zinc powder in alkaline alcoholic solution.
When it is melted with the fatty and aromatic bases on their hydrochlorates in
presence of chlorzine at 250° to 270° C. the imide compound of the fluorescëine
chloride furnishes red to blue-violet coloring matters soluble in alcohol, which by
sulphonation can be rendered soluble in water.
are neated for two hours CO 200
The product of the fusion is powdered, boiled with diluted hydrochloric acid and
dissolved in alcohol. On pouring the alcoholic solution into water the coloring matter
is precipitated.
The coloring matter that is soluble in alcohol may be converted into a coloring
matter soluble in water as follows:-
1 part of the coloring matter soluble in alcohol is introduced into 8 parts of
sulphuric acid-monohydrate while the whole is agitated and the temperature is kept
at 20 to 30° 0.
As soon as a sample gives a clear solution in alkalies, the mixture is poured into
water; the sulphonic acid that has formed, is washed with water, dissolved in soda
and the coloring matter is precipitated from the filtered solution by means of common
salt.

page_text: Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, 1 declare that what I
claim is :-
1. The production of an imide compound of fluoresceine chloride of the com-
position C, H, Cl, NO, by substituting in the fluoresceine chloride an imide (NH)
for an atom of oxygen by the action of ammonia at an elevated temperature, sub-
stantially as described.
2. The production of coloring matters by the action of primary and secondary
amines upon the imide compound of fluoresceine chloride, substantially as described.
3. The production of coloring matters soluble in water by the action of sulphuric
acid or similar agents upon the compounds produced as mentioned in the second
claim.
تيمم
1
1
1000
ABEL & IMRAY,
Agents for the Applicant.