Improvements in and relating to the Production of Coloring Matters.
Year: 1896

page_text: PROVISIONAL SPECIFICATION.
Improvements in and relating to the Production of Coloring Matters.
A communication from abroad by LA SOCIÉTÉ CHIMIQUE DES USINES DU
RHÔNE, anciennement GILLARD P. MONNET ET CARTIER, of Lyons, France,
Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis of 55 and 56
Chancery Lane in the County of London, Chartered Patent Agents do hereby
declare the nature of this invention to be as follows:-
By the condensation of alkylated meta-amido-phenols with the anhydrides of
phtalic acid, succinic acid and such like acids containing two carboxylic groups,
a large number of valuable coloring matters have been produced, specially dis-
tinguished by their dyeing and fluorescent qualities.
According to the present invention, a new series of coloring matters are pro-
duced by the condensation of meta-amido-phenols and of meta-amido-cresols or
of their mono-alkylated or dialkylated derivatives, with the anhydride of ortho-
sulphamine-benzoic acid, commonly known as saccharine, in which the second
carboxyl group of phtalic acid is replaced by a sulphonyl radicle.
Similarly to the condensation of saccharine with resorcinol, condensation pro-
ducts of saccharine with meta-amido-phenols may also be obtained, which possess
characteristic coloring properties.
For example, diethyl-meta-amidophenol may be heated with twice its weight
of saccharine until the reaction is completed, preferably for 36 hours at 165° C.
The product of the reaction is allowed to cool, then powdered, and the powder
suspended in an aqueous solution of carbonate of soda. The amount of carbonate
of soda should be equal to at least half the weight of saccharine taken. The
solution is heated to boiling, allowed to cool and filtered. By this means the
excess of saccharine employed is removed in the alkaline solution and may be
recovered therefrom by precipitation with acid. Under the above conditions
rather more than half the weight of the saccharine taken may be recovered. The
insoluble product left on cooling and filtering the solution is a brown mass with
metallic glance. In order to purify it, it may be digested for several hours with a
solution of caustic soda, whereby a powder which is only slightly colored remains,
and is filtered and washed freely with water. It is then dissolved by boiling
in water strongly acidulated with hydrochloric acid. The boiling solution,
which possesses a magnificent red color, is filtered, and the filtrate on cooling
deposits small green crystals with metallic sheen. In this condition the product
is slightly soluble in cold water which it colors however intensely violet red with
yellow fluorescence. When boiled the solution is decolorized and the coloring
matter precipitated in faintly violet-tinted flocks. The color re-appears upon
addition of an acid. If an alkali is added to the solution it is instantaneously
decolorized, the coloring matter being likewise precipitated in violet flocks. Thus

page_text: it appears that the new product has very weak basic properties, and its salts are
dissociated even by simply boiling with water.
A coloring matter possessing very similar properties to the foregoing may also
be obtained by the condensation of saccharine with dimethyl-meta-amido-phenol,
and the reaction may also be extended to other meta-amidophenols and meta-
amido-cresols, mono-alkylated or dialkylated.
Dated this 24th day of September 1896.
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London, Chartered Patent Agents.
A communication from abroad by LA SOCIÉTÉ CHIMIQUE DES USINES DU
RHÔNE, anciennement GILLIARD P. MONNET ET CARTIER, of Lyons, France,
Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis of 55 and 56
Chancery Lane in the County of London, Chartered Patent Agents do hereby
declare the nature of this invention and in what manner the same is to be per-
formed to be particularly described and ascertained in and by the following
statement:-
By the condensation of alkylated meta-amido-phenols with the anhydrides of
phtalic acid, succinic acid and such like acids containing two carboxylic groups,
a large number of valuable coloring matters have been produced, specially dis-
tinguished by their dyeing and fluorescent qualities.
According to the present invention, a new series of coloring matters are pro-
duced by the condensation of meta-amido-phenols and of meta-amido-cresols or
of their mono-alkylated or dialkylated derivatives, with the anhydride of ortho-
sulphamine-benzoic acid, commonly known as saccharine in which the second
carboxyl group of phtalic acid is replaced by a sulphonyl radicle.
Similarly to the condensation of saccharine with resorcinol, as described in my
Specification No. 21196 of 1896, condensation products of saccharine with meta-
ainido-phenols may also be obtained, which possess characteristic coloring
properties and may be approximately termed sulpho-rhodamines.
The
For example, diethyl-meta-amido-phenol may be heated with twice its weight
of saccharine until the reaction is completed, preferably for 36 hours at 165° C.
With the aid of condensation agents the reaction may be completed in a shorter
time. The product of the reaction is allowed to cool, then powdered and the powder
suspended in an aqueous solution of carbonate of soda. The amount of carbonate
of soda should be equal to at least half the, weight of saccharine taken.
solution is heated to boiling, allowed to cool and filtered. By this means the
excess of saccharine employed is removed in the alkaline solution and may be
recovered therefrom by precipitation with acid. Under, the above conditions
rather more than half the weight of the saccharine taken may be recovered. The
insoluble product left on cooling and filtering the solution is a brown mass with
metallic sheen. In order to purify it, it may be digested for several hours with a
solution of caustic soda, whereby a powder which is only slightly colored remains,
and is filtered and washed freely with water. It is then dissolved by boiling
in water strongly acidulated with hydrochloric acid. The boiling solution,
which possesses a magnificent red color, is filtered, and the filtrate on cooling

page_text: deposits small green crystals with metallic sheen. In this condition the product
is slightly soluble in cold water which it colors however intensely violet red with
yellow fluorescence. When boiled the solution is decolorized and the coloring
matter precipitated in faintly violet-tinted flocks. The color re-appears upon
addition of an acid. If an alkali is added to the solution it is instantaneously
decolorized, the coloring matter being likewise precipitated in violet tinged flocks.
Thus it appears that the new product has very weak basic properties, and its
salts are dissociated even by simply boiling with water. When re-crystallized
from benzene the base melts at 240-245° C.
A coloring matter possessing very similar properties to the foregoing may also
be obtained by the condensation of saccharine with di-methyl-meta-amido-phenol
and the reaction may also be extended to other meta-amido-phenols and meta-
amido-cresols, mono-alkylated or di-alkylated. The product from mono-ethyl
amidophenol dyes fibres with a yellower shade than the diethylated product;
that from mono-phenyl-amido-phenol is a violet dye insoluble in water, soluble
in alcohol.
Having now particularly described and ascertained the nature of the said in-
vention as communicated to me and in what manner the same is to be performed,
I declare that what I claim is:-
1. The manufacture of new coloring matters, herein before called sulpho-
rhodamines, by heating together saccharine and meta-amido-phenol or meta-
amido-cresol, or mono-alkylated or dialkylated meta-amido-phenols or meta-
amido-cresols, substantially as described.
2. As new products the new coloring matters hereinbefore called sulpho-
rhodamines which may for example be obtained by the condensation of saccharine
with meta-amido-phenol or meta-amido-cresol, or with their substitution deriva-
tives, substantially as hereinbefore described.
Dated this 24th day of June 1897.
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London, Chartered Patent Agents.