Manufacture of Phthalein Dyestuffs.
Year: 1899

page_text: Date of Application, 15th Dec.,
1899
Complete On
1000
1000
PROVISIONAL SPECIFICATION.
Manufacture of Phthalein Dyestuffs.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention (as communicated to me from abroad by The Farbwerke vormals Meister
Lucius & Brüning, of Hoechst "/Main, in the Empire of Germany, Chemical
Manufacturers.) to be as follows:-
-
My foreign correspondents have found that alkylamidooxybenzoylbenzoic acid
may be condensed with alphylated meta-amidophenol as well as with meta-oxy-
diphenylamine or with meta-oxyphenyl-para-tolylamine to phthaleins.
Thus a new series of dyestuffs is produced which, as regards their shade and
tinctorial properties behave quite differently from the rhodamines which contain
only alkyl-groups; they are of a less basic nature and dye bluer tints than the
alkylrhodamines do.
Valuable dyestuffs are obtained by sulphonating these new condensation pro-
ducts these sulphonic acids dye wool in an acid bath very fast shades, from
fuchsine to violet-red, in the manner of the violamines which they closely
resemble in their properties.
To manufacture these new phthaleins molecular proportions of dialkylamido-
oxybenzoylbenzoic acid and meta-alphylamidophenol are heated for some time with
dehydrating agents such as zinc chloride, phosphoric acid or concentrated sul-
phuric acid, if sulphuric acid of 60° Bé. specific gravity be used for condensation,
then sulphurised products are at once obtained.
Dyestuffs are thus produced from: -
1. Dimethylamido-oxybenzoylbenzoic acid + meta-oxydiphenylamine.
2. Diethylamido-oxybenzoylbenzoic acid + meta-oxyphenyl-para-tolylamine.
3. Ethylamido-oxybenzoylbenzoic acid + meta-oxydiphenylamine.
EXAMPLE I.
3 parts by weight of dimethylamido-oxybenzoylbenzoic acid 2.84 parts of meta-
oxydiphenylamine and 10 parts of zinc chloride are heated in an
enamelled vessel, with active stirring and little access of air, for from 5 to 6
hours to 160°-170° C. The mass of slight metallic lustre is pulverised when
cold, washed with dilute hydrochloric acid to remove the zinc chloride, then
filtered and dried. The dyestuff thus obtained is a dark violet powder insoluble in
water it is dissolved by heated alcohol in considerable quantity to a red-violet
solution, it dyes cotton treated with tannin violet.
EXAMPLE II.
The sulphonic acid of this dyestuff is directly obtained, if 3 parts of dimethyl-
amido-oxybenzoylbenzoic acid and 2.84 parts of meta-oxydiphenylamine are
dissolved in 30 parts of sulphuric acid of 66° Bé. specific gravity: the whole is
then heated for about 1 hour on the water bath and the deep brown-red product
[Price 8d.]

page_text: is poured into ice water, filtered, well washed, and dried. This sulphonic acid
is a substance of metallic lustre, soluble with difficulty in water; it is readily
dissolved by hot alcohol with an intense red-violet colour; it dyes wool in an
acid bath fuchsine-red shades very fast to alkali.
EXAMPLE III.
If in Examples I or II the corresponding diethyl product be substituted for the
dimethylamido-oxybenzoylbenzoic acid and meta-oxyphenyl-para-tolylamine for
meta-oxydiphenylamine, then in an analogous manner the homologous dyestuff
or its sulphonic acid may be obtained. This sulphonic acid is a substance of
strong metallic lustre, soluble in water with great difficulty it is readily dissolved
by hot alcohol, to a red-violet solution; it is soluble in dilute alkali to a similar
solution. It dyes wool blue-red tints exceedingly fast to alkali.
EXAMPLE IV.
The sulphonic acid of the dyestuff from ethylamido-oxybenzoylbenzoic acid
and meta-oxydiphenylamine, obtained according to Example II is a crystalline
substance of strong metallic lustre, soluble with difficulty in water; it readily
dissolves in alcohol to a red solution; it dyes wool fuchsine-red tints exceedingly
fast to alkalies.
Dated thin 15th
عمل
f
11000
ABEL & IMRAY,
Agents for the Applicant.
Manufacture of Phthalein Dyestuffs.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention (as communicated to me from abroad by The Farbwerke vormals Meister
Lucius & Brüning, of Hoechst /Main, in the Empire of Germany, Chemical
Manufacturers) and in what manner the same is to be performed, to be particu-
larly described and ascertained in and by the following statement:―
My foreign correspondents have found that alkylamidooxybenzoylbenzoic acids
may be condensed with alphylated meta-amido-phenols such as meta-oxydipheny-
lamine or with meta-oxyphenyl-para-tolylamine to phthaleins.
Thus a new series of dyestuffs is produced which, as regards their shade and
tinctorial properties behave quite differently from the rhodamines which contain
only alkyl-groups; they are of a less basic nature and dye bluer tints than the
alkylrhodamines do.
Valuable dyestuffs are obtained by sulphonating these condensation products,
these sulphonic acids dye wool in an acid bath very fast shades from magenta to
violet red, in the manner of the violamines which they closely resemble in their
properties.
To manufacture these new phthaleins molecular proportions of dialkylamido-
oxybenzoylbenzoic acid and meta-alphylamidophenol are heated for some time with
dehydrating agents such as zinc chloride, phosphoric acid or concentrated sul-
phuric acid, if sulphuric acid of 66° Bé. specific gravity be used for condensation,
then sulphonated products are at once obtained.
Dyestuffs are thus produced from: -
1. Dimethylamido-oxybenzoylbenzoic acid + meta-oxydiphenylamine.
2. Diethylamido-oxybenzoylbenzoic acid + meta-oxyphenyl-para-tolylamine.

page_text: 3. Ethylamido-oxybenzoylbenzoic acid + meta-oxydiphenylamine.
EXAMPLE I.
3 parts by weight of dimethylamido-oxybenzoylbenzoic acid, 2.84 parts of meta-
oxydiphenylamine and 10 parts of zinc chloride are heated in an
enamelled vessel, with active stirring and little access of air, for from 5 to 6
hours to 1600-170° C. The mass, of slight metallic lustre is pulverised when
cold, washed with dilute hydrochloric acid to remove the zinc chloride, then
filtered and dried. The dyestuff thus obtained is a dark violet powder insoluble in
water; it is dissolved by heated alcohol in considerable quantity to a red violet
solution, it dyes cotton treated with tannin violet.
EXAMPLE II.
The sulphonic acid of this dyestuff is directly obtained, if 3 parts of dimethyl-
amido-oxybenzoylbenzoic acid and 2.84 parts of meta-oxydiphenylamine are
dissolved in 30 parts of sulphuric acid of 66° Bé. specific gravity; the whole is
then heated for about 1 hour on the water bath and the deep brown-red product
is poured into ice water, filtered, well washed, and dried. This sulphonic acid
is a substance of metallic lustre, soluble with difficulty in water; it is readily
dissolved by hot alcohol with an intense red-violet colour; it dyes wool in an
acid bath magenta-red shades very fast to alkali.
EXAMPLE III.
If in Examples I or II the corresponding diethyl product be substituted for the
dimethylamido-oxybenzoylbenzoic acid and meta-oxyphenyl-para-tolylamine for
meta-oxydiphenylamine, then in an analogous manner the homologous dyestuff
or its sulphonic acid may be obtained. This sulphonic acid is a substance of
strong metallic lustre, soluble in water with great difficulty; it is readily dissolved
by hot alcohol to a red-violet solution; it is soluble in dilute alkali to a similar
solution. It dyes wool blue-red tints exceedingly fast to alkali.
EXAMPLE IV.
The sulphonic acid of the dyestuff from ethylamido-oxybenzoylbenzoic acid
and meta-oxydiphenylamine, obtained according to Example II is a crystalline
substance of strong metallic lustre, soluble with difficulty in water; it readily
dissolves in alcohol to a red solution; it dyes wool magenta tints exceedingly
fast to alkalies.
Having now particularly described and ascertained the nature of my said
invention and in what manner the same is to be performed, I declare that what
I claim is:-
1. The herein described manufacture of phthalein dyestuffs by condensing
alkylamidooxybenzoylbenzoic acids with alphylated amidophenols and by sul-
phonating the products of condensation thus obtained.
2. The dyestuffs manufactured as above set forth.
Dated this 19th day of Cantambo 1000