the Action of Phenanthrene-chinone, Isatine, or Methyle-isatine upon the Sulpho-acids of Aromatic Hydrazines.
Year: 1887

page_text: Date of Application, 6th May, 1887
Complete Left, 4th Feb., 1888
Complete Accepted, 23rd Mar., 1888
the Action of Phenanthrene-chinone, Isatine, or Methyle-isatine
upon the Sulpho-acids of Aromatic Hydrazines.
I, CHARLES DENTON ABEL of No. 28 Southampton Buildings, Chancery Lane in
the County of Middlesex Fellow of the Institute of Patent Agents do hereby declare
the nature of this invention to be as follows:-
It is known that the hydrazines of the aromatic class condense with aldehydes and
ketones under separation of water. Also phenanthrene-Chinone, isatine, and methyle-
isatine forn with bases of hydrazine such condensed products, which do not dissolve
in water and which can, therefore not be used for dyeing, although they are colored
themselves.
Now it has been found by my correspondents that by the reaction of the sulpho-
acids of aromatic hydrazines upon phenanthrene-chinone, isatine or methyle-isatine,
condensed products are obtained which give sodium-salts soluble in water and which,
therefore, are suitable for dyeing. They all dye wool from an acidulated bath in
shades which vary from yellow to red, according to the nature of the sulpho acids of
hydrazine used. These colors excel by their property of withstanding acids and
alkalies and of being completely taken up from the dye-bath by wool.
The production of these sulpho-acids of the aromatic hydrazines used for the
purposes of this invention takes place in the known manner by reducing the sulpho-
acids of the diazo-combinations by means of chloride of tin, or of sulphuric acid.
The sulpho-acids of the hydrazines which are mentioned hereinafter and which have
not been described as yet, have all been obtained very easily according to that
process.
The production of the colors is simply arrived at by heating phenanthrene-chinone,
isatine or methyle-isatine with an aqueous solution of the respoctive sulpho-acid of
hydrazine.

page_text: A. COLORS FROM PHENANTHRENE-CHINONE.
1. Phenyle-hydrazine-p-sulpho-acid, and
2. Phenyle-hydrazine-in-sulpho-acid, give with phenanthrene-chinone, colors which
dye wool in an orange shade.
3. o-tolyle-hydrazine-p-sulpho-acid, and
4. p-tolyle-hydrazine-o-sulpho-acid, which easily form in the shape of colorless
crystalline compounds by the reduction of o-diazo-toluole-p-sulpho-acid and p-diazo-
toluole-o-sulpho-acids, combine also with phenanthrene-chinone to colors which dye
in an orange shade.
5 & 6. The hydrazine combinations obtained from the ß-naththylamine-sulpho-
acid (from the ẞ naphthole-sulpho-acid of Schaeffer), and those from the so-called
B-naphthylamine-8-sulpho-acid crystallize in the shape of glittering small leaves and
give with phenanthrene-chinone colors which dye in yellow-red shades.
7. The a-hydrazine-naphthaline-sulpho-acid which is obtained from naphthionic
acid and which forms glittering crystals not easily soluble in water, condenses with
phenanthrene-chinone to a color which dyes in a dark red shade.
8. If the diphenyle-hydrazine-sulpho-acid obtained from benzidine-disulpho-acid
(from m-nitrobenzole-sulpho-acid) which also crystallizes in small leaves is heated
with phenanthrine-chinone, a color is obtained which dyes in a brown red shade.
The following example is a description of the formation of the color :
50 Kg. of a-hydrazine-naphthaline a-sulpho-acid (from naphthionic acid) and
150 Kg. of paste of phenanthrene-chinone (containing 20 Kg. of dry phenanthrene-
chinone) are entered into 1500 litres of water and well dispersed by stirring. The
mixture is then gradually heated up to boiling. As soon as a clear dark red solution
is formed it is neutralized by means of soda and the color precipitated by common
salt, filtered, pressed and dried.

page_text: Processes for the Production of Yellow, Orange, and Red Colors by
the Action of Phenanthrene-chinone, Isatine, or Methyl-isatine
upon the Sulpho Acids of Aromatic Hydrazines.
I, CHARLES DENTON ABEL of No. 28 Southampton Buildings, Chancery Lane in the
County of Middlesex, 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 :—
It is known that the hydrazines of the aromatic class condense with aldehydes and
ketones under separation of water. Also phenanthrene-chinone, isatine, and methyle-
isatine form with bases of hydrazine such condensed products, which do not dissolve
in water and which can, therefore not be used for dyeing although they are colored
themselves.
Now it has been found by my correspondents that by the reaction of the sulpho-
acids of aromatic hydrazines upon phenanthrene-chinone, isatine, or methyle-isatine,
condensed products are obtained which give sodium-salts soluble in water and which
therefore, are suitable for dyeing.
They all dye wool from an acidulated bath in shades which vary from yellow to
red, according to the nature of the sulpho-acids of hydrazine used. These colors excel
by their property of withstanding acids and alkalies and of being completely taken up
from the dye bath by wool.
The production of those sulpho-acids of the aromatic hydrazines used for the
purposes of this invention takes place in the known manner by reducing the sulpho-
acids of the diazo-combinations by means of chloride of tin or of sulphuric acid. The
sulpho-acids of the hydrazines which are mentioned hereinafter and which have not
been described as yet, have all been obtained very easily according to that process.
The production of the colors is simply arrived at by heating phenanthrene-chinone,
isatine, or methyle-isatine with an aqueous solution of the respective sulpho-acid of
hydrazine.
1.
Phenyle-hydrazine-p-sulpho-acid, and
2. Phenyle-hydrazine-m-sulpho-acid give, with phenanthrene-chinone, colors which
dye wool in an orange
shade.
3. o-tolyle-hydrazine-p-sulpho-acid, and
4. p-tolyle-hydrazine-o-sulpho-acid, which easily form in the shape of colorless
crystalline compounds by the reduction of o-diazo-toluole-p-sulpho-acid and p-diazo-
toluole-o-sulpho-acids, combine also with phenanthrene-chinone to colors which dye
in an orange shade.
5 & 6. The hydrazine combinations obtained from the ẞ-naphthylamine-sulpho-acid
(from the B-naphthole-sulpho-acid of Schaeffer) and those from the so-called

page_text: B-naphthylamine 8-sulpho-acid crystallize in the shape of glittering small leaves and
give with phenanthrene-chinone, colors which dye in yellow-red shades.
7. The a-hydrazine-naphthaline-sulpho-acid which is obtained from naphthionic
acid and which forms glittering crystals not easily soluble in water, condenses with
phenanthrene-chinone to a color which dies in a dark red shade.
8. If the diphenyle-hydrazine-sulpho-acid obtained from benzidine-disulpho-acid
(from m-nitrobenzole-sulpho-acid) which also crystallizes in small leaves is heated
with phenanthrene-chinone, a color is obtained which dyes in a brown red shade.
The following example is a description of the formation of the color:
The
50 Kg. of a-hydrazine-naphthaline-a-sulpho-acid (from naphthionic acid) and
150 Kg. of paste of phenanthrene-chinone (containing 20 Kg. of dry phenanthrene-
chinone) are entered into 1500 litres of water and well dispersed by stirring
mixture is then gradually heated up to boiling. As soon as a clear dark red solution
is formed it is neutralized by means of soda and the color precipitated by common
salt, filtered, pressed and dried.
mixture is then gradually heated up to boiling. As soon as a clear dark red solution
is formed it is neutralized by means of soda and the color precipitated by common
salt, filtered, pressed and dried.
B. COLORS FROM ISATINE AND METHYLE-ISATINE.
The shades in which the hydrazines dye, are:
m-amido-benzole-sulpho-acid
p-amido-benzole-sulpho-acid
a greenish yellow.
o-toluidine-p-sulpho-acid
p-toluidine-o-sulpho-acid
B-naphthylamine 8-sulpho-acid
a pure yellow.
benzidine-disulpho-acid
a-naphthylamine-sulpho-acid
B-naphthylamine-sulpho-acid
a yellow orange.
(from the
naphthole-sulpho-
acid of Schaeffer).
The following example is a description of the process for the production of the
color from isatine and phenyle-hydrazine-p-sulpho-acid.
10 Kg. of phenyle-hydrazine-p-sulpho-acid and 7.8 Kg. of isatine are well dispersed
in 500 litres of water and gradually heated up to boiling. The solution obtained is
then neutralized with soda and mixed with salt whereby the color precipitates. The
latter is afterwards filtered, pressed and dried.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed I declare that what
I claim is :-
:-
1. The production of coloring matters by condensation with phenanthrene-chinone
of hydrazines from m-sulphanilic acid, p-sulphanilic acid o-toluidine-sulphonic acid,
p-toluidine sulphonic acid, ß-naphthylamine-8-sulphonic acid ẞ-naphthylamine-
B-sulphonic acid, a naphthylamine-sulphonic acid and benzidine-disulphonic acid.
2. The production of coloring matters by condensation of the hydrazines referred
to in the preceding claim with isatine or methylisatine.
11
T T
1
1000
ABEL & IMRAY,
Agents for the Applicant.