THE PRODUCTION OF NEW COLORING MATTERS BY THE REACTION OF THE DIAZOIC DERIVATIVES OF NITRANILINE OR OTHER DIAZOIC DERIVATIVES UPON AMINES, AMIDES, AND PHENOLS
Year: 1878

page_text: LETTERS PATENT to John Clayton Mewburn, of 169, Fleet Street, in the City
of London, Patent Agent and Consulting Engineer, for the Invention of "THE
PRODUCTION OF NEW COLORING MATTERS BY THE REACTION OF THE DIAZOIC
DERIVATIVES OF NITRANILINE OR OTHER DIAZOIC DERIVATIVES UPON AMINES,
AMIDES, AND PHENOLS." A communication from abroad by Zacharie Roussin,
Chemist, and Alcide François Poirrier, Manufacturer, both of Paris, France.
PROVISIONAL SPECIFICATION left by the said John Clayton Mewburn at
the Office of the Commissioners of Patents on the 6th November 1878.
JOHN CLAYTON MEWBURN, of 169, Fleet Street, in the City of London, Patent
Agent and Consulting Engineer. "THE PRODUCTION OF NEW COLORING MATTERS
BY THE REACTION OF THE DIAZOIC DERIVATIVES OF NITRANILINE OR OTHER
DIAZOIC DERIVATIVES UPON AMINES, AMIDES, AND PHENOLS." [A communication
from abroad by Zacharie Roussin, Chemist, and Alcide François Poirrier, Manufac-
turer, both of Paris, France.]
This Invention consists in producing new coloring matters by the reaction of the
diazoic derivatives of nitraniline or other diazoic derivatives upon amines, amides,
and phenols.
Nitraniline obtained by known processes, and particularly by the action of
alkalies on nitrated acetanilide (acétanilide nitrée), is transformed into diazoic
derivative by its mixture in equivalent quantities with an aqueous solution of
nitrite of soda, and the addition to this mixture of sulphuric acid diluted with
water.
Preparation of the Coloring Matters:-
1st. Reaction of the above diazoic derivative on naphthionic acid (sulphuric or
sulpho-conjugated derivative of naphthylamine). An aqueous solution of an
equivalent of the diazoic derivative of nitraniline reacting cold on an equivalent of

page_text: naphthionic-acid-causes-instantaneously-the production-of-a-colored product, -little-
soluble, which is then washed, and can be transformed into sodic or ammoniacal
salt. This coloring matter will dye wool and silk red analogous to orchil.
2nd. Reaction of the diazoic derivative on phenic acid.-Phenic acid in an
alkaline solution reacting with equal equivalents on the diazoic derivative of
nitraniline causes the production instantaneously, and even when cold, of a coloring
matter which crystallizes very readily in the form of sodic-salt. This body will
dye a slightly reddish yellow.
3rd. By substituting for the alkaline phonic acid in the preceding preparation an
aqueous solution of resorcine, an orange yellow coloring matter is obtained in the
form of a precipitate which is readily washed and dried.
4th. Equal equivalents of phenylene-diamine and of the diazoic derivative of
nitraniline react instantaneously in a body of water, and produce a yellow coloring
matter which is then washed and transformed into sodic salt. This coloring matter
will dye wool, silk, and cotton a slightly reddish yellow.
5th. Reaction of the diazoic derivative on alpha and beta naphthols. By causing
an alkaline solution of the naphthols to react cold and with equal equivalents on
an acid solution of the diazoic derivative, a red precipitate is obtained insoluble in
water, acids and alkalies. This precipitate is washed and readily purified by cold
water.
By impregnating a fabric with an aqueous solution of the diazoic derivative of
nitraniline, then immersing this fabric in a solution as little alkaline as possible of
alpha or beta naphthol, the fabric is colored red. This operation can be repeated in
the same manner on the same fabric until a suitable tone is attained.{
These insoluble coloring. matters will readily sulpho-conjugate by the ordinary
processes, and then become soluble in water.
:
By causing the diazoic derivative of nitraniline to react on one or other of the
naphthols previously sulpho-conjugated there are obtained by simple mixture and
cold, and with equal equivalents of aqueous solutions of these substances, orange red
coloring matters soluble in water. These matters are collected on cloths, washed
with cold water, compressed, and then transformed into sodic salt.
The diazoic derivatives of nitronaphthlamine of the nitro-toludines and of the
nitro-xylidines act with the above substances like the diazoic derivatives of nitra
nilines, and produce analogous coloring matters.
This process is applicable to the different isomeric nitranilines.

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said John Clayton Mewburn in the Great Seal Patent Office on the
6th May 1879.
«
JOHN CLAYTON MEWBURN, of 169, Fleet Street, in the City of London, Patent
Agent and Consulting Engineer. THE PRODUCTION OF NEW COLORING MATTERS
BY THE REACTION OF THE DIAZOIC DERIVATIVES OF NITRANILINE OR OTHER
DIAZOIC DERIVATIVES UPON AMINES, AMIDES, AND PHENOLS." A communication
from abroad by Zacharie Roussin, Chemist, and Alcide, François Poirrier, Manufac-
turer, both of Paris, France.
This Invention consists in producing new coloring matters by the reaction of the
diazoic derivatives of nitraniline or other diazoic derivatives upon amines, amides,
and phenols.
Nitraniline obtained by known processes, and particularly by the action of
alkalies on nitrated acetanilide (acetanilide nitrée), is transformed into diazoic
derivative by its mixture in equivalent quantities with an aqueous solution of
nitrite of soda, and the addition to this mixture of sulphuric acid diluted with
water.
Preparation of the Coloring Matters: First. Reaction of the above diazoic deri-
vative on naphthionic acid (sulphuric or sulpho-conjugated derivative of naphthyla-
mine). An aqueous solution of an equivalent of the diazoic derivative of nitraniline
reacting cold on an equivalent of naphthionic acid causes instantaneously the
production of a colored product, little soluble, which is then washed, and can be
transformed into sodic or ammoniacal salt. This coloring matter will dye wool and
silk red, analogous to orchil.
Second, Reaction of the diazoic derivative on phenic acid.-Phenic acid in an
alkaline solution reacting with equal equivalents on the diazoic derivative of
nitraniline causes the production instantaneously, and even when cold, of a
coloring matter which crystallizes very readily in the form of sodic salt. This body
will dye a slightly reddish yellow.
Third. By substituting for the alkaline phenic acid in the preceding preparation
an aqueous solution of resorcine an orange yellow coloring matter is obtained in
the form of a precipitate which is readily washed and dried.
Fourth. Equal equivalents of phenylene-diamine and of the diazoic derivative of
nitraniline react instantaneously in a body of water, and produce a yellow coloring
matter which is then washed and transformed into sodic salt. This coloring matter
will dye wool, silk, and cotton a slightly reddish yellow.
Fifth. Reaction of the diazoic derivative on alpha and beta naphthols.-By
causing an alkaline solution of the naphthols to react cold and with equal equi-
valents on an acid solution of the diazoic derivative a red precipitate is obtained
insoluble in water, acids, and alkalies. This precipitate is washed and readily
purified by cold weter.
By impregnating a fabric with an aqueous solution of the diazoic derivative of
nitraniline, then immersing this fabric in a solution as little alkaline as possible of
alpha or beta naphthol, the fabric is colored red. This operation can be repeated
in the same manner on the same fabric until a suitable tone is attained.
These insoluble coloring matters will readily sulpho-conjugate by the ordinary
processes, and then become soluble in water.
By causing the diazoic derivative of nitraniline to react on one or other of the
naphthols previously sulpho-conjugated there are obtained by simple mixture and
cold, and with equal equivalents of aqueous solutions of these substances, orange
red coloring matters soluble in water. These matters are collected on cloths,
washed with cold water, compressed, and then transformed into sodic salt.
The diazoic derivatives of nitronaphthylamine, of the nitro-toluidines, and of the

page_text: nitro-xylidines act with the above substances, like the diazoic_derivatives_of
nitranilines, and produce analogous coloring matters.
This process is applicable to the different isomeric nitranilines.
And having now described the nature of the said Invention, and in what manner
the same is to be performed, I declare-that-I-claim,—
The production of coloring matters by the reaction of the diazoic derivatives of
nitraniline or other diazoic derivatives-upon amines, amides, and phenols, substan=
tially as hereinbefore described.
In witness whereof, I, the said John Clayton Mewbuin, have hereunto set my
hand and seal, this Sixth day of May, One thousand eight hundred and
seventy nine.