The Manufacture or Production of Colouring Matters.
Year: 1894

page_text: Date of Application, 1st Oct., 1894
Complete Specification Left, 24th June, 1895-Accepted, 27th July, 1895
[Communicated from abroad by THE FARBENFABRIKEN vormals FRIEDRICH
BAYER & Co., of Elberfeld, Germany.]
The Manufacture or Production of Colouring Matters.
1, HENRY EDWARD NEWTON of the Office for Patents, 6 Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the
nature of this invention to be as follows:-
In the Specification of Letters Patent No. 18519, dated 19th November 1889;
No. 3397, dated 4th March 1890; No. 13443 dated 26th August 1890; and
No. 5984 dated 7th April 1891, my foreign correspondents have described the
production of monoazo dye-stuffs suitable for dyeing wool. These processes consist
in combining the diazo derivatives of "amines or substituted amines" with sulpho
acids, of 1:8 dihydroxynaphthalene (a a dihydroxynaphthalene.)
32
Amongst the "substituted amines employed in the above processes, amido
carbonic acids are named.
My foreign correspondents have now found, that, in the same manner as
diazotised amidocarbonic acids, the diazo products of esters, amides, anilides
toluidides, naphthalides, derived from aromatic amidocarbonic or amidosulpho
acids, the diazo derivatives of the analogues, homologues, or substitution products
thereof, the diazo compounds of aromatic amidoketones, or substituted amido-
ketones (including amidoacetophenone), or analogous products (such as amido
sulpho benzide and the like), are also capable of reacting with sulpho acids of a₁ a
dihydroxynaphthalene, valuable dyestuffs being thereby produced.
The process of producing these new colouring matters is effected in the mauner
generally in use, viz. -the diazo derivatives of esters of aromatic amidocarbonic
carbonic acids, the diazo products of amides, apilides, or analogous alkylated
amides derived from aromatic amidocarbonic acids, or the diazo compounds of
aromatic amidoketones,,and so on, are allowed to act on the sulphoacids of a₁ a↓
dihydroxynaphthalene.
In illustration of the method of producing these dyestuffs, the following example
is given, the parts being by weight.
PRODUCTION
OF THE COLOURING MATTER FROM DIAZOTISED AMIDO-
BENZOPHENONE AND ai
a4
DIHYDROXYNAPHTHALENE-a2 MONOSULPHO
ACID.
18.5 parts of amidobenzophenone are diazotised in hydrochloric solution by
means of 7 parts of sodiumi nitrite. The resulting mixture is introduced into
a watery solution prepared by dissolving 262 parts of a, a, dihydroxynaph-
thaleue-a-monosulphonate of sodium, and about 30 parts of sodium acetate.
The formation of the dyestuff begins immediately, and is finished within a short
time. The colouring matter is isolated by filtering off, pressing, and drying,

page_text: It produces on wool, in acidulated baths, magenta-red shades. When the materials
thus dyed are treated with ammonia-liquid, they assume only a slightly bluer
colour, whilst the shades produced by means of "azo-magenta "become orange-red
when treated in the said manner.
In a manner analogous to that described in the above example, the other
dyestuffs result, viz., either by employing, in place of amidobenzophenone used in
the said example, analogous or homologous amidoketones of the aromatic series
(including amidoacetophenone), or products of an analogous composition (such as
amidosulphobenzide), or esters, amides, anilides, toluides naphthalides, or analogous
or homologous acid amides, derived from aromatic amidocarbonic or amidosulpho
acids, or by using, in place of aι a dihydroxynaphthalene-as-monosulpho acid
employed in the above example, other sulphoncids of a, a, dihydroxynaphthalene,
and coupling them with the diazo derivatives of the amido-compounds hereinbefore
defined.
In the above example, a distinct method for practically producing one of these
new dyestuffs is described. Of course my foreign correspondents do not limit
themselves to the directions given therein, as the latter can be varied, and all those
methods can be employed which are in use for the production of analogous or
similar colouring matters.
The dye-stuffs obtainable in the manner hereinbefore described, yield, in
acidulated baths, on wool, magenta-red shades, and are distinguished by great
resistance to alkalies and by their ability to produce even shades.
NEWTON & SON,
Agents for the Applicant.
The Manufacture or Production of Colouring Matters.
I HENRY EDWARD NEWTON of The Office for Patents, 6 Bream's Buildings
Chancery Lane in the County of London, Patent Agent, do hereby declare the
nature of this invention and in what mauner the same is to be performed, to be
particularly described and ascertained in and by the following statement :-
In the Specifications of Letters Patent No. 18519, dated 19th November 1889;
No. 3397, dated 4th March 1890; No. 13443, dated 26th August 1890; and
No. 5984, dated 7th April 1891, my foreign correspondents have described the
production monazo dyestuff's suitable for dyeing wool. These processes consist in
combining the diazo derivatives of "amines or substituted amines" with sulphonic
acids of 1:8 dihydroxynaphthalene or alpha, alpha, dihydroxynaphthalene.
Amido carboxylic acids are named amongst the "substituted amines" used in the
above processes.
My foreign correspondents have found that not only diazotised amidocarboxylic
acids, but also the diazo derivatives of ethereal salts or amides, or anilides, or the
like producte, derived from aromatic amidocarboxylic acids, and the diazo
compounds of aromatic amido ketones, are capable of combining with sulphonic
acids of alpha, alpha, dihydroxynaphthalene, or salts thereof, valuable dyestuff's
being thus formed.
The production of these new colouring matters is effected in the usual
manner, viz., by combining molecular proportions of sulphonic acids of alpha,
alpha, dihydroxynaphthalene, or alkaline salts thereof, with the diazo derivatives
of ethereal salts, or amides, or anilides, or the like products, derived from aromatic
amido carboxylic acids, or with the diazo compounds of aromatic amido ketones.

page_text: COLOURING-MATTER FROM DIAZOTISED AMIDO, BENZOPHENONE AND ALPHA₁
ALPHA DIHYDROXYNAPHTHALENE ALPHA, MONOSULPHONIC ACID.
19-7 parts of paramidobenzophenone are diazotised in presence of muriatic acid
by means of 7 parts of sodium nitrite, and the mixture is introduced into a solution
prepared by dissolving in water 26:2 parts of alpha, alpha dihydroxynaph-
thalene alpha, monosulphonate of sodium, together with about 30 parts of sodium. -
acetate. The formation of the dye-stuff begins immediately, and is complete
within a short time. The liquid having been rendered alkaline, the colouring
matter is separated by filtration, pressed, and dried. It produces on wool, in
acidulated baths, magenta-red sliades.
Its composition is represented by the following formula :-
DYE-STUFF OBTAINED FROM ALPHA1
ALPHA, BETA DISULPHONIC
ETHYLIC PARAMIDO BENZOATE,
ACID
ALPHA DIHYDROXYNAPHTHALENE
AND THE DIAZO DERIVATIVE
OF
The diazo compound produced from 16.5 parts of ethylic paramido benzoate,
dissolved in muriatic acid by means of 7 parts of sodium nitrite, is introduced into
an aqueous solution prepared from 36'4 parts of the sodium salt of alpha, alpha
dihydroxynaphthalene alpha, beta, disulphonic acid, and about 40 parts of sodium
acetate. When the formation of the dye-stuff is complete, the mixture is rendered
alkaline, and the finished colouring matter is isolated in the usual manner, riz., by ›

page_text: salting out, filtering off, pressing, and drying. It dyes wool, in acid baths,
magenta-red shades, and is represented by the following formula :-
The process is carried out in a manner similar to that described in the foregoing
Example B, by using, instead of the alpha, alpha, dihydroxynaphthalene alpha,
beta, disulphonate of sodium therein specified, the equivalent quantity of another
alpha alpha, dihydroxynaphthalene mono or disulphonic acid, or an alkaline salt
thereof, or if corresponding quantities of metbylic or benzylic paramido benzoate,
or of ethereal salts of other aromatic amidocarboxylic acids, are substituted for
the ethylic paramidobenzoate used in the said example, that is to say, if one
molecular proportion of the diazo derivative thereof is allowed to act on one
molecular proportion of an alpha, alpha, dihydroxynaphthalene mono or disulphonic
acid, or an alkaline salt thereof.
The dye-stuffs thus obtainable, in general, produce from magenta-red to bluish-
red shades on wool in an acidulated bath
COLOURING-MATTER FROM DIAZOTISED PARAMIDOBENZAMIDE AND ALPHA
ALPHA DIHYDROXYNAPHTHALENE BETA, BETA, DISULPHONIC ACID.
13.6 parts of paramidobenzamide are diazotised, in presence of muriatic acid, by
means of parts of sodium nitrite, and the liquid mixture is stirred into a solution
of 36-4 parts of alpha, alpha, dihydroxynaphthalene beta, beta, disulphonate of
sodium, and about 40 parts of sodium acetate. When the combination is complete,
the mixture is rendered alkaline, and the finished dye-stuff is salted out, filtered
off, pressed, and dried. It dyes wool in acid baths a bluish-red. Its composition is
represented by the formula :-

page_text: DYE
STUFF OBTAINED FROM
ALPHA
EXAMPLE D.
ALPHA ALPHA DIHYDROXYNAPHTHALENE
MONOSULPHONIC ACID AND DIAZOTISED ΡΑΚΑΜΙΡΟ BEN-
ZANILIDE.
The diazo compound prepared from 21-2 parts of paramido benzanilide, dissolved
in muriatic acid by means of 7 parts of sodium nitrite, is introduced into a solution
containing 26.2 parts of alpha, alpha, dihydroxynaphthalene-alpha-monosulphonate
of sodium and about 30 parts of sodium acetate. When the combination is
complete, the liquid mixture is rendered alkaline, and the finished dye-stuff is
separated in the usual manner, viz. :-by salting out, filtering off, pressing, and
drying. It produces magenta-red shades on wool in acid baths, and is represented.
by the following formula :-
Similar dye-stuffs are formed if, instead of alpha, alpha, dihydroxynaphthalene-
alpha-monosulphonate of sodium, the equivalent quantity of another alpha, alpha,
dihydroxynaphthalene mono or di-sulphonic acid, or an alkaline salt thereof, be
used, or if, instead of paramido benzanilide, the corresponding quantity of an
homologue or analogue thereof be taken, and if a molecular proportion of the
diazo derivative thereof be coupled with a molecular proportion of alpha, alpho
dihydroxynaphthalene mono or disulphonic acids, or an alkaline salts thereof. The
dye-stuffs thus obtainable, in general, dye wool in acid baths from magenta-red to
bluish-red shades.
In producing the dye-stuffs hereinbefore defined, all known alpha, alpha,
dihydroxynaphthalene monosulphonic acids and disulphonic acids, or alkaline salts
thereof, can be used. According to the researches of my foreign.correspondents,
the colouring-inatters thus formed, which in general shew similar properties, only
differ in that they yield on ordinary wool, in acidulated baths, either magenta-red
or bluish-red shades. Thus, for instance, the dye-stuffs derived from alpha, alpha,
dihydroxynaphthalene alpha monosulphonic acid and alpha alpha, dihydroxy-
naphthalene alpha, beta, disulphonic acid, produce magenta-red shades, whereas
the colouring matters derived from alpha, alpha, dihydroxynaphthalene beta, beta,
disulphonic acid yield bluish-red shades.
The researches of my foreign correspondents have shewn, that some of the dye-
stuffs thus obtainable are characterised by their capability of yielding shades
which almost absolutely withstand the action of alkalies.
In the above examples, certain distinct methods of practically producing some
of the dye-stuffs herein before defined are described. But my foreign.correspondents,
as a matter of course, do not limit themselves to the directions given in these
examples, as the mode of working can be varied, and in fact all those methods can
be used which are known and in use for producing analogous colouring matters.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed (as communicated to
me from abroad) I declare that what I claim is :-
1. The production of azo dye-stuffs from alpha, alpha, dihydroxynaphthalene
sulphonic acids and the diazo compounds of aromatic amido ketones, or of ethereal
salts, or amides, or anilides, or the like products, derived from aromatic amido
carboxylic acids.

page_text: 2. The process for producing azo colouring-matters, which process consists in
mbining a molecular proportion of an alpha, alpha, dihydroxynaphthalene
nosulphonic or disulphonic acid (such as alpha, alpha, dihydroxynaphthalene
ha monosulphonic acid, alpha, alpha, dihydroxynaphthalene alpha, beta, disul-
onic acid, or alpha, alpha, dihydroxynaphthalene beta, beta, disulphonic acid),
an alkaline salt thereof: 11
a) With a molecular proportion of a diazo derivative of an aromatic amido
ketone (such as paramidobenzophenone or the like); or
6) With a molecular proportion of the diazo derivative of an ethereal salt of
an aromatic amido carboxylic acid (such as methylic or ethylic or benzylic
paramido benzoate, or the like); or
c) With a molecular proportion of the diazo derivative of an amide of an
aromatic amido carboxylic acid (such as paramidobenzamide or the
like); or
d) With a molecular proportion of the diazo derivative of an anilide or
similar derivative of an aromatic amido-carboxylic acid (such as paramido-
benzanilide or the like).
3. As new products of manufacture, the new azo dye-stuffs produced by the
cess hereinbefore defined, or by any other method affording the same result.
Dated this 17th day of June 1895.
NEWTON & SON,
Agents for the Applicant.