IMPROVEMENTS IN THE MANUFACTURE OF COLORING MATTERS SUITABLE FOR DYEING AND PRINTING
Year: 1881

page_text: ETTERS PATENT to Joseph Anthony Dixon, of No. 175, West George Street,
Glasgow, in the County of Lanark, North Britain, Solicitor, for an Invention
of "IMPROVEMENTS IN THE MANUFACTURE OF COLORING MATTERS SUITABLE
FOR DYEING AND PRINTING." A communication from abroad by Dr. Carl
Koenig, of Höchst-am-Main, in the Empire of Germany, one of the Directors
of the Farbwerke vorin Meister, Lucius, and Brüning, of Höchst-am-Main
aforesaid.
PROVISIONAL SPECIFICATION. left by the said Joseph Anthony Dixon at
the Office of the Commissioners of Patents on the 12th December 1881.
JOSEPH ANTHONY DIXON of No. 175 West George Street Glasgow, in the
County of Lanark North Britain Solicitor. "IMPROVEMENTS IN THE MANU-
FACTURE OF COLORING MATTERS SUITABLE FOR DYEING AND PRINTING." [A
communication from abroad by Dr. Carl Koenig of Höchst-am-Main in the
Empire of Germany one of the Directors of the Farbwerke vorm: Meister, Lucius
and Brüning, of Höchst-ain-Main aforesaid.]
This Invention has for its object the manufacture of coloring matters suitable for
dyeing and printing from the acetylated primary and secondary aromatic bases,
such as acetanilide, acetotoluide, acetomethylanilide, acetodiphenylamine and so forth
as also from the substitution products of these compounds.
When the acetyl compounds of the primary and secondary aromatic bases or their
substitution products are exposed either by themselves or mixed with a salt of an
aromatic base at a suitable temperature to the action of certain dehydrating agents
there arise new color-bases or coloring materials.
In order to explain by example the mode or process of producing these coloring
matters I now proceed to give a description of the process for producing a yellow
coloring matter from acetanilide.
A mixture of equal parts of acetanilide and chloride of zinc or of one part of
acetanilide, two parts of hydrochlorate of aniline and two parts of chloride of zinc

page_text: are, for a space of time varying according to the quantities of materials worked
upon, heated at a temperature of 446° to 482° Fahr. (230° to 250° cent.) After the
action is completed the resulting mass is boiled in water in order to remove the
chloride of zinc. The resinous residue is next treated with a diluted acid, the
solution so obtained is filtered and the coloring matter is precipitated therefrom by
an addition of common salt.
It is a matter of course that instead of the acetanilide I can also use acetic acid
and aniline or as a rule any mixtures that can produce acetanilide, for example
hydrochlorate of aniline and acetate of zinc oxide or aniline and chloracetyl and
so forth.
The methylised, ethylised or otherwise alkylised derivatives of the said new
colouring matter (using the word "alkylised" here to include combinations with
phenyl and the like aromatic radicals as well as with alcoholic radicals) I obtain
from the coloring matter itself or from the base contained in or forming the ground-
work or source of it by the action of the chloride, bromide or iodide of the methyl
or other alcoholic or aromatic radical as aforesaid on the same according to a method
now well known to chemists.
The treatment of the new coloring matter and its methylised, ethylised or
otherwise alkylised derivatives with fuming sulphuric acid leads to their
corresponding sulpho-acids and in this case also (as well as in the formation_of_the_
-alkylised-compounds above-mentioned) I can instead of the coloring matters
themselves use the bases from which they are formed.
The sulpho acids of the methylised ethylised and otherwise alkylised derivatives
of the said coloring matters are also produced from the sulpho-acids of the non-
alkylised coloring matters above described by heating the alkali salts of these latter
with an alkaline solution of methyl iodide, ethyl iodide or other halogen compound
of the requisite alcoholic or aromatic radical.

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed
by the said Joseph Anthony Dixon in the Great Seal Patent Office on the
9th June 1882.
JOSEPH ANTHONY DIXON of 175 West George Street Glasgow in the County
of Lanark, North Britain, Solicitor. IMPROVEMENTS IN THE MANUFACTURE OF
COLOURING MATTERS SUITABLE FOR DYEING AND PRINTING." A communication
from abroad by Dr. Carl Koenig of Höchst-am-Main in the Empire of Germany
oneof the Directors of the Farbwerke vorm: Meister Lucius and Brüning of
Höchst-am-Main aforesaid.
This Invention has for its object the manufacture in manner hereinafter described
of colouring matters suitable for dyeing and printing from the mono-acetylated or
mono-acetylized primary and secondary aromatic monamine bases, such as acetanilide
(C,H,N-
anilide (CH, N.
H
H
CH, CO) acetotoluide (C, H. (CH,)N- CH CO aceto-methyl-
(CH, CO) acetodiphenylamine (C, H, N.
CH³
CH
CH, CO) and
so forth; as also from the substitution products of these compounds originating
in the substitution of other atoms or atom-groups that the NH or its derivative
groups for hydrogen of the aromatic nucleus. I comprehend these substitution.
products under the general term "aromatic bases."
When an acetyl compound of any of the said primary and secondary aromatic
monamine bases is exposed, either per se or mixed with a salt of any primary or
secondary aromatic monamine base, whether the base of the salt be the same as the
base of the said acetyl compound or not, to the action at a suitable temperature, of
dehydrating agents, there arises a new base, which is possessed of tinctorial
properties and may be used as a dyestuff, or for forming, by one or both of the
modifications hereinafter described, other dyestuffs. From mixtures of acetylated
aromatic bases there are, by the action of dehydrating agents, produced mixtures
of colouring matters. The dehydrating agent which I prefer to use is chloride of
zinc.
Further, any dyestuff produced by the action of a dehydrating agent on an acetyl
compound of a primary or secondary base as aforesaid, may be modified so as to
produce other colouring matters or dyestuffs by introducing into the original
dyestuff, after it has been formed, methyl, ethyl, or any other alkyl radicle of the
fatty series.
A further series of colouring matters produced by me consists of the sulpho acids
of either the non-alkylised or the alkylised dyestuffs above mentioned.
In order to explain by example the mode or process of producing the said
colouring matters, I proceed to describe, in the first place, the process for producing
a colouring matter prepared by dehydrating an acetylated primary base per se for
which purpose I select the case of the yellow colouring matter prepared by me
from acetanilide, and I shall then explain (also as an example) how I obtain
further colouring matters by modifications of the said yellow colouring matter.
To produce the said yellow colouring matter a mixture of equal parts of
acetanilide and chloride of zinc is, for a space of time, varying according to the
quantities of materials worked upon, heated at a temperature of 446° to 482°
Fahrenheit (230° to 250° centigrade). After the action is completed the resulting
mass is boiled in water, in order to remove the chloride of zinc. The resinous
residue is next treated with a diluted acid, the solution so obtained is filtered and
the colouring matter is precipitated therefrom by an addition of common salt.
The said yellow colouring matter may also be obtained by treating in the same

page_text: way a mixture of one part of acetanilide, two parts of hydrochlorate of auilin and
two parts of chloride of zinc.
In the processes which I have described for producing the said yellow colouring
matter, chemists will understand as a matter of course that, instead of the acctanilide
itself, I may also use acetic acid and anilin, or as a rule, any mixture that can
produce acetanilide as, for example, aniline hydro-chlorate and acetate of zinc or
anilin and chloracetyl and so forth and so instead of the other acetyl bases, I can
use any mixtures which produce thein.
I now proceed to explain the production of the second series of new colouring
matters above mentioned, which I may call the alkylised dyestuffs. Taking for
example the said yellow colouring matter I obtain the methyl, ethyl or other
alkyl compounds of it (which compounds are also dyestuffs). Let it be supposed
that I desire the methyl compound. I take the said yellow colouring matter itself
and act on it in a way well known to chemists with the chloride, bromide, or
iodide of methyl and so obtain the new dyestuff.
The sulpho acids of the colouring bases, alkylised or non-alkylised produced or
produceable by the methods above described afford a third series of new dyestuffs
which I call the sulpho acid dyestuffs. These sulpho acids are obtained by the
action of fuming sulphuric acid or other substitute therefor such as sulphuric acid
mono-chlorhydrine or in any other way known to chemists for the preparation of
organic sulpho acids.
The sulpho acids of the alkylised colouring matters may also be produced from
the sulpho acids of the non-alkylised colouring matters by heating the alkali salts
of the last mentioned sulpho acids in presence of alkalis with the iodides, bromides
or chlorides of the alcohol radicles which it is required to introduce into them.
Having now described and particularly ascertained the nature of the said
Invention and the system mode or manner in or under which the same is or may
be used or practically carried into effect, I would observe in conclusion that what
I consider to be novel and original and therefore claim as the Invention secured
'to me by the hereinbefore in part recited Letters Patent is:-
First. The production of colouring matters 'from the mono-acetyl compounds of
the primary and secondary aromatic monamine bases, whether further substituted
in the aromatic nucleus or not, by heating the said compounds in presence of a
dehydrating agent all in manner herein before described.
Second. The production of colouring matters from the said acetyl compounds by
heating the same in intermixture with the salt of a primary or secondary aromatic
monamine or with the acetyl compounds of a primary or secondary aromatic
monamine base in presence of a dehydrating agent all in manner hereinbefore
described.
Third. The production in manner herein before described of the alkylised dyestuffs
hereinbefore described.
Fourth. The production of the sulpho acid dyestuffs herein before described,
Euch dyestuffs being the sulpho acids of the colouring bases, alkylised or non-
alkylised, the production of which is claimed in claims 1. 2. and 3. all in manner
hereinbefore described.
In witness whereof I the said Joseph Anthony Dixon have hereunto set my
hand and seal this Eighteenth day of May in the year of our Lord One
thousand eight hundred and eighty two.
TANITAT
ULTANT
JOSETH ANTHONY
DIXON
(L.S.)