Production of New Dye-stuffs Derived from Amidonaphtol-sulphonic.
Year: 1892

page_text: Date of Application, 19th Aug., 1892
Complete Specification Left, 18th May, 1893-Accepted, 1st July, 1893
PROVISIONAL SPECIFICATION.
Production of New Dye-stuffs Derived from Amidonaphtol-sulphonic.
Acids.
I, GEORGE PITT, of Sutton, in the County of Surrey, Gentleman, (a com-
munication to me from abroad by Leopold Cassella & Co., of Frankfort-on-Main,
in the Empire of Germany, Manufacturing Chemists,) do hereby declare the
nature of this invention to be as follows:-
In the British Patents Nos. 16699, 19330%, 1742", it has been shown that
black, blueish-black, and blue dyestuffs are obtainable by combining amidonaphtol-
sulphonic acids with tetrazo-bodies in alkaline solutions.
By the present Specification I describe some particularly interesting new com-
binations, which can be obtained by the process or processes described in the
above named Patents.
The para-phenylenediamine can be used equally well, in place of other diamines
for the production of diamine-blacks.
The combination of tetrazophenylene with two molecules of y-amidonaphtol-
If one molecule of
sulphonic acid in alkaline solution produces a blackish groy.
this acid is replaced by one molecule of a naphtol sulphonic acid, such as a-naphtol
sulphonic acid 14, or by one molecule of a dioxynaphtalene-sulphonic acid, such as
dioxynaphtalene sulphonic acid G or S, blueish black dyestuffs result.
It is known that the production of dyestuffs deriving from paraphenylene
diamine is generally executed in two phases. First, the monoacetyle-derivative is
combined, then it is saponified, again diazotized and combined a second time. Or
paranitrodiazobenzole is first allowed to react, then the nitrated dyestuff is
reduced by sulphuret of sodium, then diazotized again and combined a second
time. The coloring matters described hereafter can be prepared by either of
these two methods.
Example I. Acetyleparaphenylenediamine I combine with one molecule of
a-naphtylamine or of Boxethyle-a-naphtylamine or of amidonaphtol sulphonic
acid, I saponify, diazotize again with two molecules of nitrite of soda and combine
The
in alkaline solution with two molecules of y amidonaphtolsulphonic acid.
result of the operation is a colouring matter dyeing unmordanted cotton a deep
black.
a
Example II.-Acetyleparaphenylenediamine I combine with one molecule of
a naphtylamine
naphtylamine or of Boxethyle a naphtylamine, or of an
Bsulphonic acid or an amidonaphtol-sulphonic acid, the resulting product is then
diazotized and combined with one molecule of a naphtol-sulphonic acid such as
the acid 14, or with one molecule of a dioxynaphtalene sulphonic acid, such as
the acids G or S, then the acetyle group is eliminated, again diazotised and finally
combined with one molecule of y amidonaphtol-sulphonic acid in alkaline solution.
The resulting coloring matters dye unmordanted cotton a blueish black.
The mixed dyestuffs deriving from dioxynaphtalene-sulphonic acids and from
amidonaphtolsulphonic acids yield products of special industrial value.
For instance: the tetrazoderivative of a paradiamine (such as benzidine,
tolidine, diamidoethoxydiphenyle, diamidodiphenolether, etc.) is combined with
one molecule of dioxynaphtalenesulphonic acid G in neutral or even slightly acid
solution; the intermediate body is introduced into the alkaline solution of one
molecule of y amidonaphtolsulphonic acid.
The shades vary from violet black to blueish black. Greener dyestuffs are
obtained by replacing the acid G by dioxynaphtalene monosulphonic acid S..
-
In the British Patent No. 7067, has been shown that in most of the secondary

page_text: azo bodies deriving from a naphtylamine, the latter can be replaced by
naphtolether (1-2).
a amido-
This substitution can likewise be used for the production of secondary (trisazoic)
diamine blacks. The tetrazo-derivatives of benzidine, tolidine diamidoethoxy-
diphenyle, diamidodiphenyle-ether etc. I combine with one molecule of
a amidonaphtolether, the intermediate bodies I diazotise again and combine
them with two molecules of y amidonaphtolsulphonic acid in alkaline solution.
In all the described processes, the y amidonaphtol-sulphonic acid can be replaced
by another amidonaphtolsulphonic acid, such as the mono- or disulpho-derivatives
of amido-naphtol 1.8. By the amidonaphtolsulpho acid H, for instance, blueish
blacks of great fastness are obtained.
All the herein described coloring matters can be diazotized and again combined,
either in the substance or on the dyed fibre.
Dated this 19th day of August 1895
COMPLETE SPECIFICATION.
Production of New Dye-stuffs Derived from Amidonaphtol-sulphonic
Acids.
1, GEORGE PITT, of Sutton, in the County of Surrey, Gentleman, (a com-
munication to me from abroad by Leopold Cassella & Co. of Frankfort-on-
Main, in the Empire of Germany, Manufacturing Chemists) 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 :-
In the British Patents Nos. 166999, 1933000, 1742", it has been shown that
black, blueish-black, and blue dyestuffs are obtainable by combining amidonaphtol-
sulphonic acids with tetrazo-bodies in alkaline solutions.
By the present Specification I describe some particularly interesting new com-
binations, which can be obtained by the process or processes described in the above
named Patents.
The para-phenylenediamine can be used equally well in place of other diamines
for the production of diamine blacks.
The combination of tetrazophenylene with two molecules of y-amidonaphtol-
sulphonic acid in alkaline solution produces a blackish grey. If one molecule of
this acid is replaced by one molecule of a naphtol sulphonic acid, such as a-naphtol
sulphonic acid 1-4, or by one molecule of a dioxynaphtalene-sulphonic acid, such as
dioxynaphtalene sulphonic acid G or S, blueish black dyestuffs result.
It is known that the production of dyestuff's deriving from paraphenylene
dianine is generally executed in two phases. First, the monoacetyle-derivative is
combined, then it is saponified, again diazotized and combined a second time. Or
paranitrodiazobenzole is first allowed to react, then the nitrated dyestuff is reduced
by sulphuret of sodium, then diazotized again and combined a second time. The
coloring matters described hereafter can be prepared by either of these two
methods.
Example I. Acetyleparaphenylenediamine I combine with one molecule of a-naph-
tylamine or of Boxethyle-a-naphtylamine or of amidonaphtol sulphonic acid, I
saponify, diazotize again with two molecules of nitrite of soda and combine in
alkaline solution with two molecules of 7-amidonaphtolsulphonic acid. The result
of the operation is a colouring matter dyeing unmordanted cotton a deep black.
Example II. Acetyleparaphenylenediamine I combine with one molecule of
a naphtylamine or of Boxethyle a naphthylamine, or of an naphtylamine
sulphonic acid or an amidonaphtol-sulphonic acid, the resulting product is then
diazotized and combined with one molecule of a naphtol-sulphonic acid such as the
acid 14, or with one molecule of a dioxynaphtalene sulphonic acid, such as the
acids G or S, then the acetyle group is eliminated, again diazotised and finally
a

page_text: combined with one molecule of y amidonaphtol-sulphonic acid in alkaline solution.
The resulting coloring matters dye unmordanted cotton a blueish black.
The mixed dyestuffs deriving from dioxynaphtalene-sulphonic acids and from
amidonaphtolsulphonic acids yield products of special industrial value.
For instance: the tetrazoderivative of a paradiamine (such as benzidine, tolidine,
diamidoethoxydiphenyle, diamidodiphenolether, etc.) is combined with one molecule
of dioxynaphtalene-sulphonic acid G in neutral or even slightly acid solution; the
intermediate body is introduced into the alkaline solution of one molecule of
y amidonaphtolsulphonic acid.
The shades vary from violet black to blueish black. Greener dyestuffs are
obtained by replacing the acid G by dioxynaphtalene mono-sulphonic acid S.
In the British Patent No. 706789 has been shown that in most of the secondary
u amido-
azo bodies deriving from a naphtylamine, the latter can be replaced by
naphtolether (1.2). This substitution can likewise be used for the production of
secondary (trisazoic) diamine blacks. The tetrazo derivatives of benzidine, tolidine
diamidoethoxydiphenyle, diamido-diphenyle-ether etc. I combine with one molecule
of a amido-naphtolether, the intermediate bodies I diazotise again and combine
them with two molecules of y amidonaphtolsulphonic acid in alkaline solution.
In all the described processes, the y amidonaphtol-sulphonic acid can be replaced
by another amidonaphtolsulphonic acid, such as the mono- or disulpho-derivatives
of amidonaphtol 1-8. By the amidonaphtolsulpho acid H, for instance, blueish
blacks of great fastuess are obtained.
All the herein described coloring matters can be diazotized and again combined,
either in the substance or on the dyed fibre.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed I declare that what
I claim is
1. The above described processes for producing disazo dyestuffs, derived from
amidonaphtolsulpho acid.
2. As articles of manufacture the new dyestuffs hereinbefore described.
Dated this 2nd day of May 1893.
CARPMAEL & Co.,
Agents for the Applicant.