Improvements in the Manufacture of Intermediate Products and Colouring Matters therefrom.
Year: 1899

page_text: PROVISIONAL SI POLT HUAHUA.
Improvements in the Manufacture of Intermediate Products and
Colouring Matters therefrom.
We, READ HOLLIDAY AND SONS LIMITED, of Turnbridge, Huddersfield, in the
County of York, Manufacturing Chemists, and JOSEPH TURNER, HARRY DEAN,
and JAMES TURNER, of the same place, Chemists, do hereby declare the nature
of this invention to be as follows:-
This invention relates to the production of certain amido sulphonic acids of
the phenolic and carboxylic series and colouring matters derived therefrom.
We have found that certain nitro bodies of the phenolic and carboxylic series
vield useful amido sulphonic acids when boiled with several times their weight
of bisulphite of soda until a sample taken shows no free nitro body. The fol-
lowing substances may be enumerated as being especially useful for the purposes
of this invention
1. Para nitro phenol.
2. Ortho nitro phenol.
3. Ortho nitro salicylic acid.
4. Para nitro salicylic acid.
5. Meta nitro benzoic acid.
We have also found that the amido sulphonic acids so produced are useful
for the production of colouring matters by diazotising and combining with
amines, phenols, amido phenols, their sulpho or carbo acids, some of which
possess the property of combining with metallic mordants and yielding shades
upon the fibre which offer considerable resistance to milling and light. The
following examples serve to illustrate the nature of this invention.
EXAMPLE 1.
100 parts by weight of ortho or para nitro salicylic acid or the products
obtained by the nitration of salicylic acid are boiled with 1000 parts by weight
of bisulphite of soda until the yellow colour of the nitro compound has dis-
appeared.
Hydrochloric acid is then added and the solution boiled until free from
sulphurous acid. On allowing the mixture to cool the amido sulpho salicylic
acid separates out in the form of a white crystalline precipitate.
EXAMPLE 2.
23.1 parts amido sulpho salicylic acid are diazotised in the usual manner and
the diazo compound run into a solution containing 18 parts of alpha naphtyl-
amine hydrochloride. After standing for some time the intermediate product
is filtered off and the precipitated amido azo compound after dissolving in soda
is further diazotised by the addition of 7 parts of sodium nitrite and 37 parts
of hydrochloric acid 30%. The diazotising is complete in a few hours and is
then run into a solution of 35 parts of beta naphtol disulphonic acid R in car-

page_text: bonate of soda. After standing a few hours the colouring matter separates in
the form of a fine black precipitate and may be filtered, pressed and dried.
EXAMPLE 3.
23.1 parts amido sulpho salicylic acid are diazotised in the usual manner
and run into a solution of 12.2 parts of meta toluylene diamine. The colouring
matter separates out and may be filtered, pressed and dried. The dyestuff so
produced dyes unmordanted wool a yellowish brown and wool mordanted with
chromium a deep reddish brown.
Dated the 3rd day of February 1899.
Improvements in the Manufacture of Intermediate Products and
Colouring Matters therefrom.
We. READ HOLLIDAY AND SONS LIMITED, of Turnbridge, Huddersfield, in the
County of York, Manufacturing Chemists, and JOSEPH TURNER, HARRY DEAN,
and JAMES TURNER, of the same place, 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:—
This invention relates to the production of certain amido sulphonic acids of
the phenolic and carboxylic series and colouring matters derived therefrom.
We have found that certain nitro bodies of the phenolic and carboxylic series
yield useful amido sulphonic acids when boiled with several times their weight
of bisulphite of soda until a sample taken shows no free nitro body. The fol-
lowing substances may be enumerated as being especially useful for the purposes
of this invention.
1. Para nitro phenol.
2. Ortho nitro phenol.
3. Ortho nitro salicylic acid.
4. Para nitro salicylic acid.
5. Meta nitro benzoic acid.
We have also found that the amido sulphonic acids so produced are useful
for the production of colouring matters by diazotising and combining with
amines, phenols, amido phenols, their sulpho or carbo acids, some of which
possess the property of combining with metallic mordants and yielding shades
upon the fibre which offer considerable resistance to milling and light. The
following examples serve to illustrate the nature of this invention.
EXAMPLE 1.
100 parts by weight of ortho or para nitro salicylic acid or the products
obtained by the nitration of salicylic acid are boiled with 1000 parts by weight
of an aqueous solution of sodium bisulphite 50° to 56° Twaddle until the
yellow colour has disappeared. Hydrochloric acid is then added and the solution
boiled until free from sulphurous acid. On allowing the mixture to cool the
amido sulpho salicylic acid separates out in the form of a white crystalline
precipitate.

page_text: 23.1 parts amido sulpho salicylic acid are diazotised in the usual manner and
the diazo compound run into a solution containing 18 parts of alpha naphtyl-
amine hydrochloride. After standing for some time the intermediate product
is filtered off and the precipitated amido azo compound after dissolving in soda
is further diazotised by the addition of 7 parts of sodium nitrite and 37 parts
of hydrochloric acid 30%. The diazotising is complete in a few hours and is
then run into a solution of 35 parts of beta naphtol disulphonic acid R in car-
bonate of soda. After standing a few hours the colouring matter separates in
the form of a fine black precipitate and may be filtered pressed and dried. The
dyestuff obtained dyes wool bluish black shades and wool mordanted with
chromium salts deep fast blacks. If in Example 2 we replace the naphthol
disulphonic acid R. by 22.4 parts a napthol sulphonic acid NW, or by 34.1 parts
acid sodium salt of amido naphtol disulphonic acid 1:8:3:6 we obtain dye-
stuffs which dye redder and bluer shades respectively.
EXAMPLE 3.
23.1 parts amido sulpho salicylic acid are diazotised in the usual manner
and run into a solution of 12.2 parts of meta toluylene diamine. The colouring
matter separates out and may be filtered, pressed and dried. The dyestuff so
produced dyes unmordanted wool a yellowish brown and wool mordanted with
chromium a deep reddish brown.
EXAMPLE 4.
23.1 parts amido sulpho salicylic acid are diazotised and the diazo body run
into a solution of 34.1 parts amido napthol disulphonic acid H in the presence
of carbonate of soda. The colour may be isolated by salting, filtering, pressing
and drying in the usual manner. It dyes wool a fine bluish red which changes
to a fine blue violet by boiling in a bath containing chromium flouride.
Having now particularly described and ascertained the nature of our said
invention and in what manner the same is to be performed we declare that
what we claim is:-
1. The production of amido sulphonic acids of the phenolic and carboxylic
series by heating with bisulphite of soda any of the following nitro compounds
viz.Ortho nitro phenol, para nitro phenol, ortho nitro salicylic acid, para
nitro salicylic acid, meta nitro benzoic acid.
2. The production of dyestuffs from amido sulpho salicylic acid produced as
herein before described by converting into its diazo compound and combining
with alpha naphtylamine, then further diazotising the intermediate amido azo
body and combining with beta naphtol disulphonic acid R, alpha naphtol
sulphonic acid NW or amido napthol disulphonic acid 1:8:3:6 in alkaline
solution.
3. The production of colouring matters by combining the diazo compound
from amido sulpho salicylic acid with meta toluylene diamine or meta phenylene
diamine in alkaline or acid solution.
4. The production of dyestuffs by combining the diazo compound from amido
sulpho salicylic acid with amido naphtol disulphonic acid 1:8:3:6 in alkaline
solution.
5. The production and use of intermediate products and colouring matters
therefrom by means substantially equivalent to those herein before described.
Dated the 2nd day of November 1800.
WM. BROOKES & SON,
55 and 56, Chancery Lane, London, Agents for the Applicants.