Improvements in the Production of a New Hydroxyquinone and the Utilization of the same in Dyeing.
Year: 1890

page_text: Date of Application, 13th May, 1890
Complete Specification Left, 12th Feb., 1891-Accepted, 14th Mar., 1891
PROVISIONAL SPECIFICATION.
Improvements in the Production of a New Hydroxyquinone and the
Utilization of the same in Dyeing.
I, ROBERT HOLLIDAY, a Director of Read, Holliday & Sons, Limited, of
Huddersfield, in the County of York, Manufacturing Chemist, do hereby declare
the nature of this invention to be as follows:--
This invention consists in producing a new hydroxy-quinone from Armstrong's
naphthalene disulphonate of soda and utilising the same when produced for the
manufacture of products for dyeing textile fibres.
I have discovered that by fusing Armstrong's naphthalene disulphonate of soda
with excess of caustic soda, for a longer time than it has hitherto been fused for
the production of Armstrong's dioxynaphthalene (AA), I produce a hydroxy-
quinone that has not yet been described and that the quantity produced by this
process renders it commercially available for use in the manufacture of products
for dyeing textile fibres, especially wool, by methods of which I now give example.
For instance, I take two and a half parts of caustic soda 70% and fuse
with a little water, when all the soda is fused, one part of finely powdered
Armstrong's naphthalene disulphonate of soda is gradually added and then well
fused. When the mixture has become a stiff dark brown paste it is allowed to
cool. The melt is broken up and introduced into a mixture of sulphuric acid
and water, the acid being in excess of the alkali in the melt. The solution is
then filtered, the filtrate contains dioxynaphthalene and the residue contains the
hydroxy-quinone. The residue is boiled with excess of sodic carbonate, filtered
and the hydroxy-quinone is reprecipitated with an acid. It can then be collected
and dried.
Two parts of this hydroxy-quinone are dissolved in a dilute solution of sodic
carbonate and to the solution is added a ten per cent, solution of nitrite of soda,
containing about one part of the salt. This mixture is well cooled and a dilute
solution of acetic acid or a mineral acid (such as hydrochloric) is added until the
mixture is acid. It is kept well agitated for some time, then the nitroso-compound
is collected.
Black and colours approaching to black are obtained by alternately treating wool
or other fibres with metallic salts, such as chrome and iron salts and with this
nitroso-hydroxy-quinone.
As example, I may boil 100 lbs. of wool in water with about 3 lbs. of bichromate
of soda and 1 lb. of sulphuric acid, for about one hour, then wash off and afterwards
pass the wool into a bath of hot water containing 3 lbs. of the nitroso-hydroxy-
quinone, then boil until the required depth of colour is obtained; or produce:-
A black on unmordanted wool from this nitroso-hydroxy-quinone (using it pre-
ferably in a paste state) by boiling it with water, rendered slightly acid with acetic
acid, then gradually adding a solution of hydrosulphite of soda, until the solution
becomes almost colourless. The fibre required to be dyed is dipped into this and
remains in according to depth of shade required. The superfluous liquid having
been returned to the dye-bath; the fibre is oxidised, either by exposure to the air
or otherwise in order to fully develop the colour.
Doted the 13th day of Mar 1800
WM. BROOKES & SON,
55 & 56, Chancery Lane, London, Agents for the Applicant.

page_text: COMPLETE SPECIFICATION.
Improvements in the Production of a New Hydroxyquinone and the
Utilization of the same in Dyeing.
I, ROBERT HOLLIDAY, a Director of Read, Holliday & Sons, Limited, ot
Huddersfield, in the County of York, Manufacturing Chemist, 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 consists in producing a new hydroxyquinone from what is known
as Armstrong's naphthalene disulphonate of soda (A,A,) and utilizing the same
when produced for the manufacture of products for dyeing textile fibres.
I have discovered that by fusing Armstrong's naphthalene disulphonate of soda
(AA) for a longer time than it has hitherto been fused for the production of
Armstrong's dioxynaphthalene (A,As), I produce a new hydroxyquinone and the
quantity so produced by my process is such as to render it commercially available
for use in the manufacture of products for dyeing textile fibres, especially wool, by
methods of which I now give example.
For instance I take two and a half parts of caustic soda 70% and fuse with
a little water when all the soda is fused, one part of finely divided Armstrong's
naphthalene disulphonate of soda is gradually added and then well fused. When
the mixture has become a stiff dark brown paste it is allowed to cool.
The
melt is broken up and introduced into a mixture of sulphuric acid and water, the
acid being in excess of the alkali in the melt. The solution is then filtered, the
filtrate contains dioxynaphthalene and the residue contains the hydroxyquinone.
The residue is boiled with excess of sodic carbonate or caustic soda solution, filtered
and the hydroxyquinone is reprecipitated with an acid. It can then be collected
and dried.
Two parts of this hydroxyquinone are dissolved in a dilute solution of sodic car-
bonate and to the solution is added a ten per cent. solution of nitrite of soda, contain-
ing about one part of the salt. This mixture is well cooled and a dilute solution of
acetic acid or a mineral acid, (such as hydrochloric or sulphuric) is added until the
mixture is acid. It is kept well agitated for some time, then the nitroso compound
is collected.
Black and colours approaching to black are obtained by alternately treating wool
or other fibres with suitable metallic salts, such as chrome and iron salts and with
this nitroso-hydroxyquinone.
As an example: I may boil 100 lbs. of wool in water with about 3 lbs. of bichro-
mate of soda and 1 lb. of sulphuric acid, for about one hour, then wash off and
introduce the wool into a bath of hot water containing 3 lbs. of the nitroso hydroxy-
quinone, then boil until the required depth of colour is obtained.
Or I produce
A black or unmordanted wool from this nitroso hydroxyquinone (using it
preferably in a paste form) by boiling it with water rendered slightly acid with
acetic acid, then gradually adding a solution of hydrosulphite of soda until the
solution becomes almost colourless. The fibre required to be dyed is dipped into
this and is allowed to remain in it according to depth of shade required. Other
suitable reducing agents such as zinc in acid, neutral or alkaline solutions may be
employed. The superfluous liquid having been returned to the dye bath, the fibre
is oxidized by exposure to the air or otherwise in order fully to develop the colour.
The quantities of wool or other fibres and the nature of the metallic salt and acid
can be varied according to the result required and the shades of colour may be
varied by using other dyeing or colouring matters along with or alternatively with
the nitroso compound.
The fibre can be dyed either in a raw, woven, felted or otherwise partly manu-
factured or manufactured state.

page_text: When cotton or other fibres which have not the same affinity as wool for metallic
oxides are required to be dyed the oxides of the metals mentioned can be fixed in
any of the ordinary manners well known to dyers.
I prefer to use the nitroso compounds in the state of precipitated paste though
they can be used combined with alkali or otherwise; if combined with alkali, the
alkali had better be neutralized in the dye bath with acetic or other suitable acid.
Having now particularly described and ascertained the nature of my said inven-
tion, and in what manner the same is to be performed, I declare that what
I claim is
1. The herein described process of producing the nitroso compound of the herein-
before mentioned hydroxyquinone.
2. The dyeing of textile fibres by forming therein the production of the combi-
nation of the oxides of chrome, iron, copper, lead or alumina with the hereinbefore
mentioned nitroso-hydroxyquinone substantially as hereinbefore described.
3. The manufacture of colouring matters by the reduction of the hereinbefore
mentioned nitroso-hydroxyquinone defined herein and the method of dyeing wool
and other fibres therewith substantially as described.
1001
WM. BROOKES & SON,
55 & 56, Chancery Lane, London, Agents for the Applicant.