The Manufacture or Production of New Anthraquinone Dye Stuffs.
Year: 1899

page_text: Date of Application, 27th Nov., 1899
Complete Specification Left, 21st Aug., 1900-Accepted, 16th Nov., 1900.
[Communicated from abroad by THE FARBENFABRIKEN vormals FRIEDRICH
BAYER & Co., of Elberfeld, Germany.]
The Manufacture or Production of New Anthraquinone Dye Stuffs.
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 to be as follows:-
My foreign correspondents have found that, by treating mono- and diamido
anthraquinone sulphonic acids, or derivatives thereof, e.g., amido-oxy-anthra-
quinone sulphonic acids, with benzylchloride, benzylated compounds of great
technical value are obtained.
The compounds thus produced dye unmordanted wool, in acid baths, more
blueish or more greenish shades than the starting materials.
Thus, for instance, from alpha amido anthraquinone sulphonic acid (see
Berichte. der deutschen chemischen Gesellschaft," volume 15, page 1519),
which yields, on unmordanted wool, brick-red shades, according to the new
process, a benzylated derivative can be obtained, which dyes unmordanted wool,
in acid baths, blueish-red shades.
In order to illustrate the new process more fully, the following examples are
given, the parts being by weight.
EXAMPLE A.
Into a solution prepared from 10 parts of mono-amido-anthraquinone sulphonic
acid, which can be obtained by sulphonation of mono-amido-anthraquinone, and
400 parts of hot water, 6 parts of benzyl-chloride (which quantity corresponds
with about one and a half molecules) are introduced, with energetic stirring,
at from 80 to 90 degrees Centigrade. The color of the solution thus obtained
assumes a bluer tint after a short time. The reaction is finished when no
change of tint is discernible. The new dye-stuff thus produced is then com-
pletely separated by the addition of common salt, pressed, and dried. It repre-
sents a blueish red powder, which dissolves in water with a bluer tint than the
starting material, and dyes unmordanted & chrome mordanted wool as above
mentioned.
EXAMPLE B.
8 parts of benzyl-chloride are slowly introduced, with energetic stirring, into
a solution prepared from 10 parts of diamidoanthrarufindisulphonic acid (see
Letters Patent No. 120112), and 500 parts of hot water, the temperature of the.
solution being kept at about from 80 to 90 degrees Centigrade. Stirring is.
continued at the same temperature until a test portion, when dissolved in con-
centrated sulphuric acid, and mixed with horic acid, is found to exhibit no
longer the characteristic absorption spectrum of the boric acid ether of the
diamidoanthrarufindisulphonic acid. When this stage is reached, the new

page_text: benzylated dye-stuff (which begins to separate partially from the reaction
mixture, even when still hot) is completely precipitated by cooling the reaction
mixture, and by the addition of a concentrated common salt solution.
The coloring matter is finally filtered off, dried, & pulverized. It is thus
obtained in the shape of a blue powder. The dye-stuff is soluble in water with
a blue color, which is more greenish-blue than that of a watery solution of the
diamidoanthrarufindisulphonic acid. On adding strong hydrochloric acid to the
watery solution of the new dye-stuff, the latter is precipitated, the color of the
solution not,, in this case, being changed into violet. The new benzylated dye-
stuff is easily soluble in alcohol. By concentrated sulphuric acid, it is dissolved
with a yellow color, which changes into green on the addition of boric acid.
The new dye-stuff dyes unmordanted wool, in acid baths, bright-blue shades,
and yields on chrome mordanted wool, greenish-blue shades.
1.
The process proceeds in an analagous manner, if other of the above defined
compounds are used, such, for instance,. as the other monoamidoanthraquinone
sulphonic acids, diamidochrysazindisulphonic acid, 1-5-diamidoanthraquinone-
disulphonic acid, 1-8-diamidoanthraquinone-disulphonic acid, diamidoanthra-
chryson-disulphonic acid, diamidoanthrarufinmonosulphonic acid, or the like.
As a matter of course, my foreign correspondents do not intend to confine
themselves to the particulars given in the above examples, as these are merely
typical, and can be varied within wide limits.
NEWTON & SON,
Agents for the Applicants.
COMPLETE SPECIFICATION.
The Manufacture or Production of New Anthraquinone Dye-stuffs.
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 manner the same is to be performed, to
be particularly described and ascertained in and by the following statement:-
My foreign correspondents have found that by treating mono- and diamido-
anthraquinone sulphonic acids or derivatives thereof, such as, amidooxyanthra-
quinone sulphonic acids with benzylchloride, benzylated compounds of great
technical value are obtained.
The compounds thus produced dye unmordanted wool in acid baths bluer or
greener shades than the starting materials.
Thus for instance from alpha-amido-anthraquinone sulphonic acid which
vields on unmordanted wool brick-red shades, according to the new process a
benzylated derivative can be obtained which dyes unmordanted wool in acid
baths blueish-red shades.
In order to illustrate the new process more fully the following examples are
given, the parts being by weight.
EXAMPLE A.
Into a solution prepared from 10 parts of monoamidoanthraquinone-sulphonic
acid and 400 parts of hot water 6 parts of benzylchloride (which quantity corre-
sponds with about one and a half molecules) are introduced with energetic
stirring at from 80 to 90 degrees Centigrade. The blueish color of the solution
thus obtained increases in intensity after a short time. The reaction is finished
when no further change of tint is discernible. The new dye-stuff thus pro-

page_text: duced is then completely separated by the addition of common salt, pressed
and dried.
It represents a blueish-red powder which dissolves in water with a bluer tint
than the starting material and dyes unmordanted and chrome mordanted wool
as above mentioned.
EXAMPLE B.
8 parts of benzylchloride are slowly introduced with energetic stirring into
a solution prepared from 10 parts of diamidoanthrarufine disulphonic acid (see
Letters Patent No. 1201.1%) and 500 parts of hot water, the temperature of the
solution being kept at about from 80 to 90 degrees Centigrade. Stirring is con-
tinued at the sanie temperature until a test portion, when dissolved in concen-
trated sulphuric acid and mixed with boric acid is found to exhibit no longer
the characteristic absorption spectrum of the boric acid ether of the diamido-
anthrarufine disulphonic acid.
When this stage is reached the new benzylated dye-stuff (which begins to
separate partially from the reaction mixture, even when still hot) is completely
precipitated by cooling the reaction mixture and by the addition of a concen-
trated common salt solution.
The coloring matter is finally filtered off, dried and pulverized. It is thus
obtained in the shape of a blue powder. The dyestuff is soluble in water with
a blue color which has a greener tint than that of a watery solution of the
diamido-anthrarufine disulphonic acid. On adding strong hydrochloric acid to
the watery solution of the new dye-stuff the latter is precipitated, the color of
the solution in this case not being changed into violet. The new benzylated
dye-stuff is easily soluble in alcohol. By concentrated sulphuric acid it is
dissolved with a yellow color which changes into green on the addition of boric
acid. The new dye-stuff dyes unmordanted wool in acid baths bright blue
shades and yields on chrome-mordanted, wool greenish-blue shades.
The process proceeds in an analogous manner if other of the above defined
compounds are used such for instance as the other mono-amido-anthraquinone
sulphonic acids, diamidochrysazinedisulphonic acid, 1-5 diamido anthraquinone
disulphonic acid, 1-8-diamidoanthraquinone disulphonic acid, diamido anthra-
chrysonedisulphonic acid, diamido-anthrarufine-monosulphonic acid, or the like.
As a matter of course my foreign correspondents do not intend to confine them-
selves to the particulars given in the above examples as these are merely typical
and can be varied within wide limits.
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 process for the production of new dye-stuffs, of the anthracene series
which process consists in treating with benzyl-chloride mono- or diamido-
anthraquinone sulphonic acids or derivatives thereof, such as monoamidooxy-
anthraquinone sulphonic acids, diamidoanthrarufine disulphonic acid, diamido-
chrysazine disulphonic acid, diamidoanthrachrysone disulphonic acid, diamido-
anthrarufine monosulphonic acid, or the like, substantially as hereinbefore
described.
2. As new articles of manufacture the products obtainable by the process
herein before described and claimed.
Dated this 17th day of August 1000