DE590956C - Process for the production of water-insoluble azo dyes - Google Patents

Description

GERMAN EMPIRE

ISSUED ON
JANUARY 13, 1934

REICH PATENT OFFICE

PATENT LETTERING

M 590956 CLASS 22 a GROUP

Patented in the German Empire on June 26, 1932

It has been found to be too valuable

water-insoluble azo dyes obtained when diazo compounds with 4,8-dioxy-i, 2, 5, 6-dibenzophenazines from the

OH

HO

which are further substituted in the benzene nuclei which do not carry the hydroxyl group can, on its own or on a coupling basis. Neither the diazo nor the azo components contain solubilizing groups.

In this way, depending on the type of diazo compounds used, one obtains from Monoamines, from aminoazo compounds or polyamines deep red-brown to black Colorations.

The new dyes can be used to make ice colors and prints on the Fiber or also for the preparation of pigments are used.

The 4, 8-Dioxy-1, 2, 5, 6-dibenzophenazines have, in contrast to the / ^ - naphthol, a certain affinity for the fiber, which makes it possible to produce the dye on the fiber without intermediate drying. The dyeings produced in this way have ^{a better fastness to water than comparable dyeings produced using B z} "3 '>3" -dioxy-1, 2, 5, 6-dibenzophenazine, which have become known from patent specification 467 634.

B e i s ρ i e 1 ι

*) The patent seeker stated as the inventor:

Dr. Arthur Zitscher in Offenbach a. M,

12.75 parts by weight of i-amino-3-chlorobenzene are diazotized in the usual way, and the diazo solution is' with a solution of 32.5 parts by weight of 4, 8-Dioxy-i, 2, 5, 6-dibenzophenazine in dilute sodium hydroxide solution, with the amount of sodium acetate sufficient to bind the excess mineral acid and 5 parts by weight of Turkish red oil is added, coupled. The retired Dye is filtered off and washed out well. For the preparation of pigments it is advantageously used in the form of a paste and, mixed with substrates, provides a dark brown varnish.

5Ö0956

Example 2

Well-boiled and dried cotton yarn is mixed with a solution containing 5 g of 4, 8-dioxy-i, 2, 5, 6-dibenzophenazine, 10 ecm of caustic soda 34 ⁰ Be, 10 ecm of Turkish red oil and 50 g of table salt per liter, im-

impregnated, well squeezed and in a diazo solution blunted with sodium acetate, which contains 1.68 g of i-amino-2-methoxy-4-nitrobenzene per liter, developed, rinsed and soaped.

A deep black-brown color is obtained in this way.

From the same azo component is obtained with diazotized

i-Amino-2,4-dimethyibenzene an olive black,

i-Amino-2-methyl-5-chlorobenzene a black brown,

i-Amino-2-phenoxy-5-chlorobenzene a dark red-brown,

i-Amino ^ -benzoylamino-S-methoxy ^ -chlorobenzene ... a brownish black,

i-Amino-4-benzoylamino-2, 5-diethoxybenzene a blackish green,

i-Amino-2-nitrobenzene a red-brown,

i-aminoanthraquinone ·. a red-brown,

4-Amino-4'-methoxydiphenylamine an olive black,

4 "Amino-3, 2'-dimethylazobenzene an olive black,

4 "Amino-2,5-dimethoxy-4'-nitroazobenzene. A green black.

Using 4,8-dioxy-Bz-2 ', 2 "-dibromo-i, 2, 5, 6-dibenzophenazine is obtained with diazotized

i-Amino-2-chlorobenzene a black olive brown,

i-Amino-2, 5-dichlorobenzene a dark brown,

i-Amino-2-methyl-5-chlorobenzene a dark olive,

i-Amino-2-methyl-3-chlorobenzene a dark olive,

i-Amino-2-methoxy-5-chlorobenzene a dark olive,

i-amino-2- (4'-chlorophenoxy) -5-chlorobenzene. a dark olive,

l-Amino-2-methoxybenzene-5-sulfonic acid diethylamide an olive,

2-aminodiphenyl sulfone a red-brown,

i-Amino-2-methyl-4-nitrobenzene a black olive,

i-Amino-2-methoxy-5-nitrobenzene a brown olive.

The dyes can also be used on other fibers, such as. B. Artificial silk from regenerated Cellulose or fibers of animal origin.

Claims (1)

Claim: Process for the production of water-insoluble azo dyes, therein standing that one diazo compounds with 4, 8-Dioxy-i, 2, 5, 6-dibenzophenazinen, which is further substituted in the benzene nuclei which do not carry the hydroxyl group may be, alone or on a coupling basis, with neither the diazo nor the azo components being soluble making groups should contain.