DE1025543B - Process for the production of Kuepen dyes - Google Patents

Description

Process for the production of vat dyes It has been found that valuable vat dyes are obtained when 1,5-di-acylamino-4-alkoxy-anthraquinone treated with sulfuric acid above room temperature and the 1,5-diamino-4-oxy-anthraquinone obtained with aromatic carboxylic acids of the general formula X-R-COOH (where R is a benzene or anthraquinone nucleus and X halogen or a nitro, amino or trifluoromethyl group means) or their functional derivatives condensed.

The dyes thus obtained correspond to the general formula where R and X have the above meaning.

They provide dyes and prints of good quality on vegetable fibers Authenticity properties.

The dyes prepared according to the invention have preference over the violet vat dye known from Example 10 of German Patent 665598 and composed of 1,5-diamino-4,8-dioxy-anthraquinone and m-trifluoromethylbenzoyl chloride; that the dyeings produced with them have significantly better boiling fastness properties, specifically with regard to bleeding onto undyed cotton treated with them and also with regard to the change in color, than the dyeings obtained with the known dye.

Another advantage of the dyes of the invention is theirs about 50% greater yield compared with the known dye.

Example 1 10 parts of 1-benzoylamino-4-methoxy-5- (p-toluenesulfamido) anthraquinone (red crystals with a melting point of 300 ° recrystallized from nitrobenzene; produced from 1-benzoylamino-4-methoxy-5-chloro-anthraquinone and p-toluenesulfamide in nitrobenzene in the presence of sodium and copper acetate) with 100 parts of 90% sulfuric acid Heated to 100 'for 2 hours. This is done by saponifying the benzoylamino and toluenesulfamido groups 1,5-diamino-4-oxy-anthraquinone obtained and dealkylation of the methoxy group crystallized from o-dichlorobenzene in bronze colored crystals that melt at 320 '. A mixture from 300 parts of o-dichlorobenzene, 6.4 parts of 1,5-diamino-4-oxy-anthraquinone and 11.9 Parts of m-fluorobenzoyl chloride is heated to 160 ° for 12 hours. The resulting dye is filtered off with suction after cooling, washed with o-dichlorobenzene and methanol and dried.

It dissolves in concentrated sulfuric acid with a bluish tinge Color and dyes and prints the vegetable fiber from brownish red vat in very clear yellowish pink tones with good fastness properties.

In this example, instead of the m-fluorobenzoyl chloride, a equimolecular amount of o-fluorobenzoyl chloride or of m-trifluoromethylbenzoyl fluoride used for condensation, dyes are obtained, the cotton in clear dye more yellowish tones than the dye of paragraph 1 of this example. The "p-trifluoromethylbenzoyl dye" has a more bluish tint than the corresponding one m connection.

The use of m- or p-chlorine or m- or p-bromobenzoyl chloride as condensation components leads to red dyes. Possess all of these dyes good fastness properties.

Example 2 A mixture of 500 parts of nitrobenzene, 17.9 parts of 1-nitroanthraquinone-2-carboxylic acid and 24 parts of thionyl chloride is heated to 120 ° for 4 hours. Then the excess becomes Thionyl chloride is distilled off in vacuo and the reaction broth with 6.4 parts of 1,5-diamino-4-oxyanthraquinone (obtained according to example 1, paragraph 1). Then it is 12 hours on 160 'heated. After cooling, the resulting dye is sucked off and on first washed with nitrobenzene and then with methanol and the vacuum cleaner dried. The light red dye powder is in concentrated sulfuric acid insoluble and dyes the fiber from the red vat in strong red embroidered Bordo tones of good fastness properties.

Claims (1)

PATENT CLAIM: Process for the production of vat dyes, thereby characterized in that 1,5-di-acylamino-4-alkoxy-anthraquinone with sulfuric acid Treated above 10 room temperature and the resulting 1,5-diamino-4-oxy-anthraquinone with aromatic carboxylic acids of the general formula X-R-COOH (where R is a benzene or anthraquinone nucleus and X halogen or a nitro, amino or trifluoromethyl group means) or their functional derivatives condensed. Considered publications: German patent specification No. 665 598. When the application is published, there are two Coloring boards have been laid out.