DE630788C - Process for the production of Kuepen dyes of the anthraquinone acridone series - Google Patents

Description

Process for the preparation of vat dyes of the anthraquinone acridone series It has been found that valuable new vat dyes of the anthraquinone acridone series which are distinguished by great fastness and color strength are obtained if anthraquinonylaminoanthraquinone acridones of the general formula are obtained in which A1 is an optionally substituted anthraquinone radical with a free 4-position, A2 is an optionally substituted anthraquinone radical with a free 2'-position and B is an optionally substituted aromatic radical, treated with acidic condensing agents. The said anthraquinonylaminoanthraquinone acridones, which are themselves already a dye, are obtained, for. B. by condensation of 3-haloanthraquinone acridones with a free q-position with a-aminoanthraquinones which are not substituted in the o-position to the a-amino group.

Suitable acidic condensing agents are, for. B. anhydrous aluminum chloride, expediently with the addition of suitable diluents, such as table salt, or against Aluminum chloride inert organic liquids, e.g. B. nitrobenzene or trichlorobenzene, is used, as well as concentrated sulfuric acid and chlorosulfonic acid.

Such anthraquinonylaminoanthraquinone acridones can be found particularly easily condense of the type mentioned, in which the A. component is in an a-position is substituted by an acylamino radical. In this case it is generally sufficient already the action of concentrated sulfuric acid to the condensation mostly to effect even at room temperature. During this process sulfur dioxide is evolved; However, here too, gentle heating can accelerate the condensation.

Processes for the production of vat dyes are already known, in which acridone derivatives of a, a'-dianthrimides with acidic condensing agents be treated. The vat dyes available in this way produce olive-brown ones on the fiber to brownish-black colorations. In the case of the present processes, on the other hand, acridone derivatives are used used by a, a'-dianthrimides. The treatment of this Ties vat dyes obtainable with acidic condensing agents give colorations that not only in the color tones are essentially different from the colorations that one advises with the known dyes. but also through much better :; distinguish their coloring properties in comparison with the starting materials.

Example 1 To i 5 parts of the condensation of 3-bromoanthraquinone acridone - Anthraquinonylaminoanthraquinone acridones available with a-Aminoan @ hrachinon, suspended in 300 parts of anhydrous nitrobenzene, are stirred at 100 ° 10 parts of anhydrous aluminum chloride are given. One then gradually warms up @ 14o ° and keeps the temperature at 14o to 15o ° for about 3 hours. After that, that will Nitrobenzene removed by steam distillation, the resulting dye in deposited in the usual way, dried and concentrated by reprecipitation Sulfuric acid brought into a fine distribution suitable for dyeing. The received The dye dissolves in concentrated sulfuric acid with a purple color and delivers brown dyeing on cotton, while the starting product is concentrated Sulfuric acid shows a greenish-blue solution color and red-violet on cotton Dye supplies.

EXAMPLE 2 18 parts of 3-chloroanthraquinone acridone are heated to boiling with 20 parts of i-amino-5-benzoylaminoanthraquinone in 24o parts of boiling nitrobenzene until the evolution of hydrochloric acid has ceased. After cooling, the precipitated reaction product is filtered off with suction and washed with nitrobenzene, then with benzene and finally with ligroin. Its constitution corresponds to the formula There is a blue solution with concentrated sulfuric acid and is separated from it in burgundy flakes when diluted with water and produces dull red-violet tones from a corinth-brown vat on cotton.

io parts of the condensation product obtained in accordance with paragraph i dissolved in 100 parts of sulfuric acid monohydrate at room temperature with stirring. As soon as no more sulfur dioxide is developed, the solution is added to water, whereupon the dye separated out in brown flakes is sucked off and neutral is washed. He delivers strong, pure brown from a yellow-brown vat on cotton . Colorations.

Example 3 18 parts of 3-chloroanthraquinone acridone are mixed with 20 parts i-Amino-4-benzoylaminoanthraquinebn in the manner indicated in Example 2, paragraph i implemented. The condensation product obtained is added with concentrated sulfuric acid a brown solution, from which it deposited in purple flakes when diluted with water and supplies dull violet dyeings from a corinth-colored vat on cotton.

io parts' of the condensation product obtained in accordance with paragraph i in 10 parts of sulfuric acid monohydrate for 2 hours with stirring at 30 ° to 40 ° heated, whereupon in the manner indicated in Example 2 paragraph: 2 is worked up. A reaction product is obtained which, with concentrated sulfuric acid, turns brownish-carmine-red There is a solution from which it precipitates in red-brown flakes when diluted with water, and delivers strong red-brown colorations from an orange-red-brown vat on cotton.

Example .4 43 parts of the z. B. 3 # 4 '# 6'-Trichloranthraquinone-2 # # 2' - (N) -benzolacridones obtainable according to the details of Example 2 of Patent Specification 582169 are about 15 with 35 parts of i-amino-5-benzoylaminoanthraquinone in 600 parts of nitrobenzene Heated to the boil for hours. After cooling, the compound which has separated out is filtered off with suction and washed with nitrobenzene, benzene, ligroin. It corresponds to the formula dissolves in concentrated sulfuric acid with a green-blue color, precipitates from the sulfuric acid solution in red-violet flakes when diluted with water and dyes cotton from the vat in pale bluish-red tones.

100 parts of the compound obtained become about 100 parts of sulfuric acid monohydrate solved and treated according to the information given in the second paragraph of example e. The dye obtained dyes cotton in strong yellow-brown shades.

The analogous to the information in the first sentence from 3 # 3'- 5'-trichloroanthraquinone-2 # i- (N) -i '# 2' - (N) -benzolacridone (obtainable by reacting i # 3-dichloroanthraquinone-2-carboxylic acid with 2 # 4-dichloroaniline and subsequent acridone ring closure) and i-amino-5-benzoylaminoanthraquinone obtainable compound supplies in the treatment with sulfuric acid monohydrate accordingly the information given in example 2 paragraph: 2 a dye that is on cotton also gives yellow-brown colorations.

Claims (1)

PATENT CLAIM: Process for the production of vat dyes of the anthraquinone acridone series, characterized in that one anthraquinonylaminoanthraquinone acridones of the general formula in which A1 is an optionally substituted anthraquinone radical with a free q.-position, A2 is an optionally substituted analachinone radical with a free z'-position and B is an optionally substituted aromatic radical, treated with acidic condensing agents.