DE664904C - Process for the preparation of dyes of the acridone series - Google Patents

Description

Procedure. for the preparation of dyes of the acridone series It has been found that valuable dyes of the acridone series are obtained if mono- or polysulfonic acids of compounds of the general structure are used in which R1 and R., hydrogen or identical or different alkyl, oxalkyl, aralkyl, cycloalhyl or aryl groups and which can also contain any other atoms or groups of atoms, converted into acridones by heating with sulfuric acid or treatment with chlorosulfonic acid. Particularly valuable dyes are obtained if one nucleus of the diphenylamine-o-carboxylic acid has a nitro group in the o- and p-position to the imino group, and the other in the p-position to the imino group has an amino or dialkylamino group. If the dyes in the amino groups contain odor-free hydrogen atoms, these can be replaced by alkyl groups by treatment with epichlorohydrin, butylene dioxide or other alkylating agents.

The new dyes are characterized by a very good leveling power on wool and leather and have very good lightfastness. Example i Man heats a mixture of 50 parts of 4'-dimethylamino-2, 4-dinitro-2'-sulfodiphenylamine-6-carboxylic acid (Obtained by reacting 3,5-dinitro-2-chlorobenzenecarboxylic acid with i-dimethylamino-4-aminobenzo1-3-sulfonic acid in weakly alkaline solution) and 40o parts of concentrated sulfuric acid for 2 hours long to about 100 °, whereby the initially yellow color of the solution changes to olive green. The solution is then poured onto ice, the resulting yellow precipitate is filtered off with suction, converts it into its ammonium salt with ammonia and dries it. The resulting Dye dyes wool in negro-brown shades of good lightfastness and leveled out very good. It has good coloring properties for leather.

Treating the 4'-amino-2, 4-dinitro-3'-sulfodiphenylamine-6-carboxylic acid (available from p-phenylenediamine monosulfonic acid and 3,5-dinitro-2-chlorobenzene-i-carboxylic acid) in the manner described in Example i with concentrated sulfuric acid one also uses a dye which gives reddish-tinged brown dyeings on wool is well leveled and lightfast.

Dissolve 18 parts of the dye thus obtained in water the solution with 9 parts of butylene dioxide and boil the mixture for a few hours, this is obtained after salting out, suctioning off and drying a dye, which is similar in color and properties to the one described in example i, but better is washable.

Example e 5 parts of q'-amino-5'-chloro'-3'-sulfo-3-nitrodiphenylamine-6-carboxylic acid are heated. in the manner described in Example i with concentrated sulfuric acid. At the Pouring the mixture on ice forms a yellow-brown precipitate, which is with Bordeaux red color dissolves in ammonia. It is deposited by salting out and colored Wool in brown-red tones and levels out very well.

Example 3 20 parts of 2, q.-Dinitro-3'-sulfodiphenylamine-6, 6'-dicarboxylic acid (available from 2-aminoq-sulfobenzene-i-carboxylic acid and 3, 5-dinitro-2-chlorobenzene-i-carboxylic acid in alkaline solution) contributes fnan to a mixture of 160 parts with cooling Chlorosulphonic acid and q.o parts of concentrated sulfuric acid gradually at - 5 ° a. The mixture is stirred for a further 12 hours and then poured onto ice. The resulting yellow precipitate is filtered off with suction and washed with inhalation solution and dried. The dye obtained in this way dyes wool in a very uniform, lightfast manner yellow tones.

Claims (1)

PATRNTANSPRUCI-I: 'Process for the preparation of dyes of the acridone series, characterized in that mono- or polysulfomic acids of compounds of the general structure where R1 and R2 denote hydrogen or identical or different alkyl, oxalkyl, aralkyl, cycloalkyl or aryl groups and which can also contain any further atoms or atomic groups; converted into acridones by heating with sulfuric acid or treatment with chlorosulfonic acid.