DE637210C - Process for the production of indigoid dyes - Google Patents

Description

Process for making indigoid vat dyes In the patent 631 655 is the manufacture of asymmetrical indigoid vat dyes, among others. described from 5-alleoxy-6,7-dichloro-3-oxythionaphthenes.

It has now been found that you can also get valuable unbalanced Vat dyes are obtained when components are used to build them up of the above by replacing one of the two chlorine atoms with a methyl group differentiate.

According to the invention, 5-alkoxy-6-methyl-7-chloro-3-oxythionaphthenes are therefore used or 5-alkoxy-6-chloro-7-methyl-3-oxythionaphthenes or their reactive ones α-derivatives condensed with the components suitable for building indigoid dyes.

The dyes obtained in this way are distinguished by their valuable opaque properties Nuances and, especially in relation to the corresponding symmetrical dyes, characterized by a good affinity for the fiber.

In some cases, post-halogenation can cause their coloring Properties, depending on the choice of components, can still be improved. The production the 5-alkoxychloromethyl-3-oxythionaphthene can be used in a manner analogous to that of the components according to the main patent, e.g. B. starting from q.-alkoxychloromethylbenzene-r-sulfonic acids or sulfochlorides.

Example ra r-Methyl-2-methoxy-6-chlorobenzene is converted into the corresponding sulfochloride by treatment with chlorosulfonic acid. This is reduced to the mercaptan with zinc dust and the latter is condensed with monochloroacetic acid. The 2-chloro-3-methyl-4-methoxybenzene-r-thioglycolic acid obtained in this way, having a melting point of 1r2 °, is condensed after conversion into the corresponding acid chloride with aluminum chloride to give oxythionaphthene. The 5-methoxy-6-methyl-7-chloro-3-oxythionaphthene thus obtained melts after recrystallization from glacial acetic acid at 185 to z86 °. Example rb 1 7 kg of q.-methyl-6-chloro-2,3-diketodihydrothionaphthene-2- (p-dimethylaminoanil) are mixed with 12 kg of 5-methoxy-6-methyl-7-chloro-3-oxythionaphthene in glacial acetic acid - condensed. The resulting dye is filtered off with suction. It dissolves in -conc. "= Sulfuric acid with. green color and gives a yellow vat with diluted soda, lye and hydrosulphite. atis, which is dyed or printed on cotton in corinthian tones of good fastness.

The same dye is obtained when the p-dimethylaminoanil des 5-methoxy-6-methyl-7-chloro-2,3-diketodihydrothionaphthens with zl-methyl-6-chloro-oxythionaphthene is implemented.

If you use the instead of 4-methyl-6-chloro-oxythionaphthene 2; 3-N aphthoxythiophene, a muted navy blue with good fastness properties is obtained.

Example 2 2 kg of 2, i-naphthisatin is converted into chlorobenzene with 2.5 kg of phosphorus pentachloride produced the isatin chloride in the usual way. On that a solution of 2.3 kg of 5-methoxy - 6 - methyl-7-chloroxythionaphthene in chlorobenzene stirred in. After stirring for one hour, the precipitated dye is filtered off with suction. -It dissolves with brown color in conc. Sulfuric acid, - combined with yellow-brown Color and draws on the fiber 'with dark green color. The colorations are good Authenticity properties.

Example 3 i 1.5 kg of 5-methoxy-6-chloro-7-methyl-3-oxythionaphthene (obtained from 2-amino-3-methoxy-i-methylbenzene-6-sulfonic acid by exchanging the amino group against chlorine according to S a n d m e y e r, conversion to the corresponding sulphurous chloride, Reduction to Merkap-'änt condensation with monochloroacetic acid 'd ring closure of the 2-Methy l-3 "^ athlor-4-methoxybenzene-i-thioglycolic acid thus obtained, from m.p. 129 ') with 17 kg of 2, 1-naphthoxythiophene-p-dimethylaminoanil and zoo kg of glacial acetic acid heated to 120 ° for 2 hours with stirring. Of the. precipitated dye is filtered off with suction. -In conc: sulfuric acid, it dissolves with purple color, goes with orange color into the vat and dyes cotton from it in brown shades with very good fastness properties, especially excellent lightfastness.

If in the above example the 2, 1-naphthoxythiophene-p-dimethylaminoanil is replaced by 8-chloro-i, 2-naphthoxythiophene-p-dimethylaminoanil, a dye is obtained which provides gray tones with good fastness properties on cotton.

Claims (1)

PATEN TANS, PRÜC1IE: i. Modification of the process according to Patent 63,1655 for the production of indigoid vat dyes, characterized in that 5-alkoxy-3-oxythionaphthenes which contain chlorine and methyl in the 6- and 7-positions or their reactive α-derivatives are used to build indigoid dyes suitable components condensed. -2. Process for the production of indigoid vat dye, characterized in that the products obtained according to claim i are post-halogenated.