DE661811C - Process for the production of asymmetrical Kuepen dyes of the thioindigo series - Google Patents

Description

Process for the production of asymmetrical vat dyes Thioindigo series It has been found that industrially valuable asymmetrical vat dyes can be obtained the thioindigo series obtained when 7-alkoxy-3-oxythionaphthene, which in the 4- and 5-positions a halogen and an alkyl (or vice versa) or such Containing substituents in the 4-position alone, with 3-oxythionaphthenes or isatins the benzene series according to known methods to bisthionaphten- (2, 2 ') -indigos or -Thionaplithen- (2) -indole- (2 ') -indigos condensed and the products thus obtained optionally post-halogenated.

The dyes obtained in this way color the vegetable fiber in purple to blue tones of excellent authenticity. They differ from the ones before known symmetrical dyes which differ from substituted 7-alkoxy-3 - Derive oxythionaphthenes (patent z45 544), due to their more valuable hue and in many cases also through better lightfastness.

Example z 23 parts of 4-methyl-5-chloro-7-methoxy-3-oxythionaphthene and 36.5 parts of 4-methyl-5, 7-dichloro-2, 3-diketodihydrothionaphthen-2 (p-dimethylamino) -anil are boiled with 500 l of glacial acetic acid for 6 hours while stirring and refluxing. After cooling, the dye is suctioned off.

It represents a violet-blue powder, which blends with yellow color and strong, vivid violet dyeings and prints of very good quality on cotton Results in authenticity properties.

The same dye is obtained if a 2-anil of 4-methyl-5-chloro-7-methoxy-2, Reacts 3-diketodihydrothionaphthene with 4-methyl-5, 7-dichloro-3-oxythionaphthene: If the 4-methyl-5-chloro-7-methoxy-3-oxythionaphthene in the example above is replaced by the Replaced 4-methyl-7-methoxy-3-oxythionaphthene, a somewhat bluer one is obtained Dye of similar properties.

The above-mentioned oxythionaphthenic derivatives are obtained in the customary manner from the corresponding thioglycolic acids, which are represented as follows: r-methyl-2-chloro-4-methoxybenzene or i-methyl-4-methoxybenzene is obtained according to the method of German patent 55514o Subjected to the action of chlorosulfonic acid, the sulfonic chloride formed is converted into the corresponding mercapto compound by reduction and this is condensed with monochloroacetic acid. Example 2 2 parts of 5-bromoisatin are converted into the α-chloride with 23 parts of phosphorus pentachloride and 4.5o parts of chlorobenzene in the usual manner. convicted. This is condensed at about 80 to 90 ° with a solution of 23 parts of 4-methyl-5-chloro-7-methoxy-3-oxythionaphthene in 250 parts of chlorobenzene.

The obtained dye dissolves with a blue-green color in concentrated form Sulfuric acid .. It turns yellow in color. The fiber turns into full reddish blue Tones colored and printed.

If 4-methyl-5-chloro-.7-ethoxy-3-oxythionaphthene is used in place of the @ O-cythionaphthene mentioned, that's how you get one. Dye of very similar properties.

The following table shows the nuances of some other dyes in this series that contain 4-methyl-5-chloro-7-methoxy-3-oxythionaphthene as a component: 2. Nuance component 5-chloro-7-methyl-3-oxythionaphthene purple 4-methyl-6-chloro-3-oxythionaphthen reddish-tinged violetf 4,7-Dimethyl-5-chloro-3-oxythionaphthene violet 5, 7-dichloroisatin a-chloride blue 5, 7-dibroinisatin-a-chlorid blue 4-methyl-5-chloro-7-methoxyisatin-a-chloride greenish blue

Claims (1)

PATRNTANSPRU CI3: Process for the production of asymmetrical indigoid Dyes, characterized in that 7-alkoxy-3-oxythionaphthenes, which in the 4-position a halogen or alkyl or in the 4th and 5-position a halogen and contain an alkyl (or vice versa) with 3-oxythionaphthenes or isatins the benzene series according to known methods to bisthionaphthen- (2, 2 ') - indigos or Thionaphthen- (2) -indole- (2`) -indigos condensed and the products thus obtained optionally post-halogenated.