DE614894C - Process for the preparation of water-insoluble monoazo dyes - Google Patents

Description

Process for the preparation of water-insoluble monoazo dyes It has been found that valuable azo dyes are obtained if the diazo compounds of the bases of the general formula are used wherein R1 is an alkyl radical, R2 is an identical or different alkyl radical, an aryl, aralkyl or hydroaromatic radical, with i- (2 ', 3'-oxynaphthoylamino) 2,5-dimethoxy-q.-chlorobenzene, wherein the diazo components should not contain any solubilizing groups, for example sulfonic acid or carboxyl groups. In this way, yellowish red tones are obtained which, in addition to being very lively, are characterized by very good fastness properties.

The dyes can be produced in bulk or on a base. Compared to the known from French patent 616 75 [, by coupling dianotized z-methyl-2-aminobenzeneq.-sulfonic acid amides with i- (2 ', 3'-oxynaphthoylam.ino) -2-methoxy-4- or -5- Azo dyes obtainable by chlorobenzene, the dyes obtainable by the present process have significantly better lightfastness. Furthermore, the present dyes stand out from those known from patents 520 241 and 552 282, using i- (2 ', 3'-oxynaphthoylamino) -;, 5-dimethoxy-4-chlorobenzene and -2, 4-dimethoxy- 5-chlorobenzene not only because of the higher weather resistance of the dyeings produced on the fiber, but also because of the significantly better fastness properties of the pigments, for example because of the better color fastness (oilyness) of the lacquers, and because of the lower bleeding of the dyes in white rubber.

Examples of dyeing processes 50 g of boiled cotton yarn are used in 35 to -40 ° C% hour primed, well drained by squeezing or spinning and dyed in the dye bath for 1/2 hour. The dye is rinsed well, soaped at the boil, rinsed and dried again.

i. a) -priming bath: 2.7 g of 1- (2, 3'-oxynaphthoylamino) -2, 5-dimethoxy-4-chlorobenzene are dissolved in 5.4 cc alcohol, 1.35 cc farmaldehyde solution 3%, 1.3 cc sodium hydroxide solution 34 ° Be and 2.7 cc of water dissolved and after 1 [2 hours poured into a mixture of 6 cc sodium hydroxide solution 34 ° C, 10 cc Turkish red oil i: 2, zoo cc water at 100 ° C and 750 cc water at 20 ° C one with water on i 1 a.

b) Dyebath: 2.14 g of 2-amino-i-methylbenzene-4-sulfonic acid dimethylamide are with 3.1 ccm hydrochloric acid 20 ° B6 and 8 ccm sodium nitrite solution i: io in the usual way Way diazotized. This is then blunted with about 72 cc of sodium acetate solution i: 5 on Congoneutrality; add 140 cc sodium chloride solution- i: 5 and fill with cold water to 1 1. A vivid, yellowish red of very is obtained good fastness to washing, chlorine and lye boiling and excellent fastness to light.

a) Primer bath: As in example i. b) Dyebath: 2.9 g of 2-amino-i-methylbenzene-4-sulfonic acid-N methylbenzylami @ d are converted into the diazo solution as in Example i.

The result is a lively, yellowish red, of very good washing, Chlorine, caustic fastness and excellent light fastness.

3. 10.7 g of 2-amino-i-methylbeneol-4-sulfonic acid dimethylamide become diazotized in the usual way. The diazo solution is then added to bond the excess hydrochloric acid with sodium acetate and stir it into a solution of 17.9 g of 1- (2, 3'-oxynaphthoylamino) -2, 5-dimethoxy-4-chlorobenzene in dilute sodium hydroxide solution a. The precipitated dye is filtered off, washed well and dried. It is a yellow-yellow powder. The one produced with it in a known manner Lacquers are oily and deliver lightfast red tones.

You can also use the coupling in the presence of a color lacquer suitable substrate. The dyes are vulcanizing and suitable therefore also used to color rubber.

The following table describes a number of further azo dyes which can be prepared according to the present invention. Diazo compound_ from 2-Amino- Coupled with shade i-methylbenzo1-.l-sulfonic acid diethylamide 1- (2 ', 3'-oxynaphthoylamino) -2, 5- scarlet fever dimethoxy-4-chlorobenzene dipropylamide and scarlet fever dibutylamide like scarlet fever diamylamide and scarlet fever hT-methylallylamide and scarlet fever N-methylpropylamide like scarlet fever T-methylisobutylamide like scarlet fever i N-ethylbenzylamide similarly vividly yellowish Red N-methylanilide the same yellowish red N-methyl-o-chloroanilide, the same yellowish red N-methyl-p-methoxybenzylamide similarly vividly yellowish _ Red N-methyl-o-chlorobenzylamide similarly vividly yellowish Red N-methyl-p-chlorobenzylamide similarly vividly yellowish Red N-methylcyclohexylamide I like scarlet fever

Claims (1)

PATENT CLAIM: A process for the preparation of water-insoluble monoazo dyes, consisting in that the diazo compounds of the bases of .der general formula wherein R1 is an alkyl radical, R2 is an identical or different alkyl radical, an aryl, aralkyl or hydroaromatic radical, with 1- (a ', 3'-oxynaphthoylamino) -a, 5-dimethoxy-4-chlorobenzene in substance or coupling on a basis, the; Diazo components should not contain any solubilizing groups.