DE912843C - Process for the preparation of monoazo dyes - Google Patents

Description

Process for the preparation of monoazo dyes The subject of patent 767 109 is a process for the preparation of monoazo dyes, which is characterized in that diazo compounds of aromatic amines of the general formula are used Y where X is an aryl, aralkyl or cycloalkyl radical or an alkyl radical with fewer than 10 carbon atoms and Y is the radical of an aliphatic or cycloaliphatic carboxylic acid free of aromatic radicals and having at least 6 carbon atoms, where X and Y together should contain at least 1z carbon atoms and the benzene nucleus can be further substituted with pyrazolone sulfonic acids or peri-acylamino-oxynaphthalene-disulfonic acids of the formula wherein ZCO or SO, and R is an aliphatic or aromatic mononuclear hydrocarbon radical, combined.

It has now been found that similarly valuable dyes can be obtained if such derivatives of peri-acylaminooxynaphthalene disulfonic acids are used as azo components used in which in the above formula R is substituted by a halogen atom Means alkyl radical.

The dyes according to the invention are superior to analogous dyes known from French patent 821 965 in terms of lightfastness and analogous dyes known from German patent 639 253 in drawability from a neutral bath and in sweat and milled fastness of the dyeings produced therewith.

Example i 34.4 parts of i-amino-4-Nn-butyl-N-cyclohexylcapronylaminobenzene of the formula are diazotized. The diazo compound obtained is combined with 39.6 parts of i-chloroacetylamino-8-oxynaphthalene-4,6-disulfonic acid in a soda-alkaline solution.

After separation and drying, a red, water-soluble one is obtained Powder, the wool from neutral or acidic baths in a very real, lively bluish-tinted red color Tones colors.

Example 2 37.2 parts of i-amino-4-N-cyclohexyl-N-laurinylaminobenzene are diazotized. The diazo compound obtained is combined with 39.6 parts of i-chloroacetylamino-8-oxynaphthalene-4, 6-disulfonic acid in a soda-alkaline solution. The deposited, dried dye is a red powder, the wool from neutral or acid bath in very real, lively colors in red tones.

Dyes with similar properties are obtained when used as diazo components i amino-4-N-cyclohexyl-N-caprinylaminobenzene or i-amino-4-N-cyclohexyl-N-cyclohexy propionylaminobenzene can be used. Example 3 36.8 parts of r-amino-2-methyl-5-N -benzyl-N-caprinylaminobenzene become diazotized. The diazo compound is combined with 39.6 parts of i-chloroacetylamino-8-oxynaphthalene-4, 6-disulfonic acid in soda-alkaline solution.

After separation and drying, a red, water-soluble one is obtained Powder, the wool or silk from acidic or neutral baths in lively bluish-tinged reds Dyes shades of very good fullness, perspiration, seawater and light fastness.

If i-.ß-Chlorpropionylamino-8-oxynaphthalene-4 is used as the azo component, 6-disulfonic acid or i - bromoacetylamino - 8 - oxynaphthalene - 4, 6 - disulfonic acid, this gives dyes with similar properties. Used as an azo component i-chloroacetylamino-8-oxynaphthalene-3, 6-disulfonic acid, a dye is obtained which dyes' olle in even more bluish red tones.

Claims (1)

PATENT CLAIM: Modification of the process for the preparation of monoazo dyes according to patent 767 Zog, characterized in that diazo compounds from aromatic amines of the general formula wherein X is an aryl, aralkyl or cycloalkyl radical or an alkyl radical with fewer than 10 carbon atoms and Y is the radical of an aliphatic or cycloaliphatic carboxylic acid free of aromatic radicals and having at least 6 carbon atoms, where X and Y together should contain at least 12 carbon atoms and the Benzene nucleus can be further substituted, here combined with those peri-acylaminooxynaphthalene disulfonic acids in which the hydrocarbon portion of the acyl radical is a haloalkyl group.