DE644535C - Process for the production of water-insoluble azo dyes - Google Patents

Description

Process for the production of water-insoluble azo dyes Es it was found that valuable water-insoluble azo dyes can be obtained, if one uses the aryl amides of 5, 6, 7, 8-tetrahydro-2-oxynaphthalene-3-carboxylic acid, which do not contain sulfonic acid amide groups, in substance or on a substrate combined with diazo compounds and thereby components without solubilizing groups chooses.

If the dyes are produced on the fiber in the manner of ice colors, in this way, brown shades with good fastness properties are generally obtained.

The arylamides used in the process are, for. B. available through Condensation of 5, 6, 7, 8-tetrahydro-2-oxynaphthalene-3-carboxylic acid with primary Mono- or diamines of the isocyclic or heterocyclic series are known per se Way. y Prior to known processes after which using deep brown ice paints of 5-oxy-2-chloro-i-methylbenzene-4th-carboxylic acid arylidene or 4-oxy-2-chloro-i-methylbenzene-5-carboxylic acid arylidene are produced, the new process has the technical progress that the azo components have a greater coupling energy.

Example i Well-boiled and dried cotton yarn is treated with a solution of 2.59 , 4, q .'- di- (5 ", 6", 7 ", 8" -tetrahydro-2 "-oxvnaphthalin-3" -carboylamino) - 3,3'-dimetlioxydiphenyl, 10 ccm sodium hydroxide solution of 34 ° Be and 10 ccm Turkish red oil impregnated 5% per liter, thoroughly wound and, without drying, in a diazo solution truncated with sodium acetate, the 2 g i-amino-3-nitrobenzene im Liter contains, developed, rinsed and soaped. You get a nice and real brown.

The same azo component gives with dianotated i-amino-2-methoxy-d.-nitrobenzene a dark brown, with dianotized i-amino-2-methyl-q.-chlorobenzene a brown and with dianotized 2-amino-1.-chloro-i, i'-diphenyl ether a strong, reddish-tinged one Brown.

Example 2 20 g of i- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxynapiithalin-3'-carboylamino) -naphthalene with 2o ccm Turkish red oil 5% and 2o ccm caustic soda of 38 ° Be well made into a paste, dissolved by pouring hot water over it and adjusted to i 1 with cold water.

Cotton thread is impregnated with this solution, squeezed off and dried. a) Part of the product impregnated in this way is developed in a diazo solution containing iig dianotated i-amino-2-methyl-.l-nitrobenzene, 9 cc of glacial acetic acid and 20 g of \ atrium acetate per liter. Then it is rinsed and soaped at the boil. A purple-tinged black-brown is obtained.

b) The other part of the impregnated cotton fabric is finitely printed with the following drink = color: 15g i-Amino-2-nietlioxv-4-ilitrobenzene iver- 'the finite 25 ccill warm U'assei and 70 g \ atriuninitrite made into a paste. The paste obtained is slowly added to a mixture of 25o cc of cold water and 26 cc of 32 percent hydrochloric acid. After 1 hour, the mixture is blunted with 15 g of atrium acetate dissolved in 30 cell water, and then 10 cc of acetic acid is added to a level of 5%. The resulting solution is stirred into 500 g starch = tragacanth thickening and adjusted to 1 kg with cold water.

The print is dried, then in a bath containing 2 ccni of sodium hydroxide solution of 38 ° Be and 2 ccm of water glass per liter, treated with boiling, rinsed, boiling soaped, rinsed again and dried. A brownish black is obtained. Example 3 Cotton fabric is printed with a printing ink which is as follows Was produced:: @ 6.5 g of the diazoamino compound from diazotized i-amino-2-chloro-4-benzoylamino -. @ `-methoxybenzene and i-methylaminobenzene-2-carboxylic acid-5-sulfonic acid and 3.19 i - (5 ', 6', 7 ', 8'-tetrahydro-2'-oxynaphthalene-3'-carboylamino) -2-ethoxybenzene are with a mixture of 3 ccm spirit, 3 ccm. Caustic soda of 38 ° Be and 15 ccm of water made into a paste, slightly warmed and in 50 g of neutral starch-tragacanth thickening stirred in, dissolved and adjusted to 100 g with water.

The print is dried in acetic acid-formic acid vapor for 5 minutes steamed, rinsed, soaped at the boil, rinsed again and dried. You get an extensive, yellowish brown.

The following table lists some of the azofax materials produced on cotton in accordance with the process and the color shades obtained. Azo component Diazo component Color shade i- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxy- naphthalene-3'-carboylamino) - -2-methoxybenzene i-amino-2-chloro-4-benzoylamino-yellow-brown 5-methoxybenzene like. i-Amino-2-methoxy-4-nitrobenzene black-green Like. 4-amino-3, 2'-dimethyl-i, i'-azo-black-brown benzene -4-nietliotybenzene i amino-2-chloro-4-benzoylamino yellow-brown 5-methoxybenzene like. Amino-3, 2'-diethyl-i, i'-azo-black-brown benzene -2-ätlioxyi) enzol i Amino-4-nitronaphthalene yellowish dark- Brown Like. i-Amino-2, 5-dimethoxy-4-nitro-red-brown benzene -2-methyl-4-methoxybenzene 4- amino-2, 4'-dimethyl-5-meth- black brown oxy-2'-nitro-i, i'-azobenzene Like. 4 - Amino - 2, 3'- dimethyl - i, i'- dark brown azobenzene -2-niethvlbenzol i Amino-2-methoxy-4-nitro-5- red sticky black- methvlbenzene brown Like. i-Amino-4-nitronaphthalene brown-black -2, 5-dimethoxybenzene i-amino-2-methoxy-4-nitrobenzene red sticky black- Brown -2-methyl-5-chlorobenzene like greenish black Like. i Amino-2-methoxy-4-nitro-5 black-gray methylbenzene -2, 5-dimethylbenzene i amino-2-methoxy-4-nitrobenzene greenish black Like. i Amino-2, 5-dimethoxy-4-nitro-violet tinged Benzene black Azo component diazo component - shade 4- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxy-2-amino-4-chloro-i, i'-diphenyl ether red-brown naphthalene -3 '- carboylamino) - di- phenyl " i- (5 ', 6', 7 ', 8'-Tetrahydro-2'-oxy-2-amino-4-chloro-i, i'-diphenyl ether red-brown naphthalene-3'-carboylamino) - naphthalene Like. i-Amino-2-methoxybenzene-5-sulfone deep bordo acid diethylamide like. i-Aminoanthraquinone violet-tinged dark Brown 2- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxy-i-amino-2-methyl-4-chlorobenzene red-brown naphthalene-3'-carboylamino) - naphthalene Like. 4-Amino-4'-methoxy-i, i'-diphenyl-red-brown amine Like. i-Amino-2,5-diethoxy-4-benzoyl black-violet aminobenzene Like. i-Aminoanthraquinone violet brown i- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxy-i-amino-3-nitrobenzene brown naphthalene-3'-carboylamino) - naphthalene Like. i-Amino-2-nitro-4-methoxybenzene reddish brown 4,4'-di- (5 ", 6", 7 ", 8" -Tetrahydro- 2 "-oxynaphthalene-3" -carboyl- amino) - -3, 3'-dimethoxydiphenyl i-aminocarbazole brown Like 2- (4'-aminophenyl) -5-methylbenzo- dark brown thiazole like. i-Amino-2-chloro-4-benzoylamino-5 yellow-brown methoxybenzene -3, 3'-dimethyldiphenyl 2-amino-i, i'-diphenylsulfone reddish brown Like. 4-Amino-3-methoxy-i, i'-diphenyl-yellowish brown amine -diphenyl 2-amino-4, 4'-dichloro-i, i'-diphenyl- orange brown ether Like. 2-Amino-4,5-dichloro-i, i'-diphenyl-reddish brown ether 2- (5 ', 6', 7 ', 8'-tetrahydro-2'-oxy-i-amino-2-chloro-4-benzoylamino-5-yellow brown naphthalene-3'-carboylamino) dimethoxybenzene phenylene oxide

Claims (1)

PATENT CLAIM Process for the production of water-insoluble azo dyes, characterized in that the aryl amides of 5, 6, 7, 8-tetrahydro-2-oxynaphthatin-3-carboxylic acid, which do not contain sulfonic acid amide groups, with diazo compounds in substance or combined on a substrate and thereby components without water-soluble groups chooses.