DE1028714B - Process for the production of water-insoluble azo dyes - Google Patents

Description

Process for the preparation of water-insoluble azo dyes It has been found that valuable water-insoluble azo dyes are obtained if the diazo compounds are prepared from amines of the general formula wherein X is an optionally substituted aminophenyl radical and Y is an aryl radical, couples with arylamides of aromatic or heterocyclic o-oxycarboxylic acids in substance or on a basis and the components are selected so that they do not contain any water-solubilizing groups such as sulfonic acid or carboxylic acid groups.

On the vegetable fiber can be made up of the mentioned components produce valuable dyes according to the known dyeing process, which are good Overall fastness is often characterized by good superoxide fastness.

Acetyl cellulose, polyamide or polyurethane fibers can be obtained likewise valuable dyeings with good fastness properties.

The dyes can and can also be produced in substance in the paint industry and printing ink technology as well as for coloring high molecular weight plastic masses are used.

The production of the diazo components used, partly in the literature not yet described derivatives of 1,3,4-triazole can according to known processes take place, for example by reacting the mononitro-N, N'-diacylhydrazines available diimide chlorides with arylamines and subsequent reduction of the after this process obtained nitro compounds to the amino compounds.

Compared to the water-insoluble known from German patent specification 933 581 Monoazo dye from dianotated 1-phenyl-S- (2'-aminophenyl) -1,2,3,4-tetrazole and 1- (2 ', 3'-Oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene are characterized according to the invention available water-insoluble monoazo dyes of analogous composition by a better solvent fastness of the cotton dyeings.

Example 1 50 g of cotton yarn are used for 45 minutes at 30 ° C in the following Treated primer bath, spun off and colored wet in the developing bath at 20 ° C. Then it is rinsed, first 15 minutes at 60 ° C, then 15 minutes at 100 ° C soap and dried. Primer Bath 3.5 g of 1- (2 ', 3'-oxynaphthoylamino) naphthalene are used in 5 cc of denatured alcohol, 1.7 cc of sodium hydroxide solution at 38 ° B6, 1.7 cc of formaldehyde solution (33 ° / g) and 5 ccm of warm water and with water at 30 ° C, 3 g of a condensation product from higher molecular weight fatty acids and protein degradation products and 10 ccm caustic soda set from 38 ° B6 to 1 1.

Development bath 3.1 g of 1,2-diphenyl-5- (2'-aminophenyl) -1,3,4-triazole of the formula (obtainable by reacting the diimide chloride from N-benzoyl-N'-2-nitrobenzoylhydrazine with aniline and reducing the 1,2-diphenyl-5- (2'-nitrophenyl) -1,3,4-triazole obtained to the corresponding amino compound) are dissolved with 3 cc of hydrochloric acid at 20 ° B6 and 20 cc of water and, while cooling, a solution of 0.75 g of sodium nitrite in 4 cc of water is added. After the end of the dianotation, the mixture is adjusted to 1 liter with the addition of cold water and 1 g of an action product of ethylene oxide on oleyl alcohol.

plan receives a scarlet fever of good overall fastnesses, in particular of good superoxide fastness. Used in place of the above specified primer bath a bath, which in a corresponding manner by dissolving 2.5 g of 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene in 5 cc of denatured Alcohol, 1.75 ccm sodium hydroxide solution at 38 ° B6, 3.75 ccm formaldehyde solution (33%) and 2.5 cc of warm water and setting to 1 1 is obtained an orange with the same authenticity properties. Beispie12 50 g cotton yarn will be Treated for 45 minutes at 30 ° C in the subsequent primer bath, rubbed off and colored wet in a developing bath at 20 ° C. Then it is rinsed, initially for 15 minutes Soaped at 60 ° C, then 15 minutes at 100 ° C and dried.

Priming bath 4.5 g of 1- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chlorobenzene are dissolved in 13.5 cc of denatured alcohol, 1.5 cc of sodium hydroxide solution at 38 ° B6, 1.5 cc of formaldehyde solution (33 ° / oig) and 4.5 ccm of warm water and adjusted with water at 30 ° C, 3 g of a condensation product of higher molecular weight fatty acids and protein degradation products and 10 ccm of sodium hydroxide solution from 38 ° B6 to 1 liter. Development bath 3.8 g. 1,2-Diphenyl-5- (2'-amino-4'-trifluoromethylphenyl) -1,3,4-triazole of the formula are dissolved with 3 cc of hydrochloric acid of 20 'B6 and 20 cc of water and, while cooling, a solution of 0.75 g of sodium nitrite in 4 cc of water is added. After the end of the diazotization, the mixture is adjusted to 1 liter with the addition of cold water and 1 g of an action product of ethylene oxide on oleyl alcohol.

An orange with good overall fastness properties is obtained, in particular good superoxide fastness. Example 3 Acetate rayon is in the liquor ratio treated from 1:30 60 minutes in a bath containing 0.5 g of 1- (2 ', 3'-oxynaphthoylamino) -3-nitrobenzene per liter and 0.6 g of 1,2-diphenyl-5- (2'-aminophenyl) -1,3,4-triazole, dissolved in 2 cc of a mixture from equal parts diglycol and monoethanolamine and 0.3 ccm sodium hydroxide solution at 38 ° B6, contains and with 10 g of sodium chloride, 3 g of a condensation product of higher molecular weight Fatty acids and protein degradation products and 1 cc of 25% ammonia solution are charged is.

It is rinsed briefly and diazotized at 10 to 15 ° C. with 1 g of sodium nitrite and 5 cc hydrochloric acid at 20 ° B6 per liter of liquor. Then at 60 ° C with 2 g sodium acetate per liter of water treated, soaped and rinsed.

An orange with good fastness properties is obtained.

The following table also contains a number of further components which can be used according to the invention and the color shades of the azo dyes obtainable therefrom, which likewise have good fastness properties Diazo component Azo component - I shade 1,2-diphenyl-5- (2'-aminophenyl) -1,3,4-triazole 1- (2 ', 3'-oxynaphthoylamino) likewise -2,4-dimethoxy-5-chlorobenzene scarlet fever also -2-methoxy-5-chlorobenzene yellowish Scarlet fever the same. -2-methoxybenzene reddish orange desgl. -2,5-dimethoxylbenzene desgl. likewise 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) -2-meth- oxybenzene scarlet fever 1,2-diphenyl-5- (2'-amino-4'-trifluoromethyl-1- (2 ', 3'-oxynaphthoylamino) phenyl) -1,3,4-triazole -2,5-dimethoxy-4-chlorobenzene orange desgl. -naphthalene desgl. the same. -2-methoxy-4-chloro-5-methylbenzene desgl. Likewise, -2-methyl-4-chlorobenzene scarlet fever likewise 2- (2 ', 3'-oxynaphthoylamino) -naphthalene orange 1,2-diphenyl-5- (3'-amino-4'-methylphenyl) - 1- (3'-oxydiphenylene oxide-2'-carboylamino) 1,3,4-triazole -2,5-dimethoxybenzene brown (Melting point 273 ° C) Diazo component Azo component I shade 1,2-diphenyl-5- (2'-amino-4'-methoxyphenyl) - 1- (2 ', 3'-oxynaphthoylamino) 1,3,4-triazole -4-ethoxybenzene bluish-tinted red (Melting point 296 to 297 ° C) same. -2-methyl-4-chlorobenzene desgl. the same. -4-methoxybenzene the same. 1,2-Diphenyl-5- (2'-amino-5'-chlorophenyl) -2-methoxy-4-chloro-5-methylbenzene Orange 1,3,4-triazole (Melting point 223 ° C) likewise -2,4-dimethoxy-5-chlorobenzene brownish red likewise -2-methoxy-5-chlorobenzene orange same. -2,5-dimethoxy-4-chlorobenzene desgl. likewise 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) -2-meth-bluish-tinted red oxybenzene 1,2-diphenyl-5- (3'-aminophenyl) -1,3,4-triazole 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-methoxybenzene scarlet fever (Melting point 291 to 294 ° C) 1,2-Diphenyl-5- (4'aminophenyl) -1,3,4-triazole, same red (Melting point 333 to 340 ° C) 2,3-Oxynaphthoylaminobenzene Full red likewise 1- (2'-oxycarbazole-3'-carboylamino) -4-chloro- benzene reddish brown 1,2-diphenyl-5- (3'-amino-4'-methoxyphenyl) - 1- (2 ', 3'-oxynaphthoylamino) 1,3,4-triazole -2,4-dimethoxy-5-chlorobenzene Full red Likewise, -2,5-dimethoxy-4-chlorobenzene, yellow-tinged red the same. 1- (3'-Oxydiphenylenoxyd-2'-carboylamino) -2,5-dimethoxybenzene greenish brown

Claims (1)

PATENT CLAIMS: Process for the preparation of water-insoluble azo dyes, characterized in that the diazo compounds are obtained from amines of the general formula where X is an optionally substituted aminophenyl radical and Y is an aryl radical, couples with arylamides of aromatic or heterocyclic o-oxycarboxylic acids in substance or on a basis and the components are chosen so that they do not contain any water-solubilizing groups, such as sulfonic acid or carboxylic acid groups. Considered publications German patent specification No. 933 581. When the application was published, a coloring table with an explanation was laid out.