DE720853C - Process for the production of water-insoluble azo dyes - Google Patents

Description

Process for the production of water-insoluble azo dyes Es it has been found that water-insoluble azo dyes with very good fastness properties can be obtained if any diazo, diazoazo or tetrazo compounds with 2- (2 ', 3'-Oxynaphthoylamino) -3-alkoxydiphenylene oxides or their substitution products for itself or on a basis couples and thereby selects the components so that they have no solubilizing groups, for example sulfonic acid or carboxylic acid groups, contain.

If one puts the azo dyes obtainable by the present process like the ice colors on the fiber, strong colors are obtained from good ones Fastness properties, especially very good lightfastness. The dyes own also as pigment dyes of technical importance. For example, the result is 2- (2 ', 3'-Oxynaphthoylamino) - 3-methoxydiphenylenoxv d as a primer on cotton vivid colors with a whole range of diazo compounds as developers, those of 2- (2 ', 3'-oxynaphthoylamino) diphenylene oxide, in particular in terms of lightfastness obtainable by the method known from British Patent 374,548 Significantly outperform the colors. In addition, the 2- (2 ', 3'-Oxynaphthoylamino) -3-meth, -oxydiphenylene oxide is distinguished by coupling with the diazonium compound of 2 amino-4, 4-dichloro-i, i'-diphenyl ether very good dye obtainable on the fiber by the present process Lightfastness is characterized by an unusually clear yellowish-red shade, such as it has not yet been produced in this authenticity with the commercially available dyes could be.

The 2- (a ', 3'-oxynaphthoylamino) -3-alkoxydiphenylene oxides used as azo components or their substitution products can be obtained by the process of patent 718,348 will.

Examples i. 4234 g of 2- (2 ', 3'-oxynaphthoylamino) -3-methoxydiphenylene oxide are dissolved in 2.5 cc of alcohol and 0.38 cc of sodium hydroxide solution at 34 ° B6 and with 0.38 cc of 300 / o formaldehyde solution and 2.5 cc. ccm glue solution i: io offset.

This mixture is mixed with 10 cc of 50% turkish grist oil and 10 cc of sodium hydroxide solution adjusted from 34 'Be and water to i 1 solution.

The arylamide pulls boiled cotton yarn from this bath to about 70 ° 1o and after treatment with a developing solution, prepared by diazotizing 3.4g of 2-amino-4, 4-dichloro-i, i'-diphenyl ether is, and then rinsing and soaking at the boil a strong unusually clear yellowish red of very good lightfastness.

2. One of 25.4 parts by weight of 2-amino-4, 4-dichloro-i, i'-diphenyl ether A conventionally prepared solution of the diazonium compound is allowed to pour into an aqueous solution Suspension of 38.3 parts by weight of 2- (2 ', 3'-oxynaphthoylamino) -3-methoxydiphenylene oxide, by dissolving this arylamide in alcoholic Caustic soda, Dilute with water and neutralize with acetic acid. The filtered off after the coupling, washed neutral and dried Dye is a red powder.

Dyes with similar fastness properties are obtained if the arylamide used in the examples is replaced by appropriate substitution products. Instead of the diazo compounds mentioned in the examples, other diazo, tetrazo or diazoazo compounds can be used. The following list describes a number of other components that can be used according to the present process, as well as the properties of the azo dyes that can be prepared from them: Diazo component Azole component 1 shade i-Amino-2-methyl-4-bromo-5-chloro-2- (2 ', 3'-Oxynaphthoylamino) - 3 - lively bluish cast- benzene methoxydiphenylene oxide red i - amino -: z - methyl - 3, 5 - dichloro like yellow-red benzene i .Amino-2-methyl-5-chlorobenzene similarly. Vivid yellowish red i-Amino-2-methyl-4-clilorbenzene similarly lively blue, tichig- Red i-Amino-4-methyl-6-nitrobenzene like boron red i. Amino-2-methyl-4-nitrobenzene like lively boron red i Amino-2-methyl-5-nitrobenzene desgl, scarlet red i-Amino-2, 5-dichlorobenzene like. Scarlet red i Amino-2-nitrobenzene similarly yellow-brown 4-Amino-5-methoxy-2, 4'-dimethyl- like dark purple 2'-nitro-i, i'-azobenzene 4., 4'-diamino-5-methoxy-2-methyl-like violet-black i, i'-azobenzene i Amino-2-methyl-4-chlorobenzene 2 - (2 ', 3'oxynaphthoylamino) = 3 - scarlet agile ethoxydiphenylene oxide i-Amino-2, 5-dichlorobenzene like yellowish scarlet Red i-Amino-2-metlioxy-4-nitrobenzene like boron red i Amino-2, 4-dimethylbenzene 2 - (2 ', 3'- Oxynaphthoylaminö) - 7 - lively bluish tinge- methyl-3-methoxydiphenylene oxide red i-Amino-2-ynethyl-4-chlorobenzene 2- (2 ', 3'-Oxynaphthoylamino) -3, 7-bororo red dimethoxydiphenylene oxide i Amino-2-methoxy-5-elilobenzene adesgl. Bordo red i Amino-2-nitro-4-methylbenzene - the same as boron red i Amino-2-nitro-4-chlorobenzene like boron red i-Amino-2-methoxy-4-nitrobenzene like boron red i-Amino-3-chlorobenzene, like brown, red i Amino-2, 5-dichlorobenzene 2 - (2 ', 3'oxynaphthoylamino) - 7 - brick chloro-3-methoxydiphenylene oxide 2-Amino-4, 4'-dichloro-i, i'-di- like yellow-red phenyl ether i-Amino-2-ethylsulfoyl-5-trifluor- like yellow-brown ' methylbenzene

Claims (1)

PATENT CLAIM: Process for the production of water-insoluble azo dyes, characterized in that any diazo, diazoazo or tetrazo compounds with 2- (2 ', 3'-oxynaphthoylamino) -3-allcoxydiphenylene oxides or their substitution products for itself or on a basis couples and thereby selects the components so that they do not contain any solubilizing groups.