Patent GB-279146-A (GB)
Title: Manufacture of new azo-dyestuffs
IPC: C09B29/20
Filed: 1926-05-20
Abstract: 279,146. Imray, O. Y., (1. G. Farbenindustrie Akt.-Ges.). May 20, 1926. Samples furnished. Azo dyes; lakes; azo dyes, forming on the material; printing .-Azo dyes are made in substance, on the fibre, or on a substratum by coupling a 2 : 3-oxynaphthoic arylide with a diazotized amine of the general formula. where X represents hydrogen or a monovalent substituent, one Y represents an alkyl, aralkyl, or aryl sulphone or ketone group or a sulphonamide or carboxyamide, and the other Y represents halogen, alkyl, aryl, oxyalkyl, oxyaralkyl, oxyaryl, thioalkyl, thioaralkyl, or thioaryl; the use of alkylaryl-, and aralkyl-amides of alkyloxy-, aralkyloxy- and aryloxy-m-aminobenzoic acids, their homologues and substitution products, being excluded. When aminoarylaralkyl and aminodiaryl sulphones or ketones are used, another amino group may be present in the aralkyl or in the second aryl residue; both amino groups may then be diazotized and the tetrazo compounds thus obtained combined with two molecules of a 2 : 3-oxynaphthoic arylide, or with one molecule of a di-2 : 3-oxynaphthoyldiamine, or one molecule of one of the latter bodies may be coupled with two molecules of a diazotized monamine of the above general formula. In examples (1) 2-aminoanisol-4-phenylsulphone is diazotized and coupled with 2 : 3-oxynaphthoic-ophenetidide; the product forms a fiery red lake with the usual substrata: (2) yarn is padded with the a- or #-naphthalide and developed with diazotized 2-aminotolyl-4-phenylsulphone or 3-amino- 4-phenoxybenzophenone, fast bluish-red or winered shades being obtained: (3) cotton material is padded with the m-chloranilide and developed with tetrazotized 3 : 3<1>-diamino-4 : 4<1>-dimethoxydiphenylsulphone to give a claret shade; (4) 2- aminotoluene-4-sulpho-N-methylanilide is diazotized and coupled with the a-naphthalide; the product yields bluish-red lakes with the usual substrata; (5) yarn is impregnated with the 4- phenetidide and dyed a clear red shade by developing with diazotized 2-aminotoluene-4-sulpho- N-methylanilide; (6) 3<1>-amino-4<1>-methylbenzoyl- 2-chloraniline is diazotized and coupled with 2 3-oxynaphthoic anilide; the product gives bluish-red lakes with the usual substrata; (7) yarn impregnated with the #-naphthalide or the 4- chlor-2-anisidide is developed with diazotized 4<1>- chlor - 3<1> - aminobenzoylaniline; yellowish - red shades are obtained. The same shades are obtained if the dyestuffs are formed on the fibre by the usual printing processes. A table gives the shades obtained on cotton from the following components :-2-aminotolyl-4-ethylsulphone and the 5-chlor-2-anisidide; 2-aminotolyl-4-benzylsulphone and the anilide, 5-chlor-2-toluidide, 3- nitranilide and #-naphthalide; 3-amino-4-chlordiphenylsulphone and the #-naphthalide, 3- nitranilide. 3-toluidide, and 2-phenetidide; 3- amino-4-ethoxydiphenylsulphone and the 5-chlor- 2-toluidide, 2-anisidide, 5-chlor-2-anisidide, and phenetidide; 2-aminotolyl-4-phenylsulphone and the 4-toluidide, 2-anisidide, 4-chlor-2-anisidide, and the dianisidide; 3-amino-4-methoxyacetophenone and the 5-chlor-2-toluidide; 3-amino-4- methoxybenzophenone and the 4-chloranilide and 5-chlor-2-anisidide; 3-amino-4-phenoxybenzophenone and the #-naphthalide; 3 : 3<1>-diamino-4 : 4'- ditolylketone and two molecular proportions of the anilide, #-naphthalide, 4-toluidide, 4-chloranilide, and 3-phenetidide; 2-aminotoluene-4- sulphodimethylamide and the 4-chlor-2-anisidide, 2-phenetidide, a- and #-naphthalide : 2-aminophenetol-4-sulplnodimethylamide and the 4-chlor- 2-anisidide a- and #-naphthalide ; 2-aminotoluene- 4-sulpho-N-methylanilide and the 3-toluidide, 4- chloranilide, 5-chlor-2-toluidide and 5-chlor-2- anisidide ; 3<1>-amino-4<1>-methylbenzoyl-3-toluidine and the 2-toluidide, 3-anisidide, 2-phenetidide, a- and #-naphthalide ; 3<1>-amino-4<1>-methylbenzoyl- 2-chloraniline and the 2-chloranilide. 2-anisidide, a- and #-naphthalide; 3<1>-amino-4<1>-methylbenzoyl- 4-chlor-2-toluidine and the 2-chloranilide, 3-toluidide, 4-toluidide, a- and #-naphthalide, 3-methoxy-2-naphthalide. and dianisidide; 3'-amino-41- methylbenzoyl-2 5-dichloraniline and the anilide, 4-anisidide, and a-naphthalide; 3<1>-amino-4<1>- methylbenzoyl-2-anisidine and the 3-chloranilide, 3-nitranilide, 2-anisidide. and #-naphthalide ; 3<1>- amino-4<1>-methhylbenzoyl-5-chlor-2-anisidine and the 3-anisidide. 4-chlor-2-anisidide, 5-chlor-2- anisidide, 2 : 5-dimethoxyanilide, a- and #-naphthalide, and dianisidide; 3<1>-amino-4<1>-methylbenzoyl-4-phenetidine and the 2-toluidide, 2-anisidide, 4-chlor-2-anisidide, 2-phenetidide and #- naphthalide; 3<1>-amino-4<1>-methylbenzoyl-aminohydroquinone dimethylether and the a-napthalide and dianisidide; 3<1>-amino-4<1>-methylbenzoyl-2- aminophenylether and the #-naphthalide; 3<1>- amino-4<1>-methylbenzoyl-a-naphthylamine and the anilide. 2-toluidide. 3-nitranilide. 2-anisidide, 2-phenetidide, 2 : 5-dimethoxyanilide, and anaphthalide; 3<1>-amino-4<1>-methylbenzoyl-#-naphthylamine, and the 4-chloranilide. 5-chlor-2-toluidide: 3-anisidide, 4-anisidide, 4-chlor-2-anisidide, 3 and 4-phenetidide ; bis-(3<1>-amino-4<1>-methylbenzoyl)-dianisidine and two molecular proportions of the 4-anisidide, #-naphthalide, and 3- methoxy.2-naphthalide; and bis-(3<1>-amino-4<1>- methylbenzoyl)-o-tolidine and two molecular proportions of the 5-chlor-2-toluidide, 2-phenetidide, a- and #-naphthalide. Specifications 6379/12; and 17279/13. [Class 15 (ii), Dyeing, Processes &c. for], are referred to. Aminoarylsulphonamides. - The above aminoarylsulphonamides are in general made by the action of nitroarylsulphochlorides on primary or secondary amines, followed by reduction of the nitro group. 2-Aminophenetol-4-sulphodimethylamide is made bv converting 3-nitro-4-chlorphenylsulphochloride into 2-nitrochlorphenyl-4- sulphodimethylamide, replacing the chlorine atom by the ethoxy group, and reducing the nitro group. Aminoarylcarboxyamides. - The above aminoarylcarboxyamides mav be made by the action of nitroarylcarboxylic chlorides with primary and secondary amines, followed by reduction of the nitro group. 2-Aminoanisol (or phenetol)-4-phenyl sulphone is made by converting 4-chlor-3-nitrophenylsulphochloride, into 4-chlor-3-nitrodiphenylsulphon, replacing the chlorine atom in the latter compound by a, methoxy or ethoxy group, and reducing the nitro group in the product. 3-Amino-4-methoxy-(or phenoxy)-benzophenone is made from 4-chlor-3.nitrobenzophenone by replacing the chlorine atom by the methoxy or phenoxy group and reducing the nitro group. 2-Aminotolyl-4-ethyl-(or benzyl)-sulphone is made by treating 2-nitrotoluene-4-sulphinic acid with p-toluenesulphonic. ethyl ester (for the ethyl compound) or with benzyl chloride, followed by reduction of the nitro group. The 2-nitrotoluene- 4-sulphinic acid is obtained by reduction of the corresponding sulphochloride- 3-Amino-4-chlordiphenylsulphone is made bv condensing 3-nitro-4-chlorphenyl-sulphochloride with benzene, followed by reduction of the nitro group. 3-Amino-4-methoxyacetophenoneis made by reducing the corresponding nitro compound.