GB579063A - Manufacture of tris-and tetra-kisazo dyestuffs yielding dyeings capable of being coppered - Google Patents

Abstract

Tris- and tetrakis-azo dyestuffs are made by coupling tetrazotised 4.41-diamino-3.31-dialkoxydiphenyl compounds, the alkoxy groups of which may be substituted, in suitable sequence with 1 mol. of an amino-mono- or dis-azo dyestuff, obtained by acid coupling of an o-carboxydiazonium compound of the benzene series (which may be further substituted) with 2 - amino - 5 - hydroxynaphthalene - 7 - sulphonic acid, and with 1 mol. of a coupling component containing a hydroxyl group, usual for the production of metallisable dyestuffs (which, if it belongs to the naphthalene series, may be substituted by one azo group, and which may be identical with the first coupling component, provided that the two coupling components together contain not more than two azo groups). The coupling may be effected in the presence of pyridine. The dyes are suitable for dyeing cellulose fibres or textile materials, e.g. of cotton or regenerated cellulose, and the dyeings may be after-treated with copper salts. In the examples, the following dyes are described: (1) dianisidine \sQ (alkaline) 2 mols. of the monoazo dye 2-aminobenzoic acid --> (acid) J-acid; the 2-aminobenzoic acid may be replaced by 5-nitro-, 4-methyl-, 3-chloro-, 3 : 6-dichloro-, 5-acetylamino- or 5-cyano-2-aminobenzoic acid or 2 - (41 - amino - 31 - carboxybenzenesulpho) aminobenzoic acid; (2) dianisidine or 4 : 41-diamino-3 : 31-dicarboxymethoxydiphenyl \sQ (alkaline) 2 mols. of the monoazo dye 4-chloro-2-aminobenzoic acid --> (acid) J-acid; (3) 2-aminobenzoic acid --> (acid) J-acid (alkaline) \sM dianisidine --> (alkaline) J-acid (acid) \sM 5-nitro-2-aminobenzoic acid; the 2-aminobenzoic acid may be replaced as in (1); (4) salicylic acid \sM dianisidine --> (alkaline) J-acid (acid) \sM 2-aminobenzoic acid or 4-chloro-, 4-methyl- or 5-acetylamino-2-aminobenzoic acid; (5) o- or m-cresotinic acid, salicylic acid or b -resorcylic acid \sM dianisidine --> (alkaline) J-acid (acid) \sM 5-nitro-2-aminobenzoic acid; (6) 5-nitro-2-aminobenzoic acid --> (acid) J-acid (alkaline) \sM dianisidine or 4 : 41-diamino-3 : 31-dicarboxymethoxydiphenyl --> 1-naphthol-2-carboxylic acid; (7) salicylic acid \sM dianisidine --> (alkaline) J-acid (acid) \sM 41-hydroxy-4-aminoazobenzene-3 : 31-dicarboxylic acid; (8) 4-chloro-2-aminobenzoic acid --> (acid) J-acid (alkaline) \sM dianisidine --> 1-naphthol-4-sulphonic acid; (9) 5-nitro-2-aminobenzoic acid or 41-hydroxy-4-aminoazobenzene-3 : 31-dicarboxylic acid --> (acid) J-acid (alkaline) \sM dianisidine --> 2-naphthol-6-sulphonic acid; (10) 2-aminobenzoic acid --> (acid) J-acid (alkaline) \sM dianisidine --> 1-amino-8-hydroxynaphthalene-2 : 4-disulphonic acid; (11) 2-(41-hydroxy-31-carboxyphenylamino) -5-hydroxynaphthalene - 7 - sulphonic acid \sM dianisidine --> (alkaline) J-acid (acid) \sM 5-nitro-2-aminobenzoic acid. Further similar combinations are specified in a table. Other components mentioned for coupling in acid solution with J-acid are 5-chloro-, 5-sulpho- and 3.5-dichloro-2-aminobenzoic acids, and for coupling with the tetrazo compound are b -naphthol, 2 : 8 - dihydroxynaphthalene - 6 - sulphonic acid, 1 - amino - 8 - hydroxynaphthalene - 4 - sulphonic acid, 1 - amino - 5 - hydroxynaphthalene - 7 - sulphonic acid, 2-amino-8-hydroxynaphthalene-6-sulphonic acid, 1-acetylamino-8-hydroxynaphthalene-2- or 4-sulphonic acid, 1-phenylamino-8-hydroxynaphthalene - 4 - sulphonic acid, 1 - benzoylamino - 8 - hydroxynaphthalene - 4 - sulphonic acid and H-acid. 5-Cyano-2-aminobenzoic acid is obtainable by diazotizing 5-amino-2-acetylaminobenzoic acid, treating the diazo compound with cuprous cyanide and saponifying the acetylamino group.