Verfahren zur Herstellung neuer Monoazofarbstoffpigmente

摘要

The invention comprises monoazo dyestuff pigments of the formula wherein R1 represents a benzene residue containing a -NO2 group in ortho-position to the azo group, R2 represents a naphthalene residue in which the azo, hydroxy and -CONH-groups are in 1,2,3-position, R3 represents a benzene residue, R4 represents an aryl residue, R5 represents an aryl or alkyl residue, X represents a -CONH- or -SO2NH- group, Y represents a -CO- group or an -SO2- group and Z represents H or a group of the formula -X-R5. They may be obtained by (a) condensing an azo dyestuff monocarboxylic acid halide free from acidic groups imparting solubility in water of the-formula with a monoamine free from water-solubilizing groups of the formula or (b) condensing an azo dyestuff monocarboxylic acid halide free from acidic groups imparting solubility in water of the formula with an arylamine free from acidic groups imparting solubility in water; or (c) condensing an azo dyestuff free from acidic groups imparting solubility in water of the formula with an arylamine in a molar ratio of 1:2, or (d) coupling a diazo compound of an amine of the formula H2N-R1-Y-NH-R4 with a naphthol of the formula or (e) coupling a diazo compound of an amine of the formula H2N-R1-Y-NH-R4 with a naphthol of the formula wherein A represents the residue of an amine. Preferred dyestuffs are those of the formula wherein X1, X2 and X3 represent H or halogen atoms or alkyl, alkoxy, CF3, CN, or carboxylic acid ester groups, Z1 represents H or halogen atom or an alkoxy group, Y3 represents H or halogen atom or alkyl, alkoxy or alkanoylamino group, Y4 represents H or halogen atom or an alkoxy group, Z4 and Z5 represent H or halogen atoms or alkyl, alkoxy, phenoxy, -NO2, -CF3, -CN, -CONH2 or -COO ester groups and Z6 represents H or halogen atom or an alkyl or alkoxy group, a benzoylamino group or -CONH2 or -COO-ester group. Numerous examples are given for the production of the dyes. They may be used as pigments for spin-dyeing of filament and staple fibre viscose rayon, cellulose ethers and esters, polyamides, polyurethanes and polyesters and in the preparation of coloured lacquers and as lake formers. Intermediate dyestuffs of the formula may be obtained by coupling a diazo compound of an amine of the formula with a 2:3-hydroxynaphthoic acid of the formula and treating the azo-carboxylic acid obtained with phosphorus halides or thionyl chloride.