GB824443A - Improvements in or relating to water-insoluble azo dyestuffs containing urea or urethane groups - Google Patents

Abstract

Dyestuffs of formula <FORM:0824443/IV(c)/1> where m is 1 or 2, x is H, Hlg, Me, Et, MeO or EtO, y is H, Hlg, Me, Et, CF3, MeO, EtO or an alkanoylamino radicle of not more than 18 C atoms, R1 an alkylene radicle of 1-4 C atoms, R2 an alkylene radicle of 2-4 C atoms, Z an oxygen or imino group, R3 a cycloaliphatic or aromatic radicle which may contain substituents other than water-solubilizing groups, or when Z is O also an aliphatic radicle, V an oxygen or imino group when Z is imino, or imino only when Z is O, M is H, Hlg, MeO, EtO, CHF2, CF3, CN or carbalkoxy or -ZCO-V-R3 where R3, Z and V are as above and m is 1, or a simple linkage when m is 2 and R4 a mononuclear aromatic, mono- or di-nuclear heterocyclic radicle containing substituents but not water-solubilizing groups. Preferred are dyestuffs of formulae <FORM:0824443/IV(c)/2> where y is H, Cl, Me, CF3 or the above alkanoylamino radicle, w is H or Me, R5 is Et, C2H4CN, C2H3F2 or C2H2F3, R3 is phenyl or ethyl and R4 is as above containing Cl, No2, CF3 or SO2Me substituents. The dystuffs are made by acid coupling appropriate diazo compounds with the required amines of formula <FORM:0824443/IV(c)/3> Indicated as diazo compounds are anilines and amino-thiophenes, -thiazoles, -thiodiazoles and -benzothiazoles containing halogen atoms or nitro, acyl, cyano and/or alkylsulphonyl groups. The dyestuffs may be mixed with such compounds as wetting, dispersing and emulsifying agents and Glauber's salt. The dyestuffs dye cellulose triacetate and secondary cellulose acetate and some of them also dye wool, silk, cellulose ester, polyamide, polyvinyl and terephthalic acid ester fibres. Some may be used as pigments, e.g. in oils, lacquers and synthetic resins. Fibres are given yellow-orange to violet shades. In examples dyestuffs are made and dyeing processes described values of x, y, m, M, z v and the R's being chosen from those listed above, the diazo compounds used being 4-nitro-and - methylsulphonyl - 2 - chloro -, 4 - nitro-2 - cyano -, - methylsulphonyl -, - fluorosulphonyl - and - trifluoromethyl -, 4 - nitro - and - methylsulphonyl - and 2,4 - bis - methylsulphonyl - 1 - aminobenzenes, 5 - nitro - thiazole, 6 - nitro - and 5 - methylsulphonyl - benzthiazole - 2 and 3 - nitro - 5 - acetyl - thiophene, the alkanoylamino groups being acetyl-, chloracetyl -, trifluoracetyl -, propyl -, butyryl-, decanoyl -, hexadecanoyl - and octa decanoyl-amino-groups, R1 is CH2, C2H4, C3H6 and C4H8, R2 is C2H4 and C3H6, R3 is methyl, ethyl, propyl, butyl, cyclohexyl, phenyl and 41-methyl-, -isopropyl, -methoxy- and 21 : 41-dimethyl-phenyl.