Azo dyes of formula (I) are new, in which R1 = -SR5, -COOR6 or opt. substd. phenyl; R2 = H, halogen, opt. substd. 1-8C alkyl, 1-8C alkoxy, phenoxy or 2-4 C alkanoylamino, R3 = H or opt. substd. 1-8 C alkyl, R4 = H, opt. substd. 1-8 C alkyl, halogen, -OH, 1-8 C alkoxy, phenoxy, -SO3H, -OSO3H or -S2O3H, X = a direct bond, -O- or -CHR7-, R5 = opt. substd. 1-8 C alkyl or opt. substd. benzyl, R6 = opt. substd. 1-8 C alkyl, R7 = H or opt. substd. 1-8 C alkyl, with the proviso that the cpd. contains at least one sulpho-, sulphato- or thiosulphato gp. Claimed cpds. (I) have X = -O- or -CHR7- where R7 = H or 1-4 C alkyl, exp. Me; R2 = H, 1-4 C alkyl, esp. Me, or 1-4 C alkoxy, esp. OMe; R3 = 1-4 C alkyl, esp. Me; R4 = H, 1-4 C alkyl, esp. Me, OH, -SO3H or -OSO3H; R1 = -SR5 where R5 = 1-4C alkyl which is opt. substd. by -SO3H, -S-(CH2)2-4-SO3H or -S-(CH2)2-3-H. Specifically claimed cpds. (I) have R1 = -SCH2CH2R8, R2 = H, Me or OMe, R3 = H or Me, R4 = -SO3H, -OSO3H or OH, R8 = H or -SO3H and X = -O- or a gp. of formula (i). USE/ADVANTAGE - e (I) are useful for dyeing and printing of fibres, yarns, fabrics and knitware made from OH- or N-contg. materials such as cellulose, silk and esp. wool and synthetic polyamides. (I) give level blue and red shades with good general fastness, esp. good light fastness, rub resistance and wet resistance.
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