Disperse azo dyes
View Patent ↗The present invention relates to disperse azo dyes of formula wherein R 1 is bromo, nitro, cyano, methyl, methoxy or trifluoromethyl; R 2 is hydrogen, chloro, bromo or trifluoromethyl; R 3 is hydrogen, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano; and R 4 is methyl, ethyl, n-propyl, 2-methoxyethyl, methoxycarbonylmethyl or 2-methoxycarbonylethyl; with the proviso that R 1 is cyano in case R 2 denotes chloro or bromo, to a process for the preparation of such dyes and to their use in the dyeing or printing of semi-synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials.
1. A dye of formula
wherein R 1 is methyl, methoxy or trifluoromethyl;
R 2 is hydrogen, chloro, or trifluoromethyl;
R 3 is hydrogen, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano; and
R 4 is 2-methoxyethyl, methoxycarbonylmethyl or 2-methoxycarbonylethyl.
2. The dye of formula (1) according to claim 1 , wherein R 1 is methyl.
3. The dye of formula (1) according to claim 1 , wherein R 2 is chloro.
4. The dye of formula (1) according to claim 1 , wherein R 3 is hydrogen.
5. A process for the preparation of the dye of formula (1) according to claim 1 , which comprises diazotising a compound of formula
and coupling the diazonium compound so obtained to a coupling component of formula
wherein R 1 , R 2 , R 3 and R 4 have the meanings given for formula (1) in claim 1 .
6. A dye mixture comprising at least one dye of formula (1) according to claim 1 and at least one further dye selected from the group consisting of C.I. Disperse Blue 60, C.I. Disperse Blue 79:1, C.I. Disperse Blue 72:2, C.I. Disperse Blue 148, C.I. Disperse Blue 149, C.I. Disperse Blue 165, C.I. Disperse Blue 165:1, C.I. Disperse Blue 207, C.I. Disperse Blue 284, C.I. Disperse Blue 295, C.I. Disperse Blue 316, C.I. Disperse Blue 337, C.I. Disperse Blue 354, C.I. Disperse Blue 366, C.I. Disperse Blue 367, C.I. Disperse Blue 368, C.I. Disperse Blue 376, C.I. Disperse Blue 378, C.I. Disperse Blue 380, C.I. Disperse Green 9, C.I. Disperse Violet 107, a compound of the formula
wherein R 1 is ethyl, R 5 is hydrogen, R 5 is acetylamino, R 7 is ethyl, 2-methoxyethyl, n-propyl, n-butyl, 2-cyanoethyl, 1-methoxycarbonylethyl, 1-methoxycarbonylmethyl, allyl, 2-methoxycarbonylethyl, hydrogen, 2-cyanoethyl, benzyl or n-butyl and
wherein when R 7 is ethyl, R 8 is methyl, ethyl, n-propyl, n-butyl, benzyl, 2-methoxyethyl, 2-cyanoethyl, 2-phenylethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-acetoxyethyl, 2-hydroxy-3-phenoxypropyl, 2-ethoxycarbonylethyl, 2-hydroxy-3-isopropoxypropyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 4-nitrobenzyl,4-methoxybenzyl, 3-methoxybenzyl, 3-phenoxypropyl or 4-acetoxybutyl and
wherein when R 7 is 2-methoxyethyl, R 8 is 2-methoxyethyl or benzyl and
wherein when R 7 is n-propyl, R 8 is n-propyl and
wherein when R 7 is n-butyl, R 8 is n-butyl and
wherein when R 7 is 2-cyanoethyl, R 8 is benzyl or 2-methoxycarbonylethyl and
wherein when R 7 is 1-methoxycarbonylethyl, R 8 is 1-methoxycarbonylmethyl and
wherein when R 7 is methoxycarbonylmethyl, R 8 is methoxycarbonylmethyl and
wherein when R 7 is allyl, R 8 is allyl and
wherein when R 7 is 2-methoxycarbonylethyl, R 8 is 2-ethoxycarbonylethyl or 2-methoxycarbonylethyl and
wherein when R 7 is hydrogen, R 8 is 1-methoxycarbonylethyl and
wherein when R 7 is 2-cyanoethyl, R 8 is 2-methoxycarbonylethyl and
wherein when R 7 is benzyl, R 8 is 2-methoxycarbonylethyl and
wherein when R 7 is n-butyl, R 8 is n-butyl or benzyl,
the compounds of formulas (101)-(106)
and the compounds of formulas II-2, II-3, II-4
7. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material which comprises applying to or incorporating into the hydrophobic fibre material at least one dye of formula (1) according to claim 1 or the dye mixture according to claim 6 .
8. A process according to claim 7 , wherein the hydrophobic fibre material contains polyester fibres.
9. A material dyed or printed according to claim 7 .