Disperse dyes of the general formula (I) where D is a diazo component derived from a substituted or unsubstituted aromatic amine, K is an aromatic radical of the formula and the substituents are each as defined in the first claim. Further described are the preparation and the use of the dyes according to the invention.
1. A disperse dye of formula (Ia)
where
D 1 is 3-phenyl-1,2,4-thiadiazolyl or conforms to one of the following formulae:
where
(a) is hydrogen, chlorine, bromine, cyano, nitro-, C 1-4 -alkoxycarbonyl or C 1-3 -alkyl-sulphonyl,
(b) is chlorine, bromine, nitro, methyl, C 1-2 -alkylsulphonyl, C 1-4 -alkylcarbonyl, aminosulphonyl, mono- or di-C 1-4 -alkylaminosulphonyl, phenylaminosulphonyl, C 1-4 -alkoxycarbonyl, benzyloxycarbonyl, tetrahydrofurfuryl-2-oxycarbonyl, C 3-4 -alkenyloxycarbonyl, C 3-4 -alkynyloxycarbonyl, aminocarbonyl, mono- or di-C 1-4 -alkylaminocarbonyl, phenylaminocarbonyl or phenylazo,
(c) is hydrogen or chlorine or when (d) is hydrogen, (c) is hydroxyl or rhodan,
(d) is hydrogen, chlorine, bromine, hydroxyl or cyano,
(e) is nitro, C 1-4 -alkylcarbonyl, C 1-4 -alkoxycarbonyl, cyano, aminocarbonyl, or mono- or di-C 1-4 -alkylaminocarbonyl,
(f) is hydrogen, chlorine, bromine, C 1-2 -alkyl or phenyl,
(g) is nitro, cyano, formyl, dicyanovinyl or a group of the formula —CH═CH—NO 2 , —CH═C(CN)CO—OC 1-4 -alkyl, H 5 C 6 —N═N—or 3- or 4-NO 2 —C 6 H 4 —N═N—,
(h) is cyano or C 1-4 -alkoxycarbonyl,
(i) is C 1-4 -alkyl or phenyl,
(j) is —CN, —CH═CH2 or phenyl,
(k) is C 1-4 -alkyl,
(l) is hydrogen, chlorine, bromine, cyano, rhodan, nitro, C 1-4 -alkoxycarbonyl or di-C 1-4 -alkylaminosulphonyl,
(p) is hydrogen, chlorine or bromine, and
(q) is C 1-4 -alkyl or C 1-4 -alkoxycarbonyl-C 1-4 -alkyl,
wherein the phenyl nuclei of these substituents optionally have one or two substituents selected from the group consisting of chlorine, bromine, methyl and C 1-2 -alkoxy,
R′ 1 is hydrogen, methyl, chlorine or acylamino,
R′ 2 is hydrogen, chlorine, C 1-2 -alkoxy, C 1-2 -alkoxyethoxy or combines with R 3 to form a group of the formula —CH(CH 3 )CH 2 C(CH 3 ) 2 —,
R 3 is hydrogen, C 1-6 -alkyl, C 3-4 -alkenyl, chloro- or bromo-C 3-4 -alkenyl, phenyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-4 -alkenyloxycarbonyl-C 1-3 -alkyl, C 3-4 -alkynyloxycarbonyl-C 1-3 -alkyl, phenoxy -C 2-4 -alkyl, halogen-, cyano-, C 1-4 -alkoxy-, C 1-4 -alkylcarbonyloxy- or C 1-4 -alkoxycarbonyloxy-substituted C 2-4 -alkyl, or a group of the formula —CH 2 —CH(R 8 )CH 2 —R 9 ,
wherein
R 8 is hydroxyl or C 1-4 -alkylcarbonyloxy,
R 9 is chlorine, C 1-4 -alkoxy, phenoxy, allyloxy or C 1-4 -alkylcarbonyloxy,
R 5 is phenyl optionally substituted by one or two substituents selected from the group consisting of methyl, chlorine, bromine and nitro or combines with R 4 to form a c-pentanone or c-hexanone ring, wherein R 4 is hydrogen or C 1-2 -alkyl, and
Y is a group of the formula —CH 2 CH 2 — or —CH 2 CH(CH 3 )—.
2. A disperse dye according of formula (Ib)
where
D 2 is the residue of a diazo component of the formula 2,6-dicyano-4-chloro-, 2,6-dicyano-4-bromo-, 2,6-dicyano-4-methyl- or 2,6-dicyano-4-nitrophenyl, 2,4-dinitro-6-chloro-, 2,4-dinitro-6-bromo- or 2,4-dinitro-6-cyanophenyl, 2-chloro-4-nitro-6-cyanophenyl, 2-bromo-4-nitro-6-cyanophenyl, 2,4-dinitrophenyl, 2,6-dichloro-4-nitrophenyl, 2,6-dibromo-4-nitrophenyl, 2-chloro-4-nitro-6-bromophenyl, 2-chloro-4-nitrophenyl, 2-cyano-4-nitrophenyl, 2,4-dinitro-5,6-dichlorophenyl, 2,5-dichloro-4-nitrophenyl, 4-nitro-phenyl, 4-phenylazophenyl, 4-C 1-4 -alkoxycarbonylphenyl, 2-C 1-4 -alkoxy-carbonyl-4-nitrophenyl, 4-benzyloxycarbonylphenyl, 4-(tetrahydrofurfuryl-2′-oxycarbonyl)phenyl, 3,5-dicyano-4-chloro-thienyl-2, 3,5-dicyano-thienyl-2, 3-cyano-5-nitro-thienyl-2, 3-acetyl-5-nitro-thienyl-2, 3,5-dinitro-thienyl-2, 3-(C 1-4 -alkoxycarbonyl)-5-nitro-thienyl-2, 5-phenylazo-3-cyano-thienyl-2, 5-phenylazo-3-cyano-4-methyl-thienyl-2, 5-nitro-thiazolyl-2, 5-nitrobenzoiso-thiazolyl-3, 3-methyl-4-cyano-isothiazolyl -5, 3-phenyl-1,2,4-thiadiazolyl-2, 5-(C 1-2 -alkylmercapto)-1,3,4-thiadiazolyl -2, 3-(C 1-2 -alkoxycarbonylethyl-mercapto)-1,2,4-thiadiazolyl-5, 1-cyanomethyl-4,5-dicyano-imidazolyl-2, 6-nitrobenzothiazolyl-2, 5-nitrobenzothiazolyl-2, 6-rhodanbenzothiazolyl-2, 6-chlorobenzothiazolyl-2, (5),6,(7)-dichlorobenzothiazolyl-2, or of the formula
and B is oxygen or a group of the formula ═(CN) 2 , ═CH—NO 2 , ═(CN)—COOC 1-4 alkyl or ═(CN)—COOC 3-4 alkenyl
and the symbols R 3 , R 5 and Y are each as defined below, and
R′ 1 is hydrogen, methyl, chlorine or acylamino,
R′ 2 is hydrogen, chlorine, C 1-2 -alkoxy, C 1-2 -alkoxyethoxy or combines with R 3 to form a group of the formula —CH(CH 3 )CH 2 C(CH 3 ) 2 —,
R 3 is hydrogen, C 1-6 -alkyl, C 3-4 -alkenyl, chloro- or bromo-C 3-4 -alkynl, phenyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-4 -alkenyloxycarbonyl-C 1-3 -alkyl, C 3-4 -alkynyloxycarbonyl-C 1-3 -alkyl, phenoxy-C 2-4 -alkyl, halogen-, cyano-, C 1-4 -alkoxy-, C 1-4 -alkylcarbonyloxy- or C 1-4 -alkoxycarbonyloxy-substituted C 2-4 -alkyl, or a group of the formuula —CH 2 —CH(R 8 )CH 2 —R 9 , wherein
R 8 is hydroxyl or C 1-4 -alkylcarbonyloxy,
R 9 is chlorine, C 1-4 -alkoxy, phenoxy, allyloxy or C 1-4 -alkylcarbonyloxy,
Y is a group of the formula —CH 2 CH 2 —or —CH 2 (CH 3 )—and
R 5 is phenyl optionally substituted by one or two substituents selected from the group consisting of methyl, chlorine, bromine and nitro or combines with R 4 to form a c-pentanone or c-hexanone ring, wherein
R 4 is hydrogen or C 1-2 -alkyl.
3. A process for preparing a dye of the formula (Ia), according to claim 1 , comprising the step of coupling a diazotized amine of the formula (II)
D 1 -NH 2 (II)
with a compound of the formula (IIIa)
H—K—N(R 3 )—Y—C(O)—O—CH(R 4)—C(O)—R 5 , (IIIa)
wherein K is an aromatic radical of the formula K 1
and wherein
R 1 is hydrogen, methyl, chlorine or acylamino,
R 2 is hydrogen, chlorine, C 1-2 -alkoxy, C 1-2 alkoxyethoxy or combines with R 3 to form a group of the formula —CH(CH 3 )CH 2 C(CH 3 ) 2 —,
R 3 is hydrogen, C 1-6 -alkyl, C 3-4 -alkenyl, chloro- or bromo-C 3-4 -alkenyl, C 3-4 -alkynl, phenyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 3-4 -alkenyloxycarbonyl-C 1-3 -alkyl, C 3-4 -alkynyloxycarbonyl-C 1-3 -alkyl, phenoxy -C 2-4 -alkyl, halogen-, cyano-, C 1-4 -alkoxy-, C 1-4 -alkylcarbonloxy- or C 1-4 -alkoxycarbonyloxy-substituted C 2-4 -alkyl, or a group of the formula —CH 2 —CH(R 8 )CH 2 -R 9 ,
R 4 is hydrogen or C 1-2 alkyl-,
R 5 is phenyl optionally substituted by one or two substituents selected from the group consisting of methyl, chlorine, bromine and nitro or combines with R 4 to form a c-pentanone or c-hexanone ring.
4. A method for dyeing or printing or both a hydrophobic fibrous material comprising the step of contacting at least one dye according to claim 1 with the hydrophobic fibrous material.
5. A method for printing a hydrophobic fibrous material comprising the step of contacting at least one dye according to claim 1 with the hydrophobic fibrous material with an ink jet printing device or a hot melt ink jet printing device.
6. A composition comprising at least one dye according to claim 1 .
7. A fibrous material printed or dyed or both with at least one dye according to claim 1 .
8. A method according to claim 4 wherein the hydrophobic fibrous material is polyester, acetate, triacetate fiber or a mixture thereof.
9. A disperse dye according to claim 1 wherein (a) is hydrogen, chlorine, cyano or nitro.