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US 4,670,486 AGranted
Polymer composition pigmented with copper or nickel complexes of ligands containing a semicarbazone moiety
AssigneeCiba-Geigy Corporation
InventorsGeorg Cseh, Paul Lienhard
Life of this patent
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Abstract
High molecular weight organic material is effectively colored by the incorporation therein of a copper or nickel complex of the ligand compound of formula I ##STR1## wherein A is an isocyclic or heterocyclic aromatic moiety, R is H, halogen, lower alkyl or alkoxy, R.sub.1 is H, lower alkyl, phenyl or substituted phenyl, and B is H, lower alkyl, ureido or substituted ureido, guanidino, anilino, benzamido or a heterocyclic aromatic moiety.
Claims8
A process for coloring high molecular weight organic material which comprises
- incorporating in the organic material an effective amount of a transition metal complex of the ligand compound of formula I or mixtures thereof ##STR63## in which A is substituted or unsubstituted phenyl, biphenyl, naphthyl or anthraquinonyl;
- or A is a heterocyclic aromatic radical derived from
- 5-aminobenzimidazolone, 5-amino-1-methylbenzimidazolone, 5-amino-1-n-butylbenzimidazolone, 5-amino-1-phenylbenzimidazolone, 5-amino-1-p-chlorophenylbenzimidazolone, 5-amino-1-p-methylphenylbenzimidazolone, 5-amino-1-p-methoxyphenylbenzimidazolone, 5-amino-6-chlorobenzimidazolone, 5-amino-6-bromobenzimidazolone, 5-amino-6-methylbenzimidazolone, 5-amino-6-methoxybenzimidazolone, 6-aminobenzoxazolone, 5-aminobenzoxazolone, 5-amino-7-chlorobenzoxazolone, 6-amino-5-chlorobenzoxazolone, 6-amino-5-methylbenzoxazolone, 6-amino-5-chlorobenzothiazolone, 6-amino-5-methylbenzothiazolone, 6-aminoquinazol-4-one, 6-amino-2-methylquinazol-4-one, 6-amino-2-methoxyquinazol-4-one, 6-amino-7-chloro-2-methylquinazol-4-one, 7-aminoquinazol-4-one, 2-(4'-aminophenyl)-quinazol-4-one, 2-(3'-aminophenyl)-quinazol-4-one, 2-(4'-amino-3'-methoxyphenyl)-quinazol-4-one, 2-(4'-amino-3-chlorophenyl)-quinazol-4-one, 2-(3'-amino-4'-methylphenyl)-quinazol-4-one, 6-amino-2,4-dihydroxyquinazoline, 7-aminophenmorphol-3-one, 6-aminophenmorphol-3-one, 7-amino-6-chlorophenmorphol-3-one, 7-amino-6-methylphenmorphol-3-one, 7-amino-6-methoxyphenmorphol-3-one, 6-aminoquinol-2-one, 6-amino-4-methylquinol-2-one, 7-amino-4-methylquinol-2-one, 7-amino-4,6-dimethylquinol-2-one, 6-amino-7-chloro-4-methylquinol-2-one, 7-amino-4-methyl-6-methoxyquinol-2-one, 6-amino-1,3-dihydroxyisoquinoline, 6-amino-2,4-dihydroxyquinoline, 6-amino-2,3-dihydroxyquinoxaline or 4-aminophthalimide, R is --H, halogen, C.sub.1 -C.sub.4 --alkyl or C.sub.1 -C.sub.4 --alkoxy, R.sub.1 is --H, C.sub.1 -C.sub.4 --alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, --CONH.sub.2, CONHR.sub.2 or C.sub.2 -C.sub.5 --N--alkylcarbamoyl, and B is --H, C.sub.1 -C.sub.4 --alkyl, --NHCONH.sub.2, --NHCONH--C.sub.1 -C.sub.4 --alkyl, --NHCONHR.sub.2, --NHCSNH.sub.2, --NHCSR.sub.3, --NHC(NH)NH.sub.2, --NHR.sub.2, --NHCOR.sub.3, --NHSO.sub.2 R3, or a heterocyclic aromatic radical derived from 5-aminobenzimidazolone, 5-amino-1-methylbenzimidazolone, 5-amino-1-n-butylbenzimidazolone, 5-amino-1-phenylbenzimidazolone, 5-amino-1-p-chlorophenylbenzimidazolone, 5-amino-1-p-methylphenylbenzimidazolone, 5-amino-1-p-methoxyphenylbenzimidazolone, 5-amino-6-chlorobenzimidazolone, 5-amino-6-bromobenzimidazolone, 5-amino-6-methylbenzimidazolone, 5-amino-6-methoxybenzimidazolone, 6-aminobenzoxazolone, 5-aminobenzoxazolone, 5-amino-7-chlorobenzoxazolone, 6-amino-5-chlorobenzoxazolone, 6-amino-5-methylbenzoxazolone, 6-amino-5-chlorobenzothiazolone, 6-amino-5-methylbenzothiazolone, 6-aminoquinazol-4-one, 6-amino-2-methylquinazol-4-one, 6-amino-2-methoxyquinazol-4-one, 6-amino-7-chloro-2-methylquinazol-4-one, 7-aminoquinazol-4-one, 2-(4'-aminophenyl)-quinazol-4-one, 2-(3'-aminophenyl)-quinazol-4-one, 2-(4'-amino-3'-methoxyphenyl)-quinazol-4-one, 2-(4'-amino-3'-chlorophenyl)-quinazol-4-one, 2-(3'-amino-4'-methylphenyl)-quinazol-4-one, 6-amino-2,4-dihydroxyquinazoline, 7-aminophenmorphol-3-one, 6-aminophenmorphol-3-one, 7-amino-6-chlorophenmorphol-3-one, 7-amino-6-methylphenmorphol-3-one, 7-amino-6-methoxyphenmorphol-3-one, 6-aminoquinol-2-one, 6-amino-4-methylquinol-2-one, 7-amino-4-methylquinol-2-one, 7-amino-4,6-dimethylquinol-2-one, 6-amino-7-chloro-4-methylquinol-2-one, 7-amino-4-methyl-6-methoxyquinol-2-one, 6-amino-1,3-dihydroxyisoquinoline, 6-amino-2,4-dihydroxyquinoline, 6-amino-2,3-dihydroxyquinoxaline or 4-aminophthalimide, R.sub.2 being phenyl which is unsubstituted or substituted by halogen, --CF.sub.3, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, --CN, --CONH.sub.2, --SO.sub.2 NH.sub.2, --CONHC.sub.1 -C.sub.4 --alkyl, --CONHC.sub.6 H.sub.5, C.sub.2 -C.sub.5 --alkoxycarbonyl, phenoxycarbonyl, C.sub.2 -C.sub.5 --N--alkylcarbamoyl, --NHCOC.sub.6 H.sub.5 or --SO.sub.2 NHC.sub.1 -C.sub.4 --alkyl or --SO.sub.2 NHC.sub.6 H.sub.5 and R.sub.3 being phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, C.sub.2 -C.sub.5 --N--alkylcarbamoyl or --NHCOC.sub.6 H.sub.5 or being a heterocyclic aromatic radical derived from furan-2-carboxylic acid, thiophene-2-carboxylic acid, pyrrole-2-carboxylic acid, pyridine-2-, -3- and -4-carboxylic acid, pyrazinecarboxylic acid, indole-2-carboxylic acid or quinoline-4-carboxylic acid, and the transition metal is a doubly positively charged metal ion of copper or nickel.
A colored composition which comprises
- (a) a high molecular weight organic material, and
- (b) an effective amount of a transition metal complex of the ligand compound of formula I or mixtures thereof ##STR65## in which A is substituted or unsubstituted phenyl, biphenyl, naphthyl or anthraquinonyl;
- or A is a heterocyclic aromatic radical derived from
- 5-aminobenzimidazolone, 5-amino-1-methylbenzimidazolone, 5-amino-1-n-butylbenzimidazolone, 5-amino-1-phenylbenzimidazolone, 5-amino-1-p-chlorophenylbenzimidazolone, 5-amino-1-p-methylphenylbenzimidazolone, 5-amino-1-p-methoxyphenylbenzimidazolone, 5-amino-6-chlorobenzimidazolone, 5-amino-6-bromobenzimidazolone, 5-amino-6-methylbenzimidazolone, 5-amino-6-methoxybenzimidazolone, 6-aminobenzoxazolone, 5-aminobenzoxazolone, 5-amino-7-chlorobenzoxazolone, 6-amino-5-chlorobenzoxazolone, 6-amino-5-methylbenzoxazolone, 6-amino-5-chlorobenzothiazolone, 6-amino-5-methylbenzothiazolone, 6-aminoquinazol-4-one, 6-amino-2-methylquinazol-4-one, 6-amino-2-methylquinazol-4-one, 6-amino-7-chloro-2-methylquinazol-4-one, 7-aminoquinazol-4-one, 2-(4'-aminophenyl)-quinazol-4-one, 2-(3'-aminophenyl)-quinazol-4-one, 2-(4'-amino-3'-methoxyphenyl)-quinazol-4-one, 2-(4'-amino-3'-chlorophenyl)-quinazol-4-one, 2-(3'-amino-4'-methylphenyl)-quinazol-4-one, 6-amino-2,4-dihydroxyquinazoline, 7-aminophenmorphol-3-one, 6-aminophenmorphol-3-one, 7-amino-6-chlorophenmorphol-3-one, 7-amino-6-methylphenmorphol-3-one, 7-amino-6-methoxyphenmorphol-3-one, 6-aminoquinol-2-one, 6-amino-4-methylquinol-2-one, 7-amino-4-methylquinol-2-one, 7-amino-4,6-dimethylquinol-2-one, 6-amino-7-chloro-4-methylquinol-2-one, 7-amino-4-methyl-6-methoxyquinol-2-one, 6-amino-1,3-dihydroxyisoquinoline, 6-amino-2,4-dihydroxyquinoline, 6-amino-2,3-dihydroxyquinoxaline or 4-aminophthalimide, R is --H, halogen, C.sub.1 -C.sub.4 --alkyl or C.sub.1 -C.sub.4 --alkoxy, R.sub.1 is --H, C.sub.1 -C.sub.4 --alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, --CONH.sub.2, CONHR.sub.2 or C.sub.2 -C.sub.5 --N--alkylcarbamoyl, and B is --H, C.sub.1 -C.sub.4 --alkyl, --NHCONH.sub.2, --NHCONH--C.sub.1 -C.sub.4 --alkyl, --NHCONHR.sub.2, --NHCSNH.sub.2, --NHCSR.sub.3, --NHC(NH)NH.sub.2, --NHR.sub.2, --NHCOR.sub.3, --NHSO.sub.2 R3, or a heterocyclic aromatic radical derived from 5-aminobenzimidazolone, 5-amino-1-methylbenzimidazolone, 5-amino-1-n-butylbenzimidazolone, 5-amino-1-phenylbenzimidazolone, 5-amino-1-p-chlorophenylbenzimidazolone, 5-amino-1-p-methylphenylbenzimidazolone, 5-amino-1-p-methoxyphenylbenzimidazolone, 5-amino-6-chlorobenzimidazolone, 5-amino-6-bromobenzimidazolone, 5-amino-6-methylbenzimidazolone, 5-amino-6-methoxybenzimidazolone, 6-aminobenzoxazolone, 5-aminobenzoxazolone, 5-amino-7-chlorobenzoxazolone, 6-amino-5-chlorobenzoxazolone, 6-amino-5-methylbenzoxazolone, 6-amino-5-chlorobenzothiazolone, 6-amino-5-methylbenzothiazolone, 6-aminoquinazol-4-one, 6-amino-2-methylquinazol-4-one, 6-amino-2-methoxyquinazol-4-one, 6-amino-7-chloro-2-methylquinazol-4-one, 7-aminoquinazol-4-one, 2-(4'-aminophenyl)-quinazol-4-one, 2-(3'-aminophenyl)-quinazol-4-one, 2-(4'-amino-3'-methoxyphenyl)-quinazol-4-one, 2-(4'-amino-3'-chlorophenyl)-quinazol-4-one, 2-(3'-amino-4'-methylphenyl)-quinazol-4-one, 6-amino-2,4-dihydroxyquinazoline, 7-aminophenmorphol-3-one, 6-aminophenmorphol-3-one, 7-amino-6-chlorophenmorphol-3-one, 7-amino-6-methylphenmorphol-3-one, 7-amino-6-methoxyphenmorphol-3-one, 6-aminoquinol-2-one, 6-amino-4-methylquinol-2-one, 7-amino-4-methylquinol-2-one, 7-amino-4,6-dimethylquinol-2-one, 6-amino-7-chloro-4-methylquinol-2-one, 7-amino-4-methyl-6-methoxyquinol-2-one, 6-amino-1,3-dihydroxyisoquinoline, 6-amino-2,4-dihydroxyquinoline, 6-amino-2,3-dihydroxyquinoxaline or 4-aminophthalimide, R.sub.2 being phenyl which is unsubstituted or substituted by halogen, --CF.sub.3, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, --CN, --CONH.sub.2, --SO.sub.2 NH.sub.2, --CONHC.sub.1 -C.sub.4 --alkyl, --CONHC.sub.6 H.sub.5, C.sub.2 -C.sub.5 --alkoxycarbonyl, phenoxycarbonyl, C.sub.2 -C.sub.5 --N--alkylcarbamoyl, --NHCOC.sub.6 H.sub.5 or --SO.sub.2 NHC.sub.1 -C.sub.4 --alkyl or --SO.sub.2 NHC.sub.6 H.sub.5 and R.sub.3 being phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 --alkyl, C.sub.1 -C.sub.4 --alkoxy, --NO.sub.2, C.sub.2 -C.sub.5 --N--alkylcarbamoyl or --NHCOC.sub.6 H.sub.5 or being a heterocyclic aromatic radical derived from furan-2-carboxylic acid, thiophene-2-carboxylic acid, pyrrole-2-carboxylic acid, pyridine-2-, -3- and -4-carboxylic acid, pyrazinecarboxylic acid, indole-2-carboxylic acid or quinoline-4-carboxylic acid, and the transition metal is a doubly positively charged ion of copper or nickel.
1 more element
Dependencies are inferred from the claim text.