Azo dye pigments containing 4-quinazolinone moieties

Claim 2

A pigmented organo macromolecular material comprising an organo macromolecular material and an azo pigment of the formula ##STR13## wherein D is the radical of an aromatic or hetero-aromatic amine which is free from sulphonic acid groups; m is the integer 1 or 2; n denotes 0, 1, 2, 3 or 4; R 1 is hydrogen or C 1 -C 4 alkyl; and R 2 is chlorine, bromine, Cl 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, trifluoromethyl, cyano, carboxamide, C 1 -C 4 -alkyl-carboxamide, phenylcarboxamide, C 1 -C 4 alkylphenylcarboxamide, C 1 -C 4 -alkoxyphenylcarboxamide, fluoro-,chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C 1 -C 4 -alkylbenzylcarboxamide, C 1 -C 4 -alkoxybenzylcarboxamide, fluoro-,chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C 1 -C 4 -alkylsulphonamide, phenylsulphonamide, C 1 -C 4 -alkylphenylsulphonamide, C 1 -C 4 -alkoxyphenylsulphonamide, fluoro-,chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C 1 -C 4 - alkylbenzylsulphonamide, C 1 -C 4 -akloxybenzylsulphonamide, fluoro-, chloro-, bromo-benzyl sulphonamide, nitrobenzylsulphonamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 -alkoxybenzoylamino, nitrobenzoylamino, phenylamino, C 1 -C 4 -alkylphenylamino, C 1 -C 4 -alkoxyphenylamino, fluoro-, chloro-, bromo-phenylamino, or nitrophenylamino.

Claim 3

A pigmented organo macromolecular material according to claim 1, wherein said azo pigment has the formula ##STR14## where R 3 is hydrogen or methyl; R 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 -alkoxy, halogen, nitro, C 1 -C 4 -alkylcarbonylamino, or C 1 -C 4 -alkylsulphonylamino; R 5 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, C 1 -C 4 -alkylsulphonyl, trifluoromethyl, carboxamide, C 1 -C 4 -alkylcarboxamide, phenylcarboxamide, C 1 -C 4 -alkylphenylcarboxamide, C 1 -C 4 -alkoxyphenylcarboxamide, fluoro-, chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C 1 -C 4 -alkylbenzylcarboxamide, C 1 -C 4 -alkoxybenzylcarboxamide, fluoro-, chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C 1 -C 4 -alkylsulphonamide, phenylsulphonamide, C 1 -C 4 -alkylphenylsulphonamide, C 1 -C 4 -alkoxyphenylsulphonamide, fluoro-, chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C 1 -C 4 -alkylbenzylsulphonamide, C 1 -C 4 -alkoxybenzylsulphonamide, fluoro-, chloro-, bromo-benzylsulphonamide, nitrobenzylsulphonamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 alkoxybenzoylamino, nitrobenzoylamino, C 1 -C 4 -alkoxycarbonyl; R 6 is hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, cyano, C 1 -C 4 -alkoxy, nitro, or trifluoromethyl; and R 7 is hydrogen, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.

Claim 4

A pigmented organo macromolecular material according to claim 1, wherein said organo macromolecular material has the formula ##STR15## wherein R 3 is hydrogen or methyl; R 4 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine, nitro, C 1 -C 4 -alkylcarbonylamino, or C 1 -C 4 -alkylsulphonylamino; R 8 denotes hydrogen, fluorine, chlorine, bromine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, benzylamino, cyclohexylamino, C 1 -C 4 -alkylmercapto, phenylmercapto, C 1 -C 4 -alkylphenylmercapto, C 1 -C 4 -alkoxyphenylmercapto, fluoro-, chloro-,bromophenylmercapto, nitrophenylmercapto, carboxamide, mono- or di- C 1 -C 4 -alkylcarboxamide, mono- or di- phenylcarboxamide, mono- or di- C 1 -C 4 -alkylphenylcarboxamide, mono- or di- C 1 -C 4 -alkoxyphenylcarboxamide, mono- or di-fluoro, chloro, bromophenylcarboxamide, mono- or di-nitrophenylcarboxamide, mono- or di-benzylcarboxamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 -alkoxybenzoylamino, nitrobenzoylamino, bromobenzoylamino, phenylamino, C 1 -C 4 -alkylphenylamino, C 1 -C 4 -alkoxyphenylamino, chlorophenylamino, nitrophenylamino, C 1 -C 4 alkylsulphonylamino, phenylsulphonylamino , C 1 -C 4 -alkylphenylsulphonylamino, C 1 -C 4 -alkoxyphenylphenylsulphonylamino, fluoro-, chloro-, bromo-phenylsulphonylamino, or nitrophenylsulphonylamino, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl; R 9 is hydrogen, chlorine or hydroxyl; R 10 is hydrogen halogen, fluorine, chlorine, bromine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, benzylamino, cyclohexylamino, C 1 -C 4 -alkylmercapto, phenylmercapto, C 1 -C 4 -alkylphenylmercapto, C 1 -C 4 -alkoxyphenylmercapto, fluoro-, chloro-, bromo-phenylmercapto, nitrophenylmercapto, carboxyl, hydroxy, carboxamide, mono- or di- C 1 -C 4 -alkylcarboxamide, mono- or di- phenylcarboxamide, mono- or di- C 1 -C 4 -alkylphenylcarboxamide, mono- or di- C 1 -C 4 -alkoxyphenylcarboxamide, mono- or di- fluoro-, chloro-, bromo-phenylcarboxamide, mono- or di- nitrophenyl carboxamide, mono- or di- benzylcarboxamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 -alkoxybenzoylamino, nitrobenzoylamino, bromobenzoylamino, phenylamino, C 1 -C 4 -alkylphenylamino, C 1 -C 4 -alkoxyphenylamino, chlorophenylamino, bromophenylamino, nitrophenylamino, C 1 -C 4 -alkylsulphonylamino, phenylsulphonylamino, C 1 -C 4 -alkylphenylsulphonylamino, C 1 -C 4 -alkoxyphenylsulphonylamino, fluoro-, chloro-, bromo-phenylsulphonylamino, or nitrophenylsulphonylamino; and R 11 is hydrogen, fluorine, chlorine, bromine or hydroxyl.

Claim 5

A pigmented organo macromolecular material according to claim 1, wherein said azo pigment has the formula: ##STR16## wherein R 12 , R 13 , R 14 and R 15 are hydrogen, chlorine, bromine, carboxyl, C 1 -C 4 -alkoxycarbonyl, carboxamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, mono- or di-nitrobenzoylamino, benzoylamino substituted with 1-5 chlorines or bromines, C 1 -C 4 -alkylsulphonylamino, phenylsulphonylamino, methylphenylsulphonylamino, methoxysulphonylamino, or chlorophenylsulphonylamino.

Claim 6

A pigmented organo macromolecular material according to claim 1, wherein said organo macromolecular material is polyacrylonitrile.

Claim 7

A spin dyed polyacrylonitrile, comprising polyacrylonitrile and an azo pigment of the formula ##STR17## wherein D is the radical of an aromatic or hetero-aromatic amine which is free from sulphonic acid groups; m is the integer 1 or 2; n denotes 0, 1, 2, 3 or 4; R 1 is hydrogen or C 1 -C 4 alkyl; and R 2 is chlorine, bromine, Cl 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, trifluoromethyl, cyano, carboxamide, C 1 -C 4 -alkyl-carboxamide, phenylcarboxamide, C 1 -C 4 -alkylphenylcarboxamide, C 1 -C 4 -alkoxyphenylcarboxamide, fluoro-, chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C 1 -C 4 -alkylbenzylcarboxamide, C 1 -C 4 -alkoxybenzylcarboxamide, fluoro-, chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C 1 -C 4 -alkylsulphonamide, phenylsulphonamide, C 1 -C 4 -alkylphenylsulphonamide, C 1 -C 4 -alkoxyphenylsulphonamide, fluoro-, chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C 1 -C 4 -alkylbenzylsulphonamide, C 1 -C 4 -alkoxybenzylsulphonamide, fluoro-, chloro-, bromo-benzyl sulphonamide, nitrobenzylsulphonamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 -alkoxybenzoylamino, nitrobenzoylamino, phenylamino, C 1 -C 4 -alkylphenylamino, C 1 -C 4 -alkoxyphenylamino, fluoro-, chloro-, bromo-phenylamino, or nitrophenylamino.

Claim 8

A spin dyed polyacrylonitrile, comprising polyacrylonitrile and an azo pigment of the formula ##STR17## wherein D is the radical of an aromatic or hetero-aromatic amine which is free from sulphonic acid groups; m is the integer 1 or 2; n denotes 0, 1, 2, 3 or 4; R 1 is hydrogen or C 1 -C 4 alkyl; and R 2 is chlorine, bromine, Cl 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, trifluoromethyl, cyano, carboxamide, C 1 -C 4 -alkyl-carboxamide, phenylcarboxamide, C 1 -C 4 -alkylphenylcarboxamide, C 1 -C 4 -alkoxyphenylcarboxamide, fluoro-, chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C 1 -C 4 -alkylbenzylcarboxamide, C 1 -C 4 -alkoxybenzylcarboxamide, fluoro-, chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C 1 -C 4 -alkylsulphonamide, phenylsulphonamide, C 1 -C 4 -alkylphenylsulphonamide, C 1 -C 4 -alkoxyphenylsulphonamide, fluoro-, chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C 1 -C 4 -alkylbenzylsulphonamide, C 1 -C 4 -alkoxybenzylsulphonamide, fluoro-, chloro-, bromo-benzyl sulphonamide, nitrobenzylsulphonamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C 1 -C 4 -alkylbenzoylamino, C 1 -C 4 -alkoxybenzoylamino, nitrobenzoylamino, phenylamino, C 1 -C 4 -alkylphenylamino, C 1 -C 4 -alkoxyphenylamino, fluoro-, chloro-, bromo-phenylamino, or nitrophenylamino.