Axomethine pigments

Claim 2

Azomethine pigments of the formula ##STR21## or of the tautomeric formula ##STR22## in which D denotes a substituent of the formula ##STR23## R 1 denotes hydrogen or C 1 -C 4 -alkyl, or both R 1 , at the same time, denote CO, R 2 denotes hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, optionally substituted carboxamide, optionally substituted sulphonamide, acylamino or arylamino, R 5 denotes hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, C 1 -C 4 -alkylsulphonyl, trifluoromethyl, C 1 -C 4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkoxycarbonyl or carboxamide or sulphonamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, phenyl or benzyl, it being possible for phenyl and benzyl to be further substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine and nitro, R 6 denotes hydrogen, halogen, C 1 -C 4 -alkyl, cyano, C 1 -C 4 -alkoxy, nitro or trifluoromethyl, R 7 denotes hydrogen, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and m denotes an integer and n denotes 0, 1, 2, 3 or 4.

Claim 3

Azomethine pigments of the formula ##STR24## wherein R 3 denotes hydrogen or methyl, R 4 denotes 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 5 denotes hydrogen, halogen, such as fluorine, chlorine and bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, C 1 -C 4 -alkylsulphonyl, trifluoromethyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, substituted benzoylamino, C 1 -C 4 -alkoxycarbonyl, carboxamide or sulphonamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, phenyl or benzyl, it being possible for phenyl and benzyl to be further substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine and nitro, R 6 denotes hydrogen, halogen, C 1 -C 4 -alkyl, cyano, C 1 -C 4 -alkoxy, nitro or trifluoromethyl, R 7 denotes hydrogen, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and m denotes an integer, preferably 1 or 2.

Claim 4

Azomethine pigments of the formula ##STR24## wherein R 3 denotes hydrogen or methyl, R 4 denotes 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 5 denotes hydrogen, halogen, such as fluorine, chlorine and bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, C 1 -C 4 -alkylsulphonyl, trifluoromethyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, substituted benzoylamino, C 1 -C 4 -alkoxycarbonyl, carboxamide or sulphonamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, phenyl or benzyl, it being possible for phenyl and benzyl to be further substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine and nitro, R 6 denotes hydrogen, halogen, C 1 -C 4 -alkyl, cyano, C 1 -C 4 -alkoxy, nitro or trifluoromethyl, R 7 denotes hydrogen, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and m denotes an integer, preferably 1 or 2.

Claim 5

Azomethine pigments of the formula ##STR25## wherein R 3 and R 4 have the meaning indicated above, R 8 denotes hydrogen, halogen, such as fluorine, chlorine and 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 which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, phenylamino which is optionally substituted by C 1 -C 4 -alkyl C 1 -C 4 -alkoxy, chlorine or nitro, carboxamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C 1 -C 4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, C 1 -C 4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, R 9 denotes hydrogen, chlorine or hydroxyl, R 10 denotes hydrogen, halogen, such as fluorine, chlorine or bromine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylmercapto, phenylmercapto which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, carboxyl, hydroxyl, carboxamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, C 1 -C 4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, flourine, chlorine, bromine or nitro, R 11 denotes hydrogen, halogen, or hydroxyl and m denotes an integer, preferably 1 or 2.

Claim 6

Azomethine pigments of the formula ##STR25## wherein R 3 and R 4 have the meaning indicated above, R 8 denotes hydrogen, halogen, such as fluorine, chlorine and 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 which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, phenylamino which is optionally substituted by C 1 -C 4 -alkyl C 1 -C 4 -alkoxy, chlorine or nitro, carboxamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, carboxyl, hydroxyl, C 1 -C 4 -alkylcarbonylamino, benzoylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, C 1 -C 4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, R 9 denotes hydrogen, chlorine or hydroxyl, R 10 denotes hydrogen, halogen, such as fluorine, chlorine or bromine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylmercapto, phenylmercapto which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, benzylamino, cyclohexylamino, phenylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, carboxyl, hydroxyl, carboxamide which is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, benzyl or phenyl, it being possible for phenyl to be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or nitro, C 1 -C 4 -alkyl, carbonylamino, benzoylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or nitro, C 1 -C 4 -alkylsulphonylamino or phenylsulphonylamino which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, flourine, chlorine, bromine or nitro, R 11 denotes hydrogen, halogen, or hydroxyl and m denotes an integer, preferably 1 or 2.

Claim 7

Azomethine pigments of the formula ##STR26## wherein R 12 , R 13 , R 14 and R 15 denote hydrogen, chlorine, bromine, carboxyl, C 1 -C 4 -alkoxycarbonyl, carboxamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino which is optionally substituted by 1 or 2 nitro groups or 1 to 5 chlorine or bromine atoms, C 1 -C 4 -alkylsulphonylamino, phenylsulphonylamino which is optionally substituted by methyl, methoxy or chlorine or a radical of the formula ##STR27##

Claim 8

Azomethine pigments of the formula ##STR26## wherein R 12 , R 13 , R 14 and R 15 denote hydrogen, chlorine, bromine, carboxyl, C 1 -C 4 -alkoxycarbonyl, carboxamide, C 1 -C 4 -alkylcarbonylamino, benzoylamino which is optionally substituted by 1 or 2 nitro groups or 1 to 5 chlorine or bromine atoms, C 1 -C 4 -alkylsulphonylamino, phenylsulphonylamino which is optionally substituted by methyl, methoxy or chlorine or a radical of the formula ##STR27##

Claim 9

Process for the preparation of azomethine pigments, characterised in that aromatic or hetero-aromatic amines D--NH.sub.2 (VI) in which D has the meaning given in claim 1, are subjected to a condensation reaction with an alkoxyethylene-bis-quinazolinone of the formula ##STR28## in which R represents a C 1 -C 4 -alkyl group and R 1 , R 2 and n have the meaning indicated in claim 1, in an organic solvent at 100°-220° C.

Claim 10

Process for the preparation of azomethine pigments, characterised in that formimino-esters of aromatic or hetero-aromatic amines, of the formula D--N═CH--OR (X) in which D has the meaning given in claim 1, and in which R represents a C 1 -C 4 -alkyl group, are subjected to a condensation reaction with methylene-bis-quinazolinones of the formula ##STR29## in which R 1 , R 2 and n have the meaning indicated in claim 1, in an organic solvent at 100°-220° C.

Claim 11

Process for the preparation of azomethine pigments, characterised in that formamidines of aromatic or heteroaromatic amines, of the formula D--N═CH--N(R).sub.2 (XXXV) in which D has the meaning given in claim 1, and in which R represents a C 1 -C 4 -alkyl group, are subjected to a condensation reaction with methylene-bisquinazolinones of the formula (VII) in an organic solvent at 100°-220° C.