Azo dye pigments containing 4-quinazolinone moieties
AssigneeBayer Aktiengesellschaft
InventorsMeinhard Rolf, Rutger Neeff, Walter Muller
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Abstract
Heterocyclic compounds of the formula ##STR1## wherein R.sub.1 denotes hydrogen or C.sub.1 -C.sub.4 -alkyl or the two R.sub.1 s together denote CO, R.sub.2 denotes a substituent and n denotes 0, 1, 2, 3 or 4, processes for their preparation, azo pigments prepared therefrom by a coupling reaction with a diazo component of an aromatic or hetero-aromatic amine free from sulphonic acid groups, and the use of these azo pigments for pigmenting organic macromolecular materials and especially in the spin dyeing of polyacrylonitrile.
Claims6
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.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.2 is chlorine, bromine, Cl.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro, trifluoromethyl, cyano, carboxamide, C.sub.1 -C.sub.4 -alkyl-carboxamide, phenylcarboxamide, C.sub.1 -C.sub.4 alkylphenylcarboxamide, C.sub.1 -C.sub.4 -alkoxyphenylcarboxamide, fluoro-,chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C.sub.1 -C.sub.4 -alkylbenzylcarboxamide, C.sub.1 -C.sub.4 -alkoxybenzylcarboxamide, fluoro-,chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C.sub.1 -C.sub.4 -alkylsulphonamide, phenylsulphonamide, C.sub.1 -C.sub.4 -alkylphenylsulphonamide, C.sub.1 -C.sub.4 -alkoxyphenylsulphonamide, fluoro-,chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C.sub.1 -C.sub.4 - alkylbenzylsulphonamide, C.sub.1 -C.sub.4 -akloxybenzylsulphonamide, fluoro-, chloro-, bromo-benzyl sulphonamide, nitrobenzylsulphonamide, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C.sub.1 -C.sub.4 -alkylbenzoylamino, C.sub.1 -C.sub.4 -alkoxybenzoylamino, nitrobenzoylamino, phenylamino, C.sub.1 -C.sub.4 -alkylphenylamino, C.sub.1 -C.sub.4 -alkoxyphenylamino, fluoro-, chloro-, bromo-phenylamino, or nitrophenylamino.
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.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.2 is chlorine, bromine, Cl.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro, trifluoromethyl, cyano, carboxamide, C.sub.1 -C.sub.4 -alkyl-carboxamide, phenylcarboxamide, C.sub.1 -C.sub.4 -alkylphenylcarboxamide, C.sub.1 -C.sub.4 -alkoxyphenylcarboxamide, fluoro-, chloro-, bromo-phenylcarboxamide, nitrophenylcarboxamide, benzylcarboxamide, C.sub.1 -C.sub.4 -alkylbenzylcarboxamide, C.sub.1 -C.sub.4 -alkoxybenzylcarboxamide, fluoro-, chloro-, bromo-benzylcarboxamide, nitrobenzylcarboxamide, sulphonamide, C.sub.1 -C.sub.4 -alkylsulphonamide, phenylsulphonamide, C.sub.1 -C.sub.4 -alkylphenylsulphonamide, C.sub.1 -C.sub.4 -alkoxyphenylsulphonamide, fluoro-, chloro-, bromo-phenylsulphonamide, nitrophenylsulphonamide, benzylsulphonamide, C.sub.1 -C.sub.4 -alkylbenzylsulphonamide, C.sub.1 -C.sub.4 -alkoxybenzylsulphonamide, fluoro-, chloro-, bromo-benzyl sulphonamide, nitrobenzylsulphonamide, C.sub.1 -C.sub.4 -alkylcarbonylamino, benzoylamino, chlorobenzoylamino, C.sub.1 -C.sub.4 -alkylbenzoylamino, C.sub.1 -C.sub.4 -alkoxybenzoylamino, nitrobenzoylamino, phenylamino, C.sub.1 -C.sub.4 -alkylphenylamino, C.sub.1 -C.sub.4 -alkoxyphenylamino, fluoro-, chloro-, bromo-phenylamino, or nitrophenylamino.
Dependencies are inferred from the claim text.