Anthraquinone-azomethine compounds, processes for their preparation and processes for dyeing synthetic fibre materials and for pigmenting organic macromolecular substances

A process for dyeing a synthetic fiber which comprises applying thereto an anthraquinone-azomethine compound of the formula ##STR65## or of the tautomeric formula ##STR66## or of the tautomeric formula ##STR67## in which A denotes an anthraquinone radical which is free from sulphonic acid groups and optionally further substituted,

• R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, carbamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl, substituted phenyl with a substituent of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, sulfamoyl, sulfamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl which in turn is optionally further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, acylamino, or arylamino, carboxyl, carboxylic acid, C.sub.1 -C.sub.4 alkyl ester or hydroxyl,
• R.sub.2 denotes hydrogen, halogen, nitro, cyano, carbamoyl, or sulfamoyl, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 to C.sub.4 alkyl, phenyl which in turn can be itself substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, fluorine, chlorine bromine or nitro or benzyl, sulfonic acid C.sub.1 -C.sub.4 alkyl ester, sulfonic acid aryl ester, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, benzoyl, benzoyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, carbamoyl or sulfamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, or bromine or nitro, or benzyl, acylamino or arylamino, alkyl or phenyl sulphone, or phenyl sulphone substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 -C.sub.4 alkyl, alkyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, or a hetero-aromatic radical of the formula ##STR68## or of the formula ##STR69## or of the formula ##STR70## R.sub.3 denotes aryl, aryl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 to C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl or heteroaryl where the aryl radical of the heteroaryl moiety can be substituted in the same manner as said substituted aryl, cycloalkyl or C.sub.1 -C.sub.12 alkyl, it being possible for the alkyl chain to be interrupted by oxygen or sulfur and/or substituted by hydroxyl, N(R.sub.5).sub.2 -- or --N(R.sub.5).sub.3.sup..sym. X.sup..crclbar. groups,
• R.sub.4 denotes halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carboxamide, sulphonamide, acylamino, or arylamino,
• R.sub.5 denotes hydrogen, C.sub.1 -C.sub.4 alkyl, cycloalkyl, aryl or substituted aryl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 -C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro, or benzyl,
• X denotes an anion,
• m denotes 1, 2, 3, or 4 and
• n denotes 0, 1, 2, 3, or 4.

An organic macromolecular composition comprising an organic macromolecular material and an anthraquinone-azomethine compound of the formula ##STR71## or of the tautomeric formula ##STR72## or of the tautomeric formula ##STR73## in which A denotes an anthraquinone radical which is free from sulphonic acid groups and optionally further substituted,

• R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, carboamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl, substituted phenyl with a substituent of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, sulfamoyl, sulfamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl which in turn is optionally further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, acylamino, or arylamino, carboxyl, carboxylic acid, C.sub.1 -C.sub.4 alkyl ester or hydroxyl,
• R.sub.2 denotes hydrogen, halogen, nitro, cyano, carbamoyl, or sulfamoyl, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 to C.sub.4 alkyl, phenyl which in turn can be itself substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl, sulfonic acid C.sub.1 -C.sub.4 alkyl ester, sulphonic acid aryl ester, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, benzoyl, benzoyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, carbamoyl or sulfamoyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, or bromine or nitro, or benzyl, acylamino or arylamino, alkyl or phenyl sulphone, or phenyl sulphone substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 - C.sub.4 alkyl, alkyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluourine, chlorine, bromime or nitro or benzyl, or a hetero-aromatic radical of the formula ##STR74## or of the formula ##STR75## or of the formula ##STR76## R.sub.3 denotes aryl, aryl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 to C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, fluorine, chlorine, bromine or nitro or benzyl or heteroaryl where the aryl radical of the heteroaryl moiety can be substituted in the same manner as said substituted aryl, cycloalkyl or C.sub.1 -C.sub.12 alkyl, it being possible for the alkyl chain to be interrupted by oxygen or sulfur and/or substituted by hydroxyl, N(R.sub.5).sub.2 -- or --N(R.sub.5).sub.3.sup..sym. X.sup.63 groups,
• R.sub.4 denotes halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carboxamide, sulphonamide, acylamino, or arylamino,
• R.sub.5 denotes hydrogen, C.sub.1 -C.sub.4 alkyl, cycloalkyl, aryl or substituted aryl substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl, cyano, carbamoyl, sulfamoyl, acylamino, arylamino, substituted carbamoyl or substituted sulfamoyl where the substituent is C.sub.1 -C.sub.4 alkyl, phenyl which in turn can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine, bromine, or nitro, or benzyl,
• X denotes an anion,
• m denotes 1, 2, 3, or 4 and
• n denotes 0, 1, 2, 3, or 4.