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AssigneeCiba-Geigy Corporation
InventorUrs Lehmann
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The heavy metal complex dyes of azo or azomethine dyes of the formula ##STR1## in which D is the radical of a dizao component of the benzene, naphthalene or heterocyclic series, K--OH is the radical of the formula ##STR2## in which the symbols A, A', B and B' each represent a carbon atom or in which one of the symbols A, A', B or B' represents a nitrogen atom while the others represent a carbon atom, R is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or substituted or unsubstituted phenyl, and the ring E can be further substituted, Y is a nitrogen atom or a CH group, and n is 0 or 1, and in which --(CO).sub.n --OH is bonded to D in a position adjacent to --N.dbd.Y--, produce dyeings having good fastnesses particular very good crock, wet, wet crock and light fastness on nitrogen-containing or hydroxyl-containing fibre materials.
A heavy metal complex of an azo or azomethine dye of the formula ##STR121## in which D--(CO).sub.n --OH is an aminophenol, aminonaphthol or aminobenzoic acid diazo component, which, in addition to the metallizable group, is unsubstituted or substituted by C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.2 -C.sub.8 -alkanoylamino, C.sub.2 -C.sub.8 -alkoxycarbonylamino, benzoylamino, amino, mono- or dialkylamino having 1 to 8 carbon atoms in the alkyl radical, phenylamino, alkoxycarbonyl having 1 to 8 carbon atoms in the alkoxy radical, nitro, cyano, trifluoromethyl, halogen, sulfamoyl, sulfamoyl which is monosubstituted or disubstituted on the nitrogen atom by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or phenyl, carbamoyl, ureido, hydroxyl, C.sub.1 -C.sub.8 -alkyl-sulfonyl, phenylsulfonyl, carboxyl, sulfomethyl, sulfo, phenylazo, naphthylazo or a fibre-reactive acryloyl, mono-, di- or trihalo-acryloyl or -methacryloyl, mono- or dihalopropionyl, phenylsulfonylpropionyl, vinylsulfonylpropionyl, .beta.-chloroethylsulfonylpropionyl, methysulfonylpropionyl or .beta.-sulfatoethylsulfonyl, mono-, di- or trihalopyrimidyl or mono- or dihalotriazinyl radical, which is bonded directed or via --NH--, --N(CH.sub.3)--, --N(C.sub.2 H.sub. 5)--, --N(C.sub.3 H.sub.7)--, ##STR122## or --CH.sub.2 --N(R)--, where R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, sulfo, sulfato or halogen, phenyl or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.6 -alkanoylamino, sulfo or halogen, K--OH is the radical of the formula ##STR123## in which the symbols A, A', B and B' each represent a carbon atom or in which one of the symbols A, A', B or B' represents a nitrogen atom while the others represent a carbon atom, R.sub.1 has the meaning given for R or R.sub.1 is a fibre-reactive radical given for D, the ring E is unsubstituted or substituted by the substituents given for d, Y is a nitrogen atom or a CH group, and n is 0 or 1, and in which --(CO).sub.n --OH is bonded to D in a position adjacent to --N.dbd.Y--.
A heavy metal complex according to claim 1 of an azo dye of the formula ##STR124## in which D is phenyl or naphthyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkoxycarbonylamino, benzoylamino, amino, mono- or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl radical, phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, nitro, cyano, trifluoromethyl, halogen, sulfamoyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl-substituted sulfamoyl, carbamoyl, ureido, hydroxyl C.sub.1 -C.sub.4 alkylsulfonyl, carboxyl, sulfomethyl, sulfo, phenylazo or a fibre-reactive radical given for D in claim 21, or D--OH is a carboxyphenyl radical which is unsubstituted or substituted by the abovementioned substituents, R' is hydrogen or C.sub.1 -C.sub.4 alkyl, and the benzo ring E is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkoxycarbonylamino, benzoylamino, amino, mono- or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl radical, phenylamino, C.sub. 1 -C.sub.4 alkoxycarbonyl, nitro, cyano, trifluoromethyl, halogen, sulfamoyl, carbamoyl, ureido, hydroxyl, C.sub.1 -C.sub.4 alkylsulfonyl, carboxyl, sulfomethyl, sulfo, a fibre-reactive radical given for D in claim 21 or phenylazo, and in which the hydroxyl group in D is in the o-position relative to the azo group.
A heavy metal complex according to claim 13, wherein D.sub.1 is phenyl or naphthyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkoxycarbonyl amino, benzoylamino, amino, mono- or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl radical, phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, nitro, cyano, trifluoromethyl, halogen, sulfamoyl, carbamoyl, ureido, hydroxyl, C.sub.1 -C.sub.4 alkylsulfonyl, carboxyl, sulfometyl, sulfo, a fibre reactive radical as given for D.sub.1 in claim 23 and phenylazo, K.sub.1 is benzene or naphthalene or 5-pyrazolone, 5-aminopyrazole, quinoline, acetoacetarylide or benzylacetarylide which are unsubstituted or are substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkoxycarbonylamino, benzoylamino, amino, mono- or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl radical, phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, nitro, cyano, trifluromethyl, halogen, sulfamoyl, carbamoyl, ureid, hydroxyl, C.sub.1 -C.sub.4 alkylsulfonyl, carboxyl, sulfomethyl, sulfo, a fibre-reactive as given for K.sub.1 in claim 23, and Y' is a nitrogen atom.
Dependencies are inferred from the claim text.