Ciba-geigy Corporation

Laurent Vuitel

Francois L'Eplattenier

Andre Pugin

Stefan Hari

James M McCrae

Alexander M Irvine

1:1-Metal complexes of azomethines of the formula I ##STR1## wherein A and B are isocyclic or heterocyclic aromatic radicals, with however only one of the radicals A and B being a benzene ring, R represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aryl radical, and the complexing metal ions are bivalent cations of the transition metals, zinc ions or cadmium ions which are useful for pigmenting high molecular organic material.

1:1-Heterocyclic azo methine-metal complex dyestuffs

1:1-Azomethine-metal-complex dyestuffs

1:1 metal complexes of bis-azomethines of the formula ##STR1## wherein R denotes an alkylene radical which contains 2-8 C atoms and is optionally interrupted by hetero-atoms, X denotes a H or halogen atom or an alkyl, alkoxy, carboxyl, alkoxy-carbonyl or phenylazo group and Y and Z denote H or halogen atoms, or wherein the substituents Y and Z form a fused benzene ring, if R contains a hetero-atom, Y and Z must not be H atoms, and if R contains 2 C atoms, X, Y and Z must not be H atoms, and a metal are valuable pigments coloring plastics and printing inks in fast yellow to range shades.

Metal complexes of bis-azomethines from hydroxy-aldehydes and alkylene

Azomethine pigments of the formula ##STR1## and metal complexes thereof, wherein A denotes an isocyclic or heterocyclic aromatic radical, R denotes a H atom, an alkyl group containing 1-6 C atoms, or an aryl radical, X.sub.2 and X.sub.4 denote H atoms or halogen atoms, X.sub.1 and X.sub.3 denote H atoms or halogen atoms, alkoxy or alkylmercapto groups containing 1-6 C atoms, cycloalkoxy groups containing 5-6 C atoms, or aralkoxy, aryloxy or arylmercapto groups, it being possible for one of the substituents X.sub.1 -X.sub.4 also to be a nitro group which are useful for pigmenting of high molecular material.

Azomethine pigments

Bis-hydrazone metal complexes of the formula ##STR1## wherein A denotes an isocyclic or heterocyclic radical, R denotes a H atom, an alkyl group or an aryl radical, M denotes a divalent transition metal and zinc or cadmium, X.sub.1 and X.sub.2 independently of one another represent alkyl, cycloalkyl, aralkyl or aryl radicals, or conjointly form a fused carbocyclic or heterocyclic aromatic ring, L denotes a ligand having one or more coordinating N or S atoms, and n denotes the number 1 - 5, are useful for coloring plastic and lacquers in fast yellow to red shades.

Metal complexes of bis-hydrazones

Process for the manufacture of bis-azomethine metal complex colorants of the formula ##STR1## wherein A denotes an isocyclic or heterocyclic aromatic radical, X denotes an isocyclic or heterocyclic aromatic radical to which the N-atoms are bonded in the o-position or peri-position, or an alkylene radical containing 2-8 C atoms, and M denotes a divalent transition metal ion, a zinc ion or cadmium ion, characterized in that an o-hydroxyaldimine compound of the formula ##STR2## wherein A has the abovementioned meaning and R denotes an alkyl, cycloalkyl or aryl radical, is reacted with a diamine of the formula

Process for the manufacture of bis-azomethine metal complex colorants

1:1- and 2:1-metal complexes of bishydrazides of the formula I ##SPC1## wherein both A's represent identical or different isocyclic or heterocyclic aromatic radicals, B represents an isocyclic or heterocyclic aromatic radical, and R represents hydrogen, an alkyl group containing 1 - 6 carbon atoms, or an alkyl radical, and the complexing metal ions are bivalent cations of the transition metals, zinc ions or cadmium ions which are useful for pigmenting high molecular organic material.

Metal complexes of bishydrazides

Azomethine pigments of the formula ##SPC1## And metal complexes thereof, wherein A denotes an isocyclic or heterocyclic aromatic radical, R denotes a H atom, an alkyl group containing 1-6 C atoms, or an aryl radical, X.sub.2 and X.sub.4 denote H atoms or halogen atoms, X.sub.1 and X.sub.3 denote H atoms or halogen atoms, alkoxy or alkylmercapto groups containing 1-6 C atoms, cycloalkoxy groups containing 5-6 C atoms, or aralkoxy, aryloxy or arylmercapto groups, it being possible for one of the substituents X.sub.1 -X.sub.4 also to be a nitro group which are useful for pigmenting of high molecular material.

Bis-azomethine metal complex colorants of the formulae ##SPC1## Wherein M denotes a divalent transition metal cation, zinc ion or cadmium ion, X denotes an isocyclic or heterocyclic aromatic radical to which the two nitrogen atoms are bonded in the o- or peri-position to one another and Y.sub.1 and Y.sub.2 denote hydrogen, halogen, alkyl, aryl, nitro, alkoxy, phenoxy or hydroxyl, which are suitable for pigmenting high-molecular organic material.

Bis-azomethine metal complex colorants from hydroxycoumarin derivatives

Bis-azomethine pigments of the formula ##SPC1## Wherein X denotes an aromatic radical on which the imino groups are in the o-position, Y denotes a hydroxyl, alkoxy, cycloalkoxy, aralkoxy or aryloxy, amino, alkylamino or arylamino group and Z denotes a H or halogen atom or an alkoxy, nitro or nitrile group, the radical X having to be free of nitro groups if Y denotes an arylamino group and Z denotes a H atom, as well as metal complexes of these bis-azomethines are useful for coloring plastics and lacquers in yellow to red shades of good fastness properties.

Growing community of inventors

Therwil, Switzerland

Laurent Vuitel