Ciba-Geigy Corporation

Francois L'Eplattenier

Andre Pugin

Laurent Vuitel

Jost Von Der Crone

Stefan Hari

Paul Lienhard

Armand Roueche

James M McCrae

Christoph Frey

Alexander M Irvine

Alexander Von Zelewsky

The isoindoline-azine nickel complex of the formula ##STR1## colors plastics, lacquers and printing inks in yellow shades of outstanding fastness properties.

Isoindoline-azine nickel complex with piperazine

Metal complexes of azomethines of the formula ##STR1## are useful for coloring plastics and lacquers in yellow to red shades of excellent fastness properties.

Metal complexes of azomethines

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

Metal complexes of azomethines and process for their manufacture

Novel metal complexes of azomethines and process for their manufacture

Mixed complexes of methine dyes of formula ##STR1## wherein M.sub.1 represents zinc, cadmium, lead or manganese, M.sub.2 represents cobalt, copper or nickel, R represents an organic radical, Z.sub.1 represents an oxygen or a sulphur atom or an imino group, X.sub.1 and Y.sub.1 represent hydrogen or halogen atoms, alkyl, alkoxy, alkoxycarbonyl, alkylsulphonyl or alkylcarbamoyl groups of 1 to 6 carbon atoms, nitro, carbamoyl or arylcarbamoyl groups, or the radicals X.sub.1 and Y.sub.1 form a fused benzene ring, X represents a hydrogen atom, Y represents a halogen atom and Z represents a nitro group or a group of formula R.sub.1 Y.sub.2 --, wherein R.sub.1 represents a hydrogen atom, an alkyl or cycloalkyl group of 1 to 6 carbon atoms, an aralkyl or aryl group, and Y.sub.2 represents an oxygen or a sulphur atom, m is 0 to 4, n is 0 to 4, p is 0 to 3, and the sum of m+n+p must be 4, and wherein the atomic ratio of M.sub.1 :M.sub.2 is between 5:95 and 95:5 which are useful for pigmenting high molecular organic material.

Mixed complexes of methine dyes

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

Azo colorants of the formula ##STR1## wherein A denotes the radical of a heterocyclic diazo component, R.sub.1 denotes a hydroxyl, alkyl, phenyl or alkoxycarbonyl group, R.sub.2 denotes a H atom or an alkyl, phenyl, acyl, nitrile, alkoxycarbonyl or carbamoyl group, and X and Y denote substituents which do not confer solubility in water are prepared. The compounds are useful for pigmenting high molecular weight organic materials, such as polyesters, polyolefins and rubber. The compounds have excellent fastness to light, weathering and migration.

Benzinaldazolyl-, quinolonyl-, or

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

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Therwil, Switzerland

Francois L'Eplattenier