Ciba-geigy Corporation

Christoph Frey

Jost Von Der Crone

Francois L'Eplattenier

Gunther Zwahlen

Remy Jeanneret

Franz Felix

Alexander Von Zelewsky

Georgios Zographos

1:2 Nickel or 1:2 copper complexes of a naphthostyril of the formula ##STR1## or of tautomers thereof, in which A, X and Y are as defined in claim 1, are suitable for pigmenting high molecular weight organic material.

Naphthostyril Ni or Cu complexes, a process for their preparation, and

An electrophotographic imaging process, wherein the electrically photosensitive particles for the image reproduction consist of a black pigment selected from the series of the anthraquinoid pigments which contain at least 2 anthraquinone radicals or at least 6 condensed rings, of the perylenetetracarboxylic diimides or of the metal complexes of the formula ##STR1## wherein A represents a nitrogen atom or the ##STR2## X represents a hydrogen or halogen atom or an alkyl group of 1 to 6 carbon atoms,

Electrophotographic imaging process using anthraquinoid black pigments

Bis-isoindoline pigments of the formula ##STR1## wherein A represents a carbocyclic or heterocyclic aromatic radical,

Isoindoline pigments

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

Iminoisoindolinone metal complexes of formula ##STR1## wherein A represents a 5- or 6-membered heterocyclic radical which contains at least one further heteroatom and can be fused or doubled with benzene nuclei, M represents a divalent metal atom excluding the alkaline earth metals, X represents a hydrogen atom, Y represents a halogen atom, Z represents a nitro group, an alkoxycarbonyl group of 2 to 6 carbon atoms or a group of formula RY.sub.2 --, wherein R represents a hydrogen atom, an alkyl group of 1 to 6 carbon atoms which is substituted by an aryl radical or is unsubstituted, a cycloalkyl group of 5 to 6 carbon atoms, or represents an aryl group, and Y.sub.2 represents an oxygen or a sulphur atom, m and n are 0 to 4, p is 0 to 2, and the sum of m+n+p must be 4, which are useful for pigmenting high molecular organic material.

Iminoisoindolinone metal complex

Isoindolinone pigments of the formula ##STR1## wherein M denotes a polyvalent metal atom other than an alkaline earth, R denotes an organic radical, X denotes an O or S atom or an imino group, X.sub.1 and Y.sub.1 denote H or halogen atoms, alkyl, alkoxy, alkoxycarbonyl, alkylsulphonyl or alkylcarbamoyl groups containing 1-6 C atoms, or nitro, carbamoyl or aralcarbamoyl groups, or the radicals X.sub.1 and Y.sub.1 form a fused benzene ring, X.sub.2 denotes an H atom, Y denotes a halogen atom and Z denotes a nitro, a carbamoyl or phenylcarbamoyl group, an alkylcarbamoyl group having 2-6 C atoms, or a group of the formula R.sub.1 Y.sub.2, wherein R.sub.1 represents an H atom, an alkyl or cycloalkyl group containing 1-6 C atoms or an aralkyl or aryl group and Y.sub.2 represents an O or S atom, m denotes 0-4, n denotes 0-4 and p denotes 0-3 and the sum of m+n+p must be 4, are useful for coloring plastics and lacquers in yellow to orange shades of excellent fastness properties.

Isoindolinone compounds useful in preparing heavy metal containing

Metal complex pigments of the formula ##SPC1## Wherein X and Y denote hydrogen or halogen atoms or alkyl or alkoxy groups containing 1-4 C atoms and V and Z denote hydrogen or halogen atoms, nitro groups or alkyl, alkoxy or alkylsulphonyl groups containing 1-6 atoms, the two radicals V and Z can furthermore form a fused benzene ring and M represents a polyvalent metal atom, except an alkaline earth metal atom which are useful for pigmenting high molecular organic material.

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Aesch, Switzerland

Christoph Frey