Ciba-geigy Corporation

Ernst Model

Andre Pugin

Jost Von Der Crone

Iminoisoindolinone pigments of the formula ##STR1## are pigments with excellent color strength and good fastness to light, atmospheric influences, heat and migration, and are suitable for pigmenting organic material of high molecular weight.

Iminoisoindolinone pigments, process for their production and use thereof

Isoindolinone pigments of the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represent hydrogen or halogen atoms, or one or two of X.sub.1 -X.sub.4 represents alkoxy groups of 1 to 4 carbon atoms of phenoxy groups and the others represent hydrogen or halogen atoms, R and R' represent hydrogen or halogen atoms or methyl or methoxy groups, R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represent hydrogen, chlorine or bromine atoms or alkyl groups of 1 to 2 carbon atoms, R.sub.3 and R.sub.6 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 2 carbon atoms or radicals of the formula ##STR2## Q represents a direct bond or a p-phenylene group, n is 1 or 2 and X represents a group of the formula ##STR3## wherein R.sub.7 and R.sub.8 represent hydrogen or chlorine atoms or methyl groups.

Tetraphenylketazines and isoindolinone pigments obtained therefrom

The invention relates to iminoisoindolinone pigments of the formula ##STR1## wherein X is halogen, Y and Z are halogen, C.sub.1 -C.sub.4 alkoxy, or aryloxy, R.sub.1 and R.sub.2 are hydrogen, halogen, C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 alkoxy, and A is phenyl which can be substituted by halogen, trifluoromethyl, C.sub.1- C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, or by a group of the formula --CONHR.sub.3 or --NHCOR.sub.4, wherein R.sub.3 is hydrogen, C.sub.1- C.sub.2 alkyl, or phenyl which can be substituted by halogen, methyl, methoxy or trifluoromethyl, and R.sub.4 is phenyl which can be substituted by halogen, methyl or methoxy, or is C.sub.1 -C.sub.2 alkyl, or A is a heterocyclic radical. These pigments are distinguished by particulary excellent color strength and fastness to migration and are suitable for pigmenting organic material of high molecular weight.

Iminoisoindolinone pigments containing

Isoindolinone pigments of the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represent hydrogen or halogen atoms, or one or two of X.sub.1 -X.sub.4 represent alkoxy groups of 1 to 4 carbon atoms or phenoxy groups and the others represent hydrogen or halogen atoms, R and R' represent hydrogen or halogen atoms or methyl or methoxy groups, R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represent hydrogen, chlorine or bromine atoms or alkyl groups of 1 to 2 carbon atoms, R.sub.3 and R.sub.6 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 2 carbon atoms or radicals of the formula ##STR2## Q represents a direct bond or a p-phenylene group, n is 1 or 2 and X represents a group of the formula ##STR3## wherein R.sub.7 and R.sub.8 represent hydrogen or chlorine atoms or methyl groups.

Isoindolinone pigments of the formula ##STR1## wherein R represents an aliphatic or cycloaliphatic radical, a cycloaliphatic, aromatic or heterocyclic radical to which the oxygen atoms are attached through alkyl or alkoxy groups, V.sub.1 and V.sub.2 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 4 carbon atoms, X represents a halogen atom, Y and Z represent halogen atoms, alkoxy or alkylmercapto groups of 1 to 6 carbon atoms, cycloalkoxy groups of 5 to 6 carbon atoms, aralkoxy, aryloxy or arylmercapto groups, and n is an integer from 2 to 6, are valuable pigments coloring plastics, lacquers and printing inks in various yellow shades of excellent fastness properties and high color strength.

Isoindolinone pigments

Isoindolinone pigments of the formula ##STR1## WHEREIN R represents an aliphatic or cycloaliphatic radical, a cycloaliphatic, aromatic or heterocyclic radical to which the oxygen atoms are attached through alkyl or alkoxy groups, V.sub.1 and V.sub.2 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 4 carbon atoms, X represents a halogen atom, Y and Z represent halogen atoms, alkoxy or alkylmercapto groups of 1 to 6 carbon atoms, cycloalkoxy groups of 5 to 6 carbon atoms, aralkoxy, aryloxy or arylmercapto groups, and n is an integer from 2 to 6, are valuable pigments coloring plastics, lacquers and printing inks in various yellow shades of excellent fastness properties and high color strength.

Isoindolinone pigments and process for their manufacture

Iminoisoindolinone dyestuffs of the formula ##STR1## wherein X denotes chlorine or bromine atoms, X.sub.1 denotes a halogen atom or an alkyl, alkoxy, nitrile, trifluoromethyl or alkylsulphonyl group, Y.sub.1 denotes a hydrogen or halogen atom or an alkyl or alkoxy group, X.sub.2 denotes a hydrogen or halogen atom or an alkyl or alkoxy group and Y.sub.2 denotes a hydrogen or halogen atom or an alkyl or alkoxy group, or the radicals X.sub.2 and Y.sub.2 together form a fused benzene ring, and wherein, in the benzene rings A and B, a hydrogen atom is present in at least one o-position relative to the azomethine group were prepared. The dyestuffs may be used for pigmenting high molecular weight organic materials such as cellulose ethers, polyamides and polyesters. The pigments have outstanding fastness to light, migration and weathering.

Methyl or methoxy substituted iminoisoindolinone pigments

Iminoisoindolinone dyestuffs of the formula ##STR1## wherein X is halogen, Y halogen, alkoxy, cycloalkoxy, aralkoxy or aryloxy, Y.sub.1 hydrogen, halogen, alkyl or alkoxy having 1 - 4 c-atoms, Y.sub.2 alkyl, alkoxy or alkanoylamino having 1 - 4 c-atoms or benzoylamino, Z chlorine or methyl and R alkyl having 1 - 4 c-atoms or aryl which are useful for pigmenting high molecular organic material.

Mono aryl azo-mono-iminoisoindolinone dyestuffs

Iminoisoinolinone pigments of the formula ##STR1## wherein R denotes an alkyl group containing 1-4 C atoms, or an aryl group, the W's denote H atoms or, conjointly denote a direct bond, the X's denote halogen atoms, the Y's and Z's denote halogen atoms, alkoxy or alkylmercapto groups containing 1-6 atoms, cycloalkoxy groups containing 5-6 C atoms, or aralkoxy, aryloxy or arylmercapto groups, which are useful for pigmenting high molecular organic material.

Iminoisoindolinone pigments

Iminoisoindolinone pigments of the formula ##SPC1## Wherein the X denote chlorine or bromine atoms are useful for coloring plastics and lacquers in fast yellow shades.

Iminoisoindolinone pigments and process for their manufacture

New Iminoisoindolinone pigments of the formula ##SPC1## Wherein R.sub.1 denotes aromatic radicals, R.sub.2 denotes an H atom, and alkyl group containing 1-6 C atoms, a cycloalkyl group containing 5-6 C atoms or an isocyclic or heterocyclic aromatic radical, X.sub.3 denotes a direct bond or an imino group, the X denote halogen atoms, and Y and Z denote halogen atoms, alkoxy or alkylmercapto groups containing 1-6 C atoms, cycloalkoxy groups containing 5-6 C atoms, aralkoxy, aryloxy or arylmercapto groups, which are useful for pigmenting high molecular organic material.

Growing community of inventors

Basel, Switzerland

Ernst Model