Ciba-geigy Corporation

Ciba-geigy Ag

Jost Von Der Crone

Andre Pugin

Francois L'Eplattenier

Bernhard Medinger

Christoph Frey

Philippe Bugnon

Kurt Burdeska

Stefan Hari

Ernst Model

Rudolf Mory

Olof Wallquist

Fridolin Babler

Edward E Jaffe

Max Jost

Werner Sieber

Heinz Neuschutz

Gonzague Overney

Marius Leimer

Peter Dario

Compounds of the formula I ##STR1## in which R is a radical of the formula --OR.sub.5 or --NHR.sub.5, A is a radical of the formula II or III ##STR2## in which B is a radical of the formula ##STR3## in which n is the number 1 or 2, R.sub.1 and R.sub.3 independently of one another are --H or Cl, R.sub.2 and R.sub.4 independently of one another are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl, or --CONH-phenyl, --NHCO-phenyl or phenyloxy which is unsubstituted or substituted on the phenyl nucleus by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.5 is alkyl having at least 10 C atoms, R.sub.6 and R.sub.7 independently of one another are --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.8 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2, are particularly suitable as pigments for coloring polyolefins.

Disazo compounds containing long-chain alkyl ester radicals or

A process for enhancing the filterability of organic pigments, which comprises adding to an aqueous pigment suspension 0.5 to 15% by weight, based on the pigment, of an unbranched aliphatic 1,2-dihydroxy compound containing 8 to 22 carbon atoms, and stirring the mixture for at least 15 minutes in the temperature range from 20.degree. to 100.degree. C. Pigments treated by the process of this invention have substantially enhanced filterability as compared with identical pigments which have not been treated with the 1,2-dihydroxy compound.

Process for enhancing the filterability of organic pigments

Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R.sub.1 and R.sub.4 are --H or --Cl, R.sub.2 and R.sub.5 are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R.sub.3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R.sub.1 and R.sub.2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NO.sub.2 and X.sub.3 is --H, --NHCO--C.sub.1 -C.sub.4 alkyl, benzoylamino or phenylcarboxamide which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms and/or one or two methyl or methoxy groups or an --NHCO--C.sub.1 -C.sub.4 alkyl group, or X.sub.2 and X.sub.3 together with the carbon atom to which they are bound are an aromatic carbocyclic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring, in which the heterocyclic ring contains 1 or 2 N atoms and can additionally have an O atom or S atom, and Y.sub.1 is --H, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NHCOCH.sub.3, with the proviso that X.sub.3 must not be H, if X is --O-- or --NH--, are highly suitable for the mass coloration of plastics, in particular of polyolefins.

Monoazo compounds containing long-chain alkyl radicals

Tetrachloro-2-cyanobenzoic acid alkyl esters of formula ##STR1## wherein R is C.sub.1 -C.sub.5 alkyl, can be very conveniently prepared by (a) reacting the ammonium salt of tetrachloro-2-cyanobenzoic acid, in the presence of water and an inert organic solvent, with a hydroxide of formula MOH, wherein M is Na or K, and removing the ammonia evolved, and

Process for the preparation of alkyl esters of

Isoindoline compounds of the formula ##STR1## in which R is C.sub.1 -C.sub.4 alkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-, C.sub.1 -C.sub.4 alkoxy- or halogen-substituted phenyl, benzyl or phenylethyl, R.sub.1 and R.sub.2, independently of one another are hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and X is one of the groups of the formulae ##STR2## in which R, R.sub.1 and R.sub.2 are as defined above, A is one of the groups, --CN, --COO--(C.sub.1 -C.sub.4 alkyl) or --CONH--R.sub.5, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen or have the same meaning as R, V is --NH-- or --O-- and Z is --O--, --S--, --NH-- or --NH(CH)--.

Isoindoline pigment compounds

A process for coloring high molecular organic material, which comprises the use of isoindolines of formula I ##STR1## wherein A is a group of formula ##STR2## wherein R is a group selected from --CONHR.sub.1, --COOR.sub.2 and ##STR3## and R.sub.1 is hydrogen, C hd 1-C.sub.4 alkyl, phenyl or phenyl which is substituted by one or more identical or different members of the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --COR.sub.3, --NHCOR.sub.4 or ##STR4## in which formulae R.sub.3 is C.sub.1 -C.sub.4 alkoxy, --NH.sub.2 or --NHR.sub.4, R.sub.4 is C.sub.1 -C.sub.4 alkyl and R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, and R.sub.2 is C.sub.1 -C.sub.4 alkyl and Q is --NH or --S--; or A is a group of formula ##STR5## wherein V is NH or O, X.sub.1 and X.sub.3 are each independently of the other halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylmercapto, or phenoxy or phenylmercapto, each unsubstituted or substituted by halogen, C hd 1-C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and X.sub.2 is halogen. The strong colorations obtained by this process are distinguished in particular by good fastness to migration, heat, light and weathering.

Process for coloring high molecular weight organic material with

Isoindolines of formula I ##STR1## wherein Y is a radical of formula II, III, IV, IVa, V or VI ##STR2## wherein Y, R.sub.1, R.sub.2, R.sub.3, A, Z, Q, X.sub.2, X.sub.3 and n are defined in claim 1, are most suitable for coloring organic material of high molecular weight.

Isoindoline pigments containing at least one triazolopyrimidone radical

Novel compositions based on tetrachloroisoindolinone pigments

Novel compositions based on isoindoline pigments

A photoelectrophoretic imaging process, wherein a suspension of photosensitive pigment particles between two electrodes, at least one of which is transparent, is subjected to the influence of an electric field and exposed to an image, which process comprises using, as photosensitive pigment, an isoindoline of the formula ##STR1## wherein R.sub.1 and R.sub.3 are cyano, --COOR or --CONHR', in which R is alkyl, cycloalkyl, aryl or a heterocyclic aromatic radical, and R' is hydrogen, alkyl, cycloalkyl, aryl or a heterocyclic aromatic radical, R.sub.2 and R.sub.4 are cyano, or wherein R.sub.3 and R.sub.4, together with the carbon atom linking them, form a heterocyclic 6-membered ring. The pigments used in this invention are distinguished by particularly good photoelectrophoretic sensitivity and low fog density.

Use of isoindoline pigments for photoelectrophoretic imaging

Isoindolinone pigments of the formula ##STR1## in which R is an aryl radical which can contain groups which do not confer solubility and X is a group of the formulae ##STR2## in which Q is a radical of the formula ##STR3## in which R.sub.1 is a di- or tri-halogenophenyl radical or a carbamoylphenyl radical or a phenyl radical which is fused with a 5-membered or 6-membered hetero-ring which contains a cyclically bonded --CONH group, are useful for coloring in yellow to orange shades of good fastness properties.

Isoindoline pigments

A process for pigmenting organic material of high molecular weight, which comprises the use of a compound of the formula ##STR1## in which X is a meta- or para-positioned fluorine, chlorine or bromine atom. The yellow to scarlet colorations obtained are distinguished by excellent fastness to light and atmospheric influences.

Composition containing a condensation product of 1,3-diiminoisoindoline

Isoindolinone pigments of the formula ##STR1## in which R is an aryl radical which can contain groups which do not confer solubility and X is a group of the formulae ##STR2## in which Q is a radical of the formula ##STR3## in which R.sub.1 is a di- or tri-halogenophenyl radical or a carbamoylphenyl radical or a phenyl radical which is fused with a 5-membered or 6-membered hereto-ring which contains a cyclically bonded -CONH group, are useful for coloring in yellow to orange shades of good fastness properties.

Isoindoline pigments of the formula ##STR1## or of a formula which is a tautomer thereof, wherein R represents a direct bond or an aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, araliphatic or aromatic radical, R.sub.1 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, or, if R represents an ethylene group, both R.sub.1 s together also represent an ethylene group, R.sub.2 and R.sub.3 represent hydrogen atoms, alkyl groups of 1 to 4 carbon atoms or phenyl groups which are unsubstituted or substituted by methyl groups or halogen atoms, X represents an oxygen atom or a NH group, and Y represents an oxygen or a sulfur atom or a NH group dye plastics in fast yellow or brown shades.

Growing community of inventors

Riehen, Switzerland

Jost Von Der Crone