Ciba-geigy Corporation

Georg Cseh

Stefan Hari

Paul Lienhard

Armand Roueche

Karl Ronco

Walter Wiedemann

Willy Mueller

Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.4, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sup.3, R.sup.4 and R.sup.5, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, are most suitable for coloring high molecular organic material.

Amine salts of azo pigments based on pyrazolone derivatives

High-molecular weight organic material containing at least one metal complex of a ligand of formula I: ##STR1## wherein A is a carbocyclic aromatic or heterocyclic aromatic radical, B is a carbocyclic aromatic radical or a heterocyclic aromatic radical containing at least one N atom, it being necessary for at least one of the radicals A and B to be heterocyclic, and R.sub.1 is --C.sub.1 -C.sub.18 -alkyl, a carbocyclic aromatic radical or a heterocyclic aromatic radical containing at least one N atom, and the metal is a transition metal cation carrying a double positive charge selected from Ni.sup.2+, Cu.sup.2+, Co.sup.2+, Zn.sup.2+, Mn.sup.2+, Fe.sup.2+, Cd.sup.2+ or Pt.sup.2+ or the radical VO.sup.2+.

High-molecular weight organic material containing a metal complex

Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.4, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sup.3, R.sup.4 and R.sup.5, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, are most suitable for coloring high molecular organic material.

Process for coloring high-molecular weight organic material using amine

Transition metal complexes of the compounds of the formulae I and II ##STR1## in which A is an isocylic or heterocyclic aromatic radical, R is --H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, R.sub.1 is --H, C.sub.1 -C.sub.4 -alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, --NO.sub.2, --CONH.sub.2, --CONHR.sub.2 or C.sub.2 -C.sub.5 -N-alkylcarbamoyl, X is --CH.dbd. or --N.dbd. and

Copper or nickel complexes of ligands containing an azomethine,

High molecular weight organic material is effectively colored by the incorporation therein of a copper or nickel complex of the ligand compound of formula I ##STR1## wherein A is an isocyclic or heterocyclic aromatic moiety, R is H, halogen, lower alkyl or alkoxy, R.sub.1 is H, lower alkyl, phenyl or substituted phenyl, and B is H, lower alkyl, ureido or substituted ureido, guanidino, anilino, benzamido or a heterocyclic aromatic moiety.

Polymer composition pigmented with copper or nickel complexes of ligands

Process for mass-coloring high-molecular organic material, which comprises using a metal complex of the formulae I and/or Ia ##STR1## in which R is a hydrogen or chlorine atom or a methyl or methoxy group, R.sub.1 is a hydrogen atom, C.sub.1 -C.sub.4 -alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, --NO.sub.2, --CONH.sub.2 --CONHR.sub.2 or C.sub.2 -C.sub.5 -N-alkylcarbamoyl, X is --CH.dbd. or --N.dbd., M is a divalent transition metal, and A is phenyl or substituted phenyl and R.sub.2 is alkyl, phenyl or substituted phenyl. The resulting colorations are distinguished by high tinctorial strength and good fastness properties, such as light, weathering and migration fastness properties.

Process for coloring high-molecular organic material, and novel metal

Monoazo pigment compounds of the formula ##STR1## wherein X is a group of the formula ##STR2## R is hydrogen or methyl, R.sub.1 and R.sub.2 are hydrogen, chlorine, methyl or methoxy, Y is methyl or phenyl, or Y is --O, --S--, --N(R.sub.3)-- or --C(R.sub.4).dbd.CH--, each of which is bound on the ring A in the ortho-position with respect to the --NHCO-- group to form a benzoxazolone, benzothiazolone, benzimidazolone or quinolone-2, with R.sub.3 and R.sub.4 being hydrogen or methyl, and m and n independently of one another are each 1 or 2, are useful as high-grade pigments, for pigmenting high-molecular weight organic material. The pigments are distinguished in particular by good fastness to light, migration and weather.

Monoazo pigments derived from aminophthalimides and substituted

A monoazo pigment of the formula ##STR1## in which A is an aromatic radical containing a 5-membered or 6-membered hetero-ring which has a -CONH group bonded as part of the ring, R is an aromatic radical and B is a H atom, an alkoxy group having 1-4 C atoms, an aliphatic radical containing at most 6 C atoms, an aryl radical, an aralkyl group having 1-4 C atoms, an amino group, an alkylamino group or an arylamino group, which shows high tinctorial strength and good fastness to light, over-lacquering, migration, weathering and heat.

Hetero-aryl azo acylamino substituted aceto-acetarylide pigments

Diazo pigments of the formula ##STR1## wherein R denotes an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radical, X denotes a hydrogen or halogen atom, an alkyl or alkoxy group containing 1 to 4 carbon atoms, or a nitro, cyano, trifluoromethyl or carboxylic acid ester group, and Y denotes a hydrogen or halogen atom, an alkyl or alkoxy group containing 1 to 4 carbon atoms or a nitro, cyano, trifluoromethyl or carboxylic acid ester group, are useful for coloring plastics and printing inks in fast yellow to orange shades.

Dicarboxylic acid ester diazo pigments

Disazo pigments of the formula ##STR1## WHEREIN A represents a carbocyclic or heterocyclic aromatic radical, in particular, those of the formula ##STR2## WHEREIN EACH OF X and Y represents a hydrogen or a halogen atom, an alkyl or alkoxy group of 1 to 6 carbon atoms, an aryloxy, trifluoromethyl, nitro, cyano, carboxylic ester or carboxy amide group, or wherein X and Y together represent a fused benzene ring are valuable pigments coloring plastics and lacquers in yellow to orange shades of excellent fastness properties.

Tetrachloro substituted disazo pigments

Disazo pigments of the formula ##STR1## wherein A denotes a phenylene or naphthylene radical, R denotes an aryl, alkyl or alkenyl group optionally substituted by halogen atoms, by hydroxyl, alkoxy or alkylmercapto groups containing 1-6 C atoms, by alkoxycarbonyl groups containing 2-6 C atoms or cyano, aryl, aryloxy, arylmercapto or heterocyclic radicals, or denotes a heterocyclic radical, and the X and Y denote H atoms or substituents which do not confer solubility in water are useful for coloring plastics lacquers and printing inks in yellow to orange shade of good fastness properties.

Disazo pigments containing acylamino groups

A disazo pigment of the formula ##STR1## WHEREIN X and Y are hydrogen, chlorine, alkyl of 1 - 4 C-atoms or one of X and Y can be alkoxy of 1 - 4 C-atoms and Z is chlorine or methyl, which is useful for pigmenting high molecular organic material and shows excellent fastness to light and weather.

Disazo pigment containing at least 2 chlorine atoms and process for

New disazo pigments of the formula ##SPC1## R being hydrogen, halogen, alkyl, alkoxy, nitrile, trifluormethyl, aryloxy, phenylsulfonyl or benzoyl, m and n 1 or 2, X hydrogen, halogen, alkyl, alkoxy, nitro, nitrile, trifluormethyl or carboxylic acid ester are prepared. The compounds are useful for pigmenting high molecular weight organic materials such as polyamides, polyurethanes and polyesters.

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Arlesheim, Switzerland

Georg Cseh