Ciba-geigy Corporation

Ciba-geigy Ag

Paul Lienhard

Abul Iqbal

Georg Cseh

Fabio Beffa

Andre Pugin

Dieter Reinehr

Edward E Jaffe

Gert Hegar

Dieter Mausezahl

Francois L'Eplattenier

Armand Roueche

Heinz Peter

Martin Tanner

Werner Saar

Walter Wiedemann

Robert Von Arx

Charles Soiron

The invention includes printing ink compositions containing an organic solution of a film-forming polymer and a dye salt of formula ##STR1## wherein R is a group of formula ##STR2## wherein R.sub.1 is C.sub.1 -.sub.4 alkyl, R.sub.2 and R.sub.3 are each independently of the other hydrogen, CH.sub.2 X, SO.sub.2 Y or NHCOZ, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.5 is CH.sub.2 X, SO.sub.2 Y or NHCOZ, X is a NHCOR.sub.6 or NR.sub.7 SO.sub.2 R.sub.6 group, Y is NR.sub.8 R.sub.9 or N(R.sub.8).sub.2, and Z is C.sub.1 -C.sub.4 alkyl or NHR.sub.9, R.sub.6 is C.sub.1 -C.sub.4 alkyl, unsubstituted phenyl or phenyl which is substituted by C.sub.1 -C.sub.4 alkyl or halogen, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.8 is hydrogen, C.sub.1 -C.sub.4 alkyl or a ##STR3## group, and R.sub.9 is hydrogen C.sub.1 -C.sub.4 alkyl or phenyl, and R', R' and R'' are alkyl radicals containing together 10 to 24 carbon atoms, or a mixture of such dye salts. These dye salts are suitable for colouring organic solutions of polymers and are distinguished by their good solubility in organic solvents as well as by their purity, high saturation, adhesion, storage stability, and fastness to light and weathering.

Dye salts of the anthraquinone dye series

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

Thermoplastic, high-molecular-weight material which can be processed in the melt and which contains at least one nickel complex derived from a ligand of the formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of one another, are --H, halogen or --CH.sub.3, R.sub.5 and R.sub.6, independently of one another, are --H or C.sub.1 -C.sub.4 alkyl, A is a para-phenylene radical of the formula II or a mixture of a para-phenylene radical of the formula II with an orthophenylene radical of the formula III ##STR2## the proportion of ortho-phenylene radical in the mixture being not more than 60% by weight, and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3 or --OC.sub.2 H.sub.5, and Y.sub.1 and Y.sub.2, independently of one another, are --H, halogen, --CH.sub.3 or --OCH.sub.3, or Y.sub.1 is a radical of the formula ##STR3## and Y.sub.2 is --H, or Y.sub.1 and Y.sub.2 together are --NHCONH-- or --CONHCO--, where R.sub.7 is --H or C.sub.1 -C.sub.4 alkyl and R.sub.8 is --H, halogen, --CH.sub.3 or --OCH.sub.3.

Thermoplastics containing a nickel complex pigment

The invention relates to novel 1:1 metal complexes of a divalent transition metal and an azo compound of the formula (1) ##STR1## wherein X is a hydrogen or a halogen atom, an alkyl, alkoxy, aryloxy, nitro, acylamino, ureido, arylureido, thioureido, thiocyano or sulfamoyl group or a phthalimido group which is unsubstituted or substituted by halogen atoms,

Metal complexes of substituted 4-(2-carboxy-phenylazo-5-pyrazolones

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

Process for mass-coloring nylon in dark brown, dark violet and black shades, which comprises using as dye either mixtures of the 1:2 chromium complex of a monoazo dye of the formula I ##STR1## and the 1:2 chromium complex of a monoazo dye of the formula II ##STR2## or a mixed 1:2 chromium complex of a monoazo dye each of the formula I and the formula II in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.

Process for mass-coloring nylon with 1:2 chromium complex azo dye

The invention relates to a simplified process for the manufacture of 1:1 metal complexes of isoindoline azines of the formula ##STR1## wherein R is hydrogen, alkyl or aryl, Q contains an isocyclic or heterocyclic radical, acyl, carbamoyl or thiocarbamoyl, and Y is the radical of an active methylene group or aromatic amine, which comprises reacting a compound HQ or a hydrazone with an ortho ester or amidine in the presence of a metal donor at elevated temperature in a polar solvent. Pigments made by this process are lightfast and are useful in coloring plastics.

Process for the manufacture of metal complexes of isoindoline azines

1:1 Nickel complexes of azines of the formula I or of a tautomer thereof ##STR1## wherein R.sub.1 is hydrogen or methyl, R.sub.2 is methyl or carbamoyl, R.sub.3 is hydrogen or chlorine, R.sub.4 is hydrogen, chlorine, methyl, trifluoromethyl or sulfamoyl, R.sub.5 is hydrogen or chlorine, R.sub.6 is hydrogen, chlorine, bromine, methyl, methoxy, trifluoromethyl, carbamoyl or alkanoylamino containing 2 to 4 carbon atoms, with the proviso that, if R.sub.2 is carbamoyl, at least two of the substituents R.sub.3 to R.sub.6 are halogen atoms and/or trifluoromethyl groups, color plastics, lacquers and printing inks in orange to red shades of outstanding fastness properties.

Nickel complex pigments of azines

The invention relates to a process for the manufacture of 1-hydrazono-isoindolines of the formula ##STR1## wherein Y is a methine or imine radical and the ring A can contain substituents which do not confer solubility in water, by reacting an iminoisoindoline of the formula ##STR2## with hydrazine or a hydrazine donor, in a polar solvent, which process comprises carrying out the reaction at temperatures below 80.degree. C. These hydrazono-isoindolines are obtained in excellent yield and purity and can be used without further purification as starting materials for further syntheses.

Process for the manufacture of hydrazono-isoindolines

Isoindoline compounds and the manufacture and use thereof

Red monoazo dyestuffs frm diazotised 1-aminobenzene-2-sulphonic acid-N-methyl-N-cyclohexylamide or 1-amino-4-,-5- or -6-methyl-benzene-2-sulphonic acid-N-methyl-N-cyclohexylamide and 2-amino-8-hydroxynaphthalene-6-sulphonic acid are disclosed which are particularly distinguished by their good migration and levelling properties and excellent fastness to light. Said dyestuffs are moreover suitable for obtaining very even combination dyeings together with known blue or yellow acid dyestuffs. These dyestuffs are particularly suited for the dyeing of carpeting, upholstery fabrics and drapery materials.

Red monoazo sulphonic acid dyestuffs for polyamide

The invention relates to a process for coloring polyamides in the melt with azo pigments of the formula ##STR1## wherein A is the radical of a diazo or tetraazo component, R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms or alkyl, cyclo alkyl, phenylalkyl or aryl radicals, and n is 1 or 2. Articles colored with the pigments have level, strong yellow shades of excellent fastness to light, wet processing, rubbing and thermofixation.

Process for coloring fibre forming polyamides in the melt with azo

Azo dyestuff sulfonic acid salts of the formula: ##STR1## wherein A represents a carbocyclic or heterocyclic aromatic radical, B represents an aliphatic, cycloaliphatic or araliphatic amine, X represents a hydrogen atom or a substituted or unsubstituted alkyl group, a cycloalkyl, aralkyl or aryl group, Y represents a hydrogen or halogen atom, a nitro, cyano, acyl, sulfonic acid, arylsulfonyl, alkoxycarbonyl group or a substituted or unsubstituted alkyl, sulfamoyl or carbamoyl group, Z represents a substituted or unsubstituted alkyl group or an aryl radical, m and n are 1 or 2; said dyestuffs salts having good solubility in organic solvents and functioning to color solutions of film forming polymers in yellow to orange shades.

Growing community of inventors

Frenkendorf, Switzerland

Paul Lienhard