Patents by Inventor Paul Lienhard
Paul Lienhard has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5416227Abstract: 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.Type: GrantFiled: February 14, 1994Date of Patent: May 16, 1995Assignee: Ciba-Geigy CorporationInventors: Martin Tanner, Dieter Mausezahl, Paul Lienhard, Robert von Arx
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Patent number: 5066695Abstract: 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+.Type: GrantFiled: June 29, 1989Date of Patent: November 19, 1991Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Paul Lienhard, Walter Wiedemann
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Patent number: 4866112Abstract: 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.Type: GrantFiled: July 29, 1988Date of Patent: September 12, 1989Assignee: Ciba-Geigy CorporationInventors: Paul Lienhard, Edward E. Jaffe
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Patent number: 4847365Abstract: 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,Y is a hydrogen or halogen atom, an alkyl or alkoxy group, andR is an alkyl, alkoxycarbonyl, carbamoyl or alkylcarbamoyl group, orwherein X and Y, together with two vicinal carbon atoms of the benzene ring, form a fused benzene or imidazolone ring.These metal complexes, in particular the nickel and copper complexes, are suitable for the mass coloration of polymer fibres, especially polyolefins, polyamides or polyesters. The colored fibres have good fastness to heat, light and weather, as well as good rub- and wetfastness properties.Type: GrantFiled: February 17, 1988Date of Patent: July 11, 1989Assignee: Ciba-Geigy CorporationInventor: Paul Lienhard
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Patent number: 4775747Abstract: 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. andB is --H, C.sub.1 -C.sub.4 -alkyl, --NHCONH.sub.2, --NHCONH-C.sub.1 -C.sub.4 -alkyl, --NHCONR.sub.2, --NHCSNH.sub.2, --NHCSR.sub.3, --NHC(NH)NH.sub.2, --NHR.sub.2, --NHCOR.sub.3, --NHSO.sub.2 R.sub.3 or a heterocyclic aromatic radical, and R.sub.2 and R.sub.3 are phenyl or substituted phenyl, are suitable for pigmenting high-molecular organic material.Type: GrantFiled: February 17, 1987Date of Patent: October 4, 1988Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Paul Lienhard
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Patent number: 4670486Abstract: 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.Type: GrantFiled: June 13, 1985Date of Patent: June 2, 1987Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Paul Lienhard
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Patent number: 4639477Abstract: 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.Type: GrantFiled: June 13, 1985Date of Patent: January 27, 1987Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Paul Lienhard
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Patent number: 4527994Abstract: 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.Type: GrantFiled: July 12, 1984Date of Patent: July 9, 1985Assignee: Ciba-Geigy CorporationInventors: Paul Lienhard, Werner Saar
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Patent number: 4496727Abstract: 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.Type: GrantFiled: September 24, 1982Date of Patent: January 29, 1985Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard
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Patent number: 4460768Abstract: 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.Type: GrantFiled: December 16, 1981Date of Patent: July 17, 1984Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard, Andre Pugin
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Patent number: 4414395Abstract: 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.Type: GrantFiled: March 6, 1981Date of Patent: November 8, 1983Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard
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Patent number: 4385174Abstract: 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.Type: GrantFiled: March 9, 1981Date of Patent: May 24, 1983Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard
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Patent number: 4378970Abstract: 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.Type: GrantFiled: October 15, 1981Date of Patent: April 5, 1983Assignee: Ciba-Geigy AGInventors: Paul Lienhard, Fabio Beffa
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Patent number: 4370431Abstract: 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.Type: GrantFiled: August 10, 1981Date of Patent: January 25, 1983Assignee: Ciba-Geigy CorporationInventors: Paul Lienhard, Armand Roueche
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Patent number: 4359418Abstract: 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.Type: GrantFiled: April 9, 1981Date of Patent: November 16, 1982Assignee: Ciba-Geigy CorporationInventors: Paul Lienhard, Gert Hegar
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Patent number: 4355159Abstract: 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.Type: GrantFiled: May 13, 1980Date of Patent: October 19, 1982Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard, Andre Pugin
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Patent number: 4349671Abstract: The invention relates to a process for the manufacture of 1:1 metal complexes of azines of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, an alkyl or aryl group, R.sub.2 is an isocyclic or heterocyclic radical containing a hydroxyl or mercapto group adjacent to the azomethine group, Y is the radical of a compound which contains active methylene groups, or of an aryl or heteroaryl amine, and the ring A can contain substituents that do not confer solubility in water, which process comprises reacting a compound of the formula ##STR2## wherein R.sub.3 is a hydrogen atom or an alkyl radical, R.sub.4 is an alkyl, aryl or heteroaryl radical or the radical of the formula ##STR3## or R.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring, and Y has the given meaning, with a hydrazone of the formula ##STR4## in the presence of a transition metal donor and in a polar organic solvent, at temperatures above 100.degree. C.Type: GrantFiled: March 5, 1981Date of Patent: September 14, 1982Assignee: Ciba-Geigy CorporationInventors: Abul Iqbal, Paul Lienhard
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Patent number: 4327212Abstract: The isoindoline-azine nickel complex of the formula ##STR1## colors plastics, lacquers and printing inks in yellow shades of outstanding fastness properties.Type: GrantFiled: May 19, 1980Date of Patent: April 27, 1982Assignee: Ciba-Geigy CorporationInventors: Paul Lienhard, Francois L'Eplattenier
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Patent number: 4312808Abstract: Red monoazo dyestuffs from diazotized 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.Type: GrantFiled: January 11, 1980Date of Patent: January 26, 1982Assignee: Ciba-Geigy AGInventors: Paul Lienhard, Fabio Beffa
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Patent number: 4290964Abstract: The invention relates to 11-aminoundecanoic acids and 11-aminoundeca-4,8-dienoic acids and the esters of these acids. They have the formula I ##STR1## wherein R.sup.1 and R.sup.3 are e.g. hydrogen and R.sup.2 and R.sup.4 are e.g. methyl and E is e.g. the radical --CH.sub.2 CH.sub.2 -- and R.sup.7 is hydrogen or an alkyl radical. The esters are suitable for the manufacture of salts of anionic dyes which are very readily soluble in organic solvents.Type: GrantFiled: February 29, 1980Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Paul Lienhard