Patents by Inventor Stefan Hari
Stefan Hari 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: 5395926Abstract: Compounds of formula ##STR1## wherein R is hydrogen or a group ##STR2## M.sub.1 and M.sub.2 are each independently of the other an alkali metal or alkaline earth metal or aluminum or a group of formula ##STR3## wherein n is 1, 2 or 3, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or C.sub.1 -C.sub.8 alkyl,X.sub.1 and X.sub.2 are each independently of the other --N.dbd. or --CH.dbd.,Q.sub.1 and Q.sub.2 are each independently of the other radicals of formula ##STR4## These compounds have excellent suitability for pigmenting organic material of high molecular weight, preferably polyolefins, and have superior lightfastness.Type: GrantFiled: September 22, 1993Date of Patent: March 7, 1995Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Olof Wallquist
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Patent number: 5380870Abstract: Mixed crystals of at least two different compounds of formula ##STR1## wherein A and B are each independently of the other a cation of formula ##EQU1## or N.sup.+ H(R.sub.1)(R.sub.2)(R.sub.3) M is a mono-, di- or trivalent metal cation, n is 1, 2 or 3, R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, C.sub.1 -C.sub.22 alkyl, C.sub.7 -C.sub.24 aralkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.6 -C.sub.18 aryl, m is 0 or 1, and R is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, in which compounds of formula I that form the mixed crystals the cations A and B constitute a composite structure ##EQU2## wherein x is a value from 0.2 to 0.8, and the X-ray diffraction pattern of said mixed crystals differs from that of the corresponding compounds in which x is 1 or 0.These mixed crystals can be used as pigments for colouring organic material of high molecular weight and have exceptional properties, especially dispersibility, heat- and lightfastness.Type: GrantFiled: December 14, 1993Date of Patent: January 10, 1995Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Olof Wallquist, Fritz Herren, Thomas Eichenberger
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Patent number: 5298609Abstract: Compounds of formula I ##STR1## wherein R is a radical of formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III ##STR2## and B is a radical of formula ##STR3## wherein n is 1 or 2,R.sub.1 is --H or --Cl,R.sub.2 is --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, --CONH--phenyl, --NHCO-phenyl or phenoxy, each unsubstituted or substituted in the phenyl nucleus by one or two chlorine atoms or by one or two methyl, methoxy or ethoxy groups,R.sub.3 is C.sub.5 -C.sub.12 cycloalkyl, which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.5 -C.sub.6 cycloalkyl groups,R.sub.4 and R.sub.5 are each independently of the other --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.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3, andX is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2,are suitable for use as pigments, especially for colouring polyolefins.Type: GrantFiled: July 14, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 5280121Abstract: Compounds of formula ##STR1## wherein R is C.sub.7 -C.sub.21 alkyl, C.sub.4 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl-substituted C.sub.1 -C.sub.4 alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, chloro, bromo, methyl or methoxy,Z is a direct bond or --O--, --S--, --NH--, --CO--, --SO.sub.2 -- or --NHCO--, andn is 0 or 1.These compounds have excellent suitability as pigments for coloring organic material of high molecular weight, especially polyvinyl chloride, polyolefins and paints.Type: GrantFiled: June 30, 1992Date of Patent: January 18, 1994Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 5151505Abstract: 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.Type: GrantFiled: November 13, 1990Date of Patent: September 29, 1992Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh
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Patent number: 5071967Abstract: 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.Type: GrantFiled: February 11, 1991Date of Patent: December 10, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Jost von der Crone
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Patent number: 4997920Abstract: 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.Type: GrantFiled: September 11, 1989Date of Patent: March 5, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Olof Wallquist, Jost von der Crone
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Patent number: 4992495Abstract: 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.Type: GrantFiled: June 16, 1988Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh
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Patent number: 4980458Abstract: Mixed crystals of at least two different compounds of formula I ##STR1## wherein R is --CH.sub.3, phenyl, --COOCH.sub.3, --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, M.sup.+ and M.sub.1.sup.+ are each independently of the other an alkali metal cation, an alkaline earth metal cation or a heavy metal cation or NH.sub.4.sup.+ ; wherein X, Y, X' and Y' are each independently hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, wherein at least two of the cations M.sup.+ and M.sub.1.sup.+ in the compounds forming the mixed crystals of formula I are different and the X-ray diffraction patterns of the mixed crystals differ from the X-ray diffraction patterns of the individual components and of their sum.Type: GrantFiled: May 8, 1989Date of Patent: December 25, 1990Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Arnold Grubenmann, Andreas Burkhard
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Patent number: 4946948Abstract: Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --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 phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --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.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.Type: GrantFiled: August 31, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Fridolin Babler
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Patent number: 4737581Abstract: Azo compounds of the formula I ##STR1## wherein X is --H, --CH.sub.3, --CF.sub.3, --NO.sub.2, --COOR.sub.1, --NHCOR.sub.2 or --COHN.sub.2, and R.sub.1 and R.sub.2 are as defined in claim 1, are suitable for pigmenting high-molecular organic material.Type: GrantFiled: April 18, 1985Date of Patent: April 12, 1988Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 4602961Abstract: A process for pigmenting high molecular weight organic material, which comprises using, as pigment, a monoazo compound of the formula ##STR1## wherein A is a carbocyclic aromatic radical, R is an aliphatic, cycloaliphatic, araliphatic or aromatic radical or an alkoxy group, and Q is a hydrogen or a halogen atom or a methyl group.The colorations obtained, for example in plastics, filaments, lacquers and prints, have very high color strength, high saturation, good dispersibility, good fastness to overspraying, migration, heat, light and atmospheric influences, and good gloss.Type: GrantFiled: September 7, 1984Date of Patent: July 29, 1986Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 4473500Abstract: 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.Type: GrantFiled: May 3, 1982Date of Patent: September 25, 1984Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Stefan Hari
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Patent number: 4400319Abstract: Compounds of the formula I ##STR1## wherein the symbols Z, R.sub.1, R.sub.2, m and n have the meanings defined in claim 1, are suitable, as high-grade pigments, for dyeing high-molecular organic material. They are characterized in particular by good fastness to migration and to cross-lacquering, as well as to weather and light.Type: GrantFiled: September 24, 1981Date of Patent: August 23, 1983Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Arnold Wick
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Patent number: 4263205Abstract: Monoazo pigments of the formula I ##STR1## in which R is the radical of a carbocyclic or heterocyclic aromatic amine and R.sub.1, R.sub.2 and R.sub.3 are hydrogen, halogen, alkyl, alkoxy, alkoxycarbonyl, substituted or unsubstituted aminocarbonyl, nitro, cyano or trifluoromethyl. These pigments are suitable for coloring high molecular weight organic material and are distinguished by their easy accessibility and good general fastness properties and in particular by high clarity of color shade.Type: GrantFiled: May 31, 1979Date of Patent: April 21, 1981Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 4220586Abstract: 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.Type: GrantFiled: October 31, 1977Date of Patent: September 2, 1980Assignee: Ciba-Geigy CorporationInventors: Georg Cseh, Armand Roueche, Stefan Hari
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Patent number: 4138568Abstract: Process for the manufacture of benzimidazolones-(2) wherein an o-phenylenediamine is reacted with optionally alkylated urea in the ratio of 1 to 1.3 moles per mole o-phenylenediamine in an organic solvent which has a solubility in water of not more than 5 g/l and has a boiling point above 100.degree. C, at a temperature between 100.degree. and 200.degree. C.Type: GrantFiled: May 31, 1977Date of Patent: February 6, 1979Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Ernesto Rinaldi, Josef Somlo
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Patent number: 4093613Abstract: Azo pigments of the formula ##STR1## in which R.sub.1 and R.sub.2 denote H atoms, alkyl groups with 1-6 C atoms or aryl radicals, Y denotes an O or S atom or an imino group, Z denotes an O atom or an imino group and Y.sub.1 -Y.sub.4 denote H or halogen atoms, alkyl or alkoxy groups containing 1-4 C atoms, or nitro, trifluoromethyl or alkoxycarbonyl groups containing 2-4 C atoms are valuable pigments coloring plastics, melts, spinning solutions, lacquers paints and printing inks in yellow to red shades of high tinctorial strength and excellent fastness properties.Type: GrantFiled: July 19, 1976Date of Patent: June 6, 1978Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Armand Roueche
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Patent number: 4088641Abstract: Azo pigments of the formula ##STR1## wherein A represents the radical of a heterocyclic diazo component are valuable pigments coloring plastics, melts, spinning solutions, lacquers paints and printing inks in yellow to red shades of great color strength and excellent fastness properties.Type: GrantFiled: February 17, 1976Date of Patent: May 9, 1978Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Rolf Muller, Rudolf Mory
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Patent number: RE35359Abstract: 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.6 -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.Type: GrantFiled: September 26, 1994Date of Patent: October 22, 1996Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh