Patents by Inventor Ivan Orban
Ivan Orban 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: 6492440Abstract: A product obtainable by 1) reacting a compound of the formula (&agr;) with a compound of the formula (&bgr;) in a molar ratio of 1.2:1 to 1.4:1; 2) reacting the end groups of the formula (&ggr;) being present in the product of the reaction 1) with e.g. dibutylamine in a molar ratio of 2:1.7 to 2:3; the reactions 1) and 2) being carried out in an organic solvent in the presence of an inorganic base; and 3) transferring the groups of the formula being present in the product of the reaction 2) to groups of the formula said transfer being carried out by reacting the product of the reaction 2) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst. The products obtained are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers such as polyolefins.Type: GrantFiled: June 9, 2000Date of Patent: December 10, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: James Peter Galbo, Nicola Lelli, Valerio Borzatta, Jean-Pierre Wolf, Michael Ackerman, Piero Piccinelli, Ivan Orban
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Patent number: 6403680Abstract: A product obtained by 1) reacting a compound of the formula (&agr;) with a compound of the formula (&bgr;) in a stoichiometric ratio to obtain a compound of the formula (&ggr;) 2) reacting the compound of the formula (&bgr;) with the compound of the formula (&ggr;) in a molar ratio of 0.4:1 to 0.75:1; 3) reacting the end groups of the formula (&dgr;) being present in the product of the reaction 2) with e.g. dibutylamine in a molar ratio of 2:1.7 to 2:3; the reactions 1) to 3) being carried out in an organic solvent in the presence of an inorganic base; and 4) transferring the groups of the formula being present in the product of the reaction 3) to groups of the formula said transfer being carried out by reacting the product of the reaction 3) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst; R1 is in particular a hydrocarbyl radical, B is e.g.Type: GrantFiled: November 18, 1999Date of Patent: June 11, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: James Peter Galbo, Nicola Lelli, Valerio Borzatta, Jean-Pierre Wolf, Michael Ackerman, Piero Piccinelli, Ivan Orban
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Patent number: 5726310Abstract: 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine is prepared by reacting cyanuric chloride with m-xylene at a temperature of 0.degree.-110.degree. C. in the presence of a Lewis acid and at least one inert chlorinated aromatic solvent to give the intermediate 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine. This intermediate, without being isolated, is then reacted with resorcinol to give the final desired product 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine in good yield.Type: GrantFiled: December 3, 1996Date of Patent: March 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ivan Orban, Martin Holer, Andre Kaufmann
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Patent number: 5688969Abstract: The invention relates to a process for the preparation of thiophene-2,5-dicarboxylic acid by reacting thionyl chloride and adipic acid, with pyridine as catalyst, which process comprisesA) adding 1 part of adipic acid to 3 to 6 parts of thionyl chloride, mixed with a catalytic amount of pyridine,B) adding a further 4 to 7 parts of thionyl chloride in the temperature range from 85.degree. to 95.degree. C.,C) removing excess thionyl chloride and volatile by-products under reduced pressure, andD) bringing the reaction to completion in the temperature range from 140.degree. to 160.degree. C., andE) preparing a salt of thiophene-2,5-dicarboxylic acid by hydrolysing the chloride obtained with an aqueous solution of an alkaline earth metal hydroxide or an alkali metal hydroxide, andF) obtaining the free acid from this salt with a mineral acid.Type: GrantFiled: November 18, 1996Date of Patent: November 18, 1997Assignee: Ciba Specialty Chemicals CorporationInventor: Ivan Orban
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Patent number: 5616787Abstract: The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.Type: GrantFiled: October 11, 1995Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventors: Rinaldo Husler, Ivan Orban, Martin Holer
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Patent number: 5436322Abstract: A process for the preparation of compounds of the formula I is described ##STR1## in which R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.7 alkyl; and R.sup.3 is hydrogen or halogen, by reaction of a diazonium salt of a 2-nitroaniline in acid aqueous solution with a phenol dispersed in water.The process comprises employing as the dispersant a C.sub.8 -C.sub.20 alkanesulfonic acid or a corresponding alkanesulfonate or a mixture of sulfonic acid and sulfonate together with a polyvinyl alcohol.The resulting compounds of the formula I can advantageously be reacted further to give benzotriazoles of the formula V ##STR2## which are used as light stabilizers.Type: GrantFiled: September 12, 1994Date of Patent: July 25, 1995Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Martin Holer
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Patent number: 5130429Abstract: Process for the methylation of compounds at least one group of the formula (I) ##STR1## by means of a mixture of formaldehyde and formic acid in a reaction medium consisting of an aromatic hydrocarbon solvent.Type: GrantFiled: November 27, 1991Date of Patent: July 14, 1992Assignee: Ciba-Geigy CorporationInventors: Piero Piccinelli, Ivan Orban, Martin Holer, Valerio Borzatta
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Patent number: 4716244Abstract: If the transesterification of esters of formula II ##STR1## with alcohols of formula III A--OH).sub.m is catalysed by treatment with catalytic amounts of an organic or inorganic zinc salt and the resultant melt is subsequently distilled in a short-time distillation apparatus under specific conditions, then compounds of the formula ##STR2## are obtained in virtually quantitative yield, in which formulae I, II and III n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, B is methyl or tert-butyl and R is methyl or ethyl. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.Type: GrantFiled: April 21, 1986Date of Patent: December 29, 1987Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4699939Abstract: Compounds of formula I ##STR1## wherein R.sub.1, R.sub.2 and A are essentially hydrocarbyl or substituted hydrocarbyl groups with at least one of R.sub.1 and R.sub.2 being cyclohexyl, n is 0, 1 or 2, m is an integer of 1 to 4 and X is oxygen or --N(R.sub.3)-- wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl.Type: GrantFiled: October 8, 1986Date of Patent: October 13, 1987Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Hans-Rudolf Meier, Paul Dubs, Samuel Evans, Peter Hofmann
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Patent number: 4683326Abstract: Seeding a melt of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with a small amount of the crystalline .beta.-, .delta.- or .lambda.-modification of this compound in an extruder, kneader or internal mixer at 70.degree.-130.degree. C. gives, within a few minutes, pure crystalline product without the use of a hitherto mandatory and environmentally undesirable solvent.Also described is a novel crystalline thermostable .lambda.-modification of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].Type: GrantFiled: July 10, 1986Date of Patent: July 28, 1987Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Werner Fussenegger
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Patent number: 4594444Abstract: If the transesterification of esters of the formula II ##STR1## with alcohols of the formula III ##STR2## is catalyzed by treatment with catalytic amounts of an oxide or an organo-metallic compound of a metal of the fourth main group or subgroup of the periodic system, and if the resulting melt is then distilled in a flash distillation apparatus under specific conditions, compounds of the formula ##STR3## are obtained in a virtually quantitative yield. In the above formulae, R is methyl or ethyl, A is a radical of an m-hydric aliphatic alcohol, E is methyl or tert-butyl, m is 1 to 4 and n is 0 to 2. The products thus obtained do not contain any interfering by-products and do not have to be additionally purified.Type: GrantFiled: December 12, 1984Date of Patent: June 10, 1986Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4536593Abstract: If the transesterification of esters of the formula ##STR1## with alcohols of the formula III A--(OH).sub.m is catalyzed by successive treatment with catalytic amounts (a) of a tin compound of a metal of the fourth main group or the fourth sub-group of the periodic system and (b) of an acid earth, compounds of the formula I ##STR2## are obtained in virtually quantitative yield. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.R is methyl or ethyl, A is a radical derived from an m-hydric aliphatic alcohol, n is 0 to 2, and m is 1 to 4.Type: GrantFiled: July 5, 1983Date of Patent: August 20, 1985Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Eduard Troxler
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Patent number: 4507463Abstract: A novel process for producing compounds of the formula I ##STR1## by polycondensation of a diol of the formula II ##STR2## with a dicarboxylic acid ester of the formula III ##STR3## R.sub.1 and R.sub.2 are independently alkylene or alkenylene, R.sub.3 is lower alkyl and n is 18 to 25.The process according to the invention is characterized in that the reaction medium is treated, in the presence of at least 0.05 mol %, relative to the diol of the formula II, of an organometallic compound of titanium or tin, at a maximum steam temperature of 75.degree. C., until the formed methanol has been almost completely distilled off; distillation is then continued for at least 3 hours, during which time the volume of the reaction solution is kept approximately constant by successive additions of solvent, at a steam temperature of between 100.degree. and 145.degree. C.; the reaction solution is subsequently concentrated by evaporation, and the melt which remains is finally ground after it has solidified.Type: GrantFiled: May 1, 1984Date of Patent: March 26, 1985Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4492791Abstract: The known reaction of dichlorotriazines of the formula II ##STR1## in which Q is an ether or amino radical, with diamines of the formula IIIPip--NH--R--NH--Pip (III)in which Pip is a radical of the formula ##STR2## in which R.sup.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -alkenyl, C.sub.7 -C.sub.11 -phenylalkyl, C.sub.2 -C.sub.8 -alkanoyl or C.sub.3 -C.sub.5 -alkenoyl and R is a divalent organic radical leads to undesirable, sparingly soluble by-products. The formation of these by-products can be suppressed if the reaction is carried out in a water-immiscible organic solvent with the addition of an aqueous base--preferably NaOH or KOH--under pressure at 140.degree.-220.degree. C.Type: GrantFiled: April 25, 1983Date of Patent: January 8, 1985Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Eduard Troxler
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Patent number: 4275211Abstract: A process for producing piperidines of the formula (I) ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, from a ketone of the formula (II) R.sub.1 --CH.sub.2 --C(O)--CH.sub.3, wherein R.sub.1 has the meaning given above, and ammonia, in which process there is used as catalyst a strongly acid ion exchanger having a medium or large mesh size or having large macropores.Type: GrantFiled: November 5, 1979Date of Patent: June 23, 1981Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Eduard Troxler
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Patent number: 3960875Abstract: 2,2,6,6-Tetramethyl-4-oxopiperidine is prepared from 2,2,4,4,6-pentamethyl-2,3,4,5-tetramethylpyrimidine (acetonine) by heating in the presence of acetone, diacetone alcohol or water. These regents may be used in excess or an organic solvent is added. The preferred modification is the heating of acetonine hydrate in an excess of acetone or in an acetone-methanol mixture to about 40.degree. to 65.degree.C for several hours. The use of diacetone alcohol permits higher reaction temperatures leading to shorter reaction times.Type: GrantFiled: June 21, 1974Date of Patent: June 1, 1976Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Hanns Lind, Heimo Brunetti, Jean Rody
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Patent number: 3959295Abstract: 2,2,6,6-Tetramethyl-4-oxopiperidine is prepared from acetone and ammonia in the presence of acidic catalysts. Suitable catalysts are Lewis acids, protionic acids and their salts with ammonia or with organic bases, as for example BF.sub.3, NH.sub.4 Cl or H.sub.2 SO.sub.4. The addition of an alcohol such as methanol as well as the use of a cocatalyst may promote the reaction. The process may be carried out in two steps, in the first of which the temperature is held below 35.degree.C. In the second step a further amount of acetone is added and the temperature is rised to about 40.degree. to 65.degree.C.Type: GrantFiled: June 21, 1974Date of Patent: May 25, 1976Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Hanns Lind, Heimo Brunetti, Jean Rody, Michael Rasberger
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Patent number: 3953459Abstract: 2,2,6,6-Tetramethyl-4-oxopiperidine is prepared from 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine by treatment with an acidic catalyst. Suitable catalysts are Lewis acids, protonic acids and their salts with ammonia or organic bases. The reaction may be carried out in organic solvents, preferably in acetone, by gentle heating, for example at 40.degree. to 65.degree.C. Yields of 95% are obtainable after a reaction of several hours.Type: GrantFiled: June 21, 1974Date of Patent: April 27, 1976Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Hanns Lind, Heimo Brunetti, Jean Rody
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Patent number: 3943139Abstract: A new process for producing triacetone-amine by reacting phoron and ammonia under pressure and higher temperature.Type: GrantFiled: October 4, 1973Date of Patent: March 9, 1976Assignee: CIBA-GEIGY CorporationInventors: Ivan Orban, Jean Rody