Patents by Inventor Paul Dubs
Paul Dubs 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: 6127327Abstract: Described are products suitable as lubricant and fuel additives which are obtainable by reacting a polyunsaturated polymer, for example polybutadiene, polyisoprene, ring-opening polymerised polycyclooctenamer or polynorbomene, with at least one enophilic compound of the groups of the dihydrocarbyidithiophosphoric acids, dihydrocarbylmonothiophosphoric acids, dihydrocarbylphosphoric acids or mercaptans.Type: GrantFiled: June 24, 1999Date of Patent: October 3, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Hugo Camenzind, Paul Dubs
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Patent number: 6046263Abstract: Products are described which are obtainable by reacting compounds of formula I with compounds of formula IIa or/and IIb and IIIa or/and IIIb and additionally, where appropriate, IV ##STR1## wherein the general symbols are as defined in claim 1, the compound of formula I being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, the compound of formula IIa being, for example, diethanolamine, the compound of formula IIIa being, for example, methyl oleate, and the compound of formula IV being, for example, sulfur. The cited products can be used as liquid antioxidants in organic materials.Type: GrantFiled: May 19, 1998Date of Patent: April 4, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Rasberger, Samuel Evans, Paul Dubs, Stephan Allenbach
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Patent number: 6015899Abstract: Products are described which can be obtained by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, and the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.Type: GrantFiled: April 21, 1997Date of Patent: January 18, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Dubs, Roger Martin, Samuel Evans
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Patent number: 5932642Abstract: A description is given of novel compounds of formula I ##STR1## wherein R.sup.1, R.sub.2, R.sub.3, and R.sup.4 are hydrogen, alkyl, phenylalkyl, or alkoxy and where R.sub.5 and R.sub.6 are hydrogen or phenyl or together with the linking carbon atoms, are cycloalkenylene or cycloalkenylene which is interrupted by oxygen or sulfur. These compounds are useful as stabilizers for organic materials against oxidative, thermal or light-induced degradation.Type: GrantFiled: December 19, 1997Date of Patent: August 3, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Paul Dubs
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Patent number: 5739341Abstract: Products are described which can be obtained by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, and the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.Type: GrantFiled: June 2, 1995Date of Patent: April 14, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Dubs, Roger Martin, Samuel Evans
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Patent number: 5668206Abstract: Products are described which can be obtained by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, and the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.Type: GrantFiled: June 6, 1995Date of Patent: September 16, 1997Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Roger Martin, Samuel Evans
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Patent number: 5663128Abstract: Products are described which can be obtained by reacting components a), b), c) and d), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II, component c) is a compound of the formula III or a mixture of compounds of the formula III and component d) is a compound of the formula IV or a mixture of compounds of the formula IV, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate and the compound of the formula IV, being for example, sulfur or diisopropyl dithiophosphate.Type: GrantFiled: September 19, 1994Date of Patent: September 2, 1997Assignee: Ciba-Geigy CorporationInventors: Samuel Evans, Paul Dubs, Hugo Camenzind
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Patent number: 5510402Abstract: The novel compounds of the formula I ##STR1## in which n is an integer from the range from 4 to 8 and m is an integer from the range from 1 to 4,A is the aliphatic, aromatic, araliphatic or heterocyclic radical of a monobasic to tetrabasic carboxylic acid, andR.sup.1 and R.sup.1', independently of one another, are C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.8 cycloalkyl, are suitable for stabilizing organic material against thermal, oxidative or actinic degradation.Type: GrantFiled: November 24, 1993Date of Patent: April 23, 1996Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
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Patent number: 5478875Abstract: Products are described which can be obtained by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,4-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, and the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate. The abovementioned products can be used as liquid antioxidants in polymers and lubricants.Type: GrantFiled: April 1, 1993Date of Patent: December 26, 1995Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Roger Martin, Samuel Evans
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Patent number: 5473003Abstract: Compositions comprising an organic material which is sensitive to thermal, oxidative and/or actinic degradation and at least one compound of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl or (C.sub.1 -C.sub.4 alkyl)phenyl andp is a number from 4 to 18,with the proviso that Z.sub.1 and Z.sub.2 are not simultaneously tertiary alkyl radicals. Some of the compounds of the formula I are novel.The compounds of the formula I can also be employed as stabilizers as a mixture with compounds of the formula VI and/or of the formula VII ##STR2## in which n and the radicals R.sup.1, R .sup.1 ' and A are as defined in claims 14 and 15.Type: GrantFiled: December 21, 1994Date of Patent: December 5, 1995Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Paul Dubs, Bernard Gilg
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Patent number: 5427701Abstract: Novel compositions are described which comprises an elastomer or a lubricant and at least one compound of the formulae I or II ##STR1## The symbols R.sub.1, R.sub.2, R.sub.3, Z.sub.1 and Z.sub.2 are as defined in claim 1.The compounds of the formula II and some of the compounds of the formula I are novel, and they are used especially as antioxidants.Type: GrantFiled: July 14, 1994Date of Patent: June 27, 1995Assignee: Ciba-Geigy CorporationInventors: Hans R. Meier, Samuel Evans, Paul Dubs
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Patent number: 5376290Abstract: Novel compositions are described which comprise an elastomer or a lubricant and at least one compound of the formulae I or II ##STR1## The symbols R.sub.1, R.sub.2, R.sub.3, Z.sub.1 and Z.sub.2 are as defined in claim 1.The compounds of the formula II and some of the compounds of the formula I are novel, and they are used especially as antioxidants.Type: GrantFiled: October 18, 1991Date of Patent: December 27, 1994Assignee: Ciba-Geigy CorporationInventors: Hans R. Meier, Samuel Evans, Paul Dubs
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Patent number: 5356976Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 n-alkyl, isopropyl, s-butyl, cyclopentyl, cyclohexyl or .alpha.-methylbenzyl, R.sub.2 is C.sub.4 -C.sub.18 tert-alkyl or .alpha.,.alpha.-dimethylbenzyl, R.sub.3 is C.sub.1 -C.sub.28 alkyl, and R.sub.4 s methyl or ethyl, with the proviso that the --CHR.sub.3 R.sub.4 group contains at least 4 carbon atoms, are suitable for stabilizing organic material which is susceptible to degradation induced by heat, oxidation or actinic light.Type: GrantFiled: July 12, 1993Date of Patent: October 18, 1994Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
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Patent number: 5328621Abstract: The invention relates to novel compounds of formulae I, II and III ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.5 -C.sub.7 cycloalkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.5 -C.sub.7 cycloalkyl, and R.sub.3 is C.sub.1 -C.sub.18 alkyl or C.sub.3 -C.sub.18 alkenyl. The compounds are used as antiwear additives for lubricants.Type: GrantFiled: October 21, 1993Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Hugo Camenzind, Paul Dubs
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Patent number: 5298178Abstract: Composition comprising an aqueous or partially aqueous functional fluid susceptible to degradation by a metal; and b) a metal deactivator having the formula I: ##STR1## in which X is a group having the formula II. ##STR2## in which R is hydrogen or C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: May 7, 1992Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventors: Robert M. O'Neil, Paul Dubs
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Patent number: 5273669Abstract: A lubricant based on a mineral or synthetic oil is stabilized against oxidative degradation by the addition of a mixture comprising at least one specified aromatic amine of the formula I or II ##STR1## and at least one sterically hindered amine. The lubricant may contain other antioxidants or other additives. It is preferably used as motor oil.Type: GrantFiled: September 25, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: Rolf Schumacher, Samuel Evans, Paul Dubs
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Patent number: 5258540Abstract: Compounds of formula Ia ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is methyl, tert-butyl or cyclohexyl, and R.sub.7 and R.sub.8 independently of one another are C.sub.1 -C.sub.18 alkyl, phenyl or C.sub.7 -C.sub.18 alkylphenyl are novel compounds having utility as stabilizers.Type: GrantFiled: July 20, 1992Date of Patent: November 2, 1993Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Werner Stegmann, Reto Luisoli, Roger Martin
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Patent number: 5258433Abstract: Sulfoxides of alkylthiomethylphenols of the formula I ##STR1## in which R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl or a radical --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is C.sub.8 -C.sub.20 alkyl which may be interrupted by --O--, --S-- or --SO-- groups, mono- or dihydroxy-substituted C.sub.2 -C.sub.12 alkyl, phenyl, benzyl, --(CH.sub.2).sub.n COOR.sub.6 or --CH(CH.sub.3)COOR.sub.6, in which R.sub.6 is C.sub.1 -C.sub.20 alkyl and n is 1 or 2, R.sub.3 is hydrogen or a group --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is as defined above, and R.sub.4 has the same meanings as R.sub.2 , with the proviso that only one of the radicals R.sub.2, R.sub.3 or R.sub.4 is the group --CH.sub.2 --SO--R.sub.5 and that, if R.sub.Type: GrantFiled: August 20, 1991Date of Patent: November 2, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Rudolf Meier, Paul Dubs
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Patent number: 5206414Abstract: A process for the preparation of compounds of the general formula ##STR1## where R.sub.1 and R.sub.2 are identical or different and are hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl, C.sub.1 -C.sub.4 alkyl-substituted phenyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl,R.sub.3 is hydrogen or methyl,m is 0, 1, 2 or 3, andn is a number from 1 to 4 or 6, andA is as defined in the description,by reacting a compound of the formula II ##STR2## where m, R.sub.1 and R.sub.2 are as defined above, with a compound of the formula III ##STR3## where A and n are as defined in the description, which comprises carrying out the reaction in the presence of a catalyst which contains, as active material, an alkali metal compound of the formula IVM.sub.m An (IV)in whichM is Li, Na, K, Rb or Cs,m is the valency of An, andAn is a fluoride, hydroxide, phosphate, formate, acetate or --OR.sub.5 radical, andR.sub.Type: GrantFiled: April 29, 1992Date of Patent: April 27, 1993Assignee: Ciba-Geigy CorporationInventors: Samuel Evans, Paul Dubs, Milos Rusek, Zdenek Mazour, Arpad Major
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Patent number: 5175312Abstract: Novel compounds of the formula I ##STR1## in which R.sub.1 is C.sub.13 -C.sub.30 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.7 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl, or is phenyl or C.sub.7 -C.sub.12 phenylalkyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl and Z is phenyl, phenyl which is substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy or chlorine, a group ##STR2## in which n is 1 or 2 or a group ##STR3## in which the radicals A independently of one another are C.sub.1 -C.sub.8 alkyl, methoxy or ethoxy, are suitable for stabilizing organic material against oxidative, thermal and actinic degradation.Type: GrantFiled: August 27, 1991Date of Patent: December 29, 1992Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud