Preparing Esters By Oligomerization Patents (Class 560/202)
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Patent number: 9289749Abstract: The invention provides a polycondensation catalyst for producing polyester by an esterification reaction or a transesterification reaction between a dicarboxylic acid or an ester-forming derivative thereof and a glycol, wherein the polycondensation catalyst comprises particles of a solid base having on the surfaces an inner coating layer of titanic acid in an amount of from 0.1 to 50 parts by weight in terms of TiO2 per 100 parts by weight of the solid base, and an outer coating layer either of an oxide of at least one element selected from aluminum, zirconium and silicon, or of a composite oxide of at least two elements selected from aluminum, zirconium and silicon on the surface of the inner coating layer in an amount of from 1 to 50 parts by weight per 100 parts by weight of the solid base.Type: GrantFiled: July 31, 2013Date of Patent: March 22, 2016Assignee: Sakai Chemical Industry Co., Ltd.Inventors: Keiichi Tabata, Akihiro Kamon, Keiichi Ikegawa, Jun Naito
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Patent number: 9074047Abstract: The invention provides a method for producing a catalyst for producing polyester by an esterification reaction or a transesterification reaction between a dicarboxylic acid or an ester-forming derivative thereof and a glycol, the method comprising hydrolyzing an organic titanium compound in an organic solvent in which particles of a solid base are dispersed thereby to form a coat layer of titanic acid on the surface of the particles of a solid base.Type: GrantFiled: December 23, 2011Date of Patent: July 7, 2015Assignee: SAKAI CHEMICAL INDUSTRY CO., LTD.Inventors: Hiromitsu Shimizu, Keiichi Tabata, Akihiro Kamon
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Publication number: 20150018574Abstract: A self-metathesis process for the production of unsaturated dicarboxylic fatty diacids and/or unsaturated dicarboxylic fatty diesters, wherein unsaturated carboxylic fatty acids and/or esters of unsaturated carboxylic fatty acids are reacted in the presence of at least one defined ruthenium based catalyst compound. A catalyst enhancer compound selected from a sacrificial catalyst or a non-catalyst enhancer may also be used. The process exhibits improved reaction times and/or the catalyst can be used at very low concentrations.Type: ApplicationFiled: March 18, 2013Publication date: January 15, 2015Applicant: CRODA INTERNATIONAL PLCInventors: Bastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
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Publication number: 20130165358Abstract: Provided is a comb polyolefin. The comb polyolefin has a copolymer of a multifunctional acrylate monomer and a ?,?-diene monomer terminated with a polyolefin substituent. There is also a process for making a comb polyolefin. There is also a polymer backbone. There is also a polyolefin blend. There is also a lubricant composition including the comb polyolefin.Type: ApplicationFiled: December 21, 2011Publication date: June 27, 2013Applicant: ExxonMobil Research and Egineering CompanyInventors: Yong Yang, Andy Haishung Tsou, Donna Jean Crowther
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Publication number: 20120264935Abstract: The invention discloses an improved process for the preparation of 2,2,5,5-tetrasubstituted hexane-1,6-dicarbonyl compounds, and in particular diethyl 2,2,5,5-tetramethylhexanedioate and dimethyl 2,2,5,5-tetramethylhexanedioate, by the alkylation of 1,2-difunctional ethane compounds with enolates of carbonyl compounds. The process provides higher yields and greater synthetic brevity than existing processes.Type: ApplicationFiled: December 21, 2010Publication date: October 18, 2012Applicant: THE UNIVERSITY OF READINGInventors: Francis William Lewis, Laurence Marius Harwood, Michael James Hudson
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Publication number: 20100041913Abstract: The invention provides a polycondensation catalyst for producing polyester by an esterification reaction or a transesterification reaction between a dicarboxylic acid or ester-forming derivative thereof and a glycol, wherein the polycondensation catalyst comprises particles of a solid base having on their surfaces either a coat layer of titanic acid in an amount of from 0.1 to 50 parts by weight in terms of TiO2 per 100 parts by weight of the solid base, or an inner coat layer of an oxide of at least one element selected from silicon, aluminum and zirconium or a composite oxide of at least two elements selected from silicon, aluminum and zirconium in an amount of from 1 to 20 parts by weight per 100 parts by weight of the solid base and an outer coat layer of titanic acid in an amount of from 0.Type: ApplicationFiled: June 28, 2006Publication date: February 18, 2010Inventors: Toshikatsu Umaba, Hiromitsu Shimizu, Kenji Mori, Keiichi Tabata
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Patent number: 6566563Abstract: A process for making OH-terminated compounds involving: (a) combining at least one CH2OH-terminated diol and a titanium-containing catalyst to form a reaction mixture; (b) heating the reaction mixture to a temperature of from 110 to 160° C. to form a heated reaction mixture; (c) continuously adding dimethyl carbonate to the heated reaction mixture; (d) continuously distilling all methanol released from the heated reaction mixture; (e) heating the reaction mixture to a temperature of from 190 to 240° C. to form an OH-terminated product; (f) removing unreleased methanol and dimethyl carbonate from the reaction mixture under a pressure of less than 100 mbar; and (g) deactivating the titanium-containing catalyst by adding from 0.8 to 2 equivalents, based on the catalyst, of a 1 to 20% by weight aqueous solution of phosphoric acid to the reaction mixture, at a temperature of from 80 to 120° C.Type: GrantFiled: May 4, 2001Date of Patent: May 20, 2003Assignee: Cognis Deutschland GmbH & Co. KGInventors: Alfred Westfechtel, Roland Gruetzmacher, Elke Grundt
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Patent number: 6566549Abstract: A continuous process for oligomers which do not contain, as polymerized units, carboxylic acid-containing monomers and their salts, including the steps of: (1) forming a reaction mixture, substantially free of carboxylic acid-containing monomers and their salts, containing: (i) 0.5 to 99.95% by weight of the reaction mixture of at least one ethylenically unsaturated monomer; and (ii) 0.05 to 25% by weight, based on the weight of the ethylenically unsaturated monomer, of at least one free-radical initiator; and (2) continuously passing the reaction mixture through a heated zone wherein the reaction mixture is maintained at a temperature of at least 150° C. and a pressure of at least 30 bars for from 0.1 seconds to 4 minutes to form terminally-unsaturated oligomers. In addition, processes for forming oligomers of vinyl acetate and oligomers of vinyl alcohol are disclosed. Mixtures of fully saturated and terminally unsaturated oligomers are also disclosed.Type: GrantFiled: December 15, 1998Date of Patent: May 20, 2003Assignee: Rohm and Haas CompanyInventors: Gary David Greenblatt, Barry Clifford Lange, Michael Damian Bowe, Richard Foster Merritt, Robert Wilczynski, Gary Robert Larson, Lori Marie Petrovich, David William Whitman
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Publication number: 20020137857Abstract: The invention relates to a curable composition and a process of preparing the curable composition. The process comprises (a) forming an oligomer from oligomerization of a mixture of a monomer A having a functional group and a monomer B at a temperature in the range of from 150° C. to 650° C., a pressure in the range of from 3 MPa to 35 MPa and the pressure is high enough to maintain the reaction mixture in a fluid state and a residence time in the range of from 0.1 second to 4 minutes; and (b) reacting a modifier having at least one reactive moiety with the oligomer through a reaction between the reactive moiety of the modifier and the functional group of the monomer A in the oligomer, and the modifier further comprises a curable group.Type: ApplicationFiled: April 13, 1999Publication date: September 26, 2002Inventors: BARRY CLIFFORD LANGE, MICHAEL DAMIAN BOWE, RICHARD FOSTER MERRITT, ROBERT WILCZYNSKI, WARD THOMAS BROWN, RONALD SCOTT BECKLEY
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Publication number: 20020111448Abstract: A continuous process for oligomers which do not contain, as polymerized units, carboxylic acid-containing monomers and their salts, including the steps of:Type: ApplicationFiled: December 19, 2001Publication date: August 15, 2002Inventors: Gary David Greenblatt, Barry Clifford Lange, Michael Damian Bowe, Richard Foster Merritt, Robert Wilczynski, Gary Robert Larson, Lori Marie Petrovich, David William Whitman
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Publication number: 20020082371Abstract: A continuous process for oligomers which do not contain, as polymerized units, carboxylic acid-containing monomers and their salts, including the steps of:Type: ApplicationFiled: December 19, 2001Publication date: June 27, 2002Inventors: Gary David Greenblatt, Barry Clifford Lange, Michael Damian Bowe, Richard Foster Merritt, Robert Wilczynski, Gary Robert Larson, Lori Marie Petrovich, David William Whitman
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Patent number: 6255523Abstract: The present invention relates to powder coating compositions which can be cured at low temperatures. The powder coating composition of the invention include a unique combination of a branched oligoester polyol and uretdione crosslinking agent which when cured results in a coating binder with desirable hardness, flexibility, solvent resistance, corrosion resistance, weatherability and gloss.Type: GrantFiled: September 18, 1998Date of Patent: July 3, 2001Assignee: McWhorter Technologies, Inc.Inventors: Kamlesh Pai Panandiker, John Michael Bronk, Franklin Paul Spitler
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Patent number: 6020520Abstract: Electrolytic hydrodimeric coupling of dialkyl maleates in alkanol solutions containing an alkanol-soluble alkali metal acetate/quatemary ammonium tetrafluoroborate mixed supporting electrolyte yields tetraalkyl 1,2,3,4-butanetetracarboxylates.Type: GrantFiled: September 24, 1998Date of Patent: February 1, 2000Assignee: Solutia Inc.Inventors: Monica C. Dutton, Melvin R. Bagley, Dennis J. Kalota
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Patent number: 5952458Abstract: Synthesis of a vinyl terminated polymer by reacting a cationically polymerizable monomer in the form of a cyclic ether with an acid chloride in a suitable solvent and in the presence of a Lewis acid. The vinyl-terminated polymers can be polymerized with other appropriate monomers resulting in thermoplastic elastomers having suitable properties for use as binders for explosives and propellants.Type: GrantFiled: September 24, 1998Date of Patent: September 14, 1999Assignee: The Government of the United States as represented by the Secretary of the NavyInventor: Mostafa A. H. Talukder
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Patent number: 5942642Abstract: The invention relates to a method for making oligomers, including homo-oligomers and cooligomers, by the free radical polymerization of at least one monomer component B) having a greater tendency to polymerize and 0-90 wt. %, calculated on the oligomers, of a monomer component A) having a lesser tendency to polymerize, at an elevated temperature and in the presence of a polymerization initiator in a conventional polymerization vessel, by adding monomer component B) to monomer component A), or to a solution of monomer component A), or merely to a solvent, so that the mol ratio of B) to A), if A) is present, passes through values of 0 to about 0.2 during the initial phase of the polymerization and takes the value 0.Type: GrantFiled: September 25, 1997Date of Patent: August 24, 1999Assignee: Roehm GmbH Chemische FabrikInventors: Claudia Beyer, Horst Pennewiss
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Patent number: 5880298Abstract: For the oligomerization of a fatty ester or fatty acid containing conjugated double bonds, the reaction uses a catalyst consisting of an activated earth, e.g., montmorillonite, at a temperature of from 100.degree.-180.degree. C., preferably from 130.degree.-160.degree. C. The process can be carried out continuously or in a batch process on a fixed bed and is particularly applicable to conjugated methyl esters obtained by conjugating and transesterifying sunflower seed oil. The oligomerized products obtained are particularly useful as lubricants or polycondensation reactants.Type: GrantFiled: January 14, 1994Date of Patent: March 9, 1999Assignees: Institut Francais du Petrole, OnidolInventors: Gerard Hillion, Robert Stern, Odile Le Borgne
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Patent number: 5731383Abstract: This invention relates to difunctional telechelic linear non-crosslinked polyolefins without pendant chain branched groups. The polyolefin compounds of this invention are useful for preparing high molecular weight polyesters, polyamides, polyureas and polyurethanes of high density without branching of the polymer chains, and with low permeability to gases and solvents.Type: GrantFiled: September 3, 1996Date of Patent: March 24, 1998Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson
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Patent number: 5559190Abstract: This invention relates to difunctional telechelic linear non-crosslinked polyolefins without pendant chain branched groups. The polyolefin compounds of this invention are useful for preparing high molecular weight polyesters, polyamides, polyureas and polyurethanes of high density without branching of the polymer chains, and with low permeability to gases and solvents.Type: GrantFiled: June 2, 1995Date of Patent: September 24, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson
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Patent number: 5347043Abstract: Dialkyl malonate/alkyl acrylate Michael addition product mixtures having at least three acceptor moieties in a substantial number of the molecules can be consistently prepared without the need for long reaction times or the use of a large excess of the acceptor when the reaction is effected by gradually adding one molar proportion of a dialkyl malonate to at least three molar proportions of an alkyl acrylate which has been preheated to 60.degree.-80.degree. C. in admixture with an initiator and a phase transfer catalyst. In a preferred embodiment, the preheated mixture is maintained at 60.degree.-80.degree. C. for at least one hour before the dialkyl malonate is added in order to increase the percentage of product composed of the heavier components.Type: GrantFiled: December 20, 1993Date of Patent: September 13, 1994Assignee: Albemarle CorporationInventors: Mahmood Sabahi, Robert G. Irwin
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Patent number: 5286879Abstract: An improved process for preparing mono-condensation derivatives of adipic acid with fewer steps and better purity is disclosed. In particular, this process comprises: (a) forming relatively concentrated and pure cyclic monomeric adipic anhydride by depolymerization and concentration starting from polymeric adipic anhydride; and (b) adding a condensation reactant having an active hydrogen, e.g., a primary or secondary amine, to said cyclic monomeric adipic anhydride to form the corresponding mono-condensation derivative of adipic acid.Type: GrantFiled: October 5, 1992Date of Patent: February 15, 1994Assignee: The Procter & Gamble CompanyInventors: James C. Letton, Larry E. Miller
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Patent number: 5245072Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula -(C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.Type: GrantFiled: February 24, 1992Date of Patent: September 14, 1993Assignee: Mobil Oil CorporationInventors: Thomas J. Giacobbe, George A. Ksenic
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Patent number: 5187308Abstract: The present invention relates to a novel process for the production of low viscosity copolymers of maleic acid monoalkyl ester and vinyl alkyl ethers characterized in that the copolymerization of alkyl vinyl ether is performed with a mixture composed of maleic acid anhydride and maleic acid monoalkyl ester. The specific viscosity is controlled by the setting of a certain maleic acid anhydride to maleic acid monoalkyl ester ratio.Type: GrantFiled: November 14, 1990Date of Patent: February 16, 1993Assignee: Giulini Chemie GmbHInventors: Zvi Pelah, Istvan Potencsik, Werner Kopp, Ernst Urmann
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Patent number: 5106541Abstract: Oligomers and addition products obtained from the reaction of a saturated or olefinically unsaturated carboxylic acid, alcohol, ether, or ester with a substituted or unsubstituted acetic anhydride in the presence of a Mn compound, and processes for their preparation.Type: GrantFiled: January 9, 1990Date of Patent: April 21, 1992Assignee: Henkel Research CorporationInventors: William E. Fristad, Alan G. Olivero, Steven Young, Christopher S. Sykes, Brock M. Siegel
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Patent number: 5099061Abstract: A process is disclosed for preparing functionalized linear olefins by dimerizing terminal olefins in the presence of a cationic rhodium compound. Novel rhodium compounds useful in this process are also disclosed.Type: GrantFiled: September 11, 1990Date of Patent: March 24, 1992Assignee: The University of North Carolina at Chapel HillInventors: Maurice S. Brookhart, Sylviane Sabo-Etienne
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Patent number: 5099048Abstract: A process is disclosed for preparing functionalized linear olefins by dimerizing terminal olefins in the presence of a cationic rhodium compound. Novel rhodium compounds useful in this process are also disclosed.Type: GrantFiled: June 11, 1991Date of Patent: March 24, 1992Assignee: The University of North Carolina at Chapel HillInventors: Maurice S. Brookhart, Sylviane Sabo-Etienne
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Patent number: 5039754Abstract: A polymeric peroxide comprising a dilvalent recurring unit having the formula: ##STR1## wherein the recurring unit of Formula I has a 10 hour half-life temperature of at least 80.degree. C. and optionally a divalent recurring unit having the formula: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, X, X.sup.1, Y, Z, y and z are as defined in the Detailed Description of the Preferred Embodiments and the polymeric peroxide has a molecular weight of 1,000 to 200,000. The polymeric peroxides are derived from hydroxy-hydroperoxides of dihydroxy dialkyl peroxides. These polymeric peroxides can be used for preparing block copolymers and compatibilizing polymer blends and alloys.Type: GrantFiled: August 30, 1990Date of Patent: August 13, 1991Assignee: Atochem North America, Inc.Inventor: Jose Sanchez
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Patent number: 4973743Abstract: This invention provides a process for preparing an oligomer of at least one polyunsaturated aliphatic C.sub.12-22 monocarboxylic acid ester in the presence of boron trifluoride resulting in a high yield or predominantly trimeric product which, upon hydrolysis, affords a high yield of polybasic, predominantly trimeric, acids. This invention further provides such a process with excellent recovery of the boron trifluoride.Type: GrantFiled: October 27, 1989Date of Patent: November 27, 1990Assignee: Henkel CorporationInventors: Stephen W. Turner, Charles W. Blewett
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Patent number: 4950785Abstract: Process of synthetizing ethylene-tetracarboxylic esters by duplication of lonic compounds of the formula: ##STR1## wherein X=COOR, Y=COOR' and R and R' represent an organic group, characterized in that the duplication is an oxidative duplication conducted in the presence of a catalyst consisting of the salt of a transition metal.Type: GrantFiled: February 21, 1989Date of Patent: August 21, 1990Assignee: Presidenza del Consilglio dei Ministri Ufficio del Ministro per il coordinamento delle iniziative per la ricerca scientifica e tecnologicaInventors: Roberto Santi, Giuseppe Cometti
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Patent number: 4927957Abstract: Alkyl acrylates are catalytically dimerized, e.g., to produce alkyl diesters of dihydromuconic acid, in the presence of a catalytically effective amount of palladium, tetrafluoroboric acid and a hydrogenophosphonium tetrafluoroborate, and wherein the palladium concentration ranges from 0.1 to 3 mmol per mole of said at least one alkyl acrylate, the reaction temperature ranges from 70.degree. to 150.degree. C. and the hydrogenophosphonium tetrafluoroborate concentration is at least 6 mmol per mole of said at least one alkyl acrylate.Type: GrantFiled: August 19, 1988Date of Patent: May 22, 1990Assignee: Rhone-Poulenc ChimieInventors: Robert Perron, Sylvain Mutez
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Patent number: 4889949Abstract: The alkyl acrylates, e.g., methyl or ethyl acrylate, are improvedly dimerized, or codimerized with a conjugated diene, by contacting same with a catalytically effective amount of (a) at least one palladium source, (b) at least one organophosphorus(III) compound, and (c) at least one hydracid HY, the anion Y.sup.- of which does not coordinate with palladium ions.Type: GrantFiled: June 28, 1988Date of Patent: December 26, 1989Assignee: Rhone-Poulenc ChimieInventors: Pierre Grenouillet, Denis Neibecker, Igor Tkatchenko
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Patent number: 4857434Abstract: This invention is directed to a thermal or radiation curable prepolymer, formulations containing same and processes of using same, said prepolymer comprising a liquid meth(acrylate) terminated polymeric hydrocarbon maleate having pendant maleate groups. Said prepolymer either per se or formulated with mono- or multi-functional unsaturated monomers and either a thermal or photoinitiator on exposure to heat or UV or high energy ionizing radiation forms a cured material utilizable as a printing plate, coating, adhesive or sealant.Type: GrantFiled: September 2, 1987Date of Patent: August 15, 1989Assignee: W. R. Grace & Co.Inventor: Lori J. Klinger
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Patent number: 4790957Abstract: This invention relates to aliphatic or aromatic polycarboxylic acid esters as defined herein which are useful as base oils alone in lubricating oil compositions or in admixture with completely synthetic, partially synthetic, or mineral oil-based lubricant compositions.Type: GrantFiled: October 9, 1987Date of Patent: December 13, 1988Assignee: BASF AktiengesellschaftInventors: Helmut Mach, Hans-Henning Vogel, Juergen Jahn
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Patent number: 4786623Abstract: The alkyl acrylates, e.g., methyl or ethyl acrylate, are improvedly dimerized, or codimerized with a conjugated diene, by contacting same with a catalytically effective amount of (a) at least one palladium source, (b) at least one organophosphorus(III) compound, and (c) at least one hydracid HY, the anion Y.sup.- of which does not coordinate with palladium ions.Type: GrantFiled: March 20, 1987Date of Patent: November 22, 1988Assignee: Rhone-Poulenc ChimieInventors: Pierre Grenouillet, Denis Neibecker, Igor Tkatchenko
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Patent number: 4778830Abstract: Disclosed are polyester polyols liquid at 25.degree. C., having an average functionality of from 2 to 3, a hydroxyl number of from 25 to 400, an acid number smaller than 10 and a viscosity at 25.degree. C. of from 200 to 10,000 mPas, which contain in bonded form units having at least one of the structures--O--CH.sub.2 --CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --O--,--O--CH.sub.2 --CH(C.sub.2 H.sub.5)--CH.sub.2 --CH.sub.2 --O--,--OC--CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --CO--and--OC--CH(C.sub.2 H.sub.5)--CH.sub.2 --CO--which are prepared by the polycondensation or transesterification of 2-methyl-1,5-pentanediol, 2-ethyl-1,4-butanediol, 2-methyl-glutaric acid and/or 2-ethyl succinic acid or their derivatives, optionally while using other organic polycarboxylic acids and multivalent aliphatic alcohols and are useful for preparing non-cellular or cellular polyurethane plastics or polyurethane-polyurea plastics.Type: GrantFiled: December 1, 1987Date of Patent: October 18, 1988Assignee: BASF AktiengesellschaftInventors: Joachim Streu, Matthias Marx, Peter Weyland, Dietrich Scherzer, Wolfgang Straehle
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Patent number: 4762946Abstract: Polymeric pour point depressants are described which are prepared from new esters of .alpha.,.beta.-olefinically unsaturated carboxylic acids of the formulaR.sub.1 --CO--[--O--A--CO--]--.sub.n ORwhereinR.sub.1 --CO-- is an .alpha.,.beta.-olefinically unsaturated carboxylic acid residue containing from 3 to 6 carbon atoms,R is a saturated or unsaturated hydrocarbon radical containing from 10 to 24 carbon atoms,--[--O--A--CO--]-- is a residue of a hydroxycarboxylic acid having from 2 to 6 carbon atoms,A is an aliphatic radical having from 1 to 5 carbon atoms, andn is a number having a value of from 1 to 18.Type: GrantFiled: April 14, 1986Date of Patent: August 9, 1988Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolfgang Ritter, Wolfgang Zoellner
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Patent number: 4692548Abstract: The dimerization of acrylate esters and of ethene and the codimerization of acrylate esters with C.sub.2-4 -alkenes or 1,3-butadiene and of 1,3-butadiene with ethene in the presence of:(a) a Pd and/or Ru compound,(b) a compound containing one trivalent N or P atom, and(c) an Ag and/or Cu salt,yields at an increased reaction rate dimers of high linearity, when a quinone is also present.Type: GrantFiled: May 14, 1986Date of Patent: September 8, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4670579Abstract: An olefin, especially an activated olefin, is telomerized by reaction with an arylamine, such as an aniline, in the presence of an alkyl nitrite, a copper catalyst, and a catalytic amount of water and/or acid and in the absence of more than about 0.5 volume part of inert solvent per volume part of olefin.Type: GrantFiled: June 30, 1986Date of Patent: June 2, 1987Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4638084Abstract: A process is disclosed for dimerizing lower alkyl acrylates or lower alkyl methacrylates utilizing a bis(ethylene) rhodium tetrafluoroborate catalyst.Type: GrantFiled: September 12, 1985Date of Patent: January 20, 1987Assignee: Shell Oil CompanyInventor: David M. Singleton
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Patent number: 4634793Abstract: A process for the dimerization in the liquid phase of an aliphatic mono-olefin having 2 to about 12 carbon atoms with a catalytic system formed by combining, in the presence of water, an alcohol or a carboxylic acid,a. a palladium compound,b. a chelate ligand having as coordinating atoms at least two Group Va atoms which are connected through a chain comprising 2 to about 6 carbon atoms, andc. a compound containing an anion of an acid, except hydrohalogenic acids.Type: GrantFiled: October 3, 1985Date of Patent: January 6, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4613679Abstract: Emulsifiable polyolefin waxes are prepared by reacting low molecular weight homo- and copolymers containing at least one alpha-olefin monomer having at least three carbon atoms with diesters of maleic acid in the presence of a free radical source. These emulsifiable polyolefin waxes having a Gardner color of less than two form excellent nonionic emulsions which are useful in low color floor polishes.Type: GrantFiled: September 13, 1979Date of Patent: September 23, 1986Assignee: Eastman Kodak CompanyInventor: Kenneth R. Mainord
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Patent number: 4594447Abstract: The invention relates to a process for the dimerization of derivatives of acrylic acid in the homogeneous phase which process is characterized in that a compound having the general formula H.sub.2 C.dbd.CR.sup.1 -COOR.sup.2, wherein R.sup.1 represents H or a linear alkyl group having from 1 to 3 carbon atoms and R.sup.2 represents a linear alkyl group having from 1 to 3 carbon atoms, is reacted in a solvent at a temperature of from -50.degree. C. to +50.degree. C. in the presence of nickel compounds as catalysts which contain complex anions X in a molar ratio Ni:X=1:1 and organic or hydride ligands and are modifed with phosphanes having the general formula PR.sub.2 R', wherein R and R' may be same or different and represent alkyl residues having from 1 to 8 carbon atoms or phenyl residues, as well as the use of the dimers formed in the dimerization.Type: GrantFiled: October 3, 1984Date of Patent: June 10, 1986Assignee: Studiengesellschaft Kohle mbHInventors: Gunther Wilke, Karin Sperling, Ludwig Stehling
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Patent number: 4547323Abstract: The process comprises dimerizing methacrylic acid derivatives in the presence of an organic Co(II) glyoxime to produce 2,2-dimethyl-4-methyleneglutaric acid and/or derivatives thereof. Methacrylic acid derivatives include methacrylic acid or derivatives of methacrylic acid. The composition produced by the process comprises a glutaric dimer acid which can be further polymerized to form high molecular weight polymer useful as a binder in protective coatings.Type: GrantFiled: March 21, 1984Date of Patent: October 15, 1985Assignee: SCM CorporationInventor: Gary M. Carlson
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Patent number: 4519954Abstract: A catalyst and a liquid phase process are provided for the dimerization of acrylic compounds. The process includes contacting an acrylic compound with the catalyst in the presence of hydrogen, wherein the catalyst comprises an inorganic oxide catalyst support, trivalent pendant atoms covalently bonded to the support and ruthenium complexed with said trivalent pendant atoms.Type: GrantFiled: December 29, 1982Date of Patent: May 28, 1985Assignee: The Standard Oil CompanyInventors: James D. Burrington, Fred A. Pesa, Elizabeth A. Maher, Robert K. Grasselli
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Patent number: 4504674Abstract: Alkyl acrylate esters are dimerized to dialkyl hexenedioates in the presence of a metal-treated ruthenium compound, an alcohol, optionally a phosphine, and optionally a carboxamide. The hexenedioate products are useful to prepare adipic acid.Type: GrantFiled: April 18, 1983Date of Patent: March 12, 1985Assignee: E. I. DuPont de Nemours & Co.Inventor: Ronald J. McKinney
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Patent number: 4485256Abstract: Process for dimerizing alkyl acrylate esters to dialkyl hexenedioates in the presence of an alkali metal-treated or alkaline earth metal-treated ruthenium compound. The hexenedioate products are useful to prepare adipic acid.Type: GrantFiled: February 28, 1983Date of Patent: November 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 4451665Abstract: Catalytic process for dimerizing a lower alkyl acrylate or methacrylate by contacting, at about 0.degree. to about 150.degree. C., the acrylate or methacrylate with the catalyst of the formula (RCN).sub.4 PdX.sub.2 wherein R is hydrocarbyl which contains no carbon-carbon unsaturation other than aromatic unsaturation and X is an anion which is incapable of displacing RCN from the cationic moiety of the palladium complex.Type: GrantFiled: December 30, 1982Date of Patent: May 29, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: William A. Nugent
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Patent number: 4229559Abstract: This invention is directed to a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of 1.7 to 2, and m is equal to 2-n. Also described herein is a composition comprising said half ester, maleic anhydride and an ethylenically unsaturated monomer, wherein at least 75 mole percent of the half ester is in the maleate form.Type: GrantFiled: May 1, 1979Date of Patent: October 21, 1980Assignee: Union Carbide CorporationInventors: Robert J. Cotter, Hugh C. Gardner
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Patent number: 4158736Abstract: Polymers of esters of acrylic acid having an average chain length of about 6 to about 30 mers are prepared by an anionic polymerization reaction, carried out in the presence of a catalytic amount of an alkoxide anion. These polymers, their hydrolysis products, and their derivatives have a wide variety of applications, including among others use as components in films, coatings, fibers, impregnants, adhesives, and binders, and use as modifiers, plasticizers, melt flow improvers, and leveling agents.Type: GrantFiled: November 5, 1975Date of Patent: June 19, 1979Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Richard A. Haggard
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Patent number: 4105855Abstract: Symmetrical carotenoids are prepared from the half-molecules by dimerizing the phosphonium salts of the half-molecules with peroxides, peroxo compounds or peroxy compounds in an alkaline medium.Type: GrantFiled: January 26, 1976Date of Patent: August 8, 1978Assignee: BASF AktiengesellschaftInventors: Bernhard Schulz, Joachim Paust, Joachim Schneider
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Patent number: 4053503Abstract: A method for dimerizing heptadiene acid esters in the presence of a catalyst which is a metal of Group IA of the Periodic System or an alcoholate, hydride, amide, or tritylate thereof, or is an alcoholate, hydride, or amide of a metal of Group IIA of the Periodic System.Type: GrantFiled: April 9, 1976Date of Patent: October 11, 1977Assignee: Schering AktiengesellschaftInventors: Christian Burba, Peter Borner