Oxirane Containing Reactant Patents (Class 554/149)
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Patent number: 10919829Abstract: A high-purity alcohol compound can be obtained by a method comprising passing a solution containing an ester compound and methanol and/or ethanol through a column packed with an anion exchange resin having methoxide and/or ethoxide as a counter anion to generate a methyl ester and/or ethyl ester, and distilling off the methyl ester and/or ethyl ester together with the methanol and/or ethanol.Type: GrantFiled: June 19, 2019Date of Patent: February 16, 2021Assignee: KANEKA CORPORATIONInventors: Koji Machida, Hiroaki Yasukouchi, Akira Nishiyama
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Patent number: 9777245Abstract: Metathesized triacylglycerol polyols, fractionated polyol variants thereof, and their related physical and thermal properties are disclosed.Type: GrantFiled: January 25, 2016Date of Patent: October 3, 2017Assignee: Trent UniversityInventors: Suresh Narine, Prasanth Kumar Sasidharan Pillai, Shaojun Li, Laziz Bouzidi, Ali Mahdevari
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Patent number: 9668955Abstract: Disclosed are petrolatum-like compositions that include metathesized unsaturated polyol esters. Also disclosed are emulsions that include metathesized unsaturated polyol esters. The petrolatum-like compositions may be used as substitutes for petroleum-based petrolatum. The emulsions may be water-in-oil or oil-in-water emulsions and may be suitable for a variety of end uses.Type: GrantFiled: July 14, 2014Date of Patent: June 6, 2017Assignee: Elevance Renewable Sciences, Inc.Inventors: Diza Pearl Braksmayer, Timothy A. Murphy, Stephen E. Russell, Michael John Tupy, Scott A. Walters
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Patent number: 9598358Abstract: Acylalkylisethionate esters are produced by reacting one or more carboxylic acids with one or more alkyl-substituted hydroxyalkyl sulfonates under esterification reaction conditions. The alkyl-substituted hydroxyalkyl sulfonates used as a raw material in producing the esters are prepared by reacting bisulfate with one or more alkylene oxides. The acylalkylisethionate esters may be used in consumer products.Type: GrantFiled: June 28, 2011Date of Patent: March 21, 2017Assignee: HUNTSMAN PETROCHEMICAL LLCInventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
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Patent number: 9056828Abstract: The present invention is directed towards a method of preparing alkoxylated fatty acid alkyl estersin a one-pot alkoxylation reaction in the presence of a catalyst which is an alkaline earth metal oxide/mineral acid combination, preferably a barium oxide/sulfuric acid combination, or a Lewis acid, preferably Sn Cl4, comprising the steps of: a) providing a fatty acid alkyl ester, b) adding a catalyst to said fatty acid alkyl ester to obtain a first mixture, wherein said catalyst is an alkaline earth metal oxide/mineral acid combination or a Lewis acid, c) adding one or more alkylene oxides to said first mixture to obtain a second mixture and (d) isolating the alkoxylated fatty acid alkyl ester.Type: GrantFiled: August 11, 2011Date of Patent: June 16, 2015Assignee: Kolb Distribution Ltd.Inventors: Christoph Kolano, Lothar Möhle, Rudolf Richner
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Patent number: 9051260Abstract: The present technology provides a process of reducing, removing or eliminating organohalo, glycidol, and oxirane species from carboxylic acid esters streams and crude and refined triglyceride oils to provide a carboxylic acid ester stream or triglyceride oil with reduced levels or essentially free of organohalo, glycidyl or other oxirane species. The process includes adding to the carboxylic acid ester stream or triglyceride oil an amount of a carboxylate anion and a cation counterion sufficient to react with the organohalo, glycidyl and oxirane species present.Type: GrantFiled: September 2, 2011Date of Patent: June 9, 2015Assignee: STEPAN SPECIALITY PRODUCTS, LLCInventors: Joseph C. Rongione, Jenifer Heydinger Galante
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Publication number: 20140329985Abstract: The present invention provides a process for producing polyether ester polyols on the basis of renewable raw materials, the polyether ester polyols produced by the process according to the invention, the use thereof for the purpose of producing polyurethanes, and also polyurethanes containing the polyether ester polyols according to the inventionType: ApplicationFiled: December 19, 2011Publication date: November 6, 2014Inventors: Klaus Lorenz, Jörg Hofmann, Bert Klesczewski, Norber Hahn
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Patent number: 8829216Abstract: Provided herein are poly-capped estolides, including those of the Formula IV in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 2; R1 is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Hydroxy estolides are also described herein, which may be suitable end products, or serve as intermediates to provide poly-capped estolides. Also provided are compositions containing poly-capped estolides and methods of making both said poly-capped estolides and compositions thereof.Type: GrantFiled: August 31, 2012Date of Patent: September 9, 2014Assignee: Biosynthetic Technologies, LLCInventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
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Patent number: 8816020Abstract: A method of producing liquid polymeric polyols from epoxidized plant oils by ring-opening polymerization in an organic solvent in the presence of a catalyst to yield the desired polyols at room temperature. The properties of the polymeric polyols depend on the type of plant oil used as starting material. Typically, polymeric content of the purified plant oil based polyols ranges from 65% to 90%. The hydroxyl value and the acid value ranges from 30 to 90 mg KOH/g sample and 1 to 14 mg KOH/g sample respectively. The average molecular weight Mn ranges from 800 Da to 16000 Da. The liquid plant oil based polymeric polyols are reacted with excess diisocyanate to produce isocyanate terminated prepolymer. Subsequently, the prepared prepolymer is reacted with diol or diamine to polyurethane and polyurea respectively.Type: GrantFiled: October 18, 2012Date of Patent: August 26, 2014Assignee: Malaysian Palm Oil BoardInventor: Hoong Seng Soi
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Patent number: 8686169Abstract: The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.Type: GrantFiled: April 8, 2013Date of Patent: April 1, 2014Assignee: Segetis, Inc.Inventor: Sergey Selifonov
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Patent number: 8674124Abstract: A process for the preparation of an organic reactive intermediate that contains a combination of epoxy groups, hydroxy groups and unsaturated groups wherein the process can be utilized to control the amounts of each of the functional groups in the final product. The reactive intermediates are prepared from natural triglyceride plant and animal oils containing unsaturation.Type: GrantFiled: April 6, 2011Date of Patent: March 18, 2014Assignee: Biobased Technologies LLCInventors: Trevor Newbold, Sandra Mae Newbold, Srikanth Yalamanchili
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Patent number: 8575380Abstract: Provided is a polyethylene glycol derivative which contains two PEG chains, which is bound to a diacylglycerol, which has high purity, and which enhances the stability of liposomes. Polyethylene glycol is represented by the following formula (1) and which is bound to a diacylglycerol: In Formula (1), R1 is a hydrocarbon group containing 1 to 7 carbon atoms, R2 is an alkyl or alkenyl group containing 9 to 21 carbon atoms, n is the average number of moles of added polyethylene glycol chains, 10?n?100, and X is a linker site between branched polyethylene glycol and the diacylglycerol and is represented by the following formula (2): —(CH2)l-Y—(CH2)m-??(2) In Formula (2), Y is an ether bond, an ester bond, a urethane bond, an amide bond, or a carbonate bond and l and m are an integer of 0 to 6.Type: GrantFiled: October 17, 2012Date of Patent: November 5, 2013Assignee: NOF CorporationInventors: Fumiaki Manabe, Yuji Yamamoto
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Publication number: 20130281688Abstract: Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.Type: ApplicationFiled: April 22, 2013Publication date: October 24, 2013Applicant: Elevance Renewable Sciences, IncInventors: Stephen A. Di Biase, Keith M. Wampler, David R. Allen, Randal J. Bernhardt, Ryan Littich
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Patent number: 8557139Abstract: The present invention is a replacement plasticizer system made from or containing an epoxidized fatty acid ester plasticizer as a primary plasticizer and a secondary plasticizer. The replacement placement system is useful with a variety of polymers in applications such as wire-and-cable insulations, wire-and-cable jackets, coatings, adhesives, and castings.Type: GrantFiled: February 12, 2009Date of Patent: October 15, 2013Assignee: Dow Global Technologies LLCInventor: Robert F. Eaton
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Publication number: 20130150601Abstract: The present invention is directed towards a method of preparing alkoxylated fatty acid alkyl estersin a one-pot alkoxylation reaction in the presence of a catalyst which is an alkaline earth metal oxide/mineral acid combination, preferably a barium oxide/sulfuric acid combination, or a Lewis acid, preferably Sn Cl4, comprising the steps of: a) providing a fatty acid alkyl ester, b) adding a catalyst to said fatty acid alkyl ester to obtain a first mixture, wherein said catalyst is an alkaline earth metal oxide/mineral acid combination or a Lewis acid, c) adding one or more alkylene oxides to said first mixture to obtain a second mixture and (d) isolating the alkoxylated fatty acid alkyl ester.Type: ApplicationFiled: August 11, 2011Publication date: June 13, 2013Applicant: KOLB DISTRIBUTION LTD.Inventors: Christoph Kolano, Lothar Möhle, Rudolf Richner
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Publication number: 20130102737Abstract: A method of producing liquid polymeric polyols from epoxidized plant oils by ring-opening polymerization without a ring opening agent in an organic solvent in the presence of a catalyst to yield the desired polyols at room temperature. The properties of the polymeric polyols depend on the type of plant oil used as starting material. Typically, polymeric content of the purified plant oil based polyols ranges from 65% to 90%. The hydroxyl value and the acid value ranges from 30 to 90 mg KOH/g sample and 1 to 14 mg KOH/g sample respectively. The average molecular weight Mn ranges from 800 Da to 16000 Da. The liquid plant oil based polymeric polyols are reacted with excess diisocyanate to produce isocyanate terminated prepolymer. Subsequently, the prepared prepolymer is reacted with diol or diamine to polyurethane and polyurea respectively.Type: ApplicationFiled: October 18, 2012Publication date: April 25, 2013Applicant: Malaysian Palm Oil BoardInventor: Hoong Seng Soi
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Publication number: 20130046102Abstract: Glyceryl ether compounds prepared by the reaction of glycerol and olefin epoxides are disclosed. The compounds are renewable biomass-based surfactants useful as detergents and emulsifiers in formulations for cleaning, laundry, personal care, cosmetics, and industrial uses.Type: ApplicationFiled: October 22, 2012Publication date: February 21, 2013Applicant: SEGETIS, INC.Inventor: SEGETIS, INC.
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Publication number: 20130005937Abstract: The present invention relates to a method for preparing polyols of formula (I?) R?1 being H or an alkyl group, R? being especially an alkyl group, A1, being an alkylene radical and R3, are being especially a group -A2-O—Y?, A2 being an alkylene radical and Y? being especially H, said method especially comprising a step of epoxidation of a compound of formula R?1 being H or an alkyl group, A1 being defined as above in formula (I?) and R4 being especially a group -A2-O—Y1?, A2 being defined as above in formula (I?) and Y?1 being especially H, in order to obtain a compound of formula A1 being defined as above, R??1 being H or an alkyl group and R5 being especially a group of formula -A2-O—Y2?, A2 being as defined above in formula (I?) and Y?2 being especially H,Type: ApplicationFiled: September 10, 2010Publication date: January 3, 2013Applicant: Centre National De La Recherche Scientifique (C.N.R.S.)Inventors: Henri Cramail, Aurélie Boyer, Eric Cloutet, Rachida Bakhiyi, Carine Alfos
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Publication number: 20120309994Abstract: Suggested is the use of adducts of 2 to 50 moles propylene oxide to hydroxy carboxylic acids as monomer or co-monomer components in the production of polyesters and polyurethanes or reactive solvents for polymers.Type: ApplicationFiled: August 13, 2012Publication date: December 6, 2012Applicant: Cognis IP Management GmbHInventors: Joaquin Bigorra Llosas, Luis Llaurado, Francesc Gusi
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Patent number: 8308975Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.Type: GrantFiled: October 25, 2011Date of Patent: November 13, 2012Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore Michael Smiecinski
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Publication number: 20120208732Abstract: This invention relates to base ester compounds and complex ester compounds that can be used as a base stock for lubricant applications or a base stock blend component for use in a finished lubricant or for particular applications, and methods of making the same. The base ester compounds and complex esters described herein comprise dimer and/or trimer esters, and their respective branched derivatives.Type: ApplicationFiled: February 13, 2011Publication date: August 16, 2012Inventors: Suresh Narine, Shaojun Li, Ali Mahdevari, Laziz Bouzidi, Stephen Augustine DiBiase, Syed Q.A. Rizvi
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Patent number: 8173825Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.Type: GrantFiled: March 13, 2007Date of Patent: May 8, 2012Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
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Patent number: 8153746Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.Type: GrantFiled: June 2, 2010Date of Patent: April 10, 2012Assignee: Cargill, IncorporatedInventors: Zoran S. Petrovic, Ivan X. Javni, Alisa Zlatanic, Andrew Xiuguang Guo
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Publication number: 20120065260Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.Type: ApplicationFiled: September 6, 2011Publication date: March 15, 2012Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
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Patent number: 8105993Abstract: Methods and compositions are provided for forming ester based compositions. The ester based compositions may be used in consumer products. In one aspect, a method is provided for producing acyl alkylisethionate esters by the esterification of a sulfonate composition having two or more sulfonate isomers with fatty acid(s). In another aspect, a method is provided for forming an ester based composition including a blend of acyl alkylisethionate and acylisethionate esters.Type: GrantFiled: May 1, 2007Date of Patent: January 31, 2012Assignee: Huntsman Petrochemical LLCInventors: Prakasa R. Anantaneni, George A. Smith, Martin J. Renner
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Patent number: 8084631Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.Type: GrantFiled: May 15, 2008Date of Patent: December 27, 2011Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
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Publication number: 20110218350Abstract: Glyceryl ether compounds prepared by the reaction of glycerol and olefin epoxides are disclosed. The compounds are renewable biomass-based surfactants useful as detergents and emulsifiers in formulations for cleaning, laundry, personal care, cosmetics, and industrial uses.Type: ApplicationFiled: May 20, 2011Publication date: September 8, 2011Applicant: SEGETIS, INC.Inventor: Sergey SELIFONOV
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Patent number: 8008239Abstract: The present invention provides acylalkylisethionate esters useful in consumer products. The acylalkylisethionate esters are produced by reacting one or more carboxylic acids with one or more alkyl-substituted hydroxyalkyl sulfonates under esterification reaction conditions. The alkyl-substituted hydroxyalkyl sulfonates used as a raw material in producing the esters are prepared by reacting bisulfite with one or more alkylene oxides.Type: GrantFiled: August 11, 2004Date of Patent: August 30, 2011Assignee: Huntsman Petrochemical LLCInventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
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Patent number: 7892599Abstract: Methods for functionalizing the surface of nanomaterials to improve processing and product manufacturing. These methods are useful for oxides, nitrides, carbides, borides, metals, alloys, chalcogenides, and other compositions.Type: GrantFiled: July 27, 2004Date of Patent: February 22, 2011Assignee: PPG Industries Ohio, Inc.Inventors: Tapesh Yadav, Karl Pfaffenbach
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Publication number: 20100311992Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.Type: ApplicationFiled: June 2, 2010Publication date: December 9, 2010Applicant: CARGILL, INCORPORATEDInventors: Zoran S. PETROVIC, Ivan Javni, Alisa Zlatanic, Andrew Guo
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Publication number: 20100292373Abstract: The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.Type: ApplicationFiled: November 22, 2006Publication date: November 18, 2010Inventor: Sergey Selifonov
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Publication number: 20100267828Abstract: The present disclosure relates to compounds of the general formula (I): wherein R1 and R2 are the same or different and are chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; or any pharmaceutically acceptable salt, solvate, complex, or pro-drug thereof; and their use as medicaments for the treatment of various diseases and conditions, for example, reduction of elevated triglyceride levels, i.e., hypertriglyceridemia, reduction of non-HDL cholesterol, reduction of glucose and HbA1c, and improvement of insulin resistance. The present disclosure also relates to a pharmaceutical composition comprising compounds of formula (I), as well as to processes for preparing compounds according to formula (I).Type: ApplicationFiled: October 30, 2008Publication date: October 21, 2010Inventors: Anne Kristin Holmeide, Ragnar Hovland
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Patent number: 7786239Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.Type: GrantFiled: June 24, 2005Date of Patent: August 31, 2010Assignee: Pittsburg State UniversityInventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
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Publication number: 20090286896Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.Type: ApplicationFiled: May 15, 2008Publication date: November 19, 2009Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
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Patent number: 7544763Abstract: The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in-situ. The process does not use any added organic or inorganic acid catalyst. The polyol produced by the process is essentially free of any cation or anion. The fatty acid ester oil epoxidation and hydroxylation reactions can occur progressively in the same reactor for essentially a one-pot reaction. The polyol produced by the process is essentially free of any cation or anion. The polyol can be used to produce polyurethanes having improved properties.Type: GrantFiled: November 7, 2006Date of Patent: June 9, 2009Assignee: Arkema Inc.Inventor: Mohammad Kazemizadeh
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Publication number: 20080281115Abstract: A novel, chemically-modified partially hydrogenated vegetable oil (PHVO) is described. The PHVO is produced by a three-step reaction process that includes epoxidation, a ring-opening reaction, followed by esterification. The modified PHVO has improved kneadability and, if mixed with fully hydrogenated fat(s), hardness comparable to unmodified PHVO.Type: ApplicationFiled: May 1, 2008Publication date: November 13, 2008Applicant: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.Inventors: Tong Wang, Liping Wang
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Publication number: 20080227993Abstract: The present invention is a method for making a class of molecules synthesized from unsaturated plant oils, and the synthesized class of molecules, such that when compounded with saturated plant oils they improve the physical properties such as low temperature behavior, measured as cold filter plug point and cloud point for biodiesel fuels and pour point for oils and lubricants, as well as other physical properties including viscosity and viscosity index, so that the physical properties of the combined materials approach the physical properties of unsaturated plant oils and find use as base material feed stocks for “Green” fuel, oil, and lubricant products.Type: ApplicationFiled: March 17, 2007Publication date: September 18, 2008Inventor: Matthew Mark Zuckerman
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Publication number: 20080154053Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.Type: ApplicationFiled: March 13, 2007Publication date: June 26, 2008Applicants: The Unites States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
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Publication number: 20070282117Abstract: A method of preparing enhanced reactive vegetable oils wherein the method comprises providing a hydroxy functional vegetable oil having a predetermined hydroxyl value and, under nitrogen, treating the hydroxyl functional vegetable oil with a catalyst using heat and pressure. Any water that is formed is removed. The mixture is heated under pressure and then an alkylene oxide is added while heating under pressure. In one embodiment, thereafter, there is added ethylene oxide and the material is heated and then the material is neutralized with acid. This process results in a primary hydroxyl functional vegetable oil polyol that is an enhanced reactive vegetable oil.Type: ApplicationFiled: June 1, 2006Publication date: December 6, 2007Inventors: Trevor Newbold, David M. Casper
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Patent number: 7279448Abstract: A novel class of chemically-modified vegetable oils is prepared by reacting epoxidized triglyceride oils with thiols. The resultant poly(hydroxy thioether) derivatives have utility as antiwear/antifriction additives for environmentally-friendly industrial oils and automotive applications.Type: GrantFiled: July 8, 2004Date of Patent: October 9, 2007Assignees: The United States of America, as represented by the Secretary of Agriculture, The PENN State Research FoundationInventors: Sevim Z. Erhan, Atanu Adhvaryu, Brajendra K. Sharma
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Patent number: 6927299Abstract: Disclosed are a fatty acid esters composition of a polyglycerine containing more than 70% of a fatty acid monoester which is defined by a specified analysis method, a process for the preparation thereof, a process for the preparation of a highly purified fatty esters composition of a polyglycerine, and a highly-purified fatty acid esters composition of a polyglycerine having an oxirane oxygen concentration of below 100 ppm which is defined by a specified analysis method. The fatty acid esters compositions of a polyglycerine are useful as additives for a variety of food-stuffs, additives for a variety of thermoplastic resins, and as additives for a variety of cosmetics or detergents.Type: GrantFiled: July 15, 2003Date of Patent: August 9, 2005Assignee: Daicel Chemical Industries, Ltd.Inventor: Toshio Endo
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Patent number: 6797753Abstract: Compositions and methods for plasticizing polyvinyl chloride polymers where the plasticizers contain fatty acids derived from vegetable oils and the fatty acids are substantially fully esterified with an alcohol (monool or polyol), the fatty acids having unsaturated bonds that are substantially fully epoxidized, and wherein the fatty acids are added substantially randomly to one or more hydroxyl sites on the alcohol. The plasticizers may be added in amounts between about 10 to 230 pph of PVC resin.Type: GrantFiled: May 4, 2001Date of Patent: September 28, 2004Assignee: Battelle Memorial InstituteInventors: Herman P. Benecke, Bhima R. Vijayendran, Joel D. Elhard
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Patent number: 6765116Abstract: A process to prepare an improved fluid rare earth phosphate catalyst composition useful in preparing alkylene oxide adducts of organic compounds having active hydrogen atoms is provided. The catalyst is prepared by dissolving a rare earth salt in a C9-C30 active hydrogen containing organic compound and then adding phosphoric acid to the organic compound rare earth mixture.Type: GrantFiled: August 23, 2002Date of Patent: July 20, 2004Assignee: Shell Oil CompanyInventor: Charles Lee Edwards
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Patent number: 6706768Abstract: Described is an alkoxylated composition that comprises a family of trans carbon-carbon double bond free compositions that generally have melting points that range from 30-80° C., preferably with melting points between 55-58° C. and with a solubility profile compatible with a broad range of cosmetic and industrial chemical bases. At room temperature (˜20° C.), this family of compositions varies from pourable liquids, to soft creams, to pasty waxes, to a brittle hard material. These compounds, whether used pure or when combined with other carrier and vehicle components (including other additives, thickeners or binders) can form excellent carrier and vehicles for delivery of compositions for use in the cosmetic, personal care and/or pharmaceutical field, including the cosmeceutical field where cosmetic compositions also provide pharmaceutical or other therapeutic benefits.Type: GrantFiled: March 21, 2002Date of Patent: March 16, 2004Assignee: International Flora Technologies, Ltd.Inventors: James H. Brown, Robert Kleiman, John C. Hill
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Patent number: 6646145Abstract: Processes for preparing alkoxylated nonionic surfactants are disclosed, wherein a compound having at least one active hydrogen atom, a carboxylic acid ester or mixtures thereof are reacted with an alkylene oxide in the presence of a hydrotalcite catalyst to form a reaction product mixture; and the reaction product mixture is combined with an acid in at least an equimolar amount based on the amount of the catalyst present.Type: GrantFiled: January 8, 2002Date of Patent: November 11, 2003Assignee: Cognis Deutschland GmbHInventors: Ansgar Behler, Horst-Dieter Schares, Almud Folge
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Patent number: 6583302Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: January 25, 2002Date of Patent: June 24, 2003Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
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Publication number: 20030088054Abstract: A method of making oleochemical oil-based polyols by mixing an acid activated or acid leached clay, an epoxidized oleochemical oil, alcohol, and acid activated or acid leached clay so the epoxidized oleochemical oil reacts with said alcohol to form a oleochemical oil-based polyol, filtering out said clay, stripping off any excess alcohol, and recovering the oleochemical oil-based polyol.Type: ApplicationFiled: October 2, 2001Publication date: May 8, 2003Inventors: Dwight W. Chasar, Michael J. Hughes
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Patent number: 6548609Abstract: The present invention is related to an improved process for obtaining oleochemical polyols from oils, principally of a vegetable origin. The polyols obtained consist of a mixture of ethers, esters, primary and secondary alcohols and have the characteristic of being self-compatible with the new blowing agents: hydrochlorofluorocarbons, HCFC's, hydrofluorocarbons, HFC's and hydrocarbons, HC's of a low molecular weight and low boiling point. The process of this invention is characterized because it uses Lewis type acids in such a way that they do not form precipitates and therefore it is not necessary to remove precipitates from the polyol. The process of the present invention makes it possible to obtain polyols with high functionality and controlled reactivity. These characteristics render the product suitable for use as a raw material in the production process of rigid foams, such as polyurethane for spraying, refrigeration and imitation wood, coatings, among others.Type: GrantFiled: November 21, 2001Date of Patent: April 15, 2003Assignee: Resinas Y Materiales S.A. De C.V.Inventors: Nicolás Ramírez-de-Arellano-Aburto, Andrés Cohen-Barki, M. Javier Cruz-Gómez
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Patent number: RE42313Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: June 7, 2005Date of Patent: April 26, 2011Assignees: The United States of America as repesented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
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Patent number: RE48861Abstract: The present technology provides a process of reducing, removing or eliminating organohalo, glycidol, and oxirane species from carboxylic acid esters streams and crude and refined triglyceride oils to provide a carboxylic acid ester stream or triglyceride oil with reduced levels or essentially free of organohalo, glycidyl or other oxirane species. The process includes adding to the carboxylic acid ester stream or triglyceride oil an amount of a carboxylate anion and a cation counterion sufficient to react with the organohalo, glycidyl and oxirane species present.Type: GrantFiled: March 20, 2020Date of Patent: December 28, 2021Assignee: STEPAN SPECIALTY PRODUCTS, LLCInventors: Joseph C. Rongione, Jenifer Heydinger-Galante