Oxirane Containing Reactant Patents (Class 554/149)
  • Patent number: 9777245
    Abstract: Metathesized triacylglycerol polyols, fractionated polyol variants thereof, and their related physical and thermal properties are disclosed.
    Type: Grant
    Filed: January 25, 2016
    Date of Patent: October 3, 2017
    Assignee: Trent University
    Inventors: Suresh Narine, Prasanth Kumar Sasidharan Pillai, Shaojun Li, Laziz Bouzidi, Ali Mahdevari
  • Patent number: 9668955
    Abstract: 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: Grant
    Filed: July 14, 2014
    Date of Patent: June 6, 2017
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Diza Pearl Braksmayer, Timothy A. Murphy, Stephen E. Russell, Michael John Tupy, Scott A. Walters
  • Patent number: 9598358
    Abstract: 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: Grant
    Filed: June 28, 2011
    Date of Patent: March 21, 2017
    Assignee: HUNTSMAN PETROCHEMICAL LLC
    Inventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
  • Patent number: 9056828
    Abstract: 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: Grant
    Filed: August 11, 2011
    Date of Patent: June 16, 2015
    Assignee: Kolb Distribution Ltd.
    Inventors: Christoph Kolano, Lothar Möhle, Rudolf Richner
  • Patent number: 9051260
    Abstract: 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: Grant
    Filed: September 2, 2011
    Date of Patent: June 9, 2015
    Assignee: STEPAN SPECIALITY PRODUCTS, LLC
    Inventors: Joseph C. Rongione, Jenifer Heydinger Galante
  • Publication number: 20140329985
    Abstract: 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 invention
    Type: Application
    Filed: December 19, 2011
    Publication date: November 6, 2014
    Inventors: Klaus Lorenz, Jörg Hofmann, Bert Klesczewski, Norber Hahn
  • Patent number: 8829216
    Abstract: 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: Grant
    Filed: August 31, 2012
    Date of Patent: September 9, 2014
    Assignee: Biosynthetic Technologies, LLC
    Inventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
  • Patent number: 8816020
    Abstract: 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: Grant
    Filed: October 18, 2012
    Date of Patent: August 26, 2014
    Assignee: Malaysian Palm Oil Board
    Inventor: Hoong Seng Soi
  • Patent number: 8686169
    Abstract: 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: Grant
    Filed: April 8, 2013
    Date of Patent: April 1, 2014
    Assignee: Segetis, Inc.
    Inventor: Sergey Selifonov
  • Patent number: 8674124
    Abstract: 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: Grant
    Filed: April 6, 2011
    Date of Patent: March 18, 2014
    Assignee: Biobased Technologies LLC
    Inventors: Trevor Newbold, Sandra Mae Newbold, Srikanth Yalamanchili
  • Patent number: 8575380
    Abstract: 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: Grant
    Filed: October 17, 2012
    Date of Patent: November 5, 2013
    Assignee: NOF Corporation
    Inventors: Fumiaki Manabe, Yuji Yamamoto
  • Publication number: 20130281688
    Abstract: 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: Application
    Filed: April 22, 2013
    Publication date: October 24, 2013
    Applicant: Elevance Renewable Sciences, Inc
    Inventors: Stephen A. Di Biase, Keith M. Wampler, David R. Allen, Randal J. Bernhardt, Ryan Littich
  • Patent number: 8557139
    Abstract: 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: Grant
    Filed: February 12, 2009
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies LLC
    Inventor: Robert F. Eaton
  • Publication number: 20130150601
    Abstract: 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: Application
    Filed: August 11, 2011
    Publication date: June 13, 2013
    Applicant: KOLB DISTRIBUTION LTD.
    Inventors: Christoph Kolano, Lothar Möhle, Rudolf Richner
  • Publication number: 20130102737
    Abstract: 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: Application
    Filed: October 18, 2012
    Publication date: April 25, 2013
    Applicant: Malaysian Palm Oil Board
    Inventor: Hoong Seng Soi
  • Publication number: 20130046102
    Abstract: 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: Application
    Filed: October 22, 2012
    Publication date: February 21, 2013
    Applicant: SEGETIS, INC.
    Inventor: SEGETIS, INC.
  • Publication number: 20130005937
    Abstract: 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: Application
    Filed: September 10, 2010
    Publication date: January 3, 2013
    Applicant: Centre National De La Recherche Scientifique (C.N.R.S.)
    Inventors: Henri Cramail, Aurélie Boyer, Eric Cloutet, Rachida Bakhiyi, Carine Alfos
  • Publication number: 20120309994
    Abstract: 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: Application
    Filed: August 13, 2012
    Publication date: December 6, 2012
    Applicant: Cognis IP Management GmbH
    Inventors: Joaquin Bigorra Llosas, Luis Llaurado, Francesc Gusi
  • Patent number: 8308975
    Abstract: 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: Grant
    Filed: October 25, 2011
    Date of Patent: November 13, 2012
    Assignee: BASF SE
    Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore Michael Smiecinski
  • Publication number: 20120208732
    Abstract: 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: Application
    Filed: February 13, 2011
    Publication date: August 16, 2012
    Inventors: Suresh Narine, Shaojun Li, Ali Mahdevari, Laziz Bouzidi, Stephen Augustine DiBiase, Syed Q.A. Rizvi
  • Patent number: 8173825
    Abstract: 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: Grant
    Filed: March 13, 2007
    Date of Patent: May 8, 2012
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
  • Patent number: 8153746
    Abstract: 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: Grant
    Filed: June 2, 2010
    Date of Patent: April 10, 2012
    Assignee: Cargill, Incorporated
    Inventors: Zoran S. Petrovic, Ivan X. Javni, Alisa Zlatanic, Andrew Xiuguang Guo
  • Publication number: 20120065260
    Abstract: 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: Application
    Filed: September 6, 2011
    Publication date: March 15, 2012
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Patent number: 8105993
    Abstract: 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: Grant
    Filed: May 1, 2007
    Date of Patent: January 31, 2012
    Assignee: Huntsman Petrochemical LLC
    Inventors: Prakasa R. Anantaneni, George A. Smith, Martin J. Renner
  • Patent number: 8084631
    Abstract: 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: Grant
    Filed: May 15, 2008
    Date of Patent: December 27, 2011
    Assignee: BASF SE
    Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
  • Publication number: 20110218350
    Abstract: 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: Application
    Filed: May 20, 2011
    Publication date: September 8, 2011
    Applicant: SEGETIS, INC.
    Inventor: Sergey SELIFONOV
  • Patent number: 8008239
    Abstract: 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: Grant
    Filed: August 11, 2004
    Date of Patent: August 30, 2011
    Assignee: Huntsman Petrochemical LLC
    Inventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
  • Patent number: 7892599
    Abstract: 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: Grant
    Filed: July 27, 2004
    Date of Patent: February 22, 2011
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Tapesh Yadav, Karl Pfaffenbach
  • Publication number: 20100311992
    Abstract: 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: Application
    Filed: June 2, 2010
    Publication date: December 9, 2010
    Applicant: CARGILL, INCORPORATED
    Inventors: Zoran S. PETROVIC, Ivan Javni, Alisa Zlatanic, Andrew Guo
  • Publication number: 20100292373
    Abstract: 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: Application
    Filed: November 22, 2006
    Publication date: November 18, 2010
    Inventor: Sergey Selifonov
  • Publication number: 20100267828
    Abstract: 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: Application
    Filed: October 30, 2008
    Publication date: October 21, 2010
    Inventors: Anne Kristin Holmeide, Ragnar Hovland
  • Patent number: 7786239
    Abstract: 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: Grant
    Filed: June 24, 2005
    Date of Patent: August 31, 2010
    Assignee: Pittsburg State University
    Inventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
  • Publication number: 20090286896
    Abstract: 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: Application
    Filed: May 15, 2008
    Publication date: November 19, 2009
    Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
  • Patent number: 7544763
    Abstract: 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: Grant
    Filed: November 7, 2006
    Date of Patent: June 9, 2009
    Assignee: Arkema Inc.
    Inventor: Mohammad Kazemizadeh
  • Publication number: 20080281115
    Abstract: 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: Application
    Filed: May 1, 2008
    Publication date: November 13, 2008
    Applicant: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
    Inventors: Tong Wang, Liping Wang
  • Publication number: 20080227993
    Abstract: 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: Application
    Filed: March 17, 2007
    Publication date: September 18, 2008
    Inventor: Matthew Mark Zuckerman
  • Publication number: 20080154053
    Abstract: 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: Application
    Filed: March 13, 2007
    Publication date: June 26, 2008
    Applicants: The Unites States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Kenneth M. Doll, Brajendra K. Sharma
  • Publication number: 20070282117
    Abstract: 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: Application
    Filed: June 1, 2006
    Publication date: December 6, 2007
    Inventors: Trevor Newbold, David M. Casper
  • Patent number: 7279448
    Abstract: 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: Grant
    Filed: July 8, 2004
    Date of Patent: October 9, 2007
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The PENN State Research Foundation
    Inventors: Sevim Z. Erhan, Atanu Adhvaryu, Brajendra K. Sharma
  • Patent number: 6927299
    Abstract: 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: Grant
    Filed: July 15, 2003
    Date of Patent: August 9, 2005
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Toshio Endo
  • Patent number: 6797753
    Abstract: 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: Grant
    Filed: May 4, 2001
    Date of Patent: September 28, 2004
    Assignee: Battelle Memorial Institute
    Inventors: Herman P. Benecke, Bhima R. Vijayendran, Joel D. Elhard
  • Patent number: 6765116
    Abstract: 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: Grant
    Filed: August 23, 2002
    Date of Patent: July 20, 2004
    Assignee: Shell Oil Company
    Inventor: Charles Lee Edwards
  • Patent number: 6706768
    Abstract: 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: Grant
    Filed: March 21, 2002
    Date of Patent: March 16, 2004
    Assignee: International Flora Technologies, Ltd.
    Inventors: James H. Brown, Robert Kleiman, John C. Hill
  • Patent number: 6646145
    Abstract: 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: Grant
    Filed: January 8, 2002
    Date of Patent: November 11, 2003
    Assignee: Cognis Deutschland GmbH
    Inventors: Ansgar Behler, Horst-Dieter Schares, Almud Folge
  • Patent number: 6583302
    Abstract: 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: Grant
    Filed: January 25, 2002
    Date of Patent: June 24, 2003
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
  • Publication number: 20030088054
    Abstract: 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: Application
    Filed: October 2, 2001
    Publication date: May 8, 2003
    Inventors: Dwight W. Chasar, Michael J. Hughes
  • Patent number: 6548609
    Abstract: 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: Grant
    Filed: November 21, 2001
    Date of Patent: April 15, 2003
    Assignee: Resinas Y Materiales S.A. De C.V.
    Inventors: Nicolás Ramírez-de-Arellano-Aburto, Andrés Cohen-Barki, M. Javier Cruz-Gómez
  • Patent number: 6531443
    Abstract: Improved modified monoethanolamide composition mixtures are provided which may be represented by the formula Wherein: R is an optionally substituted or unsubstituted, branched or straight chain, saturated or unsaturated hydrocarbon radical of 3-21 carbon atoms; B is CH3 or —CH2—CH3; and x is at least about 1. wherein the modified monoethanolamide compositions, which are liquid at ambient temperatures or lower, exhibit surfactant properties substantially the same as those exhibited by diethanolamides such as foam stabilization and viscosity building as well as other desirable characteristics.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: March 11, 2003
    Assignee: Mona Industries, Inc.
    Inventors: James E. Perella, Joseph A. Komor, Dennis L. Fost, Richard D. Katstra
  • Patent number: 6429324
    Abstract: Processes for preparing alkylene glycol esters of dimer fatty acids according to the general formula (I): H—(OR)n—O(O)C—R1—C(O)O—(RO)n—H  (I) wherein R1 represents a hydrocarbon radical of a dimer fatty acid having from about 24 to about 44 carbon atoms, and each R independently represents an alkyl radical having from about 2 to about 3 carbon atoms, and each n independently represents a number of from about 0.25 to about 3.0, are described. The processes include: (a) providing dimer fatty acids; (b) providing an alkylene oxide; and (c) reacting the dimer fatty acids and the alkylene oxide, in the presence of a catalytically-effective amount of at least one alkanolamine.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: August 6, 2002
    Assignee: Cognis Deutschland and GmbH
    Inventors: Hans-Christian Raths, Frank Bongardt, Ansgar Behler, Juergen Roeder
  • Patent number: RE42313
    Abstract: 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: Grant
    Filed: June 7, 2005
    Date of Patent: April 26, 2011
    Assignees: The United States of America as repesented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu