Abstract: Disclosed is a method for using a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is a method for using a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is a method for using a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.
Type:
Grant
Filed:
March 11, 2014
Date of Patent:
January 16, 2018
Assignee:
THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE
Inventors:
Rex E. Murray, Kenneth M. Doll, Zengshe Liu
Abstract: The invention is generally directed to conjugated linoleic acid (CLA)-rich vegetable oil production from linoleic rich oils by heterogeneous catalysis. A heterogeneous catalytic vacuum distillation process is used under high temperature conditions to isomerize linoleic acid in triacylglyceride vegetable oils to CLA to produce CLA-rich oils. After processing, the catalyst may be removed by filtration or centrifugation to obtain high quality, CLA-rich oils. The CLA-rich oils may then serve as a potent and bioactive nutraceutical and can be incorporated into various food products, such as a CLA-rich dressing, margarine or chips.
Type:
Grant
Filed:
December 3, 2012
Date of Patent:
June 23, 2015
Assignee:
Board of Trustees of the University of Arkansas
Abstract: Process for the production of saturated monocarboxylic acids and triglycerides of saturated carboxylic acids having more than one acid function starting from non-modified vegetable oils containing triglycerides of unsaturated fatty acids, comprising the oxidative cleavage of the unsaturated fatty acids.
Abstract: The invention provides processes for preparing soy-based oligomeric polyols or substituted oligomeric polyols, as well as urethane bioelasteromers comprising the oligomeric polyols or substituted oligomeric polyols.
Type:
Grant
Filed:
February 2, 2010
Date of Patent:
June 25, 2013
Assignee:
The Curators of the University of Missouri
Inventors:
Galen Suppes, Zuleica Lozada, Arnold Lubguban
Abstract: The present invention includes a polyol produced according to the process comprising reacting a multifunctional alcohol with a first multifunctional component to form a reaction product and reacting the reaction product with a vegetable oil to form a polyol. The present invention also relates to the material comprising the reaction product of an A-side and a B-side, wherein the A-side comprises an isocyanate and the B-side comprises the product formed by the process comprising the steps of reacting a multifunctional alcohol with a first multifunctional component to form a precursor polyol and then reacting the precursor polyol with a vegetable oil to form a vegetable based polyol with selectable functionality.
Type:
Grant
Filed:
October 31, 2007
Date of Patent:
December 18, 2012
Assignee:
Tandem Polymers, Inc.
Inventors:
Thomas M. Kurth, Richard A. Kurth, Robert B. Turner, Les P. Kreifels, Todd A. Van Thomme
Abstract: The invention provides processes for converting a vegetable oil to a polymer. In particular, the processing steps comprise bodying, epoxidation, hydrolysis, and oligomerization. These processes provide new processing paths for the formation of polyols for use in rigid foam and other applications.
Type:
Grant
Filed:
May 9, 2007
Date of Patent:
April 13, 2010
Assignee:
The Curators of the University of Missouri
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.
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
Abstract: The invention relates to a continuous method for producing a cross-linked unsaturated fatty acid-based or fatty acid ester-based bonding agent, an elastic bonding agent produced according to said method and the use of said elastic bonding agent.
Abstract: Novel latex or emulsion compositions containing internally plasticizing and crosslinkable monomers derived from traditional semi-drying or non-drying oils are disclosed and claimed. The monomers are ethylenically unsaturated derivatives of long-chain olefinic compounds. Preferred embodiments include latex formed from acrylate or methacrylate esters of fatty alcohols. A process for the synthesis of the latex composition is also disclosed, which involves (a) polymerization of the ethylenically unsaturated derivatives of a long-chain olefinic compound in an aqueous phase with at least one other copolymerizable monomer; and (b) blending of so formed polymer with at least one drier and a surfactant to form the novel latex or emulsion compositions. These compositions form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C.
Type:
Grant
Filed:
January 12, 2001
Date of Patent:
July 29, 2003
Assignee:
University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Olan Stanley Fruchey
Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
Type:
Application
Filed:
April 10, 2001
Publication date:
January 17, 2002
Applicant:
University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
Abstract: Novel compounds derived from traditional semi- drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
Type:
Application
Filed:
April 10, 2001
Publication date:
October 18, 2001
Applicant:
The University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
Abstract: A process for modifying an unsaturated polyol fatty acid ester stock, such as an unsaturated triacylglycerol oil, to enhance its fluidity and/or oxidative stability is provided. The method includes reacting the unsaturated polyol fatty acid ester stock with cyclopropanating agent. Lubricants containing cyclopropanated polyol fatty acid ester and methods for their production and use are also provided.
Abstract: Oils containing a triacylglycerol polyol ester and a non-glycerol polyol ester are described, as well as methods of making such oils. Methods for improving lubrication properties of a vegetable oil also are described.
Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
Type:
Grant
Filed:
December 24, 1996
Date of Patent:
May 22, 2001
Assignee:
University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
Abstract: Novel latex or emulsion compositions containing internally plasticizing and crosslinkable monomers derived from traditional semi-drying or non-drying oils are disclosed and claimed. The monomers are ethylenically unsaturated esters of long-chain olefinic compounds. Preferred embodiments include latex formed from acrylate or methacrylate esters of hydroxy fatty acid esters derived from castor oil or lesquerella oil. A process for the synthesis of the latex composition is also disclosed, which involves (a) an esterification reaction of ethylenically unsaturated carboxylic acid or its derivatives with a substituted hydroxy long-chain olefinic compound; (b) subsequent polymerization of the so formed ethylenically unsaturated ester of a long-chain olefinic compound in an aqueous phase with at least one other copolymerizable monomer; and (c) blending so formed polymer with at least one drier and a surfactant to form the novel latex or emulsion compositions.
Type:
Grant
Filed:
December 24, 1996
Date of Patent:
March 20, 2001
Assignee:
University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
Abstract: Novel latex or emulsion compositions containing internally plasticizing and crosslinkable monomers derived from traditional semi-drying or non-drying oils are disclosed and claimed. The monomers are ethylenically unsaturated derivatives of long-chain olefinic compounds. Preferred embodiments include latex formed from acrylate or methacrylate esters of fatty alcohols. A process for the synthesis of the latex composition is also disclosed, which involves (a) polymerization of the ethylenically unsaturated derivatives of a long-chain olefinic compound in an aqueous phase with at least one other copolymerizable monomer; and (b) blending of so formed polymer with at least one drier and a surfactant to form the novel latex or emulsion compositions. These compositions form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C.
Type:
Grant
Filed:
December 24, 1996
Date of Patent:
January 16, 2001
Assignee:
The University of Southern Mississippi
Inventors:
Shelby Freland Thames, Kamlesh Gopichand Panjnani, Olan Stanley Fruchey
Abstract: A process for modifying an unsaturated polyol fatty acid ester stock, such as an unsaturated triacylglycerol oil, to enhance its fluidity and/or oxidative stability is provided. The method includes reacting the unsaturated polyol fatty acid ester stock with cyclopropanating agent. Lubricants containing a modified unsaturated polyol fatty acid ester and methods for their production and use are also provided.
Abstract: The invention provides a method of conjugating double bonded drying oil so that a relatively low cost linseed oil, for example, can replace the more expensive, naturally conjugated tung oil which has been used heretofore. The conjugation is brought about by the use of ruthenium as a catalyst, with formic or a similar acid providing a synergistic augmentation of the reaction. The conjugated oil may have many uses, but a major object is to provide a way to enhance a phenolic resin adhesive used on wood and wood products.
Abstract: A non-volatile compound useful as a solvent and a method of manufacturing the compound. The compound is formed from heating a combination of a lactide and a drying oil which has conjugated double bonds. The compound is particularly useful as a resin solvent for use with coatings, paints and printing inks. In addition, it can be used as a compatibilizing agent.
Abstract: A non-volatile compound useful as a solvent and a method of manufacturing the compound. The compound is formed from heating a combination of a lactide and a drying oil which has conjugated double bonds. The compound is particularly useful as a resin solvent for use with coatings, paints and printing inks. In addition, it can be used as a compatibilizing agent.