United States of America, As Represented by the Secretary of Agriculture

The United States of America As Represented by the Secretary of

Terry A Isbell

Steven C Cermak

Thomas P Abbott

Benjamin A Lowery

Kenneth Michael Doll

David L Compton

Rogers E Harry-O'kuru

James A Kenar

Robert Kleiman

Joseph E Lohr, Jr

Melissa S Mund

John A Dworak

Svajus Asadauskas

Amber L Durham

Beth A Plattner

The invention relates to methods for the synthesis of hydroxy fatty acids from unsaturated fatty acids via epoxidation and catalytic hydrogenation.

Hydroxy fatty acid synthesis

Disclosed are compositions containing at least one of the following:

Polyethylene diester viscosity modifiers

Levulinic-capped estolides having improved physical properties that make them more desirable and suitable as bio-based industrial or commercial products are disclosed. The physical properties of the disclosed estolide compositions have surprisingly low pour points that are substantially lower than previously known estolide compounds and superior to petroleum-based compounds designed for similar applications.

Bio-based estolide compositions

Disclosed herein are the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. The estolides containing a cyclic carbonate may be used to produce urethane containing estolides.

Carbonated estolides and methods of making and using the same

A class of UVA- and UVB-absorbing esters has been derived by modifying hydroxy triglycerides and other acyltriglycerides with any of a variety of cinnamic acids. The esterification reactions are preferably conducted at elevated temperatures without a catalyst. The resultant agents have the advantage of being synthesized from natural materials, while providing a value-added use for the oil. They are readily formulated into standard UV-absorbing daily-wear cosmetic, hair and skin care, and sunscreen formulations.

Sunscreen reagents from hydroxy-substituted acylglycerides

Esters of estolides derived from oleic acids and C-6 to C-14 saturated fatty acids are characterized by superior properties for use as lubricant base stocks. These estolides may also be used as lubricants without the need for fortifying additives normally required to improve the lubricating properties of base stocks.

Biodegradable oleic estolide ester having saturated fatty acid end group useful as lubricant base stock

Fatty ether compounds and a process for their production is disclosed. The compounds possess low viscosity and low temperature melting point properties and may be used as viscosity modifiers in the creation of cosmetics and complete vegetable oil based biodegradable fluids such as hydraulic fluids and dielectric fluids. Formation of these fatty ether compounds is by reaction of the appropriate hydroxy fatty acid or lactone with a nucleophilic alcohol in the presence of an acid catalyst to produce fatty ether esters. Following their formation, the fatty ether esters may be recovered for subsequent use, or in the alternative, they may either be hydrolyzed to produce fatty ether acids or transesterified with a different nucleophilic alcohol in the presence of an acid catalyst to produce alternate ester variants.

Preparation of secondary ether fatty acids and esters from their hydroxy fatty acid equivalents

Improved shampoos and conditioners are disclosed which provide enhanced rinseability, wet feel, detangling, dry comb feel, style management, shine and/or body to human hair. This improved performance may be achieved by incorporation of fatty acid estolides into the shampoo or conditioner. Thus, the improved shampoos of this invention include aqueous compositions of a surfactant cleansing agent, and a thickener, in combination with one or more fatty acid estolides. Similarly, the improved conditioners of this invention include aqueous compositions of a hair conditioning agent in combination with one or more fatty acid estolides.

Shampoos and conditioners containing estolides

An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.9 to .DELTA..sup.15 unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20 to 70.degree. C. Moreover, yields of the .delta.-lactones may be increased even further by reaction in the presence of dipolar, non-participating, non-aqueous solvents. The unsaturated fatty acids may be free or esterified with glycerol or other aliphatic alcohols, and the .delta.-lactones may be produced by reacting mono-, di- or triglycerides of the unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the instant process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steam splitting. Optionally, the .delta.-lactones so formed may be further reacted to produce 5-hydroxy fatty acids. These 5-hydroxy fatty acids may be produced by reaction of the .delta.-lactones with an alkali in an aqueous solution.

Method for the development of .delta.-lactones and hydroxy acids from

Esters of estolides derived from oleic acids are characterized by superior properties for use as lubricant base stocks. These estolides may also be used as lubricants without the need for fortifying additives normally required to improve the lubricating properties of base stocks.

Biodegradable oleic estolide ester base stocks and lubricants

An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.

Growing community of inventors

Elmwood, IL, United States of America

Terry A Isbell