Battelle Memorial Institute

Solazyme, Inc.

Jeffrey T Cafmeyer

Daniel B Garbark

Bhima Rao Vijayendran

Herman P Benecke

Ramanathan S Lalgudi

Mark J Perry

Joel D Elhard

Amy M Heintz

Michael Clingerman

Katherine P Mitchell

Megan Moore

Jerry L King, Ii

Vincent Daniel McGinniss

Steven Risser

Jay R Sayre

Risha Lindig Bond

Robert J Cain

Diza Braksmayer

Phillip N Denen

James L White

J David Robbins

Abhishek Gupta

Elizabeth Drotleff

Joan T Muellerleile

Manoj Kumar Valluri

Albert J Darling

Michael C Clingerman

Wayne B Robbins

Anne-Claire Christiaen

Frederyk Ngantung

Herman Paul Benecke

Steven M Risser

Joan Muellerleile

Vincent D Mcginniss

Bio-based surfactants have great opportunity for use in a variety of applications such as laundry detergents, industrial cleaners, adjuvants, and oil & gas. Surfactants in these applications can be nonionic, anionic, cationic, or amphoteric. Utilizing high oleic soybean oil as a platform chemical, a variety of surfactants and properties can be produced. While early work focused solely on surfactant use in laundry cleaning and fracking, recent work has expanded functional groups and application evaluations in hard surface cleaning. The current invention expands on Battelle's high oleic soybean oil (HOSO) surfactant technology. Use of HOSO overcomes the limitations of regular soybean oil and significantly reduces or eliminates undesirable byproducts in most chemistries. However, with use of select reagents, a few candidates were achievable with regular epoxidized soybean oil (ESO). The HOSO surfactant platform offers several key advantages including: a highly water miscible (not typical of C18 surfactants) and water stable surfactant; ability to adjust and vary hydrophilic-lipophilic (HLB) values for stain removal performance; and increased biodegradability without toxic or persistent by-products.

Bio-based surfactants

Powder coating resins and coatings made using the powder coating resins are described. The powder coating resins are based on the use of Cto Cdiesters. The Cto Cdiesters are reacted with a reactant having an alcohol functionality and an amine functionality to form an intermediate polyol, followed by reaction with a diacid to a carboxylic acid terminated polymer having ester and amide functionality.

Soybean-based powder coating resins from C16-C23 diesters

Powder coating resins and coatings made using the powder coating resins are described. The powder coating resins are based on the use of Cto Cdiacids. The Cto Cdiacids are reacted with a reactant having an alcohol functionality and an amine functionality to form a carboxylic acid terminated polymer having ester and amide functionality. Alternatively, the Cto Cdiacids are reacted with a reactant having an alcohol functionality and an amine functionality to form an intermediate polyol, which is then reacted with acetoacetic acid or an ester thereof to form an acetoacetate-terminated polymer.

Powder coating resins from C12—C23 diacids

An alkoxylated bio-oil composition is provided. The alkoxylated bio-oil composition may include an alkoxylated bio-oil prepared from an alkoxylation of dewatered bio-oil. A method for preparing an alkoxylated bio-oil composition is provided. A copolymer composition is provided. The copolymer composition may include an alkoxylated bio-oil copolymer unit. A method for preparing a copolymer composition is provided.

Direct alkoxylation of bio-oil

Methods are provided for producing bio-oil polyols, alkoxylating bio-oil polyols to provide polyols, and for employing the alkoxylated bio-oil polyols for making polymers or copolymers of polyesters or polyurethanes.

Alkoxylated bio-oil polyol compositions

Fatty acid based surfactants and methods for producing fatty acid based surfactants are described. The method includes reacting a fatty acid ester epoxide with a hydroxy acid, a hydroxy ester, a polyoxyalkyl diol, or a polyamine. Any remaining esters from the original fatty acid ester epoxide or hydroxy ester can optionally be hydrolyzed. Methods for making citric acid derived surfactants are also described.

Laundry builders and surfactants derived from bio-based hydroxyacids and epoxides

Linear &#x3b1;, &#x3c9;-nonadecanediester derivatives and methods of making the derivatives are described. The methods include reacting a linear &#x3b1;, &#x3c9;-nonadecanediester or a linear &#x3b1;, &#x3c9;-nonadecanedicarboxylic acid with a reactant optionally in the presence of at least one of a solvent and a catalyst to form the &#x3b1;, &#x3c9;-nonadecanediester derivative. Methods of making linear &#x3b1;, &#x3c9;-nonadecanediester or diester derivatives are also described.

Methods of making 1,19-nonadecanediester and derivatives thereof

A method is described for preparing carbon nanotube dispersions in organic solvents such as chloroform and methyl ethyl ketone. Structures resulting from organic dispersions are also disclosed. The dispersing agents used in this method comprise long chain hydrocarbons, halogen-substituted hydrocarbons, fluorocarbons, or a mixture of hydrocarbons, halogen-substituted hydrocarbons, and fluorocarbons; wherein the hydrocarbons, halogen-substituted hydrocarbons and fluorocarbons have from 6 to 40 carbons in a chain, at least one alkene or alkyne moiety, and at least one pendant carboxylic acid, phosphonic acid, and/or sulfonic acid group or an ester of these acids.

Methods of dispersing carbon nanotubes

Lubricants based on renewable feedstocks and methods of making them. 

Modified vegetable oil lubricants

Provided are microalgal oils having a low polyunsaturated fatty acid profile and derivatives of the oils, including acids, esters, epoxides, hydroxylated acids and esters, urethanes, amides, and polymers thereof. Also provided are compositions comprising the oils and their derivatives and their uses in foodstuffs and in industrial and material applications. The compositions include flexible polyurethane foams prepared from the microalgal oils.

Low polyunsaturated fatty acid oils and uses thereof

A series of resins were synthesized using a range of bio-based materials to control the molecular architecture, and therefore the properties, of the inventive resins. The utility of these resins was demonstrated in the formulation of powder coatings, such as &#x3b2;-hydroxy amide crosslinked and hybrid types. Generally, the bio-based resins flowed out on heating faster than conventional petrochemically-based resins, allowing the use of lower temperatures in the curing oven than is typically possible and a more active catalyst system, especially in the carboxylic acid-epoxy crosslinked hybrid coating formulations.

Resins, low temperature formulations, and coatings derived therefrom

An electrically conductive coating composition is provided for use on aircraft and other substrate surfaces to prevent the formation of ice or to melt ice. The conductive coating composition may include a nanomaterial such as carbon nanotubes dispersed in a solvent which may be applied to a substrate surface to form a thin film which is resistively heatable. The conductive coating may also comprise a nanomaterial formed from carbon nanotubes or fullerenes grafted to a polymer containing an active functional group which renders a substrate surface icephobic and is also resistively heatable.

Electrically conductive coating composition

A lubricant from plant and/or animal oils and fats; methods for producing a lubricating oil, and the oil produced thereby. The lubricant is derived from an animal or plant fat or oil having an iodine number above about 7, and produced by epoxi-dising the fat or oil and (1) reacting the epoxidised fat or oil with a carboxylic acid anhydride in the presence of a basic catalyst to produce a diester, or (2) hydrogenating the epoxidised fat or oil to generate mono-alcohols and acylating the alcohol functionality with acid anhydrides, acid chlorides or carboxylic acids to produce a mono-ester.

Growing community of inventors

Columbus, OH, United States of America

Jeffrey T Cafmeyer