Abstract: This disclosure is directed to compound of formula (1): wherein R1 is a C7-18 alkyl, R2 is hydrogen or a C1-3 alkyl, each R3, R4, R5, R6, and R7 is independently hydrogen or a C1-6 alkyl, a is 2-3, and b is 0-1, its method of preparation and uses thereof in water-borne coating compositions, cleaning compositions, fragrance, and personal care compositions.
Abstract: A water-reducible coating composition includes a water-reducible polymer binder; water; and a ketal adduct of formula (1) as well as coated substrates and films formed from the compositions. The films are useful as paints, stains, and clear-coats.
Type:
Grant
Filed:
October 18, 2011
Date of Patent:
May 20, 2014
Assignee:
Segetis, Inc.
Inventors:
Dorie J. Yontz, Daniel Warren Gilbert, Lee R. Rieth, Cora M. Leibig, Mike Jackson
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.
Abstract: The reaction of alcohols with oxocarboxylates to form acetals or ketals is catalyzed by unexpectedly low levels of protic acids. By employing low acid catalyst levels compared to amounts conventionally used, rapid formation of acetal or ketal is facilitated while the formation of oxocarboxylate esters is minimized. Further employing a significant molar excess of oxocarboxylate in conjunction with low acid catalyst level gives rise to the rapid and clean formation of acetals and ketals from oxocarboxylates and alcohols.
Type:
Grant
Filed:
April 9, 2010
Date of Patent:
December 10, 2013
Assignee:
Segetis, Inc.
Inventors:
Sergey Selifonov, Scott D. Rothstein, Brian D. Mullen
Abstract: Novel ketal compounds can be made from an oxocarboxylate and a triol. Novel polymeric structures are, in turn, synthesized from the ketal compounds. Such ketal compounds and associated polymers are useful in a broad range of applications as a substitute for materials derived from petroleum or other such nonrenewable resources.
Type:
Grant
Filed:
September 4, 2008
Date of Patent:
December 10, 2013
Assignee:
Segetis, Inc.
Inventors:
Douglas Alan Wicks, Charles Todd Williams, Sergey A. Selifonov
Abstract: Various esterified alkyl ketal ester or hydroxyalkyl ketal ester products are useful as components of organic polymer compositions. The ketal esters are produced in certain transesterifications between alkyl ketal esters and/or hydroxyalkyl ketal esters and polyols, aminoalcohols, polyamines, and/or polycarboxylic acids. The products are excellent plasticizers for a variety of organic polymers, notable poly(vinyl chloride) plastisols. The products are also very good lubricants for many lubrication applications.
Type:
Application
Filed:
July 24, 2013
Publication date:
November 21, 2013
Applicant:
SEGETIS, Inc.
Inventors:
Brian D. Mullen, Chunyong Wu, Tara J. Mullen, Marc D. Scholten, Vivek Badarinarayana
Abstract: The present disclosure relates to the preparation of acrylate, alkacrylate, allyl, and polycarbonate derivatives of hydroxy ketal esters, and uses thereof.
Type:
Grant
Filed:
September 25, 2009
Date of Patent:
November 5, 2013
Assignee:
Segetis, Inc.
Inventors:
Sergey Selifonov, Brian Daniel Mullen, Douglas Alan Wicks, Vivek Badarinarayana
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.
Abstract: The reaction of alcohols with oxocarboxylates to form acetals or ketals is catalyzed by unexpectedly low levels of protic acids. By employing low acid catalyst levels compared to amounts conventionally used, rapid formation of acetal or ketal is facilitated while the formation of oxocarboxylate esters is minimized. Further employing a significant molar excess of oxocarboxylate in conjunction with low acid catalyst level gives rise to the rapid and clean formation of acetals and ketals from oxocarboxylates and alcohols.
Type:
Grant
Filed:
April 9, 2010
Date of Patent:
October 29, 2013
Assignee:
Segetis, Inc.
Inventors:
Sergey Selifonov, Scott D. Rothstein, Brian D. Mullen
Abstract: A thermosetting composition comprises in combination an ethylenically unsaturated polymer, and a lactone reactive diluent of the formula wherein b=0 or 1. A method of manufacture of a thermoset polymer comprises reacting the unsaturated polymer and the lactone to form the thermoset polymer. The thermoset polymers are described, as well as articles comprising the thermoset polymers.
Type:
Application
Filed:
March 28, 2013
Publication date:
October 3, 2013
Applicant:
SEGETIS, Inc.
Inventors:
Brian D. Mullen, Marc D. Rodwogin, Dorie J. Yontz
Abstract: The invention relates to polyketal compounds. The compounds are synthesized by the selective ketalization of oxocarboxylic acids, e.g. keto acids and semialdehydes, and esters thereof with tetrols and higher polyols that products two or more cyclic ketal ester moieties per molecule, wherein the cyclic ketal moieties are situated in a bis-, tris-, or polyketal conformation. The invention further relates to applications of these compounds and subsequent reactions thereof.
Type:
Grant
Filed:
October 9, 2008
Date of Patent:
October 1, 2013
Assignee:
Segetis, Inc.
Inventors:
Sergey Selifonov, Scott D. Rothstein, Douglas A. Wicks, Brian D. Mullen, Tara J. Mullen, Jason D. Pratt, Charles T. Williams, Chunyong Wu, Ning Zhou
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.
Abstract: Ketocarboxylic acids such as levulinic acid can be efficiently purified in high yield by esterification with a hydrocarbon polyol to the corresponding polyketocarboxylic ester, which can be readily purified, for example recrystallized. After purification, the ketocarboxylic ester can be hydrolyzed to provide pure ketocarboxylic acid, or a salt thereof, after removal of the esterifying hydrocarbon polyol, or used for other synthetic transformations. Advantageously, the polyketocarboxylic esters, ketocarboxylic acids, and salts thereof produced by this method are obtained in high purity.
Type:
Grant
Filed:
November 11, 2011
Date of Patent:
August 13, 2013
Assignee:
Segetis, Inc.
Inventors:
Brian D. Mullen, Cora M. Leibig, Leo E. Manzer
Abstract: The present disclosure relates to the preparation of ketal compounds from glycerol and levulinic acid and esters, and uses thereof, in particular the manufacture of polyurethanes.
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.
Abstract: The invention describes methods of preparation and compositions of plasticizers. The plasticizers include at least 2 alkyl ketal ester moieties and have a molecular weight of greater than 300. In one aspect, the alkyl ketal ester moieties are levulinic ester ketals. Certain compositions contain at least one of an antioxidant, a UV stabilizer, a thermal stabilizer or mixtures thereof, present in the composition from about 0.01 to about 5.0 percent by weight of the total composition.