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:
July 3, 2013
Date of Patent:
December 29, 2015
Assignee:
SEGETIS, INC.
Inventors:
Brian D. Mullen, Leo E. Manzer, Cora M. Leibig
Abstract: Disclosed herein is a polyketal adduct obtained by forming an ester between a hydrocarbon polyol and a ketocarboxylic acid to produce an intermediate polyketocarboxylic ester. The intermediate polyketocarboxylic ester can be purified via crystallization to achieve purities of greater than 99.0% and then ketalized to produce the polyketal adduct, which can be used in polymer compositions. The polyketal adduct I is obtained at high purity and at high yield.
Type:
Grant
Filed:
November 11, 2011
Date of Patent:
December 15, 2015
Assignee:
SEGETIS, INC.
Inventors:
Brian D. Mullen, Marc D. Scholten, Tara J. Mullen, Cora M. Leibig, Vivek Badarinarayana, Matthew J. Tjosaas
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:
November 1, 2013
Date of Patent:
December 8, 2015
Assignee:
SEGETIS, INC.
Inventors:
Sergey Selifonov, Brian Daniel Mullen, Douglas Alan Wicks, Vivek Badarinarayana
Abstract: Disclosed herein is a polyhydroxy ketal adduct obtained by the esterification of a hydrocarbon polyol by at least 1.5 equivalents of a ketocarboxy to produce an intermediate ketocarboxylic ester. The intermediate polyketocarboxylic ester is then ketalized to produce the polyhydroxyketal adduct, which can be used to provide a polymeric composition.
Type:
Grant
Filed:
November 11, 2011
Date of Patent:
November 17, 2015
Assignee:
SEGETIS, INC.
Inventors:
Brian D. Mullen, Marc D. Scholten, Dorie J. Yontz, Cora M. Leibig, Matthew J. Tjosaas
Abstract: Disclosed herein is a crosslinkable polyketal ester obtained by the esterification of a hydrocarbon polyol by at least 2 equivalents of a ketocarboxylic acid to produce an intermediate polyketocarboxylic ester. The intermediate polyketocarboxylic ester is then ketalized to produce the crosslinkable polyketal ester, which can then be used in compositions or crosslinked.
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 cleaning or personal care composition containing at least one of 1,4-pentanediol and a ketal alcohol of formula (1) wherein R2 is hydrogen or C1-3 alkyl, each R3, R4, and R5 is independently hydrogen or C1-6 alkyl, R6 and R7 are each independently hydrogen or C1-6 alkyl, a=0-3, and b=0-1. R2 is hydrogen or C1-3 alkyl, each R3, R4, and R5 is independently hydrogen or C1-6 alkyl, each R6 and R7 is independently hydrogen, C1-6 alkyl optionally substituted with at least one hydroxyl groups, a=1-6, and b=0-2.
Type:
Application
Filed:
September 20, 2013
Publication date:
September 10, 2015
Applicant:
SEGETIS, INC.
Inventors:
Lee R. Rieth, Satyanarayana Majeti, Erich J. Molitor
Abstract: A latex coating composition is disclosed, comprising a latex polymer binder; water; and a ketal adduct of formula (1) wherein R1 is C1-6 alkyl, R2 is hydrogen or C1-3 alkyl, each R3, R4, and R5 is independently hydrogen or C1-6 alkyl, R6 and R7 are each independently hydrogen or C1-6 alkyl, a is 0-3, and b is 0-1.
Type:
Grant
Filed:
August 12, 2011
Date of Patent:
July 7, 2015
Assignee:
SEGETIS, INC.
Inventors:
Lee R. Rieth, Cora M. Leibig, Jason D. Pratt, Mike Jackson
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:
Grant
Filed:
July 24, 2013
Date of Patent:
May 5, 2015
Assignee:
SEGETIS, Inc.
Inventors:
Brian D. Mullen, Chunyong Wu, Tara J. Mullen, Marc D. Scholten, Vivek Badarinarayana
Abstract: Personal care formulations containing alkyl ketal esters having the structure wherein a is 0 or an integer of 1 to 12; b is 0 or 1; R2 is a divalent C1-8 group optionally substituted with up to 5 hydroxyl groups; and R1 is C1-6 alkyl.
Type:
Application
Filed:
November 7, 2014
Publication date:
March 5, 2015
Applicant:
SEGETIS, INC.
Inventors:
Dorie J. YONTZ, Lee Richard RIETH, Nicholas MORANTE, Irwin PALEFSKY
Abstract: Disclosed herein are ketal amide compounds. The ketal amide compounds are synthesized by the reaction of ketal acids or ketal esters with amine functional compounds. Also disclosed are methodologies useful to make the ketal amide compounds. Also disclosed herein are formulations and articles containing the ketal amide compounds.
Type:
Grant
Filed:
February 10, 2012
Date of Patent:
March 3, 2015
Assignee:
Segetis, Inc.
Inventors:
Sergey Selifonov, Adam E. Goetz, Marc D. Scholten, Ning Zhou
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: A ketal ester of an oxocarboxylic acid and a process to make the same, where the ketal ester is of Structure (I): wherein a is 0 or an integer from 1 to 12; n is 0 or 1; R1 is a linear alkyl, aryl, arylalkylene, or branched alkyl group with 1-18 carbon atoms; R2 and R5 can be hydrogen, C1-6 straight chain or branched alkyl, phenyl, substituted phenyl, C1-6 alkyl substituted with up to four OH groups, C1-6 alkyl, or acetyl optionally substituted hydrocarbon radicals, or R2 and R4 together with the ?-carbon form a cycloaliphatic or heterocyclic ring with 3-6 carbon atoms and 0-3 heteroatoms, provided that only one of R2 and R5 is hydrogen; R3 is a linear alkyl or branched alkyl group with 1-18 carbon atoms; and R4 is hydrogen, or an alkyl, aryl, aralkyl or branched alkyl group with 1-10 carbon atoms.
Type:
Grant
Filed:
September 13, 2010
Date of Patent:
November 18, 2014
Assignee:
Segetis, Inc.
Inventors:
Douglas A. Wicks, Sergey Selifonov, Marc Davis Scholten
Abstract: Disclosed herein is a dispersion comprising a liquid or semi-solid continuous phase, a dispersed solid phase comprising a plurality of organic, inorganic or inorganic-organic particles, and an alkyl ketal ester having the structure wherein a is 0 or an integer of 1 to 12, specifically 1 to 6, more specifically 1 to 4; b is 0 or 1; R2 is a divalent C1-8 group optionally substituted with up to 5 hydroxyl groups; and R1 is C1-6 alkyl, and wherein at least a portion of the alkyl ketal ester is present in the continuous phase, on a surface of at least some of the dispersed particles, or a combination thereof.
Type:
Application
Filed:
March 31, 2014
Publication date:
October 2, 2014
Applicant:
SEGETIS, INC.
Inventors:
Lee Richard RIETH, Dorie J. YONTZ, Nicholas MORANTE
Abstract: An ionic polymer of formula VI wherein each b=0 or 1; X is hydrogen, 1/z of a metal ion of charge z, a protonated nitrogen base, or a tetrasubstituted organic ammonium compound; the molar ratio of q:r:s:t=(100-0.1):(0-99.9):(0-50):(0-30); R1, R2 and R3 are hydrogen or C1-4 alkyl; R4, R5, R6 and R7 are hydrogen, C1-4 alkyl or F, wherein F is a functional group that imparts a property to polymer VI, at least one and no more than two of R4, R5, R6 and R7 are F and F is the same or different; G is a single bond or a C1-30 hydrocarbyl group; and for each instance of t when t is not zero, c=0-5 and d=0-5, provided that c+d=1-5, and wherein q, r and s as present in c are independent of any other value of q, r and s.
Type:
Grant
Filed:
November 11, 2011
Date of Patent:
September 30, 2014
Assignee:
Segetis, Inc.
Inventors:
Dorie J. Yontz, Brian D. Mullen, Cora M. Leibig, Marc D. Rodwogin, Vivek Badarinarayana, Feng Jing, Friederike T. Stollmaier
Abstract: A removal composition is described, having a plurality of abrasive particles, an organic amine, antioxidant, biocide, colorant, corrosion inhibitor, cosolvent, defoamer, dye, enzyme, light stabilizer, odor masking agent, plasticizer, preservative, rust inhibitor, surfactant, thickener, or a combination comprising at least one of the foregoing; from 0 to 1% water, based on the total weight of the removal composition; and a ketal adduct of formula (1) wherein R1 is C1-6 alkyl, R2 is hydrogen or C1-3 alkyl, each R3, R4, and R5 is independently hydrogen or C1-6 alkyl, R6 and R7 are each independently hydrogen or C1-6 alkyl, a=0-3, and b=0-1.
Type:
Grant
Filed:
August 12, 2011
Date of Patent:
September 9, 2014
Assignee:
Segetis, Inc.
Inventors:
Lee R. Rieth, Matthew J. Tjosaas, Dorie J. Yontz
Abstract: The present disclosure relates to the preparation of acrylate, alkacrylate, allyl, and polycarbonate derivatives of hydroxy ketal esters, and uses thereof.
Type:
Application
Filed:
November 1, 2013
Publication date:
June 12, 2014
Applicant:
SEGETIS, INC.
Inventors:
Sergey SELIFONOV, Brian Daniel MULLEN, Douglas Alan WICKS, Vivek BADARINARAYANA
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.