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WO 2009/032905 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 12 March 2009 (12.03.2009) WO 2009/032905 Al (51) International Patent Classification: Hwy 7, Apt. 224, St. Louis Park, MN 55416 (US). SELI- C08G 63/42 (2006.01) C08G 18/77 (2006.01) FONOV, Sergey [RU/US]; 4625 Merrimac Lane North, C08G 18/56 (2006.01) C07D 493/18 (2006.01) Plymouth, MN 55446 (US). (21) International Application Number: (74) Agent: KOWALCHYK, Katherine, M.; Merchant & PCT/US2008/075225 Gould PC, P.O. Box 2903, Minneapolis, MN 55402-0903 (US). (22) International Filing Date: (81) Designated States (unless otherwise indicated, for every 4 September 2008 (04.09.2008) kind of national protection available): AE, AG, AL, AM, AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, (25) Filing Language: English CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, (26) Publication Language: English IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, (30) Priority Data: MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, 60/935,839 4 September 2007 (04.09.2007) US RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TJ, 60/935,843 4 September 2007 (04.09.2007) US TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 60/935,838 4 September 2007 (04.09.2007) US ZW 60/935,877 5 September 2007 (05.09.2007) US 60/935,882 5 September 2007 (05.09.2007) US (84) Designated States (unless otherwise indicated, for every 60/935,881 5 September 2007 (05.09.2007) US kind of regional protection available): ARIPO (BW, GH, 60/935,880 5 September 2007 (05.09.2007) US GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 60/935,875 5 September 2007 (05.09.2007) US ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), 60/960,627 9 October 2007 (09.10.2007) US European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, (71) Applicant (for all designated States except US): NO, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, SEGETIS, INC. [US/US]; 680 Mendelsshon Avenue CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). N., Golden Valley, MN 55427 (US). Published: (72) Inventors; and — with international search report (75) Inventors/Applicants (for US only): WICKS, Douglas, — before the expiration of the time limit for amending the Alan [US/US]; 1425 Maryland Avenue N., Golen Valley, claims and to be republished in the event of receipt of MN 55427 (US). WILLIAMS, Charles [US/US]; 5707 amendments (54) Title: KETAL COMPOUNDS FROM POLYOLS AND OXOCARB OXYLATES (57) 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. KETAL COMPOUNDS FROM POLYOLS AND OXOCARBOXYLATES This application is being filed on 04 September 2008, as a PCT International Patent application in the name of Segetis, Inc., a U.S. national corporation, applicant for the designation of all countries except the US, and Douglas Alan Wicks, Charles Williams, both citizens of the U.S., and Sergey Selifonov, a citizen of the Russian Federation, applicants for the designation of the US only. This application claims the benefit of United States Patent Application No. 60/935,839 entitled "Bishydroxy alkyl ketal compounds", filed on September 4, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of United States Provisional Patent Application No. 60/935,838 entitled "Polyketal-ester polyols", filed on September 4, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of United States Provisional Patent Application No. 60/935,843 entitled "NCO prepolymers", filed on September 4, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/935,882 entitled "Copolyesters of ketal-ester compounds", filed on September 5, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/935,881 entitled "Copolyesters prepared from bishydroxyalkyl ketal compounds", filed on September 5, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/935,877 entitled "Polyhydroxy functional polyesters prepared from bishydroxyalkyl ketal compounds", filed on September 5, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/935,880 entitled "Polyhydroxy functional polyesters prepared from oligo ketal-ester compounds", filed on September 5, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/935,875 entitled "Thermoplastic polyurethanes prepared from bishydroxyalkyl ketal compounds", filed on September 5, 2007, which is incorporated by reference in its entirety herein; this application further claims the benefit of the United States Provisional Patent Application No. 60/960,627 entitled "Polymeric levulinic ketals of polyhydric alcohols and their use", filed on October 9, 2007, which is incorporated by reference in its entirety herein. TECHNICAL FIELD The present disclosure relates to the preparation of ketal compounds from triols and oxocarboxylic acids or esters thereof, and polymeric materials prepared from the ketal compounds. BACKGROUND Many known chemical products such as surfactants, plasticizers, solvents, and polymers are currently manufactured from non-renewable, expensive, petroleum-derived or natural gas-derived feedstock compounds. High raw material costs and uncertainty of future supplies requires the discovery and development of surfactants, plasticizers, solvents, and polymers that can be made from inexpensive renewable biomass-derived feedstocks and by simple chemical methods. Certain polyol compounds can be inexpensive and renewable compounds that are readily available. Oxocarboxylic acids such as pyruvic, acetoacetic, and levulinic acid (and related useful derivatives such as esters) represent another abundant feedstock that is prepared on an industrial scale. Chemical products produced from these two types of materials can fill a need for inexpensive, renewable consumer and industrial products not based on petroleum or other nonrenewable resource. SUMMARY Ketal compounds can be prepared from a triol and an oxocarboxylic acid or derivative thereof. The details of one or more embodiments of the invention are set forth in the description below. Other features, objects, and advantages of the invention will be apparent from the description and from the claims. DETAILED DESCRIPTION The present disclosure provides a series of triol-derived compounds that are based on the formation of a ketal or acetal of an oxocarboxylate. Such compounds can be produced by reacting approximately one molar equivalent of triol with approximately one molar equivalent of oxocarboxylate in the presence of a catalyst, and under conditions obtaining or allowing for removal of water, typically by distillation. Such ketal compounds include structure (Ia): wherein a is 0 or 1, b is 0 or 1, R3 is hydrogen or an alkyl group having between 1 and 12 carbons, R4 is an alkyl group having between 1 and 12 carbons, and X is any substituent. Substituents R3 and R4 may further be substituted with one or more functional groups, such as halogen, ether, cyano, and the like. Such compounds also include those having structure (Ib): wherein R3 is hydrogen or an alkyl group having between 1 and 12 carbons, R4 is an alkyl group having between 1 and 12 carbons, and X is any substituent. Substituents R3 and R4 may further be substituted with one or more functional groups, such as halogen, ether, cyano, and the like. The compounds of the invention have, in embodiments, one or more isomers. Where an isomer can exist, it should be understood that the invention embodies all isomers thereof, including stereoisomers, conformational isomers, and cis, trans isomers; isolated isomers thereof; and mixtures thereof. Where R3 is hydrogen, the compounds are acetals. Where R3 is an alkyl group, the compounds are ketals. For the purpose of the invention, both acetals and ketals are referred to as "ketals" for brevity. The formation of ketals is preferably carried out using the methods outlined in U.S. Patent Application No. 61/048,339, the contents of which are incorporated herein in their entirety. However, other methods, such as those set forth in WO 2007/0621 18A2, may also be used. The preferable method of making the compounds of the invention depend on the exact structures employed in the synthesis. During the course of the reaction between about one equivalent of triol and one equivalent of oxocarboxylate, two equivalents of water are formed. Water can conveniently be removed by distillation, or by an azeotropic distillation in the presence of a suitable
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