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(12) United States Patent (10) Patent No.: US 8.492.576 B2 Lai Et Al

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(12) United States Patent (10) Patent No.: US 8.492.576 B2 Lai Et Al US008492.576B2 (12) United States Patent (10) Patent No.: US 8.492.576 B2 Lai et al. (45) Date of Patent: Jul. 23, 2013 (54) HYDROXYL-TERMINATED 6,395,850 B1 5, 2002 Charmot et al. THOCARBONATE CONTAINING 6,545,098 B1 * 4/2003 Bouhadir et al. ............. 525,244 COMPOUNDS, POLYMERS, AND 6,596,899 B1 7, 2003 Lai COPOLYMERS, AND POLYURETHANES AND FOREIGN PATENT DOCUMENTS URETHANE ACRYLCS MADE THEREFROM EP O713132 12/2000 GB 1223524 2, 1971 (75) Inventors: John Ta-Yuan Lai, Broadview Heights, WO 98/O 1478 1, 1998 OH (US); Ronald P. Shea, Akron, OH WO 99.05099 2, 1999 WO 99.31144 6, 1999 (US) WO 99.35.177 7, 1999 (73) Assignee: Lubrizol Advanced Materials, Inc., WO 2004-037780 5, 2004 Cleveland, OH (US) OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this World Polymer Congress, 37th International Symposium on Macro patent is extended or adjusted under 35 molecules, Jul. 12-17, 1998, Gold Coast, Australia, pp. 1-10. U.S.C. 154(b) by 918 days. John Chiefari, et al., Living Free-Radical Polymerization by Revers ible Addition-Fragmentation Chain Transfer: The Raft Process, (21) Appl. No.: 12/478,220 CSIRO Molecular Science, Bag 10, Clayton South, Clayton, Victoria 3169, Australia, Received Mar. 27, 1998, Revised Manuscript (22) Filed: Jun. 4, 2009 Received Jun. 10, 1998. H. C. Godt, Jr et al. The Synthesis of Organic Trithiocarbonates, Prior Publication Data Journal of Organic Chemistry, vol. 26, pp. 4047-4050, 1961. (65) Iacopo Degani et al., Phase-Transfer Synthesis of Symmetrical and US 2009/0312496 A1 Dec. 17, 2009 Unsymmetrical Dialkyl Trithiocarbonates, Synthesis, pp. 894-899, 1986. Julia Krstina et al., A New Form of Controlled Growth Free Radical Related U.S. Application Data Polymerization, CSIRO, Division of Chemicals and Polymers, Clayton South MDC, Clayton South, Victoria 3169. Australia, (60) Division of application No. 10/913,972, filed on Aug. Macromol. Symp. III, pp. 13-23, 1996. 6, 2004, now Pat. No. 7,557,235, which is a Albert W. M. Lee et al., One Pot Phase Transfer Synthesis of continuation-in-part of application No. 10/681,679, Trithiocarbonates from Carbon Disulphide and Alkyl Halides, Syn filed on Oct. 8, 2003, now Pat. No. 7,335,788, which is thetic Comm., vol. 18, No. 13, pp. 1531-1536, 1988. a continuation-in-part of application No. 10/278.335, Man-Kit Leung et al., A Novel One-Step Synthesis of Symmetrical filed on Oct. 23, 2002, now Pat. No. 7,205,368, which Dialkyl Trithiocarbonates, Journal of Chemical Research(s), pp. 478 is a continuation-in-part of application No. 479, 1995. 09/505,749, filed on Feb. 16, 2000, now Pat. No. Daniel Taton et al., Direct Synthesis of Double Hydrophilic Statisti 6,596,899. cal Di- and Triblock Copolymers Comprised of Acrylamide and Acrylic Acid Units via the MADIX Process, Macromolecular Rapid (51) Int. C. Communication, vol. 22, pp. 1497-1503, 2001. C07C329/00 (2006.01) M. Destarac et al., Dithiocarbamates as Universal Reversible Addi C07C333/00 (2006.01) tion-Fragmentation Chain Transfer Agents, Macromolecular Rapid Communication, vol. 21, pp. 1035-1039, 2000. (52) U.S. C. Roshan T. A. Mayadunne et al., Living Radical Polymerization with USPC ............ 558/243; 558/224;558/245; 558/248 Reversible Addition-Fragmentation Chain Transfer (RAFT Polymer (58) Field of Classification Search ization) Using Dithiocarbamates as Chain Transfer Agents, Macro USPC .................. 558/243, 224, 245: 525/535, 244, molecules, vol. 32, pp. 6977-6980, 1999. 525/261, 308 Yusuf Yagci et al., Light-Induced Synthesis of Block and Graft See application file for complete search history. Copolymers, Progress in Polymer Science, vol. 15, pp. 551-601, 1990. (56) References Cited Polymer Handbook. Third Edition, J. Brandrup et al., John Wiley & Sons, New York. 6. Perester and Peroxy Carbonates, pp. II/53, 1989. U.S. PATENT DOCUMENTS (Continued) 3,285,945 A 11, 1966 Wember 3,285,949 A 11, 1966 Siebert 3,770,698 A 11, 1973 Rew Primary Examiner — Ling Choi 3,860,641 A 1/1975 Zengel et al. 3,928,491 A 12, 1975 Waters Assistant Examiner — Monique Peets 3,992,432 A 1 1/1976 Napier et al. (74) Attorney, Agent, or Firm — Thoburn T. Dunlap 4,769,419 A 9/1988 Dawdy 5,055,515 A 10, 1991 Backderf 5,140,068 A 8, 1992 Siebert et al. (57) ABSTRACT 5,157,077 A 10, 1992 Siebert et al. 5, 198,510 A 3, 1993 Siebert et al. Carboxylate terminated thiocarbonates are reacted with a 5,258.445 A 1 1/1993 Sperk, Jr. et al. 5,280,068 A 1/1994 Siebert et al. polyfunctional alcohol to form a hydroxyl-terminated thio 5,312.956 A 5, 1994 BertSch carbonate compound. 5,385,963 A 1/1995 McBain et al. 6,153,705 A 11/2000 Corpart et al. 6,380,335 B1 4/2002 Charmot et al. 7 Claims, No Drawings US 8.492.576 B2 Page 2 OTHER PUBLICATIONS Lamar Field et al., Preparation and Chlorinolysis of Alpha Graeme Moadet al., The Chemistry of Free Radical Polymerization, Mercaptodiethylacetic Acid, Journal of the American Chemical Soci Pergamon, London, pp. 53-95, 1995. ety, vol. 74, No. 18, pp. 4707-4708, 1952. Eric J. Goethals, Telechelic Polymers: Synthesis and Applications, F. Andreaniet al., New Alpha-Substituted Arylthioacetic Derivatives CRC Press, Boca Raton, Florida, Chapter 4 Telechelics by Free Forming Analogues of Clofibrate, II Farmaco, Edizione Scientifica, Radical Polymerization Reactions, pp. 61-94; and Chapter 10 Ter vol. 30, No. 10, pp. 847-858, 1975. minal Transformation of Telechelics, pp. 229-259, 1989. R. J. Stoodley et al., Studies Related to Penicillins. Part II. The A. Bistrzycki et al., Synthesis of Derivatives of 1.3-Oxathiophane, Rearrangement of 6-B-Aminopencillanic Acid to 2,3-Dihydro-6- Helvetica Chimica Acta, vol. 3, pp. 447-467, 1920. Methoxycarbonyl-2,2-Dimethyl-1,4-Thiazin-3-One, Journal of C. W. Pluijgers et al., Plant Growth-Regulating Activity of American Chemical Society, Section C: Organic Chemistry, No. 23. S-Carboxymethyl-N,N-Dimethyldithiocarbamate and Related Com pp. 2891-2894, 1968. pounds, Recuel Des Travaux Chimiques Des Pays-Bas, vol. 80, No. 9/10, pp. 1089-11 10, 1961. * cited by examiner US 8,492.576 B2 1. 2 HYDROXYL-TERMINATED SUMMARY OF THE INVENTION THIOCARBONATE CONTAINING COMPOUNDS, POLYMERS, AND In one embodiment, carboxylate-terminated di- or trithio COPOLYMERS, AND POLYURETHANES AND carbonates are reacted with a polyfunctional alcohol Such as URETHANE ACRYLCS MADE THEREFROM 5 a diol or other polyol to form hydroxyl terminated di- or trithiocarbonates. In a further embodiment, one or more CROSS-REFERENCE monomers, which are the same or different, are reacted into the backbone of the thiocarbonate compound either before or This patent application is a divisional application of U.S. after reaction with the polyol. application Ser. No. 10/913,972, filed Aug. 6, 2004 now U.S. 10 The hydroxyl terminated thiocarbonate containing poly Pat. No. 7,557.235, which is a continuation-in-part applica mers or copolymers are reacted through the hydroxyl groups tion of U.S. application Ser. No. 10/681,679, filed Oct. 8, along with optional isocyanate reactive compounds, with a 2003, now U.S. Pat. No. 7,335,788, which is a continuation mono or desirably a polyisocyanate compound to form a in-part application of U.S. application Ser. No. 10/278.335, thermoplastic or thermoset polyurethane. The urethane can filed Oct. 23, 2002, now U.S. Pat. No. 7,205,368, which is a 15 continuation-in-part of U.S. application Ser. No. 09/505,749, be prepared in bulk, Solvent or be an aqueous dispersion and filed Feb. 16, 2000, now U.S. Pat. No. 6,596,899. optionally contain an acrylic copolymer. FIELD OF THE INVENTION DETAILED DESCRIPTION OF THE INVENTION Hydroxyl-terminated thiocarbonate containing com Thiocarbonate Compounds pounds (HTT) are utilized to form polymers and copolymers The thiocarbonate compounds utilized in the present useful for numerous applications. HTT are utilized to form invention are preferably polythiocarbonates such as dithio hydroxyl terminated polymers or copolymers which are used carbonate or trithiocarbonate compounds and derivatives in one embodiment to form thermoplastic polyurethane in 25 thereof. By the term “thiocarbonate it is meant a compound bulk. Waterborne polyurethane dispersions are also formed having at least one segment having the formula utilizing HTT. In yet another embodiment, solvent based polyurethanes are described. The bulk, dispersion, and sol vent based urethanes can contain acrylic repeat units. Various S methods are also described for preparing the various thiocar 30 -X-C-S- bonate containing polymers and copolymers of the present invention. where “x' comprises OR, SR, or NR, with R being various BACKGROUND OF THE INVENTION hydrocarbon, hetero atom and/or hydrogen containing struc 35 tures or the like as illustrated hereinbelow, but not limited U.S. Pat. No. 6,596,899 issued Jul. 22, 2003 relates to a thereto. s.s'-bis-O.C.'-disubstituted-O"-acetic acid)-trithiocarbonate Suitable trithiocarbonate compounds for use in the present and derivatives thereof can be used as an initiator, chain invention, but not limited thereto, are disclosed in U.S. Pat. transfer agent, or terminator for polymerization of monomers No. 6,596,899 to Lai, and U.S. patent application Ser. No. Such as free radical polymerizable monomers. Homopoly 40 10/219,403, filed Aug. 15, 2002, both hereby fully incorpo mers, copolymers, and the like as well as block copolymers rated by reference including the preparation thereof. In one can be made utilizing the trithio carbonate compound Such as embodiment, trithiocarbonate compounds have the following in a living free radical polymerization as well as to form general formula: telechelic polymers.
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