Polyurethanes and polycarbonates are widely used in a variety of applications including engineering, optical devices, and high-performance adhesives and coatings, etc., and are expected to find use also in the biomedical field owing to their biocompatibility and low toxicity. However, these polymers are currently produced using hazardous phosgene and isocyanates, which are derived from the reaction between an amine and phosgene. Extensive safety procedures are required to prevent exposure to phosgene and isocyanate because of its high toxicity. Therefore, the demand for the production of isocyanate-free polymers has now emerged. Among the alternative greener routes that have been proposed, a popular way is the ring-opening polymerization (ROP) of cyclic carbonate in bulk or solution, usually using metallic catalyst, metal-free initiator, or biocatalyst. This review presents the recent developments in the preparation and application of cyclic carbonates as monomers for ROP, with emphasis on phosgene- and isocyanate-free polymerization to produce aliphatic polycarbonates and polyurethanes and their copolymers.
References
1 10.1089/teb.2007.0133, S. A. Guelcher. Tissue Eng., Part B14, 3 (2008).Search in Google Scholar
2 10.1002/mabi.200900039, Y. Yamamoto, S. Kaihara, K. Toshima, S. Matsumura. Macromol. Biosci.9, 968 (2009).Search in Google Scholar
3 10.1016/j.biomaterials.2005.09.017, Z. Zhang, R. Kuijer, S. K. Bulstra, D. W. Grijpma, J. Feijen. Biomaterials27, 1741 (2006).Search in Google Scholar
4 10.1007/b137240, L. S. Nair, C. T. Laurencin. Adv. Biochem. Eng./Biotechnol.102, 47 (2006).Search in Google Scholar
5 P. Gunatillake, R. Mayadunne, R. Adhikari. In Biotech. Ann. Rev., M. R. El-Gewely (Ed.), pp. 301–347, Elsevier (2006).10.1016/S1387-2656(06)12009-8Search in Google Scholar
6 10.1016/S0141-0229(96)00084-1, T. Suyama, Y. Tokiwa. Enzyme Microb. Technol.20, 122 (1997).Search in Google Scholar
7 10.1111/j.1574-6968.1998.tb12956.x, T. Suyama, H. Hosoya, Y. Tokiwa. FEMS Microbiol. Lett.161, 255 (1998).Search in Google Scholar
8 An Ullmann Encyclopedia: Industrial Organic Chemicals: Starting Materials and Intermediates, Wiley-VCH, New York (1999).Search in Google Scholar
9 10.1007/s00253-005-0269-2, S. Matsumura, Y. Soeda, K. Toshima. Appl. Microbiol. Biotechnol.70, 12 (2006).Search in Google Scholar
10 10.1039/c0gc00136h, D. J. Darensbourg, A. Horn Jr., A. I. Moncada. Green Chem.12, 1376 (2010).Search in Google Scholar
12 J. Fahlén, R. Martinsson, B. Midelf. Eur. Coat. J.6, 28 (2007).Search in Google Scholar
11 10.1016/S0964-8305(02)00051-3, G. T. Howard. Int. Biodeterior. Biodegrad.49, 245 (2002).Search in Google Scholar
13 K. L. Dunlap. In Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley, New York (2000).Search in Google Scholar
14 J. Borak, W. F. Diller. J. Occup. Environ. Med.43, 110 (2001).Search in Google Scholar
15 10.1111/j.1399-3038.2005.00295.x, C. A. Krone, T. D. Klingner. Pediatr. Allergy Immunol.16, 368 (2005).Search in Google Scholar
16 10.1034/j.1600-0536.2002.470509.x, A. Goossens, T. Detienne, M. Bruze. Contact Dermatitis47, 304 (2002).Search in Google Scholar
17 H. Ulrich. Chemistry and Technology of Isocyanates, John Wiley, New York (1996).Search in Google Scholar
18 10.1039/b902425p, F. Ragaini. Dalton Trans. 6251 (2009).Search in Google Scholar
19 F. Merger, F. Towae. U.S. Patent 4713476 (1987).Search in Google Scholar
20 C. E. Schweitzer. U.S. Patent 2409712 (1946).Search in Google Scholar
21 S. Kohlstruk, M. Kreczinski, R. Elm, H.-W. Michalczak. U.S. Patent 7307186 (2007).Search in Google Scholar
22 L. Rosenstock. In Textbook of Clinical, Occupational And Environmental Medicine, M. R. Cullen (Ed.), pp. 794–796, Saunders, Philadelphia (1994).Search in Google Scholar
23 10.1080/10473220290107101, S. M. Tarlo, G. M. Liss. Appl. Occup. Environ. Hygiene17, 902 (2002).Search in Google Scholar
24 10.1080/713611031, M. G. Ott, W. F. Diller, A. T. Jolly. Crit. Rev. Toxicol.33, 1 (2003).Search in Google Scholar
25 10.1016/S1081-1206(10)61647-X, Q. Liu, A. V. Wisnewski. Ann. Allerg., Asthma Immunol.90, 35 (2003).Search in Google Scholar
26 NIOSH. Recommendations for Occupational Safety and Health, Compendium of Policy Documents and Statements, U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control, Cincinnati, OH (1992).Search in Google Scholar
27 29 CFR 1910.1000, Air Contaminants (1989).Search in Google Scholar
28 Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices, ACGIH, Cincinnati, OH (1999).Search in Google Scholar
29 10.1039/b003655m, Y.-M. Roh, R. P. Streicher, M. K. Ernst. Analyst125, 1691 (2000).Search in Google Scholar
30 J. Bosman. In The Polyurethanes Book, D. Randall, S. Lee (Eds.), pp. 113–120, 366–377, John Wiley, West Sussex, UK (2002).Search in Google Scholar
31 10.2174/157017806779025960, A.-C. Simao, B. Lynikaite-Pukleviciene, C. Rousseau, A. Tatibouet, S. Cassel, A. Sackus, A. P. Rauter, P. Rollin. Lett. Org. Chem.3, 744 (2006).Search in Google Scholar
32 10.1039/b710561d, A. Behr, J. Eilting, K. Irawadi, J. Leschinski, F. Lindner. Green Chem.10, 13 (2008).Search in Google Scholar
33 10.1039/b707343g, C.-H. Zhou, J. N. Beltramini, Y.-X. Fan, G. Q. Lu. Chem. Soc. Rev.37, 527 (2008).Search in Google Scholar PubMed
34 K. S. Jung, J.-H. Kim, J. H. Cho, D. K. Kim. U.S. Patent 0209979 (2010).Search in Google Scholar
35 10.1021/ja01364a045, W. H. Carothers, F. J. V. Natta. J. Am. Chem. Soc.52, 314 (1930).Search in Google Scholar
36 10.1021/ja01339a055, J. W. Hill, W. H. Carothers. J. Am. Chem. Soc.55, 5031 (1933).Search in Google Scholar
37 10.1021/ja01339a057, W. H. Carothers, J. W. Hill. J. Am. Chem. Soc.55, 5043 (1933).Search in Google Scholar
38 W. J. Blank, C. Wilton. U.S. Patent 4820830 (1989).Search in Google Scholar
39 10.1039/b501597a, G. Rokicki, P. Rakoczy, P. Parzuchowski, M. Sobiecki. Green Chem.7, 529 (2005).Search in Google Scholar
40 10.1039/b903529j, Y. Patel, J. George, S. M. Pillai, P. Munshi. Green Chem.11, 1056 (2009).Search in Google Scholar
41 10.1016/j.jorganchem.2005.02.011, J. Sun, S.-i. Fujita, M. Arai. J. Organomet. Chem.690, 3490 (2005).Search in Google Scholar
42 10.1016/j.molcatb.2007.08.007, S. C. Kim, Y. H. Kim, H. Lee, D. Y. Yoon, B. K. Song. J. Mol. Catal., B49, 75 (2007).Search in Google Scholar
43 J. George, Y. Patel, S. M. Pillai, P. Munshi. J. Mol. Catal., A304, 1 (2009).10.1016/j.molcata.2009.01.010Search in Google Scholar
44 10.1023/A:1019050205502, C. Vieville, J. W. Yoo, S. Pelet, Z. Mouloungui. Catal. Lett.56, 245 (1998).Search in Google Scholar
45 J. R. Ochoa-Gómez, O. Gómez-Jiménez-Aberasturi, B. Maestro-Madurga, A. Pesquera-Rodríguez, C. Ramírez-López, L. Lorenzo-Ibarreta, J. Torrecilla-Soria, M. C. Villarán-Velasco. Appl. Catal., A366, 315 (2009).10.1016/j.apcata.2009.07.020Search in Google Scholar
46 10.1002/adsc.200900280, P. U. Naik, L. Petitjean, K. Refes, M. Picquet, L. Plasseraud. Adv. Synth. Catal.351, 1753 (2009).Search in Google Scholar
47 10.1021/ie020678i, J. H. Clements. Ind. Eng. Chem. Res.42, 663 (2003).Search in Google Scholar
48 10.1039/c0dt01389g, C. Hammond, J. A. Lopez-Sanchez, R. M. H. Ab, N. Dimitratos, R. L. Jenkins, A. F. Carley, Q. He, C. J. Kiely, D. W. Knight, G. J. Hutchings. Dalton Trans.40, 3927 (2011).Search in Google Scholar PubMed
49 10.1002/hc.20640, T. Mizuno, T. Nakai, M. Mihara. Heteroat. Chem.21, 541 (2010).Search in Google Scholar
50 J. Hu, J. Li, Y. Gu, Z. Guan, W. Mo, Y. Ni, T. Li, G. Li. Appl. Catal., A386, 188 (2010).10.1016/j.apcata.2010.07.059Search in Google Scholar
51 10.1016/j.tet.2009.07.095, J. Rousseau, C. Rousseau, B. Lynikaite, A. Sa?kus, C. de Leon, P. Rollin, A. Tatibouët. Tetrahedron65, 8571 (2009).Search in Google Scholar
52 10.1002/app.1719, M.-R. Kim, H.-S. Kim, C.-S. Ha, D.-W. Park, J.-K. Lee. J. Appl. Polym. Sci.81, 2735 (2001).Search in Google Scholar
53 D. A. Wicks, R. R. Gutierrez. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 44, 50 (2003).Search in Google Scholar
54 10.1002/app.20049, B. Tamami, S. Sohn, G. L. Wilkes. J. Appl. Polym. Sci.92, 883 (2004).Search in Google Scholar
55 10.1071/CH9721513, S. Angyal, M. Evans. Austr. J. Chem.25, 1513 (1972).Search in Google Scholar
56 10.1021/ja01570a038, D. B. Pattison. J. Am. Chem. Soc.79, 3455 (1957).Search in Google Scholar
57 10.1021/ma971227q, J. Matsuo, K. Aoki, F. Sanda, T. Endo. Macromolecules31, 4432 (1998).Search in Google Scholar
58 10.1080/10101329208054106, A. C. Albertsson, M. Sjoeling. J. Macromol. Sci., Pure Appl. Chem. A29, 43 (1992).Search in Google Scholar
59 K. Miyazaki, T. Endo, F. Sanda, O. Moriya, T. Fukushima, J. M. Antonucci. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)38, 165 (1997).Search in Google Scholar
60 10.1002/mabi.200350013, H. Tasaki, K. Toshima, S. Matsumura. Macromol. Biosci.3, 436 (2003).Search in Google Scholar
61 B. Joseph, P. W. Ramteke, G. Thomas, N. Shrivastava. Biotechnol. Mol. Biol. Rev.2, 039 (2007).Search in Google Scholar
62 10.1016/S0958-1669(02)00341-5, K.-E. Jaeger, T. Eggert. Curr. Opin. Biotechnol.13, 390 (2002).Search in Google Scholar
63 10.1126/science.6729453, A. Zaks, A. M. Klibanov. Science224, 1249 (1984).Search in Google Scholar PubMed
64 10.1073/pnas.82.10.3192, A. Zaks, A. M. Klibanov. Proc. Natl. Acad. Sci. USA82, 3192 (1985).Search in Google Scholar PubMed PubMed Central
65 10.1016/j.molcatb.2006.09.002, C. Orellana-Coca, J. M. Billakanti, B. Mattiasson, R. Hatti-Kaul. J. Mol. Catal., B44, 133 (2007).Search in Google Scholar
66 10.1007/s11746-009-1504-2, R. Ye, S.-H. Pyo, D. Hayes. J. Am. Oil Chem. Soc.87, 281 (2010).Search in Google Scholar
67 10.1007/s11746-009-1381-8, S.-H. Pyo, D. Hayes. J. Am. Oil Chem. Soc.86, 521 (2009).Search in Google Scholar
68 10.1039/c0gc00783h, S.-H. Pyo, P. Persson, S. Lundmark, R. Hatti-Kaul. Green Chem.13, 976 (2011).Search in Google Scholar
69 10.1016/j.molcatb.2011.07.019, S.-H. Pyo, K. Nuszkiewicz, P. Persson, S. Lundmark, R. Hatti-Kaul. J. Mol. Catal., B: Enzym.73, 67 (2011).Search in Google Scholar
70 10.1002/btpr.504, A. E. V. Hagström, U. Törnvall, M. Nordblad, R. Hatti-Kaul, J. M. Woodley. Biotechnol. Prog.27, 67 (2011).Search in Google Scholar
71 10.1002/1521-3935(20000901)201:14<1632::AID-MACP1632>3.0.CO;2-P, S. Matsumura, S. Harai, K. Toshima. Macromol. Chem. Phys.201, 1632 (2000).Search in Google Scholar
72 10.1002/1521-3927(200102)22:3<215::AID-MARC215>3.0.CO;2-#, S. Matsumura, S. Harai, K. Toshima. Macromol. Rapid Commun.22, 215 (2001).Search in Google Scholar
73 10.1007/s00449-010-0431-9, K. Lee, C.-H. Park, E. Lee. Bioprocess Biosys. Eng.33, 1059 (2010).Search in Google Scholar
74 10.1007/s10529-011-0627-3, J. Min, E. Lee. Biotechnol. Lett. (2011).Search in Google Scholar
75 10.1002/1099-0518(20010101)39:1<162::AID-POLA180>3.0.CO;2-O, H. Tomita, F. Sanda, T. Endo. J. Polym. Sci., Part A: Polym. Chem.39, 162 (2001).Search in Google Scholar
76 10.1295/polymj.32.381, G. Rokicki, T. Kowalczyk, M. Glinski. Polym. J. (Tokyo)32, 381 (2000).Search in Google Scholar
77 10.1016/j.eurpolymj.2007.07.009, L. Liao, C. Zhang, S. Gong. Eur. Polym. J.43, 4289 (2007).Search in Google Scholar
78 10.1016/j.porgcoat.2005.06.005, P. Löwenhielm, D. Nyström, M. Johansson, A. Hult. Prog. Org. Coat.54, 269 (2005).Search in Google Scholar
79 10.1002/macp.200400006, P. Löwenhielm, H. Claesson, A. Hult. Macromol. Chem. Phys.205, 1489 (2004).Search in Google Scholar
80 10.1016/S0079-6700(00)00006-X, G. Rokicki. Prog. Polym. Sci.25, 259 (2000).Search in Google Scholar
81 10.1021/ma9914321, J.-C. Lee, M. H. Litt. Macromolecules33, 1618 (2000).Search in Google Scholar
82 10.1002/macp.1990.021910301, L. Vogdanis, B. Martens, H. Uchtmann, F. Hensel, W. Heitz. Makromol. Chem.191, 465 (1990).Search in Google Scholar
83 10.1002/pol.1976.130140309, K. Soga, S. Hosada, Y. Tazuke, S. Ikeda. J. Polym. Sci., Polym. Lett. Ed.14, 161 (1976).Search in Google Scholar
84 10.1002/pol.1977.170150120, K. Soga, Y. Tazuke, S. Hosoda, S. Ikeda. J. Polym. Sci., Polym. Chem. Ed.15, 219 (1977).Search in Google Scholar
85 10.1002/marc.1986.030070901, L. Vogdanis, W. Heitz. Makromol. Chem., Rapid Commun.7, 543 (1986).Search in Google Scholar
86 H. Sawada, K. F. O’Driscoll. In Thermodynamics of Polymerization, p. 149, New York (1976).Search in Google Scholar
87 10.1002/pola.21073, T. Hino, N. Inoue, T. Endo. J. Polym. Sci., Part A: Polym. Chem.44, 395 (2006).Search in Google Scholar
88 10.1002/marc.1997.030180602, T. Takata, F. Sanda, T. Ariga, H. Nemoto, T. Endo. Macromol. Rapid Commun.18, 461 (1997).Search in Google Scholar
89 R. K. Sadhir, R. M. Luck. Expanding Monomers: Synthesis, Characterization and Applications, CRC, Boca Raton (1992).Search in Google Scholar
90 T. Endo, F. Sanda. In Polymeric Materials Encyclopedia, J. C. Salamone (Ed.), p. 7554, CRC Press, Boca Raton (1996).Search in Google Scholar
91 10.1016/0079-6700(93)90019-9, T. Takata, T. Endo. Prog. Polym. Sci.18, 839 (1993).Search in Google Scholar
92 10.1021/ma0100302, S. Kéki, J. Török, G. Deák, M. Zsuga. Macromolecules34, 6850 (2001).Search in Google Scholar
93 10.1016/0032-3861(96)81627-2, H. R. Kricheldorf, B. Weegen-Schulz. Polymer36, 4997 (1995).Search in Google Scholar
94 10.1002/(SICI)1099-0518(199706)35:8<1375::AID-POLA5>3.0.CO;2-Z, J. Matsuo, F. Sanda, T. Endo. J. Polym. Sci., Part A: Polym. Chem.35, 1375 (1997).Search in Google Scholar
95 10.1021/ma961862g, S. Matsumura, K. Tsukada, K. Toshima. Macromolecules30, 3122 (1997).Search in Google Scholar
96 10.1002/marc.1997.030180707, S. Kobayashi, H. Kikuchi, H. Uyama. Macromol. Rapid Commun.18, 575 (1997).Search in Google Scholar
97 10.1002/(SICI)1099-0518(199810)36:14<2463::AID-POLA4>3.0.CO;2-U, J. Matsuo, S. Nakano, F. Sanda, T. Endo. J. Polym. Sci., Part A: Polym. Chem.36, 2463 (1998).Search in Google Scholar
98 10.1002/1521-3935(20000801)201:13<1405::AID-MACP1405>3.0.CO;2-T, M. Sepulchre, M.-O. Sepulchre, M.-A. Dourges, M. Neblai. Macromol. Chem. Phys.201, 1405 (2000).Search in Google Scholar
99 10.1021/ma9708858, K. S. Bisht, Y. Y. Svirkin, L. A. Henderson, R. A. Gross, D. L. Kaplan, G. Swift. Macromolecules30, 7735 (1997).Search in Google Scholar
100 10.1002/pola.1993.080311113, N. Kihara, T. Endo. J. Polym. Sci. Part A: Polym. Chem.31, 2765 (1993).Search in Google Scholar
101 10.1016/S0300-9440(00)00114-4, D. C. Webster, A. L. Crain. Prog. Org. Coat.40, 275 (2000).Search in Google Scholar
102 D. A. Wicks, R. R. Gutierrez. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)44, 50 (2003).Search in Google Scholar
103 10.1002/marc.200300064, L. Ubaghs, N. Fricke, H. Keul, H. Hoecker. Macromol. Rapid Commun.25, 517 (2004).Search in Google Scholar
104 10.1007/s10562-008-9415-7, G. Wang, N. Yu, L. Peng, R. Tan, H. Zhao, D. Yin, H. Qiu, Z. Fu, D. Yin. Catal. Lett.123, 252 (2008).Search in Google Scholar
105 10.1007/BF02699710, O. Figovsky, L. Shapovalov, F. Buslov. Surf. Coat. Int., Part B88, 67 (2005).Search in Google Scholar
106 10.1016/j.porgcoat.2010.07.010, Z. Hosgör, N. Kayaman-Apohan, S. Karatas, Y. Menceloglu, A. Güngör. Prog. Org. Coat.69, 366 (2010).Search in Google Scholar
107 10.1002/pola.21103, B. Ochiai, S. Inoue, T. Endo. J. Polym. Sci., Part A: Polym. Chem.43, 6613 (2005).Search in Google Scholar
108 10.1021/la703328z, P. Alessio, D. M. Ferreira, A. E. Job, R. F. Aroca, A. Riul Jr., C. J. L. Constantino, G. E. R. Perez. Langmuir24, 4729 (2008).Search in Google Scholar
109 10.1002/(SICI)1521-3935(20000101)201:1<107::AID-MACP107>3.0.CO;2-W, C. A. P. Joziasse, H. Grablowitz, A. J. Pennings. Macromol. Chem. Phys.201, 107 (2000).Search in Google Scholar
110 10.1002/pola.11001, Z.-L. Liu, Y. Zhou, R.-X. Zhuo. J. Polym. Sci., Part A: Polym. Chem.41, 4001 (2003).Search in Google Scholar
111 10.1016/j.eurpolymj.2009.04.022, Y. Zhou, G.-L. Wu, R.-X. Zhuo, Z.-L. Liu. Eur. Polym. J.45, 1868 (2009).Search in Google Scholar
112 10.1021/bm060795n, F. Nederberg, B. G. G. Lohmeijer, F. Leibfarth, R. C. Pratt, J. Choi, A. P. Dove, R. M. Waymouth, J. L. Hedrick. Biomacromolecules8, 153 (2007).Search in Google Scholar
113 10.1016/S0032-3861(02)00071-X, G. Rokicki, A. Piotrowska. Polymer43, 2927 (2002).Search in Google Scholar
114 10.1016/j.eurpolymj.2008.11.006, J. Feng, H.-F. Wang, X.-z. Zhang, R.-X. Zhuo. Eur. Polym. J.45, 523 (2009).Search in Google Scholar
115 10.1021/cr900165z, S. Kobayashi, A. Makino. Chem. Rev.109, 5288 (2009).Search in Google Scholar PubMed
116 10.2183/pjab.86.338, S. Kobayashi. Proc. Jpn. Acad. Series B86, 338 (2010).Search in Google Scholar PubMed PubMed Central
117 10.1246/cl.1993.1149, H. Uyama, S. Kobayashi. Chem. Lett. 1149 (1993).Search in Google Scholar
118 10.1002/pola.1993.080310518, D. Knani, A. L. Gutman, D. H. Kohn. J. Polym. Sci., Part A: Polym. Chem.31, 1221 (1993).Search in Google Scholar
119 10.1021/ma00125a002, H. Uyama, K. Takeya, N. Hoshi, S. Kobayashi. Macromolecules28, 7046 (1995).Search in Google Scholar
120 10.1007/BF00129728, S. Matsumura, H. Beppu, K. Tsukada, K. Toshima. Biotechnol. Lett.18, 1041 (1996).Search in Google Scholar
121 M. Vert, J. Feijen, A. Albertsson, G. Scott, E. Chiellini. In Biodegradable Polymers and Plastics, p. 11, Royal Society, London (1992).Search in Google Scholar
122 10.1351/pac200779111855, M. Selva. Pure Appl. Chem.79, 1855 (2007).Search in Google Scholar
123 10.1351/pac200173071117, P. Tundo. Pure Appl. Chem.73, 1117 (2001).Search in Google Scholar
124 10.1016/j.tet.2007.04.039, R. Bernini, E. Mincione, M. Barontini, F. Crisante, G. Fabrizi, A. Gambacorta. Tetrahedron63, 6895 (2007).Search in Google Scholar
125 10.1002/pol.1977.130151007, K. Soga, S. Hosoda, S. Ikeda. J. Polym. Sci., Polym. Lett. Ed.15, 611 (1977).Search in Google Scholar
126 10.1016/j.biotechadv.2009.07.003, R. K. Saxena, P. Anand, S. Saran, J. Isar. Biotechnol. Adv.27, 895 (2009).Search in Google Scholar
127 10.1002/mabi.200400042, Y. Soeda, K. Toshima, S. Matsumura. Macromol. Biosci.4, 721 (2004).Search in Google Scholar
128 10.1021/bm9007343, C. Bonduelle, B. Martin-Vaca, D. Bourissou. Biomacromolecules10, 3069 (2009).Search in Google Scholar
129 10.1021/ma990639r, T. F. Al-Azemi, K. S. Bisht. Macromolecules32, 6536 (1999).Search in Google Scholar
130 10.1002/masy.200390128, J. Feng, R. Zhuo, F. He, X. Wang. Macromol. Symp.195, 237 (2003).Search in Google Scholar
131 10.1021/bm800696q, R. Wu, T. F. Al-Azemi, K. S. Bisht. Biomacromolecules9, 2921 (2008).Search in Google Scholar
132 10.1016/j.eurpolymj.2004.06.026, X.-H. Yu, R.-X. Zhuo, J. Feng, J. Liao. Eur. Polym. J.40, 2445 (2004).Search in Google Scholar
133 10.1002/(SICI)1521-3935(19980101)199:1<97::AID-MACP97>3.0.CO;2-D, J. Matsuo, F. Sanda, T. Endo. Macromol. Chem. Phys.199, 97 (1998).Search in Google Scholar
134 10.1002/app.27440, J. Liu, C. Zhang, L. Liu. J. Appl. Polym. Sci.107, 3275 (2008).Search in Google Scholar
135 10.1021/ma049562j, P. V. Persson, J. Schroeder, K. Wickholm, E. Hedenstroem, T. Iversen. Macromolecules37, 5889 (2004).Search in Google Scholar
136 10.1021/bm005552o, T. F. Al-Azemi, J. P. Harmon, K. S. Bisht. Biomacromolecules1, 493 (2000).Search in Google Scholar
137 10.1021/bm060070j, F. He, H.-L. Jia, G. Liu, Y.-P. Wang, J. Feng, R.-X. Zhuo. Biomacromolecules7, 2269 (2006).Search in Google Scholar
138 10.1002/pol.1969.110070408, S. Inoue, H. Koinuma, T. Tsuruta. J. Polym. Sci., Part B: Polym. Lett.7, 287 (1969).Search in Google Scholar
139 S. M. Kim, I. Kim, D. W. Park, C.-S. Ha. In Studies in Surface Science and Catalysis, J.-S. C. Sang-Eon Park, L. Kyu-Wan (Eds.), pp. 255–258, Elsevier (2004).10.1016/S0167-2991(04)80259-3Search in Google Scholar
140 10.1002/app.28887, E. Foy, J. B. Farrell, C. L. Higginbotham. J. Appl. Polym. Sci.111, 217 (2009).Search in Google Scholar
141 10.1351/pac200678101823, H. Sugimoto, S. Inoue. Pure Appl. Chem.78, 1823 (2006).Search in Google Scholar
142 10.1351/pac200476030541, K. Nozaki. Pure Appl. Chem.76, 541 (2004).Search in Google Scholar
143 D. Thorpe. In The Polyurethanes Book, D. Randall, S. Lee (Eds.), p. 88, John Wiley, West Sussex, UK (2002).Search in Google Scholar
144 10.1002/1521-3927(20000801)21:13<869::AID-MARC869>3.0.CO;2-U, H. Keul, H. Hocker. Macromol. Rapid Commun.21, 869 (2000).Search in Google Scholar
145 10.1021/ma9610774, S. Neffgen, H. Keul, H. Höcker. Macromolecules30, 1289 (1997).Search in Google Scholar
146 10.1021/ma000535c, J. Kusan, H. Keul, H. Hoecker. Macromolecules34, 389 (2001).Search in Google Scholar
147 10.1021/ma049668e, L. Ubaghs, M. Waringo, H. Keul, H. Hoecker. Macromolecules37, 6755 (2004).Search in Google Scholar
148 10.1002/anie.200352215, O. Ihata, Y. Kayaki, T. Ikariya. Angew. Chem., Int. Ed.43, 717 (2004).Search in Google Scholar PubMed
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