Green polycarbonates prepared by the copolymerization of CO2 with epoxides

Journal of Applied Polymer Science

Volumn 131, Issue 21, 2014, Pages

  Taherimehr, Masoumeh ^a   Pescarmona, Paolo P ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

biodegradable; catalysts; characterization; copolymers; polycarbonates; properties

Indexed keywords

CARBON DIOXIDE; CATALYSTS; CHARACTERIZATION; COPOLYMERIZATION; POLYCARBONATES;

BIODEGRADABLE; GREEN POLYMERS; PHYSICOCHEMICAL PROPERTY; PROPERTIES; RENEWABLE FEEDSTOCKS;

COPOLYMERS;

EID: 84906101802     PISSN: 00218995     EISSN: 10974628     Source Type: Journal    
DOI: 10.1002/app.41141     Document Type: Review

References (112)

1. Beckman, E. J., J. Supercrit. Fluids 2004, 28, 121.
2. Leitner, W., Acc. Chem. Res. 2002, 35, 746.
3. Sakakura, T.,;, Choi, J.-C.,;, Yasuda, H., Chem. Rev. 2007, 107, 2365.
4. Tsuji, Y.,;, Fujihara, T., Chem. Commun. 2012, 48, 9956.
5. Cokoja, M.,;, Bruckmeier, C.,;, Rieger, B.,;, a Herrmann, W.,;, Kühn, F. E., Angew. Chem. Int. Ed. 2011, 50, 8510.
6. Boretti, A., Int. J. Hydro. Energy 2013, 38, 1806.
7. Peters, M.,;, Köhler, B.,;, Kuckshinrichs, W.,;, Leitner, W.,;, Markewitz, P.,;, Müller, T. E., ChemSusChem 2011, 4, 1216.
8. Taherimehr, M.,;, Decortes, A.,;, Al-Amsyar, S. M.,;, Lueangchaichaweng, W.,;, Whiteoak, C. J.,;, Escudero-Adán, E. C.,;, Kleij, A. W.,;, Pescarmona, P. P., Catal. Sci. Technol. 2012, 2, 2231.
9. Phung, C.,;, Ulrich, R. M.,;, Ibrahim, M.,;, Tighe, N. T. G.,;, Lieberman, D. L.,;, Pinhas, A. R., Green Chem. 2011, 13, 3224.
10. Kember, M. R.,;, Buchard, A.,;, Williams, C. K., Chem. Commun. 2011, 47, 141.
11. Miao, C.,;, Wang, J.,;, He, L., Open Org. Chemstry J. 2008, 2, 68.
12. Azechi, M.,;, Matsumoto, K.,;, Endo, T., J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 1651.
13. Clements, J. H., Ind. Eng. Chem. Res. 2003, 42, 663.
14. Nie, M.,;, Chalasani, D.,;, Abraham, D. P.,;, Chen, Y.,;, Bose, A.,;, Lucht, B. L., J. Phys. Chem. C 2013, 117, 1257.
15. Aresta, M.,;, Dibenedetto, A.,;, Tommasi, I., Appl. Organometal. 2000, 14, 799.
16. Fukuoka, S.,;, Kawamura, M.,;, Komiya, K.,;, Tojo, M.,;, Hachiya, H.,;, Hasegawa, K.,;, Aminaka, M.,;, Okamoto, H.,;, Fukawa, I.,;, Konno, S., Green Chem. 2003, 5, 497.
17. Polycarbonate sustainability, Retrieved on 28 April 2014 from http://www.bisphenol-a-europe.org/
18. Pescarmona, P. P.,;, Taherimehr, M., Catal. Sci. Technol. 2012, 2, 2169.
19. Coates, G. W.,;, Moore, D. R., Angew. Chem. Int. Ed. 2004, 43, 6618.
20. Kielland, N.,;, Whiteoak, C. J.,;, Kleij, A. W., Adv. Synth. Catal. 2013, 355, 2115.
21. North, M.,;, Pasquale, R.,;, Young, C., Green Chem. 2010, 12, 1514.
22. Darensbourg, D. J.,;, Wilson, S., J. Green Chem. 2012, 14, 2665.
23. Klaus, S.,;, Lehenmeier, M. W.,;, Anderson, C. E.,;, Rieger, B., Coord. Chem. Rev. 2011, 255, 1460.
24. Bok, T.,;, Noh, E. K.,;, Lee, B. Y., Bull. Korean Chem. Soc 2006, 27, 1171.
25. Ren, W.-M.,;, Zhang, X.,;, Liu, Y.,;, Li, J.-F.,;, Wang, H.,;, Lu, X.-B., Macromolecules 2010, 43, 1396.
26. Darensbourg, D. J.,;, Chung, W.,;, Wilson, S., J. ACS Catal. 2013, 3, 3050.
27. Taherimehr, M.,;, Al-Amsyar, S. M.,;, Whiteoak, C. J.,;, Kleij, A. W.,;, Pescarmona, P. P., Green Chem. 2013, 15, 3083.
28. Cohen, C. T.,;, Coates, G. W., J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 5182.
29. Darensbourg, D., J. Chem. Rev. 2007, 107, 2388.
30. Qin, Z.,;, Thomas, C. M.,;, Lee, S.,;, Coates, G. W., Angew. Chem. Int. Ed. 2003, 42, 5484.
31. Wu, G.-P.,;, Xu, P.-X.,;, Zu, Y.-P.,;, Ren, W.-M.,;, Lu, X.-B., J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 874.
32. Na, S. J.,;, Sujith, S.,;, Cyriac, A.,;, Kim, B. E.,;, Yoo, J.,;, Kang, Y. K.,;, Han, S. J.,;, Lee, C.,;, Lee, B. Y., Inorg. Chem. 2009, 48, 10455.
33. Lu, X.-B.,;, Darensbourg, D., J. Chem. Soc. Rev. 2012, 41, 1462.
34. Lu, X.-B.,;, Shi, L.,;, Wang, Y.-M.,;, Zhang, R.,;, Zhang, Y.-J.,;, Peng, X.-J.,;, Zhang, Z.-C.,;, Li, B., J. Am. Chem. Soc. 2006, 128, 1664.
35. Darensbourg, D. J.,;, Yarbrough, J. C.,;, Ortiz, C.,;, Fang, C. C., J. Am. Chem. Soc. 2003, 125, 7586.
36. Elmas, S.,;, Subhani, M. A.,;, Harrer, M.,;, Leitner, W.,;, Sundermeyer, J.,;, Müller, T. E., Catal. Sci. Technol., 2014, 4, 1652.
37. Dean, R. K.,;, Pressing, K. D.,;, Dawe, L. N.,;, Kozak, C. M., Dalton. Trans. 2013, 42, 9233.
38. Darensbourg, D. J.,;, Wilson, S. J., J. Am. Chem. Soc. 2011, 133, 18610.
39. Luinstra, G. A.,;, Borchardt, E., Adv. Polym. Sci. 2012, 245, 29.
40. Chisholm, M. H.,;, Navarro-Llobet, D.,;, Zhou, Z., Macromolecules 2002, 35, 6494.
41. Zhu, Q.,;, Meng, Y.,;, Tjong, S.,;, Zhao, X.,;, Chen, Y., Polym. Int. 2002, 51, 1079.
42. Jobi, K. V.,;, Jeong, J.,;, Na, S.,;, Sudevan, S.,;, Ok, M.,;, Han, Y.,;, Chung, K.,;, Lee, B., US Pat. 20,120,232,245 A1, 2012.
43. Buchard, A.,;, Kember, M. R.,;, Sandeman, K. G.,;, Williams, C. K., Chem. Commun. 2011, 47, 212.
44. Koning, C.,;, Wildeson, J.,;, Parton, R.,;, Plum, B.,;, Steeman, P.,;, Darensbourg, D., J. Polymer 2001, 42, 3995.
45. Wei, R. J.,;, Zhang, X.-H.,;, Du, B.-Y.,;, Sun, X.-K.,;, Fan, Z.-Q.,;, Qi, G.-R., Macromolecules 2013, 46, 3693.
46. Wu, G.-P.,;, Zu, Y.-P.,;, Xu, P.-X.,;, Ren, W.-M.,;, Lu, X.-B., Chem. Asian J. 2013, 8, 1854.
47. Wu, G.-P.,;, Xu, P.-P.,;, Lu, X.-B.,;, Zu, Y.-P.,;, Wei, S.-H.,;, Ren, W.-M.,;, Darensbourg, D., J. Macromolecules 2013, 46, 2128.
48. Li, B. O.,;, Wu, G.-P.,;, Ren, W.-M.,;, Wang, Y.-M.,;, Rao, D.-Y.,;, Lu, X.-B., J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 6102.
49. Harrold, N. D.,;, Li, Y.,;, Chisholm, M. H., Macromolecules 2013, 46, 692.
50. Chisholm, M. H.,;, Zhou, Z., J. Am. Chem. Soc. 2004, 126, 11030.
51. Allen, S. D.,;, Moore, D. R.,;, Lobkovsky, E. B.,;, Coates, G. W., J. Am. Chem. Soc. 2002, 124, 14284.
52. Byrnes, M. J.,;, Chisholm, M. H.,;, Hadad, C. M.,;, Zhou, Z., Macromolecules 2004, 37, 4139.
53. Wu, G.-P.,;, Ren, W.-M.,;, Luo, Y.,;, Li, B.,;, Zhang, W.-Z.,;, Lu, X.-B., J. Am. Chem. Soc. 2012, 134, 5682.
54. Cohen, C. T.,;, Thomas, C. M.,;, Peretti, K. L.,;, Lobkovsky, E. B.,;, Coates, G. W., Dalton Trans. 2006, 237.
55. Ren, W.-M.,;, Wu, G.-P.,;, Lin, F.,;, Jiang, J.-Y.,;, Liu, C.,;, Luo, Y.,;, Lu, X.-B., Chem. Sci. 2012, 3, 2094.
56. Abbina, S.,;, Du, G., Organometallics 2012, 31, 7394.
57. Ren, W.-M.,;, Liu, Z.-W.,;, Wen, Y.-Q.,;, Zhang, R.,;, Lu, X.-B., J. Am. Chem. Soc. 2009, 131, 11509.
58. Lu, X.-B.,;, Wang, Y., Angew. Chem. Int. Ed. 2004, 43, 3574.
59. Wu, G.-P.,;, Wei, S.-H.,;, Ren, W.-M.,;, Lu, X.-B.,;, Li, B.,;, Zu, Y.-P.,;, Darensbourg, D., J. Energy Environ. Sci. 2011, 4, 5084.
60. Wu, G.-P.,;, Wei, S.-H.,;, Lu, X.-B.,;, Ren, W.-M.,;, Darensbourg, D., J. Macromolecules 2010, 43, 9202.
61. Wu, G.-P.,;, Jiang, S.,;, Lu, X.-B.,;, Ren, W.-M.,;, Yan, S., Chin. J. Polym. Sci. 2012, 30, 487.
62. Cyriac, A.,;, Lee, S. H.,;, Varghese, J. K.,;, Park, J. H.,;, Jeon, J. Y.,;, Kim, S. J.,;, Lee, B. Y., Green Chem. 2011, 13, 3469.
63. Aresta, M., Carbon Dioxide as Chemical Feedstock, 1st ed.; Wiley-VCH: Weinheim, 2012.
64. Kember, M. R.,;, Williams, C. K., J. Am. Chem. Soc. 2012, 134, 15676.
65. Inoue, S., J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 2861.
66. Peng, S.,;, An, Y.,;, Chen, C.,;, Fei, B.,;, Zhuang, Y.,;, Dong, L., Polym. Degrad. Stab. 2003, 80, 141.
67. Zhang, Z.,;, Mo, Z.,;, Zhang, H.,;, Wang, X.,;, Zhao, X., Macromol. Chem. Phys. 2003, 204, 1557.
68. Niu Y.,;, Li, H., Colloid Polym. Sci. 2013, 291, 2181.
69. Thorat, S. D.,;, Phillips, P. J.,;, Semenov, V.,;, Gakh, A., J. Appl. Polym. Sci. 2003, 89, 1163.
70. Varghese, J. K.,;, Cyriac, A.,;, Lee, B. Y., Polyhedron 2012, 32, 90.
71. Salmeia, K. A.,;, Vagin, S.,;, Anderson, C. E.,;, Rieger, B., Macromolecules 2012, 45, 8604.
72. Robert, P. A. L.,;, Young, J., Introduction to Polymers, 3rd ed.; CRC Press: Boca Raton, FL, 2011.
73. Cyriac, A.,;, Lee, S. H.,;, Varghese, J. K.,;, Park, E. S.,;, Park, J. H.,;, Lee, B. Y., Macromolecules 2010, 43, 7398.
74. Qin, Y.,;, Wang, X.,;, Zhang, S.,;, Zhao, X.,;, Wang, F., J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 5959.
75. Ren, W.-M.,;, Liu, Y.,;, Wu, G.-P.,;, Liu, J.,;, Lu, X.-B., J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 4894.
76. Rieger, B.,;, Künkel, A.,;, Coates, G. W.,;, Reichardt, R.,;, Dinjus, E.,;, Zevaco, Th.A., Eds., Advances in Polymer Science; Springer: Berlin, 2012; Vol. 245.
77. Nakano, K.,;, Hashimoto, S.,;, Nakamura, M.,;, Kamada, T.,;, Nozaki, K., Angew. Chem. Int. Ed. 2011, 50, 4868.
78. Hsu. T.-J.,;, Tan, C.-S., Polymer 2002, 43, 4535.
79. Seong, J. E.,;, Na, S. J.,;, Cyriac, A.,;, Kim, B.-W.,;, Lee, B. Y., Macromolecules 2010, 43, 903.
80. Stretz, H. a.,;, Cassidy, P. E.,;, Paul, D. R., J. Appl. Polym. Sci. 1999, 74, 1508.
81. Thompson, R.,;, Moore, C.,;, Andrady, A.,;, Gregory, M.,;, Takada, H.,;, Weisberg, S., Science 2005, 310, 1117.
82. Artham, T.,;, Doble, M., Macromol. Biosci. 2008, 8, 14.
83. Liu, B.,;, Chen, L.,;, Zhang, M.,;, Yu, A., Macromol. Rapid Commun. 2002, 23, 881.
84. Siemann, U., Progr. Colloid Polym. Sci. 2005, 130, 1.
85. Sarbu, T.,;, Styranec, T.,;, Beckman, E., Nature 2000, 405, 165.
86. Zhong, X.,;, Dehghani, F., Green Chem. 2012, 14, 2523.
87. Mullen, B. D.,;, Tang, C. N.,;, Storey, R. F., Polym. Chem. 2003, 41, 1987.
88. Zhuo, R., J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 4001.
89. Darensbourg, D. J.,;, Fang, C. C.,;, Rodgers, J. L., Organometallics 2004, 23, 924.
90. Kim, J. G.,;, Cowman, C. D.,;, LaPointe, A. M.,;, Wiesner, U.,;, Coates, G. W., Macromolecules 2011, 44, 1110.
91. Byrne, C. M.,;, Allen, S. D.,;, Lobkovsky, E. B.,;, Coates, G. W., J. Am. Chem. Soc. 2004, 126, 11404.
92. Darensbourg, D. J.,;, Moncada, A. I., Macromolecules 2010, 43, 5996.
93. Darensbourg, D. J.,;, Moncada, A. I., Macromolecules 2009, 42, 4063.
94. Gu, L.,;, Qin, Y.,;, Gao, Y.,;, Wang, X.,;, Wang, F., J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 2834.
95. Cyriac, A.,;, Lee, S. H.,;, Lee, B. Y., Polym. Chem. 2011, 2, 950.
96. Nakano, K.,;, Kamada, T.,;, Nozaki, K., Angew. Chem. Int. Ed. 2006, 45, 7274.
97. 2 aids Bayer's sustainablility efforts, 2013; Available at http://www.plasticsnews.com/article/20131016/NEWS/131019950/co2-aids-bayers- sustainablility-efforts, accessed on May 5, 2014.
98. Lu, X. L.,;, Du, F. G.,;, Ge, X. C.,;, Xiao, M.,;, Meng, Y. Z., J. Biomed. Mater. Res. 2006, 77A, 653.
99. Jeon, J. Y.,;, Lee, J. J.,;, Varghese, J. K.,;, Na, S. J.,;, Sujith, S., Go, M. J.,;, Lee, J.,;, Ok, M.-A.,;, Lee, B. Y., Dalton Trans. 2013, 42, 9245.
100. Center console trays [.], 2014; Available at http://www.tpu.bayer.com/en/ Case-studies/Interior/Center-console-trays.aspx, accessed on May 5, 2014.
101. Simoneau, C. A.,;, Allen, S. D.,;, Farmer, J., J. WO Pat. 2012154849 A1, 2012.
102. Engels, H.-W.,;, Pirkl, H.-G.,;, Albers, R.,;, Albach, R. W.,;, Krause, J.,;, Hoffmann, A.,;, Casselmann, H.,;, Dormish, J., Angew. Chem. Int. Ed. 2013, 52, 9422.
103. Farmer, J. J.,;, Allen, S. D.,;, Cherian, A. E.,;, Simoneau, C. A., WO Pat. 2011163133 A1, 2011.
104. Stevens, J. W.,;, Allen, S. D.,;, Simoneau, C. A.,;, Salladay, J. M.,;, Hatfield, D. M., US Pat. 20,110,218,127 A1, 2011.
105. CO2 based plastics and polymers; Available at http://www.novomer.com/? action=tech-overview2014, accessed on May 10, 2014.
106. Koning, C. E.,;, Sablong, R. J.,;, Nejad, E. H.,;, Duchateau, R.,;, Buijsen, P., Prog. Org. Coatings 2013, 76, 1704.
107. Allen, S. D., Pat. EP2451860A2, 2012.
108. Ford, M. E.,;, Mantell, G. J.,;, Dixon, D. D., J. Polym. Sci. Polym. Lett. Ed. 1980, 18, 131.
109. Kim, G.,;, Ree, M.,;, Kim, H.,;, Kim, I. J.,;, Kim, J. R.,;, Lee, J. I., Macromol. Res. 2008, 16, 473.
110. Luinstra, G. A., Polym. Rev. 2008, 48, 192.
111. Salamone, J. C., Concise Polymeric Materials Encyclopedia; CRC Press: Boca Raton, FL, 1998.
112. Coating resins, Available at http://www.novomer.com/?action=CO2-coatings; accessed on May 12, 2014.