Iodine transfer radical polymerization of vinyl acetate in fluoroalcohols for simultaneous control of molecular weight, stereospecificity, and regiospecificity

Macromolecules

Volumn 39, Issue 12, 2006, Pages 4054-4061

  Koumura, Kazuhiko ^a   Satoh, Kotaro ^a   Kamigaito, Masami ^a   Okamoto, Yoshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; MOLECULAR WEIGHT; MOLECULAR WEIGHT DISTRIBUTION; MONOMERS; POLYMERIZATION; SOLVENTS;

FLUOROALCOHOLS; IODINE TRANSFER RADICAL POLYMERIZATION; REGIOSPECIFICITY; SYNDIOTACTICITY;

POLYVINYL ACETATES;

EID: 33745777999     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0602775     Document Type: Article

References (87)

1. Finch, C. A., Ed.; Polyvinyl Alcohols Developments; Wiley: Chichester, 1992.
2. Miyasaka, K. Adv. Polym. Sci. 1993, 108, 91-129.
3. Chiellini, E.; Corti, A.; Corti, A.; D'Antone, S.; Solaro, R. Prog. Polym. Sci. 2003, 28, 963-1014.
4. Jayasekara, R.; Harding, I.; Bowater, I.; Lonergan, G. J. Polym. Environ. 2005, 13, 231-251.
5. Drury, J. L.; Mooney, D. J. Biomaterials 2003, 24, 4337-4351.
6. Miyata, T.; Uragami, T.; Nakamae, K. Adv. Drug Delivery Rev. 2002, 54, 79-98.
7. Lee, K. Y.; Mooney, D. J. Chem. Rev. 2001, 101, 1869-1879.
8. Amiya, S.; Uetsuki, M. Macromolecules 1982, 15, 166-170.
9. Amiya, S.; Uetsuki, M. Anal. Sci. 1985, 1, 91-92.
10. Ovenall, D. W. Macromolecules 1984, 17, 1458-1464.
11. (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987-2988.
12. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66-72.
13. (a) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185-11186.
14. (b) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
15. (a) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721-1723.
16. (b) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3745.
17. (c) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rec. 2004, 4, 159-175.
18. (a) Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
19. (b) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
20. Percec, V.; Barboiu, B. Macromolecules 1995, 28, 7970-7972.
21. Granel, C.; Dubois, Ph.; Jérôme, R.; Teyssié, Ph. Macromolecules 1996, 29, 8576-8582.
22. Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J.; Shooter, A. J. Macromolecules 1997, 30, 2190-2193.
23. (a) Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J. Jeffery, K.; Tam, P. T. Le.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559-5562.
24. (b) Chong, Y. K.; Kristina, J.; Tam, P. T. Le.; Moad, O.; Postma, A.; Rizzardo, E.; Thang, S. H. Macromolecules 2003, 36, 2256-2272.
25. (c) Chiefari, J.; Mayadunne, R. T. A.; Moad, C. L.; Moad, G.; Rizzardo, E.; Postma, A.; Skidmoe, M. A.; Thang, S. H. Macromolecules 2003, 36, 2273-2283.
26. (d) Le, T. P.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 98/01478.
27. (e) Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 99/31144.
28. (a) Destarac, M.; Bzducha, W.; Taton, D.; Gauthier-Gillaizeau, I.; Zard, S. Z. Macromol. Rapid Commun. 2002, 23, 1049-1054.
29. (b) Charmot, D.; Corpart, P.; Michelet, D.; Zard, S.; Biadatti, T. PCT Int. Appl. WO 98/58974.
30. (c) Destarac, M.; Charmot, D.; Zard, S.; Franck, X. PCT Int. Appl. WO 00/75207.
31. Rizzardo, E.; Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Thang, S. H. ACS Symp. Ser. 2000, 786, 278-296.
32. Charmot, D.; Corpart, P.; Adam, H.; Zard, S. Z.; Biadatti, T.; Bouhadir, G. Macromol. Symp. 2000, 150, 23-32.
33. Destarac, M.; Charmot, D.; Franck, X.; Zard, S. Z. Macromol. Rapid Commun. 2000, 21, 1035-1039.
34. Stenzel, M. H.; Cummins, L.; Roberts, G. E.; Davis, T. P.; Vana, P.; Bamer-Kowollik, C. Macromol. Chem. Phys. 2003, 204, 1160-1168.
35. (b) Stenzel, M. H.; Davis, T. P.; Barner-Kowollik, C. Chem. Commun. 2004, 1546-1547.
36. Coote, M. L.; Radom, L. Macromolecules 2004, 37, 590-596.
37. Favier, A.; Barner-Kowollik, C.; Davis, T.; Stenzel, M. H. Macromol. Chem. Phys. 2004, 205, 925-936.
38. Simms, R. W.; Davis, T. P.; Cunningham, M. F. Macromol. Rapid Commun. 2005, 26, 592-596.
39. Boschmann, D.; Vana, P. Polym. Bull. (Berlin) 2005, 53, 231-242.
40. Russum, J. P.; Barbre, N. D.; Jones, C. W.; Schork, F. J. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2188-2193.
41. Wakioka, M.; Baek, K.-Y.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 2002, 35, 330-333.
42. (a) Ueda, N.; Kamigaito, M.; Sawamoto, M. The 37th IUPAC International Symposium on Macromolecules, Preprints, Gold Coast, Australia, 1998; p 237.
43. (b) Ueda, N. JP Patents 10,060,021 (Aug 13, 1996); 11,147,914 (Nov 17, 1997); 11,171,926 (Dec 11, 1997).
44. Iovu, M. C.; Matyjaszewski, K. Macromolecules 2003, 36, 9346-9534.
45. Borkar, S.; Sen, A. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3728-3736.
46. (a) Debuigne, A.; Caille, J.-R.; Jérôme, R. Angew. Chem., Int. Ed. 2005, 44, 1101-1104.
47. (b) Debuigne, A.; Caille, J.-R.; Jérôme, R. Macromolecules 2005, 38, 5452-5458.
48. (c) Debuigne, A.; Caille, J.-R.; Detrembleur, C.; Jérôme, R. Angew. Chem., Int. Ed. 2005, 44, 3439-3442.
49. (c) Debuigne, A.; Caille, J.-R.; Willet, N.; Jérôme, R. Macromolecules 2005, 38, 9488-9496.
50. Kaneyoshi, H.; Matyjaszewski, K. Macromolecules 2005, 38, 8163-8169.
51. (a) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 2874-2875.
52. (b) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 13666-13667.
53. (c) Yamago, S.; Ray, B.; Iida, K.; Yoshida, J.; Tada, T.; Yoshizawa, K.; Kwak, Y.; Goto, A.; Fukuda, T. J. Am. Chem. Soc. 2004, 126, 13908-13909.
54. (d) Yamago, S. Proc. Jpn. Acad. Ser. B 2005, 81, 117-128.
55. (e) Yamago, S. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1-12.
56. Habaue, S.; Okamoto, Y. Chem. Rec. 2001, 1, 46-52.
57. (a) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605.
58. (b) Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2677-2683.
59. (c) Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 220-228.
60. (d) Yamada, K.; Nakano, T.; Okamoto, Y. Polym. J. 2000, 32, 707-710.
61. (a) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1999, 32, 5979-5981.
62. (b) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 58, 4693-4703.
63. (c) Isobe, Y.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1463-1471.
64. (a) Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 7180-7181.
65. (b) Habaue, S.; Isobe, Y.; Okamoto, Y. Tetrahedron 2002, 58, 8205-8209.
66. (c) Suito, Y.; Isobe, Y:; Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2496-2500.
67. (d) Isobe, Y.; Suito, Y.: Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1027-1033.
68. (e) Ray, B,; Isobe, Y.; Habaue, S.; Kamigaito, M.; Okamoto, Y. Polym. J. 2004, 36, 728-736.
69. (a) Hirano, T.; Ishii, S.; Kitajima, H.; Seno, M.; Sato, T. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 50-62.
70. (b) Hirano, T.; Miki, H.; Seno, M.; Sato, T. Polymer 2005, 46, 3693-3699.
71. Kamigaito, M.; Satoh, K.; Wan, D.; Sugiyama, Y.; Koumura, K.; Shibata, T.; Okamoto, Y. ACS Symp. Ser. 2006, 944, 26-39.
72. (a) Ray, B.; Isobe, Y.; Morioka, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2003, 36, 543-545.
73. (b) Ray, B.; Isobe, Y.; Matsumoto, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2004, 37, 1702-1710.
74. (c) Ray, B.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M.; Seno, K.; Kanaoka, S.; Aoshima, S. Polym. J. 2005, 37, 234-237.
75. Sugiyama, Y.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2086-2098.
76. (a) Lutz, J.-F.; Neugebauer, D.; Matyjaszewski, K. J. Am. Chem. Soc. 2003, 125, 6986-6993.
77. (b) Lutz, J.-F.; Jakubowski, W.; Matyjaszewski, K. Macromol. Rapid Commun. 2004, 25, 486-492.
78. (a) Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. Macromolecules 2005, 38, 1041-1403.
79. (b) Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1436-1446.
80. Shibata, T.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3609-3615.
81. Wan, D.; Satoh, K.; Kamigaito, M.; Okamoto, Y. Macromolecules 2005, 38, 10397-10405.
82. Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831.
83. Wu, T. K.; Sheer, M. L. Macromolecules 1977, 10, 529-531.
84. Hikichi, K.; Yasuda, M. Polym. J. 1987, 19, 1003-1012.
85. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability, Wiley: New York, 1987; pp 24-28.
86. Gil, V. M. S.; Oliveira, N. C. J. Chem. Educ. 1990, 67, 473-478.
87. Macomber, R. S. J. Chem. Educ. 1992, 69, 375-378.