Xanthate-mediated radical polymerization of N-vinylpyrrolidone in fluoroalcohols for simultaneous control of molecular weight and tacticity

Macromolecules

Volumn 38, Issue 25, 2005, Pages 10397-10405

  Wan, Decheng ^a   Satoh, Kotaro ^a   Kamigaito, Masami ^a   Okamoto, Yoshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; FLUORINE COMPOUNDS; HYDROGEN BONDS; LIVING POLYMERIZATION; MOLECULAR WEIGHT; THERMAL EFFECTS;

FLUOROALCOHOLS; INDUCTION PERIODS; SYNDIOSPECIFIC POLYMERIZATION; TACTICITY CONTROL;

NITROGEN COMPOUNDS;

EID: 29444447760     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0515230     Document Type: Article

References (88)

1. Kirsh, Y. E. Water Soluble Poly-N-Vinylamides, Synthesis and Physicochemical Properties; John Wiley & Sons: Chichester, 1998.
2. Robinson, B. V.; Sullivan, F. M.; Borzelleca, J. F.; Schwartz, S. L. PNVP, A Critical Review of the Kinetics and Toxicology of Polyvinylpyrrolidone (Povidone); Lewis: Michigan, 1990.
3. Barabas, E. S. In Concise Encyclopedia of Polymer Science and Engineering; Kroschwitz, J. I., Ed.; Wiley: New York, 1990; pp 1236-1241.
4. (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987-2988.
5. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66-72.
6. (a) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185-11186.
7. (b) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
8. (a) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721-1723.
9. (b) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3745.
10. (c) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rec. 2004, 4, 159-175.
11. (a) Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
12. (b) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
13. Percec, V.; Barboiu, B. Macromolecules 1995, 28, 7970-7972.
14. Granel, C.; Dubois, Ph.; Jérôme, R.; Teyssié, Ph. Macromolecules 1996, 29, 8576-8582.
15. Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J.; Shooter, A. J. Macromolecules 1997, 30, 2190-2193.
16. (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.
17. (b) Chong, Y. K.; Kristina, J.; Tam, P. T. Le.; Moad, G.; Postma, A.; Rizzardo, E.; Thang, S. H. Macromolecules 2003, 36, 2256-2272.
18. (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.
19. (d) Le, T. P.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 98/01478.
20. (e) Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 99/31144.
21. (a) Destarac, M.; Bzducha, W.; Taton, D.; Gauthier-Gillaizeau, I.; Zard, S. Z. Macromol. Rapid Commun. 2002, 23, 1049-1054.
22. (b) Charmot, D.; Corpart, P.; Michelet, D.; Zard, S.; Biadatti, T. PCT Int. Appl. WO 98/58974.
23. (c) Destarac, M.; Charmot, D.; Zard, S.; Franck, X. PCT Int. Appl. WO 00/75207.
24. Rizzardo, E.; Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Thang, S. H. ACS Symp. Ser. 2000, 786, 278-296.
25. Charmot, D.; Corpart, P.; Adam. H.; Zard, S. Z.; Biadatti, T.; Bouhadir, G. Macromol. Symp. 2000, 150, 23-32.
26. Destarac, M.; Charmot, D.; Franck, X.; Zard, S. Z. Macromol. Rapid Commun. 2000, 21, 1035-1039.
27. Stenzel, M. H.; Cummins, L.; Roberts, G. E.; Davis, T. P.; Vana, P.; Barner-Kowollik, C. Macromol. Chem. Phys. 2003, 204, 1160-1168.
28. Coote, M. L.; Radom. L. Macromolecules 2004, 37, 590-596.
29. Favier, A.; Barner-Kowollik, C.; Davis, T.; Stenzel, M. H. Macromol. Chem. Phys. 2004, 205, 925-936.
30. Wakioka, M.; Baek, K.-Y.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 2002, 35, 330-333.
31. (a) Ueda, N.; Kamigaito, M.; Sawamoto, M. Polym. Prepr. Jpn. 1996, 45 (7), 1267-1268;
32. Ueda, N.; Kamigaito, M.; Sawamoto, M. Polym. Prepr. Jpn. 1997, 46 (2), 149;
33. Ueda, N.; Kamigaito, M.; Sawamoto, M. Polym. Prepr. Jpn. 1998, 47 (2), 134.
34. (b) Ueda, N.; Kamigaito, M.; Sawamoto, M. The 37th IUPAC International Symposium on Macromolecules, Preprints, Gold Coast, Australia, 1998; p 237.
35. (c) Ueda, N. JP Patents 10, 060, 021 (Aug 13, 1996); 11, 147, 914 (Nov 17, 1997); 11, 171, 926 (Dec 11, 1997).
36. Iovu, M. C.; Matyjaszewski, K. Macromolecules 2003, 36, 9346-9534.
37. (a) Debuigne, A.; Caille, J.-R.; Jérôme, R. Angew. Chem., Int. Ed. 2005, 44, 1101-1104.
38. (b) Debuigne, A.; Caille, J.-R.; Jérôme, R. Macromolecules 2005, 38, 5452-5458.
39. (a) Assandei, A. D.; Percec, V. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3392-3418.
40. (b) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Monteiro, M.; Barboiu, B.; Weichold, O.; Assandei, A. D.; Mitchell, C. M. J. Am. Chem. Soc. 2002, 124, 4940-4941.
41. (c) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Weichold, O. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3283-3299.
42. (a) Percec, V.; Popov, A. V.; Ramirez-Castillo, E. Weichold, O. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 6267-6289.
43. (b) Percec, V.; Popov, A. V.; Ramirez-Castillo, E. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 287-295.
44. (c) Percec, V.; Popov, A. V.; Ramirez-Castillo, E. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 773-778.
45. (d) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Coelcho, J. F. J.; Hinojosa-Falcon, L. A. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 779-788.
46. (e) Percec, V.; Ramirez-Castillo, E.; Hinojosa-Falcon, L. A.; Popov, A. V. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2185-2187.
47. (a) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 2874-2875.
48. (b) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 13666-13667.
49. 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.
50. Shi, L.; Chapman, T. M.; Beckman, E. J. Macromolecules 2003, 36, 2563-2567.
51. Habaue, S.; Okamoto, Y. Chem. Rec. 2001, 1, 46-52.
52. (a) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605.
53. (b) Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2677-2683.
54. (c) Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 220-228.
55. (d) Yamada, K.; Nakano, T.; Okamoto, Y. Polym. J. 2000, 32, 707-710.
56. (a) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1999, 32, 5979-5981.
57. (b) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4693-4703.
58. (c) Isobe, Y.; Nakano, T.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1463-1471.
59. (a) Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 7180-7181.
60. (b) Habaue, S.; Isobe, Y.; Okamoto, Y. Tetrahedron 2002, 58, 8205-8209.
61. (c) Suito, Y.; Isobe, Y.; Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2496-2500.
62. (d) Isobe, Y.; Suito, Y.; Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1027-1033.
63. (e) Ray, B.; Isobe, Y.; Habaue, S.; Kamigaito, M.; Okamoto, Y. Polym. J. 2004, 36, 728-736.
64. (a) Hirano, T.; Ishii, S.; Kitajima, H.; Seno, M.; Sato, T. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 50-62.
65. (b) Hirano, T.; Miki, H.; Seno, M.; Sato, T. Polymer 2005, 46, 3693-3699.
66. Cheng, H. N.; Smith, T. E.; Vitus, D. M. J. Polym. Sci., Polym. Lett. 1981, 19, 29-31.
67. Ebdon, J. R.; Huckerby, T. N.; Senogles, E. Polymer 1983, 24, 338-341.
68. (a) Ray, B.; Isobe, Y.; Morioka, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2003, 36, 543-545.
69. (b) Ray, B.; Isobe, Y.; Matsumoto, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2004, 37, 1702-1710.
70. (c) Ray, B.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M.; Seno, K.; Kanaoka, S.; Aoshima, S. Polym. J. 2005, 37, 234-237.
71. (a) Sugiyama, Y.; Kamigaito, M.; Okamoto, Y. Polym. Prepr. Jpn. 2004, 53, 430.
72. (b) Sugiyama, Y.; Satoh, K.; Kamigaito, M.; Okamoto, Y. Polym. Prepr. Jpn. 2004, 53, 5410-2411.
73. (a) Lutz, J.-F.; Neugebauer, D.; Matyjaszewski, K. J. Am. Chem. Soc. 2003, 125, 6986-6993.
74. (b) Lutz, J.-F.; Jakubowski, W.; Matyjaszewski, K. Macromol. Rapid Commun. 2004, 25, 486-492.
75. Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. Macromolecules 2005, 38, 1041-1403.
76. Quinn, J. F.; Rizzardo, E.; Davis, T. P. Chem. Commun. 2001, 1044.
77. Barner-Kowollik, C.; Coote, M. L.; Davis, T. P.; Radom, L.; Vana, P. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2828-2832.
78. Wang, A. R.; Zhu, S.; Kwak, Y.; Goto, A.; Fukuda, T.; Monteiro, M. S. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2833-2839.
79. Barner-Kowollik, C.; Quinn, J. F.; Nguyen, T. L. U.; Heuts, J. P. A.; Davis, T. P. Macromolecules 2001, 34, 7849-7857.
80. Feldermann, A.; Toy, A. A.; Davis, T. P.; Stenzel, M. H. Polymer 2005, 46, 8448-8457.
81. Chernikova, E.; Morozov, A.; Leonova, E.; Garina, E.; Golubev, V.; Bui, C.; Charleux, B. Macromolecules 2004, 37, 6329-6339.
82. Quinn, J. F.; Barner, L.; Barner-Kowollik, C.; Rizzardo, E.; Davis, T. P. Macromolecules 2002, 35, 7620-7627.
83. (a) Blanda, M. T.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1989, 54, 4626-4636.
84. (b) Gil, V. M. S. J. Chem. Educ. 1990, 67, 473-478.
85. (c) Macomber, R. S. J. Chem. Educ. 1992, 69, 375-378.
86. Filler, R.; Schure, R. M. J. Org. Chem. 1967, 32, 1217-1219.
87. Hamaura, T.; Newton, M. J. Pharm. Sci. 1999, 88, 1228-1233
88. Zhang, J.; Zografi, G. J. Pharm. Sci. 2000, 89, 1063-1072.