Recent developments in synthesis of stimuli-responsive polymers by living polymerization

Kobunshi Ronbunshu

Volumn 63, Issue 2, 2006, Pages 71-85

  Aoshima, Sadahito ^a   Kanaoka, Shokyoku ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Block copolymer; Fast living Polymerization; LCST; Living cationic polymerization; Living radical polymerization; Physical gelation; Poly (NIPAM); Poly(vinyl ether); Self association; Stimuli responsive polymer

Indexed keywords

FAST LIVING POLYMERIZATION; LIVING CATIONIC POLYMERIZATION; LIVING RADICAL POLYMERIZATION; PHYSICAL GELATION; SELF-ASSOCIATION; STIMULI-RESPONSIVE POLYMER;

BLOCK COPOLYMERS; CATIONIC POLYMERIZATION; ETHERS; GELATION; LIVING POLYMERIZATION; SYNTHESIS (CHEMICAL); VINYL RESINS;

ORGANIC POLYMERS;

POLYMER; POLYMERIZATION; SYNTHESIS;

EID: 33645811925     PISSN: 03862186     EISSN: None     Source Type: Journal    
DOI: 10.1295/koron.63.71     Document Type: Review

References (184)

1. A. S. Hoffman, Macromol. Symp., 98, 645 (1995).
2. Japanese source. 50, 446 (2001).
3. H. G. Schild, Prog. Polym. Sci., 17, 163 (1992).
4. B. Jeong and A. Gutowska, Trends in Biotechnol., 20, 305 (2002).
5. K. Matyjaszewski, "Controlled Radical Polymerization", K. Matyjaszewski ed., ACS Symp. Ser., 685, American Chemical Society, Washington, DC (1998).
6. K. Matyjaszewski, "Controlled/Living Radical Polymerization", K. Matyjaszewski ed., ACS Symp. Ser., 768, American Chemical Society, Washington, DC (2000).
7. K. Matyjaszewski, "Advances in Controlled/Living Radical Polymerization", K. Matyjaszewski ed., ACS Symp. Ser., 854, American Chemical Society, Washington, DC (2003).
8. T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127 (1982).
9. M. K. George, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 2987 (1993).
10. C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994).
11. M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995).
12. J. S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
13. J. Chiefari, Y. K. B. Chong, F. Ercole, J. Krstina, J. Jeffery, T. P. T. Le, R. T. A. Mayadunne, G. F. Meijs, C. L. Moad, G. Moad, E. Rizzardo, and S. H. Thang, Macromolecules, 31, 5559 (1998).
14. F. Ganachaud, M. J. Monteiro, R. G. Gilbert, M. Dourges, S. H. Thang, and E. Rizzardo, Macromolecules, 33, 6738 (2000).
15. C. Schilli, M. G. Lanzendörfer, and A. H. E. Müller, Macromolecules, 35, 6819 (2002).
16. Japanese source, 49, (2000 p. 1737).
17. J. Convertine, N. Ayres, C. W. Scales, A. B. Lowe, and C. L. McCormick, Biomacromolecules, 5, 1177 (2004).
18. A. Goto, Y. Kwak, T. Fukuda, S. Yamago, K. Iida, M. Nakajima, and J. Yoshida, J. Am. Chem. Soc., 125, 8720 (2003).
19. S. Yamago, B. Ray, K. Iida, J. Yoshida, T. Tada, K. Yoshizawa, Y. Kwak. A. Goto, and T. Fukuda, J. Am. Chem. Soc., 126, 13908 (2004).
20. A. W. Bosman, R. Vestberg, A. Heumann, J. M. J. Fréchet, and C. J. Hawker, J. Am. Chem. Soc., 125, 715 (2003).
21. G. Masci, L. Giacomelli, and V. Crescenzi, Macromol. Rapid Commun., 25, 559 (2004).
22. Y. Xia, X. Yin, N. A. D. Burke, and H. D. H. Stöver, Macromolecules, 38, 5937 (2005).
23. B. Ray, Y. Isobe, K. Morioka, S. Habaue, Y. Okamoto, M. Kamigaito, and M. Sawamoto, Macromolecules, 36, 543 (2003).
24. B. Ray, Y. Isobe, K. Matsumoto, S. Habaue, Y. Okamoto, M. Kamigaito, and M. Sawamoto, Macromolecules, 37, 1702 (2004).
25. B. Ray, Y. Okamoto, M. Kamigaito, M. Sawamoto, K. Seno, S. Kanaoka, and S. Aoshima, Polym. J., 37, 234 (2005).
26. C. M. Schilli, A. H. E. Müller, E. Rizzardo, S. H. Thang, and Y. K. Chong, "Advances in Controlled/Living Radical Polymerization", K. Matyjaszewski ed., ACS Symp. Ser., 854, American Chemical Society, Washington, DC (2003) pp. 603.
27. T. Ishizone and M. Ito, J. Polym. Sci., Part A: Polym. Chem., 40, 4328 (2002).
28. T. Kitayama, W. Shibuya, and K. Katsukawa, Polym. J., 34, 405 (2002).
29. M. Kobayashi, T. Ishizone, and S. Nakahama, J. Polym. Sci., Part A: Polym. Chem., 38, 4677 (2000).
30. M. D. C. Topp, P. J. Dijkstra, H. Talsma, and J. Feijen, Macromolecules, 30, 8518 (1997).
31. S. Cammas, K. Suzuki, C. Sone, Y. Sakurai, K. Kataoka, and T. Okano, J. Controlled Release, 48, 157 (1997).
32. F. Kohori, K. Sakai, T. Aoyagi, M. Yokoyama, Y. Sakurai, and T. Okano, J. Controlled Release, 55, 87 (1998).
33. C. Y. Hong, Y. Z. You, and C. Y. Pan, J. Polym. Sci., Part A: Polym. Chem., 42, 4873 (2004).
34. Y. You, C. Hong, W. Wang, W. Lu, and C. Pan, Macromolecules, 37, 9761 (2004).
35. C. M. Schilli, M. Zhang, E. Rizzardo, S. H. Thang, B. Y. K. Chong, K. Edwards, G. Karlsson, and A. H. E. Müller, Macromolecules, 37, 7861 (2004).
36. S. Yusa, Y. Shimada, Y. Mitsukami, T. Yamamoto, and Y. Morishima, Macromolecules, 37, 7507 (2004).
37. B. Liu and S. Perrier, J. Polym. Sci., Part A: Polym. Chem., 43, 3643 (2005).
38. M. Nuopponen, J. Ojala, and H. Tenhu, Polymer, 45, 3643 (2004).
39. G. Moad, Y. K. Chong, A. Postma, E. Rizzardo, and S. H. Thang, Polymer, 46, 8458 (2005).
40. M. Nakayama and T. Okano, Biomacromolecules, 6, 2320 (2005).
41. M. Arotçaréna, B. Heise, S. Ishaya, and A. Laschewsky, J. Am. Chem. Soc., 124, 3787 (2002).
42. H. Lin and Y. Cheng, Macromolecules, 34, 3710 (2001).
43. Y. Z. You, C. Y. Hong, C. Y. Pan, and P. H. Wang, Adv. Mater. (Weinheim, Ger.), 16, 1953 (2004).
44. S. Carter, B. Hunt, and S. Rimmer, Macromolecules, 38, 4595 (2005).
45. X. S. Feng and C. Y. Pan, Macromolecules, 35, 4888 (2002).
46. T. Hu, Y. You, C. Pan, and C. Wu, J. Phys. Chem. B, 106, 6659 (2002).
47. D. J. Kim, J. Y. Heo, K. S. Kim, and I. S. Choi, Macromol. Rapid Commun., 24, 517 (2003).
48. S. Tsuji and H. Kawaguchi, Langmuir, 20, 2449 (2004).
49. C. Y. Hong, Y. Z. You, and C. Y. Pan, Chem. Mater., 17, 2247 (2005).
50. J. Shan, M. Nuopponen, H. Jiang, E. Kauppinen, and H. Tenhu, Macromolecules, 36, 4526 (2003).
51. N. Tsubokawa, Bull. Chem. Soc. Jpn., 75, 2115 (2002).
52. K. Haraguchi, T. Takehisa, and S. Fan, Macromolecules, 35, 10162 (2002).
53. As a review, see: K. te Nijenhuis: Adv. Polym. Sci., 130, 1 (1997).
54. K. Mortensen and J. S. Pedersen, Macromolecules, 26, 805 (1993).
55. B. Jeong, Y. H. Bae, D. S. Lee, and S. W. Kim, Nature, 388, 860 (1997).
56. H. Li, G.-E. Yu, C. Price, C. Booth, E. Hecht, and H. Hoffmann, Macromolecules, 30, 1347 (1997).
57. K. Mortensen, Prog. Colloid Polym. Sci., 93, 72 (1993).
58. S. Han, M. Hagiwara, and T. Ishizone, Macromolecules, 36, 8312 (2003).
59. S. Aoki, A. Koide, S. Imabayashi, and M. Watanabe, Chem. Lett., 31, 1128 (2002).
60. Japanese source, 53, (2004) p. 4186.
61. A. B. Lowe, N. C. Billingham, and S. P. Armes, Macromolecules, 31, 5991 (1998).
62. M. Akashi, S. Nakano, and A. Kishida, J. Polym. Sci., Part A: Polym. Chem., 34, 301 (1996).
63. Y. Nagasaki, E. Honzawa, M. Kato, K. Kataoka, and T. Tsuruta, Macromolecules, 27, 4848 (1994).
64. Japanese source, 49, (2000) p. 3079.
65. Japanese source, 72, 909 (2003).
66. W. A. Petka, J. L. Harden, K. P. McGrath, D. Wirtz, and D. A. Tirrell, Science, 281, 389 (1998).
67. C. Wang, R. J. Stewart, and J. Kopecek, Nature, 397, 417 (1999).
68. S. Kulkarni, C. Schilli, A. H. E. Müller, A. S. Hoffman, and P. S. Stayton, Bioconjugate Chem., 15, 747 (2004).
69. Japanese source, (1971).
70. M. Miyamoto, M. Sawamoto, T. Higashimura, Macromolecules, 17, 265, 2228 (1984).
71. S. Aoshima, T. Nakamura, N. Uesugi, M. Sawamoto, and T. Higashimura, Macromolecules, 18, 2097 (1985).
72. T. Higashimura, S. Aoshima, and M. Sawamoto, Macromol. Symp., 3, 99 (1986).
73. M. Sawamoto, S. Aoshima, and T. Higashimura, Macromol. Symp., 13/14, 513 (1988).
74. K. Matyjaszewski and M. Sawamoto, "Cationic Polymerizations: Mechanisms, Synthesis, and Applications", K. Matyjaszewski ed., Marcel Dekker, New York (1996), Chapter 4.
75. S. Aoshima and T. Higashimura, Polym. Bull. (Heidelberg, Ger.), 15, 417 (1986).
76. S. Aoshima and T. Higashimura, Macromolecules, 22, 1009 (1989).
77. Y. Kishimoto, S. Aoshima, and T. Higashimura, Macromolecules, 22, 3877 (1989).
78. G. Kaszas, J. E. Puskas, C. C. Chen, and J. P. Kennedy, Macromolecules, 23, 3909 (1990).
79. C. G. Cho, B. A. Feit, and O. W. Webster, Macromolecules, 23, 1918 (1990).
80. D. Y. Sogah and O. W. Webster, Macromolecules, 19, 1775 (1986).
81. M. Kamigaito, Y. Maeda, M. Sawamoto, T. Higashimura, Macromolecules, 26, 1643 (1993).
82. Y. Ishihama, M. Sawamoto, and T. Higashimura, Polym. Bull. (Heidelberg, Ger.), 24, 201 (1990).
83. T. Higashimura, Y. Ishihama, and M. Sawamoto, Macromolecules, 26, 744 (1993).
84. K. Matyjaszewski and C. H. Lin, J. Polym. Sci., Part A: Polym. Chem., 29, 1439 (1991).
85. "Cationic Polymerizations: Mechanisms, Synthesis, and Applications", K. Matyjaszewski ed., Marcel Dekker, New York (1996).
86. J. P. Kennedy and B. Iván, "Designed Polymers by Carbocationic Macromolecular Engineering: Theory and Practice", Hanser Publishers, München (1992).
87. R. Faust and J. P. Kennedy, J. Polym. Sci., Part A, Polym. Chem., 25, 1847 (1987).
88. J. P. Kennedy, J. Polym. Sci., Part A: Polym. Chem., 37, 2285 (1999).
89. M. Sawamoto, J. Polym. Sci., Part A: Polym. Chem., 34, 3439 (1996).
90. J. P. Kennedy, J. Macromol. Sci., Chem., A3, 885 (1969).
91. K. Sato, M. Kamigaito, and M. Sawamoto, Macromolecules, 33, 5836 (2000).
92. K. Sato, M. Kamigaito, and M. Sawamoto, Macromolecules, 33, 5405 (2000).
93. K. Sato, M. Kamigaito, and M. Sawamoto, Macromolecules, 34, 396 (2001).
94. "Ionic Liquids in Synthesis", P. Wasserscheid and T. Welton eds., Wiley-VCH, Weinheim (2003).
95. Japanese source, 52, (2003), p. 167.
96. M. Ouchi, M. Kamigaito, M. Sawamoto, Macromolecules, 32, 6407 (1999).
97. D. C. Pepper, "Friedel-Crafts and Related Reactions", G. A. Olah ed., John Wiley & Sons Inc., New York (1964), Chapter 30.
98. G. D. Yadav and S. Sengupta, Org. Process. Res. Dev., 6, 256 (2002).
99. M. H. Sarvari and H. Sharghi, J. Org. Chem., 69, 6953 (2004).
100. M. L. Kantam, K. V. S. Rranganath, M. Sateesh, K. B. S. Kumar, and B. M. Choudary, J. Mol. Catal. A: Chem., 225, 15 (2005).
101. J. Izumi and T. Mukaiyama, Chem. Lett., 1996, 739.
102. I. Hachiya, M. Moriwaki, and S. Kobayashi, Bull. Chem. Soc. Jpn., 68, 2053 (1995).
103. S. Kobayashi and S. Iwamoto, Tetrahedron Lett., 39, 4697 (1998).
104. T. Tsuchimoto, K. Tobita, T. Hiyama, and S. Fukuzawa, J. Org. Chem., 62, 6997 (1997).
105. M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, and K. Ishii, J. Org. Chem., 68, 9340 (2003).
106. K. Mertins, I. Iovel, J. Kischel, A. Zapf, and M. Beller, Angew. Chem. Int. Ed., 44, 238 (2005).
107. M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, J. Org. Chem., 67, 5386 (2002).
108. M. Bandini, A. Melloni, S. Tommasi, and A. Umani-Ronchi, Synlett, 2005, 1199.
109. A. Fürstner, D. Voigtländer, W. Schrader, D. Giebel, and M. T. Reetz, Org. Lett., 3, 417 (2001).
110. S. Gmouh, H. Yang, and M. Vaultier, Org. Lett., 5, 2219 (2003).
111. R. G. Pearson, J. Am. Chem. Soc., 85, 3533 (1963).
112. T.-L. Ho, Chem. Rev., 75, 1 (1975).
113. Y. Zhang, Inorg. Chem., 21, 3889 (1982).
114. G. A. Olah, S. Kobayashi, and M. Tashiro, J. Am. Chem. Soc., 94, 7448 (1972).
115. S. Kobayashi, S. Nagayama, and T. Busujima, J. Am. Chem. Soc., 120, 8287 (1998).
116. S. Kobayashi, T. Busujima, and S. Nagayama, Chem. Eur. J., 6, 3491 (2000).
117. T. Yoshida, T. Tsujino, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 468 (2005).
118. N. Aoyama, K. Manabe, and S. Kobayashi, Chem. Lett., 33, 312 (2004).
119. C. Bolm, J. Legros, J. L. Paih, and L Zani, Chem. Rev., 104, 6217 (2004).
120. M. Baaz and V. Gutmann, "Friedel-Crafts and Related Reactions", G. A. Olah ed., John Wiley & Sons Inc., New York (1964), Vol. I, pp. 382-383.
121. Japanese source, 54, (2005), p. 216.
122. A. Kanazawa, T. Yoshida, S. Kanaoka, and S. Aoshima, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 46 (2), 908 (2005).
123. N. Chatani, M. Oshita, M. Tobisu, Y. Ishii, and S. Murai, J. Am. Chem. Soc., 125, 7812 (2003).
124. Japanese source, 54, (2005), p. 2499.
125. S. Aoshima, Y. Shachi, and E. Kobayashi, Makromol. Chem., 192, 1759 (1991).
126. T. Yoshida, A. Kanazawa, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 4288 (2005).
127. B. J. Bauer, F. J. Fetters, Rubber Chem. Technol., 51, 406 (1978).
128. S. Bywater, Adv. Polym. Sci., 30, 90 (1979).
129. M. Sawamoto, S. Kanaoka, and T. Higashimura, "Hyper-Structured Molecules I: Chemistry, Physics, and Applications", H. Sasabe ed., Gordon and Breach Science Publishers, Amsterdam (1999), pp. 43-61.
130. Japanese source, 50, 10 (2001).
131. S. Kanaoka, M. Sawamoto, and T. Higashimura, Macromolecules, 25, 6414 (1992).
132. S. Kanaoka, M. Sawamoto, and T. Higashimura, Makromol. Chem., 194, 2035 (1993).
133. S. Kanaoka, S. Nakata, H. Yamaoka, Macromolecules, 35, 4564 (2002).
134. Japanese source, 52, (2003 9), p. 1328.
135. T. Shibata, S. Kanaoka, and S. Aoshima, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 45(2), 634 (2004).
136. Japanese source, 54, (2005), p. 2790.
137. Japanese source, 4, 44 (2004).
138. S. Aoshima, M. Ikeda, K. Nakayama, E. Kobayashi, H. Ohgi, and T. Sato, Polym. J., 33, 610 (2001).
139. J. P. Kennedy, J. Polym. Sci., Part A: Polym. Chem., 43, 2951 (2005).
140. J. E. Puskas and G. Kaszas, Rubber Chem. Technol., 69, 462 (1996).
141. Japanese source, 52, 465 (1999).
142. Japanese source, 21, (2004) p. 41.
143. J. E. Puskas and Y. Chen, Biomacromolecules, 5, 1142 (2004).
144. J. E. Puskas, Y. Chen, Y. Dahman, and D. Padavan, J. Polym. Sci., Part A: Polym. Chem., 42, 3091 (2004).
145. L. Sipos, A. Som, and R. Faust, Biomacromolecules, 6, 2570 (2005).
146. Y. Zhou, R. Faust, R. Richard, and M. Schwarz, Macromolecules, 38, 8183 (2005).
147. I. S. Isayeva, B. T. Kashibhatla, K. L. Rosenthal, and J. P. Kennedy, Biomaterials, 24, 3483 (2003).
148. G. Langstein, O. Nuyken, W. Obrecht, J. E. Puskas, and K. Weiss, U. S. Patent 6156859 (2000).
149. J. E. Puskas, Y. Chen, P. Antony, Y. Kwon, M. Kovar, R. R. Harbottle, K. D. Jong, P. R. Norton, P. Cadieux, J. Burton, G. Reid, D. Beiko, J. D. Watterson, and J. Denstedt, Polym. Adv. Technol., 14, 763 (2003).
150. S. Aoshima, H. Oda, and E. Kobayashi, J. Polym. Sci., Part A: Polym. Chem., 30, 2407 (1992).
151. Japanese source, 49, 933 (1992).
152. Japanese source, 40, 446 (2004).
153. S. Aoshima, S. Sugihara, M. Shibayama, and S. Kanaoka, Macromol. Symp., 215, 151 (2004).
154. S. Aoshima, "Macromolecular Nanostructured Materials", N. Ueyama, A. Harada eds., Kodansha, Springer, Berlin (2004), pp. 138-154.
155. S. Sugihara, K. Hashimoto, Y. Matsumoto, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 41, 3300 (2003).
156. Japanese source, 54, (2005) p. 175.
157. S. Sugihara, S. Kanaoka, and S. Aoshima, Macromolecules, 37, 1711 (2004).
158. Japanese source, 52, (2003) p. 442.
159. Japanese source, 52, (2003) p. 1239.
160. T. Yoshida, K. Seno, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 1155 (2005).
161. T. Yoshida, S. Kanaoka, H. Watanabe, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 2712 (2005).
162. A. Date, S. Kanaoka, T. Kato, and S. Aoshima, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 46(2), 977 (2005).
163. Japanese source, 53, (2003) p. 770.
164. T. Tsujino, S. Kanaoka, and S. Aoshima, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 46(2), 865 (2005).
165. T. Yoshida, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 5138 (2005).
166. T. Yoshida, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 4292 (2005).
167. T. Yoshida, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 5337 (2005).
168. Japanese source, 52, (2003) p. 3242.
169. Japanese source, 52, (2003), p. 1325.
170. S. Sugihara, S. Matsuzono, H. Sakai, M. Abe, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 39, 3190 (2001).
171. C. Fuse, S. Okabe, M. Shibayama, S. Sugihara, and S. Aoshima, Macromolecules, 37, 7791 (2004).
172. S. Aoshima and K. Hashimoto, J. Polym. Sci., Part A: Polym. Chem., 39, 746 (2001).
173. S. Sugihara, K. Hashimoto, S. Okabe, M. Shibayama, S. Kanaoka, and S. Aoshima, Macromolecules, 37, 336 (2004).
174. S. Okabe, S. Sugihara, S. Aoshima, and M. Shibayama, Macromolecules, 35, 8139 (2002).
175. S. Okabe, S. Sugihara, S. Aoshima, and M. Shibayama, Macromolecules, 36, 4099 (2003).
176. S. Aoshima and S. Sugihara, J. Polym. Sci., Part A: Polym. Chem., 38, 3962 (2000).
177. S. Sugihara, S. Kanaoka, and S. Aoshima, Macromolecules, 38, 1919 (2005).
178. S. Sugihara, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 42, 2601 (2004).
179. Japanese source, 62, 87 (2005).
180. T. Yoshida, M. Doi, S. Kanaoka, and S. Aoshima, J. Polym. Sci., Part A: Polym. Chem., 43, 5704 (2005).
181. Japanese source, 62, 92 (2005).
182. S. Okabe, K. Seno, S. Kanaoka, S. Aoshima, and M. Shibayama, Macromolecules, in press.
183. K. Kono, T. Murakami, T. Yoshida, Y. Haba, S. Kanaoka, T. Takagishi, and S. Aoshima, Bioconjugate Chem., 16, 1367 (2005).
184. Japanese source, 54, (2005) p. 5169.