Abstract
This review summarizes the data on catalytic addition polymerization of norbornene and its derivatives catalyzed by various transition-metal complexes. Studies on the copolymerization of norbornene with α-olefins are considered. The survey mostly covers papers published in 2000–2006.
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K. L. Makovetskii, Polymer Science, Ser. B 41, 269 (1999) [Vysokomol. Soedin., Ser. B 41, 1525 (1999)].
C. Janiak and P. G. Lassahn, J. Mol. Catal., Chem. 166, 193 (2001).
B. L. Goodall, in Late Transition Metal Polymerization Catalysis, Ed. by B. Rieger, L. S. Baugh, S. Kasker, and S. Striegler (Wiley, Weinheim, 2003), p. 101.
P. G. Lassahn, V. Lozan, and C. Janiak, J. Chem. Soc., Dalton Trans., No. 5, 927 (2003).
A. D. Hennis, J. D. Polley, G. S. Long, et al., Organometallics 20, 2802 (2001).
J. Lipian, R. A. Mimna, J. C. Fordran, et al., Macromolecules 35, 8969 (2002).
P. G. Lassahn, V. Lozan, B. Wu, et al., J. Chem. Soc., Dalton Trans., No. 23, 4437 (2003).
H. Liang, J. Liu, X. Li, and Y. Li, Polyhedron 23, 1619 (2004).
D. M. Shin, S. U. Son, B. K. Hong, et al., J. Mol. Catal., Chem. 210, 35 (2004).
B. Berchtold, V. Lozan, P.-G. Lassahn, and C. Janiak, J. Polym. Sci., Part A: Polym. Chem. 40, 3604 (2002).
J. K. Funk, C. E. Andes, and A. Sen, Organometallics 23, 1680 (2004).
B. S. Heinz, F. P. Alt, and W. Heitz, Macromol. Chem., Rapid Commun. 19, 251 (1998).
B.-G. Shin, M.-S. Jang, D. Y. Yoon, and W. Heitz, Macromol. Rapid Commun. 25, 728 (2004).
A. S. Abu-Surrah, K. Lappalainen, M. Kettunen, et al., Macromol. Chem. Phys. 202, 599 (2001).
G. Myagmarsuren, K.-S. Lee, O.-Y. Jeong, and S.-K. Ihm, Polymer 45, 3227 (2004).
N. G. Gaylord, A. B. Desphande, B. M. Mandel, and M. Martan, J. Macromol. Sci., Chem. 11, 1053 (1977).
G. Myagmarsuren, K.-S. Lee, O.-Y. Jeong, and S.-K. Ihm, Polymer 46, 3585 (2005).
G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 296, 21 (2005).
G. Myagmarsuren, J.-I. Park, and S.-K. Ihm, Polymer 47, 8474 (2006).
M. Arndt and M. Gossmann, Polym. Bull. (Berlin) 41, 433 (1998).
E. Sh. Finkel’shtein, K. L. Makovetskii, M. L. Gringol’ts, et al., Dokl. Akad. Nauk 407, 496 (2006).
E. Sh. Finkelshtein, K. L. Makovetskii, M. I. Gringolts, et al., J. Mol. Catal., Chem. 257, 9 (2006).
E. Sh. Finkelshtein, K. L. Makovetskii, M. I. Gringolts, et al., Macromolecules 39, 7022 (2006).
C.-T. Zhao, M. R. Ribeiro, M. F. Portela, et al., Eur. Polym. J. 37, 45 (2001).
C.-T. Zhao, M. R. Ribeiro, M. N. De Pinho, et al., Polymer 42, 2455 (2001).
C.-F. Huang, S.-K. Wang, S.-W. Kuo, et al., J. Appl. Polym. Sci. 92, 1824 (2004).
C.-T. Zhao, M. R. Ribeiro, and M. F. Portela, J. Mol. Catal., Chem. 185, 81 (2002).
K. L. Makovetskii, L. I. Gorbacheva, T. G. Golenko, et al., in Proceedings of Russia Conference “Metallocomplex Catalysis of Polymerization Processes”, Chernogolovka, 1998, p. 33.
Y.-R. Li, Y.-S. Li, and B.-C. Shi, Chin. J. Appl. Chem. 19, 617 (2002).
H. Yang, W. H. Sun, F. Chang, and Y. Li, Appl. Catal., A 252, 261 (2003).
T. Hu, Y.-G. Li, Y.-S. Li, and N.-H. Hu, J. Mol. Catal., Chem. 253, 155 (2006).
X.-F. Li and Y.-S. Li, J. Polym. Sci., Part A: Polym. Chem. 40, 2680 (2002).
W.-H. Sun, H. Yang, Z. Li, and Y. Li, Organometallics 22, 3678 (2003).
W.-H. Wang and G.-X. Jin, Inorg. Chem. Commun. 8, 109 (2005).
F. Chang, D. Zhang, G. Xu, et al., J. Organomet. Chem. 689, 936 (2004).
Y.-Z. Zhu, J.-Y. Liu, Y.-S. Li, and Y.-J. Tong, J. Organomet. Chem. 689, 1295 (2004).
D. Zhang, G.-X. Jin, L.-H. Weng, and F. Wang, Organometallics 23, 3270 (2004).
H. Gao, W. Guo, F. Bao, et al., Organometallics 23, 6273 (2004).
X. Mi, Z. Ma, N. Cui, et al., J. Appl. Polym. Sci. 88, 3273 (2003).
X. Mi, Z. Ma, L. Wang, et al., Macromol. Chem. Phys. 204, 868 (2003).
Y.-S. Li, Y.-R. Li, and X.-F. Li, J. Organomet. Chem. 667, 185 (2003).
A. O. Patil, S. Zushma, R. T. Stibrany, et al., J. Polym. Sci., Part A: Polym. Chem. 41, 2095 (2003).
E. Nelkenbaum, M. Kapon, and M. S. Eisen, Organometallics 24, 2645 (2005).
L. Y. Wang, Y. F. Li, F. M. Zhu, and Q. Wu, Eur. Polym. J. 42, 322 (2006).
W.-H. Wang, S. Liu, and G.-X. Jin, Organometallics 23, 6002 (2004).
M. C. Sacchi, M. Sonzogni, S. Losio, et al., Macromol. Chem. Phys. 202, 2052 (2001).
J. Hou, W.-H. Sun, D. Zhang, et al., J. Mol. Catal., Chem. 231, 221 (2005).
G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 255, 203 (2003).
G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 275, 271 (2004).
Y. Jang, H.-K. Sung, S. Lee, and C. Bae, Polymer 46, 11301 (2005).
Y. Jang, H.-K. Sung, and H. Kwag, Eur. Polym. J. 42, 1250 (2006).
B. Y. Lee, Y. H. Kim, H. J. Shin, and C. H. Lee, Organometallics 21, 3481 (2002).
D. A. Barnes, G. M. Benedict, B. L. Goodall, et al., Macromolecules 36, 2623 (2003).
B. L. Goodall, D. A. Barnes, G. M. Benedict, et al., Proc. Am. Chem. Soc., Div. Polym. Mater. Sci. Eng. 75, 56 (1997).
Sh. Kaita, K. Matsushita, M. Tobita, et al., Macromol. Chem., Rapid Commun. 27, 1752 (2006).
W. L. Truett, D. R. Johnson, J. M. Robinson, and B. A. Montague, J. Am. Chem. Soc. 82, 2337 (1960).
G. Sartori, F. Ciampelli, and W. Gameli, Chim. Ind. (Milan) 45, 1478 (1963).
A. L. McKnight and R. M. Waymouth, Macromolecules 32, 2816 (1999).
R. Manivannan, G. Sundararajan, and W. Kaminsky, J. Mol. Catal., Chem. 160, 85 (2000).
Y.-Y. Lu, Q. Wu, and Z.-J. Lu, Chem. J. Chin. Univ. 22, 160 (2001).
Q. Wu and Y. Lu, J. Polym. Sci., Part A: Polym. Chem. 40, 1421 (2002).
T. Hasan, K. Nishii, T. Shiono, and T. Ikeda, Macromolecules 35, 8933 (2002).
T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 37, 7432 (2004).
U. Peucker and W. Heitz, Macromol. Chem. Phys. 202, 1289 (2001).
T. J. Woodman, Y. Sarazin, S. Garrat, et al., J. Mol. Catal., Chem. 235, 88 (2005).
F. Pelaskini, F. Peruch, P. J. Lutz, et al., Macromol. Symp. 213, 265 (2004).
Y. Sato, Y. Nakayama, and H. Yasuda, J. Organomet. Chem. 689, 744 (2004).
X.-F. Hou, Y.-Q. Cheng, X. Wang, and G.-X. Jin, J. Organomet. Chem. 690, 1855 (2005).
Zh. Hou, Y. Luo, and X. Li, J. Organomet. Chem. 691, 3114 (2006).
C. Carlini, S. Giaiacopi, F. Marchetti, et al., Organometallics 25, 3692 (2006).
F. Bao, R. Ma, and Y. Jiao, Appl. Organomet. Chem. 20, 368 (2006).
W. Kaminsky, M. Arndt, and A. Bark, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 32, 467 (1991).
I. Tritto, L. Boggioni, and D. R. Ferro, Coord. Chem. Rev. 250, 212 (2006).
J. C. Jansen, R. Mendichi, P. Locatelli, and I. Tritto, Macromol. Chem., Rapid Commun. 22, 1394 (2001).
S. Y. Park, K. Y. Choi, K. H. Song, and B. G. Jeong, Macromolecules 36, 4216 (2003).
I. Tritto, L. Boggioni, J. C. Jansen, et al., Macromolecules 35, 616 (2002).
M.-J. Young, W.-S. Chang, and C.-C. Ma, Eur. Polym. J. 39, 165 (2003).
W. Kaminsky, O. Sperber, and R. Werner, Coord. Chem. Rev. 250, 110 (2006).
R. A. Wendt and G. Fink, J. Mol. Catal., Chem. 203, 101 (2003).
H. Lee, S.-D. Hong, Y.-W. Park, et al., J. Organomet. Chem. 689, 3402 (2004).
R. A. Wendt and G. Fink, Macromol. Chem. Phys. 201, 1365 (2000).
R. A. Wendt and G. Fink, Macromol. Chem. Phys. 203, 1071 (2002).
R. A. Wendt, K. Angermund, V. Jensen, et al., Macromol. Chem. Phys. 205, 308 (2004).
W. Kaminsky, A. Bark, and I. Daeke, in Proceedings of International Symposium on Recent Development in Olefin Polymerization, Catalysis (Elsevier, Amsterdam, 1990), p. 425.
J. P. Koinzer, U. Langbein, and E. Taeger, DE Patent No. 109 224 (1973).
E. Brauer, H. Wiegleb, and M. Helmstedt, Polym. Bull. (Berlin) 15, 551 (1986).
E. Brauer, C. Wild, and H. Wiegleb, Polym. Bull. (Berlin) 18, 73 (1987).
D. Ruchatz and G. Fink, Macromolecules 31, 4674 (1998).
D. Ruchatz and G. Fink, Macromolecules 31, 4681 (1998).
B. A. Harrington and D. J. Crowther, J. Mol. Catal., Chem. 128, 79 (1998).
N. Ekizoglou, K. Thorshaug, M. Cerrada, et al., J. Appl. Polym. Sci. 89, 3358 (2003).
K. Thorshaug, R. Mendichi, L. Boggioni, et al., Macromolecules 35, 2903 (2002).
F.-D. Tran and W. Kaminsky, J. Zhejiang Univ. Sci. 4, 121 (2003).
T. Hasan, T. Shiono, and T. Ikeda, Macromol. Symp. 213, 122 (2004).
T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 37, 8503 (2004).
Y. Yoshida, J. Saito, M. Mitani, et al., Chem. Commun., No. 12, 1298 (2002).
Y. Yoshida, J. Mori, S. Ishii, et al., J. Am. Chem. Soc. 126, 12023 (2004).
Y. Yoshida, S. Matsui, and T. Fujita, J. Organomet. Chem. 690, 4382 (2005).
W.-Q. Hu, X.-L. Sun, C. Wang, et al., Organometallics 23, 1684 (2004).
L.-M. Tang, T. Hu, Y.-J. Bo, et al., J. Organomet. Chem. 690, 3125 (2005).
K. L. Makovetsky, E. Sh. Finkelshtein, V. I. Bykov, et al., WO Patent No. 98 563 837 A1 (1998); US Patent No. 5 929 181 (1999).
K. L. Makovetskii, V. I. Bykov, A. Kh. Bagdasar’yan, et al., Polymer Science, Ser. A 47, 77 (2005) [Vysokomol. Soedin., Ser. A 47, 197 (2005)].
K. L. Makovetskii, V. I. Bykov, and E. Sh. Finkel’shtein, Kinet. Katal. 47, 243 (2006).
G. Benedikt, E. Elce, B. L. Goodall, et al., Macromolecules 35, 8978 (2002).
T. R. Younkin, E. F. Connor, J. I. Henderson, et al., Science (Washington, D. C.) 287, 460 (2000).
E. F. Connor, T. R. Younkin, J. I. Henderson, et al., J. Polym. Sci., Part A: Polym. Chem. 40, 2842 (2002).
S. Sujith, D. J. Joe, S. J. Na, et al., Macromolecules 38, 10027 (2005).
S. J. Diamanti, P. Ghosh, F. Shimizu, and G. C. Bazan, Macromolecules 36, 9731 (2003).
S. J. Diamanti, V. Khanna, A. Hotta, et al., Macromolecules 36, 3270 (2003).
F. M. Bauers and S. Mecking, Macromolecules 34, 1165 (2001).
B. L. Goodall and L. H. McIntosh III, US Patent No. 6 265 506 B1 (2001).
J. Kiesewetter and W. Kaminsky, Chem.-Eur. J. 9, 1750 (2003).
J. Kiesewetter, B. Arikan, and W. Kaminsky, Polymer 47, 3302 (2006).
K. M. Skupov, P. R. Marella, J. L. Hobbs, et al., Macromolecules 39, 4279 (2006).
U. Peucker and W. Heitz, Macromol. Chem. Phys. 202, 1289 (2001).
X. Li, J. Baldamus, and Z. Hou, Angew. Chem., Int. Ed. Engl. 44, 962 (2005).
W. Wang and K. Nomura, Macromolecules 38, 5905 (2005).
C. Lorber, F. Wolff, R. Choukroun, and L. Vendier, Eur. J. Inorg. Chem, No. 14, 2850 (2005).
J. Yamada, M. Fujiki, and K. Nomura, Organometallics 24, 2248 (2005).
O. Henschke, F. Koeller, and M. Arnold, Macromol. Rapid. Commun. 18, 617 (1997).
T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 38, 2031 (2005).
Z. Cai, Y. Nakayama, and T. Shiono, Macromolecules 39, 1071 (2006).
H. Y. Jung, S.-D. Hong, M. W. Jung, et al., Polyhedron 24, 1269 (2005).
E. Aitola, T. Repo, C. Bergstroem, and Leskelae, J. Appl. Polym. Sci. 84, 2743 (2002).
H. Gao, Y. Chen, F. Zhu, and Q. Wu, J. Polym. Sci., Part A: Polym. Chem. 44, 5237 (2006).
H. Suzuki, Sh. Matsumura, Y. Satoh, et al., React. Funct. Polym. 58, 77 (2004).
H. Suzuki, Sh. Matsumura, Y. Satoh, et al., React. Funct. Polym. 59, 253 (2004).
L. Wang, Y. Li, F. Zhu, and Q. Wu, Polym. Bull. (Berlin) 57, 73 (2006).
B. L. Goodall and L. H. McIntosh III, US Patent No. 6 303 724 B1 (2001).
H. V. Tran, R. J. Hung, T. Chiba, et al., Macromolecules 35, 6539 (2002).
D. P. Sanders, E. F. Connor, R. H. Grubbs, et al., Macromolecules 36, 1534 (2003).
B. C. Trinque, C. R. Chambers, B. P. Osborn, et al., J. Fluorine Chem. 122, 17 (2003).
A. E. Feiring, M. K. Crawford, W. B. Farnham, et al., Macromolecules 39, 3252 (2006).
A. E. Feiring, M. K. Crawford, W. B. Farnham, et al., J. Fluorine Chem. 122, 11 (2003).
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Original Russian Text © K.L. Makovetskii, 2008, published in Vysokomolekulyarnye Soedineniya, Ser. C, 2008, Vol. 50, No. 7, pp. 1322–1343.
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Makovetskii, K.L. Catalytic addition polymerization of norbornene and its derivatives and copolymerization of norbornene with olefins. Polym. Sci. Ser. C 50, 22–38 (2008). https://doi.org/10.1134/S1811238208010025
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DOI: https://doi.org/10.1134/S1811238208010025