Skip to main content
Log in

Catalytic addition polymerization of norbornene and its derivatives and copolymerization of norbornene with olefins

  • Published:
Polymer Science Series C Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. K. L. Makovetskii, Polymer Science, Ser. B 41, 269 (1999) [Vysokomol. Soedin., Ser. B 41, 1525 (1999)].

    Google Scholar 

  2. C. Janiak and P. G. Lassahn, J. Mol. Catal., Chem. 166, 193 (2001).

    Article  CAS  Google Scholar 

  3. 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.

    Chapter  Google Scholar 

  4. P. G. Lassahn, V. Lozan, and C. Janiak, J. Chem. Soc., Dalton Trans., No. 5, 927 (2003).

  5. A. D. Hennis, J. D. Polley, G. S. Long, et al., Organometallics 20, 2802 (2001).

    Article  CAS  Google Scholar 

  6. J. Lipian, R. A. Mimna, J. C. Fordran, et al., Macromolecules 35, 8969 (2002).

    Article  CAS  Google Scholar 

  7. P. G. Lassahn, V. Lozan, B. Wu, et al., J. Chem. Soc., Dalton Trans., No. 23, 4437 (2003).

  8. H. Liang, J. Liu, X. Li, and Y. Li, Polyhedron 23, 1619 (2004).

    Article  CAS  Google Scholar 

  9. D. M. Shin, S. U. Son, B. K. Hong, et al., J. Mol. Catal., Chem. 210, 35 (2004).

    Article  CAS  Google Scholar 

  10. B. Berchtold, V. Lozan, P.-G. Lassahn, and C. Janiak, J. Polym. Sci., Part A: Polym. Chem. 40, 3604 (2002).

    Article  CAS  Google Scholar 

  11. J. K. Funk, C. E. Andes, and A. Sen, Organometallics 23, 1680 (2004).

    Article  CAS  Google Scholar 

  12. B. S. Heinz, F. P. Alt, and W. Heitz, Macromol. Chem., Rapid Commun. 19, 251 (1998).

    CAS  Google Scholar 

  13. B.-G. Shin, M.-S. Jang, D. Y. Yoon, and W. Heitz, Macromol. Rapid Commun. 25, 728 (2004).

    Article  CAS  Google Scholar 

  14. A. S. Abu-Surrah, K. Lappalainen, M. Kettunen, et al., Macromol. Chem. Phys. 202, 599 (2001).

    Article  CAS  Google Scholar 

  15. G. Myagmarsuren, K.-S. Lee, O.-Y. Jeong, and S.-K. Ihm, Polymer 45, 3227 (2004).

    Article  CAS  Google Scholar 

  16. N. G. Gaylord, A. B. Desphande, B. M. Mandel, and M. Martan, J. Macromol. Sci., Chem. 11, 1053 (1977).

    Article  Google Scholar 

  17. G. Myagmarsuren, K.-S. Lee, O.-Y. Jeong, and S.-K. Ihm, Polymer 46, 3585 (2005).

    Article  CAS  Google Scholar 

  18. G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 296, 21 (2005).

    Article  CAS  Google Scholar 

  19. G. Myagmarsuren, J.-I. Park, and S.-K. Ihm, Polymer 47, 8474 (2006).

    Article  CAS  Google Scholar 

  20. M. Arndt and M. Gossmann, Polym. Bull. (Berlin) 41, 433 (1998).

    Article  CAS  Google Scholar 

  21. E. Sh. Finkel’shtein, K. L. Makovetskii, M. L. Gringol’ts, et al., Dokl. Akad. Nauk 407, 496 (2006).

    Google Scholar 

  22. E. Sh. Finkelshtein, K. L. Makovetskii, M. I. Gringolts, et al., J. Mol. Catal., Chem. 257, 9 (2006).

    Article  CAS  Google Scholar 

  23. E. Sh. Finkelshtein, K. L. Makovetskii, M. I. Gringolts, et al., Macromolecules 39, 7022 (2006).

    Article  CAS  Google Scholar 

  24. C.-T. Zhao, M. R. Ribeiro, M. F. Portela, et al., Eur. Polym. J. 37, 45 (2001).

    Article  CAS  Google Scholar 

  25. C.-T. Zhao, M. R. Ribeiro, M. N. De Pinho, et al., Polymer 42, 2455 (2001).

    Article  CAS  Google Scholar 

  26. C.-F. Huang, S.-K. Wang, S.-W. Kuo, et al., J. Appl. Polym. Sci. 92, 1824 (2004).

    Article  CAS  Google Scholar 

  27. C.-T. Zhao, M. R. Ribeiro, and M. F. Portela, J. Mol. Catal., Chem. 185, 81 (2002).

    Article  CAS  Google Scholar 

  28. 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.

  29. Y.-R. Li, Y.-S. Li, and B.-C. Shi, Chin. J. Appl. Chem. 19, 617 (2002).

    CAS  Google Scholar 

  30. H. Yang, W. H. Sun, F. Chang, and Y. Li, Appl. Catal., A 252, 261 (2003).

    Article  CAS  Google Scholar 

  31. T. Hu, Y.-G. Li, Y.-S. Li, and N.-H. Hu, J. Mol. Catal., Chem. 253, 155 (2006).

    Article  CAS  Google Scholar 

  32. X.-F. Li and Y.-S. Li, J. Polym. Sci., Part A: Polym. Chem. 40, 2680 (2002).

    Article  CAS  Google Scholar 

  33. W.-H. Sun, H. Yang, Z. Li, and Y. Li, Organometallics 22, 3678 (2003).

    Article  CAS  Google Scholar 

  34. W.-H. Wang and G.-X. Jin, Inorg. Chem. Commun. 8, 109 (2005).

    Article  CAS  Google Scholar 

  35. F. Chang, D. Zhang, G. Xu, et al., J. Organomet. Chem. 689, 936 (2004).

    Article  CAS  Google Scholar 

  36. Y.-Z. Zhu, J.-Y. Liu, Y.-S. Li, and Y.-J. Tong, J. Organomet. Chem. 689, 1295 (2004).

    Article  CAS  Google Scholar 

  37. D. Zhang, G.-X. Jin, L.-H. Weng, and F. Wang, Organometallics 23, 3270 (2004).

    Article  CAS  Google Scholar 

  38. H. Gao, W. Guo, F. Bao, et al., Organometallics 23, 6273 (2004).

    Article  CAS  Google Scholar 

  39. X. Mi, Z. Ma, N. Cui, et al., J. Appl. Polym. Sci. 88, 3273 (2003).

    Article  CAS  Google Scholar 

  40. X. Mi, Z. Ma, L. Wang, et al., Macromol. Chem. Phys. 204, 868 (2003).

    Article  CAS  Google Scholar 

  41. Y.-S. Li, Y.-R. Li, and X.-F. Li, J. Organomet. Chem. 667, 185 (2003).

    Article  CAS  Google Scholar 

  42. A. O. Patil, S. Zushma, R. T. Stibrany, et al., J. Polym. Sci., Part A: Polym. Chem. 41, 2095 (2003).

    Article  CAS  Google Scholar 

  43. E. Nelkenbaum, M. Kapon, and M. S. Eisen, Organometallics 24, 2645 (2005).

    Article  CAS  Google Scholar 

  44. L. Y. Wang, Y. F. Li, F. M. Zhu, and Q. Wu, Eur. Polym. J. 42, 322 (2006).

    Article  CAS  Google Scholar 

  45. W.-H. Wang, S. Liu, and G.-X. Jin, Organometallics 23, 6002 (2004).

    Article  CAS  Google Scholar 

  46. M. C. Sacchi, M. Sonzogni, S. Losio, et al., Macromol. Chem. Phys. 202, 2052 (2001).

    Article  CAS  Google Scholar 

  47. J. Hou, W.-H. Sun, D. Zhang, et al., J. Mol. Catal., Chem. 231, 221 (2005).

    Article  CAS  Google Scholar 

  48. G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 255, 203 (2003).

    Article  CAS  Google Scholar 

  49. G. Myagmarsuren, O.-Y. Jeong, and S.-K. Ihm, Appl. Catal., A 275, 271 (2004).

    Article  CAS  Google Scholar 

  50. Y. Jang, H.-K. Sung, S. Lee, and C. Bae, Polymer 46, 11301 (2005).

  51. Y. Jang, H.-K. Sung, and H. Kwag, Eur. Polym. J. 42, 1250 (2006).

    Article  CAS  Google Scholar 

  52. B. Y. Lee, Y. H. Kim, H. J. Shin, and C. H. Lee, Organometallics 21, 3481 (2002).

    Article  CAS  Google Scholar 

  53. D. A. Barnes, G. M. Benedict, B. L. Goodall, et al., Macromolecules 36, 2623 (2003).

    Article  CAS  Google Scholar 

  54. B. L. Goodall, D. A. Barnes, G. M. Benedict, et al., Proc. Am. Chem. Soc., Div. Polym. Mater. Sci. Eng. 75, 56 (1997).

    Google Scholar 

  55. Sh. Kaita, K. Matsushita, M. Tobita, et al., Macromol. Chem., Rapid Commun. 27, 1752 (2006).

    Article  CAS  Google Scholar 

  56. W. L. Truett, D. R. Johnson, J. M. Robinson, and B. A. Montague, J. Am. Chem. Soc. 82, 2337 (1960).

    Article  CAS  Google Scholar 

  57. G. Sartori, F. Ciampelli, and W. Gameli, Chim. Ind. (Milan) 45, 1478 (1963).

    CAS  Google Scholar 

  58. A. L. McKnight and R. M. Waymouth, Macromolecules 32, 2816 (1999).

    Article  CAS  Google Scholar 

  59. R. Manivannan, G. Sundararajan, and W. Kaminsky, J. Mol. Catal., Chem. 160, 85 (2000).

    Article  CAS  Google Scholar 

  60. Y.-Y. Lu, Q. Wu, and Z.-J. Lu, Chem. J. Chin. Univ. 22, 160 (2001).

    CAS  Google Scholar 

  61. Q. Wu and Y. Lu, J. Polym. Sci., Part A: Polym. Chem. 40, 1421 (2002).

    Article  CAS  Google Scholar 

  62. T. Hasan, K. Nishii, T. Shiono, and T. Ikeda, Macromolecules 35, 8933 (2002).

    Article  CAS  Google Scholar 

  63. T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 37, 7432 (2004).

    Article  CAS  Google Scholar 

  64. U. Peucker and W. Heitz, Macromol. Chem. Phys. 202, 1289 (2001).

    Article  CAS  Google Scholar 

  65. T. J. Woodman, Y. Sarazin, S. Garrat, et al., J. Mol. Catal., Chem. 235, 88 (2005).

    Article  CAS  Google Scholar 

  66. F. Pelaskini, F. Peruch, P. J. Lutz, et al., Macromol. Symp. 213, 265 (2004).

    Article  CAS  Google Scholar 

  67. Y. Sato, Y. Nakayama, and H. Yasuda, J. Organomet. Chem. 689, 744 (2004).

    Article  CAS  Google Scholar 

  68. X.-F. Hou, Y.-Q. Cheng, X. Wang, and G.-X. Jin, J. Organomet. Chem. 690, 1855 (2005).

    Article  CAS  Google Scholar 

  69. Zh. Hou, Y. Luo, and X. Li, J. Organomet. Chem. 691, 3114 (2006).

    Article  CAS  Google Scholar 

  70. C. Carlini, S. Giaiacopi, F. Marchetti, et al., Organometallics 25, 3692 (2006).

    Article  CAS  Google Scholar 

  71. F. Bao, R. Ma, and Y. Jiao, Appl. Organomet. Chem. 20, 368 (2006).

    Article  CAS  Google Scholar 

  72. W. Kaminsky, M. Arndt, and A. Bark, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 32, 467 (1991).

    CAS  Google Scholar 

  73. I. Tritto, L. Boggioni, and D. R. Ferro, Coord. Chem. Rev. 250, 212 (2006).

    Article  CAS  Google Scholar 

  74. J. C. Jansen, R. Mendichi, P. Locatelli, and I. Tritto, Macromol. Chem., Rapid Commun. 22, 1394 (2001).

    Article  CAS  Google Scholar 

  75. S. Y. Park, K. Y. Choi, K. H. Song, and B. G. Jeong, Macromolecules 36, 4216 (2003).

    Article  CAS  Google Scholar 

  76. I. Tritto, L. Boggioni, J. C. Jansen, et al., Macromolecules 35, 616 (2002).

    Article  CAS  Google Scholar 

  77. M.-J. Young, W.-S. Chang, and C.-C. Ma, Eur. Polym. J. 39, 165 (2003).

    Article  CAS  Google Scholar 

  78. W. Kaminsky, O. Sperber, and R. Werner, Coord. Chem. Rev. 250, 110 (2006).

    Article  CAS  Google Scholar 

  79. R. A. Wendt and G. Fink, J. Mol. Catal., Chem. 203, 101 (2003).

    Article  CAS  Google Scholar 

  80. H. Lee, S.-D. Hong, Y.-W. Park, et al., J. Organomet. Chem. 689, 3402 (2004).

    Article  CAS  Google Scholar 

  81. R. A. Wendt and G. Fink, Macromol. Chem. Phys. 201, 1365 (2000).

    Article  CAS  Google Scholar 

  82. R. A. Wendt and G. Fink, Macromol. Chem. Phys. 203, 1071 (2002).

    Article  CAS  Google Scholar 

  83. R. A. Wendt, K. Angermund, V. Jensen, et al., Macromol. Chem. Phys. 205, 308 (2004).

    Article  CAS  Google Scholar 

  84. W. Kaminsky, A. Bark, and I. Daeke, in Proceedings of International Symposium on Recent Development in Olefin Polymerization, Catalysis (Elsevier, Amsterdam, 1990), p. 425.

    Book  Google Scholar 

  85. J. P. Koinzer, U. Langbein, and E. Taeger, DE Patent No. 109 224 (1973).

  86. E. Brauer, H. Wiegleb, and M. Helmstedt, Polym. Bull. (Berlin) 15, 551 (1986).

    Article  CAS  Google Scholar 

  87. E. Brauer, C. Wild, and H. Wiegleb, Polym. Bull. (Berlin) 18, 73 (1987).

    Article  CAS  Google Scholar 

  88. D. Ruchatz and G. Fink, Macromolecules 31, 4674 (1998).

    Article  CAS  Google Scholar 

  89. D. Ruchatz and G. Fink, Macromolecules 31, 4681 (1998).

    Article  CAS  Google Scholar 

  90. B. A. Harrington and D. J. Crowther, J. Mol. Catal., Chem. 128, 79 (1998).

    Article  CAS  Google Scholar 

  91. N. Ekizoglou, K. Thorshaug, M. Cerrada, et al., J. Appl. Polym. Sci. 89, 3358 (2003).

    Article  CAS  Google Scholar 

  92. K. Thorshaug, R. Mendichi, L. Boggioni, et al., Macromolecules 35, 2903 (2002).

    Article  CAS  Google Scholar 

  93. F.-D. Tran and W. Kaminsky, J. Zhejiang Univ. Sci. 4, 121 (2003).

    Article  CAS  Google Scholar 

  94. T. Hasan, T. Shiono, and T. Ikeda, Macromol. Symp. 213, 122 (2004).

    Article  CAS  Google Scholar 

  95. T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 37, 8503 (2004).

    Article  CAS  Google Scholar 

  96. Y. Yoshida, J. Saito, M. Mitani, et al., Chem. Commun., No. 12, 1298 (2002).

  97. Y. Yoshida, J. Mori, S. Ishii, et al., J. Am. Chem. Soc. 126, 12023 (2004).

  98. Y. Yoshida, S. Matsui, and T. Fujita, J. Organomet. Chem. 690, 4382 (2005).

    Article  CAS  Google Scholar 

  99. W.-Q. Hu, X.-L. Sun, C. Wang, et al., Organometallics 23, 1684 (2004).

    Article  CAS  Google Scholar 

  100. L.-M. Tang, T. Hu, Y.-J. Bo, et al., J. Organomet. Chem. 690, 3125 (2005).

    Article  CAS  Google Scholar 

  101. 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).

  102. 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)].

    Google Scholar 

  103. K. L. Makovetskii, V. I. Bykov, and E. Sh. Finkel’shtein, Kinet. Katal. 47, 243 (2006).

    Article  CAS  Google Scholar 

  104. G. Benedikt, E. Elce, B. L. Goodall, et al., Macromolecules 35, 8978 (2002).

    Article  CAS  Google Scholar 

  105. T. R. Younkin, E. F. Connor, J. I. Henderson, et al., Science (Washington, D. C.) 287, 460 (2000).

    Article  CAS  Google Scholar 

  106. E. F. Connor, T. R. Younkin, J. I. Henderson, et al., J. Polym. Sci., Part A: Polym. Chem. 40, 2842 (2002).

    Article  CAS  Google Scholar 

  107. S. Sujith, D. J. Joe, S. J. Na, et al., Macromolecules 38, 10027 (2005).

  108. S. J. Diamanti, P. Ghosh, F. Shimizu, and G. C. Bazan, Macromolecules 36, 9731 (2003).

    Article  CAS  Google Scholar 

  109. S. J. Diamanti, V. Khanna, A. Hotta, et al., Macromolecules 36, 3270 (2003).

    Article  CAS  Google Scholar 

  110. F. M. Bauers and S. Mecking, Macromolecules 34, 1165 (2001).

    Article  CAS  Google Scholar 

  111. B. L. Goodall and L. H. McIntosh III, US Patent No. 6 265 506 B1 (2001).

  112. J. Kiesewetter and W. Kaminsky, Chem.-Eur. J. 9, 1750 (2003).

    Article  CAS  Google Scholar 

  113. J. Kiesewetter, B. Arikan, and W. Kaminsky, Polymer 47, 3302 (2006).

    Article  CAS  Google Scholar 

  114. K. M. Skupov, P. R. Marella, J. L. Hobbs, et al., Macromolecules 39, 4279 (2006).

    Article  CAS  Google Scholar 

  115. U. Peucker and W. Heitz, Macromol. Chem. Phys. 202, 1289 (2001).

    Article  CAS  Google Scholar 

  116. X. Li, J. Baldamus, and Z. Hou, Angew. Chem., Int. Ed. Engl. 44, 962 (2005).

    Article  CAS  Google Scholar 

  117. W. Wang and K. Nomura, Macromolecules 38, 5905 (2005).

    Article  CAS  Google Scholar 

  118. C. Lorber, F. Wolff, R. Choukroun, and L. Vendier, Eur. J. Inorg. Chem, No. 14, 2850 (2005).

  119. J. Yamada, M. Fujiki, and K. Nomura, Organometallics 24, 2248 (2005).

    Article  CAS  Google Scholar 

  120. O. Henschke, F. Koeller, and M. Arnold, Macromol. Rapid. Commun. 18, 617 (1997).

    Article  CAS  Google Scholar 

  121. T. Hasan, T. Ikeda, and T. Shiono, Macromolecules 38, 2031 (2005).

    Article  CAS  Google Scholar 

  122. Z. Cai, Y. Nakayama, and T. Shiono, Macromolecules 39, 1071 (2006).

    Google Scholar 

  123. H. Y. Jung, S.-D. Hong, M. W. Jung, et al., Polyhedron 24, 1269 (2005).

    Article  CAS  Google Scholar 

  124. E. Aitola, T. Repo, C. Bergstroem, and Leskelae, J. Appl. Polym. Sci. 84, 2743 (2002).

    Article  CAS  Google Scholar 

  125. H. Gao, Y. Chen, F. Zhu, and Q. Wu, J. Polym. Sci., Part A: Polym. Chem. 44, 5237 (2006).

    Article  CAS  Google Scholar 

  126. H. Suzuki, Sh. Matsumura, Y. Satoh, et al., React. Funct. Polym. 58, 77 (2004).

    Article  CAS  Google Scholar 

  127. H. Suzuki, Sh. Matsumura, Y. Satoh, et al., React. Funct. Polym. 59, 253 (2004).

    Article  CAS  Google Scholar 

  128. L. Wang, Y. Li, F. Zhu, and Q. Wu, Polym. Bull. (Berlin) 57, 73 (2006).

    Article  CAS  Google Scholar 

  129. B. L. Goodall and L. H. McIntosh III, US Patent No. 6 303 724 B1 (2001).

  130. H. V. Tran, R. J. Hung, T. Chiba, et al., Macromolecules 35, 6539 (2002).

    Article  CAS  Google Scholar 

  131. D. P. Sanders, E. F. Connor, R. H. Grubbs, et al., Macromolecules 36, 1534 (2003).

    Article  CAS  Google Scholar 

  132. B. C. Trinque, C. R. Chambers, B. P. Osborn, et al., J. Fluorine Chem. 122, 17 (2003).

    Article  CAS  Google Scholar 

  133. A. E. Feiring, M. K. Crawford, W. B. Farnham, et al., Macromolecules 39, 3252 (2006).

    Article  CAS  Google Scholar 

  134. A. E. Feiring, M. K. Crawford, W. B. Farnham, et al., J. Fluorine Chem. 122, 11 (2003).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. L. Makovetskii.

Additional information

Original Russian Text © K.L. Makovetskii, 2008, published in Vysokomolekulyarnye Soedineniya, Ser. C, 2008, Vol. 50, No. 7, pp. 1322–1343.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1811238208010025

Keywords

Navigation