Hostname: page-component-cd9895bd7-gbm5v Total loading time: 0 Render date: 2024-12-25T13:36:40.010Z Has data issue: false hasContentIssue false

State of the art of cyclic olefin polymers

Published online by Cambridge University Press:  13 March 2013

Laura Boggioni
Affiliation:
Istituto per lo Studio delle, Macromolecole, CNR, Italy; [email protected]
Incoronata Tritto
Affiliation:
Istituto per lo Studio delle, Macromolecole, CNR, Italy; [email protected]
Get access

Abstract

Highly active metallocenes and other single site catalysts as well as Grubbs and Schrock metathesis catalytic systems have opened up the possibility to polymerize cycloolefins or to copolymerize them with ethene or propene. The polymers obtained show exciting structures and properties. Cycloolefins such as cyclopentene, cyclooctene, norbornene, and their substituted derivatives are incorporated into the polymer chain either by double bonds or by ring-opening metathesis polymerization. Materials with elastomeric properties or tactic polymers with high glass transition temperatures and melting points are obtained with a wide range of microstructures. For example, cycloolefin copolymers and other homo- and copolymers of norbornene are of great academic and industrial interest because of their properties and applications in optoelectronics, lenses, and coatings.

Type
Research Article
Copyright
Copyright © Materials Research Society 2013

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1. Truett, W.L., Johnson, D.R., Robinson, I.M., Montague, B.A., J. Am. Chem. Soc. 82, 2337 (1960).Google Scholar
2. Sartori, G., Ciampelli, F.C., Cameli, N., Chim. Ind. 45, 1478 (1963).Google Scholar
3. Natta, G., Dall’Asta, G., Mazzanti, G., Pasquon, I., Valvassori, A., Zambelli, A., Makromol. Chem. 54, 95 (1962).Google Scholar
4. Dall’Asta, G., Mazzanti, G., Natta, G., Porri, L., Makromol. Chem. 56, 224 (1962).CrossRefGoogle Scholar
5. Natta, G., Dall’Asta, G., Mazzanti, G., Angew. Chem. Int. Ed. 3,723 (1964).CrossRefGoogle Scholar
6. Ivin, K.J., Saegusa, T., Cycloalkenes and Bicycloalkenes Ring-Opening Polymerization (Elsevier, London, 1984), vol. 1.Google Scholar
7. Grubbs, R.H., Handbook of Metathesis (Wiley-VCH: Weinheim, 2003).Google Scholar
8. Kaminsky, W., Arndt-Rosenau, M., in Metallocene-based Polyolefins, Scheirs, J., Kaminsky, W., Eds. (Wiley, Chichester, 2000), p. 91.Google Scholar
9. Tritto, I., Boggioni, L., Ferro, D.R., Coord. Chem. Rev. 250, 212 (2006).CrossRefGoogle Scholar
10. Blank, F., Janiak, C., Coord. Chem. Rev. 253, 827 (2009).Google Scholar
11. Kaminsky, W., Boggioni, L., Tritto, I., in Polymer Science: A Comprehensive Reference, Matyjaszewski, K., Möller, M., Eds. (Elsevier B.V., The Netherlands, 2012), vol. 3, pp. 843873.CrossRefGoogle Scholar
12. Kaminsky, W., Bark, A., Arndt, M., Macromol. Symp. 47, 83 (1991).Google Scholar
13. Buchmeiser, M.R., Chem. Rev. 100, 1565 (2000).CrossRefGoogle Scholar
14. Trnka, T.M., Grubbs, R.H., Acc.Chem. Res. 34, 18 (2001).CrossRefGoogle Scholar
15. Schrock, R.R., Chem. Rev. 102, 14 (2002).Google Scholar
16. Schrock, R.R., Angew. Chem. Int. Ed. 45, 3748 (2006).Google Scholar
17. Grubbs, R.H., Angew. Chem. Int. Ed. 45, 3760 (2006).CrossRefGoogle Scholar
18. Bielawski, C.W., Grubbs, R.H., Prog. Polym. Sci. 32, 1 (2007).Google Scholar
19. Schrock, R.R., Dalton Trans. 40, 7484 (2011).CrossRefGoogle Scholar
20. Keitz, B.K., Fedorov, A., Grubbs, R.H., J. Am. Chem. Soc. 134, 2040 (2012).Google Scholar
21. Wang, W., Fujiki, M., Nomura, K., J. Am. Chem. Soc. 127, 4582 (2005).Google Scholar
22. Arndt, M., Grundlagen und Mechanismen der Polymerisation von Cycloolefinen unter Verwendung homogener Ziegler-Natta Katalysatoren (Verlag Shaker, Aachen, 1994).Google Scholar
23. Arndt, M., Kaminsky, W., Macromol. Symp. 95, 167 (1995).Google Scholar
24. Arndt, M., Engehausen, R., Kaminsky, W., Zoumis, K., J. Mol. Catal. A: Chem. 101, 171 (1995).CrossRefGoogle Scholar
25. Collins, S., Kelly, W.M., Macromolecules 25, 233 (1992).Google Scholar
26. Kelly, W.M., Taylor, N.J., Collins, S., Macromolecules 27, 4477 (1994).Google Scholar
27. McLain, S.J., Feldman, J., McCord, E.F., Gardner, K.H., Teasley, M.F., Coughlin, E.B., Sweetman, K.J., Johnson, L.K., Brookhart, M., Macromolecules 31, 6705 (1998).CrossRefGoogle Scholar
28. Rush, S., Reinmuth, A., Risse, W., O’Brien, J., Ferro, D.R., Tritto, I., J. Am. Chem. Soc. 118, 12230 (1996).Google Scholar
29. Curran, K., Risse, W., Boggioni, L., Tritto, I., Macromol. Chem. Phys. 209, 707 (2008).Google Scholar
30. Sen, A., Lai, T.-W., J. Am. Chem. Soc. 103, 4627 (1981).Google Scholar
31. Mehler, C., Risse, W., Macromolecules 25, 4226 (1992).Google Scholar
32. Breunig, S., Risse, W., Makromol. Chem. 193, 2915 (1992).Google Scholar
33. Goodall, B.L., McIntosh, L.H. III, Rhodes, L.F., Macromol. Symp. 89, 421 (1995).Google Scholar
34. Goodall, B.L., Benedikt, G.M., McIntosh, L.H. III, Barnes, D.A., US Patent 5,468,819 (1995).Google Scholar
35. Goodall, B.L., Barnes, D.A., Benedikt, G.M., McIntosh, L.H. III, Rhodes, L.F., Polym. Mater. Sci. Eng. 76, 56 (1997).Google Scholar
36. Hennis, A.D., Polley, J.D., Long, G.S., Sen, A., Yandulov, D., Lipian, J., Benedikt, G.M., Rhodes, L.F., Huffman, J., Organometallics 20, 2802 (2001).Google Scholar
37. Goodall, B.L., in Late Transition Metal Polymerization Catalysis, Rieger, B., Baugh, L.S., Kacker, S., Striegler, S., Eds. (Wiley-VCH, Weinheim, 2003), p. 101.Google Scholar
39. Kaminsky, W., Bark, A., Arndt, M., Makromol. Chem. Macromol. Symp. 47, 83 (1991).Google Scholar
40. Kaminsky, W., Sperber, O., Werner, R., Coord. Chem. Rev. 250, 110 (2006).Google Scholar
41. Jerschow, A., Ernst, E., Hermann, W., Müller, N., Macromolecules 28, 7095 (1995).Google Scholar
42. Naga, N., Imanishi, Y., Macromol. Chem. Phys. 203, 159 (2002).Google Scholar
43. Naga, N., Imanishi, Y., Polymer 43, 2133 (2002).Google Scholar
44. Fujita, M., Coates, G.W., Macromolecules 35, 9640 (2002).Google Scholar
45. Lavoie, A.R., How, M.H., Waymouth, R.M., Chem. Commun. 864 (2003).CrossRefGoogle Scholar
46. Lavoie, A.R., Waymouth, R.M., Tetrahedron 60, 7147 (2004).CrossRefGoogle Scholar
47. Li, X., Hou, Z.M., Coord. Chem. Rev. 252, 1842 (2008).Google Scholar
48. Ruchatz, D., Fink, G., Macromolecules 31, 4674 (1998).CrossRefGoogle Scholar
49. Ruchatz, D., Fink, G., Macromolecules 31, 4681 (1998).Google Scholar
50. Harrington, B.A., Crowther, D.J., J. Mol. Catal. A: Chem. 128, 79 (1998).Google Scholar
51. McKnight, A.L., Waymouth, R.M., Macromolecules 32, 2816 (1999).Google Scholar
52. Lee, B.Y., Kim, Y.H., Won, Y.C., Han, J.W., Suh, W.H., Lee, I.S., Chung, Y.K., Song, K.H., Organometallics 21, 1500 (2002).Google Scholar
53. Domski, G.J., Rose, J.M., Coates, G.W., Bolig, A.D., Brookhart, M., Prog. Polym. Sci. 32, 30 (2007).Google Scholar
54. Jansen, J.C., Mendichi, R., Locatelli, P., Tritto, I., Macromol. Rapid Commun. 22, 1394 (2001).3.0.CO;2-B>CrossRefGoogle Scholar
55. Bhriain, N.N., Brintzinger, H.H., Ruchatz, D., Fink, G., Macromolecules 38, 2056 (2005).Google Scholar
56. Thorshaug, K., Mendichi, R., Boggioni, L., Tritto, I., Trinkle, S., Friedrich, C., Mülhaupt, R., Macromolecules 35, 2903 (2002).CrossRefGoogle Scholar
57. Marconi, R., Ravasio, A., Boggioni, L., Tritto, I., Macromol. Rapid Commun. 30, 39 (2008).Google Scholar
58. Hasan, T., Shiono, T., Ikeda, T., Macromolecules 23, 8503 (2004).Google Scholar
59. Shiono, T., Polym. J. 43, 331 (2011), and references therein.CrossRefGoogle Scholar
60. Yoshida, Y., Matsui, S., Fujita, T., J. Organomet. Chem. 690, 4382 (2005).Google Scholar
61. Nomura, K., Dalton Trans. 41, 8811 (2009), and references therein.CrossRefGoogle Scholar
62. Matsui, S., Yoshida, Y., Takagi, Y., Spaniol, T.P., Okuda, J.J., Organomet. Chem. 689, 1155 (2004).Google Scholar
63. Bergstrom, C.H., Seppala, J.V., J. Polym. Sci., Part A: Polym. Chem. 63, 1063 (1997).Google Scholar
64. Tritto, I., Boggioni, L., Sacchi, M.C., Locatelli, P., Macromol. Chem. Phys. 279 (1999).Google Scholar
65. Tritto, I., Marestin, C., Boggioni, L., Zetta, L., Provasoli, A., Ferro, D.R., Macromolecules 33, 8931 (2000).Google Scholar
66. Wendt, R.A., Fink, G., Macromol. Chem. Phys. 202, 3490 (2001).Google Scholar
67. Provasoli, A., Ferro, D.R., Tritto, I., Boggioni, L., Macromolecules 32, 6697 (1999).Google Scholar
68. Hou, Z., Luo, Y., Li, X., J. Organomet. Chem. 691, 2734 (2006).Google Scholar
69. Li, X., Baldamus, J., Hou, Z., Angew. Chem. Int. Ed. 44, 962 (2005).Google Scholar
70. Ravasio, A., Zampa, C., Boggioni, L., Tritto, I., Hitzbleck, J., Okuda, J., Macromolecules 41, 9565 (2008).Google Scholar
71. Younkin, T.R., Connor, E.F., Henderson, J.I., Friedrich, S.K., Grubbs, R.H., Bansleben, D.A., Science 287, 460 (2000).Google Scholar
72. Kiesewetter, J., Kaminsky, W., Chem. Eur. J. 9, 1750 (2003).Google Scholar
73. Kiesewetter, J., Arikan, B., Kaminsky, W., Polymer 47, 3302 (2006).Google Scholar
74. Bauers, F.M., Mecking, S., Macromolecules 34, 1165 (2001).Google Scholar
75. Connor, E.F., Younkin, T.R., Henderson, J.I., Hwang, S.J., Grubbs, R.H., Roberts, W.P., Litzau, J.J., J. Polym. Sci., Part A: Polym. Chem. 40, 2842 (2002).Google Scholar
76. Sujith, S., Joe, D.J., Na, S.J., Park, Y.-W., Choi, C.H., Lee, B.Y., Macromolecules 38, 10027 (2005).Google Scholar
77. Wehrmann, P., Zuideveld, M., Thomann, R., Mecking, S., Macromolecules 39, 5995 (2006).Google Scholar
78. Benedikt, G.M., Elce, E., Goodall, B.L., Kalamarides, H.A., McIntosh, L.H., Rhodes, L.F., Selvy, K.T., Andes, C., Oyler, K., Sen, A., Macromolecules 35, 8978 (2002).Google Scholar
79. Skupov, K.M., Marella, P.R., Hobbs, J.L., McIntosh, L.H., Goodall, B.L., Claverie, J.P., Macromolecules 39, 4279 (2006).Google Scholar
80. Liu, S., Borkar, S., Newsham, D., Yennawar, H., Sen, A., Organometallics 26, 210 (2007).Google Scholar
81. Ravasio, A., Boggioni, L., Tritto, I., Macromolecules 44, 4180 (2011).Google Scholar
82. Diamanti, S.J., Ghosh, P., Shimizu, F., Bazan, G.C., Macromolecules, 36, 9731 (2003).Google Scholar
83. Diamanti, S.J., Kanna, V., Hotta, A., Yamakava, D., Shimizu, F., Kramer, E.J., Fredrikson, G.H., Bazan, G.C., J. Am. Chem. Soc. 126, 10528 (2004).CrossRefGoogle Scholar
84. Coffin, R.C., Diamanti, S.J., Hotta, A., Khanna, V., Kramer, E.J., Fredrickson, G.H., Bazan, G.C., Chem. Commun. 3550 (2007).CrossRefGoogle Scholar
85. Yoshida, Y., Mohri, J., Ishii, S., Mitani, M., Saito, J., Matsui, S., Makio, H., Nakano, T., Tanaka, H., Onda, M., Yamamoto, Y., Mizuno, A., Fujita, T., J. Am. Chem. Soc. 126, 12023 (2004).Google Scholar
86. Ravasio, A., Boggioni, L., Bertini, F., Tritto, I., J. Polym. Sci., Part A: Polym. Chem. 50, 867 (2012).Google Scholar
87. Henschke, O., Köller, F., Arnold, M., Makromol. Rapid Commun. 18, 617 (1997).Google Scholar
88. Boggioni, L., Bertini, F., Zannoni, G., Tritto, I., Carbone, P., Ragazzi, M., Ferro, D.R., Macromolecules 36, 882 (2003).Google Scholar
89. Carbone, P., Ragazzi, M., Tritto, I., Boggioni, L., Ferro, D.R., Macromolecules 36, 891 (2003).Google Scholar
90. Kaminsky, W., Derlin, S., Hoff, M., Polymer 48, 7271 (2007).Google Scholar
91. Zampa, C., Ravasio, A., Tritto, I., Ferro, D.R., Macromolecules 41, 5107 (2008).Google Scholar
92. Boggioni, L., Ravasio, A., Zampa, C., Ferro, D.R., Tritto, I., Macromolecules 43, 4532 (2010).Google Scholar
93. Boggioni, L., Ravasio, A., Boccia, A.C., Ferro, D.R., Tritto, I., Macromolecules 43, 4543 (2010).CrossRefGoogle Scholar
94. Hasan, T., Ikeda, T., Shiono, T., Macromolecules 38, 1071 (2005).CrossRefGoogle Scholar
95. Kaminsky, W., Bark, A., Polym. Int. 2, 251 (1992).Google Scholar
96. Kaminsky, W., Beulich, I., Arndt-Rosenau, M., Macromol. Symp. 173, 211 (2001).Google Scholar
97. Dougnac, V.N., Quijada, R., Palza, H., Galland, G.B., Eur. Polym. J. 45, 102 (2009).CrossRefGoogle Scholar
98. Lee, D.-H., Yoon, K.-B., Park, J.-R., Lee, B.-H., Eur. Polym. J. 33, 447 (1997).CrossRefGoogle Scholar
99. Naga, N.J., J. Polym. Sci., Part A: Polym. Chem. 43, 1285 (2005).Google Scholar
100. Simanke, A.G., Mauler, R.S., Galland, G.B., J. Polym. Sci., Part A: Polym. Chem. 40, 471 (2002).Google Scholar
101. Suzuki, J., Kino, Y., Uozumi, T., Sano, T., Teranishi, T., Jin, J., Soga, K., Shiono, T., J. Appl. Polym. Sci. 72, 103 (1999).Google Scholar
102. Li, X.F., Hou, Z.M., Macromolecules 38, 6767 (2005).Google Scholar
103. Cho, D.J., Wu, C.J., Sujith, S., Han, W.-S., Kang, S.O., Lee, B.Y., Organometallics 25, 2133 (2006).Google Scholar
104. Na, S.J., Wu, C.J., Yoo, J., Kim, B.E., Lee, B.Y., Macromolecules 41, 4055 (2008).Google Scholar
105. Yu, S.T., Na, S.J., Lim, T.S., Lee, B.Y., Macromolecules 43, 725 (2010).CrossRefGoogle Scholar
106. Hong, M., Cui, L., Liu, S., Li, Y., Macromolecules 45, 5397 (2012).Google Scholar