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.
Similar content being viewed by others
References
W.L. Truett, D.R. Johnson, I.M. Robinson, B.A. Montague, J. Am. Chem. Soc. 82, 2337 (1960).
G. Sartori, F.C. Ciampelli, N. Cameli, Chim. Ind. 45, 1478 (1963).
G. Natta, G. Dall’Asta, G. Mazzanti, I. Pasquon, A. Valvassori, A. Zambelli, Makromol. Chem. 54, 95 (1962).
G. Dall’Asta, G. Mazzanti, G. Natta, L. Porri, Makromol. Chem. 56, 224 (1962).
G. Natta, G. Dall’Asta, G. Mazzanti, Angew. Chem. Int. Ed. 3, 723 (1964).
K.J. Ivin, T. Saegusa, Cycloalkenes and Bicycloalkenes Ring-Opening Polymerization (Elsevier, London, 1984), vol. 1.
R.H. Grubbs, Handbook of Metathesis (Wiley-VCH: Weinheim, 2003).
W. Kaminsky, M. Arndt-Rosenau, in Metallocene-based Polyolefins, J. Scheirs, W. Kaminsky, Eds. (Wiley, Chichester, 2000), p. 91.
I. Tritto, L. Boggioni, D.R. Ferro, Coord. Chem. Rev. 250, 212 (2006).
F. Blank, C. Janiak, Coord. Chem. Rev. 253, 827 (2009).
W. Kaminsky, L. Boggioni, I. Tritto, in Polymer Science: A Comprehensive Reference, K. Matyjaszewski, M. Möller, Eds. (Elsevier B.V., The Netherlands, 2012), vol. 3, pp. 843 – 873.
W. Kaminsky, A. Bark, M. Arndt, Macromol. Symp. 47, 83 (1991).
M.R. Buchmeiser, Chem. Rev. 100, 1565 (2000).
T.M. Trnka, R.H. Grubbs, Acc.Chem. Res. 34, 18 (2001).
R.R. Schrock, Chem. Rev. 102, 14 (2002).
R.R. Schrock, Angew. Chem. Int. Ed. 45, 3748 (2006).
R.H. Grubbs, Angew. Chem. Int. Ed. 45, 3760 (2006).
C.W. Bielawski, R.H. Grubbs, Prog. Polym. Sci. 32, 1 (2007).
R.R. Schrock, Dalton Trans. 40, 7484 (2011).
B.K. Keitz, A. Fedorov, R.H. Grubbs, J. Am. Chem. Soc. 134, 2040 (2012).
W. Wang, M. Fujiki, K. Nomura, J. Am. Chem. Soc. 127, 4582 (2005).
M. Arndt, Grundlagen und Mechanismen der Polymerisation von Cycloolefinen unter Verwendung homogener Ziegler-Natta Katalysatoren (Verlag Shaker, Aachen, 1994).
M. Arndt, W. Kaminsky, Macromol. Symp. 95, 167 (1995).
M. Arndt, R. Engehausen, W. Kaminsky, K. Zoumis, J. Mol. Catal. A: Chem. 101, 171 (1995).
S. Collins, W.M. Kelly, Macromolecules 25, 233 (1992).
W.M. Kelly, N.J. Taylor, S. Collins, Macromolecules 27, 4477 (1994).
S.J. McLain, J. Feldman, E.F. McCord, K.H. Gardner, M.F. Teasley, E.B. Coughlin, K.J. Sweetman, L.K. Johnson, M. Brookhart, Macromolecules 31, 6705 (1998).
S. Rush, A. Reinmuth, W. Risse, J. O’Brien, D.R. Ferro, I. Tritto, J. Am. Chem. Soc. 118, 12230 (1996).
K. Curran, W. Risse, L. Boggioni, I. Tritto, M acromol. Chem. Phys. 2 09, 707 (2008).
A. Sen, T.-W. Lai, J. Am. Chem. Soc. 103, 4627 (1981).
C. Mehler, W. Risse, Macromolecules 25, 4226 (1992).
S. Breunig, W. Risse, Makromol. Chem. 193, 2915 (1992).
B.L. Goodall, L.H. McIntosh III, L.F. Rhodes, Macromol. Symp. 89, 421 (1995).
B.L. Goodall, G.M. Benedikt, L.H. McIntosh III, D.A. Barnes, US Patent 5,468,819 (1995).
B.L. Goodall, D.A. Barnes, G.M. Benedikt, L.H. McIntosh III, L.F. Rhodes, Polym. Mater. Sci. Eng. 76, 56 (1997).
A.D. Hennis, J.D. Polley, G.S. Long, A. Sen, D. Yandulov, J. Lipian, G.M. Benedikt, L.F. Rhodes, J. Huffman, Organometallics 20, 2802 (2001).
B.L. Goodall, in Late Transition Metal Polymerization Catalysis, B. Rieger, L.S. Baugh, S. Kacker, S. Striegler, Eds. (Wiley-VCH, Weinheim, 2003), p. 101.
W. Kaminsky, A. Bark, M. Arndt, Makromol. Chem. Macromol. Symp. 47, 83 (1991).
W. Kaminsky, O. Sperber, R. Werner, Coord. Chem. Rev. 250, 110 (2006).
A. Jerschow, E. Ernst, W. Hermann, N. Müller, Macromolecules 28, 7095 (1995).
N. Naga, Y. Imanishi, Macromol. Chem. Phys. 203, 159 (2002).
N. Naga, Y. Imanishi, Polymer 43, 2133 (2002).
M. Fujita, G.W. Coates, Macromolecules 35, 9640 (2002).
A.R. Lavoie, M.H. How, R.M. Waymouth, Chem. Commun. 864 (2003).
A.R. Lavoie, R.M. Waymouth, Tetrahedron 60, 7147 (2004).
X. Li, Z.M. Hou, Coord. Chem. Rev. 252, 1842 (2008).
D. Ruchatz, G. Fink, Macromolecules 31, 4674 (1998).
D. Ruchatz, G. Fink, Macromolecules 31, 4681 (1998).
B.A. Harrington, D.J. Crowther, J. Mol. Catal. A: Chem. 128, 79 (1998).
A.L. McKnight, R.M. Waymouth, Macromolecules 32, 2816 (1999).
B.Y. Lee, Y.H. Kim, Y.C. Won, J.W. Han, W.H. Suh, I.S. Lee, Y.K. Chung, K.H. Song, Organometallics 21, 1500 (2002).
G.J. Domski, J.M. Rose, G.W. Coates, A.D. Bolig, M. Brookhart, Prog. Polym. Sci. 32, 30 (2007).
J.C. Jansen, R. Mendichi, P. Locatelli, I. Tritto, Macromol. Rapid Commun. 22, 1394 (2001).
N.N. Bhriain, H.H. Brintzinger, D. Ruchatz, G. Fink, Macromolecules 38, 2056 (2005).
K. Thorshaug, R. Mendichi, L. Boggioni, I. Tritto, S. Trinkle, C. Friedrich, R. Mülhaupt, Macromolecules 35, 2903 (2002).
R. Marconi, A. Ravasio, L. Boggioni, I. Tritto, Macromol. Rapid Commun. 30, 39 (2008).
T. Hasan, T. Shiono, T. Ikeda, Macromolecules 23, 8503 (2004).
T. Shiono, Polym. J. 43, 331 (2011), and references therein.
Y. Yoshida, S. Matsui, T. Fujita, J. Organomet. Chem. 690, 4382 (2005).
K. Nomura, Dalton Trans. 41, 8811 (2009), and references therein.
S. Matsui, Y. Yoshida, Y. Takagi, T.P. Spaniol, J.J. Okuda, Organomet. Chem. 689, 1155 (2004).
C.H. Bergstrom, J.V. Seppala, J. Polym. Sci., Part A: Polym. Chem. 63, 1063 (1997).
I. Tritto, L. Boggioni, M.C. Sacchi, P. Locatelli, Macromol. Chem. Phys. 279 (1999).
I. Tritto, C. Marestin, L. Boggioni, L. Zetta, A. Provasoli, D.R. Ferro, Macromolecules 33, 8931 (2000).
R.A. Wendt, G. Fink, Macromol. Chem. Phys. 202, 3490 (2001).
A. Provasoli, D.R. Ferro, I. Tritto, L. Boggioni, Macromolecules 32, 6697 (1999).
Z. Hou, Y. Luo, X. Li, J. Organomet. Chem. 691, 2734 (2006).
X. Li, J. Baldamus, Z. Hou, Angew. Chem. Int. Ed. 44, 962 (2005).
A. Ravasio, C. Zampa, L. Boggioni, I. Tritto, J. Hitzbleck, J. Okuda, Macromolecules 41, 9565 (2008).
T.R. Younkin, E.F. Connor, J.I. Henderson, S.K. Friedrich, R.H. Grubbs, D.A. Bansleben, Science 287, 460 (2000).
J. Kiesewetter, W. Kaminsky, Chem. Eur. J. 9, 1750 (2003).
J. Kiesewetter, B. Arikan, W. Kaminsky, Polymer 47, 3302 (2006).
F.M. Bauers, S. Mecking, Macromolecules 34, 1165 (2001).
E.F. Connor, T.R. Younkin, J.I. Henderson, S.J. Hwang, R.H. Grubbs, W.P. Roberts, J.J. Litzau, J. Polym. Sci., Part A: Polym. Chem. 40, 2842 (2002).
S. Sujith, D.J. Joe, S.J. Na, Y.-W. Park, C.H. Choi, B.Y. Lee, Macromolecules 38, 10027 (2005).
P. Wehrmann, M. Zuideveld, R. Thomann, S. Mecking, Macromolecules 39, 5995 (2006).
G.M. Benedikt, E. Elce, B.L. Goodall, H.A. Kalamarides, L.H. McIntosh, L.F. Rhodes, K.T. Selvy, C. Andes, K. Oyler, A. Sen, Macromolecules 35, 8978 (2002).
K.M. Skupov, P.R. Marella, J.L. Hobbs, L.H. McIntosh, B.L. Goodall, J.P. Claverie, Macromolecules 39, 4279 (2006).
S. Liu, S. Borkar, D. Newsham, H. Yennawar, A. Sen, Organometallics 26, 210 (2007).
A. Ravasio, L. Boggioni, I. Tritto, Macromolecules 44, 4180 (2011).
S.J. Diamanti, P. Ghosh, F. Shimizu, G.C. Bazan, Macromolecules, 36, 9731 (2003).
S.J. Diamanti, V. Kanna, A. Hotta, D. Yamakava, F. Shimizu, E.J. Kramer, G.H. Fredrikson, G.C. Bazan, J. Am. Chem. Soc. 126, 10528 (2004).
R.C. Coffin, S.J. Diamanti, A. Hotta, V. Khanna, E.J. Kramer, G.H. Fredrickson, G.C. Bazan, Chem. Commun. 3550 (2007).
Y. Yoshida, J. Mohri, S. Ishii, M. Mitani, J. Saito, S. Matsui, H. Makio, T. Nakano, H. Tanaka, M. Onda, Y. Yamamoto, A. Mizuno, T. Fujita, J. Am. Chem. Soc. 126, 12023 (2004).
A. Ravasio, L. Boggioni, F. Bertini, I. Tritto, J. Polym. Sci., Part A: Polym. Chem. 50, 867 (2012).
O. Henschke, F. Köller, M. Arnold, Makromol. Rapid Commun. 18, 617 (1997).
L. Boggioni, F. Bertini, G. Zannoni, I. Tritto, P. Carbone, M. Ragazzi, D.R. Ferro, Macromolecules 36, 882 (2003).
P. Carbone, M. Ragazzi, I. Tritto, L. Boggioni, D.R. Ferro, Macromolecules 36, 891 (2003).
W. Kaminsky, S. Derlin, M. Hoff, Polymer 48, 7271 (2007).
C. Zampa, A. Ravasio, I. Tritto, D.R. Ferro, Macromolecules 41, 5107 (2008).
L. Boggioni, A. Ravasio, C. Zampa, D.R. Ferro, I. Tritto, Macromolecules 43, 4532 (2010).
L. Boggioni, A. Ravasio, A.C. Boccia, D.R. Ferro, I. Tritto, Macromolecules 43, 4543 (2010).
T. Hasan, T. Ikeda, T. Shiono, Macromolecules 38, 1071 (2005).
W. Kaminsky, A. Bark, Polym. Int. 2, 251 (1992).
W. Kaminsky, I. Beulich, M. Arndt-Rosenau, Macromol. Symp. 173, 211 (2001).
V.N. Dougnac, R. Quijada, H. Palza, G.B. Galland, Eur. Polym. J. 45, 102 (2009).
D.-H. Lee, K.-B. Yoon, J.-R. Park, B.-H. Lee, Eur. Polym. J. 33, 447 (1997).
N.J. Naga, J. Polym. Sci., Part A: Polym. Chem. 43, 1285 (2005).
A.G. Simanke, R.S. Mauler, G.B. Galland, J. Polym. Sci., Part A: Polym. Chem. 40, 471 (2002).
J. Suzuki, Y. Kino, T. Uozumi, T. Sano, T. Teranishi, J. Jin, K. Soga, T. Shiono, J. Appl. Polym. Sci. 72, 103 (1999).
X.F. Li, Z.M. Hou, Macromolecules 38, 6767 (2005).
D.J. Cho, C.J. Wu, S. Sujith, W.-S. Han, S.O. Kang, B.Y. Lee, Organometallics 25, 2133 (2006).
S.J. Na, C.J. Wu, J. Yoo, B.E. Kim, B.Y. Lee, Macromolecules 41, 4055 (2008).
S.T. Yu, S.J. Na, T.S. Lim, B.Y. Lee, Macromolecules 43, 725 (2010).
M. Hong, L. Cui, S. Liu, Y. Li, Macromolecules 45, 5397 (2012).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Boggioni, L., Tritto, I. State of the art of cyclic olefin polymers. MRS Bulletin 38, 245–251 (2013). https://doi.org/10.1557/mrs.2013.53
Published:
Issue Date:
DOI: https://doi.org/10.1557/mrs.2013.53