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Study of Dimethoxysilacycloalkanes as External Donors in Ziegler-Natta Stereospecific Propylene Polymerisation

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Summary

A series of cyclic dimethoxysilanes has been prepared using a one-step strategy which consists in reacting magnesium dibromoalkanes with tetramethoxysilane. The dimethoxysilacycloalkanes obtained were evaluated as the external electron donor in Ziegler–Natta catalysts for propylene polymerisation. Comparison of the experimental results with theoretical predictions using a molecular model confirmed the essential structural characteristics that are required to achieve stereospecific polymerisation of propylene. Very good activity and stereospecificity were obtained with 2,6-diethyl-1,1-dimethoxysilacyclohexane which led to results close to that of actual industrial external electron donors, cyclohexylmethyldimethoxysilane and dicyclopentyl dimethoxysilane.

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References

  1. Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 541.

  2. Ziegler, K.; Gellert, H. G.; Zosel, K.; Lehmkuhl, W.; Pfohl, W. Angew. Chem. 1955, 67, 424.

    Google Scholar 

  3. Natta, G.; Pino, P.; Corradini, P.; Danusso, F.; Mantica, E.; Mazzanti, G.; Moraglio, G. J. Am. Chem. Soc. 1955, 77, 1708.

    Google Scholar 

  4. Natta, G. J. Polym. Sci. 1955, 16, 143.

    Google Scholar 

  5. Garoff, T.; Virkkunen, V.; Jaaskelainen, P.; Vestberg, T. Eur. Polym. J. 2003, 39, 1679.

    Google Scholar 

  6. Liu, B.; Nitta, T.; Nakatani, H.; Terano, M. Macromol. Symp. 2004, 213, 7.

    Google Scholar 

  7. Guyot, A.; Spitz, R.; Journaud, C.; Eisenstein, O. Macromol. Symp. 1995, 89, 39.

    Google Scholar 

  8. Seth, M.; Ziegler, T. Macromolecules 2003, 36, 6613.

    Google Scholar 

  9. Seth, M.; Margl, P. M.; Ziegler, T. Macromolecules 2002, 35, 7815.

    Google Scholar 

  10. Liu, B.; Nitta, T.; Nakatani, H.; Terano, M. Macromol. Chem. Phys. 2003, 204, 395.

    Google Scholar 

  11. Shimozawa, K.; Saito, M.; Kataoka, T.; Chujo, R. Polymer International 2002, 51, 530.

    Google Scholar 

  12. Morini, G.; Albizzati, E.; Balbontin, G.; Mingozzi, I.; Sacchi, M. C.; Forlini, F.; Tritto, I. Macromolecules 1996, 29, 5770.

    Google Scholar 

  13. Sacchi, M. C.; Forlini, F.; Tritto, I.; Locatelli, P.; Morini, G.; Noristi, L.; Albizzati, E. Macromolecules 1996, 29, 3341.

    Google Scholar 

  14. Busico, V.; Corradini, P.; De Martino, L.; Graziano, F.; Iadicicco, A. Makromol. Chem. 1991, 192, 49.

    Google Scholar 

  15. Lee, D. H.; Jeong, Y. T.; Soga, K. Ind. Eng. Chem. Res. 1992, 31, 2642.

    Google Scholar 

  16. Lee, D. H.; Jeong, Y. T.; Soga, K.; Shiono, T. J. Appl. Polym. Sci. 1993, 47, 1449.

    Google Scholar 

  17. Proto, A.; Oliva, L.; Pellecchia, C.; Sivak, A. J.; Cullo, L. A. Macromolecules 1990, 23, 2904.

  18. Sacchi, M. C.; Tritto, I.; Locatelli, P. Eur. Polym. J. 1988, 24, 137.

    Google Scholar 

  19. Ikeuchi, H.; Yano, T.; Ikai, S.; Sato, H.; Yamashita, J. J. Mol. Catal. A 2003, 193, 207.

    Google Scholar 

  20. EP 1054015, ATOFINA, Grison, C.; Batt-Coutrot, D.; Coutrot, P.; Saudemont, T.; Malinge, J.

  21. US 2003036616, ATOFINA, Grison, C.; Barthel, V.; Batt-Coutrot, D.; Coutrot, P.; Saudemont, T.; Brusson, J.-M.; Malinge, J.; Brun, C.; Meynard, C.

  22. Soga, K.; Shiono, T.; Doi, Y. Makromol. Chem. 1988, 189, 1531.

    Google Scholar 

  23. Harkonen, M.; Kuutti, L.; Seppala, J. V. Makromol. Chem. 1992, 193, 1413.

    Google Scholar 

  24. Harkonen, M.; Seppala, J. V.; Vaananen, T. Stud. Surf. Sci. Catal. 1990, 56, 87.

    Google Scholar 

  25. Okano, T.; Chida, K.; Furuhashi, H.; Nakano, A.; Ueki, S. Stud. Surf. Sci. Catal. 1990, 56, 177.

    Google Scholar 

  26. Seppala, J. V.; Harkonen, M. Polym. Sci., [Symp. Proc. Polym. ’91] 1991, 1, 235.

  27. Harkonen, M.; Seppala, J. V. Makromol. Chem. 1991, 192, 2857.

    Google Scholar 

  28. Chadwick, J. C.; van Kessel, G. M. M.; Sudmeijer, O. Macromol. Chem. Phys. 1995, 196, 1431.

    Google Scholar 

  29. Kang, K. K.; Shiono, T.; Jeong, Y.-T.; Lee, D.-H. J. Appl. Polym. Sci. 1999, 71, 293.

    Google Scholar 

  30. EP 362705, Himont, Inc., Barbe, P. C.; Noristi, L.; Scordamaglia, R.; Barino, L.; Albizzati, E.; Giannini, U.; Morini, G.

  31. Grison, C.; Batt-Coutrot, D.; Malinge, J.; Saudemont, T.; Coutrot, P. C. R. Acad. Sci. Paris, Chimie/Chemistry 2001, 4, 893.

    Google Scholar 

  32. Chadwick, J. C.; Morini, G.; Albizzati, E.; Balbontin, G.; Mingozzi, I.; Christofori, A.; Sudmeijer, O.; Van Kessel, G. M. M. Macromol. Chem. Phys. 1996, 197, 2501.

    Google Scholar 

  33. Guyot, A.; Spitz, R.; Journaud, C.; Eisenstein, O. International symposium on synthetic, Structural and Industrial Aspects of the Stereospecific Polymerization 1994, Milan.

  34. Barthel, V., PhD Thesis, University of Nancy I, 1995.

  35. Batt-Coutrot, D., PhD Thesis, University of Nancy I, 2000.

  36. Sacchi, M. C.; Forlini, F.; Tritto, I.; Mendichi, R.; Zannoni, G.; Noristi, L. Macromolecules 1992, 25, 5914.

  37. West, R. J. Am. Chem. Soc. 1954, 76, 6012.

    Google Scholar 

  38. Walton, K. L. Rubber Chemistry and Technology 2004, 77, 552.

  39. Mitani, M.; Kojoh, S.-I.; Kashiwa, N.; Fujita, T. Current Trends in Polymer Science 2001, 6, 85.

    Google Scholar 

  40. Kaminsky, W.; Laban, A. Applied Catalysis, A: General 2001, 222, 47.

    Google Scholar 

  41. Sacchi, M. C.; Fan, Z.-Q.; Forlini, F.; Tritto, I.; Locatelli, P. Macromol. Chem. Phys. 1994, 195, 2805.

    Google Scholar 

  42. Albizzati, E.; Dall’Occo, T.; Galimberti, M.; Morini, G. Stud. Surf. Sci. Catal. 1994, 89, 139.

    Google Scholar 

  43. Yang, C. B.; Hsu, C. C. J. Appl. Polym. Sci. 1995, 58, 1245.

    Google Scholar 

  44. Yang, C. B.; Hsu, C. C. J. Appl. Polym. Sci. 1995, 55, 621.

    Google Scholar 

  45. Xu, J.; Feng, L.; Yang, S.; Yang, Y.; Kong, X. Macromolecules 1997, 30, 7655.

  46. Fregonese, D.; Di Noto, V.; Peloso, A.; Bresadola, S. Macromol. Chem. Phys. 1999, 200, 2122.

    Google Scholar 

  47. Barino, L.; Scordamaglia, R. Macromol. Symp. 1995, 89, 101.

    Google Scholar 

  48. Barino, L.; Scordamaglia, R. Macromolecular Theory and Simulations 1998, 7, 407.

  49. Scordamaglia, R.; Barino, L. Macromolecular Theory and Simulations 1998, 7, 399.

  50. Yao, S.; Tanaka, Y. Macromolecular Theory and Simulations 2001, 10, 850.

    Google Scholar 

  51. Hansenne, C.; Pattou, D.; Standaert, A.; Debras, G.; Leherte, L.; Vercauteren, D. P. Abstracts of Papers, 223rd ACS National Meeting, Orlando, FL, United States, April 7–11, 2002 2002, POLY.

  52. Seth, M.; Ziegler, T. Macromolecules 2004, 37, 9191.

    Google Scholar 

  53. Mori, H.; Yamahiro, M.; Terano, M.; Takahashi, M.; Matsukawa, T. Angewandte Makromolekulare Chemie 1999, 273, 40.

    Google Scholar 

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Authors and Affiliations

  1. Laboratoire de Chimie Organique Biomoléculaire, Institut Nancéien de Chimie Moléculaire, FR CNRS 1742, UMR 7565, Université Henri Poincaré (Nancy-1), BP 239, 54506, Vandoeuvre-lès-Nancy Cedex, France

    Delphine Batt-Coutrot, Valérie Wolf, Claude Grison & Philippe Coutrot

  2. Groupement de Recherches de Lacq, BP 34, 64170, Artix, France

    Jean Malinge & Thierry Saudemont

  3. Laboratoire de Chimie Biomoléculaire, UMR 5032, ENSCM, 8, rue de l’Ecole Normale, 34296, Montpellier, France

    Claude Grison

  4. Laboratoire de Chimie Macromoléculaire, UMR 5076, ENSCM, 8, rue de l’Ecole Normale, 34296, Montpellier, France

    Delphine Batt-Coutrot

  5. Clariant Huningue, Avenue de Bâle, 68331, Huningue, France

    Valérie Wolf

  6. ATOFINA Research, Parc Industriel – Zone C, B - 7181, Feluy, Belgium

    Thierry Saudemont

Authors
  1. Delphine Batt-Coutrot
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  2. Valérie Wolf
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  3. Jean Malinge
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  4. Thierry Saudemont
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  5. Claude Grison
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  6. Philippe Coutrot
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Correspondence to Delphine Batt-Coutrot.

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Batt-Coutrot, D., Wolf, V., Malinge, J. et al. Study of Dimethoxysilacycloalkanes as External Donors in Ziegler-Natta Stereospecific Propylene Polymerisation. Polym. Bull. 54, 377–385 (2005). https://doi.org/10.1007/s00289-005-0399-9

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  • DOI: https://doi.org/10.1007/s00289-005-0399-9

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