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Recent Progress in the Use of Phase Transfer Catalysis for Polycondensation Reactions. Application to the Preparation of Polyethers, Polycarbonates and Polyesters.

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Recent Advances in Mechanistic and Synthetic Aspects of Polymerization

Part of the book series: NATO ASI Series ((ASIC,volume 215))

Abstract

Phase transfer catalysis has been applied to the synthesis by polycondensation of polyethers, polycarbonates and polyesters, either using a liquid-liquid process (polyethers and polycarbonates) or a solid-liquid process (polyesters). The kinetics and mechanism were discussed, and the influence of several parameters such as the nature of the solvent and the stoichiometry and concentration of the reagents was investigated. It was possible to prepare polycondensates having high enough molecular weights, low polydispersities and well-controlled end groups, starting from dihalogeno compounds and diphenols (liquid-liquid system) or alkaline dicarboxylates (synthesis of polyesters). Further physico-chemical experiments were carried out with the resulting polymers. End-to-end cyclization dynamics in dilute solution was studied for a polycarbonate. Interesting thermal properties were found in the case of polyesters for which an odd-even effect was detected.

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References

  1. Laboratoire de Chimie Macromoléculaire associé au CNRS UA 24.

    Google Scholar 

  2. A.K. Banthia, D.C. Webster and J.E. Mc.Grath, Org. Coatings and Plastics Chem. Prep., 42, 127 (1980).

    CAS  Google Scholar 

  3. A.K. Banthia, D. Lundsford, D.C. Webster and J.E. McGrath, J. Macromol. Sci. Chem. A15, 943 (1981).

    Article  Google Scholar 

  4. R. Kellman, D.G. Gerbi, R.F. Williams and J.L. Morgan, Polym. Prep. 21 (2), 164 (1980).

    CAS  Google Scholar 

  5. T.D. N’guyen, Thèse de doctorat d’Etat, Paris (1981).

    Google Scholar 

  6. G.G. Cameron and K.S. Law, Makromol. Chem. Rapid. Commum. 3, 99 (1982).

    Article  CAS  Google Scholar 

  7. J.L. Jin and J.H. Chang, Polym. Prep. 23, 156 (1982); ‘Phase transfer polycondensation of bisphenolate anions and 1,6-dibromohexane’. Crown ethers and phase transfer catalysis in polymer science (L.J. Mathias and C.E. Carraher,Jr, editors) Plenum Press p. 91 (1984).

    Google Scholar 

  8. O. Mahamat, Thèse de doctorat de 3e cycle, Paris (1983).

    Google Scholar 

  9. N. Yamazaki and Y. Imai, Polym. J. 15, 603 (1983).

    Article  CAS  Google Scholar 

  10. T.D. N’guyen and S. Boileau, ‘Synthesis of polyethers by phase transfer catalyzed polycondensation’ Crown ethers and phase transfer catalysis in polymer science (L.J. Mathias and C.E. Carraher, Jr, editors), Plenum Press, p. 59 (1984).

    Google Scholar 

  11. H. Sleiman, Thèse de doctorat de 3e cycle, Paris (1985).

    Google Scholar 

  12. Y. Imai, M. Ueda and M. II, J. Polym. Sci. Polym. Lett. Ed. 17, 85 (1979).

    Article  CAS  Google Scholar 

  13. N. Yamazaki and Y. Imai, Polym. J. 17 (2), 377 (1985).

    Article  CAS  Google Scholar 

  14. D.J. Gerbi, R.F. Williams, R. Kellman and J.L. Morgan, Polym. Prep. 22, 385 (1981).

    CAS  Google Scholar 

  15. D.G. Gerbi, G. Dimotsis, J.L. Morgan, R.F. Williams and R. Kellman, J. Polym. Sei. Polym. Lett. Ed. 23, 551 (1985).

    Article  CAS  Google Scholar 

  16. A.S. Hay, F.J. Williams, H.M. Relles, B.M. Boulette, P.E. Donahue and D.S. Johnson, J. Polym. Sci. Polym. Lett. Ed. 21, 449 (1983).

    Article  CAS  Google Scholar 

  17. A.S. Hay, F.J. Williams, H.M. Relles, J.C. Carnahan, G.R. Loucks, B.M. Boulette, P.E. Donahue and D.S. Johnson, New monomers and polymers (B.M. Culberts0n and C.U. Pittman,Jr, editors) Plenum Press p. 67 (1984).

    Google Scholar 

  18. A.S. Hay, F.J. Williams, H.M. Relles and B.M. Boulette, J. Macromol. Sci. Chem. A21, 1065 (1984).

    Article  Google Scholar 

  19. V. Percec and B.C. Auman, Polym. Bull. 10, 385 (1983).

    Article  CAS  Google Scholar 

  20. V. Percec, B.C Auman and P.L. Rinaldi, Polym. Bull. 10, 391 (1983).

    Article  CAS  Google Scholar 

  21. V. Percec and B.C. Auman, Makromol. Chem. 185, 617 (1984).

    Article  CAS  Google Scholar 

  22. V. Percec and H. Nava, Makromol. Chem. Rapid. Commun. 5, 319 (1984).

    Article  CAS  Google Scholar 

  23. V. Percec and B.C. Auman, Polym. Bull. 12, 253 (1984).

    Article  CAS  Google Scholar 

  24. T.D. Shaffer and V. Percec, Makromol. Chem. Rapid. Commun., 6, 97 (1985).

    Article  CAS  Google Scholar 

  25. T.D. Shaffer and V. Percec, J. Polym. Sci. Polym. Lett. Ed. 23, 185 (1985).

    Article  CAS  Google Scholar 

  26. T.D. Shaffer, M. Jamaludin and V. Percec, J. Polym. Sci. Polym. Chem. Ed. 23, 2913 (1985).

    Article  CAS  Google Scholar 

  27. T.D. Shaffer, M. Jamaludin and V. Percec, J. Polym. Sci. Polym. Chem. Ed., 24, 15 (1986).

    Article  CAS  Google Scholar 

  28. T.D. Shaffer and V. Percec, Makromol. Chem. 187, 111 (1986).

    Article  Google Scholar 

  29. T.D. Shaffer and V. Percec, Makromol. Chem. 187, 1431 (1986).

    Article  CAS  Google Scholar 

  30. A.M. Muñoz, F.R. Diaz and L.H. Tagle, Polym. Bull., 11, 493 (1984).

    Article  Google Scholar 

  31. P. Keller, Makromol. Chem. Rapid Commun. 6, 255 (1985).

    Article  CAS  Google Scholar 

  32. P.H. Parsania, P.P. Shah, K.C. Patel and R.D. Patel, J. Macromol. Sci. Chem. A22 (11), 1495 (1985).

    Article  Google Scholar 

  33. K. Soga, S. Hosoda and S. Ikeda, J. Polym. Sci. Polym. Lett. Ed. 15, 611 (1977).

    Article  CAS  Google Scholar 

  34. K. Soga, Y. Toshida, S. Hosoda and S. Ikeda, Makromol. Chem. 178, 2747 (1977).

    Article  CAS  Google Scholar 

  35. K. Soga, Y. Toshida, S. Hosoda and S. Ikeda, Makromol. Chem. 179, 2379 (1978).

    Article  CAS  Google Scholar 

  36. G. Rokicki, W. Kuran and J. Kielkiewicz, J. Polym. Sci. Polym. Chem. Ed., 20, 967 (1982).

    Article  CAS  Google Scholar 

  37. G.Rokicki, B. Pogorzelska-Marciniak and W. Kuran, Polym. J. 14, 847 (1982).

    Google Scholar 

  38. J.M.J. Frechet, F. Bouchard, F.M. Houlihan, E. Eichler, B. Kryczka and C.G. Willson, Makromol. Chem. Rapid Commun., 7, 121 (1986).

    Article  CAS  Google Scholar 

  39. M. Majdoub, Thèse de doctorat de 3e cycle, Paris (1985).

    Google Scholar 

  40. J.A. Mykroyannidis, Eur. Polym. J., 21, 895 (1985).

    Article  Google Scholar 

  41. J.A. Mykroyannidis, Eur. Polym. J., 21, 1031 (1985).

    Article  Google Scholar 

  42. Z.K. Brzozowski, J. Kielkiewicz and Z. Goclawski, Angew. Makromol. Chem. 44, 1 (1975).

    Article  CAS  Google Scholar 

  43. Z.K. Brozozowski, J. Dubczynski and J. Petrus, J. Macromol. Sci. Chem. A13, 875 (1979).

    Article  Google Scholar 

  44. Z.K. Brzozowski, J. Dubczynski and J. Petrus, J. Macromol. Sci. Chem., A13, 887 (1979).

    Article  Google Scholar 

  45. Y. Imai and S. Tassavori, J. Polym. Sci. Polym. Chem. Ed., 22, 1319 (1984).

    Article  CAS  Google Scholar 

  46. J.S. Riffle, A.K. Banthia, D.C. Webster and J.E. Mcgrath, Org. Coatings and Plastics Che. Prep., 42, 122 (1980).

    CAS  Google Scholar 

  47. J.S. Riffle, R.G. Freelin, A.K. Banthia and J.E. McGrath, J. Macromol. Sci. Chem., A15, 967 (1981).

    Article  Google Scholar 

  48. F.L. Keohan, R.G. Freelin, J.S. Riffle, I. Yilgör and J.E. McGrath, J. Polym. Sci. Polym. Chem. Ed., 22, 679 (1984).

    Article  CAS  Google Scholar 

  49. G.G. Cameron and K.S. Law, Polymer, 22, 272 (1981).

    Article  CAS  Google Scholar 

  50. J. Kielkiewicz, W. Kuran and B. Pogorzelska, Makromol. Chem. Rapid Commun., 2, 255 (1981).

    Article  CAS  Google Scholar 

  51. R. Dorigo, Rapport d’activité de DEA, Paris (1986).

    Google Scholar 

  52. C.G. Cameron, G.M. Buchan and K.S. Law, Polymer, 22, 558 (1981)

    Article  CAS  Google Scholar 

  53. Société Nationale des Poudres et Explosifs, 12 quai Henri IV 75181 Paris Cédex 04 FRANCE.

    Google Scholar 

  54. Laboratoire de Physique et de Chimie des Hauts Polymères de l’Université Catholique de Louvain la Neuve, Belgique.

    Google Scholar 

  55. Laboratoire de Physicochimie Structurale et Macromoléculaire de l’ESPCI, 10 rue Vauquelin 75005 Paris, France.

    Google Scholar 

  56. E. Shchori and J.E. McGrath, Appl. Polym. Symp., 34, 103 (1978)

    CAS  Google Scholar 

  57. M. Haamdi, Rapport d’activité de DEA, Paris (1985).

    Google Scholar 

  58. F. Mechin, unpublished results.

    Google Scholar 

  59. S. Boileau, F. Mechin and M.A. Winnik, unpublished results.

    Google Scholar 

  60. M. A. Winnik, Acc. Chem. Res., 18, 73 (1985).

    Article  CAS  Google Scholar 

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© 1987 D. Reidel Publishing Company

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Mahamat, O., Majdoub, M., Méchin, F., Sleiman, H., Boileau, S. (1987). Recent Progress in the Use of Phase Transfer Catalysis for Polycondensation Reactions. Application to the Preparation of Polyethers, Polycarbonates and Polyesters.. In: Fontanille, M., Guyot, A. (eds) Recent Advances in Mechanistic and Synthetic Aspects of Polymerization. NATO ASI Series, vol 215. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3989-9_15

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  • DOI: https://doi.org/10.1007/978-94-009-3989-9_15

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8270-9

  • Online ISBN: 978-94-009-3989-9

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