Advertisement

Macrozwitterion polymerization

  • David Samuel Johnston
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 42)

Abstract

In the vast majority of ionic polymerizations reported in the literature the counterion is ionically bound to the polymer chain. When the counterion is covalently bound to the chain, the polymerization is termed macrozwitterionic. This review surveys what is known about this relatively unexplored area of polymer chemistry. A brief history of the topic is followed by a summary of the literature. The evidence presented in each report for the formation of macrozwitterions is critically assessed. Then an attempt is made to draw out features common to all monomer/initiator combinations which can thus be considered characteristic of macrozwitterion polymerization. These are contrasted to what would be thought typical of an ion pair polymerization. Macrozwitterionic polymerization offers a convenient route to macrocyclic ligands and, when polymeric initiators are used, a range of novel graft copolymers.

Keywords

Tertiary Amine Monomer Concentration Polymerization Rate Aliphatic Amine Anionic Polymerization 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

5 References

  1. 1.
    Ayres, D. C.: “Carbanions in Synthesis”, London: Oldbourne 1966, p. 112Google Scholar
  2. 2.
    Walker, B. J.: “Organophosphorus Chemistry”, Penguin 1972, p. 67Google Scholar
  3. 3.
    Gresham, T. L., Jansen, J. E., Shaver, F. W., Bankert, R. A., Fiedorek, F. T.: J. Am. Chem. Soc. 73, 3168 (1951)CrossRefGoogle Scholar
  4. 4.
    Hunter, W. H., Yohe, R. V.: J. Am. Chem. Soc. 55, 1248 (1933)CrossRefGoogle Scholar
  5. 5.
    Williams, H.: J. Chem. Soc. 1940, 775Google Scholar
  6. 6.
    Price, C. C.: “Reactions at Carbon-Carbon Double Bonds”, Interscience, New York, 1946Google Scholar
  7. 7.
    Horner, L., Jurgeleit, H., Klupfel, K.: Justus Liebigs Ann. Chem. 59, 108 (1955)Google Scholar
  8. 8.
    Swarc, M.: Makromol. Chem. 35, 132 (1960)CrossRefGoogle Scholar
  9. 9.
    Klippert, H., Ringsdorf, H.: Preprints I.U.P.A.C. Helsinki, Symposium on Macromolecules, 1–35, 211 (1972)Google Scholar
  10. 10.
    Klippert, H., Ringsdorf, H.: Makromol. Chem. 153, 289 (1972)CrossRefGoogle Scholar
  11. 11.
    Ranogayets, F., Kotchetov, Ye. V., Markevich, M. A., Enikolopyan, N. S.: Pol. Sci. U. S. S. R. 15, 1508 (1973)CrossRefGoogle Scholar
  12. 12.
    Ranogajec, F., Kotchetov, E. V., Markevich, M. A., Enikolopyan, N. S.: J. Polym. Sci., Polym. Symp. 42, 531 (1973)Google Scholar
  13. 13.
    Markevich, M. A., Kotchetov, E. V., Ranogajec, F., Enikolopyan, N. S.: J. Macromol. Sci. Chem. 8(2), 265 (1972)Google Scholar
  14. 14.
    Ranogajec, F., Kotchetov, E. V., Markevich, M. A., Enikolopyan, N. S., Dvornik, I.: Croatica Chimica Acta 46(2), 83 (1974)Google Scholar
  15. 15.
    Ogawa, T., Taninaka, T.: J. Polym. Sci. Part A-1, 10, 2005 (1972)CrossRefGoogle Scholar
  16. 16.
    Ogawa, T., Romero, J.: Eur. Polym. J. 13, 419 (1977)CrossRefGoogle Scholar
  17. 17.
    Ogawa, T., Quintana, P.: J. Polym. Sci. 13, 2517 (1975)Google Scholar
  18. 18.
    Kotchetov, Ye. V., Berlin, A. A., Enikolopyan, N. S.: Pol. Sci. U.S.S.R. 8, 1122 (1966)CrossRefGoogle Scholar
  19. 19.
    Kotchetov, Ye. V., Berlin, A. A., Enikolopyan, N. S.: Pol. Sci. U.S.S.R. 8, 1117 (1966)CrossRefGoogle Scholar
  20. 20.
    Kotchetov, Ye. V., Berlin, A. A., Masal'skaya, Yet. M., Enikolopyan, N. S.: Pol. Sci. U. S. S. R. 12, 1264 (1970)CrossRefGoogle Scholar
  21. 21.
    Markevich, M. A., Kotchetov, Ye. V., Enikolopyan, N. S.: Pol. Sci. U.S.S.R. 13, 1163 (1971)CrossRefGoogle Scholar
  22. 22.
    Jaacks, V., Eisenbach, C. D., Kern, W.: Makromol. Chem. 161, 139 (1972)CrossRefGoogle Scholar
  23. 23.
    Saegusa, T., Kobayashi, S., Kimura, Y.: Macromolecules 7, 257, (1974)Google Scholar
  24. 24.
    Vofsi, D., Katchalsky, A.: J. Polym. Sci. 26, 127 (1957)CrossRefGoogle Scholar
  25. 25.
    Grodzinsky, J., Katchalsky, A., Vofsi, D.: Makromol. Chem. 44–46, 591 (1961)CrossRefGoogle Scholar
  26. 26.
    Jagur-Grodzinsky, J.: “Encyclopedia of Polymer Science and Technology”, Vol. 9, p. 315Google Scholar
  27. 27.
    Grodzinsky, J., Thesis, Ph. D.: Hebrew University 1961Google Scholar
  28. 28.
    Butler, G. B., Sivaramakrishnan, K. N.: Polym. Prepr. 17(2), 608 (1976)Google Scholar
  29. 29.
    Hopf, H., Lüssi, H., Allisson, S.: Makromol. Chem. 44–46, 95 (1961)CrossRefGoogle Scholar
  30. 30.
    Jaacks, V., Franzmann, G.: Makromol. Chem. 143, 283 (1971)CrossRefGoogle Scholar
  31. 31.
    Donnelly, E. F., Johnston, D. S., Pepper, D. C., Dunn, D. J.: J. Polym. Sci., Polym. Lett. Ed. 15, 399 (1977)Google Scholar
  32. 32.
    Pepper, D. C.: J. Polym. Sci., Polym. Symp. 62, 65 (1978)Google Scholar
  33. 33.
    Johnston, D. S., Pepper, D. C.: Makromol. Chem. 182, 393 (1981)CrossRefGoogle Scholar
  34. 34.
    Johnston, D. S., Pepper, D. C.: Makromol. Chem. 182, 407 (1981)CrossRefGoogle Scholar
  35. 35.
    Johnston, D. S., Pepper, D. C.: Makromol. Chem. 182, 421 (1981)CrossRefGoogle Scholar
  36. 36.
    Oguni, N., Kamachi, M., Stille, J. K.: Macromolecules 7, 435 (1974)CrossRefGoogle Scholar
  37. 37.
    Tarvin, R. F., Aoki, S., Stille, J. K.: Macromolecules 5, 663, (1972)CrossRefGoogle Scholar
  38. 38.
    Machacek, Z., Mejzlik, J., Pac, J.: J. Polym. Sci. 52, 309 (1961)CrossRefGoogle Scholar
  39. 39.
    Enikolopyan, N. S.: J. Polym. Sci. 58, 1301 (1962)CrossRefGoogle Scholar
  40. 40.
    Mathes, N., Jaacks, V.: Makromol. Chem. 135, 49 (1970)CrossRefGoogle Scholar
  41. 41.
    Künzel, E., Giefer, A., Kern, W.: Macromol. Chem. 96, 17 (1966)CrossRefGoogle Scholar
  42. 42.
    Etienne, Y., Soulas, R.: J. Polym. Sci., Part C, 4, 1061 (1963)Google Scholar
  43. 43.
    Jaacks, V., Mathes, N.: Makromol. Chem. 131, 295 (1970)CrossRefGoogle Scholar
  44. 44.
    Mathes, N., Jaacks, V.: Makromol. Chem. 142, 209 (1971)CrossRefGoogle Scholar
  45. 45.
    Mayne, N. R.: A.C.S. Advan. Chem. Ser. 29, 175 (1973)Google Scholar
  46. 46.
    Wilson, D. R., Beaman, R. G.: J. Polym. Sci., Part A-1, 8, 2161 (1970)Google Scholar
  47. 47.
    Fisher, R. F.: J. Polym. Sci. 44, 155 (1960)CrossRefGoogle Scholar
  48. 48.
    Wieland, Th.: Angew. Chem. 66, 507 (1954)Google Scholar
  49. 49.
    Kricheldorf, H. R., Bosinger, K.: Makromol. Chem. 177, 1243 (1976)CrossRefGoogle Scholar
  50. 50.
    Seeney, C. E., Harwood, H. J.: “Ionic Polymerisation, Unsolved Problems”, Furukawa, J. and Vogl, O. Eds., Dekker, New York 1976, p. 144Google Scholar
  51. 51.
    Kern, W., Jaacks, V.: J. Polym. Sci. 48, 399 (1960)Google Scholar
  52. 52.
    Schmidt, D. L., Smith, H. B., Yoshimine, M., Hatch, M. J.: J. Polym. Sci., Part A-1, 10, 2951 (1972)Google Scholar
  53. 53.
    Chapiro, A., Du Lieu, J., Laborie, F.: Paper presented at 3rd International Symposium on Radiation Chemistry, Tihany 1971Google Scholar
  54. 54.
    Schmidt, D. L.: Polym. Prepr. 18(1), 121 (1977)Google Scholar
  55. 55.
    Brandi, A., De Sarlo, F., Guarna, A.: J. Chem. Soc., Perkin I 1827 (1976)Google Scholar
  56. 56.
    Kantor, S. W., Osthoff, R. C.: J. Am. Chem. Soc. 75, 931 (1953)Google Scholar
  57. 57.
    Hamann, K.: Z. Elektrochem. 60, 317 (1956)Google Scholar
  58. 58.
    Huisgen, R.: Angew. Chem. 67, 439 (1955)Google Scholar
  59. 59.
    Bawn, C. E. H., Ledwith, A., Matthies, P.: J. Polym. Sci. 34, 93 (1959)Google Scholar
  60. 60.
    Plesch, P. H.: Ricerca Sci. 25, 140 (1955)Google Scholar
  61. 61.
    Saegusa, T.: Chem. Technol. 5, 295 (1975)Google Scholar
  62. 62.
    Saegusa, T., Kobayashi, S., Yokoyama, T.: Polym. Prepr. 18(1), 125 (1977)Google Scholar
  63. 63.
    Saegusa, T., Kobayashi, S., Hayashi, K.: Macromolecules 11, 360 (1978)Google Scholar
  64. 64.
    Overberger, C. G.: “Encyclopedia of Polymer Science and Technology”, Vol. 11, p. 96Google Scholar
  65. 65.
    Swarc, M.: “Carbanions, Living Polymers and Electron Transfer Processes”, Interscience New York 1968, p. 596Google Scholar
  66. 66.
    Walker, B. J.: “Organophosphorus Chemistry”, Penguin 1972, p. 49Google Scholar
  67. 67.
    Mayer, U.: Pure Appl. Chem. 41, 291 (1975)Google Scholar
  68. 68.
    Johnston, D. S., Thesis, Ph. D., University of Dublin 1978Google Scholar
  69. 69.
    Miura, M., Akatsu, F., Ito, H., Nagakuko, K.: J. Polym. Sci., Polym. Chem. Ed. 17, 1568 (1979)Google Scholar
  70. 70.
    Westfahl, J. C., Gresham, T. L.: J. Am. Chem. Soc. 76, 1076 (1954)Google Scholar
  71. 71.
    De Sarlo, F., Guarna, A., Speroni, A.: Chem. Abstr. 88, 89 639 c (1978)Google Scholar

Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • David Samuel Johnston
    • 1
  1. 1.Chemical LaboratoryTrinity CollegeDublin 2Ireland

Personalised recommendations