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Macromonomers: Synthesis, characterization and applications

  • Paul F. Rempp
  • Emile Franta
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 58)

Abstract

The first part of this review critically examines the various attempts to prepare macromonomers: Anionic and cationic polymerization for synthesizing living polymers have been preferred whenever possible but two-step radical polymerizations making use of efficient transfer agents have also been applied.

In the second part, homopolymerization of the macromonomers — yielding highly branched structures — as well as copolymerization with a classical monomer — readily producing graft copolymers — are presented. The versatility of these methods is demonstrated by preparing original amphiphilic products. The properties of these segregated products are described in the few cases where they are available.

Keywords

Methyl Methacrylate Glycidyl Methacrylate Anionic Polymerization Cationic Polymerization Terminal Double Bond 
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.

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5 References

  1. 1.
    Cho, I.: Polym. (Korea) 4, 210 (1980)Google Scholar
  2. 2.
    Yamashita, Y.: Kobunshi, High Polymers Japan 31, 988 (1982); J. Appl. Polym. Sci. 36, 193 (1981)Google Scholar
  3. 3.
    Saegusa, T.: Top. Current Chem. 100, 75 (1982)Google Scholar
  4. 4.
    Vlegels, M.: Chem. en Kunstof 8, 12 (1982)Google Scholar
  5. 5.
    Rempp, P. et al.: Plaste und Kautschuk 28, 365 (1981)Google Scholar
  6. 6.
    Vogl, O.: J. Polym. Sci., Polym. Symp. 64, 1 (1978)Google Scholar
  7. 7.
    Greber, G., Reese, E.: Makromol. Chem. 55, 96 (1962)Google Scholar
  8. 8.
    Greber, G., Balciunas, A.: Makromol. Chem. 69, 193 (1963)Google Scholar
  9. 9.
    Greber, G., Balciunas, A.: Makromol. Chem. 79, 149 (1964)Google Scholar
  10. 10.
    Gillman, K. F., Senogles, E.: Polym. Lett. 5, 477 (1967)Google Scholar
  11. 11.
    ICI Ltd. Neth. Appl. 6, 409, 047 (1965)Google Scholar
  12. 12.
    Szwarc, M.: Carbanions, Living Polymers and Electron Transfer Process New York, Interscience Publishers 1968Google Scholar
  13. 13.
    Waack, R., Doran, M. A.: Polym. 2, 365 (1961)Google Scholar
  14. 14.
    Waack, R.: U.S. Patent 3, 235, 626 (1966)Google Scholar
  15. 15.
    Waack, R., Doran, M. A.: J. Org. Chem. 32, 3395 (1967)Google Scholar
  16. 16.
    Masson, P. et al.: Polym. Bull. 7, 17 (1982)Google Scholar
  17. 17.
    Kobayashi, S. et. al.: Polym. Bull. 9, 169 (1983)Google Scholar
  18. 18.
    Milkovich, R.: ACS. Polym. Preprints 21, 40 (1980) Milkovich, R., Chiang, M. T.: U.S. Patent 3, 786, 116 (1974) Other Patents by Milkovich R. and Chiang M. T. include U.S. Patents 3 846 393, 3 832 423, 3 842 050, 3 842 057, 3 842 058, 3 842 059 (1974); 3 862 098, 3 862 101, 3 862 102, 3 862 267 (1975); 4 085 168 (1978)Google Scholar
  19. 19.
    Rempp, P., Loucheux, M. H.: Bull. Soc. Chim. Fr. 1958, 1497Google Scholar
  20. 20.
    Anderson, B. C. et al.: Macromol. 14, 1599 (1981)Google Scholar
  21. 21.
    Asami, R.: IUPAC 28th. Symp. On Macromolecules, Amherst 1982, Preprints p. 71Google Scholar
  22. 22.
    Freyss, D., Leng, M., Rempp, P.: Bull. Soc. Chim. Fr. 1964, 221Google Scholar
  23. 23.
    Brody, M., Richards, D. H., Szwarc, M.: Chem. and Ind. (London) 1958, 1473Google Scholar
  24. 24.
    Masson, P., Franta, E., Rempp, P.: Makromol. Chem., Rapid Commun. 3, 499 (1982)Google Scholar
  25. 25.
    Candau, F. et al.: C.R. Acad. Sci. 284, 837 (1977)Google Scholar
  26. 26.
    Sigwalt, P.: Angew. Makromol. Chem. 94, 161 (1981)Google Scholar
  27. 27.
    Nametkine, N. S., Topchiev, A. V., Dourgarian, S. G.: J. Polym. Sci. c 4, 1053 (1963)Google Scholar
  28. 28. a)
    Ph. Chaumont, Herz, J., Rempp, P.: Europ. Polym. J. 15, 537 (1979)Google Scholar
  29. 28. b)
    Ph. Chaumont al.: Europ. Polym. J. 15, 459 (1979)Google Scholar
  30. 29.
    Kawakami, Y. et al.; Polym. J. 14, 913 (1982)Google Scholar
  31. 30.
    Katz, D., Zewi, I. G.: J. Polym. Sci. (Chem. Ed.) 16, 597 (1978)Google Scholar
  32. 31.
    Quirk, R. P., Chien, W. C.: Makromol. Chem. 183, 2071 (1982)Google Scholar
  33. 32.
    Schulz, D. N., Sanda, J. C., Willoughby, B. G.: Anionic Polymerization, ACS Symp. Series 166, 427 (1981)Google Scholar
  34. 33.
    Graetz, C. W.: Europ. Pat. Appl. 12524 (1980)Google Scholar
  35. 34.
    Gramain, P., Frere, Y.: to be publishedGoogle Scholar
  36. 35.
    Stowe, S. C.: U.S. Pat. 3 190 925 (1965)Google Scholar
  37. 36.
    Hamaide, T. et. al.: to be published in: Nouveau Journal de ChimieGoogle Scholar
  38. 37.
    Spach, G., Levy, M., Szwarc, M.: J. Chem. Soc. 1962, 355Google Scholar
  39. 38.
    Königsberg, I., Jagur-Grodzinski, J.: J. Polym. Sci. (Chem. Ed.), submitted for publicationGoogle Scholar
  40. 39.
    Dreyfuss, P., Dreyfuss, M. P.: Adv. Polym. Sci. 4, 528 (1967)Google Scholar
  41. 40.
    Penczek, S., Kubisa, P., Matyjaszewski, K.: Cationic Ring-Opening Polymerization of Heterocyclic Monomers, in: Adv. Polym. Sci. 37, 1980Google Scholar
  42. 41.
    Brown, W. B., Szwarc, M.: Trans. Farad. Soc. 54, 416 (1958)Google Scholar
  43. 42.
    Franta, E. et al.: J. Polym. Sci. Symp. 56, 139 (1976)Google Scholar
  44. 43.
    Smith, S., Hubin, A. J.: J. Macromol. Sci. (A) 7, 1399 (1973)Google Scholar
  45. 44.
    Croucher, T. G., Wetton, R. E.: Polym. 17, 205 (1976)Google Scholar
  46. 45.
    Zilliox, J. G. et al.: IUPAC Symp. Mainz 1979, Preprint p. 56Google Scholar
  47. 46.
    Sierra-Vargas, J. et al.: Polym. Bull. 3, 83 (1980)Google Scholar
  48. 47.
    Saegusa, T., Matsumoto, S.: J. Polym. Sci. (A)6, 1559 (1968)Google Scholar
  49. 48.
    Brzezinska, K. et al.: Makromol. Chem. 178, 2491 (1977)Google Scholar
  50. 49.
    Burgess, F. J. et. al.: Polym. 19, 334 (1978)Google Scholar
  51. 50.
    Asami, R., Takaki, M.: 27th. IUPAC Symp. on Macromolecules Strasbourg 1981, Preprints I, p. 240Google Scholar
  52. 51.
    Asami, R. et al.: Polym. Bull. 2, 713 (1980)Google Scholar
  53. 52.
    Sierra-Vargas, J. et al.: Polym. Bull. 7, 277 (1982)Google Scholar
  54. 53.
    Abadie, M. et. al.: Polym. 23, 445 (1982)Google Scholar
  55. 54.
    Richards, D. H.: Brit. Polym. J. 12, 89 (1980)Google Scholar
  56. 55.
    Takaki, M., Asami, R., Kuwabara, T.: Polym. Bull. 7, 521 (1982)Google Scholar
  57. 56.
    Reibel, L. et. al.: Polymeric Amines and Ammonium Salts (ed.) E. Goethals, p. 89, Oxford, New York, Pergamon Press 1980Google Scholar
  58. 57.
    Franta, E., Rempp, P., Reibel, L.: to be publishedGoogle Scholar
  59. 58.
    Munir, A., Goethals, E. J.: J. Polym. Sci. (Chem. Ed.) 19, 1985 (1981) Goethals, E. J., Munir, A.: Polymeric Amines and Ammonium Salts (ed.) E. Goethals p. 19, Oxford, New York, Pergamon Press 1980Google Scholar
  60. 59.
    Goethals, E. J., Vlegels, M.: Polym. Bull. 4, 521 (1981)Google Scholar
  61. 60.
    Smith, S., Schultz, W. J., Newmark, R. A.: ACS Symp. Series, 59, 13 (1977)Google Scholar
  62. 61.
    Goethals, E. J.: 28th IUPAC Symp. on Macromolecules, Amherst 1982, Preprint p. 204Google Scholar
  63. 62.
    Tanizaki, Y. et al.: ACS/CSJ Chem. Congress, Worldwide Prog. of the Petrochem. Org. and Polym. Chem. Indust. Honolulu, 1979Google Scholar
  64. 63.
    Heitz, W., Kress, H. J., Stix, W.: 28th. IUPAC Symp. on Macromolecules. Amherst 1982, Preprint p. 74Google Scholar
  65. 64.
    Kress, H. J., Heitz, W.: Makromol. Chem., Rapid Commun. 2, 427 (1981)Google Scholar
  66. 65.
    Kennedy, J. P.: Cationic Polymerization of Olefins: A Critical Inventory, New York, Wiley Intersci. Publ. 1974Google Scholar
  67. 65a.
    Kennedy, J. P., Marechal, E.: Carbocationic Polymerization, New York, Wiley Intersci. Publ. 1982Google Scholar
  68. 66.
    Kennedy, J. P.: Polym. J. 12, 609 (1980)Google Scholar
  69. 67.
    Kennedy, J. P.: 5th. Int. Symp. on Cationic Polym., Kyoto 1980, Preprints p. 6Google Scholar
  70. 68.
    Kennedy, J. P., Smith, R. A.: ACS Polym. Prepr. 20, 316 (1979)Google Scholar
  71. 69.
    Kennedy, J. P., Frisch, K. Jr.: IUPAC Symp. on Macromolecules, Firenze 1980 Preprints II, 162Google Scholar
  72. 70.
    Chang, V., Kennedy, J. P.: Polym. Bull. 5, 379 (1981)Google Scholar
  73. 71.
    Ivan, B., Kennedy, J. P., Chang, V.: J. Polym. Sci. (Chem. Ed.) 18, 1523, 1539, 3177 (1980)Google Scholar
  74. 72.
    Kennedy, J. P., Liao, J. P.: Polym. Bull 5, 11 (1981); 6, 135 (1981)Google Scholar
  75. 73.
    Percec, V. et al.: Polym. Bull. 8, 25 (1982)Google Scholar
  76. 74.
    Kennedy, J. P. et al.: Polym. Bull. 1, 575 (1979)Google Scholar
  77. 75.
    Tessier, M.: Thesis, Paris 1982Google Scholar
  78. 76.
    Kennedy, J. P., Huang, S. Y., Smith, R. A.: Polym. Bull. 1, 371 (1979); J. Macromol. Sci. (Chem.) (A)14, 1085 (1980)Google Scholar
  79. 77.
    Kennedy, J. P., Lo, C. Y.: ACS Polym. Prepr. 23, 99 (1982)Google Scholar
  80. 78.
    Kennedy, J. P. et al.: Polym. Bull. 8, 551, 557, 563, 571 (1982)Google Scholar
  81. 79.
    Narita, T., Yamagushi, Y., Tsuruta, T.: Bull. Chem. Soc. Japan 46, 3825 (1973)Google Scholar
  82. 80.
    Imai, N., Narita, T., Tsuruta, T.: Tetrahedron Lett. 38, 3517 (1971); Bull. Chem. Soc. Japan 46, 1242 (1973)Google Scholar
  83. 81.
    Tsuruta, T.: Polymeric Amines and Ammonium Salts (ed.) Goethals, E. J., p. 163, Oxford, New York, Pergamon Press 1980Google Scholar
  84. 82.
    Tsuruta, T., Narita, T., Nitadori, Y.: Makromol. Chem. 177, 3255 (1976)Google Scholar
  85. 83.
    Nitadori, Y., Tsuruta, T.: Makromol. Chem. 180, 1877 (1979)Google Scholar
  86. 84.
    Nishimura, T. et. al.: Makromol. Chem., Rapid Commun. 1, 573 (1980); Makromol. Chem. 183, 29 (1982)Google Scholar
  87. 85.
    Tsuruta, T.: 28th IUPAC Symp. on Macromolecules, Amherst 1982, Preprint p. 73Google Scholar
  88. 86.
    Maeda, M., Nitadori, Y., Tsuruta, T.: Makromol. Chem. 181, 2245 (1980)Google Scholar
  89. 87.
    Maeda, M., Nitadori, Y., Tsuruta, T.: Makromol. Chem. 181, 2251 (1980)Google Scholar
  90. 88.
    Maeda, M., Inoue, S.: Makromol. Chem., Rapid Commun. 2, 537 (1981)Google Scholar
  91. 89.
    Kimura, M. et. al.: Makromol. Chem. 183, 1393 (1982)Google Scholar
  92. 90.
    Ferruti, P. et. al.: J. Polym. Sci. (Chem. Ed.) 15, 2151 (1977)Google Scholar
  93. 91.
    Osmond, D. W., Waite, F. A., Walbridge, D. J.: Brit. Pat. 1 122 397 (1968)Google Scholar
  94. 92.
    Hudecek, S. et. al.: Polym. Bull. 3, 143 (1981)Google Scholar
  95. 93.
    Thompson, M. W., Waite, F. A.: U.S. Pat. 3 390 206 (1968) U.S. Pat. 3 627 239 (1971); Brit. Pat. 10 96 912 (1967)Google Scholar
  96. 94.
    Konter, W. et. al.: Makromol. Chem. 182, 2619 (1981)Google Scholar
  97. 95.
    Bamford, C. H., Jenkins, A. D.: Nature 176, 78 (1955)Google Scholar
  98. 96.
    Bamford, C. H., Jenkins, A. D., Johnston, R.: Trans. Farad. Soc. 55, 179 (1959)Google Scholar
  99. 97.
    Brosse, J. C., Baunier, M., Legeay, G.: Makromol. Chem. 182, 3457 (1981); 183, 303 (1982)Google Scholar
  100. 99.
    Yamashita, Y. et. al.: Polym. Bull. 5, 335 (1981)Google Scholar
  101. 98.
    Ito, K., Usami, N., Yamashita, Y.: Macromol. 13, 216 (1980)Google Scholar
  102. 100.
    Waite F. A.: J. Oil Col. Chem. Ass. 54, 342 (1971)Google Scholar
  103. 101.
    Yamashita, Y. et al.: Polym. J. 14, 255 (1982)Google Scholar
  104. 102.
    Kawakami, Y. et al.: J. Polym. Sci. (Polym. Lett.) 19, 629 (1981)Google Scholar
  105. 103.
    Simms, J. A., Walus, A. N.: U.S. Pat. 3 716 506 (1973)Google Scholar
  106. 104.
    Ashby, T. L., Parrish, D. B.: U.S. Pat. 3 480 601 (1969)Google Scholar
  107. 105.
    Yamashita, Y. et. al.: Polym. Bull. 5, 361 (1981)Google Scholar
  108. 106.
    Chujo, Y., Tastuda, T., Yamashita, Y.: Polym. Bull. 8, 239 (1982)Google Scholar
  109. 107.
    Asher, M., Vofsi, D.: J. Chem. Soc. (B) 1963, 1887 1964, 4962Google Scholar
  110. 108.
    Boutevin, B., Pietrasanta, Y.: J. Polym. Sci. (Chem. Ed.) 19, 499, 511 (1981)Google Scholar
  111. 109.
    Boutevin, B. et. al.: Europ. Polym. J. 14, 353 (1978)Google Scholar
  112. 110.
    Boutevin, B., Pietrasanta, Y., Taha, M.: Makromol. Chem. 183, 2977, 2985, 2995 (1982)Google Scholar
  113. 111.
    El Sarraf, T. et. al.: to be published in: Die Makromolekulare ChemieGoogle Scholar
  114. 112.
    Boutevin, B., Pietrasanta, Y., Sideris, A.: J. Fluorine Chem. 20, 727 (1982)Google Scholar
  115. 113.
    Kahrs, K. H., Zimmermann, J. W.: Makromol. Chem. 58, 75 (1962), see also Bui Duc Hao, Thesis, Strasbourg 1978Google Scholar
  116. 114.
    Grubisic, Z., Rempp, P., Benoit, H.: J. Polym. Sci., Polym. Let. 5, 753 (1967)Google Scholar
  117. 115.
    Asami, R. et. al.: Polym. J. 13, 141 (1981)Google Scholar
  118. 116.
    Zilliox, J. G.: Makromol. Chem. 156, 121 (1972)Google Scholar
  119. 117.
    Sierra-Vargas, J., Franta, E., Rempp, P.: Makromol. Chem. 182, 2603 (1981)Google Scholar
  120. 118.
    Kennedy, J. P., Lo, C. Y.: Polym. Bull. 8, 63 (1982)Google Scholar
  121. 119.
    Revillon, A., Hamaide, T.: Polym. Bull. 6, 235 (1982)Google Scholar
  122. 120.
    Kelen, T., Tüdös, F.: J. Macromol. Sci. Chem. 9, 1 (1975)Google Scholar
  123. 121.
    Rempp, P., Franta, E.: J. Herz, ACS Symp. Series, Anionic Polymerization (ed.) McGrath, p. 59, 1981Google Scholar
  124. 122.
    Gallot, Y., Rempp, P. Parrod, J.: J. Polym. Sci., Polym. Lett. 1, 329 (1963)Google Scholar
  125. 123.
    Candau, F., Afshar-Taromi, F., Rempp, P.: Polym. 18, 1253 (1977)Google Scholar
  126. 124.
    Rempp, P., Franta, E.: Pure Appl. Chem. 30, 229 (1972)Google Scholar
  127. 125.
    Kennedy, J. P.: Cationic Graft Copolymerization, Appl. Polym. Symp., J. Appl. Polym. Sci. 30, (1977)Google Scholar
  128. 126.
    Smets, G., Beylen, M. van: Makromol. Chem. 69, 140 (1963)Google Scholar
  129. 127.
    Bamford C. H. et al.: Polym. 10, 759, 771, 885 (1969); 13, 57 (1972)Google Scholar
  130. 128.
    Masson, P., Rempp, P., Franta, E.: to be publishedGoogle Scholar
  131. 129.
    Masson, P.: Thesis, Strasbourg 1982Google Scholar
  132. 130.
    Asami, R. et. al.: Polym. J. 13, 141 (1981)Google Scholar
  133. 131.
    Schulz, G. O., Milkovich, R.: J. Appl. Polym. Sci. 27, 4773 (1982)Google Scholar
  134. 132.
    Yamashita, Y.: 28th. IUPAC Symp. on Macromolecules, Amherst. 1982, Preprint p. 93Google Scholar
  135. 133.
    Owen, M. J., Kendrick, T. C.: Macromol. 3, 458 (1970)Google Scholar
  136. 134.
    Braun, J. M., Guillet, J. E.: Adv. Polym. Sci. 21, 107 (1976); Gray, D. G.: Progr. Polym. Sci. 5, 1 (1977)Google Scholar
  137. 135.
    Nishimura, T. et. al.: Makromol. Chem., Rapid Commun. 1, 573 (1980)Google Scholar
  138. 136.
    Mathias, L. J., Canterberry, J. B., South, M.: J. Polym. Sci., Polym. Lett. 20, 473 (1982)Google Scholar

Copyright information

© Spring-Verlag 1984

Authors and Affiliations

  • Paul F. Rempp
    • 1
  • Emile Franta
    • 1
  1. 1.Centre de Recherches sur les Macromolécules (CNRS)Strasbourg CedexFrance

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