Graft Copolymers

  • B. C. Trivedi
  • B. M. Culbertson

Abstract

Considerable effort has been spent on developing methods for grafting MA or MA copolymers to the backbone of a variety of saturated and unsaturated polymeric materials. In general, MA grafting has been and is continuing to be explored as a technique to improve the physicochemical properties of various polymers, by providing polarity to promote hydrophilicity, adhesion, and dyeability, give functionality for crosslinking and other chemical modifications, promote compatibility with other polymers and fillers, and provide improved heat resistance. In rubber chemistry, grafting has been investigated for producing materials with improved green strength, vulcanization and fatigue properties, as well as decreasing the oxidizability of the materials. The techniques explored have included free radical, “ene” (see Chapter 5), and Diels-Alder (see Chapter 4) type reactions. In graft copolymers the backbone and side chains may both be homopolymeric; the backbone may be homopolymeric and the side chains copolymeric; or vice versa; or both the backbone and side chains may be copolymeric but of different chemical composition. To varying extent, all these conditions have been explored for MA, with much of the effort disclosed in the patent literature. These grafting studies are reviewed and discussed, along with providing a comprehensive patent listing on MA graft copolymers showing the many possible uses that exist for such materials.

Keywords

Natural Rubber Graft Copolymer Maleic Anhydride Patent Literature Peroxide Initiator 
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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References

  1. 1.
    V. G. Protasov and N. K. Baramboim, Plast. Massy 2, 8 (1969);Google Scholar
  2. 1a.
    V. G. Protasov and N. K. Baramboim, Chem. Abstr. 70, 107029p (1969).Google Scholar
  3. 2.
    V. G. Protasov and N. K. Baramboim, Plast. Massy 8, 22 (1972);Google Scholar
  4. 2a.
    V. G. Protasov and N. K. Baramboim, Chem. Abstr. 77, 153349k (1972).Google Scholar
  5. 3.
    V. G. Protasov and N. K. Baramboim, Nauch Tr. Mosk. Technol. Inst. Legk. Prom. 38, 176, 186 (1972);Google Scholar
  6. 3a.
    V. G. Protasov and N. K. Baramboim, Chem. Abstr. 79, 6057b (1973).Google Scholar
  7. 4.
    V. G. Protasov and N. K. Baramboim, Plaste. Kaut. 12(2), 89 (1972);Google Scholar
  8. 4a.
    V. G. Protasov and N. K. Baramboim, Chem. Abstr. 76, 141634r (1972).Google Scholar
  9. 5.
    V. G. Protasov and N. K. Baramboim, Plaste. Kaut. 23(3), 185 (1976);Google Scholar
  10. 5.
    V. G. Protasov and N. K. Baramboim,Chem. Abstr. 84, 181024p (1976).Google Scholar
  11. 6.
    W. Gabara and S. Porejko, J. Polym. Sci. A-1 5(7), 1547 (1967).Google Scholar
  12. 7.
    S. Porejko, W. Gabara, T. Blazejewics, and M. Leika, J. Polym Sci. A-1 7(7), 1647 (1968).Google Scholar
  13. 8.
    W. Gabara and S. Porejko, Polimery 12(4), 151 (1967);Google Scholar
  14. 8a.
    W. Gabara and S. Porejko, Chem. Abstr. 68, 30540x (1968);Google Scholar
  15. 8b.
    W. Gabara and S. Porejko, W. Gabara and S. Porejko, Polimery 12(5), 196 (1967);Google Scholar
  16. 8c.
    W. Gabara and S. Porejko, W. Gabara and S. Porejko, Chem. Abstr. 68, 115336k (1968).Google Scholar
  17. 9.
    Union Carbide, U.S. Pat. 3,216,885 (1965).Google Scholar
  18. 10.
    J. Z. Onszagh and W. Gabara,Nukleonika 11(9), 669 (1966);Google Scholar
  19. 10a.
    J. Z. Onszagh and W. Gabara, Chem. Abstr. 66, 116107g (1967).Google Scholar
  20. 11.
    V. G. Protasov, N. K. Baraboim, L. P. Baranova, and I. D. Sterligov, Izv. Visshikh Uchebn. Zanedenii Tekhnol Legk. Prom. 1, 54 (1966);Google Scholar
  21. 11a.
    V. G. Protasov, N. K. Baraboim, L. P. Baranova, and I. D. Sterligov, Chem. Abstr. 64, 17797f (1966).Google Scholar
  22. 12.
    A. Baszkin and L. T. M. Saraga, J. Colloid. Interface Sci. 43(2), 473 (1973).Google Scholar
  23. 13.
    N. G Gaylord, Am. Chem. Soc. Div. Org. Coat. Plast. Prepr. 40, 456 (1979).Google Scholar
  24. 14.
    R. M. Joshi, J. Appl. Polym. Sci. 24(2), 595 (1979).Google Scholar
  25. 15.
    A. Romarov, Plaste Kaut. 12(9), 521 (1965);Google Scholar
  26. 15a.
    A. Romarov, Chem. Abstr. 64, 11378a (1966).Google Scholar
  27. 16.
    A. Romarov, Plaste Kaut. 14(1), 9 (1967)Google Scholar
  28. 16a.
    A. Romarov,Chem. Abstr. 66, 66104f (1967).Google Scholar
  29. 17.
    F. Ide, A. Hasegawa, and K. Kamada, Kobunshi Kagaku 25(277), 298 (1968);Google Scholar
  30. 17a.
    F. Ide, A. Hasegawa, and K. Kamada,Chem. Abstr. 69, 78043k (1968).Google Scholar
  31. 18.
    M. Neda, S. Mizunuma, M. Oba, and Y. Minoura, Kogyo Kagaku Zasshi 71(3), 432 (1968);Google Scholar
  32. 18a.
    M. Neda, S. Mizunuma, M. Oba, and Y. Minoura,Chem. Abstr. 69, 28223y (1968).Google Scholar
  33. 19.
    A. I. Kurilenko and V. I. Glukhov, Probl. Fiz. Khim. Mekh. Volaknistykh Poristykh Dispersynzkh Strukt. Mater., Mater. Konf. Riga, 605 (1965);Google Scholar
  34. 19a.
    A. I. Kurilenko and V. I. Glukhov, Chem. Abstr. 68, 79474t (1968).Google Scholar
  35. 20.
    F. Ide, A. Hasegawa, and K. Kamada, Kobunshi Kagaku 25(275), 167 (1968);Google Scholar
  36. 20a.
    F. Ide, A. Hasegawa, and K. Kamada, Chem. Abstr. 69, 59758f (1968);Google Scholar
  37. 20b.
    F. Ide, A. Hasegawa, and K Kamada, Chem. Abstr. 25(274), 107 (1968);Google Scholar
  38. 20c.
    F. Ide, A. Hasegawa, and K. Kamada, Chem Abstr. 69, 11031m (1968).Google Scholar
  39. 21.
    Hercules, Inc., U.S. Pat. 3,437,550 (1969).Google Scholar
  40. 22.
    Y. Minoura, M. Ueda, S. Mizunuma, and M. Oba, J. Appl. Polym. Sci. 13(8), 1625 (1969).Google Scholar
  41. 23.
    V. G. Protasov, N. L. Makhmudbekova, and N. K. Baramboim, Nauch Tr. Mosk. Tekhnol. Inst. Legk. Prom. 3663 (1969);Google Scholar
  42. 23a.
    V. G. Protasov, N. L. Makhmudbekova, and N. K. Baramboim,Chem. Abstr. 75, 77464k (1971).Google Scholar
  43. 24.
    V. D. Sukhoverkhov, V. M. Bludilin, O. L. Glavati,and N. PMysak Sb. Tr. Vses, Obedin Neftekhim 5, 105 (1973);Google Scholar
  44. 24a.
    V. D. Sukhoverkhov, V. M. Bludilin, O. L. Glavati, and N. P. MysakC.’hemn. Abstr. 83, 28654d (1975).Google Scholar
  45. 25.
    M. S. Akutin, R. I. Mustafaev, and V. M. Momedov, Plast. Massy 9, 50 (1975);Google Scholar
  46. 25a.
    M. S. Akutin, R. I. Mustafaev, and V. M. Momedov, Chem. Abstr. 84, 18257h (1976).Google Scholar
  47. 26.
    N. K. Baramboim and B. V. Sautin, Vysokomol. Soedin. 2, 1196 (1960);Google Scholar
  48. 26a.
    N. K. Baramboim and B. V. Sautin, Chem. Abstr. 55, 21635g (1961).Google Scholar
  49. 27.
    M. Narita, M. Aikiyama, and M. Okawara, Kogyo Kagaku Zasshi 70(8), 1432 (1967);Google Scholar
  50. 27a.
    M. Narita, M. Aikiyama, and M. Okawara, Chem. Abstr. 68, 50789p (1968).Google Scholar
  51. 28.
    N. K. Baramboim and V. I. Rakityanskii, Nauchn. Tr. Mosk. Telchnol. Inst. Legk. Prom. Sci. 41, 46 (1977);Google Scholar
  52. 28a.
    N. K. Baramboim and V. I. Rakityanskii, Chem. Abstr. 90, 152888s (1979).Google Scholar
  53. 29.
    M. Okawara, Asahi Garasu Kogyo Gijutsu Shorei-kai Kenkyu Hokaku, 14, 185 (1968);Google Scholar
  54. 29a.
    M. Okawara, Chem. Abstr. 71, 113561t (1969).Google Scholar
  55. 30.
    P. Hrdlovic and I. Lukac, J. Polym. Sci. Polym. Symp. 47, 319 (1974).Google Scholar
  56. 31.
    P. Hrdlovic, L. Zahumensky, I. Lukac, and P. Slama, J. Polym. Sci. 16, 877 (1978).Google Scholar
  57. 32.
    D. Pone, S. Zarane, and L. Jirgens, Modif. Polim. Mater. 2, 86 (1969);Google Scholar
  58. 32a.
    D. Pone, S. Zarane, and L. Jirgens, Chem. Abstr. 75, 64760d (1971).Google Scholar
  59. 33.
    G. Natta, G. Crespi, and M. Bruzzone, Kautschuk U. Gummi 14, 54 (1961);Google Scholar
  60. 33a.
    G. Natta, G. Crespi, and M. Bruzzone, Chem. Abstr. 55, 12903e (1961).Google Scholar
  61. 34.
    C. Andrei, D. Mihaita, I. Hogea, and D. Munteanu, Rev. Roum. Chim. 15(2), 239 (1970);Google Scholar
  62. 34a.
    C. Andrei, D. Mihaita, I. Hogea, and D. Munteanu, Chem. Abstr. 73, 15685h (1970).Google Scholar
  63. 35.
    C. Andrei, E. Rizesau, and V. Paransonu, Mater. Plast. Elastomeri 37(4), 348 (1971);Google Scholar
  64. 35a.
    C. Andrei, E. Rizesau, and V. Paransonu, Chem. Abstr. 75, 37133v (1971).Google Scholar
  65. 36.
    Mitsui Polychemical, W. Ger. Pat. 2,023,154 (1970)Google Scholar
  66. 37.
    Toyo Soda Mfg. Co., W. Ger. Pat. 2,131,444 (1972).Google Scholar
  67. 38.
    Showa Denko Co., W. Ger. Pat. 2,302,473 (1973).Google Scholar
  68. 39.
    Toyo Soda Mfg. Co., W. Ger. Pat. 2,329,780 (1974).Google Scholar
  69. 40.
    Mitsui Petrochemical, Jap. Pat. 60,342 (1974).Google Scholar
  70. 41.
    J. LeBras, Rev. Gen. Caoutchouc 19(2), 43 (1942);Google Scholar
  71. 41a.
    J. LeBras, Rev. Gen. Caoutchouc 5, 605, 931 (1958).Google Scholar
  72. 42.
    S. Kambara, Y. Muramatsu, and S. Kuroda, J. Soc. Chem. Ind. Jap. 45, 1010 (1942);Google Scholar
  73. 42a.
    S. Kambara, Y. Muramatus, and S. Kuroda, J. Soc. Chem. Ind. Jap. 47, 141 (1944).Google Scholar
  74. 43.
    J. LeBras, Rubber Chem. Tech. 19, 313 (1946).Google Scholar
  75. 44.
    E. H. Farmer, Proc. 1st Rubber Technol Conf. 256 (1938).Google Scholar
  76. 45.
    I Gancarz and W. Laskawski, J. Polym. Sci. Polym. Chem. Ed. 17(3), 683 (1979);Google Scholar
  77. 45a.
    I. Gancaraz and W. Laskawski, J. Polym. Sci. Polym. Chem. Ed. 17(5), 1523 (1979).Google Scholar
  78. 46.
    J. LeBras, Bull. Soc. Chem. France 11, 553 (1944).Google Scholar
  79. 47.
    United States Rubber Co., Brit Pat. 739,634 (1955).Google Scholar
  80. 48.
    J. LeBras and J. de Merlier, Compt. Rend. 231, 230 (1950);Google Scholar
  81. 48a.
    J. LeBras and J. de Merlier, Chem. Abstr. 44, 11153d (1950).Google Scholar
  82. 49.
    J. LeBras, P. Compagnon, and A. Delalande, Compt. Rend. 241, 61 (1955);Google Scholar
  83. 49a.
    J. LeBras, P. Compagnon, and A. Delalande, Chem Abstr 50, 597a (1956).Google Scholar
  84. 50.
    J. LeBras, P. Compagnon, and A. Delalande, Rev. Gen. Caoutchouc 33, 148 (1956)Google Scholar
  85. 50a.
    J. LeBras, P. Compagnon, and A. Delalande, Chem. Abstr. 50, 7493b (1956).Google Scholar
  86. 51.
    J. LeBras, C. Pinazzi, and G. Milbert, Compt. Rend. 246, 1214 (1958);Google Scholar
  87. 51a.
    J. LeBras, C. Pinazzi, and G. Milbert, Chem Abstr. 52, 11454g (1958);Google Scholar
  88. 51b.
    J. LeBras, C. Pinazzi, and G. Milbert, Rev. Gen. Caoutchouc 36, 215 (1959);Google Scholar
  89. 51c.
    J. LeBras, C. Pinazzi, and G. Milbert, Chem. Abstr. 55, 25311 (1960).Google Scholar
  90. 52.
    Eastman Kodak Co., U.S. Pat. 3,433,777 (1969),Google Scholar
  91. 52a.
    Eastman Kodak Co., U.S. Pat. 3,481,910 (1969)Google Scholar
  92. 52b.
    Eastman Kodak Co., U.S. Pat. 3,480,580 (1969Google Scholar
  93. 52c.
    Eastman Kodak Co., U.S. Pat. 3,519,609 (1970).Google Scholar
  94. 53.
    I. A. Tutorskii, L. S. Krokhina, and B. A. Dogadkin, Kouchuk i Rezina 19(5), 3 (1960).Google Scholar
  95. 54.
    R. J Ceresa, Rev. Gen. Caoutchouc 37, 1331 (1960).Google Scholar
  96. 55.
    C. P. Pinazzi, R. Pautrat, and J. C. Danjard, Rev. Gen. Caoutchouc 37, 663 (1960);Google Scholar
  97. 55a.
    C. P. Pinazzi, R. Pautrat, and J. C. Danjard, Rev. Gen. Caoutchouc 37, 1008 (1960);Google Scholar
  98. 55b.
    C. P. Pinazzi, R. Pautrat, and J. C. Danjard,Chem. Abstr. 55, 19293b (1961).Google Scholar
  99. 56.
    C. P. Pinazzi, J. C. Danjard, and R. Pautrat, Bull. Soc. Chem. France 2, 433 (1961);Google Scholar
  100. 56a.
    C. P. Pinazzi, J. C. Danjard, and R. Pautrat,Chem. Abstr. 57, 1002g (1962).Google Scholar
  101. 57.
    J. LeBras, Kaitschuk Gummi 15, WT 407-WT 418 (1962);Google Scholar
  102. 57a.
    J. LeBras, Chem. Abstr. 58, 5861h (1963).Google Scholar
  103. 58.
    G. Milbert, Thesis, University of Paris (1959).Google Scholar
  104. 59.
    J. D. Merlier and J. LeBras, Ind. Eng. Chem. Prod. Res. Develop. 2, 22 (1963).Google Scholar
  105. 60.
    C. Simionescu, Mechanochemistry of the Macromolecular Compounds, Acad. Rep. Soc. Rum., Bucharest, 1967.Google Scholar
  106. 61.
    A. Casale, R. S. Porter, and J. F. Johnson, Rubber Chem. Technol. 44, 534 (1971).Google Scholar
  107. 62.
    A. S. Prashchikina, A. E. Grinberg, and A. R. Makeeva, Kauchuk Rezina 22(4), 23 (1963);Google Scholar
  108. 62a.
    A. S. Prashchikina, A. E. Grinberg, and A. R. Makeeva, Chem. Abstr. 59, 4148e (1964).Google Scholar
  109. 63.
    J. LeBras, Kautschuk Gummi Kunstoffe 18(9), 561 (1965);Google Scholar
  110. 63a.
    J. LeBras,Chem. Abstr. 63, 18409c (1965).Google Scholar
  111. 64.
    W. J. S. Naunton, The Applied Science of Rubber, pp. 133–134, E. Arnold, London (1961).Google Scholar
  112. 65.
    V. Krishnan and B. K. Shah, Pop. Plast. 11(2), 20 (1966);Google Scholar
  113. 65a.
    V. Krishnan and B. K. Shah, Chem. Abstr. 66, 3486r (1967).Google Scholar
  114. 66.
    J. Moraud, Rev. Gen. Caout. Plast. 44(4), 499 (1967);Google Scholar
  115. 66a.
    J. Moraud, Chem. Abstr. 67, 44602k (1967).Google Scholar
  116. 67.
    N. L. Makhmudbekova and N. K. Baramboim, Mekhanoemissiya Mekhonkhim. Tverd. Tel. (Dokl. Vser Simp), 2nd, 244 (1969);B. V. Deryagin, ed., Frunz USSR.Google Scholar
  117. 68.
    N. L. Makhmudbekova and N. K. Barambpim, Vipokomol. Soedin A 16(6), 1296 (1974);Google Scholar
  118. 68a.
    N. L. Makhmudbekova and N. K. Barambpim, Chem. Abstr. 81, 106959g (1974).Google Scholar
  119. 69.
    P. Luijk and J. M. Rellage, Kaut. Gummi. Kunstst. 26(10), 446 (1973),Google Scholar
  120. 69a.
    P. Luijk and J. M. Rellage, Chem. Abstr. 80, 84421a (1974).Google Scholar
  121. 70.
    N. K. Baramboim, N. L. Makhmvdbekova, Y. F. Kurdubov, and B. N. Dinsburg, Izv. Vyssh. Ucheb. Zaved. Tekhnol. Legk. Prom. 1 , 37 (1971);Google Scholar
  122. 70a.
    N. K. Baramboim, N. L. Makhmvdbekova, Y. F. Kurdubov, and B. N. DinsburgChem. Abstr. 74, 143028d (1971).Google Scholar
  123. 71.
    R. S Frenkel, Kauch. Rezina. 28(3), 9 (1969);Google Scholar
  124. 71a.
    R. S. Frenkel,Chem. Abstr. 70, 107292u (1969).Google Scholar
  125. 72.
    E. H Farmer, Trans. Faraday Soc. 38, 340 (1942).Google Scholar
  126. 73.
    E. H. Farmer and R. G. R. Bacon, Rubber Chem. Technol. 12, 200 (1939).Google Scholar
  127. 74.
    K. Alder, F. Pascher, and A. Schmitz, Ber. 76, 27 (1943).Google Scholar
  128. 75.
    R. Delaby, Bull. Soc. Chim. France 41, 765 (1957).Google Scholar
  129. 76.
    R. Priester, Fette, Seifen Anstrichm. 69(4), 251 (1967);Google Scholar
  130. 76a.
    R. Priester, Chem. Abstr. 67, 33867z (1967).Google Scholar
  131. 77.
    G. Green and E. F. Sverdrup, Ind. Eng. Chem. 48, 2138 (1956).Google Scholar
  132. 78.
    U.S. Rubber Co., U.S. Pat. 2,879,245 (1959).Google Scholar
  133. 79.
    P. O Tawney, Rubber Age 83, 127 (1958).Google Scholar
  134. 80.
    W. W. Crouch and J. A. Shotton, Ind. Eng. Chem. 47, 2091 (1955).Google Scholar
  135. 81.
    J. L Binder, J. Polym. Sci. A-1 1, 47 (1963).Google Scholar
  136. 82.
    H. R. Schloss, Recent Advances in Adhesives Proceedings of the American Chemical Society Symposium, p. 485, L. H. Lee, ed., Gordon and Breach, London, England (1971).Google Scholar
  137. 83.
    V. I. Burdinand S. A. Pvalov, Kozh.-Obuv. Prom. 13(2), 49 (1971);Google Scholar
  138. 83a.
    V. I. Burdinand S. A. Pvalov, Chem. Abstr. 75, 6383x (1971).Google Scholar
  139. 84.
    S. Tazauke and H. Kimura, J. Polym. Sci. 15, 2707 (1977).Google Scholar
  140. 85.
    N. K. Baramboim and N. L. Makhmudbekova, Vysokomal. Soedin. B 13(6), 428 (1971);Google Scholar
  141. 85a.
    N. K. Baramboim and N. L. Makhmudbekova, Chem. Abstr. 75, 89219x (1971).Google Scholar
  142. 86.
    I. Weissand D. Zuchowska, Polimery 18(10), 530 (1973);Google Scholar
  143. 86a.
    I. Weissand D. Zuchowska, Chem. Abstr. 81, 122900m (1974).Google Scholar
  144. 87.
    D. Zuchowska, A. Gasprowicz, and W. Laskowski, Polimery 19(7), 322 (1974);Google Scholar
  145. 87a.
    D. Zuchowska, A. Gasprowicz, and W. Laskowski, Chem. Abstr. 82, 140929c (1975).Google Scholar
  146. 88.
    C. E. Sroog, S. Tocker, and V. L. Bell, Kinet. Mech. Polyreactions Int. Symp. Macromol Chem. Prepr. 5, 125 (1969);Google Scholar
  147. 88a.
    C. E. Sroog, S. Tocker, and V. L. Bell, Chem. Abstr. 75, 77352x (1971).Google Scholar
  148. 89.
    Y. K. Kirilenko, A. I. Meos, and L. A. Volf, Zh. Prikl. Khim. 38(9), 2091 (1965);Google Scholar
  149. 89a.
    Y. K. Kirilenko, A. I. Meos, and L. A. Volf, Chem. Abstr. 63, 18334d (1965).Google Scholar
  150. 90.
    Dow Chemical Co., U.S.S. Pat. 3,541,058 (1970).Google Scholar
  151. 91.
    K. Higashiura and M. Oiwa, Kogyo Kagaku Zasshi 69(1), 109 (1966);Google Scholar
  152. 91a.
    K. Higashiura and M. Oiwa, Chem. Abstr. 65, 3966k (1966).Google Scholar
  153. 92.
    A. A. Berlin, E. F. Vainshtein, M. I. Cherkashin, and Y. S Moshkovskii Vysakomol. Soedin. 5(9), 1354 (1963);Google Scholar
  154. 92a.
    A. A. Berlin, E. F. Vainshtein, M. I. Cherkashin, and Y. S Moshkovskii Chem. Abstr. 60, 667h (1964).Google Scholar
  155. 93.
    A. A. Berlin, M. I. Cherkashin, Y. G. Aseev, and I. M. Shcherbakova, Vysokomol. Soedin. 6(10), 1773 (1964);Google Scholar
  156. 93a.
    A. A. Berlin, M. I. Cherkashin, Y. G. Aseev, and I. M. Shcherbakova, Chem. Abstr. 62, 2832e (1965).Google Scholar
  157. 94.
    B. G. Zadonstsev, M. I. Cherkashin, and A. A. Berlin, Izv. Akad. Nauk USSR Ser. Khim. 9, 2065 (1967);Google Scholar
  158. 94a.
    B. G. Zadonstsev, M. I. Cherkashin, and A. A. Berlin, Chem. Abstr. 67, 117342m (1967)Google Scholar
  159. 95.
    A. A. Berlin, M. I. Cherkashin, and B. G. Zadontsev, Vysokomol. Soedin. B 9(2), 91 (1967);Google Scholar
  160. 95a.
    A. A. Berlin, M. I. Cherkashin, and B. G. Zadontsev, Chem. Abstr. 66, 95747y (1967)Google Scholar
  161. 96.
    V. G. Zadontsev, M. I. Cherkashin, and A. A. Berlin, Kinet. Mech. Polyreactions Int. Symp. Macromol. Chem. Prepr. 4, 302 (1969).Google Scholar
  162. 97.
    A. A. Berlin, M. I. Cherkashin, and P. O. Kisilitsa, Izv. Akad. Nauk. SSSR Ser. Khim. 10, 1875 (1965);Google Scholar
  163. 97a.
    A. A. Berlin, M. I. Cherkashin, and P. O. Kisilitsa, Chem. Abstr. 64, 5219b (1966)Google Scholar
  164. 98.
    Bridgestone Tire Company, Jap. Pat. 53,490 (1975).Google Scholar
  165. 99.
    P. E. Matkovskie, N. D. Zavorokhin, N. M. Chirkov, Y. V. Kissin, and I. D. Leonov, Vysokomol. Soedin. 8(10), 1712 (1966);Google Scholar
  166. 99a.
    P. E. Matkovskie, N. D. Zavorokhin, N. M. Chirkov, Y. V. Kissin, and I. D. Leonov, Chem. Abstr. 66, 11193d (1967)Google Scholar
  167. 100.
    N. K. Baramboim and G. K. Pytov, Nauchn. Tr. Mosk., Tekhnol. Inst. Legk. Prom. 18, 48 (1960);Google Scholar
  168. 100a.
    N. K. Baramboim and G. K. Pytov, Chem. Abstr. 5757, 6119d (1962)Google Scholar
  169. 101.
    B. B. Troitskii, V. N. Myakov, and G. A. Razubaev, Vysokomol. Soedin. 8(11), 2032 (1966);Google Scholar
  170. 101a.
    B. B. Troitskii, V. N. Myakov, and G. A. Razubaev, Chem. Abstr. 66, 29489q (1967)Google Scholar
  171. 102.
    Y. Iwami, H. Ishikawa, and Y. Minoura, Kogyo Kagaku Zasshi 72(11), 2482 (1969);Google Scholar
  172. 102a.
    Y. Iwami, H. Ishikawa, and Y. Minoura, Chem. Abstr. 72, 674366 (1970)Google Scholar
  173. 103.
    The General Tire and Rubber Co., U.S. Pat 3,896,091 (1975).Google Scholar
  174. 104.
    K. Boto and H. Fujii, Nippon Gomu Kyokaishi 32, 90 (1959);Google Scholar
  175. 104a.
    K. Boto and H. Fujii, Chem. Abstr. 54, 4033g (1960).Google Scholar
  176. 105.
    B. B. Troitskii and B. N. Myakov, Plast. Massy 3, 13 (1967).Google Scholar
  177. 106.
    S. Van Der Ven and W. F. DeWit, Angew. Makromol. Chem. 8, 143 (1969).Google Scholar
  178. 107.
    J. Malac, J. Polym. Sci. ,B-9 85 (1971).Google Scholar
  179. 108.
    K. Thinius, R. Schlimper and E. Kestner, Plast. Kaut. 18(1), 33 (1971);Google Scholar
  180. 108a.
    K. Thinius, R. Schlimper and E. Kestner, Chem. Abstr. 74, 64806c (1971).Google Scholar
  181. 109.
    I. K. Varma, S. Patnaik, and J. C. Sahoo, Proceedings of the 2nd International Symposium on Poly(vinyl chloride) at Lyon, Villeurbanne (France), July 5–9, 1976.Google Scholar
  182. 110.
    I. K. Varma and K. K. Sharma, Angew. Makromol. 66, 105 (1978);Google Scholar
  183. 110a.
    I. K. Varma and K. K. Sharma, Angew. Makromol, 79, 147 (1979).Google Scholar
  184. 111.
    S. W. Lee and K. Sugayama, Lairyo 27(302), 1079 (1978);Google Scholar
  185. 111a.
    S. W. Lee and K. Sugayama, Chem. Abstr. 90, 39491u (1979).Google Scholar
  186. 112.
    Y. Landler, J. Cell. Plast. 3(9), 404 (1967).Google Scholar
  187. 113.
    M. L. Miller, R. H. Postal, P. N. Sawyer, J. G. Martin, and M. J. Kaplit, J. Appl. Polym. Sci. 14(2), 257 (1970).Google Scholar
  188. 114.
    K. Budevska, Izv. Otd. Khim. Nauk. Bulg. Akad. Nauk. 3(2), 303 (1970);Google Scholar
  189. 114a.
    K. Budevska, Chem. Abstr. 74, 13537h (1971).Google Scholar
  190. 115.
    N. G. Shelkunov, I. B. Klimenko, V. V. Girdyuk, and L. A. Vol’f, Khim. Geterotsikl Soedin. 5, 775 (1969);Google Scholar
  191. 115a.
    N. G. Shelkunov, I. B. Klimenko, V. V. Girdyuk, and L. A. Vol’f, Chem. Abstr. 72, 67586a (1970).Google Scholar
  192. 116.
    K. Ohkita, N. Kitahara, and I. Tserbata, Kogyo Kagaku Zasshi 67(2), 391 (1964);Google Scholar
  193. 116a.
    K. Ohkita, N. Kitahara, and I. Tserbata, Chem. Abstr. 62, 1796c (1965).Google Scholar
  194. 117.
    N. L. Makhmudbekova, N. K. Baramboim, N. S. Khromova, and T. S. Zaikina, Izv. Vyssh. Ucheb. Zaved, Tekhnol. Legk. Prom. 4, 56 (1971);Google Scholar
  195. 117a.
    N. L. Makhmudbekova, N. K. Baramboim, N. S. Khromova, and T. S. Zaikina,Chem. Abstr. 76, 35011a (1972).Google Scholar
  196. 118.
    M. Brie and C. LeGressus, Fibre Sci. Technol. 6(1), 47 (1973);Google Scholar
  197. 118a.
    M. Brie and C. LeGressus, Chem. Abstr. 78, 85250q (1973).Google Scholar
  198. 119.
    M. Brie, J. Cazard, F. M. Laug, and G. Riess, Bull. Inform. Sci. Tech. Commis. Energ. At. 155, 31 (1971);Google Scholar
  199. 119a.
    M. Brie, J. Cazard, F. M. Laug, and G. Riess, Chem. Abstr. 75, 118889y (1971)Google Scholar
  200. 120.
    New Technology Development Organization, Jap. Pat. 3,826 (1969).Google Scholar
  201. 121.
    Ashai Chemical Company, Jap. Pat. 68,892 (1973).Google Scholar
  202. 122.
    N. G. Gaylord, E. Oikawa, and A. T. Akahashi, J. Polym. Sci. B-9, 379 (1971).Google Scholar
  203. 123.
    N. G. Gaylord, A. Autropiusova, and B. K. Patuaik, J. Polym. Sci. B-9, 387 (1971).Google Scholar
  204. 124.
    Mitsui Petrochemical, Jap. Pat. 20,833 (1973).Google Scholar
  205. 125.
    Basf A.G., W. Ger. Pat. 2,303,745 (1974) and 2,305,023 (1974).Google Scholar
  206. 126.
    Gaylord Associates, W. Ger. Pat. 2,108,749 (1971).Google Scholar
  207. 127.
    N. G Gaylord, Am. Chem. Soc. Div. Polym. Chem. Prepr. 13(1), 505 (1972).Google Scholar
  208. 128.
    Gaylord Research Institute, U.S. Pat. 3,781,232 (1973).Google Scholar
  209. 129.
    N. G Gaylord, Nouvo Chim. 49(1), 81 (1973);Google Scholar
  210. 129a.
    N. G. Gaylord,Chem. Abstr. 78 136716F (1973).Google Scholar
  211. 130.
    BASF A.G., W. Ger. Pat. 2,255,466 (1974).Google Scholar
  212. 131.
    Furukawa Electric Co., Jap. Pat. 686 (1973).Google Scholar
  213. 132.
    Idemitsu Kosan Co., Jap. Pat. 55,790 (1974).Google Scholar
  214. 133.
    N. G. Gaylord, Advan. Chem. Ser. 129, 209 (1973).Google Scholar
  215. 134.
    N. G. Gaylord, Belg. Pat. 762,854 (1971).Google Scholar
  216. 135.
    M. Umezawa and K. Hirota, Nippon Hoshasen Kobunshi Kenkyai Kyokai Nempo 4, 241 (1962);Google Scholar
  217. 135a.
    M. Umezawa and K. Hirota, Chem. Abstr. 62, 6609c (1965).Google Scholar
  218. 136.
    M. Umezawa and K. Hirota, Kobunshi Kogaku 21(6), 352 (1964);Google Scholar
  219. 136a.
    M. Umezawa and K. Hirota, Chem. Abstr. 62, 6608h (1965).Google Scholar
  220. 137.
    H. Yamakita and K. Hayakawa, J. Polym. Sci. B, 10(10), 823 (1972).Google Scholar
  221. 138.
    Agency of Industrial Science and Technology, Jap. Pat. 97,990 (1973).Google Scholar
  222. 139.
    Kansai Paint Co., Jap. Pat. 96,693 (4) (1977).Google Scholar
  223. 140.
    M.Agostini and P. Lebel, J. Polym. Sci. C. 16(6), 3349 (1965).Google Scholar
  224. 141.
    J. S Danon, J. Polym. Sci. C 16(7), 4071 (1965).Google Scholar
  225. 142.
    P. Lebel and C. Job, J. Polym. Sci. C 4, 649 (1963).Google Scholar
  226. 143.
    V. Einsele and H. Adidarma, Text. Prax. Inst. 29(2), 188 (1974);Google Scholar
  227. 143a.
    V. Einsele and H. Adidarma, Chem. Abstr. 81, 79204y (1974).Google Scholar
  228. 144.
    G. M. Brauer and D. J. Termini, J. Biomed. Mater. Res. 8(6), 451 (1974).Google Scholar
  229. 145.
    L. A. Miller and R. E. Whitfield, Textile Research J. 31, 451 (1961).Google Scholar
  230. 146.
    G. E. J Reynolds, J. Polym. Sci. C 16, 3957 (1968).Google Scholar
  231. 147.
    Anon., Mod. Plast. 45(2), 94 (1967).Google Scholar
  232. 148.
    P. J. Flory, Principles of Polymer Chemistry, pp. 160–161, Cornell University Press, New York (1953).Google Scholar
  233. 149.
    F. Ide and A. Hasegawa. J Appl. Polym. Sci. 18(4), 963 (1974).Google Scholar
  234. 150.
    Shell Int., Ger. Pat. 1,745,439 (1979).Google Scholar
  235. 151.
    Mitsubishi Petrochemical, Jap. Pat. 99,193 (1979).Google Scholar
  236. 152.
    Sumitomo Chemical, Jap. Pat. 77,688 (1979) and 74,893 (1979).Google Scholar
  237. 153.
    Nippon Oil Co., U.S. Pat. 4,072,536 (1978)Google Scholar
  238. 153a.
    Nippon Oil Co., Jap. Pat. 71,123 (1979).Google Scholar
  239. 154.
    Ciba-Geigy, Swiss Pat. 571,033 (1975).Google Scholar
  240. 155.
    Dow Chemical, Brit. Pat. 844,231 (1960).Google Scholar
  241. 156.
    A. F. Nikolaev, E. S. Shulgina, L. K. Khrustaleva, G. M. Lavrenova, Z. R. Uspenskaya, and N. V. Lavrova, U.S.S.R. Pat. 679,596 (1979).Google Scholar
  242. 157.
    J. R. Wolfe, Rubber Age 103(6), 60 (1971).Google Scholar
  243. 158.
    Kuraray Chemical Co., Jap. Pat. 96,551 and 96,596 (1979).Google Scholar
  244. 159.
    Toyo Soda Chemical Co., W. Ger. Pat. 2,350,331 (1979).Google Scholar
  245. 160.
    S. M. Miller, R. Robers, and R. L. Vale, J. Polym. Sci. 58, 737 (1962).Google Scholar
  246. 161.
    Monsanto Co., Eur. Pat. 2,961 (1979).Google Scholar
  247. 162.
    Montecatini Edison S.P.A., U.S. Pat. 3,427,183 (1969).Google Scholar
  248. 163.
    Hercules, Inc., U.S. Pat. 3,255,130 (1966).Google Scholar
  249. 164.
    Shell Int., Neth. Pat. 2,969 (1965).Google Scholar
  250. 165.
    Esso Research, U.S. Pat. 3,511,816 (1970).Google Scholar
  251. 166.
    G. M. Panchenkov, P. S. Belov, A. P. Polyakov, I. Y. Gulyaev, and Y.I . Lazyan, Nauchn. Osn. Pererab. Nefti Gaza Neftekhim. Tezisy Dokl. Vses. Konf., 192 (1977); Chem. Abstr. 92, 41291p (1980).Google Scholar
  252. 167.
    D. B. Boguslovskii, U.S.S.R. Pat. 384,362 (1979) and 410,038 (1974).Google Scholar
  253. 168.
    N. G. Gaylord, H. Ender, L. Davis, and A. Takahashi, ACS Symp. Ser. (Modif. Polym) 121, 469 (1980).Google Scholar
  254. 169.
    G. P. Gashko, M. V. Boddanov, P. L. Klimenko, O. L. Glavati, and Y. E. Garun, Khim. Tekhnol. Topl Masel 7, 57 (1980);Google Scholar
  255. 169a.
    G. P. Gashko, M. V. Boddanov, P. L. Klimenko, O. L. Glavati, and Y. E. Garun, Chem. Abstr. 93, 150952w (1980).Google Scholar
  256. 170.
    I. Gancarz and W. Laskawski, Chem. Stosow. 23(3), 349 (1979);Google Scholar
  257. 170a.
    I. Gancarz and W. Laskawski, Chem. Abstr. 92, 147465p (1980).Google Scholar
  258. 171.
    A. Wirsen and P. Flodin, J. Appl. Poly. Sci. 23(7), 2005 (1979).Google Scholar
  259. 172.
    K. W. Dinges, Annu. Meet. Proc. Int. Inst. Synth. Rubber Prod. 20, Paper No. 10 (1979).Google Scholar
  260. 173.
    V. Barboiu, A. Natansohn, C. Andrei, and M. Gavril, Mater. Plast. (Bucharest) 16(4), 211 (1979);Google Scholar
  261. 173a.
    V. Barboiu, A. Natansohn, C. Andrei, and M. Gavril, Chem. Abstr. 92, 164937a (1980).Google Scholar
  262. 174.
    N. I. Lonina, E. E. Potapov, and I. A. Tutorskii, Tr. Mosk. In-ta Tonk. Khim. Tekhnol. 9(2), 107 (1979);Google Scholar
  263. 174a.
    N. I. Lonina, E. E. Potapov, and I. A. Tutorskii, Chem. Abstr. 92, 95352c (1980).Google Scholar
  264. 175.
    Petrochemical Institute, U.S.S.R. Pat. 747,864 (1980).Google Scholar
  265. 176.
    Azerb Sumgait, U.S.S.R. Pat. 713,873 (1980).Google Scholar
  266. 177.
    Nippon Oil, Jap. Pat. 27,336 (1980).Google Scholar
  267. 178.
    Toyo Soda Mfg. Co., Jap. Pat. 43,110 (1980).Google Scholar
  268. 179.
    Idemitsu Kosan, Jap. Pat. 50,007 (1980).Google Scholar
  269. 180.
    Mitsui Toatsu Chemicals, Jap. Pat. 23,134 (1980) and 34,224 (1980).Google Scholar
  270. 181.
    Sekisui Chemicals Ind., Jap. Pat. 75,408 (1980).Google Scholar
  271. 182.
    V. E. Gul, E. M. Glukhova, O. V. Vasileva, M. N. Tolmacheva, G. M. Ishevskii, and T. G. Itskova, U.S.S.R. Pat. 732,306 (1980).Google Scholar
  272. 183.
    Rhone-Poulenc Ind., Fr. Pat. 2,429,804 (1980).Google Scholar
  273. 184.
    Rhone-Poulenc Ind., Fr. Pat. 2,429,819 (1980).Google Scholar
  274. 185.
    Rhone-Poulenc Ind., W. Ger. Pat. 2,935,882 (1980).Google Scholar
  275. 186.
    TBA Ind. Products Ltd., U.S. Pat. 4,212,792 (1980).Google Scholar
  276. 187.
    D. B. Boguslavskii, L. M. Volchenok, K. N. Borodushkina, and E. A. Dzyura, Int. Polym. Sci. Tech. 6(12) T57 (1979).Google Scholar
  277. 188.
    A. S. Prashckikina, M. S. Feldshtein, and L. V. Andreev, Int. Polym. Sci. Tech. 7(1), T47 (1980).Google Scholar
  278. 189.
    TRW Inc., U.S. Pat. 4,216,297 (1980).Google Scholar
  279. 190.
    Fujitsu Ltd., Jap. Pat. 73,749 (1980).Google Scholar
  280. 191.
    Asahi Chemical Ind., W. Ger. Pat. 2,939,989 (1980).Google Scholar
  281. 192.
    Bayer A.G., Brit. Pat. 1,562,175 (1980).Google Scholar
  282. 193.
    Standard Oil (Ohio), W. Ger. Pat. 2,143,890 (1980).Google Scholar
  283. 194.
    I. Hogea, C. Andrei, and G. Musca, Mater. Plast. (Bucharest) 17(4), 230–3 (1980).Google Scholar
  284. 195.
    R. Titeica, I. Hogea, and C. Andrei, Rev. Roum. Phys. 25(7), 815,821 (1980).Google Scholar
  285. 196.
    B. Ivan, J. P. Kennedy, T. Kelen, and F. Tudos, Polym. Bull (Berlin) 3(1–2), 45–52 (1980).Google Scholar

Copyright information

© Springer Science+Business Media New York 1982

Authors and Affiliations

  • B. C. Trivedi
    • 1
  • B. M. Culbertson
    • 1
  1. 1.Ashland Chemical CompanyDublinUSA

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