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Aromatic polybenzimidazoles. Syntheses, properties, and applications

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Synthesis and Degradation Rheology and Extrusion

Part of the book series: Advances in Polymer Science ((POLYMER,volume 47))

Abstract

Outstanding performance characteristics under unusual and demanding operating conditions are the hallmarks of a class of macromolecular compounds commonly referred to as polyheteroaromatics. The all-aromatic polybenzimidazoles, which rank among the leading representatives of this class, are the topic of the present article. Beginning with the early report of a successful synthesis of poly(1,4-phenylene-5,5′(6′)-bibenzimidazole-2,2′-diyl) from Carl Marvel's laboratory, a 20-years' span of worldwide research activities has until now provided a wealth of synthetic information in the field of aromatic benzimidazole polymers, which is critically surveyed. The problems involved in the conventional high-temperature processing technology are pointed out, and recent preparative developments permitting a two-stage “prepolymer” approach are reviewed. Structure-property relationships are treated in detail, with special attention paid to the problem of high-temperature stability and flame retardancy. A major section of the article presents a discussion of application and performance data in some of the more advanced segments of materials technology.

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References

  1. Mulvaney, J. E.: Encycl. Polym. Sci. Tech. 7, 478 (1967)

    Google Scholar 

  2. Frazer, A. H.: High Temperature Resistant Polymers, Wiley, New York 1968

    Google Scholar 

  3. Koton, M. M.: Advan. Macromol. Chem. 2, 175 (1970)

    Google Scholar 

  4. Pezdirtz, G. F., Johnson, N. J.: Thermally Stable Macromolecules, in: Chemistry in Space Research, Landel, R., Rembaum, A., Eds., Elsevier, New York 1972

    Google Scholar 

  5. Cotter, R. J., Matzner, M.: Ring-Forming Polymerizations, Pt. B, Vol. 1, Heterocyclic Rings, Academic Press, New York 1972

    Google Scholar 

  6. Neuse, E. W.: Mater. Sci. Eng. 11, 121 (1973)

    Google Scholar 

  7. Cassidy, P. E.: Thermally Stable Polymers, Dekker, New York 1980

    Google Scholar 

  8. Levine, H. H.: Encycl. Polym. Sci. Tech. 11, 188 (1969)

    Google Scholar 

  9. Vogel, H., Marvel, C. S.: J. Polym. Sci. 50, 511 (1961); Marvel, C. S., Vogel, H.: US Pat. 3,174,947 (1965); Chem. Abstr.: 63, 7137 (1965)

    Google Scholar 

  10. Plummer, L., Marvel, C. S.: J. Polym. Sci., Part A 1, 1531 (1963)

    Google Scholar 

  11. Plummer, L., Marvel, C. S.: J. Polym. Sci., Part A 2, 2559 (1964)

    Google Scholar 

  12. Foster, R. T., Marvel, C. S.: J. Polym. Sci., Part A 3, 417 (1965)

    Google Scholar 

  13. Mitsuhashi, K., Marvel, C. S.: ibid. pg. 1661

    Google Scholar 

  14. Lakshmi Narayan, T. V., Marvel, C. S.: J. Polym. Sci., Part A-1, 5, 1113 (1967); Bracke, W., Marvel, C. S.: J. Polym. Sci., Part A-1, 8, 3177 (1970)

    Google Scholar 

  15. Korshak, V. V. et al.: Dokl. Akad. Nauk USSR 149, 104 (1963); Korshak, V. V. et al.: Vysokomol. Soedin., Ser. B 6, 1251 (1964); Izyneev, A. A., Mazurevskii, V. P., Korshak, V. V.: Vysokomol. Soedin., Ser. A 17, 1200 (1975)

    Google Scholar 

  16. Korshak, V. V., Izyneev, A. A., Mazurevskii, V. P.: Dokl. Akad. Nauk SSSR 220, 372 (1975)

    Google Scholar 

  17. Green, J.: Symp. High Polymers, Am. Chem. Soc. West. Reg. Meet., Los Angeles, Cal., Nov. 1965; Proc. L-1; Green, J., Mayes, N.: J. Macromol. Sci., Chem. 1, 135 (1967)

    Google Scholar 

  18. Gitina, R. M. et al.: Vysokomol. Soedin., Ser. B 9, 447 (1967)

    Google Scholar 

  19. Conciatori, A. B., Chenevey, E. C.: Macromol. Synt. 3, 24 (1968); US Pat. 3,433,772 (1969); Chem. Abstr.: 70, 97414 (1969); Conciatori, A. B. et al.: J. Polym. Sci., Part C 19, 49 (1967)

    Google Scholar 

  20. Kourtides, D. A., Parker, J. A.: Polym. Eng. Sci. 15, 415 (1975)

    Google Scholar 

  21. Breed, L. W., Wiley, J. C.: J. Polym. Sci., Polym. Chem. Ed. 14, 83 (1976); Banihashemi, A., Kiaizadeh, F.: Makromol. Chem. 181, 325 (1980)

    Google Scholar 

  22. Babé, S. G., de Abajo, J.: Rev. Plasticos Modernos 22 [182], 1 (1971)

    Google Scholar 

  23. Wrasidlo, W., Levine, H. H.: J. Polym. Sci., Part A 2, 4795 (1964)

    Google Scholar 

  24. Gerber, A. H.: J. Polym. Sci., Polym. Chem. Ed. 11, 1703 (1973); see also Gerber, A. H.: US Pat. 3,943,125 (1976); Chem. Abstr.: 85, 33936 (1976)

    Google Scholar 

  25. Korshak, V. V. et al.: Macromolecules 5, 807 (1972)

    Google Scholar 

  26. Tugushi, D. S. et al.: Vysokomol. Soedin., Ser. A 15, 969 (1973)

    Google Scholar 

  27. Tugushi, D. S. et al.: Tr. Mosk. Khim.-Tekhnol. Inst. [70], 182 (1972); Chem. Abstr.: 79, 19161 (1973)

    Google Scholar 

  28. Pravednikov, A. N. et al.: Plaste Kautsch. 22, 476 (1975)

    Google Scholar 

  29. Zurakowska-Orszagh, J., Kurzela, M., Kaminski, J.: Polimery (Warsaw), 25, 51 (1980); Chem. Abstr.: 93, 168651 (1980)

    Google Scholar 

  30. Korshak, V. V. et al.: Vysokomol. Soedin. Ser. A 21, 122 (1979); Korshak, V. V. et al.: USSR Pat. 652,193 (1979); Chem. Abstr. 90, 205176 (1979); Korshak, V. V. et al.: Izv. Akad. Nauk Gruz. SSR, Ser. Khim. 6, 122 (1980); Chem. Abstr. 94, 66132 (1981); Korshak, V. V., Rusanov, A. L., Tugushi, D. S.: USSR Pat. 749,859 (1980); Chem. Abstr. 94, 16350 (1981)

    Google Scholar 

  31. Korshak, V. V. et al.: Soobshch. Akad. Nauk Gruz. SSR 96, 341 (1979); Chem. Abstr. 92, 164327 (1980)

    Google Scholar 

  32. Iwakura, Y., Uno, K., Imai, Y.: J. Polym. Sci., Part A 2, 2605 (1964)

    Google Scholar 

  33. Imai, Y., Uno, K., Iwakura, Y.: Makromol. Chem. 83, 179 (1965)

    Google Scholar 

  34. Srinivasan, P. R., Mahadevan, V., Srinivasan, M.: Makromol. Chem. 180, 1845 (1979)

    Google Scholar 

  35. Iwakura, Y., Uno, K., Chau, N.: Makromol. Chem. 176, 23 (1975)

    Google Scholar 

  36. Neuse, E. W., Horlbeck, G.: Polym. Eng. Sci. 17, 821 (1977)

    Google Scholar 

  37. Korshak, V. V. et al.: Vysokomol. Soedin, Ser. A 18, 2585 (1976)

    Google Scholar 

  38. Varma, I. K., Veena: J. Polym. Sci., Polym. Chem. Ed. 14, 973 (1976); J. Macromol. Sci., Chem. 11, 845 (1977)

    Google Scholar 

  39. Sivriev, H., Borissov, G.: Eur. Polym. J. 13, 25 (1977)

    Google Scholar 

  40. Korshak, V. V. et al.: Vysokomol. Soedin., Ser. A 22, 1209 (1980)

    Google Scholar 

  41. Kojima, T.: J. Polym. Sci., Polym. Phys. Ed. 18, 1685 (1980)

    Google Scholar 

  42. Banihashemi, A., Fabro, D., Marvel, C. S.: J. Polym. Sci. Part A-1, 7, 2293 (1969)

    Google Scholar 

  43. Banihashemi, A., Marvel, C. S.: Iranian J. Sci. Tech. 2, 203 (1972)

    Google Scholar 

  44. Marvel, C. S.: Techn. Rep. ML-TDR-64-39, Part I (1964)

    Google Scholar 

  45. Kokelenberg, H., Marvel, C. S.: J. Polym. Sci., Part A-1, 8, 3199 (1970)

    Google Scholar 

  46. Hedberg, F. L., Marvel, C. S.: J. Polym. Sci., Polym. Chem. Ed. 12, 1823 (1974); Nuova Chim. 50, 51 (1974)

    Google Scholar 

  47. Dudgeon, C. D., Vogl, O.: J. Polym. Sci., Polym. Chem. Ed. 16, 1815, 1831 (1978); Dudgeon, C. D.: PhD Thesis, Univers. of Massachusetts (1976). A related, low-molecular-mass polymer containing the purine ring system was prepared by the same basic method: Dudgeon, C. D., Vogl, O.: J. Macromol. Sci. Chem. 11, 1989 (1977)

    Google Scholar 

  48. Gray, D. N., Rouch, L. L., Strauss, E. L.: Polym. Prepr. 8, 1138 (1967)

    Google Scholar 

  49. Higgins, J., Marvel, C. S.: J. Polym. Sci., Part A-1, 8, 171 (1970)

    Google Scholar 

  50. D'Alelio, G. F.: US t. 3,763,107 (1963); Chem. Abstr.: 80, 71350 (1974)

    Google Scholar 

  51. Neuse, E. W.: Chem. Ind. (London), 1975, 315

    Google Scholar 

  52. Unpublished results from the author's laboratory

    Google Scholar 

  53. Coville, N. J., Neuse, E. W.: J. Org. Chem. 42, 3485 (1977)

    Google Scholar 

  54. Although not as yet demonstrated for the polymer case, H2O2 has been shown to be the byproduct in analogous nonpolymeric reactions: Grellmann, K. H., Tauer, E.: J. Am. Chem. Soc. 95, 3104 (1973)

    Google Scholar 

  55. The method was first employed by Grellmann and Tauer (preceding ref.) in a study of certain o-substituted benzylideneanilines

    Google Scholar 

  56. Iwakura, Y. et al.: Makromol. Chem. 77, 41 (1964)

    Google Scholar 

  57. Korshak, V. V. et al.: Rev. Roum. Chim. 22, 1521 (1977)

    Google Scholar 

  58. Hara, S., Senoo, M., Taketani, Y.: Japan. Kokai 1974, 74 78,798

    Google Scholar 

  59. Manecke, G., Brandt, L., Kossmehl, G.: Makromol. Chem. 178, 1745 (1977)

    Google Scholar 

  60. Denyes, R. O.: Techn. Rep. AFML-TR-66-167, Vols. I–III (1966)

    Google Scholar 

  61. Marvel, C. S.: J. Macromol. Sci. — Revs. Macromol. Chem. 13, 219 (1975)

    Google Scholar 

  62. Covacs, H. N., Delman, A. D., Simms, B. B.: J. Polym. Sci., Part A-1, 6, 2103 (1968)

    Google Scholar 

  63. Izyneev, A. A. et al.: Dokl. Akad. Nauk SSSR 231, 1126 (1976)

    Google Scholar 

  64. Osgerby, J. M., Pauson, P. L.: J. Chem. Soc., 4604 (1961); Omote, Y., Kobayashi, R., Nakara, Y., Sugiyama, N.: Bull. Chem. Soc. Jpn. 46, 3315 (1973)

    Google Scholar 

  65. Kojima, T.: Polym. J. 13, 85 (1981)

    Google Scholar 

  66. Kojima, T. et al.: J. Polym. Sci., Polym. Phys. Ed. 18, 1673 (1980)

    Google Scholar 

  67. Ryan, M. T., Helminiak, T. E.: Polym. Prepr., Am. Chem. Soc. Div. Polym. Chem. 14, 1317 (1973)

    Google Scholar 

  68. Kojima, T.: J. Polym. Sci., Polym. Phys. Ed. 18, 1791 (1980)

    Google Scholar 

  69. Belohlav, L. R.: Angew. Makromol. Chem. 40/41, 465 (1974)

    Google Scholar 

  70. Leal, J. R.: Mod. Plastics 52, 60 (1975)

    Google Scholar 

  71. Levine, H. H., Stacy, R. D.: Techn. Rep. AFML-TR-65-350 (1966)

    Google Scholar 

  72. Gibbs, W. E., Helminiak, T. E.: Polymers for Use at High and Low Temperatures in: Polymer Science, Vol. 2, North-Holland Publishing, New York 1972

    Google Scholar 

  73. Slade, P. E., Jenkins, L. T.: Thermal Characterization Techniques, Vols. 1 and 2, Marcel Dekker, New York 1966 and 1970

    Google Scholar 

  74. Neuse, E. W.: J. Organomet. Chem. 6, 92 (1966)

    Google Scholar 

  75. Shulman, G. P., Lochte, W.: Polymer Prepr. 6, 773 (1965); J. Macromol. Sci. Chem. 1, 413 (1967). For more recent, complementary results see Chatfield, D. A., Einhorn, I. N.: J. Polym. Sci., Polym. Chem. Ed. 19, 601 (1981)

    Google Scholar 

  76. Dubey, G., Kane, J. J.: Am. Chem. Soc., Div. Org. Coat. Plast. Chem. Papers 30, 187 (1970)

    Google Scholar 

  77. Reed, R., Hidde, R.: Techn. Rep. AFML-TR-65-146, Vols. I and II (1965)

    Google Scholar 

  78. Levine, H. H., Delano, C. B., Kjoller, K. J.: Polym. Prepr. 5, 160 (1964)

    Google Scholar 

  79. Marks, B. S., Shoff, L. E., Watsey, G. W.: Techn. Rep. NASA CR-1723 (1971)

    Google Scholar 

  80. Kalnin, I. L., Breckenridge, G. J.: US Pat. 4,113,683 (1978); Chem. Abstr.: 90, 24256 (1979)

    Google Scholar 

  81. Wirsen, D.: Kem. Tidskr. 91, 16 (1979)

    Google Scholar 

  82. Matsushita Electric Works, Ltd., Jpn. Tokyo Koho, Jap. Pat. 80 28,438 (1980); Chem. Abstr.: 94, 23967 (1981)

    Google Scholar 

  83. Minges, M. L.: High Temp. — High Pressures 1, 607 (1969). Marks, B. S., Rubin, L.: J. Macromol. Sci. Chem. 3, 555 (1969); Dickey, R. R., Lundell, J. H., Parker, J. A.: Macromol. Sci., Chem. 3, 573 (1969); D'Alelio, G. F., Parker, J. A.: Ablative Plastics, Marcel Dekker, New York 1971

    Google Scholar 

  84. Lipskis, A. et al.: Liet. TSR Mokslu Akad. Darb., Ser. B 1972, 159; Chem. Abstr.: 79, 92894 (1973)

    Google Scholar 

  85. Dunay, M.: US Pat. 3,775,213 (1973); Chem. Abstr.: 80, 71793 (1974). Sheratte, M. B.: US Pat. 4,154,919 (1979); Chem. Abstr.: 91, 92439 (1979).

    Google Scholar 

  86. Verzwyvelt, S. A.: Fr. Dem. 2440084 (1978); Chem. Abstr. 94, 124660 (1981). Martin, R. E.: Technical Rep. NASA-CR-159653, FCR-1017 (1978); Yaffe, M. R., Murray, J. N.: Proc. DOE Chem./Hydrogen Energy Syst. Contract. Rev. (CONF-781142), 37 (1978; publ. 1979); Chem. Abstr. 94, 22105 (1981)

    Google Scholar 

  87. Reed, R., Hidde, R.: J. Polym. Sci., Part A 1, 1531 (1963); Technical Report AFML-TR-65-136 (1965)

    Google Scholar 

  88. Hergenrother, P. M.: SAMPE Quarterly 3 [1], 1 (1971)

    Google Scholar 

  89. Gosnell, R. B., Levine, H. H.: J. Macromol. Sci. Chem. 3, 1381 (1969)

    Google Scholar 

  90. Ross, J. H., Opt, P. C.: Appl. Polym. Symp. [9], 23 (1969), and earlier reports from this group; Singleton, R. W.: Appl. Polym. Symp. [9] 133 (1969)

    Google Scholar 

  91. Conciatori, A. B., Smart, C. L.: US Pat. 3,502,606 (1970); Chem. Abstr. 72, 112737 (1970). Bohrer, T. C., Rosenthal, A. J.: US Pat. 3,502,756 (1970); Chem. Abstr. 72, 112727 (1970)

    Google Scholar 

  92. Tesoro, G., Moussa, A.: Fire Retard., Proc. Eur. Conf. Flammability, Fire Retard., 2nd, 159 (1978; pub. 1980); Chem. Abstr. 92, 182415 (1980)

    Google Scholar 

  93. Defosse, T. C., Welch, I. H.: Mod. Text. 52, 65 (1971)

    Google Scholar 

  94. Chenevey, E. C.: Technical Rep. NASA-CR-152281 (1978); Technical Report NASA-CR-159644 (1979)

    Google Scholar 

  95. Kalnin, I. L., Powers, E. J.: US Pat. 3,903,248 (1975); Chem. Abstr. 83, 195038 (1975)

    Google Scholar 

  96. Ezekiel, H. M., Spain, R. G.: US Pat. 3,528,774 (1970); Chem. Abstr. 73, 110796 (1970). Stuetz, D. E.: Am. Chem. Soc., Div. Org. Coat. Plast. Chem. Papers 31, 389–99 (1971)

    Google Scholar 

  97. Model, F. S., Lee, L. A.: Polybenzimidazole Reverse Osmosis Membranes, in: Reverse Osmosis Membrane Research, Lonsdale, H. K., and Podall, H. E., Eds., Plenum Publishing Co., New York 1972

    Google Scholar 

  98. Tan, M., Davis, H. J.: Techn. Rep. W 79-07571, OWRT-7527(1) (1978); Chem. Abstr. 92, 99356 (1980); Goldsmith, R. L. et al.: Technical Rep. W 79-09314, OWRT-7509(1) (1979); Chem. Abstr. 92, 203270 (1980). Senoo, M., Mori, K., Taketani, Y.: Ger. Pat. 2,559,931 (1979); Chem. Abstr. 92, 111507 (1980)

    Google Scholar 

  99. Suzuki, H. et al.: Bull. Chem. Soc. Jpn. 48, 1922 (1975)

    Google Scholar 

  100. Rodé, V. V. et al.: Izv. Akad. Nauk SSSR, Ser. Khim. 1968, 2662

    Google Scholar 

  101. Le Maux, P. et al.: J. Org. Chem. 45, 4524 (1980), and refs. cited therein

    Google Scholar 

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Neuse, E.W. (1982). Aromatic polybenzimidazoles. Syntheses, properties, and applications. In: Synthesis and Degradation Rheology and Extrusion. Advances in Polymer Science, vol 47. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0038530

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  • DOI: https://doi.org/10.1007/BFb0038530

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