Chemistry of Heterocyclic Compounds

, Volume 33, Issue 8, pp 883–897 | Cite as

Properties and application of aryl-substituted azines (review)

  • V. P. Borovik
  • O. P. Shkurko


Aryl-substituted six-membered azaaromatic heterocycles have a range of properties that make it possible to use them in scientific investigations and in modern regions of technology. The possibilities of using arylazines in chemical analysis, in catalytic processes, and as optical and photochromic materials in polymer chemistry are surveyed.


Polymer Chemical Analysis Organic Chemistry Catalytic Process Scientific Investigation 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    T. Shibamoto, Koryo,111, 69 (1975); Chem. Abstr.,84, 149375 (1976).Google Scholar
  2. 2.
    O. G. Vitzthum, P. Werkhoff, and P. Hubert, J. Food Sci.,40, 911 (1975); Chem. Abstr.,83, 130246 (1975).Google Scholar
  3. 3.
    M. Duenger, S. African Patent No. 6,906,582; Chem. Abstr.,73, 106474 (1970).Google Scholar
  4. 4.
    A. F. Thomas and F. Bassols, J. Agric. Food Chem.,40, 2236 (1992); Chem. Abstr.,117, 211047 (1992).Google Scholar
  5. 5.
    M. Ishihara, T. Tsuneya, M. Shiga, S. Kawashima, K. Yamagishi, F. Yoshida, H. Sato, and K. Uneyama, J. Agric. Food Chem.,40, 1647 (1992); Chem. Abstr.,117, 137400 (1992).Google Scholar
  6. 6.
    X. A. Dominguez, G. Fuente, A. G. Gonzalez, M. Reina, and I. Timon, Heterocycles,27, 35 (1988).Google Scholar
  7. 7.
    J. J. Brophy and G. W. K. Cavill, Heterocycles,14, 477 (1980).Google Scholar
  8. 8.
    G. Ohloff and I. Flament,11, 663 (1978).Google Scholar
  9. 9.
    O. Nishimura, H. Masuda, and S. Mihara, Koryo,165, 91 (1990); Chem. Abstr.,113, 210350 (1990).Google Scholar
  10. 10.
    W. M. Coleman, J. Chromatogr. Sci.,30, 159 (1992).Google Scholar
  11. 11.
    S. Matsushima, T. Ohsumi, and S. Sugawara, Agric. Biol. Chem.,47, 507 (1983); Chem. Abstr.,98, 195196 (1983).Google Scholar
  12. 12.
    E. Leete, Biogenesis of Natural Compounds, P. Bernfeld (ed.), Pergamon, Oxford (1963), Chapt. 17.Google Scholar
  13. 13.
    W. R. Kem, R. N. Scott, and J. H. Duncan, Experientia,32, 684 (1976); Chem. Abstr.,85, 59926 (1976).Google Scholar
  14. 14.
    M. P. Cruskie, J. A. Zoltewicz, and K. A. Abboud, J. Org. Chem.,60, 7491 (1995).Google Scholar
  15. 15.
    B. D. Alreja, S. L. Kattige, B. Lal, and N. J. de Souza, Heterocycles,24, 1637 (1986).Google Scholar
  16. 16.
    M. Aoki, T. Ohtsuka, Y. Itezono, K. Yokose, K. Furihata, and H. Seto, Tetrahedron Lett.,32, 221 (1991).Google Scholar
  17. 17.
    L. N. Tokareva, G. D. Gal'pern, A. V. Kotova, and I. D. Leonov, Neftekhimiya,7, 790 (1967).Google Scholar
  18. 18.
    L. A. Summers, Adv. Heterocycl. Chem.,35, 281 (1984).Google Scholar
  19. 19.
    Y. Sakon, T. Ohnuma, M. Hashimoto, T. Saito, T. Tsutsui, and C. Adachi, US Patent No. 5,077,142; Chem. Abstr.,117, 16862 (1992).Google Scholar
  20. 20.
    S. Bohm, A. Stadlik, J. Kuthan, and O. Richter, Czech. Patent No. 255,764; Chem. Abstr.,111, 194603 (1989).Google Scholar
  21. 21.
    A. Kurfuerst, P. Lhotak, J. Kuthan, and O. Richter, Czech. Patent No. 256,977; Chem. Abstr.,111, 115053 (1989).Google Scholar
  22. 22.
    A. Krufürst, P. Lhotak, M. Petru, and J. Kuthan, Coll. Czech. Chem. Commun.,54, 462 (1989).Google Scholar
  23. 23.
    R. Pater, J. Heterocyclic Chem.,7, 1113 (1970).Google Scholar
  24. 24.
    CIBA Ltd., French Patent No. 1,396,684; Chem. Abstr.,63, 9964 (1965).Google Scholar
  25. 25.
    L. Maskiya, Additives for Plastics [Russian translation], Khimiya, Moscow (1978), p. 144.Google Scholar
  26. 26.
    G. Reinert and K. Burdeska, Eur. Pat. Appl. 280,654; Chem. Abstr.,110, 77445 (1989).Google Scholar
  27. 27.
    J. E. A. Otterstedt and R. Pater, J. Heterocyclic Chem.,9, 225 (1972).Google Scholar
  28. 28.
    J. E. A. Otterstedt and R. Pater, US Patent No. 3,787,428; Ref. Zh. Khim., 4N261P (1975).Google Scholar
  29. 29.
    B. Helmo, H. P. Jakob, and H. Heller, US Patent No. 3,896,125; Chem. Abstr.,84, 5828 (1976).Google Scholar
  30. 30.
    M. Slongo, J. L. Birbaum, J. Rody, and A. Valet, Eur. Pat. Appl. 453,405; Chem. Abstr.,116, 41487 (1992).Google Scholar
  31. 31.
    M. Sudo, T. Muraki, E. Kawaki, E. Kawachi, and Y. Kawachi, Jpn. Pat. Appl. 03,190,864; Chem. Abstr.,115, 280067 (1991).Google Scholar
  32. 32.
    A. Grobowska and L. Kaczmarek, Pol. J. Chem.,66, 715 (1992); Chem. Abstr.,117, 211699 (1992).Google Scholar
  33. 33.
    H. Brunetti, German Patent No. 2,155,453; Chem. Abstr.,77, 62782 (1972).Google Scholar
  34. 34.
    T. Ozeki, T. Yagi, H. Haruna, and H. Takahashi, Jpn. Pat Appl. 61,179,245; Chem. Abstr.,106, 34036 (1987).Google Scholar
  35. 35.
    V. I. Kelarev, R. A. Karakhanov, V. R. Mkrtchan, and A. S. Kokosova, Khim. Tekhnol. Topliv. i Masel, No. 5, 32 (1990); Chem. Abstr.,113, 100538 (1990).Google Scholar
  36. 36.
    T. S. Tran, M. D. Vu, and H. Thai, Tap Chi Hoa Hoc,24, 22 (1986); Chem. Abstr.,106, 177380 (1987).Google Scholar
  37. 37.
    M. Horio and T. Misumi, Jpn. Pat. Appl. 02,300,259; Chem. Abstr.,114, 230115 (1991).Google Scholar
  38. 38.
    M. Yanagawa, US Patent No. 4,501,689; Chem. Abstr.,102, 222327 (1985).Google Scholar
  39. 39.
    Yokohama Rubber Co., Jpn. Pat Appl. 59,159,872; Chem. Abstr.,102, 133162 (1985).Google Scholar
  40. 40.
    E. Takahashi, T. Morikawa, and H. Haruta, Jpn. Pat. Appl. 03,256,048; Chem. Abstr.,116, 162556 (1992).Google Scholar
  41. 41.
    K. Ogi, T. Yoshizawa, and H. Sakamoto, Jpn. Pat. Appl. 01,229,241; Chem. Abstr.,112, 169016 (1990).Google Scholar
  42. 42.
    T. Kamamura, S. Goto, and Y. Suda,111, 105859 (1989).Google Scholar
  43. 43.
    A. Ezaki, H. Akamatsu, and N. Kagawa, Jpn. Pat. Appl. 62,196,648; Chem. Abstr.,108, 121982 (1988).Google Scholar
  44. 44.
    H. Sakamoto, Y. Kaneko, and H. Ninomiya, Jpn. Pat. Appl. 62,187,837; Chem. Abstr., 29973 (1988).Google Scholar
  45. 45.
    H. Sakamoto, Y. Kaneko, and H. Ninomiya, Jpn. Pat. Appl. 62,156,654; Chem. Abstr.,107, 225938 (1987).Google Scholar
  46. 46.
    A. S. Trofimov, V. I. Eroshkin, V. P. Krivopalov, T. A. Andreeva, and V. P. Mamaev, Inventor's Certificate No. 1,173,375; Byull. Izobret., No. 30, 193 (1985).Google Scholar
  47. 47.
    T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, V. P. Mamaev, and A. S. Trofimov, Avtometriya, No. 4, 3 (1991).Google Scholar
  48. 48.
    T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, E. B. Nikolaenkova, and V. P. Mamaev, Inventor's Certificate No. 1,819,004; Byull. Izobret., No. 10, 252 (1995).Google Scholar
  49. 49.
    M. I. Dobrikov, E. L. Mishchenko, and G. V. Shiskin, Izv. Sibirsk. Otd. Akad. Nauk SSSR. Ser. Khim., No. 3, 133 (1989).Google Scholar
  50. 50.
    S. Truchlik, V. Kabatova, M. Dimun, and S. Zerman, Thermochim. Acta,92, 205 (1985); Chem. Abstr.,105, 42130 (1986).Google Scholar
  51. 51.
    NASA Contact Rep. 1975; Sci. Tech. Aerosp. Rep.,14, No. 76-22397; Chem. Abstr.,85, 145386 (1976).Google Scholar
  52. 52.
    Ricoh Co., Jpn. Pat. Appl. 59,177,566; Chem. Abstr.,102, 87608 (1985).Google Scholar
  53. 53.
    V. M. Ostrovskaya, O. T. Lushina, L. V. Lomakina, M. S. Aksenova, I. A. Krasavin, V. A. Inshakova, E. K. Mamaeva, V. P. Mamaev, V. P. Krivopalov, and O. A. Zagulyaeva, German Patent No. 3,902,453; Chem. Abstr.,114, 258778 (1991).Google Scholar
  54. 54.
    V. M. Ostrovskaya, L. V. Lomakova, N. A. Fomin, M. S. Aksenova, O. N. Garicheva, A. V. Ivashchenko, V. P. Mamaev, V. P. Krivopalova, and I. G. Gakh, Inventor's Certificate No. 1,178,819; Byull. Izobret., No. 34, 94 (1985).Google Scholar
  55. 55.
    V. M. Ostrovskaya, L. V. Lomakina, N. A. Fomin, M. S. Aksenova, O. N. Garicheva, A. V. Ivashchenko, V. P. Mamaev, V. P. Krivopalov, and I. G. Gakh, German Patent No. 3,309,000; Chem. Abstr.,102, 89346 (1985).Google Scholar
  56. 56.
    A. V. Ivashchenko, Dichroic Dyes for Liquid Crystal Displays, CRC Press, London (1994), p. 190.Google Scholar
  57. 57.
    G. Pelzl, H. Zaschke, and D. Demus, Displays,6, No. 3, 141 (1985); Chem. Abstr.,104, 12916 (1986).Google Scholar
  58. 58.
    D. Demus, H. Zaschke, G. Pelzl, H. Enzenberg, and A. Isenberg, German Patent No. 3,408,042; Chem. Abstr.,102, 158242 (1985).Google Scholar
  59. 59.
    H. Zaschke, H. Schubert, F. Kuschel, F. Dinger, and D. Demus, DDR Patent No. 95,892; Chem. Abstr.,80, 32446 (1974).Google Scholar
  60. 60.
    G. Kraus and A. Kolbe, J. Chromatogr.,147, 17 (1978); Chem. Abstr.,88, 79522 (1978).Google Scholar
  61. 61.
    L. Sojak, G. Kraus, I. Ostrovsky, E. Kralovicova, and J. Krupcik, J. Chromatogr.,206, 475 (1981); Chem. Abstr.,94, 219065 (1981).Google Scholar
  62. 62.
    K. Isomura, Y. Oozono, K. Takehara, M. Era, T. Tsutsui, and S. Saito, Thin Solid Films,178, 351 (1989).Google Scholar
  63. 63.
    Y. Shudo, K. Ujiie, M. Sasaki, and M. Hashimoto, Jpn. Pat. Appl. 01,185,527; Chem. Abstr.,112, 87907 (1990).Google Scholar
  64. 64.
    D. Dorsch, R. Eidenschink, B. Rieger, and G. Marowsky, German Patent Appl. 3,641,024; Chem. Abstr.,110, 15768 (1989).Google Scholar
  65. 65.
    C. C. Frazier, M. P. Cockerham, E. A. Chauchard, and C. H. Lee, J. Opt. Soc. Am., B, Opt. Phys.,4, 1899 (1987); Chem. Abstr.,108, 46448 (1988).Google Scholar
  66. 66.
    L. A. Lee, US Patent No. 4,506,368; Chem. Abstr.,102, 229283 (1985).Google Scholar
  67. 67.
    M. Matsuo, T. Sakaguchi, Y. Muroyama, and N. Akamatsu, Jpn. Pat. No. 7,414,849; Chem. Abstr.,82, 45070 (1975).Google Scholar
  68. 68.
    H. M. Muramatsu, K. Shibata, and M. Matsui, Jpn. Pat. Appl. 04,279,568; Chem. Abstr.,118, 61532 (1993).Google Scholar
  69. 69.
    D. R. Waring, Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees (eds.), Vol. 1, Part 1, Pergamon, Oxford (1984), p. 339.Google Scholar
  70. 70.
    H. Zollinger, Color Chemistry, VCH, Weinheim (1987), pp. 191, 207.Google Scholar
  71. 71.
    J. R. Allan, B. R. Carson, D. L. Gerrard, and J. Birnie, Eur. Polymer J.,26, 241 (1990); Chem. Abstr.,112, 236361 (1990).Google Scholar
  72. 72.
    A. T. Pilipenko and E. R. Falendysh, Usp. Khim.,41, 2094 (1972).Google Scholar
  73. 73.
    W. A. Butte and F. H. Case, J. Org. Chem.,26, 4690 (1961).Google Scholar
  74. 74.
    J. J. Lafferty and F. H. Case, J. Org. Chem.,32, 1591 (1967).Google Scholar
  75. 75.
    A. A. Schult, J. F. Wu, and F. H. Case, Talanta,23, 543 (1976).Google Scholar
  76. 76.
    R. Belcher, M. Y. Kuchawar, and W. I. Stephen, J. Chem. Soc. Pak.,11, 185 (1989); Chem. Abstr.,113, 40625 (1990).Google Scholar
  77. 77.
    M. Y. Kuchawar and Z. P. Memon, J. Chem. Soc. Pak.,5, 55 (1983); Chem. Abstr.,99, 224246 (1983).Google Scholar
  78. 78.
    B. M. Kelly-Basetti, D. J. Cundy, S. M. Pereira, W. H. F. Sasse, G. P. Savage, and G. W. Simpson, Bioorg. Med. Chem. Lett.,5, 2989 (1995).Google Scholar
  79. 79.
    E. Solem, U. B. Seiffert, U. B. Jalner, M. Kaul, L. J. Behnken, K. Froehlich, and M. Zirker, J. Clin. Chem. Clin. Biochem.,26, 697 (1988); Chem. Abstr.,110, 53997 (1989).Google Scholar
  80. 80.
    B. G. Stephens and H. A. Suddeth, Analyst,95, No. 1126, 70 (1970); Chem. Abstr.,72, 96408 (1970).Google Scholar
  81. 81.
    E. Yoneda, M. Takehisa, K. Kochi, and H. Yashima, Hiroshima-Kenritsu Byoin Nempo,10, 97 (1978); Chem. Abstr.,90, 134683 (1979).Google Scholar
  82. 82.
    T. W. Stephens, PCT Int. Patent Appl. 8,302,670; Chem. Abstr.,99, 209285 (1983).Google Scholar
  83. 83.
    B. R. Day, D. R. Williams, and C. A. Marsh, Clin. Biochem.,12, 22 (1979); Chem. Abstr.,90, 147988 (1979).Google Scholar
  84. 84.
    M. Unoki, M. Fujiwara, T. Aoyama, A. Kaku, and S. Shin, Jpn. Pat. Appl. 79,134,694; Chem. Abstr.,92, 72293 (1980).Google Scholar
  85. 85.
    Wako Pure Chem. Ind. Ltd., Jpn. Pat. Appl. 5,932,867; Chem. Abstr.,100, 171198 (1984).Google Scholar
  86. 86.
    D. G. Sankar, C. S. P. Sastry, M. N. Reddy, and M. Aruna, Indian J. Pharm. Sci.,50, 178 (1988); Chem. Abstr.,109, 237154 (1988).Google Scholar
  87. 87.
    S. Tsurubou and T. Sakai, Gifu Shika Daigaku Shingakubu Kenkyu Hokoku,9, 91 (1983); Chem. Abstr.,100, 131635 (1984).Google Scholar
  88. 88.
    M. C. Mehra, M. Satake, L. F. Chang, and H. B. Singh, Microchem. J.,31, 392 (1985); Chem. Abstr.,103, 115224 (1985).Google Scholar
  89. 89.
    T. Nagahiro, M. Satake, and B. K. Puri, Zh. Anal. Khim.,40, 1601 (1985).Google Scholar
  90. 90.
    Y. Sasaki, Anal. Chem. Acta,98, 335 (1978); Chem. Abstr.,89, 70395 (1978).Google Scholar
  91. 91.
    C. Musikas, P. Vitorge, R. Fitoussi, M. Bonnin, and D. Pateevialard-Goudou, Radioact. Waste Manage.,6, 255 (1982); Chem. Abstr.,98, 61821 (1983).Google Scholar
  92. 92.
    M. Bonnin, C. Musikas, and P. Vitorge, Eur. Patent Appl. 70,226; Chem. Abstr.,98, 206331 (1983).Google Scholar
  93. 93.
    C. Musikas, Actinide/Lanthanide Sep., Proc. Int. Symp. (1984), p. 19; Chem. Abstr.,104, 97383 (1986).Google Scholar
  94. 94.
    X. Vitart, C. Musikas, J. Y. Pasquiou, and P. Hoel, J. Less Common Met.,122, 275 (1986); Chem. Abstr.,105, 230344 (1986).Google Scholar
  95. 95.
    T. Okutani, Y. Oishi, K. Uchida, and N. Arai, Nippon Kagaku Kaishi, No. 7, 853 (1986); Chem. Abstr.,105, 145145 (1986).Google Scholar
  96. 96.
    B. K. Puri, M. Satake, G. Kano, and S. Usami, Anal. Chem.,59, 1850 (1987); Chem. Abstr.,107, 50990 (1987).Google Scholar
  97. 97.
    W. C. Hoyle and J. Benga, Talanta,27(11B), 963 (1980); Chem. Abstr.,94, 135331 (1981).Google Scholar
  98. 98.
    H. Kato, S. Tomura, and Y. Wada, Jpn. Pat. Appl. 79,159,383; Chem. Abstr.,93, 35032 (1980).Google Scholar
  99. 99.
    S. Yasuda, T. Kurohara, and A. Taguro, British Patent Appl. 2,095,253; Chem. Abstr.,98, 7905 (1983).Google Scholar
  100. 100.
    H. Kagawa, Jpn. Pat. Appl. 61,133,227; Chem. Abstr.,106, 68436 (1987).Google Scholar
  101. 101.
    Fuji-Xerox Co., Jpn. Pat. Appl. 57,171,343; Chem. Abstr.,99, 222378 (1983).Google Scholar
  102. 102.
    J. L. Lin, M. Satake, and B. K. Puri, Analysis,13, 141 (1985); Chem. Abstr.,102, 230982 (1985).Google Scholar
  103. 103.
    T. Nagahiro, K. Uesugi, M. Satake, and B. K. Puri, Bull. Chem. Soc. Jpn.,58, 1115 (1985); Chem. Abstr.,102, 230998 (1985).Google Scholar
  104. 104.
    T. Nagashiro, M. Satake, and B. K. Puri, Indian J. Chem. Sect. A,25A, 99 (1986); Chem. Abstr.,105, 17316 (1986).Google Scholar
  105. 105.
    M. C. Mehra, T. Nagahiro, and M. Satake, Microchem. J.,33, 198 (1986); Chem. Abstr.,105, 34724 (1986).Google Scholar
  106. 106.
    J. L. Lin, J. Chin. Chem. Soc.,31, 395 (1984); Chem. Abstr.,102, 231038 (1985).Google Scholar
  107. 107.
    T. Sakai, N. Ohno, N. Ichinobe, and H. Sasaki, Anal. Chim. Acta,221, 109 (1989); Chem. Abstr.,112, 68943 (1990).Google Scholar
  108. 108.
    T. Nagahiro, M. Satake, B. K. Puri, and J. L. Lin, Microchim. Acta,1, 85 (1984); Chem. Abstr.,100, 95754 (1984).Google Scholar
  109. 109.
    T. Nagahiro, K. Uesugi, M. C. Mehra, and M. Satake, Talanta,31, 1112 (1984); Chem. Abstr.,102, 71944 (1985).Google Scholar
  110. 110.
    S. Tsurubou and T. Sakai, Analyst,109, 1397 (1984); Chem. Abstr.,102, 105280 (1985).Google Scholar
  111. 111.
    F. E. Smith, J. Herbert, J. Gaudin, D. Henessy, and G. R. Reid, Clin. Biochem.,17, 306 (1984); Chem. Abstr.,102, 2800 (1985).Google Scholar
  112. 112.
    P. Fossati, H. Heidenreich, K. Wehling, and H. Hugl, European Patent Appl. 331,065; Chem. Abstr.,112, 232275 (1990).Google Scholar
  113. 113.
    T. Sakai, N. Ohno, T. Mori, and H. Sasaki, Bunseki Kagaku,37, 488 (1988); Chem. Abstr.,109, 176300 (1988).Google Scholar
  114. 114.
    S. Tsurubou and T. Sakai, Bunseki Kagaku,33, 139 (1984); Chem. Abstr.,100, 202606 (1984).Google Scholar
  115. 115.
    L. L. Stookey, Anal Chem.,42, 779 (1970).Google Scholar
  116. 116.
    J. D. Artiss, D. R. Strandbergh, and B. Zak, Microchem. J.,28, 275 (1983); Chem. Abstr.,98, 194474 (1983).Google Scholar
  117. 117.
    Toshiba Corp., Jpn. Pat. Appl. 59,211,564; Chem. Abstr.,102, 135950 (1985).Google Scholar
  118. 118.
    T. Nagahiro, K. Uesugi, and M. Satake, Anal. Sci.,1, 359 (1985); Chem. Abstr.,104, 141262 (1986).Google Scholar
  119. 119.
    G. Denti, S. Campagna, L. Sabatino, S. Serroni, M. Ciano, and V. Balzani, Inorg. Chem.,29, 4750 (1990); Chem. Abstr.,113, 223397 (1990).Google Scholar
  120. 120.
    K. I. Zamaraev and V. N. Parmon, Usp. Khim.,52, 1433 (1983); Russ. Chem. Rev.,52, 817 (1983).Google Scholar
  121. 121.
    F. P. Rotzinger, S. Munavalli, P. Comte, J. K. Hurst, M. Gratzel, F. J. Pern, and A. J. Frank, J. Am. Chem. Soc.,109, 6619 (1987).Google Scholar
  122. 122.
    I. Willner, R. Maidan, D. Mandler, H. Dürr, C. Dörr, and K. Zengerle, J. Am. Chem. Soc.,109, 6080 (1987).Google Scholar
  123. 123.
    J. F. Knifton, US Patent No. 4,605,677; Chem. Abstr.,105, 174807 (1986).Google Scholar
  124. 124.
    A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida, and A. Misano, J. Am. Chem. Soc.,90, 1878 (1968).Google Scholar
  125. 125.
    G. W. Gokel, Crown Ethers and Cryptands, Royal Soc. Chem. (1994), pp. 55, 167.Google Scholar
  126. 126.
    D. Luneau, J. Laugier, P. Rey, G. Ulrich, R. Ziessel, P. Legoli, and M. Drillon, J. Chem. Soc. Chem. Commun., No. 6, 741 (1994).Google Scholar
  127. 127.
    W. Sliwa, L. Chrzastek, and M. Mielniczak, Heterocycles,36, 1645 (1993).Google Scholar
  128. 128.
    P. D. Beer and P. D. Rotin, J. Chem. Soc. Chem. Commun., No. 1, 52 (1988).Google Scholar
  129. 129.
    K. T. Potts, K. A. G. Raiford, and K. M. Keshavarz, J. Am. Chem. Soc.,115, 2793 (1993).Google Scholar
  130. 130.
    J. M. Lehn and A. Rigault, Angew. Chem. Int. Ed.,27, 1095 (1988).Google Scholar
  131. 131.
    J. M. Lehn and J. B. R. de Vains, Helv. Chim. Acta,75, 1221 (1992).Google Scholar
  132. 132.
    T. M. Garrett, U. Koert, J. M. Lehn, A. Rigault, D. Meyer, and J. Fischer, J. Chem. Soc. Chem. Commun., No. 7, 557 (1990).Google Scholar
  133. 133.
    M. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, Polyimides — a Group of Thermally Stable Polymers [in Russian], Nauka, Leningrad (1983).Google Scholar
  134. 134.
    V. V. Korshak, A. L. Rusanov, and I. Batirov, News in the Region of Thermally Stable Polymers [in Russian], Donish, Dushanbe (1986).Google Scholar
  135. 135.
    V. V. Korshak and A. L. Dushanbe, Usp. Khim.,52, 812 (1983).Google Scholar
  136. 136.
    D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother (eds.), Polyimides, Blackie, Glasgow, London (1990).Google Scholar
  137. 137.
    M. M. Koton, Vysokomol. Soed.,13A, 1348 (1971).Google Scholar
  138. 138.
    M. M. Koton, V. P. Mamaev, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Borovik, T. K. Meleshko, V. N. Artem'eva, and E. N. Dergacheva, Zh. Prikl. Khim.,60, 1851 (1987).Google Scholar
  139. 139.
    M. M. Koton, V. P. Mamaev, A. M. Dubnova, and E. M. Nekrasova, Vysokomol. Soed.,20B, 792 (1978).Google Scholar
  140. 140.
    V. P. Mamaev, V. P. Borovik, M. M. Koton, T. M. Kiseleva, E. M. Nekrasova, E. N. Dergacheva, S. N. Nikolaeva, and G. N. Fedorova, Vysokomol. Soed.,25B, 102 (1983).Google Scholar
  141. 141.
    Yu. N. Sazanov, G. N. Fedorova, E. M. Nekrasova, and T. M. Kiseleva, Vysokomol. Soed.,25A, 949 (1983).Google Scholar
  142. 142.
    V. P. Mamaev, V. P. Borovik, M. M. Koton, and E. M. Nekrasova, Inventor's Certificate No. 853,316; Byul. Izobret., No. 44, 271 (1985).Google Scholar
  143. 143.
    M. M. Koton, V. V. Kudryavtsev, V. N. Artem'eva, E. M. Nekrasov, V. P. Slizkova, T. A. Maricheva, N. D. Kozhurnikova, L. A. Laius, I. V. Gofman, E. N. Dergacheva, V. E. Smirnova, Yu. N. Sazanov, G. N. Fedorova, O. P. Shkurko, and V. P. Borovik, Russian Federation Patent No. 2,034,862; Byul. Izobret., No. 13, 184 (1995).Google Scholar
  144. 144.
    G. M. Mikhailov, L. N. Korzhavin, V. V. Kudryavtsev, M. M. Koton, T. A. Maricheva, M. A. Ivanova, N. V. Bobrova, S. V. Bronnikov, N. A. Grigor'eva, O. P. Shkurko, V. P. Borovik, S. M. Yakopson, and O. S. Karchmarchik, Russian Federation Patent No. 2,034,861; Byull. Izobret., No. 13, 184 (1995).Google Scholar
  145. 145.
    V. N. Artem'eva, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Slizkova, Yu. G. Baklagina, N. V. Lukasheva, O. P. Shkurko, and V. P. Borovik, Izv. Akad. Nauk. Ser. Khim., No. 10, 2288 (1992).Google Scholar
  146. 146.
    V. N. Artem'eva, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Slizkova, L. A. Shibaev, N. G. Stepanov, Yu. N. Sazanov, G. N. Fedorova, O. P. Shkurko, and V. P. Borovik, Izv. Akad. Nauk. Ser. Khim., No. 10, 2297 (1992).Google Scholar
  147. 147.
    D. M. Mognonov, V. P. Borovik, L. D. Radnaeva, S. O. Botoeva, O. P. Shkurko, and A. A. Izynev, Sibirsk. Khim. Zh., No. 4, 99 (1991).Google Scholar
  148. 148.
    Y. Yamazaki, T. Ishikawa, T. Suzuki, and Y. Irie, Nippon Kagaku Kaishi, No. 3, 502 (1976); Chem. Abstr.,85, 6434 (1976).Google Scholar
  149. 149.
    T. Teshirogi, Jpn. Pat. Appl. 0,348,666; Chem. Abstr.,115, 49064 (1991).Google Scholar
  150. 150.
    R. Seltzer and D. A. Gordon, US Patent No. 3,729,448; Ref. Zh. Khim., 4S 362 (1974).Google Scholar
  151. 151.
    R. Seltzer, D. A. Gordon, and P. D. Sherman, US Patent No. 3,814,719; Ref. Zh. Khim., 10S 363 (1975).Google Scholar
  152. 152.
    R. Seltzer and D. A. Gordon, German Patent No. 2,321,527; Chem. Abstr.,80, 83918 (1974).Google Scholar
  153. 153.
    É. S. Avanesyan, V. N. Zaplishnyi, and G. M. Pogosyan, Arm. Khim. Zh.,31, No. 8, 627 (1978).Google Scholar
  154. 154.
    V. V. Korshak, V. P. Mamaev, S. V. Vinogradova, Ya. S. Vygodskii, and E. P. Fokin, Inventor's Certificate No. 267,893; Byull. Izobret., No. 13, 71 (1970).Google Scholar
  155. 155.
    R. Pfaendner, J. P. Wolf, and K. Hoffmann, German Patent No. 4,237,768; Chem. Abstr.,120, 77946 (1994).Google Scholar
  156. 156.
    C. Paal and C. Demeler, Berichte,30, 1499 (1897).Google Scholar
  157. 157.
    K. Yamaguchi, Y. Yoshikawa, K. Sugimoto, Y. Tanabe, and A. Yamaguchi, European Patent Appl. 282,658; Chem. Abstr.,110, 95968 (1989).Google Scholar
  158. 158.
    K. Kurita and R. L. Williams, J. Polym. Sci. Polym. Chem. Ed.,11, 3125 (1973); Chem. Abstr.,81, 25974 (1974).Google Scholar
  159. 159.
    K. Kurita and R. L. Williams, J. Polym. Sci. Polym. Chem. Ed.,12, 1809 (1974); Chem. Abstr.,82, 58168 (1975).Google Scholar
  160. 160.
    M. M. Koton, T. M. Kiseleva, T. I. Zhukova, S. N. Nikolaeva, L. A. Laius, and Yu. N. Sazanov, Vysokomol. Soed.,23A, 1736 (1981).Google Scholar
  161. 161.
    L. H. Li (ed.), Adhesives and Adhesion Joints [Russian translation], Mir, Moscow (1988), p. 81.Google Scholar
  162. 162.
    R. Singh and A. S. Hay, Macromolecules,25, 1025 (1992); Chem. Abstr.,116, 60138 (1992).Google Scholar
  163. 163.
    S. Kondo, M. Kadowaki, M. Mase, T. Kakuno, and Y. Yuki, J. Macromol. Sci. Pure Appl. Chem.,30A, 315 (1993); Chem. Abstr.,118, 102651 (1993).Google Scholar
  164. 164.
    S. Sako, Jpn. Pat. Appl. 03,107,986; Chem. Abstr.,116, 117133 (1992).Google Scholar
  165. 165.
    N. Sawa, N. Kato, T. Masuda, S. Miura, and T. Suzuki, Jpn. Pat. Appl. 03,284,675; Chem. Abstr.,116, 235660 (1992).Google Scholar
  166. 166.
    T. Yamamoto, T. Maruyama, Z.-h. Zhou, T. Ito, T. Fukuda, Y. Yoneda, F. Begum, T. Ikeda, S. Sasaki, H. Takezoe, A. Fukuda, and K. Kubota, J. Am. Chem. Soc.,116, 4832 (1994).Google Scholar
  167. 167.
    H. Nagasaka and K. Ohta, European Patent Appl. 379200; Chem. Abstr.,114, 33166 (1991).Google Scholar
  168. 168.
    J. D. Coyle, A. M. Horton, R. S. Davidson, R. Bowser, and P. M. Morgan, European Patent Appl. 389,236; Chem. Abstr.,114, 218124 (1991).Google Scholar
  169. 169.
    H. Nagasaka and K. Ohta, Jpn. Pat. Appl. 02,189,548; Chem. Abstr.,114, 52934 (1991).Google Scholar
  170. 170.
    M. Oie, M. Kawada, and T. Yamada, Jpn. Pat. Appl. 03,107,164; Chem. Abstr.,115, 244064 (1991).Google Scholar
  171. 171.
    M. Hirose, Jpn. Pat. Appl. 03,154,058; Chem. Abstr.,116, 31460 (1992).Google Scholar
  172. 172.
    Y. Adachi, H. Nakai, T. Akiyama, M. Sasaki, and J. Nakamura, Jpn. Pat. Appl. 0,459,657; Chem. Abstr.,117, 160973 (1992).Google Scholar
  173. 173.
    N. Kita and M. Koike, German Patent No. 3,822,909; Chem. Abstr.,110, 183029 (1989).Google Scholar
  174. 174.
    G. Buhr, German Patent No. 3,337,024; Chem. Abstr.,103, 96424 (1985).Google Scholar
  175. 175.
    E. D. Laganis, G. K. Lalka, and W. K. Smothers, PCT Int. Patent Appl. 9,214,765; Chem. Abstr.,118, 171074 (1993).Google Scholar
  176. 176.
    M. Miyabe, H. Kohara, and T. Nakayama, German Patent No. 3,939,186; Chem. Abstr.,114, 72343 (1991).Google Scholar
  177. 177.
    Y. Takeda, M. Miyabe, and T. Nakayama, Jpn. Pat. Appl. 02,217,855; Chem. Abstr.,114, 111918 (1991).Google Scholar
  178. 178.
    H. Nakai, S. Goto, K. Kishida, and K. Naito, Jpn. Pat. Appl. 03,225,343; Chem. Abstr.,117, 58950 (1992).Google Scholar
  179. 179.
    T. Usami and T. Shimomura, Jpn. Pat. Appl. 0,321,495; Chem. Abstr.,115, 73775 (1991).Google Scholar
  180. 180.
    K. Imai and T. Asano, Jpn. Pat. Appl. 04,182,650; Chem. Abstr.,117, 242891 (1992).Google Scholar
  181. 181.
    K. Iwakura and H. Matsumoto, Jpn. Pat. Appl. 04,195,044; Chem. Abstr.,118, 49448 (1993).Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • V. P. Borovik
  • O. P. Shkurko

There are no affiliations available

Personalised recommendations