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Anionic copolymerization of cyclic ethers with cyclic anhydrides

  • Jozef Lustoň
  • František Vašš
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 56)

Abstract

This article summarizes and analyzes the results obtained for the anionic copolymerization of cyclic ethers with cyclic anhydrides. This reaction is of great practical importance, especially as curing reaction of epoxy resins and is also used for the preparation of linear polyesters with special functional pendant groups.

Our attention was concentrated mainly on the kinetics and mechanisms of copolymerization, the effect of epoxide and anhydride structure in copolymerization, the effect of type and structure of initiatior on the rate, and the course of copolymerization. The probable mechanisms are discussed. The copolymerization in the presence of proton-donor compounds as well as the effect of protondonors are also considered. For a better understanding of the processes, data and theoretical views on the non-catalyzed reaction are included.

Keywords

Tertiary Amine Proton Donor Carboxylate Anion Phthalic Anhydride Cyclic Ether 
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.

List of Abbreviations

BA

benzoic acid

BuE-PA

monobutylester of phthalic acid

BE-HET

monobenzylester of hexachloroendomethylenetetrahydrophthalic acid

BE-HHPA

monobenzylester of hexahydrophthalic acid

BE-MA

monobenzylester of maleic acid

BE-PA

monobenzylester of phthalic acid

BE-SA

monobenzylester of succinic acid

CA

citraconic anhydride

CHX

cyclohexanol

DMA

N,N-dimethylaniline

DMBA

dimethylbenzylamine

DY 062

high boiling tertiary amine (Ciba Geigy AG)

GA

glutaric anhydride

HEB

2-hydroxy-4-(2,3-epoxypropoxy)benzophenone

HHPA

hexahydrophthalic anhydride

HMTA

hexamethylenetetramine

MA

maleic anhydride

MTHPA

methyltetrahydrophthalic anhydride

NMA

nadic methyl anhydride (methylbicyclo[2.2.1]heptene-2,3-dicarboxylic anhydride isomers)

PA

phthalic anhydride

PGE

phenylglycidyl ether

PLA

palmitic acid

p-CH3 PGE

p-methylphenylglycidyl ether

p-Cl PGE

p-chlorophenylglycidyl ether

p-CO2CH3 PGE

p-acetyloxyphenylglycidyl ether

p-NO2 PGE

p-nitrophenylglycidyl ether

p-OCH3 PGE

p-methoxyphenylglycidyl ether

SA

succinic anhydride

TAP

tris-2,4,6-dimethylaminomethylphenol

TBA

tri-n-butylamine

TEA

triethanolamine

THA

tri-n-hexylamine

THPA

tetrahydrophthalic anhydride

X 157/2378

liquid acid anhydrides of acid number 392 (Ciba Geigy AG)

DGEBA

diglycidyl ether of bisphenol A-based epoxy resin of epoxy content 0.52 eq./100 g

ED-5

Soviet epoxy resin with epoxy content of 20 wt-%

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5 References

  1. 1.
    Weinschenk, A.: Chem. Ztg. 29, 1311 (1905)Google Scholar
  2. 2.
    Nishikubo, T., Imaura, M., Takaoka, T.: Nippon Kagaku Kaishi 1974, 185Google Scholar
  3. 3.
    Hilt, A., Hamann, K., Keifer, S.: Ger. Pat. 1 570 411 (1965)Google Scholar
  4. 4.
    Nollen, K., Kaden, V., Hamann, K.: Angew. Makromol. Chem. 6, 1 (1969)Google Scholar
  5. 5.
    Kroker, R., Hamann, K.: Angew. Makromol. Chem. 13, 1 (1970)Google Scholar
  6. 6.
    Lustoň, J., Guniš, J., Maňásek, Z.: J. Macromol. Sci.-Chem. A7, 587 (1973)Google Scholar
  7. 7.
    Lustoň, J., Schubertová, N., Maňásek, Z.: J. Polym. Sci., Symp. No. 40, 33 (1973)Google Scholar
  8. 8.
    Nishikubo, T. et al.: Nippon Kagaku Kaishi 1973, 1851Google Scholar
  9. 9.
    Matsuda, H.: J. Polym. Sci., Polym. Chem. Ed. 14, 1783 (1976)Google Scholar
  10. 10.
    Matsuda, H.: J. Appl. Polym. Sci. 22, 2093 (1978)Google Scholar
  11. 11.
    Matsuda, H., Minoura, Y.: J. Appl. Polym. Sci. 24, 811 (1979)Google Scholar
  12. 12.
    Matsuda, H.: J. Appl. Polym. Sci. 25, 1915 (1980)Google Scholar
  13. 13.
    Matsuda, H.: J. Appl. Polym. Sci. 25, 2339 (1980)Google Scholar
  14. 14.
    Lee, H., Neville, K.: Handbook of Epoxy Resins. New York: McGraw Hill 1967Google Scholar
  15. 15.
    Sorokin, M. F., Shode, L. G.: Lakokrasoch. Mater. Ikh Primen. 1968, 76; C. A. 68, 87768 (1968)Google Scholar
  16. 16.
    Ishii, Y., Sakai, S., in: Ring Opening Polymerization. Frisch, K. C., Reegen, S. L. (eds.). New York: Marcel Dekker 1968Google Scholar
  17. 17.
    Tanaka, Y., Mika, T. F., in: Epoxy Resins. May, C. A., Tanaka, Y. (eds.). New York: Marcel Dekker 1973Google Scholar
  18. 18.
    Reichert, K.-H. W.: Chimia 29, 453 (1975)Google Scholar
  19. 19.
    Arnold, R. J.: Mod. Plast. 41 (8), 149 (1964)Google Scholar
  20. 20.
    Fisch, W., Hofmann, W.: Makromol. Chem. 44, 8 (1961)Google Scholar
  21. 21.
    Kaplan, S. L., McAllister, L. E., Stewart, A. T.: Polym. Eng. Sci. 6, 65 (1966)Google Scholar
  22. 22.
    Fisch, W., Hofmann, W.: J. Polym. Sci. 12, 497 (1954)Google Scholar
  23. 23.
    Fisch, W., Hofmann, W., Koskikallio, J.: J. Appl. Chem. 6, 429 (1956)Google Scholar
  24. 24.
    Fisch, W., Hofmann, W., Koskikallio, J.: Chem. Ind. (London) 1956, 756Google Scholar
  25. 25.
    Dearborn, E. C., Fuoss, R. M., White, A. F.: J. Polym. Sci. 16, 201 (1955)Google Scholar
  26. 26.
    Schechter, L., Wynstra, J.: Ind. Eng. Chem. 48, 86 (1956)Google Scholar
  27. 27.
    Weiss, H. K.: Ind. Eng. Chem. 49, 1089 (1957)Google Scholar
  28. 28.
    Shimazaki, A., Kozima, M.: J. Chem. Soc. Jpn., Ind. Chem. Sec. (Kogyo Kagaku Zashi) 66, 1610 (1963)Google Scholar
  29. 29.
    Shimazaki, A.: J. Chem. Soc. Jpn., Ind. Chem. Sec. (Kogyo Kagaku Zashi) 67, 1304 (1964)Google Scholar
  30. 30.
    Kannebley, G.: Kunststoffe 47, 693 (1957)Google Scholar
  31. 31.
    Sorokin, M. F., Shode, L. G., Gershanova, E. L.: Lakokrasoch. Mater. Poluprod. 1967 (5), 67; C.A. 68, 96461 (1968)Google Scholar
  32. 32.
    Sorokin, M. F., Shode, L. G., Gershanova, E. L.: Chem. Prum. 17/42, 590 (1967)Google Scholar
  33. 33.
    Schechter, L., Wynstra, J., Kurkjy, R. P.: Ind. Eng. Chem. 49, 1107 (1957)Google Scholar
  34. 34.
    Pirozhnaya, L. M.: Plast. Massy 1961 (6), 56Google Scholar
  35. 35.
    Tanaka, Y., Kakiuchi, H.: J. Appl. Polym. Sci. 7, 1063 (1963)Google Scholar
  36. 36.
    Tanaka, Y., Kakiuchi, H.: J. Polym. Sci. A2, 3405 (1964)Google Scholar
  37. 37.
    Doszlop, S., Vargha, V., Horkay, F.: Periodica Polytech. (Budapest) 22, 253 (1978)Google Scholar
  38. 38.
    Patat, F., Wojtech, B.: Makromol. Chem. 37, 1 (1960)Google Scholar
  39. 39.
    Fischer, R. F.: J. Polym. Sci. 44, 155 (1960)Google Scholar
  40. 40.
    Fischer, R. F.: Ind. Eng. Chem. 52, 321 (1960)Google Scholar
  41. 41.
    Schwenk, E. et al.: Makromol. Chem. 51, 53 (1962)Google Scholar
  42. 42.
    Hilt, A., Reichert, K.-H. W., Hamann, K.: Makromol. Chem. 101, 246 (1967)Google Scholar
  43. 43.
    Šňupárek, J., Mleziva, J.: Chem. Prum. 18/43, 473 (1968)Google Scholar
  44. 44.
    Tanaka, Y., Haung, C. M.: Makromol. Chem. 120, 1 (1968)Google Scholar
  45. 45.
    Lustoň, J., Maňásek, Z., Kulíčková, M.: J. Macromol. Sci.-Chem. A12, 995 (1978)Google Scholar
  46. 46.
    Dreyfuss, P., Dreyfuss, M. P., in: Ring-Opening Polymerization. Frisch, K. C., Reegen, S. L. (eds.), p. 112. New York: Marcel Dekker 1968Google Scholar
  47. 47.
    Ref. 16, p. 17Google Scholar
  48. 48.
    Ref. 17, p. 13Google Scholar
  49. 49.
    Nelson, R. A., Jessup, R. S.: J. Res. Natl. Bur. Std. 48, 206 (1952)Google Scholar
  50. 50.
    Chapman, N. B., Isaacs, N. S., Parker, R. E.: J. Chem. Soc. 1959, 1925Google Scholar
  51. 51.
    Parker, R. E., Isaacs, N. S.: Chem. Rev. 59, 737 (1959)Google Scholar
  52. 52.
    Tanaka, Y., Kakiuchi, H.: J. Macromol. Chem. 1, 307 (1966)Google Scholar
  53. 53.
    Tsirkin, M. Z., Molotkov, R. V., Kazanskaia, V. F.: Plast. Massy 1963 (7), 17Google Scholar
  54. 54.
    Hilt, A., Trivedi, J., Hamann, K.: Makromol. Chem. 89, 177 (1965)Google Scholar
  55. 55.
    Hilt, A., Hamann, K.: Makromol. Chem. 92, 55 (1966)Google Scholar
  56. 56.
    Lustoň, J., Maňásek, Z.: Makromol. Chem. 181, 545 (1980)Google Scholar
  57. 57.
    Lustoň, J., Maňásek, Z.: J. Macromol. Sci. Chem. A12, 983 (1978)Google Scholar
  58. 58.
    Klaban, J., Smrčka, J., Mleziva, J.: Makromol. Chem. 111, 1 (1968)Google Scholar
  59. 59.
    Dobinson, B., Hofmann, W., Stark, B. P.: The Determination of Epoxide Groups, p. 18. London: Pergamon Press 1969Google Scholar
  60. 60.
    Szwarc, M.: Carbanions, Living Polymers and Electron Transfer Processes, Chap. VII. New York: Interscience Publishers 1968Google Scholar
  61. 61.
    Herold, B. J.: Catal. Rev., Sci. Eng. 17, 1 (1978)Google Scholar
  62. 62.
    Kazanskii, K. S.: Main lecture at the 21st Prague Microsymposium on Macromolecules, Ring-Opening Polymerization of Heterocycles, Karlovy Vary 1980, Pure Appl. Chem. 55, 1645 (1981)Google Scholar
  63. 63.
    Smith, J. D. B.: J. Appl. Polym. Sci. 23, 1385 (1979)Google Scholar
  64. 64.
    Červinka, O., Dědek, V., Ferles, M.: Organická chemie (Organic Chemistry), p. 609. Prague: SNTL 1969Google Scholar
  65. 65.
    Antipova, L. M. et al.: Plast. Massy 1973, 12Google Scholar
  66. 66.
    Mayahi, M. F., El-Bermani, M. F.: Can. J. Chem. 51, 3539 (1973)Google Scholar
  67. 67.
    Antoon, M. K., Koenig, J. L.: J. Polym. Sci., Polym. Chem. Ed. 19, 549 (1981)Google Scholar
  68. 68.
    Matějka, L. et al.: J. Polym. Sci., Polym. Chem. Ed. 21, (1983)Google Scholar
  69. 69.
    Lustoň, J., Maňásek, Z.: React. Kinet. Catal. Lett. 9, 47 (1978)Google Scholar
  70. 70.
    Alvey, F. B.: J. Appl. Polym. Sci. 13, 1473 (1969)Google Scholar
  71. 71.
    Bogatkov, S. V., Popov, A. F., Litvinenko, L. M.: Reakts. Sposobn. Org. Soedin. 6, 1011 (1969)Google Scholar
  72. 72.
    Bogatkov, S. V., Zaslavskii, V. G., Litvinenko, L. M.: Dokl. Akad. Nauk SSSR 210, 97 (1973)Google Scholar
  73. 73.
    Feltzin, J. et al.: J. Macromol. Sci.-Chem. A3, 261 (1969)Google Scholar
  74. 74.
    Lustoň, J., Maňásek, Z.: J. Macromol. Sci.-Chem. A13, 853 (1979)Google Scholar
  75. 75.
    Fedtke, M., Mirsojew, I.: Plaste und Kautschuk 28, 369 (1981)Google Scholar
  76. 76.
    Yandovskii, V. N., Ershov, B. A.: Usp. Khim. 41, 785 (1972)Google Scholar
  77. 77.
    Sorokin, M. F., Shode, L. G., Steinpress, A. B.: Vysokomol. Soedin. A13, 747 (1971)Google Scholar
  78. 78.
    Pirozhnaya, L. N.: Vysokomol. Soedin. A12, 2446 (1970)Google Scholar
  79. 79.
    Burness, D. M.: J. Org. Chem. 29, 1862 (1964)Google Scholar
  80. 80.
    McClure, J. D.: J. Org. Chem. 35, 2059 (1970)Google Scholar
  81. 81.
    Katsura, I., Kawaguchi, H., Yamamoto, T.: Nippon Kagaku Kaishi 1973, 1733Google Scholar
  82. 82.
    Nagy, J. B., Bruylants, A., Nagy, O. B.: Tetrahedron Lett. 54, 4825 (1969)Google Scholar
  83. 83.
    Menger, F. M.: J. Am. Chem. Soc. 90, 4378 (1968)Google Scholar
  84. 84.
    Ref. 17, p. 190Google Scholar
  85. 85.
    Narracot, E. S.: Brit. Plastics 26, 120 (1953)Google Scholar
  86. 86.
    Shechter, L., Wynstra, J.: Ind. Eng. Chem. 48, 86 (1956)Google Scholar
  87. 87.
    Kushch, P. P., Komarov, B. A., Rozenberg, B. A.: Vysokomol. Soedin. A21, 1697 (1979)Google Scholar
  88. 88.
    Sorokin, M. F., Shode, L. G., Steinpress, A. B.: Vysokomol. Soedin. B11, 172 (1969)Google Scholar
  89. 89.
    Harlow, G. A.: Anal. Chem. 34, 1487 (1962)Google Scholar
  90. 90.
    Boos, H. J., Hauschildt, K. R.: Angew. Makromol. Chem. 84, 51, (1980)Google Scholar
  91. 91.
    Malavašič, T., et al.: Angew. Makromol. Chem. 44, 89 (1975)Google Scholar
  92. 92.
    Fava, R. A.: Polymer 9, 137 (1968)Google Scholar
  93. 93.
    Peyser, P., Bascom, W. D.: Analytical Calorimetry, Porter, R. S., Johnson, J. F. (eds.), Vol. 3, p. 537. New York: Plenum Press 1974Google Scholar
  94. 94.
    Peyser, P., Bascom, W. D.: J. Appl. Polym. Sci. 21, 2359 (1977)Google Scholar
  95. 95.
    Taratorin, B. I., Alekseeva, N. N.: Vysokomol. Soedin. A10, 2569 (1968)Google Scholar
  96. 96.
    Evtushenko, G. T., Moshinskii, L. Ya., Beletskaya, T. V.: Vysokomol. Soedin. A16, 1343 (1974)Google Scholar
  97. 97.
    Yaralov, L. K., Obanesova, G. S.: Izv. Vysch. Ucheb. Zaved. Khim. Khim. Tekhnol. 18, 1571 (1975), C.A. 84, 60394 (1976)Google Scholar
  98. 98.
    Kudyukov, Yu. P. et al.: Khim. Khim. Tekhnol. Sint. Issled. Plenkoobraz. Veshtchestv. Pigm. 1976, 32; C.A. 89, 130229 (1978)Google Scholar
  99. 99.
    Ref. 16, p. 94Google Scholar
  100. 100.
    Kamon, T. et al.: Kogyo Kagaku Zashi 72, 2677 (1969)Google Scholar

Copyright information

© Springer-Verlag 1984

Authors and Affiliations

  • Jozef Lustoň
    • 1
  • František Vašš
    • 1
  1. 1.Polymer InstituteSlovak Academy of SciencesBratislavaCzechoslovakia

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