Advertisement

Epoxy Structural Adhesives

  • Charles D. Wright
  • John M. Muggee
Part of the Topics in Applied Chemistry book series (TAPP)

Abstract

Among the various structural adhesives commercially available today, epoxies are the most widely accepted and used. A recent market study1 showed that epoxy structural adhesives account for approximately 41% of all structural adhesives sold, and it is expected that they will maintain this market share over at least the next several years. Numerous references exist, both in the patent and journal literature, describing every facet of these adhesives. It is not the intention to review all of the available information. Rather, this chapter will concentrate on three main areas: (1) A general description of epoxy adhesives; (2) A discussion of commercially available raw materials, formulations, properties, and uses of epoxy adhesives; (3) A review of developments in epoxy adhesives since 1979. Earlier work has been discussed in several reviews, and will not be covered in detail in this chapter.2–12

Keywords

Tertiary Amine Maleic Anhydride Epoxy Adhesive Heat Cure Peel Strength 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adhesives IV,A Multiple-Client Study, Skeist Laboratories Inc., Livingston, New Jersey. (1981).Google Scholar
  2. 2.
    H. Lee and K. Neville, Handbook of Epoxy Resins, McGraw-Hill, New York (1967).Google Scholar
  3. 3.
    C. E. Chastain and C. V. Cagle, in: Handbook of Adhesive Bonding ( C. V. Cagle, ed.), McGraw-Hill, New York (1973).Google Scholar
  4. 4.
    M. W. Ranney, Epoxy Resins and Products Recent Advances, Chemical Technology Review # 97, Noyes Data Corp., Park Ridge, New Jersey (1977).Google Scholar
  5. 5.
    R. F. Gould, ed., Epoxy Resins Advances in Chemistry Series,No.92, American Chemical Society, Washington D.C. (1970).Google Scholar
  6. 6.
    J. I. DiStasio, ed., Epoxy Resin Technology Developments Since 1979, Noyes Data Corp., Park Ridge, New Jersey (1982).Google Scholar
  7. 7.
    W. G. Potter, Epoxide Resins, Springer-Verlag, London (1970).Google Scholar
  8. 8.
    N. J. DeLollis, Adhesives Adherends,Adhesion, R. E. Krieger Publishing Co., Inc., Huntington, New York (1980).Google Scholar
  9. 9.
    M. Savla, in: Handbook of Adhesives,2nd Ed. ( I. Skeist, ed.), Van Nostrand Reinhold Co., New York (1977).Google Scholar
  10. 10.
    J. C. Bolger, in: Adhesives in Manufacturing ( G. L. Schneberger, ed.), Marcel Dekker, New York (1983).Google Scholar
  11. 11.
    T. Draskovics, in: Adhesion: Technology,Performance,and Trends, Society of Plastics Industry, Inc., Epoxy Resin Formulators Division, Spring Meeting, Williamsburg, Virginia (May, 1983 ).Google Scholar
  12. 12.
    Y. Tanaka and C. A. May, eds., Epoxy Resins: Chemistry and Technology, Marcel Dekker, New York (1973).Google Scholar
  13. 13.
    E. W. Garnish, Developments in Adhesives Chap. 3, p. 77, Applied Science Publishers, London (1977).Google Scholar
  14. 14.
    Epoxy Resin Manual, Comparative Data, 1979 Edition reproduced by permission of the Dow Chemical Co.Google Scholar
  15. 15.
    Comparison Chart of Competitive Epoxy Curing Agents, Pacific Anchor Chemical Corp. Trade Publication (1980).Google Scholar
  16. 16.
    H. G. Waddill, U.S. Patent 4,187, 367 (1980).Google Scholar
  17. 17.
    Technical Bulletin, MY940, Ciba-Geigy (1982).Google Scholar
  18. 18.
    C. M. Andrews and B. Dobinson, U.S. Patent 4,026, 858 (1977).Google Scholar
  19. 19.
    B. Schultz and A. Thompson, U.S. Patent 3,179, 143 (1965).Google Scholar
  20. 20.
    G. Matson and F. Deckert, U.S. Patent 3,642, 937 (1972).Google Scholar
  21. 21.
    F. J. McGarry and A. M. Willner, Res. Rept. R68–8, School of Engineering, Massachusetts Institute of Technology, Cambridge, Mass. (1968).Google Scholar
  22. 22.
    J. N. Sultan and F. J. McGarry, Res. Rept. R69–59, School of Engineering, Massachusetts Institute of Technology, Cambridge, Mass. (1969).Google Scholar
  23. 23.
    E. H. Rowe, A. R. Siebert, and R. S. Drake Mod. Plast. 417, 110 (1970).Google Scholar
  24. 24.
    A. R. Siebert and C. K. Riew, “The Chemistry of Rubber Toughened Epoxy Resins I,” 161st National Meeting, Am. Chem. Soc., Div. Org. Coat. Plast. Chem. ( March, 1971 ).Google Scholar
  25. 25.
    C. K. Riew and R. W. Smith, J. Polym. Sci., Part A-1 9, 2737 (1971).Google Scholar
  26. 26.
    E. H. Rowe and C. K. Riew, Plast. Eng., 45 (March, 1975 ).Google Scholar
  27. 27.
    A. V. Pocius, “Elastomer Modification of Structural Adhesives”, Rubber Div., Am. Chem. Soc., Denver, Co. (Oct., 1984 ).Google Scholar
  28. 28.
    L. Ching, Ger. Offen. 3,240,285 [CA 99,23613 (1983)].Google Scholar
  29. 29.
    Asahi Denka Kogyo K.K., Jpn. Kokai Tokkyo Koho 57,195,116 [CA 98,180381 (1982)].Google Scholar
  30. 30.
    K. Tsubaki, H. Morinaga, and J. Yukawa, Ger. Offen. 3,303,473 [CA 99,141014 (1983)].Google Scholar
  31. 31.
    J. Bertran and E. Woo, U.S. Patent 4,367, 328 (1983).Google Scholar
  32. 32.
    F. Gutekunst, H. Lehmann, and R. Schmid, Eur. Pat. Appl. 18,950 [CA 94,85168 (1979)].Google Scholar
  33. 33.
    Sakamoto Yakuhior Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 58,19,325 [CA 99,71343 (1983)].Google Scholar
  34. 34.
    I. Minato, K. Shibata, and K. Fujinami, Eur. Pat. Appl. 53,365 [CA 97,93661 (1982)].Google Scholar
  35. 35.
    P. Johncock, Eur. Pat. Appl. 76,584 [CA 99, 23528 (1983)].Google Scholar
  36. 36.
    Mitsubishi Petrochemical Co., Jpn. Kokai Tokkyo Koho 57,141,419 [CA 98,90429 (1982)].Google Scholar
  37. 37.
    D. Morris and P. Erickson, U.S. Patent 4,336,367 [CA 97, 73659 (1982)]Google Scholar
  38. 38.
    H. Waddill, Ger. Offen. 2,910,110 [CA 92,59724 (1979)].Google Scholar
  39. 39.
    A. Umeda and Y. Iwase, Eur. Pat. Appt 74,798 [CA 98,199314 (1983)].Google Scholar
  40. 40.
    S. Akiyama, H. Kawamoto, and S. Ishimura, Jpn. Kokai Tokkyo Koho 79,148,099 [CA 92,164726 (1979)].Google Scholar
  41. 41.
    Y. Sumiya and H. Kawamoto, Jpn. Kokai Tokkyo Koho 79,148,896 [CA 92,130002 (1979)].Google Scholar
  42. 42.
    I. Shinozuka, H. Kawamoto, and S. Fujikawa, Jpn. Kokai Tokkyo Koho 79,148,897 [CA 92,129999 (1979)].Google Scholar
  43. 43.
    N. Aoyanagi, H. Kawamoto, and S. Ishimura, Jpn. Kokai Tokkyo Koho 79,148,898 [CA 92,130000 (1979)].Google Scholar
  44. 44.
    A. Miyamoto, K. Sato, S. Mine, and T. Kasuya, Eur. Pat. Appl. 66,447 [CA 98,90548 (1982)].Google Scholar
  45. 45.
    D. Brandt, Eur. Pat. Appl. 81,146 [CA 99,89714 (1983)].Google Scholar
  46. 46.
    M. Lidarik, S. Lunak, J. Horacek, and J. Cermak, Czech. Patent 200,848 [CA 98,199272 (1983)].Google Scholar
  47. 47.
    C. Burba, H. Lucas, and B. Neffgen, Ger. Offen. 3,151,592 [CA 99,123622 (1983)].Google Scholar
  48. 48.
    E. Kluger, U.S. Patent 4,352, 920 (1982).Google Scholar
  49. 49.
    E. Kluger, U.S. Patent 4,352, 921 (1982).Google Scholar
  50. 50.
    E. Kluger, U.S. Patent 4,362, 856 (1982).Google Scholar
  51. 51.
    E. Kluger E. Kluger, U.S. Patent 4,362, 894 (1982).Google Scholar
  52. 52.
    J. Gillham, Nat. SAMPE Symp. Exhib. [Proc.], 28th, p. 564 (1983).Google Scholar
  53. 53.
    M. Bowditch, Brit. Patent 1,598,432 [CA 96, 182382 (1981)].Google Scholar
  54. 54.
    T. Cassutt, J. Messerly, and R. Senderling, U.S. Patent 4, 260, 700.Google Scholar
  55. 55.
    R. Dick and E. Hobaica, U.S. Patent Appl. 314,334 [CA 98,35751 (1982)].Google Scholar
  56. 56.
    F. Dimmick, U.S. Patent 4,221, 890 (1980).Google Scholar
  57. 57.
    Takeda Chemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 57,91,966 [CA 98,127080 (1982)].Google Scholar
  58. 58.
    H. Staniak, S. Rzemislawski, and U. Surdyk, Pol. Patent 114,237 [CA 98,73961 (1982)].Google Scholar
  59. 59.
    C. Wang and E. Zhao, Tuliao Gongye 64, 14 (1981).Google Scholar
  60. 60.
    C. Delano, A. McCleod, F. Riel, and R. Greer, Nat. SAMPE Tech. Conf., 13th, p. 134 (1981)Google Scholar
  61. 61.
    C. Andrews, Ger. Offen. 3,224,079 [CA 98,144504 (1983)].Google Scholar
  62. 62.
    C. Andrews, Ger. Offen. 3,224,289 [CA 98,144503 (1983)].Google Scholar
  63. 63.
    W. Weliner, J. Pedain, and H. Gruber, Eur. Pat. Appl. 66,167 [CA 98,145183 (1982)].Google Scholar
  64. 64.
    Mitsubishi Petrochemical Co., Ltd., Jpn. Kokai Tokkyo Koho 80,102,624 [CA 93,240579 (1980)].Google Scholar
  65. 65.
    D. Morris and P. Erickson, U.S. Patent 4,336, 367 (1982).Google Scholar
  66. 66.
    G. Green, Ger. Offen. 2,829,235 [CA 90,105051 (1979)].Google Scholar
  67. 67.
    J. Crivello, U.S. Patent 4,138, 255 (1979).Google Scholar
  68. 68.
    Dainippon Printing Co., Ltd., Jpn. Kokai Tokkyo Koho 82,92,023 [CA 97, 199210 (1982)].Google Scholar
  69. 69.
    J. Cella, A. Schwabacher, and A. Schulz, Ind. Eng. Chem. Prod. Res. Dev. 22(1), 20 (1983)CrossRefGoogle Scholar
  70. 70.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 58,15,527 [CA 99,39332 (1983)].Google Scholar
  71. 71.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 58,57,424 [CA 99,141060 (1983)].Google Scholar
  72. 72.
    Mitsubishi Chemical Industries Co., Ltd., Jpn. Kokai Tokkyo Koho 82,80,470 [CA 97, 128649 (1982)].Google Scholar
  73. 73.
    Hitachi, Ltd., Jpn. Kokai Tokkyo Koho 81,104,925 [CA 96,36438 (1981)].Google Scholar
  74. 74.
    D. Scola, Polym. Comp. 4(3), 154 (1983)CrossRefGoogle Scholar
  75. 75.
    D. Scola, Sci-Tech-Aerosp. Rep. 21(9),Abstr. * N83–18909 [CA 99, 106201 (1982)]Google Scholar
  76. 76.
    B. Achar, G. Fohlen, and J. Parker, J. Polym. Sci., Polym. Chem. Ed. 21(5), 1505 (1983)CrossRefGoogle Scholar
  77. 77.
    S. Lunak, J. Smrcka, K. Jelinek, J. Cermak, J. Horacek, M. Lidarik, and F. Hovorka, Czech. Patent 196,156 [CA 98,73403 (1982)].Google Scholar
  78. 78.
    P. McBride and R. Good, U.K. Pat. Appl. 2,100,718 [CA 98,161823 (1983)].Google Scholar
  79. 79.
    G. Nicola and G. Badulescu, Rom. Patent 71,345 [CA 96, 86514 (1980)].Google Scholar
  80. 80.
    M. Tokizawa, N. Wakabayashi, and S. Sato, Jpn. Kokai Tokkyo Koho 79,26,000 [CA91,22007 (1979)].Google Scholar
  81. 81.
    D. Sponseller, E. Melby, and H. Fabris, U.S. Patent 4,377, 680 (1983).Google Scholar
  82. 82.
    S. Lunak, J. Smrcka, K. Jelinek, J. Klaban, and M. Lidarik, Czech. Patent 179,623 [CA 92,112379 (1979)].Google Scholar
  83. 83.
    F. Lohse and H. Zondler, Eur. Pat. Appl. 87,393 [CA 99,196090 (1983)].Google Scholar
  84. 84.
    H. Zondler and R. Moser, Eur. Pat. Appl. 17,623 [CA 94,14066 (1980)].Google Scholar
  85. 85.
    F. Koyama and T. Narahara, Jpn. Kokai Tokkyo Koho 79,83,096 [CA 91,212190 (1979)].Google Scholar
  86. 86.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 58,15,526 [CA 99,39333 (1983)].Google Scholar
  87. 87.
    Daicel Chemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 81,02,316 [CA 94, 209752 (1981)].Google Scholar
  88. 88.
    Asahi Denka Kogyo K. K., Jpn. Kokai Tokkyo Koho 57,195,120 [CA 98,180462 (1982)].Google Scholar
  89. 89.
    Dainippon Jushi Kenkyusho, Jpn. Kokai Tokkyo Koho 58,01,717 [CA 99, 23561 (1983)].Google Scholar
  90. 90.
    Ajinomoto Co., Inc., Jpn. Kokai Tokkyo Koho 57,192,428 [CA 98,180466 (1982)].Google Scholar
  91. 91.
    H. Niino, S. Noguchi, Y. Nakano, and S. Tazuke, J. Appl. Polym. Sci. 27(7), 2361 (1982)CrossRefGoogle Scholar
  92. 92.
    Nitto Electric Industrial Co., Ltd., Jpn. Kokai Tokkyo Koho 57,102,920 [CA 98,5080 (1982)].Google Scholar
  93. 93.
    H. Lehmann, Eur. Pat. Appl. 29,008 [CA 95,134025 (1982)].Google Scholar
  94. 94.
    Mitsui Petrochemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 57,167,370 [CA 98,180658 (1982)].Google Scholar
  95. 95.
    Sumitomo Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,164,117 [CA 98,90519 (1982)].Google Scholar
  96. 96.
    Ube Industries, Ltd., Jpn. Kokai Tokkyo Koho 58,25,327 [CA 99,89708 (1983)].Google Scholar
  97. 97.
    D. Ray-Chaudhuri, W. Chiao, and J. Schoenberg, U.S. Patent 4,268, 656 (1981).Google Scholar
  98. 98.
    Nitto Electric Industrial Co., Ltd., Jpn. Kokai Tokkyo Koho 80,62,921 [CA 93, 115602 (1980)].Google Scholar
  99. 99.
    Daicel Chemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 57,164,118 [CA 99, 106271 (1982)].Google Scholar
  100. 100.
    E. Catsiff, H. Dee, J. DiPrima, and R. Seltzer, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 22(2), 111 (1981)Google Scholar
  101. 101.
    S. Lin, U.S. Patent 4, 379, 728.Google Scholar
  102. 102.
    Asahi Denka Kogyo K. K., Jpn. Kokai Tokkyo Koho 57,174,316 [CA 98,161759 (1982)].Google Scholar
  103. 103.
    Yokohama Rubber Co., Ltd., Jpn. Kokai Tokkyo Koho 57,202,365 [CA 98,216761 (1982)].Google Scholar
  104. 104.
    T. Miyoshi, K. Hasunuma, and H. Watanabe, Jpn. Kokai Tokkyo Koho 78,114,884 [CA 90,55944 (1978)].Google Scholar
  105. 105.
    Shikoku Chemicals Corp., Jpn. Kokai Tokkyo Koho 57,117,525 [CA 98,17551 (1982)].Google Scholar
  106. 106.
    S. Kimura, Jpn. Kokai Tokkyo Koho 79,163,931 [CA 92,216252 (1979)].Google Scholar
  107. 107.
    Yokohama Rubber Co., Ltd., Jpn. Kokai Tokkyo Koho 80,147,580 [CA 95,63174 (1980)].Google Scholar
  108. 108.
    D. Shimp, Eur. Pat. Appl. 86,102 [CA 99,176993 (1983)].Google Scholar
  109. 109.
    F. Schuelde, J. Obendorf, and V. Kulisch, Ger. Offen. 2,731,335 [CA 90,122578 (1979)].Google Scholar
  110. 110.
    A. Farkas and P. Ströhm, J. Appl. Polym. Sci. 12, 159 (1968).CrossRefGoogle Scholar
  111. 111.
    J. Barton and P. Shepherd, Makromol. Chem. 176, 919 (1975).CrossRefGoogle Scholar
  112. 112.
    F. Ricciardi, W. Romanchick, and M. Joullié, J. Polym. Sci., Polym. Chem. Ed. 21(5), 1475 (1983).CrossRefGoogle Scholar
  113. 113.
    F. Doura, M. Nakabayashi, and T. Morimoto, Fr. Demande 2,498,619 [CA 98, 17603 (1982)].Google Scholar
  114. 114.
    Hitachi Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,207,617 [CA 98,217284 (1982)].Google Scholar
  115. 115.
    T. Matsubara, Y. Uramoto, and S. Ishibashi, Jpn. Kokai Tokkyo Koho 79,142,244 [CA 92,148077 (1979)].Google Scholar
  116. 116.
    T. Matsubara, Y. Uramoto, and S. lshibashi, Jpn. Kokai Tokkyo Koho 79,161,649 [CA92,216435 (1979)].Google Scholar
  117. 117.
    T. Matsubara, Y. Uramoto, and S. Ishibashi, Jpn. Kokai Tokkyo Koho 80,09,639 [CA 93, 47836 (1980)].Google Scholar
  118. 118.
    T. Matsubara, Y. Uramoto, and S. Ishibashi, Jpn. Kokai Tokkyo Koho 80,38,831 [CA 93, 72957 (1980)].Google Scholar
  119. 119.
    S. Kiyono, Jpn. Kokai Tokkyo Koho 81,02,317 [CA 94,193179 (1981)].Google Scholar
  120. 120.
    K. Nakashimi, T. Saito, T. Nakahara, and S. Tanaka, Eur. Pat. Appl. 68,474 [CA 98,144523 (1983)].Google Scholar
  121. 121.
    I. Wiesner, Czech. Patent 204,616 [CA 99,54583 (1981)].Google Scholar
  122. 122.
    B. Wen, U.K. Pat. Appl. 2,075,512 [CA 96,105477 (1981)].Google Scholar
  123. 123.
    Ube Industries, Ltd., Jpn. Kokai Tokkyo Koho 57,98,522 [CA 98,90462 (1982)].Google Scholar
  124. 124.
    E. Crandall and W. Mih, Chemorheology of Thermosetting Polymers, Am. Chem. Soc. Symp. Ser., No. 227, p. 113, American Chemical Society, Washington, D.C. (1983).Google Scholar
  125. 125.
    M. Fedtke and F. Domaratius, Plaste Kautsch. 30(3), 136 (1983).Google Scholar
  126. 126.
    Hitachi Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,190,018 [CA 98,199212 (1982)].Google Scholar
  127. 127.
    I. Tanaka, E. Yanagihara, and T. Isogai, Jpn. Kokai Tokkyo Koho 79,146,823 [CA 92,202478 (1979)].Google Scholar
  128. 128.
    New Japan Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,198,725 [CA 98,108483 (1982)].Google Scholar
  129. 129.
    F. Gude, H. Haferkorn, H. Riemer, and F. Mutzberg, Ger. Offen. 3,205,820 [CA 99,176994 (1983)].Google Scholar
  130. 130.
    Daicel Chemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 57,164,119 [CA 98,144501 (1982)].Google Scholar
  131. 131.
    Hitachi Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,205,421 [CA 99,39915 (1982)].Google Scholar
  132. 132.
    P. Moore, U.S. Patent 4,371, 688 (1983).Google Scholar
  133. 133.
    R. Gounder and J. Geary, U.S. Patent 4,366, 302 (1982).Google Scholar
  134. 134.
    B. Culbertson, L. Post, and A. Aulabaugh, U.S. Patent 4,374, 235 (1983).Google Scholar
  135. 135.
    Ashland Oil, Inc., Belg. Patent 895,533 [CA 99,71325 (1983)].Google Scholar
  136. 136.
    B. Culbertson, L. Post, and A. Aulabaugh, U.S. Patent 4,388, 451 (1983).Google Scholar
  137. 137.
    B. Culbertson and A. Aulabaugh, U.S. Patent 4,384, 393 (1983).Google Scholar
  138. 138.
    Dainippon Jushi Kenkyusho, Jpn. Kokai Tokkyo Koho 57,145,121 [CA 98,90477 (1982)].Google Scholar
  139. 139.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 57,133,121 [CA 98,35551 (1982)].Google Scholar
  140. 140.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 57,133,122 [CA 98,35550 (1982)].Google Scholar
  141. 141.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 58,21,418 [CA 99, 106274 (1983)].Google Scholar
  142. 142.
    Toshiba Corp., Jpn. Kokai Tokkyo Koho 58,47,016 [CA 99, 89143 (1983)].Google Scholar
  143. 143.
    B. Siadat and C. Morgan, Ger. Offen. 3,237,914 [CA 99, 54765 (1983)].Google Scholar
  144. 144.
    C. Morgan, U.K. Pat. Appl. 2,108,509 [CA 99, 89712 (1983)].Google Scholar
  145. 145.
    Asahi Denka Kogyo K. K., Jpn. Kokai Tokkyo Koho 57,102,922 [CA 98,35521 (1982)].Google Scholar
  146. 146.
    Asahi Denka Kogyo K. K., Jpn. Kokai Tokkyo Koho 58,37,003 [CA 99, 141034 (1983)].Google Scholar
  147. 147.
    Asahi Denka Kogyo K. K., Jpn. Kokai Tokkyo Koho 58,37,004 [CA 99,141033 (1983)].Google Scholar
  148. 148.
    Asahi Denka Kokyo K. K., Jpn. Kokai Tokkyo Koho 81,152,833 [CA 96, 182205 (1981)].Google Scholar
  149. 149.
    Okura Industrial Co., Ltd., Jpn. Kokai Tokkyo Koho 57,123,221 [CA 98,17546 (1982)].Google Scholar
  150. 150.
    J. Gannon, U.S. Patent 4,389, 520 (1983).Google Scholar
  151. 151.
    J. Bertram, G. Doorakian, and L. Duquette, U.S. Patent 4,405, 766 (1983).Google Scholar
  152. 152.
    S. Kunz-Douglas, P. Beaumont, and M. Ashby, J. Mater. Sci. 15, 1109 (1980).CrossRefGoogle Scholar
  153. 153.
    S. Kunz and P. Beaumont, J. Mater. Sci. 16, 3141 (1981).CrossRefGoogle Scholar
  154. 154.
    C. Bucknall and T. Yoshii, Br. Polym. J. 10, 53 (1978).CrossRefGoogle Scholar
  155. 155.
    J. Sutton and F. McGarry, Polym. Eng. Sci. 13, 29 (1973).CrossRefGoogle Scholar
  156. 156.
    E. Rowe and C. Riew, Plast. Eng. 45 (March, 1975 ).Google Scholar
  157. 157.
    C. Riew, E. Rowe, and A. Siebert, Toughness and Brittleness of Plastics, Advances in Chemistry Series, No. 154, American Chemical Society, Washington, D.C. (1976).CrossRefGoogle Scholar
  158. 158.
    A. Pocius, Rubber Chem. Technol., 58 (3), 622 (1985).CrossRefGoogle Scholar
  159. 159.
    A. Kinloch, S. Shaw, D. Tod, and D. Hunston, Polymer 24, 1341 (1983).CrossRefGoogle Scholar
  160. 160.
    A. Yee and R. Pearson, NASA Contractor Report # 3718 (August, 1983 ).Google Scholar
  161. 161.
    Mitsubishi Petrochemical Co., Ltd., Jpn. Kokai Tokkyo Koho 57,153,039 [CA 98,108351 (1982)].Google Scholar
  162. 162.
    J. Fock and D. Schedlitzki, Ger. Offen. 3,202,408 [CA 99, 141086 (1983)].Google Scholar
  163. 163.
    J. Jarusek and J. Mleziva, Angew Makromol. Chem. 111, 213 (1983).CrossRefGoogle Scholar
  164. 164.
    Nippon Zeon Co., Ltd., Jpn. Kokai Tokkyo Koho 81,49,727 [CA 95,98849 (1981)].Google Scholar
  165. 165.
    Daicel Chemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 81,70,023 [CA 95,170377 (1981)].Google Scholar
  166. 166.
    Nippon Oil Co., Ltd., Jpn. Kokai Tokkyo Koho 58,45,223 [CA 99,141636 (1983)].Google Scholar
  167. 167.
    J. Fock, D. Schedlitzki, and E. Esselborn, Ger. Offen. 3,202,299 [CA 99,71656 (1983)].Google Scholar
  168. 168.
    J. Fock and D. Schedlitzke, Ger. Offen. 3,202,300 [CA 99,141098 (1983)].Google Scholar
  169. 169.
    M. Sugimori, K. Sanji, H. Tomoyasu, and T. Sakakibara, Ger. Offen. 3,237,986 [CA 99, 54588 (1983)].Google Scholar
  170. 170.
    Yokohama Rubber Co., Ltd. Jpn. Kokai Tokkyo Koho 57,192,427 [CA 99,160045 (1983)].Google Scholar
  171. 171.
    Nitto Electric Industrial Co., Ltd. Jpn. Kokai Tokkyo Koho 58,49,719 [CA 99,160045 (1983)].Google Scholar
  172. 172.
    N. Paul, P. Pearce, D. Richards, and D. Thompson, Adhesion (K. W. Allen, ed.) Vol. 3, p. 65, Applied Science Publishers, London (1979).Google Scholar
  173. 173.
    J. Pitt, P. Pearce, T. Rosewarne, R. Davidson, B. Ennis, and C. Morris, J. Marcomol Sci., Chem. A17(2), 227 (1982).CrossRefGoogle Scholar
  174. 174.
    R. Drake and A. Siebert, Org. Coat. Appl. Polym. Sci. Proc. 48, 491 (1983)Google Scholar
  175. 175.
    Ciba-Geigy A.-G., Brit. Patent 1,556,988 [CA 92,148107 (1979)].Google Scholar
  176. 176.
    Asahi Chemical Industry Co., Ltd. Jpn. Kokai Tokkyo Koho 57,149,369 [CA 98,90708 (1982)].Google Scholar
  177. 177.
    Asahi Chemical Industry Co., Ltd. Jpn. Kokai Tokkyo Koho 57,149,370 [CA 98,90707 (1982)].Google Scholar
  178. 178.
    M. Shimbo, M. Ochi, K. Sasaki, and M. Okazaki, Nippon Setchaka Kyokaishi 16(7),271 (1980) [CA 94,4548 (1980)].Google Scholar
  179. 179.
    J. Bell, Eur. Pat. Appl. 77,096 [CA 99, 23616 (1983)].Google Scholar
  180. 180.
    K. Kim, Eur. Pat. Appl. 78,527 [CA 99,71912 (1983)].Google Scholar
  181. 181.
    S. Gazit and J. Bell, Epoxy Resin Chem. 2, Am. Chem. Soc., Symp. Ser., No. 221, p. 55, American Chemical Society, Washington, D.C. (1983).Google Scholar
  182. 182.
    Mitsui Petrochemical Industries, Ltd., Jpn. Kokai Tokkyo Koho 58,40,378 [CA 99,213706 (1983)].Google Scholar
  183. 183.
    K. Marubashi and S. Fujii, Jpn. Kokai Tokkyo Koho 79,70,392 [CA 91,141700 (1979)].Google Scholar
  184. 184.
    H. Waddill, Natl. SAMPE Tech. Conf., 11th,p. 282 (1979) [CA 92,77306 (1979)].Google Scholar
  185. 185.
    H. Ebneth, L. Preis, H. Giesecke, and G. Wolf, Eur. Pat. Appl. 76,414 [CA 99,39363 (1983)].Google Scholar
  186. 186.
    Otsuka Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 82,40,576 [CA 97,7338 (1982)].Google Scholar
  187. 187.
    K. Kornett, K. Ruhsland, P. Schoene, and W. Bader, East German Patent DD 200,675 [CA 99,177209 (1983)].Google Scholar
  188. 188.
    J. O’Neill and C. Wood, Eur. Pat. Appl. 30,102 [CA 95, 151839 (1981)].Google Scholar
  189. 189.
    Kawasaki Steel Corp., Jpn. Kokai Tokkyo Koho 57,159,866 [CA 98,127334 (1982)].Google Scholar
  190. 190.
    Aisin Kako Co., Ltd., Jpn. Kokai Tokkyo Koho 58,74,773 [CA 99,177166 (1983)].Google Scholar
  191. 191.
    Sekisui Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho 81,55,474 [CA 95,151823 (1981)].Google Scholar
  192. 192.
    E. Chandross and L. Sharpe, Belg. Patent 878,071 [CA 92,182105 (1979)].Google Scholar
  193. 193.
    K. Fujimura, S. Sekiya, K. Kamio, K. Okuno, S. Haraguchi, K. Ohasi, and H. Yamaguchi, Ger. Offen. 3,217,723 [CA 98,73586 (1982)].Google Scholar
  194. 194.
    Hitachi, Ltd., Jpn. Kokai Tokkyo Koho 81,147,875 [CA 96, 86676 (1981)].Google Scholar
  195. 195.
    Nihon Dempa Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 82,40,572 [CA 97, 24896 (1982)].Google Scholar
  196. 196.
    Matsushita Electric Industrial Co., Ltd., Jpn. Kokai Tokkyo Koho 80,160,072 [CA 94,157986 (1980)].Google Scholar
  197. 197.
    M. Billias and M. Borders, U.S. Patent 4,428, 867 (1984).Google Scholar
  198. 198.
    Nitto Electric Industrial Co., Ltd., Jpn. Kokai Tokkyo Koho 57,162,747 [CA 98,90752 (1982)].Google Scholar
  199. 199.
    H. Cochrane and D. Miller, Adhes. Age 25(11), 22 (1982).Google Scholar
  200. 200.
    H. Nozu and T. Kamibo, Jpn. Kokai Tokkyo Koho 79,159,450 [CA 92,182229 (1979)].Google Scholar
  201. 201.
    Matsushita Electric Works, Ltd., Jpn. Kokai Tokkyo Koho 58,122,936 [CA 99, 159487 (1983)].Google Scholar
  202. 202.
    F. Ivan, Romanian Patent RO 76,542 [CA 99,176955 (1983)].Google Scholar
  203. 203.
    S. Lunak, J. Smrcka, K. Jelinek, J. Ruzickova, and F. Hovorka, Czeckoslovakian Patent CS 202,400 [CA 99,89713 (1983)].Google Scholar
  204. 204.
    C. Andrews, Eur. Pat. Appl. 79,857 [CA 99,89155 (1983)].Google Scholar
  205. 205.
    Fuji Electric Co., Ltd., Jpn. Kokai Tokkyo Koho 58,19,324 [CA 99, 54560 (1983)].Google Scholar
  206. 206.
    H. Waddill, Ger. Offen. 2,940,912 [CA 93, 72980 (1980)].Google Scholar
  207. 207.
    H. Waddill and H. Schulze, U.S. Patent 4,146, 700 (1979).Google Scholar
  208. 208.
    H. Waddill, U.S. Patent 4,187, 367 (1980).Google Scholar
  209. 209.
    Yokohama Rubber Co., Ltd., Jpn. Kokai Tokkyo Koho 80,71,771 [CA 94,16739 (1980)].Google Scholar
  210. 210.
    Yokohama Rubber Co., Ltd., Jpn. Kokai Tokkyo Koho 80,71,772 [CA 94,66869 (1980)].Google Scholar
  211. 211.
    Toyo Kohan Co., Ltd., Jpn. Kokai Tokkyo Koho 82,31,974 [CA 97, 93385 (1982)].Google Scholar
  212. 212.
    O. Latzusch, ZIS Mitt. 24(7), 774 (1982).Google Scholar
  213. 213.
    M. Aisman and M. Schatz, Plasty Kauc. 16(12), 353 (1979).Google Scholar
  214. 214.
    A. DeNicola, Jr., and J. Bell, Epoxy Resin Chem. 2, Am. Chem. Soc. Symp. Ser., No. 221, p. 119, American Chemical Society, Washington, D.C. (1983).Google Scholar
  215. 215.
    H. Waddill, Ger. Offen. 2,828,152 [CA 90,105039 (1979)].Google Scholar
  216. 216.
    H. Waddill, U.K. Pat. Appl. 2,015,000 [CA 92,130186 (1979)].Google Scholar
  217. 217.
    P. McLean, R. Scott, and A. Garton, Br. Polym. J. 15(1), 66 (1983).CrossRefGoogle Scholar
  218. 218.
    H. Kakiuchi and K. Okamoto, Netsu Kokasei Jushi 3(3), 113 (1982).Google Scholar
  219. 219.
    Fuji Electric Co., Ltd., Jpn. Kokai Tokkyo Koho 57,174,365 [CA 98,180673 (1982)].Google Scholar
  220. 220.
    Hitachi, Ltd., Jpn. Kokai Tokkyo Koho 82,02,326 [CA 96, 163692 (1982)].Google Scholar
  221. 221.
    H. Takagishi, M. Wakabayashi, Y. Takagi, F. Goto, and E. Okuno, Ger. Offen. 2,923,314 [CA 92 148080 (1979)].Google Scholar
  222. 222.
    Y. Takagi, F. Goto, H. Okuno, H. Takagishi, and M. Wakabayashi, Jpn. Kokai Tokkyo Koho 79,160,454 [CA 92 164766 (1979)].Google Scholar
  223. 223.
    E. Garnish and R. Wilson, U.S. Patent 4,126, 505 (1978).Google Scholar
  224. 224.
    C. Watson, Jr. and M. Eichner, U.S. Patent 3, 226, 969 (1980).Google Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • Charles D. Wright
    • 1
  • John M. Muggee
    • 1
  1. 1.Adhesives, Coatings and Sealers Division3MSt. PaulUSA

Personalised recommendations