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Polyurethane Structural Adhesives

  • B. H. Edwards
Part of the Topics in Applied Chemistry book series (TAPP)

Abstract

Polyurethanes were first discovered by Otto Bayer and coworkers at I. G. Farbenindustrie, Germany, in the late 1930s. The first products were obtained by reacting an aliphatic diisocyanate with an aliphatic diamine or dio1.1,2 These materials soon found commercial uses and were marketed under the trade names of Irgamid U, for plastics, and Perlon U for synthetic fibers and bristles. Very soon after this, it was discovered that isocyanates could be used to bond rubber to metal, which in turn led to the development of urethane adhesives based on polyester diols; these adhesives were commercialized under the trade name Polystal. For a more complete account of the history of polyurethanes, see refs. 2, 4, and 5.

Keywords

Crosslink Density Hard Segment Soft Segment Hydrolytic Stability Isocyanate Group 
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.
    O. Bayer, Angew. Chem. A59, 275 (1947).Google Scholar
  2. 2.
    J. H. Saunders and K. C. Frisch, Polyurethanes: Chemistry and Technology, Part I. Chemistry, Interscience, New York (1962).Google Scholar
  3. 3.
    J. H. Saunders and K. C. Frisch, Polyurethanes: Chemistry and Technology, Part II. Technology, Interscience, New York (1964).Google Scholar
  4. 4.
    B. A. Dombrow, Polyurethanes, 2nd Ed., Reinhold Publishing Corporation, New York (1965).Google Scholar
  5. 5.
    P. Wright and A. P. C. Cumming, Solid Polyurethane Elastomers, Gordon and Breach, New York (1969).Google Scholar
  6. 6.
    C. Hepburn, Polyurethane Elastomers, Applied Science Publishers Ltd., London (1982).Google Scholar
  7. 7.
    Ref. 2, pp. 76, 82.Google Scholar
  8. 8.
    K. C. Frisch and L. P. Rumao, J. Macromol. Sci., Rev. Macromol. Chem. C5, 103 (1970).Google Scholar
  9. 9.
    S. L. Reegan and K. C. Frisch, Adv. Urethane Sci. Technol. 1, 1 (1971).Google Scholar
  10. 10.
    J. Robins, B. H. Edwards, and S. K. Tokach, Adv. Urethane Sci. Technol. 9, 65 (1984).Google Scholar
  11. 11.
    C. I. Kogon, J. Org. Chem. 23, 1594 (1958).Google Scholar
  12. 12.
    Ref. 2, p. 94.Google Scholar
  13. 13.
    H. Ulrich in: Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Ed., p. 576, John Wiley and Sons, Inc., New York (1983).Google Scholar
  14. 14.
    A. A. R. Sayigh, Adv. Urethane Sci. Technol. 3, 141 (1974).Google Scholar
  15. 15.
    J. Robins and D. R. O’Keefe, Adv. Urethane Sci. Technol. 8, 185 (1981).Google Scholar
  16. 16.
    D. Klempner, K. C. Frisch, and C. L. Wang, Adv. Urethane Sci. Technol. 9, 102 (1984).Google Scholar
  17. 17.
    W. Neumann, H. Holtschmidt, J. Peter, and P. Fischer, U.S. Patent 3,193,522 [CA 63, 753 (1963)].Google Scholar
  18. 18.
    W. Neumann, J. Peter, H. Holtschmidt, and W. Kallert, Proc. Rubber Technol. Conf. 4th, London, 59 (1962) [CA 60, 9456 (1964)].Google Scholar
  19. 19.
    G. Magnus, R. A. Dunleavy, and F. E. Critchfield, Rubber Chem. Technol. 39, 1328 (1966).Google Scholar
  20. 20.
    C. S. Schollenberger and F. S. Stewart, J. Elastoplastics 3, 28 (1971).Google Scholar
  21. 21.
    S. L. Cooper and A. V. Tobolsky, J. Appl. Polym. Sci. 10, 1837 (1966).Google Scholar
  22. 22.
    J. W. C. Van Bogart, A. Lilaonitkul, and S. L. Cooper, Adv. Chem. Ser. 176, 3 (1979).Google Scholar
  23. 23.
    C. Duquatre, Y. Chamberlin, C. Pillot, and J. P. Pascault, Angew. MakromoL Chem. 72, 11 (1978).Google Scholar
  24. 24.
    Y. Minoura, S. Yamashita, H. Okamoto, T. Matsuo, M. Izawa, and S-I. Kohmoto, J. AppL Polym. Sci. 22, 1817 (1978).Google Scholar
  25. 25.
    A. L. Chang and E. L. Thomas, Adv. Chem. Ser. 176, 31 (1979).Google Scholar
  26. 26.
    Z. H. Ophir and G. L. Wilkes, Adv. Chem. Ser. 176, 53 (1979).Google Scholar
  27. 27.
    C. S. Schollenberger, Adv. Chem. Ser. 176, 83 (1979).Google Scholar
  28. 28.
    G. A. Senich and W. A. MacKnight, Adv. Chem. Ser. 176, 97 (1979).Google Scholar
  29. 29.
    C. B. Hu, R. S. Ward, Jr., and N. S. Schneider, J. AppL Polym. Sci. 25, 2167 (1982).Google Scholar
  30. 30.
    Y. Chamberlin and J. P. Pascault, J. Polym. Sci., Polym. Chem. Ed. 21, 415 (1983).Google Scholar
  31. 31.
    J. Blackwell and C. D. Lee, Polym. Mater. Sci. Eng. 49, 49 (1983).Google Scholar
  32. 32.
    S. B. Lin, K. K. S. Hwang, K. S. Wu, S. Y. Tsay, and S. L. Cooper, Polym. Mater. Sci. Eng. 49, 53 (1983).Google Scholar
  33. 33.
    R. Russo and E. L. Thomas, J. Macromol. Sci., Phys. B22, 553 (1983).Google Scholar
  34. 34.
    W. Nierzwicki, J. AppL Polym. Sci. 29, 1203 (1984).Google Scholar
  35. 35.
    J. Blackwell and C. D. Lee, J. Polym. Sci., Polym. Phys. Ed. 22, 759 (1984).Google Scholar
  36. 36.
    G. M. Estes, S. L. Cooper, and A. V. Tobolsky, J. Macromol. Sci., Rev. Macromol. Chem. C4, 313 (1970).Google Scholar
  37. 37.
    J. T. Korberstein and R. S. Stein, Polymer 25, 171 (1984).Google Scholar
  38. 38.
    J. Koutsky, Polym. Lett. 8, 353 (1970).Google Scholar
  39. 39.
    N. S. Schneider, C. R. Despar, J. L. Illinger, A. O. King, and D. Barr, J. Macromol. Sci., Phys. B11, 527 (1975).Google Scholar
  40. 40.
    R. E. Camargo, C. W. Macosko, M. V. Tirrell, and S. T. Wellinghoff, Polym. Eng. Sci. 12, 719 (1982).Google Scholar
  41. 41.
    A. L. Chang, R. M. Briber, E. L. Thomas, R. S. Zdrahala, and F. E. Chritchfield, Polymer 23, 1060 (1982).Google Scholar
  42. 42.
    R. A. Assink, J. Polym. Sci., Polym. Phys. Ed. 15, 59 (1977).Google Scholar
  43. 43.
    R. A. Assink and G. L. Wilkes, Polym. Eng. Sci. 17, 606 (1977).Google Scholar
  44. 44.
    R. W. Seymour and S. L. Cooper, Adv. Urethane Sci. Technol. 3, 66 (1974).Google Scholar
  45. 45.
    J. C. West and S. L. Cooper, J. Polym. Sci., Polym. Symp. 60, 127 (1977).Google Scholar
  46. 46.
    C. S. Paik Sung and N. S. Schneider, Macromolecules 10, 452 (1977).Google Scholar
  47. 47.
    V. W. Srichatrapimuk and S. L. Cooper, J. Macromol. Sci., Phys. B15, 267 (1978).Google Scholar
  48. 48.
    C. S. Paik Sung and C. B. Hu, Adv. Chem. Ser. 176, 69 (1979).Google Scholar
  49. 49.
    C. S. Paik Sung, T. W. Smith, and N. H. Sung, Macromolecules 13, 117 (1980).Google Scholar
  50. 50.
    R. E. Camargo, C. W. Macosko, M. Tirrell, and S. T. Wellinghoff, Proc. IUPAC, I. U.P.A. C., Macromol. Symp. 28th, p. 711 (1982) [CA 99, 176385 (1983)].Google Scholar
  51. 51.
    R. Bonart, J. Macromol. Sci., Phys. B2, 115 (1968).Google Scholar
  52. 52.
    R. Bonart, L. Morbitzer, and G. Hentze, J. Macromol. Sci., Phys. B3, 337 (1969).Google Scholar
  53. 53.
    S. L. Samuels and G. L. Wilkes, J. Polym. Sci., Part C43, 149 (1973).Google Scholar
  54. 54.
    Z. Ophir and G. L. Wilkes, J. Polym. Sci., Polym. Phys. Ed. 18, 1469 (1980).Google Scholar
  55. 55.
    R. M. Briber and E. L. Thomas, J. Macromol. Sci., Phys. B22, 509 (1983).Google Scholar
  56. 56.
    L. Born, J. Crone, H. Hespe, E. H. Müller, and K. H. Wolf, J. Polym. Sci., Polym. Phys. Ed. 22, 163 (1984).Google Scholar
  57. 57.
    L. M. Leung and J. T. Korberstein, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 24 (2), 243 (1983).Google Scholar
  58. 58.
    J. A. Miller, S. L. Cooper, C. C. Han, and G. Prukmayer, Macromolecules 17, 1063 (1984).Google Scholar
  59. 59.
    F. Cangelosi and M. T. Shaw, Polym.-Plast. Technol. Eng. 21, 13 (1983).Google Scholar
  60. 60.
    K. Hayashi and C. S. Marvel, J. Polym. Sci. A2, 2571 (1964).Google Scholar
  61. 61.
    J. A. Verdol, D. J. Carrow, P. W. Ryan, and K. L. Kunel, Rubber Age 98 (7), 57 (1966).Google Scholar
  62. 62.
    J. A. Verdol, D. J. Carrow, P. W. Ryan, and K. L. Kunel, Rubber Age 98 (8), 62 (1966).Google Scholar
  63. 63.
    C. Arnold, Jr., Elastomers Plastics 6, 238 (1974).Google Scholar
  64. 64.
    Anon, Stable Polyurethane Coatings for Electronic Circuits, NASA Tech Briefs, Vol. 7, No. 1, MFS-25663, (Fall, 1982).Google Scholar
  65. 65.
    B. B. Idage, S. P. Vernekar, and N. D. Ghatge, J. Appl. Polym. Sci. 28, 3559 (1983).Google Scholar
  66. 66.
    M. Xu, W. J. MacKnight, C. H. Y. Chen, and E. L. Thomas, Polymer 24, 1327 (1983).Google Scholar
  67. 67.
    C. H. Y. Chen, R. M. Briber, E. L. Thomas, M. Xu, and W. J. MacKnight, Polymer 24, 1333 (1983).Google Scholar
  68. 68.
    T. R. Walton, Proc. Am. Chem. Soc. Div. Polym. Mater. Sci. Eng. 51, 655 (1984).Google Scholar
  69. 69.
    J. P. Kennedy, Polyurethane: New Paths Prog., Mark, Technol., Proc. SPI Int. Tech./ Mark. Conf 6th, p. 514 (1983) [CA 100, 69642 (1984)].Google Scholar
  70. 70.
    E. Müller, Angew. Makromol. Chem. 14, 75 (1970).Google Scholar
  71. 71.
    E. Müller, W. Kallert, and J. Ivanyi, Brit. Patent 1,149,815; U.S. Patent 3,544,524 [CA 71, 4340 (1969)].Google Scholar
  72. 72.
    M. H. Hamb and S. B. Gorman, Polyurethane: New Paths Prog., Mark, Technol., Proc. SPI Int. Tech./ Mark Conf, 6th, p. 494 (1983) [CA 100, 104843 (1984)].Google Scholar
  73. 73.
    PPG Technical Bulletin No. 951, PPG Industries Inc., Chicago Illinois (1983).Google Scholar
  74. 74.
    Ref. 2, Ch. VI.Google Scholar
  75. 75.
    Ref. 5, Ch. 2.Google Scholar
  76. 76.
    Ref. 6, Ch. 3.Google Scholar
  77. 77.
    H. J. Fabris, Adv. Urethane Sci. Technol. 6, 173 (1978).Google Scholar
  78. 78.
    W. J. Pentz and R. G. Krawiec, Rubber Age 107 (12), 39 (1975).Google Scholar
  79. 79.
    K. A. Pigott, B. F. Frye, K. R. Allen, S. Steingiser, W. C. Darr, J. H. Saunders, and E. E. Hardy, J. Chem. Eng. Data 5, 391 (1960).Google Scholar
  80. 80.
    C. F. Blaich, Jr. and A. J. Sampson, Abstr. Papers, Am. Chem. Soc. Meeting, 138th, p. 3U No. 6 (1960).Google Scholar
  81. 81.
    E. E. Gruber and O. Keplinger, Ind. Eng. Chem. 51, 151 (1959).Google Scholar
  82. 82.
    T. Conley, Thermal Stability of Polymers, Vol. 1, Marcel Dekker, New York (1970).Google Scholar
  83. 83.
    G. Mathur, J. E. Kresta, and K. C. Frisch, Adv. Urethane Sci. Technol. 6, 103 (1978).Google Scholar
  84. 84.
    P. N. Tilley, H. G. Nadeau, H. E. Reymore, P. H. Waszeciak, and A. A. R. Sayigh, J. Cell. Plast. 4 (1), 22 (1968).Google Scholar
  85. 85.
    P. N. Tilley, H. G. Nadeau, H. E. Reymore, P. H. Waszeciak, and A. A. R. Sayigh, J. Cell. Plast. 4 (2), 56 (1968).Google Scholar
  86. 86.
    T. K. Bakus, D. L. Bernard, W. C. Dan, and J. H. Saunders, J. Appl. Polym. Sci. 12, 1053 (1968).Google Scholar
  87. 87.
    I. M. Robinson, U.S. Patent 4,371,687 [CA 98, 161359 (1983)].Google Scholar
  88. 88.
    Products Research and Chemical Corporation, Rubber and Plastics News, April 23, 9 (1984).Google Scholar
  89. 89.
    H. C. Beachell, C. P. Ngoc Son, J. Polym. Sci. A2, 4773 (1964).Google Scholar
  90. 90.
    F. W. Abbate, W. J. Farrissey, Jr., and A. A. R. Sayigh, J. Appl. Polym. Sci. 16, 1213 (1972).Google Scholar
  91. 91.
    B. E. Brokenbrow, D. Sims, and J. Wright, Rubber J. (9), 45 (1971).Google Scholar
  92. 92.
    C. L. Wang, D. Klempner, and K. C. Frisch, Proc. Am. Chem. Soc. Div. Polym. Mater. Sci. Eng. 49, 38 (1983).Google Scholar
  93. 93.
    N. Allbee, Plastics Compounding May/June, 70 (1984).Google Scholar
  94. 94.
    N. D. Apukhitina, in: Soviet Urethane, Technology (A. M. Schiller, ed.), Soviet Progress in Urethane Technology, Vol. 1, p. 198 Technomic Publishing Co., Westport, Connecticut (1973).Google Scholar
  95. 95.
    Ruco Polymer Corp. Tech. Infor., Lab Report 82–11 (June 28, 1982 ).Google Scholar
  96. 96.
    D. W. Brown, R. E. Lowry, and L. E. Smith, Proc. Am. Chem. Soc. Div. Polym. Mater. Sci. Eng. 51, 155 (1984).Google Scholar
  97. 97.
    A. E. Brachman, U.S. Patent 3,804,809 [CA 81, 38657 (1974)].Google Scholar
  98. 98.
    G. Groegler, U.S. Patent 3,795,638; Ger. Patent 2,106,726 [CA 78, 17061 (1973)].Google Scholar
  99. 99.
    L. G. Hole, U.S. Patent 3,798,198; Ger. Patent 2,062,979 [CA 75, 99041 (1971)].Google Scholar
  100. 100.
    H. Hagemann, E. Müller, and P. Fischer, U.S. Patent 3,692,813 [CA 73, 88888 (1970)].Google Scholar
  101. 101.
    J. Backes, R. Gipp, G. Groegler, and E. Müller, Ger. Patent 2,331,796 [CA 82, 141023 (1975)].Google Scholar
  102. 102.
    S. Kaizerman and A. Singh, Brit. Patent 1,425,529 [CA 81, 170567 (1974)].Google Scholar
  103. 103.
    F. C. Loew and D. Price, Brit. Patent 1,338,551 [CA 75, 141773 (1971)].Google Scholar
  104. 104.
    A. Reischl, H. Holtschmidt, W. Neumann, and W. Simmler, Ger. Patent 1,190,176 [CA 63, 753 (1965)].Google Scholar
  105. 105.
    F. C. Loew, U.S. Patent 3,711,439 [CA 78, 85386 (1973)].Google Scholar
  106. 106.
    A. Singh and R. Saxon, Rubber Age 4, 53 (1975).Google Scholar
  107. 107.
    M Scotch-Weld Product specification: 3532 B/ A, 3535 B/ A, 3549 B/A Structural Adhesives, Adhesives, Coatings and Sealers Division/3M, 223–6NE, 3M Center, St. Paul, MN 55144 (September 1, 1982).Google Scholar
  108. 108.
    G. M. Maclver and D. P. Thompson II, in: Adhesives in Manufacturing ( G. L. Schneberger, ed.), p. 195, Marcel Dekker, New York (1983).Google Scholar
  109. 109.
    Goodyear Chemical Product Information, Pliogrip Adhesive System for Structural Bonding. Pliogrip Adhesive Systems are now owned by Ashland Chemical Co., Div. Ashland Oil, Inc., PO Box 2219, Columbus, OH 43216.Google Scholar
  110. 110.
    Accuthane UR-1100 Product Specification, H. B. Fuller Co., Assembly Products Division, 5520 Main Street NE, Minneapolis, MN 55421 (May, 1983).Google Scholar
  111. 111.
    J. Delmonte and E. C. Sarna, Appl. Polym. Symp. 19, 195 (1972).Google Scholar
  112. 112.
    Product Information: Tyrite 7500A Urethane Structural Adhesive System, Lord Corp., Industrial Adhesives Division, 2000 West Grandview Blvd., PO Box 10038, Erie, PA 16514 (July 10, 1984).Google Scholar
  113. 113.
    H. J. Fabris, E. M. Maxey, and H. Uelzmann, U.S. Patent 3,714,127 [CA 78,137415 (1973)].Google Scholar
  114. 114.
    W. M. Larson and N. R. Bender, U.S. Patent 3,812,003 [CA 81, 50668 (1974)].Google Scholar
  115. 115.
    H. J. Fabris, D. R. Sponseller, and A. E. Schmucker, U.S. Patent 3,886,122 [CA 83, 116025 (1975)].Google Scholar
  116. 116.
    N. R. Bender and W. M. Larson, U.S. Patent 3,935,051 [CA 84, 136670 (1976)].Google Scholar
  117. 117.
    D. S. Schwarz, U.S. Patent 4,336,298 [CA 97, 128832 (1982)].Google Scholar
  118. 118.
    T. G. Rabito, U.S. Patent 4,444,976 [CA 101, 8438 (1984)].Google Scholar
  119. 119.
    D. M. Hoffman in: Chemorheology of Thermosetting Polymers (C. A. May, ed.), Am. Chem. Soc. Symp. Ser., No. 227, p. 169, American Chemical Society, Washington, D.C. (1983).Google Scholar
  120. 120.
    G. W. DeSantis, U.S. Patent 3,707,521 [CA 78, 86134 (1973)].Google Scholar
  121. 121.
    G. F. Schumacher, Eur. Patent 103,453 [CA 101, 56597 (1984)].Google Scholar
  122. 122.
    Introductory Data Sheet, 3 M Brand Windo-Weld Super Fast Urethane, Adhesives, Coatings and Sealers Division/3M, 223–6NE, 3M Center, St. Paul, MN 55144 (October 25, 1983).Google Scholar
  123. 123.
    W. D. Emmons, U.S. Patent 3,743,626 [CA 76, 4548 (1972)].Google Scholar
  124. 124.
    J. Pedain, W. Wellner, H. Gruber, and M. Dietrich, U.S. Patent 4,118,376 [CA 88, 138097 (1979)].Google Scholar
  125. 125.
    G. Naples, U.S. Patent 4,381,388 [CA 99, 39954 (1983)].Google Scholar
  126. 126.
    H-G. Zengel, M. Wallrabenstein, and W. Brodowski, U.S. Patent 4,289,869 [CA 95, 44888 (1981)].Google Scholar
  127. 127.
    M. Hajek, K. Wagner, W. Uerdingen, and W. Wellner, U.S. Patent 4,404,379 [CA 91, 125036 (1979)].Google Scholar
  128. 128.
    Z. W. Wicks, Jr. Prog. Org. Coat. 3, 73 (1975).Google Scholar
  129. 129.
    Z. W. Wicks, Jr. Prog. Org. Coat. 9, 3 (1981).Google Scholar
  130. 130.
    H. Ulrich, B. W. Tucker, and R. H. Richter, J. Org. Chem. 43, 1544 (1978).Google Scholar
  131. 131.
    R. H. Richter, B. W. Tucker, and H. Ulrich, U.S. Patent 4,138,398 [CA 90, 169565 (1979)].Google Scholar
  132. 132.
    R. H. Richter, B. W. Tucker, and H. Ulrich, U.S. Patent 4,154,931 [CA 91, 57068 (1979)].Google Scholar
  133. 133.
    R. H. Richter, B. W. Tucker, and H. Ulrich, U.S. Patent 4,190,599 [CA 90, 169565 (1979)].Google Scholar
  134. 134.
    R. H. Richter, B. W. Tucker, and H. Ulrich, U.S. Patent 4,217,436 [CA 90, 169565 (1979)].Google Scholar
  135. 135.
    E. A. Barsa, C-Y. Lin, and F. A. Stuber, U.S. Patent 4,349,663 [CA 97, 94107 (1982)].Google Scholar
  136. 136.
    E. A. Barsa and P. W. Sherwood, U.S. Patent 4,448,816 [CA. 101, 131840 (1984)].Google Scholar
  137. 137.
    R. H. Richter, B. W. Tucker, and H. Ulrich, U.S. Patent 4,339,381 [CA 97, 198188 (1982)].Google Scholar
  138. 138.
    I. C. Kogon, U.S. Patent 3,891,606 [CA 82, 172350 (1975)].Google Scholar
  139. 139.
    M. E. Kimball, U.S. Patent 4,247,676 [CA 95, 26256 (1981)].Google Scholar
  140. 140.
    M. E. Kimball, U.S. Patent 4,330,454 [CA 97, 56737 (1982)].Google Scholar
  141. 141.
    C. O. Pyron, U.S. Patent 3,488,302 [CA 72, 56811 (1970)].Google Scholar
  142. 142.
    S. LaBelle and J. A. E. Hagquist, U.S. Patent 4,390,678 [CA 99, 89403 (1983)].Google Scholar
  143. 143.
    S. LaBelle and J. A. E. Hagquist, U.S. Patent 4,412,033 [CA 96, 218841 (1982)].Google Scholar
  144. 144.
    Accuthane UR-1100 Adhesives Specifications and Test Data, H. B. Fuller Co., Marketing Department, 3530 Lexington Ave. No., St. Paul, MN 55112 (1983).Google Scholar
  145. 145.
    R. Blum, A. Lehner, and H-U. Schenck, U.S. Patent 4,400,497 [CA 98, 5554 (1983)].Google Scholar
  146. 146.
    H-U. Buschhaus, K. Findeisen, H-J. Traenckner, and W. Beer, U.S. Patent 4,439,591 [CA 100, 35275 (1984)].Google Scholar
  147. 147.
    J. W. Saracsan, U.S. Patent 4,452,964 [CA 101, 131865 (1984)].Google Scholar
  148. 148.
    Anon, Chem. Week, March 28, 10 (1984).Google Scholar
  149. 149.
    G. L. Schneberger in: Handbook of Adhesives, 2nd Ed. (I. Skeist, ed.), p. 782, Van Nostrand Reinhold Co., New York (1977).Google Scholar
  150. 150.
    G. M. Maclver, Soc. Auto. Eng. Trans., 810766 (1981).Google Scholar
  151. 151.
    F. J. Meyer and G. B. Chapman, Adhes. Age 23 (4), 21 (1980).Google Scholar
  152. 152.
    F. J. Meyer and R. J. Zienert, Adhes. Age 24 (4), 31 (1981).Google Scholar
  153. 153.
    M. E. Kimball, Polym. News 9, 198 (1984).Google Scholar
  154. 154.
    E. C. Hornaman, Rubber World 88, 28 (1983).Google Scholar
  155. 155.
    M. E. Kimball and G. M. Maclver, Proc. Ann. Conf, Reinf. Plast./Comp. Inst., Soc. Plast. Ind., 37th, Sess. 13E, Conf. 627, 1 (1982).Google Scholar
  156. 156.
    R. J. Schafer and W. A. Oplesch in: Urethane Chemistry and Applications (K. N. Edwards, ed.), Am. Chem. Soc. Symp. Ser., No. 172, p. 57, American Chemical Society, Washington, D.C. (1981).Google Scholar
  157. 157.
    Anon, Elastomerics 111, 59 (1979).Google Scholar
  158. 158.
    A. J. Kinloch, ed., Durability of Structural Adhesives, Applied Science Publishers, London (1983).Google Scholar
  159. 159.
    N. J. De Lollis, Adhesives, Adherends, Adhesion, Robert E. Krieger Publishing Co., New York (1980).Google Scholar
  160. 160.
    F. D. Swanson and S. J. Price, Adhes. Age 15 (3), 26 (1972).Google Scholar
  161. 161.
    D. M. Brewis in: Durability of Structural Adhesives (A. J. Kinloch, ed.), p. 215, Applied Science Publishers, London (1983).Google Scholar
  162. 162.
    A. V. Pocius, D. A. Wangsness, C. J. Aimer, and A. G. McKown in: Adhesive Chemistry—Developments and Trends (L-H. Lee, ed.), p. 617, Plenum Press, New York (1984).Google Scholar
  163. 163.
    J. D. Minford in: Durability of Structural Adhesives (A. J. Kinloch, ed.), p. 197, Applied Science Publishers, London (1983).Google Scholar
  164. 164.
    Ref. 159, p. 63.Google Scholar
  165. 165.
    Denki Kagaku Kogyo K. K., Jpn. Patent 58,187,477 [CA 101, 39482 (1984)].Google Scholar
  166. 166.
    F-T. H. Lee and J. Green, U.S. Patent 4,456,743 [CA 101, 153179 (1984)].Google Scholar
  167. 167.
    F. D. Swanson and S. J. Price, Adhes. Age 16 (6), 23 (1973).Google Scholar
  168. 168.
    G. M. Seiter, U.S. Patent 3,627,722 [CA 76, 115009 (1972)].Google Scholar
  169. 169.
    E. Chu and L. R. Harper, U.S. Patent 3,711,445 [CA 78, 137384 (1973)].Google Scholar
  170. 170.
    L. R. Barron and H. M. Turk, U.S. Patent 4,067,844 [CA 89, 199260 (1978)].Google Scholar
  171. 171.
    B. Brinkmann and H-J. Lucas, U.S. Patent 4,456, 718 (1984).Google Scholar
  172. 172.
    H. Koski and G. L. Schneberger, Adhes. Age 27 (5), 8 (1984).Google Scholar
  173. 173.
    Adhesives a Desk-Top Data Bank, pp. 486, 777, The International Plastics Selector, Inc., San Diego (1980).Google Scholar
  174. 174.
    G. Eagle, Plast. Eng. 36 (7), 29 (1980).Google Scholar
  175. 175.
    W. A. Pletcher, Soc. Auto. Eng. Trans., June 8–12, 810767 (1981).Google Scholar
  176. 176.
    Ref. 3, p. 649.Google Scholar
  177. 177.
    R. M. Rowell and W. D. Ellis in: Urethane Chemistry and Applications (K. N. Edwards, ed.), Am. Chem. Soc. Symp. Ser., No. 172, p. 263, American Chemical Society, Washington D.C. (1981).Google Scholar
  178. 178.
    R. M. Rowell and W. D. Ellis, Wood Sci. 12, 52 (1979).Google Scholar
  179. 179.
    A. McLaughlin, L. M. Alberino, W. J. Farrissey, and D. P. Waszeciak, Proc. 1980 Symp. Wood Adhes.—Res., Appl., Needs, University of Wisconsin, Sept. 23–25, p. 112 (1980).Google Scholar
  180. 180.
    P. R. Steiner, S. Chow, and S. Vadja, For. Prod. J. 30 (7), 21 (1980).Google Scholar
  181. 181.
    D. Crawford, M. DiNard, D. Dwight, and T. Rials, Proc. 7th Ann. Meeting The Adhesion Soc., Feb. 13–15, p. 73 (1984).Google Scholar
  182. 182.
    O. Wittmann, Holz Roh-Werkst. 34, 427 (1976).Google Scholar
  183. 183.
    K. C. Frisch, L. P. Rumao, and A. Pizzi in: Wood Adhesives Chemistry and Technology (A. Pizzi, ed.), p. 289, Marcel Dekker, New York (1983).Google Scholar
  184. 184.
    W. E. Johns, J. Adhes. 15, 59 (1982).Google Scholar
  185. 185.
    W. E. Johns, Proc. Wash. State Int. Symp. Particleboard, 14th, p. 177 (1980).Google Scholar
  186. 186.
    J. W. Frink and H. I. Sachs in: Urethane Chemistry and Applications (K. N. Edwards, ed.), Am. Chem. Soc. Symp. Ser., No. 172, p. 285 American Chemical Society, Washington, D.C. (1981).Google Scholar
  187. 187.
    J. A. Sharp, U.S. Patent 3,440,189 [CA 70, 21132 (1969)].Google Scholar
  188. 188.
    A. A. Marra, U.S. Patent 3,557,263 [CA 74, 65166 (1971)].Google Scholar
  189. 189.
    H. J. Diehr, K. J. Kraft, and H. I. Sachs, U.S. Patent 3,870,665 [CA 83, 45059 (1975)].Google Scholar
  190. 190.
    P. D. Shoemaker and H. O. McQueary, U.S. Patent 3,919,017 [CA 84, 46415 (1976)].Google Scholar
  191. 191.
    P. D. Shoemaker and H. O. McQueary, U.S. Patent 3,930,110 [CA 84, 91906 (1976)].Google Scholar
  192. 192.
    R. U. Dreher and K. Ernst, Ger. Patent 2,615, 288 (1977).Google Scholar
  193. 193.
    H. J. Deppe and K. Ernst, Holz Roh- Werkst. 29, 45 (1971).Google Scholar
  194. 194.
    H. J. Deppe, Holz Roh- Werkst. 35, 295 (1977).Google Scholar
  195. 195.
    G. W. Ball and R. P. Redman, Spanplatten-Heute Morgen, (Int. Spanplatten-Symp.), p. 121 (1978; pub. 1979) [CA 93, 9729 (1980)].Google Scholar
  196. 196.
    W. Reuther, A. Segnitz, O. Wittman, and H. Schatz, U.S. Patent 4,260,532 [CA 92, 148848 (1980)].Google Scholar
  197. 197.
    R. Van Ael and R. G. Hughes, Brit. Patent 2,039,780 [CA 94, 209734 (1981)].Google Scholar
  198. 198.
    H. Reiff and H. I. Sachs, Ger. Patent 2,921,681 [CA 94, 123462 (1981)].Google Scholar
  199. 199.
    W. Reuther, A. Segnitz, O. Wittmann, and J. Winter, Ger. Patent 2,724,364 [CA 89, 131444 (1978)].Google Scholar
  200. 200.
    W. Reuther, A. Segnitz, O. Wittmann, and J. Winter, Ger. Patent 2,724,363 [CA 89, 131444 (1978)].Google Scholar
  201. 201.
    W. Reuther, A. Segnitz, O. Wittmann, and J. Winter, Ger. Patent 2,703,271 [CA 89, 131444 (1978)].Google Scholar
  202. 202.
    F. Bosscher, J. Penfold, K. W. Reich, nd A. Zandvoort, Eur. Patent 95,594 [CA 100, 86632 (1984)].Google Scholar
  203. 203.
    A. L. Lambuth, U.S. Patent 4,279,788 [CA 95, 117378 (1981)].Google Scholar
  204. 204.
    S. Sakurada, Y. Miyazaki, T. Hattori, M. Shiraishi, and T. Inoue, U.S. Patent 3,931,088 [CA 81, 26869 (1974)].Google Scholar
  205. 205.
    Edai Co. Ltd., Jpn. Patent 57,170,973 [CA 98, 180662 (1983)].Google Scholar
  206. 206.
    H. F. Pagel and E. R. Luckman, Proc. 1980 Symp. Wood Adhes.-Res., Appl., Needs, University of Wisconsin, Sept. 23–25, p. 122 (1980).Google Scholar
  207. 207.
    A. D. Adams, Proc. Wash. State Univ. Int. Symp. Particleboard, 14th, p. 195 (1980).Google Scholar
  208. 208.
    H. F. Pagel and E. R. Luckman, J. Appl. Polym. Sci., Appl. Polym. Symp. 40, 191 (1984).Google Scholar
  209. 209.
    J. R. Robertson, S. C. Cohen, and K. M. McNelis, J. Elastomers Plast. 15, 113 (1983).Google Scholar
  210. 210.
    G. W. Ball, R. P. Redman, and A. D. Adams, For. Ind. 106 (4), 76, 117 (1979).Google Scholar
  211. 211.
    R. J. Hoyle, Adhes. Age 24 (6), 43 (1981).Google Scholar
  212. 212.
    B. H. River, Adhes. Age 27 (2), 16 (1984).Google Scholar
  213. 213.
    D. Caster, Proc. 1980 Symp. Wood Adhes.-Res., Appl., Needs, University of Wisconsin, Sept. 23–25, p. 179 (1980).Google Scholar
  214. 214.
    J. B. Wilson, Adhes. Age 24 (5), 41 (1981).Google Scholar
  215. 215.
    J. B. Wilson, Proc. Wash. State Int. Symp. Particleboard, 14th, p. 185 (1980).Google Scholar
  216. 216.
    O. G. Udvardy, Proc. Wash. State Univ. Symp. Particleboard, 13th, p. 159 (1979).Google Scholar
  217. 217.
    G. Loew and H. I. Sachs, Proc. Wash. State Univ. Symp. Particleboard, 11th, p. 473 (1977).Google Scholar
  218. 218.
    H. J. Deppe, Proc. Wash. State Univ. Symp. Particleboard 11th, p. 13 (1977).Google Scholar
  219. 219.
    H. Lobenhoffer and K. Ernst, Ger. Patent 2,500, 884 (1976).Google Scholar
  220. 220.
    K. Ernst, Ger. Patent 2,306, 771 (1974).Google Scholar
  221. 221.
    P. D. Shoemaker and H. O. McQueary, U.S. Patent 4,046,952 [CA 87, 153660 (1977)].Google Scholar
  222. 222.
    G. P. Ellingson, Proc. Wash. State Univ. Symp. Particleboard 11, 369 (1977).Google Scholar
  223. 223.
    A. M. Wooler, U.S. Patent 4,110,397 [CA 88, 154701 (1978)].Google Scholar
  224. 224.
    K. Ernst and S. Haberland, Ger. Patent 1,653, 178 (1970).Google Scholar
  225. 225.
    A. McLaughlin, R. H. Richter, and H. E. Reymore, U.S. Patent 4,257,995 [CA 94, 210595 (1981)].Google Scholar
  226. 226.
    W. J. Farrissey, Jr., A. McLaughlin, R. H. Richter, C. P. Smith, and B. W. Tucker, U.S. Patent 4,257,996 [CA 94, 210594 (1981)].Google Scholar
  227. 227.
    R. A. Prather, U.S. Patent 4,352,696 [CA 97, 218371 (1982)].Google Scholar
  228. 228.
    R. A. Prather, U.S. Patent 4,376, 088 (1983).Google Scholar
  229. 229.
    B. R. Bogner and F. C. Grant-Acquah, U.S. Patent 4,376, 089 (1983).Google Scholar
  230. 230.
    J. P. Brown, G. Gibbins, and R. S. Hampson, U.S. Patent 4,388, 138 (1983).Google Scholar
  231. 231.
    G. W. Ball, J. P. Brown, G. Gibbins, and R. S. Hampson, U.S. Patent 4,396, 673 (1983).Google Scholar
  232. 232.
    H. Motoki and T. Sagioka, Mokuzai To Gijutsu 36, 6 (1979) [CA 93, 97154 (1980)].Google Scholar
  233. 233.
    H. J. Deppe and R. Stolzenburg, J. Appl. Polym. Sci., Polym. Symp. Ser. 40, 41 (1984).Google Scholar
  234. 234.
    J. M. Dinwoodie, J. Inst. Wood Sci. 8 (2), 59 (1978).Google Scholar
  235. 235.
    E. Roffael and W. Rauch, Holz Roh- Werkst. 31, 402 (1973).Google Scholar
  236. 236.
    H. Motoki and T. Sagioka, Mokuzai To Gijutsu 38, 9 (1979) [CA 93, 97153 (1980)].Google Scholar
  237. 237.
    H. Lehnert, W. Eisele, and O. Wittmann, Ger. Patent 2,444,002 [CA 88, 154702 (1978)].Google Scholar
  238. 238.
    M. Gamo, S. Kocho, M. Kondo, and Y. Katsuzawa, Nippon Setchaku Kyokai Shi 14, 420 (1978) [CA 90, 153659 (1979)].Google Scholar
  239. 239.
    A. Pizzi, J. Macromol. Sci., Chem. A16, 1243 (1981).Google Scholar
  240. 240.
    A. Pizzi, Holz Roh- Werkst. 40, 293 (1982).Google Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • B. H. Edwards
    • 1
  1. 1.Adhesives, Coatings, and Sealers Division3MSt. PaulUSA

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