The Chemistry of Structural Adhesives: Epoxy, Urethane, and Acrylic Adhesives

  • Denis J. Zalucha
  • Kirk J. Abbey


Adhesives have been used successfully in a variety of applications for centuries. Today, adhesives are more important than ever in our daily lives, and their usefulness is increasing rapidly. In the past few decades there have been significant advances in materials and in bonding technology. People now routinely trust their fortunes and their lives to adhesively bonded structures and rarely think about it.


Diglycidyl Ether Bond Line Isocyanate Group Acrylic Monomer Structural Adhesive 
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.
    The Adhesion Society,, 2 Davidson Hall-0201, Blacksburg, VA 24061, phone: 540-231-7257, fax: 540-231-3971, e-mail: adhesoc@vt.eduGoogle Scholar
  2. 2.
    Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol 1, Theory, Marcel Dekker, New York, 1967.Google Scholar
  3. 3.
    Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol 2, Materials, Marcel Dekker, New York, 1969.Google Scholar
  4. 4.
    Kaelble, D. H., Physical Chemistry of Adhesion, Wiley-Interscience, New York, 1971.Google Scholar
  5. 5.
    Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol. 3, Marcel Dekker, New York, 1973.Google Scholar
  6. 6.
    Skeist, L. (Ed.), Handbook of Adhesives, 2nd ed., Van Nostrand Reinhold, New York, 1977.Google Scholar
  7. 7.
    Wake, W. C., Adhesion and the Formulation of Adhesives, 2nd ed., Applied Science, New York, 1982.Google Scholar
  8. 8.
    Lee, L.-H., Adhesive Chemistry, Developments and Trends, Plenum, New York, 1984.Google Scholar
  9. 9.
    Panek, J. R. and Cook, J. P., Construction Sealants and Adhesives, 2nd ed., Wiley-Interscience, New York, 1984.Google Scholar
  10. 10.
    Adams, R. D. and Wake, W. C., Structural Adhesive Joints in Engineering, Elsevier, New York, 1984.Google Scholar
  11. 11.
    Hartshorn, S. R. (Ed.), Structural Adhesives Chemistry and Technology, Plenum Press, New York, 1986.Google Scholar
  12. 12.
    Kinloch, A. J., Adhesion and Adhesives Science and Technology, Chapman and Hall, London, 1987.Google Scholar
  13. 13.
    Tong, L. and Steven, G. P., Analysis and Design of Structural Bonded Joints, Kluwer Academic, Boston, 1999.Google Scholar
  14. 14.
    Ward, N. and Young, T., The Complete Guide to Glues and Adhesives, Krause, Iola, WI, 2001.Google Scholar
  15. 15.
    Gierenz, G. (Ed.), Adhesives and Adhesive Tapes, John Wiley & Sons, New York, NY, 2001.Google Scholar
  16. 16.
    Moore, D. R. (Ed.), Fracture Mechanics Testing Methods for Polymers, Adhesives and Composites, Elsevier, Amsterdam, 2001.Google Scholar
  17. 17.
    Veselovskii, R. A., Kestelman, V. N., and Veselovsky, R. A., Adhesion of Polymers, McGraw-Hill, New York, 2001.Google Scholar
  18. 18.
    Pocius, A. V., Adhesion and Adhesives Technology, Hanser Gardner, 2002.Google Scholar
  19. 19.
    Pocius, A. V, and Dillard, D., and Chaudhury, M., Surfaces, Chemistry and Applications: Adhesion Science and Engineering, Elsevier Science & Technology, Amsterdam, 2002.Google Scholar
  20. 20.
    Pizzi, A. (Ed.), Handbook of Adhesive Technology, Marcel Dekker, New York, 2003.Google Scholar
  21. 21.
    Swanson, D. W., Adhesive Materials for Electronic Applications: Polymers, Bonding, and Reliability, William Andrew, Norwich, NY, 2005.Google Scholar
  22. 22.
    Fisher, L. W., Selection of Engineering Materials and Adhesives, CRC, Boca Raton, FL, 2005.Google Scholar
  23. 23.
    Packham, D. E., Handbook of Adhesion, John Wiley & Sons, Hoboken, NJ, 2005.CrossRefGoogle Scholar
  24. 24.
    Chemical Abstracts Service, American Chemical Society, 2005.Google Scholar
  25. 25.
    Fowkes, F. M., and Mostafa, M. A., Ind. Eng. Chem. Prod. Res. Dev. 37, 605 (1978).Google Scholar
  26. 26.
    Fowkes, F. M., Physicohemical Aspects of Polymer Surfaces, Vol. 2, Mittal, K. L. (Ed.), Plenum, New York, p. 583.Google Scholar
  27. 27.
    Mark, H. F., “Future Improvements in the Cohesive and Adhesive Strength of Polymers-Part I,” Adhes. Age, 22(7), 35–40 (1979).Google Scholar
  28. 28.
    Mark, H. F., “Future Improvements in the Cohesive and Adhesive Strength of Polymers-Part II,” Adhes. Age, 22(9), 45–50 (1979).Google Scholar
  29. 29.
    May, C.A. (Ed), Epoxy Resins: Chemistry And Technology, 2nd ed., Marcel Dekker, New York, 1988.Google Scholar
  30. 30.
    Castan, P., Process of Preparing Synthetic Resins, U.S. Patent No. 2,324,483, 1943.Google Scholar
  31. 31.
    Dow Chemical, Dow Liquid Epoxy Resins, Form No. 296-00224-0199 WC+M, 1999, ( Scholar
  32. 32.
    Resolution Performance Products, EPON Resins and Modifiers SC:3059-01, 2002, ( Scholar
  33. 33.
    Reichhold, Inc, ( Scholar
  34. 34.
    Cognis Corp., ( Scholar
  35. 35.
    Huntsman Corp., ( Scholar
  36. 36.
    Resolution Performance Products, Eponol™ Resin 53-BH-35.Google Scholar
  37. 37.
    Partansky, A. M., Amer. Chem. Soc., Div. Org. Coatings Plast. Chem. 28(1), 366 (1968).Google Scholar
  38. 38.
    Partansky, A. M., Advan. Chem. Sen, Epoxy Resins, 92, 29 (1970).CrossRefGoogle Scholar
  39. 39.
    Hine, J., Linden, S.-M., and Kanagasabapathy, V. M., J. Org. Chem. 50(25), 5096 (1985).CrossRefGoogle Scholar
  40. 40.
    Matejka, L., Pororny, S., Dusek, K., Polym. Bull. (Berlin) 7(2–3), 123–8 (1982).Google Scholar
  41. 41.
    Dusek, K. and Matejka, L., “Transesterification and Gelation of Polyhydroxy Esters Formed from Diepoxides and Dicarboxylic Acids,” in Rubber Modified Thermoset Resins, Riew, C. K. and Gillham, J. K. (Eds), Am. Chem. Soc., Adv. Chem. Series 208 (1984), pp. 15–26.Google Scholar
  42. 42.
    Abbey, K. J., Pressley, M. W., and Durso, S. R., “Controlled Cure of Thiol-Epoxy Systems,” in Proceedings of the 22nd Annual Meeting of The Adhesion Society, Panama City Beach, FL, February 21–14, 1999, David R. Speth (Ed.).Google Scholar
  43. 43.
    Crivello, J. V., Heat Curable Compositions, U.S. Patent No. 4,173,551, 1979.Google Scholar
  44. 44.
    Crivello, J. V., Heat Curable Cationically Polymerizable Compositions and Method of Curing Same with Onium Salts and Reducing Agents, U.S. Patent No. 4,216,288, 1980.Google Scholar
  45. 45.
    Crivello, J. V., UV Curable Compositions and Substrates Treated Therewith, U.S. Patent No. 4,319,974, 1982.Google Scholar
  46. 46.
    Crivello, J. V. and Ashby, B. A., Methods of Adhesive Bonding Using Visible Light Cured Epoxies, U.S. Patent No. 4,356,050, 1982.Google Scholar
  47. 47.
    Crivello, J. V. and Lee, J. L., Photocurable Compositions, U.S. Patent No. 4,442,197, 1984.Google Scholar
  48. 48.
    Yagci, Y.; Reetz, I., “Externally stimulated initiator systems for cationic polymerization,” Progr. Polym. Sci. 23(8), 1485–1538 (1998).CrossRefGoogle Scholar
  49. 49.
    Tarbutton, K. S. and Robins, J., Acid Catalyzed, Toughened Epoxy Adhesives, U.S. Patent No. 4,846,905, 1989.Google Scholar
  50. 50.
    Jorissen, S. A., Ferguson, G. A., and Imirowicz, K., Epoxy Compound Blend with Di(aminoalkyl) Ether of Diethylene Glycol. U.S. Patent No. 5,548,026, 1996.Google Scholar
  51. 51.
    Baldwin, J. M. and Robins, J., Epoxy Adhesive Composition Comprising a Calcium Salt and Mannich Base, U.S. Patent No. 5,629,380, 1997.Google Scholar
  52. 52.
    Markevka, V. C., Griggs, A. L., and Tarbutton, K. S., Epoxy Adhesives with Dithiooxamide Adhesion Promoters, U.S. Patent 5,712,039, 1998.Google Scholar
  53. 53.
    Harold, S. and Schmitz, H.-R., Phosphorus-modified Epoxy Resins Comprising Epoxy Resins and Phosphorus-containing Compounds, U.S. Patent 5,830,973, 1998.Google Scholar
  54. 54.
    Mowrere, N. R., Kane, J. F., and Hull, C. G., Siloxane-modified Adhesive/Adherend Systems, U.S. Patent 5,942,073, 1999.Google Scholar
  55. 55.
    Rijsdijk, H., Overbergh, N., DeBlick, G., Miles, G., and Kennan, A., Curable Adhesive System, U.S. Patent No. 5,952,071, 1999.Google Scholar
  56. 55.
    Bayer, O., German Patent No. 728.981, 1937.Google Scholar
  57. 56.
    Saunders, J. H. and Frisch, K. C., Polyurethanes, Chemistry and Technology, Vols. 1 and 2, Interscience, New York, 1962, 1964.Google Scholar
  58. 57.
    Oertel, G. (Ed.), Polyurethane Handbook, 2nd E., Hanser, Munich, 1994.Google Scholar
  59. 58.
    Randall, D., Lee, S. (Eds.), The Polyurethane Book, John Wiley & Sons, New York, 2003.Google Scholar
  60. 59.
    Dunn, D. J., Engineering and Structural Adhesives, Rapra Review Reports, 15(1), Report 169, Rapra Technology Ltd., Shropshire, UK, 2004.Google Scholar
  61. 60.
    Polyurethane Adhesives, Rapra Published Search Number 114, Rapra Technology Ltd., Shropshire, UK.Google Scholar
  62. 61.
    Fabris, H. J., Maxey, E. M., and Uelzmann, H., Urethane Adhesive Having Improved Sag Resistance, U.S. Patent No. 3,714,127, 1973.Google Scholar
  63. 62.
    Goel, A. B., Sag Resistant Urethane Adhesives with Improved Antifoaming Property, U.S. Patent No. 4,728,710, 1988.Google Scholar
  64. 63.
    Baueriedel, H., Adhesives Based on Polyurethane Prepolymers Having a Low Residual Monomer Content, U.S. Patent No. 4,623,709, 1986.Google Scholar
  65. 64.
    Ono, H.-K., Jones, F. N., and Pappas, S. P., “Relative Reactivity of Isocyanate Groups of Isophorone Diisocyanate. Unexpected High Reactivity of the Secondary Isocyanate Group,” J. Polym. Sci., Polym. Lett. Ed., 23, 509–515 (1985).CrossRefGoogle Scholar
  66. 65.
    Okawa, T., Process for Producing Isocyanate Compound, U.S. Patent No. 5,166,414, 1992.Google Scholar
  67. 66.
    Nagata, T., Yamashita, H., Kusumoto, M., and Okazaki, K., Stabilizing Method of Isocyanate Compounds and Isocyanate Compositions Stabilized Thereby, U.S. Patent No. 5,302,749, 1994.Google Scholar
  68. 67.
    Ohashi, Y., Matsuda, H., Nishi, E., and Nishida, T., Moisture Curing Urethane Adhesive Composition, U.S. Patent No. 5,698,656, 1997.Google Scholar
  69. 68.
    Fukatsu, S. and Hattori, Y, Moisture Curable Polymer Composition and Process for Production Thereof U.S. Patent No. 5,767,197, 1998.Google Scholar
  70. 69.
    Schoener, T. E. and Housenick, J. B., Polyurethane Reaction System Having a Blocked Catalyst Combination, U.S. Patent No. 6,348,121, 2002.Google Scholar
  71. 70.
    Ambrose, R., Retsch, W. R., Jr., and Chasser, A., Blocked Isocyanate-based Compounds and Compositions Containing the Same, U.S. Patent No. 6,288,199, 2001.Google Scholar
  72. 71.
    Bader, E., U.S. Patent 33,333,025 (1967).Google Scholar
  73. 72.
    Bauer, W. Jr., “Acrylic Acid and Derivatives,” in Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2003.Google Scholar
  74. 73.
    Wilczynski, R. and Juliette, J. J., “Methacrylic Acid and Derivatives,” in Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2003.Google Scholar
  75. 74.
    Huang, J.-P., Righettini, R. F, and Dennis, F. G., Adhesive Formulations, U.S. Patent 6,225,408 (2001).Google Scholar
  76. 75.
    Briggs, P. C. and Muschiatti, L. C., U.S. Patent 3,890,407 (1975).Google Scholar
  77. 76.
    Zalucha, D. J., Sexsmith, F. H., Hornaman, E. C., and Dawdy, T. H., Structural Adhesive Formulations, U.S. Patent No. 4,223,115, (1981).Google Scholar
  78. 77.
    Dawdy, T. H., Epoxy Modified Structural Adhesives Having Improved Heat Resistance, U.S. Patent 4,467,071 (1984).Google Scholar
  79. 78.
    McCormick, F. B., Drath, D. J., Gorodisher, I., Kropp, M. A., Palazzotto, M. C., and Sahyun, M. R. V., Energy-curable Cyanate/Ethylenically Unsaturated Compositions, U.S. Patent No. 6,029,219 (2000).Google Scholar
  80. 79.
    Righettini, R. R. and Dawdy, T. H., Free Radical Polymerizable Compositions Including Para-Halogenated Aniline Derivatives,” U.S. Patent 5,932,638 (1999).Google Scholar
  81. 80.
    Edelman, R. and Catena, W., Rapid Curing Structural Acrylic Adhesive, U.S. Patent No. 5,865,936 (1999).Google Scholar
  82. 81.
    Usifer, D. A. and Broderick, I. C., Urethane Adhesive Compositions, U.S. Patent No. 5,426,166 (1995).Google Scholar
  83. 82.
    Usifer, D. A. and Broderick, I. C., Urethane Adhesive Compositions, U.S. Patent No. 5,484,864 (1996).Google Scholar
  84. 83.
    Imai, Y., Fujisawa, S., Matsui, H., Yamazaki, H., Masuhuara, E. Japanese Kokai 69-100477, 1973.Google Scholar
  85. 84.
    Fujisawa, S.; Imai, Y; Masuhara, E. Iyo Kizai Hokoku, Tokyo Ika Shika Daigaku 1969, 3, 64–71.Google Scholar
  86. 85.
    Zharov, J. V; Krasnov, J. N., Polymerizable Compositions Made with Polymerization Initiator Systems Based on Organoborane Amine Complexes, U.S. Patent 5,539,070, 1996.Google Scholar
  87. 86.
    3M Technical Literature for DP-8010; January 2002.Google Scholar
  88. 87.
    Sonnenschein, M. F., Webb, S. P., and Rondan, N. G., Amine Organoborane Complex Polymerization Initiators and Polymerizable Compositions, U.S. Patent 6,706,831, 2004.Google Scholar
  89. 88.
    Leaversuch, R., “Long-Glass PP Makes Inroadsln Automotive Front Ends,” Plastics Technol., online article,, Gardner.Google Scholar
  90. 89.
    Kendall, J. L. and Abbey, K. J., Internally Coordinated Organoboranes, U.S. Patent Application 20040242817.Google Scholar
  91. 90.
    Abbey, K. J. and Kendall, J. L., “Internally coordinated organoboranes: Stability and activation in polyolefin adhesives,” Polym. Mater. Sci. Eng. 2004(2).Google Scholar
  92. 91.
    Pohl, E. and Osterholz, F. D., Novel Vulcanizable Silane-Terminated Polyurethane Polymers, U.S. Patent 4,645,816, 1987.Google Scholar
  93. 92.
    Brownstein, A. M., Anaerobic Adhesive, U.S. Patent 3,428,614, 1969.Google Scholar
  94. 93.
    Su, W.-F., A., UV Curable High Tensile Strength Resin Composition, U.S. Patent 4,618,632, 1986.Google Scholar
  95. 94.
    Hawkins, J. M., Epoxy Resin Adhesive Compositions Containing an Isocyanate Terminated Polyurethane Prepolymer and a Chain Extender, US. Patent No. 3,636,133, 1972.Google Scholar
  96. 95.
    Trieves, R. and Pratley, K. G. M., U.S. Patent No. 4,623,702, 1986, November.Google Scholar
  97. 96.
    Anderson, G. J. and Zimmel, J. M., Thermally Stable Hot Melt Moisture-cure Polyurethane Adhesive Composition, US. Patent No. 5,939,499, 1999.Google Scholar
  98. 97.
    Mclnnis, E. L., Santosusso, T. M., and Quay, J. R., Hot Melt Adhesives Comprising Low Free Monomer, Low Oligomer Isocyanate Prepolymers, U.S. Patent No. 6,280,561, 2001.Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Denis J. Zalucha
  • Kirk J. Abbey

There are no affiliations available

Personalised recommendations