Skip to main content

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

  • Chapter
Kent and Riegel’s Handbook of Industrial Chemistry and Biotechnology

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 249.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. The Adhesion Society, www.adhesionsociety.org, 2 Davidson Hall-0201, Blacksburg, VA 24061, phone: 540-231-7257, fax: 540-231-3971, e-mail: adhesoc@vt.edu

    Google Scholar 

  2. Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol 1, Theory, Marcel Dekker, New York, 1967.

    Google Scholar 

  3. Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol 2, Materials, Marcel Dekker, New York, 1969.

    Google Scholar 

  4. Kaelble, D. H., Physical Chemistry of Adhesion, Wiley-Interscience, New York, 1971.

    Google Scholar 

  5. Patrick, R. L. (Ed.), Treatise on Adhesion and Adhesives, Vol. 3, Marcel Dekker, New York, 1973.

    Google Scholar 

  6. Skeist, L. (Ed.), Handbook of Adhesives, 2nd ed., Van Nostrand Reinhold, New York, 1977.

    Google Scholar 

  7. Wake, W. C., Adhesion and the Formulation of Adhesives, 2nd ed., Applied Science, New York, 1982.

    Google Scholar 

  8. Lee, L.-H., Adhesive Chemistry, Developments and Trends, Plenum, New York, 1984.

    Google Scholar 

  9. Panek, J. R. and Cook, J. P., Construction Sealants and Adhesives, 2nd ed., Wiley-Interscience, New York, 1984.

    Google Scholar 

  10. Adams, R. D. and Wake, W. C., Structural Adhesive Joints in Engineering, Elsevier, New York, 1984.

    Google Scholar 

  11. Hartshorn, S. R. (Ed.), Structural Adhesives Chemistry and Technology, Plenum Press, New York, 1986.

    Google Scholar 

  12. Kinloch, A. J., Adhesion and Adhesives Science and Technology, Chapman and Hall, London, 1987.

    Google Scholar 

  13. Tong, L. and Steven, G. P., Analysis and Design of Structural Bonded Joints, Kluwer Academic, Boston, 1999.

    Google Scholar 

  14. Ward, N. and Young, T., The Complete Guide to Glues and Adhesives, Krause, Iola, WI, 2001.

    Google Scholar 

  15. Gierenz, G. (Ed.), Adhesives and Adhesive Tapes, John Wiley & Sons, New York, NY, 2001.

    Google Scholar 

  16. Moore, D. R. (Ed.), Fracture Mechanics Testing Methods for Polymers, Adhesives and Composites, Elsevier, Amsterdam, 2001.

    Google Scholar 

  17. Veselovskii, R. A., Kestelman, V. N., and Veselovsky, R. A., Adhesion of Polymers, McGraw-Hill, New York, 2001.

    Google Scholar 

  18. Pocius, A. V., Adhesion and Adhesives Technology, Hanser Gardner, 2002.

    Google Scholar 

  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. Pizzi, A. (Ed.), Handbook of Adhesive Technology, Marcel Dekker, New York, 2003.

    Google Scholar 

  21. Swanson, D. W., Adhesive Materials for Electronic Applications: Polymers, Bonding, and Reliability, William Andrew, Norwich, NY, 2005.

    Google Scholar 

  22. Fisher, L. W., Selection of Engineering Materials and Adhesives, CRC, Boca Raton, FL, 2005.

    Google Scholar 

  23. Packham, D. E., Handbook of Adhesion, John Wiley & Sons, Hoboken, NJ, 2005.

    Book  Google Scholar 

  24. Chemical Abstracts Service, American Chemical Society, 2005.

    Google Scholar 

  25. Fowkes, F. M., and Mostafa, M. A., Ind. Eng. Chem. Prod. Res. Dev. 37, 605 (1978).

    Google Scholar 

  26. Fowkes, F. M., Physicohemical Aspects of Polymer Surfaces, Vol. 2, Mittal, K. L. (Ed.), Plenum, New York, p. 583.

    Google Scholar 

  27. Mark, H. F., “Future Improvements in the Cohesive and Adhesive Strength of Polymers-Part I,” Adhes. Age, 22(7), 35–40 (1979).

    CAS  Google Scholar 

  28. Mark, H. F., “Future Improvements in the Cohesive and Adhesive Strength of Polymers-Part II,” Adhes. Age, 22(9), 45–50 (1979).

    CAS  Google Scholar 

  29. May, C.A. (Ed), Epoxy Resins: Chemistry And Technology, 2nd ed., Marcel Dekker, New York, 1988.

    Google Scholar 

  30. Castan, P., Process of Preparing Synthetic Resins, U.S. Patent No. 2,324,483, 1943.

    Google Scholar 

  31. Dow Chemical, Dow Liquid Epoxy Resins, Form No. 296-00224-0199 WC+M, 1999, (http://epoxy.dow.com/index.htm).

    Google Scholar 

  32. Resolution Performance Products, EPON Resins and Modifiers SC:3059-01, 2002, (http://www.resins.com/resins/am/products/Epon.html).

    Google Scholar 

  33. Reichhold, Inc, (http://www.reichhold.com/coatings/products/brand.cfm?ID=24).

    Google Scholar 

  34. Cognis Corp., (http://www.cognis.com/framescout.html7/ProductCatalog/FindYourProduct.html).

    Google Scholar 

  35. Huntsman Corp., (http://www.huntsman.com/structural-composites/).

    Google Scholar 

  36. Resolution Performance Products, Eponol™ Resin 53-BH-35.

    Google Scholar 

  37. Partansky, A. M., Amer. Chem. Soc., Div. Org. Coatings Plast. Chem. 28(1), 366 (1968).

    CAS  Google Scholar 

  38. Partansky, A. M., Advan. Chem. Sen, Epoxy Resins, 92, 29 (1970).

    Article  CAS  Google Scholar 

  39. Hine, J., Linden, S.-M., and Kanagasabapathy, V. M., J. Org. Chem. 50(25), 5096 (1985).

    Article  CAS  Google Scholar 

  40. Matejka, L., Pororny, S., Dusek, K., Polym. Bull. (Berlin) 7(2–3), 123–8 (1982).

    CAS  Google Scholar 

  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. 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. Crivello, J. V., Heat Curable Compositions, U.S. Patent No. 4,173,551, 1979.

    Google Scholar 

  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. Crivello, J. V., UV Curable Compositions and Substrates Treated Therewith, U.S. Patent No. 4,319,974, 1982.

    Google Scholar 

  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. Crivello, J. V. and Lee, J. L., Photocurable Compositions, U.S. Patent No. 4,442,197, 1984.

    Google Scholar 

  48. Yagci, Y.; Reetz, I., “Externally stimulated initiator systems for cationic polymerization,” Progr. Polym. Sci. 23(8), 1485–1538 (1998).

    Article  CAS  Google Scholar 

  49. Tarbutton, K. S. and Robins, J., Acid Catalyzed, Toughened Epoxy Adhesives, U.S. Patent No. 4,846,905, 1989.

    Google Scholar 

  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. 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. 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. 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. 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. 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. Bayer, O., German Patent No. 728.981, 1937.

    Google Scholar 

  57. Saunders, J. H. and Frisch, K. C., Polyurethanes, Chemistry and Technology, Vols. 1 and 2, Interscience, New York, 1962, 1964.

    Google Scholar 

  58. Oertel, G. (Ed.), Polyurethane Handbook, 2nd E., Hanser, Munich, 1994.

    Google Scholar 

  59. Randall, D., Lee, S. (Eds.), The Polyurethane Book, John Wiley & Sons, New York, 2003.

    Google Scholar 

  60. Dunn, D. J., Engineering and Structural Adhesives, Rapra Review Reports, 15(1), Report 169, Rapra Technology Ltd., Shropshire, UK, 2004.

    Google Scholar 

  61. Polyurethane Adhesives, Rapra Published Search Number 114, Rapra Technology Ltd., Shropshire, UK.

    Google Scholar 

  62. 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. Goel, A. B., Sag Resistant Urethane Adhesives with Improved Antifoaming Property, U.S. Patent No. 4,728,710, 1988.

    Google Scholar 

  64. Baueriedel, H., Adhesives Based on Polyurethane Prepolymers Having a Low Residual Monomer Content, U.S. Patent No. 4,623,709, 1986.

    Google Scholar 

  65. 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).

    Article  CAS  Google Scholar 

  66. Okawa, T., Process for Producing Isocyanate Compound, U.S. Patent No. 5,166,414, 1992.

    Google Scholar 

  67. 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. 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. 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. 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. 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. Bader, E., U.S. Patent 33,333,025 (1967).

    Google Scholar 

  73. Bauer, W. Jr., “Acrylic Acid and Derivatives,” in Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2003.

    Google Scholar 

  74. 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. Huang, J.-P., Righettini, R. F, and Dennis, F. G., Adhesive Formulations, U.S. Patent 6,225,408 (2001).

    Google Scholar 

  76. Briggs, P. C. and Muschiatti, L. C., U.S. Patent 3,890,407 (1975).

    Google Scholar 

  77. 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. Dawdy, T. H., Epoxy Modified Structural Adhesives Having Improved Heat Resistance, U.S. Patent 4,467,071 (1984).

    Google Scholar 

  79. 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. 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. Edelman, R. and Catena, W., Rapid Curing Structural Acrylic Adhesive, U.S. Patent No. 5,865,936 (1999).

    Google Scholar 

  82. Usifer, D. A. and Broderick, I. C., Urethane Adhesive Compositions, U.S. Patent No. 5,426,166 (1995).

    Google Scholar 

  83. Usifer, D. A. and Broderick, I. C., Urethane Adhesive Compositions, U.S. Patent No. 5,484,864 (1996).

    Google Scholar 

  84. Imai, Y., Fujisawa, S., Matsui, H., Yamazaki, H., Masuhuara, E. Japanese Kokai 69-100477, 1973.

    Google Scholar 

  85. Fujisawa, S.; Imai, Y; Masuhara, E. Iyo Kizai Hokoku, Tokyo Ika Shika Daigaku 1969, 3, 64–71.

    CAS  Google Scholar 

  86. 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. 3M Technical Literature for DP-8010; January 2002.

    Google Scholar 

  88. 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. Leaversuch, R., “Long-Glass PP Makes Inroadsln Automotive Front Ends,” Plastics Technol., online article, http://www.plasticstechnology.com/articles/200207cu1.html, Gardner.

    Google Scholar 

  90. Kendall, J. L. and Abbey, K. J., Internally Coordinated Organoboranes, U.S. Patent Application 20040242817.

    Google Scholar 

  91. 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. Pohl, E. and Osterholz, F. D., Novel Vulcanizable Silane-Terminated Polyurethane Polymers, U.S. Patent 4,645,816, 1987.

    Google Scholar 

  93. Brownstein, A. M., Anaerobic Adhesive, U.S. Patent 3,428,614, 1969.

    Google Scholar 

  94. Su, W.-F., A., UV Curable High Tensile Strength Resin Composition, U.S. Patent 4,618,632, 1986.

    Google Scholar 

  95. 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. Trieves, R. and Pratley, K. G. M., U.S. Patent No. 4,623,702, 1986, November.

    Google Scholar 

  97. 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. 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 

Download references

Authors

Editor information

James A. Kent Ph.D. (Professor of Chemical Engineering and Dean of Engineering)

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer Science+Business Media, LLC

About this chapter

Cite this chapter

Zalucha, D.J., Abbey, K.J. (2007). The Chemistry of Structural Adhesives: Epoxy, Urethane, and Acrylic Adhesives. In: Kent, J.A. (eds) Kent and Riegel’s Handbook of Industrial Chemistry and Biotechnology. Springer, Boston, MA. https://doi.org/10.1007/978-0-387-27843-8_14

Download citation

Publish with us

Policies and ethics