Abstract
New thermosetting materials were developed for reworkable adhesive applications by introducing acetal ester groups as thermally degradable linkages into maleimide compounds. The synthesis of compounds containing maleimide functionality and acetal ester linkages was conducted by a one-step neat reaction from commercially available materials. The polymerization process and thermal degradation of the synthesized materials were studied. It was found that the acetal ester linkage degraded rapidly above 225°C and introduction of this linkage into the adhesive formulation led to improved reworkability of adhesively bonded substrates. A mechanism for reworkability was proposed based on insight provided by experimental and modeling work.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References and Notes
Shirai, M. Prog. Org. Coat. 2007, 58, 158.
Woods, J. G.; Morrill, S. D. (Henkel Corporation) U.S. Patent 6,916,890, July 12, 2005.
Woods, J. G.; Torres-Filho, A.; Yaeger, E. K.; Wang, J. (Henkel Corporation) U.S. Patent 6,887,737, May 3, 2005.
Tesero, G. C.; Sastri, V. J. Appl. Polym. 1990, 39, 1425.
Sastri, V. J.; Tesero, G. C. J. Appl. Polym. 1990, 39, 1439.
Yang, S.; Chen, J. S.; Korner, H.; Breiner, T.; Ober, C. K. Chem. Mater. 1998, 10, 1475.
Ogino, K.; Chen, J. S.; Ober, C. K. Chem. Mater. 1998, 10, 3833.
Ramis, X.; Salla, J. M.; Mas, C.; Mantecón, A.; Serra, A. J. Appl. Polym. Sci. 2004, 92, 381.
Giménez, R.; Fernandez-Francos, X.; Salla, J. M.; Serra, A.; Mantecón, A.; Ramis, X. Polymer 2005, 46, 10637.
Mas, C.; Ramis, X.; Salla, J. M.; Mantecón, A.; Serra, A. J. Polym. Sci. Part A Polym. Chem. 2006, 44, 1711.
Loy, D. A.; Wheeler, D. R.; Russick, E. M.; McElhannon, J. R.; Saunders, R. S. (Sandia Corporation) U.S. Patent 6,337,384, January 8, 2002.
Chen, X.; Wudl, F.; Mal, A. K.; Shen, H.; Nutt, S. R. Macromolecules 2003, 36, 1802.
Wang, L.; Wong, C. P. J. Polym. Sci. Part A Polym. Chem. 1999, 37, 2991.
Wang, L.; Li, H.; Wong, C. P. J. Polym. Sci. Part A Polym. Chem. 2000, 38, 3771.
Li, H.; Wang, L.; Jacob, K.; Wong, C. P. J. Polym. Sci. Part A Polym. Chem. 2002, 40, 1796.
Mison, P.; Sillion, B. Adv. Polym. Sci. 1999, 140, 137.
Gacal, B.; Cianga, L.; Agag, T.; Takeichi, T.; Yagci, Y.; J. Polym. Sci. Part A Polym. Chem. 2007, 45, 2774.
Liu, Y. L.; Hsieh, C. Y.; J. Polym. Sci. Part A Polym. Chem. 2006, 44, 905.
Agag, T.; Takeichi, T.; J. Polym. Sci. Part A Polym. Chem. 2006, 44, 1424.
Li, R. C.; Broyer, R. M.; Maynard, H. D.; Polym. Sci. Part A Polym. Chem. 2006, 44, 5004.
Themistou, E.; Kanari, A.; Patrickios, C. S.; Polym. Sci. Part A Polym. Chem. 2007, 45, 5811.
Jain, R.; Stanley, S. M.; Fréchet, J. M. J. Macromolecules, 2007, 40, 452.
Buchwalter, S. L.; Kosbar, L. L. J. Polym. Sci. Part A Polym. Chem. 1996, 34, 249.
Luo, S.; Wong, C. P.; J. Adh. Sci. Technol. 2004, 18, 275.
The polymerization of compound 2 was not conducted because its high viscosity made the mixing process difficult.
Compound 6 was synthesized according to the procedure: Musa, O. (National Starch and Chemical Company) U.S. Patent 6,803,406, October 12, 2004.
The die shear tests were conducted at 150°C because the upper temperature limit for the die shear testing equipment is 150°C. Exposure to 250°C for 2 min prior to the die shear measurements is to simulate the rework condition.
Smith, M. B.; March, J. In March's Advanced Organic Chemistry; Fifth Edition, Wiley, New York, 2001; Chapter 17, pp. 1328–1329.
The significance of the reaction medium on reaction rate has been reported by Thames, S. J. Coatings Technol. 1990, 62(784), 51.
The cured sample was prepared by heating a mixture of 98 wt% compound 1 and 2 wt% USP-90MD at 120°C for 10 min.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2009 Springer Science+Business Media B.V.
About this paper
Cite this paper
Musa, O.M. et al. (2009). Thermally Degradable Maleimides for Reworkable Adhesives. In: Khosravi, E., Yagci, Y., Savelyev, Y. (eds) New Smart Materials via Metal Mediated Macromolecular Engineering. NATO Science for Peace and Security Series A: Chemistry and Biology. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3278-2_24
Download citation
DOI: https://doi.org/10.1007/978-90-481-3278-2_24
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-3276-8
Online ISBN: 978-90-481-3278-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)