Abstract
Thermal reactions of N-phenylmaleimide (PMI) and o-allylphenol (AP) or diallylbisphenol-A (DABA) were investigated using 13C NMR and GPC in order to obtain information on the curing of bismaleimidodiphenylmethane (BMI) with DABA, widely used as thermosetting bismaleimide resins. In the thermal reactions of PMI and AP, 1:1 and 3:1 adducts were generated through ene-reaction and sequential Diels-Alder reactions accompanying the polymer of PMI and AP. The products from PMI and DABA were the ene-adduct and polymer but the Diels-Alder adduct could not be detected, in contrast to PMI/AP system. This difference in reactivity for PMI-AP and PMI-DABA may be due to steric repulsion of DABA and is discussed briefly by AM1 molecular orbital calculations.
Similar content being viewed by others
Article PDF
References
S. Zahir, M. A. Chaudhari, and J. King, Makromol. Chem., Macromol. Symp., 25, 141 (1989).
K. A. Barett, M. A. Chaudhari, and B. H. Lee, SAMPE J., 25, 17 (1989).
K. R. Carduner and M. S. Chattha, Polym. Mater. Sci. Eng., 56, 660 (1987).
K. R. Carduner and M. S. Chattha, Am. Chem. Soc., Symp. Ser., 367, 379 (1988).
T. Abraham, J. Polym. Sci., Part C: Polym. Lett., 26, 521 (1988).
T. Wagner-Jauregg, Tetrahedron Lett., 13, 1175 (1967).
T. Enoki, K. Ishii, H. Okubo, and S. Shibahara, Netsukoukasei Jushi, 12, 9 (1991).
T. Enoki, T. Takeda, and K. Ishii, High Perform. Polym., 7, 399 (1995).
D. Reyx, I. Campistron, and C. Caillaud, Macromol. Chem. Phys., 196, 775 (1995).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shibahara, S., Yamamoto, T., Yamaji, T. et al. Thermal Reactions of N-Phenylmaleimide and Mono- or Di-functional Allylphenols. Polym J 30, 404–409 (1998). https://doi.org/10.1295/polymj.30.404
Issue Date:
DOI: https://doi.org/10.1295/polymj.30.404
Keywords
This article is cited by
-
Bio-based thermosetting resins composed of cardanol novolac and bismaleimide
Polymer Journal (2013)
-
High-performance bio-based bismaleimide resins using succinic acid and eugenol
Polymer Journal (2011)