Abstract
Fluorine content dependency on the melting point and thermal polymerization reactivity of fluorine-containing phenylmaleimides were investigated by differential scanning calorimetry and are discussed on the basis of molecular structure calculations. The syntheses of fluorine-containing maleimides were carried out by thermal dehydration. Their yields tended to be lower with increasing fluorine content. This was due to lowered nucleophilic reactivity of the amino group. The fluorine-containing maleimides tended to have a high melting point with increasing fluorine content. But symmetry in the chemical structure was a more important factor influencing the melting point. The thermal polymerization temperature of double bonds became higher with increasing fluorine content. This thermal polymerization reactivity could be explained from results of molecular structure calculations. The decreased thermal polymerization reactivity of fluorine-containing maleimides could be attributed to molecular stabilization or the difficulty of activated biradical formation as shown by MNDO or MM method calculations. This is in agreement with that of fluorine-containing bismaleimides.
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References
T. Kataoka, Plastics, 33 (8), 70 (1982).
A. Takahashi, S. Yokozawa, M. Wajima, and K. Tsukanishi, “Proceedings of Printed Circuit World Convention III”, The Institute for Interconnecting and Packaging Electronic Circuits (IPC), Evanston, IL, U.S.A., 1984, W.C. 111-14.
A. Takahashi, N. Ooki, A. Nagai, H. Akahoshi, A. Mukoh, and M. Wajima, IEEE Trans. CHMT, 15, 418 (1992).
J. V. Crivello, J. Polym. Sci., Polym. Chem. Ed., 11, 1185 (1973).
C. D. Giulio, M. Gautier, and B. Jasse, J. Appl. Polym. Sci., 29, 1771 (1984).
A. Nagai, A. Takahashi, M. Wajima, and K. Tsukanishi, Polym. J., 20, 125 (1988).
A. Nagai, A. Takahashi, M. Suzuki, and A. Mukoh, J. Appl. Polym. Sci., 44, 159 (1992).
S. Nishimura, A. Nagai, A. Takahashi, T. Narita, T. Hagiwara, and H. Hamana, Polym. J., 22, 171 (1990).
A. C. Mirsa, G. C. Tesoro, G. Hougham, and S. Pendharker, Polymer, 33, 1078 (1992).
A. Nagai, A. Takahashi, M. Suzuki, J. Katagiri, and A. Mukoh, J. Appl. Polym. Sci. 41, 2241 (1990).
N. E. Searle, US patent, 2444536 (1948).
J. M. Barrales-Rienda, J. G. Ramos, and M. S. Chaves, J. Fluorine Chem., 9, 293 (1977).
Ya. S. Vygodskii, V. A. Adigezalov, A. A. Askadskii, G. L. Slonimskii, Sh. T. Bagirov, V. V. Korshak, S. V. Vinogradova, and Z. M. Nagiev, Polym. Sci. U.S.S.R., 21, 2951 (1980).
A. C. Misra and G. Tesoro, Polymer, 33, 1083 (1992).
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985).
A. Matsumoto, T. Kubota, and T. Otsu, Macromolecules 23, 4508 (1990).
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Nagai, A., Takahashi, A. Preparation and Thermal Behavior of Fluorine-Containing Phenylmaleimides. Polym J 26, 357–362 (1994). https://doi.org/10.1295/polymj.26.357
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DOI: https://doi.org/10.1295/polymj.26.357