Abstract
An anhydride monomer containing ether oxide bridge, 7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboxylic anhydride (ONA), was successfully synthesized by Diels-Alder reaction of furan and maleic anhydride. The ONA was also studied as an end-cap for the polymerization of monomer reactant (PMR) type polyimides. Three molecular weight levels of the ONA end-capped PMR resins were evaluated. The effects of process conditions of these novel PMR resins on thermal and mechanical properties were investigated. It was demonstrated that the imidized prepolymers using the end-cap have good processability, and the cured polyimide specimens exhibited good thermal stability. The initial decomposition temperature, T d (ca. 580°C) and glass transition temperature, T g (330°C) of the novel resin (PI-20), prepared under optimum process conditions, compare favorably with the T d (ca. 620°C) and T g (ca. 348°C) of the state-of-the-art resin (PI′-20), respectively.
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Serafini, T.T., Delvigs, P. and Lightsey, G.R., J. Appl. Polym. Sci., 1972, 16: 905
Meador, M.A., Annu. Rev. Mater. Sci., 1998, 28: 599
Serafini, T.T. in “Polyimides: synthesis, characterization and applications”, ed. by Mittal, K.L., Plenum Press, New York, 1982, p. 645
Simone, C.D., Xiao, Y., Sun, X.D. and Scola, D.A., High Perform. Polym., 2005, 17: 51
Meador, M.A., Johnston, J.C., Cavano, P.J., Frimer A.A., Gilinsky-Sharon, P. and Gottlieb, H.E., Chem. Mater., 2001, 13: 2649
Meador, M.A., Johnston, J.C. and Cavano, P.J., Macromolecules, 1997, 30: 515
Diels, O. and Alder, K., Liebigs Ann. Chem., 1928, 460: 98
Fleming, I., “Frontier molecular orbitals and organic chemical reactions”, Wiley, London, 1976, p. 513
Rulisek, L., Sebek, P., Havlas, Z., Hrabal, R., Capek, P. and Svatos, A., J. Org. Chem. 2005, 70: 6295
Yang, C.P. and Chen, W.T., Macromolecules, 1993, 26: 4865
Labronici, M. and Ishida, H., Polym. Compos., 1999, 20: 515
Gao, S.Q., Zhang, Y.L., Li, J.Z. and Yang, S.Y., High Perform. Polym., 1999, 11: 167
Hu, A.J., Hao, J.Y., He, T. and Yang, S.Y., Macromolecules. 1999, 32: 8046
Meador, M.A., Frimer, A.A. and Johnston, J.C., Macromolecules, 2004, 37: 1289
Daniels, R. and Fisher, J.L., J. Org. Chem. 1963, 28: 320
Scola, D.A., “ASM Handbook, Vol. 21”, ASM International, Ohio, 2001, p. 111
Scola, D.A. and Stevens, P.M., J. Appl. Polym. Sci., 1981, 26: 231
Lubowitz, H.R., ACS Org. Coat Plast. Chem., 1971, 31: 560
Young, P.R. and Chang, A,C., J. Heterocycli. Chem., 1983, 20: 177
Wong, A.C. and Ritchey, W.M., Spectrosc. Lett., 1980, 13: 503
Wong, A.C., Garroway A.N. and Ritchey W.M., Macromolecules, 1981, 14: 832
Màas, J., Vidaurre, A., Meseguer, J.M., Romero, F., Pradas, M.M., Ribelles, J.L.G., Maspoch, M.L.L., Santana, O.O., Pagàes, P. and Pàerez-Folch, J., J. Appl. Polym. Sci., 2002, 83: 1507
Nair, T.M., Kumaran, M.G., Unnikrishnan, G. and Pillai, V.B., J. Appl. Polym. Sci., 2009, 112: 72
Pan, H. and Qiu, Z., Macromolecules, 2010, 43, 1499
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This work was financially supported by the Research Foundation of State Key Laboratory of Applied Organic Chemistry.
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Gong, Cl., Li, Yf., Yang, Hx. et al. Characterization and thermal stability of PMR polyimides using 7-oxa-bicyclo[2,2,1]hept-5-ene-2, 3-dicarboxylic anhydride as end caps. Chin J Polym Sci 29, 741–749 (2011). https://doi.org/10.1007/s10118-011-1089-8
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DOI: https://doi.org/10.1007/s10118-011-1089-8