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Synthesis and polymerization of novel epoxy compounds having an adamantane ring and evaluation of their heat resistance and transparency



Three adamantane derivatives substituted by epoxy groups, 1,3-bis(glycidyloxy)adamantane (2a), 5,7-dimethyl-1,3-bis(glycidyloxy)adamantane (2b), 1,3,5-tris(glycidyloxy)adamantane (2c), were synthesized from the corresponding adamantanediol or triol in good yields. These three epoxy compounds were polymerized with an acid anhydride, and the heat resistance of the resulting resins was evaluated. The resin prepared from 2c exhibited high heat resistance with the glass transition temperature (Tg) of 208°C and low degree of coloring by heating. The epoxy compounds were also found to be potentially useful as the precursors of high heat-resistant resins by thermal homopolymerization. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009