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A novel reaction of epoxy resins with polyfunctional active esters

Authors

  • Tadatomi Nishikubo,

    Corresponding author
    1. Laboratory of Polymer Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221, Japan
    • Laboratory of Polymer Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221, Japan
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  • Kazumi Tanaka

    1. Laboratory of Polymer Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221, Japan
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Abstract

Addition reactions of commercial epoxy resins such as bisphenol-A diglycidylether (BADGE), ethylene glycol diglycidylether (EGGE), and N,N-diglycidylaniline (GAN) with various active esters such as di[S-(benzothizolyl)] thioadipate (BTAD), di(4-nitrophenyl) adipate (NPAD), di(S-phenyl) thioadipate (PTAD), and 4-nitrobenzoyl esters of polyfunctional phenols were carried out in neat using quaternary salts or crown ether-salts complexes as a catalyst at 50–130°C. The rate of addition reaction of BTAD was faster than that with other esters under the same reaction conditions. Furthermore, it was found that the rate of addition reaction of the epoxy resins with some active esters was strongly affected by the kind of epoxy resin, the structural formula of carboxylic acid, and the kind of catalyst. The reaction of epoxy resins with polyfunctional active esters proceeded quantitatively at the elevated temperatures. However, some of the mixtures of epoxy resin, polyfunctional active ester and the catalyst showed excellent storage stability at 30°C.

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