Journal of Polymer Research

, 25:234 | Cite as

Photo-thermally cured eugenol-derived epoxy resins by simultaneous thiol-ene/thiol-epoxy/thiol-maleimide triple “click” reactions

  • Mitsuhiro ShibataEmail author
  • Kaito Sugane
  • Ayumu Satoh


Polyglycidyl ether of eugenol novolac (PGEEGN) was synthesized by the glycidylation reaction of eugenol novolac (EGN) with an average degree of polymerization of ca. 3. A mixture of PGEEGN and a pentaerythritol-based tetrathiol (S4P) was photo-polymerized at room temperature and subsequently thermally cured at 100–150 °C to produce a two-component cured product (PGEEGN-S4P). A similar curing reaction of glycidyl ether of eugenol (GEEG) and S4P produced another two-component cured product (GEEG-S4P). Furthermore, a mixture of PGEEGN, S4P and 4,4′-bismaleimidodiphenylmethane (BMI) was photo-polymerized at room temperature and subsequently thermally cured at 100–230 °C to produce a three-component cured product (PGEEGN-S4P-BMI). The FT-IR spectral analysis revealed that the thiol-ene and thiol-epoxy reactions progressed for GEEG-S4P and PGEEGN-S4P, and the thiol-ene, thiol-epoxy and thiol-maleimide reactions progressed for PGEEGN-S4P-BMI. The 5% weight loss temperatures of PGEEGN-S4P and PGEEGN-S4P-BMI were higher than that of GEEG-S4P. A higher order of Tg, tensile strength and modulus was PGEEGN-S4P-BMI > PGEEGN-S4P > GEEG-S4P. The oligomerization of eugenol units and incorporation of BMI were effective to improve thermal and mechanical properties of the GEEG/S4P curing system.


Renewable resources Photo-thermal dual curing Glycidyl ether of eugenol novolac Bismaleimide Tetrathiol Thiol-ene/thiol-epoxy/thiol-maleimide reactions 



We thank Dr. Naozumi Teramoto and Dr. Toshiaki Shimasaki of our department for the helpful suggestions.


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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of Life and Environmental Sciences, Faculty of EngineeringChiba Institute of TechnologyChibaJapan

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