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Thermal and mechanical properties of bio-based polymer networks by thiol-ene photopolymerizations of gallic acid and pyrogallol derivatives

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Abstract

Allylated pyrogallol (A3PG) and acrylated pyrogallol (Ac3PG) as bio-based trienes, and allylated gallic acid (A4GA) and acrylated allyl gallate (Ac3A1GA) as bio-based tetraenes were synthesized from pyrogallol and gallic acid, respectively. Thiol-ene photopolymerizations of the bio-based polyenes and a pentaerythritol-based primary tetrathiol (pS4P) at the allyl/SH ratio of 1/1 produced photo-cured resins (A3PG-pS4P, Ac3PG-pS4P, A4GA-pS4P and Ac3A1GA-pS4P). The FT-IR spectral analysis revealed that thiol-ene reactions of thiol/allyl and thiol/acryloyl groups smoothly proceeded. Gel fractions of acryl-based cured resins were a little higher than those of allyl-based cured resins. The swelling test and dynamic mechanical analysis revealed that GA- and acryl-based cured resins exhibited higher crosslinking densities than PG- and allyl-based cured resins, respectively. A higher order of tan δ peak temperature was Ac3PG-pS4P (48.3 ° C) > Ac3A1GA-pS4P (24.1 ° C) > A4GA-pS4P (22.1 ° C) > A3PG-pS4P (−7.8 ° C). Ac3PG-pS4P displayed the highest 5 % weight loss temperature, tensile strength and tensile modulus among all of the cured resins.

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Authors and Affiliations

  1. Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, 2-17-1, Tsudanuma, Narashino, Chiba, 275-0016, Japan

    Yuta Uemura, Toshiaki Shimasaki, Naozumi Teramoto & Mitsuhiro Shibata

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  1. Yuta Uemura
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  2. Toshiaki Shimasaki
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  3. Naozumi Teramoto
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  4. Mitsuhiro Shibata
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Correspondence to Mitsuhiro Shibata.

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Uemura, Y., Shimasaki, T., Teramoto, N. et al. Thermal and mechanical properties of bio-based polymer networks by thiol-ene photopolymerizations of gallic acid and pyrogallol derivatives. J Polym Res 23, 216 (2016). https://doi.org/10.1007/s10965-016-1105-3

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  • DOI: https://doi.org/10.1007/s10965-016-1105-3

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