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Gelation behavior and thermal and mechanical properties of polymer network formed by the Diels-Alder reaction of furan- and maleimide-terminated four-arm star-shaped ethylene glycol oligomers

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Abstract

Furan-terminated four-arm star-shaped ethylene glycol oligomer (F4EGO n ) was synthesized by the esterification reaction of furfuryl alcohol and succinate-terminated four-arm star-shaped ethylene glycol oligomer (S4EGO n ) which was prepared by the reaction of succinic anhydride and hydroxy-terminated four-arm star-shaped ethylene glycol oligomer (H4EGO n ) having the approximate degree of polymerization per one oligo(ethylene glycol) chain, n = 4 or 11. Also, maleimide-terminated four-arm star-shaped ethylene glycol oligomer (M4EGO n ) was synthesized by the reaction of H4EGO n and 4-(maleimidophenyl)isocyanate. Solutions of F4EGO4/M4EGO4 and F4EGO11/M4EGO11 in 1,4-dioxane (DOX) or N,N-dimethylformamide (DMF) displayed thermo-reversible sol-gel transitions by the repeated Diels-Alder (DA) reactions at room temperature and retro DA reaction at 80 °C. Although F4EGO4/M4EGO4 was insoluble in water-containing solvents, F4EGO11/M4EGO11 was soluble in DMF/water or DOX/water 1/1, and the solution showed a sol-gel transition but only once or twice. Fourier transform infrared (FT-IR) analysis revealed that the conversion of DA reaction for the F4EGO n /M4EGO n (n = 4 or 11) film dried at 50 °C (F4EGO n -M4EGO n ) was 87 % (n = 4) or 90 % (n = 11). The glass transition temperature and tensile strength of F4EGO4-M4EGO4 were higher than those of F4EGO11-M4EGO11. Both F4EGO4-M4EGO4 and F4EGO11-M4EGO11 were swellable to water, DOX/water 1/1, or DMF/water 1/1.

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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

    Yoshiki Yoshioka, Daisuke Oikawa, Toshiaki Shimasaki, Naozumi Teramoto & Mitsuhiro Shibata

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  1. Yoshiki Yoshioka
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  2. Daisuke Oikawa
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  3. Toshiaki Shimasaki
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  4. Naozumi Teramoto
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  5. Mitsuhiro Shibata
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Correspondence to Mitsuhiro Shibata.

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Yoshioka, Y., Oikawa, D., Shimasaki, T. et al. Gelation behavior and thermal and mechanical properties of polymer network formed by the Diels-Alder reaction of furan- and maleimide-terminated four-arm star-shaped ethylene glycol oligomers. Colloid Polym Sci 293, 1059–1071 (2015). https://doi.org/10.1007/s00396-014-3492-5

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  • DOI: https://doi.org/10.1007/s00396-014-3492-5

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