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Synthesis and properties of degradable gels and porous polymers including acetal group in the network structure by addition reaction of multi-functional phenols and divinyl ether compounds

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Abstract

Gels containing acetal group have been synthesized by addition reaction of multi-functional phenols, 1,1,1-tris(4-hydroxyphenyl)ethane (THPE) or tannic acid (TA) and divinylethers, diethylene glycol divinyl ether (DEGVE) or polyethylene glycol divinyl ether (PEGVE) in tetrahydrofuran (THF) or 1,4-dioxane (DO) using pyridinium p-toluenesulfonate as a catalyst under nitrogen atmosphere. The gels synthesized from DEGVE showed higher Young’s modulus, breaking stress, and lower breaking strain than the gels synthesized from PEGVE. The gels in DO showed higher mechanical properties than those in THF due to the high affinity between the network structure and the solvent used. The gels with TA showed lower Young’s modulus than those with THPE derived from flexible molecular structure of TA. The reaction of THPE and PEGVE in acetonitrile induced phase separation, and yielded porous polymer formed by connected globules about 10 μm diameter. The dried porous polymers showed remarkable increase in the Young’s modulus in comparison with the corresponding gels in THF or DO. The gels and porous polymers were degraded under atmospheric conditions caused by hydrolytic degradation of acetal groups in the network structure. The present hydrolytic degradable materials would be applicable for drug carriers or sensors for humidity or water.

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Acknowledgement

This work was partially supported by JSPS KAKENHI Grant Number 24550261.

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Authors and Affiliations

  1. Department of Applied Chemistry, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Koto-ku, Tokyo, 135-8548, Japan

    Naofumi Naga

  2. Graduate School of Engineering and Science, Shibaura Institute of Technology, 3-7-5 Toyosu, Koto-ku, Tokyo, 135-8548, Japan

    Naofumi Naga & Kazuma Hasegawa

  3. Institute for Catalysis and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo, 001-0021, Japan

    Hassan Nageh & Tamaki Nakano

  4. Integrated Research Consortium On Chemical Sciences, Institute for Catalysis, Hokkaido University, N 21, W 10, Kita-ku, Sapporo, 001-0021, Japan

    Tamaki Nakano

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  1. Naofumi Naga
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Naga, N., Hasegawa, K., Nageh, H. et al. Synthesis and properties of degradable gels and porous polymers including acetal group in the network structure by addition reaction of multi-functional phenols and divinyl ether compounds. Polym. Bull. 77, 5631–5645 (2020). https://doi.org/10.1007/s00289-019-03033-1

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  • DOI: https://doi.org/10.1007/s00289-019-03033-1

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