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Synthesis of network polymers by ring-opening addition reaction of multi-functional epoxy and dithiol compounds

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Abstract

Network polymers have been successfully synthesized by ring-opening addition reaction of multi-functional epoxy with α,ω-dithiol compounds in the presence of triethyl amine as a base catalyst. The reactions with alkane dithiol in dimethyl sulfoxide yielded transparent gels. Young’s modulus of the gels, which was evaluated by compression test, increased with increasing in number of epoxy group of the multi-functional epoxy compound and decreasing in methylene length of the alkane dithiol compound used due. The reaction of pentaerythritol polyglycidyl ether (PPE) with a dithiol compound having polyethylene glycol linkage, 1,2-bis(2-mercaptoethoxy)ethane (BME), in ethanol induced phase separation during the polymerization and produced the porous polymer under the appropriate conditions (temperature, monomer concentration, and catalyst amount). The porous polymers showed the surface morphology formed by connected particles in the diameters ranged from about 2 to 30 μm. The particles size tended to decrease with increasing of the monomer concentration and decreasing of the catalyst concentration. The PPE-BME porous polymers were not breakable under the compression of 50 N, and their Young’s moduli increased with increasing in the monomer concentration and the amount of the catalyst in the preparation reaction systems.

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Funding

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 & Yuto Hosoi

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

    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

Authors
  1. Naofumi Naga
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Contributions

Conceptualization, N.N. and T.N.; analysis, N.N. and Y.H.; investigation, N.N. and Y.H.; writing—original draft preparation, N.N.; writing—review and editing, T.N.; supervision, N.N. and T.N.; project administration, N.N.; funding acquisition, N.N. All authors have read and agreed to the published version of the manuscript.

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Correspondence to Naofumi Naga.

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Naga, N., Hosoi, Y. & Nakano, T. Synthesis of network polymers by ring-opening addition reaction of multi-functional epoxy and dithiol compounds. J Polym Res 30, 42 (2023). https://doi.org/10.1007/s10965-022-03429-0

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