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Ring-Opening Polymerization of Triaziridine Compounds in Water: An Extremely Facile Method to Synthesize a Porous Polymer through Polymerization-Induced Phase Separation

  • Naofumi Naga*
    Naofumi Naga
    Department of Applied Chemistry, College of Engineering, Shibaura Institute of Technology, 3-7-4 Toyosu, Koto-ku, Tokyo 135-8548, Japan
    Graduate School of Engineering and Science, Shibaura Institute of Technology, 3-7-4 Toyosu, Koto-ku, Tokyo 135-8548, Japan
    *E-mail: [email protected]
    More by Naofumi Naga
  • Tomoya Takenouchi
    Tomoya Takenouchi
    Graduate School of Engineering and Science, Shibaura Institute of Technology, 3-7-4 Toyosu, Koto-ku, Tokyo 135-8548, Japan
  • , and 
  • Tamaki Nakano
    Tamaki Nakano
    Institute for Catalysis and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan
    Integrated Research Consortium on Chemical Sciences, Institute for Catalysis, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan
Cite this: ACS Macro Lett. 2022, 11, 5, 603–607
Publication Date (Web):April 12, 2022
https://doi.org/10.1021/acsmacrolett.2c00110
Copyright © 2022 American Chemical Society

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    Abstract

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    Dissolution of trifunctional aziridine compounds, 2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate] (3AZ) and tetramethylolmethane-tri-β-aziridinylpropionate (3AZOH), in water initiates a ring-opening polymerization and successful yields the corresponding network polymers via cationic polymerization. The polymerization of 3AZ induced phase separation and produced porous polymers under a wide range of monomer concentrations and polymerization temperatures. The phase separation rate in the 3AZ/water system was estimated by quantifying the turbidity by means of light transmission where transmittance decreased with an increase in the content of phase-separated materials. The rate increased with an increase in reaction temperature. The 3AZ porous polymers showed characteristic surface morphologies, which were formed by connected particles with diameters of about 4–5 μm. The porous polymers were not breakable by the compression test under 50 N. The Young’s modulus of the 3AZ porous polymers increased with an increase in polymerization temperature, which may be accounted for by cross-linking through the formation of quaternary ammonium salt formed by a termination reaction. The 3AZ porous polymer absorbed various solvents.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsmacrolett.2c00110.

    • Detailed experimental procedures, illustration of a microscope with a photoregister to monitor the transmitted light intensity through the reaction system, a plausible model of phase separation via spinodal decomposition during the ring-opening polymerization of 3AZ in water, stress–strain curves of 3AZ porous polymers prepared from the reaction systems with different monomer concentrations, and absorbance capacity of 3AZ porous polymer (PDF)

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