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Synthesis and radical polymerization of styrene bearing 2-oxazolidone moiety derived from α-amino acid and investigation of its phenol adsorption behavior

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Abstract

We describe the synthesis and radical polymerization of series of styrenes with 2-oxazolidone moieties inherited from α-amino acids on the side chain. The 2-oxazolidone 2 was readily synthesized through the reaction of diphenyl carbonate with amino alcohols 1 that were prepared through the reduction of the corresponding α-amino acids (glycine, l-alanine, l-phenylalanine, l-valine, and l-methionine), in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene as a base catalyst. The subsequent N-substitution reaction of 2-oxazolidone with 4-(chloromethyl) styrene in the presence of sodium hydride produced high yield of the corresponding styrenic compounds 3. Free radical polymerization of these monomers 3 smoothly proceeded in the quantitative monomer-conversion using benzoyl peroxide as a radical initiator to give the corresponding polymers (P3). The thermal properties of the resulting polymers were evaluated by differential scanning calorimetry and thermogravimetric analysis. These oxazolidone-containing polymers effectively adsorbed phenols from aqueous solution, and were also miscible with poly(4-vinylphenol) in the equimolar ratio mixture, because of the effective hydrogen bond interaction involving a carboxyl group of oxazolidone moieties and a hydroxyl group of the phenol.

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Acknowledgements

The high-resolution mass spectrometry (HRMS) experiment was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices”.

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Authors and Affiliations

  1. Molecular Engineering Institute, Kindai University, 11-6 Kayanomori, Iizuka, Fukuoka, 820-8555, Japan

    Shuhei Yamada, Saori Nagai, Koichi Soraku & Takeshi Endo

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  1. Shuhei Yamada
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  2. Saori Nagai
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  3. Koichi Soraku
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  4. Takeshi Endo
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Correspondence to Takeshi Endo.

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Yamada, S., Nagai, S., Soraku, K. et al. Synthesis and radical polymerization of styrene bearing 2-oxazolidone moiety derived from α-amino acid and investigation of its phenol adsorption behavior. Polym. Bull. 74, 2671–2683 (2017). https://doi.org/10.1007/s00289-016-1858-1

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