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<p>2-Methylene-4H-benzo[d][1,3]dioxin-4-one, a cyclic hemiacetal ester prepared via the intramolecular esterification of acetyl salicylic acid, is an electron-rich vinyl monomer that can undergo radical polymerization to afford vinyl polymers with excellent thermal and mechanical properties. In this study, the aromatic ring was substituted with various substituents. Substitution with electron-donating groups resulted in instability and low yields, whereas substitution with two <i>tert</i>-butyl groups at the 6- and 8-positions increased the stability against moisture and reduced the reactivity in radical polymerization. Thus, the monomer afforded an almost ideal alternating copolymer with dimethyl maleate. Compared with the copolymers with nonsubstituted monomers, the copolymers with vinyl acetate presented a higher glass transition temperature, suggesting that the two <i>tert</i>-butyl groups effectively increased the thermal stability.</p>

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Synthesis and polymerization of modified dehydroaspirin with increased stability and polymer solubility

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年7月31日

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  • Yasuhiro Kohsaka,
  • Hanae Torisawa,
  • Akane Kazama

摘要

2-Methylene-4H-benzo[d][1,3]dioxin-4-one, a cyclic hemiacetal ester prepared via the intramolecular esterification of acetyl salicylic acid, is an electron-rich vinyl monomer that can undergo radical polymerization to afford vinyl polymers with excellent thermal and mechanical properties. In this study, the aromatic ring was substituted with various substituents. Substitution with electron-donating groups resulted in instability and low yields, whereas substitution with two tert-butyl groups at the 6- and 8-positions increased the stability against moisture and reduced the reactivity in radical polymerization. Thus, the monomer afforded an almost ideal alternating copolymer with dimethyl maleate. Compared with the copolymers with nonsubstituted monomers, the copolymers with vinyl acetate presented a higher glass transition temperature, suggesting that the two tert-butyl groups effectively increased the thermal stability.