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Abstract <p>A novel family of chlorine-containing monomers for high-performance polyimides and phthalonitrile resins was synthesized using 2,6-dichlorophenol. The key strategy involved the reduction of 2,6-dichloro-4-nitrophenol to a stable aminophenol hydrochloride, which served as a versatile nucleophile for nucleophilic aromatic substitution with various aromatic electrophiles. This approach provided access to <i>para</i>-aminophenoxyphthalonitriles. The synthesized aminophenoxyphthalonitriles act as self-catalyzing components for phthalonitrile resins. One such phthalonitrile was further functionalized with maleic anhydride to yield a derivative with a cross-linkable imide moiety. The synthesized phthalonitriles served as precursors to AB-type polyimide monomers. In a parallel synthetic route, the aminophenol hydrochloride was used to obtain a novel chlorinated unsymmetrical diamine. Structural diversity was demonstrated by obtaining monomers with chlorine atoms on either the aminophenoxy or phthalic acid core; the latter was found to adopt a zwitterionic-like state. The scope was expanded to include thioether bridge.</p>

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Synthesis of Chlorinated Monomers from 2,6-Dichlorophenol for Polyimides and Phthalonitrile Resins

  • 期刊论文

  • 发表日期：

    2026年7月9日

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  • Vyacheslav L. Baklagin,
  • Vladimir V. Bukhalin,
  • Igor G. Abramov

摘要

Abstract

A novel family of chlorine-containing monomers for high-performance polyimides and phthalonitrile resins was synthesized using 2,6-dichlorophenol. The key strategy involved the reduction of 2,6-dichloro-4-nitrophenol to a stable aminophenol hydrochloride, which served as a versatile nucleophile for nucleophilic aromatic substitution with various aromatic electrophiles. This approach provided access to para-aminophenoxyphthalonitriles. The synthesized aminophenoxyphthalonitriles act as self-catalyzing components for phthalonitrile resins. One such phthalonitrile was further functionalized with maleic anhydride to yield a derivative with a cross-linkable imide moiety. The synthesized phthalonitriles served as precursors to AB-type polyimide monomers. In a parallel synthetic route, the aminophenol hydrochloride was used to obtain a novel chlorinated unsymmetrical diamine. Structural diversity was demonstrated by obtaining monomers with chlorine atoms on either the aminophenoxy or phthalic acid core; the latter was found to adopt a zwitterionic-like state. The scope was expanded to include thioether bridge.