Polymerization of Hindered Hydroquinone Derivatives

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  • KONISHI Gen-ichi
    Division of Material Engineering, Faculty of Natural Science & Technology, Kanazawa University
  • MIZUTANI Takeshi
    Division of Material Engineering, Faculty of Natural Science & Technology, Kanazawa University
  • NOJIRI Yamato
    Division of Material Engineering, Faculty of Natural Science & Technology, Kanazawa University
  • NAKAMOTO Yoshiaki
    Division of Material Engineering, Faculty of Natural Science & Technology, Kanazawa University

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  • かさ高い置換基を有するヒドロキノン誘導体の重合
  • カサダカイ チカンキ オ ユウスル ヒドロキノン ユウドウタイ ノ ジュウゴウ

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Description

Synthesis and thermal properties of new novolacs from hindered hydroquinone derivatives are described. Sulfuric acid-catalyzed condensation of 3, 5-di-tert-butyl-4-hydroxyanisole (1) or 2, 5-di-tertbutylhydroquinone (2) with paraaldehyde (acetaldehyde) (3) or paraformaldehyde (formaldehyde) (4) in 2-ethoxyethanol afforded the corresponding linear novolac (5) - (8) in high yields. The resulting novolacs were well-soluble in the common organic solvents such as chloroform, tetrahydrofuran, and acetone. The structures of 5-8 were determined by 1H & 13C NMR and IR analyses. From TGA analyses, hydroquinoneacetaldehyde novolac (5 and 7) were less heat-stable than hydroquinone-formaldehyde novolac (6 or 8). These novolacs had easier processability than that of phenol or cresol novolac and will be expected for reactive polymers, cured resins and resist materials.

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