Preparation of <I>p</I>-cresol resin with dimethylene ether linkage and its solution properties

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  • YAMAGISHI Tada-Aki
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • IMAI Kensuke
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • OBAYASHI Junko
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • KUROIWA Harunobu
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • NAKAMOTO Yoshiaki
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • ISHIDA Shin-ichiro
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University

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Other Title
  • ジメチレンエーテル結合を有するパラクレゾール樹脂の合成とその溶液物性
  • ジメチレンエーテル ケツゴウ オ ユウスル パラクレゾール ジュシ ノ ゴウセ

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Description

p-Cresol resin with only methylene linkage (PCR-0) was prepared by the condensation of p-cresol with paraformaldehyde in acetic acid, using HCl as catalyst. p-Cresol resins with dimethylene ether linkage (PCR-30, PCR-50, and PCR-80 : the number is the dimethylene ether linkage content in mol-%) were prepared by the condensation of monomethylol p-cresol and dimethylol p-cresol under N2 and reduced pressure at 130-150°C. The solution properties of the p-cresol and acetylated p-cresol (Ac-PCR-0, Ac-PCR-50, and Ac-PCR-80) resins were determined by solution viscosity and solvation number in THF and CHCl3. The molecular conformation of PCR-0 was compact in both THF and CHCl3. However, the conformation of PCR-30, PCR-50, and PCR-80 more expanded as the fraction of dimethylene ether linkage in-creased. This trend was more remarkable in CHCl3 than in THF. On the other hand, the conformation of Ac-PCR-0, Ac-PCR-50, and Ac-PCR-80 expanded in both THF and CHCl3, independent of the fraction of dimethylene ether linkage. The strength of the hydrogen bond between phenolic hydroxyl groups in p-cresol resins was determined by IR spectroscopy. The strength in both THF and CHCl3 was decreasing with increasing the fraction of dimethylene ether linkage. This trend was more remarkable in CHCl3. This suggested that the hydrogen bond was formed between neighboring phenolic hydroxyl groups in the chain and the strength was weaker as the distance between neighboring phenolic hydroxyl groups was longer by introducing dimethylene ether linkage. Therefore, it was considered that the conformation of p-cresol resins was affected strongly by the intramolecular hydrogen bonds. The unperturbed dimension of Ac-PCR-50 was determined and it was larger than those of high-ortho novolak and acetylated o-cresol resin. It was found that the chain with dimethylene ether linkage expanded due to the weakness of intramolecular hydrogen bond and also to the nature of the skeleton of dimethylene ether linkage.

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