Synthesis and Ring-Oligomer Recovery of an Environmentally Benign Malate-Containing Polyurethane Using Enzymatic Process

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  • MURAKAMI Saeko
    Chemical Engeneering Division, Kanagawa Industrial Technology Center
  • AOKI Nobuyoshi
    Chemical Engeneering Division, Kanagawa Industrial Technology Center

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Other Title
  • 酵素重合したリンゴ酸共重合体を前駆体とする環境低負荷型ポリウレタンの合成と環状オリゴマーへの酵素分解
  • コウソ ジュウゴウ シタ リンゴサン キョウ ジュウゴウタイ オ ゼンクタイ ト スル カンキョウ テイフカガタ ポリウレタン ノ ゴウセイ ト カンジョウ オリゴマー エ ノ コウソ ブンカイ

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Abstract

Oligo[(hexanediol-L-malate)-co-(hexanediol-succinate)] [oligo(HM-co-HS)] was prepared by the lipase-catalyzed polymerization of dimethyl L-malate, dimethyl succinate and 1,6-hexanediol in an environmentally benign bioprocess. These monomers can be derived from biomass resources. The contents of free hydroxyl groups in the oligomers was varied by changing the feed ratio of L-malate and succinate. Polyurethanes containing malic acid were synthesized by the reaction of enzymatically prepared oligo(HM-co-HS) and hexamethylene diisocyanate. The thermal properties of polyurethanes with different contents of L-malate and succinate were evaluated. Melting was observed for polyurethanes containing the oligomers with less than 20% L-malate. The glass transition temperatures of the polyurethanes increased with increasing contents of L-malate having a free hydroxyl group. The malate-containing polyurethanes were enzymatically degraded by lipase and the degradation products exclusively contained cyclic oligomers which may be repolymerized.

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 70 (10), 565-571, 2013

    The Society of Polymer Science, Japan

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