Preparation and Biodegradation Behavior of Copolymers of Trimethylene Carbonate with Lactones

• SHIRAHAMA Hiroyuki

  Department of Applied Chemistry, Faculty of Engineering, Hiroshima University

• KANETANI Akinori

  Department of Applied Chemistry, Faculty of Engineering, Hiroshima University

• YASUDA Hajime

  Department of Applied Chemistry, Faculty of Engineering, Hiroshima University

Bibliographic Information

Other Title

• トリメチレンカーボネート/ラクトン共重合体の調製と生分解挙動
• トリメチレンカーボネート ラクトン キョウ ジュウゴウタイ ノ チョウセイ ト

Abstract

Random and block copolymers of cyclic trimethylene carbonate (TMC) with lactone [ε-caprolactone (CL) or δ-valerolactone (VL)] were synthesized for the first time in this study using a weak cationic catalyst [AlEt₃/H₂O (1 : 0.75)]. Elimination of carbonic acid from TMC unit did not occur during (co) polymerization, thus making it possible to obtain high molecular weight carbonate (co) polymers in high yield, with no ether linkage in the main chains. Measurement of NMR and thermal properties of the polymers indicated that these copolymers could be prepared separately.<BR>The degradability of (co) polymers by enzymes [lipoprotein lipase and cholesterol esterase (both from Pseudomonas sp.)] was examined and that of TMC/lactone copolymers was generally more extensive compared to the TMC (or lactone) homopolymer and the degradability of random copolymers was greater than that of block copolymers. The greater degradability of polymers by lipoprotein lipase than that by cholesterol esterase was particularly evident for TMC-rich block copolymers, suggesting substrate specificity of the lipase for TMC unit to exceed that of esterase.<BR>Water-soluble products of TMC/CL (=17/83) random copolymer degraded by lipoprotein lipase were fractionated using HPLC and a fraction collector. The ¹H NMR spectra of the products indicated the TMC/CL copolymer to ultimately be degraded into 1, 3-propanediol and 6-hydroxycaproic acid.

Journal

• Journal of Japan Oil Chemists' Society

  Journal of Japan Oil Chemists' Society 47 (11), 1251-1260,1280, 1998

  Japan Oil Chemists' Society

Keywords

• random copolymers
• block copolymers
• trimethylene carbonate
• lactone
• enzymatic degradation
• degraded products

Details

• CRID: 1390282679068180352
• NII Article ID: 10002277816
• NII Book ID: AN10512582
• DOI: 10.5650/jos1996.47.1251
• ISSN: 18841996
• ISSN: 13418327
• NDL BIB ID: 4604485
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4604485
• Web Site: https://www.jstage.jst.go.jp/article/jos1996/47/11/47_11_1251/_pdf
• Data Source:
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  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed