Chemoenzymatic synthesis and chemical recycling of sustainable polyurethanes

Yoshio Yanagishita, Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Two novel types of chemically recyclable ester-containing polyurethanes, namely, a diol-diacid-type poly(diester-urethane) (PDEU) and a hydroxy acid type poly(ester-urethane) (PEU), were prepared by a green synthetic route that avoids the use of hazardous diisocyanate. The urethane linkage was introduced by the reaction of ethylene carbonate with amino alcohols and amino acids to form urethanediol and urethane-containing hydroxy acids, respectively. The urethanediol underwent polymerization with dimethyl adipate in the presence of lipase to produce a high-molecular-weight PDEU, while PEU was prepared by the lipase-catalyzed direct polycondensation of the urethane-containing hydroxy acid monomer. The periodic introduction of ester linkages into the polyurethane chain afforded primary biodegradation points and chemically recyclable segments. Both PDEU and PEU were readily degraded in the presence of lipase into oligomers which were readily repolymerized in the presence of the same enzyme.

Original languageEnglish
Pages (from-to)133-142
Number of pages10
JournalChemSusChem
Volume1
Issue number1-2
DOIs
Publication statusPublished - 2008 Feb 22

Fingerprint

Polyurethanes
Urethane
Lipases
Recycling
ester
Esters
recycling
Hydroxy Acids
Acids
acid
Lipase
Amino alcohols
Polycondensation
Biodegradation
Oligomers
polymerization
ethylene
Amino acids
alcohol
Carbonates

Keywords

  • Biodegradables
  • Enzymes
  • Polymers
  • Polyurethane

ASJC Scopus subject areas

  • Energy(all)
  • Environmental Chemistry
  • Materials Science(all)
  • Chemical Engineering(all)
  • Medicine(all)

Cite this

Chemoenzymatic synthesis and chemical recycling of sustainable polyurethanes. / Yanagishita, Yoshio; Kato, Makoto; Toshima, Kazunobu; Matsumura, Shuichi.

In: ChemSusChem, Vol. 1, No. 1-2, 22.02.2008, p. 133-142.

Research output: Contribution to journalArticle

Yanagishita, Yoshio ; Kato, Makoto ; Toshima, Kazunobu ; Matsumura, Shuichi. / Chemoenzymatic synthesis and chemical recycling of sustainable polyurethanes. In: ChemSusChem. 2008 ; Vol. 1, No. 1-2. pp. 133-142.
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