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Chemoenzymatic Synthesis and Chemical Recycling of Poly(ester-urethane)s
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
* Author to whom correspondence should be addressed.
Received: 27 July 2011; in revised form: 21 August 2011 / Accepted: 22 August 2011 / Published: 29 August 2011
Abstract: Novel poly(ester-urethane)s were prepared by a synthetic route using a lipase that avoids the use of hazardous diisocyanate. The urethane linkage was formed by the reaction of phenyl carbonate with amino acids and amino alcohols that produced urethane-containing diacids and hydroxy acids, respectively. The urethane diacid underwent polymerization with polyethylene glycol and a,w-alkanediols and also the urethane-containing hydroxy acid monomer was polymerized by the lipase to produce high-molecular-weight poly(ester-urethane)s. The periodic introduction of ester linkages into the polyurethane chain by the lipase-catalyzed polymerization afforded chemically recyclable points. They were readily depolymerized in the presence of lipase into cyclic oligomers, which were readily repolymerized in the presence of the same enzyme. Due to the symmetrical structure of the polymers, poly(ester-urethane)s synthesized in this study showed higher Tm, Young’s modulus and tensile strength values.
Keywords: enzyme-catalyzed polymerization; chemical recycling; green polymer; polyurethane; poly(ester-urethane)
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Hayashi, H.; Yanagishita, Y.; Matsumura, S. Chemoenzymatic Synthesis and Chemical Recycling of Poly(ester-urethane)s. Int. J. Mol. Sci. 2011, 12, 5490-5507.
Hayashi H, Yanagishita Y, Matsumura S. Chemoenzymatic Synthesis and Chemical Recycling of Poly(ester-urethane)s. International Journal of Molecular Sciences. 2011; 12(9):5490-5507.
Hayashi, Hiroto; Yanagishita, Yoshio; Matsumura, Shuichi. 2011. "Chemoenzymatic Synthesis and Chemical Recycling of Poly(ester-urethane)s." Int. J. Mol. Sci. 12, no. 9: 5490-5507.