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 α,ω-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.
Highlights
Polyurethane is widely used in many products, such as the manufacture of plastic foams, sponges, paints, coatings and fibers
The urethane linkage was formed by the reaction of amine and phenyl carbonate, while ester linkages were periodically introduced into the main chain of the polymer by lipase to afford efficient chemical recycling segments
In spite of the diisocyanate-free method for the synthesis of the urethane linkage, phenyl chloroformate is produced by the reaction of phenol and phosgene
Summary
Polyurethane is widely used in many products, such as the manufacture of plastic foams, sponges, paints, coatings and fibers. Diisocyanate- and phosgene-free methods for the production of the generation of polyurethanes, as well as fast chemical recyclability and high performance, must be addressed. There have been some attempts to develop diisocyanate- and phosgene-free methods for the production of polyurethanes, such as the reaction of cyclic or phenyl carbonates and amines to form a urethane linkage [1,2,3,4,5,6]. Poly(ester-urethane)s having moderate elongation properties and Tms of around 100 °C were designed and synthesized by green processes. Their thermal and mechanical properties and chemical recyclabilities by lipase were reported
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