Here we describe the synthesis of thermoplastic polyurethanes (TPUs) from polyols and amidodiol chain extenders, each of which is prepared from glucose-derived β-methyl-δ-valerolactone (MVL). Utilizing these novel chain extenders, we prepared TPUs with ca. 42–44 wt% hard segment content, comprising 72–75 wt% MVL-derived atoms. This compares favorably with an analogous sample prepared using 1,4-butanediol as the chain extender having 57 wt%. These TPUs are ductile (600–900% strain at break) and have high tensile strength (14–33 MPa stress at break). By virtue of the nature of the diamidodiol used as chain extenders, the hard segments contain a greater density of hydrogen bonding –NHC(=O)– functional groups relative to those prepared using traditional short chain 1,n-alkanediols.
Bibliographical noteFunding Information:
We thank Professor Marc A. Hillmyer for advice on aspects of these studies as well as for providing access to instrumentation. We thank Dr. Deborah K. Schneiderman for helpful discussions and review of the manuscript. Financial support for this research was provided by the Center for Sustainable Polymers at the University of Minnesota, an NSF-supported Center for Chemical Innovation (CHE-1413862). Some of the NMR data were recorded on an instrument purchased with support of the NIH Shared Instrumentation Grant program (S10OD011952).
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