Thermoplastic polyurethanes from β-methyl-δ-valerolactone-derived amidodiol chain extenders

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.