Biodegradable thermoplastic elastomers synthesized from C7–C10 aliphatic dicarboxylic acids, 2-methyl-1,3-propanediol, and L-lactide

Abstract

Elastic materials with high biodegradability should replace those with low biodegradability in some applications. We previously reported biodegradable thermoplastic elastomers (TPEs) composed of poly(l-lactide) (PLLA) as a hard segment and aliphatic polyesters from 2-methyl-1,3-propanediol (MP) and short aliphatic dicarboxylic acids as soft segments. In this study, we synthesized the biodegradable thermoplastic elastomers using longer aliphatic dicarboxylic acids to develop the TPEs with lower glass-transition temperature (T_g) and high biodegradability. A series of aliphatic polyesters were prepared by polycondensation of MP and aliphatic dicarboxylic acids bearing 7–10 carbons. Among them, poly(2-methyl-1,3-propylene azelate) (PMP9) was found to have lower T_g, amorphous nature, and high biodegradability in seawater. The ring-opening polymerization of l-lactide (LLA) using PMP9 as a macroinitiator afforded triblock copolymers, PLLA-b-PMP9-b-PLLA (TPE9). The successive addition of LLA to in-situ generated PMP9 resulted in the successful one-pot synthesis of high molecular weight TPE9. The TPE9s showed both low T_g of the PMP9 segment and high melting temperature of the PLLA segment. The TPE9s exhibited elastic behavior showing elongation at break of up to 2500 % in tensile tests and also high biodegradability in seawater. Thus, we developed potentially practical TPE with tunable physical properties and high biodegradability obtainable from easily available and renewable starting materials.