Poly(alditol sebacate)-PLA copolymers: enhanced degradability and tunable surface properties

Abstract

The synthesis of aliphatic, degradable polyesters based on biobased alditols was investigated. Mannitol and dulcitol were employed as biobased building blocks for the synthesis of aliphatic polyesters in combination with sebacoyl chloride. In order to achieve optimal control over the macromolecular architecture of the polymer, multifunctional monomers were converted to bifunctional species through a straightforward protection strategy. Bifunctional di-O-isopropylidene derivatives were synthesized starting from mannitol and dulcitol in a one-step procedure and exploited as monomers to yield linear poly(mannitol sebacate) (PMS) and poly(dulcitol sebacate) (PDS) derivatives. The use of a bifunctional monomer allowed an optimal control over the macromolecular architecture and the synthesis of PMS and PDS-based polyols. These polyols were then employed as initiators for the synthesis of PLA-based copolymers. Two different concentrations of PMS and PDS were tested and the related effects investigated, regarding the molecular weight and thermal properties of the resulting PLA-based copolymers. Deprotection of the isopropylidene moieties on the polyol backbone was then evaluated in order to determine the influence of liberation of free OH- groups on the wettability of the materials. Finally, degradation tests were performed in different aqueous environments, showing the influence of PMS and PDS on the degradation rate of PLA-based materials.