Exploration of mandelic acid-based polymethacrylates: Synthesis,properties, and stereochemical effects

Mandelic acid (MA) was utilized as a chiral biomass-based precursor to synthesize methacrylic monomers suitable for radical polymerization. A series of polymers were made that incorporated varying feeds of monomer stereopurity and the properties of these materials were investigated. High molar masses (>90 kg/mol) were achieved and the chirality in each polymer closely reflected the stereopurity of the monomer feeds. It was discovered that stereochemical effects had very little influence on the thermal and viscoelastic properties of the polymers produced, however, the steric bulk of the chiral pendants resulted in glassy, amorphous, and thermally stable materials with very low degrees of entanglement. The synthesis, thermal, and viscoelastic properties are discussed.