Synthesis and Characterization of Biodegradable Polymers Based on Glucose Derivatives.

Abstract

Syntheses of two new monomers, namely the glucose derivatives 2,3,4,6-tetra-O-acetyl-1 methacryloyl-glucopyranose (MGlc) and 2,3,4,6 tetra-O-acetyl-1-acryloylglucopyranose (AGlc), are presented. Their chemical structures were determined by the FTIR, 1H and 13C NMR spectroscopies, the single-crystal X-ray analysis, supported by the powder X-ray diffraction, and the DSC analyses. Molecules of both monomers exist in the β-anomeric form in the solid state. The variable temperature X-ray diffraction studies, supported by the DSC analyses, revealed AGlc's propensity for polymorphism and temperature-induced phase transitions. MGlc and AGlc crystallised from methanol were polymerized or copolymerized with methyl methacrylate and N-vinylpyrrolidone. The biodegradabilities of polymers as well as thermal and optical properties were studied. The results show that some properties of the obtained homopolymers and copolymers resemble those of PMMA. The main difference is that the AGlc and MGlc homopolymers are biodegradable while PMMA is not. The ternary copolymers, i.e., MGlc/AGlc-MMA-NVP lose more than 10% of their weight after six months.