Synthesis, characterization and polymerization of novel sugars based on methacrylate

Abstract

The present study describes the synthesis and characterizations of polymerizable vinyl sugars. Glucose, mannose, galactose and fructose are abundant and sustainable natural compounds. As it is not possible to make many derivatives of sugars without using protective groups, first of all, diacetone derivatives [diacetone-d-glucose (1), diacetone-d-mannose (2), diacetone-d-galactose (3) and diacetone-d-fructose (4)] were synthesized according to the literature as starting compounds. The remaining free hydroxyl groups on C-3 (diacetone glucose), C-6 (diacetone galactose), C-1 (diacetone fructose) and C-1 (diacetone mannose), were reacted with epichlorohydrin (1-chloro-2,3-epoxypropane) to produce then “-O-(2′,3′-epoxypropane-1′-yl)” ether derivatives (5, 6, 7, and 8) which are epoxy sugars in the basic medium. Next, the epoxy rings of the ethers (5, 6, 7, and 8) were opened with methacrylic acid in DMF to produce new sugar based methacrylates (9, 10, 11, and 12). Finally, free radical polymerization of these sugar based methacrylate monomers was performed, producing related polymers (13, 14, 15 and 16). The polymerizations were carried out using AIBN as an initiator at 70 °C in DMF. All the products were characterized by FTIR, 1HNMR and 13CNMR techniques. Thermal properties of all polymers were investigated by TG, DTG and DSC. The data obtained has suggested that thermal stability of the synthesized polymers has changed with the structure of the sugar and increase in molecular weight.