Synthesis, Characterization, and Polymerization of Glycidyl Methacrylate Derivatized Dextran

Abstract

Glycidyl methacrylate derivatized dextran (dex-GMA) was synthesized by coupling of GMA to dextran in the presence of 4-(N,N-dimethylamino)pyridine using DMSO as an aprotic solvent and characterized by GPC, FTIR, and NMR. The structure of the product was established with 1H and CHCOSY NMR. The degree of substitution, as determined by NMR, can be controlled by varying the molar ratio of GMA and dextran. Almost quantitative incorporation of GMA (>90%) was established. Hydrogels were prepared by radical polymerization of aqueous solutions of dex-GMA, using ammonium peroxydi-sulfate (APS) and N,N,N′,N,′-tetramethylethylenediamine (TEMED) as the initiating system. The polymerization rate, as determined by FTIR analysis, was dependent on the APS, the TEMED, and the dex-GMA concentration. By proper selection of the polymerization conditions, hydrogels could be obtained in which more than 95% of the methacrylate groups had reacted within 20 min.