Sugar derivatives are excellent candidates for the building blocks of biobased plastics. This thesis focuses on the preparation of new monomers derived from bicyclic sugar derivatives and the polymerization thereof to afford useful polymer materials. The first area of research presented is the preparation of two new monovinyl monomers acetylated methacrylic isosorbide and acetylated acrylic isosorbide (AMI and AAI). PAMI and PAAI prepared by radical polymerization of were found to have high Tg and good thermal stability. Reversible Addition Fragmentation chain Transfer polymerization was used to prepare PAMI and PAAI block copolymer samples with low Tg polyacrylates. These block copolymers were investigated as pressure sensitive adhesives and were found to exhibit desirable adhesive properties consistent with high shear removable pressure sensitive adhesives. The second area of research focuses on the synthesis and polymerization of two new dimethacrylate monomers from glucarodilactone and mannarodilactone (GDMA and MDMA). Thermally initiated free radical polymerization of these monomers in the bulk afforded highly crosslinked and rigid thermoset materials. Tensile testing of PGDMA demonstrated mechanical properties similar to those reported for commercially available poly(dimethacrylates) from rigid monomers. PGDMA was found to degrade to water-soluble components after 17 days in the presence of base, but remained stable under acidic and neutral conditions. Applications investigated were P(GDMA-co-MDMA) coatings and copolymer microspheres from GDMA and methyl methacrylate.