Trehalose vinylbenzyl ether was synthesized from trehalose and p-chloromethylstyrene (CMS) in DMSO in the presence of powdered NaOH. The structure of the product was characterized by IR and H-1 NMR spectroscopy. Degree of substitution (DS) on a trehalose unit calculated from the H-1 NMR spectrum varied from 2.4 to 3.2 by changing the feed ratio of p-chloromethylstyrene to trehalose. Thermal properties of the resin were analyzed by differential scanning calorimetry (DSC). DSC analysis revealed that the resin DS 2.4 has one exothermal peak at 132degreesC, whereas the resins DS 2.8 and 3.0 have two exothermal peaks. Furthermore, the resin DS 3.2 was found to have only one exothermal peak at 191degreesC. Dynamic mechanical analysis (DMA) and thermomechanical analysis (TMA) revealed that the cured resin has one transition, implying a glass transition. Biodegradability was assayed by the BOD method, and several percent of the cured resin was found to be degraded with activated sludge for 50 days. Further degradation, however, was not observed. (C) 2003 Wiley Periodicals, Inc.