To functionalize polyurethane, a novel synthetic reaction of diol compounds derived from methacrylates with various functional groups was investigated. The methacrylates were reacted with alpha-thioglycerol via a Michael-type addition to obtain the corresponding diol compounds under mild conditions. In this reaction, diisopropylamine was a much better catalyst than triethylamine. The conversion was dependent on the functional group in the methacrylate. The fluoroalkyl group in 2,2,2-trifluoroethyl methacrylate was better than the alkyl group in butyl methacrylate. No reaction was observed in the case of styrene. Using these diol compounds, polyurethanes were prepared by polyaddition with 4,4-diphenylmethane diisocyanate. When the polyurethanes were casted on the substrate, the functional groups influenced surface hydrophilicity and protein adsorption resistance property of the polyurethane significantly. In particular, phosphorylcholine group was the best to reduced protein adsorption. Based on these findings, the variety of these diol compounds synthesized from methacrylates has the potential for use in the production of novel polyurethanes. (C) 2011 Elsevier Ltd. All rights reserved.