Ibuprofen-linked 2-hydroxypropyl acrylate, a new acrylic derivative of ibuprofen in which the drug is separated from the polymerizable double bond by two hydrolytically labile ester bonds, was directly synthesized from the reaction between 2-hydroxypropyl acrylate and ibuprofen. This drug containing monomer was easily homo-polymerized by free radical polymerization. The characterization of the resulting products by nuclear magnetic resonance (NMR), size exclusion chromatography (SEC), Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) indicated that the polymeric prodrugs were successfully synthesized. In addition, the flexible acrylate backbone provides the polymers low-glass transition temperatures and in consequence good processability. Ibuprofen release from the polymer was preliminary evaluated at different pH conditions to show the capacity of these compounds to release the drug under hydrolytic conditions. (C) 2010 Wiley Periodicals, Inc. J Appl Polym Sci 117: 3271-3276, 2010