Novel methacrylate and acrylate monomers having an isothiocyanate structure, 2-isothiocyanatoethyl methacrylate (ITEMA) and 2-isothiocyanatoethyl acrylate (ITEA), were synthesized, and their radical polymerizations were examined, respectively. ITEMA and ITEA were synthesized by addition of carbon disulfide to 2-aminoethyl methacryrate or 2-aminoethyl acrylate, followed by treatment with ethyl chloroformate. Radical polymerizations of the obtained monomers (ITEMA, ITEA) were carried out methyl ethyl ketone using 2,2'-azobisisobutyronitrile (AIBN) as an initiator to obtain the corresponding polymers. The glass transition temperatures of the poly-ITEMA and poly-ITEA were determined to be 55 and 2 degrees C by differential scanning calorimetry, respectively. The 5 wt % decomposition temperatures of the poly-ITEMA and poly-ITEA were determined to be 277 and 269 degrees C by thermogravimetric analysis, respectively. Isothiocyanato groups in the monomers did not react with water in acetone solution at 60 degrees C for 24 h to be tolerable to water. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4522-4529