The synthesis of a series of radiation-curable poly(urethane methacrylate) oligomers are reported, which, on exposure to electron-beam irradiation, result in adhesive films with pressure-sensitive properties. Variation of the chain terminator component of the formulation and the effect of this on adhesive properties were investigated. Adhesive systems utilizing Dowfax 9N6 nonylphenolethoxylate, 1-(2-hydroxyethyl)-2-pyrrolidinone, 2-hydroxyethyl salicylate, or 4-(2-hydroxyethyl)morpholine as alternative chain terminators performed in a manner that may make them suitable for medical applications. Terminators with higher ethoxylation levels (Brij 35, 58) conferred high hydrophilicity on the resulting adhesives.