A urethane methacrylate (UMA) with a cyclohexyl terminal group, 2-((cyclohexylcarbamoyl)oxy)ethyl methacrylate (CEM), were incorporated in a series of homogeneous and two-phase acrylic latexes. All synthetic latexes were prepared by semi -batch emulsion polymerization. The effect of CEM content on latex performance was investigated. The latexes and corresponding films were characterized using minimum film formation temperature (MFFT) tester, differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), tensile tests and Fourier transform infrared spectroscopy (FTIR). The increasing CEM content led to the improvement in performances including Young ' s modulus and hydrogen bonding strength. In addition, another series of homogeneous acrylic latexes that contained increasing content of UMA with a methyl terminal group, 2-((methylcarbamoyl)oxy)ethyl methacrylate (MEM), was also included to investigate the effect of terminal group bulkiness. The bulkiness of the terminal group appeared to lead to a more substantial increase in Young ' s modulus compared to hydrogen bonding.