A new halo-ester diol has been synthesized by esterification reaction of trichloroacetic acid and pentaerythritol by using p-Toluenesulfonic acid as a catalyst. The synthesized diol was reacted with isophorone diisocyanates, polyester polyol, di-methylol propionic acid to form polyurethane dispersion. The antimicrobial properties of polyurethane dispersions were evaluated against Gram-negative E. coli and Gram-positive bacteria L. plantarum by Kirby-Bauer test. The structure of the diol was examined using Fourier transform infrared spectroscopy, H-1 nuclear magnetic resonance and mass spectroscopy. The physical, chemical and thermal properties such as viscosity, particle size, chemical resistance and DSC, XRD, SEM and GPC of polyurethane dispersion were evaluated. The significant effect of diol and its chain length, particle size and zeta potential properties of resulting polyurethane dispersion were investigated.