A series of hydroxy terminated polybutadiene (HTPB) based polyurethane elastomers (PUEs) were synthesized by using tolylene diisocyanate via prepolymer methodology. The chains of prepolymers were extended with aliphatic diols (ethane-1,2-diol, propane-1,3-diol, butane-1,4- diol, pentane-1,5-diol and hexane-1,6-diol). The final polyurethane elastomers were analyzed by using fourier transformed infrared spectroscopy while solubility, contact angle measurement and evaluation of water absorption percentage (%) were executed to analyze the surface as well as the nature of polymers. Spectroscopic study confirmed the synthesis of polyurethane elastomers while surface characterization and solubility revealed that these polymers were hydrophobic and crosslinked. Furthermore, their hydrophobicity was depended on the number of methylene units of aliphatic alkane diols.