This study is concerned with preparation of chlorine resistant (CR) thin layer composite (TFC) membranes. The novel method for making CR membranes from commercially available RO membranes is based on sol-gel condensation of trialkoxyalkylsilane derivatives. The silane coupling agents used in this study have different number of alkyl carbon chain group (methyltriethoxysilane; METES and octyltriethoxysilane; OCTES). The OCTES composite membranes have a significant tolerance to chlorine compared to commercial polyamide RO membrane or METES composite membranes. The surface properties of membranes were examined to explain a significant difference of chlorine tolerance between OCTES composite membrane and the other two membranes. In this study, we tried several surface analyses to explain difference of chlorine tolerance. The element composition results of surface analysis by EDX confirmed that both silane fixed on polyamide firmly, The surface roughness and contact angle results showed long chain alkyl group of OCTES enhancing hydrophobicity considerably than METES. The hydrophobicity plays an important role in chlorine resistance of membrane.