cotton fabric was prepared by grafting polymerization using vinyl-containing polydimethylsiloxane (VPDMS) and octavinyloctasilasesquioxane (VPOSS) as raw materials, and cerium ammonium nitrate (CAN) as initiator.Moreover, thiol/ene click reaction was adopted to introduce long chain alkyl monomers and fluorine-containing monomer onto fabric that had vinyl remained. The chemical structure and morphology of the modified fabric were characterized by infrared spectrometer (FTIR), X-ray photoelectron spectrometer (XPS) and scanning electron microscope (SEM). The results showed that VPDMS and VPOSS were grafted onto fibers successfully, besides, the secondary modification was realized by thiol/ene click reaction. The hydrophobic properties of the modified fabric were characterized by the contact angle measuring instrument. It was found that the contact angle reached 153° when MVPDMS10% and VPOSS were copolymerized, and the contact angle reached 164° after the secondary modification by PFDCMC.Abrasion test, laundering test and acid resistant test were used to test the durability of hydrophobic modification. It was found that PFDCMC secondary modification fabric had the best hydrophobic performance. Furthermore, self-healing property was also observed.