Antibacterial agent N-halamine, 7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5]-decane-2,4-dione (TTDD), was synthesized, and it was added into the polyvinyl chloride (PVC) nanoweb. A versatile, and relatively simple method, electrospinning, was used to fabricate continuous and uniform nanowebs. 7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5]-decane-2,4-dione (TTDD) is a cyclic N-halamine that can be chlorinated easily due to three functional groups (imide, amide, and amine). Therefore, TTDD was preferred for PVC regarding having high stability, non-toxic, non-irritant for skin, and renewable. The rechargeable chlorination process was applied to webs using dilute hypochlorite solution. The antibacterial activity of the webs were evaluated using the ASTM 2149 procedure. FTIR, TGA, and SEM were used to investigate the morphology, thermal characteristics, and chemical structures of PVC webs. Scanning electron microscopy (SEM) displayed that the average diameter of the fibers increased with TTDD concentration. The thermal properties of the PVC webs did not changed significantly. All chlorinated webs indicated highly effective antibacterial activities against both Staphylococcus aureus and Escherichia coli with increased inactivation. Furthermore, the antibacterial efficacy of nanowebs is reformed again by the rechargeable process. The rechargeable chlorination capacity of obtained PVC non-wovens is over > 60% (within 6 hours, in pH 5), for four rechargeable chlorine cycles. The new antibacterial PVC nanowebs have the potential for especially useful in medical applications.