To evaluate the properties of novel hydrolytic resistant antibacterial monomers and to determine the properties of resin adhesives containing these monomers. Methacrylamide-based QAC (Quaternary Ammonium Compound) monomers, 1-(11-Methacryla-midoundecyl)pyridine-1-ium bromide (MAUPB) and 1-(12-Methacryl-amidododecyl)pyridine-1-ium bromide (MADPB), and their methacrylate-derivatives, N-(1-Methacryloylundecanyl)pyridinium bromide (MUPB) and N-(1-Methacryloyldodecanyl)pyridinium bromide (MDPB), were synthesized and characterized. The minimum inhibitory (MIC) and bactericidal (MBC) concentrations were determined against S.mutans and E.faecalis. Cytotoxicity of unpolymerized monomers were evaluated using L-929 and MDPC-23. Each monomer was incorporated into experimental resins (BisGMA/TEGDMA/CQ/EDMAB or BisGMA/HEMA/CQ/EDMAB) at 10wt%. FTIR Spectra were collected for degree of conversion (DC%) measurement. Bacterial attachment on resin disks were determined by fluorescent microscope. Mechanical properties of experimental resins were evaluated by flexural strength & modulus and shear bond strength testing. The antibacterial activity of MDPB≥MUPB>MADPB>MAUPB. The TC50 of MAUPB> MADPB>MUPB >MDPB. Incorporation of MAUPB in BisGMA/TEGDMA-based resin, had no significant effect on DC%, while significantly increase DC% in BisGMA/HEMA-based Resin. MUPB and MAUPB containing resins showed less viable bacterial attachment than pure resins. After 3-month storage, resins containing MAUPB illustrated higher flexural strength than their corresponding resins containing MUPB. BisGMA/HEMA-based resin containing MAUPB illustrated significantly higher resin-dentin shear bond strength than that of MUPB and pure resin. Methacrylamide monomer containing QAC, MAUPB, possessed antibacterial properties and superior physical and mechanical properties when incorporated in resin adhesives as compared to their corresponding methacrylate monomer, MUPB. Methacrylamide-based QAC monomers are potentially used to formulate antibacterial hydrolytic resistant resin adhesives and enhance resin-dentin bond strength.