Novel Orthodontic Cement Comprising Unique Imidazolium-Based Polymerizable Antibacterial Monomers

White spot lesions (WSLs) can develop quickly and compromise the successful outcome of the orthodontic treatment. Orthodontic bonding cement with the capability to prevent or mitigate WSLs could be beneficial, especially for patients with high risk of caries. This study explored novel mono- and di-imidazolium-based polymerizable antibacterial monomers and evaluated orthodontic cement compositions comprising such novel monomers. Their antibacterial potentials, mechanical properties, and shear bond strength (SBS) to bovine enamel were investigated. Statistical tests were applied to SBS and mechanical tests (one-way ANOVA and Tukey’s test). For antibacterial resins C (ABR-C) and E (ABR-E), their minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against cariogenic Streptococcus mutans bacterial strain UA159 were found to be 4 μg/mL and 8 μg /mL, respectively. The loss of dry mass from completely demineralized dentin beams in buffer solutions pre-dipped into ABR-C and ABR-E resins is much less than that in control buffer (artificial saliva) only. For unfilled resins comprising up to 12 wt % ABR-C, no significant decreases in flexural strength or modulus were observed. For experimental cements incorporating 1–4 wt % ABR-C, there was no drastic compromise to the SBS to enamel except for 3 wt % ABR-C. Furthermore, their SBS was all comparable to the commercially available orthodontic cements. The ISO-22196 antimicrobial test against S. aureus showed significant levels of antibacterial effects—up to over 5 logs of microorganism reduction exhibited by ABR-C-containing experimental cements. The imidazolium-based polymerizable monomers could be utilized to functionalize orthodontic bonding cement with steady antibacterial activity and develop a potential strategy to counteract WSLs.