The development of compounds with dual or multi-functions or activities is being paid attention in the scientific community. Herein, two series of phthalimide-containing copolymers were synthesized and structurally characterized and their potency against selected microbial strains was evaluated. Our study mainly focused on evaluating both the antimicrobial and surface activities of new corresponding polymeric cationic surfactants for removing petroleum thin films with their increased dispersing capacity. The synthesis process includes the formation of N-methacryloyloxytetrachlorophthalimide monomer, homopolymerization, and exchange reactions with various amino-and hydroxy-compounds for the synthesis of copolymers. Lastly, polymeric surfactants were obtained via the quaternization of some copolymers with dimethyl sulfate. Among the tested derivatives, compounds 5a, 5b, 6c, 6d, and 7b showed higher