Fast-Acting Antibacterial, Self-Deactivating Polyionene Esters

Biocidal compounds that quickly kill bacterial cells and are then deactivated in the surrounding without causing environmental problems are of great current interest. Here, we present new biodegradable antibacterial polymers based on polyionenes with inserted ester functions (PBI esters). The polymers are prepared by polycondensation reaction of 1,4-dibromobutene and different tertiary diaminodiesters. The resulting PBI esters are antibacterially active against a wide range of bacterial strains and were found to quickly kill these cells within 1 to 10 min. Because of hydrolysis of the ester groups, the PBI esters are degraded and deactivated in aqueous media. The degradation rate depends on the backbone structure and the pH. The structure of the polymers also controls the deactivation mechanism. While the more hydrophilic polymers require hydrolyses of only 19 to 30% of the ester groups to become practically inactive, the more hydrophobic PBI esters require up to 85% hydrolysis to achieve the same result. Thus, depending on the environmental conditions and the chemical nature, the PBI esters can be active for only 20 min or for at least one week.