Covalent attachment of quaternary ammonium compounds to a polyethylene surface via a hydrolyzable ester linkage: Basis for a controlled‐release system of antiseptics from an inert surface

Abstract

AbstractThe colonization of medical devices such as catheters, topical wound dressings, and surgical implants by micro‐organisms is an ongoing problem, particularly as many strains of bacteria are becoming resistant to antibiotics. Such a problem may be addressed by a material surface that is able to provide a slow release of a disinfectant during its period of usage. To achieve this objective, a novel material was prepared in which a quaternary ammonium salt was covalently bound onto a polyethylene backbone via a hydrolyzable ester linkage, which provided a slow release of the disinfecting agent. A low‐density polyethylene film was treated with glow discharge followed by the graft polymerization of acrylic acid. A tertiary amine function was introduced onto the film by the esterification of the carboxylic acid groups, via an acid chloride intermediate, with 4‐hydroxy‐N‐methyl piperidine. The tertiary amine on the piperidine was then quaternized with a series of alkyl bromides of various chain lengths. The quaternary ammonium salt was released slowly by the hydrolysis of the ester bond over a 4‐h period. To test the efficacy of the quaternary ammonium function itself, soluble compounds were prepared as follows. 4‐Hydroxy‐N‐methyl piperidine was esterified with acetic anhydride and a corresponding series of quaternary ammonium salts prepared again by a reaction with alkyl bromides of various chain lengths. A preliminary microbiological survey of the materials included an investigation of the effect of the chain length as well as the efficacy of the soluble quaternary salts themselves. As expected, only the longer alkyl chains provided quaternary ammonium salts with bactericidal properties, chain lengths of less than 10 carbon atoms proving ineffective. Both the polymer‐bound and soluble long‐chain quaternary ammonium salts were effective against suspensions of Staphylococcus aureus and Escherichia coli. The results therefore indicate that such a system may well be useful in the development of biomedical materials such as surgical implants or dressings in which a slow release of a disinfectant or other physiologically active agent such as an anti‐inflammatory drug may be required. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 538–545, 2006