Preparation of the Resins Containing Phosphonium Residues from Glycidyl Methacrylate- 1, 4-Divinylbenzene Copolymer Beads and Antibacterial Activity of the Resins

Abstract

Copolymer beads having 2-chloro-3-hydroxypropyl group (RCG) were prepared by treating macroreticular glycidyl methacrylate (GMA)- 1, 4-divinylbenzene (DVB) copolymer beads (RG) with hydrogen chloride. RCG-TEP, RCG-TBP, and RCG-TOP were prepared by treating RCG with triethylphosphine (TEP), tributylphosphine (TBP), trioctylphosphine (TOP), respectively. Decyldimethylphosphine (DMDP) dodecyldimethylphosphine (DMDDP), tetradecyldimethylphosphine (DMTDP), and hexadecyldimethylphosphine (DMHDP) were used as alkyldimethylphosphines which had an alkyl group with different length. Tris (3-aminopropyl) phosphine (TAPP) and tris (3-hydroxypropyl)phosphine (THPP) were also used as phosphines. The antibacterial activity was examined against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). Antibacterial activity was evaluated by measuring the decrease in the number of viable cells in the bacteria suspension after contacting with the resins for prescribed time.
RCG-TOP exhibite d high antibacterial activity against E. coli and S. aureus in water, however RCGTEP and RCG-TBP did not. RCG-TAPP had high antibacterial activity, while RCG-THPP did not. All the resins which were made by treating RCG with alkyldimethylphosphines described above had high antibacterial activity for bacteria. The resins which exhibited high antibacterial activity had high adsorption ability for anionic compounds such as dodecylbenzensulfonic acid. These results indicate that the antibacterial activity of the resins against bacteria was not only affected by the amount of phosphonium introduced but also the length of alkyl groups and functional groups in the phosphonium residues.