Synthesis of non-water soluble polymeric guanidine derivatives and application in preparation of antimicrobial regenerated cellulose

Abstract

In order to prepare antimicrobial regenerated cellulose fibers from blended spinning solutions, three non-water soluble polymeric guanidine derivatives, polyhexamethylene guanidine dodecyl benzene sulfonate (PHGDBS), polyhexamethylene guanidine dodecyl sulfate (PHGDSA), and polyhexamethylene guanidine laurylsulfonate (PHGLSO) were synthesized. And the chemical structure of these agents was verified by element analysis, Fourier transform infrared spectroscopy (FTIR), and proton nuclear magnetic resonance (1H-NMR). The antimicrobial activity of the three agents as well as cellulose films containing PHGDBS was also studied. The results showed that the compounds we prepared had strong properties against both bacterial and fungus, including Staphylococcus aureus (S. aureus), Escherichia coli (E. coli), Candida albicans, and Aspergillus niger. Moreover, it was found that three antimicrobial agents were insoluble in water but they can dissolve in solvents of cellulose such as 1-butyl-3-methylimidazolium chloride ([BMIM]Cl) and N-methylmorpholine-N-oxide monohydrate (NMMO·H2O). Meanwhile, it was also proved that [BMIM]Cl had little effect on the antimicrobial properties of these agents. The cellulose films containing only 1.0 wt% PHGDBS showed 99.94 % and 96.95 % bacterial reduction rates for S. aureus and E. coli, respectively. Moreover, still over 91 % of bacterial reduction was maintained after 15 laundering cycles. It suggests that the three agents will be suitable to prepare antimicrobial regenerated cellulose fibers or films.