Rosin-based Quaternary Ammonium Salt Synthesis And Antibacterial Activity

Rosin is an important natural resource of China.All kinds of resin acids are the main components of it,which have been put on more and more attention for their special chemical structures and wide range of biological activities.Four types of quarternary ammoniums based on rosin were prepared by rosin or sodium rosinate.The N-(4-abietoxymethyl)benzyl-N,N,N-trimethylammonium chloride and N-(4-a bietoxymethyl)benzyl-N,N,N-trimethylammonium chloride were synthesized for the first time,and also are the innovation point of this paper.In addition,several intermediates were syntheisized,which can provide new ways to obtain quarternary ammoniums.Finally,the antibacterial activity of them was preliminarily studied.The N-(3-abietoxy-2-hydroxy)propyl-N,N,N-triethylammonium chloride was obtained by two ways.One of them is new and has some advantages.N-(4-abietoxymethyl)benzyl-N,N,N-trimethylammonium chloride and N-(4-abietoxy methyl)benzyl-N,N,N-trimethylammonium chloride and their intermediates were successfully prepared.Effects of various factors to the reaction of the former's intermediate were optimized by the single factor experiments.The optimal reaction conditions are as follows: the molar radio of 1,4-bis(chloromethyl)benzene to triethylamine is 1.5∶1,the solvent ethanol content is 60%(mass fraction),the triethylamine's dropping time isn't less than 10 min,the reaction time is 6 h,the temperature is 65℃,and the conversion rate can reach 62.7%。By the filter-paper method,the antibacterial activities of the quartemary ammonium based on rosin were inverstigated.Escherichia coli and aspergillus niger were selected in this experiment.It has been found that all of them show high antibacterial activity,and even the activity of N-(4-abietoxymethyl)benzyl-N,N,N-trimethylammonium chloride is higher than the benzalkonium bromide's activity.