Synthesis and properties of double epoxy groups double quaternary ammonium salts

Double epoxy group double quaternary ammonium salts (DEpDQAS) were synthesized by epichlorohydrin (ECH) reacting with N,N,N'N'-tetramethylethylenediamine (TMEDA) and N,N,N'N'-tetramethyl-1,6-hexanediamine (TMHDA), respectively. The results of orthogonal experiments showed that temperature and time were the key factors influencing on epoxy value and quaternarization ratio respectively. The optimal condition for higher epoxy value was the reaction temperature at 15 °C and methanol as solvent. The reaction kinetic process was determined by conductivity, which showed that the reaction had a short induction period and appeared discontinuity in progress that the reaction rate of the first stage was almost constant, while the reaction rate of the second stage decreased gradually. The product was characterized by infrared spectroscopy (FTIR) and nuclear magnetic resonance (1H NMR). The results of surface tension testing showed that DEpDQAS-6 with longer spacer chain had better surface activity and lowered the solution surface tension to 26 mN·m−1 at 25 °C and CMC 0.27 mol·L−1. The thermodynamic parameters of micellization were obtained basing on charged pseudo-phase model. The studies of cytotoxicity in vitro and antibacterial activity showed that DEpDQAS was biocompatible and its antibacterial activity was more effective against Escherichia coli than against Staphylococcus aureus.