Synthesis and characterization of the epoxy-functionalized quaternary ammonium chloride

A kind of surface active epoxy-functionalized quaternary ammonium salt, N,N-dimethyl-N-dodecyl-N-(1,2-epoxy propyl) ammonium chloride (DDEAC), was synthesized. The surface activity and aggregation behavior were investigated by surface tension, dynamic light scattering, conductivity, steady state fluorescence measurements and by molecular dynamics simulations. As a control, the surface properties of dodecyl trimethyl ammonium chloride (DTAC) were also studied. Compared to DTAC, DDEAC showed higher surface activity and more ready aggregation formation as well as larger Ca2+ and Na+ tolerance. The data from molecular dynamics simulations showed that the DDEAC hydrated more easily than DTAC. The conductivity results indicated that the micellization of DDEAC is enthalpy-driven, however that of DTAC is enthalpy-driven only at temperatures higher than 25 degrees C and entropy-driven at temperatures lower than 25 degrees C. The reaction between DDEAC and chitosan implied that DDEAC could endow chitosan both hydrophilicity and hydrophobicity by one step reaction method and expand the application of chitosan. (C) 2016 Elsevier B.V. All rights reserved.