SYNTHESIS AND SURFACE-ACTIVE AND ANTIMICR OBIAL PROPERTIES OF N-(2-[2-(ALKYLAMINO)ETHYL] AMINOETHYL)GLYCINE TRIHYDROCHLORIDES

The title compounds, R - (NHCH2CH2)2-NHCH2COOH . 3 HCl ([1]; R = n-C10 H21-, n-C12H25-, n-C14 H29-, and n-C16H33), were prepared by the react ion of the corresponding N-alkyl-N'-(2-aminoethyl)-1,2-ethanediamines with sodium chloroacetate (60-degrees-C, 4 h) in a mixture of water-me thanol (1:1 v/v) while the pH value of the reaction mixture being main tained between 9-10. Compounds [1] . 3 HCl were a colorless crystallin e substance with definite melting points, and soluble in water and eth anol, and insoluble in acetone, chloroform, ether, ethyl acetate, benz ene, and hexane. The critical micelle concentrations (CMC) for [1] . 3 HCl were determined at 30-degrees-C by the surface tension method and the electric conductivity measurement. The surface-active and antimic robial properties of [1] . 3 HCl were also evaluated. The trihydrochlo rides [1] . 3 HCl were found to be surface-active compounds. Thus, the dodecyl C12-, tetradecyl C14-, and hexadecyl derivatives C16-[1] . 3 HCl reduced surface tension to 29.9-33.7 dyn/cm at their CMCs (5.6, 4. 3, and 4.0 mmol/l, respectively); C12-, C14-, and C16-[1] . 3 HCl show ed a foaming ability and a solubilizing power which were comparable or superior to sodium dodecyl sulfate (SDS) and sodium dodecylbenzenesul fonate (DBS). C12- and C14-[1] . 3 HCl showed a good antibacterial act ivity against Escherichia coli HUT 8047 and Staphylococcus aureus HUT 8051, and C14-[1] . 3 HCl possessed a good antifungal activity against Aspergillus oryzae HUT 2061.