N-acyloxyethylcarboxybetaine 형 양성계면활성제의 합성과 물성에 관한 연구

A Study on the Synthesis and Physical Properties of N-acyloxyethyl carboxybetaine Type Amphoteric Surfactants

Five novel amphoteric surfactants of N-acyloxyethylcarboxybetaine series were synthesized via Schotten-Baumman reaction between five acid chlorides containing 10, 12, 14, 16 and 18 carbon atoms in their N-alkyl groups and dimethylaminoethanol to give the intermediate products, 2-dimethylaminoethylalkanoates(2). Quaternization of these products(2) was permitted to from 2-(acyloxyethyldimethylammonic)- acetates(3), whose structures were identified by elemental analysis, IR spectrophotometry and ¹Hnmr spectrometry. The yield of the final products was shown in the range of 77-80% based on the intermediate products. The surface tension of the aqueous solution of (3) was measured, and the critical micelle concentrations (cmc) were shown in the range of 2.1×10×⁻³-3.3×10⁻⁴mol/l, and the surface tension at cmc was 28-36 dyne/cm. Cmc was lowered gradually by the increment of the length of N-alkyl ester containing group. The isoelectric point was shown in the range of 4.44-5.20. It showed a tendency to lean toward the acidic site and its range was broadened as increase of the hydrophobic group length. A linear relationship between log cmc and the number of carbon atoms(N) in the hydrophobic alkyl chain was shown in the relative equation of log cmc=-1.75-0.1N, and the contribution rate of N on the standard free energy change in micellization, Δ(ΔG°m)/ΔN, was calculated as -0.23 RT.