Synthesis and physicochemical properties of bolaamphiphiles from dimeric acid

Abstract

The physicochemical behaviour of bolaamphiphile derivatives with an anionic, a cationic, or a non-ionic polar group and their mixtures is studied mainly by surface tension measurements, quasi-elastic light-scattering studies, 1H NMR spectroscopy, and surface monolayers. Bolaamphiphiles are synthesized by classical methods from a non-expensive mixture of α,ω-dicarboxylic acids, obtained by thermal Diels–Alder type cyclization of methyl 10-E,12-E linoleate, obtained from tall oil. The anionic and cationic bolaamphiphiles synthesized are water soluble and form stable monolayers when they are compressed. The anionic and the cationic bolaamphiphiles with an iodide atom as counter-anion show a behaviour between liquid-condensed and liquid-expanded. The other synthesized cationic bolaamphiphiles and the (1:1) mixtures of anionic–cationic bolaamphiphiles behave as liquid-condensed.