Solution properties and emulsifcation properties of amino acid-based gemini surfactants derived from cysteine

Abstract

Amino acid-based anionic gemini surfactants (2CndiCys, where n represents an alkyl chain with a length of 10, 12, or 14 carbons and "di" and "Cys" indicate adipoyl and cysteine, respectively) were synthesized using the amino acid cysteine. Biodegradability, equilibrium surface tension, and dynamic light scattering were used to characterize the properties of gemini surfactants. Additionally, the effects of alkyl chain length, number of chains, and structure on these properties were evaluated by comparing previously reported gemini surfactants derived from cystine (2CnCys) and monomeric surfactants (CnCys). 2CndiCys shows relatively higher biodegradability than does CnCys and previously reported sugar-based gemini surfactants. Both critical micelle concentration (CMC) and surface tension decrease when alkyl chain length is increased from 10 to 12, while a further increase in chain length to 14 results in increased CMC and surface tension. This indicates that long-chain gemini surfactants have a decreased aggregation tendency due to the steric hindrance of the bulky spacer as well as premicelle formation at concentrations below the CMC and are poorly packed at the air/water interface. Formation of micelles (measuring 2 to 5 nm in solution) from 2CndiCys shows no dependence on alkyl chain length. Further, shaking the mixtures of aqueous 2CndiCys surfactant solutions and squalane results in the formation of oil-in-water type emulsions. The highly stable emulsions are formed using 2C12diCys or 2C14diCys solution and squalane in a 1:1 or 2:1 volume ratio. © 2013 by Japan Oil Chemists' Society.