Adsorption of Novel Alkylaminoamide Sugar Surfactants at Tailor‐made Surfaces

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Abstract
N,N‐di(3‐aminopropyl)dodecylamine (C12‐Y‐amine), N‐dodecyl‐N,N‐di[(3‐d‐gluconylamido)propyl]amine (C12‐DGA), N‐dodecyl‐N,N‐bis[(3‐lactobionylamido)propyl]amine (C12‐DLA), N‐dodecyl‐N‐[(3‐lactobionylamido)propyl]amine (C12‐LA), and ethoxylated N,N‐di(3‐aminopropyl)dodecylamine [C12‐Y‐amine with 4 and 8 ethylene oxide (EO)] have been synthesized, and their physical‐chemical properties have been studied. Adsorption was measured at the air–water interface by the du Noüy ring method and at solid surfaces consisting of self‐assembled monolayers (SAMs) of alkanethiols on gold using surface plasmon resonance. Results from surface tension measurements showed that adsorption at the air–water interface is pH dependent. At low pH, reduction in surface tension is less pronounced as a result of protonation of the amino groups of the surfactants. At the SAM model surfaces, generated by adsorption of alkanethiols or mixtures of alkanethiols on gold presenting methyl, hydroxyl, and carboxyl groups, the highest amount of adsorbed surfactant was obtained on a surface composed of a mixture of methyl and carboxyl groups. In general, the sugar‐derived surfactants, DGA, DLA, and LA, adsorbed less than the ethoxylates. Surfactant biodegradation was investigated by the closed bottle test. Only C12‐Y‐amine was found to be readily biodegradable. However, the polyol surfactants were more biodegradable than the ethoxylates.
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  • University of Wyoming

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