Adsorption behavior of surface-chemically pure N-alkyl-N-(2-hydroxyethyl)aldonamides at the air/water interface.

N-alkyl-N-(2-hydroxyethyl)aldonamides (alkyl: n-C6H13, n-C8H17, n-C10H21, n-C12H25, and n-C14H29) were obtained in the reaction of long-chain N-alkyl-N-(2-hydroxyethyl)amines with D-glucono-1,5-lactone and D-glucoheptono-1,4-lactone. The adsorption isotherms were obtained from surface tension measurements of aqueous solutions of surface-chemically pure surfactants. The experimental equilibrium surface tension versus concentration isotherms were evaluated by the Frumkin adsorption equation to get the adsorption parameters, namely, standard free energy of adsorption, deltaG(o)ad, saturation adsorption, gammainfinity minimum surface area demand per molecule adsorbed, Amin, and interaction parameter, Hs. The investigated functionalized alkylaldonamides show improved solubility in comparison with the corresponding sugar derivatives of the primary amines. The introduction of the -CHOH moiety into the saccharide headgroup causes a noticeable increase of the hydrophobic character of surfactant. The minimum surface area demand, Amin, is slightly greater for glucoheptonamides than for the corresponding gluconamides. The practically constant Amin value within the homologue series of the aldonamides indicates that the obtuse hydroxyethyl residue is the determining factor for the arrangement of the adsorbed surfactants in the interfacial layer.