Surface and micellar properties of new nonionic gemini aldonamide-type surfactants.

A new group of gemini aldonamide-type surfactants-N,N'-bisalkyl-N,N'-bis[(3-gluconylamide)propyl]ethylenediamines, N,N'-bisdodecyl-N,N'-bis[(3-glucoheptonylamide)propyl]ethylenediamine, and N,N'-bisalkyl-N,N'-bis[(3-lactobionylamide)propyl]ethylenediamines, (alkyl: n-C(8)H(17), n-C(12)H(25)), were synthesized and characterized. The surface properties, such as surface excess concentration, Gamma(cmc), surface area demand per molecule, A(min), efficiency in surface tension reduction, pC(20), the effectiveness of surface tension reduction, gamma(cmc), critical micelle concentration, cmc, and a measure of the tendency of the surfactant to adsorb at the aqueous/air interface relative to its tendency to form micelles in the bulk surfactant solution, cmc/C(20), and standard free energy of micellization, DeltaG(mic)(0), have been obtained by means of surface tension measurements. The standard fluorescence shift technique using PRODAN as a probe provide confirmation of the cmc values by an alternative method. Additionally, the micellar properties for the concentration near above the cmc have been characterized by the aggregation number, N(agg). The presence of the dimeric segments with the aldonamide hydrophilic units in the surfactant molecule is found to be the source of their unusual physicochemical behavior. They are very efficient at adsorbing at the free surface and at forming micelles in water. Their critical micelle concentration values are remarkably low. They reveal remarkably low A(min) values in relation to conventional nonionic surfactants, which is unexpected from the molecular dimensions for the molecule but which is possible if one assumes some type of multilayer structure or a coherent interfacial film.