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Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group
DIFAR—Department of Pharmacy, University of Genoa, Viale Cembrano 4, 16147 Genoa, Italy
STEBICEF—Department of Biologic, Chemical and Pharmaceutical Science and Technology, University of Palermo, Viale delle Scienze, P.co d'Orleans II, Pad. 17-I90128 Palermo, Italy
Centro Grandi Apparecchiature-UniNetLab, University of Palermo, Via F. Marini, 14-I90128 Palermo, Italy
* Author to whom correspondence should be addressed.
Received: 1 February 2013; in revised form: 16 March 2013 / Accepted: 1 April 2013 / Published: 12 April 2013
Abstract: A series of new gemini surfactants without a spacer group, disodium 2,3-dialkyl-1,2,3,4-butanetetracarboxylates, were synthesized in a green chemistry context minimizing the use of organic solvents and applying microwaves (MW) when activation energy was required. Once the desired architecture was confirmed by means of the nuclear magnetic resonance technique (1H-NMR, 1H-1H COSY) for all the studied surfactants, the critical micellization concentration was determined by conductance measurements. The diffusion coefficient of micelles formed by the four compounds was characterized using pulsed field gradient (PFG)-NMR. Diffusion coefficients were found to be dependent on the concentration and on the number of carbon atoms in the alkyl chain. The absence of the spacer group, peculiar to this new series of gemini surfactants, may confer relatively low flexibility to the molecules, with potential implications on the interfacial properties, namely on micellization. These gemini surfactants might have interesting applications in the preparation of composite materials, in nanotechnology, in gene transfection and mainly, due to the low CMCs, as new interesting ingredients of cosmetics and toiletries.
Keywords: gemini surfactants; green synthesis; microwave; cosmetic detergents; critical micelle concentration; PFG-NMR; diffusion coefficient
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MDPI and ACS Style
Villa, C.; Baldassari, S.; Martino, D.F.C.; Spinella, A.; Caponetti, E. Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group. Materials 2013, 6, 1506-1519.
Villa C, Baldassari S, Martino DFC, Spinella A, Caponetti E. Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group. Materials. 2013; 6(4):1506-1519.
Villa, Carla; Baldassari, Sara; Martino, Delia F.C.; Spinella, Alberto; Caponetti, Eugenio. 2013. "Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group." Materials 6, no. 4: 1506-1519.