Synthesis and Properties of Sugar-Based Gemini Surfactants

Abstract

Abstract A series of new gemini surfactants having hydrophilic glucosides were synthesized from glucose via two different synthesis roads, including N,N′-didodecyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl)-p-phthaloyl amide [B(DG)PA], N,N′-didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-2,5-dicarboxylate p-phthaloyl amide [B(DGC)PA], N,N′-didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl) ethylenediamine [B(DG)EA], and N,N′-didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl) hexanediamine [B(DG)HA]. The final products were characterized by IR and NMR spectral measurements and by interfacial tension measurements. The critical micellar concentrations (cmc) of these gemini surfactants were determined to be 2.49 × 10−6, 1.93 × 10−6, 2.47 × 10−6 and 1.66 × 10−6 mol L−1, respectively, which are about one order of magnitude lower than the corresponding monomeric surfactants (GHPDA). The results showed that these synthesized sugar-based gemini surfactants had high abilities to reduce the surface or oil-water interface tension. The high surface activity of these synthesized molecules was attributed to their unique structure where two optimally spaced hydrophobic chains and hydrophilic groups were present.