Studies of N-Dodecyllactobionamide, Maltose 6‘-O-Dodecanoate, and Octyl-β-glucoside with Surface Tension, Surface Force, and Wetting Techniques

Abstract

Three different types of sugar surfactants, octyl-β-glucoside, maltose 6′-O-dodecanoate, and Ndodecyllactobionamide have been investigated to examine the effect of the structure of the sugar headgroup on the adsorption to liquid/vapor and solid/liquid interfaces using a number of techniques (surface tension, surface force apparatus, MASIF, and wetting). It was found that all the surfactants form monolayers when adsorbed to a hydrophobic interface at high concentrations. Increased headgroup flexibility leads to the adsorption of higher amounts on both the liquid/vapor and solid/liquid interfaces, resulting in a higher van der Waals attraction between two such monolayers. Increased hydrogen bonding within layers of more flexible surfactants is suggested to explain this difference. The most flexible surfactant, N-dodecyllactobionamide, is the least efficient wetting agent with the highest γSL. The behavior of the receding contact angles indicates the importance of intralayer hydrogen bonds between larger and more flexible sugar headgroups. LA001309Z

Synthesis, preliminary characterization, and application of novel surfactants from highly branched xyloglucan oligosaccharides

“…CMC values obtained from the break-points of the surface tension isotherms (estimated as the intersection of lines fitted to the descending and flat portions of the curves) were in good agreement with those obtained by the dye-inclusion method (Table I). The minimum surface tension, γ min , was in the range 47-53 mN/m, which is remarkably high compared to many sugar-based surfactants (Augé and LubinGermain, 2000;Ericsson et al, 2004;Ferrer et al, 2002;Garofalakis et al, 2000;Kjellin et al, 2001;Persson et al, 2000;Söderberg et al, 1995;Waltermo et al, 1996). An anomalously high γ min value can result when the Krafft point of the surfactant is passed at high concentration, which effectively results in the precipitation of the surfactant from solution.…”

“…where N A is Avogadro's number Garofalakis et al, 2000;Kjellin et al, 2001;Söderberg et al, 1995). The standard free energy of micellization was calculated from CMCs determined by the dye-inclusion method using the relationship (Augé and Lubin-Germain, 2000;Eastoe et al, 1996) ∆G mic = RT ln(CMC/55.5)…”

“…In particular, recent fundamental studies have sought to elucidate the behavior of the simple alkylglucosides in the context of other well-characterized nonionic surfactants, namely, those based on poly(ethene oxide) head groups (Ericsson et al, 2004). Interest in surfactants derived from sugars other than glucose has been extended to include other monosaccharides, as well as linear di-, tri-, and tetrasaccharides (Costes et al, 1995;Ferrer et al, 2002;Garofalakis et al, 2000;Kjellin et al, 2001;Plou et al, 2002;Söderberg et al, 1995). The use of branched oligosaccharide head groups has been little explored, presumably due to the difficulties associated with isolating or synthesizing pure compounds.…”

Surfactant Properties of Enzymatically Synthesized Monolauroyl Disaccharides

“…The maximum solubilizing capacity was estimated from the intersection of the two lines drawn at the low and high concentrations. Figure 4 shows the concentration of octanoic acid solubilized into the micelle at the various surfactant (monolauroyl disaccharide) concentrations for the four monolauroyl di- (Ferrer et al, 2002) and 0.33 mmol/L at 22℃ (Kjellin et al, 2001), and those of the monolauroyl sucrose were 0.45 mmol/L at 20℃ (Söderberg et al, 1995), 0.25 mmol/L at 25℃ (Ferrer et al, 2002), and 0.21 mmol/L at 32℃ (Garofalakis et al, 2000). The CMC values of the monolauroyl disaccharides synthesized in this study were almost the same as the reported ones.…”

“…Fatty acid esters of other di-, monoand trisaccharides have also been shown to be surface active (Söderberg et al, 1995;Garofalakis et al, 2000;Kjellin et al, 2001;Douglas and Tao, 2002;Ferrer et al, 2002;Zhang et al, 2003;Chen et al, 2005;Chen et al, 2007;Piao et al, 2007;Sun et al, 2009). Recently, enzymatic synthesis in organic solvents has attracted attention as an alternative to conventional chemical synthesis of esters (Carrea and Riva, 2000).…”