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.
Kurzfassung
Eine Reihe von neuen Gemini-Tensiden mit hydrophilen Glycosiden wurde auf zwei verschiedenen Wegen aus Glukose synthetisiert, dazu gehören N,N′-Didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-p-phthaloylamid [B(DG)PA], N,N′Didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-2,5-dicarboxylat-p-phthaloylamid [B(DGC)PA], N,N′-Didodecanoyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)ethylendiamin [B(DG)EA] und N,N′-Didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl)hexandiamin [B(DG)HA]. Die Endprodukte wurden durch IR- und NMR-Spektralmessungen sowie Messungen der Grenzflächenspannung charakterisiert. Die kritischen Mizellbildungskonzentrationen (cmc) dieser Gemini-Tenside wurden zu 2,49 × 10−6, 1,93 × 10−6, 2,47 × 10−6 und 1,66 × 10−6 mol L−1 bestimmt, die jeweils eine Größenordnung niedriger sind als die entsprechenden monomeren Tenside (GHPDA). Die Ergebnisse zeigen, dass diese zuckerbasierten Gemini-Tenside ein hohes Vermögen zur Reduzierung der Oberflächen- oder Öl-Wasser-Grenzflächenspannung besitzen. Die hohe Oberflächenaktivität dieser synthetisierten Moleküle ist auf die vorliegende einzigartige Struktur, mit zwei räumlich optimierten hydrophoben Ketten und hydrophilen Gruppen, zurückzuführen.
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