Another new family of "extended" glucidoamphiphiles. Synthesis and surfactant properties for different sugar head groups and spacer arm lengths

Abstract

Following a new four-step route, we prepared a family of "extended" glucidoamphiphiles from D-glucose, D-galactose, and xylitol in which the n-dodecyl chain is attached to the glucidic moiety by the linkage Z = O-Et-O-Et-O-(α-PP-O-)n' where -O-(α-PP-O-)n is a poly-(α-propyloxy) commercial oligomeric mixture (with average length n = 6, 10, and 14). This amphiphilic behavior study showed that (i) the glucose derivative exhibits water solubility and hydrophilic-lipophilic balance values that are close to those found for the glucose compound with Z = -O-(α-PP-O-)n (without the Et-O-Et group), (ii) all these compounds are more strongly hydrophilic than the corresponding glucidic derivatives with Z = O, (iii) the increase of the poly-(α-propyloxy) chain length from ñ = 6 to ñ = 14 tends to reduce the hydrophilicity slightly.