Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

A series of 13 well-defined alkylglucuronamides [AGUA] surfactants with hydrophobic chains consisting of fatty alcohols (C8, C12, or C16) involved in a glucosidic bond has been synthesized in two steps from glucuronic acid or glucuronolactone. The nonionic polar heads are a sugar unit with an amide function derived from five different amines, i.e., methylamine, ammonia, ethanolamine, ethoxyethanolamine, and aminopropanediol. Their CMC values present variations from 0.03 to 29 mM, and their hydrophilic/lipophilic behaviors have been compared to conventional dodecyl polyethoxylated surfactants (C12Ej) using the PIT-slope methodology. They cover a large scale of the corresponding C12Ej with j varying from 5 to 8. Regarding functional properties, the novel alkylglucuronamides exhibit good foaming properties. Last but not least, two of them could be classified as easily biodegradable according to respirometric tests.