Design and Properties of a Novel Family of Nonionic Biobased Furanic Hydroxyester and Amide Surfactants

Abstract

A series of original amphiphiles prepared by Morita–Baylis–Hillman (MBH) coupling biobased furanic aldehydes with hydrophobic alkenes is explored. Structural variations result from the level of polarity on the furanic substrate, the type of activated alkenes (ester of amide), the alkyl chain length, and the presence of an unsaturation. The physicochemical properties such as the Krafft point, critical micellar concentration (CMC), and hydrophilic lipophilic behavior determined with the PIT-slope method have been explored. The glucosyloxymethyl furfural (GMF) derivatives exhibit higher water solubility than the succinyl hydroxymethyl furfural (SMF) and the HMF-derived ones. Saturation of the acrylic linkage results in slightly lower CMC for GMF-derived compounds by the enhanced solvation of the unsaturation. As expected, increasing the alkyl chain length diminishes the water solubility, the CMC, and the hydrophilicity. The decreasing hydrophilic behavior of surfactants is as follows: Gi > GiH > HSi. For the shorter HMF amphiphiles, the order is HiN > Hi ≈ HiH. These surfactants cover a wide range of HLB values. The dodecyl GMF─G12─is as hydrophilic as C12E6, and the hexadecyl SMF─HS16─is much more hydrophobic than SPAN 40. Formation of stable emulsions with two cosmetic oils of different polarity is very encouraging for a possible application of this new family of biobased surfactants.