Synthesis and surface properties of new dicephalic saccharide-derived surfactants

A new group of nonionic dicephalic saccharide amides, N-dodecyl-N,N-bis[(3-D-gluconylamido)propyl]- amine, N-dodecyl-N,N-bis[(3-D-glucoheptonylamido)propyl]- amine, and N-alkyl-N,N-bis [(3-lactobionylamido)propyl]amines (alkyl: n-C12H25, n-C16H33' n-C18H37) were synthesized and characterized. Their structure and purity were confirmed by means of H-1 and C-13 nuclear magnetic resonance analysis and electrospray ionization mass spectrometry. Carbon spectra were verified using a DEFT experiment. The surface and interracial properties such as critical micelle concentration (CMC), standard free energy of micellization, Delta G(CMC') surface excess concentration, Gamma(CMC), and surface area demand per molecule, A(CMC), were determined. The tertiary nitrogen atom seems to have a surprising effect on surfactant packing at the interface.