Rc. Bazito et Oa. El Seoud, Sugar-based anionic surfactants: synthesis and micelle formation of sodiummethyl 2-acylamido-2-deoxy-6-O-sulfo-D-glucopyranosides, CARBOHY RES, 332(1), 2001, pp. 95-102
The following sequence of reactions has been employed to synthesize the tit
le anionic surfactants:
[GRAPHICS]
where R=C7H15; C11H23; and C15H31, respectively, and Py refers to pyridine.
Aggregation of the surfactants synthesized (predominantly alpha anomers) i
n water was studied at 40 degreesC by conductivity measurements. Increasing
the chain length of R decreases the critical micelle concentration (CMC) a
nd the degree of counter-ion dissociation. The dependence of the Gibbs free
energy of micellization and CMC on the length of R is similar to other ion
ic surfactants, but the head-group, i.e., the sulfated sugar moiety is less
hydrophilic than the structurally related group -(OCH2-CH2)(2)-OSO3-Na+, m
ost probably because of intermolecular H-bonding in the micellar pseudo-pha
se (C) 2001 Elsevier Science Ltd. All rights reserved.