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J Colloid Interface Sci. 2019 Jul 01;547:275-290. doi: 10.1016/j.jcis.2019.03.068. Epub 2019 Mar 28.

Worm-like micelles and vesicles formed by alkyl-oligo(ethylene glycol)-glycoside carbohydrate surfactants: The effect of precisely tuned amphiphilicity on aggregate packing.

Journal of colloid and interface science

Jackson E Moore, Thomas M McCoy, Anna V Sokolova, Liliana de Campo, Graeme R Pearson, Brendan L Wilkinson, Rico F Tabor

Affiliations

  1. School of Chemistry, Monash University, Clayton, VIC 3800, Australia.
  2. Australian Centre for Neutron Scattering, ANSTO, Lucas Heights, NSW 2234, Australia.
  3. Axieo Pty Ltd, Level 3, 35 Cotham Road, Kew, VIC 3101, Australia.
  4. School of Science & Technology, University of New England, Armidale, NSW 2351, Australia.
  5. School of Chemistry, Monash University, Clayton, VIC 3800, Australia. Electronic address: [email protected].

PMID: 30959261 DOI: 10.1016/j.jcis.2019.03.068

Abstract

Carbohydrates are appealing non-ionic surfactant head-groups as they are naturally abundant, generally biocompatible and biodegradable, and readily functionalized. Recent work has produced a promising molecular candidate for the formation of viscoelastic worm-like micellar solutions: a tri(ethylene glycol)-linked oleyl-β-D-glucoside surfactant (GlcC18:1) exhibited near ideal Maxwell behavior at low concentrations (2.9 wt%) without additives at room temperature. Here, fourteen surfactants have been synthesized with structural variations based around GlcC18:1. Each contain an oligo(ethylene glycol) linker of varying length (2, 3, 4, 6 EO units) between a carbohydrate head-group (glucose, galactose, mannose, maltose, lactose, cellobiose) and a cis-unsaturated alkyl tail-group (oleyl, linoleyl, erucyl). The aqueous adsorption kinetics and self-assembly of these surfactants was explored using tensiometry and small-angle neutron scattering (SANS), respectively. With SANS we observed the formation of worm-like micelles for four surfactants, and vesicles for two surfactants which exhibited behavior similar to insoluble lipids. We also observed temperature-induced micellar elongation due to dehydration of the oligo(ethylene glycol) linker, resulting in a further three surfactants forming worm-like micelles at 50 °C. Worm-like micellar fluids were further characterized using rheology to reveal two surfactants with vastly superior viscoelastic properties compared to GlcC18:1, with >2 orders of magnitude increase in viscosity and >3 orders of magnitude increase in stress relaxation time. These results provide insight into structure-function relationships for non-ionic surfactants and demonstrate a class of designed amphiphiles with a special propensity for forming viscoelastic worm-like micellar solutions at low concentrations.

Crown Copyright © 2019. Published by Elsevier Inc. All rights reserved.

Keywords: Alkyl-glycosides; Carbohydrate surfactants; Rheology; Small-angle neutron scattering; Vesicles; Worm-like micelles

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