Beilstein Journal of Organic Chemistry (Nov 2020)

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

  • David Liese,
  • Hans Henning Wenk,
  • Xin Lu,
  • Jochen Kleinen,
  • Gebhard Haberhauer

DOI
https://doi.org/10.3762/bjoc.16.232
Journal volume & issue
Vol. 16, no. 1
pp. 2820 – 2830

Abstract

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We report new dirhamnolipid ester forming reverse wormlike micelles in nonpolar solvents without the addition of any primer. Therefore, these compounds represent a rare case of a binary system showing this gel-like behavior. In this study, the influence of the concentration of the rhamnolipid ester and the ester alkyl chain length on the rheological properties of the reverse wormlike micelles in toluene was investigated in detail. Highly viscoelastic solutions were obtained even at a relatively low concentration of less than 1 wt %. The phase transition temperatures indicate that the formation of reverse wormlike micelles is favored for dirhamnolipid esters with shorter alkyl chain lengths. Oscillatory shear measurements for the viscoelastic samples reveal that the storage modulus (G') and the loss modulus (G'') cross each other and fit the Maxwell model very well in the low-ω region. As is typical for wormlike micelle systems, the normalized Cole–Cole plot of G''/G''max against G'/G''max was obtained as a semicircle centered at G'/G''max = 1. The formation of network structures was also verified by polarized light microscopy. The sample was birefringent at ambient temperature and anisotropic at an elevated temperature. Differential scanning calorimetry analysis yielded a transition enthalpy of about ΔHSG/GS = ±7.2 kJ/mol. This value corresponds to a strong dispersion energy and explains the formation of the highly viscous gels by the entanglement of wormlike micelles through the interaction of the alkyl chains.

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