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

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...

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Autores principales: Liese, David, Wenk, Hans Henning, Lu, Xin, Kleinen, Jochen, Haberhauer, Gebhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7684688/
https://www.ncbi.nlm.nih.gov/pubmed/33281985
http://dx.doi.org/10.3762/bjoc.16.232
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author Liese, David
Wenk, Hans Henning
Lu, Xin
Kleinen, Jochen
Haberhauer, Gebhard
author_facet Liese, David
Wenk, Hans Henning
Lu, Xin
Kleinen, Jochen
Haberhauer, Gebhard
author_sort Liese, David
collection PubMed
description 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 ΔH(SG/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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spelling pubmed-76846882020-12-04 Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system Liese, David Wenk, Hans Henning Lu, Xin Kleinen, Jochen Haberhauer, Gebhard Beilstein J Org Chem Full Research Paper 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 ΔH(SG/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. Beilstein-Institut 2020-11-19 /pmc/articles/PMC7684688/ /pubmed/33281985 http://dx.doi.org/10.3762/bjoc.16.232 Text en Copyright © 2020, Liese et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Liese, David
Wenk, Hans Henning
Lu, Xin
Kleinen, Jochen
Haberhauer, Gebhard
Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title_full Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title_fullStr Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title_full_unstemmed Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title_short Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
title_sort dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7684688/
https://www.ncbi.nlm.nih.gov/pubmed/33281985
http://dx.doi.org/10.3762/bjoc.16.232
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