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Widely adaptable oil-in-water gel emulsions stabilized by an amphiphilic hydrogelator derived from dehydroabietic acid

Yan, T T; Song, B L; Pei, X M; Cui, Z G; Cui, Z G; Binks, B P; Yang, H Q; Yan, B L; Song, X M; Pei; Binks; Yang, H Q

Authors

T T Yan

B L Song

X M Pei

Z G Cui

Z G Cui

H Q Yang

B L Yan

X M Song

Pei

H Q Yang



Abstract

A novel surfactant, 6-((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxamido)-N,N-dimethylhexan-1-amine oxide (abbreviated as R-6-AO) derived from dehydroabietic acid has been synthesized which behaves as a highly efficient low molecular weight hydrogelator with an extremely low critical gelation concentration (CGC) of 0.18 wt.% (4 mM). As a typical surfactant, R-6-AO not only stabilizes oil-in-water (O/W) emulsions at concentrations above its critical micelle concentration (cmc) of 0.6 mM, but also forms gel emulsions at concentrations beyond the CGC with the oil volume fraction freely adjustable between 2% and 95%. Cryo-TEM images reveal that R-6-AO molecules self-assemble into left-handed helical fibers with cross-sectional diameters of about 10 nm in pure water which can be turned to very stable hydrogels at concentrations above the CGC. Compared with traditional high internal phase emulsions, the gel emulsions stabilized by R-6-AO can be prepared with different oils such as n-dodecane, n-decane, n-octane, soybean oil, olive oil and tricaprylin, due to the tricyclic diterpene hydrophobic structure in their molecules which enable them to adopt a unique arrangement in the fibers. The intriguing properties of gel emulsions stabilized by R-6-AO are believed to be significant and helpful for the preparation of new soft materials and other applications.

Journal Article Type Article
Print ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
APA6 Citation Yan, T. T., Song, B. L., Pei, X. M., Cui, Z. G., Binks, B. P., & Yang, H. Q. (in press). Widely adaptable oil-in-water gel emulsions stabilized by an amphiphilic hydrogelator derived from dehydroabietic acid. Angewandte Chemie, https://doi.org/10.1002/anie.201907774
DOI https://doi.org/10.1002/anie.201907774
Keywords Gel emulsions; Low molecular weight hydrogelator; Self-assemble fibers; Dehydroabietic acid; Amine oxide
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