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Esters of oligo-(glycerol carbonate-glycerol): New biobased oligomeric surfactants

Holmiere, Sébastien and Valentin, Romain and Maréchal, Philippe and Mouloungui, Zéphirin Esters of oligo-(glycerol carbonate-glycerol): New biobased oligomeric surfactants. (2017) Journal of Colloid and Interface Science, 487. 418-425. ISSN 0021-9797

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Official URL: https://doi.org/10.1016/j.jcis.2016.10.072


Glycerol carbonate is one of the most potentially multifunction glycerol-derived compounds. Glycerol is an important by-product of the oleochemical industry. The oligomerization of glycerol carbonate, assisted by the glycerol, results in the production of polyhydroxylated oligomers rich in linear carbonate groups. The polar moieties of these oligomers (Mw<1000Da) were supplied by glycerol and glycerol carbonate rather than ethylene oxide as in most commercial surfactants. The insertion of linear carbonate groups into the glycerol-based skeleton rendered the oligomers amphiphilic, resulting in a decrease in air/water surface tension to 57mN/m. We improved the physical and chemical properties of the oligomers, by altering the type of acylation reaction and the nature of the acyl donor. The polar head is constituted of homo-oligomers and hetero-oligomers. Homo-oligomers are oligoglycerol and/or oligocarbonate, hetero-oligomers are oligo(glycerol-glycerol carbonate). Coprah oligoesters had the best surfactant properties (CMC<1mg/mL, πcmc<30mN/m), outperforming molecules of fossil origin, such as ethylene glycol monododecyl ether, glycol ethers and fatty acid esters of sorbitan polyethoxylates. The self-assembling properties of oligocarbonate esters were highlighted by their ability to stabilize inverse and multiple emulsions. The oligo-(glycerol carbonate-glycerol ether) with relatively low molecular weights showed properties of relatively high-molecular weight molecules, and constitute a viable “green” alternative to ethoxylated surfactants.

Item Type:Article
HAL Id:hal-01421815
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:Université de Toulouse > Institut National Polytechnique de Toulouse - Toulouse INP (FRANCE)
French research institutions > Institut National de la Recherche Agronomique - INRA (FRANCE)
Other partners > Stéarinerie DUBOIS (FRANCE)
Laboratory name:
Deposited On:29 Nov 2019 10:23

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