Self-association of short-chain nonionic amphiphiles in binary and ternary systems: comparison between the cleavable ethylene glycol monobutyrate and its ether counterparts.
In the context of environmental concerns for the production of surface active species, the introduction of a carbonyl function into the skeleton of ethyleneglycol-derived solvo-surfactants is a way to access cleavable compounds with presumed enhanced biodegradability. Ethylene glycol monobutyrate (C(3)COE(1)) was synthesized and compared to its ether counterparts, ethylene glycol monopropyl (C(3)E(1)) and monobutyl ethers (C(4)E(1)), to assess the effect of the insertion of a carbonyl function in the skeleton of short-chain ethoxylated amphiphilic compounds. In aqueous solutions, the ester has intermediate behavior between that of the two ethers with regard to surface tension, solubilization of Me-naphtalene in water, and self-diffusion by PGSE NMR. In ternary systems, C(3)COE(1) and C(3)E(1) have the same optimal oil (EACN = 2.8), which is much more polar than that of C(4)E(1) (EACN = 8.5). With regard to the ability to form structured systems, the behavior in water does not differ significantly for the three compounds, and the transition between nonassociating solvents and amphiphilic solvents, sometimes called solvo-surfactants, is gradual. In ternary systems, however, only C(4)E(1) and C(3)COE(1) form a third phase near the optimal formulation, which tends to show that C(3)COE(1) possesses the minimum amphiphilicity to get a structuration. Self-diffusion NMR studies of the one-phase domains do not, however, allow us to distinguish between different degrees of organization in the three systems.
Zhu
Ying
Y
LCOM, Equipe "Oxydation et Formulation", UMR CNRS 8009, ENSCL BP 90108, F-59652 Villeneuve d'Ascq Cedex, France.
Fournial
Anne-Gaëlle
AG
Molinier
Valérie
V
Azaroual
Nathalie
N
Vermeersch
Gaston
G
Aubry
Jean-Marie
JM
D002087:Butyrates / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D019855:Ethylene Glycol / Q000737:chemistry*; D015394:Molecular Structure; D009821:Oils / Q000737:chemistry; D010316:Particle Size; D012996:Solutions; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry; D014867:Water / Q000737:chemistry
D002087:Butyrates; D004987:Ethers; D009821:Oils; D012996:Solutions; D013501:Surface-Active Agents; D014867:Water; D019855:Ethylene Glycol