Effect of Chain Unsaturation on the Self-Association of Tri- and Tetraethylene Glycol Octyl Ethers Obtained by Butadiene Telomerization

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• 作者：Jonathan Lai ; Val茅rie Molinier ; Mathieu Sauthier ; Laurianne Moity ; Yves Castanet ; Andr茅 Mortreux ; Jean-Marie Aubry
• 刊名：Langmuir
• 出版年：2012
• 出版时间：January 10, 2012
• 年：2012
• 卷：28
• 期：1
• 页码：242-250
• 全文大小：902K
• 年卷期：v.28,no.1(January 10, 2012)
• ISSN：1520-5827

文摘

2,7-Octadienyl ethers of tri- and tetraethylene glycol (C_8:2E₃ and C_8:2E₄) have been synthesized by the atom-economical butadiene telomerization of the corresponding poly(ethylene glycols). On one hand, this synthetic path is attractive because it is expeditious and environmentally benign, and on the other hand, it provides unconventional amphiphiles for which the lipophilic chains possess two double bonds. These two unsaturations increase the global hydrophilicity of the compound, which is also highlighted by the modelization of the compounds using the conductor-like screening model for real solvents (COSMO-RS). The behavior of C_8:2E₃ and C_8:2E₄ in binary amphiphile/water and ternary amphiphile/oil/water systems is therefore greatly modified compared to that of the conventional fully saturated homologues (C₈E₃ and C₈E₄) that are easily obtained after hydrogenation. This results in a lowered efficiency of the unsaturated compounds for oil solubilization. The usual Winsor-type microemulsion systems are formed, and for the same oil, the DLS investigation of the microstructure of the Winsor I microemulsion does not highlight any difference in the self-association between the unsaturated and saturated compounds.