TY - JOUR
T1 - Synthesis and characterization of choline–fatty-acid-based ionic liquids
T2 - A new biocompatible surfactant
AU - Ali, Md Korban
AU - Moshikur, Rahman Md
AU - Wakabayashi, Rie
AU - Tahara, Yoshiro
AU - Moniruzzaman, Muhammad
AU - Kamiya, Noriho
AU - Goto, Masahiro
N1 - Funding Information:
The present work is financially supported by a Grant-in-Aid for Scientific Research (S) JP16H06369 from the Ministry of Education, Culture, Sports, Science, and Technology of Japan . A.M.K. thanks the Government of Japan (MEXT, Japan) for providing a scholarship. We also thank Dr. M. Watanabe for supporting the NMR and DSC facility. We thank Edanz Group ( www.edanzediting.com/ac ) for editing a draft of this manuscript.
Publisher Copyright:
© 2019 Elsevier Inc.
PY - 2019/9/1
Y1 - 2019/9/1
N2 - Ionic liquid (IL)surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline–fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs)was performed by 1 H and 13 C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2–4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG 0 m , ΔH 0 m , and ΔS 0 m )indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole]shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications.
AB - Ionic liquid (IL)surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline–fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs)was performed by 1 H and 13 C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2–4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG 0 m , ΔH 0 m , and ΔS 0 m )indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole]shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications.
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U2 - 10.1016/j.jcis.2019.04.095
DO - 10.1016/j.jcis.2019.04.095
M3 - Article
C2 - 31075635
AN - SCOPUS:85065148168
VL - 551
SP - 72
EP - 80
JO - Journal of Colloid and Interface Science
JF - Journal of Colloid and Interface Science
SN - 0021-9797
ER -