11-苄硒基十一羧酸铵盐的双重刺激响应性质

doi:10.13218/j.cnki.csdc.2018.03.001

摘要/Abstract

摘要： 合成了一种对氧化还原(Redox)和CO₂/N₂具有双重刺激响应的表面活性剂11-苄硒基十一羧酸铵盐(BSeUA),分别利用傅里叶红外光谱、核磁共振和电喷雾质谱等手段研究了BSeUA在Redox和CO₂/N₂刺激响应前后的分子结构变化特征。结果表明,在过氧化氢和水合肼交替作用下,BSeUA分子中二价硒醚基团(-Se-)与相应的四价硒亚砜基团(-Se=O)之间可以氧化还原可逆互变,在CO₂和N₂交替作用下,BSeUA分子中羧酸根(-COO^-)与相应的羧酸(-COOH)之间可以可逆互变,从而实现BSeUA对Redox和CO₂/N₂具有双重刺激响应。分别在Redox和CO₂/N₂刺激作用下,由BSeUA稳定的乳液可以在破乳和再乳化2种状态下开关可逆循环至少5次,且乳液粒径和稳定性未发生明显变化。

关键词: 阴离子表面活性剂, 乳液, 刺激响应, CO₂/N₂, 氧化还原

Abstract: A kind of redox and CO₂/N₂ dual stimuli-responsive surfactant ammonium 11-benzylselanyl undecanoate (BSeUA) was synthesized.The molecular structure change of BSeUA triggered by redox and CO₂/N₂ was studied with Fourier Transform Infrared Spectroscopy (FT-IR),Nuclear Magnetic Resonance (NMR) and Electrospray Ionization Mass Spectrometry (ESI-MS).Results show that the selenium-containing group can be reversibly switched between bivalent selenide (-Se-) and tetravalent selenoxide (-Se=O) by alternately adding hydrogen peroxide and hydrazine hydrate,and the CO₂-sensitive group can be reversibly switched between carboxylate (-COO^-) and carboxylic acid (-COOH) by bubbling CO₂ and N₂.Thus,the BSeUA-stabilized emulsion can be switched reversibly between de-emulsification and re-emulsification over five times at least.No obvious adverse changes in droplet size and the relative stability of the regenerated emulsions are observed.

Key words: anionics surfactant, emulsion, stimuli-responsive, CO₂/N₂, redox

中图分类号:

TQ423

秦飞, 刘雪锋. 11-苄硒基十一羧酸铵盐的双重刺激响应性质[J]. 日用化学工业, 2018, 48(3): 123-128.

QIN Fei, LIU Xue-feng. Dual stimuli-responsive properties of ammonium 11-benzylselanyl undecanoate[J]. China Surfactant Detergent & Cosmetics, 2018, 48(3): 123-128.

参考文献

[1] Brown P,Butts C P,Eastoe J.Stimuli-responsive surfactants [J].Soft Matter,2013,9(8):2365-2374.
[2] Lu H,Guan X,Dai S,et al.Application of CO₂-triggered switchable surfactants to form emulsion with Xinjiang heavy oil [J].Journal of Dispersion Science & Technology,2014,35(5):655-662.
[3] Salager J L,Forgiarini A M.Emulsion stabilization,breaking,and inversion depends upon formulation:advantage or inconvenience in flow assurance [J].Energy & Fuels,2012,26(7):4027-4033.
[4] Takahashi Y,Koizumi N,Kondo Y.Active demulsification of photo-responsive emulsions using cationic-anionic surfactant mixtures [J].Langmuir,2016,32(3):683-688.
[5] Lu H,Xue M,Wang B,et al.pH-regulated surface property and pH-reversible micelle transition of a tertiary amine-based gemini surfactant in aqueous solution [J].Soft Matter,2015,11(47):9135-9143.
[6] Kong W,Guo S,Wu S,et al.Redox-controllable interfacial properties of zwitterionic surfactant featuring selenium atoms [J].Langmuir,2016,32(38):9846-9853.
[7] Zhang Y M,Zhang Y D,Wang C,et al.CO₂-responsive microemulsion:reversible switching from an apparent single phase to near-complete phase separation [J].Green Chemistry,2016,18(2):392-396.
[8] Lu H,Guan X,Wang B,et al.CO₂-switchable oil/water emulsion for pipeline transport of heavy oil [J].Journal of Surfactants & Detergents,2015,18(5):773-782.
[9] Ceschia E,Harjani J,Liang C,et al.Switchable anionic surfactants for the remediation of oil-contaminated sand by soil washing [J].Rsc Advances,2013,4(9):4638-4645.
[10] Xu P,Wang Z,Xu Z,et al.Highly effective emulsification/demulsification with a CO₂-switchable superamphiphile [J].Journal of Colloid & Interface Science,2016,480:198-204.
[11] Xu W,Gu H,Zhu X,et al.CO₂-controllable foaming and emulsification properties of the stearic acid soap systems [J].Langmuir,2015,31(21):5758-5766.
[12] Hu G,Yang H,Hou Q,et al.A pH and salt dually responsive emulsion in the presence of amphiphilic macromolecules [J].Soft Matter,2018,DOI:10.1039/c7sm01760j.
[13] Vermathen M,Stiles P,Bachofer S J,et al.Investigations of monofluoro-substituted benzoates at the tetradecyltrimethylammonium micellar interface [J].Langmuir,2002,18(4):1030-1042.
[14] Zhang Y,Chen H,Liu X,et al.Effective and reversible switching of emulsions by an acid/base-mediated redox reaction [J].Langmuir,2016,32(51):13728-13735.
[15] Fan Y,Zhang Y,Liu X,et al.Recovery and recycling of CO₂/N₂-switchable anionic surfactants in emulsions [J].Journal of Surfactants & Detergents,2017,20(6):1301-1309.