pH-Responsive Nanoemulsions Based on a Dynamic Covalent Surfactant

Developing solid-free nanoemulsions with pH responsiveness is desirable in enhanced oil recovery (EOR) applications. Here, we report the synthesis of an interfacial activity controllable surfactant (T−DBA) through dynamic imine bonding between taurine (T) and p-decyloxybenzaldehyde (DBA). Instead of macroemulsions, nanoemulsions can be prepared by using T−DBA as an emulsifier. The dynamic imine bond of T−DBA enables switching between the active and inactive states in response to pH. This switching of interfacial activity was used to gate the stability of nanoemulsions, thus enabling us to turn the nanoemulsions off and on. Using such dynamic imine bonds to govern nanoemulsion stability could enable intelligent control of many processes such as heavy oil recovery and interfacial reactions.

[1]  C. Ochoa-Martínez,et al.  Polysaccharide-Based Multilayer Nano-Emulsions Loaded with Oregano Oil: Production, Characterization, and In Vitro Digestion Assessment , 2021, Nanomaterials.

[2]  Hongbin Yang,et al.  Fabrication of a pH-responsive emulsifier for heavy oil recovery based on dynamic imine bond , 2021 .

[3]  Yongming Zhang,et al.  Oxidation-Induced Breakage of the Imine Bond and Aggregate Transition in a Se-Containing Dynamic Covalent Surfactant. , 2021, Langmuir : the ACS journal of surfaces and colloids.

[4]  I. Gates,et al.  Dual Stimuli-Responsive Pickering Emulsions from Novel Magnetic Hydroxyapatite Nanoparticles and Their Characterization Using a Microfluidic Platform. , 2021, Langmuir : the ACS journal of surfaces and colloids.

[5]  Siqi Zhang,et al.  Light-tuning amphiphility of host-guest Alginate-based supramolecular assemblies for photo-responsive Pickering emulsions. , 2021, Carbohydrate polymers.

[6]  S. Onaizi,et al.  Crude oil/water nanoemulsions stabilized by biosurfactant: Stability and pH-Switchability , 2020 .

[7]  W. Xia,et al.  Redox-Responsive Oil-In-Dispersion Emulsions Stabilized by Similarly Charged Ferrocene Surfactants and Alumina Nanoparticles. , 2020, Langmuir : the ACS journal of surfaces and colloids.

[8]  A. Mandal,et al.  Enhanced oil recovery performance of gemini surfactant-stabilized nanoemulsions functionalized with partially hydrolyzed polymer/silica nanoparticles , 2020 .

[9]  S. Onaizi.  Demulsification of crude oil/water nanoemulsions stabilized by rhamnolipid biosurfactant using enzymes and pH-swing , 2020 .

[10]  Anlian Zhu,et al.  Light-switched reversible emulsification and demulsification of oil-in-water Pickering emulsions. , 2020, Angewandte Chemie.

[11]  R. Manica,et al.  Enhancing oil–solid and oil–water separation in heavy oil recovery by CO 2 ‐responsive surfactants , 2020 .

[12]  Hongbin Yang,et al.  Effects of surface modification Nano-SiO2 and its combination with surfactant on interfacial tension and emulsion stability , 2020 .

[13]  D. Mcclements,et al.  One-step dynamic imine chemistry for preparation of chitosan-stabilized emulsions using a natural aldehyde: Acid trigger mechanism and regulation, and gastric delivery. , 2020, Journal of agricultural and food chemistry.

[14]  Xiaoquan Yang,et al.  Sodium caseinate as a particulate emulsifier for making indefinitely recycled pH-responsive emulsions† , 2020, Chemical science.

[15]  Wanli Kang,et al.  Silica-based amphiphilic Janus nanofluid with improved interfacial properties for enhanced oil recovery , 2020 .

[16]  B. Binks,et al.  Aqueous Foams in the Presence of Surfactant Crystals. , 2020, Langmuir : the ACS journal of surfaces and colloids.

[17]  Zhiyu Huang,et al.  Redox and pH Dual-Responsive Emulsion Using Ferrocenecarboxylic acid and N,N-Dimethyldodecylamine. , 2020, Langmuir : the ACS journal of surfaces and colloids.

[18]  Jiaming Geng,et al.  pH-Responsive crude oil-in-water Pickering emulsion stabilized by polyacrylamide nanogels , 2019 .

[19]  Narendra Kumar,et al.  Gemini surfactant/polymer/silica stabilized oil-in-water nanoemulsions: Design and physicochemical characterization for enhanced oil recovery , 2019 .

[20]  T. Swager,et al.  Dynamic Imine Chemistry at Complex Double Emulsion Interfaces. , 2019, Journal of the American Chemical Society.

[21]  Zhenghe Xu,et al.  Nanoemulsion formation by the phase inversion temperature method using polyoxypropylene surfactants. , 2019, Journal of colloid and interface science.

[22]  Narendra Kumar,et al.  Oil-in-water nanoemulsion stabilized by polymeric surfactant: Characterization and properties evaluation for enhanced oil recovery , 2018, European Polymer Journal.

[23]  To Ngai,et al.  Emulsions stabilized by pH-responsive PNIPAM-based microgels: Effect of spatial distribution of functional carboxylic groups on the emulsion stability , 2018, Journal of the Taiwan Institute of Chemical Engineers.

[24]  Zhenghe Xu,et al.  Dynamic Covalent Silica Nanoparticles for pH-Switchable Pickering Emulsions. , 2018, Langmuir : the ACS journal of surfaces and colloids.

[25]  F. Shirini,et al.  Taurine as a green bio-organic catalyst for the preparation of bio-active barbituric and thiobarbituric acid derivatives in water media. , 2018, Bioorganic chemistry.

[26]  M. Sangermano,et al.  Polymeric nanocapsules via interfacial cationic photopolymerization in miniemulsion , 2018 .

[27]  P. Venema,et al.  Interfacial properties of whey protein and whey protein hydrolysates and their influence on O/W emulsion stability , 2017 .

[28]  Xiao-liang Sun,et al.  Design of pH-responsive “on-off” emulsions using CTAB/PPA emulsifiers by simulations and experiments , 2017 .

[29]  Yongming Zhang,et al.  CO2 and Redox Dual Responsive Pickering Emulsion. , 2017, Langmuir : the ACS journal of surfaces and colloids.

[30]  Zhenghe Xu,et al.  pH Switchable Emulsions Based on Dynamic Covalent Surfactants. , 2017, Langmuir.

[31]  Zhenghe Xu,et al.  Highly effective emulsification/demulsification with a CO2-switchable superamphiphile. , 2016, Journal of colloid and interface science.

[32]  G. Cheraghian.  Improved Heavy Oil Recovery by Nanofluid Surfactant Flooding - An Experimental Study , 2016 .

[33]  M. Eswaramoorthy,et al.  Reversible control of pore size and surface chemistry of mesoporous silica through dynamic covalent chemistry: philicity mediated catalysis. , 2015, Nanoscale.

[34]  K. Tam,et al.  Stimuli-responsive Pickering emulsions: recent advances and potential applications. , 2015, Soft matter.

[35]  W. Hou,et al.  Magnetic demulsification of diluted crude oil-in-water nanoemulsions using oleic acid-coated magnetite nanoparticles , 2015 .

[36]  Ying Guan,et al.  Multiple responsive hydrogel films based on dynamic Schiff base linkages , 2014 .

[37]  P. Mukherjee,et al.  Molecular marriage through partner preferences in covalent cage formation and cage-to-cage transformation. , 2013, Journal of the American Chemical Society.

[38]  W. Richtering.  Responsive emulsions stabilized by stimuli-sensitive microgels: emulsions with special non-Pickering properties. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[39]  J. Hao,et al.  Highly stable concentrated nanoemulsions by the phase inversion composition method at elevated temperature. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[40]  J. Boekhoven,et al.  Responsive vesicles from dynamic covalent surfactants. , 2011, Angewandte Chemie.

[41]  Guangtong Wang,et al.  A pH-responsive superamphiphile based on dynamic covalent bonds. , 2011, Chemistry.

[42]  P. Jessop,et al.  A synthesis of acetamidines. , 2011, The Journal of organic chemistry.

[43]  Yujun Feng,et al.  A Facile Route towards thePreparation of Ultra-Long-Chain Amidosulfobetaine Surfactants , 2009 .

[44]  K. Tam,et al.  Review on the dynamics and micro-structure of pH-responsive nano-colloidal systems. , 2008, Advances in colloid and interface science.

[45]  W. Richtering,et al.  Magnetic, Thermosensitive Microgels as Stimuli‐Responsive Emulsifiers Allowing for Remote Control of Separability and Stability of Oil in Water‐Emulsions , 2007 .

[46]  C. Eckert,et al.  Switchable Surfactants , 2006, Science.

[47]  C. Gourdon,et al.  Emulsification by ultrasound: drop size distribution and stability. , 1999, Ultrasonics sonochemistry.