Progress in the Synthesis of Zwitterionic Gemini Surfactants

Zhou, Ming; Li, Sisi; Zhang, Ze; Wang, Chengwen; Luo, Gang; Zhao, Jinzhou

doi:10.1007/s11743-017-2014-0

Cited by 28 publications

(13 citation statements)

References 40 publications

(56 reference statements)

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“…Zwitterions (ZIs) are small molecule ampholytes, or covalently bonded cations and anions, of zero net charge . Their ionic properties and hydrophilicity have made them targets for use in organic electronics, catalysis, battery electrolytes, surfactants, drug‐delivery, and antifouling coatings, among other applications . ZI‐incorporated polymers (polyZIs) have also been investigated as novel materials for chromatography, drug‐delivery, self‐assembled microstructures, and battery electrolytes …”

Section: Introductionmentioning

confidence: 99%

Ion transport mechanisms in salt‐doped polymerized zwitterionic electrolytes

Keith

Ganesan

2020

Journal of Polymer Science

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Polyzwitterions (polyZIs), macromolecules with repeating ampholytic monomers, are a novel class of materials with attractive properties for battery electrolytes. In this study, we probe the ion transport characteristics and underlying mechanisms in two salt‐doped (Li+‐TFSI−) polyZIs of similar composition with contrasting zwitterion (ZI) ionic organization: pendant monomers organized via backbone‐anion‐cation (B‐ZI−‐ZI+, Motif B) and backbone‐cation‐anion (B‐ZI+‐ZI−, Motif C). Within both Motifs B and C, the counterion of the pendant‐end ZI moiety shows higher mobility. Similarly, when comparing Li+ or TFSI− across motifs, it is seen that the respective pendant‐end counterion possesses higher mobility than its backbone‐adjacent counterpart. Furthermore, when comparing counterions to same‐position ZI moieties, TFSI− is seen to possess higher mobility than Li+ in each case, a result rationalized by invoking the lower interaction strength between the TFSI− and ZI+. Analysis of ion‐transport mechanisms demonstrate that the mobility of countercharges to the pendant‐end ZI moiety correlates with the ion‐association relaxation timescale, similar to ideas noted in polymerized ionic liquids in past studies. However, the mobility of countercharges to the backbone‐adjacent ZI moiety is shown to be correlated with a cage relaxation time, which incorporates the combined effects of frustrated motion due to the presence of the polymer backbone and pendant‐end ZI moiety and the higher mobility in a population of lightly ZI‐coordinated ions. © 2020 Wiley Periodicals, Inc. J. Polym. Sci. 2020, 58, 578–588

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Section: Introductionmentioning

confidence: 99%

Ion transport mechanisms in salt‐doped polymerized zwitterionic electrolytes

Keith

Ganesan

2020

Journal of Polymer Science

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“…Head groups with positive and negative charges could chelate metal ions including Ca 2+ and Mg 2 by electrostatic interactions. The quaternary ammonium groups and four hydroxyls avoided the formation of a reversed micelle structure and the so‐called “calcium soap” precipitation (Zhou et al, ). The salinity resistance of sulfobetaine gemini surfactants PPM‐10, PPM‐12, and PPM‐14 with hydroxyl is superior to those of cationic gemini surfactants and sulfonate gemini surfactants reported in the literature (El‐Aila, ; Kalyansundaram and Thomas, ).…”

Section: Resultsmentioning

confidence: 99%

Section: Salinity Resistance Experimentsmentioning

confidence: 98%

Synthesis of New Sulfobetaine Gemini Surfactants with Hydroxyls and Their Effects on Surface‐Active Properties

Zhou

et al. 2018

J Surfact & Detergents

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Sulfobetaine gemini surfactants, bis{[(N‐methyl‐N‐(3‐alkoxy‐2‐hydroxyl) propyl‐N‐(2‐hydroxyl‐3‐sulfonic acid sodium) propyl] methylene} ammonium chlorides (n = 10, 12, 14), were synthesized by etherification, ring‐opening reaction, and quaternization with epichlorohydrin, linear‐saturated alcohol, N,N′‐dimethylethylenediamine, and 3‐chloro‐2‐hydroxypropane sulfonic acid sodium as main raw materials. The structures of the sulfobetaine gemini surfactants with hydroxyls were characterized using Fourier transform infrared spectroscopy (FTIR), 1H‐Nuclear Magnetic Resonance (NMR), mass spectroscopy (MS), and elemental analysis. With increasing length of the carbon chain, the values of the critical micelle concentration (CMC) initially decreased. These compounds exhibit superior surface‐active properties compared to single‐chain sulfobetaine surfactants such as dodecyl dimethyl hydroxyl sulfopropyl betaine surfactants. The efficiency of adsorption at the water/air interface (pC20) of these surfactants is very high. The shorter hydrophobic chain length of sulfobetaine gemini surfactants, the faster the surface tension reduction, and the smaller the aggregation number of sulfobetaine gemini surfactants. The micelle diameter and the maximum wetting angle of pure water drop/air increased, but the maximum wetting angle of water phase/n‐decane decreased with the increase of the hydrophobic chain length. With the increase of the hydrophobic chain length, salinity resistance went up and the corresponding interfacial tension reduced. Their foam volume and foam half‐life were investigated. Our studies have indicated that synthesized gemini surfactants can effectively reduce the oil/water interfacial tension to ultralow interfacial tension of hexane (IFT) (10−3 mN m−1 orders of magnitude) under the conditions of high temperature and high salinity.

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“…Alkanediyl‐α,ω‐bis‐type gemini surfactants have two head groups and hydrocarbon tails joined through a spacer near or close to head groups (Menger and Keiper, ; Zhou et al, ). Compared to the traditional monomeric surfactants, geminis show advanced properties due to introduction of spacers, such as low cmc, emulsification, unfamiliar aggregation behavior, and high surface activity (Akram et al, ; Kumar and Rub, ; Kumar and Rub, 2019a; Rosen and Tracy, ; Wang et al, ; Zana, ).…”

Section: Introductionmentioning

confidence: 99%

Interaction of Metal Ion‐Coordinated Dipeptide Complex and Ninhydrin in the Alkanediyl‐α,ω‐bis‐Type Gemini Surfactant System

Kumar

Rub

2019

J Surfact & Detergents

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In the current study, interaction of a metal ion‐coordinated dipeptide complex and ninhydrin was examined in the alkanediyl‐α,ω‐bis‐type gemini surfactant system. This work was performed as a function of reactants (ninhydrin and metal‐dipeptide complex), surfactants, temperature, and pH. Different techniques including UV–vis spectrophotometry were used to carry out the experiments. The kψ–values were evaluated in the presence of alkanediyl‐α,ω‐bis‐type gemini surfactants. A first‐order path in the metal‐dipeptide complex and a fractional‐order path in ninhydrin were noticed. To illustrate the quantitative analysis of kψ–[gemini] profiles, a pseudophase model of micelles was employed. Thermodynamic parameters were also evaluated and explained. By the observed outcomes, a probable mechanism was suggested and discussed in detail.

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Progress in the Synthesis of Zwitterionic Gemini Surfactants

Cited by 28 publications

References 40 publications

Ion transport mechanisms in salt‐doped polymerized zwitterionic electrolytes

Ion transport mechanisms in salt‐doped polymerized zwitterionic electrolytes

Synthesis of New Sulfobetaine Gemini Surfactants with Hydroxyls and Their Effects on Surface‐Active Properties

Interaction of Metal Ion‐Coordinated Dipeptide Complex and Ninhydrin in the Alkanediyl‐α,ω‐bis‐Type Gemini Surfactant System

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