Synthesis and physicochemical properties of ester-bonded gemini pyrrolidinium surfactants and a comparison with single-tailed amphiphiles

Liang, Yaqin; Li, Hui; Li, Min; Mao, Xiaoming; Li, Yan; Wang, Zhihui; Xue, Liuyan; Chen, Xinghua; Hao, Xiaojing

doi:10.1016/j.molliq.2019.02.018

Cited by 33 publications

(18 citation statements)

References 36 publications

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“…This indicated that the formation of micelles in the solution and the adsorption behavior at the air/water interface of this series of glycosides were spontaneous. In addition, as the alkyl chain length increased, both of Δ G mic and Δ G ads values showed a decreasing trend, which indicated that the driving force of micellization and adsorption came from the hydrophobic interaction between the hydrocarbon tails . These results should echo the upward tendency of the pC 20 value described above.…”

Section: Results and Discussionmentioning

confidence: 63%

“…In addition, as the alkyl chain length increased, both of ΔG mic and ΔG ads values showed a decreasing trend, which indicated that the driving force of micellization and adsorption came from the hydrophobic interaction between the hydrocarbon tails. 52 These results should echo the upward tendency of the pC 20 value described above. Indeed, the ΔG mic values (−14.41 to −30.03 kJ mol −1 ) were higher than the corresponding ΔG ads values (−22.96 to −42.66 kJ mol −1 ) with the same alkyl chain length, indicating that such surfactants were more easily adsorbed at the air−water interface instead of micellization in solution when their concentration was below the critical micelle concentration.…”

Section: Emulsification Powermentioning

confidence: 52%

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Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

Zhang

Chen

et al. 2021

J. Agric. Food Chem.

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Hydrophilic alkyl polyglycosides (APGs) and alkyl glycosides (AGs) with anomeric pure are a class of important substitutes for petroleum-based surfactants. Improving their water solubility should make such hydrophilic glycosurfactants have more excellent potential application value. To solve the inherent problem of poor water solubility of traditional alkyl β-Dglucopyranoside (5), a series of alkyltetra(oxyethyl) β-D-glucopyranosides (4a−4g, n = 7−18) were successfully synthesized by introducing tetra(oxyethylene) fragments to carry out the structural modification. The relationship between the related structure and the physicochemical properties was further investigated, including their hydrophilic−lipophilic balance (HLB), water-solubility, foaming performance, emulsification, hygroscopicity, surface activity, and thermotropic/lyotropic liquid crystal phase behavior. The results showed that the water solubility gradually decreased as the alkyl chain length increased due to the gradual decrease of their HLB number. Octadecyltetra(oxyethyl) β-D-glucopyranoside (4g, n = 18) was found to be insoluble in water at 25 °C. Taken together, long-chain alkyl glycosides had good foaming properties and excellent emulsifying properties. Among them, dodecyltetra(oxyethyl) β-D-glucopyranoside (4d, n = 12) had the best foaming performance. In the rapeseed oil/water system, cetyltetra(oxyethyl) β-D-glucopyranoside (4f, n = 16) had the best emulsifying ability. With the increase of the alkyl chain length, the critical micelle concentration (C cmc ), γ cmc , Γ max , and hygroscopicity of this series of glycosides showed a downward trend. Differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) showed that the thermal stability increased with the increase of the alkyl chain length, and alkyltetra(oxyethyl) β-D-glucopyranosides (4d−4g, n = 12−18) had the corresponding melting points and clearing points. Alkyltetra(oxyethyl) β-D-glucopyranosides (4b−4g, n = 8−18) formed a smectic phase with a typical fan-shaped and focal conic texture during the cooling process. In the water contact experiments, it was found that glycosides (4b−4g, n = 8−18) at high concentrations transformed into various lyotropic liquid crystal including hexagonal phase, bicontinuous cubic phase, and lamellar phase phases. Therefore, such green nonionic glycosurfactants alkyltetra(oxyethyl) β-D-glucopyranosides should have potential practical application prospects.

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Section: Results and Discussionmentioning

confidence: 63%

Section: Emulsification Powermentioning

confidence: 52%

Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

Zhang

Chen

et al. 2021

J. Agric. Food Chem.

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“…These results suggest that gemini surfactants readily formed aggregates. Aggregation may have been facilitated by strong hydrophobic synergism between the two hydrophobic chains of these surfactants [ 31 ]. The CMC of 6a was similar to that of 6b , indicating that the spacer was not the main determinant of CMC.…”

Section: Resultsmentioning

confidence: 99%

Promoting Efficacy and Environmental Safety of Pesticide Synergists via Non-Ionic Gemini Surfactants with Short Fluorocarbon Chains

Wang

Xu²,

Shi³

et al. 2022

Molecules

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Improving the utilization rate of pesticides is key to achieve a reduction and synergism, and adding appropriate surfactant to pesticide preparation is an effective way to improve pesticide utilization. Fluorinated surfactants have excellent surface activity, thermal and chemical stability, but long-chain linear perfluoroalkyl derivatives are highly toxic, obvious persistence and high bioaccumulation in the environment. Therefore, new strategies for designing fluorinated surfactants which combine excellent surface activity and environmental safety would be useful. In this study, four non-ionic gemini surfactants with short fluorocarbon chains were synthesized. The surface activities of the resulting surfactants were assessed on the basis of equilibrium surface tension, dynamic surface tension, and contact angle. Compared with their monomeric counterparts, the gemini surfactants had markedly lower critical micelle concentrations and higher diffusivities, as well as better wetting abilities. We selected a single-chain surfactant and a gemini surfactant with good surface activities as synergists for the glyphosate water agent. Both surfactants clearly improved the efficacy of the herbicide, but the gemini surfactant had a significantly greater effect than the single-chain surfactant. An acute toxicity test indicated that the gemini surfactant showed slight toxicity to rats.

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“…A Zetasizer Nano ZS laser nanoparticle size analyzer (Malvern Co., UK) was used to measure the particle size at 25 C. The hydrodynamic diameter of the particles is expressed as the average of at least three measurements, and size distribution curves were obtained. 34…”

Section: Dynamic Light Scatteringmentioning

confidence: 99%

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

Qiu

Chen

Wei

et al. 2020

J of Applied Polymer Sci

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An environmental friendly oil-soluble surfactant colophony xylitol ester (CXE) is first synthesized from natural colophony and xylitol with the use of hotcompressed water and subcritical CO 2 in a steel autoclave. In this solvent-free system, the conversion of the reaction was up to 90.30% in 4 h. Thermal gravimetric analysis determine that its thermal stability was as high as 310 C. CXE is effective in reducing the surface tension of six different organic solvents. The greatest effect of surface tension reduction by CXE is in the case of dimethyl sulfoxide, the surface tension of the surfactant solution was as low as 36.26 mN/m at its critical micelle concentration value of 7.49 mM; The greatest effect of interfacial tension reduction by CXE is in the case of turpentine and water, the interfacial tension low to 1.51 mN/m. Furthermore, transmission electron microscope and particle size measurement showed that CXE is successfully self-assembled into micelles, vesicles, and heteromorphic vesicles in six kinds of organic solvents. Finally, the critical micelle concentration curves at different temperatures provided the thermodynamic parameters of the aggregate formation, found that 4G 0 agg , 4H 0 agg , and 4S 0 agg are negative and increased as the temperature increased. K E Y W O R D S colophony xylitol ester, interfacial properties, micelle, thermodynamics, vesicle 1 | INTRODUCTION Colophony is a renewable natural resin consisting of a series of tricyclic diterpenoid resin acids. 1 Colophony and its products are used in welding, paper, and coatings, as well as polymer and food industries. 2,3 Modification of brittle colophony to colophony esters can produce materials with good antioxidant properties and mechanically pliable. 4 Furthermore, owing to the hydrophobic structure of the tricyclic skeleton, surfactants can be prepared by introducing hydrophilic groups into the molecules. 5 Unlike long chain fatty acids, the rigid structure of colophony can enhance the thermal, chemical, and mechanical stability of the resulting surfactants. 6 Xylitol is widely found in fruits, vegetables, cereals, mushrooms, and other plants. 7 It is also an intermediate metabolite in the human body and has good biocompatibility and biodegradability. Fatty acid xylitol esters are a class of nonionic surfactants with important physiological activities. 8,9 Some derivates have been shown to have antitumor activity 10 and plant growth inhibition. 11 Enzymatic syntheses of xylitol esters in organic solvents have been reported. 12,13

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Synthesis and physicochemical properties of ester-bonded gemini pyrrolidinium surfactants and a comparison with single-tailed amphiphiles

Cited by 33 publications

References 36 publications

Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

Promoting Efficacy and Environmental Safety of Pesticide Synergists via Non-Ionic Gemini Surfactants with Short Fluorocarbon Chains

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

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