Aggregation behavior of N-alkyl perfluorooctanesulfonamides in dimethyl sulfoxide solution

Li, Guoli; Gao, Yanan; Li, Xinwei; Liu, Jie; Zheng, Liqiang; Xing, Hang; Xiao, Jin‐Xin

doi:10.1016/j.jcis.2009.10.058

Cited by 11 publications

(13 citation statements)

References 59 publications

(84 reference statements)

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“…On the other hand, dipole–dipole interactions among solvent molecules cause an association structure to form in the solvent. A temperature increase disrupts the structure of solvent molecules around the association structure, which is unfavorable for aggregate formation 45 . These results indicate that, the latter factor dominates the cmc value.…”

Section: Resultsmentioning

confidence: 83%

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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Section: Resultsmentioning

confidence: 83%

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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“…These results indicate that micellization was driven by entropy and enthalpy simultaneously. However, for Stevia-G, the values of both Δ H mic and Δ S mic were positive, which shows that the micellization was only driven by entropy. , …”

Section: Resultsmentioning

confidence: 90%

Investigation of Physiological Properties of Transglycosylated Stevia with Cationic Surfactant and Its Application To Enhance the Solubility of Rebamipide

et al. 2018

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The poor water solubility of rebamipide was enhanced by the mixed micelles of transglycosylated stevia (Stevia-G) and trimethylammonium chloride with varying carbon chain length (C n TAC, n = 14, 16, and 18). Fluorometry, isothermal titration calorimetry (ITC) and dynamic light scattering techniques examined the aggregation properties of Stevia-G and C n TAC. Synergism was found between Stevia-G and C n TAC using the approaches of Clint and Rubingh. The negative interaction parameter (average β m = −4.17, −5.47, and −7.07) and excess free energy (average ΔG° ex = −2.47, −3.06, and −3.88 kJ mol–1) increased with increasing chain length of C n TAC. The negative B 1 values by the Maeda approach suggested that chain–chain interactions contribute to the formation of a mixed micelle. The solubilization of rebamipide in the mixed micelle was evaluated in the term of the molar solubilization ratio (MSR) and partition coefficient (K m). The K m from the Stevia-G/C16TAC system was highest at a low mole fraction of C n TAC (0.2–0.6). In conclusion, the solubilization of rebamipide was more favorable between Stevia-G and C16TAC, although the stability of the mixed micelle was enhanced by an increase in hydrophobicity of the longer chain lengths used in C n TAC.

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“…A temperature increase causes a decrease in solvation of the solvophilic groups (PG core), which enhances the solvophobicity force and favors the formation of aggregates; however, increasing temperature also causes destruction of structured DMSO molecules surrounding the solvophobic group (PTFEMA chains), and this is unfavorable for the formation of aggregates [29]. The effect of temperature on the CAC of PG-b-PTFEMA in DMSO can be analyzed in terms of two opposing factors.…”

Section: Surface Tensionmentioning

confidence: 99%

“…The effect of temperature on the CAC of PG-b-PTFEMA in DMSO can be analyzed in terms of two opposing factors. A temperature increase causes a decrease in solvation of the solvophilic groups (PG core), which enhances the solvophobicity force and favors the formation of aggregates; however, increasing temperature also causes destruction of structured DMSO molecules surrounding the solvophobic group (PTFEMA chains), and this is unfavorable for the formation of aggregates [29]. As shown in Table 3, the variation of CAC with temperature indicates that the second effect is dominant.…”

Section: Surface Tensionmentioning

confidence: 99%

Synthesis and Surface‐Active Behavior of New Fluorinated Hyperbranched Polymer

Zhang

Wang

Zhang

et al. 2014

J Surfact & Detergents

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In this article, a series of novel hyperbranched fluorinated polymer with polyglycerol (PG) as the hydrophilic core and poly(2,2,2‐trifluoroethyl methacrylate) (PTFEMA) as solvophobic arms were synthesized. When the atom transfer radical polymerization was carried out using N,N‐dimethylformamide (DMF) as the solvent, [M]/[I] ratio of 200, and [CuBr]/[NBr] ratio of 0.1 at 30 °C, controlled polymerization was achieved. The surface active properties of the polymer at the dimethyl sulfoxide (DMSO)/air and chloroform/water interface were studied by pendant drop measurements. The results showed that the copolymers could reduce surface tension (interfacial tension) in a manner analogous to the conventional surfactant in aqueous solutions. Thermodynamic analysis suggested that the solvophobic PTFEMA chains play an important role in determining the driving force of the aggregate formation in DMSO.

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Aggregation behavior of N-alkyl perfluorooctanesulfonamides in dimethyl sulfoxide solution

Cited by 11 publications

References 59 publications

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

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

Investigation of Physiological Properties of Transglycosylated Stevia with Cationic Surfactant and Its Application To Enhance the Solubility of Rebamipide

Synthesis and Surface‐Active Behavior of New Fluorinated Hyperbranched Polymer

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