Synthesis, surface activities, and aggregation behavior of phenyl-containing carboxybetaine surfactants

Zhang

Lan

et al. 2019

Ind. Eng. Chem. Res.

Self Cite

A novel series of sulfobetaine surfactants, 3-((4-(alkoxy)-3,5-dimethylbenzyl) dimethylammonio)-2-hydroxypropane-1-sulfonate (C n OBSb, n = 12, 14, and 16), were synthesized for the first time. The chemical structures of products were characterized by high-resolution mass spectra, 1 H NMR, and 13 C NMR spectrometry. The physicochemical properties of C n OBSb were studied by thermogravimetric analysis, equilibrium surface tension measurement, steady-state fluorescence, dynamic light scattering (DLS), and cryogenic transmission electron microscopy (cryo-TEM). The results demonstrated that surface tension values of C n OBSb are in the range of 28.32−30.14 mN/m at a fairly low critical micelle concentration (cmc).The adsorption and micellization properties of C n OBSb were dependent on the hydrocarbon chain length and presence of phenyl group. The results of DLS and cryo-TEM measurements revealed that C n OBSb molecules spontaneously formed vesicles in aqueous solution above the cmc. Furthermore, the application properties indicated that C n OBSb possessed superior interfacial tension capability, outstanding wetting ability, and good foaming and emulsifying properties.

Section: Experimental Methodsmentioning

confidence: 99%

Synthesis and Physicochemical Properties of Novel Phenyl-Containing Sulfobetaine Surfactants

Zhang

Lan

et al. 2019

Ind. Eng. Chem. Res.

Self Cite

“…The ESI-HRMS spectrum was determined by a Bruker FT-ICR-MS spectrometer. The alkylbetaine surfactants (ASB 12 and ACB 12 ) were reported in several preceding articles , and synthesized for comparison, while the novel phenyl-containing betaine surfactants with a hydrocarbon chain length of 10 (BSB 10 and BCB 10 ) were prepared according to our previous works. , The synthesis routes and procedures of four betaine surfactants are shown in the Supporting Information along with the 1 H and 13 C NMR spectra of products . Their molecule structural data were given as follows.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…It is well known that the chemical structures of betaine surfactants are a crucial part in determining their physicochemical properties and even their application fields. To obtain comprehensive understanding of betaine surfactants, many studies have been carried out to synthesize novel kinds of betaine surfactants. − Most studies have concentrated on investigating the effect of hydrophobic moieties modifications, − the hydrocarbon chain length, − and the types of hydrophilic headgroups , on physicochemical properties. For example, Kelleppan et al synthesized five long-chain amidopropyl betaines with C18 tailgroups and found that different degrees of unsaturation and branching significantly affect aggregation structures.…”

Section: Introductionmentioning

confidence: 99%

Studies on Physicochemical Properties and Aggregation Behavior of Two Pairs of Betaine Surfactants

Zhang

Lan

et al. 2019

Ind. Eng. Chem. Res.

Self Cite

Two pairs of betaine surfactants with the same hydrophobic moieties but different hydrophilic headgroups, including alkylbetaine surfactants (ACB12 and ASB12) and phenyl-containing betaine surfactants (BCB10 and BSB10), were synthesized, and their chemical structures were confirmed by ESI-HRMS, 1H NMR, and 13C NMR. Their surface activities and aggregate morphologies were also systematically investigated. Phenyl-containing betaine surfactants exhibit better surface activities than alkylbetaine surfactants, including higher short-term thermal stabilities, lower critical micelle concentrations (CMC) and surface tensions, and greater tendencies of adsorption and aggregation. The minimum interfacial tension (IFTmin) of BSB10 and BCB10 solution against Xinjiang crude oil achieved an ultralow value (10–3 mN/m), while the IFTmin only reached a 100–10–1 mN/m order of magnitude for ASB12 and ACB12. In addition, phenyl-containing betaine surfactants displayed considerably higher wetting ability than alkylbetaine surfactants, while the contact angles of BSB10 and BCB10 solution on a paraffin film decreased to 31.89 and 25.19°, respectively. Moreover, DLS and cryo-TEM measurements verified that phenyl-containing betaine surfactant molecules could spontaneously form vesicles in an aqueous solution above the CMC, while alkylbetaine surfactant molecules only aggregate into small micelles in the solution. The BSB10 and BCB10 molecules could further assemble into larger vesicles with increasing surfactant concentration.

“…A higher magnitude of DG q ads is observed as compared to DG q m values, showing that adsorption process favorably occurs until all the air/solution interface is occupied, and then surfactants molecules begin to aggregate and form micelles in the bulk solution. 58,59 DG q m and DG q ads become more negative with increasing alkyl chain length or solution temperature. This may be due to the increased hydrophobicity of ILs, which can destroy the structure of water and increase free energy of the system, and improve the propensity of ILs molecules to migrate to the interface.…”

Section: Thermodynamics Of Micellizationmentioning

confidence: 97%

“…Thus the values of DG q m and DG q ads are more negative. 59 Rising temperature can cause the decrease of hydration around hydrophilic groups, which results in the increase of the system energy, improves protably to adsorption in the interface and formation of micelles in order to decrease energy of the surfactant system. 16,37,38 60,61 The hydrophobic effect is related to the water removal from the nonpolar surface in order to diminish the extent of less favorable hydrophobic hydration in comparison to clustered water in the bulk.…”

Section: Thermodynamics Of Micellizationmentioning

confidence: 99%

Micellization, surface activities and thermodynamics study of pyridinium-based ionic liquid surfactants in aqueous solution

Huang

et al. 2019

RSC Adv.