Partitioning behavior of an acid-cleavable, 1,3-dioxolane alkyl ethoxylate, surfactant in single and binary surfactant mixtures for 2- and 3-phase microemulsion systems according to ethoxylate head group size

Rio, Javier A. Gomez del; Hayes, Douglas G.; Urban, Volker S.

doi:10.1016/j.jcis.2010.08.076

Cited by 16 publications

(6 citation statements)

References 34 publications

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“…SDS (>99% pure) was obtained from Avantor Performance Materials (Center Valley, PA, USA). O-[(2-tridecyl, 2-ethyl-1,3-dioxolan-4-yl) methoxy]-O-methoxy poly(ethylene glycol), or "cyclic ketal" alkyl ethoxylate surfactants, having average ethoxylate monomeric units of 5.6 (CK-2,13-E 5.6 ), was synthesized employing a previously published procedure by our group (Gomez del Rio et al, 2010;Iyer et al, 2001). Briefly, 3-hexadecanone was conjugated with glycerol CK-2,13 to form cyclic ketal (1,3-dioxolane) linkages in toluene under reflux using p-toluene sulfonic acid as a catalyst and employing a Dean-Stark trap to collect the coproduct water.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…All surfactants and cosurfactants are water-insoluble. The average degree of polymerization for the ethoxylate group, n, is 5.6; but the size distribution is broad, spanning the range 3 ≤ n ≤ 10 (Gomez del Rio et al, 2010;Iyer et al, 2001). AOT/CK-2,13 microemulsion systems are temperature-insensitive, reflecting the synergism between the two surfactants (Gomez del Rio et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

“…The average degree of polymerization for the ethoxylate group, n, is 5.6; but the size distribution is broad, spanning the range 3 ≤ n ≤ 10 (Gomez del Rio et al, 2010;Iyer et al, 2001). AOT/CK-2,13 microemulsion systems are temperature-insensitive, reflecting the synergism between the two surfactants (Gomez del Rio et al, 2010). Synergy between surfactants in binary surfactant mixtures, including alcohol ethoxylates and sulfonate surfactants, is an important topic in surfactant science made possible by the experimental and theoretical contributions of Dr. Milton J. Rosen and coworkers (Hua and Rosen, 1982;Rosen, 1992;Rosen and Hua, 1982).…”

Section: Introductionmentioning

confidence: 99%

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Incorporation of Membrane Proteins Into Bicontinuous Microemulsions Through Winsor‐III System‐Based Extraction

Hayes

Anunciado

et al. 2021

J Surfact & Detergents

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The membrane proteins (MP) α-synuclein (ASYN) and bacteriorhodopsin (BR) were readily incorporated into bicontinuous microemulsions (BμEs) formed by two microemulsion systems: water/heptane/Aerosol-OT (AOT)/CK-2,13 and water/dodecane/sodium dodecyl sulfate (SDS)/1-pentanol. (CK-2,13 is an alkyl ethoxylate possessing two alkyl tail groups of carbon chain length 2 and 13 and an average degree of ethoxylation of 5.6.) MP were encapsulated in BμEs through preparation of Winsor-III systems at optimal salinity, with the anionic surfactants AOT and SDS providing the driving force for extraction. Dissolution of ASYN in BμEs greatly increased the former's α-helicity, similar to ASYN's behavior in the presence of biomembranes, while BμE-and vesicleencapsulated BR possessed similar secondary structure. Small-angle neutron scattering (SANS) results clearly demonstrated the direct interaction of MP with the surfactants, resulting in a decrease of surface area per volume for surfactant monolayers due to decreased surfactant efficiency. The SANS signal for ASYN was isolated through the use of neutron contrast matching for the surfactants through partial deuteration of water and oil, one of the first reports of contrast matching for BμEs in the literature. The SANS results of the contrast-matched sample reflected similar aggregation for ASYN in BμEs as was reported previously for vesicles and SDS solution. This study demonstrates the potential use of BμEs as MP host systems for conducting biochemical reactions such as the conversion of sunlight into adenosine triphosphate by BR and studying the fundamental behavior of MP, such as the role of ASYN dysfunction in Parkinson's disease, as well as for isolation and purification of MP via Winsor-III-based extraction.Keywords α-synuclein Á bacteriorhodopsin Á bicontinuous microemulsions Á membrane proteins Á smallangle neutron scattering Á Winsor-III microemulsion systems

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Section: Experimental Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Incorporation of Membrane Proteins Into Bicontinuous Microemulsions Through Winsor‐III System‐Based Extraction

Hayes

Anunciado

et al. 2021

J Surfact & Detergents

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“…Among the environmentally benign surfactants that generated industrial and research interest, − a type of cleavable surfactant featured with acetal or ketal structure is quite stable in alkaline, neutral, and oxidizing conditions but decomposes in acidic conditions by the cleavage of the acetal bond. Some natural compounds with aldehyde group are the perfect raw material candidates of such green surfactants.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Cleavable Vanillin-Based Polyoxyethylene Surfactant and Its Pilot Application in Cotton Fabric Pretreatment

Feng-mei

Zhou

et al. 2019

ACS Sustainable Chem. Eng.

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A novel series of nonionic surfactants (vanillin-1,2-octanediol acetal ethoxylates, VAEO) was synthesized. VAEO was based on natural edible flavor vanillin. These new eco-friendly surfactants contain cleavable acetal bonds which decompose easily under acidic conditions. VAEO was synthesized via a two-step reaction and its structure was characterized by 1 H nuclear magnetic resonance, 13 C nuclear magnetic resonance, and liquid chromatography-mass spectrometry. VAEO n with a series number of EO units (n = 4−12) showed good surface activities, wettability, emulsibility, and low-foaming properties, which were comparable with NPEO 10 (nonylphenol ethoxylates).VAEO n were applied to cotton fabric pretreatment and satisfactory fabric performances were obtained. A pilot application of VAEO 6 in cotton fabric pretreatment was successfully conducted. The capillary effect and whiteness of the treated cotton fabrics met the quality criteria well. Furthermore, the toxicity experiments showed that VAEO is a low-to-moderately toxic chemical. The rapid biodegradability test showed its biodegradation rate in 28 days is 92%. And the endocrine disrupting effects trial proved that VAEO has no endocrine-disrupting effects. Therefore, VAEO meets DfE criteria for safer surfactants.

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“…When an aqueous surfactant solution comes into contact with an immiscible organic liquid in one environment, such as water-oil-metal pipe environments, surfactant monomers may prefer partitioning into the organic liquid until equilibrium is reached, [13][14][15] which usually depletes the surfactants available in the aqueous phase for adsorption on the metal surface and for corrosion inhibiton. 4 Considering the behavior of surfactant partitioning in oil-water environments and associated interfacial phenomena, the determination of surfactant partitioning between water and oil usually serves as the basis of the hydrophobic-hydrophilic balance 13,14,16,17 and is critical for the evaluation of corrosion inhibition efficiency of surfactants. 4 For pure surfactant, the partitioning is usually characterized by the partitioning coefficient, which is defined as the ratio of monomeric surfactant concentration in oil to that in aqueous phase.…”

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confidence: 99%

Experimental Investigation and Modeling of the Performance of Pure and Mixed Surfactant Inhibitors: Partitioning and Distribution in Water-Oil Environments

Zhu

Free

2015

J. Electrochem. Soc.

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A critical model of water-oil surfactant distribution has been developed and validated for the evaluation of mixed surfactant partitioning and distribution in water-oil environments. The surfactant distribution model, which is a combination of surfactant partitioning sub-model, partitioning coefficient calculation method, and a developed critical micelle concentration (cmc) prediction sub-model based on previous work, provides a very powerful tool to evaluate the partitioning of mixed surfactants in water-oil environments. Different methods to calculate partitioning coefficients are introduced, which includes transfer free energy method and group contribution method. The partitioning data from model prediction and from experiment agree very well. The mixed micelles start to form in water-oil environments only after the apparent cmc is reached during partitioning. The selective partitioning of one particular surfactant in mixed surfactants can be explained by its apparent cmc which is interpreted as one characteristic of the hydrophobicity/hydrophilicity of that surfactant in water-oil environments. It is believed that the partitioning and distribution of non-homologous mixed surfactants in oil-water environments are evaluated theoretically and experimentally for the first time. The effect of partitioning on corrosion inhibition of mixed surfactants was initially evaluated by modified Langmuir adsorption and by electrochemical measurements. The corrosion inhibition efficiency from model prediction and from experimental measurements is comparable. The use of surfactant inhibitors has received extensive attention in the oil and gas industry for corrosion inhibition of production and transportation pipes (metallic materials, such as steel and copper) in a way that surfactant molecules usually adsorb on steel surface and form a protective film which acts as a barrier to prevent corrosive media penetration and attack. [1][2][3][4] Compared to the production and use of pure surfactants, surfactant mixtures are well known due to the superior physicochemical properties and capabilities in efficient solubilization, adsorption, suspension, and transportation. [5][6][7][8] The solutions of surfactant mixtures can often be conveniently tuned to achieve desired properties by adjusting the mixed surfactant types and molar ratios. More surface-active and expensive surfactants are often mixed with less surface-active and cheaper surfactants to reduce cost.9,10 Natural mixtures of surfactants are sometimes used to avoid the investment in separation processes. However, further studies are required in order to optimize inhibition efficiency of surfactant mixtures and minimize environmental impact.Surfactant molecules have hydrophilic and hydrophobic sections, 7,11,12 which are critical to the adsorption on metal surface and associated corrosion inhibition.2-4 The hydrophilic functional group of surfactant molecules strongly prefers interaction with polar entities such as metals, which is helpful in corrosion inhibition. The hydroph...

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Partitioning behavior of an acid-cleavable, 1,3-dioxolane alkyl ethoxylate, surfactant in single and binary surfactant mixtures for 2- and 3-phase microemulsion systems according to ethoxylate head group size

Cited by 16 publications

References 34 publications

Incorporation of Membrane Proteins Into Bicontinuous Microemulsions Through Winsor‐III System‐Based Extraction

Incorporation of Membrane Proteins Into Bicontinuous Microemulsions Through Winsor‐III System‐Based Extraction

Synthesis of a Cleavable Vanillin-Based Polyoxyethylene Surfactant and Its Pilot Application in Cotton Fabric Pretreatment

Experimental Investigation and Modeling of the Performance of Pure and Mixed Surfactant Inhibitors: Partitioning and Distribution in Water-Oil Environments

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