Sugar-based Surfactants Research Articles

Spacer effect on triazole-linked sugar-based surfactants

ABSTRACTA series of alkyl triazole glycoside surfactants, ATGs, differing in the length of the alkyl linker between the sugar and the triazole, was synthesized and investigated on their surfactant properties and phase behavior in water. The results indicate no significant impact of the linker on surface and interphase properties, whereas the phase behavior is affected. Higher affinity for the bicontinuous cubic phase potentially favors methylene-linked ATGs over higher homologs for drug-delivery applications. A comparison of glucose and xylose reveals a tendency for high Krafft points for propargyl xyloside based ATGs. This disfavors these surfactants with respect to both glucose analogs and higher homologs.

Micellization of Lactosylammonium Surfactants with Different Counter Ions and Their Interaction with DNA

So far, the studies about the physical chemical properties of sugar-based surfactants have been still unsystematic; most of the studies have been focused on nonionic sugar-based surfactants. In the present work, we studied the micellization of four lactose-based surfactants, with the same headgroup (lactosylammonium) and the same hydrophobic alkyl chain (dodecyl) but different counterions (malonate, adipate, propionate, and hexanoate), at 25.0 and/or 50.0 °C. We found that these four surfactants could decrease the surface tension of water to ca. 30 mN/m. When the number of carboxylate groups in the counterion was the same, the counterion having a shorter alkyl chain could lead to a smaller minimum area per surfactant molecule. Moreover, the surfactants with monocarboxylates as counterions had much lower critical micelle concentrations than those with dicarboxylates as counterions, and the micelles from the former surfactants had a lower counterion binding degree. The lactosylammonium surfactants could bin...

Experimental investigation the effect of nanoparticles on micellization behavior of a surfactant: Application to EOR

ABSTRACTChemical stimulation such as surfactant flooding in petroleum reservoirs makes efforts to produce remained oil and improve sweep efficiency by means of different phenomena such as lowering interfacial tension and wettability alteration of reservoir rock. Implementing concentration of surfactant through surfactant flooding is one of the big challenges while interfacial tension between surfactant solution and oil after certain concentration involves little changes such as critical micelle concentration (CMC). This article highlights the effect of nanosilica on CMC of Zyziphus Spina Christi, as sugar-based surfactant, in aqueous solutions for enhanced oil recovery and reservoir stimulation purposes. A conductivity approach was selected to assess the CMC of the introduced surfactant in aqueous solution at 25°C. The influence of nanosilica concentrations on CMC variation of introduced surfactant is considered. It is found that CMC of introduced surfactant decreased while the concentration of the nanosilica increased. Results from this study can aim in optimum condition selection of surfactant flooding as an enhanced oil recovery ends.

Transition from Micelle to Vesicle of a Novel Sugar-Based Surfactant Containing Trisiloxane

Abstract Vesicles form spontaneously in aqueous solution of a novel sugar-based surfactant containing trisiloxane [Si(3)N-GHA]. The transition was monitored among the monomer, micelle and vesicle through the variation of surface tension, accompanied by surface tension measurements. The vesicles of a trisiloxane containing sugar-based surfactant have been characterized by dynamic light scattering (DLS) and negative-stained transmission electron microscopy (TEM). The vesicle aggregation can be explained by the critical packing parameter derived from an analysis of chemical structure.

Synthesis and properties of Alkyl α-D-Galactopyranoside

ABSTRACTAlkyl α-D-galactopyranosides are sugar-based nonionic surfactants, and it is necessary to research their structure–property relationships since it is not quite clear that the change of the alkyl chain length has effects on a series of physicochemical properties. Here, alkyl α-D-galactopyranosides were prepared by galactose and alcohols through three steps including acetylation, coupling with alcohols in the presence of a catalyst stannic chloride, and deprotection. Furthermore, their water solubility and other properties were investigated. Alkyl α-D-galactopyranosides (4a ∼ 4e, n = 6 ∼ 10) were water soluble, and their dissolution process in water was an endothermic process. Nonyl α-D-galactopyranoside (4d) showed excellent foaming ability and foam stability. Octyl α-D-galactopyranoside (4c) had the strongest emulsifying ability for toluene and nonyl α-D-galactopyranoside (4d) had the strongest emulsifying ability for rapeseed oil. The critical micelle concentration (CMC) values and surface tension at the CMC were decreasing with increasing alkyl chain length. Their standard free energy of adsorption (ΔGads) was more negative than their standard free energy of micellization (ΔGmic). The moisture-absorption abilities were weakening with increasing alkyl chain length. Alkyl α-D-galactopyranosides (4a ∼4f) were thermally stable below 280°C. Alkyl α-D-galactopyranosides (4c ∼4f) had the optical texture of the thermotropic liquid crystal smectic A phase.

Physico-chemical properties and cytotoxic effects of sugar-based surfactants: Impact of structural variations

Surfactants derived from the biorefinery process can present interesting surface-active properties, low cytotoxicity, high biocompatibility and biodegradability. They are therefore considered as potential sustainable substitutes to currently used petroleum-based surfactants. To better understand and anticipate their performances, structure-property relationships need to be carefully investigated. For this reason, we applied a multidisciplinary approach to systematically explore the effect of subtle structural variations on both physico-chemical properties and biological effects. Four sugar-based surfactants, each with an eight carbon alkyl chain bound to a glucose or maltose head group by an amide linkage, were synthesized and evaluated together along with two commercially available standard surfactants. Physico-chemical properties including solubility, Krafft point, surface-tension lowering and critical micellar concentration (CMC) in water and biological medium were explored. Cytotoxicity evaluation by measuring proliferation index and metabolic activity against dermal fibroblasts showed that all surfactants studied may induce cell death at low concentrations (below their CMC). Results revealed significant differences in both physico-chemical properties and cytotoxic effects depending on molecule structural features, such as the position of the linkage on the sugar head-group, or the orientation of the amide linkage. Furthermore, the cytotoxic response increased with the reduction of surfactant CMC. This study underscores the relevance of a methodical and multidisciplinary approach that enables the consideration of surfactant solution properties when applied to biological materials. Overall, our results will contribute to a better understanding of the concomitant impact of surfactant structure at physico-chemical and biological levels.

Natural dye bolaform sugar-based surfactant: Self aggregation and mixed micellization with ionic surfactants

The self aggregation behavior of crocin (natural bolaform sugar based dye) and their micellization with sodium dodecyl sulfate (SDS), and cetyltrimethylammonium bromide (CTAB) were reported for the first time. Dynamic light scattering, and transmission electron microscopic techniques were employed to the morphology determination of crocin in an aqueous media for different concentrations. Vesicles were formed in pure crocin whereas vesicles -to- micelles transformation was observed in presence of CTAB. Time-resolved fluorescence emission and UV–visible spectra suggests that CTAB is a better sensitizing agent for the spectral analysis of crocin. Hydrodynamic radius of bola interacted with cationic micelles were assessed. Micellization thermodynamic parameters were calculated, and discussed. The crocin + CTAB mixed system have been observed to form both micelles and vesicles. Crocin completely solubilized into the CTAB micelles, and leads to the formation mixed micelles having wicket-like conformation at the air/water interface.

Synthesis, characterization, and application of polysodium N-alkylenyl α-d-glucopyranoside surfactants for micellar electrokinetic chromatography-tandem mass spectrometry.

Sugar-based ionic surfactants forming micelles are known to suppress ESI of various compounds due to decrease in surface tension upon micelle formation . For the first time, poly (sodium N-undecylenyl-α-d-glucopyranoside 4,6-hydrogen phosphate, (poly-α-d-SUGP) based surfactants with different chain lengths and head groups have been successfully synthesized, characterized, and applied as compatible chiral selector for MEKC-ESI-MS/MS. First, the effect of polymerization concentrationof the monomer, α-d-SUGP, was evaluated by enantioseparation of one anionic compound (1,1'-binaphthyl-2,2'diyl-hydrogen phosphate) and one zwitterionic compound (dansylated phenylalanine) in MEKC-UV to find the optimum molar surfactant concentration for polymerization. Next, MEKC-UV and MEKC-MS were compared for the enantioseparation of 1,1'-binaphthyl-2,2'diyl-hydrogen phosphate. The influence of polymeric glucopyranoside based surfactant head groups and carbon chain lengths on chiral Rs was evaluated for two classes of cationic drugs (ephedrine alkaloids and β-blockers). Finally, enantioselective MEKC-MS of ephedrine alkaloids and β-blockers were profiled at their optimum pH 5.0 and 7.0, respectively, using 20 mM NH4 OAc, 25 mM poly-α-d-SUGP at 30 kV and 25°C under optimum spray chamber conditions. The LOD for most of the enantiomers ranges from 10 to 100 ng/mL with S/N of at least ≥3.0.

Biocompatible natural sugar-based surfactant assisted oxidation of citric acid by MnO4−in absence and presence of SDS

Crocin, a natural carotenoid with antioxidant properties, was used in the present investigation as a surfactant in the citric acid–MnO4−redox system for the first time.

Multidimensional Mass Spectrometry Coupled with Separation by Polarity or Shape for the Characterization of Sugar-Based Nonionic Surfactants.

Mass spectrometry (MS) and tandem mass spectrometry (MS/MS) were interfaced with ultra-performance liquid chromatography (UPLC) and ion mobility (IM) separation to characterize a complex nonionic surfactant, consisting of a methylated glucose core (glucam) conjugated with poly(ethylene oxide) (PEO(n)) branches that were partially esterified with stearic acid to form ethoxylated glucam (PEO(n)-glucam) stearates. Reverse-phase LC-MS afforded fast separation according to polarity into five major fractions. Accurate mass measurements of the ions in the mass spectra extracted from these fractions enabled conclusive identification of six components in the surfactant, including PEO(n)-glucam mono-, di-, and tristearates as well as free and esterified PEO(n) as byproducts. MS/MS experiments provided corroborating evidence for the fatty acid content in each fraction based on the number of stearic acid losses observed. With IM-MS, the total surfactant ions were separated according to charge and shape into four distinct bands. Extracted mass spectra confirmed the presence of two disaccharide stearates in the surfactant, which were undetectable by LC-MS. PEO(n)-glucam tristearates were, however, not observed upon IM-MS. Hence, LC-MS and IM-MS unveiled complementary compositional insight. With each method, certain components were particularly well separated from other ingredients (by either polarity or shape), to be detected with confidence. Consequently, combined LC-MS and IM-MS offer a superior approach for the characterization of surfactants and other amphiphilic polymers and for the differentiation of similarly composed amphiphilic blends. It is finally noteworthy that NH4(+) charges minimized chemical noise in MS mode and Li(+) charges maximized the fragmentation efficiency in MS/MS mode.

Oxyethylene chain length affects the physicochemical properties of sugar-based anionic surfactants with phosphates groups

In this study we prepared a series of novel sugar based anionic-polyoxyethylene stearyl ether surfactants through reactions of propylene glycol dextrin with oxirane-containing polyoxyethylene stearyl ethers and phosphorus oxychloride. These surfactants, which contain polyoxyethylene chains and sodium phosphonate groups as hydrophilic moieties, exhibited surface activities superior to those of traditional surfactants containing only one nonpolar or hydrophobic moiety and one polar head unit. The critical micelle concentration (cmc), surface excess concentration at the surface (Γcmc) and standard free energy of micellization per mole (ΔGm°) of these surfactants decreased upon increasing the length of their polyoxyethylene chain. In addition, we used UV–vis spectroscopy to study the interactions of dyes with these sugar based anionic surfactants in solution, the results shows that the interaction of the dye and surfactant molecules and the type of dye–surfactant aggregate formed will depend upon chemical structure of dye and surfactant.

Multi-technique approach on the interaction between sugar-based surfactant n-dodecyl β-d-maltoside and bovine serum albumin

A multi-technique approach which comprises various basic and advanced techniques, such as surface tensiometry, synchronous, intrinsic and extrinsic fluorescence, far and near-UV circular dichroism (CD), dynamic light scattering (DLS), Fourier transform infra-red (FTIR) and UV–visible spectrophotometries was applied to understand the interaction between biocompatible sugar-based surfactant n-dodecyl β-d-maltoside (C12G2) and bovine serum albumin (BSA). Formation of complex between surfactant and protein was initially confirmed by surface tension and UV absorption spectroscopy. The presence of BSA shifted the critical micelle concentration of the surfactant at higher concentration and in a similar way the UV spectrum of the BSA was altered by addition of small amount of surfactant. The interfacial properties of the complex such as πcmc (the surface pressure at the cmc), Γmax (the maximum surface excess) and Amin (the minimum surface area per molecule) were also calculated. Addition of surfactant causes the quenching of BSA fluorescence and a large blue-shift at both excitation wavelengths (280 and 295nm) owing to the hydrophobic interaction between surfactant and protein. The quenching took place via static mechanism. Extrinsic fluorescence of 1-anilino-8-naphthalene sulfonate (ANS) increased as a result of the unfolding of the protein. The secondary and tertiary structure of BSA also influenced as revealed by the collective information obtained by far-UV CD, near-UV CD and FTIR spectroscopies. The increase in the size of the complex as a results of the partial unfolding was also confirmed by DLS measurements as well as resonance Rayleigh scattering (RRS).

Interaction of biocompatible sugar based surfactant n-dodecyl β-d-maltoside with lysozyme

The interaction of lysozyme with biocompatible sugar-based surfactant n-dodecyl β-d-maltoside (C12G2) was investigated by using surface tensiometry, synchronous and intrinsic fluorescence, circular dichroism (CD), Fourier-transform infra-red (FTIR), dynamic light scattering (DLS), and UV–visible absorption spectroscopies. The results of absorption spectra showed that formation of a complex has taken place between lysozyme and surfactant. Surface tension measurements revealed that the complex was surface active and the interfacial properties of the complex such as πcmc (the surface pressure at the cmc), Γmax (the maximum surface excess) and Amin (the minimum surface area per molecule) were calculated. The hyperchromic shift in the case of intrinsic and synchronous fluorescence measurements suggested that the fluorophores were more exposed on the addition of the surfactant to the protein. Far- and near-UV CD study in combination with FTIR measurements has shown that the interaction between lysozyme and C12G2 resulted in the partial unfolding of protein for which α-helical contents have been analyzed and discussed. The increase in the size of the complex on the partial unfolding was also confirmed by DLS measurements.

GlycoSurf finalizes licence agreement to produce sugar-based surfactants for cosmetics

GlycoSurf finalizes licence agreement to produce sugar-based surfactants for cosmetics

Surface modification of polyurethane via covalent immobilization of sugar-based trisiloxane surfactants

Sugar-based trisiloxane surfactants (N-siloxanegluconamides and N-siloxanelactobionamides, denoted as Si(3)NGA and Si(3)NLA) with the amphiphilic structures were successfully prepared. Polyurethane (PU) was grafted with 2-carboxyethyl acrylate (CEA) by the means of UV-induced graft polymerization, and further introduction of the Si(3)NGA and Si(3)NLA by conjugating the amino groups and acid groups. The surface graft polymerization was confirmed by attenuated total reflection Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy, respectively. Water contact angle, protein adsorption, and platelet adhesion measurements were used to evaluate the hydrophilicity and hemocompatibility of the films. It was found that the Si(3)NGA-modified substrates obviously suppressed protein adsorption and platelet adhesion, while Si(3)NLA-modified substrates exhibited a higher protein adsorption and a coagulating performance of blood.

The interaction between sugar-based surfactant with zigzag single-walled carbon nanotubes: insight from a computational study

A promising new development in therapeutic nanomedicine includes drug and biomolecule delivery system using carbon nanotubes dispersed in surfactant, such as glycolipid. To study the interaction between carbon nanotube and surfactant, here we report on a density functional theory (DFT) calculation at the B3LYP/6-31G level of theory performed for the purpose of predicting the reactivity governing the nucleophilic and electrophilic attacks on the external surface of a single-walled carbon nanotube (SWNTs). The DFT-based local reactivity descriptor, Fukui function, local softness and dual reactivity have been examined to predict the reactivity of different carbon atom sites of the SWNTs understudy. In addition, binding energy, high occupied molecular orbital (HOMO), lowest occupied molecular orbital (LUMO) and energy difference between carbon nanotube and the complex (SWNT-surfactant) are determined. The computational results predicted that glycolipid, as a non-ionic surfactant, could result in a strong interaction on the surface of the SWNT in both gas and aqueous phases.

Sugar-based surfactants as alternative to synthetic ones

AbstractFrom year to year natural surfactants are gaining ever growing awareness because of their valuable properties (in the absence of negative impact on the environment, as with the use of synthetic surface active agents). In the group of surfactants of natural origin there are surface active agents produced by microorganisms (biosurfactants) or compounds having a natural part (hydrophilic head and/or hydrophobic tail) [1]. This review includes the short characteristic of surfactants with sugar-head group in their structure called sugar-based surfactants. The structure, properties and some applications of these surfactants are described in this paper.

Lipase immobilized in microemulsion based organogels (MBGs) as an efficient catalyst for continuous-flow esterification of protected fructose

Sugar-based surfactants are important esters for the cosmetic, food and pharmaceutical industries due to their intrinsic properties.

Micelle size modulation and phase behavior in MEGA-10/Triton X-100 mixtures

This paper reports the effect of temperature and NaCl addition on micelle size and phase behavior in mixtures of N-decanoyl-N-methylglucamide (MEGA-10) and p-tert-octyl-phenoxy polyethylene (9.5) ether (Triton X-100 or TX100). The size of mixed micelles, as determined by dynamic light scattering (DLS), was found to increase with temperature but to be less pronounced at higher proportions of MEGA-10 in the solution. The cloud point was found to increase with an initial increase in the percentage of sugar-based surfactant in the mixture. This phase separation was sensitive to the presence of NaCl in the micellar solution, which induced a cloud point depression, thereby suggesting that the presence of electrolyte produces a marked alteration of the hydration layer of micelles. A thermodynamic analysis was performed assuming the clouding phenomenon to be a liquid–liquid phase-separation process. The resulting ΔGCP0 values were positive for all solutions. The cloud point process was exothermic in nature for the mixed micellar system, as proven by the negative value of ΔHCP0. The process was more exothermic as the proportion of sugar-based surfactant in the mixed micelle increased (with and without NaCl in the solution). Furthermore, the negative values of ΔSCP0 indicate that the association of micelles in the clouding phenomenon is entropically unfavorable. It was observed from the enthalpy–temperature plots that the change in heat capacity is negative, thus indicating the important role played by dehydration in this thermodynamic process. This study found that the enthalpy–entropy compensation relationship holds for this process. The micelle–water interactions were characterized from the compensation temperatures.

New Y-shaped surfactants from renewable resources

A series of sugar-based surfactants, involving a single hydrophobic chain (C12) and two side-by-side arranged head groups, was prepared form simple glucose precursors. All surfactants were highly water soluble and exhibited exclusively micellar assemblies. This behavior makes them interesting candidates for oil in water emulsifiers.