Equilibrium Surface Tension, Dynamic Surface Tension, and Micellization Properties of Lactobionamide-Type Sugar-Based Gemini Surfactants

Yoshimura, Tomokazu; Umezawa, Shin; Fujino, Akihiko; Torigoe, Kanjiro; Sakai, Kenichi; Sakai, Hideki; Abe, Masahiko; Esumi, Kunio

doi:10.5650/jos.62.353

Cited by 24 publications

(7 citation statements)

References 27 publications

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“…Whereas an Amin increase related to a bigger size of the molecules is reported by some authors [44,54] in other cases an Amin reduction is attributed to a more tight packing because of hydrophobic interactions between the larger alkyl chains [44]. However, in many cases a regular tendency is not produced [55,56]. In the present study, the Amin decreases with increasing the alkyl chain length.…”

Section: Tablecontrasting

confidence: 42%

Cationic gemini surfactants containing an O-substituted spacer and hydroxyethyl moiety in the polar heads: Self-assembly, biodegradability and aquatic toxicity

Kaczerewska

Brycki

Ribosa

et al. 2018

Journal of Industrial and Engineering Chemistry

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Micellization and some ecological properties of new cationic gemini surfactants with oxygensubstituted spacer and hydroxyethyl groups connected to the polar heads have been studied. The incorporation of a hydroxyethyl group in the polar head favors self-aggregation whereas the presence of the oxygen in the spacer increases critical micelle concentration. Surfactants investigated are not biodegradable due to their toxic effect on microorganisms responsible for biodegradation. Aquatic toxicity increases with the hydrophobic chain and decreases by increasing the hydrophilicity of spacer and polar heads. New gemini surfactants are less toxic to the aquatic environment than monomeric surfactants and non-oxygen-containing gemini surfactants.

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Section: Tablecontrasting

confidence: 42%

Cationic gemini surfactants containing an O-substituted spacer and hydroxyethyl moiety in the polar heads: Self-assembly, biodegradability and aquatic toxicity

Kaczerewska

Brycki

Ribosa

et al. 2018

Journal of Industrial and Engineering Chemistry

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“…2, the CMC of 7a, 7b, 7c, and 7d can be determined as 7.52 × 10 −5 , 4.88 × 10 −5 , 4.17 × 10 −5 , and 3.80 × 10 −5 mol L −1 . With the increase of the lipophilic group from C8 (7a) to C16 (7d), the CMC showed a gradual reduction, which was often observed in common surfactants with a homologous compound (Komorek and Wilk, 2004;Wang et al, 2010;Yoshimura et al, 2013). The CMC values are much lower than those of mono alkyl glucosides, 0.21 to 5.32 mM for C10-C16, and basically comparable to those of gemini alkyl glucosides, 0.029 to 0.22 mM for C10-C16 as reported by Liu et al (2013).…”

Section: Resultsmentioning

confidence: 92%

“…According to some previous reports (Li et al, 2014a;Tian et al, 2012;Wang et al, 2011), the small aggregates of R h of around 1 nm are generally regarded as micelles, and the large aggregates of R h of 70-110 nm are vesicles. Yoshimura et al (2013) investigated the aggregates of 2CnLac gemini surfactants with a diameter of 4-12 nm, which were confirmed as micelles based on their size. The coexistence of small micelles with large vesicles is also reported for other gemini surfactants (Pisarcik et al, 1998).…”

Section: Adsorption Propertiesmentioning

confidence: 99%

“…* Changsheng Gan gancs7894@163.com During the last decade, some gemini surfactants containing sugar moieties in their headgroups were designed and synthesized, mainly nonionic and cationic amphiphiles, some of which exhibited excellent physicochemical and biological activities, and it is likely that these surfactants will be further investigated and used in applications such as personal care products, industrial products, and biological and medicinal research (Fielden et al, 2001;Han and Zhang, 2004;Johnsson et al, 2003aJohnsson et al, , 2003bKomorek and Wilk, 2004;Laska et al, 2006;Laska and Wilk, 2004;Liu et al, 2013;Negm and Mohamed, 2008;Sakai et al, 2008;Wang et al, 2014;Warwel et al, 2004;Wilk et al, 2002;Yoshimura et al, 2013;Zhang and Han, 2009). In this article, we report on the synthesis of novel types of sugarbased gemini surfactants.…”

Section: Introductionmentioning

confidence: 99%

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Novel Sugar‐Based Gemini Surfactants and Their Surface Properties

Gan

Liang

Cai

2018

J Surfact & Detergents

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A group of novel sugar‐based gemini surfactants, N, N′‐bis(2‐hydroxy‐3‐alkyloxylpropyl) ‐N, N′‐bis(gluconylamide)‐ethylenediamine (alkyl: n‐C8H17, n‐C12H25, n‐C14H29, n‐C16H33), were synthesized and characterized. Their surface properties, including surface tension, γ, critical micelle concentration, CMC, maximum surface excess, Гmax, minimum area per molecule, Amin, and standard free energy of micellization and adsorption, normalΔGm0 and normalΔGads0, were investigated. The members of this family could reduce the surface tension of water to approximately 20–25 mN m−1 at the concentration level of 10−5 mol L−1, considerably lower than that commonly achieved with monomeric surfactants. Their adsorption and aggregation behavior were further studied by means of dynamic light scattering and X‐ray diffraction. The relationship of the aggregate size of the synthesized gemini surfactants with the length of the hydrocarbon chain and their concentration was discussed.

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“…Glycolipids amphiphilic nature allows them to spontaneously aggregate and arrange in structures like micelles, whose capacity to form bilayers and/or vesicles has been also reported . In particular, the aggregation behavior of glycolipids like alkyl polyglycosides, sorbitan esters, and sucrose esters can be found in literature …”

Section: Introductionmentioning

confidence: 97%

Alkyl‐mannoside derivatives: Glycolipids able to form big size aggregates

Sandoval-Altamirano

Sánchez

Pizarro

et al. 2018

J of Physical Organic Chem

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Three different series of alkyl mannoside derivatives have been synthesized, designing the hydrophobic portion to provide different topology to the surfactant and, hence, modulating their aggregation properties. The aggregates formed were characterized using both physical and photophysical methodologies, such as surface tension, dynamic light scattering, and emission of selected fluorescent probes. The non‐ionic sugar surfactants have been widely used in studies of membrane solubilization and protein purification. Indeed, mannoside unit, nonionic and hydrophilic, can be selectively recognized by several lectins, which are proteins present in different membranes. Then, the specific interactions of these derivatives incorporated into synthetic bilayers with lectins have been studied and reported. In this work, monoalkyl derivatives with a presumably conical shape and dialkyl derivatives with cylindrical ones, including also a third family with a hydrophilic spacer were studied. These compounds are able to self‐aggregate to form micelle like structures or bilayers despite their topology. Additionally, they are able to form bilayers, using cosurfactants like cholesterol.

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Equilibrium Surface Tension, Dynamic Surface Tension, and Micellization Properties of Lactobionamide-Type Sugar-Based Gemini Surfactants

Cited by 24 publications

References 27 publications

Cationic gemini surfactants containing an O-substituted spacer and hydroxyethyl moiety in the polar heads: Self-assembly, biodegradability and aquatic toxicity

Cationic gemini surfactants containing an O-substituted spacer and hydroxyethyl moiety in the polar heads: Self-assembly, biodegradability and aquatic toxicity

Novel Sugar‐Based Gemini Surfactants and Their Surface Properties

Alkyl‐mannoside derivatives: Glycolipids able to form big size aggregates

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