Nonionic Bolaamphiphiles and Gemini Surfactants Based on Carbohydrates

Pestman, J.M; Terpstra, K.; Stuart, Marc C. A.; Doren, H.A. van; Brisson, Alain; Kellogg, R. M.; Engberts, Jan B. F. N.

doi:10.1021/la970681k

Cited by 83 publications

(69 citation statements)

References 21 publications

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“…Acylation with anhydrides to form 43 proceeds cleanly (attempts to increase the atom economy by using an acid chloride led to unsatisfactory results). 37 The bolaamphiphiles 42 are in general too insoluble to be useful. The gemini compounds 43 obtained after acylation do not suffer from this problem.…”

Section: Scheme 17mentioning

confidence: 99%

Mesogenic sugars. From aldoses to liquid crystals and surfactants

et al. 2000

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Amphiphilic sugar derivatives, formed by condensation of functionalized aliphatic chains with aldoses, form liquid crystals, in most cases smectic. A puzzling observation was the failure of the S,S-acetals of 6-deoxy sugars, L-rhamnose and D-fucose, to form such phases. A satisfactory model to explain this behavior involves-in most cases-the formation of columns, which are destabilized with the deoxy sugars in which the apolar end methyl groups are pushed together.Despite the abundance of chiral centers in the mono-and disaccharides used the smectic phases themselves in general display no chirality. By appropriate molecular design in which the amphiphilic character was deliberately suppressed it was possible to prepare glucose derivatives that exhibit chiral nematic phases as well as impressive helical twisting powers. Simple condensation chemistry is used to produce such derivatives.The amphiphilic character can be deliberately enhanced, and this is readily achieved in double headed 'gemini' derivatives formed by condensation of glucose or lactose with a long chain diamine followed by reduction followed by acylation of the nitrogen atoms with long chain acyl anhydrides. The thermodynamics of micellization of precursors to these derivatives have been studied. The gemini derivatives themselves display remarkable properties including the formation of giant vesicles and an appreciable capacity for the solubilization of hydrocarbons.

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Section: Scheme 17mentioning

confidence: 99%

Mesogenic sugars. From aldoses to liquid crystals and surfactants

et al. 2000

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“…Those that have been studied in greatest depth, in terms of their physicochemical behavior, have been the cationic gemini surfactants (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), although research on anionic (14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24), zwitterionic (25), and nonionic (26)(27)(28)(29)(30)(31)(32)(33)(34)(35) dimeric surfactants also has been conducted.…”

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Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Zhang

2004

J Surfact & Detergents

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A new family of glucosamide-based trisiloxane gemini surfactants of the general formula (CH 2 OCH 2 ) n (Me 3 SiOSiMeR 1 OSiMe 3 ) 2 (where R 1 = (CH 2 ) 3 NR 2 (CH 2 ) 2 NHCO (CHOH) 4 CH 2 OH; R 2 = CH 2 CH(OH)CH 2 OCH 2 ; and n = 0, 1, or 2) was prepared and characterized, both structurally and as aqueous surfactants. The monomer was prepared by amidation of the precursor amine functional trisiloxane with D-gluconic acid δ-lactone. Gemini surfactants were then prepared by the alkylation of the precursor secondary amine with oligoethylene glycol diglycidyl ethers. They were structurally characterized by proton and 13 C nuclear magnetic resonance and elemental analysis. Members of this family reduced the surface tension of water to approximately 21 mN/m at concentration levels of 10 −5 mol/L. These gemini compounds showed two critical aggregation concentration values. This behavior resulted from the formation of premicellar aggregates before true micelles were formed.In recent years, silicone surfactants have attracted considerable interest because of their many technical applications. Owing to their unique molecular structure compared with that of normal hydrocarbon surfactants, they have excellent surface-active properties for special purposes. They can also reduce the surface tension of water to lower values than can be obtained using traditional organic surfactants. Furthermore, because of their bulkiness and molecular structure, the adhesion forces between the individual molecules in interfacial films are small; for this reason, the compounds act as good wetting agents. Silicone surfactants are also known for their low physiological risk in cosmetic applications.In contrast, sugar-based surfactants have been known for many years. In recent years, they have begun to be produced on an industrial scale and their use has gradually increased because of their valuable properties, such as good dermatological compatibility, excellent biodegradability, and the absence of toxic effects.Over a decade ago, gemini (dimeric) surfactants, a new class of surfactants consisting of two hydrophobic chains and two hydrophilic headgroups connected by a relatively short (rigid or flexible) spacer, were developed. These dimeric compounds show improved surfactant properties compared with monomeric surfactants. Gemini surfactants have attracted considerable interest, since these compounds have much smaller critical micelle concentration (CMC) values, much greater efficiency in reducing surface tension than expected, and better aggregation behavior. Gemini surfactants have been generating increasing interest owing to their tunable molecular geometry and their superior performance in applications (the CMC of the gemini is very low, so less gemini may be needed to reduce the surface tension of the solution).The unique surfactant properties of gemini surfactants have prompted investigations by a number of researchers. Those that have been studied in greatest depth, in terms of their physicochemical behavior, have been the cationic gemin...

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“…Because of these valuable features, many research groups have directed their studies to various aspects of synthetic methodologies and properties of a wide range of saccharide surfactants that vary in their molecular architecture, such as single-chain, single-head entities (5)(6)(7)(8)(9)(10)(11)(12), di-chained (13,14) and dicephalic compounds (15,16) as well as bolaamphiphiles and gemini structures (17,18). Accordingly, all of these saccharide-derived materials exhibit similar general trends in surface-active behavior as reported for polyoxyethylene-based nonionics.…”

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Preparation and properties of new lactose‐based surfactants

Wilk

Syper

Burczyk

et al. 2001

J Surfact & Detergents

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A new group of nonionic saccharide-based surfactants, N-alkanoyl-N-methyllactitolamines (alkanoyl: decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl), were synthesized and characterized. Surface properties such as critical micelle concentration, standard free energy of adsorption, standard free energy of micellization, surface tension reduction efficiency, effectiveness of surface tension reduction, surface excess concentration, and surface area demand per molecule as well as foaming properties (i.e., foam volume and foam stability), contact angle, antimicrobial activity, and biodegradability were determined. The selected performance properties were evaluated in relation to commercially available alkyl polyglucosides (Glukopon 600 EC(HH)-a Henkel product), and oligooxyethylenated decyl (C 10 E 4 ) and dodecyl (C 12 E 5 ) alcohols. The foaming-stabilizing effect and contact angle suggest that the lactose-derived surfactants that were studied share some common properties with alkyl polyglucosides that are different from those with an oligooxyethylene grouping. All tested N-alkanoyl-N-methyllactitolamines were practically nontoxic to bacteria and yeasts. These compounds are readily biodegradable in the Closed Bottle test inoculated with activated sludge. N-Alkanoyl-N-methyllactitolamines with lower chain lengths (C 10 -C 14 ) biodegraded at a slightly faster rate. Biological properties showed that this class of compounds fulfills all requirements needed for environmental acceptance.Paper no. S1211 in JSD 4, 155-161 (April 2001).KEY WORDS: N-Alkanoyl-N-methyllactitolamines, antimicrobial activity, biodegradability, contact angle, foaming ability, nonionic lactose-derived surfactants, surface activity.Nonionic surfactants bearing a carbohydrate moiety as the hydrophilic part (so-called saccharide or sugar surfactants) have recently received increasing interest because they have improved surface and performance properties, reduced environmental impact, and they have potential pharmaceutical and biomedical applications (1-4). Because of these valuable features, many research groups have directed their studies to various aspects of synthetic methodologies and properties of a wide range of saccharide surfactants that vary in their molecular architecture, such as single-chain, single-head entities (5-12), di-chained (13,14) and dicephalic compounds (15,16) as well as bolaamphiphiles and gemini structures (17,18). Accordingly, all of these saccharide-derived materials exhibit similar general trends in surface-active behavior as reported for polyoxyethylene-based nonionics. However, the absence of a cloud point for aqueous solutions of saccharidebased nonionics indicates that the carbohydrate segments do not undergo dehydration with increasing temperature and that their interactions with water molecules are more favorable than the corresponding interactions between water molecules and polyoxyethylene segments. As a continuation of our studies (8,12,15,16) related to nonionic surfactants comprising various carbohydrate hydrop...

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Nonionic Bolaamphiphiles and Gemini Surfactants Based on Carbohydrates

Cited by 83 publications

References 21 publications

Mesogenic sugars. From aldoses to liquid crystals and surfactants

Mesogenic sugars. From aldoses to liquid crystals and surfactants

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Preparation and properties of new lactose‐based surfactants

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