Sugar based surfactants

For a pertinent review, see Hill, K. Rhode, O. Sugar-based surfactants for consumer products and technical applications, Lipid/Fett, 1999, 101, 23-33. 

Ruiz, C. C., Sugar-Based Surfactants, CRC Press, New York, 2008. 

Many new sugar based products present the advantage of being non-toxic and biodegradable. The products resulting from the telomerization of 1 with appropriate nucleophiles such as alcohols, amines, water, or carbon dioxide serve generally as useful intermediates in the synthesis of various natural products and fine chemicals [60-63], as precursors for plasticizer alcohols [56, 64], components of diesel fuels [65], surfactants [11, 66], corrosions inhibitors, and non-volatile herbicides [67]. 

Pfannemtiller et al. showed that it is possible to obtain carbohydrate-containing amphiphiles with various alkyl chains via amide bond formation. For this, mal-tooligosaccharides were oxidized to the corresponding aldonic acid lactones, which could subsequently be coupled to alkylamines [128-136]. Such sugar-based surfactants are important industrial products with applications in cosmetics, medical applications etc. [137-139]. The authors were also able to extend the attached mal-tooligosaccharides by enzymatic polymerization using potato phosphorylase, which resulted in products with very interesting solution properties [140, 141]. 

I. Sodeberg, C. J. Drummond, D. N. Furlong, S. Godkin, and B. Matthews, Non-ionic sugar-based surfactants Self assembly and air/water interfacial activity, Colloids Surf. A, 102 (1995) 91-97. 

The CBF/NBF transition at pH discussed above was performed at constant ionic strength and capillary pressure. Obviously, such a transition can also be realised when the capillary pressure is altered, for instance, with the Thin Liquid Film-Pressure Balance Technique (see Section 2.1.8). Thus, it is possible to conduct the experiments at lower ionic strength which proves to be important when ri(/i) isotherms of Ci0(EO)4 and NP20 [285], and non-ionic sugar-based surfactants [260] are plotted with respect to pH (see Section 3.4.1). 

Sugar-Based Surfactants Fundamentals and Applications, edited by Cristobal Carnero Ruiz... 

Hill, K., and O. Rhode, Sugar-Based Surfactants for Consumer Products and Technical Applications, Fett/Lipid 101 25-33 (1999). 

Since nonionic carbohydrate-derived surfactants are available in sufficient quantities and at competitive costs at present, anionic versirais of these chemicals such as carboxylates, sulfates, and phosphates are less common. Until now there have been only a few products (anionic derivatives of APG) established in the market [29]. Indeed, the derivatization of neutral sugar-based surfactants to furnish anionic compounds is not easy at a competitive cost with the sulfate (alcohol ether sulfates, AES) and sulfonate (linear alkylbenzene sulfcaiates, LAS) surfactants derived from petrochemicals. Within this context, uronate derivatives possessing carboxylate functionality represent attractive starting materials for the preparation of negatively charged surfactants. 

The principal motivation for studying these sugar-based microemulsion glasses came from the observation that water-oil-surfactant mixtures are extensively for nanomaterials synthesis with the central idea of switching dynamic self-assembly into chemically and mechanically stable supramolecular materials. Template polymerisations are classified as synergistic or transcriptive templating depending on whether the template itself participates in the reaction. 

A highly unexpected result, first reported in 2(X)3, was the efficient adsorption of hydroxide ions at pH values slightly above 7.5 to (almost) uncharged hydrophobic snrfaces and vesicular surfaces formed by reduced-sugar based gemini surfactants. The origin of this phenomenon has been investigated in some detail. ... 

Figure 16.11 Molecular structures of the reduced sugar-based gemini surfactants CSI (a) and CS2 (b). Note the different stereochemistry of the sugar moieties...

L. Wasungu, M. Scarzello, G. van Dam, G. Molema, A. Wagenaar, J. B. F. N. Engberts, D. Hoekstra, Transfection mediated by pH-sensitive sugar-based gemini surfactants potential for in vivo gene therapy applications, J. Mol. Med., 2006, 84, llA-1%4. 

The interest in mesogens based on carbohydrates started only recently, although since 1911 several reports on double melting points of sugar based surfactants are documented in the literature. For the first review on this particular field see [4]. 

Neutron Diffraction - The one example reported this year involved an exploration of the structural features of the liquid-air interface affected by adsorbed sugar-based ionic surfactant 7,7-bis[(l,2,3,4,5-pentahydroxyhexana-mido)-methyl]-n-tridecane. ... 

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