New Ethoxylated Inositol Surfactant

Abstract

Carbohydrates are an attractive class of starting materials for organic syntheses because they are of natural origin, environmentally friendly, and highly functionalized, in this way promoting a sustainable chemistry. A somewhat exotic but nevertheless readily available family of carbohydrates allowing a fascinating chemistry are inositols (cyclohexane-1,2,3,4,5,6-hexols), which we currently use for the synthesis of new surfactants. In our previous work, we reported on the synthesis of a number of new regiochemically defined myo-inositol ethers and esters and studied their surface activity in aqueous solution as well as their ability to form thermotropic liquid crystals. It turned out that the hydrophilicity of the myo-inositol head group alone does not ensure sufficient water solubility of these surfactants. To improve the water solubility, we increased the inositol head group by the introduction of a tri(ethylene oxide) unit. The resulting surfactant is the first representative of a new class of inositol-based surfactants (CiEjIk) that combine the properties of classical sugar surfactants (CnGm) and oligo(ethylene oxide) alkyl ether surfactants (CiEj).

Mixtures of n-dodecyl-β-d-maltoside and hexaoxyethylene dodecyl ether — Surface properties, bulk properties, foam films, and foams

“…Another type of hitherto marginally studied surfactants is surfactants in which carbohydrate and oxyethylene units are chemically combined into one hydrophilic head group [73]. This leads to new properties and a different behaviour of the resulting "hybrid surfactants" since in many respects the two molecular groups (carbohydrates or oxyethylene units, respectively) usually behave in opposite ways as outlined in the Introduction.…”

“…A surfactant with a head group consisting of three ethylene oxide units and an inositol unit is an interesting alternative to the classical glucose units as it has the same molecular formula as conventional hexoses C 6 H 12 O 6 , but a different molecular structure (see Section 6.3 for details). Surface tension studies on this surfactant revealed that its surface activity is "between" that of the pure C 12 E 6 and β-C 12 G 2 , respectively [73], which is a very nice example of a "structureproperty-relationship" and opens the arena for a new family of surfactants [71,72]. Molecular simulation techniques cannot only be used to complement these studies but they also offer a more time and cost effective means compared with experiment.…”

Synthesis and photoswitching properties of liquid crystals derived from myo-inositol

“…The most prominent form is cis-1,2,3,5-trans-4,6-cyclohexanehexol or myoinositol, having one axial and ve equatorial hydroxyl functions, which is a cheap and easily available compound with stable conformational geometry of the chair conformation. 1,2 Although the thermotropic liquid crystalline properties of inositol alkyl ethers have been studied by several researchers, [3][4][5] there are a limited number of reports on the liquid crystal behaviour of materials derived from inositol molecules. Inositol-based molecules have diverse options for modication and tuning of specic properties in biological and chemical systems.…”

Syntheses, Amphitropic Liquid Crystallinity, and Surface Activity of New Inositol-Based Amphiphiles

“…It is noteworthy that since the beginning of the eighties amphiphilic carbohydrates, cyclitol monoethers, and cyclitol monoesters have attracted increasing attention because of their thermotropic and lyotropic properties, because of their surface activity, and because of the fact that they are environmentally benign. Inositols have been used as hydrophilic headgroups in amphiphilic molecules, but up to now mainly the thermotropic liquid crystalline properties of the respective alkyl monoethers have been studied in detail. − Furthermore, some regioisomeric mixtures of myo- inositol monoesters with long side chains have been synthesized, and the surface activity of these compounds has been studied . It was only recently that the properties of a regiochemically pure inositol derivative in aqueous solution were studied.…”

“…It was only recently that the properties of a regiochemically pure inositol derivative in aqueous solution were studied. The combination of a polyethylene glycol and an inositol unit in the hydrophilic headgroup of this derivative led to very interesting features …”