Synthesis and surface measurements of surfactants derived from dehydroabietic acid

Abstract

Dehydroabietates with poly(ethylene oxide) chains of average m = 12, 17, and 45 units [DeHab(E) m ] were synthesized. The adsorption at the liquid-vapor interface was measured, and the adsorbed amount and critical micelle concentrations (CMC) were determined. The foamability, the foam stability, wetting properties, and cloud points, with and without salt content, were studied. The results were compared with common linear alkyl ethoxylates, nonylphenol ethoxylates, and cholesterol ethoxylates. The dehydroabietic acid as hydrophobe was found to result in the same CMC as a linear dodecyl chain. DeHab(E) 45 was found to be insoluble above 400 mg/L, but the surface tensions at lower concentrations were similar to those of the C 11-13 E 38-40 surfactants, which exhibit CMC in aqueous media. The foaming behavior of the DeHab(E) 12 and DeHab(E) 17 surfactants was about the same as for common linear C n E m surfactants. The foamability as well as the foam stability increased with ethylene oxide (EO) chain length. The cloud point was depressed by increased salt concentration and increased with the number of EO units in the head group. The cloud point was significantly lower than for the corresponding surfactant with a dodecyl chain with similar EO chain length. The wetting results, obtained by measuring the contact angle at similar surface tensions, indicate that surfactants of the DeHab(E) m type are more efficient wetting agents than both disaccharide sugar surfactants and C n E m type surfactants.Paper no. S1290 in JSD 6, 125-130 (April 2003).Surfactants derived from natural products, including sugars (1-10) and linear alkyl polyoxyethylene-based surfactants, have been well investigated. On the other hand, there have been relatively few investigations dealing with surfactants based on large natural and rigid skeleton hydrophobes. Recently, sterols (11) and fatty acids (12) have been investigated. Polyoxyethylene-based surfactants using cholesterol (13) and phytosterol (14) have also been investigated. Biological studies of the natural surfactant class of sterolins (15) have been done, but no physicochemical properties have been reported. Surface measurements of a natural saponin, gypsoside (16), and a polyoxyethylene-based rosin acid, dehydroabietic acid (17), also have been carried out.Very little is known about the properties of carbohydrate derivatives of sterols. Such derivatives were, however, recently shown to possess useful synergistic effects in reducing the critical micellar concentration (CMC) of sodium dodecyl sulfate. Furthermore, the derivatives, much like cholesterol, were able to stabilize lipid membranes in liposomes (18).There have been reports of several beneficial biological properties of polyoxyethylene-based sterols. For example, oligo(ethylene oxide)-based phytosterol surfactants have been shown to be both antiprurignous and antiphlogistic, similar to cortisones (19), whereas oligo(ethylene oxide)-based cholesterol and sitosterol surfactants have been shown to lower the uptake of cholesterol when a...

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

“…Only the characteristic spectral peaks of new compounds are presented. More analytical data are found in other sources (13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

“…Alkyl/aryl-D-gluconamides (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) (14,19). In a 50-mL round bottle with stirrer D-(+)-glucono-1,5-lactone (1.78 g, 10 mmol, 1 eq) and a primary or secondary amine (20.0 mmol, 2 eq) are dissolved in dimethylsulfoxide (DMSO) (20 mL).…”

“…The cationic surfactant 19 and the previously reported ethylene oxide-based surfactants 21 and 22 (17) were included for comparison with the novel sugar-based surfactant, 20.…”

Surface properties of surfactants derived from natural products. Part 2: Structure/property relationships—Foaming, dispersion, and wetting

“…Using our new synthetic method, we prepared and characterized a set of glucose amine surfactants (2), 2-deoxy-2-n-octylamino-D-glucose (2) and 1,2-dialkylamino-1,2-dideoxy-D-(N)-β-glucosides: R = bensyl (3), R = octyl (4), and R = hexyl (5). The previously known analog, 1-deoxy-octylamino-D-glucitol (1) (3), was prepared for comparison.…”

Microwave‐Assisted Synthesis and Properties of a Novel Cationic Gemini Surfactant with the Hydrophenanthrene Structure

“…To the best of our knowledge, previous investigations of dehydroabietic acid-based surfactants have been small [20,21]. In this paper, we describe a rapid and convenient approach for synthesis of a biquaternary ammonium salt gemini surfactant with a rosin-based ester bond.…”