Functionally polymerized surfactant vesicles. Synthesis and characterization

Abstract

ethyl]dimethylammonium bromide (1), bis [2-(10-undecenoyloxycarbonyl)ethyl](2-hydroxyethyl)methylammonium bromide (2), bis [2-(10-undecenoyloxycarbonyl)ethyl]amidophosphoric acid (3), bis[2-(10-undecenoyloxycarbonyl)ethyl]-2-sulfoethylamine (4), allylbis[2-(dodecanoyloxycarbonyl)ethyl]methylammonium bromide (5), and dimethyl-«-hexadecyl [10-(p-vinylcarboxanilido)decyl]ammonium bromide (6) have been synthesized. The predominantly single compartment bilayer vesicles formed from these surfactants could be polymerized either by exposure to ultraviolet irradiation or by the use of azoisobutyronitrile (AIBN) as an initiator. The presence of vesicles (unpolymerized and polymeric) has been demonstrated by electron micrography, 'H NMR, gel filtration, phase transition, turbidity changes, substrate entrapment, and permeability. Rates of light initiated polymerization of vesicles prepared from 6 have been found to be first order (k = 0.10 min"1 at 25 °C; [6] = 0.33 and 0.20 mg/1.0 mL of H20) and independent of the concentration of 6. Under identical conditions, polymerization of 6 in methanol has occurred at a very much slower rate, and no polymerization has been observed at higher concentrations (2 mg of 6/2 mL of MeOH). Polymerized vesicles are considerably more stable and less permeable and have reduced rates of turbidity changes compared to their unpolymerized counterparts.Completely synthetic surfactant vesicles1 are increasingly being utilized in photochemical solar energy conversion,2 reactivity

Morphology and viscoelasticity of bilayer aqueous colloids of low-molecular and macromolecular amphiphiles

“…Allylbis [2-(dodecanoyloxycarbonyt)ethyl]methylammonium bromide (ADM) was synthesized according to the procedure shown [10,14]. Preparation and purification of ADM were confirmed with 1HNMR, IR and elemental analysis.…”

Complementary Liposomes Based on Phosphatidylcholine: Interaction Effectiveness vs Protective Coating

“…Specifically the PC-CHOL liposomes were disrupted by the addition of about 25% (v/v) ethanol, while liposomes containing recognizable moieties were disrupted by the addition of 40-50% (v/v) ethanol. Since normally the addition of ethanol leads to a decrease of absorbance (49,50), the observed enhancement of absorbance due to the disruption of the liposomes can only be attributed to the liberation of cholesterol crystallites. The latter remain dispersed in the resulting water/ethanol mixture, giving rise to the increased absorbance.…”

“…The stability of the initially prepared liposomes was evaluated by the well-established turbidity method reported several years ago (49,50). Thus in Fig.…”

Interaction between amphiphiles and water molecules in concentrated bilayer aqueous colloids

“…DMA was purchased from Kanto Chemical (Tokyo). ADM was synthesized according to the procedure shown in Tundo et al [15]. Preparation and purification of ADM were confirmed with NMR, IR, and elemental analysis.…”