Nonionic ortho ester surfactants as cleavable emulsifiers.

Acid labile surfactants containing an ortho ester link are used as emulsifiers for an aliphatic oil, squalane. The emulsions were made in the presence of a cationic polymer, either polyamine or the corresponding hydrophobically modified polyamine. Spontaneous hydrolysis of the surfactant resulted in emulsions stabilized by polymer together with degradation products from the surfactant. The effect of breakdown of the surfactant on the emulsion was evaluated by means of droplet size measurements and kinetic stability. One linear and one branched nonionic ortho ester surfactant with the same number of oxyethylene units were characterized and used for the purpose. The ortho ester surfactants are complex mixtures of components, ranging from very hydrophilic to very hydrophobic species. The chemical shift of the central methine proton in the ortho ester link is extremely sensitive to the substitution pattern and it was possible to identify by (1)H NMR the components that make up the surfactants, as has been reported earlier. The change in emulsion stability, the change in droplet size and the rate of surfactant hydrolysis were studied at acidic pH at room temperature. Both gas chromatography and (1)H NMR were used in order to monitor the surfactant degradation. The presence of a polymer gave a more sluggish breakdown of the surfactants, probably due to hydrophobic shielding by the polymer. There was a good correlation between increase of droplet size and degree of surfactant decomposition.