Multifunctional quaternary ammonium surfactants with controlled release of carbonyl perfumes

Abstract

The development of structurally diversified surfactants with multifunctional performance is an important task. Herein, we report a series of quaternary ammonium salts (QAS) as surfactants with hydrazone linker between a long chain and a triggered release of various fragrances. The resulting QAS with build-in aldehydes as a carrier of fragrances exhibited excellent amphiphilicity in water, their surface activity is evaluated by testing surface tension of the micelles in water with γ-CMC values ranging from 16.19 to 38.02 mN/m. Releasing performance by hydrolysis of hydrazones, meanwhile the formation of hydrazine derivatives as dynamic mixtures in acidic aqueous solutions, is investigated by headspace solid-phase micro-extraction (SPME) in combination with gas chromatography (GC) analysis, the results showed significant retention capacity for volatile aldehydes in up to 25 times higher than the neat reference of the corresponding aldehydes. The antibacterial performance of QAS is expressed by the minimum inhibitory concentration (MIC) values, along with an excellent activity on Gram-positive bacteria in the lowest concentration of 2 μg/mL. These QAS could be regarded as suitable fragrance delivery system in potential applications.