Design of Stimuli‐Responsive Dynamic Covalent Delivery Systems for Volatile Compounds (Part 2): Fragrance‐Releasing Cleavable Surfactants in Functional Perfumery Applications

Abstract

Amphiphilic imines prepared by condensation of a hydrophobic fragrance aldehyde with a hydrophilic amine derived from a poly(propylene oxide) and poly(ethylene oxide) diblock copolymer were investigated as cleavable surfactant profragrances in applications of functional perfumery. In water, the cleavable surfactants assemble into micelles that allow solubilization of perfume molecules that are not covalently attached to the surfactant. Dynamic headspace analysis on a glass surface showed that solubilized perfume molecules evaporated in a similar manner in the presence of the cleavable surfactant as compared with a non-cleavable reference surfactant. Under application conditions, the cleavable surfactant imine hydrolysed to release the covalently linked fragrance aldehyde. The profragrances were stable during storage in aqueous media, and upon dilution showed a blooming effect for the hydrolytical fragrance release and a more balanced performance of a solubilized perfume by retaining the more volatile fragrances and boosting the evaporation of the less volatile fragrances.

Construction of Supramolecular Systems That Achieve Lifelike Functions

“…Giuseppone and co-workers reported that aldehydes, which are components of fragrances, attach to the terminal amine of polyethylene glycol-polyphenylene oxide surfactants to form micelles and that the fragrance components are released from the micelles when hydrolysis proceeds under specific pH conditions [ 54 ]. When various oil components were solubilized as fragrances, the more volatile oil components were more easily retained inside the micelles, and evaporation of the less volatile components was accelerated [ 55 ]. This is an interesting example of how the balance of release of solubilized fragrance components can be controlled.…”

Controlled Hydrolysis of Odorants Schiff Bases in Low-Molecular-Weight Gels

“…In this scenario, Schiff bases (SB) represent valid profragrances that can be synthesized starting from odorant aldehydes and primary amines through a condensation reaction [ 14 , 15 , 16 ]. The reaction is reversible, and the SB can be readily hydrolyzed to the starting materials in aqueous environments, mainly in acidic conditions [ 17 ].…”

Responsive packaging based on imine-chitosan films for extending the shelf-life of refrigerated fresh-cut pineapple

“…Currently, the use of reversible covalent bonds is being explored in different fields for multiple purposes (Huang et al, 2020) including the design of smart release systems of bioactives (Chen et al, 2020;Fadida, Selilat-Weiss, & Poverenov, 2015;Rizzo & Kehr, 2021;Tchakalova et al, 2021;Zentner, Anson, Thayumanavan, & Swager, 2019).…”