Amphiphilic Graft Copolymers for Time-Delayed Release of Hydrophobic Fragrances.

Abstract

When a controlled or retarded release of perfumes is required such as in cosmetics or cleaning products, polymers can be applied as encapsulation agents. With regard to such applications, we investigated two amphiphilic graft copolymers featuring a polydehydroalanine (PDha) backbone and different hydrophobic side chains. Hereby, grafting of aliphatic octyl side chains (PDha-g-EOct) enabled the adsorption of the aliphatic fragrance tetrahydrolinalool with moderate loads, whereas benzyl side chains (PDha-g-BGE) allowed taking up aromatic fragrances, for example, amylsalicylate-n with exceptionally high loads of up to 8 g g-1. The side-chain density was studied as well but had no significant influence on the loading. In addition, the characterization and quantification of the load by NMR and thermogravimetric analysis were compared, and it was also possible to load the aromatic model fragrance into the graft copolymer with aliphatic side chains. After 3 months, the load had decreased by 40-50% and, hence, such systems are of interest for a long-term release of perfumes over months. Although this study is a proof-of-concept, we foresee that such polyampholytic graft copolymers can be tailored for the adsorption of a variety of hydrophobic perfumes simply by altering polarity and chemistry of the side chain.