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Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery
Division Recherche & Développement, Firmenich SA, Route des Jeunes 1, B.P. 239, Genève 8 1211, Switzerland
* Author to whom correspondence should be addressed.
Received: 23 January 2013; in revised form: 18 February 2013 / Accepted: 19 February 2013 / Published: 22 February 2013
Abstract: Poly(styrene-co-maleic anhydride)s were modified with poly(propylene oxide (PO)-co-ethylene oxide (EO)) side chains (Jeffamine®) with different EO/PO molar ratios, varying between 0.11 and 3.60. These copolymers were then further functionalized with a β-mercapto ketone of δ-damascone. The obtained poly(maleic acid monoamide)-based β-mercapto ketones were then studied as delivery systems for the controlled release of δ-damascone by retro 1,4-addition. The release of δ-damascone, a volatile, bioactive molecule of the family of rose ketones, was studied by dynamic headspace analysis above a cotton surface after deposition of a cationic surfactant containing fabric softening formulation, as a function of the ethylene oxide (EO)/propylene oxide (PO) molar ratio of the grafted copolymer side chains. The polarity of the EO/PO side chain influenced the release efficiency of the damascone in a typical fabric softening application. PO-rich copolymers and the corresponding poly(styrene-co-maleic anhydride) without Jeffamine® side chains were found to be less efficient for the desired fragrance release than the corresponding bioconjugate with a EO/PO ratio of 3.60 in the side chain. This copolymer conjugate seemed to represent a suitable balance between hydrophilicity and hydrophobicity to favor the release of the δ-damascone and to improve the deposition of the conjugate from an aqueous environment onto a cotton surface.
Keywords: controlled release; damascones; fragrances; headspace analysis; Jeffamines; polymer conjugates; poly(maleic anhydride); profragrances; retro 1,4-additions; thioethers
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Berthier, D.L.; Paret, N.; Trachsel, A.; Fieber, W.; Herrmann, A. Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery. Polymers 2013, 5, 234-253.
Berthier DL, Paret N, Trachsel A, Fieber W, Herrmann A. Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery. Polymers. 2013; 5(1):234-253.
Berthier, Damien L.; Paret, Nicolas; Trachsel, Alain; Fieber, Wolfgang; Herrmann, Andreas. 2013. "Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery." Polymers 5, no. 1: 234-253.