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Polymers 2013, 5(1), 234-253; doi:10.3390/polym5010234
Article

Controlled Release of Damascone from Poly(styrene-co-maleic anhydride)-based Bioconjugates in Functional Perfumery

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Received: 23 January 2013; in revised form: 18 February 2013 / Accepted: 19 February 2013 / Published: 22 February 2013
(This article belongs to the Special Issue Bioconjugates/Biohybrid Polymers)
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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 controlled release; damascones; fragrances; headspace analysis; Jeffamines; polymer conjugates; poly(maleic anhydride); profragrances; retro 1,4-additions; thioethers
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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