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Molecular Design of Microcapsule Shells for Visible Light-Triggered Release

Department of Chemical Engineering, Rovira i Virgili University, Av. Països Catalans 26, 43007 Tarragona, Spain
Centre Tecnològic de la Química de Catalunya, Carrer Marcelli Domingo s/n, 43007 Tarragona, Spain
Procter & Gamble Services Company n.v., Temselaan 100, 1853 Strombeek-Bever, Belgium
Department of Chemical, Materials, and Production Engineering (DICMAPI), University of Naples “Federico II”, P. le Tecchio, 80, 80125 Napoli, Italy
The Procter and Gamble Company, 6210 Center Hill Avenue, Cincinnati, OH 45224, USA
Author to whom correspondence should be addressed.
Polymers 2019, 11(5), 904;
Received: 23 April 2019 / Revised: 13 May 2019 / Accepted: 14 May 2019 / Published: 17 May 2019
(This article belongs to the Special Issue Photoresponsive Polymeric Materials)
PDF [5794 KB, uploaded 17 May 2019]


The development of photo-responsive capsules to tune and control the sustained-release of encapsulated actives is a fascinating and challenging route to improve the performances and effectiveness of a wide range of delivery applications. In this work, we report the preparation of visible light-responsive capsules obtained via oil-in-water interfacial polycondensation between modified diacyl-chloride azobenzene moiety and diamine flexible spacer in the presence of cross-linkers with different structures and functionalities. The effect on the release profile of the encapsulated perfume oil was investigated using three flexible spacers with different lengths (1,8-diaminooctane; 1,6-diaminohexane and 1,4-diaminobutane) and two types of cross-linkers (1,3,5-benzenetricarbonyl trichloride and melamine). We analyzed how the properties of microcapsules can be tailored changing the design of the shell structure. Fine tuning of the perfume release profiles was obtained. The changes in capsules size and morphology due to visible light irradiation were monitored via light scattering, optical microscopy and atomic force microscopy. Perfume release was 50% faster in the systems prepared with melamine as the cross-linker. Modelling studies were carried out to support the discussion of the experimental results. View Full-Text
Keywords: encapsulation; photo-triggered release; modified azobenzene encapsulation; photo-triggered release; modified azobenzene

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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 (CC BY 4.0).

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Pirone, D.; Marturano, V.; Del Pezzo, R.; Fernández Prieto, S.; Underiner, T.; Giamberini, M.; Tylkowski, B. Molecular Design of Microcapsule Shells for Visible Light-Triggered Release. Polymers 2019, 11, 904.

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