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Materials 2017, 10(8), 913; https://doi.org/10.3390/ma10080913

Hydrophobic Coatings by Thiol-Ene Click Functionalization of Silsesquioxanes with Tunable Architecture

1
Department of Industrial Engineering, University of Trento, via Sommarive 9, 30123 Trento, Italy
2
Sorbonne Universités, UPMC University Paris 06—CNRS—College de France, UMR 7574, Laboratoire de Chimie de la Matière Condensée de Paris, 4 place Jussieu, 75005 Paris, France
*
Authors to whom correspondence should be addressed.
Received: 28 July 2017 / Revised: 4 August 2017 / Accepted: 5 August 2017 / Published: 8 August 2017
(This article belongs to the Special Issue Sol-Gel Chemistry Applied to Materials Science)
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Abstract

The hydrolysis-condensation of trialkoxysilanes under strictly controlled conditions allows the production of silsesquioxanes (SSQs) with tunable size and architecture ranging from ladder to cage-like structures. These nano-objects can serve as building blocks for the preparation of hybrid organic/inorganic materials with selected properties. The SSQs growth can be tuned by simply controlling the reaction duration in the in situ water production route (ISWP), where the kinetics of the esterification reaction between carboxylic acids and alcohols rules out the extent of organosilane hydrolysis-condensation. Tunable SSQs with thiol functionalities (SH-NBBs) are suitable for further modification by exploiting the simple thiol-ene click reaction, thus allowing for modifying the wettability properties of derived coatings. In this paper, coatings were prepared from SH-NBBs with different architecture onto cotton fabrics and paper, and further functionalized with long alkyl chains by means of initiator-free UV-induced thiol-ene coupling with 1-decene (C10) and 1-tetradecene (C14). The coatings appeared to homogeneously cover the natural fibers and imparted a multi-scale roughness that was not affected by the click functionalization step. The two-step functionalization of cotton and paper warrants a stable highly hydrophobic character to the surface of natural materials that, in perspective, suggests a possible application in filtration devices for oil-water separation. Furthermore, the purification of SH-NBBs from ISWP by-products was possible during the coating process, and this step allowed for the fast, initiator-free, click-coupling of purified NBBs with C10 and C14 in solution with a nearly quantitative yield. Therefore, this approach is an alternative route to get sol-gel-derived, ladder-like, and cage-like SSQs functionalized with long alkyl chains. View Full-Text
Keywords: silsesquioxanes; thiol-ene click reaction; in situ water production; hydrophobic coatings; cotton fabric; paper; NMR; wettability silsesquioxanes; thiol-ene click reaction; in situ water production; hydrophobic coatings; cotton fabric; paper; NMR; wettability
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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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Dirè, S.; Bottone, D.; Callone, E.; Maniglio, D.; Génois, I.; Ribot, F. Hydrophobic Coatings by Thiol-Ene Click Functionalization of Silsesquioxanes with Tunable Architecture. Materials 2017, 10, 913.

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