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Open AccessFeature PaperArticle

Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing

1
CNRS, IS2M UMR 7361, Université de Haute-Alsace, F-68100 Mulhouse, France
2
Université de Strasbourg, 67081 Strasbourg, France
3
Laboratory of Materials, Catalysis, Environment and Analytical Methods (MCEMA) and LEADDER Laboratory, Faculty of Sciences, Doctoral School of Sciences and Technology (EDST), Lebanese University, Beirut 6573-14, Lebanon
4
SATIE-IFSTTAR, Université Gustave Eiffel, Campus de Marne-La-Vallée, F-78000 Versailles, France
5
CNRS, ICR UMR 7273, Aix Marseille Université, F-13397 Marseille, France
*
Authors to whom correspondence should be addressed.
Catalysts 2020, 10(10), 1202; https://doi.org/10.3390/catal10101202
Received: 26 September 2020 / Revised: 9 October 2020 / Accepted: 13 October 2020 / Published: 17 October 2020
(This article belongs to the Section Catalysis in Organic and Polymer Chemistry)
This work is devoted to investigate three coumarin derivatives (Coum1, Coum2, and Coum3), proposed as new photoinitiators of polymerization when combined with an additive, i.e., an iodonium salt, and used for the free radical polymerization (FRP) of acrylate monomers under mild irradiation conditions. The different coumarin derivatives can also be employed in three component photoinitiating systems with a Iod/amine (ethyl 4-dimethylaminobenzoate (EDB) or N-phenylglycine (NPG)) couple for FRP upon irradiation with an LED @ 405 nm. These compounds showed excellent photoinitiating abilities, and high polymerization rates and final conversions (FC) were obtained. The originality of this work relies on the comparison of the photoinitiating abilities of monofunctional (Coum1 and Coum2) vs. difunctional (Coum3) compounds. Coum3 is a combined structure of Coum1 and Coum2, leading to a sterically hindered chemical structure with a relatively high molecular weight. As a general rule, a high molecular weight should reduce the migration of initiating molecules and favor photochemical properties such as photobleaching of the final polymer. As attempted, from the efficiency point of view, Coum3 can initiate the FRP, but a low reactivity was observed compared to the monofunctional compound (Coum1 and Coum2). Indeed, to study the photochemical and photophysical properties of these compounds, different parameters were taken into account, e.g., the light absorption and emission properties, steady state photolysis, and fluorescence quenching. To examine these different points, several techniques were used including UV-visible spectroscopy, real-time Fourier Transform Infrared Spectroscopy (RT-FTIR), fluorescence spectroscopy, and cyclic voltammetry. The photochemical mechanism involved in the polymerization process is also detailed. The best coumarins investigated in this work were used for laser writing (3D printing) experiments and also for photocomposite synthesis containing glass fibers. View Full-Text
Keywords: free radical polymerization; mild irradiation conditions; coumarins; composite materials; LED; 3D printing free radical polymerization; mild irradiation conditions; coumarins; composite materials; LED; 3D printing
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MDPI and ACS Style

Rahal, M.; Mokbel, H.; Graff, B.; Toufaily, J.; Hamieh, T.; Dumur, F.; Lalevée, J. Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing. Catalysts 2020, 10, 1202.

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