3-Hydroxyflavone and N-Phenylglycine in High Performance Photoinitiating Systems for 3D Printing and Photocomposites Synthesis

Assi Al Mousawi 1 Patxi Garra 1 Michael Schmitt 1, 2 Joumana Toufaily 3 Tayssir Hamieh 3 Bernadette Graff 1 Jean Pierre Fouassier 1 Frédéric Dumur 4 Jacques Lalevee 1
1 IS2M - Institut de Science des Matériaux de Mulhouse
2 UNISTRA - Université de Strasbourg
3 MCEMA - Laboratory of Materials, Catalysis, Environment and Analytical Methods
4 ICR - Institut de Chimie Radicalaire
Abstract : We propose to use 3-hydroxyflavone as a versatile high performance visible light photoinitiator (PI) in combination with an amino acid (N-phenylglycine) for the free radical polymerization (FRP) of methacrylates in thick samples (e.g., 3D printing) or composites upon visible light exposure (light-emitting diode LED@405 nm or LED@477 nm). The high originality of this approach is the use of safer compounds in photoinitiating systems (combination flavone derivative/amino acid). 3-Hydroxyflavone can also be used in three-component systems with an iodonium salt and an amine for the cationic polymerization of epoxides upon exposure to near-UV light LED@385 nm. Also interestingly, a charge transfer complex (CTC) between N-phenylglycine NPG and iodonium salt gives also remarkable initiating performance for free radical polymerization of methacrylates upon mild light irradiation conditions (LED@405 nm). High polymerization initiating abilities are found, and high final reactive function conversions are obtained. The use of the new proposed initiating systems as materials for laser write or 3D printing experiments was also especially carried out with the formation of printed green fluorescent photopolymers. This green fluorescence obtained with naturally occurring 3-hydroxyflavone compound can be ascribed to the excited state intramolecular proton transfer ESIPT character. A full picture of the included photochemical mechanisms is given. Remarkably, the 3-hydroxyflavone/amino acid system is also very efficient for photocomposites synthesis with glass fibers (thick samples with good depth of cure) using UV or LED@395 nm conveyor.
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Journal articles
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https://hal-amu.archives-ouvertes.fr/hal-02091898
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Submitted on : Saturday, April 6, 2019 - 5:17:29 PM
Last modification on : Wednesday, November 13, 2019 - 11:50:04 AM

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Assi Al Mousawi, Patxi Garra, Michael Schmitt, Joumana Toufaily, Tayssir Hamieh, et al.. 3-Hydroxyflavone and N-Phenylglycine in High Performance Photoinitiating Systems for 3D Printing and Photocomposites Synthesis. Macromolecules, American Chemical Society, 2018, 51 (12), pp.4633--4641. ⟨10.1021/acs.macromol.8b00979⟩. ⟨hal-02091898⟩

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