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Methacrylated Quinizarin Derivatives for Visible-Light Mediated Photopolymerization: Promising Applications in 3D-Printing Biosourced Materials under LED@405 nm AITranslate

Institut de Chimie et des Matériaux Paris-Est (ICMPE) − UMR-CNRS 7182, Equipe Systèmes Polymères Complexes (SPC); Slovak University of Technology in Bratislava; Slovak University of Technology in Bratislava;Nano Medical Engineering Laboratory;Nano Medical Engineering Laboratory;Politechnico di Torino, Dipartimento di Scienza Applicata e Tecnologia; Université Paris-Est Créteil (UPEC);Institut de Chimie et des Matériaux de Mulhouse (IS2M) -UMR 7361, 15 rue Jean Starcky;Institut de Chimie et des Matériaux Paris-Est (ICMPE) − UMR-CNRS 7182, Equipe Systèmes Polymères Complexes (SPC)
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Publisher: ACS
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Abstract AITranslate

The high initiating properties of mono- (Q-1Ac) and dimethacrylated (Q-2Ac) quinizarin derivatives under visible-light irradiation are reported here. Associated with various co-initiators, such as iodonium salt (electron acceptor), an amine derivative (electron donor), or thiol cross-linker (H-donor), the quinizarin-derived photosensitizers lead to high conversions by radical photopolymerization in laminate or under air. Mechanisms of photoinitiation were deeply investigated by fluorescence, laser flash photolysis (LFP) and electron paramagnetic resonance (EPR) experiments. The use of soybean oil acrylate (SOA) as biobased monomer leads to highly cross-linked materials under visible-light, with comparable mechanical properties than UV-induced ones previously described in literature. Copolymerization of the photosensitizer (PS) with the polymer matrix not only prevents leakage, but also ensures antiadhesion properties of SOA materials against Staphylococcus aureus (S. aureus) under visible-light activation. Finally, complex 3D biobased structures are successfully obtained by 3D-printing under visible-light irradiation (LED@405 nm), opening opportunities to design photoinduced biosourced materials.

KeyWords AITranslate

radical photopolymerization quinizarin 3Dphotoprinting visiblelight irradiation LED irradiation antiadhesion properties
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DOI:https://doi.org/10.1021/acsapm.1c01210

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Citation Information:

The high initiating properties of mono- (Q-1Ac) and dimethacrylated (Q-2Ac) quinizarin derivatives under visible-light irradiation are reported here. Associated with various co-initiators, such as iodonium salt (electron acceptor), an amine derivative (electron donor), or thiol cross-linker (H-donor), the quinizarin-derived photosensitizers lead to high conversions by radical photopolymerization in laminate or under air. Mechanisms of photoinitiation were deeply investigated by fluorescence, laser flash photolysis (LFP) and electron paramagnetic resonance (EPR) experiments. The use of soybean oil acrylate (SOA) as biobased monomer leads to highly cross-linked materials under visible-light, with comparable mechanical properties than UV-induced ones previously described in literature. Copolymerization of the photosensitizer (PS) with the polymer matrix not only prevents leakage, but also ensures antiadhesion properties of SOA materials against Staphylococcus aureus (S. aureus) under visible-light activation. Finally, complex 3D biobased structures are successfully obtained by 3D-printing under visible-light irradiation (LED@405 nm), opening opportunities to design photoinduced biosourced materials.

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GB/T 7714-2015 [1] Louise Breloy, Vlasta Brezová, Zuzana Barbieriková, et al. ACS Applied Polymer Materials, 2022(4). DOI:10.1021/acsapm.1c01210.
MLA [1] Louise Breloy, et al., ACS Applied Polymer Materials, no. 4, 2022, https://doi.org/10.1021/acsapm.1c01210.
APA [1] Louise Breloy, Vlasta Brezová, Zuzana Barbieriková, Yoshihiro Ito, Jun Akimoto, Annalisa Chiappone, Samir AbbadAndaloussi, JeanPierre Malval, & DavyLouis Versace. (2022). ACS Applied Polymer Materials(4). https://doi.org/10.1021/acsapm.1c01210
IEEE [1] Louise Breloy, Vlasta Brezová, Zuzana Barbieriková, Yoshihiro Ito, Jun Akimoto, Annalisa Chiappone, Samir AbbadAndaloussi, JeanPierre Malval, and DavyLouis Versace, ACS Applied Polymer Materials, no. 4, 2022, doi: 10.1021/acsapm.1c01210. keywords: {radical photopolymerization;quinizarin;3Dphotoprinting;visiblelight irradiation;LED irradiation;antiadhesion properties}