Oligomeric Photocatalysts in Photoredox Catalysis: Toward High Performance and Low Migration Polymerization Photoinitiating Systems.

Ay, Emel; Raad, Zaher; Dautel, Olivier; Dumur, Frédéric; Wantz, Guillaume; Gigmès, Didier; Fouassier, Jean‐Pierre; Lalevée, Jacques

doi:10.1021/acs.macromol.5b02760

Cited by 26 publications

(19 citation statements)

References 75 publications

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“…[20,21] In recent years, some photoinitiators decorated by polymerizable groups have been reported. [22][23][24] Thomas Griesser [25] and co-workers designed two type I photoinitiators substituted by alkyne groups, which can participate in thiol/alkyne addition reactions, and thus show low migration properties in such formulations. Zhao [22] prepared a bifunctional polymerizable photoinitiator by introducing two acrylate groups onto a cyclopentanone derivative.…”

Section: Introductionmentioning

confidence: 99%

Polymerizable Oxime Esters: An Efficient Photoinitiator with Low Migration Ability for 3D Printing to Fabricate Luminescent Devices

Qiu

Zhu²,

Dietliker

et al. 2020

ChemPhotoChem

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The development of novel visible light photoinitiators (PIs) with low mobility for 3D printing will open up new applications for photopolymerization. In this work, a polymerizable visible light PI DCCA containing an oxime acryloyl ester structure was designed and synthesized. Its linear absorption has a maximum in the visible region (400-480 nm), overlapping well with the emission spectra of conventional blue light sources, and it can effectively induce acrylate polymerization under irradiation with a 450 nm LED lamp. In addition, migration of DCCA in the 3D printed samples is very low compared with DCCB, which has a similar structure but a phenyl moiety instead of the copolymerizable acrylate as the oxime ester group. The utility of DCCA in 3D printing was demonstrated by printing a 3D object with challenging geometric features with high resolution and accuracy.

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Section: Introductionmentioning

confidence: 99%

Polymerizable Oxime Esters: An Efficient Photoinitiator with Low Migration Ability for 3D Printing to Fabricate Luminescent Devices

Qiu

Zhu²,

Dietliker

et al. 2020

ChemPhotoChem

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“…This low migration property of ketone-5 is probably ascribed to both the highly crosslinked network of polymer structure and the presence of reactive C=C double bond in the peripheral substituting group, which could be involved in a copolymerization reaction with the acrylate functions of TA. 19 Therefore, the 1,3bis(allyloxy)benzene substituted ketone derivatives introduced in this work can demonstrate satisfactory migration stability.…”

Section: Migration Study Of Ketonesmentioning

confidence: 82%

“…Despite the promising prospect of high photoinitiation efficiency, the extractability of small molecule-based initiators remains a key issue, since the migration of unreacted species to the surface of photocured polymers can cause potential impediment for the future application of resulting polymer materials. 18,19 The ketone moiety is well-known for its absorption in the visible/near UV region. Previously, we have developed several series of ketones derivatives as photoinitiators for the photopolymerization upon visible LED irradiation.…”

Section: Introductionmentioning

confidence: 99%

Allyloxy ketones as efficient photoinitiators with high migration stability in free radical polymerization and 3D printing

Noirbent

Brunel

et al. 2021

Dyes and Pigments

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Five ketone derivatives (ketone-1~ketone-5) never synthesized in the literature and containing the same peripheral 1,3-bis(allyloxy)benzene substituting group but different central cyclohexanone cores were designed and proposed as highperformance photoinitiators for the free radical polymerization of acrylates under mild conditions. In combination with an amine and an iodonium salt (Iod), these ketones could initiate the photopolymerization of di(trimethylolpropane) tetraacrylate (TA), a tetrafunctional acrylates monomer, upon visible LED irradiation at room temperature in both thick films (1.4 mm) and thin films (25 μm) conditions. The distinct photopolymerization profiles of acrylates were studied by real time Fourier transform infrared spectroscopy, which indicated that the ketone-2/amine/Iod system could induce the highest final conversion of acrylates in thick films condition, while ketone-5/amine/Iod system could induce the highest final conversion of acrylates in thin films condition. Photoreactivity of ketone-2 and ketone-5 was systematically investigated by steady state photolysis and fluorescence quenching experiments in the presence of an amine and an iodonium salt, respectively. Moreover, eminent migration stability of ketones in photocured TA was observed. Finally, the ketone-2 and ketone-5-based three-component photoinitiating systems were applied for the laser writing experiments of TA, and macroscopically tridimensional patterns were fabricated with an excellent spatial resolution.

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“…Recently, this strategy was also used to design the polymerizable oligomer system. Jacques Lalevée reported an oligomeric and copolymerizable photocatalyst PVD2 with a proper molecular weight and the reactive double bonds as end groups. Results showed that PVD2 not only exhibited excellent photopolymerization performance in free radical polymerization, cationic polymerization, and in the synthesis of interpenetrating polymer networks, but also could ensure a very low migration of the catalyst from the synthesized polymer.…”

Section: Introductionmentioning

confidence: 99%

High‐Performance and Low Migration One‐Component Thioxanthone Visible Light Photoinitiators

Tang

Xiong

et al. 2017

Macro Chemistry & Physics

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Two thioxanthone based acrylated one‐component visible light photoinitiators, 2‐(methyl(4‐((methyl(9‐oxo‐9H‐thioxanthen‐2‐yl)amino)methyl)benzyl)amino)ethyl acrylate (TX‐EA) and ((4‐((methyl(9‐oxo‐9H‐thioxanthen‐2‐yl)amino)methyl)benzyl)azanediyl)bis(ethane‐2,1‐diyl)diacrylate (TX‐BDA), are designed and synthesized. The results of photopolymerization and migration study demonstrate that TX‐EA and TX‐BDA are more effective one‐component visible light photoinitiators for free radical polymerization with excellent migration stability than 4‐((methyl(9‐oxo‐9H‐thioxanthen‐2‐yl)amino)methyl)phenyl acrylate. The mass fraction of the extracted TX‐BDA in a cured 1,6‐hexanediol diacrylate polymer film is as low as 0.55% and the residual amount is estimated to be only 90 ppm. TX‐BDA would have great potential to be used in visible light curing systems, particularly in the food packing or biomedical fields. Results demonstrate that the synergistic effect of hydrogen donors and polymerizable groups in photoinitiator plays an important role in realizing high performance and low migration in photopolymerization system.

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Oligomeric Photocatalysts in Photoredox Catalysis: Toward High Performance and Low Migration Polymerization Photoinitiating Systems.

Cited by 26 publications

References 75 publications

Polymerizable Oxime Esters: An Efficient Photoinitiator with Low Migration Ability for 3D Printing to Fabricate Luminescent Devices

Polymerizable Oxime Esters: An Efficient Photoinitiator with Low Migration Ability for 3D Printing to Fabricate Luminescent Devices

Allyloxy ketones as efficient photoinitiators with high migration stability in free radical polymerization and 3D printing

High‐Performance and Low Migration One‐Component Thioxanthone Visible Light Photoinitiators

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