Coumarin Derivatives as Photoinitiators in Photo-Oxidation and Photo-Reduction Processes and a Kinetic Model for Simulations of the Associated Polymerization Profiles

Abdallah, Mira; Hijazi, Akram; Lin, Jenn-Wei; Graff, Bernadette; Dumur, Frédéric; Lalevée, Jacques

doi:10.1021/acsapm.0c00340

Cited by 32 publications

(46 citation statements)

References 47 publications

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“…These obtained patterns were further observed and analyzed by numerical optical microscopy, as shown in Figure 8. The step width between the photocured and non‐cured resin was about 50 μm, which is in accordance with the spot size of the laser, thus exemplifying an excellent spatial resolution for the products 36,37 . The 3D printing results of TA induced by ketone–1, in turn, reflect the high photoinitiation efficiency of ketone derivatives and broaden the potential application prospect.…”

Section: Resultssupporting

confidence: 60%

“…The scale bar is 4,000 μm [Color figure can be viewed at wileyonlinelibrary.com] 50 μm, which is in accordance with the spot size of the laser, thus exemplifying an excellent spatial resolution for the products. 36,37 The 3D printing results of TA induced by ketone-1, in turn, reflect the high photoinitiation efficiency of ketone derivatives and broaden the potential application prospect.…”

Section: D Printing Experiments Through Direct Laser Writementioning

confidence: 93%

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Design of ketone derivatives as highly efficient photoinitiators for free radical and cationic photopolymerizations and application in 3D printing of composites

Ding

Zhu

et al. 2020

Journal of Polymer Science

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Herein, thirteen ketone derivatives composed of different cyclohexanone cores and peripheral moieties are designed, among which 10 ketones have never been synthesized before. These ketones are proposed as high‐performance photoinitiators for both free radical polymerizations and cationic polymerizations under soft conditions (visible LED@405 nm irradiation at room temperature). In combination with an amine and an iodonium salt (Iod), these ketones could be used in three−component photoinitiating systems to initiate the free radical polymerization of acrylates with distinct final conversions, among which the ketone−1/amine/Iod combination proved to be the most efficient one. Besides, the ketone−1/Iod two−component system also showed a remarkable photoinitiation ability for the cationic polymerization of epoxides. The photochemical sensitivity of ketone−1 in the presence of an amine and an iodonium salt was systematically investigated by steady state photolysis and excited state fluorescence quenching characterizations, respectively. Interestingly, macroscopic 3D patterns with excellent spatial resolution could be generated using the ketone−1/amine/Iod photoinitiating system for the free radical polymerization of acrylates. This high performance is also found useful to overcome the light penetration issue for the access to filled samples (silica) and the preparation of composites.

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Section: Resultssupporting

confidence: 60%

Section: D Printing Experiments Through Direct Laser Writementioning

confidence: 93%

Design of ketone derivatives as highly efficient photoinitiators for free radical and cationic photopolymerizations and application in 3D printing of composites

Ding

Zhu

et al. 2020

Journal of Polymer Science

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“…Associated with the photolysis of BPC1/Iod and BPC1/EDB/Iod, the photoredox catalytic cycle was proposed in three-component PI/EDB/Iod system ( Scheme 3 , r5 and r6). The regeneration of PI speeds up the photopolymerization and slows down the consumption of PI in the photolysis experiments [ 41 , 42 ].…”

Section: Discussionmentioning

confidence: 99%

Monocomponent Photoinitiators based on Benzophenone-Carbazole Structure for LED Photoinitiating Systems and Application on 3D Printing

et al. 2020

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In this article, different substituents (benzoyl, acetyl, styryl) are introduced onto the carbazole scaffold to obtain 8 novel carbazole derivatives. Interestingly, a benzoyl substituent, connected to a carbazole group, could form a benzophenone moiety, which composes a monocomponent Type II benzophenone-carbazole photoinitiator (PI). The synergetic effect of the benzophenone moiety and the amine in the carbazole moiety is expected to produce high performance photoinitiating systems (PISs) for the free radical photopolymerization (FRP). For different substituents, clear effects on the light absorption properties are demonstrated using UV-Visible absorption spectroscopy. Benzophenone-carbazole PIs can initiate the FRP of acrylates alone (monocomponent Type II photoinitiator behavior). In addition, fast polymerization rates and high function conversions of acrylate are observed when an amine and/or an iodonium salt are added in systems. Benzophenone-carbazole PIs have good efficiencies in cationic photopolymerization (CP) upon LED @ 365 nm irradiation in the presence of iodonium salt. In contrast, other PIs without synergetic effect demonstrate unsatisfied photopolymerization profiles in the same conditions. The best PIS identified for the free radical photopolymerization were used in three-dimensional (3D) printing. Steady state photolysis and fluorescence quenching experiments were carried out to investigate the reactivity and the photochemistry and photophysical properties of PIs. The free radicals, generated from the studied PISs, are detected by the electron spin resonance - spin trapping technique. The proposed chemical mechanisms are provided and the structure/reactivity/efficiency relationships are also discussed. All the results showed that the benzophenone-carbazole PIs have a good application potential, and this work provides a rational design route for PI molecules. Remarkably, BPC2-BPC4, C6, C8 were never synthetized before; therefore, 5 of the 8 compounds are completely new.

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“…In this paper, nine coumarin derivatives (noted Coum in Scheme 1 ) varying by the substitution pattern at the 3- and 7-positions of the coumarin core were synthesized and evaluated as photoinitiators for the FRP of acrylate and methacrylate monomers. In fact, coumarin derivatives have already been tested as photoinitiators of FRP and they have shown good polymerization profile (Rp and FC) as well as good photochemical and photophysical properties [ 15 , 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

3-Carboxylic Acid and Formyl-Derived Coumarins as Photoinitiators in Photo-Oxidation or Photo-Reduction Processes for Photopolymerization upon Visible Light: Photocomposite Synthesis and 3D Printing Applications

et al. 2021

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In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical photopolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2) was also examined.

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Coumarin Derivatives as Photoinitiators in Photo-Oxidation and Photo-Reduction Processes and a Kinetic Model for Simulations of the Associated Polymerization Profiles

Cited by 32 publications

References 47 publications

Design of ketone derivatives as highly efficient photoinitiators for free radical and cationic photopolymerizations and application in 3D printing of composites

Design of ketone derivatives as highly efficient photoinitiators for free radical and cationic photopolymerizations and application in 3D printing of composites

Monocomponent Photoinitiators based on Benzophenone-Carbazole Structure for LED Photoinitiating Systems and Application on 3D Printing

3-Carboxylic Acid and Formyl-Derived Coumarins as Photoinitiators in Photo-Oxidation or Photo-Reduction Processes for Photopolymerization upon Visible Light: Photocomposite Synthesis and 3D Printing Applications

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