Novel ketone derivative-based photoinitiating systems for free radical polymerization under mild conditions and 3D printing

Xu, Yangyang; Noirbent, Guillaume; Brunel, Damien; Ding, Zhaofu; Gigmès, Didier; Graff, Bernadette; Xiao, Pu; Dumur, Frédéric; Lalevée, Jacques

doi:10.1039/d0py00990c

Cited by 40 publications

(19 citation statements)

References 43 publications

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“…In combination with the iodonium salt, the final consumption of ketone−1 was about 78%, while the final consumption of ketone−2 was just 32%. The above steady state photolysis characterizations suggested a strong interaction among the ketone/amine/Iod three−component systems, and an oxidation–reduction photochemical mechanism was already proposed by our group for other photoinitators 21,27 . Moreover, the dramatic difference in the final consumptions of ketones, in the presence of the iodonium salt, indicated that ketone−1 illustrated a much higher photochemical reactivity than ketone−2 under the same irradiation conditions, which could be useful to explain their different photoinitiation abilities for both the free radical polymerization and cationic polymerization.…”

Section: Resultssupporting

confidence: 62%

“…However, for ketone−5 ~ ketone−13, lower ε 405 nm values are observed, which are in a wide range from 900 M −1 cm −1 to 16, 000 M −1 cm −1 . It's believed that the different absorption properties of these ketones would play a very important role in their photoinitiation abilities for the free radical and cationic photopolymerizations 27 …”

Section: Resultsmentioning

confidence: 99%

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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: 62%

Section: Resultsmentioning

confidence: 99%

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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“…To minimize the negative influence of the well‐known oxygen inhibition effect for free radical polymerization, the photopolymerization of acrylates was performed in laminate upon the irradiation of LED@405 nm (110 mW cm −2 ) at room temperature (the thickness is given in the figure caption). [ 9 ] Typical acrylate function conversion profiles against the LED irradiation time are illustrated in Figure for thin samples. All the photopolymerizations were very fast and reached a plateau within 50 s of LED irradiation.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Iron Filler‐Based Photocomposites and Application in 3D Printing

Ding

Zhu

et al. 2020

Macro Materials & Eng

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The introduction of metallic fillers to polymers via the photopolymerization approach can endow the composite materials with some unique properties, but the relevant research is still scarce due to the issue of light penetration and inner filter effect. Herein, for the first time the fabrication of photocomposites based on fine iron powder (i.e., a typical kind of metallic filler) is reported in this work. The free radical polymerization of two different acrylate monomers, poly(ethylene glycol) diacrylate and trimethylolpropane triacrylate, is performed in the presence of iron filler under mild conditions (i.e., light emitting diode (LED)@405 nm irradiation at room temperature under air). And the real‐time Fourier transform infrared spectroscopy reveals remarkable photopolymerization kinetics of acrylates with high final conversions and fast polymerization rates despite the increasing contents of iron filler in the composites. Interestingly, the 3D printing technique is applied to the iron filler‐based composites to produce tridimensional patterns with excellent spatial resolution. This work not only paves the way for the investigation of photocomposites based on metallic fillers through photochemical methods, but also broadens the potential application prospects.

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“…[161] Besides, at present, their use as photoinitiators of polymerization remains scarce. [162][163][164][165][166] In 2020, the first ferrocene-based chalcones (chalcone 1-chalcone 6) were reported as visible light photoinitiators of polymerization (See Figure 34). Considering that no natural chalcones comprise a ferrocene unit, the six chalcones examined in this work can be considered as bioinspired photoinitiators.…”

Section: Ferrocene-based Chalconesmentioning

confidence: 99%

Recent advances on iron-based photoinitiators of polymerization

Dumur

2020

European Polymer Journal

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With regards to the environmental and safety concerns raised nowadays by the polymer industry, polymerization processes requiring light as the activation source are currently knowing a revival of interest after decades of disinterest. Recent progresses in photopolymerization are notably sustained by the development of new polymerization application namely 3D and 4D printing enabling an unprecedented access to structures of incredible complexity. Parallel to the manufacturing process, the polymer material itself and its composition are also facing numerous questions concerning their environmental and human health impacts. Beyond the monomers, the different additives introduced in the resin can also be potentially toxic so that a great deal of efforts is currently done to develop new photoinitiators with a toxicity assessed as being insignificant. In this field, iron-based metal complexes are candidates of choice due to the clinical demonstration of their very low toxicities. Among iron complexes, ferrocene is among the most widely studied iron-based metallocene. Due to its unique and reversible electrochemical properties as well as their absorption centred in the visible range, numerous photoinitiators have been developed with ferrocene or its oxidized form i.e. ferrocenium. Parallel to this, the remarkable electrochemical properties of ferrocenium made it an excellent candidate for its incorporation in photoinitiating systems. However, interest for iron-based photoinitiators was not limited to ferrocene and ferrocenium, and Schiff base complexes were also successfully used as initiators of polymerization. In this review, an overview of the different iron-based photoinitiating systems reported to date is presented. More precisely, if iron-based photoinitiators are developed since 50 years, a special focus will be done on photoinitiators designed for recent polymerization conditions, namely, under visible light and low light intensity.

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Novel ketone derivative-based photoinitiating systems for free radical polymerization under mild conditions and 3D printing

Abstract: Photopolymerization of acrylates under mild conditions is promising not only for academic research, but also for industrialization applications. However, it still remains a huge challenge to develop effective photoinitiators or...

Cited by 40 publications

References 43 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

Preparation of Iron Filler‐Based Photocomposites and Application in 3D Printing

Recent advances on iron-based photoinitiators of polymerization

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