Vanillin derivative as performing type I photoinitiator

Breloy, Louise; Négrell, Claire; Mora, A.; Li, W. S. Jennifer; Brezová, Vlasta; Caillol, Sylvain; Versace, Davy‐Louis

doi:10.1016/j.eurpolymj.2020.109727

Cited by 43 publications

(54 citation statements)

References 40 publications

(52 reference statements)

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“…[8][9] Recently, photopolymerization has known a revival of interest with the development of the 3D/4D printing technologies, and a great deal of efforts has thus been devoted to elaborate dyes strongly absorbing at 405 nm, which is the wavelength currently under use in 3D printers. [10][11][12][13][14][15][16][17][18] With aim at reducing the environmental impact of photopolymerization, greener processes are now widely explored and the use of biosourced photoinitiators and monomers, [19][20][21][22][23][24][25][26][27][28][29] or the use of sunlight as the irradiation source to initiate polymerization processes are now extensively studied. [30][31][32][33][34][35] The progress in these two fields is considerable.…”

Section: Introductionmentioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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Photoinitiators of polymerization with reversible electrochemical properties are actively researched as these molecules can advantageously be used in photocatalytic systems, enabling to reduce the photoinitiators content within the photocurable resins. In this field, ferrocene which is extensively used by electrochemists as a reference compound for cyclic voltammetry also exhibits a significant absorption in the visible range as well as a low oxidation potential so that this metallocene was used as a potential candidate for the design of photoinitiators of polymerization. Over the years, ferrocene has been examined in numerous polymerization processes going from anionic to cationic polymerizations, but also for the freeradical polymerization of acrylates or as a sacrificial electron donor in free radical polymerization processes. Parallel to this, the development of cheap, compact and energysaving irradiation setups based on light-emitting diodes (LEDs) have clearly favored the development of visible light photoinitiators and this technology has nowadays the potential to replace the well-established UV photopolymerization. In this review, an overview of the recent development of the ferrocene-based photoinitiating systems is provided. To evidence the interest of the ferrocene derivatives recently developed, comparisons with benchmark photoinitiators will be provided.

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Section: Introductionmentioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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“…Comparison of the photoinitiating ability of PM with benchmark photoinitiator revealed PM to be on par with BAPO for the polymerization of TMPTA in laminate (72% conversion of PM vs. 70% for BAPO), also producing benzoyl and phosphinoyl radicals upon photodecomposition (See Figure 33) [178]. This conversion is higher than that of another type I photoinitiator, namely DMPA (60% TMPTA conversion).…”

Section: Scheme 2 Synthetic Route To Pmmentioning

confidence: 97%

“…[177] In 2020, vanillin was used as the starting materials for the design of a type-I photoinitiator. [178] It has to be noticed that prior to its use as raw materials for the design of photoinitiators, vanillin has also employed as starting materials for the design of different monomers. [179][180] Type-I photoinitiators are a specific kind of photoinitiators capable to undergo a homolytic cleavage of a single bond upon photoexcitation, furnishing two radical fragments from the original photoinitiator.…”

Section: Vanillin-based Type-i Photoinitiatormentioning

confidence: 99%

Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes

Noirbent

Dumur

2021

European Polymer Journal

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The development of new procedures aiming at reducing the environmental impact of polymerization processes is a major societal issue. In this field, light-assisted polymerization and especially visible light photopolymerization can address this issue by enabling in the future, Sun, to be used as the irradiation source. Presently, numerous visible light photoinitiators (xanthene dyes, porphyrins and phthalocyanines) are used in industry but their toxicities constitute a major issue for future uses of polymers. Therefore, photopolymerization is facing a short-term challenge and the development of visible light photoinitiators of polymerization has become a blooming field of research during the last decade. An ever-growing effort is thus done to develop new structures, effort which is also supported by the recent applications of photopolymerization in 3D-printing. Depending on the applications, use of synthetic photoinitiators can constitute a severe limitation for future applications of photopolymers so that the use of natural products has been identified as a promising alternative to address the toxicity or the biocompatibility issues. In this review, an overview of the different visible-light photoinitiators based on natural products is provided.

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“…Some studies have also investigated the photoreactivity of natural flavones [ 20 ] (i.e., quercetin, myricetin, and chrysin) in acrylate and epoxy blend mixture for dental and antibacterial applications [ 21 ]. Very recently, vanillin was used as the initial building block to design a new type I cleavable photoinitiator [ 22 ] in the UV range. In 2020, two natural dyes [ 23 ], namely 5-hydroxy-1,4-naphthoquinone and 2-hydroxy-1,4-naphthoquinone were examined as co-initiators in two- or three-component photoinitiating systems for FRP of acrylates under visible-light irradiation at low light intensity.…”

Section: Introductionmentioning

confidence: 99%

Lawsone Derivatives as Efficient Photopolymerizable Initiators for Free-Radical, Cationic Photopolymerizations, and Thiol—Ene Reactions

et al. 2021

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Two new photopolymerizable vinyl (2-(allyloxy) 1,4-naphthoquinone, HNQA) and epoxy (2-(oxiran-2yl methoxy) 1,4-naphthoquinone, HNQE) photoinitiators derived from lawsone were designed in this paper. These new photoinitiators can be used as one-component photoinitiating systems for the free-radical photopolymerization of acrylate bio-based monomer without the addition of any co-initiators. As highlighted by the electron paramagnetic resonance (EPR) spin-trapping results, the formation of carbon-centered radicals from an intermolecular H abstraction reaction was evidenced and can act as initiating species. Interestingly, the introduction of iodonium salt (Iod) used as a co-initiator has led to (1) the cationic photopolymerization of epoxy monomer with high final conversions and (2) an increase of the rates of free-radical polymerization of the acrylate bio-based monomer; we also demonstrated the concomitant thiol–ene reaction and cationic photopolymerizations of a limonene 1,2 epoxide/thiol blend mixture with the HNQA/Iod photoinitiating system.

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Vanillin derivative as performing type I photoinitiator

Cited by 43 publications

References 40 publications

Recent advances on ferrocene-based photoinitiating systems

Recent advances on ferrocene-based photoinitiating systems

Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes

Lawsone Derivatives as Efficient Photopolymerizable Initiators for Free-Radical, Cationic Photopolymerizations, and Thiol—Ene Reactions

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