New 1,8-Naphthalimide Derivatives as Photoinitiators for Free-Radical Polymerization Upon Visible Light

Bonardi, Aude-Héloise; Zahouily, Soraya; Dietlin, Céline; Graff, Bernadette; Morlet‐Savary, Fabrice; Ibrahim‐Ouali, Malika; Gigmès, Didier; Hoffmann, Norbert; Dumur, Frédéric; Lalevée, Jacques

doi:10.3390/catal9080637

Cited by 41 publications

(30 citation statements)

References 33 publications

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“…The photoinitiating system used in this work has been inspired from that reported in Reference [5] and comprises two additives. The iodonium salt, i.e., bis(4-tert-butylphenyl)iodonium hexafluorophosphate (Ar 2 I + /PF 6 − or also Speedcure 938), was obtained from Lambson Ltd., (Wetherby, UK), and a phosphine, 4-(diphenylphosphino)benzoic acid (4-dppba), has been supplied by Tokyo Chemical Industry Co., Ltd., (TCI) Japan.…”

Section: Additivesmentioning

confidence: 99%

“…A 1,8-naphthalimide derivative (Napht) has been chosen as the dye. This chromophore has been studied for its efficiency to initiate the free radical photopolymerization of a methacrylate resin in a previous study [5]. The chemical structure of this dye is presented in the Figure 5.…”

Section: Non-commercial Productsmentioning

confidence: 99%

“…In order to estimate the initiation ability of the different systems described in the present work, kinetics of the consumption of the characteristic methacrylate C=C bond in the MIX-MA resin (observed at 6100-6220 cm −1 ; see in [5]) has been monitored using a real-time Fourier-transform infrared device FTIR 4100 from JASCO (Tokyo, Japan).…”

Section: Free Radical Photopolymerization (Frp)mentioning

confidence: 99%

“…In the present paper, as an originality, a thermal initiator, i.e., an alkoxyamine, has been used in addition to a three-component photoinitiating system based on the dye/iodonium salt/phosphine combination. The three-component photoinitiating system examined in this study has already been proposed for a pure photochemical initiation, with a naphthalimide derivative used as the photoinitiator [5]. This system was capable of efficiently initiating the photopolymerization of methacrylates upon blue light irradiation, under air and with good-to-excellent monomer conversions.…”

Section: Introductionmentioning

confidence: 99%

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Thermal Initiators as Additives for Photopolymerization of Methacrylates upon Blue Light

et al. 2020

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Free radical polymerization is often performed by thermal initiation but also more and more by light-assisted polymerization processes. This second approach allows the polymerization to be carried out under mild conditions (under air, upon blue light exposure, under low light intensity). The aim and the originality of the present paper is to perform photopolymerization in the presence of a thermal initiator, i.e., we can take advantage of the exothermicity of the photopolymerization process to decompose the thermal initiator, leading to enhanced polymerization rates. The performance of the photoinitiating system is discussed in the present study based on real-time Fourier-transform infrared spectroscopy measurements (following the C=C bond content evolution vs. time) and by thermal imaging experiments. Mechanisms of the new system proposed in this work are also fully detailed using cyclic voltammetry, electron spin resonance (ESR) spin trapping, and UV-visible absorption properties.

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Section: Additivesmentioning

confidence: 99%

Section: Non-commercial Productsmentioning

confidence: 99%

Section: Free Radical Photopolymerization (Frp)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermal Initiators as Additives for Photopolymerization of Methacrylates upon Blue Light

et al. 2020

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“…A breakthrough can be achieved by using chromophores other than phenyl or naphthalene so that the absorption spectra can be clearly displace towards the visible region, what is possible with naphthalimides. Choice of this chromophore was supported by previous works done by our groups evidencing nahphtalimide to be an excellent candidate for the design of type II photoinitiators [50][51][52][53][54][55][56][57][58][59][60].…”

Section: Introductionmentioning

confidence: 96%

Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes

et al. 2019

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Iodonium salts are well established photoacid generators, cationic photoinitiators, as well as additives commonly used in photoredox catalytic cycles. However, as a strong limitation, iodonium salts are characterized by low light absorption properties for λ > 300 nm so that these latter cannot be activated with cheap, safe, and eco-friendly near UV or even visible light emitting diodes (LEDs). To overcome this drawback, the covalent linkage of an iodonium salt to a chromophore absorbing at longer wavelength is actively researched. With aim at red-shifting the absorption spectrum of the iodonium salt, the synthesis of new compounds combining within a unique chemical structure both the chromophore (here the naphthalimide scaffold) and the iodonium salt is presented. By mean of this strategy, a polymerization could be initiated at 365 nm with the modified iodonium salts whereas no polymerization could be induced with the benchmark iodonium salt i.e., Speedcure 938 at this specific wavelength. To examine the effect of the counter-anion on the photoinitiating ability of these different salts, five different counter-anions were used. Comparison between the different anions revealed the bis(trifluoromethane)sulfonimide salt to exhibit the best photoinitiating ability in both the free radical polymerization of acrylates and the cationic polymerization of epoxides. To support the experimental results, molecular orbital calculations have been carried out. By theoretical calculations, the initiating species resulting from the photocleavage of the iodonium salts could be determined. The cleavage selectivity and the photochemical reactivity of the new iodoniums are also discussed.

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Naphthalimide‐Based Dyes as Photoinitiators under Visible Light Irradiation and their Applications: Photocomposite Synthesis, 3D printing and Polymerization in Water

et al. 2021

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In this work, six new fluorescent dyes derived from the naphthalimide scaffold (Napht1–Napht6) were synthesized and used as high‐performance photoinitiating systems (PISs) in two and three‐component systems (combined with iodonium salt (Iod) and/or an electron donor amine (such as N‐phenylglycine[NPG])) for the radical photopolymerization of acrylate and methacrylate monomers under visible light using a light‐emitting diode at 405 nm. Markedly, these dyes were never synthesized before. In fact, these PISs showed high initiation efficiency with both demonstrating high final reactive function conversions and high polymerization rates. A further interest of our study is to determine the effect of the different substituents (chromophoric group) on the naphthalimide function, concerning the efficiency of initiation of the free radical polymerization. In order to improve the mechanical properties of the obtained polymers, these derivatives were also tested for the photopolymerization of a blend of acrylate/epoxy monomers (TA/EPOX); these latter properties were characterized by traction tests. To demonstrate the initiation efficiency of these dyes, several methods and characterization techniques were used, including steady state photolysis, real‐time Fourier transform infrared spectroscopy, emission spectroscopy as well as cyclic voltammetry. In our study, these naphthalimides were used for the synthesis of photocomposites (one and multiple layers of glass fibres) using a UV@395 nm (4 W/cm2) conveyor, as well as in the preparation of 3D printed polymers. Markedly, one of the naphthalimide derivatives (Napht‐4) can be used as a new high‐performance water soluble photoinitiator for photopolymerization in water and hydrogel synthesis.

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New 1,8-Naphthalimide Derivatives as Photoinitiators for Free-Radical Polymerization Upon Visible Light

Cited by 41 publications

References 33 publications

Thermal Initiators as Additives for Photopolymerization of Methacrylates upon Blue Light

Thermal Initiators as Additives for Photopolymerization of Methacrylates upon Blue Light

Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes

Naphthalimide‐Based Dyes as Photoinitiators under Visible Light Irradiation and their Applications: Photocomposite Synthesis, 3D printing and Polymerization in Water

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