Acridone derivatives as high performance visible light photoinitiators for cationic and radical photosensitive resins for 3D printing technology and for low migration photopolymer property

Abdallah, Mira; Le, Huong Thi Thu; Hijazi, Akram; Schmitt, Michael; Graff, Bernadette; Dumur, Frédéric; Bui, Thanh‐Tuân; Goubard, Fabrice; Fouassier, Jean‐Pierre; Lalevée, Jacques

doi:10.1016/j.polymer.2018.11.021

Cited by 62 publications

(31 citation statements)

References 18 publications

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“…The percentage of ketone migration was calculated as: extracted (%) = [mextracted / minitial] × 100 (2) where mextracted and minitial are the weight of ketones extracted from the polymer and the weight of ketones present initially in the polymer pellet, respectively. 28…”

Section: Photoinitiator Migration Studymentioning

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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Section: Photoinitiator Migration Studymentioning

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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“…The triplet state energy was evaluated after full geometry optimization of both S0 and T1. The computational procedure was described by us in [36].…”

Section: Computational Proceduresmentioning

confidence: 99%

High performance dyes based on triphenylamine, cinnamaldehyde and indane-1,3-dione derivatives for blue light induced polymerization for 3D printing and photocomposites

et al. 2020

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In this research, high performance dyes based on triphenylamine, cinnamaldehyde and indane-1,3-dione derivatives have been designed/synthesized and evaluated as photoinitiators for visible light photopolymerization. The introduction of light-emitting diodes (LEDs) as low-cost and secured sources of irradiation is one of the major purposes in this study, where a LED at 405 nm was used for both the cationic polymerization (CP) of thin epoxide samples and the free radical polymerization (FRP) of thin TMPTA films. The proposed dyes showed very high efficiencies in the presence of the two-component photoinitiating systems based on Dye/Iodonium salt (Iod) couples or Dye/Amine (such as N-Phenylglycine (NPG) or ethyl 4-(dimethylamino)benzoate (EDB)) couples for the FRP and/or CP, highlighting their importance through a photo-oxidation (with Iod) process but also through a photo-reduction (with amine) process. The examined dyes are also able to initiate the FRP of thin acrylate films in the presence of the three-component (Dye/Iod/NPG) systems where very high rates of polymerization (Rp) and great final reactive function conversions (FCs) were achieved. Objectives of this work concern the study of the photoinitiating abilities of the different photoinitiating systems using FTIR technique but also the

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“…Concomitant to the development of visible light photoinitiating systems, cheap, compact and lightweight irradiation setups have been developed such as the Light-emitting Diodes (LEDs) or the Laser diodes making the traditional irradiation systems obsolete. Over the years and in order their absorption spectra to perfectly fit with the emission spectra of the different visible light sources, a wide range of structures have been examined as visible light photoinitiators such as acridones 1, [18,19] acridine-1,8-dione 2, [20,21] benzophenones 3, [22][23][24][25] camphorquinones 4, [26,27] carbazoles 5, [28][29][30][31][32][33] chalcones 6, [34,35] chromones 7, [36][37][38] coumarins 8, [39][40][41][42][43] copper complexes 9, [44][45][46][47][48][49][50][51][52][53][54] cyclohexanones 10, [55][56][57] dihydroanthraquinone 11, [58] 2,3-diphenylquinoxaline derivatives 12, [59] diketopyrrolopyrrole 13, [60]…”

Section: Introductionmentioning

confidence: 99%

Recent advances on push–pull organic dyes as visible light photoinitiators of polymerization

Pigot

Noirbent

Brunel

et al. 2020

European Polymer Journal

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HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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Acridone derivatives as high performance visible light photoinitiators for cationic and radical photosensitive resins for 3D printing technology and for low migration photopolymer property

Cited by 62 publications

References 18 publications

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

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

High performance dyes based on triphenylamine, cinnamaldehyde and indane-1,3-dione derivatives for blue light induced polymerization for 3D printing and photocomposites

Recent advances on push–pull organic dyes as visible light photoinitiators of polymerization

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