scholarly journals 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

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1753
Author(s):  
Mahmoud Rahal ◽  
Bernadette Graff ◽  
Joumana Toufaily ◽  
Tayssir Hamieh ◽  
Guillaume Noirbent ◽  
...  
Keyword(s):  
3D Printing ◽  
Visible Light ◽  
High Performance ◽  
High Rate ◽  
Visible Absorption ◽  
Free Radical Photopolymerization ◽  
Rate Of Polymerization ◽  
Direct Laser ◽  
Iodonium Salt ◽  
Very High

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.

scholarly journals Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

Catalysts ◽  
2020 ◽  
Vol 10 (4) ◽  
pp. 463 ◽  
Author(s):  
Ke Sun ◽  
Corentin Pigot ◽  
Hong Chen ◽  
Malek Nechab ◽  
Didier Gigmes ◽  
...  
Keyword(s):  
Free Radical ◽  
3D Printing ◽  
High Performance ◽  
Chemical Mechanisms ◽  
Esr Spin Trapping ◽  
Free Radical Photopolymerization ◽  
Spin Resonance ◽  
Component Systems ◽  
Iodonium Salt ◽  
First Time

The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on push–pull structures. In the present paper, we chose two series of new dyes which possess indane-1,3-dione and 1H-cyclopenta naphthalene-1,3-dione groups as the electron-withdrawing groups, since they have the great potential to behave as sensitive and remarkable photoinitiators in vat photopolymerization/3D printing. When incorporated with a tertiary amine (ethyl dimethylaminobenzoate EDB, used as electron/hydrogen donor) and an iodonium salt (used as electron acceptor) as the three-component photoinitiating systems (PISs), and among a series of 21 dyes, 10 of them could efficiently promote the free radical photopolymerization of acrylates. Interestingly, steady state photolysis experiments revealed different behaviors of the dyes. Fluorescence experiments and free energy change calculations for redox processes were also carried out to investigate the relevant chemical mechanisms. Additionally, the formation of radicals from the investigated PISs was clearly observed by electron spin resonance (ESR) spin-trapping experiments. Finally, stereoscopic 3D patterns were successfully fabricated by the laser writing technique. In this work, the use of push–pull dyes based on the naphthalene scaffold as photoinitiators of polymerization is reported for the first time in a systematic study aiming at investigating the structure–performance relationship for irradiation carried out at 405 nm. By carefully selecting the electron donors used in the two series of push–pull dyes, novel and high-performance photoinitiating systems operating at 405 nm are thus proposed.

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

Polymers ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 1394 ◽  
Author(s):  
Shaohui Liu ◽  
Hong Chen ◽  
Yijun Zhang ◽  
Ke Sun ◽  
Yangyang Xu ◽  
...  
Keyword(s):  
Free Radical ◽  
3D Printing ◽  
Rational Design ◽  
Photophysical Properties ◽  
Synergetic Effect ◽  
Type Ii ◽  
Visible Absorption ◽  
Free Radical Photopolymerization ◽  
Iodonium Salt ◽  
Resonance Spin

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.

scholarly journals Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2063 ◽  
Author(s):  
Mira Abdallah ◽  
Akram Hijazi ◽  
Frédéric Dumur ◽  
Jacques Lalevée
Keyword(s):  
3D Printing ◽  
Visible Light ◽  
Blue Light ◽  
Laser Diode ◽  
Cationic Polymerization ◽  
High Performance ◽  
Printing Technology ◽  
3D Printing Technology ◽  
Visible Irradiation

In this study, eight coumarins (coumarins 1–8) are proposed as near-UV and blue light sensitive photoinitiators/photosensitizers for the cationic polymerization (CP) of epoxysilicones when combined with 4-isopropyl-4’-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (IOD). Among these coumarins, four of them (coumarins 1, 2, 6 and 8) have never been reported in the literature, i.e., these structures have been specifically designed to act as photoinitiators for silicones upon near UV and visible irradiation. Good final reactive epoxy function conversions (FCs) and also high rates of polymerization (Rp) were achieved in the presence of the newly proposed coumarin-based systems. The polymers generated from the photopolymerization of epoxysilicones can be considered as attractive candidates for several applications such as: elastomers, coatings, adhesives, and so on. The goal of this study focuses also on the comparison of the new proposed coumarins with well-established photosensitizers i.e., 1-chloro-4-propoxythioxanthone (CPTX), 9,10-dibutoxyanthracene (DBA) or some commercial coumarins (Com. Coum). As example of their high performance, the new proposed coumarins were also used for laser write experiments upon irradiation with a laser diode at 405 nm in order to develop new cationic 3D printing systems.

scholarly journals Phenothiazine derivatives as photoredox catalysts for cationic and radical photosensitive resins for 3D printing technology and photocomposite synthesis

2019 ◽  
Vol 10 (45) ◽  
pp. 6145-6156 ◽  
Author(s):  
Mira Abdallah ◽  
Thanh-Tuân Bui ◽  
Fabrice Goubard ◽  
Dimitra Theodosopoulou ◽  
Frédéric Dumur ◽  
...  
Keyword(s):  
3D Printing ◽  
Visible Light ◽  
High Performance ◽  
Phenothiazine Derivatives ◽  
Printing Technology ◽  
3D Printing Technology

New phenothiazine derivatives are synthesized and proposed as high performance visible light photoinitiators.

Zinc Tetraphenylporphyrin as High Performance Visible Light Photoinitiator of Cationic Photosensitive Resins for LED Projector 3D Printing Applications

2017 ◽  
Vol 50 (3) ◽  
pp. 746-753 ◽  
Author(s):  
Assi Al Mousawi ◽  
Cyril Poriel ◽  
Frédéric Dumur ◽  
Joumana Toufaily ◽  
Tayssir Hamieh ◽  
...  
Keyword(s):  
3D Printing ◽  
Visible Light ◽  
High Performance

scholarly journals Water-Soluble Visible Light Sensitive Photoinitiating System Based on Charge Transfer Complexes for the 3D Printing of Hydrogels

Polymers ◽  
2021 ◽  
Vol 13 (18) ◽  
pp. 3195
Author(s):  
Hong Chen ◽  
Mehdi Vahdati ◽  
Pu Xiao ◽  
Frédéric Dumur ◽  
Jacques Lalevée
Keyword(s):  
Charge Transfer ◽  
3D Printing ◽  
Visible Light ◽  
Water Solubility ◽  
Charge Transfer Complex ◽  
Water Soluble ◽  
Charge Transfer Complexes ◽  
Free Radical Photopolymerization ◽  
Potential Applications ◽  
A Charge

The development of visible-light 3D printing technology by using water-soluble initiating systems has attracted widespread attention due to their potential applications in the manufacture of hydrogels. Besides, at present, the preparation of water-soluble photoinitiators suitable for visible light irradiation (such as LEDs) still remains a challenge. Therefore, this work is devoted to developing water-soluble photoinitiators (PI)/photoinitiating systems (PIS) upon irradiation with a LED @ 405 nm. In detail, a new water-slightly-soluble chalcone derivative dye [(E)-3-(4-(dimethylamino) phenyl)-1-(4-(2-(2-(2-methoxyethoxy) ethoxy) ethoxy) phenyl) prop-2-en-1-one] was synthesized here and used as a PI with a water-soluble coinitiator, i.e., triethanolamine (TEA) which was also used as an electron donor. When combined together, a charge transfer complex (CTC) formed immediately which exhibited excellent initiating ability for the free radical photopolymerization of poly(ethyleneglycol)diacrylate (PEG-DA). In light of the powerful CTC effect, the [dye-TEA] CTC could not only exhibit enhanced water solubility and mechanical properties but could also be effectively applied for 3D printing. This CTC system is environmentally friendly and cost-saving which demonstrates a great potential to prepare hydrogels via photopolymerization.

scholarly journals Development of new high‐performance visible light photoinitiators based on carbazole scaffold and their applications in 3d printing and photocomposite synthesis

2019 ◽  
Vol 57 (20) ◽  
pp. 2081-2092 ◽  
Author(s):  
Mira Abdallah ◽  
Diego Magaldi ◽  
Akram Hijazi ◽  
Bernadette Graff ◽  
Frédéric Dumur ◽  
...  
Keyword(s):  
3D Printing ◽  
Visible Light ◽  
High Performance

High Performance Visible-light-responsive TiO2/CuxO/Cu Photocatalyst

2016 ◽  
Vol 136 (8) ◽  
pp. 551-552
Author(s):  
Sumio Kogoshi ◽  
Nao Kato ◽  
Yu Katsui ◽  
Noboru Katayama ◽  
Syota Yazawa ◽  
...  
Keyword(s):  
Visible Light ◽  
High Performance
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