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

Author

Mira Abdallah, Akram Hijazi, Frédéric Dumur, and Jacques Lalevée

Subjects
cationic polymerization, coumarin, epoxy-silicone, light-emitting diode, LED, photoinitiator, Organic chemistry, QD241-441
Abstract

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.

Published
2020
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3. Coumarin Derivatives as Photoinitiators in Photo-Oxidation and Photo-Reduction Processes and a Kinetic Model for Simulations of the Associated Polymerization Profiles

Author

Frédéric Dumur, Mira Abdallah, Jacques Lalevée, Bernadette Graff, Jui-Teng Lin, Akram Hijazi, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Université Libanaise, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Molecular model, 02 engineering and technology, Coumarin, 010402 general chemistry, Photochemistry, 01 natural sciences, chemistry.chemical_compound, Kinetic model, Process Chemistry and Technology, Organic Chemistry, Light irradiation, simulation, 021001 nanoscience & nanotechnology, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, Photopolymer, chemistry, Polymerization, photopolymerization, photocomposite, photoinitiator, 0210 nano-technology, Photoinitiator, 3D polymer patterns
Abstract

International audience; In this work, the design of an original series of coumarin derivatives (CoumC1-CoumC13) is presented. Chemical structures of these coumarins were selected by molecular modelling to ensure both excellent light absorption properties and high potential photoreactivity (high excited state energy). As a striking result of this in-silico design, 8 of the 13 proposed coumarins were never presented and were specifically proposed for this work, evidencing the interest of the structures. New multi-component photoinitiating systems (PISs) based on these coumarins are proposed for the free radical polymerization (FRP) of (meth)acrylates and examined upon visible light irradiation using the light emitting diode (LED) as a safe and economical irradiation source. The proposed systems are based on coumarins which act as remarkable photoinitiators/photosensitizers (PIs/PSs) combined with N-phenylglycine (NPG) and/or iodonium salt (Iod) as co-initiators in order to generate the reactive species (radicals) that will initiate the photopolymerization recation. Investigation of the chemical mechanisms suggested by the different interactions that take place as well as the photophysical and photochemical properties of coumarins are provided. The access 2 to high polymerization rates (Rp), excellent photoinitiating abilities and great reactive function conversions (FC) is possible with these structures based on the coumarin core. Coumarins show high efficiency for the FRP of (meth)acrylates by reaction with iodonium salt (a photo-oxidation process) or with amine (a photo-reduction process). These compounds were used in 3D printing resins but also for the preparation of photocomposites. In this latter case, an excellent depth of cure was noted as remarkable behavior. To rationalize the experimental results, a kinetic model for a three-component system has been established to analyze the role of oxygen in the monomer conversions and the conversion enhancement observed while using an amine as a co-initiator.

Published
2020
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4. In Silico Design of Nitrocoumarins as Near-UV Photoinitiators: Toward Interesting Opportunities in Composites and 3D Printing Technologies

Author

Mira Abdallah, Jacques Lalevée, Akram Hijazi, Frédéric Dumur, Bernadette Graff, Jean-Pierre Fouassier, Ecole Doctorale des Sciences et de la Technologie (EDST), Lebanese University [Beirut] (LU), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université Libanaise, Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)

Subjects
Materials science, Polymers and Plastics, business.industry, Process Chemistry and Technology, In silico, Organic Chemistry, Radical polymerization, Cationic polymerization, 3D printing, Nanotechnology, [CHIM.MATE]Chemical Sciences/Material chemistry, Coumarin, law.invention, Photocomposite, Photopolymer, law, Light-emitting diode, Molecular orbital, business
Abstract

International audience; In this research, 31 nitrocoumarins (including 27 structures never reported in the literature) were designed through molecular orbital calculations and synthesized as high-performance near-UV−visible light photoinitiators of polymerization for a better understanding of their sructure/ eactivity/ efficiency relationship. Based on their photoinitiating abilities examined during the free-radical polymerization (FRP) of acrylates, different coumarins examined in this work can be classified into three main categories: (1) very reactive ones (Coum6,7,11,12&26); (2) moderately reactive nitrocoumarins (Coum1,2,16,20,21,23,25,27&28); and (3) nitrocoumarins of low reactivity (Coum3,4,5,8,9,10,13,14,15,17,18,19,22,24,29,30&31). Different techniques were used in order to understand their photoinitiating abilities as well as the associated chemical mechanisms. The real-time Fourier transform infrared technique has been used to follow the polymerization profiles (reactive function conversion (FCs) vs irradiation time). Different two- and three-component photoinitiating systems based on nitrocoumarin/iodonium salt (or N-phenylglycine (NPG) or ethyl 4-(dimethylamino)benzoate) and nitrocoumarin/iodonium salt/NPG were examined for the FRP of acrylates or/and the cationic polymerization of epoxides upon irradiation with a light-emitting diode at 405 nm as an unharmed and inexpensive irradiation source. Moreover, cyclic voltammetry, fluorescence spectroscopy, UV−visible spectroscopy, and electron spin resonance techniques were also used to provide a full picture of the involved chemical mechanisms. Excellent polymerization performances (i.e., high final reactive FCs and also great rates of polymerization (Rp)) were obtained using these derivatives. Some applications in threedimensional printing and composite synthesis are reported to highlight the interest of the proposed structures in modern technologies.

Published
2020
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5. Design of new phenothiazine derivatives as visible light photoinitiators

Author

Mira Abdallah, Tayssir Hamieh, Bernadette Graff, Joumana Toufaily, Thanh-Tuân Bui, Frédéric Dumur, Jacques Lalevée, Fabrice Goubard, Mahmoud Rahal, Université de Strasbourg (UNISTRA), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Département de Photochimie Générale (DPG), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Lebanese University [Beirut] (LU), and Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Materials science, Polymers and Plastics, Organic Chemistry, Radical polymerization, Cationic polymerization, Bioengineering, [CHIM.MATE]Chemical Sciences/Material chemistry, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Biochemistry, Fluorescence spectroscopy, 0104 chemical sciences, chemistry.chemical_compound, Photopolymer, Polymerization, chemistry, Phenothiazine, Fourier transform infrared spectroscopy, 0210 nano-technology, Spectroscopy, ComputingMilieux_MISCELLANEOUS
Abstract

In this article, four new phenothiazine derivatives (denoted as PT1, PT2, PT3 and PT4) are specifically in silico designed by molecular modelling for good light absorption properties @405 nm. The most interesting structures showing both intense violet/blue light absorption and high potential photochemical reactivity were synthesized for detailed investigations as photoinitiators/photosensitizers in the presence of an iodonium salt for the free radical photopolymerization of (meth)acrylates and the cationic polymerization of epoxides upon near-UV or visible light irradiation. Remarkably, two of the proposed structures (PT3 and PT4) from this in silico design were never synthesized prior to this work and were thus specifically designed for this work. Three-component photoinitiating systems based on PT/iodonium/amine (N-phenylglycine or ethyl 4-dimethylaminobenzoate) are also developed for the free radical polymerization of acrylates. Both excellent polymerization rates and high final reactive function conversions were obtained. A full picture of the photochemical mechanisms is provided using different techniques: real-time Fourier transform infrared spectroscopy, UV-visible spectroscopy, fluorescence spectroscopy, and cyclic voltammetry. Finally, the high performance of the phenothiazine derivatives is also shown in 3D printing experiments as well as in photocomposite synthesis using glass fibres (thick sample; using a LED@395 nm conveyor).

Published
2020
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6. A water soluble and highly reactive bisphosphonate functionalized thioxanthone-based photoinitiator

Author

Tugce Nur Eren, Mira Abdallah, Turkan Gencoglu, Jacques Lalevée, Duygu Avci, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)

Subjects
Polymers and Plastics, General Physics and Astronomy, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, Photo differential scanning calorimetry, chemistry.chemical_compound, Thioxanthone, Hexafluorophosphate, Materials Chemistry, Water soluble photoinitiator, Bisphosphonate, Reactivity (chemistry), Photopolymerization, Chemistry, Organic Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Photopolymer, Polymerization, Flash photolysis, 0210 nano-technology, [CHIM.OTHE]Chemical Sciences/Other, Photoinitiator, Ethylene glycol
Abstract

International audience; A new water soluble bisphosphonate functionalized thioxanthone (TXBP2) is synthesized from aza-Michael addition reaction of 2-(2-aminoethoxy)-9H-thioxanthen-9-one and tetraethyl vinylidene bisphosphonate. This photoinitiator shows excellent water-solubility of 86 g L−1 compared to Irgacure 2959 (5 g L−1). It has a λmax in the near UV–visible region, ~400 nm. The photoinitiation effectiveness of TXBP2 is studied by photo-DSC for photopolymerization of trimethylolpropane triacrylate and poly(ethylene glycol) diacrylate (PEGDA, Mn = 575 D). It shows very high polymerization rates and conversions with bis-(4-tert-butylphenyl)-iodonium hexafluorophosphate or ethyl 4-(dimethylamino)benzoate, compared to thioxanthone. The photochemical mechanisms investigated by laser flash photolysis and fluorescence indicate that the reaction involves both singlet and triplet pathway. Water solubility, biocompatibility and high reactivity make this photoinitiator a promising candidate for biomedical applications.

Published
2020
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7. High performance dyes based on triphenylamine, cinnamaldehyde and indane-1,3-dione derivatives for blue light induced polymerization for 3D printing and photocomposites

Author

Mira Abdallah, Frédéric Dumur, Bernadette Graff, Akram Hijazi, Jacques Lalevée, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Département de Photochimie Générale (DPG), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), and Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Materials science, General Chemical Engineering, Radical polymerization, Indane, 02 engineering and technology, TMPTA, 010402 general chemistry, Photochemistry, Triphenylamine, 01 natural sciences, chemistry.chemical_compound, Dyes, Acrylate, Photoinitiator, Photopolymerization, 3D printing resin, Process Chemistry and Technology, Cationic polymerization, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Photopolymer, chemistry, Polymerization, Free Radical Polymerization, 0210 nano-technology
Abstract

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. A new dye (Dye 4) is proposed here for the first time (never synthesized before) and a new synthetic pathway for Dye 3 is also established. Objectives of this work concern the study of the photoinitiating abilities of the different photoinitiating systems using FTIR technique but also the study of the chemical mechanisms which was mainly examined in solution. The use of the investigated systems for 3D printing experiments (using LED projector or laser diode @405 nm) is particularly outlined. Finally, the production of thick glass fiber photocomposites presenting excellent depth of cure is also accomplished in the presence of these dyes (using near-UV conveyor: LED@395 nm).

Published
2020
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8. Keto‐coumarin scaffold for photoinitiators for 3D printing and photocomposites

Author

Giacomo Rodeghiero, Akram Hijazi, Mira Abdallah, Jacques Lalevée, Andrea Gualandi, Frédéric Dumur, Pier Giorgio Cozzi, Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Alma Mater Studiorum Università di Bologna [Bologna] (UNIBO), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Dipartimento di Chimica 'G. Ciamician', Alma Mater Studiorum, Università di Bologna, Bologna, Italy, Abdallah M., Dumur F., Hijazi A., Rodeghiero G., Gualandi A., Cozzi P.G., Lalevee J., and Dumur, Frederic

Subjects
Scaffold, Materials science, Polymers and Plastics, 3D printing, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, law.invention, chemistry.chemical_compound, law, Materials Chemistry, Physical and Theoretical Chemistry, [CHIM.MATE] Chemical Sciences/Material chemistry, 3D printing resin, business.industry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Coumarin, 0104 chemical sciences, Photopolymer, chemistry, photopolymerization, light-emitting diode, photocomposite, photoinitiator, keto-coumarin, 0210 nano-technology, business, Photoinitiator, Light-emitting diode
Abstract

The purposes of this paper are moving toward (a) the development of a new series of photoinitiators (PIs) which are based on the keto-coumarin (KC) core, (b) the introduction of light-emitting diodes (LEDs) as inexpensive and safe sources of irradiation, (c) the study of the photochemical mechanisms through which the new PIs react using different techniques such as Fourier transform infrared, UV–visible or fluorescence spectroscopy, and so on, (d) the use of such compounds (presenting good reactivity and excellent photopolymerization initiating abilities) for two specific and high added value applications: 3D printing (@405 nm) and preparation of thick glass fiber photocomposites with excellent depth of cure, and finally (e) the comparison of the performance of these KC derivatives versus other synthesized coumarin derivatives. In this study, six well-designed KC derivatives (KC-C, KC-D, KC-E, KC-F, KC-G, and KC-H) are examined as high-performance visible-light PIs for the cationic polymerization of epoxides as well as the free-radical polymerization of acrylates upon irradiation with LED@405 nm. Excellent polymerization rates are obtained using two different approaches: a photo-oxidation process in combination with an iodonium (Iod) salt and a photo-reduction process when associated with an amine (N-phenylglycine or ethyl 4-(dimethylamino)benzoate). High final reactive conversions were obtained. A full picture of the involved photochemical mechanisms is provided.

Published
2020
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9. Acridone derivatives as high performance visible light photoinitiators for cationic and radical photosensitive resins for 3D printing technology and for low migration photopolymer property

Author

Akram Hijazi, Huong Le, Jean-Pierre Fouassier, Jacques Lalevée, Bernadette Graff, Fabrice Goubard, Thanh-Tuân Bui, Mira Abdallah, Michael Schmitt, Frédéric Dumur, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Université Libanaise, Université de Strasbourg (UNISTRA), Institut de Chimie Radicalaire (ICR), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Organic Chemistry, Radical polymerization, Cationic polymerization, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, Acridone, chemistry.chemical_compound, Monomer, Photopolymer, chemistry, Polymerization, Materials Chemistry, [CHIM]Chemical Sciences, Amine gas treating, 0210 nano-technology, Visible spectrum
Abstract

WOS:000451818000007; This paper is devoted to study two acridone derivatives (A-2DPA and A-2PTz). These acridone compounds are synthesized and proposed as high performance visible light photoinitiators, in the presence of an iodonium salt or/and an amine (NPG or EDB), for both the free radical polymerization of (meth)acrylates and the cationic polymerization of epoxides upon irradiation with LED@405 nm. Excellent polymerization initiating abilities are found, and high final monomer conversions are obtained. A full picture of the involved photochemical mechanisms is provided. This paper is also concerned with the use of these acridone-based systems in new 3D printing resins. Finally, the usage of the new acridone derivatives for photopolyrners with low migration properties is particularly outlined.

Published
2018
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10. Coumarins as Powerful Photosensitizers for the Cationic Polymerization of Epoxy-Silicones under Near-UV and Visible Light and Applications for 3D Printing Technology

Author

Frédéric Dumur, Akram Hijazi, Mira Abdallah, Jacques Lalevée, Dumur, Frederic, Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université Libanaise, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)

Subjects
Light, Polymers, Silicones, Pharmaceutical Science, 02 engineering and technology, Photochemistry, 01 natural sciences, coumarin, Analytical Chemistry, Polymerization, Coumarins, Drug Discovery, Spectroscopy, Fourier Transform Infrared, cationic polymerization, chemistry.chemical_classification, Anthracenes, Photosensitizing Agents, Polymer, 021001 nanoscience & nanotechnology, Photopolymer, Chemistry (miscellaneous), visual_art, Printing, Three-Dimensional, visual_art.visual_art_medium, Molecular Medicine, light-emitting diode, photoinitiator, 0210 nano-technology, Oxidation-Reduction, Algorithms, Visible spectrum, [CHIM.POLY] Chemical Sciences/Polymers, Materials science, Ultraviolet Rays, Xanthones, 010402 general chemistry, Elastomer, Article, lcsh:QD241-441, epoxy-silicone, lcsh:Organic chemistry, Cations, Physical and Theoretical Chemistry, Epoxy Resins, Lasers, Organic Chemistry, LED, Cationic polymerization, Epoxy, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Thioxanthenes, photopolymerization, Epoxy Compounds, Photoinitiator
Abstract

In this study, eight coumarins (coumarins 1&ndash, 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&rsquo, 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.

Published
2020
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11. Boron Compounds as Additives for the Cationic Polymerization Using Coumarin Derivatives in Epoxy Silicones

Author

Mira Abdallah, Akram Hijazi, Pier Giorgio Cozzi, Frédéric Dumur, Jacques Lalevée, Andrea Gualandi, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Alma Mater Studiorum University of Bologna (UNIBO), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Dumur, Frederic, Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Abdallah M., Hijazi A., Cozzi P.G., Gualandi A., Dumur F., and Lalevee J.

Subjects
Boron Compounds, boron compound, [CHIM.POLY] Chemical Sciences/Polymers, Materials science, Polymers and Plastics, Cationic polymerization, Dark Polymerization, Radical polymerization, chemistry.chemical_element, 02 engineering and technology, Coumarin, Borane, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Polymer chemistry, Materials Chemistry, Reactivity (chemistry), Physical and Theoretical Chemistry, Boron, Borate, Organic Chemistry, Epoxy, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, coinitiator, [CHIM.POLY]Chemical Sciences/Polymers, Monomer, chemistry, Polymerization, visual_art, visual_art.visual_art_medium, Co-initiator, 0210 nano-technology
Abstract

International audience; This work aims at using two borane derivatives, namely Borane A: B(C6F5)3 and Borate B: C32H12BF24Na as additives for the cationic polymerization of epoxy silicones under visible light, in the presence of coumarins as photosensitizers and 4‐isopropyl‐4′‐methyldiphenyl iodonium tetrakis(pentafluorophenyl)borate (SC939). The effect of boron compounds on the absorption and the emission spectra of a coumarin is particularly outlined. These two boron compounds can improve both the polymerization rate and the final monomer conversion. Moreover, the effect of adding water on the reactivity of the system is studied. It should be noted that the studied boron additives are able to enhance in an interesting way the polymerization rate when light irradiation is switched off through a dark polymerization (DP) mechanism. This latter behavior is highly desired for practical applications. Finally, the very high photoreactivity of boron compounds is employed for the development of new cationic 3D printing resins upon exposure to a light emitting diode (LED) projector at 405 nm, as well as for direct laser write experiments, by means of a laser diode at 405 nm. The 3D polymerization occurs through a cationic process which can be quite useful in order to reduce the shrinkage usually observed in radical polymerization.

Published
2020
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12. In-silico based development of photoinitiators for 3D printing and composites: Search on the coumarin scaffold

Author

Frédéric Dumur, Akram Hijazi, Jean-Pierre Fouassier, Jacques Lalevée, Bernadette Graff, Mira Abdallah, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Molecular model, Cationic polymerization, General Chemical Engineering, Radical polymerization, General Physics and Astronomy, Alkyne, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Thiophene, Composite material, Nitrocoumarins, chemistry.chemical_classification, free radical polymerization, Rational design, [CHIM.MATE]Chemical Sciences/Material chemistry, General Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Monomer, chemistry, Polymerization, photopolymerization, light-emitting diode, 0210 nano-technology
Abstract

International audience; In this work, the in-silico rational design of new photoinitiators by molecular modeling for specific wavelength (here 405 nm) and specific applications (3D printing, composites) is reported. A large number of (keto)coumarin derivatives were investigated by molecular modeling and their synthesis and more detailed photochemical investigations are based on obtaining structures having both excellent predicted light absorption properties @ 405 nm and high excited state energy levels (to ensure high photochemical reactivity). More particularly, four new families of coumarins were designed (4 of the 19 proposed coumarins were never synthesized (N2,M6,T1,T6)): the first family is based on Nitrocoumarins (N1-N6), the second one on Methoxybenzene-based coumarins and Ethoxycoumarins (M1-M6), the third one on Thiophene-based coumarins (T1-T6) and the last family studied concerns Alkyne-based coumarin (A1). The purpose of this work concerns the study of the photoinitiating ability of these compounds in different monomers for different polymerization processes (free radical, cationic) using FTIR technique. The different compounds reported in this work are very efficient to initiate the free radical polymerization of (meth)acrylates but also the cationic polymerization of epoxides upon mild irradiation conditions using a Light Emitting Diode (LED) at 405 nm as visible light source. Nitrocoumarins were identified as the best candidates for photoinitiation among the different families of coumarins investigated in this work. More precisely, nitrocoumarins are characterized by very good polymerization profiles, great final reactive function conversions (FC) and also high rates of polymerization (Rp). The electrochemical and pho-tochemical properties of the different compounds were also studied to get a deeper insight into the photo-chemical mechanisms supporting the initiation process. A full picture of the involved photochemical mechanisms is provided. Thanks to the astounding polymerization initiating ability of these coumarins, their use in 3D printing applications can be worthwhile. Remarkably, using these compounds, the preparation of photo-composites was possible even in difficult light penetration conditions resulting from the presence of fibers inside the resins.

Published
2020
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13. Charge Transfer Complexes as Dual Thermal and Photochemical Polymerization Initiators for 3D Printing and Composites Synthesis

Author

Bernadette Graff, Jean-Pierre Fouassier, Patxi Garra, Sami Lakhdar, Mira Abdallah, Dengxia Wang, Jacques Lalevée, Haifaa Mokbel, Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA)), Université de Strasbourg (UNISTRA), Laboratoire de chimie moléculaire et thioorganique (LCMT), Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU), Département de Photochimie Générale (DPG), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)

Subjects
chemistry.chemical_classification, Materials science, Polymers and Plastics, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Process Chemistry and Technology, Organic Chemistry, Radical polymerization, Glass fiber, 02 engineering and technology, Electron acceptor, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, Methacrylate, 01 natural sciences, 0104 chemical sciences, Photopolymer, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymerization, Composite material, 0210 nano-technology, Curing (chemistry), ComputingMilieux_MISCELLANEOUS, Visible spectrum
Abstract

The development of visible light 3D printing technology and the preparation of high-tech composites under mild conditions remain a huge challenge. This article is devoted to the development of dual thermal/photochemical initiators both for visible light 3D printing and composite preparation under mild conditions. Dual thermal and photochemical polymerization initiators are presented, a dual ability scarcely encountered in the literature. In detail, here, a series of charge transfer complexes (CTCs) that are demonstrated to be formed between phosphines (electron donors) and iodonium salt as electron acceptor are investigated as dual thermal and photochemical free radical polymerization (FRP) initiators. The CTCs exhibit excellent photo and/or thermal initiating properties for the benchmarked methacrylate resin and can be efficiently used for the curing of glass fibers or carbon fiber composites. To the best of our knowledge, this is the first access to high-tech carbon fiber composites using dual photo/the...

Published
2019
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14. Development of New High-Performance Visible Light Photoinitiators Based on Carbazole Scaffold and Their Applications in 3D Printing and Photocomposite Synthesis

Author

Diego Magaldi, Frédéric Dumur, Mira Abdallah, Akram Hijazi, Bernadette Graff, Thanh-Tuân Bui, Fabrice Goubard, Jacques Lalevée, Jean-Pierre Fouassier, Université de Strasbourg (UNISTRA), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA)), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Institut de Chimie de Strasbourg, Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), and Gigmes, Didier

Subjects
Materials science, Polymers and Plastics, Heteroatom, light-emitting diodes, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, composites, Fluorescence spectroscopy, 3D resins, chemistry.chemical_compound, [CHIM] Chemical Sciences, Materials Chemistry, [CHIM]Chemical Sciences, photoinitiators, Carbazole, Organic Chemistry, Photodissociation, Cationic polymerization, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Photopolymer, chemistry, Polymerization, photopolymerization, 0210 nano-technology, Visible spectrum
Abstract

WOS:000483262400001; International audience; In this article, new compounds based on the carbazole scaffold (DMs = DM1 and DM2, constituted by a carbazole unit connected on positions 3 and 6 to a two 4,4 '-dimethoxydiphenylamine groups and differing by the substituent present on the nitrogen heteroatom of the carbazole core) were synthesized and proposed as high-performance visible light photoinitiators/photosensitizers for both the free-radical polymerization of methacrylates and the cationic polymerization of epoxides upon visible light exposure using LED@405 nm. Remarkably, DM2 leads to higher final conversions than DM1. In order to study the photophysical and photochemical properties of the carbazole derivatives, different parameters were taken into account such as the light absorption, the steady-state photolysis, and the fluorescence spectroscopy. Using different techniques such as fluorescence quenching, redox behavior, and cyclic voltammetry, we are able to discuss the photosensitization/photoinitiation reactions providing a full coherent picture of the involved chemical mechanisms. The photosensitization of the carbazole derivatives occurred predominantly via singlet excited states at the rate of the diffusion limit. Upon exposure to laser diode at 405 nm, DMs show high performance in initiating systems for 3D resins. Remarkably, DM2 can also be used in photocomposite synthesis using light-emitting diode conveyor. (c) 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019

Published
2019
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15. Diethoxyacetate Salts as Co-initiators for Radical Photosensitive Resins: Towards Aromatic Amine-Free Systems?

Author

Assi Al Mousawi, Malek Nechab, Jean-Pierre Fouassier, Jacques Lalevée, Frédéric Dumur, Akram Hijazi, Mira Abdallah, Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Université Libanaise, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), and Gigmes, Didier

Subjects
chemistry.chemical_classification, [CHIM.POLY] Chemical Sciences/Polymers, Chemistry, Organic Chemistry, Radical polymerization, Aromatic amine, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, [CHIM.POLY]Chemical Sciences/Polymers, Polymerization, Physical and Theoretical Chemistry, 0210 nano-technology, Visible spectrum
Abstract

WOS:000495969700014; International audience; Diethoxyacetate salts are investigated as new co-initiators for the free radical polymerization (FRP) of (meth)acrylates upon visible light exposure, with light emitting diodes (LEDs; 405 nm, 477 nm) being employed for this purpose. Interestingly, the impact of the counter cation on their initiating ability is clearly highlighted. When these co-initiators are combined with commercial photoinitiators such as 2-isopropylthioxanthone (ITX) or camphorquinone (CQ), good to excellent free radical polymerization initiating performances are found and high final reactive function conversions are achieved. In the absence of these co-initiators, no or poor polymerization occurs, clearly highlighting the importance of these co-initiators for an efficient process. These systems can be interesting for the replacement of aromatic amines opening the way for amine-free Type II photoinitiating systems.

Published
2019
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16. Coumarin derivatives as versatile photoinitiators for 3D printing, polymerization in water and photocomposite synthesis

Author

Jacques Lalevée, Frédéric Dumur, Andrea Gualandi, Jean-Pierre Fouassier, Bernadette Graff, Giacomo Rodeghiero, Akram Hijazi, Mira Abdallah, Pier Giorgio Cozzi, Abdallah M., Hijazi A., Graff B., Fouassier J.-P., Rodeghiero G., Gualandi A., Dumur F., Cozzi P.G., Lalevee J., Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA)), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Alma Mater Studiorum Università di Bologna [Bologna] (UNIBO), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Gigmes, Didier, Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Radical polymerization, Coumarin derivatives, Bioengineering, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Fluorescence spectroscopy, chemistry.chemical_compound, SYSTEMS, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, FLUORESCENCE, LEDS, Organic Chemistry, Photodissociation, Cationic polymerization, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Photopolymer, Monomer, LIGHT, chemistry, Polymerization, 0210 nano-technology, Photoinitiator, DYES, PHOTOPOLYMERIZATION
Abstract

WOS:000458566800006; International audience; The goal of this paper concerns the first evaluation of two recently reported coumarins to initiate photopolymerization reactions. These two compounds (CoumA and CoumB) are proposed as high performance visible light photoinitiators and evaluated as photoredox catalysts (PCs), in the presence of an iodonium salt or with an amine, for both the free radical polymerization (FRP) of (meth) acrylates and the cationic polymerization (CP) of epoxides upon visible light exposure using an LED at 405 nm. These coumarin derivatives showed a high photoinitiation ability i. e. excellent polymerization rates and high final monomer conversions were obtained. The photophysical and photochemical properties of the coumarin derivatives were studied in terms of absorption, steady state photolysis and fluorescence spectroscopy. The photoinitiation mechanisms of the coumarin derivatives were discussed from fluorescence quenching, redox behavior and cyclic voltammetry experiments. A full picture of the involved photochemical mechanisms is provided. Coumarin-based systems are high performance photoinitiators, and their use in new photosensitive 3D printing resins will also be presented. Remarkably, CoumB is also found to be very efficient for the preparation of hydrogels under mild conditions due to its high solubility in water i. e. CoumB corresponds to a high-performance water soluble photoinitiator. Finally, the usage of the new coumarin derivatives for photocomposite synthesis with glass fibers (thick samples with a good depth of cure) using a near-UV conveyor (LED @ 395 nm) is particularly outlined.

Published
2019
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17. Phenothiazine derivatives as photoredox catalysts for cationic and radical photosensitive resins for 3D printing technology and photocomposite synthesis

Author

Thanh-Tuân Bui, Dimitra Theodosopoulou, Jean Pierre Fouassier, Jacques Lalevée, Fabrice Goubard, Mira Abdallah, Akram Hijazi, Frédéric Dumur, Gigmes, Didier, Université de Strasbourg (UNISTRA), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA)), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Institut de Chimie de Strasbourg, Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)

Subjects
chemistry.chemical_classification, Materials science, Polymers and Plastics, Organic Chemistry, Radical polymerization, Cationic polymerization, Bioengineering, 02 engineering and technology, Polymer, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Biochemistry, Fluorescence spectroscopy, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Polymerization, Phenothiazine, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, Cyclic voltammetry, 0210 nano-technology, Visible spectrum
Abstract

WOS:000498229100004; International audience; This study highlights the use of four new phenothiazine derivatives (denoted as B compounds: B106, B107, B108, and B111), which are synthesized and proposed as high performance visible light photoinitiators, in combination with an iodonium salt, in both the free radical polymerization (FRP) of acrylates and the cationic polymerization (CP) of epoxides upon visible light exposure using a cheap and safe Light Emitting Diode (LED) at 405 nm. Remarkably, two of them (B108 and B111) are also evaluated as photoredox catalysts (PCs). These phenothiazine compounds can also be used in three-component photoinitiating systems with an iodonium salt and an amine (e.g. N-phenylglycine (NPG)) for the FRP of acrylates upon irradiation with a LED@405 nm. They showed an outstanding polymerization photoinitiation ability; that is, excellent polymerization rates and high final reactive function conversions were obtained. The photoinitiation mechanisms were investigated through different techniques including RT-FTIR, UV-visible spectroscopy, fluorescence spectroscopy, cyclic voltammetry and electron paramagnetic resonance. A full picture of the involved photochemical mechanisms is provided. As high performance photoinitiators, phenothiazine-based systems are especially used in new radical photosensitive 3D printing resins to improve the depth of cure, ensuring the formation of very thick 3D printed polymers. Finally, the use of these new phenothiazine derivatives for the access to thick glass fiber composites using a near-UV conveyor (LED@395 nm) is outlined i.e. thick and filled samples again requiring improved depth of cure.

Published
2019
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