Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
Assi Al Mousawi,
Patxi Garra,
Frédéric Dumur,
Thanh-Tuan Bui,
Fabrice Goubard,
Joumana Toufaily,
Tayssir Hamieh,
Bernadette Graff,
Didier Gigmes,
Jean Pierre Fouassier,
Jacques Lalevée
Affiliations
Assi Al Mousawi
Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, France
Patxi Garra
Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, France
Frédéric Dumur
Institut de Chimie Radicalaire—CNRS, Aix-Marseille University, UMR 7273, F-13397 Marseille, France
Thanh-Tuan Bui
Laboratory of Physico-chemistry of Polymers and Interfaces LPPI, University of Cergy-Pontoise, 5 Mail Gay Lussac, Neuville-sur-Oise, 95031 Cergy-Pontoise CEDEX, France
Fabrice Goubard
Laboratory of Physico-chemistry of Polymers and Interfaces LPPI, University of Cergy-Pontoise, 5 Mail Gay Lussac, Neuville-sur-Oise, 95031 Cergy-Pontoise CEDEX, France
Joumana Toufaily
Laboratory of Materials, Catalysts, Environment and Analytical Methods (MCEMA-CHAMSI), EDST, Lebanese University, Campus Hariri, Hadath, Beyrouth, Lebanon
Tayssir Hamieh
Laboratory of Materials, Catalysts, Environment and Analytical Methods (MCEMA-CHAMSI), EDST, Lebanese University, Campus Hariri, Hadath, Beyrouth, Lebanon
Bernadette Graff
Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, France
Didier Gigmes
Institut de Chimie Radicalaire—CNRS, Aix-Marseille University, UMR 7273, F-13397 Marseille, France
Jean Pierre Fouassier
Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, France
Jacques Lalevée
Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, France
Radical chemistry is a very convenient way to produce polymer materials. Here, an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides utilizing Light Emitting Diodes LEDs @405 nm. Excellent polymerization-initiating abilities are found and high final reactive function conversions are obtained. Interestingly, these new derivatives display much better near-UV polymerization-initiating abilities compared to a reference UV absorbing carbazole (CARET 9H-carbazole-9-ethanol) demonstrating that the new substituents have good ability to red shift the absorption of the proposed photoinitiators. All the more strikingly, in combination with iodonium salt, Cd1–Cd7 are likewise preferred as cationic photoinitiators over the notable photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO) for mild irradiation conditions featuring their remarkable reactivity. In particular their utilization in the preparation of new cationic resins for LED projector 3D printing is envisioned. A full picture of the included photochemical mechanisms is given.
