Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
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 pol...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/22/12/2143 |
| _version_ | 1818066043154726912 |
|---|---|
| author | 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 |
| author_facet | 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 |
| author_sort | Assi Al Mousawi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-10T15:01:30Z |
| format | Article |
| id | doaj.art-39ba3ab4bbfd4745ae391d34d1d8827d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T15:01:30Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-39ba3ab4bbfd4745ae391d34d1d8827d2022-12-22T01:44:10ZengMDPI AGMolecules1420-30492017-12-012212214310.3390/molecules22122143molecules22122143Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D PrintingAssi Al Mousawi0Patxi Garra1Frédéric Dumur2Thanh-Tuan Bui3Fabrice Goubard4Joumana Toufaily5Tayssir Hamieh6Bernadette Graff7Didier Gigmes8Jean Pierre Fouassier9Jacques Lalevée10Institute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, FranceInstitute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, FranceInstitut de Chimie Radicalaire—CNRS, Aix-Marseille University, UMR 7273, F-13397 Marseille, FranceLaboratory of Physico-chemistry of Polymers and Interfaces LPPI, University of Cergy-Pontoise, 5 Mail Gay Lussac, Neuville-sur-Oise, 95031 Cergy-Pontoise CEDEX, FranceLaboratory of Physico-chemistry of Polymers and Interfaces LPPI, University of Cergy-Pontoise, 5 Mail Gay Lussac, Neuville-sur-Oise, 95031 Cergy-Pontoise CEDEX, FranceLaboratory of Materials, Catalysts, Environment and Analytical Methods (MCEMA-CHAMSI), EDST, Lebanese University, Campus Hariri, Hadath, Beyrouth, LebanonLaboratory of Materials, Catalysts, Environment and Analytical Methods (MCEMA-CHAMSI), EDST, Lebanese University, Campus Hariri, Hadath, Beyrouth, LebanonInstitute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, FranceInstitut de Chimie Radicalaire—CNRS, Aix-Marseille University, UMR 7273, F-13397 Marseille, FranceInstitute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, FranceInstitute of Science and Materials of Mulhouse IS2M—UMR, The National Center for Scientific Research (CNRS) 7361—UHA, 15, Rue Jean Starcky, 68057 Mulhouse CEDEX, FranceRadical 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.https://www.mdpi.com/1420-3049/22/12/2143cationic polymerizationfree radical polymerizationlight emitting diodes (LEDs)photoinitiators3D printing |
| spellingShingle | 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 Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing Molecules cationic polymerization free radical polymerization light emitting diodes (LEDs) photoinitiators 3D printing |
| title | Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing |
| title_full | Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing |
| title_fullStr | Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing |
| title_full_unstemmed | Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing |
| title_short | Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing |
| title_sort | novel carbazole skeleton based photoinitiators for led polymerization and led projector 3d printing |
| topic | cationic polymerization free radical polymerization light emitting diodes (LEDs) photoinitiators 3D printing |
| url | https://www.mdpi.com/1420-3049/22/12/2143 |
| work_keys_str_mv | AT assialmousawi novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT patxigarra novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT fredericdumur novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT thanhtuanbui novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT fabricegoubard novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT joumanatoufaily novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT tayssirhamieh novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT bernadettegraff novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT didiergigmes novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT jeanpierrefouassier novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting AT jacqueslalevee novelcarbazoleskeletonbasedphotoinitiatorsforledpolymerizationandledprojector3dprinting |