The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization
Abstract In this work, new naphthoquinone‐based photoinitiators are synthesized and applied for the first time in free radical photopolymerization. In the presence of acrylate monomers, these PIs display excellent photoinitiation capabilities under blue‐light LED@405 nm irradiation in a two‐componen...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-03-01
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| Series: | Advanced Materials Interfaces |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/admi.202202352 |
| _version_ | 1797772491301584896 |
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| author | Timur Borjigin Michael Schmitt Nicolas Giacoletto Alexandre Rico Hugo Bidotti Malek Nechab Yijun Zhang Bernadette Graff Fabrice Morlet‐Savary Pu Xiao Frédéric Dumur Jacques Lalevée |
| author_facet | Timur Borjigin Michael Schmitt Nicolas Giacoletto Alexandre Rico Hugo Bidotti Malek Nechab Yijun Zhang Bernadette Graff Fabrice Morlet‐Savary Pu Xiao Frédéric Dumur Jacques Lalevée |
| author_sort | Timur Borjigin |
| collection | DOAJ |
| description | Abstract In this work, new naphthoquinone‐based photoinitiators are synthesized and applied for the first time in free radical photopolymerization. In the presence of acrylate monomers, these PIs display excellent photoinitiation capabilities under blue‐light LED@405 nm irradiation in a two‐component photoinitiating system in which the additive is a common iodonium salt (bis‐(4‐tert‐butylphenyl)iodonium hexafluorophosphate ‐ Iod) or a tertiary amine (ethyl 4‐dimethylaminobenzoate ‐ EDB). In controlled tests, the polymerization performance of dye4/Iod is equal to or better than that of common commercial Type II photoinitiators (2‐isopropylthioxanthone and benzophenone). Meanwhile, only a trace amount of photoinitiator is required (as low as 0.05%) to initiate the photopolymerization. It is worth noting that some of these compounds can also be used in one‐component photoinitiating system (monocomponent Type II behavior) and exhibit high photoinitiation ability. A series of complementary characterization analyses of two new naphthoquinone dyes (i.e. dye 1 and dye 4) with very similar chemical structures are carried out to investigate the relevant photochemical mechanism. Finally, 3D printing experiments are carried out by a simple and convenient Direct Laser Write (DLW) technique. |
| first_indexed | 2024-03-12T21:52:40Z |
| format | Article |
| id | doaj.art-e4c541f128c74da0b47a2c9e7887017e |
| institution | Directory Open Access Journal |
| issn | 2196-7350 |
| language | English |
| last_indexed | 2024-03-12T21:52:40Z |
| publishDate | 2023-03-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | Advanced Materials Interfaces |
| spelling | doaj.art-e4c541f128c74da0b47a2c9e7887017e2023-07-26T01:36:15ZengWiley-VCHAdvanced Materials Interfaces2196-73502023-03-01108n/an/a10.1002/admi.202202352The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical PhotopolymerizationTimur Borjigin0Michael Schmitt1Nicolas Giacoletto2Alexandre Rico3Hugo Bidotti4Malek Nechab5Yijun Zhang6Bernadette Graff7Fabrice Morlet‐Savary8Pu Xiao9Frédéric Dumur10Jacques Lalevée11Université de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceUniversité de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceAix Marseille Univ CNRS ICR UMR 7273 Marseille F‐13397 FranceAix Marseille Univ CNRS ICR UMR 7273 Marseille F‐13397 FranceAix Marseille Univ CNRS ICR UMR 7273 Marseille F‐13397 FranceAix Marseille Univ CNRS ICR UMR 7273 Marseille F‐13397 FranceUniversité de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceUniversité de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceUniversité de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceResearch School of Chemistry Australian National University Canberra ACT 2601 AustraliaAix Marseille Univ CNRS ICR UMR 7273 Marseille F‐13397 FranceUniversité de Haute‐Alsace CNRS IS2M UMR 7361 Mulhouse F‐68100 FranceAbstract In this work, new naphthoquinone‐based photoinitiators are synthesized and applied for the first time in free radical photopolymerization. In the presence of acrylate monomers, these PIs display excellent photoinitiation capabilities under blue‐light LED@405 nm irradiation in a two‐component photoinitiating system in which the additive is a common iodonium salt (bis‐(4‐tert‐butylphenyl)iodonium hexafluorophosphate ‐ Iod) or a tertiary amine (ethyl 4‐dimethylaminobenzoate ‐ EDB). In controlled tests, the polymerization performance of dye4/Iod is equal to or better than that of common commercial Type II photoinitiators (2‐isopropylthioxanthone and benzophenone). Meanwhile, only a trace amount of photoinitiator is required (as low as 0.05%) to initiate the photopolymerization. It is worth noting that some of these compounds can also be used in one‐component photoinitiating system (monocomponent Type II behavior) and exhibit high photoinitiation ability. A series of complementary characterization analyses of two new naphthoquinone dyes (i.e. dye 1 and dye 4) with very similar chemical structures are carried out to investigate the relevant photochemical mechanism. Finally, 3D printing experiments are carried out by a simple and convenient Direct Laser Write (DLW) technique.https://doi.org/10.1002/admi.2022023523D printingblue‐LED‐sensitivitydirect laser writefree radical photopolymerizationnaphthoquinone derivativesphotoinitiator |
| spellingShingle | Timur Borjigin Michael Schmitt Nicolas Giacoletto Alexandre Rico Hugo Bidotti Malek Nechab Yijun Zhang Bernadette Graff Fabrice Morlet‐Savary Pu Xiao Frédéric Dumur Jacques Lalevée The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization Advanced Materials Interfaces 3D printing blue‐LED‐sensitivity direct laser write free radical photopolymerization naphthoquinone derivatives photoinitiator |
| title | The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization |
| title_full | The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization |
| title_fullStr | The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization |
| title_full_unstemmed | The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization |
| title_short | The Blue‐LED‐Sensitive Naphthoquinone‐Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization |
| title_sort | blue led sensitive naphthoquinone imidazolyl derivatives as type ii photoinitiators of free radical photopolymerization |
| topic | 3D printing blue‐LED‐sensitivity direct laser write free radical photopolymerization naphthoquinone derivatives photoinitiator |
| url | https://doi.org/10.1002/admi.202202352 |
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