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Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems

1
Institut de Science des Matériaux de Mulhouse IS2M, UMR CNRS 7361, UHA, 15 rue Jean Starcky, 68057 Mulhouse CEDEX, France
2
Dentsply Sirona, De-Trey-Straβe 1, 78462 Konstanz, Germany
3
Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6, Boulevard Maréchal Juin, 14000 Caen, France
*
Author to whom correspondence should be addressed.
Academic Editor: John C. Walton
Molecules 2019, 24(16), 2913; https://doi.org/10.3390/molecules24162913
Received: 22 July 2019 / Revised: 7 August 2019 / Accepted: 9 August 2019 / Published: 11 August 2019
(This article belongs to the Special Issue Advances in Radical Chemistry)
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Abstract

Diaryliodonium salts are well-established compounds in free radical chemistry and are already used as photoinitiators (free radical or cationic polymerization), but the presence of counter anions is a strong drawback. Indeed, a counter anion is always required (e.g., SbF6) leading to potential toxicity issues or release of HF. In the present paper, counter anion-free and fluoride-free aryliodonium salts are proposed, that is, aryliodonium ylides (AY) are studied here as new and efficient additives for radical chemistry and an example is provided for the camphorquinone (CQ)/amine based photoinitiating systems (PISs) for the polymerization of thick (1.4 mm) and thin (20–13 µm) methacrylates under air and blue light irradiation. The newly proposed PISs, for example, CQ/amine/AY, presented excellent polymerization performances and good bleaching properties were obtained after polymerization. Real-time Fourier transform infrared spectroscopy (RT-FTIR) was used to monitor the photopolymerization profiles. The chemical mechanisms involved were investigated using electron spin resonance (ESR). View Full-Text
Keywords: photoinitiator; iodonium salt; radical initiation; photopolymerization photoinitiator; iodonium salt; radical initiation; photopolymerization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Kirschner, J.; Paillard, J.; Bouzrati-Zerelli, M.; Becht, J.-M.; Klee, J.E.; Chelli, S.; Lakhdar, S.; Lalevée, J. Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems. Molecules 2019, 24, 2913.

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