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

Molecules. 2019 Aug 11;24(16):2913. doi: 10.3390/molecules24162913.

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).

Keywords: iodonium salt; photoinitiator; photopolymerization; radical initiation.

MeSH terms

  • Camphor / analogs & derivatives*
  • Camphor / chemistry
  • Free Radicals
  • Light*
  • Methacrylates / chemistry*
  • Photochemical Processes*

Substances

  • Free Radicals
  • Methacrylates
  • Camphor
  • camphorquinone