Synthesis and Applications of Onium Salts for Photopolymerization Reactions
DOI:
https://doi.org/10.6000/1929-5995.2024.13.04Keywords:
Photopolymerization, 2-methyleneanthraquinonium, 9-methylanthracenium salts, Cyclohexene oxide, styrene, p-methyl styrene, N-vinylcarbazoleAbstract
The synthesis and characterization of phosphonium and arsonium salts having anthraquinone and anthracene moiety was carried out by reacting equimolar amounts of halomethyl anthracene or anthraquinone with triphenylphosphine or triphenyl arsine in toluene solvent. The halide counter (Cl or Br) ion was exchanged with hexafluoro antimonate (SbF6-) which proved to be a useful photoinitiator for polymerizing cyclohexene oxide, styrene, p-methyl styrene, and N-vinylcarbazole. The experimental results demonstrate the effects of salt, monomer structures, and the photolysis time on the rate of polymerization and the number average molecular weight of the obtained polymer. These salts are easy to handle, nonhygroscopic under laboratory conditions, and they have good solubility in halogenated solvents such as dichloromethane and chloroform.
References
Yagci Y, Jockusch S, Turro NJ. Photoinitiated Polymerization: Advances, Challenges, and Opportunities. Macromolecules 2010; 43(15): 6245-6260. https://doi.org/10.1021/ma1007545 DOI: https://doi.org/10.1021/ma1007545
Deng L, Qu J. Design of novel phenothiazine-based push-pull photoinitiators for visible light with high activity, good solubility, and low migration. Progress in Organic Coatings 2023; 183: 107766. https://doi.org/10.1016/j.porgcoat.2023.107766 DOI: https://doi.org/10.1016/j.porgcoat.2023.107766
Davidson RS. The chemistry of photoinitiators - some recent developments. Journal of Photochemistry and Photobiology A: Chemistry Review 1993; 73(2): 81-96. https://doi.org/10.1016/1010-6030(93)80037-A DOI: https://doi.org/10.1016/1010-6030(93)80037-A
Zhang L, Li L, Chen Y, Pi J, Liu R, Zhu Y. Recent Advances and Challenges in Long-Wavelength Sensitive Cationic Photoinitiating Systems. Polymers 2023; 15(11): 2524-2052. https://doi.org/10.3390/polym15112524 DOI: https://doi.org/10.3390/polym15112524
Abu-Abdoun II. Cationic Photopolymerization by Polymeric Triphenyl Phosphonium Salts. Chemical Science International Journal 2019; 27(4): 1-7. https://doi.org/10.9734/CSJI/2019/v27i430118 DOI: https://doi.org/10.9734/CSJI/2019/v27i430118
Dumura F. Recent Advances on Anthracene-based Photoinitiators of Polymerization. European Polymer Journal 2022; 169(111139): 1-32. https://doi.org/10.1016/j.eurpolymj.2022.111139 DOI: https://doi.org/10.1016/j.eurpolymj.2022.111139
Zhu Y, Pi J, Zhang Y, Xu D, Yagci Y, Liu R. A new anthraquinone derivative as a near UV and visible light photoinitiator for free-radical, thiol–ene and cationic polymerizations. Polymer Chemistry 2021; 12(22): 3299-3306. https://doi.org/10.1039/D1PY00347J DOI: https://doi.org/10.1039/D1PY00347J
Abu-Abdoun II, Ledwith A. Cationic polymerization photochemically and thermally induced by phenothiazine cation radical salts. European Polymer Journal 1997; 33(10-12): 1671-1677. https://doi.org/10.1016/S0014-3057(97)00044-X DOI: https://doi.org/10.1016/S0014-3057(97)00044-X
Abu-Abdoun II, Ledwith A. Photoinitiated cationic polymerization of epoxide and vinyl monomers by p-trimethoxytrityl salts. Journal of Polymer Research 2007; 14(4): 99-105. https://doi.org/10.1007/s10965-006-9086-2 DOI: https://doi.org/10.1007/s10965-006-9086-2
Abu-Abdoun II, Thijs L, Neckers DC. Nonketonic perester photoinitiators. Macromolecules 1984: 17(3): 282-288. https://doi.org/10.1021/ma00133a004 DOI: https://doi.org/10.1021/ma00133a004
Abu-Abdoun II, Aale-Ali. Cationic photopolymerization of cyclohexene oxide. European Polymer Journal 1992; 28(1): 73-78. https://doi.org/10.1016/0014-3057(92)90239-X DOI: https://doi.org/10.1016/0014-3057(92)90239-X
Neckers DC, Abu-Abdoun II. p, p'-Bis ((triphenylphosphonio) methyl) benzophenone salts as photoinitiators of free radical and cationic polymerization. Macromolecules 1984; 17(12): 2468-2473. https://doi.org/10.1021/ma00142a003 DOI: https://doi.org/10.1021/ma00142a003
Abu-Abdoun II, Aale-Ali. Cationic photopolymerization of p-methyl styrene initiated by phosphonium and arsonium salts. European Polymer Journal 1993; 29(11): 1439-1443. https://doi.org/10.1016/0014-3057(93)90055-K DOI: https://doi.org/10.1016/0014-3057(93)90055-K
Abu-Abdoun II, Aale-Ali. Cationic photopolymerization of styrene by phosphonium and arsonium salts. Macromolecular Reports 1993; 30(3-4): 327-336.
Abu-Abdoun II, Aale-Ali. Photopolymerization of cyclohexene oxide by phosphonium and arsonium salts. European Polymer Journal 1993; 29(11): 1445-1450. https://doi.org/10.1016/0014-3057(93)90056-L DOI: https://doi.org/10.1016/0014-3057(93)90056-L
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