Mechanism of Cyclic Dye Regeneration During Eosin-Sensitized Photoinitiation in the Presence of Polymerization Inhibitors.

Journal of Polymer Science. Part A, Polymer Chemistry
Heather J Avens, Christopher N Bowman

Abstract

A visible light photoinitiator, eosin, in combination with a tertiary amine coinitiator is found to initiate polymerization despite the presence of at least 1000-fold excess dissolved oxygen which functions as an inhibitor of radical polymerizations. Additionally, 0.4 µM eosin is able to overcome 100-fold excess (40 µM) 2,2,6,6-Tetramethyl-1-piperidinyloxy (TEMPO) inhibitor, initiating polymerization after only a 2 minute inhibition period. In contrast, 40 µM Irgacure-2959, a standard cleavage-type initiator, is unable to overcome even an equivalent amount of inhibitor (40 µM TEMPO). Through additional comparisons of these two initiation systems, a reaction mechanism is developed which is consistent with the kinetic data and provides an explanation for eosin's relative insensitivity to oxygen, TEMPO and other inhibitors. A cyclic mechanism is proposed in which semi-reduced eosin radicals react by disproportionation with radical inhibitors and radical intermediates in the inhibition process to regenerate eosin and effectively consume inhibitor. In behavior similar to that of eosin, rose bengal, fluorescein, and riboflavin are also found to initiate polymerization despite the presence of excess TEMPO, indicating that cyclic regen...Continue Reading

References

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Citations

Dec 17, 2015·Chemical Society Reviews·K Kaastrup, H D Sikes
Feb 26, 2016·Journal of the American Chemical Society·Jiangtao XuCyrille Boyer
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Jan 17, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jong-Ho BackMin Sang Kwon
Jul 15, 2020·Chemical Reviews·Mihyun LeeMarcy Zenobi-Wong

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