Photoinitiators with functional groups. VII. Covalently bonded camphorquinone-amines

Camphorquinone (CQ), a widely used photoinitiator (PI) in dental applications, was covalently bonded to aromatic amines to enhance the rate of electron and proton transfer effect due to the close vicinity of the diketone and the amine group. 10‐bromocamphorquinone and 10‐bromomethylcamphorquinone we...

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Published in:Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2004-10, Vol.42 (19), p.4948-4963
Main Authors: Ullrich, G., Herzog, D., Liska, R., Burtscher, P., Moszner, N.
Format: Article
Language:English
Subjects:
Applied sciences
camphorquinone
differential scanning calorimetry (DSC)
Exact sciences and technology
photoinitiators
photopolymerization
Physicochemistry of polymers
Polymerization
Polymers and radiations
radical polymerization
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Summary:Camphorquinone (CQ), a widely used photoinitiator (PI) in dental applications, was covalently bonded to aromatic amines to enhance the rate of electron and proton transfer effect due to the close vicinity of the diketone and the amine group. 10‐bromocamphorquinone and 10‐bromomethylcamphorquinone were selected as suitable precursors for esterification with the carboxyl group containing aromatic amines based on 4‐dimethylaminobenzoic acid. Properties of the new photoinitiating systems were investigated by UV spectroscopy and differential scanning photocalorimetry in lauryl acrylate. Compared to physical mixtures, in all cases similar or even better performance was obtained. Surprisingly, 10‐acetyl derivatives 7–9 and 18 especially, were found to be highly reactive. Compared to CQ/ethyl 4‐dimethylaminobenzoate, the rate of photopolymerization was increased by a factor of up to 2. Intramolecular reaction was confirmed by photo‐differential scanning calorimetry experiments with varying PI concentrations. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4948–4963, 2004 Camphorquinone (CQ), a widely used photoinitiator (PI) in dental applications, was covalently bonded to aromatic amines to enhance the rate of electron and proton transfer effect due to the close vicinity of the diketone and the amine group. Properties of the new photoinitiating systems were investigated by UV spectroscopy and photodifferential scanning calorimetry in lauryl acrylate. Compared to physical mixtures, in all cases similar or even better performance were obtained. Surprisingly, 10‐acetyl derivatives 7–9 and 18 especially doubled the rate of polymerization. Intramolecular reaction was confirmed by photo‐differential scanning calorimetry experiments with varying PI concentrations.
ISSN:0887-624X
1099-0518
DOI:10.1002/pola.20318