Camphorquinone

Camphorquinone, also known as 2,3-bornanedione, is a photoinitiator used in curing dental composites.[1]

Camphorquinone
Names
IUPAC name
2,6-Bornanedione
Other names
Camphorquinone
6-Oxocamphor
CQ
CPQ
Identifiers
3D model (JSmol)
ECHA InfoCard 100.030.728
UNII
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Melting point 197-203
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Polymerization is induced very slowly by camphorquinone, so amines such as N,N-dimethyl-p-toluidine, 2-ethyl-dimethylbenzoate, N-phenylglycine are generally added to increase the rate of curing.[1]

It absorbs very weakly at 468 nm (extinction coefficient of 40 M−1·cm−1) giving it a pale yellow color.[1] Photoexcitation results in nearly quantitative formation of its triplet state through intersystem crossing and very faint fluorescence.[2]

It can be hydrolyzed by the enzyme 6-oxocamphor hydrolase.

References
  1. Jakubiak, J.; Allonas, X.; Fouassier, J.P.; Sionkowska, A.; Andrzejewska, E.; Linden, L.Å.; Rabek, J.F. (August 2003). "Camphorquinone–amines photoinitating systems for the initiation of free radical polymerization". Polymer. 44 (18): 5219–5226. doi:10.1016/S0032-3861(03)00568-8.
  2. Allonas, Xavier; Fouassier, Jean-Pierre; Angiolini, Luigi; Caretti, Daniele (19 September 2001). "Excited-State Properties of Camphorquinone Based Monomeric and Polymeric Photoinitiators". Helvetica Chimica Acta. 84 (9): 2577. doi:10.1002/1522-2675(20010919)84:9<2577::AID-HLCA2577>3.0.CO;2-Q.
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