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Stability of silorane dental monomers in aqueous systems.

Eick JD, Smith RE, Pinzino CS, Kostoryz EL

University of Missouri-Kansas City, School of Dentistry, Kansas City, MO 64108, USA.

Siloranes (silicon-based monomers with oxirane functionality) are investigated as matrix resins for new low shrinkage/stress dental composites. Compounds containing oxirane groups are known to be reactive with water, which could impart instability to the composite. OBJECTIVE: To test the stability of siloranes by measuring changes in the chemical structure of the oxirane group in aqueous environments. METHODS: Two siloranes (PH-SIL and TET-SIL) and their 1:1 mixture (SIL-MIX) were evaluated (n=2-3). Siloranes were mixed in aqueous solutions with and without 1% tetrahydrofuran (THF) containing either liver esterase or epoxide hydrolase at pH 7.4, or dilute HCl at pH 1.4. The stability of conventional dioxiranes 3,4-epoxycyclohexyl-methyl-3,4-epoxycyclohexane carboxylate (ECHM-ECHC), and bisphenol A diglycidyl ether (BADGE) were also monitored under similar conditions. NMR was used to estimate the extent of reaction and give structural information about reaction products. RESULTS: Siloranes were found to be stable for 24h in all aqueous environments tested. In contrast, ECHM-ECHC reacted at pH 1.4 to form species containing oxirane, ester, hydroxyl and carboxylic acid groups. Water hydrolyzed the ester group of ECHM-ECHC in the presence of liver esterase. In the presence of epoxide hydrolase, BADGE oxirane groups were hydrolyzed to diols, hydrolysis ranged from 0 to 34% depending on the aqueous environment. CONCLUSION: The stability and insolubility of siloranes in biological fluid simulants suggests that these may be more suitable for use in the oral environment than conventional oxirane-functional monomers.

Published 7 July 2006 in J Dent, 34(6): 405-10.
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