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Synthesis And Photopolymerization Of Thiol-Modified Triazine-Based Monomers And Oligomers For The Use In Thiol-Ene-Based Dental Composites

Sebastian Reinelt, M. Tabatabai, N. Moszner, U. Fischer, A. Utterodt, H. Ritter
Published 2014 · Chemistry

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Thiol-ene photopolymerizations combine the unique features of step-growth reactions and photoinitiated polymerizations, so that they experience a growing interest for applications such as coatings or dental restoratives. Most studies have making use of a relatively fl exible ester and the hydrolytically labile derivative pentaerythritoltetra(3-mercaptopropionate) ( PETMP ) as the thiol component in common. In this study, the performance of hydrolytically stable 1,3,5-tris(3mercaptopropyl)-1,3,5-triazine-2,4,6-trione ( 4a ), 1,3,5-tris(2-methyl-3-mercapto-propyl)-1,3,5-triazine-2,4,6-trione ( 4b ), and oligomers thereof in thiol-ene photopolymerizations is investigated. The oligomers are prepared via thiol-Michael or thiol-isocyanate additions by using 4a and suitable diacrylates or diisocyanates containing a rigid core structure. Compared with PETMP , the thiol derivative 4a shows better fl exural strength and modulus of elasticity in thiol-ene photopolymerizations with 1,3,5-triallyl-1,3,5-triazine-2,4,6trione ( TATATO ) as the -ene derivative. This phenomenon becomes especially evident after storage in water at 37 °C for 24 h. Furthermore, the performance regarding the fl exural strength, the Young’s modulus of elasticity, the polymerization shrinkage stress of 4a , and the polyadducts thereof in dental fi lling composites is evaluated and discussed.
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