Beilstein Journal of Organic Chemistry p. 1733 - 1740 (2014)
Update date:2022-07-30
Topics:
Reinelt, Sebastian
Tabatabai, Monir
Fischer, Urs Karl
Moszner, Norbert
Utterodt, Andreas
Ritter, Helmut
Thiol-ene photopolymerizations gain a growing interest in academic research. Coatings and dental restoratives are interesting applications for thiol-ene photopolymerizations due to their unique features. In most studies the relative flexible and hydrophilic ester derivative, namely pentaerythritoltetra(3-mercaptopropionate) (PETMP), is investigated as the thiol component. Thus, in the present study we are encouraged to investigate the performance of more hydrophobic ester-free thiol-modified bis-and trisphenol derivatives in thiol-ene photopolymerizations. For this, six different thiol-modified bis-and trisphenol derivatives exhibiting four to six thiol groups are synthesized via the radical addition of thioacetic acid to suitable allyl-modified precursors and subsequent hydrolysis. Compared to PETMP better flexural strength and modulus of elasticity are achievable in thiol-ene photopolymerizations employing 1,3,5-triallyl-1,3,5-triazine-2,4,6-trione (TATATO) as the ene derivative. Especially, after storage in water, the flexural strength and modulus of elasticity is twice as high compared to the PETMP reference system.
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