Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

Autor: Sebastian Reinelt, Monir Tabatabai, Urs Karl Fischer, Norbert Moszner, Andreas Utterodt, Helmut Ritter
Jazyk: angličtina
Rok vydání: 2014
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 1733-1740 (2014)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.10.180
Popis: 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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