Publication: Eugenol-DOPO: A bio-based phosphorous-containing monomer for thiol-ene photocurable thermosets
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Date
2023-01-01
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Abstract
The adverse health and environmental effects of petroleum-based materials have become a driving force for the fabrication of bio-based monomers. In this study, we synthesized a novel bio-based reactive phosphorus-containing; eugenol-DOPO, which was prepared in one step by the reaction of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and eugenol via Atherton–Todd reaction. Moreover, a diallyl compound was also prepared by using eugenol and piperazine. All monomers were characterized by nuclear magnetic resonance (NMR), mass, and Fourier-transform infrared (FTIR) spectroscopies. Thiol-ene photocured polysulfide thermoset networks were prepared by using these newly synthesized bio-based monomers. Thermal and thermomechanical properties of the thermosets were measured. Photo-crosslinked networks displayed over 88% gel content values. The thermal stability of the networks as well as the resulting char yields were improved as the percentage of eugenol-DOPO was increased in the formulations. The presence of N and P played a synergistic effect and the limiting oxygen index (LOI) values for the thermoset materials were enhanced. We believe eugenol-DOPO is not only a good alternative monomer for the preparation of thermally stable photocurable thermosets, but it is also a suitable bio-based additive for other polymers as well. Graphical Abstract: [Figure not available: see fulltext.].
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Kimya, Fizikokimya, Polimer Karakterizasyonu, Temel Bilimler, Mühendislik ve Teknoloji, Chemistry, Physical Chemistry, Characterization of Polymers, Natural Sciences, Engineering and Technology, Mühendislik, Bilişim ve Teknoloji (ENG), Temel Bilimler (SCI), Mühendislik, Malzeme Bilimi, MÜHENDİSLİK, ÇEVRE, POLİMER BİLİMİ, MALZEME BİLİMİ, ÇOKDİSİPLİNLİ, Engineering, Computing & Technology (ENG), Natural Sciences (SCI), ENGINEERING, MATERIALS SCIENCE, CHEMISTRY, ENGINEERING, ENVIRONMENTAL, POLYMER SCIENCE, MATERIALS SCIENCE, MULTIDISCIPLINARY, Çevre Mühendisliği, Fizik Bilimleri, Polimerler ve Plastikler, Malzeme Kimyası, Environmental Engineering, Physical Sciences, Polymers and Plastics, Materials Chemistry, DOPO, Eugenol, Piperazine, Thermoset, Thiol-ene
Citation
Özükanar Ö., ÇAKMAKÇI E., Sagdic G., Günay U. S., Durmaz H., Kumbaracı İ. V., "Eugenol-DOPO: A Bio-Based Phosphorous-Containing Monomer for Thiol-ene Photocurable Thermosets", Journal of Polymers and the Environment, 2023