Eugenol-DOPO: A Bio-Based Phosphorous-Containing Monomer for Thiol-ene Photocurable Thermosets

Ozge Ozukanar, Emrah Çakmakçi*, Gokhan Sagdic, Ufuk Saim Gunay, Hakan Durmaz, Volkan Kumbaraci*

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10 Atıf (Scopus)

Özet

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.].

Orijinal dilİngilizce
Sayfa (başlangıç-bitiş)3259-3271
Sayfa sayısı13
DergiJournal of Polymers and the Environment
Hacim31
Basın numarası7
DOI'lar
Yayın durumuYayınlandı - Tem 2023

Bibliyografik not

Publisher Copyright:
© 2023, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.

Finansman

This work was supported by the Scientific Research Projects Department of Istanbul Technical University (ITU-BAP) (Project number: TGA-2022-43637).

FinansörlerFinansör numarası
Istanbul Teknik Üniversitesi
Bilimsel Araştırma Projeleri Birimi, İstanbul Teknik ÜniversitesiTGA-2022-43637

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