Ambient temperature cross-linking of a sustainable, cardanol-based cyanate ester via synergistic thiol–ene copolymerization

Cardanol, a low-cost component of cashew nut shell oil, is a phenolic compound with a 15-carbon unsaturated chain in the position meta to the hydroxyl group. This biorenewable substrate was converted to a cyanate ester resin and blended with a trifunctional thiol at different ratios. Irradiation of...

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Bibliographic Details
Published inPolymer chemistry Vol. 13; no. 21; pp. 3091 - 3101
Main Authors Muldoon, Jake A., Garrison, Michael D., Savolainen, Markku A., Harvey, Benjamin G.
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 31.05.2022
Subjects
Ambient temperature
Copolymerization
Crosslinking
Cyanates
Elastomers
Esters
Hydroxyl groups
Phenols
Polymer chemistry
Self healing materials
Substrates
Ultraviolet radiation
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Summary:Cardanol, a low-cost component of cashew nut shell oil, is a phenolic compound with a 15-carbon unsaturated chain in the position meta to the hydroxyl group. This biorenewable substrate was converted to a cyanate ester resin and blended with a trifunctional thiol at different ratios. Irradiation of the blend with UV light (254 nm) facilitated thiol–ene reactions with concomitant cyclotrimerization of the cyanate ester group without additional heating. This novel synergistic approach allowed for cyanate ester cure under ambient conditions, while enhancing the degree of cross-linking. Through this approach, an elastomeric cross-linked network with a T g of −2.4 °C was prepared. This material may have potential applications as a toughener for rigid cyanate esters or self-healing materials that can take advantage of the reversible nature of thiol–ene chemistry.
ISSN:1759-9954
1759-9962
DOI:10.1039/D2PY00160H