Learning from the trees: biomimetic crosslinking of silicones by phenolic coupling

Phenolic compounds undergo radical coupling under oxidizing conditions. Silicone oils were modified with eugenol using hydrosilylation to create oils and elastomers that exhibited antioxidant activity due to the presence of phenols, as shown by DPPH and other oxidative assays. At room temperature, p...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-07, Vol.25 (13), p.5267-5275
Main Authors: Li, Angela Yayun, Melendez-Zamudio, Miguel, Yepremyan, Akop, Brook, Michael A
Format: Article
Language:English
Subjects:
Antioxidants
Biomimetic materials
Biomimetics
Coupling (molecular)
Crosslinking
Elastomers
Eugenol
Gels
Green chemistry
Hydrosilylation
Oxidants
Oxidation
Oxidizing agents
Phenolic compounds
Phenols
Physical properties
Recombination
Room temperature
Silicones
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Summary:Phenolic compounds undergo radical coupling under oxidizing conditions. Silicone oils were modified with eugenol using hydrosilylation to create oils and elastomers that exhibited antioxidant activity due to the presence of phenols, as shown by DPPH and other oxidative assays. At room temperature, phenolic coupling was not observed, as judged by lack of changes in viscosity or formation of gels. By contrast, peroxide oxidants at temperatures above 90 °C led to crosslinked materials whose physical properties (related to crosslink density) correlated with eugenol content, equivalents of peroxide added and reaction time. The product elastomers were also efficient antioxidants, although there was some attenuation of activity in higher crosslinked materials, consistent with diverse radical recombination processes. In a biomimetic process phenolic compounds tethered to silicone polymers undergo radical coupling (and crosslinking) under oxidizing conditions.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc01282d