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Journal article
Epoxidation of Cardanol's Terminal Double Bond
Polymers, v 12(9), p2104
01 Sep 2020
PMID: 32947830
Abstract
In this investigation, the terminal double bonds of the side chain epoxidized cardanol glycidyl ether (SCECGE) molecule were further epoxidized in the presence of Oxone(R) (potassium peroxomonosulfate) and fluorinated acetone. Regular methods for the double bond epoxidation are not effective on the terminal double bonds because of their reduced electronegativity with respect to internal double bonds. The terminal double bond functionality of the SCECGE was epoxidized to nearly 70%, increasing the epoxy functionality of SCECGE from 2.45 to 2.65 epoxies/molecule as measured using proton magnetic nuclear resonance (H-1-NMR). This modified material-side chain epoxidized cardanol glycidyl ether with terminal epoxies (TE-SCECGE)-was thermally cured with cycloaliphatic curing agent 4-4 '-methylenebis(cyclohexanamine) (PACM) at stoichiometry, and the cured polymer properties, such as glass transition temperature (T-g) and tensile modulus, were compared with SCECGE resin cured with PACM. The T-g of the material was increased from 52 to 69 degrees C as obtained via a dynamic mechanical analysis (DMA) while the tensile modulus of the material increased from 0.88 to 1.24 GPa as a result of terminal double bond epoxidation. In addition to highlighting the effects of dangling side groups in an epoxy network, this modest increase in T-g and modulus could be sufficient to significantly expand the potential uses of amine-cured cardanol-based epoxies for fiber reinforced composite applications.
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Details
- Title
- Epoxidation of Cardanol's Terminal Double Bond
- Creators
- Emre Kinaci - Drexel UniversityErde Can - Yeditepe UniversityJohn J. La Scala - United States Army Research LaboratoryGiuseppe R. Palmese - Drexel University
- Publication Details
- Polymers, v 12(9), p2104
- Publisher
- Mdpi
- Number of pages
- 12
- Grant note
- W911NF-13-2-0046 / US Army Research Laboratory (ARL) under the Center for Sustainable Corrosion Prevention (CSCP)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemical and Biological Engineering
- Web of Science ID
- WOS:000582171800001
- Scopus ID
- 2-s2.0-85092029264
- Other Identifier
- 991019169545204721
InCites Highlights
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Polymer Science