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A High-Performance Renewable Thermosetting Resin Derived from Eugenol

Authors

  • Dr. Benjamin G. Harvey,

    Corresponding author
    1. Research Department, Materials Chemistry Branch, US Navy, Naval Air Warfare Center, Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA)
    • Research Department, Materials Chemistry Branch, US Navy, Naval Air Warfare Center, Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA)===

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  • Dr. Christopher M. Sahagun,

    1. National Research Council Postdoctoral Fellow, Air Force Research Laboratory, Edwards AFB, CA, 93524 (USA)
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  • Dr. Andrew J. Guenthner,

    1. Air Force Research Laboratory, Rocket Propulsion Division, Edwards AFB, CA, 93524 (USA)
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  • Dr. Thomas J. Groshens,

    1. Research Department, Materials Chemistry Branch, US Navy, Naval Air Warfare Center, Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA)
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  • Dr. Lee R. Cambrea,

    1. Research Department, Materials Chemistry Branch, US Navy, Naval Air Warfare Center, Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA)
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  • Dr. Josiah T. Reams,

    1. ERC, Inc. Edwards AFB, CA, 93524 (USA)
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  • Dr. Joseph M. Mabry

    1. Air Force Research Laboratory, Rocket Propulsion Division, Edwards AFB, CA, 93524 (USA)
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Abstract

A renewable bisphenol, 4,4′-(butane-1,4-diyl)bis(2-methoxyphenol), was synthesized on a preparative scale by a solvent-free, Ru-catalyzed olefin metathesis coupling reaction of eugenol followed by hydrogenation. After purification, the bisphenol was converted to a new bis(cyanate) ester by standard techniques. The bisphenol and cyanate ester were characterized rigorously by NMR spectroscopy and single-crystal X-ray diffraction studies. After complete cure, the cyanate ester exhibited thermal stability in excess of 350 °C and a glass transition temperature (Tg) of 186 °C. As a result of the four-carbon chain between the aromatic rings, the thermoset displayed a water uptake of only 1.8 % after a four day immersion in 85 °C water. The wet Tg of the material (167 °C) was only 19 °C lower than the dry Tg, and the material showed no significant degradation as a result of the water treatment. These results suggest that this resin is well suited for maritime environments and provide further evidence that full-performance resins can be generated from sustainable feedstocks.

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