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Updated: Apr 30, 2026

Stereolithographic 3D Printing with Renewable Acrylates
Published on: September 12, 2018
A high-performance renewable thermosetting resin derived from eugenol.
Benjamin G Harvey1, Christopher M Sahagun, Andrew J Guenthner
1Research Department, Materials Chemistry Branch, US Navy, Naval Air Warfare Center, Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA). benjamin.g.harvey@navy.mil.
A novel renewable bisphenol was synthesized and converted into a high-performance cyanate ester resin. This sustainable material demonstrates excellent thermal stability and low water uptake, ideal for demanding applications.
Area of Science:
- Polymer Chemistry
- Materials Science
- Sustainable Chemistry
Background:
- Traditional bisphenols raise environmental and health concerns.
- There is a growing need for high-performance resins derived from renewable resources.
Purpose of the Study:
- To synthesize a renewable bisphenol and its corresponding cyanate ester.
- To evaluate the thermal and water resistance properties of the resulting thermoset.
Main Methods:
- Solvent-free, ruthenium-catalyzed olefin metathesis of eugenol.
- Hydrogenation, purification, and conversion to a bis(cyanate) ester.
- Characterization using NMR spectroscopy and X-ray diffraction.
Main Results:
- The synthesized bisphenol and cyanate ester were rigorously characterized.
- The cured cyanate ester exhibited thermal stability >350°C and a glass transition temperature (Tg) of 186°C.
- The thermoset showed low water uptake (1.8%) and maintained a high wet Tg (167°C).
Conclusions:
- The renewable cyanate ester resin offers excellent thermal stability and moisture resistance.
- The material's properties make it suitable for maritime applications.
- Sustainable feedstocks can yield high-performance thermosetting resins.
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