High-performance resins and polymers from vanillin

Low cost, efficient, simple chemical process


Natural vanillin is extracted from the seed pods of Vanilla planifolia, a vining orchid native to Mexico. Vanilla planifolia, 1887 illustration from Köhler’s Medicinal Plants.

Scientists at the U.S. Naval Air Warfare Center Weapons Division in China Lake, California, have recently invented a way to convert vanillin to bis(cyanate) ester monomers to produce high-performance resins and related polymers. The patented technology is available via patent license agreement to companies that would make, use, or sell it commercially.

Fossil fuel-based resins and polymers are subject to global market fluctuations and availability. There is a growing need for domestically sourced composite resins that come from sustainable and renewable sources. For example, the military requires new high-performance composite resins with low water uptake for a weapon, aircraft, and sea platforms. However, nearly every industry can benefit from this discovery.

Until now, making high-performance composite resins from renewable resources (bio-aromatics) in an efficient and cost-effective manner has been limited. Recently, a team of Navy scientists have developed a class of resins based on vanillin, a naturally occurring organic molecule that is widely available from biomass waste and lignin. Samples have been produced that demonstrate vanillin as a powerful precursor to high-performing and related polymer systems.

Using a minimum number of chemical steps to transform the readily available bio feedstock vanillin into cyanate ester monomers, researchers anticipate the development of new and useful high-performance composite resins.

The invention includes multiple approaches for making vanillin-based bisphenols, followed by conversion of these compounds to make a series of new bis(cyanate) esters, and details on the thermal curing chemistry of vanillin-based bis(cyanate) esters as well as the physical properties of the cured resins.

The conversion process is accomplished by treating vanillin with a reductive coupling agent to form at least one olefin. The olefin(s) are treated with hydrogen and a metal catalyst to hydrogenate. The hydrogenated olefin(s) are treated with at least one cyanogen halide and a base in an organic solvent to produce at least one olefin monomer. The olefin monomer(s) is purified by recrystallization or precipitation from an organic solvent.

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