Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives

Higginson, Cody J.; Malollari, Katerina G.; Xu, Yunqi; Kelleghan, Andrew V.; Ricapito, Nicole G.; Messersmith, Phillip B.

doi:10.1002/anie.201906008

Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives

Journal Article · Wed Jul 24 00:00:00 EDT 2019 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201906008· OSTI ID:1572038

^[1]; ^[1]; Xu, Yunqi ^[1]; Kelleghan, Andrew V. ^[1]; ^[2]; ^[3]

Univ. of California, Berkeley, CA (United States)
Zymergen, Inc., Emeryville, CA (United States)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

A synthetic strategy to incorporate catechol functional groups into benzoxazine thermoset monomers was developed, leading to a family of bioinspired small-molecule resins and main-chain polybenzoxazines derived from biologically available phenols. Lap-shear adhesive testing revealed a polybenzoxazine derivative with greater than 5 times improved shear strength on aluminum substrates compared to a widely studied commercial benzoxazine resin. Derivative synthesis identified the catechol moiety as an important design feature in the adhesive performance and curing behavior of this bioinspired thermoset. Favorable mechanical properties comparable to commercial resin were maintained, and glass transition temperature and char yield under nitrogen were improved. Blending of monomers with bioinspired main-chain polybenzoxazine derivatives provided formulations with enhanced shear adhesive strengths up to 16 MPa, while alloying with commercial core-shell particle-toughened epoxy resins led to shear strengths exceeding 20 MPa. These results highlight the utility of bioinspired design and the use of biomolecules in the preparation of high-performance thermoset resins and adhesives with potential utility in transportation and aerospace industries and applications in advanced composites synthesis.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1572038

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 35 Vol. 58; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
adhesives
bioinspired materials
polybenzoxazines
polymers
surfacechemistry

Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives

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References (54)

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