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Title: Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives

Abstract

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.

Authors:
ORCiD logo [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [3]
  1. Univ. of California, Berkeley, CA (United States)
  2. Zymergen, Inc., Emeryville, CA (United States)
  3. Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1572038
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 58; Journal Issue: 35; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; adhesives; bioinspired materials; polybenzoxazines; polymers; surfacechemistry

Citation Formats

Higginson, Cody J., Malollari, Katerina G., Xu, Yunqi, Kelleghan, Andrew V., Ricapito, Nicole G., and Messersmith, Phillip B. Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives. United States: N. p., 2019. Web. doi:10.1002/anie.201906008.
Higginson, Cody J., Malollari, Katerina G., Xu, Yunqi, Kelleghan, Andrew V., Ricapito, Nicole G., & Messersmith, Phillip B. Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives. United States. doi:10.1002/anie.201906008.
Higginson, Cody J., Malollari, Katerina G., Xu, Yunqi, Kelleghan, Andrew V., Ricapito, Nicole G., and Messersmith, Phillip B. Wed . "Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives". United States. doi:10.1002/anie.201906008. https://www.osti.gov/servlets/purl/1572038.
@article{osti_1572038,
title = {Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives},
author = {Higginson, Cody J. and Malollari, Katerina G. and Xu, Yunqi and Kelleghan, Andrew V. and Ricapito, Nicole G. and Messersmith, Phillip B.},
abstractNote = {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.},
doi = {10.1002/anie.201906008},
journal = {Angewandte Chemie (International Edition)},
number = 35,
volume = 58,
place = {United States},
year = {2019},
month = {7}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 10 works
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Works referenced in this record:

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Simple but Strong: A Mussel-Inspired Hot Curing Adhesive Based on Polyvinyl Alcohol Backbone
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Polyphosphoprotein from the Adhesive Pads of Mytilus edulis
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A comprehensive metabolic map for production of bio-based chemicals
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Synthesis and properties of thermosetting resin based on urushiol
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Catechol oxidation: considerations in the design of wet adhesive materials
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Selective cleavage of tert-butyldimethylsilyl ethers with neutral alumina
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Hybrid polybenzoxazine with tunable properties
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Breaking the symmetry of dibenzoxazines: a paradigm to tailor the design of bio-based thermosets
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  • DOI: 10.1039/C5GC03102H

Enhancing the Adhesion of a Biomimetic Polymer Yields Performance Rivaling Commercial Glues
journal, January 2014

  • Meredith, Heather J.; Jenkins, Courtney L.; Wilker, Jonathan J.
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  • DOI: 10.1002/adfm.201303536

Enhanced Thermal Property and Flame Retardancy via Intramolecular 5-Membered Ring Hydrogen Bond-Forming Amide Functional Benzoxazine Resins
journal, November 2018


Cardanol benzoxazines – interplay of oxazine functionality (mono to tetra) and properties
journal, January 2015

  • Shukla, Swapnil; Mahata, Arup; Pathak, Biswarup
  • RSC Advances, Vol. 5, Issue 95
  • DOI: 10.1039/C5RA14214H

Mussel-Inspired Thiol–Ene Polymer Networks: Influencing Network Properties and Adhesion with Catechol Functionality
journal, September 2012

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  • DOI: 10.1021/cm302301e

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Natural monomers: A mine for functional and sustainable materials – Occurrence, chemical modification and polymerization
journal, May 2019


Development of Fully Biobased High-Performance Bis-Benzoxazine under Environmentally Friendly Conditions
journal, March 2018

  • Kotzebue, Lloyd R. V.; de Oliveira, Jéssica R.; da Silva, Joane B.
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 4
  • DOI: 10.1021/acssuschemeng.8b00340

Surface Roughness and Bond Strength of Adhesives
journal, May 1972


Mussel-Inspired Adhesives and Coatings
journal, August 2011


A mussel-inspired polybenzoxazine containing catechol groups
journal, December 2018


Synthetic Biomaterials from Metabolically Derived Synthons
journal, January 2016


Tough, Bio-Inspired Hybrid Materials
journal, December 2008


Heterogeneous Oxidation of Catechol
journal, October 2015

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Physical and mechanical characterization of near-zero shrinkage polybenzoxazines
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A Study on Hydrogen-Bonded Network Structure of Polybenzoxazines
journal, April 2002

  • Kim, Ho-Dong; Ishida, Hatsuo
  • The Journal of Physical Chemistry A, Vol. 106, Issue 14
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Mussel adhesion – essential footwork
journal, February 2017

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Primary Amine-Functional Benzoxazine Monomers and Their Use for Amide-Containing Monomeric Benzoxazines
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Physical and mechanical properties of flexible polybenzoxazine resins: Effect of aliphatic diamine chain length
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The efficiency of various toughening agents in novel phenolic type thermoset resin systems
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High-Performance Bio-Based Benzoxazines from Enzymatic Synthesis of Diphenols
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Nanoparticles as curing and adhesive aid for biobased and petrobased polybenzoxazines
journal, June 2017


Phenolic materials via ring-opening polymerization of benzoxazines: Effect of molecular structure on mechanical and dynamic mechanical properties
journal, April 1994


Bioinspired polymeric woods
journal, August 2018


Bioinspired structural materials
journal, October 2014

  • Wegst, Ulrike G. K.; Bai, Hao; Saiz, Eduardo
  • Nature Materials, Vol. 14, Issue 1
  • DOI: 10.1038/nmat4089

    Works referencing / citing this record:

    The Present and Future of Biologically Inspired Adhesive Interfaces and Materials
    journal, December 2011

    • Brubaker, Carrie E.; Messersmith, Phillip B.
    • Langmuir, Vol. 28, Issue 4
    • DOI: 10.1021/la300044v

    Nanoparticles as curing and adhesive aid for biobased and petrobased polybenzoxazines
    journal, June 2017


    Selective cleavage of tert-butyldimethylsilyl ethers with neutral alumina
    journal, January 1992

    • Feixas, Joan; Capdevila, Anna; Camps, Francisco
    • Journal of the Chemical Society, Chemical Communications, Issue 19
    • DOI: 10.1039/c39920001451

    Heterogeneous Oxidation of Catechol
    journal, October 2015

    • Pillar, Elizabeth A.; Zhou, Ruixin; Guzman, Marcelo I.
    • The Journal of Physical Chemistry A, Vol. 119, Issue 41
    • DOI: 10.1021/acs.jpca.5b07914

    Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives
    journal, August 1972

    • Corey, E. J.; Venkateswarlu, A.
    • Journal of the American Chemical Society, Vol. 94, Issue 17
    • DOI: 10.1021/ja00772a043

    Mussel adhesion – essential footwork
    journal, February 2017

    • Waite, J. Herbert
    • The Journal of Experimental Biology, Vol. 220, Issue 4
    • DOI: 10.1242/jeb.134056

    The Chemistry Of Adrenochrome And Related Compounds
    journal, April 1959


    High-performance mussel-inspired adhesives of reduced complexity
    journal, October 2015

    • Ahn, B. Kollbe; Das, Saurabh; Linstadt, Roscoe
    • Nature Communications, Vol. 6, Issue 1
    • DOI: 10.1038/ncomms9663

    Enhancing the Adhesion of a Biomimetic Polymer Yields Performance Rivaling Commercial Glues
    journal, January 2014

    • Meredith, Heather J.; Jenkins, Courtney L.; Wilker, Jonathan J.
    • Advanced Functional Materials, Vol. 24, Issue 21
    • DOI: 10.1002/adfm.201303536

    Enhanced Thermal Property and Flame Retardancy via Intramolecular 5-Membered Ring Hydrogen Bond-Forming Amide Functional Benzoxazine Resins
    journal, November 2018


    The molecular mechanisms underlying mussel adhesion
    journal, January 2019


    The biochemistry and control of enzymatic browning
    journal, June 1995


    Hybrid polybenzoxazine with tunable properties
    journal, January 2013

    • Xu, Hongli; Zhang, Wenli; Lu, Zaijun
    • RSC Advances, Vol. 3, Issue 11
    • DOI: 10.1039/c3ra22247k

    Physical and mechanical characterization of near-zero shrinkage polybenzoxazines
    journal, April 1996


    Polyphosphoprotein from the Adhesive Pads of Mytilus edulis
    journal, March 2001

    • Waite, J. Herbert; Qin, Xiaoxia
    • Biochemistry, Vol. 40, Issue 9
    • DOI: 10.1021/bi002718x

    3,4-Dihydro-1,3,2H-Benzoxazines. Reaction of p -Substituted Phenols with N,N-Dimethylolamines
    journal, February 1949

    • Burke, W. J.
    • Journal of the American Chemical Society, Vol. 71, Issue 2
    • DOI: 10.1021/ja01170a063

    Jack of all trades: versatile catechol crosslinking mechanisms
    journal, January 2014

    • Yang, Juan; Cohen Stuart, Martien A.; Kamperman, Marleen
    • Chem. Soc. Rev., Vol. 43, Issue 24
    • DOI: 10.1039/c4cs00185k

    Enzymatic polymerization of catechol under high-pressure homogenization for the green coloration of textiles
    journal, November 2018


    High-Performance Bio-Based Benzoxazines from Enzymatic Synthesis of Diphenols
    journal, November 2018

    • Bonnaud, Leïla; Chollet, Benjamin; Dumas, Ludovic
    • Macromolecular Chemistry and Physics, Vol. 220, Issue 1
    • DOI: 10.1002/macp.201800312

    Mussel-Inspired Adhesives and Coatings
    journal, August 2011


    A simple surface treatment and characterization of AA 6061 aluminum alloy surface for adhesive bonding applications
    journal, November 2012


    A mussel-inspired polybenzoxazine containing catechol groups
    journal, December 2018


    Surface Roughness and Bond Strength of Adhesives
    journal, May 1972


    A Study on Hydrogen-Bonded Network Structure of Polybenzoxazines
    journal, April 2002

    • Kim, Ho-Dong; Ishida, Hatsuo
    • The Journal of Physical Chemistry A, Vol. 106, Issue 14
    • DOI: 10.1021/jp010606p

    Simple but Strong: A Mussel-Inspired Hot Curing Adhesive Based on Polyvinyl Alcohol Backbone
    journal, January 2016


    Smart and sustainable design of latent catalyst-containing benzoxazine-bio-resins and application studies
    journal, January 2020

    • Zhang, Kan; Liu, Yuqi; Han, Mengchao
    • Green Chemistry, Vol. 22, Issue 4
    • DOI: 10.1039/c9gc03504d

    Hydroxyarginine-containing Polyphenolic Proteins in the Adhesive Plaques of the Marine Mussel Mytilus edulis
    journal, August 1995

    • Papov, Vladimir V.; Diamond, Thomas V.; Biemann, Klaus
    • Journal of Biological Chemistry, Vol. 270, Issue 34
    • DOI: 10.1074/jbc.270.34.20183

    A comprehensive metabolic map for production of bio-based chemicals
    journal, January 2019


    Mechanical characterization of copolymers based on benzoxazine and epoxy
    journal, September 1996


    Primary Amine-Functional Benzoxazine Monomers and Their Use for Amide-Containing Monomeric Benzoxazines
    journal, March 2010

    • Agag, Tarek; Arza, Carlos R.; Maurer, Frans H. J.
    • Macromolecules, Vol. 43, Issue 6
    • DOI: 10.1021/ma902556k

    Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzoxazines
    journal, July 1999


    The efficiency of various toughening agents in novel phenolic type thermoset resin systems
    journal, October 2006

    • Dipl. -Ing. Gietl, T.; Dr. -Ing. Lengsfeld, H.; Dr. -Ing. Altstädt, V.
    • Journal of Materials Science, Vol. 41, Issue 24
    • DOI: 10.1007/s10853-006-0879-9

    Phenolic materials via ring-opening polymerization of benzoxazines: Effect of molecular structure on mechanical and dynamic mechanical properties
    journal, April 1994


    Bioinspired polymeric woods
    journal, August 2018


    Phenolic Naphthoxazines as Curing Promoters for Benzoxazines
    journal, February 2018


    A reversible underwater glue based on photo- and thermo-responsive dynamic covalent bonds
    journal, January 2020

    • Wang, Zhao; Guo, Lifeng; Xiao, Hongyan
    • Materials Horizons, Vol. 7, Issue 1
    • DOI: 10.1039/c9mh01148j

    Bioinspired structural materials
    journal, October 2014

    • Wegst, Ulrike G. K.; Bai, Hao; Saiz, Eduardo
    • Nature Materials, Vol. 14, Issue 1
    • DOI: 10.1038/nmat4089

    Physical and mechanical properties of flexible polybenzoxazine resins: Effect of aliphatic diamine chain length
    journal, January 2006

    • Allen, Douglas J.; Ishida, Hatsuo
    • Journal of Applied Polymer Science, Vol. 101, Issue 5
    • DOI: 10.1002/app.22501

    Breaking the symmetry of dibenzoxazines: a paradigm to tailor the design of bio-based thermosets
    journal, January 2016

    • Puchot, L.; Verge, P.; Fouquet, T.
    • Green Chemistry, Vol. 18, Issue 11
    • DOI: 10.1039/c5gc03102h

    Catechol oxidation: considerations in the design of wet adhesive materials
    journal, January 2018

    • Maier, Greg P.; Bernt, Christopher M.; Butler, Alison
    • Biomaterials Science, Vol. 6, Issue 2
    • DOI: 10.1039/c7bm00884h

    Tough, Bio-Inspired Hybrid Materials
    journal, December 2008


    Study on benzoxazine-based film adhesive and its adhesion properties with CFPR composites
    journal, January 2017


    Natural monomers: A mine for functional and sustainable materials – Occurrence, chemical modification and polymerization
    journal, May 2019


    Mussel-Inspired Thiol–Ene Polymer Networks: Influencing Network Properties and Adhesion with Catechol Functionality
    journal, September 2012

    • Sparks, Bradley J.; Hoff, Ethan F. T.; Hayes, LaTonya P.
    • Chemistry of Materials, Vol. 24, Issue 18
    • DOI: 10.1021/cm302301e

    Intrinsic self-initiating thermal ring-opening polymerization of 1,3-benzoxazines without the influence of impurities using very high purity crystals
    journal, July 2017

    • Han, Lu; Salum, María Laura; Zhang, Kan
    • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 55, Issue 20
    • DOI: 10.1002/pola.28723

    Polybenzoxazines: new players in the bio-based polymer arena
    journal, January 2014

    • Lligadas, Gerard; Tüzün, Alev; Ronda, Juan C.
    • Polym. Chem., Vol. 5, Issue 23
    • DOI: 10.1039/c4py00914b

    Synthesis and properties of thermosetting resin based on urushiol
    journal, January 2012

    • Xu, Hongli; Lu, Zaijun; Zhang, Guangzhao
    • RSC Advances, Vol. 2, Issue 7
    • DOI: 10.1039/c2ra00829g

    Cardanol benzoxazines – interplay of oxazine functionality (mono to tetra) and properties
    journal, January 2015

    • Shukla, Swapnil; Mahata, Arup; Pathak, Biswarup
    • RSC Advances, Vol. 5, Issue 95
    • DOI: 10.1039/c5ra14214h

    Synthetic Biomaterials from Metabolically Derived Synthons
    journal, January 2016


    Understanding the surface properties of polybenzoxazines: Interaction of polybenzoxazine model compounds with metal ions and water
    journal, July 2016

    • Shen, D.; Liu, C.; Sebastián, R. M.
    • Journal of Applied Polymer Science, Vol. 133, Issue 42
    • DOI: 10.1002/app.44099

    Development of Fully Biobased High-Performance Bis-Benzoxazine under Environmentally Friendly Conditions
    journal, March 2018

    • Kotzebue, Lloyd R. V.; de Oliveira, Jéssica R.; da Silva, Joane B.
    • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 4
    • DOI: 10.1021/acssuschemeng.8b00340

    Silyl Ether as a Robust and Thermally Stable Dynamic Covalent Motif for Malleable Polymer Design
    journal, October 2017

    • Nishimura, Yoshio; Chung, Jaeyoon; Muradyan, Hurik
    • Journal of the American Chemical Society, Vol. 139, Issue 42
    • DOI: 10.1021/jacs.7b08826