Cooperativity of Catechols and Amines in High‐Performance Dry/Wet Adhesives

The outstanding adhesive performance of mussel byssal threads has inspired materials scientists over the past few decades. Exploiting the amino‐catechol synergy, polymeric pressure‐sensitive adhesives (PSAs) have now been synthesized by copolymerizing traditional PSA monomers, butyl acrylate and acr...

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Bibliographic Details
Published in:Angewandte Chemie 2020-09, Vol.132 (38), p.16759-16767
Main Authors: Tiu, Brylee David B., Delparastan, Peyman, Ney, Max R., Gerst, Matthias, Messersmith, Phillip B.
Format: Article
Language:English
Subjects:
Acrylic acid
Acrylics
Adhesion
Adhesives
AFM force spectroscopy
Amines
Atomic force microscopy
bioinspired materials
Catechol
catechol–amine
Chemistry
Copolymerization
Coupling (molecular)
Decoupling
Lysine
Mollusks
Monomers
mussels
Spectroscopy
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Summary:The outstanding adhesive performance of mussel byssal threads has inspired materials scientists over the past few decades. Exploiting the amino‐catechol synergy, polymeric pressure‐sensitive adhesives (PSAs) have now been synthesized by copolymerizing traditional PSA monomers, butyl acrylate and acrylic acid, with mussel‐inspired lysine‐ and aromatic‐rich monomers. The consequences of decoupling amino and catechol moieties from each other were compared (that is, incorporated as separate monomers) against a monomer architecture in which the catechol and amine were coupled together in a fixed orientation in the monomer side chain. Adhesion assays were used to probe performance at the molecular, microscopic, and macroscopic levels by a combination of AFM‐assisted force spectroscopy, peel and static shear adhesion. Coupling of catechols and amines in the same monomer side chain produced optimal cooperative effects in improving the macroscopic adhesion performance. Making it stick: The design and synthesis of amino‐catechol adhesives by copolymerization of traditional monomers with mussel‐inspired monomers is presented. The coexistence of catechol and amine moieties in a hybrid monomer architecture can lead to optimization of the overall performance of the catechol–amine adhesives and the development of pressure‐sensitive adhesives with remarkable resistance to flow under shear.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202005946