The versatile chemistry exhibited by catechols (e.g. covalent cross-linking, metal chelating) has led to a number of groups exploring the incorporation of catechol functionality into synthetic backbones. These systems are inspired by the peptide sequence of the mussel foot proteins, which exhibit good adhesion under wet and dirty environments. These interfacial proteins exhibit nearly a third of the repeat units consist of 3,4-dihydroxyphenylalanine (DOPA) which have pendent catechols. We have synthesized a library of poly(meth)acrylate-co-1-[2-(3,4-dihydroxyphenyl)ethyl]-maleimides(PAMs for acrylates, PMAMs for methacrylates) that vary in their aliphatic side-chain length and comonomer composition on a common polymer backbone, allowing for control over Tg and backbone polarity. We have observed modest adhesive performance from the library on alumina substrates, with minimal performance shifts with Tg change or side-chain polarity. When blended with more traditional epoxy-based adhesives, however, the PAMs were found to improve hot/wet adhesion without a silane pretreatment. It is hoped that these materials will provide fundamental insight to improve performance at the adhesive/substrate interface, allowing for the rational design of improved performance in adverse environments.

Catechol-functionalized acrylates and methacrylates: Comonomer influence on adhesive properties

2019 Fall National Meeting

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