The formation of cysteinyldopa as biogenic connectivity in proteins is used to inspire a chemical pathway toward mussel‐adhesive mimics. The mussel‐inspired polymerization (MIPoly) exploits the chemically diverse family of bisphenol monomers that is oxidizable with 2‐iodoxybenzoic acid to give bisquinones. Those react at room temperature with dithiols in Michael‐type polyadditions, which leads to polymers with thiol–catechol connectivities (TCC). A set of TCC polymers proved adhesive behavior even on challenging poly(propylene) substrates, where they compete with commercial epoxy resins in dry adhesive strength. MIPoly promises facile scale up and exhibits high modularity to tailor adhesives, as proven on a small library where one candidate showed wet adhesion on aluminum substrates in both water and sea water models.

The mussel-inspired polymerization (MIPoly) of bisquinone (AA type) and dithiol (BB type) monomers utilizes room temperature Michael-type polyaddition to form polymers with adhesive thiol–catechol connectivities (TCCs) in their backbone. The combination of five bisquinones and eight dithiols proves the generic character of this robust polymerization and leads to a TCC-polymer library with 40 different polymers. The set of adhesives is investigated in detail, and structure–property relationships are studied, analyzing material properties and adhesive capabilities. Dry adhesive tests are carried out under hot-melt-like conditions, revealing adhesive strengths up to 2.40 MPa for gluing aluminum and 1.26 MPa for polypropylene. A selected set of TCC adhesives is further studied under seawater-model conditions for the wet-gluing and wet-curing of technical aluminum substrates. The library approach offers access to novel adhesives in the field of mussel-inspired glues as shown by seawater-tolerant adhesives that are providing adhesive strengths of up to 1.25 MPa under hostile high-salt conditions.

A His-rich domain of preCollagen-D found in byssal threads is derivatized by Cys and Dopa residues to allow for mussel-inspired polymerization. Artificial mussel foot proteins are accessed that combine cystenyldopa...

Die muschelinspirierte Polymerisation (MIPoly) stellt, inspiriert durch die Bildung von Cysteinyldopa als biogene Verknüpfungseinheit, eine Möglichkeit dar, um synthetisch adhäsive Polymere herzustellen. Hierbei wird die große Familie der chemisch vielfältigen Bisphenolmonomere eingesetzt, die durch 2‐Iodoxybenzoesäure zu Dichinonen aktiviert werden kann. Diese Dichinone reagieren in Michael‐artigen Polyadditionen mit Dithiolen, wobei Polymere mit adhäsiven Thiol‐Catechol‐Verknüpfungen (thiol–catechol connectivities, TCC) gebildet werden. Eine Reihe verschiedener TCC‐Polymere zeigte adhäsive Eigenschaften auf Aluminium und Polypropylen, wobei diese auf dem anspruchsvollen Polypropylen konkurrenzfähige Haftfestigkeiten zu handelsüblichen Epoxidharzen aufwiesen. Die MIPoly verspricht eine einfache Skalierbarkeit und hohe Modularität, wodurch maßgeschneiderte Klebstoffe hergestellt werden könnten. Dies wurde anhand einer kleinen Stoffbibliothek nachgewiesen, aus der ein Kandidat bereits eine Unterwasserklebung von Aluminium erlaubte.