Accessing the Next Generation of Synthetic Mussel‐Glue Polymers via Mussel‐Inspired Polymerization
| Autor: | Hans G. Börner, Jana M. Krüger |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Bisphenol
Biomimetic Glues | Hot Paper 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Dopa mimics adhesive library Mussel-inspired glue chemistry.chemical_classification 010405 organic chemistry Chemistry Communication General Chemistry Epoxy Adhesion Polymer Cysteinyldopa Communications 0104 chemical sciences Monomer 540 Chemie und zugeordnete Wissenschaften Polymerization Chemical engineering visual_art ddc:540 visual_art.visual_art_medium ddc:660 Adhesive Biomimetic adhesives 660 Chemische Verfahrenstechnik und verwandte Technologien |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| DOI: | 10.18452/23238 |
| Popis: | 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 synthesis of mussel‐glue‐inspired polymers by using simple one‐pot chemistry based on commodity monomers that are available in large scale offers many opportunities. A chemical oxidation route to convert commodity monomers to bisquinones is presented. These can be polymerized in Michael‐type polyaddition reactions with various dithiols, which provides a modular set of glues with adhesive thiol–catechol connectivities in their backbones. |
| Databáze: | OpenAIRE |
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