Bio-based elastomeric composites for antibacterial and antifouling applications : methodology for the synthesis and grafting of functionalized oligomers issued from natural rubber

Abstract : This manuscript presents the synthesis of new elastomeric materials based on natural rubber derived building blocks and organic monomers having antifouling and/or antibacterial properties, covalently bound to the polymer network. Original acrylate monomers bearing an organic bioactive moiety (a Guanidinium group or Zosteric acid derivates) were synthesized and co-polymerized with telechelic acrylate oligomers from polyisoprene. No significant leaching of the bioactive monomers occurred and the material resisted to long water immersions. Freestanding films prepared from acrylate oligoisoprenes also showed a weak antibiofouling activity which was drastically increased by integrating the guanidinium and the Zosteric acid monomers. The coatings were active against several strains of pathogenic bacteria among which Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis and Staphylococcus epidermidis. In order to covalently graft oligoisoprenes to surfaces, new bifunctional oligoisoprenes bearing an alkoxy-silane end moiety were designed and coupled with silicon-containing materials. An alternative approach was followed by prefunctionalizing the surface with amino groups and by covalently grafting oligomers with carbonyl chain-ends. Post-polymerization from the surface free chain-ends resulted in a thick oligoisoprene coating with strong resistance to solvent immersion (water, THF). In this way, we were able to build dense and tethered molecular layers, thin films and thick coatings.
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Thi Nguyet Tran. Bio-based elastomeric composites for antibacterial and antifouling applications : methodology for the synthesis and grafting of functionalized oligomers issued from natural rubber. Material chemistry. Université du Maine, 2018. English. ⟨NNT : 2018LEMA1024⟩. ⟨tel-02196348⟩

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