Azlactone Telechelic Polyolefins as Precursors to Polyamides A Combination of Metathesis Polymerization and Polyaddition Reactions

Abstract : Expanding on our strategy to design telechelic polyolefins through the catalyzed ring-opening metathesis polymerization/cross metathesis/ring-closing metathesis polymerization of cyclic olefins using bifunctional symmetric alkene chain transfer agents (CTAs), we have now explored the metathesis of cyclooctene (COE), 1,5,9-cyclododecatriene (CDT), and norbornene (NB), using azlactone (AZL)-functional CTAs, toward the synthesis of original AZL telechelic polyolefins. The monofunctional 2-vinyl-4,4-dimethylazlactone predominantly gives, as anticipated, (isomerized) monofunctional and/or difunctional PCOEs. On the other hand, the new symmetric AZL-based CTAs 1–3, namely, (E)-2,2′-(ethene-1,2-diyl)bis(4,4-dimethyloxazol-5(4H)-one) (1), (E)-2,2′-(but-2-ene-1,4-diyl)bis(4,4-dimethyloxazol-5(4H)-one) (2), and (E)-2,2′-(but-2-ene-1,4-diyl)bis(3-oxa-1-azaspiro[4.5]dec-1-en-4-one) (3), selectively give α,ω-di(AZL) telechelic PCOEs, along with minor amounts of cyclic PCOE. The synthesis of related AZL telechelic CDT and NB copolymers has also been implemented through such a tandem metathesis approach. Subsequently, the inherent AZL reactivity toward (di)amines has been evidenced using a triethylene glycol diamine, in first the model reaction with CTA 3 and next upon reacting with the new α,ω-di(CTA 3)-P(NB-co-CDT) copolymers, thereby enabling the preparation of original polyolefins/polyamides
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Cyril Chauveau, Elise Vanbiervliet, Stéphane Fouquay, Guillaume Michaud, Frédéric Simon, et al.. Azlactone Telechelic Polyolefins as Precursors to Polyamides A Combination of Metathesis Polymerization and Polyaddition Reactions. Macromolecules, American Chemical Society, 2018, 51 (20), pp.8084-8099. ⟨10.1021/acs.macromol.8b01628⟩. ⟨hal-01935366⟩

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