Ring-opening metathesis polymerization (ROMP) of substituted cis-cyclooctenes (COEs) followed by hydrogenation of the resulting unsaturated linear polymers represents a powerful method to access functional linear polyolefins (POs). The excellent synthetic control over controllable molar mass, architecture, and functionality afforded by this strategy facilitates the synthesis of myriad polymeric materials with tunable physical properties. Here we describe the synthesis and polymerization of a new COE monomer, (Z)-5,5-dimethylcyclooct-1-ene (DMC), which affords linear amorphous hydroxy-telechelic poly(ethylene-co-isobutylene) (PEIB) in the presence of multifunctional chain transfer agents. To highlight the utility of this material, we discuss polyurethane (PU) elastomers synthesized using low molar mass telechelic PEIB as a soft segment, as well as PO thermoplastics and elastomers based on high molar mass PEIB derivatives. These materials are characterized by excellent chemical stability and mechanical performance. In the copolymerization of DMC with COE, also described, we find the monomer feed ratio can be used to adjust the equivalent isobutylene content and branching density of the copolymer. Oxidative degradation studies, conducted under accelerated in vitro conditions indicate PEIB-based materials are characterized by higher oxidative stability than a commercial polyether urethane, Elasthane 80A, and a structurally similar PO, poly(ethylene-co-1-butylene). The facile synthesis, improved stability, and the excellent mechanical performance of PEIB and PEIB-based PUs, suggest that they are promising materials for use in various biomedical applications.

New polyolefins via ring-opening metathesis polymerization for biomedical applications

253rd National Meeting (2017)

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