Functional Telechelic Polymer Synthesis via Admet Polymerization

Acyclic Diene METathesis (ADMET) polymerization of 1,9-decadiene with epoxy-containing monoolefins using ruthenium based Grubbs' catalyst gave epoxy terminated telechelic polymers. The number of methylene spacers between the olefin and the epoxy from the oxygen side of the epoxy-containing monoolefins was varied from one to three. The optimal condition for the present ADMET polymerization was determined as monomer/catalyst ratio of 200/1 for 96 hr at 90°C. All polymer structures were characterized by FT-IR and 1H NMR spectroscopy. It is quite interesting that even 1,2-epoxy-4-pentene with one methylene spacer metathesizes successfully using ruthenium catalyst despite this monoolefin suffers a stronger negative neighboring group effect than the other monoolefins. The telechelic polymer was reacted with toluene diisocyanate to give a higher molecular weight segmented copolymer connected with oxazolidone linkage.