SYNTHESIS OF ESTER TERMINATED TELECHELIC POLYMER VIA ADMET POLYMERIZATION

Abstract

Ester terminated telechelic polymers were synthesized by the Acyclic Diene METathesis (ADMET) polymerization of 1,9-decadiene with ester-containing monoolefins using ruthenium based Grubbs catalyst. The number of methylene spacers between the olefin and the ester from the oxygen side of the ester-containing monoolefins were varied from one to three. The optimal condition of the present ADMET polymerization was determined as monomer/catalyst ratio of 400/1 for 72 hours at 90°C. All polymer structures were characterized by FT-IR and ¹H-NMR spectroscopy. It is quite interesting that even allyl n-butyrate with one methylene spacer metathesizes successfully using ruthenium catalyst despite this monoolefin suffers stronger negative neighboring group effect than the other monoolefins. Mechanism of the ADMET polymerization of 1,9-decadiene with ester-containing monoolefin was examined comparing the reactions for each of the monomers. Deprotection of terminal ester group was successful to give alcohol terminated telechelic polymer which is useful for production of block copolymer.

Keywords:

• Metathesis
• ADMET Polymerization
• Grubbs Catalyst
• Telechelic Polymer

ACKNOWLEDGEMENTS

We acknowledge support of this work from the Kansai University Overseas Research Program. We also acknowledge to Dr. K. B. Wagener for his helpful and devoted discussions and suggestions.