Abstract
The synthesis of carboxylated derivatives of poly(isobutylene-co-isoprene) (isobutylene–isoprene rubber, IIR) with substitution levels ranging from 1 to 4 mol% and different spacer lengths was accomplished through azide–alkyne Huisgen cycloaddition. Azido-functionalized IIR was first prepared by reacting brominated IIR with sodium azide to full conversion in a 90:10 tetrahydrofuran/N,N-dimethylacetamide mixture. The click reaction of azido-functionalized IIR with acetylenic acids, which was carried out using the copper(I) bromide/N,N,N′,N″,N″-pentamethyldiethylenetriamine catalyst system in tetrahydrofuran, yielded carboxylated IIRs. The products were characterized by 1H NMR and FT-IR spectroscopy, and their molecular weight was determined by size exclusion chromatography analysis. The conversion to carboxylated groups reached up to 100% as determined by NMR spectroscopy but was highly dependent on the type of solvent and the amounts of catalysts and reactants used in the procedures.
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Acknowledgements
The authors thank ARLANXEO Canada Inc. and the Natural Sciences and Engineering Research Council (NSERC) of Canada for their generous support of this work. We are also grateful to the late Dr. Lorenzo Ferrari and to Dr. Dana Adkinson for useful discussions in relation to this research.
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Deepak, V.D., Mahmud, I. & Gauthier, M. Synthesis of carboxylated derivatives of poly(isobutylene-co-isoprene) by azide–alkyne “click” chemistry. Polym J 51, 327–335 (2019). https://doi.org/10.1038/s41428-018-0130-y
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DOI: https://doi.org/10.1038/s41428-018-0130-y
