Summary
Di-tert-butyl fumarate (DtBF) was found to homopolymerize easily with 1,1′-azobisisobutyronitrile and benzoyl peroxide as radical initiators at 50~80°C to give a nonflexible rod-like polymer, poly(tert-butoxycarbonylmethylene) with number-average molecular weight of more than 100,000. The colorless powderlike polymer thus obtained was soluble in benzene, toluene, carbon tetrachloride and tetrahydrofuran, and gave a transparent film or fiber from its toluene solution. This polymer did not melt, but it underwent degradation with a quantitative elimination of isobutene at 180~190°C. The remaining polymer was confirmed to be a pure poly(fumaric acid), poly(hydroxycarbonylmethylene). Therefore, the degradation of poly(DtBF) in solution at 180~190°C was found to be a new route for synthesizing of a high molecular weight poly(fumaric acid).
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Polymers from 1,2-Disubstituted Ethylenic Monomers. XI. Parts I~X of this series are Refs. 1~10.
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Otsu, T., Yasuhara, T., Shiraishi, K. et al. Radical high polymerization of di-tert-butyl fumarate and novel synthesis of high molecular weight poly(fumaric acid) from its polymer. Polymer Bulletin 12, 449–456 (1984). https://doi.org/10.1007/BF00255433
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DOI: https://doi.org/10.1007/BF00255433