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- W1991636698 abstract "An efficient synthesis of (1Z)-1-amino-1,2-dicyano-3-aza-1,3,5-hexatriene (acrodamn), via condensation of acrolein and diaminomaleonitrile (DAMN), is described. A larger laboratory-scale synthesis of 4,5-dicyano-2-vinylimidazole (vinazene) is described in detail. The alkylation of vinazene proceeds with strong electrophiles. The compound, 4,5-dicyano-1-methyl-2-vinylimidazole (1-methylvinazene), undergoes Michael addition with pyrrolidine, morpholine, and thiophenol and at higher temperatures with itself, resulting in step-growth oligomerization. Direct measurements of kinetic rates for vinylic radical addition polymerization of vinazene yielded kapp = kp/2√ktfkd values of (7.2 ± 0.25) × 10-3 and (6.6 ± 0.27) × 10-3. Direct measurements of kinetic rates for 1-methylvinazene yielded kapp = kp/2√ktfkd values of (4.3 ± 0.31) × 10-3 and (3.7 ± 0.06) × 10-3. Indirect measurements show the polymerization obeys first-order kinetics. The poly(vinazene) is an acidic material with molecular weights ranging from 100 000 to 200 000 and polydispersities between 2.0 and 2.9. The Mark−Houwink constants for poly(vinazene) in 0.05 M LiBr in N-methylpyrrolidinone were K = 3.35 × 10-5 and a = 0.889. The titration behavior is similar to poly(methacrylic acid)." @default.
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- W1991636698 date "2000-10-21" @default.
- W1991636698 modified "2023-10-09" @default.
- W1991636698 title "An Improved Synthesis of 2-Vinyl-4,5-dicyanoimidazole and Characterization of Its Polymers" @default.
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- W1991636698 doi "https://doi.org/10.1021/ma000779x" @default.
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