M. E. Wright, S. Fallis, A. Guenthner
Nov 5, 2005
Citations
0
Influential Citations
10
Citations
Journal
Macromolecules
Abstract
Two new monomers were prepared of the formula 3,X-bis(4-aminophenoxy)benzenemethanol (where X = 5, 3a; X = 4, 3b) and each copolymerized with 2,2-bis(4-aminophenyl)hexafluoropropane, 6-FDA, and 6 mol % of phthalic anhydride as an end-cap to afford polyimides 4 and 5, respectively. The CH2OH group in the polymers could be modified with excess 1,6-hexanediisocyanate to afford 100% modification of polymer 6 concomitant with formation of a pendent and reactive isocyanate group. This latter polymer was shown to react with disperse red 1 (DR-1) to produce a polyimide-supported dye (7, Tg 199 °C) via formation of a urethane linkage. Treatment of the polymers 4 and 5 with excess adipoyl chloride afforded polymers 8 and 9, respectively, with a pendent acid chloride functional group. Further reaction with disperse red 1 (DR-1) in the presence of DMAP led to rapid esterification, yielding high-Tg dye-attached polyimides 11 (Tg 168 °C) and 12 (Tg 175 °C). Treatment of polymer 4 with sebacoyl chloride (a longer spacer...