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Synthesis of de-crosslinkable polyamide having hexaarylbisimidazolyl moieties

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Abstract The e-caprolactam monomer having a triphenylimidazole moiety such as DL-3-[α-4-(4,5-diphenyl-1H-imidazole-2-yl)-phenylacryloyl-amine]-e-caprolactam (1) was synthesized by the Heck reaction of 2-(4-bromophenyl)-1-(methoxymethyl)-4,5-diphenylimidazole and the e-caprolactam derivative having an acryloyl group in a… Click to show full abstract

Abstract The e-caprolactam monomer having a triphenylimidazole moiety such as DL-3-[α-4-(4,5-diphenyl-1H-imidazole-2-yl)-phenylacryloyl-amine]-e-caprolactam (1) was synthesized by the Heck reaction of 2-(4-bromophenyl)-1-(methoxymethyl)-4,5-diphenylimidazole and the e-caprolactam derivative having an acryloyl group in a good yield. The copolymerization of 1 and e-caprolactam was carried out at 250 °C by using H2O as an initiator to give copolymer (4) in a good yield. The crosslinking reaction of the obtained 2 proceeded with K3[Fe(CN)6] and KOH in a mixed solvent of ethanol and phenol. The resulting crosslinked polymer (5) was de-crosslinked under irradiation with visible light. Consequently, the thiol-capped de-crosslinked polymer (6) was obtained in a good yield.

Keywords: hexaarylbisimidazolyl moieties; good yield; synthesis crosslinkable; crosslinkable polyamide; polyamide hexaarylbisimidazolyl; caprolactam

Journal Title: Polymer
Year Published: 2018

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