Synthesis of novel poly(thioether-naphthalimide)s that utilize hydrazine as the diamine

Abstract

A series of bis(4‐thio‐1,8‐naphthalic anhydride)s and the corresponding bis(N‐amino naphthalimide) derivatives were synthesized from readily available compounds in high yield. A series of novel poly(thioether‐naphthalimide)s, which utilized hydrazine as the diamine, were synthesized by a one‐step polymerization reaction in m‐cresol. Poly(thioether‐naphthalimide)s with inherent viscosities of 0.57–1.73 dL/g were obtained. The polymers were soluble in CHCl3 and were determined to have high molecular weights by means of gel permeation chromatographic analysis. They were soluble in m‐cresol and could be cast into tough films from m‐cresol solution. The glass‐transition temperature (Tg) values of the polyimides ranged from 320 to 353 °C. Polyimides from the bisphenol dianhydride, derived from 9,9‐bis(4‐hydroxyphenyl)fluorene, did not show a clear transition in the DSC analysis. Degradation temperatures for 5% weight loss all occurred above 430 °C in nitrogen. The series of monomers were successfully copolymerized with each other. Monomers 6a and 7a, containing the bisphenol A moiety, could also be copolymerized with perylenetetracarboxylic dianhydride. These copolymers had high Tg's and were thermally stable. The UV–vis absorption properties of the polymers were also examined. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1040–1050, 2001

Enhanced hydrolytic stability of sulfonated polyimide ionomers using bis(naphthalic anhydrides) with low electron affinity

“…The reaction was cooled to room temperature and poured into a dilute hydrochloric acid solution to precipitate a yellow solid, which was Benzophenone-4,4 0 -bis(4-thio-1,8-naphthalic anhydride) (BPBTNA). BPBTNA was prepared by previously reported methods: 50 To a stirred solution of 4-bromo-1,8-naphthalic anhydride (3.05 g, 11 mmol) in DMAc (80 mL), 4,4 0 -dimercaptobenzophenone (1.23 g, 5 mmol) and triethylamine (TEA) (1.53 mL, 11 mmol) were added. The reaction mixture was heated at 80 C under a nitrogen atmosphere for 5 h. The reaction was cooled to room temperature and poured into a dilute hydrochloric acid solution (800 mL) to precipitate a yellow solid, which was ltered, thoroughly washed with water to pH inlet, 0.61 g (1.65 mmol) ODADS, 0.40 g (3.95 mmol) triethylamine, and 15 mL m-cresol were introduced.…”

Synthesis and properties of polyimides from isomeric bis(dicarboxylphenylthio)diphenyl sulfone dianhydrides

“…Polythioetherimides derived from bis(thioetheranhydride)s have been reported since the work of Williams in 1970s [22][23][24][25]. As a part of the work about isomeric polyimides in our lab, we present the comparative study on the synthesis and properties of polyimides based on isomeric bis(dicarboxylphenylthio)diphenyl sulfone dianhydrides(PTPSDAs) in this paper.…”

Synthesis and characterization of thioether-containing polyimides with high refractive indices

“…The sulfur-containing dianhydride 2SDEA was synthesized using nucleophilic substitution reaction from 1,4-benzenedithiol and 4-bromophthalic anhydride with a yield of 65%, as reported in the literature [24,[32][33][34]. Due to the high reactivity of the thiophenol group in 1,4-benzenedithiol, 4-bromophthalic anhydride can react with it directly to synthesize the dianhydride.…”