Synthesis and characterization of new thermally stable poly(ester‐imide)s derived from 2,2′‐bis(4‐trimellitimidophenoxy)biphenyl and 2,2′‐bis(4‐trimellitimidophenoxy)‐1,1′‐binaphthyl and various aromatic dihydroxy compounds

Abstract

A series of new alternating aromatic poly(ester-imide)s were prepared by the polycondensation of the preformed imide ring-containing diacids, 2,2 -bis(4-trimellitimidophenoxy)biphenyl (2a) and 2,2bis(4-trimellitimidophenoxy)-1,1 -binaphthyl (2b) with various aromatic dihydroxy compounds in the presence of pyridine and lithium chloride. A model compound (3) was also prepared by the reaction of 2b with phenol, its synthesis permitting an optimization of polymerization conditions. Poly(esterimides) were fully characterized by FTIR, UV-vis and NMR spectroscopy. Both biphenylene-and binaphthylene-based poly(ester-imide)s exhibited excellent solubility in common organic solvents such as tetrahydrofuran, m-cresol, pyridine and dichloromethane. However, binaphthylene-based poly(esterimide)s were more soluble than those of biphenylene-based polymers in highly polar organic solvents, including N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide and dimethyl sulfoxide. From differential scanning calorimetry thermograms, the polymers showed glass-transition temperatures between 261 and 315 • C. Thermal behaviour of the polymers obtained was characterized by thermogravimetric analysis, and the 10 % weight loss temperatures of the poly(ester-imide)s was in the range 449-491 • C in nitrogen. Furthermore, crystallinity of the polymers was estimated by means of wide-angle X-ray diffraction. The resultant poly(ester-imide)s exhibited nearly an amorphous nature, except poly(ester-imide)s derived from hydroquinone and 4,4 -dihydroxybiphenyl. In general, polymers containing binaphthyl units showed higher thermal stability but lower crystallinity than polymers containing biphenyl units.

Synthesis and properties of new aromatic poly(ester‐imide)s derived from 4‐p‐biphenyl‐2,6‐bis(4‐trimellitimidophenyl) pyridine and various dihydroxy compounds

“…Alongside these studies, we successfully prepared series of aromatic copolyimides, such as poly(amideimide)s, 16 poly(ester-imide)s, 17 poly(urethaneimide)s, 18 and poly(urea-imide)s, 19 from a number of new imide-ring-containing dicarboxylic acids. In these research activities, direct polycondensation reactions were mainly used and the polymers were obtained by one-pot reactions.…”

Direct synthesis of new soluble and thermally stable poly(urethane‐imide)s from an imide ring‐containing dicarboxylic acid using diphenylphosphoryl azide

“…In our previous studies, we successfully prepared a series of wholly aromatic poly(amide‐imide)s, poly(ester‐imide)s, and poly(urethane‐imide)s from a number of new imide‐containing dicarboxylic acids 22–27. Among them, a dicarboxylic acid bearing two imide rings 4‐ p ‐biphenyl‐2,6‐bis(4‐trimellitimidophenyl)pyridine, 1 , was used for some polymerization purposes.…”

Materials containing benzocyclobutene units with low dielectric constant and good thermostability prepared from star‐shaped molecules

“…Characterization 1 H-NMR, 13 C-NMR, and 29 Si-NMR spectra were obtained with a Bruker Avance-600 (Karlsruhe, Germany) using deuterated chloroform as the solvent and tetramethylsilane as the internal reference. Fourier transform infrared (FTIR) measurements at 400-4000 cm −1 were conducted on a Nicolet FTIR 5700 spectrophotometer (Waltham, MA) at room temperature, and the sample films were prepared by casting the solution on KBr plates.…”

“…In the past decades, tremendous effort has been made to decrease the dielectric constant and improve the thermal stability of interlayer materials . A number of polymeric low ‐k materials have been discussed, including polyimides, poly(naphthylene)s, SiLK (product of Dow Chemical), and benzocyclobutene resins, and their performance is shown in Table .…”