Preparation, characterization, and properties of poly(thioether ether ketone imide)s from isomeric bis(chlorophthalimide)s

Abstract

A series of novel poly(thioether ether ketone imide)s (PTEKIs) bearing the thioether and ketone groups with high molecular weights (Mw: 87,800–150,100 g/mol) were synthesized by aromatic nucleophilic substitution reaction. The polymers were characterized by Fourier transform infrared spectra (FT‐IR), 1H NMR, GPC, and elemental analysis. The composition of the copolymers varied systematically in order to study its relation with polymer properties. Increase in the content of 3‐substituted phthalimide moiety in the polymer backbone improves the solubility in tested solvents, and increases the glass transition temperature (Tg), whereas copolymers with high content of 3‐substituted phthalimide demonstrated to be inferior thermal stability. The PTEKI films also exhibited good optical transparency, including the cutoff wavelengths lower than 400 nm and transmittances higher than 77% at 450 nm. Copyright © 2010 John Wiley & Sons, Ltd.

Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

“…3, the T 5 % values of PTIs (a-e) in nitrogen were in the range 506-531°C, and gradually increased following the order: a \ b \ c \ d \ e, which could be interpreted by the fact that the 3-phthalimide unit has lower thermal stability than 4-phthalimide unit [24]. The inferior thermal stability of the PTI (a) derived from isomer 1 may be ascribed to the structural stress caused by nonplanar configuration of the 3-substituted phthalimide moiety [22,23]. As presented in Fig.…”

“…This phenomenon was probably because the restricted C-S bond between 3-substituted phthalimide and benzene ring rotated much more difficultly than the C-S bond between 4-substituted phthalimide and benzene ring [22][23][24]. As shown in Fig.…”

“…What is more, the copolyimides PTIs (b-d) had slightly better solubility than the homopolyimides PTIs (a, e) in m-cresol and phenol. That was because unsymmetrical 3-and 4-substituted phthalimide unit disturbed the regularity of molecular chain, which reduced the intermolecular interaction and hindered molecular chain close stacking and, therefore, improved the solubility of isomeric PTIs [20][21][22][23][24][25][26].…”

“…Recently, our group has successfully synthesized series of isomeric polythioetherimides by the polycondensation of isomeric dianhydrides and diamines [18][19][20][21] or by aromatic nucleophilic substitution reactions of isomeric bis(chlorophthalimide)s with bisthiophenols [22][23][24][25]. Isomeric polyimides, which possess geometrically asymmetric and noncoplanar moieties, were found to be endowed with improved solubility, low melt viscosity, comparable thermal and mechanical properties [26].…”

Preparation, characterization, and properties of poly(thioether ether imide)s from isomeric bis(chlorophthalimide)s and bis(4-mercaptophenyl) ether

“…25,26 These results suggested that the T g of isomeric polymers could be regulated by controlling the content of the isomeric unit. As shown in Figure 4, the 5% weight loss temperature (T 5% ) values of PTEIs (a-e) under nitrogen atmosphere were in the range of 525-539 C and gradually increased following the order: a < b < c < d < e, which could be interpreted by the fact that the 3-phthalimide unit has lower thermal stability than 4-phthalimide unit.…”