Novel organosoluble and colorless poly(ether imide)s based on 3,3‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]phthalide dianhydride and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups

Abstract

A novel series of colorless and highly organosoluble poly(ether imide)s were prepared from 3,3-bis [4-(3,4-dicarboxyphenoxy)phenyl]phthalide dianhydride with various fluorinated aromatic bis(ether amine)s via a conventional two-stage process that included ring-opening polyaddition to form the poly(amic acid)s followed by cyclodehydration to produce the polymer films. The poly(ether imide)s showed excellent solubility, with most of them dissoluble at a concentration of 10 wt % in amide polar solvents, in ether-type solvents, and even in chlorinated solvents. Their films had a cutoff wavelength between 358 and 373 nm, and the yellowness index ranged from 3.1 to 9.5. The glass-transition temperatures of the poly(ether imide) series were recorded between 237 and 297 8C, the decomposition temperatures at 10% weight loss were all above 494 8C, and the residue was more than 54% at 800 8C in nitrogen. These films showed high tensile strength and also were characterized by higher solubility, lighter color, and lower dielectric constants and moisture absorption than an analogous nonfluorinated polyimide series. a L* indicates lightness. A positive a* values means red, whereas a negative a* value indicates green. A positive b* value means yellow, whereas a negative b* value implies blue. b 8c, 8f, and 8g were derived from 6FDA and diamine 4. c 3148 YANG AND SU

Synthesis of high performance phenolphthalein-based cardo poly(ether ketone imide)s via aromatic nucleophilic substitution polymerization

“…It is sharply contrasted with the typical aromatic polyimide film derived from PMDA and ODA, which showed deep yellow color and exhibited λ 0 of 445 nm and transmittance at 450 nm of 2%. The excellent optical transparency of these films was attributed to the incorporation of the bulky cardo phthalide groups in the polymer structure, which inhibited close packing, thereby increasing the free volume among the molecular chains and suppressing the inter-and intramolecular charge transfer interactions effectively [27,28]. As comparing the coloration of these films, it is interestingly observed that optical transparency slightly increased with decreasing the content of phthalimide unit in the polymer backbone.…”

“…The PEKI-C films about 20 µm thick exhibited good mechanical properties with tensile strengths of about 100 MPa, elongations at break of more than 9.7 %, and tensile moduli of more than 2.2 GPa. It is noted that the tensile strengths, elongations at break, and tensile moduli increased with increasing the content of the phthalimide unit, which effectively contributed to the inter-chain interactions [27,28].…”

“…This phenomena was probably attributed to the decreasing content of the five-member heterocyclic phthalimide unit, which effectively contributed to the inter-and intramolecular charge transfer interactions [27,28].…”

“…Polyimides containing phenolphthalein-based cardo groups were also studied in recent years, especially Yang and coworkers have reported a series of research work on poly(ether imide)s with phthalide cardo groups [25][26][27][28][29][30][31][32][33][34][35][36]. Compared with M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT conventional liner polyimides, cardo polyimides from phenolphthalein-based tetracarboxylic dianhydrides or phenolphthalein-based diamines have better solublility, higher glass transition temperature and higher transmittance in the visible region.…”

Synthesis and characterization of novel polyhydrazides containing pendant amide-imide-pyridine moiety

“…The solubility and thermal characteristics of the polymers can be enhanced by having cyclic side groups, such as fluorene, phthalide, and phthalimidine groups on the polymer backbone [6][7][8]. Thus, the introduction of phthalimide groups into the macromolecular chains of polyhydrazides improves the properties of the resulting materials.…”