Syntheses and properties of organosoluble poly(ether imide)s from 1,1‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]cyclohexane dianhydride and aromatic diamines

Abstract

A bis(ether anhydride) monomer, 1,1-bis [4-(3,4-dicarboxyphenoxy)phenyl-]cyclohexane dianhydride (IV-A), was synthesized from the nitro displacement of 4-nitrophthalodinitrile by the phenoxide ion of 1,1-bis(4-hydroxyphenyl)cyclohexane (I-A), followed by alkaline hydrolysis of the intermediate bis(ether dinitrile) and dehydration of the resulting bis(ether acid). A novel series of organosoluble poly(ether imide)s (VI a-i )(PEIs) bearing cyclohexylidene cardo groups was prepared from the bis(ether anhydride) IV-A with various aromatic diamines V a-i via a conventional two-stage process. The PEIs had inherent viscosities in the range of 0.48 -1.02 dL/g and afforded flexible and tough films by solution-casting because of their good solubilities in organic solvents. Most PEIs showed yield points in the range of 89 -102 MPa at stress-strain curves and had tensile strengths of 78 -103 MPa, elongations at breaks of 8 -62%, and initial moduli of 1.8 -2.2 GPa. The glass-transition temperatures (T g 's) of these PEIs were recorded between 200 -234°C. Decomposition temperatures of 10% weight loss all occurred above 490°C in both air and nitrogen atmospheres, and their residues were more than 43% at 800°C in nitrogen atmosphere. The cyclohexane cardo-based PEIs exhibited relatively higher T g 's, better solubilities in organic solvents, and better tensile properties as compared with the corresponding Ultem PEI system.

Fluorene‐Containing Poly(ester imide)s and their Application to Positive‐Type Photosensitive Heat‐Resistant Materials

“…In addition, these ester‐linked monomers also possess another merit, i.e., its simple one‐step synthetic process. In contrast, the ether‐linked monomers (BPF‐PA and BCF‐PA) require much more steps: (i) ether synthesis by the nitro displacement reaction20, 42, 43 from 4‐nitrophthalonitrile and FL‐containing diols (BPFL and BCFL), (ii) hydrolysis of the dicyano groups and neutralization, and (iii) dehydration. Therefore, TABPFL can be also useful as a comonomer for property improvement.…”

Fluorene‐Containing Poly(ester imide)s and their Application to Positive‐Type Photosensitive Heat‐Resistant Materials

“…In addition, these ester‐linked monomers also possess another merit, i.e., its simple one‐step synthetic process. In contrast, the ether‐linked monomers (BPF‐PA and BCF‐PA) require much more steps: (i) ether synthesis by the nitro displacement reaction20, 42, 43 from 4‐nitrophthalonitrile and FL‐containing diols (BPFL and BCFL), (ii) hydrolysis of the dicyano groups and neutralization, and (iii) dehydration. Therefore, TABPFL can be also useful as a comonomer for property improvement.…”

Poly(ether imide)s containing cyano substituents and thin films made from them

“…Bis(ether anhydride)s ( 2 ) were synthesized by a multistep reaction, according to the literature 19–22. In the first step, 4‐nitrophtalonitril reacts with different aromatic diols containing isopropylidene, hexafluoroisopropylidene, phthalide, or cyclohexane units, in dimethylformamide as solvent and in the presence of potassium carbonate.…”

Synthesis, spectral and thermal characterization of polyester derived from 1,1-bis(4-hydroxyphenyl)cyclohexane

“…Also, the dense packing of the polymer chain may be disturbed and, consequently, the solvent molecules penetrate easily to solubilize the chains. 31 The molecular weight and intrinsic viscosities of the polyesters are given in Table 2. The intrinsic viscosity of the polyesters P1 to P4 was found to be in the range of 0.35-0.43 g dL À1 .…”

Fluorene‐Containing Poly(ester imide)s and their Application to Positive‐Type Photosensitive Heat‐Resistant Materials

“…In addition, these ester‐linked monomers also possess another merit, i.e., its simple one‐step synthetic process. In contrast, the ether‐linked monomers (BPF‐PA and BCF‐PA) require much more steps: (i) ether synthesis by the nitro displacement reaction20, 42, 43 from 4‐nitrophthalonitrile and FL‐containing diols (BPFL and BCFL), (ii) hydrolysis of the dicyano groups and neutralization, and (iii) dehydration. Therefore, TABPFL can be also useful as a comonomer for property improvement.…”

Poly(ether imide)s containing cyano substituents and thin films made from them

“…Bis(ether anhydride)s ( 2 ) were synthesized by a multistep reaction, according to the literature 19–22. In the first step, 4‐nitrophtalonitril reacts with different aromatic diols containing isopropylidene, hexafluoroisopropylidene, phthalide, or cyclohexane units, in dimethylformamide as solvent and in the presence of potassium carbonate.…”

Synthesis, spectral and thermal characterization of polyester derived from 1,1-bis(4-hydroxyphenyl)cyclohexane

“…Also, the dense packing of the polymer chain may be disturbed and, consequently, the solvent molecules penetrate easily to solubilize the chains. 31 The molecular weight and intrinsic viscosities of the polyesters are given in Table 2. The intrinsic viscosity of the polyesters P1 to P4 was found to be in the range of 0.35-0.43 g dL À1 .…”

Fluorene‐Containing Poly(ester imide)s and their Application to Positive‐Type Photosensitive Heat‐Resistant Materials

“…In addition, these ester‐linked monomers also possess another merit, i.e., its simple one‐step synthetic process. In contrast, the ether‐linked monomers (BPF‐PA and BCF‐PA) require much more steps: (i) ether synthesis by the nitro displacement reaction20, 42, 43 from 4‐nitrophthalonitrile and FL‐containing diols (BPFL and BCFL), (ii) hydrolysis of the dicyano groups and neutralization, and (iii) dehydration. Therefore, TABPFL can be also useful as a comonomer for property improvement.…”

Poly(ether imide)s containing cyano substituents and thin films made from them

“…Bis(ether anhydride)s ( 2 ) were synthesized by a multistep reaction, according to the literature 19–22. In the first step, 4‐nitrophtalonitril reacts with different aromatic diols containing isopropylidene, hexafluoroisopropylidene, phthalide, or cyclohexane units, in dimethylformamide as solvent and in the presence of potassium carbonate.…”

Synthesis, spectral and thermal characterization of polyester derived from 1,1-bis(4-hydroxyphenyl)cyclohexane

“…Also, the dense packing of the polymer chain may be disturbed and, consequently, the solvent molecules penetrate easily to solubilize the chains. 31 The molecular weight and intrinsic viscosities of the polyesters are given in Table 2. The intrinsic viscosity of the polyesters P1 to P4 was found to be in the range of 0.35-0.43 g dL À1 .…”