Investigation of polyimides containing naphthalene units. II. Model compounds synthesis

Sęk, Danuta; Wanic, Andrzej; Schab‐Balcerzak, Ewa

doi:10.1002/pola.1995.080330321

Cited by 27 publications

(18 citation statements)

References 9 publications

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“…The first one is similar to the proposed mechanism for phthalic imide ring formation: the anhydride reacts with the amine leading to an amid-acid intermediate which is then transformed into imide (scheme 1a) [2]. The other assumption involves an isoimide intermediate in the presence of an acidic medium, typically benzoic acid, which is further transformed into imide in the presence of basic medium, typically isoquinoline (scheme 1b) [5,6].…”

Section: Introductionmentioning

confidence: 91%

Mechanistic Aspects of Polynaphthalimide Synthesis from NMR Analysis

Piroux

Merçier

Picq

2009

High Performance Polymers

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Section: Introductionmentioning

confidence: 91%

Mechanistic Aspects of Polynaphthalimide Synthesis from NMR Analysis

Piroux

Merçier

Picq

2009

High Performance Polymers

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“…An acidic catalyst such as benzoic acid (BA) has been added in the first step, and it may promote the formation of the trans ‐isoimide. It has been proposed that a basic catalyst is then needed to convert the trans ‐isoimide into a naphthalimide 12…”

Section: Introductionmentioning

confidence: 99%

Sulfonated naphthalene dianhydride based polyimide copolymers for proton‐exchange‐membrane fuel cells. I. Monomer and copolymer synthesis

Einsla

Hong

Kim

et al. 2004

J. Polym. Sci. A Polym. Chem.

171

109

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A novel sulfonated diamine, 3,3′‐disulfonic acid‐bis[4‐(3‐aminophenoxy)phenyl]sulfone (SA‐DADPS), was prepared from m‐aminophenol and disodium‐3,3′‐disulfonate‐4,4′‐dichlorodiphenylsulfone. The conditions necessary to synthesize and purify SA‐DADPS in high yields were investigated in some detail. This disulfonated aromatic diamine, containing ether and sulfone linkages, was used to prepare N‐methyl‐2‐pyrrolidinone‐soluble, six‐membered ring polyimide copolymers containing pendent sulfonic acid groups by a catalyzed one‐step high‐temperature polycondensation in m‐cresol. These materials showed much improved hydrolytic stability with respect to phthalimides. High‐molecular‐weight film‐forming statistical copolymers with controlled degrees of disulfonation were prepared through variations in the stoichiometric ratio of disulfonated diamine (SA‐DADPS) in its soluble triethylamine salt form to several unsulfonated diamines. Three unsulfonated diamines, bis[4‐(3‐aminophenoxy)phenyl] sulfone, 4,4′‐oxydianiline, and 1,3‐phenylenediamine, were used to prepare the copolymers. The characterization of the copolymers by 1H NMR, Fourier transform infrared, ion‐exchange capacity, and thermogravimetric analysis demonstrated that SA‐DADPS was quantitatively incorporated into the copolymers. Solution‐cast films of the sulfonated copolymers were prepared and afforded tough, ductile membranes with high glass‐transition temperatures. Methods were developed to acidify the triethylammonium salt membranes into their disulfonic acid form, this being necessary for proton conduction in a fuel cell. The synthesis and characterization of these materials are described in this article. Future articles will describe the performance of these copolymers as proton‐exchange membranes in hydrogen/air and direct methanol fuel cells. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 862–874, 2004

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“…An acidic catalyst such as benzoic acid was added, which promotes the formation of the trans ‐isoimide. It has been proposed that a basic catalyst such as isoquinoline was needed to convert the trans ‐isoimide into polyimide 34, 35…”

Section: Resultsmentioning

confidence: 99%

Synthesis and properties of new poly(ether imides) based on pyridine‐containing aromatic dianhydride and diamine monomers

Wang

Gong

et al. 2009

J of Applied Polymer Sci

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A series of novel aromatic poly(ether imides) with inherent viscosities of 0.48-0.70 dL/g and weight-average molecular weights of 18,800-40,500 g/mol were successfully prepared from two dianhydride and two diamine monomers containing pyridine moiety via both two-step method and one-step method. Comparison of the one-step and the two-step methods for the preparation of poly(ether imides) was carried out and shown that poly (ether imides) obtained via one-step method exhibited higher molecular weights than the similar polymers prepared through two-step process. Poly(ether imide) resins obtained via both one-step and two-step methods with subsequent chemical dehydration showed good solubility not only in high boiling point solvents but also in low boiling point solvents. High-quality poly(ether imide) films could be obtained via the two-step method with subsequent thermal imidization, which exhibited excellent thermal properties with glass transition temperatures of 239-278 C, initial decomposition temperatures of 540-574 C, residual weight percent at 800 C of 64.5-69.3% under nitrogen, good thermo-oxidative stability with initial decomposition temperatures of 521-544 C, residual weight percent at 800 C of 33.6-51.1% under air atmosphere, outstanding mechanical properties with tensile strengths in the range of 104.6-109.4 MPa, tensile modulus in the range of 1.92-2.58 GPa, and elongation at break from 6.9 to 8.0%, as well as good transparency with cutoff wavelengths of 386-392 nm and low dielectric constants of 2.80-2.92 at 1 MHz.

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Investigation of polyimides containing naphthalene units. II. Model compounds synthesis

Cited by 27 publications

References 9 publications

Mechanistic Aspects of Polynaphthalimide Synthesis from NMR Analysis

Mechanistic Aspects of Polynaphthalimide Synthesis from NMR Analysis

Sulfonated naphthalene dianhydride based polyimide copolymers for proton‐exchange‐membrane fuel cells. I. Monomer and copolymer synthesis

Synthesis and properties of new poly(ether imides) based on pyridine‐containing aromatic dianhydride and diamine monomers

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