Carbazole‐based poly(aryl ether ketone) containing crosslinkable allyl groups on the side chains: synthesis, characterization and properties

Abstract

This paper presents a feasible method for introducing crosslinkable groups into a polymer to achieve excellent chemical resistance and improved thermal stability. Here, 3,6-bi(4-fluorobenzenzoyl)-N-allylcarbazole, a novel allyl-containing difluoroketone monomer, is synthesized and characterized. The resulting monomer is polymerized with phenolphthalein through the aromatic nucleophilic substitution reaction at 160 ∘ C to provide the soluble poly(aryl ether ketone) (PAEK) with a pendant allyl group. The obtained PAEK is characterized using Fourier transform infrared spectroscopy, NMR and gel permeation chromatography. The crosslinking reaction of the polymer occurs at 270 ∘ C, and it imparts excellent solvent resistance. DSC analysis shows that the glass transition temperature (T g ) of the cured polymer increases to 262-306 ∘ C when the curing temperature is elevated or when the curing time is extended within certain limits. The rate of increase of T g and the rate of the crosslinking reaction decrease as the curing time is extended under all of the investigated curing temperatures. The cured PAEKs possess good thermal stability with 5% weight loss temperatures up to 450 ∘ C. The tensile strength and Young's modulus of the polymer film cured at 300 ∘ C for 2 h are 65 MPa and 1.4 GPa, respectively. In addition, the polymer films before and after curing exhibit similar UV−visible absorption and blue light emission.

High‐performance soluble copolyarylate based on phenolphthalein: synthesis, characterization and properties

“…Phenolphthalein (PP) has bulky pendent groups and an asymmetric structure. Many high‐performance polymers with PP‐based cardo groups have been synthesized, including poly(arylene ether sulfone)s, poly(arylene ether ketone)s, poly(arylene ether nitrile)s and PARs . Among them, PP‐based cardo PARs are the most widely studied.…”

Synthesis and Characterization of a Self-Polycondensation Diazaphthalanone Monomer and Its Polymers from Polycondensation Reactions

“…Nitrogenous heterocyclic poly(aryl ether ketone) is a new kind of special performance heterocyclic polymer, and its excellent performance is attributed to the rigid and asymmetric phenyl and nitrogen-containing groups in the main chain of the polymerization [7]. Asymmetric phenyl and nitrogen-containing groups show non-planar structures to each other in spatial configuration so that the polymer retains rigidity and increases the characteristics of its non-planar structure [8], and the gap and free volume of the main chain become larger. Since Hay et al [9] synthesized the first nitrogen-containing polymer by N-C coupling reaction using 2-dihydro-4-(4-hydroxyphenyl)-1 (2H)-phthalazone and activation of the halogen compound as monomers in 1993, more and more attention has been paid to nitrogen-containing polymers.…”

“…Poly(aryl ether ketone) resin is usually made of bisphenol monomer and active bishalogen monomer as the raw materials [8,24,25] (Aa, Bb double monomer polycondensation) under the catalysis of potassium carbonate, known as solution polycondensation [26,27]. This kind of self-polymerizing monomer contains two functional groups that can react with each other, so the influence of the number of groups of two monomers on the degree of polymerization can be avoided during polymerization [28], and theoretically, high molecular weight polymers can be obtained.…”

New poly(aryl ether ketone)s containing 2,6-diphenylpyridyl units and diphenylphosphinophenyl pendant groups

“…4 Although traditional PEKs such as PEEK and PEKK show excellent performance, their poor solubility in common organic solvents and their high melting temperatures make them difficult to process and fabricate. To overcome these limitations, several approaches have been investigated to improve the solubility and processability of PEKs without significantly weakening their desired properties, such as the introduction of flexible linkages, 5 –7 bulky units, 8 –11 alicyclic moieties, 12 –15 and noncoplanar structures 16 –18 into the main chains of PEKs. Incorporating pendant groups into the PEK backbones is also an effective structural modification method.…”