Synthesis and properties of novel poly(aryl ether ketone)s containing both 2,6‐naphthylene moieties and amide linkages in the main chains

Abstract

A new monomer, 2,6-bis(4-phenoxybenzoyl)naphthalene (BPOBON), was easily synthesized via simple synthetic procedures from readily available materials. A series of novel poly(aryl ether ketone)s containing both 2,6-naphthylene moieties and amide linkages in the main chains were prepared by the Friedel-Crafts acylation solution copolycondensation of isophthaloyl chloride with a mixture of BPOBON and N,N'-bis(4-phenoxybenzoyl)-1,4-phenylenediamine (BPBPPD), over a wide range of BPOBON/BPBPPD molar ratios, in the presence of anhydrous AlCl 3 and N-methylpyrrolidone in 1,2-dichloroethane. All the polymers are semicrystalline and had remarkably increased T g s over the conventional PEEK and PEKK due to the incorporation of naphthalene and amide linkages in the main chains. The polymers with 50-70 mol % BPOBON had not only high T g s of 179-186C, but also moderate T m s of 321-328 C, which are very suitable for the melt processing. These polymers had tensile strengths of 101.5-107.1 MPa, Young's moduli of 2.13-2.39 GPa, and elongations at break of 11.8-13.7% and exhibited excellent thermal stability and good resistance to organic solvents.

Synthesis and properties of poly(aryl ether ketone)s containing both biphenylene moieties and sulfone linkages in the main chain

“…To further expand the application of PAEKs, their melt processabilities and thermal properties need to be improved by reducing the melting temperature and enhancing the glass transition temperature. Recently, we described the preparation of novel poly(aryl ether ketone)s containing amide linkages in main chains by the electrophilic Friedel‐Crafts acylation copolycondensation, the resulting copolymers with low content of amide linkages had not only much higher T g s than the conventional PEEK and PEKK due to the existence of intermolecular hydrogen bonding, but also moderate T m s, which are suitable for melt processing, but the resistance to organic solvents and the thermal decomposition temperature ( T d ) decreased with the introduction of amide linkages . In this article, we synthesized two monomers 4,4′‐ bis (4‐phenoxybenzoyl) biphenyl (BPOBBP) and 4,4′‐diphenoxydiphenyl sulfone (DPODPS), via simple synthetic procedures from readily available materials.…”

Synthesis and properties of novel soluble polyamides containing both fluorene or xanthene cardo moieties and fluorinated phenoxy pendant groups

“…However, it appears that aromatic polyamides containing both cardo moieties and fluorinated phenoxy pendant groups have not been reported in detail in the open literature. In a continuation of our studies on easily processable high‐performance polymers , we report herein the synthesis of a series of novel aromatic polyamides containing both fluorene or xanthene cardo structures and fluorinated phenoxy pendant groups from two fluorinated isophthaloyl chlorides and four diamines containing cardo groups by the low‐temperature solution polycondensation in N,N ‐dimethylacetamide (DMAc). We expected that the incorporation of both bulky fluorene or xanthene cardo structures and flexible fluorinated phenoxy pendant groups into polyamide backbone would endow the resulting polyamides excellent solubility, high thermal stability, and optical transparency as well as good electrical insulating and dielectric properties.…”

Synthesis and properties of novel copolymers of poly(ether ketone ether ketone ketone) and poly(ether ketone ketone ether ketone ketone) containing 1,4-naphthylene moieties

“…To expand the application of p ‐PEKEKK, its melt processability needs to be improved by reducing the melting temperature. Recently, we reported the synthesis of novel poly(aryl ether ketone)s containing amide linkages in main chains by the electrophilic Friedel‐Crafts acylation copolycondensation, the copolymers obtained with low content of amide linkages had not only much higher T g s than the conventional PEEK and PEKK due to the existence of intermolecular hydrogen bonding, but also moderate T m s, which are suitable for melt processing, but the resistance to organic solvents and the thermal stability decreased with the incorporation of amide linkages . In continuing our efforts to modify the conventional PAEK properties, in this paper, we prepared a new monomer, 1,4‐bis(4‐phenoxybenzoyl)naphthalene (BPOBN), via a simple synthetic procedure from readily available materials.…”