A new monomer, N,N′‐bis(4‐phenoxybenzoyl)‐m‐phenylenediamine (BPMPDA), was prepared via the reaction of m‐phenylenediamine with 4‐phenoxybenzoyl chloride in N,N‐dimethylacetamide. Novel copolymers of poly(ether ketone ether ketone ketone) and poly(ether amide amide ether ketone ketone) (PEAAEKK) were synthesized by the modified electrophilic Friedel–Crafts acylation copolycondensation of terephthaloyl chloride with a mixture of 4,4′‐diphenoxybenzophenone (DPOBPN) and BPMPDA, over a wide range of DPOBPN/BPMPDA molar ratios. The resulting copolymers were characterized by Fourier transform infrared spectroscopy, wide‐angle X‐ray diffraction, differential scanning calorimetry, and thermogravimetric analysis, and so on. The results indicated that the copolymers with 10–30 mol% BPMPDA were semicrystalline and had remarkably increased glass transition temperatures (Tgs) over the conventional poly(ether ether ketone) and poly(ether ketone ketone) due to the incorporation of amide linkages in the main chains. The copolymers III and IV with 20–30 mol% BPMPDA had not only high Tgs of 177–180°C, but also moderate melting temperatures (Tms) of 324–333°C, having good potential for the melt processing. The copolymers III and IV had tensile strengths of 101.8–104.4 MPa, Young's moduli of 2.32–2.46 GPa, and elongations at break of 10.8–12.2% and exhibited high thermal stability and excellent resistance to organic solvents. POLYM. ENG. SCI., 53:2353–2359, 2013. © 2013 Society of Plastics Engineers

A new monomer containing naphthalene, namely 4,4 0 -di(1-naphthoxy)benzophenone (DNOBN), was prepared by the condensation reaction of 4,4 0 -difluorobenzophenone with 1-naphthol in the presence of base in N-methylpyrrolidone (NMP). Novel poly(aryl ether ketone)s containing both 2,6-naphthylene and 1,4-naphthylene units were synthesized by the electrophilic Friedel-Crafts acylation polycondensation of terephthaloyl chloride with a mixture of 2,6-bis(4-phenoxybenzoyl)naphthalene (BPOBN) and DNOBN, over a wide range of BPOBN/DNOBN molar ratios, in the presence of anhydrous AlCl 3 and NMP in 1,2-dichloroethane (DCE). The copolymers obtained were characterized by different physicochemical techniques. The copolymers with 10-20 mol% DNOBN are semicrystalline and had remarkably increased T g s over commercially available poly(ether ether ketone) and poly(ether ketone ketone) due to the incorporation of 2,6-naphthylene and 1,4-naphthylene moieties in the main chains. The copolymer IV with 20 mol% DNOBN had not only high T g of 189 C, but also moderate T m of 338 C, having good potential for melt processing. The copolymer IV had tensile strength of 102.2 MPa, Young's modulus of 3.25 GPa, and elongation at break of 18.5% and exhibited high thermal stability and excellent resistance to organic solvents.

A new monomer, 1,4-bis(4-phenoxybenzoyl)naphthalene (BPOBN), was conveniently synthesized via a simple synthetic procedure from readily available materials. A series of novel copolymers of poly(ether ketone ether ketone ketone) and poly(ether ketone ketone ether ketone ketone) containing 1,4naphthylene moieties were prepared by the Friedel-Crafts acylation solution copolycondensation of terephthaloyl chloride (TPC) with a mixture of BPOBN and 4,4 0 -diphenoxybenzophenone (DPOBPN), over a wide range of BPOBN/DPOBPN molar ratios, in the presence of anhydrous AlCl 3 and N-methylpyrrolidone in 1,2-dichloroethane. The copolymers with 10-40% BPOBN are semicrystalline and had remarkably increased T g s over the conventional PEEK and PEKK due to the incorporation of 1,4-naphthylene moieties in the main chains. The copolymers with 30-40 mol% BPOBN had not only high T g s of 176-1778C, but also moderate T m s of 332-3388C, which are suitable for the melt processing. These polymers had tensile strengths of 101.5-104.7 MPa, Young's moduli of 2.49-2.65 GPa, and elongations at break of 13.3-15.7% and exhibited high thermal stability and excellent resistance to organic solvents. POLYM. ENG. SCI., 56:566-572, 2016.