Study On Synthesis And Properties Of Novel Poly(Aryl Ether Ketone)s Containing Imide Groups In Main Chain

Two aromatic diacid dichlorides containing imide groups, bis(4-chloroformyl-1,2- benzenedioyl)-N,N,N',N'-4,4'-diaminodiphenyl ether (DIDC-E) and bis(4-chloro- formyl-1,2-benzenedioyl)-N,N,N',N'-4,4'-diaminodiphenyl sulfone (DIDC-S), were prepared by the imidization reaction of trimellitic anhydride (TMA) with 4,4'- diaminodiphenyl ether or 4,4'-diaminodiphenyl sulfone, followed by reaction with thionyl chloride in the presence of DMF, respectively. They were characterized by FT-IR, 1H NMR, 13C NMR and the results showed that DIDC-E and DIDC-S have the expected structures. Novel poly(aryl ether ketones) containing imide groups were synthesized by electrophilic Friedel-Crafts solution polycondensation of DIDC-E or DIDC-S with 4,4'-dinaphthoxydiphenyl sulfone (DNODPS) or 4,4'-dinaphthoxy- benzophenone (DNOBP) in the presence of anhydrous aluminum chloride and N-methylpyrrolidone (NMP) in 1,2-dichloroethane (DCE). The polymers were characterized by different physico-chemical techniques such as FT-IR, DSC, TG, WAXD, etc.. The results showed that these polymers are amorphous and had high glass transition temperatures (219-276°C) and excellent thermal stability.A new aromatic ether monomer containing imide groups, bis[4-(p-phenoxy- benzoyl)-1,2-benzenedioyl]-N,N,N',N'-4,4'-diaminodiphenyl ether (DPEDIDC-E), was prepared by Friedel-Crafts acylation reaction of DIDC-E with diphenyl ether (DPE) and characterized by FT-IR, 1H NMR, 13C NMR. Novel poly(ether ketone imide) (PEKI)/poly(ether ketone ketone) (PEKK) copolymers were synthesized by electrophilic Friedel-Crafts solution copolycondensation of terephthaloyl chloride (TPC) with a mixture of DPE and DPEDIDC-E, in the presence of anhydrous aluminum chloride and N-methylpyrrolidone (NMP) in 1,2-dichloroethane (DCE).The copolymers were characterized by FT-IR, DSC, TG, WAXD, etc.. The results showed that the glass transition temperatures of copolymers increased with increase in concentration of DPEDIDC-E in the copolymer, while the melting temperatures and crystallinity decreased with increase in concentration of DPEDIDC-E in the copolymer. The copolymers with 10-40 mol% DPEDIDC-E are semicrystalline and all the polymers exhibited outstanding thermal stability.A novel aromatic ether monomer containing imide and sulfone groups, bis[4-(p-phenoxybenzoyl)-1,2-benzenedioyl]-N,N,N',N'-4,4'-diaminodiphenyl sulfone (DPEDIDC-S), was prepared by Friedel-Crafts acylation reaction of DIDC-S with diphenyl ether (DPE) and characterized by FT-IR, 1H NMR, 13C NMR. Novel poly(ether ketone sulfone imide) (PEKSI)/poly(ether ketone ketone) (PEKK) copolymers were synthesized by electrophilic Friedel-Crafts solution copolycon- densation of terephthaloyl chloride (TPC) with a mixture of DPE and DPEDIDC-S, in the presence of anhydrous aluminum chloride and N-methylpyrrolidone (NMP) in 1,2-dichloroethane (DCE). The copolymers were characterized by FT-IR, DSC, TG, WAXD, etc.. The results showed that the glass transition temperatures of copolymers increased with increase in concentration of DPEDIDC-S in the copolymer, while the melting temperatures decreased with increase in concentration of DPEDIDC-S in the copolymer. The copolymers with 10-30 mol% DPEDIDC-S are semicrystalline and all the polymers exhibited excellent thermal stability.Similarly, another aromatic ether monomer containing imide and sulfone groups, bis[4-[4-(p-phenoxyphenylsulfonylphenoxy)benzoyl]-1,2-benzenedioyl]-N,N,N',N'-4,4'-diaminodiphenyl ether (DPODPSDIDC-E), was prepared by Friedel-Crafts acylation reaction of DIDC-E with 4,4'-diphenoxydiphenyl sulfone (DPODPS) and characterized by FT-IR, 1H NMR, 13C NMR. A series of poly(ether ketone sulfone imide) (PEKSI)/poly(ether ketone ketone) (PEKK) copolymers were synthesized by electrophilic Friedel-Crafts solution copolyconensation of terephthaloyl chloride (TPC) with a mixture of DPE and DPODPSDIDC-E, in the presence of anhydrous aluminum chloride and N-methylpyrrolidone (NMP) in 1,2-dichloroethane (DCE). The copolymers were characterized by FT-IR, DSC, TG, WAXD, etc.. The results showed that the glass transition temperatures of copolymers increased with increase in concentration of DPODPSDIDC-E in the copolymer, while the melting temperatures decreased with increase in concentration of DPODPSDIDC-E in the copolymer. The copolymers with 10-25 mol% DPODPSDIDC-E are semicrystalline and all the polymers exhibited good thermal stability.