N, N′-Bis(4-phenoxybenzoyl)-4,4′-diaminodiphenyl sulfone (BPBDAS) was prepared by the condensation of 4,4′-diaminodiphenyl sulfone with 4-phenoxybenzoyl chloride in N, N-dimethylacetamide. Novel copolymers of poly(ether ketone ketone) (PEKK) and poly(ether ether ketone ketone) containing amide and sulfone linkages (PEASAEKK) were synthesized by electrophilic Friedel–Crafts copolycondensation of terephthaloyl chloride with a mixture of diphenyl ether (DPE) and BPBDAS over a wide range of DPE/BPBDAS molar ratios, in the presence of anhydrous AlCl3 and N-methylpyrrolidone in 1,2-dichloroethane. The influences of the reaction conditions on the preparation of copolymers were examined. The copolymers obtained were characterized by different physicochemical techniques. The copolymers containing 10–25 mol% BPBDAS are semicrystalline and had remarkably increased Tgs compared to the commercially available poly(ether ether ketone) and PEKK due to the incorporation of amide and sulfone linkages in the main chains. The copolymer V with 25 mol% BPBDAS had not only high Tg of 187°C but also moderate Tm of 343°C, with good potential for melt processing. The copolymer V had a tensile strength of 102.7 MPa, Young’s modulus of 2.19 GPa, and elongation at break of 14.1%, and it also exhibited high thermal stability and good resistance to organic solvents.
RoseJB. Preparation and properties of poly(arylene ether sulphones). Polymer1974; 15: 456–465.
2.
OhnoMTakataTEndoT. Synthesis of a novel naphthalene-based poly(arylene ether-ketone) by polycondensation of 1,5-bis(4-fluorobenzoyl)-2,6-dimethylnaphthalene with bisphenol. J Polym Sci Polym Chem Ed1995; 33: 2647–2655.
3.
JiXLYuDHZhangWJWuZW. The multiple melting behavior of immiscible poly(ether ether ketone)/poly(ether diphenyl ether ketone) blend. Polymer1997; 38: 3501–3504.
4.
RoseJB. In: SeymourRBKirshenbaumGS (eds) High performance polymers: their origin and development. New York, NY: Elsevier, 1986, pp. 187–193.
5.
MullinsMJWooEP. The synthesis and properties of poly(aromatic ketones). J Macromol Sci Rev Macromol Chem Phys1987; C27: 313–341.
CotterRJ. Engineering plastics: a handbook of polyarylethers. Basel, Switzerland: Gordon and Breach Science Publishers, 1995.
8.
ChanKPWangYHayAS. Convenient synthesis and facile polymerization of cyclic aryl ether ketones containing the 1,2-dibenzoylbenzene moiety. Macromolecules1995; 28: 653–655.
9.
SinghRHayAS. Synthesis of novel poly(ether ketone)s containing the o-dibenzoylbenzene moiety. Macromolecules1991; 24: 2637–2639.
10.
Ben-HaidaAColquhounHMHodgePWilliamsDJ. Synthesis of a catechol-based poly(ether ether ketone) (“o-PEEK”) by classical step-growth polymerization and by entropically driven ring-opening polymerization of macrocyclic oligommers. Macromolecules2006; 39: 6467–6472.
11.
WangJGaoYHlilARHayAS. Synthesis of high molecular weight poly(phthalazinone ether)s by ullmann C–N and C–O condensation reactions. Macromolecules2008; 41: 298–300.
12.
ColquhounHMHodgePPaoloniFPVTerry McGrailPCrossP. Reversible, nondegradative conversion of crystalline aromatic poly (ether ketone)s into organo-soluble poly(ether dithioketal)s. Macromolecules2009; 42: 1955–1963.
13.
SakaguchiYTokaiMKatoY. Synthesis of poly(ether ketone) by friedel-crafts acylation: effects of reaction conditions. Polymer1993; 34: 1512–1515.
14.
ZolotukhinMGDosieretMFougniesCVillersDGilevaNGFatykhovAA. Aromatic homopolymers obtained by precipitation polycondensation: 1. synthesis of naphthalene-containing polyketones. Polymer1995; 36: 3575–3583.
15.
KrishnaswamyRKKalikaDS. Glass transition characteristics of poly(aryl ether ketone ketone) and its copolymers. Polymer1996; 37: 1915–1923.
16.
ZolotukhinMGRuedaDRBalta CallejaFJCagiaoMESedovaEAGilevaNG. Aromatic polymers obtained by precipitation polycondensation: 4*. Synthesis of poly(ether ketone ketone)s. Polymer1997; 38: 1471–1476.
17.
RuedaDRZolotukhinMGCagiaoMEBalta CallejaFJVillersDDosiereM.Aromatic polymers obtained by precipitation polycondensation. 3. Thermal behavior and microstructure of PEKEKK particles. Macromolecules1996; 29: 7016–7021.
18.
ZolotukhinMGColquhounHMSestiaaLGRuedaDRFlotD. One-pot synthesis and characterization of soluble poly(aryl ether-ketone)s having pendant carboxyl groups. Macromolecules2003; 36: 4766–4771.
19.
RitterHThorwirthRMullerG. Comb-like poly(aryl-ether-ketones) containing naphthalene moieties in the main chain. Makromol Chem1993; 194: 1469–1481.
20.
OhnoMTakataTEndoT. Synthesis of a novel naphthalene-based poly(arylene ether ketone) with high solubility and thermal stability. Macromolecules1994; 27: 3447–3448.
21.
LiuBWangGHuWJinYChenCJiangZ. Poly(aryl ether ketone)s with (3-Methyl)phenyl and (3-Trifluoromethyl)phenyl side groups. J Polym Sci Polym Chem Ed2002; 40: 3392–3398.
22.
ZhangYSunXXuRNiuYWangGJiangZ. Synthesis and characterization of novel fluorine-containing poly(aryl ether ketone)s containing 1,4-naphthylene units. Mater Chem Phys2006; 99: 465–469.
23.
LiuBHuWChenCJiangZZhangWWuZMatsumotoT. Soluble aaromatic poly(ether ketone)s with a pendant 3,5-ditrifluoromethylphenyl group. Polymer2004; 45: 3241–3247.
24.
LiuBRobertsonGPKimDSGuiverMDHuWJiangZ. Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules2007; 40: 1934–1944.
25.
ShibataMCaoJYosomiyaR. Synthesis and properties of the block copolymers of poly(ether ether ketone) and the poly(aryl ether sulfone) containing biphenylene moiety. Polymer1997; 38: 3103–3108.
