Soluble aromatic poly(ether ketone)s with a pendant 3,5-ditrifluoromethylphenyl group

Liu, Baijun; Hu, Wei; Chen, Chunhai; Jiang, Zhenhua; Zhang, Wanjin; Wang, Zhongwen; Matsumoto, Toshihiko

doi:10.1016/j.polymer.2004.03.015

Cited by 107 publications

(66 citation statements)

References 22 publications

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“…The T g of the polyketone having 1,4-phenylene moiety (19) is almost the same with that of the polyketone having 4,4 0 -biphenylylene moiety (46). On the other hand, T g of the isomeric polyketone having 1,3-phenylene moiety (20) is lower than that of the isomeric polyketone having 1,4-phenylene moiety (19).…”

Section: Ar-armentioning

confidence: 81%

“…Along with this trend, the synthetic approach also shifted to the preparation of substituted aromatic poly(ether ketone)s, especially those bearing perfluoroalkyl groups, [46][47][48][49] and aromatic copoly(ether ketone)s having naphthylene moieties 50,51 or additional functional groups. 52 Application of aromatic poly(ether ketone)s as high-performed coating material is one of the main usages of this type of polymer.…”

Section: O N Aromatic Ringmentioning

confidence: 99%

“…However, the latter polymerization proceeded rather moderately. The obtained polymer (48) from monomer 47 is assumed to have lower molecular weight.The obtained polyketones (46 and 48) are amorphous and able to give flexible cast film.The cause of the difference in polymerizability of two monomers is not clarified at the present stage.On the other hand, the molecular structures and the T g 's of the isomeric or homologous four wholly aromatic polyketones (19,20,46, and 48) obtained by aromatic coupling polycondensation and AlCl 3 -mediated electrophilic aromatic aroylation polycondensation show curious relationship. Figure 6 demonstrates the molecular structure of the repeating unit of the wholly aromatic polyketones mentioned above.…”

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confidence: 99%

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Synthesis of Wholly Aromatic Polyketones

Yonezawa

Okamoto

2009

Polym. J.

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The structural design strategy and the synthetic approaches for the wholly aromatic polyketones and the monomers are described. Electrophilic aromatic aroylation substitution polycondensation and aromatic coupling polycondensation have been investigated as synthetic routes for wholly aromatic polyketones by the author's group. Acyl-acceptant arene molecules as the electrophilic aromatic aroylation substitution polycondensation type monomers and the aromatic nuclei for bis(chlorobenzoylated) compounds as the aromatic coupling polycondensation one were designed and synthesized employing 2,2 0 -dioxybiphenyl, 2,2 0 -dioxy-1,1-binaphtyl, and o-terphenyl skeletons. Determining factors for monomers, which enable regioselective polycondensation, are also discussed. The properties of polyketones are also discussed briefly on the basis of polymer repeating unit structures. Aromatic polyketones are a group of aromatic polymers having ketonic carbonyl groups as the major linkage in the aromatic polymer main chain. Though there have been reported many examples of aromatic polyketones, almost all of them belong to the category of ''aromatic poly(ether ketone)s.'' [1][2][3][4][5] In fact, the term ''aromatic polyketone'' is generally apt to be regarded identical to ''aromatic poly(ether ketone).'' As a representative material of this category of aromatic polymer, PEEK Ò (1), a poly(ether ether ketone), is well-known super engineering plastics showing superior thermal stability, mechanical strength, and chemical resistance. Figure 1 shows the structure of PEEK Ò (1). The repeating unit of the polymer is composed of three 1,4-phenylene moieties bonded with two ether linkages and one ketonic carbonyl group. The structure suggests that PEEK Ò (1) might have properties more attributable to aromatic ether rather than aromatic ketone.On the other hand, aromatic polymers that have main chain structure composed of only aromatic rings and ketonic carbonyl groups are another type of aromatic polyketones (Figure 2). 6 The authors' group has been investigating the synthesis of aromatic polyketones free from main chain hetero linkages, wholly aromatic polyketones, during recent one and a half decades. Contrary to aromatic poly(ether ketone)s, wholly aromatic polyketones were seldom reported before.Prior to discussion of synthetic chemistry of wholly aromatic polyketones, the overview of aromatic polyketones including aromatic poly(ether ketone)s is briefly summarized to discriminate between aromatic poly(ether ketone)s and wholly aromatic polyketones.Aromatic polyketones are obliged to have copolymer structure composed of aromatic rings and ketonic carbonyl groups. From this point, aromatic polyketones are regarded as polyarylenes bearing inserted carbonyl groups. These polymers are classified into wholly aromatic polyketones or others according to the absence or presence of hetero linkages in the main chain. Aromatic poly(ether ketone) is the representative polymer of the latter type.As a natural consequence of the structural characterist...

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Section: Ar-armentioning

confidence: 81%

Section: O N Aromatic Ringmentioning

confidence: 99%

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confidence: 99%

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Synthesis of Wholly Aromatic Polyketones

Yonezawa

Okamoto

2009

Polym. J.

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“…The resulting solution was filtered and added dropwise to a mixture of 1,4-benzoquinone (2.16 g, 0.02 mol), sodium bicarbonate (16.80 g, 0.2 mol), and water (100 mL). After that, the reaction mixture was stirred at [10][11][12][13][14][15] o C for about 2 h and then at room temperature for 2 h. Then the precipitate was collected by filtration and washed thoroughly with water and kept at 60 o C in a vacuum oven. Brown crystals were obtained after recrystallization from n- J=8.0Hz, 1H).…”

Section: Monomer Synthesismentioning

confidence: 99%

“…On the other hand, in the last few years more and more attention has been paid to their functionalization [9][10][11][12][13][14][15][16], which could be achieved either by chemical modification of the polymer or by direct synthesis using functional monomers. The cyano group on the aromatic ring (PEN) appears to promote adhesion of the polymer to many substrates [17][18], possibly through reaction or polar interaction with other functional groups [19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel cyanofunctionalized poly(aryl ether ketone)s

Zhang¹,

Ren²,

Guan³

et al. 2009

E-Polymers

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Abstract:A series of cyanophenyl-substituted poly(aryl ether ketone)s (PAEKs) have been successfully synthesized from two new bisphenol monomers, (3,4-dicyano) phenylhydroquinone and (4-cyano) phenylhydroquinone respectively, and the thermal behaviour and the solubility have been characterized. These polymers exhibited high glass transition temperatures and excellent thermal stability. The glass transition temperatures ranged from 173 to 217 o C, and 5% weight-loss temperatures were above 470 o C. The solubilities of these polymers have been remarkably improved in common organic solvents over PEEK and PEN. Some polymers formed transparent, strong, and flexible films, with tensile strength of 106.5-125.2 MPa, Young's moduli of 2.68-3.20 GPa, and elongations at break of 9-16 %.

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Synthesis and properties of novel organosoluble aromatic poly(ether ketone)s containing pendant methyl groups and sulfone linkages

Sheng

Luo

Yi-Huo

et al. 2007

J of Applied Polymer Sci

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Several novel aromatic poly(ether ketone)s containing pendant methyl groups and sulfone linkages with inherent viscosities of 0.62-0.65 dL/g were prepared from 2-methyldiphenylether and 3-methyldiphenylether with 4,4 0 -bis(4-chloroformylphenoxy)diphenylsulfone and 4,4 0 -bis (3-chloroformylphenoxy)diphenylsulfone by electrophilic Friedel-Crafts acylation in the presence of N,N-dimethylformamide with anhydrous AlCl 3 as a catalyst in 1,2-dichloroethane. These polymers, having weight-average molecular weights in the range of 57,000-71,000, were all amorphous and showed high glass-transition temperatures ranging from 160.5 to 1678C, excellent thermal stability at temperatures over 4508C in air or nitrogen, high char yields of 52-57% in nitrogen, and good solubility in CHCl 3 and polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone at room temperature. All the polymers formed transparent, strong, and flexible films, with tensile strengths of 84.6-90.4 MPa, Young's moduli of 2.33-2.71 GPa, and elongations at break of 26.1-27.4%.

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Soluble aromatic poly(ether ketone)s with a pendant 3,5-ditrifluoromethylphenyl group

Cited by 107 publications

References 22 publications

Synthesis of Wholly Aromatic Polyketones

Synthesis of Wholly Aromatic Polyketones

Synthesis and characterization of novel cyanofunctionalized poly(aryl ether ketone)s

Synthesis and properties of novel organosoluble aromatic poly(ether ketone)s containing pendant methyl groups and sulfone linkages

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