Preparation of poly(ether ketone)s having phenyl,biphenyl,and terphenyl side groups and comparison of their properties

Abstract

Three kinds of bis(aromatic fluoride) compounds, 3,5-bis(4-fluorobenzoyl)biphenyl (1), 3,5-bis(4-fluorobenzoyl)-1,1′:4′,1″-terphenyl (2), and 3,5-bis(4-fluorobenzoyl)-1,1′:4′,1″:4″,1′′′-quaterphenyl (3), were synthesized by cross-coupling of the corresponding triflates with phenylboronic acid. Linear poly(ether ketone)s (1x, 2x, and 3x) having phenyl, biphenyl, and terphenyl side groups, respectively, were prepared by the polycondensation of the bis(aromatic fluoride) compounds with bisphenol A (a) and 4,4′-dihydroxybiphenyl (b) in N-methyl-2-pyrrolidone. The obtained poly(ether ketone)s were characterized by X-ray diffraction, differential scanning calorimetry, and thermogravimetry. The structure–property relationships of these poly(ether ketone)s were examined and compared with those of poly(ether ketone)s (4x) having no side group, which were prepared from 3,5-bis(4-fluorobenzoyl)benzene (4). The properties of the poly(ether ketone)s, solubilities, and thermal properties were compared and discussed based on the length of the side groups.

Keywords

Poly(ether ketone)s 3,5-bis(4-fluorobenzoyl)biphenyl 3,5-bis(4-fluorobenzoyl)-1,1′:4′,1″-terphenyl 3,5-bis(4-fluorobenzoyl)-1,1′:4′,1″:4″,1′′′-quaterphenyl

Get full access to this article

View all access options for this article.

References

Keksey

Robeson

Clendinng

. ‘Defect-free,’ crystalline aromatic poly(ether ketones): a synthetic strategy based on acetal monomers. Macromolecules 1987; 20: 1204–1212.

Hergenrother

Jensen

Hayens

. Poly(arelene ethers). Polymer 1988; 29: 358–369.

Yonezawa

Okamoto

. Synthesis of wholly aromatic polyketones. Polym J 2009; 41: 899–982.

Patel

Hull

McCabe

. Mechanism of thermal decomposition of poly(ether ether ketone) (PEEK) from a review of decomposition studies. Polym Degrad Stabil 2010; 95: 709–718.

Tokai

Sakaguchi

Kato

. Preparation and properties of poly(ether ketone)s derived from 2,6-naphthalenedicarboxylic acid chloride. High Perform Polym 1995; 7: 267–274.

Tunca

. Synthesis of aromatic poly(ether ketone)s with ferrocene units in main chain. Angew Macromol Chem 1997; 253: 89–97.

Tunca

Hidal

. Synthesis and characterization of aromatic poly(ether ketone)s containing cyclotriphosphazane units. J Polym Sci A Polym Chem 1998; 36: 1227–1232.

Cai

Ding

. Synthesis and properties of copolymers of poly(ether ketone ketone) and poly(ether ether ketone ketone) containing naphthalene moieties and pendant cyano groups. High Perform Polym 2010; 22: 299–331.

Chen

Zhou

Yan

. Synthesis and properties of novel poly(aryl ether ketone)s containing both 2,6-naphthalene and 1,4-naphthalene units. High Perform Polym 2014; 26: 230–239.

10.

Keitoku

Kakimoto

Imai

. Synthesis and properties of aromatic poly (ether sulfone)s and poly(ether ketone)s based on methyl-substituted biphenyl-4,4′-diols. J Polym Sci A Polym Chem 1994; 32: 317–322.

11.

Kimura

Tabuchi

Yamashita

. Synthesis of novel fluorine-containing poly(aryl ether ketone)s. Polym Adv Technol 2000; 11: 757–765.

12.

Wang

Hay

. Synthesis of poly(arylene ether)s based on 9,9-bis(3,5-diphenyl-4-hydroxyphenyl) fluorene. J Polym Sci A Polym Chem 1991; 29: 1045–1052.

13.

Kawasaki

Yamada

Kobori

. Synthesis and chemical, physical, and optical properties of 9,9-diarylfluorene-based poly(ether-ether-ketone). Macromolecules 2007; 40: 5284–5289.

14.

Sheng

Hung

. Synthesis and characterization of novel soluble cardo poly(arylene ether ketone)s containing xanthene structures. J Appl Polym Sci 2009; 114: 570–576.

15.

Okuda

Koyama

Kojima

. 9,9-Diaryl-4,5-diazafluorene-based cardo polymer; Synthesis and characteristic properties. J Polym Sci A Polym Chem 2013; 51: 4541–4549.

16.

Liu

Chen

Guo

. Synthesis of high performance phenolphthalein-based cardo poly(ether ketone imide)s via aromatic nucleophilic substitution polymerization. Polymer 2015; 70: 30–37.

17.

Taguchi

Uyama

Kobayashi

. Synthesis and properties of alkyl-substituted poly(aryl ether ketone)s showing high solubility toward organic solvents. J Polym Sci A Polym Chem 1996; 34: 561–565.

18.

Dai

Wang

. A new class of aromatic poly(ether-ketone benzoxazole) copolymers by nucleophilic polycondensation: synthesis and properties. Eur Polym J 2008; 44: 483–492.

19.

Maeyama

Maeda

Ogino

. Synthesis of optical active aromatic poly(ether ketone)s containing 2,2′-bis(4-benzolphenoxy)-1,1′-binaphthyl-6,6′-ene backbone. React Funct Polym 2005; 65: 229–237.

20.

Shibasaki

Araki

Nagahata

. Control of molecular weight distribution in polycondensation polymers 2. Poly(ether ketone) synthesis. Eur Polym J 2005; 41: 2428–2433.

21.

Percec

Grigoras

Clough

. Synthesis of high molecular weight poly(ether ketone)s by polycondensation of activated bis(ary chloride)s with bisphenolate. J Polym Sci A Polym Chem 1995; 33: 331–344.

22.

Watanabe

Kobayashi

Kakimoto

. Synthesis and characterization of new aromatic polyesters and polyethers derived from 1,2-bis(4-hydroxyphenyl)-1,2-diphenylethylene. J Polym Sci A Polym Chem 1994; 32: 909–915.

23.

Akutsu

Inoki

Kondo

. Synthesis and properties of novel polyarylates and poly(ether ether ketone)s derived from 2,7-triptycenediol. Polym J 1997; 29: 1023–1028.

24.

Liu

Chen

. Soluble aromatic poly(ether ketone)s with a pendant 3,5-difluoromethylphenyl group. Polymer 2004; 45: 3241–3247.

25.

Wang

C-Y

P-H

. High optical transparency and low dielectric constant of novel organosoluble poly(ether ketone amide)s derived from an unsymmetrical diamine containing trifluoromethyl and methyl pendant groups. Colloid Polym Sci 2009; 287: 495–500.

26.

Liu

Cheng

. Synthesis and properties of poly(aryl ether ketone)s with 2,6-diphenylpyridyl moieties and 4-trifluoromethylphenyl side groups. J Fluorine Chem 2014; 157: 30–34.

27.

Maeyama

Kamura

Saito

. Convenient synthesis of aromatic poly(ether ketone)s containing alicyclic units. Polym J 2008; 40: 861–866.

28.

Wang

Geng

Zue

. Synthesis and characterization of soluble low-κ poly(aryl ether ketone) copolymers with pendent adamantyl groups. High Perform Polym 2010; 22: 779–798.

29.

Genq

Zhanq

. Ultra low dielectric constant hybrid films via side chain grafting reaction of poly(ether ether ketone) and phosphotungstic acid. J Mater Chem 2012; 22: 23534–23540.

30.

Geng

Zhang

. Design and preparation of poly(aryl ether ketone)/phosphotungstic acid hybrid films with low dielectric constant. J Appl Polym Sci 2013; 129: 3219–3225.

31.

Ueda

Ichikawa

. Synthesis of aromatic poly(ether ketone)s by nickel-catalyzed coupling polymerization of aromatic dichlorides. Macromolecules 1990; 23: 926–930.

32.

Ueda

Seino

Haneda

. Synthesis of tert-butyl-substituted poly(ether ketone) by nickel-catalyzed coupling polymerization of aromatic dichloride. J Polym Sci A Polym Chem 1994; 32: 675–681.

33.

Maeyama

Yamashita

Saito

. Synthesis of aromatic poly(ether ketone)s bearing optically active macrocycles through Suzuki coupling polymerization. Polym J 2012; 44: 315–320.

34.

Maeyama

Tsukamoto

Suauki

. Nanosized palladium-catalyzed Suzuki–Miyaura coupling polymerization: synthesis of soluble aromatic poly(ether ketone)s. Polym J 2013; 45: 401–405.

35.

Liu

Robertson

Kim

. Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules 2007; 40: 1934–1944.

36.

Bae

Miyatake

Watanabe

. Sulfonated poly(arylene ether sulfone) multiblock copolymers with highly sulfonated brock, synthesis and properties. Macromolecules 2010; 43: 2684–2691.

37.

Morikawa

. Preparation and properties of hyperbranched poly(ether ketones) with a various number of phenylene units. Macromolecules 1998; 31: 5999–6009.

38.

Hou

Jensen

Bai

. Linear viscoelastic properties of a poly(arylene ether ketone) with various molecular weights. High Perform Polym 1989; 1: 41–59.

39.

Mani

Zimmerman

Bhatnager

. Poly(aryl ether ketone) synthesis via competing S_NAR and S_RN1 reactions: 1,3-bis(p-chlorobenzoyl)benzene and 1,3-bis(p-fluorobenzoyl)benzene with hydroquinone and 4,4′-isopropylidenediphenol. Polymer 1993; 34: 171–181.

40.

Morikawa

. Comparison of properties among dendritic and hyperbranched poly(ether ether ketone)s and linear poly(ether ketone)s. Molecules 2016; 21(2): 219. DOI:10.3390/molecules21020219.