Synthesis of Aromatic Poly(ether sulfone)s by Nickel-Catalyzed Coupling Polymerization of Aromatic Dichlorides

Ueda, Mitsuru; Ito, Takashi

doi:10.1295/polymj.23.297

Cited by 25 publications

(12 citation statements)

References 5 publications

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“…Poly(ether ether sulfone)s 2 were chosen by Colon as the first system to be studied because they are generally amorphous and soluble in dipolar aprotic solvents such as N,N-dimethylacetamide (DMAc) and 1-methyl-2-pyrrolidinone (NMP) at the relatively low temperatures (70 °C) required to produce high polymer. Further studies of this system, 3 in addition to a variety of poly(arylene ether ketone)s, have been investigated by Ueda et al 4 Ueda utilized Ni(0) coupling of aromatic dichlorides containing ether-ketone structures to prepare high molecular weight poly(arylene ether ketone)s. This method proved advantageous compared with conventional methods because of the high rates and the mild conditions of the reaction.…”

Section: Price Codementioning

confidence: 99%

Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Phillips¹,

Sheares²,

Samulski³

et al. 1994

Macromolecules

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Section: Price Codementioning

confidence: 99%

Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Phillips¹,

Sheares²,

Samulski³

et al. 1994

Macromolecules

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“…Sulfonated monomer for flame retarding materials was prepared by Robeson and Matzner [ 24 ] the pioneering scientists in this field. Recently, Ueda et al [ 25,26 ] reported the sulfonation of 4,4′-dichlorodiphenyl sulfone and other researchers [ 27–34 ] modified this procedure for the disulfonation of monomer.…”

Section: Introductionmentioning

confidence: 99%

Effect of sulfonation degree on molecular weight, thermal stability, and proton conductivity of poly(arylene ether sulfone)s membrane

Pirali-Hamedani

Mehdipour‐Ataei

2016

Designed Monomers and Polymers

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Direct copolymerization of sulfonated and non-sulfonated difluorodiphenyl sulfones as dihalide monomers with hydroquinone and also 4,4′-(4,4′-sulfonylbis-(1,4-phenylene)bis(oxy)) diphenol as diols led to preparation of two series of poly(arylene ether sulfone)s. Copolymers with different degrees of sulfonation (40, 50 and 60%) were synthesized in order to evaluate their potential for fuel cell application. 1H-NMR, FT-IR, and mass spectroscopy were used for characterization of prepared monomers and copolymers. Differential scanning calorimetry and thermogravimetric analysis were applied for investigation and comparison of the thermal properties of copolymers. Laser light scattering (LLS) was employed to calculate zeta potential, conductivity, and molecular weight of copolymers. Copolymers were obtained in high and sufficient molecular weight that was basic need to reach reasonable physical and thermal properties for applications as fuel cell membrane. The effect of similar structural repeating units with different sizes on the final properties of sulfonated poly(ether sulfone)s was investigated to compare their potential in fuel cell membrane.

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“…3 Ueda et al 4 have reported the synthesis of aromatic poly(ether sulfone)s from nickel complex-mediated aromatic coupling polymerization of aromatic dichloride. An alternative way of making poly(arylene sulfone)s involves oxidation of poly(arylene thioether)s with hydrogen peroxide in formic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Property of Poly(arylene sulfone)s Containing 9,9-Diarylfluorene Moiety in the Main Chain

Seesukphronrarak

Takata

2007

Polym J

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ABSTRACT:Poly(arylene sulfone)s (PASs) were synthesized in quantitative yields by the oxidations of the corresponding fluorene-containing poly(arylene thioether)s, derived from 9,9-diarylfluorene-based dithiols and dihaloarenes, with 30% hydrogen peroxide in formic acid. PASs had good solubility in common organic solvents such as chloroform, N-methylpyrrolidone (NMP), and N,N-dimethylformamide (DMF). Highly transparent films were obtained by casting the chloroform solutions of PASs. PASs exhibited high glass transition and high decomposition temperatures (T g 248-355C, T d5 > 400 C under nitrogen). [doi:10.1295/polymj.PJ2006211] KEY WORDS Poly(arylene thioether) / Poly(arylene sulfone) / 9,9-Diarylfluorene / Thermal Stability / Solubility / Increasing interest has been devoted to the syntheses of high performance polymers with special property including poly(arylene sulfone)s as amorphous engineering thermoplastics. Poly(arylene sulfone)s possess excellent properties such as mechanical strength, hydrolytic stability, low flammability, and oxidative stability, making them wildely useful in various applications.1 For example, they could be the basic materials for porous and dense polymeric membranes required for gas separation or fuel cell application.2 Some polysulfones are commercially available as high performance engineering plastics such as UDEL Ò , VICTREX Ò , RADEL Ò , and so on. Aromatic polysulfones are often synthesized by direct polymerization via aromatic nucleoplilic substitution of the corresponding bis(fluoroaryl)sulfones and bisphenols as monomers.3 Ueda et al. 4 have reported the synthesis of aromatic poly(ether sulfone)s from nickel complex-mediated aromatic coupling polymerization of aromatic dichloride. An alternative way of making poly(arylene sulfone)s involves oxidation of poly(arylene thioether)s with hydrogen peroxide in formic acid. 5,6 By the replacement of thioether function with sulfone function in polymer main chain, it is expected that sulfone polymer shows, e.g., glass transition temperature (T g ) higher than the corresponding thioether polymer. Meanwhile, polymers containing 9,9-diarylfluorene moieties in the main chain have collected much interest because of their excellent properties such as high solubility and good optical properties based on the cardo structure of the 9,9-diarylfluorene moiety.7 Since polysulfones are usually hard to be soluble in ordinary organic solvents, the introduction of the fluorene skeleton seems to improve the solubility of polysulfones in addition to endowment of good optical property. We have recently prepared 9,9-diarylfluorene-based poly(arylene thioether)s with excellent physical and optical properties.8 As far as we know, no data has been reported by using of poly(arylene thioether)s containing 9,9-diarylfluorene to obtained poly(arylene sulfone)s. Therefore, we have undertaken the synthesis of poly-(arylene sulfone)s by the oxidation of the poly(arylene thioether)s, judging from the ease of procedure. This report describes the synthesis and cha...

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Synthesis of Aromatic Poly(ether sulfone)s by Nickel-Catalyzed Coupling Polymerization of Aromatic Dichlorides

Cited by 25 publications

References 5 publications

Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Effect of sulfonation degree on molecular weight, thermal stability, and proton conductivity of poly(arylene ether sulfone)s membrane

Synthesis and Property of Poly(arylene sulfone)s Containing 9,9-Diarylfluorene Moiety in the Main Chain

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