Synthesis of All Aromatic Poly(Thioether-Ketone)s, Sulfur-Containing High Performance Polymers with High Solubility

Matsumura, Sumiko; Kihara, Nobuhiro; Takata, Toshikazu

doi:10.1088/0954-0083/13/2/325

Cited by 9 publications

(10 citation statements)

References 9 publications

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“…The thermal stability of PAS was always lower than that of the corresponding PTE in most cases, probably because PTE has thermosetting property in contrast to PAS. 9 The DSC study of PASs with a scanning rate of 10 C/ min under a nitrogen atmosphere indicated that all PASs were not crystalline but amorphous. The glass transition temperature T g of PASs was in a range from 248 to 355 C, depending on their structures.…”

Section: Resultsmentioning

confidence: 97%

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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Section: Resultsmentioning

confidence: 97%

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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“…The phase-transfer-catalyzed polycondensation and the polycondensation using masked dithiol and dichloroketone are also investigated (98,99). Poly(thioeter ketone)s have well-balanced properties, namely, good processibility, high electrical insulation, good mechanical properties, high thermostability, and excellent flame resistance.…”

Section: Poly(monosulfide Ketone)s Aromatic Poly(monosulfide Ketone)smentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys

2010

Encyclopedia of Polymer Science and Technology

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Sulfur-containing polymers, when considering their structure, make up a complex group of macromolecular compounds of varied and often remarkable features that determine their versatile applications.The presence of sulfur atoms in polymer structure, depending on the kind of functional group, can improve some important properties, such as mechanical, electrical, and optical, and then adhesion to metals, resistance to heat, chemicals, radiation, and bacteria, biocompatibility, and so on. These are their more important functional groups: sulfide -S-, polysulfide -S n -, sulfonyl -SO 2 -, sulfinyl -SO-, sulfo -SO 3 H, as well as some organic groups containing sulfur atoms, such as thioester -Sulfur-containing polymers can be used as high performance engineering plastics, chemically stable ion-exchange membranes in electromembrane processes, proton-conducting electrolytes, as well as optical, optoelectronic, and photochemical materials. Some polymers are employed in biomedical applications, for example, sulfopolymers as biomembranes and blood-compatible materials, and polysulfates and polysulfonates as antithrombotic or antiviral agents. The presence of sulfur, particularly in the form of disulfide bridges, plays an important role in biopolymers.The purpose of this review is mainly to present recent advances in the area of sulfur-containing polymers that may not yet have commercial applications. Nevertheless, older but still significant material has been included at the beginning of the discussion of each class. Poly(monosulfide)sPolymers containing a monosulfide linkage in both the main chain and the pendent group are the subject of many detailed studies. A few reviews of the synthesis and properties of all types of polymers have been published (1-4); like the one covering polymer with sulfur in the main chain that appeared in 1992 (3). Polysulfides with controlled and well-defined structures can be easily prepared. Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)].

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“…12,13 Crude polymer was purified by repeated reprecipitation of chloroform solution into methanol. Inorganic impurities were removed by washing with boiling methanol.…”

Section: Preparation Of Ptek and Pekmentioning

confidence: 99%

“…12,13 PTEK, which has so far been viewed as a mere sulfur analog of PEKs, has not been paid much attention. Only the solubility, thermal properties, and crystallinity of PTEK [12][13][14][15][16][17] have been studied, although a few reports have included information on tensile properties, oxygen index, and melt index. 6,18 The effect of sulfur atoms on the properties of PTEK has been neglected because PTEK and the corresponding PEK have similar solubility, thermal properties, and crystallinity.…”

Section: Introductionmentioning

confidence: 99%

“…6,18 The effect of sulfur atoms on the properties of PTEK has been neglected because PTEK and the corresponding PEK have similar solubility, thermal properties, and crystallinity. 6,12,13,[15][16][17] However, the properties of the sulfur-containing functional group are far different from those of the corresponding oxygen-containing functional group. PTEK may show a lower water ab-sorption property than the corresponding PEK because sulfide is more hydrophobic than its corresponding ether.…”

Section: Introductionmentioning

confidence: 99%

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Properties of a few aromatic poly(thioether ketones) as sulfur‐containing high‐performance polymers

Matsumura

Kihara

Takata

2004

J of Applied Polymer Sci

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Several basic physical properties of poly-(thioether ketones) (PTEKs) were studied in comparison with corresponding ether analogs, poly(ether ketones) (PEKs), and various typical engineering plastics. The water absorption of PTEK (0.13%) was lower than that of the corresponding PEK (0.16%), probably because of the hydrophobic nature of the sulfide group. The dielectric breakdown strengths of PTEK and PEK were much greater than that of commercially available polymers. PTEK had higher dielectric breakdown strength than PEK. Although the volume resistivity of PEK considerably decreased after water absorption, that of PTEK remained high even after water absorption. PTEK exhibited a remarkably high refractive index (n D 23 1.66). ␣-Transition corresponding to T g was observed at a high temperature (PTEK-1, 235°C; PTEK-2, 269°C) in the dynamic mechanical analysis. Young's modulus and tensile strength of PTEK were comparable to those of commercial high-performance polymers. PTEK also exhibited excellent flame resistance. Although the linear thermal expansion coefficient of PTEK was greater than that of PEEK, it was still within a practically acceptable level

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Synthesis of All Aromatic Poly(Thioether-Ketone)s, Sulfur-Containing High Performance Polymers with High Solubility

Cited by 9 publications

References 9 publications

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

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

Sulfur‐Containing Polymers

Properties of a few aromatic poly(thioether ketones) as sulfur‐containing high‐performance polymers

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