Synthesis of aromatic polysulfide from bis(4‐chloro‐3‐nitrophenyl) sulfone and 4,4′‐oxydibenzenethiol under mild conditions

Imai, Yoshio; Ueda, Mitsuru; Komatsu, Masanobu; Urushibata, Hirotomo

doi:10.1002/marc.1980.030011105

Cited by 17 publications

(3 citation statements)

References 10 publications

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“…Sulfolane was the best solvent to yield the highest molecular weight of PTEK-2 in quantitative yields (runs 2, 4, and 5). The phasetransfer-catalysed polycondensation of dithiols and dihalosulfones was investigated and gave high molecular weight PTES at room temperature [8]. We also studied the phase-transfercatalysed polycondensation.…”

Section: Polycondensation Of Aromatic Dithiol and Aromatic Dichloroketone: Effect Of Reaction Conditionsmentioning

confidence: 99%

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

Matsumura¹,

Kihara²,

Takata

2001

High Performance Polymers

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Novel aromatic poly(thioether-ketone)s (PTEKs) bearing the 2,6-dimethyl-1,5-naphthylene unit were synthesized by the polycondensation of aromatic dihaloketones and aromatic dithiols in the presence of K 2 CO 3 . High molecular weight (Mn ∼ 65 000, Mw ∼ 350 000) PTEKs were obtained in quantitative yields. The molecular weight and yield of PTEK obtained from dichloroketone and dithiol were much higher than those of the corresponding poly(ether-ketone) obtained from dichloroketone and biphenol. The use of the fluoroketone as a monomer did not increase the Mn of PTEK. The effect of reaction conditions on the yield and the molecular weight of PTEKs was investigated. The phasetransfer-catalysed polycondensation and the polycondensation using masked dithiol and dichloroketone were also investigated. The PTEKs prepared have high solubility in ordinary organic solvents. Flexible, transparent, and strong cast films were prepared. The PTEKs had high glass transition temperatures (PTEK-1, 245 • C and PTEK-2, 215 • C) and 5% weight loss temperatures (PTEK-1, 435 • C and PTEK-2, 436 • C).

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Section: Polycondensation Of Aromatic Dithiol and Aromatic Dichloroketone: Effect Of Reaction Conditionsmentioning

confidence: 99%

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

Matsumura¹,

Kihara²,

Takata

2001

High Performance Polymers

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“…PPS is produced by the high-temperature solution polycondensation of p-dichlorobenzene with sodium sulfide, while a number of aromatic polysulfides are usually synthesized from monomer pairs of aromatic dithiols and activated aromatic dihalides 1,2) . The solution polycondensation using anhydrous potassium or sodium carbonate [3][4][5][6] and the phase-transfer-catalyzed polycondensation 7) have been reported as typical synthetic methods of aromatic polysulfides. Still another method using potassium fluoride as the base has been known as a more simple synthetic route 8,9) , because this method does not require the removal of water during the preparation of potassium salts of dithiols from the reaction system prior to the polycondensation.…”

Section: Introductionmentioning

confidence: 99%

Cesium fluoride-mediated synthesis of aromatic polysulfides from aromatic dithiols and activated aromatic dihalides

Imai¹,

Yamanaka

Ishikawa

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: The solution polycondensation of aromatic dithiols with activated aromatic dihalides like bis(4-fluorophenyl) sulfone with use of cesium fluoride as a base in polar aprotic solvents readily affords aromatic polysulfides having inherent viscosities as high as 1.0 dL/g. The polycondensation proceeds under essentially neutral and milder reaction conditions compared with the conventional method using potassium carbonate and with the cesium fluoride-assisted synthesis of aromatic polyethers as well.

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“…These polymers are ordinarily prepared8 by the polycondensation of p ‐dichlorobenzene with sodium sulfide in NMP at elevated temperatures. Imai et al9 reported the synthesis of poly(aromatic sulfide) by the polycondensation of potassium salt of aromatic dithiol in aqueous solution with active aromatic dihalide in nitrobenzene at room temperature using quaternary onium salts or crown ethers as the PTC. Ueda and coworkers10 also reported the synthesis of poly(aliphatic sulfide)s by the polycondensation of dibromoalkanes with sodium sulfide in the presence of quaternary onium salts as the PTC.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polymers in aqueous solutions: Synthesis of polysulfide by reaction of bis(4-mercaptophenyl) sulfide with bis(4-chloro-3-nitrophenyl) sulfone using various bases in aqueous solutions

Kimura

Sato

Kameyama

et al. 2000

J. Polym. Sci. A Polym. Chem.

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The polycondensation of bis(4‐mercaptophenyl) sulfide (BMPS) with bis(4‐chloro‐3‐nitrophenyl) sulfone (BCNPS) was examined using various organic or inorganic bases in mixed solvents of N‐methyl‐2‐pyrrolidone (NMP) with water or in plain water. The reaction of BMPS with BCNPS proceeded smoothly to give the corresponding polysulfide in mixed solvents of NMP with water at 60 °C using 1,8‐diazabicyclo[5.4.0]undecene‐7 as a base, although the rate of the reaction decreased gradually as the water in the solvent increased. Polysulfide can also be obtained by reaction in plain water using appropriate organic bases such as tripropylamine (TPA) or quinoline. The polysulfide with a number‐average molecular weight of 45,100 was synthesized in 62% yield when the reaction of BMPS with BCNPS was performed using TPA as a base at 60 °C for 48 h in plain water. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 3399–3404, 2000

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Synthesis of aromatic polysulfide from bis(4‐chloro‐3‐nitrophenyl) sulfone and 4,4′‐oxydibenzenethiol under mild conditions

Cited by 17 publications

References 10 publications

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

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

Cesium fluoride-mediated synthesis of aromatic polysulfides from aromatic dithiols and activated aromatic dihalides

Synthesis of polymers in aqueous solutions: Synthesis of polysulfide by reaction of bis(4-mercaptophenyl) sulfide with bis(4-chloro-3-nitrophenyl) sulfone using various bases in aqueous solutions

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