Synthesis and Properties of Novel Aromatic Poly(thioether−ketone)s as Sulfur-Containing High-Performance Polymers

Abstract

Novel aromatic poly(thioether-ketone)s (PTEKs) bearing the 2,6-dimethyl-1,5-naphthylene units were synthesized by the polycondensation of aromatic dihaloketones and aromatic dithiols in the presence of K 2CO3. PTEKs with molecular weight (Mn ∼ 65 000, Mw ∼ 350 000) were obtained in quantitative yields. The molecular weights and yields of PTEKs obtained from aromatic dichloroketone and aromatic dithiols were much higher than those of the corresponding poly(ether-ketone)s (PEKMNs) obtained from aromatic dichloroketone and biphenols and were nearly the same as those of PTEKs obtained from aromatic difluoroketone and aromatic dithiols. The effect of reaction conditions on yield and molecular weight of PTEKs was investigated. The PTEKs had high solubility in ordinary organic solvents. Flexible, transparent, and strong films were cast from CHCl 3 solution. PTEK-1 and PTEK-2 had high glass transition temperatures (Tg; PTEK-1 245°C, PTEK-2 215°C) and 5% weight loss temperatures (Td5; PTEK-1 435°C, PTEK-2 436°C).

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

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

“…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.…”

“…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.…”

Direct Synthesis of Fully Sulfonated Polyarylenethioether Sulfones as Proton‐Conducting Polymers for Fuel Cells

“…[7][8][9] The synthesis and characterization of sulfonated high-performance polymers based on arylene ether and arylenethioether linkages in the backbone for potential fuel cell applications have also been reported. [10,11] All the sulfonated high-performance polymers have good thermal stability and chemical resistance. The reported water uptake and proton conductivity data of the polymers are promising enough for PEM candidates in fuel cells.…”

Rate constants for the reaction of ozone with n-butyl, s-butyl and t-butyl methyl sulfides

“…Aryl, alkenyl and alkyl thioethers are important synthetic reagents and intermediates in organic synthesis. They have been employed in the synthesis of novel biologically active compounds [6] , polymer materials [7] and used as extracting reagents [8] . Thioethers are also mixed into LPG (liquefied petroleum gas) and fuel cell as leakage sensor odorants [9] .…”