Poly(aryl ether sulfide)s by sulfide-activated nucleophilic aromatic substitution polymerization

Knauss, Daniel M.; Edson, Joseph B.

doi:10.1016/j.polymer.2006.02.073

Cited by 23 publications

(19 citation statements)

References 65 publications

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“…Sulfolane and fluorobenzene were distilled under vacuum prior to use. Bis(4fluorophenyl)sulfoxide was synthesized as reported [42] and purified twice by recrystallization from hexane.…”

Section: Methodsmentioning

confidence: 99%

Deoxybenzoin-containing polysulfones and polysulfoxides: Synthesis and thermal properties

Mir

Wagner

Krämer

et al. 2016

Polymer

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Novel poly(arylene ether) sulfones, sulfoxides, and sulfides containing deoxybenzoin subunits were synthesized by step growth polymerization involving bishydroxydeoxybenzoin (BHDB) and the corresponding sulfur-containing monomers. The isolated polymers demonstrated good solubility in organic solvents, making them easily processible into transparent, flexible, and creasable films upon solution casting. All of the polymers prepared exhibited exceptionally low flammability characteristics, with total heat release (THR) values as low as 6 J/g-K, and char yield values as high as 54%. Integration of deoxybenzoin monomers into polysulfones with 4,4'biphenyl led to heat release capacity (HRC) values less than half that of commercial polysulfones in use today, placing deoxybenzoin-based polysulfones and polysulfoxides into the ultra-low flammability category.Polymer flammability represents a pressing and persistent societal problem of growing importance with increasing global polymer production, consumption, and waste accumulation.[1] The abundance of synthetic polymers in construction, and transportation vehicles places safety concerns, such as flammability, at a high priority. Efforts to overcome the inherent flammability of high volume polymer materials, as well as specialty products, can improve the safety of polymers and reduce the frequency of fire-related catastrophic events. [2]

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“…Sulfolane and fluorobenzene were distilled under vacuum prior to use. Bis(4fluorophenyl)sulfoxide was synthesized as reported [42] and purified twice by recrystallization from hexane.…”

Section: Methodsmentioning

confidence: 99%

Deoxybenzoin-containing polysulfones and polysulfoxides: Synthesis and thermal properties

Mir

Wagner

Krämer

et al. 2016

Polymer

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“…It is synthesized by the intramolecular cyclization of a methylsulfinyl substituted poly(m-phenylene sulfide). It can be condensed with a bisphenol to yield poly(aryl ether thianthrene)s. 45,52 The poly(aryl ether thianthrene)s are flame resistant and exhibit a high refractive index of 1.61-1.70, depending on the wavelength and the corresponding bisphenol. 50 The basic reaction is the same as shown in Figure 5 Poly(imide)s with the dithiathianthrene group are accessible from the reaction of thianthrene-2,3,7,8-tetracarboxylic dianhydride aromatic diamines.…”

Section: Poly(dithiathianthrene)smentioning

confidence: 99%

Poly(phenylene sulfide)

Fink

2008

High Performance Polymers

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“…More obscure groups have also been identified such as benzoxazoles, oxadiazoles, phenylquinoxalines, and even perfluoroalkanes . This research group has previously studied other sulfur containing groups that activate S N Ar such as sulfides, thianthrenes, and sulfonamides …”

Section: Introductionmentioning

confidence: 99%

Poly(ether sulfone)s using a rigid dibenzothiophene dioxide heterocycle

Kortan¹,

Cannizzaro²,

Robb³

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Poly(aryl ether)s were prepared by nucleophilic aromatic substitution using conformationally restricted dichloroand difluorodibenzothiophene dioxide heterocyclic monomers with bisphenol A or bisphenol AF. The heterocyclic monomers were prepared from the bis(4-halophenyl) sulfones in two steps via lithiation followed by copper catalyzed intramolecular coupling and characterized by 1 H, 13 C, 19F NMR spectroscopy and GC/MS. Reactivity of the fluorine containing monomer was examined using semi-empirical methods and NMR spectroscopy measurements and found to be potentially more reactive than bis(4-fluorophenyl) sulfone, even with a conformationally locked sulfone as the electron withdrawing group. Successful polymerizations of both the fluorine and chlorine containing monomers with bisphenol A and bisphenol AF nucleophiles were accomplished, providing polymers with number average molecular weights of approximately 45 kg/mol (difluoro monomer) and 10-20 kg/mol (dichloro monomer). The polymers exhibited high T g s ranging from 238 to 256 8C and displayed good thermal stability with 5% degradation temperatures in air from 453-510 8C, depending on molecular weight and bisphenol composition.

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Poly(aryl ether sulfide)s by sulfide-activated nucleophilic aromatic substitution polymerization

Cited by 23 publications

References 65 publications

Deoxybenzoin-containing polysulfones and polysulfoxides: Synthesis and thermal properties

Deoxybenzoin-containing polysulfones and polysulfoxides: Synthesis and thermal properties

Poly(phenylene sulfide)

Poly(ether sulfone)s using a rigid dibenzothiophene dioxide heterocycle

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