Chain‐growth polycondensation of monomer consisting of two aromatic rings: Synthesis of well‐defined poly(ether sulfone) from 4‐fluoro‐4′‐hydroxydiphenyl sulfone

Yokozawa, Tsutomu; Taniguchi, Takahisa; Suzuki, Yukimitsu; Yokoyama, Akihiro

doi:10.1002/pola.10429

Cited by 44 publications

(45 citation statements)

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“…[49] Such a þM effect across 4-hydroxy-4 0 -fluorobenzophenone and 4-hydroxy-4 0 -fluorodiphenylsulfone had already been observed by two other research groups. [68,69] Analogously, a wellcontrolled chain polymerization was realized with an alkyl-substituted 2-cyano-4-hydroxyfluoro benzene (28 and Equation (52), Scheme 17).…”

Section: Frommentioning

confidence: 66%

Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison

Kricheldorf

2007

Macromol. Rapid Commun.

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Characteristic similarities and differences in polycondensations of ‘a − b’ and ‘a2 + b2’ monomers are described including cyclic ‘a − b’ and cyclic ‘a2’ monomers. Polycondensations of ‘ab3’ monomers that yield (hyper)branched polymers are compared with polycondensations of ‘a2 + b3’ monomers that yield (hyper)branched, multicylic, or crosslinked polymers. In all cases the influence of cyclization reactions on structure and molecular weight of the reaction products is considered. Furthermore, the definitions of polycondensation and condensative chain polymerization are discussed along with a differentiation between kinetically controlled and thermodynamically controlled polycondensations.magnified image

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Section: Frommentioning

confidence: 66%

Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison

Kricheldorf

2007

Macromol. Rapid Commun.

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“…55 Monomer 13 is different from other monomers for chain-growth polycondensation in that the monomer consists of two benzene rings and that the nucleophilic site and the electrophilic site are on each benzene ring, respectively. It is then interesting whether the substituent effect of the nucleophilic site can be conveyed effectively to the electrophilic site through two benzene rings connected with the sulfonyl group.…”

Section: Poly(ether Sulfone)mentioning

confidence: 99%

Chain-Growth Polycondensation: Living Polymerization Nature in Polycondensation and Approach to Condensation Polymer Architecture

Yokozawa

Yokoyama

2004

Polym J

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ABSTRACT:In this review article, polycondensation that proceeds in a chain-growth polymerization manner (''chain-growth polycondensation'') for well-defined condensation polymers are described. Our approach to chaingrowth polycondensation is (1) activation of polymer end group by substituent effects changed between monomer and polymer and (2) phase-transfer polymerization in biphase composed of monomer store phase and polymerization phase. In the approach (1), a variety of condensation polymers such as aromatic polyamides, aromatic polyesters, aromatic polyethers, poly(ether sulfone), and polythiophene with defined molecular weights and low polydispersities were obtained. Their polycondensations had all of the characteristics of living polymerization: a linear correlation between molecular weights and monomer conversion maintaining low polydispersities, and control over molecular weights by the feed ratio of monomer to initiator. Taking advantage of the nature of living polymerization in this polycondensation, we synthesized diblock copolymers of different kinds of aromatic polyamides and of aromatic polyamide and conventional polymers such as poly(ethylene glycol), polystyrene, and poly(tetrahydrofuran), as well as triblock copolymers and star polymers containing aromatic polyamide units. Some copolymers were arranged in a supramolecular self-assembly. In the approach (2), the polycondensation of solid monomer dispersed in organic solvent with a phase transfer catalyst (PTC) was carried out, where solid monomer did not react with each other, and the monomer transferred to organic solvent with PTC reacted with an initiator and the polymer end group selectively in organic solvent, to yield well-defined polyesters.KEY WORDS Chain-Growth Polycondensation / Polycondensation / Living Polymerization / Controlled Polymerization / Architecture / Polyamides / Polyesters / Polyethers / Polythiophenes / Polymerization can be classified into two categories: chain polymerization and step polymerization. Chain polymerization is initiated by the reaction of monomer and initiator, and then monomers react with the propagating group of polymers. If the chain polymerization proceeds in a living polymerization manner, the molecular weight of polymer is controlled by the feed ratio of monomer to initiator and the molecular weight distribution is narrow. In addition, the molecular weight increases in proportion to monomer conversion while retaining low polydispersity over the whole conversion range.On the other hand, step polymerization is initiated by the reaction of monomers with each other, and propagation involves the reactions of all kinds of oligomers with themselves, as well as the reactions of those oligomers with monomers. Therefore, it is difficult to control the molecular weight of polymer, and polymer possesses a broad molecular weight distribution. Plotting the molecular weight values and the polydispersity against monomer conversion, the molecular weight does not increase much in the initial and middle stage and is acce...

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“…3 A polysulfide is a polymer that contains the −S−S− group in the backbone. However, a poly(sulfide), with sulfide in brackets, such as poly(phenylene sulfide) or 6,7 4,4 -Dichlorodiphenyl sulfone and bisphenol A disodium salt 8 4,4 -Dichlorodiphenyl sulfone and 4,4 -dihydroxydiphenyl sulfone 6 4-Fluorobenzenesulfinate catalyzed by 4,4 -difluorodiphenyl sulfone 9 4-Fluoro-4 -hydroxydiphenyl sulfone, and (fluorophenyl)-(trifluorophenyl) sulfone as initiator 10 4,4 -Difluorodiphenyl sulfone, and silylated 4-tert-butylcatechol 11 5-[(4-fluorophenyl)sulfonyl]-2-fluorobenzoic acid and bis-(4-hydroxyphenyl)-sulfone 12 2. Hydrolysis of dibromodiphenyl, or 3.…”

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confidence: 99%

Poly(arylene ether sulfone)s

Fink

2008

High Performance Polymers

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Chain‐growth polycondensation of monomer consisting of two aromatic rings: Synthesis of well‐defined poly(ether sulfone) from 4‐fluoro‐4′‐hydroxydiphenyl sulfone

Abstract: The polycondensation of 1a in the presence of 2 as an initiator and 18‐crown‐6 proceeded in a chain‐polymerization manner in sulfolane at 120 °C to yield poly(ether sulfone) having defined molecular weights and low polydispersities.

Cited by 44 publications

References 51 publications

Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison

Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison

Chain-Growth Polycondensation: Living Polymerization Nature in Polycondensation and Approach to Condensation Polymer Architecture

Poly(arylene ether sulfone)s

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Chain‐growth polycondensation of monomer consisting of two aromatic rings: Synthesis of well‐defined poly(ether sulfone) from 4‐fluoro‐4′‐hydroxydiphenyl sulfone

Abstract: The polycondensation of 1a in the presence of 2 as an initiator and 18‐crown‐6 proceeded in a chain‐polymerization manner in sulfolane at 120 °C to yield poly(ether sulfone) having defined molecular weights and low polydispersities.

Cited by 44 publications

References 51 publications

Polycondensation of ‘a − bn’ or ‘a2 + + bn’ Monomers ‐ A Comparison

Polycondensation of ‘a − bn’ or ‘a2 + + bn’ Monomers ‐ A Comparison

Chain-Growth Polycondensation: Living Polymerization Nature in Polycondensation and Approach to Condensation Polymer Architecture

Poly(arylene ether sulfone)s

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Product

Resources

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Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison

Polycondensation of ‘a − b_n’ or ‘a₂ + + b_n’ Monomers ‐ A Comparison