Poly(arylene ether sulphones) by polyetherification: 2. Polycondensations

Attwood, T.E.; Barr, D. A.; King, T.; Newton, A.B.; Rose, Jeremy

doi:10.1016/0032-3861(77)90083-0

Cited by 85 publications

(30 citation statements)

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“…[1][2][3][4] Therefore, PEEKs and PEEKKs are currently receiving considerable attention for potential applications in aviation, automobile manufacturing, electronic/electrical, medical care, fuel cell, gas separation, and food processing sectors. PEEKs and PEEKKs can be prepared via electrophilic or nucleophilic substitution reaction.…”

Section: Introductionmentioning

confidence: 99%

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Honkhambe

Pasale

Bhairamadgi

et al. 2011

J of Applied Polymer Sci

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Section: Introductionmentioning

confidence: 99%

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Honkhambe

Pasale

Bhairamadgi

et al. 2011

J of Applied Polymer Sci

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“…Fluorinated poly(arylene ether ketone)s (FPAEK) [1][2][3][4][5] are conventionally prepared by the polycondensation of the phenol groups of hexafluorobisphenol A (6F-BPA) with para-fluorines of bis(pentafluorophenyl) ketone (BPK) using a nucleophilic aromatic substitution reaction (S N Ar), [6][7][8][9][10] which has been traditionally used for the preparation of nonfluorinated poly(arylene ether)s. [11,12] The major problem of this reaction when applied to the preparation of FPAEK is the high tendency of a side reaction at the ortho-fluorines of BPK, [3,4] which are activated by the strong electronwithdrawing effect of the ketone group. [10] This side reaction leads to the formation of branched and eventually crosslinked structures.…”

Section: Introductionmentioning

confidence: 99%

Highly Fluorinated Poly(arylene ether ketone) Prepared by a CaH₂‐Mediated Polycondensation Reaction

Ding

Day

Robertson

et al. 2004

Macro Chemistry & Physics

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Summary: A new reaction procedure has been developed for the polycondensation of hexafluorobisphenol A (6F‐BPA) with bis(pentafluorophenyl) ketone (BPK) in dimethylacetamide (DMAc). In this reaction, CaH2 has been used as a base to facilitate the formation of the phenolate; an alkali metal fluoride was used as a catalyst. Unlike the conventional polycondensation reactions, this procedure avoided producing water during the reaction, and hence, azeotropic distillation with the assistant of a low‐polar co‐solvent is not required. This improvement maintains the high polarity of the reaction medium; consequently, the selectivity of the reaction at the para‐position of BPK is significantly enhanced and polymers with high molecular weights ($\overline M _{\rm n}$ ca. 30 000 Da) can be obtained with very low branching contents (less than 3 mol‐%) and free of any cross‐linked gel particles. In addition to avoiding the formation of water in the reaction, the use of CaH2 also reduced the concentration of the fluoride ion in the solution. These effects minimize chain degradation reactions such as hydrolysis. The use of CaO instead of CaH2 for this reaction produces similar effects. In the case of CaO, traces of water can be introduced into the reaction. The presence of trace amounts of water increases the polycondensation rate, probably due to the enhanced ionization of the phenolate. However, it also causes a hydrolysis of polymer chains, resulting in the elimination of the ketone group in the polymer backbone. Fortunately, this side reaction is highly water and temperature dependent, and can be efficiently prevented by using CaH2 or conducting the reaction at a lower temperature (<65 °C).CaH2‐mediated polycondensation for the preparation of highly fluorinated poly(arylene ether ketone).imageCaH2‐mediated polycondensation for the preparation of highly fluorinated poly(arylene ether ketone).

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“…8,9 This method also allows the formation of polymers incorporating two different functionalities at the chain ends. 10 Therefore, two different reactions can be performed at each end, enabling the preparation of AB-and ABC-type block copolymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(ether sulfone)s by self-polycondensation of AB-type monomers

Matsumoto

Komuro

Kai

et al. 2013

Polym J

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Self-polycondensation of AB-type monomers is an advantageous route to produce high-molecular-weight polymers without considerable adjustment in the mole ratio of the functionalities. Furthermore, the resulting polymers incorporate two different functional groups at the chain ends that enable the preparation of AB-and ABC-type block copolymers. In this study, poly(ether sulfone)s (PESs) were prepared via self-polycondensation of four AB-type monomers. The reactivity of the AB-type monomers was systematically investigated through model reactions and nuclear magnetic resonance measurements, which suggested that the novel AB-type monomers, 4-chloro-4 0 -(hydroxyphenyloxy)diphenylsulfone (monomer C) and 4-fluoro-4 0 -(hydroxyphenyloxy)diphenylsulfone (monomer D), are highly susceptible to nucleophilic aromatic substitution (S N Ar) reactions. High-molecular-weight PESs (M w 4110 000) were obtained via the self-polycondensation of monomers C and D. The resulting PESs exhibited excellent thermal properties comparable with PESs prepared from A 2 -and B 2 -type monomers.

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Poly(arylene ether sulphones) by polyetherification: 2. Polycondensations

Cited by 85 publications

References 4 publications

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Highly Fluorinated Poly(arylene ether ketone) Prepared by a CaH₂‐Mediated Polycondensation Reaction

Synthesis of poly(ether sulfone)s by self-polycondensation of AB-type monomers

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Poly(arylene ether sulphones) by polyetherification: 2. Polycondensations

Cited by 85 publications

References 4 publications

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing cardo decahydronaphthalene groups: Synthesis and characterization

Highly Fluorinated Poly(arylene ether ketone) Prepared by a CaH2‐Mediated Polycondensation Reaction

Synthesis of poly(ether sulfone)s by self-polycondensation of AB-type monomers

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Highly Fluorinated Poly(arylene ether ketone) Prepared by a CaH₂‐Mediated Polycondensation Reaction