Synthesis and Characterization of Poly(Aryl Ether-Bissulfone)s

Cummings, D. R.; Mani, R. S.; Balanda, Peter B.; Howell, Bob A.; Mohanty, Dillip K

doi:10.1080/00222339108054057

Cited by 10 publications

(3 citation statements)

References 10 publications

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“…As an example polymer 6 a showed a T g at 207 38) . The same effect can be observed comparing polymer 6 b with polymer 8 obtained starting from F-v-SO 2 -vv-SO 2 -v-F and BPA 39) , in fact the substitution of the sulfone groups with the 1,3,4-oxadiazole units resulted, also in this case, in a polymer with higher T g value (Tab. 2).…”

Section: Resultssupporting

confidence: 82%

Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Bottino¹,

Pasquale

Pollicino

1999

Macromol. Rapid Commun.

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SUMMARY: Starting from some new 2,5-disubstituted-1,3,4-oxadiazole difluorides, synthesized by cyclocondensation of dihydrazides with 4-fluorobenzoic acid, novel poly(arylene ether)s were prepared by halo displacement polymerizations with bisphenol A in the presence of potassium carbonate. Model reactions demonstrated the unsuitableness for halo displacement reactions of the difluoride containing the SO 2 group. The synthesis and characterization of polymers are discussed and the thermal properties are compared with those of other polymers reported in literature.

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Section: Resultssupporting

confidence: 82%

Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Bottino¹,

Pasquale

Pollicino

1999

Macromol. Rapid Commun.

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“…In all cases, the loss of starting materials with concurrent production of oligomeric products were observed. Similar results were obtained when a sulfone-containing monomer, 4,4'-bis(4-chlorosulfonyl)biphenyl 16) was allowed to react with potassium carbonate in NMP. These results suggest that NMP is not a suitable solvent for the polymerization reactions (in the presence of an excess of weak base) of monomers containing one activating group per replaceable halogen atom if the polymerization is carried out at elevated temperatures.…”

Section: Series Of Productssupporting

confidence: 68%

Competing processes for poly(aryl ether‐ketone) synthesis, 3. Polymerization reactions of 1,3‐bis(4‐chlorobenzoyl)benzene and 1,3‐bis(4‐fluorobenzoyl)benzene in N‐methyl‐2‐pyrrolidinone

Bhatnagar

Mani

King

et al. 1996

Macro Chemistry & Physics

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The effects of N-methyl-2-pyrrolidinone (NMP) as solvent on the polymerizaton reactions of 1,3-bis(4-chlorobenzoyl)benzene (1,3-CBB) and 1,3-bis(4-fluorobenzoyl)benzene (1,3-FBB) with 4,4'-isopropylidenediphenol (bisphenol-A) were examined. The failure of these reactions to produce high molecular weight polymers in the presence of anhydrous potassium carbonate is due to dehalogenation of 1,3-CBB via substitution radical-nucleophilic unimolecular (SRNl) processes. On the other hand, 1,3-FBB undergoes nucleophilic aromatic substitution reactions (SNAR) with the carbonate anion at elevated temperatures. However, it is possible to synthesize high molecular weight polymers from 1,3-FBB and bisphenol-A in NMP either by first forming the bisphenoxide with stoichiometric amounts of aqueous sodium hydroxide or in the presence of anhydrous potassium carbonate at a lower reaction temperature.

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“…18 The synthesis and characterization of a series of poly( aryl ether-bissulfone )s containing a biphenyl moiety in the repeat unit have been reported. These polymers exhibit excellent thermal stabilities and some of the highest known Tgs for poly(aryl ether)s. 19 On the other hand, poly(aryl ether-ketone)s containing a biphenyl group are usually prepared from 4,4' -biphenol and readily available aromatic haloketone such as 4,4' -difluorobenzophtnone, 7a or 7b. These polymers are semicrystalline in nature and exhibit high melting points.…”

mentioning

confidence: 99%

Synthesis and Characterization of Isomeric Biphenyl Containing Poly(aryl ether-bisketone)s II. Polymers Derived from 3,3′-(4-Fluorobenzoyl)biphenyl and Bisphenols

Mani

Weeks

Bhatnagar

et al. 1994

Polym J

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ABSTRACT:A series of amorphous and semicrystalline poly(aryl ether-bisketone)s have been synthesized from bisphenols and 3,3' -( 4-fluorobenzoyl)biphenyl via nucleophilic aromatic substitution reactions. Model compound studies were carried out with a variety of substituted phenols, 3,3' -( 4-fluorobenzoyl)biphenyl and 3,3' -( 4-chlorobenzoyl)biphenyl. The bishalide monomers were prepared by the reaction of 3,3' -bi phenyl dicarboxylic acid with thionyl chloride followed by Friedel-Crafts reaction with the appropriate aryl halide. Potassium carbonate mediated reaction of these monomers with a variety of bisphenols in dimethylacetamide or diphenylsulfone gave moderate to high molecular weight polymers in excellent yield. The high molecular weight polymers afforded tough films by compression molding. The glass transition temperatures, melting points and the thermal behaviors of the polymers were compared with the corresponding polymers derived from 4,4'-(4-fluorobenzoyl)biphenyl.KEY WORDS Nucleophilic Aromatic Substitution / Glass-Transition Temperatures / Annealing / Poly(aryl ether-ketone)s belong to a class of materials known as engineering thermoplastics.1·2 The introduction of crystallinity into a poly(aryl ether-ketone) backbone results in improving the solvent resistance and modulus. PEEK™, (1, poly(ether ether ketone)) an aromatic poly(ether-ketone) exhibits a relatively high degree of crystallinity and a melting point (Tm) of 335°C. 3 a, 4 , 5 On the other hand, PEEK suffers from poor creep behavior above its relatively low glass transition temperature (Tg) of 145°C. 6 Therefore, attempts have been made to either increase the glass transition temperature or to introduce crosslink sites into the PEEK backbone. 7 -9 The amorphous poly(aryl ether-ketone)s, characterized by backbones containing sp 3 or sp 3 d 2 hybridized atoms (e.g., 2 and 3, respectively), exhibit lower glass transition temperatures than the analogous amorphous poly(aryl ether-sulfone)s, 4 and 5. 10 · 11 In order to achieve higher Tgs and/or higher Tms, two carbonyl groups, (in contrast to PEEK which contain one such group) have been incorporated into the polymer repeat unit (e.g., 6a and 6b). 2 • 12 -15 Polymer 6a was synthesized by the reaction of bisphenol-A with either 7a or 7b via nucleophilic aromatic substitution reactions. Electrophilic aromatic substitution reactions have been used also for the synthesis of poly(aryl ether-ketone)s (e.g., Sa and Sb) containing two keto substituents. 16 • 17

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Synthesis and Characterization of Poly(Aryl Ether-Bissulfone)s

Cited by 10 publications

References 10 publications

Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Competing processes for poly(aryl ether‐ketone) synthesis, 3. Polymerization reactions of 1,3‐bis(4‐chlorobenzoyl)benzene and 1,3‐bis(4‐fluorobenzoyl)benzene in N‐methyl‐2‐pyrrolidinone

Synthesis and Characterization of Isomeric Biphenyl Containing Poly(aryl ether-bisketone)s II. Polymers Derived from 3,3′-(4-Fluorobenzoyl)biphenyl and Bisphenols

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