Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units

Boyles, David A.; Filipova, Tsvetanka; Bendler, John T.; Longbrake, Guy; Reams, Josiah T

doi:10.1021/ma048616m

Cited by 19 publications

(19 citation statements)

References 35 publications

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“…The literatures reported that high‐molecular‐weight polycarbonates can be obtained using convenient triphosgene on a laboratory scale, but usually limited in diphenolic monomers owing to the lower nucleophilicity of alcoholic moieties . In addition, the copolymerization of diphenolic monomers and dialcoholic monomers could not realize by neither interfacial polycondensation with triphosgene nor direct polycondensation with carbonyl sources such as diphenyl carbonate .…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis and electro‐optic activities of new polycarbonates containing tricyanofuran‐based nonlinear optical chromophores

Deng

Zhou

et al. 2013

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

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Electro‐optic (EO) polycarbonates are prepared through copolymerization of diol nonlinear optical chromophores and bisphenol A with bisphenol A bis(chloroformate) in solution. The obtained polycarbonates exhibit good film‐forming properties and good thermal stability. The poled films of the resultant electro‐optic polycarbonates reveal the maximum EO coefficient of 75 pm/V. The obtained poled films also possess better temporal stability. These good performances endow the resultant EO polycarbonates with device application in photonics.

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Section: Introductionmentioning

confidence: 99%

Facile synthesis and electro‐optic activities of new polycarbonates containing tricyanofuran‐based nonlinear optical chromophores

Deng

Zhou

et al. 2013

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

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“…In this article, DR is used to study molecular motions in BPA‐PC and then to compare these motions with those found in two new high‐temperature polycarbonates with small cross‐sectional areas, MCSAs, small packing lengths, p , and low entanglement weights, M e 50‐54. Because the unique mechanical properties of BPA‐PC are believed to be due to both high entanglement density (i.e., small packing length p or MCSA) and to facile, cooperative molecular motions in the glassy state, DR is used in the following study to determine whether the glassy‐state motions in the new polycarbonates are comparable to those in BPA‐PC itself and, therefore, likely to endow the new polymers with high‐impact properties as well.…”

Section: Introductionmentioning

confidence: 99%

Dielectric studies of tetraaryl and triaryl polycarbonates and comparisons with bisphenol A‐polycarbonate

Fontanella

Boyles

Filipova

et al. 2011

J Polym Sci B Polym Phys

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The relative permittivity, loss, and breakdown strength are reported for a commercial sample of bisphenol Apolycarbonate (comm-BPA-PC) and a purified sample of the same polymer (rp-BPA-PC) as well as for two new polycarbonates having low molecular cross-sectional areas, namely a copolymer of tetraaryl polycarbonate and BPA-PC (TABPA-BPA-PC) and a triaryl polycarbonate homopolymer (TriBPA-PC). The glass transition temperatures of the new polymers are higher than the T g of BPA-PC (187 and 191 C vs. 148 C). Relative permittivity and loss measurements were carried out from 10 to 10 5 Hz over a wide temperature range, and results for the aand c-relaxation regions are discussed in detail. For the a-relaxation, the isochronal peak position, T a , scales approximately with T g . On the other hand, the peak temperature for the crelaxation is approximately constant, independent of T g . Also, in contrast to what is observed for a, c exhibits a strong increase in peak height as temperature/frequency increases and a significant difference is found between Arrhenius plots determined from isochronal and isothermal data analyses. Next, the c-relaxation region for comm-BPA-PC and associated activation parameters show strong history/purity effects. The activation parameters also depend on the method of data analysis. The results shed light on discrepancies that exist in the lit-erature for BPA-PC.

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“…5,6 The dicyanate monomers were brought to chromatographic purity by flash chromatography through silica gel. The structures of the dicyanates were confirmed with NMR and IR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…The Suzuki asymmetric aryl coupling reaction was used to synthesize precursor bisphenols to afford biphenyl units as previously reported. 5,6 Because of the commercial availability of para-, meta-, and orthosubstituted boronic acids for the Suzuki reaction, pure target bisphenol precursors free of contaminating isomers were readily obtainable. These bisphenols were subsequently converted into their corresponding cyanate esters by the usual method using nucleophilic substitution by the respective phenoxide ion on cyanogen bromide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of biphenylated cyanate esters: Thermomechanical resin comparisons within two isomeric series

Reams

Boyles

2011

J of Applied Polymer Sci

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Three isomeric tetraaryl cyanate esters containing biphenyl moieties {bis-[4-(4 0 -cyanatophenyl)phenyl]propane, 2,2-bis-[4-(3 0 -cyanatophenyl)phenyl]propane, and 2,2-bis-[4-(2 0 -cyanatophenyl)phenyl]propane} and three isomeric triaryl cyanate esters {2-(4propane} were synthesized from their corresponding bisphenols. The structures of the monomers were confirmed with IR and 1 H-NMR spectroscopy. The curing behavior was investigated with differential scanning calorimetry. Cyanate esters were cured thermally in the absence of a catalyst and were characterized by dynamic mechanical analysis. The results were compared to the properties of commercial bisphenol A polycyanurate. Of the three tetraaryl isomers, 2,2-bis-[4-(2 0 -cyanatophenyl)phenyl]propane had the highest melting point, and its corresponding resin had the lowest glass-transition temperature (T g ). The para isomer displayed the highest T g value of the three novel tetraaryl resins. The triaryl dicyanate isomers were low-melting solids, with the ortho and meta isomers existing as liquids at room temperature. The T g value of the paratriaryl isomer was the highest of the three triaryl isomers and was about the same as that of bisphenol A polycyanurate.

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Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units

Cited by 19 publications

References 35 publications

Facile synthesis and electro‐optic activities of new polycarbonates containing tricyanofuran‐based nonlinear optical chromophores

Facile synthesis and electro‐optic activities of new polycarbonates containing tricyanofuran‐based nonlinear optical chromophores

Dielectric studies of tetraaryl and triaryl polycarbonates and comparisons with bisphenol A‐polycarbonate

Synthesis of biphenylated cyanate esters: Thermomechanical resin comparisons within two isomeric series

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