Copolyesters based on bibenzoic acids

Edling, Hans Eliot; Liu, Haoyu; Sun, Huarui; Mondschein, Ryan J.; Schiraldi, David A.; Long, Timothy Edward; Turner, S. Richard

doi:10.1016/j.polymer.2017.12.004

Cited by 12 publications

(34 citation statements)

References 28 publications

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“…The presence of 3,4′BB in the copolyester structure also strongly disrupts crystallinity due to the meta substitution producing a kink in the polyester backbone that does not readily fit into crystalline domains. Much like with NPG, incorporation of 3,4′BB produces an amorphous polyester when substituted into PET for more than 10 mol % DMT or when substituted for 4,4′BB in 4,4′BB‐EG by more than 45 mol % …”

Section: Resultsmentioning

confidence: 72%

“…Substitution of NPG for EG has little to no effect on T g while simultaneously disrupting crystallization much more effectively, allowing the production of high T g amorphous materials. The copolyesters containing both EG and CHDM exhibited unusually low T g ’s given the values typically observed for copolyesters containing 3,4′BB and 4,4′BB, and CHDM traditionally enhances the T g above EG. Copolyester composition 4,4′BB‐50‐NPG‐50‐CHDM produced an amorphous copolyester with the highest T g value in the series.…”

Section: Resultsmentioning

confidence: 99%

“…This is believed to be caused by an inhibited ability to rotate due to non‐symmetrical ring substitution in the 3,4′BB moiety . Recent research indicates a correlation between restricted molecular mobility in the 3,4′BB moiety and lower gas diffusivity . Similarly, we observe an increase in sub‐ T g relaxation intensity with higher CHDM content.…”

Section: Resultsmentioning

confidence: 99%

“…The meta substitution of the 3,4′BB moiety produces a “kink” in the polymer backbone that disrupts crystallization and decreases the T g relative to 4,4′BB based polyesters. This is apparent in the 3,4′BB‐EG homopolyester, which is completely amorphous and has improved tensile strength and modulus relative to amorphous 4,4′BB based copolyesters …”

Section: Introductionmentioning

confidence: 99%

“…Early patents by Monsanto claimed copolyester compositions where PET was modified with 4,4′BB comonomer, however, very little property analysis was reported on these compositions. Over the years, both 3,4′BB and 4,4′BB were investigated for their potential to enhance gas barrier, and our recently reported work modified PET with 4,4′BB, 3,4′BB, and isophthalate moieties in an effort to improve its thermal, mechanical, and barrier properties . PET copolyesters containing 15 – 40 mol % 4,4′BB were amorphous with T g ’s ranging from 89 to 98 °C.…”

Section: Introductionmentioning

confidence: 99%

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Amorphous copolyesters based on bibenzoic acids and neopentyl glycol

Edling

Mondschein

Davis

et al. 2018

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

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High Tg amorphous copolyester thermoplastics were synthesized by incorporating 4,4′‐bibenzoate (4,4′BB) and 3,4′‐bibenzoate moieties into the polyester backbone via melt polycondensation. The high levels of crystallinity typically associated with 4,4′BB containing polyesters were suppressed through copolymerization of ethylene glycol, 1,4‐cyclohexane dimethanol, and neopentyl glycol (NPG) diols. NPG was shown to be highly effective in suppressing crystallization and was used to produce amorphous compositions with Tg’s as high as 129 °C. Diol ratios were determined by 1H NMR spectroscopy and molecular weights were assessed with inherent viscosity (ηinh). Thermogravimetric analysis showed single‐step weight losses in the range of 395–419 °C. Differential scanning calorimetry was used to determine melting points and glass transition temperatures over a wide range of copolyester compositions and identified amorphous compositions. Dynamic mechanical analysis confirmed Tg’s and was used to study β‐relaxations below the Tg. Rheological analysis revealed the effect of NPG structures on shear thinning and thermal stability. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 579–587

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Section: Resultsmentioning

confidence: 72%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Amorphous copolyesters based on bibenzoic acids and neopentyl glycol

Edling

Mondschein

Davis

et al. 2018

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

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Designing novel semi‐aromatic polyesters with dimethyl 3,3′‐bibenzoate

Heifferon

Weyhrich

Mondschein

et al. 2023

Polymer International

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Melt polycondensation of dimethyl 3,3′‐bibenzoate (3,3'BB) with various linear and cycloaliphatic diols enabled the synthesis of a series of semi‐aromatic polyesters. Size exclusion chromatography analysis confirmed high molecular weight (Mn > 20 kg mol−1). Compression molding resulted in ductile films and further established molecular weights desirable for mechanical performance. 1H NMR spectroscopy confirmed polymer structure and retainment of the cis/trans ratios for the cyclohexyldimethylene‐based polyesters before and after polymerization. Thermogravimetric analysis revealed high onset of weight loss temperatures for the novel semi‐aromatic polymers (Td,5% > 380 °C). Differential scanning calorimetry and dynamic mechanical analysis were used to determine glass transition temperatures and melting temperatures. Further evaluation of these thermal transitions against previously synthesized 4,4'BB, 3,4'BB, and isophthalate‐based polymers elucidated the structure–property relationships of these systems. © 2023 Society of Industrial Chemistry.

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Synthesis and crystallization behavior of rigid copolyesters with biphenyl‐4,4′‐dicarboxylate and 2,6‐naphthalenedicarboxylate in the main chain

Edling

Vincent

Marand

et al. 2019

J Polym Sci B Polym Phys

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Structurally rigid copolyester thermoplastics were synthesized from 1,4-cyclohexanedimethanol and the diesters dimethyl biphenyl-4,4 0 -dicarboxylate and dimethyl 2,6-naphthalenedicarboxylate (DMN) via conventional melt transesterification. Conventional differential scanning calorimetry (CDSC) showed all compositions to exhibit multiple endotherms upon heating. Wideangle X-ray diffraction analysis showed copolyester compositions to exhibit the crystalline structure of either the homopolyester Poly(1,4-cyclohexylenedimethylene 2,6-naphthalate) (PCN) or the homopolyester Poly(1,4-cyclohexylenedimethylene 4,4 0bibenzoate) (PCB), but not both simultaneously. Further thermal analysis using CDSC and fast DSC investigated the origin of the multiple endotherm behavior. While three endotherms are observed for low heating rates, the upper two endotherms appear to merge at heating rates about 1-5 C s −1 and a single endotherm remains above heating rates about 10-50 C s −1 . While the behavior of the upper two endotherms is undeniably consistent with the mechanism of meltingrecrystallization-remelting (MRR), we suggest that the low endotherm is likely associated with the melting of constrained secondary crystals, although MRR effects cannot be ruled out.

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Copolyesters based on bibenzoic acids

Cited by 12 publications

References 28 publications

Amorphous copolyesters based on bibenzoic acids and neopentyl glycol

Amorphous copolyesters based on bibenzoic acids and neopentyl glycol

Designing novel semi‐aromatic polyesters with dimethyl 3,3′‐bibenzoate

Synthesis and crystallization behavior of rigid copolyesters with biphenyl‐4,4′‐dicarboxylate and 2,6‐naphthalenedicarboxylate in the main chain

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