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

Katherine V. Heifferon; Cody W. Weyhrich; Ryan J. Mondschein; Timothy E. Long

doi:10.1002/pi.6535

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

Katherine V. Heifferon, Cody W. Weyhrich, Ryan J. Mondschein, Timothy E. Long

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-review

Abstract

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 (M_n > 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 (T_d,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.

Original language	English (US)
Pages (from-to)	687-692
Number of pages	6
Journal	Polymer International
Volume	72
Issue number	8
DOIs	https://doi.org/10.1002/pi.6535
State	Published - Aug 2023

Keywords

bibenzoate
melt polymerization
polyester
regioisomers

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1002/pi.6535

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title = "Designing novel semi-aromatic polyesters with dimethyl 3,3′-bibenzoate",

abstract = "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.",

keywords = "bibenzoate, melt polymerization, polyester, regioisomers",

author = "Heifferon, {Katherine V.} and Weyhrich, {Cody W.} and Mondschein, {Ryan J.} and Long, {Timothy E.}",

note = "Funding Information: The authors thank Emily Wilts and Clay Arrington for insightful discussions. This work was sponsored by ExxonMobil Chemical Company. Publisher Copyright: {\textcopyright} 2023 Society of Industrial Chemistry.",

year = "2023",

month = aug,

doi = "10.1002/pi.6535",

language = "English (US)",

volume = "72",

pages = "687--692",

journal = "Polymer International",

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AU - Heifferon, Katherine V.

AU - Weyhrich, Cody W.

AU - Mondschein, Ryan J.

AU - Long, Timothy E.

N1 - Funding Information: The authors thank Emily Wilts and Clay Arrington for insightful discussions. This work was sponsored by ExxonMobil Chemical Company. Publisher Copyright: © 2023 Society of Industrial Chemistry.

PY - 2023/8

Y1 - 2023/8

N2 - 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.

AB - 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.

KW - bibenzoate

KW - melt polymerization

KW - polyester

KW - regioisomers

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

Abstract

Keywords

ASJC Scopus subject areas

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