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Issue 14, 2020
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Synthesis of poly(bicyclohexyldimethylene terephthalate): effect of regioisomer ratios on physical properties

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Abstract

A series of novel polyesters was synthesized from dimethyl terephthalate (DMT) and various ratios of two regioisomers of bicyclohexyldimethanol (BCD), 4,4′-BCD and 3,4′-BCD. NMR spectroscopy confirmed successful incorporation of all monomers into the polymer backbone. Differential scanning calorimetry revealed that the regioisomer content dictated the polymer morphology: Materials with a 4,4′-BCD content above 80% were semi-crystalline with melting temperatures ranging from 142 to 216 °C, while polymers with lower 4,4′-BCD content were amorphous. The amorphous density of the materials increased with increasing 3,4′-BCD content, which also corresponded to an increase in Young's modulus. High thermal stabilities were observed for all materials as evidenced by a consistent Td,5% around 390 °C. Dynamic mechanical analysis revealed glass transition temperatures of 108–114 °C for all compositions and sub-Tg β-relaxations with similar intensities, suggesting that the unsaturated rings play a key role in energy absorption at low temperatures. Tensile mechanical testing revealed that the 50% composition of both diols possessed the longest elongation at break at 34%, while homopolymers of either regioisomer had considerably less elasticity with elongations at break measured at <5%.

Graphical abstract: Synthesis of poly(bicyclohexyldimethylene terephthalate): effect of regioisomer ratios on physical properties

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Supplementary files

Article information


Submitted
04 Jan 2020
Accepted
28 Feb 2020
First published
06 Mar 2020

Polym. Chem., 2020,11, 2485-2491
Article type
Paper

Synthesis of poly(bicyclohexyldimethylene terephthalate): effect of regioisomer ratios on physical properties

T. N. Thompson, A. S. Coley and M. D. Schulz, Polym. Chem., 2020, 11, 2485
DOI: 10.1039/D0PY00012D

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