Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin
2-Pyrone-4,6-dicarboxylic acid (PDC), a chemically stable metabolic intermediate of lignin, was for the first time utilized to prepare polyesters. Condensation polymerization at about 200 °C with 1,2-ethanediol, 1,3-propanediol or bis(2-hydroxyethyl) terephthalate was effectively promoted by the cat...
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Published in | Polymer journal Vol. 40; no. 1; pp. 68 - 75 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
London
Nature Publishing Group UK
01.01.2008
Society of Polymer Science Nature Publishing Group |
Subjects | |
Online Access | Get full text |
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Summary: | 2-Pyrone-4,6-dicarboxylic acid (PDC), a chemically stable metabolic intermediate of lignin, was for the first time utilized to prepare polyesters. Condensation polymerization at about 200 °C with 1,2-ethanediol, 1,3-propanediol or bis(2-hydroxyethyl) terephthalate was effectively promoted by the catalytic amount of Sb
2
O
3
. The corresponding polyesters, P(PDC2), P(PDC3) or P(PDCB)
x
(x: PDC unit content, and
x
≤0.5), became insoluble when the number-average molecular weight exceeded about 4×10
3
. Due to the pseudo-aromatic nature of PDC ring, these polyesters were thermally stable up to 210 °C. From the measurements of strain-stress characteristics, Yong’s modulus of P(PDC2) or P(PDC3) was as high as 250 MPa and 2 times larger than that of amorphous PET. The accelerated hydrolysis of P(PDC2) or P(PDC3) in basic, acidic, and pure water at 60 °C gave 60–100% degradation in 1.5–3 weeks. The degradability could be controlled by changing the PDC content “x” in the case of P(PDCB)
x
, because the lactone ring cleavage as well as ester hydrolysis were considered to be the major events in the main-chain scission. |
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ISSN: | 0032-3896 1349-0540 |
DOI: | 10.1295/polymj.PJ2007158 |