Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics

J. Wu; P. Eduard; S. Thiyagarajan; B.A.J. Noordover; D.S. van Es; C.E. Koning

doi:10.1002/cssc.201402935

Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics

J. Wu
, P. Eduard
, S. Thiyagarajan
, B.A.J. Noordover
, D.S. van Es
, C.E. Koning

Chemical Engineering and Chemistry

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

61 Citations (Scopus)

713 Downloads (Pure)

Abstract

New carbohydrate-based polyesters were prepared from isoidide-2,5-dimethanol (extended isoidide, XII) through melt polymerization with dimethyl esters of terephthalic acid (TA) and furan-2,5-dicarboxylic acid (FDCA), yielding semi-crystalline prepolymers. Subsequent solid-state post-condensation (SSPC) gave high molecular weight (Mn=30 kg¿mol-1 for FDCA) materials, the first examples of high Mn, semi-aromatic homopolyesters containing isohexide derivatives obtained via industrially relevant procedures. NMR spectroscopy showed that the stereo-configuration of XII was preserved under the applied conditions. The polyesters are thermally stable up to 380¿°C. The TA- and FDCA-based polyesters have high Tg (105¿°C and 94¿°C, resp.) and Tm (284¿°C and 250¿°C, resp.) values. Its reactivity, stability, and ability to afford high Tg and Tm polyesters make XII a promising diol for the synthesis of engineering polymers.

Original language	English
Pages (from-to)	67-72
Number of pages	6
Journal	ChemSusChem
Volume	8
Issue number	1
DOIs	https://doi.org/10.1002/cssc.201402935
Publication status	Published - 2015

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title = "Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics",

abstract = "New carbohydrate-based polyesters were prepared from isoidide-2,5-dimethanol (extended isoidide, XII) through melt polymerization with dimethyl esters of terephthalic acid (TA) and furan-2,5-dicarboxylic acid (FDCA), yielding semi-crystalline prepolymers. Subsequent solid-state post-condensation (SSPC) gave high molecular weight (Mn=30 kg¿mol-1 for FDCA) materials, the first examples of high Mn, semi-aromatic homopolyesters containing isohexide derivatives obtained via industrially relevant procedures. NMR spectroscopy showed that the stereo-configuration of XII was preserved under the applied conditions. The polyesters are thermally stable up to 380¿°C. The TA- and FDCA-based polyesters have high Tg (105¿°C and 94¿°C, resp.) and Tm (284¿°C and 250¿°C, resp.) values. Its reactivity, stability, and ability to afford high Tg and Tm polyesters make XII a promising diol for the synthesis of engineering polymers.",

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T1 - Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics

AU - Wu, J.

AU - Eduard, P.

AU - Thiyagarajan, S.

AU - Noordover, B.A.J.

AU - van Es, D.S.

AU - Koning, C.E.

PY - 2015

Y1 - 2015

N2 - New carbohydrate-based polyesters were prepared from isoidide-2,5-dimethanol (extended isoidide, XII) through melt polymerization with dimethyl esters of terephthalic acid (TA) and furan-2,5-dicarboxylic acid (FDCA), yielding semi-crystalline prepolymers. Subsequent solid-state post-condensation (SSPC) gave high molecular weight (Mn=30 kg¿mol-1 for FDCA) materials, the first examples of high Mn, semi-aromatic homopolyesters containing isohexide derivatives obtained via industrially relevant procedures. NMR spectroscopy showed that the stereo-configuration of XII was preserved under the applied conditions. The polyesters are thermally stable up to 380¿°C. The TA- and FDCA-based polyesters have high Tg (105¿°C and 94¿°C, resp.) and Tm (284¿°C and 250¿°C, resp.) values. Its reactivity, stability, and ability to afford high Tg and Tm polyesters make XII a promising diol for the synthesis of engineering polymers.

AB - New carbohydrate-based polyesters were prepared from isoidide-2,5-dimethanol (extended isoidide, XII) through melt polymerization with dimethyl esters of terephthalic acid (TA) and furan-2,5-dicarboxylic acid (FDCA), yielding semi-crystalline prepolymers. Subsequent solid-state post-condensation (SSPC) gave high molecular weight (Mn=30 kg¿mol-1 for FDCA) materials, the first examples of high Mn, semi-aromatic homopolyesters containing isohexide derivatives obtained via industrially relevant procedures. NMR spectroscopy showed that the stereo-configuration of XII was preserved under the applied conditions. The polyesters are thermally stable up to 380¿°C. The TA- and FDCA-based polyesters have high Tg (105¿°C and 94¿°C, resp.) and Tm (284¿°C and 250¿°C, resp.) values. Its reactivity, stability, and ability to afford high Tg and Tm polyesters make XII a promising diol for the synthesis of engineering polymers.

U2 - 10.1002/cssc.201402935

DO - 10.1002/cssc.201402935

M3 - Article

C2 - 25382180

SN - 1864-5631

VL - 8

SP - 67

EP - 72

JO - ChemSusChem

JF - ChemSusChem

IS - 1

ER -

Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics

Abstract

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