- J. Haveren van (5)
- A. Heise (1)
- L. Jasinska Walc (1)
- C.E. Koning (6)
- C. Konning (1)
- M. Mak (1)
- F. Micciche (1)
- W. Ming (2)
- B.A.J. Noordover (7)
- E.A. Oostveen (1)
- R.J. Sablong (2)
- V.G. Staalduinen van (1)
- D. Tang (1)
- S. Thiyagarajan (2)
- J.G.J. Weijnen (1)
- J. Wu (2)
Semi-Aromatic Polyesters Based on a Carbohydrate-Derived Rigid Diol for Engineering Plastics
Wu, J. ; Eduard, P. ; Thiyagarajan, S. ; Noordover, B.A.J. ; Es, D.S. van; Koning, C.E. - \ 2015
ChemSusChem 8 (2015)1. - ISSN 1864-5631 - p. 67 - 72.
acetalized galactaric acid - poly(butylene terephthalate) - renewable resources - aromatic polyesters - thermal-properties - pet copolyesters - bicyclic diol - d-mannitol - isosorbide - isohexide
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 kgmol 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 3808C. The TA- and FDCA-based polyesters have high Tg (105 8C and 948C, resp.) and Tm (284 8C and 250 8C, 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.
Fully Isohexide-Based Polyesters: Synthesis, Characterization, and Structure-Properties Relations
Wu, J. ; Jasinska Walc, L. ; Eduard, P. ; Noordover, B.A.J. ; Es, D.S. van; Koning, C.E. - \ 2013
Macromolecules 46 (2013)2. - ISSN 0024-9297 - p. 384 - 394.
chiral building-blocks - renewable resources - poly(butylene terephthalate) - coating applications - melting behavior - succinic acid - polymers - isosorbide - crystallization - crystallinity
Here we present a novel series of biobased polyesters solely based on renewable isohexide building blocks, synthesized via melt polymerization. The recently developed isoidide dicarboxylic acid (IIDCA) was polymerized with rigid renewable diols such as isosorbide (IS), isomannide (IM), isoidide (II), and the novel 2,5-methylene-extended isoidide dimethanol (IIDML). Both IIDCA and IIDML were developed to increase the reactivity of the isohexide building block, while retaining rigidity and hence the beneficial effects on Tg. Compared to the parent isohexides, IIDML showed a markedly higher reactivity, resulting in three to four times higher weight-average molecular weight (Mw) values of the synthesized polyesters. The molecular structure of the novel polyesters was analyzed by 1H, 13C and 2D-COSY NMR techniques, confirming that the stereoconfigurations of the isohexide moieties were preserved under the applied polymerization conditions. The II/IS-based polyesters have high Tg values noted of 70 and 85 °C, respectively, while the IIDML-based polyester has a lower Tg of approximately 45 °C, yet with an higher degree of crystallinity than the parent isohexide-based polyesters. A systematic study on structure-thermal properties relations comparing these novel polyesters with, e.g., aliphatic polyesters reveals that, when incorporated into polyesters, both IIDCA and IIDML are able to increase the Tg by approximately 70 °C, which is comparable to the parent isohexides. Given the enhanced reactivity, high thermal stability and the retained ability to increase the Tg, IIDML is a promising renewable building block for performance polymers.
|Biodegradable thermoplastic polyurethanes from renewable resources : BITPURER (DPI 653)
Tang, D. ; Noordover, B.A.J. ; Sablong, R.J. ; Koning, C.E. ; Thiyagarajan, S. ; Es, D.S. van; Haveren, J. van - \ 2010
Process for the production of a dianhydrohexitol based polyester
Noordover, B.A.J. ; Sablong, R.J. ; Duchateau, R. ; Benthem, R.A.T.M. van; Ming, W. ; Konning, C. ; Haveren, J. van - \ 2008
Octrooinummer: WO2008031592, verleend: 2008-03-20.
Process for the production of a polyester by the polycondensation of a mixture comprising isoidide, and a dicarboxylic acid or dicarboxylic acid anhydride, wherein the reaction is performed in the melt of the monomers and wherein these monomers are not activated. The polyesters based on one or more of the three isomers of dianhydrohexitol, being isosorbide, isomannide and isoidide, have properties which makes them suitable to be used in powder coatings, toner compositions as well as engineering plastics. The polyesters include a polyester according to the following formula, wherein n ranges from 3 to 300.
Resins and additives for powder coatings and alkyd paints, based on renewable resources
Haveren, J. van; Oostveen, E.A. ; Micciche, F. ; Noordover, B.A.J. ; Koning, C.E. ; Benthem, R.A.T.M. van; Frissen, A.E. ; Weijnen, J.G.J. - \ 2007
Journal of Coatings Technology and Research 4 (2007)2. - ISSN 1547-0091 - p. 177 - 186.
combination - acid - linoleate - oxidation
Due to limited fossil resources and an increased need for environmentally friendly, sustainable technologies, the importance of using renewable feedstocks in the paint and coatings area will increase in the decades to come. This paper highlights some of the perspectives in this area. Alkyd resins for high-solid paints and reactive diluents, completely based on commercially available renewable resources, were prepared and characterized. Alkyd resins based on sucrose and unsaturated fatty acids or oils showed a low intrinsic viscosity, making them suitable to be used in high-solid alkyd paints. Reactive diluents based on similar starting materials showed excellent properties with regard to thinning behavior and effect on drying characteristics. Powder coating polyester resins were synthesized, starting from isosorbide and diacids. Polyester resins with glass transition temperatures up to 70°C were obtained. Incorporation of small amounts of other diols and trifunctional components was found to improve color and coating properties. In order to create completely renewable resin systems, the development of renewable drying agents for alkyds and crosslinkers for powder coatings is in progress.
Biobased functional polyesters for coatings applications : synthesis, characterization and application
Noordover, B.A.J. ; Duchateau, R. ; Koning, C.E. ; Benthem, R.A.T.M. van; Ming, W. ; Haveren, J. van; Es, D.S. van - \ 2007
Abstracts of papers of the American Chemical Society 233 (2007). - ISSN 0065-7727 - p. CELL - 172.
Co- and Terpolyesters based on isosorbide and succinic acid for coating applications : synthesis and characterization
Noordover, B.A.J. ; Staalduinen, V.G. van; Duchateau, R. ; Koning, C.E. ; Benthem, R.A.T.M. van; Mak, M. ; Heise, A. ; Frissen, A.E. ; Haveren, J. van - \ 2006
Biomacromolecules 7 (2006)12. - ISSN 1525-7797 - p. 3406 - 3416.
end-groups - polyesters - esterification - poly(ethylene-terephthalate) - 1,4/3,6-dianhydro-d-glucitol - 1,4-3,6-dianhydrosorbitol - blends - uv
Co- and terpolyesters based on succinic acid and isosorbide in combination with other renewable monomers such as 2,3-butanediol, 1,3-propanediol, and citric acid were synthesized and characterized. Linear polyesters were obtained via melt polycondensation of nonactivated dicarboxylic acids with OH functional monomers. Polymer end functionality (i.e., hydroxyl or carboxylic acid) was controlled by adjusting the monomer stoichiometry. The glass transition temperatures of the resulting polyesters could be effectively adjusted by varying the polymer composition and molar mass. By adding polyfunctional monomers such as trimethylolpropane or citric acid, polyesters with enhanced functionality were obtained. These biobased polyesters displayed functionalities and Tg values in the appropriate range for (powder) coating applications. The polyesters were cross-linked using conventional curing agents. Coatings from branched polyesters-hydroxyl as well as acid functional-showed significantly improved mechanical and chemical resistance compared to those formulated from linear polymers. These renewable polyesters proved to be suitable materials for coating applications with respect to solvent resistance, impact resistance, and hardness.