Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin

Michinobu, Tsuyoshi; Hishida, Masakiyo; Sato, Masae; Katayama, Yoshihiro; Masai, Eiji; Nakamura, Masaya; Otsuka, Yuichiro; Ohara, Seiji; Shigehara, Kiyotaka

doi:10.1295/polymj.pj2007158

Cited by 55 publications

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“…In the past few years, a series of PDC polyesters was synthesized by the direct dehydrated polycondensation with various diol co-monomers, and their excellent biodegradable, mechanical and adhesive properties were demonstrated. [10][11][12][13][14][15][16] However, the major problem of the PDC polyesters was their relatively low molecular weights. In order to improve the polymer properties, other efficient base-free polymerization methods were desired.…”

Section: Introductionmentioning

confidence: 99%

Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

Michinobu

Hiraki

Inazawa

et al. 2011

Polym J

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Novel biomass-based polymers composed of 2-pyrone-4,6-dicarboxylic acid (PDC), which was isolated from lignin as a chemically stable metabolic intermediate, were synthesized by the copper (Cu) (I)-catalyzed, but ligand-free azide-alkyne cycloaddition reaction. The polymerization progress was monitored by the gel permeation chromatography profiles and IR spectroscopies. Very high-molecular-weight polymers with sufficient solubilities in organic solvents were obtained after the polymerization for 70 h, and their chemical structures were fully characterized. The in-situ prepared PDC polymers displayed adhesive properties to various metal surfaces. Among the investigated metals, the tensile strength with Cu, prepared at 70 1C for 4 h, was the highest (3.70 MPa). This specific adhesion to Cu is probably due to the promoted polymerization using the leached Cu I as a catalyst and the crosslinking ability through the interactions with the formed triazole rings. Polymer Journal (2011) 43, 648-653; doi:10.1038/pj.2011.40; published online 11 May 2011Keywords: adhesive; biomass; click chemistry; polyaddition INTRODUCTION Biomass-based renewable materials have attracted considerable attention as a source of green plastics. [1][2][3][4][5] Lignin is a waste biomass that has three-dimensional network structures containing aromatic rings, and its conversion into versatile soluble monomers has been requested. In a previous study, we succeeded in the metabolic conversion of lignin into 2-pyrone-4,6-dicarboxylic acid (PDC) on a large scale via protocatechuate by a transformed bacterium. 6 PDC consists of a polar pseudo-aromatic ring and two carboxylic acids, suggesting the potential use as a bifunctional monomer for polycondensation and polyaddition. As PDC was not accessible from petrochemicals, its chemical reactivity and physical properties were comprehensively investigated. 7-9 During the course of the synthetic studies of PDC polymers, it was found that PDC is unstable under basic conditions. Thus, all the PDC polymers reported so far were synthesized by base-free reactions. In the past few years, a series of PDC polyesters was synthesized by the direct dehydrated polycondensation with various diol co-monomers, and their excellent biodegradable, mechanical and adhesive properties were demonstrated. 10-16 However, the major problem of the PDC polyesters was their relatively low molecular weights. In order to improve the polymer properties, other efficient base-free polymerization methods were desired.

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Section: Introductionmentioning

confidence: 99%

Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

Michinobu

Hiraki

Inazawa

et al. 2011

Polym J

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“…1, left). By using its bifunctional character as a polycondensation monomer, our group has synthesized the biomass-based copolyester from the mixture of PDC and BHT [bis (2-hydroxyethyl) terephthalate] [16,17]. During the course, the strong adhesive property of PDC polyester to polar surfaces such as metal and glass surfaces by heating at 250 was found [17].…”

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confidence: 99%

Tenacious Epoxy Adhesives Prepared from Lignin-derived Stable Metabolic Intermediate

et al. 2009

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“…temperature) �250°C [22]. Such too narrow temperature margin for thermoplastic processing, i.e., only 10~20°C gap between the softening temperature (Tsf) and Td5, discouraged the versatility of these bio-based polymers.…”

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“…Such too narrow temperature margin for thermoplastic processing, i.e., only 10~20°C gap between the softening temperature (Tsf) and Td5, discouraged the versatility of these bio-based polymers. (Co)Polyesters with [bis(hydroxylethyl) terephthalate or] ethylene glycol gave mechanically tough materials, however, the temperature gap was +20~-20°C (minus means Td5< Tsf) depending on the composition [22]. Incorporation of long alkylene chains instead of ethylene units or lactate units as comonomer not only reduced Tsf but also caused very low Tg (glass transition temperature) or sometimes spherulite-like brittleness of the resulting polymers [27].…”

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<b>Thermoplastic Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin</b>

et al. 2013

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Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin

Cited by 55 publications

References 20 publications

Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

Tenacious Epoxy Adhesives Prepared from Lignin-derived Stable Metabolic Intermediate

<b>Thermoplastic Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin</b>

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