Synthesis of New Poly(ether ketone)s Derived from Biobased Diols

Abderrazak, Hana Ben; Fildier, Aurélie; Romdhane, Hatem Ben; Chatti, Saber; Kricheldorf, Hans R.

doi:10.1002/macp.201300015

Cited by 17 publications

(13 citation statements)

References 43 publications

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“…Thus, it has limited the expansion of renewable thermoplastics in industry and has created an opportunity in academia 1 . The condensation polymers for thermoplastics from bio-derived cyclic compounds have a relatively low molecular weight of <50 kg mol −1 , even though they could achieve a T g as high as SEPs due to their rigid cyclic structure (Supplementary Table 1) 55–58 . The high melt viscosity of the bio-derived cyclic-compound-based polymers causes diffusion limitations, which actually hinder the chain growth 45 .…”

Section: Introductionmentioning

confidence: 99%

Sustainable and recyclable super engineering thermoplastic from biorenewable monomer

et al. 2019

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Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals. However, previously reported bio-derived thermosets or thermoplastics rarely offer thermal/mechanical properties, scalability, or recycling that match those of petrochemical SEPs. Here we use a phase transfer catalyst to synthesise an isosorbide-based polymer with a high molecular weight >100 kg mol −1 , which is reproducible at a 1-kg-scale production. It is transparent and solvent/melt-processible for recycling, with a glass transition temperature of 212 °C, a tensile strength of 78 MPa, and a thermal expansion coefficient of 23.8 ppm K −1 . Such a performance combination has not been reported before for bio-based thermoplastics, petrochemical SEPs, or thermosets. Interestingly, quantum chemical simulations show the alicyclic bicyclic ring structure of isosorbide imposes stronger geometric restraint to polymer chain than the aromatic group of bisphenol-A.

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Section: Introductionmentioning

confidence: 99%

Sustainable and recyclable super engineering thermoplastic from biorenewable monomer

et al. 2019

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“…The nucleophilic aromatic substitution polymerizations were usually carried out in aprotic polar solvents such as NMP and DPS with slight excess of catalyst such as K 2 CO 3 to bisphenols . In general, the molar ratio of K 2 CO 3 to bisphenol ([K 2 CO 3 ]/[Bisphenol]) was suitable to be about 2.2, and it was also desirable to carry out the polymerization under higher monomer concentration condition .…”

Section: Resultsmentioning

confidence: 99%

“…From the viewpoint of the suppression of the petroleum consumption to establish the sustainable development society, it is of great importance to replace the monomers from the petroleum‐based materials to the bio‐based materials, which are renewable resources. Although, bio‐based PEKs have been synthesized from 1,4:3,6‐dianhydrohexitol and 4,4′‐difluorobenzophenone, wholly aromatic PEKs have not been synthesized from bio‐based monomers so far.…”

Section: Introductionmentioning

confidence: 99%

Preparation of poly(ether ketone)s derived from 2,5‐furandicarboxylic acid via nucleophilic aromatic substitution polymerization

Kanetaka

Yamazaki

Kimura

2016

J. Polym. Sci. Part A: Polym. Chem.

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From the viewpoint of the suppression of the petroleum consumption, aromatic poly(ether ketone)s (PEKs) were prepared by the nucleophilic aromatic substitution polymerization of 2,5-bis(4-fluorobenzoyl)furan (BFBF) synthesized from biomass and aromatic bisphenols. The model reaction of BFBF and p-methoxyphenol revealed that BFBF possessed enough reactivity for the nucleophilic aromatic substitution reactions. The polymerizations of BFBF and aromatic bisphenols afforded high molecular weight polymers with good yields in N-methylpyrrolidone and diphenyl sulfone for several hours. The longer polymerization time brought about the formation of insoluble parts in any solvents and reduction of molecular weight. The obtained PEKs were thermoplastics and exhibited good thermal stability, mechanical properties, and chemical resistance comparable to common high-performance polymers. The thermal properties were tunable with the structure of bisphenols. V C

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“…ISB has properties that are more attractive than those of BPA, and in particular, it is known to offer better superior mechanical properties, as well as optical properties. In addition, there have been reports of ISB monomers being used for the synthesis of poly(arylene ether)s, a type of SEP [38,39,40,41,42]. However, the results of such efforts have shown the inability of surpassing a molecular weight (MW) of 10,000 due to the difficulty of moisture control and low reactivity of ISB.…”

Section: Introductionmentioning

confidence: 99%

Study on the Synthetic Characteristics of Biomass-Derived Isosorbide-Based Poly(arylene ether ketone)s for Sustainable Super Engineering Plastic

Park

et al. 2019

Molecules

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Demand for the development of novel polymers derived from biomass that can replace petroleum resources has been increasing. In this study, biomass-derived isosorbide was used as a monomer in the polymerization of poly(arylene ether ketone)s, and its synthetic characteristics were investigated. As a phase-transfer catalyst, crown ether has increased the weight-average molecular weight of polymers over 100 kg/mol by improving the reaction efficiency of isosorbide and minimizing the effect of moisture. By controlling the experimental parameters such as halogen monomer, polymerization solvent, time, and temperature, the optimal conditions were found to be fluorine-type monomer, dimethyl sulfoxide, 24 h, and 155 °C, respectively. Biomass contents from isosorbide-based polymers were determined by nuclear magnetic resonance and accelerator mass spectroscopy. The synthesized polymer resulted in a high molecular weight that enabled the preparation of transparent polymer films by the solution casting method despite its weak thermal degradation stability compared to aromatic polysulfone. The melt injection molding process was enabled by the addition of plasticizer. The tensile properties were comparable or superior to those of commercial petrochemical specimens of similar molecular weight. Interestingly, the prepared specimens exhibited a significantly lower coefficient of thermal expansion at high temperatures over 150 °C compared to polysulfone.

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Synthesis of New Poly(ether ketone)s Derived from Biobased Diols

Cited by 17 publications

References 43 publications

Sustainable and recyclable super engineering thermoplastic from biorenewable monomer

Sustainable and recyclable super engineering thermoplastic from biorenewable monomer

Preparation of poly(ether ketone)s derived from 2,5‐furandicarboxylic acid via nucleophilic aromatic substitution polymerization

Study on the Synthetic Characteristics of Biomass-Derived Isosorbide-Based Poly(arylene ether ketone)s for Sustainable Super Engineering Plastic

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