Solid‐state polymerization and characterization of a copolyamide based on adipic acid, 1,4‐butanediamine, and 2,5‐furandicarboxylic acid

Endah, Yohana Kurnia; Han, Sang Hoon; Kim, Jae-Hoon; Kim, Nak Kyoon; Kim, Woo Nyon; Lee, Minsoo; Lee, Hyunjoo

doi:10.1002/app.43391

Cited by 34 publications

(18 citation statements)

References 34 publications

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“…The work, therefore, focused mainly on the development of the synthesis method itself. Thus, one can find publications describing, among others, solution polymerization of the diamines with various FDCA derivatives [22][23][24][25][26], direct polycondensation method [25,27,28], interfacial polymerization [25,26,29,30] as well as solid-state polymerization [31,32]. The byproducts produced during the syntheses make that a method that would allow obtaining a large amount of pure material with high molecular weight is still sought after.…”

Section: Graphical Abstract Introductionmentioning

confidence: 99%

Structure, thermal and mechanical properties of copoly(ester amide)s based on 2,5‐furandicarboxylic acid

et al. 2021

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In this work, new bio-based copoly(ester amide)s were synthesized by a two-step melt polycondensation process, using 2,5-furanedicarboxylic acid dimethyl ester (DMFDC), 1,3-propanediol (PDO), and 1,3-diaminopropane (DAP), with different DAP content. The chemical structure of the obtained poly(trimethylene 2,5-furandicarboxylate)-co-poly(propylene furanamide) (PTF-co-PPAF) copolymers was confirmed by nuclear magnetic resonance (1H NMR) and Fourier-transform infrared (FTIR) spectroscopy. Gas chromatography/mass spectrometry was used to provide more details of the polycondensation process. Thermal properties of the obtained materials were characterized by means of differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and dynamic–mechanical thermal analysis (DMTA). The copolymers were amorphous and their glass transition temperature increased with the increase in the poly(propylene furanamide) (PPAF) content. The synthesized PTF-co-PPAF copolymers exhibited improved thermal and thermo-oxidative stability up to 300 °C. In addition, from the performed mechanical tests, it was found that along with the increase in PPAF content, Young's modulus increased, while at the same time, the value of elongation at break decreased. Graphical Abstract

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Section: Graphical Abstract Introductionmentioning

confidence: 99%

Structure, thermal and mechanical properties of copoly(ester amide)s based on 2,5‐furandicarboxylic acid

et al. 2021

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“…8−14 thermore, crystallization from the molten state is only observed in exceptional cases. 15,16 Hence, the thermal and mechanical performance of those materials derived from renewable feedstock is generally inferior to that incorporating nonrenewable aromatic monomers. Wilsens et al investigated this phenomenon with the help of a diamide−diester that was obtained from methyl 4-aminobenzoate and 2,5-furandicarboxylic acid chloride.…”

Section: ■ Introductionmentioning

confidence: 99%

A Facile Method to Synthesize Semicrystalline Poly(ester amide)s from 2,5-Furandicarboxylic Acid, 1,10-Decanediol, and Crystallizable Amido Diols

Kluge

Papadopoulos

Magaziotis

et al. 2020

ACS Sustainable Chem. Eng.

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The synthesis of polyamides and poly(ester amide)s derived from 2,5-furandicarboxylic acid frequently leads to amorphous polymeric materials. Formation of intramolecular hydrogen bonds between the oxygen heteroatom in the furan ring and hydrogens of the amide bonds reduces the intermolecular hydrogen bonds that are usually responsible for the high thermal and mechanical performance of these materials. To circumvent this problem, aliphatic–aromatic poly(ester amide)s were synthesized in this study from dimethyl 2,5-furandicarboxylate, 1,10-decanediol, and a preformed aliphatic diol containing two internal amide bonds (amido diol). Wide-angle X-ray diffraction and differential scanning calorimetry experiments revealed that polymers obtained were semicrystalline over the whole composition range and crystallized rapidly from the molten state, indicating that intramolecular H-bonding is effectively suppressed. Depending on the ratio of 1,10-decanediol and amido diol, the thermal properties could be adjusted over a wide temperature range. The polymers exhibit T g and T m in a range of −4 to 27 °C and 102 to 175 °C, respectively. Elastic modulus and hardness increased almost linearly with the amount of ester–amide moieties. The method presented herein allows for the successful synthesis of semicrystalline poly(ester amide)s from 2,5-furandicarboxylic acid without undesired intramolecular hydrogen bonds. This finding could set the stage for further bio-based poly(ester amide)s from 2,5-furandicarboxylic acid suitable for high-performance applications.

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“…It is due to the side reactions, including decarboxylation occurring around 200 °C and the N-methylation of FDCA, that occur [ 12 ], whereby the synthesized PEAs have a low molecular weight and are amorphous or have a low degree of crystallinity [ 13 ]. Therefore, in the last few years, several attempts to synthesize polyamides and PEAs based on FDCA and its derivatives have been described (e.g., solution polymerization [ 14 ], enzymatic polymerization [ 12 , 15 , 16 ], direct polycondensation [ 17 ], and solid-state polymerization [ 13 , 18 ]). One of the strategies involves enzymatic polymerization, which uses an immobilized form of Candida Antarctica lipase b, which serves as a catalyst for polycondensation between dimethyl furan 2,5-dicarboxylate DMFDC and aliphatic diamines [ 15 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

The Properties of Poly(ester amide)s Based on Dimethyl 2,5-Furanedicarboxylate as a Function of Methylene Sequence Length in Polymer Backbone

et al. 2022

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A series of poly(ester amide)s based on dimethyl furan 2,5-dicarboxylate (DMFDC), 1,3-propanediol (PDO), 1,6-hexylene glycol (HDO), and 1,3-diaminopropane (DAP) were synthesized via two-step melt polycondensation. The phase transition temperatures and structure of the polymers were studied by differential scanning calorimetry (DSC). The positron annihilation lifetime spectroscopy (PALS) measurement was carried out to investigate the free volume. In addition, the mechanical properties of two series of poly(ester amide)s were analyzed. The increase in the number of methylene groups in the polymer backbone resulted in a decrease in the values of the transition temperatures. Depending on the number of methylene groups and the content of the poly(propylene furanamide) (PPAF), both semi-crystalline and amorphous copolymers were obtained. The free volume value increased with a greater number of methylene groups in the polymer backbone. Moreover, with a lower number of methylene groups, the value of the Young modulus and stress at break increased.

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Solid‐state polymerization and characterization of a copolyamide based on adipic acid, 1,4‐butanediamine, and 2,5‐furandicarboxylic acid

Cited by 34 publications

References 34 publications

Structure, thermal and mechanical properties of copoly(ester amide)s based on 2,5‐furandicarboxylic acid

Structure, thermal and mechanical properties of copoly(ester amide)s based on 2,5‐furandicarboxylic acid

A Facile Method to Synthesize Semicrystalline Poly(ester amide)s from 2,5-Furandicarboxylic Acid, 1,10-Decanediol, and Crystallizable Amido Diols

The Properties of Poly(ester amide)s Based on Dimethyl 2,5-Furanedicarboxylate as a Function of Methylene Sequence Length in Polymer Backbone

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