Poly(ester amide)s from poly(alkylene succinate)s and rapid crystallizing amido diols: Synthesis, thermal properties and crystallization behavior

Kluge, Marcel; Rennhofer, Harald; Lichtenegger, Helga C.; Liebner, Falk; Robert, Tobias

doi:10.1016/j.eurpolymj.2020.109622

Cited by 13 publications

(21 citation statements)

References 46 publications

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“…There are no indications that the ester segments are able to organize into crystalline domains, as the reflections of PPF are absent from the rest of the materials. These results are constant with the findings of other studies on PEAs based on poly(decylene furanoate) 29 , poly(ethylene succinate) 34 and poly(propylene succinate) 45 .…”

Section: Thermal Transitions and Crystallinity Assessmentsupporting

confidence: 91%

“…The chemicals were used without further purification. N,N′-(butane 1,4diyl)bis(6-hydroxyhexanamide) (amido diol, AD) was synthesized as previously reported 29,34 .…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of the amido diol was previously described. 34,36 In brief, it involves the ring-opening of ε-caprolactone by 1,4-diaminobutane. In the supporting info, details about the synthesis of this monomer can be found.…”

Section: Polymer Synthesismentioning

confidence: 99%

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Unlocking the potential of furan-based poly(ester amide)s: an investigation of crystallization, molecular dynamics and degradation kinetics of novel poly(ester amide)s based on renewable poly(propylene furanoate)

et al. 2021

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Section: Thermal Transitions and Crystallinity Assessmentsupporting

confidence: 91%

“…The chemicals were used without further purification. N,N′-(butane 1,4diyl)bis(6-hydroxyhexanamide) (amido diol, AD) was synthesized as previously reported 29,34 .…”

Section: Methodsmentioning

confidence: 99%

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Unlocking the potential of furan-based poly(ester amide)s: an investigation of crystallization, molecular dynamics and degradation kinetics of novel poly(ester amide)s based on renewable poly(propylene furanoate)

et al. 2021

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“…N,N'-(butane-1,4-diyl)bis(6-hydroxyhexanamide) (amido diol, AD) was synthesized as described before. 1,2 In brief, a certain amount of 1,4-diaminobutane was placed in a three-necked flask equipped with mechanical stirrer and cooler and dissolved in 2-propanol (200 mL mol-1). ε-Caprolactone (2 equivalents) in 2-propanol (50 mL mol-1) was slowly added to the diamine solution at room temperature using a pump (0.6 mL min-1), stirring was continued overnight.…”

Section: Synthesismentioning

confidence: 99%

“…Further information on the characterization of the monomer ( 1 H and 13 C NMR spectra, elemental analysis, FTIR, DSC and TGA) can be found in our previous publications. 1,2…”

Section: Synthesismentioning

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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Poly(ester amide) from 6‐amino‐1‐hexanol and terephthalic acid: preparation and properties

Xiao,

Cheng,

Liu

et al. 2024

Polymers for Advanced Techs

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Poly(ester amide)s (PEAs) have received extensive attention due to their unique chemical structure and excellent properties. In this paper, a novel PEA (P6T6T) was prepared through melt polycondensation of terephthalic acid (PTA) and 6T6‐diamide‐diol (6T6), which was from the amidation of 6‐amino‐1‐hexanol and PTA. The structures were characterized by nuclear magnetic resonance, fourier transform infrared, and wide‐angle X‐Ray diffraction, and the thermal properties were evaluated by differential scanning calorimetry and thermal gravimetric analysis for P6T6T. It was found that the melting point of P6T6T was 217°C, which was about 37°C lower than that of PET (254°C), while the initial decomposition temperature was maintained at about 381°C. P6T6T had a fast crystallization rate (the half time of crystallization (t1/2) range from 35 to 60 s) and great crystallization properties. The saturated water absorption of the P6T6T was measured to be 2.53 wt%, which was three times that of PET (0.83 wt%). Furthermore, the water contact angle of P6T6T was determined to be 57.3°C, much lower than that of PET (94.7°C). All these results suggest that the incorporation of amide was an efficient method to improve the water absorption of polyester fibers.

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Poly(ester amide)s from poly(alkylene succinate)s and rapid crystallizing amido diols: Synthesis, thermal properties and crystallization behavior

Cited by 13 publications

References 46 publications

Unlocking the potential of furan-based poly(ester amide)s: an investigation of crystallization, molecular dynamics and degradation kinetics of novel poly(ester amide)s based on renewable poly(propylene furanoate)

Unlocking the potential of furan-based poly(ester amide)s: an investigation of crystallization, molecular dynamics and degradation kinetics of novel poly(ester amide)s based on renewable poly(propylene furanoate)

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

Poly(ester amide) from 6‐amino‐1‐hexanol and terephthalic acid: preparation and properties

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