Biobased copolyesters: synthesis, crystallization behavior, thermal and mechanical properties of poly(ethylene glycol sebacate-co-ethylene glycol 2,5-furan dicarboxylate)

A serials of fully bio-based poly(ethylene dodecanedioate-2,5-furandicarboxylate) (PEDF) were synthesized from Dodecanedioic acid (DDCA), 2,5-Furandicarboxylic acid (2,5-FDCA), and ethylene glycol through a two-step procedure consisted of transesterification and polycondensation. After their chemical structures were confirmed by Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy, their thermal, mechanical, and biodegradation properties were investigated in detail. Results showed that the chemical composition of PEDFs could be easily controlled by the feeding mole ratio of DDCA to FDCA and they possessed the characteristic of random copolyester with the intrinsic viscosity ranged from 0.82 to 1.2 dL/g. With the varied mole ratio of DDCA to FDCA, PEDFs could be changed from semicrystalline thermoplastic to the completely amorphous elastomer, indicated by the elongation at break ranged from 4 for poly(ethylene 2,5-furandicarboxylate) to 1500% for amorphous PEDF-40. The amorphous PEDF-30 and PEDF-40 showed satisfactory shape recovery after cyclic tensile test, which was the typical behavior for elastomer. Enzymatic degradation test indicated that all the PEDFs were biodegradable and the degradation rate was heavily affected by their chemical compositions.

Section: Resultssupporting

confidence: 79%

Fully bio‐based polyesters derived from 2,5‐furandicarboxylic acid (2,5‐FDCA) and dodecanedioic acid (DDCA): From semicrystalline thermoplastic to amorphous elastomer

Jia

Wang

Sun

et al. 2017

“…This phenomenon confirmed the calculated results of crystallinity from first heating scan of DSC and explained the depressing effect of furan ring on PBT crystallization, and the similar phenomenon could be found in other literatures about furan-based copolyesters. [32,33] In Figure 5b, after isothermal crystallization of the specimens at 140 C for 60 min, PBTF-30, PBTF-45, PBTF-90, and PBF also displayed strong diffraction peaks, which indicated their good crystalline state, but PBTF-60 and PBTF-75 still kept amorphous state, that was also in agreement with DSC test results.…”

Section: First Heatingsupporting

confidence: 83%

High molecular weight poly(butylene terephthalate‐co‐butylene 2,5‐furan dicarboxylate) copolyesters: From synthesis to thermomechanical and barrier properties

Zhang

Shen

et al. 2020

Poly(butylene terephthalate‐co‐butylene 2,5‐furandicarboxylate) copolyesters (PBTFs) were synthesized from 1,4‐butanediol, dimethyl terephthalate (DMT), and 2,5‐furandicarboxylic acid (FDCA) by a two‐step polymerization method. Their chemical structures were confirmed by Fourier‐transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and carbon nuclear magnetic resonance before thermal properties were explored with differential scanning calorimeter and thermogravimetric analyzer. Results showed that PBTFs changed from semi‐crystalline to completely amorphous when the content of FDCA unit was increased to 45 mol% at first, and then became crystallographic again with the further increment of FDCA unit to 75 mol%. For their mechanical properties, the tensile modulus and strength showed the similar trend, decreasing firstly and then increasing later. Their barrier to carbon dioxide and oxygen became better with the increasing of furan content due to the rigidity and higher polarity of furan ring. The performance of PBTFs copolyesters was investigated clearly, and the relative content of FDCA and DMT can be adjusted to satisfy different performance requirements.

“…2,5‐Furandicarboxylic acid (FDCA) and 2,5‐thiophenedicarboxylic acid (TDCA) are two important bio‐based monomers with similar structures (Figure ). Many FDCA‐based polyesters have been synthesized successfully from FDCA . Compared with poly(ethylene terephthalate) (PET), poly(ethylene furanoate) (PEF) and poly(propylene 2,5‐furandicarboxylate) exhibit higher tensile strength and barrier properties, which are considered as the ideal substitutes for PET.…”

Section: Introductionmentioning

confidence: 99%

High T_g and tough poly(butylene 2,5‐thiophenedicarboxylate‐co‐1,4‐cyclohexanedimethylene 2,5‐thiophenedicarboxylate)s: Synthesis and characterization

Wang

Yin

Jiang

et al. 2019

Self Cite

The purpose of this study was to enhance the glass-transition temperature of poly(butylene 2,5-thiophenedicarboxylate) (PBTF). A series of poly(butylene-co-1,4-cyclohexanedimethylene 2,5-thiophenedicarboxylate)s (PBCTFs) were synthesized from 2,5-thiophenedicarboxylic acid, 1,4-cyclohexanedimethanol (CHDM), and 1,4-butanediol. CHDM can increase the chain rigidity and lead the β relaxation temperature shift to lower temperature. Consequently, PBCTFs showed not only the high glass-transition temperature, but also high elongations at break. PBTF was a crystalline polyester. However, differential scanning calorimetry and wide-angle Xray diffraction results suggested PBCTFs were amorphous polyesters. Thermogravimetric analysis results indicated the thermal stability of copolyesters was gradually enhanced with increasing the CHDM content. When the CHDM content was 95 mol %, PBCTF95 exhibited high glass-transition temperature (69.2 C), tensile strength (44.4 MPa), and elongation at break (205%).