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Poly(butylene 2,5-thiophenedicarboxylate): An Added Value to the Class of High Gas Barrier Biopolyesters.

ABSTRACT: Many efforts are currently devoted to the design and development of high performance bioplastics to replace traditional fossil-based polymers. In response, this contribution presents a new biobased aromatic polyester, i.e., poly(butylene 2,5-thiophenedicarboxylate) (PBTF). Here, PBTF is characterized from the molecular, thermo-mechanical and structural point of view. Gas permeability is evaluated at different temperatures, in the range below and above glass transition, providing a full insight into the performances of this material under different operating conditions, and demonstrating the superior gas barrier behavior of PBTF with respect to other polyesters, such as PEF and PET. The combination of calorimetric and diffractometric studies allows for a deep understanding of the structure of PBTF, revealing the presence of a not-induced 2D-ordered phase (meso-phase), responsible for its outstanding gas permeability behavior. The simple synthetic strategy adopted, the exceptional barrier properties, combined with the interesting mechanical characteristics of PBTF open up new scenarios in the world of green and sustainable packaging materials.

SUBMITTER: Guidotti G

PROVIDER: S-EPMC6414998 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Furanoate-Based Nanocomposites: A Case Study Using Poly(Butylene 2,5-Furanoate) and Poly(Butylene 2,5-Furanoate)-co-(Butylene Diglycolate) and Bacterial Cellulose.

Project description:Polyesters made from 2,5-furandicarboxylic acid (FDCA) have been in the spotlight due to their renewable origins, together with the promising thermal, mechanical, and/or barrier properties. Following the same trend, (nano)composite materials based on FDCA could also generate similar interest, especially because novel materials with enhanced or refined properties could be obtained. This paper presents a case study on the use of furanoate-based polyesters and bacterial cellulose to prepare nanocomposites, namely acetylated bacterial cellulose/poly(butylene 2,5-furandicarboxylate) and acetylated bacterial cellulose/poly(butylene 2,5-furandicarboxylate)-co-(butylene diglycolate)s. The balance between flexibility, prompted by the furanoate-diglycolate polymeric matrix; and the high strength prompted by the bacterial cellulose fibres, enabled the preparation of a wide range of new nanocomposite materials. The new nanocomposites had a glass transition between -25⁻46 °C and a melting temperature of 61⁻174 °C; and they were thermally stable up to 239⁻324 °C. Furthermore, these materials were highly reinforced materials with an enhanced Young's modulus (up to 1239 MPa) compared to their neat copolyester counterparts. This was associated with both the reinforcing action of the cellulose fibres and the degree of crystallinity of the nanocomposites. In terms of elongation at break, the nanocomposites prepared from copolyesters with higher amounts of diglycolate moieties displayed higher elongations due to the soft nature of these segments.

| S-EPMC6403708 | biostudies-literature

Partially Renewable Poly(butylene 2,5-furandicarboxylate-co-isophthalate) Copolyesters Obtained by ROP.

Project description:Cyclic butylene furandicarboxylate (c(BF)n) and butylene isophthalate (c(BI)n) oligomers obtained by high dilution condensation reaction were polymerized in bulk at 200 °C with Sn(Oct)₂ catalyst via ring opening polymerization to give homopolyesters and copolyesters (coPBFxIy) with weight average molar masses in the 60,000⁻70,000 g·mol-1 range and dispersities between 1.3 and 1.9. The composition of the copolyesters as determined by NMR was practically the same as that of the feed, and they all showed an almost random microstructure. The copolyesters were thermally stable up to 300 °C and crystalline for all compositions, and have Tg in the 40⁻20 °C range with values decreasing almost linearly with their content in isophthalate units in the copolyester. Both melting temperature and enthalpy of the copolyesters decreased as the content in butylene isophthalate units increased up to a composition 30/70 (BF/BI), at which the triclinic crystal phase made exclusively of butylene furanoate units changed to the crystal structure of PBI. The partial replacement of furanoate by isophthalate units decreased substantially the crystallizability of PBF.

| S-EPMC6415514 | biostudies-literature

Co-Polymers based on Poly(1,4-butylene 2,5-furandicarboxylate) and Poly(propylene oxide) with Tuneable Thermal Properties: Synthesis and Characterization.

Project description:Poly(ether ester)s (PEEs) represent a promising class of segmented co-polymers, nevertheless the synthesis of PEEs based on renewable 2,5-furandicarboxylic acid (FDCA) is still scarce. In this context, a series of poly(1,4-butylene 2,5-furandicarboxylate)-co-poly(poly(propylene oxide) 2,5-furandicarboxylate) co-polyesters with different composition of stiff poly(1,4-butylene 2,5-furandicarboxylate) (PBF) and soft poly(poly(propylene oxide) 2,5-furandicarboxylate) (PPOF) moieties were synthesized, via a two-step bulk polytransesterification reaction. The molar ratio of PBF/PPOF incorporated was varied (10 to 50 mol%) in order to prepare several novel materials with tuned properties. The materials were characterised in detail through several techniques, namely ATR FTIR, ¹H and 13C NMR, TGA, DSC, DMTA and XRD. Their hydrolytic and enzymatic degradation evaluation was also assessed. These new co-polymers showed either a semi-crystalline nature when higher PBF/PPOF ratios were used, and for approximately equal amounts of PBF and PPOF an amorphous co-polyester was obtained instead.

| S-EPMC6356699 | biostudies-literature

Poly(Alkylene 2,5-Thiophenedicarboxylate) Polyesters: A New Class of Bio-Based High-Performance Polymers for Sustainable Packaging.

Project description:In the present study, 100% bio-based polyesters of 2,5-thiophenedicarboxylic acid were synthesized via two-stage melt polycondensation using glycols containing 3 to 6 methylene groups. The so-prepared samples were characterised from the molecular point of view and processed into free-standing thin films. Afterward, both the purified powders and the films were subjected to structural and thermal characterisation. In the case of thin films, mechanical response and barrier properties to O2 and CO2 were also evaluated. From the results obtained, it emerged that the length of glycolic sub-units is an effective tool to modulate the chain mobility and, in turn, the kind and amount of ordered phases developed in the samples. In addition to the usual amorphous and 3D crystalline phases, in all the samples investigated it was possible to evidence a further phase characterised by a lower degree of order (mesophase) than the crystalline one, whose amount is strictly related to the glycol sub-unit length. The relative fraction of all these phases is responsible for the different mechanical and barrier performances. Last, but not least, a comparison between thiophene-based homopolymers and their furan-based homologues was carried out.

| S-EPMC8348809 | biostudies-literature

Poly(butylene 2,4-furanoate), an Added Member to the Class of Smart Furan-Based Polyesters for Sustainable Packaging: Structural Isomerism as a Key to Tune the Final Properties.

Project description:High-molecular-weight poly(butylene 2,4-furanoate) (2,4-PBF), an isomer of well-known poly(butylene 2,5-furanoate) (2,5-PBF), was synthesized through an eco-friendly solvent-free polycondensation process and processed in the form of an amorphous film by compression molding. Molecular characterization was carried out by NMR spectroscopy and GPC analysis, confirming the chemical structure and high polymerization degree. Thermal analyses evidenced a reduction of both glass-to-rubber transition and melting temperatures, as well as a detriment of crystallization capability, for 2,4-PBF with respect to 2,5-PBF. Nevertheless, it was possible to induce crystal phase formation by annealing treatment. Wide-angle X-ray scattering revealed that the crystal lattices developed in the two isomers are distinct from each other. The different isomerism affects also the thermal stability, being 2,4-PBF more thermally inert than 2,5-PBF. Functional properties, such as wettability, mechanical response, and gas barrier capability, were tested on both amorphous and semicrystalline 2,4-PBF films and compared with those of 2,5-PBF. Reduced hydrophilicity was determined for 2,4-isomer, in line with its lower average dipole moment, suggesting better chemical resistance to hydrolysis. Stress-strain tests have evidenced the higher flexibility and toughness of 2,4-PBF with respect to those of 2,5-PBF and the possibility of improving its mechanical resistance by annealing. Finally, the different isomerism deeply affects the gas barrier performance, being the O2- and CO2-transmission rates of 2,4-PBF 50 and 110 times lower, respectively, than those of 2,5-PBF. The gas barrier properties turned out to be outstanding under a dry atmosphere as well as in humid conditions, suggesting the presence of interchain hydrogen bonds. The gas blocking capability decreases after annealing because of the presence of disclination associated with the formation of crystals.

| S-EPMC8424682 | biostudies-literature

Poly(butylene succinate-co-butylene acetylenedicarboxylate): Copolyester with Novel Nucleation Behavior.

Project description:Big spherulite structure and high crystallinity are the two main drawbacks of poly(butylene succinate) (PBS) and hinder its application. In this work, a new type of copolyester poly(butylene succinate-co-butylene acetylenedicarboxylate) (PBSAD) is synthesized. With the incorporation of acetylenedicarboxylate (AD) units into PBS chains, the crystallization temperature and crystallinity are depressed by excluding AD units to the amorphous region. In contrast, the primary nucleation capability is significantly strengthened, without changing the crystal modification or crystallization kinetics, leading to the recovery of total crystallization rate of PBSAD under the same supercooling condition. The existence of specific interaction among AD units is found to be crucial. Although it is too weak to contribute to the melt memory effect at elevated temperature, the interaction continuously strengthens as the temperature falls down, and the heterogeneous aggregation of AD units keeps growing. When the aggregating process reaches a certain extent, it will induce the formation of a significant amount of crystal nuclei. The unveiled nucleation mechanism helps to design PBS copolymer with good performance.

| S-EPMC7865284 | biostudies-literature

Synthesis and Characterization of High Glycolic Acid Content Poly(glycolic acid-co-butylene adipate-co-butylene terephthalate) and Poly(glycolic acid-co-butylene succinate) Copolymers with Improved Elasticity.

Project description:Poly(glycolic acid) (PGA) is a biodegradable polymer with high gas barrier properties, mechanical strength, and heat deflection temperature. However, PGA's brittleness severely limits its application in packaging, creating a need to develop PGA-based copolymers with improved elasticity that maintain its barrier properties and hydrolytic degradability. In this work, a series of PGBAT (poly(glycolic acid-co-butylene) adipate-co-butylene terephthalate) copolymers containing 21-92% glycolic acid (nGA) with Mw values of 46,700-50,600 g mol-1 were synthesized via melt polycondensation, and the effects of altering the nGA on PGBAT's thermomechanical properties and hydrolysis rate were investigated. Poly(glycolic acid-co-butylene succinate) (PGBS) and poly(glycolic acid-co-butylene terephthalate) (PGBT) copolymers with high nGA were synthesized for comparison. DSC analysis revealed that PGBAT21 (nGA = 21%) and PGBAT92 were semicrystalline, melting between 102.8 and 163.3 °C, while PGBAT44, PGBAT86-89, PGBT80, and PGBS90 were amorphous, with Tg values from -19.0 to 23.7 °C. These high nGA copolymers showed similar rates of hydrolysis to PGA, whereas those containing <50% GA showed almost no mass loss over the testing period. Their mechanical properties were highly dependent upon their crystallinity and improved significantly after annealing. Of the high nGA copolymers, annealed PGBS90 (Mw 97,000 g mol-1) possessed excellent mechanical properties with a modulus of 588 MPa, tensile strength of 30.0 MPa, and elongation at break of 171%, a significant improvement on PGA's elongation at break of 3%. This work demonstrates the potential of enhancing PGA's flexibility by introducing minor amounts of low-cost diols and diacids into its synthesis.

| S-EPMC10586444 | biostudies-literature

Isothermal Kinetics of Poly(butylene adipate-co-butylene itaconate) Copolyesters with Ethylenediaminetetraacetic Acid.

Project description:A series of aliphatic copolyesters, poly(butylene adipate-co-butylene itaconate) (PBABI), have been synthesized using melt polycondensation of adipic acid (AA), itaconic acid (IA), 1,4-butanediol (1,4-BDO), and the tetra-functional group of ethylenediaminetetraacetic acid (EDTA, 0.1 mol %) to form partially cross-linking density as novel thermoplastic unsaturated copolyesters in our previous research. The crystal phase of PBABI copolyesters tended to prefer thermodynamics in the presence of a small amount of EDTA. The isothermal crystallization analysis revealed that the PBABI with EDTA exhibited a higher crystallization rate and a shorter half-time of crystallization than neat PBABI copolyesters. All of the sizes of spherulite/sheet crystals in the BA/BI = 9/1 are smaller than at BA/BI = 10/0 with or without a cross-linking agent, which demonstrated that the morphology behavior tended to form a small sheet crystal in the presence of 10 mol % IA, which played a dominant role in determining the average size of the crystal. These results deepen our understanding of the relationship among the cross-linking agent, the crystal form, and solidification time in PBABI copolyesters, making these kinds of polymers applicable to reinforce three-dimensional (3D) air-permeable polyester-based smart textiles.

| S-EPMC7033981 | biostudies-literature

Poly(lactide)-g-poly(butylene succinate-co-adipate) with High Crystallization Capacity and Migration Resistance.

Project description:Plasticized polylactide (PLA) with increased crystallization ability and prolonged life-span in practical applications due to the minimal plasticizer migration was prepared. Branched plasticized PLA was successfully obtained by coupling poly(butylene succinate-co-adipate) (PBSA) to crotonic acid (CA) functionalized PLA. The plasticization behavior of PBSA coupled PLA (PLA-CA-PBSA) and its counterpart PBSA blended PLA (PLA/PBSA) were fully elucidated. For both PLA-CA-PBSA and PLA/PBSA, a decrease of Tg to around room temperature and an increase in the elongation at break of PLA from 14% to 165% and 460%, respectively, were determined. The crystallinity was increased from 2.1% to 8.4% for PLA/PBSA and even more, to 10.6%, for PLA-CA-PBSA. Due to the inherent poor miscibility between the PBSA and PLA, phase separation occurred in the blend, while PLA-CA-PBSA showed no phase separation which, together with the higher crystallinity, led to better oxygen barrier properties compared to neat PLA and PLA/PBSA. A higher resistance to migration during hydrolytic degradation for the PLA-CA-PBSA compared to the PLA/PBSA indicated that the plasticization effect of PBSA in the coupled material would be retained for a longer time period.

| S-EPMC5503035 | biostudies-other

Selective photoelectrochemical oxidation of glycerol to high value-added dihydroxyacetone.

Project description:It is highly profitable to transform glycerol - the main by-product from biodiesel production to high value-added chemicals. In this work, we develop a photoelectrochemical system based on nanoporous BiVO4 for selective oxidation of glycerol to 1,3-dihydroxyacetone - one of the most valuable derivatives of glycerol. Under AM 1.5G front illumination (100 mW cm-2) in an acidic medium (pH = 2) without adscititious oxidant, the nanoporous BiVO4 photoanode achieves a glycerol oxidation photocurrent density of 3.7 mA cm-2 at a potential of 1.2 V versus RHE with 51% 1,3-dihydroxyacetone selectivity, equivalent to a production rate of 200 mmol of 1,3-dihydroxyacetone per m2 of illumination area in one hour.

| S-EPMC6467901 | biostudies-other

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