Synthesis of highly thermally stable divanillic acid-derived polyamides and their mechanical properties
TL;DR: In this paper, vanillic acid (DVA)-based polyamides with different side-chains were synthesized from methyl vanillate, and they showed good solubility in common polar organic solvents; their cast films were prepared from dimethylformamide (DMF) solution.
About: This article is published in Polymer.The article was published on 2021-07-16. It has received 10 citations till now. The article focuses on the topics: Condensation polymer & Differential scanning calorimetry.
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TL;DR: In this article, an excellent performance of poly(decamethylene furanamide) (PA10F) was synthesized via bulk polymerization with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst.
9 citations
TL;DR: In this article , an excellent performance of poly(decamethylene furanamide) (PA10F) was synthesized via bulk polymerization with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst.
9 citations
TL;DR: In this article, a series of homo-and copolyesters composed of a methylated dialkoxydivanillic acid monomer with an alkoxy side-chain length of 1 or 4 carbon units, cyclohexanedimethanol, and an alkanediol with a chain length of 6, 8, or 12 carbon units was synthesized.
6 citations
TL;DR: Fully divanillic acid (DVA)-based aromatic polyamides (R-R′-DVAPAs) having methyl or butyl side chains (R = -(CH2)n-1-CH3; n = 1 or 4) were synthesized by polycondensation of alkylated DVA-based dicarboxylic acid monomers and diamine monomers as mentioned in this paper .
5 citations
TL;DR: In this paper , a potentially biodegradable bio-based polyesters (P6DVAs) were synthesized from 1,6-hexanediol and divanillic acid with free hydroxyl groups.
4 citations
References
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TL;DR: In this article, the authors showed that poly(ethylene furanoate) (PEF) can provide a fully biosourced alternative to PET with greatly improved barrier properties and attractive thermal and mechanical properties.
Abstract: Poly(ethylene furanoate) (PEF), the furan-derived analogue to poly(ethylene terephthalate) (PET), can provide a fully biosourced alternative to PET with greatly improved barrier properties and attractive thermal and mechanical properties. The improved barrier for PEF compared to PET is unexpected due to the higher free volume of PEF vs PET. Segmental motions related to penetrant diffusion in both polyesters were studied using dynamic mechanical analysis, 13C–CP/MAS solid-state NMR variable contact-time experiments, and centerband-only detection of exchange (CODEX) measurements. Unlike the active phenyl ring-flipping mechanism in PET, furan ring-flipping is greatly suppressed, thereby reducing β relaxation motions and diffusion in PEF due to the energy penalty associated with the nonlinear axis of ring rotation and ring polarity. Preliminary work also shows similar oxygen solubilities for PEF and PET, thereby proving that the drastic permeability reduction results from a decrease in diffusion coefficient c...
442 citations
TL;DR: This review discusses the synthesis and properties of thermosets and thermoplastic polymers prepared from vanillin, ferulic acid, guaiacol, syringaldehyde, or 4-hydroxybenzoic acid.
Abstract: Nowadays, the synthesis of (semi)aromatic polymers from lignin derivatives is of major interest, as aromatic compounds are key intermediates in the manufacture of polymers and lignin is the main source of aromatic biobased substrates. Phenols with a variety of chemical structures can be obtained from lignin deconstruction; among them, vanillin and ferulic acid are the main ones. Depending on the phenol substrates, different chemical modifications and polymerization pathways are developed, leading to (semi)aromatic polymers covering a wide range of thermomechanical properties. This review discusses the synthesis and properties of thermosets (vinyl ester resins, cyanate ester, epoxy, and benzoxazine resins) and thermoplastic polymers (polyesters, polyanhydrides, Schiff base polymers, polyacetals, polyoxalates, polycarbonates, acrylate polymers) prepared from vanillin, ferulic acid, guaiacol, syringaldehyde, or 4-hydroxybenzoic acid.
275 citations
TL;DR: In this paper, a detailed differential scanning calorimetry study on the crystallization behavior of high molecular weight poly(ethylene 2,5-furanoate) allowed to calculate the equilibrium melting temperature of 239.3 and 239.7 °C for the first and second melting peak, respectively.
Abstract: Furan-2,5-dicarboxylic acid (FDCA) is a widely advocated renewable substitute for terephthalic acid (TA). Preparation of high molecular weight FDCA based polyesters by an industrially common combination of melt polymerization and subsequent solid state post condensation is described. Ultimately, poly(ethylene 2,5-furanoate) (PEF) with absolute Mn = 83,000 g mol−1 is obtained, determined by triple detection Size Exclusion Chromatography. The bulk polymer properties of FDCA based polyesters, necessary to evaluate their industrial potential were determined the Young's modulus of PEF is determined to be 2450 ± 220 MPa and the maximum stress 35 ± 8 MPa. The influence of crystallinity on the mechanical properties as function of temperature was determined by dynamic mechanical thermal analysis. A detailed differential scanning calorimetry study on the crystallization behavior of high molecular weight PEF allowed to calculate the equilibrium melting temperature (Tm0) of 239.3 and 239.7 °C for the first and second melting peak, respectively. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4191–4199
239 citations
TL;DR: The use of vanillin for the preparation of renewable polymers is a burning issue that is actively investigated as mentioned in this paper, and vanillin is currently one of the only biobased and aromatic compounds that are industrially available.
235 citations
TL;DR: In this article, vanillin and acetic anhydride are subjected to the Perkin reaction and then hydrogenation to afford acetyldihydroferulic acid, which exhibits thermal properties functionally similar to those of polyethylene terephthalate (PET).
191 citations