Phloretic acid as an alternative to the phenolation of aliphatic hydroxyls for the elaboration of polybenzoxazine

Trejo-Machin, Acerina; Verge, Pierre; Puchot, Laura; Quintana, Robert

doi:10.1039/c7gc02348k

Cited by 65 publications

(56 citation statements)

References 41 publications

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“…Nevertheless, it appears that the weight losses due to the first stage of degradation and recorded by TGA do not affect dramatically the curing of PDC‐Fa, BDC‐Fa, and IDC‐Fa as it proved possible to achieve bulk materials without significant problems and defects. Moreover, these results are in accordance with data reported in the literature for similar types of precursors …”

Section: Resultssupporting

confidence: 93%

“…Moreover, these results are in accordance with data reported in the literature for similar types of precursors. [43,45,50] To complete DSC and TGA analyses, rheological measurements were performed to further evaluate the polymerization ability of the resins and determine their processing window. Two types of tests were considered.…”

Section: Polymerization Of the Bio-based Benzoxazine Precursorsmentioning

confidence: 99%

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High‐Performance Bio‐Based Benzoxazines from Enzymatic Synthesis of Diphenols

Bonnaud

Chollet

Dumas

et al. 2018

Macro Chemistry & Physics

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This paper reports the preparation, characterization, and performance of three low viscosity fully bio‐based benzoxazine resins synthesized from bio‐based furfurylamine, paraformaldehyde, and three new enzymatic originated diphenols obtained through a sustainable and highly selective lipase‐catalyzed enzymatic process from p‐coumaric acid, and three bio‐based diols (propanediol, butanediol, and isosorbide, respectively). The enzymatic method is used for the first time, to the authors’ knowledge, to design specific diphenolic structures dedicated to the preparation of benzoxazine thermosetting resins whose precursors exhibit easy handling within a wide processing window (from room temperature up to 200 °C). The resulting cross‐linked materials present high glass transition temperature (T g > 200 °C) and inherent charring ability upon pyrolysis (≈50 wt% at 1000 °C). These results open a valuable and new pathway to develop enhanced benzoxazines and bring them new properties.

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Section: Resultssupporting

confidence: 93%

Section: Polymerization Of the Bio-based Benzoxazine Precursorsmentioning

confidence: 99%

High‐Performance Bio‐Based Benzoxazines from Enzymatic Synthesis of Diphenols

Bonnaud

Chollet

Dumas

et al. 2018

Macro Chemistry & Physics

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“…[15] Up to now,alarge quantity of biobased benzoxazines have already been prepared from the renewable cardanol, [16,17] diphenolic acid, [18,19] phloretic acid, [20] furfurylamine, [21,22] stearylamine, [23] coumarin, [24,25] umbelliferone, [26] and more recently the lignin derivatives (guaiacol, [27][28][29][30] vanillin, [31][32][33] and eugenol [34][35][36][37][38] ). [15] Up to now,alarge quantity of biobased benzoxazines have already been prepared from the renewable cardanol, [16,17] diphenolic acid, [18,19] phloretic acid, [20] furfurylamine, [21,22] stearylamine, [23] coumarin, [24,25] umbelliferone, [26] and more recently the lignin derivatives (guaiacol, [27][28][29][30] vanillin, [31][32][33] and eugenol [34][35][36]…”

Section: Introductionmentioning

confidence: 99%

Biobased Benzoxazine Derived from Daidzein and Furfurylamine: Microwave‐Assisted Synthesis and Thermal Properties Investigation

et al. 2018

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A biobased benzoxazine resin (Dz-f) demonstrating excellent thermal properties was synthesized from daidzein and furfurylamine by using a microwave heating method. The chemical structure of synthesized benzoxazine monomer was identified by FTIR and NMR ( H and C NMR) before it was cured and its thermal properties evaluated by differential scanning calorimetry (DSC), TGA, and dynamic mechanical analysis (DMA). The cured resin p(Dz-f) exhibited a glass transition temperature (T ) of 391 °C, a very high char yield of 68.7 %, and outstanding thermal stability; the T value obtained was the highest thermal stability value ever reported for polybenzoxazine with a high biobased content. Moreover, Dz-f demonstrated a satisfying processability, which was rare for the high-performance thermosetting resins. This work provided us with a new strategy for the preparation of high biocontent resins with excellent thermal properties. In addition, the combination of biobased feedstocks with a microwave-assisted heating method as well as the potential application of this approach in high-end fields might perpetuate remarkable progress towards the sustainable development of the polymeric industry.

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“…Furthermore, another synthetic route to phloretic acid may be available by biosynthesis from lignin . An additional advantage of phloretic acid is that it is thermally more stable than its unsaturated counterparts, p ‐coumaric acid or ferulic acid …”

Section: Introductionmentioning

confidence: 99%

“…20 An additional advantage of phloretic acid is that it is thermally more stable than its unsaturated counterparts, p-coumaric acid or ferulic acid. 21 Though 1 H and 13 C NMR spectra of tetrapolyesters related to polyethylene terephthalate or polylactic acid have been discussed in detail in the literature, such work has been lacking for other polyesters, such as those involving p-hydroxybenzoic acid or p-hydroxycinammic acid and their derivatives. In this work, we will present the detailed peak assignments of the 1 H and 13C NMR spectra, including a dyad analysis.…”

Section: Introductionmentioning

confidence: 99%

Highly renewable, thermoplastic tetrapolyesters based on hydroquinone, p‐hydroxybenzoic acid or its derivatives, phloretic acid, and dodecanedioic acid

Bloom

Vicentin

Honeycutt

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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A series of tetrapolyesters were obtained by polymerizing phloretic acid, hydroquinone, p‐hydroxybenzoic acid, or its derivatives, that is, vanillic acid or syringic acid, and dodecanedioic acid. Each monomer was polymerized in its acetylated form, except for the diacid to undergo polymerization by acidolysis. Initial polymerizations had shown that the use of phloretic acid resulted in better polymer properties than with p‐coumaric acid. The predominantly renewable polymers were obtained by melt polymerization using a two‐stage condensation process whereby antimony(III) oxide was applied as catalyst. Monomer conversions were typically close to 90%. 1H and 13C NMR, DSC, TGA, solution viscometry, and GPC were applied, as well as polarized microscopy to determine polymer microstructure and composition, transition temperatures, decomposition temperatures, intrinsic viscosities, and other molecular weight properties, and when applicable the liquid crystalline behavior of the polymers. All peaks, including end group peaks in the 13C NMR spectra were assigned, the monomer sequence distribution was verified to be random, and a complete dyad analysis involving nine dyads and eight peaks was performed. By using p‐hydroxybenzoic acid and its derivatives without any, one or two methoxy groups and varying the copolymer compositions, melting temperatures could be tuned between 106 and 181 °C. The tetrapolyesters, which included residues of p‐hydroxybenzoic acid, formed nematic liquid crystals. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1498–1507

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Phloretic acid as an alternative to the phenolation of aliphatic hydroxyls for the elaboration of polybenzoxazine

Abstract: Phloretic acid: a sustainable building block to promote the solvent-free elaboration of benzoxazine and its polymerization into fully bio-based thermosets.

Cited by 65 publications

References 41 publications

High‐Performance Bio‐Based Benzoxazines from Enzymatic Synthesis of Diphenols

High‐Performance Bio‐Based Benzoxazines from Enzymatic Synthesis of Diphenols

Biobased Benzoxazine Derived from Daidzein and Furfurylamine: Microwave‐Assisted Synthesis and Thermal Properties Investigation

Highly renewable, thermoplastic tetrapolyesters based on hydroquinone, p‐hydroxybenzoic acid or its derivatives, phloretic acid, and dodecanedioic acid

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