Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring

Van, Amy; Chiou, Kevin; Ishida, Hatsuo

doi:10.1016/j.polymer.2014.01.041

Cited by 157 publications

(126 citation statements)

References 66 publications

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“…Reports have shown that this formyl group tends to oxidize easily forming carboxylic group which catalyze the ring-20 opening polymerization of benzoxazines. Moreover, their curing temperatures are similar to that of commercial benzoxazines which generally exhibits exothermic ring-opening reaction between 200-250 o C 18,19 . The possible structure of the cured polymer [POSS-EPbz] is shown in Scheme 4.…”

Section: Polymerization Behavior Of Poss-bzo Monomersmentioning

confidence: 67%

New benzoxazines containing polyhedral oligomeric silsesquioxane from eugenol, guaiacol and vanillin

2015

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Polybenzoxazine-tethered polyhedral oligomeric silsesquioxane nanocomposites with well-defined architecture were prepared by the reaction of bio-phenols: eugenol, guaiacol, vanillin; poss-octaamine with paraformaldehyde. FT-IR measurements evidenced the 10 occurrence of Mannich reaction between phenolic group of bio-phenols and amino group of POSS molecule, with the consequent formation of a heterocyclic benzoxazine ring binding POSS in its backbone. Their chemical structures were proved by 1 H and 13 C-NMR analysis. Thermo-mechanical properties and thermal stability of the POSS-polybenzoxazine hybrid networks were determined by DSC, DMA and TGA. SEM, EDX, AFM and TEM micrographs show that POSS-Pbz nanocomposites exhibit featureless morphologies with no discernible phase separation, suggesting that the POSS nanoparticles are dispersed homogeneously throughout the matrix. The 15 homogeneity of these networks with octafunctional POSS is also indicated by their moduli in the range of 2.63 to 2.91 GPa. Moreover, their dielectric values [both dielectric constant (1.85) and dielectric loss (0.28)] and moisture absorption values are very low (<0.01%) which makes them suitable materials for use in microelectronics packaging.

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Section: Polymerization Behavior Of Poss-bzo Monomersmentioning

confidence: 67%

New benzoxazines containing polyhedral oligomeric silsesquioxane from eugenol, guaiacol and vanillin

2015

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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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“…As aromatic compounds including phenolic derivates are the second most abundant class of organic compounds in nature representing about 25% of the earth's biomass, quite a large number of renewable phenol derivatives have been tested in recent years to synthesize benzoxazine precursors such as diphenolic acid, cardanol, vanillin, eugenol, chavicol, guaiacol, “lignin‐like” naturally occurring phenolic compounds (coumaric acid, ferulic acid, and phloretic acid), umbelliferone, arbutin, urushiol, catechol, etc. A special interest is focused on difunctional benzoxazine structure because it leads to cross‐linking.…”

Section: Introductionmentioning

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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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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Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring

Cited by 157 publications

References 66 publications

New benzoxazines containing polyhedral oligomeric silsesquioxane from eugenol, guaiacol and vanillin

New benzoxazines containing polyhedral oligomeric silsesquioxane from eugenol, guaiacol and vanillin

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

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

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