Resveratrol-based tri-functional benzoxazines: Synthesis, characterization, polymerization, and thermal and flame retardant properties

Zhang, Kan; Han, Mengchao; Han, Lu; Ishida, Hatsuo

doi:10.1016/j.eurpolymj.2019.04.036

Cited by 93 publications

(46 citation statements)

References 43 publications

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“…Polybenzoxazines from resveratrol-based tri-functional monomers exhibit a similarly high performance characteristic. Such polymer systems exhibit low polymerization temperature, very high thermal stability and exceptionally high char yield [ 26 ]. Polybenzoxazine matrix is also a key component in an increasing number of novel high-performance composites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

et al. 2020

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A series of cresol-based benzoxazines were synthesized for potential application as a polymer matrix in abrasive composites. The chemical structures of the obtained benzoxazine resins were investigated in detail using Fourier transform infrared spectroscopy (FTIR) and hydrogen-1 as well as carbon-13 nuclear magnetic resonance spectroscopy (1H NMR, 13C NMR) with an additional analysis using two-dimensional NMR techniques (2D NMR 1H-1H COSY, 1H-13C gHSQC and gHMBC). Structural analysis confirmed the presence of vibrations of -O-C-N- at ~950 cm−1 wavenumber, characteristic for an oxazine ring. The thermal properties of benzoxazine monomers were examined using differential scanning calorimetry (DSC) analysis. The polymerization enthalpy varied from 143.2 J/g to 287.8 J/g. Thermal stability of cresol-based benzoxazines was determined using thermogravimetry (TGA) analysis with additional analysis of the amount of volatile organic compounds (VOC) emitted from the synthesized benzoxazines during their crosslinking by static headspace coupled with gas chromatography technique (HS-GC). The amount of residual mass significantly differed between all synthesized polybenzoxazines in the range from 8.4% to 21.2%. The total VOC emission for benzoxazines decreased by 46–77% in reference to a conventional phenolic binder. The efficiency of abrasive composites with the benzoxazine matrix was evaluated based on abrasion tests. Performed analyses confirmed successful synthesis and proper chemical structure of cresol-based benzoxazines. All the experiments indicated that benzoxazines based on different cresol isomers significantly differ from each other. Good thermal performance and stability of the abrasive composites with the polybenzoxazine matrix and significantly lower VOC emission allow us to state that benzoxazines can be a promising and valuable alternative to the phenolics and a new path for the development of modern, eco-friendly abrasives.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

et al. 2020

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“…1,3-Benzoxazine, a monomer of newly developed thermosetting resins called polybenzoxazines (PBZ), can be synthesized conveniently from primary amine, formaldehyde, and phenol by one-pot Mannich condensation [1,2]. Due to the wide range of selectivity of raw materials, it provides benzoxazines with molecular design flexibility and can meet the practical requirement by designing different monomer structures [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. For example, the tetra-functional fluorene-based benzoxazine resin (t-BF-a-c) was synthesized, which exhibits an exothermal peak at 276°C, and displays good processability and wide process window(60°C) due to the incorporation of cardanol [21].…”

Section: Introductionmentioning

confidence: 99%

Low melting point, high thermal stable branched benzoxazines resin derived from mixed-substituted phosphazene core

Ma¹,

Qiu²,

Liu³

2020

Express Polym. Lett.

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Six fluorine-containing, mix-substituted phosphazene-based branched benzoxazine monomers with a low melting point were successfully prepared and their chemical structures were verified by 1 H, 13 C, 31 P and 19 F nuclear magnetic resonance (NMR). These branched benzoxazine resins underwent thermal ring-opening polymerization to form cured polymers with high thermal stability both in N 2 atmosphere and in air. The co-substituents, both m-CF 3 PhOH and p-CF 3 PhOH, imposed significant effects on processing, thermal, and surface properties of corresponding polybenzoxazines. Non-isothermal differential scanning calorimetry (DSC) under diverse heating rates was adopted to investigate the curing kinetics and determine the activation energy of polymerization. DSC results indicate that the m-CF 3 PhO-/p-CF 3 PhO-groups have the potential to lower ring-opening polymerization temperature. Glass transition temperatures (T g s) of polybenzoxazines derived from p-CF 3 PhOH are higher than that of polymers derived from m-CF 3 PhOH due to different steric hindrance and crosslinking density. More interesting, all polybenzoxazines show relatively high dielectric constant but exhibit low dielectric loss at ambient temperature.

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“…The detailed structure of NAR-a was conrmed by combining the results of FT-IR ( Fig. S1 †), and 1 H, 13 C and 2D NMR spectroscopies as well as elemental analysis and HR-MS. Generally, the typical 1 H and 13 C NMR signals for the methylene pairs in bisbenzoxazine monomers consist of two singlets attributed to the symmetry of the chemical structure. 19,20 As shown in Fig.…”

Section: Synthesis Of Nar-amentioning

confidence: 99%

“…8,9 Interestingly, the manipulation of intramolecular hydrogen bonding in the structure of curing agents can signicantly enhance the shelf life of epoxy resins. 10 Polybenzoxazine is a relatively new type of cross-linked polymer, which has been drawing particularly strong interest from both academic researchers and industrial engineers due to its excellent features, such as near-zero shrinkage during curing, 11,12 high thermal stability, [13][14][15] low-k (dielectric constant) values, 16,17 low surface free energy 18 and exible macromolecular design capability. 19,20 Besides, polybenzoxazine can be directly prepared by the thermally activated ring-opening polymerization of 1,3-benzoxazine.…”

Section: Introductionmentioning

confidence: 99%

A naringenin-based benzoxazine with an intramolecular hydrogen bond as both a thermal latent polymerization additive and property modifier for epoxy resins

2020

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Resveratrol-based tri-functional benzoxazines: Synthesis, characterization, polymerization, and thermal and flame retardant properties

Cited by 93 publications

References 43 publications

Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

Synthesis and Characterization of Low-Cost Cresol-Based Benzoxazine Resins as Potential Binders in Abrasive Composites

Low melting point, high thermal stable branched benzoxazines resin derived from mixed-substituted phosphazene core

A naringenin-based benzoxazine with an intramolecular hydrogen bond as both a thermal latent polymerization additive and property modifier for epoxy resins

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