Modification of benzoxazine with aryl-ether-ether-ketone diphenol: preparation and characterization

Xia, Yuhan; Lin, Yi‐Feng; Ran, Qichao; Zhu, Rongshu; Gu, Yi

doi:10.1039/c6ra27493e

Cited by 16 publications

(11 citation statements)

References 54 publications

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“…Characteristic absorption band of –NH 2 was observed at 3460 and 3381 cm −1 [30]. In Figure 2b, the characteristic absorption band of antisymmetric oxazine ring stretch appeared at 953 cm −1 [16,31]. Moreover, a wide absorption band at around 3412 cm −1 was observed, which can be assigned to the intermolecular association of hydroxyl bonds, generated from the trace hydrogen and nitrogen atoms in benzoxazine rings.…”

Section: Resultsmentioning

confidence: 99%

“…To improve the brittleness of thermosetting composites, various methods were attempted, including the physical blending of thermoplastic and thermosetting resins, the chemical bonding of long molecular segments into the thermosetting resin by molecular designing. High-performance thermoplastic polymers such as poly(ether imide), polyaryletherketone, poly(arylene ether nitrile) and amines (octanediamine and m -xylylenediamine) were blended with benzoxazine resins to enhance the toughness [15,16,17,18]. Results indicated that the brittleness of the composites was improved, but the incompatible also led to the decrease in thermodynamic performance.…”

Section: Introductionmentioning

confidence: 99%

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Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Chen

Ren

et al. 2019

Polymers

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Benzoxazine containing fluorinated aromatic ether nitrile linkage (FAEN-Bz) had been synthesized from 2,6-dichlorobenzonitrile, 4,4’-(hexafluoroisopropylidene)diphenol (bisphenol AF), 3-Aminophenol, formaldehyde, phenol by condensation polymerization and Mannich ring-forming reaction. Structures of the monomer were verified by Proton NMR spectrum (1H-NMR) and Fourier transform infrared spectroscopy (FTIR). Curing behaviors and curing kinetics of designed monomers were investigated and discussed. The activation energy was calculated and possible polymerization mechanisms were also proposed. Then, properties of cured polymers including crosslinking degrees, thermal decomposition, surface wettability and energy, and dielectric properties were studied and discussed. Additionally, programmed integral decomposition temperature (IPDT) was also used to evaluate the thermal stability of final polymers. Results indicated that the incorporation of benzoxazine and nitrile resulted in increased thermal stability and char yields. Moreover, the surface wettability and dielectric properties of poly(FAEN-Bz) can be easily controlled by tuning the curing temperatures and time.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Chen

Ren

et al. 2019

Polymers

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“…Besides, many efforts have also been made in chemical tailoring of benzoxazine monomer based on the molecular design flexibility . Despite the obvious toughening effects reported, this method is complex and arduous in synthesis of the benzoxazine precursors.…”

Section: Introductionmentioning

confidence: 99%

Significant Improvement on Polybenzoxazine Toughness Achieved by Amine/Benzoxazine Copolymerization‐Induced Phase Separation

Zhao

et al. 2018

Macro Chemistry & Physics

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Two commercially available amines, octanediamine (ODM) and m‐xylylenediamine (MXDM), are chosen for tough polybenzoxazine resin due to their controllable capability to cause phase separation during the copolymerization with benzoxazine monomers. The toughening behavior and phase separation of the cured resins are investigated using tensile tests and analyses of dynamic mechanical analysis (DMA), scanning electron microscope, and thermal gravimetry–gas chromatography/mass spectroscopy. The resulting networks show remarkable toughness without obvious degradation in thermomechanical performance. Especially, when ODM/MXDM molar ratio is 1:1, an elongation rate of 10.55% and a breaking strength of 82.67 Mpa, which are 86% and 128% higher than that of the neat benzoxazine resin, respectively, are achieved. These findings open a new way to improve toughness of brittle polybenzoxazine resins.

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“…Blending with other polymers such as liquid rubber 14 and thermoplastic resins [15][16][17] has been reported to effectively improve the toughness of various polybenzoxazine resins. Phase-separated structures were induced, while the impact energy was absorbed and the toughening properties of polymers were improved.…”

Section: Introductionmentioning

confidence: 99%

Improvement of aldehyde‐functional polybenzoxazine processability and mechanical properties achieved by 5‐aminoindole/benzoxazine copolymerization

Yang

Liu

et al. 2020

Polymer International

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5-Aminoindole is designed for aldehyde-functional benzoxazine (PHB-a) copolymerization due to the special reaction between the indole and aldehyde groups, and the copolymerization with benzoxazine monomers. The curing and mechanical behavior and thermal properties of the cured resins are investigated using Fourier transform infrared spectroscopy, 1 H NMR spectroscopy, differential scanning calorimetry, scanning electron microscopy, dynamic mechanical analysis, tensile tests and thermogravimetric analysis. The resulting networks show better processability and mechanical properties without obvious degradation in thermal performance. The low curing temperature (70°C) of PHB-a is achieved after incorporation of 5-aminoindole. An elongation rate of 2.54% and a forcing break of around 72.3 MPa are achieved, while neat poly(PHB-a) is brittle and failed in the grips. Furthermore, its glass transition temperature is maintained up to 234°C. These findings open a new way to realize low-temperature curing and to improve the mechanical properties of brittle polybenzoxazine resins under the premise of maintaining good thermal stability.

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Modification of benzoxazine with aryl-ether-ether-ketone diphenol: preparation and characterization

Abstract: A modified benzoxazine resin system with “high strength, high modulus and high toughness” was prepared by introducing an efficient modifier (m-DHPBP) with high catalytic activity and an aryl-ether-ether-ketone (PEEK) structure.

Cited by 16 publications

References 54 publications

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Significant Improvement on Polybenzoxazine Toughness Achieved by Amine/Benzoxazine Copolymerization‐Induced Phase Separation

Improvement of aldehyde‐functional polybenzoxazine processability and mechanical properties achieved by 5‐aminoindole/benzoxazine copolymerization

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