Dual-curing propargyl-phthalonitrile imide-based thermoset: Synthesis, characterization and curing behavior

Kolesnikov, Timofey I.; Орлова, А. М.; Tsegelskaya, A. Yu.; Cherkaev, G. V.; Kechek’yan, A. S.; Бузин, А. И.; Dmitryakov, Petr V.; Белоусов, С. И.; Абрамов, И. Г.; Serushkina, O. V.; Кузнецов, А. А.

doi:10.1016/j.eurpolymj.2021.110865

Cited by 20 publications

(6 citation statements)

References 60 publications

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“…37 The experimental data was corresponding to literature data. 38 NMR spectra were recorded on a Bruker AVANCE-400 SB (400 MHz). The UV-visible absorption spectra were recorded on a Shimadzu UV-1900 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Kaskevich,

Simonova,

Romasheva

et al. 2024

Journal of Polymer Science

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A series of molecular brushes with a polyfluorene (PF) backbone and polymethacrylic acid side chains of varying lengths were prepared by atom transfer radical polymerization. The structure and composition of the synthesized compounds were confirmed by 1H NMR and IR spectroscopy. Effect of the length of the backbone on spectral and conformational parameters of the macromolecules in solutions was analyzed. The grafting density of side chains was about 90%. Spectral methods have been used to determine the dependence of side chain grafting on the luminescent properties of polymer solutions, including quantum yields. It was shown that an optimal length of polymethacrylic acid side chains provides solubility of the polymer brushes. Solutions of PF‐graft‐polymethacrylic acid complexes with the model substance curcumin were investigated. It was established that the molecular brushes containing curcumin form monomolecular micelles. Molecular brushes with zinc phthalocyanine, potential systems for photodynamic, and photothermal therapy, were studied.

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Section: Methodsmentioning

confidence: 99%

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Kaskevich,

Simonova,

Romasheva

et al. 2024

Journal of Polymer Science

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“…It has been demonstrated that crosslinking reaction between specific functional groups, such as alkene, alkyne, and cyano units is an effective way to compensate for the loss of thermal properties and solvent resistance. 11,36,37 Accordingly, it has been extensively employed during modification of a wide variety of polymer materials including polyimide, 38,39 polyamide, 40 and polysulfone 41 to achieve optimal performance.…”

Section: Introductionmentioning

confidence: 99%

Synergistic enhancement of interfacial adhesion for CF/PEEK composites through carbene chemistry and water‐based self‐catalyzed cross‐linkable PENK‐NH₂ sizing agent

Guo,

Pei,

Dai

et al. 2024

Polymer Composites

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To address the issue of inadequate interfacial adhesion in carbon fiber/poly ether ether ketone (CF/PEEK) composites, an innovative approach that combines carbene chemistry and sizing treatment was meticulously designed to achieve remarkable synergistic enhancement. Specifically, cyano groups were chemical‐grafted on CF surface via carbene reaction. Meanwhile, a water‐based self‐catalyzed cross‐linkable PENK‐NH2 sizing agent with good storage stability was prepared. Noteworthy, the presence of amino groups as blocking agents of sizing agent significantly accelerated the rate of cyano‐crosslinking, thus effectively avoiding the adverse effects of excessively prolonged cross‐linking period during composites preparation. As a result, robust interaction between cyano‐modified CF and PEEK was established by cross‐linking reaction, along with chemical bonds generated between amino groups of sizing agent and ketone groups in PEEK. The maximum interlaminar shear strength (ILSS) of CF‐CN‐1.5/PEEK composites was 22.0% and 57.0% higher than CF‐1.5/PEEK and CF/PEEK composites. Furthermore, the presence of cyano‐cross‐linked structure endowed interphase with outstanding solvent‐resistance, the mechanical properties of CF composites after solvent treatment were well‐preserved. The strong synergistic interfacial interactions facilitated by chemical bonds in different components provide an effective and fascinating methodology for producing high‐performance CF/composites.Highlights Water‐based self‐catalyzed cross‐linkable PENK‐NH2 sizing agents for CF/PEEK were prepared. NH2 was introduced to avoid the adverse effects of prolonged cyano‐crosslinking. Designed carbenoid motif with cyano group was grafted on CF via carbene chemistry. The interaction between sizing agent and CF was boosted by the cyano‐crosslinking. Mechanical properties of sized composites corroded by solvent were well‐preserved.

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“…Besides, one-component PN resins could effectively avoid the disadvantages of curing agent degradation or volatilization at a high temperature, 38 which would cause processing difficulties and led to voids and defects. 39,40 In this work, a phthalonitrile monomer 4,4′-((disulfanediylbis(4,1-phenylene))bis(oxy))diphthalonitrile (DPBPN) containing disulfide segments was synthesized by a simple nucleophilic substitution reaction, and its curing reaction was promoted by disulfide segments. The monomer 4,4′-((thiobis(4,1-phenylene))bis(oxy))diphthalonitrile (TPBPN) without disulfide segments was synthesized as a control.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Furthermore, it may serve as direct evidence of the free radical curing process of PN resins. Besides, one-component PN resins could effectively avoid the disadvantages of curing agent degradation or volatilization at a high temperature, which would cause processing difficulties and led to voids and defects. , …”

Section: Introductionmentioning

confidence: 99%

Self-Curing Phthalonitrile Resin with Disulfide Bond as the Curing Group

Hu,

Pu,

Zhou

et al. 2023

ACS Appl. Polym. Mater.

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To further investigate the presence of a radical mechanism in the curing process of phthalonitrile resins, a conventional radical initiation unit (disulfide segment) was introduced into phthalonitrile resins for the first time. A disulfide-bond-containing phthalonitrile monomer (DPBPN) was successfully synthesized. Its self-curing reaction could be promoted by disulfide segments in the precursor. Rheological measurements and differential scanning calorimetry showed that DPBPN exhibited a low melting point (124.5 °C) and a wide processing window (120 °C). Infrared spectroscopy confirmed the formation of isoindoline, triazine, and phthalocyanine structures in the product. Thermal gravimetric analysis and dynamic mechanical analysis suggested the outstanding thermal stability and high glass transition temperature (T g) of the cured resin with a moderate curing process.

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Dual-curing propargyl-phthalonitrile imide-based thermoset: Synthesis, characterization and curing behavior

Cited by 20 publications

References 60 publications

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Synergistic enhancement of interfacial adhesion for CF/PEEK composites through carbene chemistry and water‐based self‐catalyzed cross‐linkable PENK‐NH₂ sizing agent

Self-Curing Phthalonitrile Resin with Disulfide Bond as the Curing Group

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Dual-curing propargyl-phthalonitrile imide-based thermoset: Synthesis, characterization and curing behavior

Cited by 20 publications

References 60 publications

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Synergistic enhancement of interfacial adhesion for CF/PEEK composites through carbene chemistry and water‐based self‐catalyzed cross‐linkable PENK‐NH2 sizing agent

Self-Curing Phthalonitrile Resin with Disulfide Bond as the Curing Group

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Product

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Synergistic enhancement of interfacial adhesion for CF/PEEK composites through carbene chemistry and water‐based self‐catalyzed cross‐linkable PENK‐NH₂ sizing agent