A new addition thermosetting resin from phthalonitrile functionalized [2.2]paracyclophane

Lv, Juan; Xiao, Hang; Liang, Bo; Chen, Li; He, Xiancong; Zeng, Ke; Ye, Gang

doi:10.1016/j.polymer.2021.124123

Cited by 13 publications

(5 citation statements)

References 37 publications

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“…Our previous work reported a heat-induced synergistic polymerization effect between aromatic methylene and phthalonitrile, 24 and this curing system was successfully applied in the crosslinking modification of polyimide. 25 According to the summary of these works, [24][25][26][27][28][29] we speculate that scope of this synergistic polymerization effect could be extended from phthalonitrile to intrinsic aromatic cyano. Meanwhile, it may provide some new inspirations for the curing of mono-cyano.…”

Section: Introductionmentioning

confidence: 90%

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Crosslinking modification of poly(arylene ether nitriles) (PEN) based on the synergistic polymerization of aromatic methylene and mono‐cyano

Hong

Zhu

et al. 2022

Journal of Polymer Science

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In order to improve the heat‐resistance of poly(arylene ether nitriles) (PEN), a novel mono‐cyano crosslinking strategy—heat‐induced synergistic polymerization of aromatic methylene and mono‐cyano is proposed and applied in the PEN system. A self‐crosslinkable PEN containing aromatic methylene moieties (PEN‐F) is synthesized by a simple solution polycondensation. PEN‐F can significantly crosslink during relatively mild heat treatment at 300–325°C without any catalyst, transferring from thermoplastic polymers to thermosetting polymers. XRD, FTIR, TGA, DSC and DMA are applied to evaluate the crystallinity, structural evolution and thermal properties of PEN‐F before and after crosslinking. The results suggest that the uncured PEN‐F is amorphous and soluble in some common solvents (THF, DMAc, NMP, etc.). After curing, the heat and solvent resistance of PEN‐F improve remarkably. Especially, the resulting crosslinked product PEN‐F‐325 exhibits a high glass transition temperature (Tg) value of 320°C measured by DMA, increased by 148°C compared to uncured PEN‐F (Tg = 172°C), potentially applicable for high temperature services.

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Section: Introductionmentioning

confidence: 90%

“…It suggested that the intrinsic nitrile in PEN was stable within the heat treatment temperature range used in this work. According to our previous work and some research on cyano reaction in foundation chemistry, 24,26,28,29,[33][34][35] the possible reaction process was illustrated in Scheme 3.…”

Section: Structural Analysis Of Pen Filmsmentioning

confidence: 99%

Crosslinking modification of poly(arylene ether nitriles) (PEN) based on the synergistic polymerization of aromatic methylene and mono‐cyano

Hong

Zhu

et al. 2022

Journal of Polymer Science

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“…[3] However, PN resins still have some disadvantages, such as high monomer melting point and narrow processing window, which limit its further applications. [4] Low melting point phthalonitrile monomers were successfully synthesized by introducing oxyether bond, [5] thioether bond, [6] oxyphosphorus bond [7] and silicon oxygen bond [8] in the main chain, and also various rigid structures like paracyclophane group, [9] adamantane group, [10] spirocycle acetal group, [11] triazine group [12] and fluorene group [13] were introduced into the main chain to improve thermal oxidative stability of the resin. He et al [14] prepared a phthalonitrile resin based on tyrosine which showed a T 5% of 515 °C and weight retention of 73 % at 800 °C under N 2 with a T g around 430 °C.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Pyrimidine‐Based Novel Phthalonitrile Resins with Excellent Processing Performance and High Glass Transition Temperature

Zhang

Rong

et al. 2023

ChemistrySelect

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Three phthalonitrile monomers containing pyrimidine ring and benzene ring side group were successfully synthesized with 4, 6‐dichloro‐2‐phenylpyrimidine, three kinds of phenols (resorcinol, bisphenol A and bisphenol AF) and 4‐nitrophthalonitrile via nucleophilic substitution reaction. All the phthalonitrile monomers exhibited excellent processing performance due to low melting points (Tm) (below 100 °C) and wide processing windows (difference between melting temperature and curing temperature) above 140 °C. By introducing pyrimidine ring and benzene ring side group, the lower melting point of monomers did not affect the thermal stability and thermal mechanical properties of the phthalonitrile resins based on different bisphenols. In particular, 5 % thermal decomposition temperature (T5%) and glass transition temperature (Tg) of phthalonitrile resin based on resorcinol surpassed 455 and 400 °C while storage modulus (E′) was 3209 MPa. Therefore, phthalonitrile resin containing pyrimidine ring and benzene ring side group have potential applications in the field of high temperature resistant polymers and composites.

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“…However, high melting point and curing temperature of PN monomers resulted in their poor processability. − It meant higher equipment requirements and more energy consumption during processing. Introducing flexible aliphatic segments and asymmetric structures was an effective strategy to reduce the melting point of PN monomers.…”

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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A new addition thermosetting resin from phthalonitrile functionalized [2.2]paracyclophane

Cited by 13 publications

References 37 publications

Crosslinking modification of poly(arylene ether nitriles) (PEN) based on the synergistic polymerization of aromatic methylene and mono‐cyano

Crosslinking modification of poly(arylene ether nitriles) (PEN) based on the synergistic polymerization of aromatic methylene and mono‐cyano

Synthesis and Characterization of Pyrimidine‐Based Novel Phthalonitrile Resins with Excellent Processing Performance and High Glass Transition Temperature

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

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