Reduced curing kinetic energy and enhanced thermal resistance of phthalonitrile resins modified with inorganic particles

Song, Yuanyuan; Zong, Lishuai; Bao, Feng; Li, Guiyang; Wu, Zuoqiang; Li, Nan; Wang, Jinyan; Jian, Xigao

doi:10.1002/pat.4301

Cited by 22 publications

(9 citation statements)

References 45 publications

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“…At the same time, no obvious exothermic phenomenon was observed, indicating that the BOPN monomer would not undergo bulk polymerization in the absence of catalyst containing active hydrogen. Due to the introduction of high‐density aromatic ether bond into the structure of the monomer, the melting point of the BOPN monomer is lower than those of other ordinary phthalonitrile monomers . After addition of the curing agent, the curve of the mixture showed an exothermic peak at 253 °C owing to the exothermic curing of BOPN monomer.…”

Section: Resultsmentioning

confidence: 99%

A Phthalonitrile Resin with a Low Melting Point and High Storage Modulus Containing High‐Density Aromatic Ether Bonds

Shi

Bai

et al. 2020

ChemistrySelect

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A low melting point phthalonitrile monomer named 4,4'-((((((2cyano-1,3-phenylene)bis(oxy))bis(4,1-phenylene))bis(oxy))bis (4,1-phenylene))bis(oxy))diphthalonitrile (BOPN), was synthesized by nucleophilic substitution of 4,4'-oxydiphenol with 2,6dichlorobenzonitrile. The BOPN resin containing high-density aromatic ether bonds were prepared via bulk addition polymerization. Two kinds of polymers were prepared from BOPN monomer by using 4-(aminophenoxy)phthalonitrile (APPH) as the curing agent under different curing procedures. The chemical structure of the monomer was determined by Nuclear Magnetic Resonance spectroscopy (NMR) and Fourier Transform Infrared spectroscopy (FTIR). Dynamic Mechanical Analysis (DMA) demonstrated that the storage modulus of the resin at room temperature was 3712 MPa and the glass transition temperature was above 400°C. Differential Scanning Calorimetric (DSC) analysis and rheological test indicated that the melting point and processing window of the monomer were 92°C and 118°C, respectively. The temperature for 95 % weight retention of the polymer in air was 529°C.

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Section: Resultsmentioning

confidence: 99%

A Phthalonitrile Resin with a Low Melting Point and High Storage Modulus Containing High‐Density Aromatic Ether Bonds

Shi

Bai

et al. 2020

ChemistrySelect

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“…BPPN was prepared according to Song’s method: FTIR (KBr, cm −1 ): 2231 (CN); 1246, 1174 (C–O–C); 1 H-NMR (DMSO, δ , ppm) 8.15–8.13 (2 H, d); 7.87 (2 H, s); 7.84–7.81 (4 H, d); 7.48–7.45 (2 H, d); and 7.32–7.30 (4 H, d). 17 The structure of the BPPN monomer is shown in Figure 2.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of a novel silicon-containing phthalonitrile resin and its quartz-fiber-reinforced composites

Deng

et al. 2020

High Performance Polymers

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A novel silicon-containing phthalonitrile monomer named bis(4-(4′-(4′-phenoxy)phenyl)phenyl)dimethylsilane phthalonitrile (SiBPPN) was successfully designed and synthesized. The chemical structure was characterized by proton nuclear magnetic resonance and Fourier transform infrared (FTIR) analyses, and its molecular weight was determined by mass spectrometry. Its melting point is lower than that of 4,4′-bis(3,4-dicyanophenoxy)biphenyl (BPPN), which has no silicon atom, and its solubility is also much better than that of BPPN. The curing behavior of SiBPPN was studied by differential scanning calorimetry and FTIR analyses in detail. The thermal and thermomechanical properties of the polymer and laminate were studied by thermogravimetric analysis and dynamic mechanical analysis. The results show that the cured SiBPPN (c-SiBPPN) possesses excellent thermal and mechanical properties. Under nitrogen atmosphere, its residual weight ratio at 800°C is 81.5% and the 5% thermal degradation temperature is 546°C. In addition, quartz-fiber (QF)-reinforced c-SiBPPN composites exhibit mechanical properties superior to those of QF-reinforced cured BPPN composites. The interlaminar shear strength and bending strength of the composite are 30.44 and 389 MPa at room temperature, and the interlaminar shear strength and bending strength of the composite are 22.25 and 339 MPa at 300°C.

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“…Remarkably, the combination of both organic and inorganic constituents opened an efficient way to fabricate phthalonitrile resin [ 3 , 24 , 25 ]. As a polyhedral cage boron cluster compound, carborane was formed when some boron atoms in the cluster were replaced by carbon atoms [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Polymerization of Phthalonitrile Resins by Carborane with Enhanced Thermal Oxidation Resistance: Experimental and Molecular Simulation

Jia

Bu²,

Dong

et al. 2022

Polymers

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Biphenyl phthalonitrile (BPh) resins with good thermal and thermo-oxidative stability demonstrate great application potential in aerospace and national defense industries. However, BPh monomer has a high melting point, poor solubility, slow curing speed and high curing temperature. It is difficult to control the polymerization process to obtain the resins with high performance. Here, a BPh prepolymer (BPh-Q) was prepared by reacting 1,7-bis(hydroxymethyl)-m-carborane (QCB) with BPh monomers. The BPh-Q exhibited much better solubility, faster curing speed and lower curing temperature compared with pure BPh and BPh modified with bisphenol A (BPh-B, a common prepolymer of BPh). Thus, the polymerization process of BPh was greatly accelerated at a low temperature, resulting in a BPh resin with enhanced thermostability and oxidation resistance. The experimental and theoretical models revealed the promotion effect of B-H bond on the curing reaction of phthalonitrile via Markovnikov addition reaction due to the special steric structure of carborane. This study provided an efficient method to obtain low-temperature curing phthalonitrile resins with high thermal and thermo-oxidative resistance, which would be potentially useful for the preparation of high-performance cyanide resin-based composites.

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Reduced curing kinetic energy and enhanced thermal resistance of phthalonitrile resins modified with inorganic particles

Cited by 22 publications

References 45 publications

A Phthalonitrile Resin with a Low Melting Point and High Storage Modulus Containing High‐Density Aromatic Ether Bonds

A Phthalonitrile Resin with a Low Melting Point and High Storage Modulus Containing High‐Density Aromatic Ether Bonds

Synthesis and properties of a novel silicon-containing phthalonitrile resin and its quartz-fiber-reinforced composites

Catalytic Polymerization of Phthalonitrile Resins by Carborane with Enhanced Thermal Oxidation Resistance: Experimental and Molecular Simulation

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