Novel high-performance poly(benzoxazole-co-imide) resins with low dielectric constants and superior thermal stabilities derived from thermal rearrangement of ortho-hydroxy polyimide oligomers

Li, Xiuting; Liu, Tian; Jiao, Yuzhang; Gan, Feng; Zhao, Xin; Dong, Jie

doi:10.1016/j.cej.2018.11.175

Cited by 96 publications

(59 citation statements)

References 40 publications

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“…At the same time, fluorine-containing groups with larger volume were introduced into polymer molecules to increase the free volume between molecular chains to reduce the dielectric constants and loss. Moreover, the introduction of fluorinated groups can improve the thermal properties of polymers to a certain extent because of the high binding energy of C–F bonds (489 kJ/mol) [23,24].…”

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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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: 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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“…The two aromatic diamines were synthesized and used to incorporate the ortho -hydroxyl-substituted benzamide units into the derived PIs, which was thought to be one of the most promising precursors for PBO synthesis. Generally, benzoxazole rings could be formed through several routes, such as the decarbonation (–CO 2 ) and rearrangement reactions via ortho -hydroxyl substituted imide rings [ 30 , 31 ], the dehydration reaction via ortho -hydroxyl substituted benzamide [ 32 ], and so on. Compared with the former technical route of decarbonation, the latter dehydration route usually requires more mild thermodynamic and kinetic conditions to form benzoxazole.…”

Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Electrospun Fluoro-Containing Poly(imide-benzoxazole) Nano-Fibrous Membranes with Low Dielectric Constants and High Thermal Stability

et al. 2021

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The rapid development of advanced high-frequency mobile communication techniques has advanced urgent requirements for polymer materials with high-temperature resistance and good dielectric properties, including low dielectric constants (low-Dk) and low dielectric dissipation factors (low-Df). The relatively poor dielectric properties of common polymer candidates, such as standard polyimides (PIs) greatly limited their application in high-frequency areas. In the current work, benzoxazole units were successfully incorporated into the molecular structures of the fluoro-containing PIs to afford the poly(imide-benzoxazole) (PIBO) nano-fibrous membranes (NFMs) via electrospinning fabrication. First, the PI NFMs were prepared by the electrospinning procedure from organo-soluble PI resins derived from 2,2’-bis(3,4-dicarboxy-phenyl)hexafluoropropane dianhydride (6FDA) and aromatic diamines containing ortho-hydroxy-substituted benzamide units, including 2,2-bis[3-(4-aminobenzamide)-4-hydroxylphenyl]hexafluoropropane (p6FAHP) and 2,2-bis[3-(3-aminobenzamide)-4-hydroxyphenyl]hexafluoropropane (m6FAHP). Then, the PI NFMs were thermally dehydrated at 350 °C in nitrogen to afford the PIBO NFMs. The average fiber diameters (dav) for the PIBO NFMs were 1225 nm for PIBO-1 derived from PI-1 (6FDA-p6FAHP) precursor and 816 nm for PIBO-2 derived from PI-2 (6FDA-m6FAHP). The derived PIBO NFMs showed good thermal stability with the glass transition temperatures (Tgs) over 310 °C and the 5% weight loss temperatures (T5%) higher than 500 °C in nitrogen. The PIBO NFMs showed low dielectric features with the Dk value of 1.64 for PIBO-1 and 1.82 for PIBO-2 at the frequency of 1 MHz, respectively. The Df values were in the range of 0.010~0.018 for the PIBO NFMs.

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“…Conventional PIs are known as infusible polymer with poor processability, but synthesized fluorinated PIs had excellent solubility with various organic solvents. Especially, fully fluorinated PIs (2,3,6) using AHHFP and TFDB were well dissolved at room temperature in common solvents, such as CHCl 3 and toluene [32]. In addition, some hydrothermally synthesized PIs were dissolved in ethanol which is known as representative non-solvent of PIs [33].…”

Section: Solubility and Processabilitymentioning

confidence: 99%

“…Aromatic polyimides (PIs) are the most valuable super engineering polymer with its excellent thermal stability, mechanical properties, insulating ability and chemical resistance. Due to those excellent characteristics, they are widely applied and studied in high-tech industries [1][2][3][4]. The most typical application of PIs is the semiconductor and aerospace field as an insulator, due to their thermal resistance to the extreme condition; they are also utilized as a substrate or as cover window for a device with their flexibility and excellent mechanical strength [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Highly Soluble Fluorinated Polyimides Synthesized with Hydrothermal Process towards Sustainable Green Technology

et al. 2021

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Polyimides, a widely used engineering plastic, require use of large amounts of toxic and hazardous organic solvents which threaten our daily lives, calling for new and easy synthetic methods for sustainable environmentally friendly development. In this paper, highly soluble fluorinated polyimides based on 4,4′-(hexafluoroisopropylidene) diphthalic anhydride were synthesized via hydrothermal process without using any toxic organic solvents and the advantages of the newly demonstrated synthetic methods are shown by comparative analysis performed with the two conventional synthetic methods using organic solvent: thermal and chemical imidization. Lower temperature is required (~200 °C) compared to thermal imidization and functional groups for high fusibility formed more easily compared to chemical imidization. According to the comparative analysis, hydrothermally synthesized PIs showed excellent solubility and maintained high thermal stability (>500 °C) and glass transition temperature (>300 °C) compared to conventional PI. The hydrothermally synthesized polyimide is much more convenient to store and manage than other form of polyimide which is much more stable when it is exposed to humidity as it is a powder form. The hydrothermal synthetic method is verified to be a “Green” and facile method for sustainable PI synthesis.

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Novel high-performance poly(benzoxazole-co-imide) resins with low dielectric constants and superior thermal stabilities derived from thermal rearrangement of ortho-hydroxy polyimide oligomers

Cited by 96 publications

References 40 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

Preparation and Characterization of Electrospun Fluoro-Containing Poly(imide-benzoxazole) Nano-Fibrous Membranes with Low Dielectric Constants and High Thermal Stability

Highly Soluble Fluorinated Polyimides Synthesized with Hydrothermal Process towards Sustainable Green Technology

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