High Glass Transition of Fluorinated Polyimides Derived from 4‐(3,4‐Difluorophenyl)‐2,6‐bis(4‐aminophenyl)pyridine

Xu, Xu; Chen, Beicai; Li, Hua; Huang, Xiaohua; Wei, Chun

doi:10.1002/cjoc.201600615

Cited by 5 publications

(2 citation statements)

References 29 publications

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“…via nitrification and reduction, as we previously described. 31 The specific steps of the synthesis and the results of the characterization data are described in the supporting material (Scheme S1, Figure S1 to S5).…”

Section: Monomer Synthesismentioning

confidence: 99%

Preparation and characterisation of heat‐resistant fluorinated co‐polyimides and their gas transport characteristics

Shi,

Li,

et al. 2024

High Performance Polymers

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A series of fluorinated co-polyimide films based on the 6FDA-FTPPA/BAFL backbone were prepared from 4-(3-fluoro-4-(trifluoromethyl)phenyl)-2,6-bis(4-aminophenyl)pyridine (FTPPA),commercial 9,9-bis(4-aminophenyl)fluorene (BAFL), and 4,4’-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), with varying ratios of FTPPA:BAFL units (3:1, 2:1, 1:1, 1:2, and 1:3). Co-polyimides not only exhibit high thermal stability ( Tg > 357°C), good optical properties (λcutoff > 327 nm) and hydrophobicity (contact angle >91.4°), but also favorable solubility properties in both high and low boiling organic solvents. The fractional free volume of the polymers was simulated using molecular mechanics and molecular dynamics and correlated with experimental gas separation data. The presence of bulky groups led to high FFVs (>17.8%) and the formation of large microcavities with diameters ranging from 5.48 to 5.72 Å, which efficiently increased gas permeability. In pure gas permeation experiments, the permeability coefficients of CO2 and He for the 6FDA-FTPPA/BAFL (3:1) film were 41.48 and 79.38 bar, respectively, which were superior to those of commercial Matrimid and Kapton in terms of gas permeability. In especial, the 6FDA-FTPPA/BAFL (1:2) and 6FDA-FTPPA/BAFL (1:3) in co-polyimide membranes exhibited the most attractive separation performance for O2/N2 gas pairs, approaching the 1991 Roberson upper limit.

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Section: Monomer Synthesismentioning

confidence: 99%

Preparation and characterisation of heat‐resistant fluorinated co‐polyimides and their gas transport characteristics

Shi,

Li,

et al. 2024

High Performance Polymers

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“…In general, the introduction of rigid heteroaromatic pyridine ring into the polymer chain could endow aromatic polyimides with excellent thermal stability. 35 –37 Guan et al 37 reported a series of polyimides containing pyridine and sulfur units with outstanding thermal stability, excellent mechanical, and good optical properties.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of high heat-resistant, soluble, and hydrophobic fluorinated polyimides containing pyridine and trifluoromethylthiophenyl units

Huang

Liu

et al. 2017

High Performance Polymers

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In this study, a novel diamine monomer, 4-(4-trifluoromethylthiophenyl)-2,6-bis(4-aminophenyl)pyridine (FTPAP) was synthesized through two-step reaction from 4-trifluoromethylthiobenzaldehyde and 4-nitroacetophenone as raw materials, and then the structure of FTPAP was characterized by Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance, and mass spectrometry. A series of fluorinated polyimides were prepared from FTPAP with five commercial dianhydrides, namely, pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, oxydiphtahalic anhydride, benzophenone tetracarboxylic dianhydride, and 4,4′-(hexafluoroisopropylidene) diphthalic anhydride. The structure and performance of the fluorinated polymers were fully characterized by FTIR, differential scanning calorimetry, thermogravimetric analysis, and wide-angle X-ray diffraction (WAXD). The inherent viscosity of polymers ranged from 0.41 to 1.45 dL g−1. These polymers displayed good solubility in polar aprotic solvents, such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone, at room temperature or on heating. Furthermore, they exhibited outstanding thermal stability with glass transition temperatures beyond 305°C, and the temperature of 10% weight loss was in the range of 514–573°C with more than 56% residue at 800°C under nitrogen. Moreover, they showed high optical transparency with the cutoff wavelengths in the range of 385–457 nm and excellent hydrophobic property with contact angle in the range of 82.8–97.6°. In addition, the results of WAXD indicated that all of the polymers presented amorphous structure.

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Fabrication and characterization of soluble, high thermal, and hydrophobic polyimides based on 4‐(3,5‐dimethoxyphenyl)‐2,6‐bis(4‐aminophenyl)pyridine

Huang

Chen

Liu

et al. 2017

J of Applied Polymer Sci

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A novel aromatic diamine monomer, 4-(3,5-dimethoxyphenyl)-2,6-bis(4-aminophenyl)pyridine (DPAP) was successfully synthesized by 4 0 -nitroacetophenone and 3,5-dimethoxybenzaldehyde as raw material. The structure of DPAP was confirmed by Fourier transform infrared, nuclear magnetic resonance, and mass analysis. A series of polyimides (PIs) were obtained by polycondensation with various dianhydrides via the conventional two-step method. These PIs showed good solubility in organic solvents. They also presented high thermal stability, the glass transition temperatures (T g ) of polymers were in the range of 325-388 8C, and the temperature at 10% weight loss was in the range of 531-572 8C. Furthermore, these polymers also exhibited outstanding hydrophobicity with the contact angles in the range of 89.18-93.58. Moreover, the results of wide-angle X-ray diffraction (WAXD) confirmed these polymers showed amorphous structure.

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High Glass Transition of Fluorinated Polyimides Derived from 4‐(3,4‐Difluorophenyl)‐2,6‐bis(4‐aminophenyl)pyridine

Cited by 5 publications

References 29 publications

Preparation and characterisation of heat‐resistant fluorinated co‐polyimides and their gas transport characteristics

Preparation and characterisation of heat‐resistant fluorinated co‐polyimides and their gas transport characteristics

Design and synthesis of high heat-resistant, soluble, and hydrophobic fluorinated polyimides containing pyridine and trifluoromethylthiophenyl units

Fabrication and characterization of soluble, high thermal, and hydrophobic polyimides based on 4‐(3,5‐dimethoxyphenyl)‐2,6‐bis(4‐aminophenyl)pyridine

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