Synthesis and characterization of fluorinated polyimides derived from 1,4-bis-[4-amino-2-(trifluoromethyl)-phenoxy] benzene/tetrafluoride benzene

Gao, Yueyi; Zhou, Yuming; He, Min; Wang, Haiyun; Cui, Yiping; Zhang, Tong

doi:10.1080/15685551.2014.907615

Cited by 11 publications

(4 citation statements)

References 32 publications

(28 reference statements)

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“…For example, poor solubility in most organic solvents, high softening and meting temperatures, and deeply color that often limit their widespread application in various advanced technologies [13,14,15,16,17,18,19]. Thus, many efforts have been devoted to improving the solubility, processability, and highly optical transparent of PIs by the incorporation of flexible or twist linkages [20,21,22,23], asymmetric noncoplanar units [24,25,26], bulky pendant groups [27,28,29], and fluorinated substituents [30,31,32,33,34] into the polymer backbones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

et al. 2017

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Abstract:A novel aromatic diamine monomer, 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine (PPAPP) containing pyridine rings, pyrrolidine groups, and ether linkages, was successfully synthesized using 4-hydroxyacetophenone and 1-chloro-4-nitrobenzene as starting materials by three-step reactions, and then used to synthesize a series of polyimides by polycondensation with various aromatic dianhydrides via a two-step method. The structure of PPAPP was characterized by NMR, FT-IR, and mass spectrometry analysis methods. These polymers showed good solubility in common organic solvents (e.g., NMP, DMF, DMSO, and DMAc) at room temperature or on heating. Moreover, they presented a high thermal stability with the glass transition temperature (T g s) exceeding 316 • C, as well as the temperature of 10% weight loss ranged from 552 to 580 • C with more than 67% residue at 800 • C under nitrogen. Furthermore, they also exhibited excellent hydrophobicity with a contact angle in the range of 85.6 • -97.7 • , and the results of Wide-Angle X-ray Diffraction (WAXD) indicated that all of the polymers revealed an amorphous structure.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

et al. 2017

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“…Unfortunately, it will sacrifice some of their advantageous properties by the modification method, such as thermal stability and mechanical property. It must be emphasized that much efforts have been devoted to synthesizing fluorinated polyimide by incorporation of fluorinated substituent, especially the trifluoromethyl group [24][25][26][27][28]. The optical transparency and solubility of fluorinated polyimide has been significantly improved, which resulted from low polarizability of the bond and the increase in free volume.…”

Section: Introductionmentioning

confidence: 98%

Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties

et al. 2015

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A series of novel organo-soluble and optical transparent polyimides were synthesized via conventional one-step polycondensation from a novel diamine, 3,3′-diterbutyl-4,4′-diaminodiphenyl-4″-morpholinophenylmethane (TAMPM) and various commercial aromatic dianhydrides. The structures of monomer and polymers were confirmed by FT-IR and NMR. The solubility, thermal stability, optical transparency, dielectric and hydrophobic properties of polyimides were investigated. The results showed polymers presented excellent solubility in common organic solvents, such as N,Ndimethylformamide (DMF), N,N-dimethyl acetamide (DMAc), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), chloroform (CHCl 3 ), tetrahydrofuran (THF) and dichloromethane (CH 2 Cl 2 ). The polymers exhibited prominent thermal stability and high optical transparency with the glass transition temperature (T g ) in the range of 311-355°C, and the cutoff wavelengths in the range of 287-344 nm. Furthermore, all of the polymers also presented low dielectric constants in the range of 2.85-3.16 at 1 MHz, and outstanding hydrophobic properties with the contact angle in the rang of 85.1-94.2 o .

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“…It is well known that fluorinated polyimide (FPIs) presented excellent solubility, outstanding mechanical properties, good thermal stability, high optical transparency, prominent hydrophobicity, low dielectric constants, low birefringence, and low refractive index. 23 –29 These overall properties of FPIs are attributed to the special characteristics of fluorine, such as small dipole, high electron negativity, oxidization resistance, hydrophobicity, and low polarizability. Tapaswi et al 28 designed and synthesized two new perfluorodecylthio-substituted aromatic diamines, 2,4-diamino-1-(1 H ,1 H ,2 H ,2 H -perfluorodecathio)benzene and 2,2′-bis((1 H ,1 H ,2 H ,2 H -perfluorodecyl)thio) (1,1′-biphenyl)4,4′-diamine, and then polycondensed with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) to prepare two new perfluorinated PIs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of organosoluble, transparent, and hydrophobic fluorinated polyimides derived from 3,3′-diisopropyl-4,4′-diaminodiphenyl-4′′-trifluoromethyltoluene

Liu

Pei

Mei

et al. 2016

High Performance Polymers

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A novel aromatic fluorinated diamine monomer, 3,3′-diisopropyl-4,4′-diaminodiphenyl-4′′-trifluoromethyltoluene, was synthesized by coupling of 2-isopropylaniline and 4-(trifluoromethyl)benzaldehyde and its structure was confirmed by Fourier transform infrared spectroscopy, nuclear magnetic resonance, elemental analysis, and mass spectrometry, and then used to prepare a series of fluorinated polyimides (FPIs) by polycondensation reaction with various commercial dianhydrides via conventional one-step method. The obtained FPIs present excellent solubility in most organic solvents and enough to cast into tough and flexible films. All the FPI films show good optical transparency and light color with the cutoff wavelengths in range of 307–362 nm and the average transmittance above 86%. These polymer films also exhibit high glass transition temperature in range of 261–331°C and thermal stability with 10% weigh loss above 463°C under nitrogen atmosphere. Furthermore, they exhibit outstanding mechanical properties with tensile strengths of 65.9–94.3 MPa, elongation at break of 11.4–13.8%, Young’s modulus of 1.6–1.9 GPa, and low dielectric constants in range of 2.75–3.10 at 1 MHz as well as prominent hydrophobicity with the contact angle in the range of 87.3–93.9°.

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Synthesis and characterization of fluorinated polyimides derived from 1,4-bis-[4-amino-2-(trifluoromethyl)-phenoxy] benzene/tetrafluoride benzene

Cited by 11 publications

References 32 publications

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties

Synthesis and characterization of organosoluble, transparent, and hydrophobic fluorinated polyimides derived from 3,3′-diisopropyl-4,4′-diaminodiphenyl-4′′-trifluoromethyltoluene

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