Synthesis and characterization of novel fluorinated pyridine-based polyimides derived from 4-(4-trifluoromethylphenyl)-2,6-bis(4-aminophenyl)pyridine and dianhydrides

2017 ◽  
Vol 30 (4) ◽  
pp. 500-508 ◽  
Author(s):  
Shui-Xiu Huang ◽  
Xiao-Ling Liu ◽  
Mei-Hong Wei ◽  
Zhen-Zhong Huang ◽  
Shou-Ri Sheng

A series of new fluorinated pyridine-based polyimides (PIs) was synthesized by polycondensation of 4-(4-trifluoromethylphenyl)-2,6-bis(4-aminophenyl)pyridine with various aromatic dianhydrides in N, N-dimethylacetamide (DMAc) via the conventional two-step method. The inherent viscosities of the resulting poly(amic acid)s and PIs were 0.54–0.94 and 0.58–0.88 dLg−1, respectively. The obtained PIs were predominantly amorphous and soluble in polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, and DMAc at room temperature or upon heating at 70°C. They also displayed good thermal stability with the glass transition temperature of 324–416°C, the temperature at 5% weight loss of 546–584°C, and the residue of 58–69% at 750°C under nitrogen, as well as outstanding mechanical properties with tensile strengths of 69132 MPa, tensile moduli of 1.1–2.0 GPa, and elongations at break of 7–27%. Meanwhile, these PI films had dielectric constants of 2.95–3.22 (1 MHz), low water uptake 0.44–0.71%, and high optical transparency with the ultraviolet cutoff wavelength in the 388–406 nm range and the wavelength of 80% transparency in the range of 550–680 nm.

2020 ◽  
Vol 32 (9) ◽  
pp. 1001-1009
Author(s):  
Yi-Sheng Luo ◽  
Qiu-Ying Wang ◽  
Xue-Chun Mao ◽  
Shou-Ri Sheng

A new aromatic diamine, 10,10-bis[4-(4-aminophenoxy)phenyl]-9(10 H)-anthrone (BAPA) has been synthesized from anthrone via three-step procedure. Direct phosphorylation polycondensation of BAPA with various aromatic dicarboxylic acids produced a series of cardo poly(ether amide)s with inherent viscosities of 0.97–1.29 dL g−1. All the polymers were readily soluble in polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide (DMAc), and pyridine at room temperature, and afforded transparent, strong, and flexible films upon casting from DMAc solvent. The resulting poly(ether amide)s had glass transition temperatures of 254–316°C, 10% weight loss temperatures of 495–524°C, and char yields of 55–70% at 800°C in nitrogen. These polymers were amorphous and their films exhibited tensile strengths of 81.6–104.7 MPa, tensile moduli of 1.8–2.4 GPa, and elongations at break of 8–15%.


1993 ◽  
Vol 5 (3) ◽  
pp. 187-196 ◽  
Author(s):  
Frank W Mercer

A general method for the preparation of amide-containing aromatic polyether ketones has been developed. Polymerization is based on a ketone-activated halo displacement in amide-containing bis(4-fluorobenzoyl) moieties by phenoxides. N,N-Bis[4-(4-fluorobenzoyl)-(4-phenoxyphenylJ]terephthalamide and 4-[(4-fiuorobenzoyl)-(4-phenoxyphenylcarbamoyl)]-N-[(4-fluorobenzoyl)-(4-phenoxyphenyl)]phthalimide were prepared by reaction of 4-fluoro-benzoyl chloride with N,N.bis(4-phenoxyphenyl)terephthalamide and 4-(4.phenoxy-phenylcarbamoyl)-N-(4-phenoxyphenyl)phthalimide, respectively, in dichloromethane in the presence of aluminum chloride. Reaction of N,N-bis[4-(4-fluorobenzoyl)-(4-phenoxyphenyl)]-terephthalamide and 4-[(4-fluorobenzoyl(4-phenoxyphenylcarbamoyl)]-N-[(4-fluorobenzoyl)-(4-phenoxyphenyl)]phthalimide with diphenols in an aprotic solvent in the presence of potassium carbonate gave a series of aromatic poly(ether ketone amide)s. Films of the aromatic poly(ether ketone amide)s displayed good thermal stability, flexibility, and T, values ranging from 134 to 186 CC. The dielectric constants of the films were characterized as a function of relative humidity (RH).


2018 ◽  
Vol 31 (5) ◽  
pp. 485-496 ◽  
Author(s):  
Xiao-Lan Zhang ◽  
Xiao-Ling Liu ◽  
Qiu-Ying Wang ◽  
Zhen-Zhong Huang ◽  
Shou-Ri Sheng

4-(4-Trifluoromethylphenyl)-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine (9FPBAPP), as a new aromatic diamine, was prepared by a modified Chichibabin reaction of 4-(4-nitro-2-trifluoromethylphenoxy)acetophenone with 4-triflouromethylbenzaldehyde, followed by a catalytic reduction. A series of fluorinated poly(ether imide)s containing pyridine and/or phenylphosphine oxide moieties were prepared from bis(3-aminophenyl)phenylphosphine oxide (BAPPO), 2,2′-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), and 9FPBAPP via a conventional two-step thermal imidization procedure with various mole ratios of BAPPO and 9FPBAPP. All the polymers were amorphous and soluble in common organic solvents such as N, N-dimethylacetamide and N-methyl-2-pyrrolidone and had Tg’s of 277–285°C, 5% weight loss temperature of 521–550°C in nitrogen. Furthermore, high char yields and good limited oxygen index values indicated that these polymers exhibited good thermal stability and flame-retardant property. Tough and flexible polymer films also had good mechanical properties with tensile strengths of 75–99 MPa, tensile moduli of 1.1–1.6 GPa, and elongations at break of 12%–24% and low dielectric constants of 2.81–3.53 (1 MHz), as well as high optical transparency with the ultraviolet cutoff wavelength in the range of 350–384 nm.


e-Polymers ◽  
2008 ◽  
Vol 8 (1) ◽  
Author(s):  
Chin-Ping Yang ◽  
Sheng-Huei Hsiao ◽  
Yu-Yang Su ◽  
Chun-Hung Lin ◽  
Mei-Yuan Hsu

AbstractA series of novel fluorinated poly(ether imide)s (PEIs) IVa-h were synthesized from 4,4’-(2,5-tolylenedioxy)diphthalic anhydride (I) and various trifluoromethyl-substituted aromatic bis(ether amine)s (IIa-h) via a conventional two-step method with thermal or chemical imidization of the precursor poly(amic acid)s. These PEIs were readily soluble in a variety of organic solvents; they were soluble with a concentration higher than 10% in amide-type polar solvents, ether type solvents, and chlorinated hydrocarbons. The solution-cast films showed a high optical transparency and low color intensity, with an ultraviolet-visible absorption edge of 371- 377 nm and low b* values (a yellowness index) of 4.9-7.5. These films were strong and tough with tensile strength of 90-103 MPa. They exhibited glass-transition temperatures (Tg) in the range of 207-293oC, with 10% weight loss temperature in excess of 500oC in air or nitrogen atmosphere. They also showed low-dielectric constants (2.95-3.37 at 1 MHz) and low moisture absorption (0.20- 0.67 wt %).


1993 ◽  
Vol 5 (1) ◽  
pp. 69-76 ◽  
Author(s):  
Frank W Mercer

A general method for the preparation of oxadiazole containing aromatic poly(ether ketone)s has been developed. Polymerization is based on a ketone-activated halo displacement in oxadiazole containing bis(4-fluorobenzoyl) moieties by phenoxides. 2,5-bis[4-(4-fluorobenzoyl-(4-phenoxyphenyl)]-1,3,4-oxadiazole was prepared by reaction of 4-fluorobenzoyl chloride with 2,5-bis(4-phenoxyphenyl)-1,3,4-oxadiazole in dichloromethane in the presence of aluminium chloride. Reaction of 2,5-bis[4-(4-fiuorobenzoyl)-(4-phenoxyphenyl)]-1,3,4-oxadiazole with diphenols in an aprotic solvent in the presence of potassium carbonate gave a series of aromatic poly(ether ketone oxadiazole)s. Films of the aromatic poly(ether ketone oxadiazole)s displayed good thermal stability, flexibility, and Ts s ranging from 172 to 218 C. The dielectric constants of the films were characterized as a function of relative humidity (RH).


2011 ◽  
Vol 415-417 ◽  
pp. 1789-1793
Author(s):  
Xiang Li Meng ◽  
Peng Wang ◽  
Ling Jiang

Polyimides prepared from 5-amino-2(p-aminophenyl) benzoxazole (AAPB) with pyromellitic dianhydride(PMDA), 2,2’3,3’-biphenyl tetracarboxylic dianhydride(i-BPDA), 4,4’-oxdiphthalic anhydride(ODPA), 1,4-bis(3,4-dicarbosyphenoxy) benzene dianhydride(HQDPA) and 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) were synthesized successfully via a conventional two-stage method. Their structures and properties were characterized by FT-IR, DSC, TG and XRD. The intermediate poly(amic acid)s had inherent viscosity range of 0.86~2.18 dL/g and could be thermally converted into light yellow polyimide films. The polyimides showed excellent solvent resistance and good thermal stability. The glass transition temperatures (Tg) were found to be 336oC~369 oC .The decomposition started at a temperature above 530oC in N2 atmosphere.


2018 ◽  
Vol 31 (8) ◽  
pp. 909-918 ◽  
Author(s):  
Xiao-Lan Zhang ◽  
Cheng Song ◽  
Mei-Hong Wei ◽  
Zhen-Zhong Huang ◽  
Shou-Ri Sheng

9,9-Bis(4-aminophenyl)xanthene (BAPX) was prepared simply and effectively via one-pot, two-step procedure using xanthenone and aniline as main substrates. The monomer BAPX was reacted with six aromatic dianhydrides in N, N-dimethylacetamide (DMAc) to yield the corresponding polyimides (PIs) via the poly(amic acid) precursors and subsequent thermal or chemical imidization. The resulting PIs exhibited good thermal stability with glass transition temperatures of 308–348°C, initial decomposition temperatures of 470–510°C, 10% weight loss temperatures of 540–565°C, and char yields of 55–59% at 800°C in nitrogen, respectively. All polymers were amorphous and readily soluble in organic solvents such as N-methyl-2-pyrrolidone and DMAc. The PI films had tensile strengths of 71–92 MPa, tensile moduli of 1.91–2.35 GPa, and elongations at break of 5–13%. Meanwhile, these polymer films also had high optical transparency with a cutoff wavelength in the range of 367–415 nm, lower dielectric constants (3.02–3.34 at 10 MHz), and low water uptake of 0.30–0.52%.


RSC Advances ◽  
2021 ◽  
Vol 11 (22) ◽  
pp. 13245-13255
Author(s):  
Mehdi Davoodi ◽  
Fatemeh Davar ◽  
Mohammad R. Rezayat ◽  
Mohammad T. Jafari ◽  
Mehdi Bazarganipour ◽  
...  

New nanocomposite of zeolitic imidazolate framework-67@magnesium aluminate spinel (ZIF-67@MgAl2O4) has been fabricated by a simple method at room temperature with different weight ratios.


2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Evelyn Carolina Martínez Ceballos ◽  
Ricardo Vera Graziano ◽  
Gonzalo Martínez Barrera ◽  
Oscar Olea Mejía

Poly(dichlorophosphazene) was prepared by melt ring-opening polymerization of the hexachlorocyclotriphosphazene. Poly[bis(2-hydroxyethyl-methacrylate)-phosphazene] and poly[(2-hydroxyethyl-methacrylate)-graft-poly(lactic-acid)-phosphazene] were obtained by nucleophilic condensation reactions at different concentrations of the substituents. The properties of the synthesized copolymers were assessed by FTIR,1H-NMR and31P-NMR, thermal analysis (DSC-TGA), and electron microscopy (SEM). The copolymers have a block structure and show twoTg's below room temperature. They are stable up to a temperature of 100°C. The type of the substituents attached to the PZ backbone determines the morphology of the polymers.


2013 ◽  
Vol 27 (3) ◽  
Author(s):  
Y. Wang ◽  
R. Wang ◽  
S. Liu ◽  
K. Yang ◽  
L. Zhou ◽  
...  

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