Preparation and properties of novel polyimides derived from 4‐aryl‐2,6 bis(4‐amino phenyl)pyridine

Tamami, Bahman; Yeganeh, Hamid

doi:10.1002/pola.10025

Cited by 66 publications

(47 citation statements)

References 27 publications

(23 reference statements)

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“…Tamami and Yeganeh [22,23] and Liaw et al [24,25] have used this method for the preparation of novel pyridinecontaining diamines. Related PIs were synthesized from polycondensation of these diamines with some dianhydrides.…”

Section: Introductionmentioning

confidence: 99%

Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides

et al. 2010

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A novel pyridine-containing aromatic diamine monomer, 4-phenyl-2,6-bis[3-(4-aminophenoxy)phenyl]pyridine (m,p-PAPP), was successfully synthesized by a modified Chichibabin reaction of benzaldehyde and a substituted acetophenone, 3-(4-nitrophenoxy)acetophenone (m,p-NPAP), followed by a reduction of the resulting dinitro compound 4-phenyl-2,6-bis[3-(4-nitrophenoxy)phenyl]pyridine (m,p-PNPP) with Pd/C and hydrazine monohydrate. The aromatic diamine was employed to synthesize a series of pyridine-containing polyimides (PIs) by polycondensation with various aromatic dianhydrides in N,N-dimethylformamide (DMF) via the conventional two-step method, and further thermal or chemical imidization forming PIs. The inherent viscosities of the resulting poly(amic acid)s and PIs were 0.59-0.73 and 0.56-0.68 dL/g; most of the PIs obtained by chemical imidization were readily soluble in common organic solvents such as DMF, N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetrahydrofuran (THF), etc. Meanwhile, strong and flexible PI films were obtained, which had good thermal stability, with the glass transition temperature (T g ) of 204.5-237.4°C and the temperature at 10% weight loss of 527.7-552.0°C in nitrogen atmosphere, as well as outstanding mechanical properties with tensile strengths of 88.6-90.4 MPa, a tensile moduli of 1.04-1.56 GPa, and elongations at break of 7.2-8.7%. The PI films also were found to possess low water uptake of 0.89-0.98%.

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Section: Introductionmentioning

confidence: 99%

Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides

et al. 2010

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“…Compounds 1 and 2 were synthesized in our laboratory according to reported procedure [33,37]. All solvents were dried before use.…”

Section: Methodsmentioning

confidence: 99%

“…A quartz crystal was used as the reference sample. [33,37] In a round-bottomed flask (250 ml) equipped with a reflux condenser, a mixture of 4-methoxy-benzaldehyde (4.08 g, 30.0 mmol), 4-nitro-acetophenone (9.91 g, 60.0 mmol), ammonium acetate (30 g) and glacial acetic acid (75 ml) was refluxed for 3 h. Upon cooling, the resulted solid was filtered and washed first with acetic acid (50%) and then with cold ethanol and then dried at 60°C under vacuum. Yield: 60% (7.87 g).…”

Section: Instrumentsmentioning

confidence: 99%

“…Yield: 60% (7.87 g). [33,37] In a 250-ml two-necked round-bottomed flask equipped with a reflux condenser and dropping funnel, a suspension of 1 (5.13 g, 12.0 mmol), palladium on carbon (5%, 0.4 g) and ethanol (200 ml) was prepared. The mixture was warmed and, while being stirred magnetically, hydrazine hydrate (80%, 10 ml) in ethanol (20 ml) was added drop-wise over a period of 1.5 h while maintaining a temperature of about 50°C.…”

Section: Instrumentsmentioning

confidence: 99%

“…However, solubility is a very important factor, simplifying applications of polyimides. Recently, new polyimides and co-polyimides based on pyridine containing monomers were reported [32][33][34][35][36]. Both solubility and thermal stability of these polymers were good.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Characterization of New Disperse-Red Functionalized Polyimide for Use as Nonlinear Optical Material

Koohmareh

2012

Designed Monomers and Polymers

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A new thermally-stable second-order nonlinear optical polyimide with side-chain second-order nonlinear optical (NLO) chromophore was synthesized. First a diamine functionalized azo chromophore (9) was synthesized and then polymerized by reaction with 4,4 -hexafluro isopropylidene-diphthalic anhydride. The synthesized polymer had a glass transition temperature of 215°C. The corona poling process of the NLOsubstituted polyimide was also studied in detail by measuring the second harmonic generation (SHG) from the polymer films. The second harmonic measurement indicate long-term stability of the dipole orientation (>500 h at 150°C) for this polyimide.

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Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

Xia

Guo

Qiu

et al. 2006

J of Applied Polymer Sci

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A series of novel homo-and copolyimides containing pyridine units were prepared from the heteroaromatic diamines, 2,5-bis (4-aminophenyl) pyridine and 2-(4-aminophenyl)-5-aminopyridine, with pyromelltic dianhydride (PMDA), and 3,3Ј, 4,4Ј-biphenyl tertracarboxylic dianhydride (BPDA) via a conventional two-step thermal imidizaton method. The poly(amic acid) precursors have inherent viscosities of 1.60 -9.64 dL/g (c ϭ 0.5 g/dL in DMAC, 30°C) and all of them can be cast and thermally converted into flexible and tough polyimide films. All of the polyimides show excellent thermal stability and mechanical properties. The polyimides have 10% weight loss temperature in the range of 548 -598°C in air. The glass transition temperatures of the PMDA-based samples are in the range of 395-438°C, while the BPDA-based polyimides show two glass transition temperatures (T g 1 and T g 2), ranging from 268 to 353°C and from 395 to 418°C, respectively. The flexible films possess tensile modulus in the range of 3.42-6.39 GPa, strength in the range of 112-363 MPa and an elongation at break in the range of 1.2-69%. The strong reflection peaks in the wide-angle X-ray diffraction patterns indicate that the polyimides have a high packing density and crystallinity. The polymer films are insoluble in common organic solvents exhibiting high chemical resistance.

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Preparation and properties of novel polyimides derived from 4‐aryl‐2,6 bis(4‐amino phenyl)pyridine

Cited by 66 publications

References 27 publications

Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides

Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides

Synthesis and Characterization of New Disperse-Red Functionalized Polyimide for Use as Nonlinear Optical Material

Syntheses and properties of polyimides derived from diamines containing 2,5‐disubstituted pyridine group

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