Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Saritha, B.; Thiruvasagam, P.

doi:10.1177/0954008314563995

Cited by 13 publications

(7 citation statements)

References 28 publications

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“…A typical procedure adopted for the synthesis of diol monomer N,N 0 -bis(2-hydroxy ethyl)bisphenol-A diimide was as follows. [15][16][17][18] To a stirred solution of ethanolamine (IIa, 2.44 g, 0.04 mol) in DMF (20 mL), BPADA (I) (10.41 g, 0.02 mol) was added under nitrogen atmosphere and was stirred at RT for 6 h. To this, toluene (20 mL) was added, and the resulting mixture was refluxed at 120 C for 6 h while removing water azeotropically using Dean-Stark trap. The temperature of the reaction mixture was raised to distill off the residual toluene.…”

Section: Monomer Synthesismentioning

confidence: 99%

Poly(ether–imide)s with flexible linkages and kinks

Thiruvasagam

Saritha

Hari

2016

High Performance Polymers

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Four new aromatic diimide-diol monomers were synthesized from bisphenol A dianhydride and hydroxyamines. The poly(ether-imide)s (PEI-1 to PEI-4) were synthesized from these diols and 4,4 0 -difluorobenzophenone-IV via carbonylactivated aromatic nucleophilic fluoro displacement reaction. The chemical structures of the monomers and PEIs were confirmed by Fourier transform infrared spectrometer and proton nuclear magnetic resonance spectroscopies. The PEIs synthesized here were amorphous and soluble in polar aprotic solvents and low-boiling organic solvents. The PEIs had good thermal stability, 10% weight loss occurred in the temperatures range of 400-448 C, and char yields at 800 C under nitrogen atmosphere was in the range of 14-22%. The limiting oxygen index values of PEIs were in the range of 23.1-26.3, and such PEIs can be used as self-extinguishing polymers. The dielectric constants of the PEIs were in the range of 3.30-4.00, and such PEIs can be used as electrical insulation materials for systems operating at high temperature for long time.

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Section: Monomer Synthesismentioning

confidence: 99%

Poly(ether–imide)s with flexible linkages and kinks

Thiruvasagam

Saritha

Hari

2016

High Performance Polymers

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“…The thermal properties of TPU can be improved by using blending [10,11,12], copolymers [13], and cross-linked structures [14]. Another approach is the functionalized introduction of fluorine-containing chemicals to form fluoroacrylate polyurethane (FPU), which is expected to have properties similar to those of other fluorinated polymers [15], including biocompatibility, excellent environmental stability, hydrolysis resistance, thermal stability [16,17], chemical resistance, low interface free energy, and water and oil resistance [18]. The interaction of organic fluorine is known to involve π–πF, C–F∙∙∙H, F∙∙∙F, C–F∙∙∙πF, C–F∙∙∙π, C–F∙∙∙M+, C–F∙∙∙C=O, and anion–πF [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Novel Polyurethanes Containing Long-Segment Fluorinated Chain Extenders

Lee

Tsai

et al. 2018

Polymers

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In this study, novel biodegradable long-segment fluorine-containing polyurethane (PU) was synthesized using 4,4′-diphenylmethane diisocyanate (MDI) and 1H,1H,10H,10H-perfluor-1,10-decanediol (PFD) as hard segment, and polycaprolactone diol (PCL) as a biodegradable soft segment. Nuclear magnetic resonance (NMR) was used to perform 1H NMR, 19F NMR, 19F–19F COSY, 1H–19F COSY, and HMBC analyses on the PFD/PU structures. The results, together with those from Fourier transform infrared spectroscopy (FTIR), verified that the PFD/PUs had been successfully synthesized. Additionally, the soft segment and PFD were changed, after which FTIR and XPS peak-differentiation-imitating analyses were employed to examine the relationship of the hydrogen bonding reaction between the PFD chain extender and PU. Subsequently, atomic force microscopy was used to investigate the changes in the microphase structure between the PFD chain extender and PU, after which the effects of the thermal properties between them were investigated through thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis. Finally, the effects of the PFD chain extender on the mechanical properties of the PU were investigated through a tensile strength test.

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“…5 –10 Many studies have been conducted to modify the structures to improve the transparency, such as the introduction of unsymmetrical, flexible segments, and heterocyclic units into the polymer backbone. 11 –19…”

Section: Introductionmentioning

confidence: 99%

Highly transparent and soluble polyimides with synergistic effects of pyridine and cyclohexane

Yao

Wang

Zhao

et al. 2017

High Performance Polymers

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In order to prepare novel polyimides (PI) with high transparency and solubility in common solvents, three diamine monomers containing pyridine or methyl-substituted pyridine and cyclohexane, 1,1′-bis[4-(5-amino-2-pyridinoxy)phenyl]cyclohexane (IIIa), 1,1′-bis[4-(5-amino-3-methyl-2-pyridinoxy)phenyl]cyclohexane (IIIb), and 1,1′-bis[4-(5-amino-2-methyl-6-pyridinoxy)phenyl]cyclohexane (IIIc), were synthesized and characterized. The diamine monomer (IIIa) was subsequently polymerized with 3,3′,4,4′-oxydiphthalic anhydride, 4,4′-(hexafluoroisopropylidene)-diphthalic anhydride (6FDA) to obtain PIs, PI-1 and PI-2. Furthermore, PI-3 (IIIb/6FDA) and PI-4 (IIIc/6FDA) were prepared for structure–property comparison studies. The structures of the resulting PIs were characterized by fourier transform infrared spectroscopy (FT-IR), X-ray diffraction, and elemental analysis. The physical properties of the PI films were investigated by thermogravimetric analysis, differential scanning calorimetric analysis, dynamic mechanical analysis, and ultraviolet–visible spectroscopy. In general, the PIs showed excellent thermal properties and good mechanical properties. Most had good solubility in polar organic solvents such as N, N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone (NMP), m-cresol, and even soluble in low boiling solvents such as tetrahydrofuran (THF) and CHCl3. The PI films also exhibited high optical transmittance of 94–97% at 500 nm and cut-off wavelength at 345–359 nm. In summary, the introduction of methyl, cyclohexane, and pyridine groups into the backbone was shown to improve the solubility and transparency of PI films.

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Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Cited by 13 publications

References 28 publications

Poly(ether–imide)s with flexible linkages and kinks

Poly(ether–imide)s with flexible linkages and kinks

Synthesis and Properties of Novel Polyurethanes Containing Long-Segment Fluorinated Chain Extenders

Highly transparent and soluble polyimides with synergistic effects of pyridine and cyclohexane

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