Synthesis and properties of fluorinated polyimides from novel 2,2'-bis(fluoroalkoxy)benzidines

Feiring, Andrew E.; Auman, Brian C.; Wonchoba, E. R.

doi:10.1021/ma00063a022

Cited by 152 publications

(106 citation statements)

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“…It should be noted that although the as-coated films based on the 3,3-diamonomers are given along with those of the analogous materials based on the 4,4-monomers from minobiphenyl monomers did not give low CTE or high modulus, it may be possible to achieve these previous work. 4,5 The polymers based on the fluorinated 3,3-monomers gave substantially higher via stretching or otherwise orientating the films. The same may be true for fibers based on these CTE and lower modulus vs. their 4,4-analogs.…”

Section: Resultsmentioning

confidence: 99%

“…For this reason, we have been actively exploring fluorinated polyimides. [4][5][6][7] We have found that the combination of a rod-like structure with a fluorinated backbone can give an ideal com- To a solution containing 565 mL of fuming sulfu-9,9-Bis(trifluoromethyl)-(6FCDA) and 9-trifluric acid and 107.36 g (0.423 mol) of iodine, 50.07 oromethyl-9-phenyl-(3FCDA) -2,3,6,7-xanthene g (0.3 mol) of m-nitrobenzoic acid were added. tetracarboxylic dianhydrides were prepared by…”

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confidence: 99%

“…It was then allowed to stir at (4,4-TFMB) and 4,4-bis(trifluoromethoxy)ben-85ЊC for 24 h. After cooling, the reaction mixture zidine (4,4-TFMOB) were described previously. 4,5 was poured over ice with stirring. The ice/water Terephthaloyl chloride (TCl) and isophthaloyl mixture was extracted with methylene chloride.…”

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confidence: 99%

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Synthesis and characterization of polyimides based on new fluorinated 3,3?-diaminobiphenyls

Auman

Myers

Higley

1997

J. Polym. Sci. A Polym. Chem.

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Two new fluorinated diamine monomers, 3,3′‐diamino‐5,5′‐bis(trifluoromethyl)biphenyl and 3,3′‐diamino‐6,6′‐bis(trifluoromethoxy)biphenyl, as well as a known nonfluorinated analog, 3,3′‐diaminobiphenyl, were synthesized. Reaction of these diamines with rigid, highly rod‐like dianhydrides produced poly(amic acid)s and polyimides, which were spin coated and thermally treated to produce polyimide films for evaluation in electronics applications. It was hoped that these polyimide films would exhibit an ideal combination of low thermal expansion, reduced water absorption, and low dielectric constant but with improved elongation due to the “crankshaft” nature of the 3,3′‐biphenyl unit. Unlike polyimide films from analogous 4,4′‐diaminobiphenyls, however, the 3,3′‐diaminobiphenyl‐based polyimides did not yield low in‐plane thermal expansion coefficient in spin‐coated films. In some cases high elongation was achieved, but with high thermal expansion. These new diamines may nevertheless find utility in polyimides and polyaramides for membrane, fiber, and other applications. Additionally, they may be useful in modifying the properties of polymer backbones via copolymerization. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 2441–2451, 1997

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Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of polyimides based on new fluorinated 3,3?-diaminobiphenyls

Auman

Myers

Higley

1997

J. Polym. Sci. A Polym. Chem.

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“…Feiring et al 47 have previously reported a TEC of Ϫ3.0 ppm/°C for approximately 10-m-thick films prepared on substrates. The TEC (Ϫ2.5 ppm/°C) measured in the present study is in reasonably good agreement with their result.…”

Section: Thermal Expansivitymentioning

confidence: 95%

Synthesis and characterization of fully rodlike poly(4,4?-biphenylene pyromellitimide)s with various short side groups

Pyo

Kim

Shin

et al. 1999

J. Polym. Sci. A Polym. Chem.

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“…A fluorinated PI with stiff chain backbone was reported to exhibit these combined properties [10]. On the other hand, we have developed four PI systems containing cycloaliphatic units as target materials, i.e., s-BPDA/CHDA, PMDA/CHDA, CBDA/TFMB, and CBDA/CHDA, where CBDA = 1,2,3,4-cyclobutanetetracarboxylic dianhydride, TFMB = bis(2,2'-trifluorometyl)benzidine).…”

Section: Introductionmentioning

confidence: 99%

Solution-processable Low-CTE Polybenzoxazoles

Hasegawa

Kobayashi

Vladimirov

2004

J. Photopol. Sci. Technol.

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Polybenzoxazoles (PBO) are also expected as low-K & low-CTE dielectric materials as well as polyimides. High molecular weight PBO precursors, polyhydroxyamides (PHAs), were prepared from silylated bis(3-hydroxy-4-amino)biphenyl(p-HAB) and dichlorides of terephthalic acid (TPA) or trans-1,4-cyclohexanedicarboxylic acid in DMAc/HMPA in the presence of pyridine and LiCl. After precipitation of the PHA solution into water to remove the salts, it was difficult to re-dissolve into salt-free aprotic solvents. Therefore, the salt-containing PHA solution was cast on a glass plate and washed with water to remove salt, then the dried films fixed in a frame were heated at 400ºC/1h to ensure complete transformation to PBO. The obtained PBO films showed a much lower K, a lower CTE and a higher Tg than the corresponding PIs. The use of a fluorine-containing bis(o-aminophenol) as a comonomer for the homo p-HAB/TPA system improved significantly the solubility into salt-free solvents. Another PHA derived from an isomer of p-HAB, bis(4-hydroxy-3-amino)biphenyl (m-HAB) and TPA also showed a high solubility. These new PBO systems made possible the convenient film formation process (cast-drying-thermal treatment like PI systems) for microelectronic applications. Simultaneously, these PBO films maintained comparatively low K values, considerable low CTEs, and high Tg's as in the homo p-HAB/TPA systems.

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Synthesis and properties of fluorinated polyimides from novel 2,2'-bis(fluoroalkoxy)benzidines

Cited by 152 publications

References 4 publications

Synthesis and characterization of polyimides based on new fluorinated 3,3?-diaminobiphenyls

Synthesis and characterization of polyimides based on new fluorinated 3,3?-diaminobiphenyls

Synthesis and characterization of fully rodlike poly(4,4?-biphenylene pyromellitimide)s with various short side groups

Solution-processable Low-CTE Polybenzoxazoles

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