Synthesis of Fluorine-Containing Wholly Alicyclic Polyimides by In Situ Silylation Method

Oishi, Yoshiyuki; Onodera, Shu; Oravec, Juraj; Ando, Shinji; Terui, Yoshiharu; Maeda, Kengo

doi:10.2494/photopolymer.16.263

Cited by 25 publications

(17 citation statements)

References 8 publications

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“…The optical dielectric constants of the fluorinated PIs, estimated from n av according to a modified form of Maxwell's equation (dielectric constant = 1.10 n 2 )36 to be 2.50–2.68, agreed well with the measured ones (Table IV). For example, PI‐3 exhibited an estimated dielectric constant of 2.65, which was a little lower than the measured value of 2.68.…”

Section: Resultssupporting

confidence: 75%

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

Zhao

Liu

et al. 2008

J of Applied Polymer Sci

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A novel aromatic diamine, 1,1-bis(4-amino-3,5-dimethylphenyl)-1-(3,4,5-trifluorophenyl)-2,2,2-trifluoroethane, containing a pendant polyfluorinated phenyl group, a trifluoromethyl group, and methyl groups orthosubstituted to the amino groups in the structure was synthesized and characterized. The diamine was polymerized with several aromatic dianhydrides, including 3,3 0 ,4,4 0 -biphenyltetracarboxylic dianhydride, 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride, 4,4 0 -oxydiphthalic anhydride, and 4,4 0 -hexafluoroisopropylidene diphthalic anhydride, via a high-temperature one-step procedure to afford four polyimides (PIs) with inherent viscosities of 0.47-0.70 dL/g. The PIs exhibited excellent solubilities in a variety of organic solvents. They were soluble not only in polar aprotic solvents but in many common solvents, such as cyclopentanone, tetrahydrofuran, and even toluene at room temperature. The tough and flexible PI films cast from the PI solutions exhibited good thermal stabilities and acceptable tensile properties. The glass-transition temperatures were in the range 312-365 C, and the 5% weight loss temperatures were all higher than 480 C in nitrogen. The films had tensile strengths in the range 76-99 MPa, tensile moduli of 2.2-2.8 GPa, and elongations at break of 5-8%. In addition, the PI films exhibited excellent transparency in the visible light region with cutoff wavelength as low as 302 nm and transmittance higher than 88% at the wavelength of 450 nm. The PI films showed low dielectric constants ranging from 2.50-2.68 and low moisture absorptions of less than 0.56%. The good combined properties of the PIs mainly resulted from the synergic effects of the different substituents. V

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Section: Resultssupporting

confidence: 75%

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

Zhao

Liu

et al. 2008

J of Applied Polymer Sci

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“…Optical anisotropy (Δ n ) is given as the difference between n TE and n TM . The dielectric constants of the material at optical frequencies could be estimated from the refractive index, n , according to Maxwell's equation17, 19: ε · n 2 . The value of ε, around 1 MHz, was evaluated as ε · 1.10 n

_{AV}^{2}

, including an additional contribution from the infrared absorption of approximately 10%.…”

Section: Resultsmentioning

confidence: 99%

A novel positive‐type photosensitive polyimide based on soluble block copolyimide showing low dielectric constant with a low‐temperature curing process

Jin¹,

Ishii²

2006

J of Applied Polymer Sci

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A soluble block copolyimide (Bco-PI) was prepared by direct one-pot polycondensation of 2,2-bis-(3-amino-4-hydroxyphenyl)hexafluoropropane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, and cyclohexane-tetracarboxylic dianhydride in the presence of ␥-valerolactone and a pyridine catalyst system using ␥-butyrolactone as the solvent. The thermal transmission temperature (T g ) of Bco-PI was 282°C. By having the curing process occur at 250°C, which was below the T g , colorless and transparent films could be obtained. The film showed excellent optical characteristics. Such properties could not be attained by the conventional high-temperature thermal imidization process of poly(amic acid). The hydroxy groups in the polyimide backbone gave the Bco-PI the potential to become alkaline. To the Bco-PI was added 15 wt % ester of 2,3,4-trihydroxybenzophenone with 1,2-naphthoquinone-(2) diazide-5-sulfonic acid (NT200) as the photoreactive compound. The system worked as a positive-type photosensitive polyimide (PSPI). The sensitivity and contrast of the PSPI system were 220 mJ/cm 2 and 1.27, respectively, when exposed to UV light, followed by development with a 5% tetramethylammonium hydroxide (TMAH) aqueous solution at room temperature. After curing at 250°C for 1 h, the average refractive index of Bco-PI with and without NT200 was 1.5543 and 1.5563, and the optically estimated dielectric constant of the polyimides was 2.66 and 2.67, respectively.

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“…Unlike the widely used sol–gel process of physically interlocking polyimide and siloxanes with the chances of preferential hydrolysis, microheterogeneity, cracking, and delamination,45 we have applied one‐step poly (condensation/addition) reaction for synthesizing fully APISiO. Recently, the syntheses of wholly APIs from N ‐silylated alicyclic diamines and by in situ silylation method have been reported 46, 47. But, due to the complexity of the methods reported previously, we chose the simple one‐step synthesis and were able to obtain APISiOs with reasonable molecular weights and effective chemical bonding in expected ratios of APTMS and alicyclic diamine.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and characterization of novel fully aliphatic polyimidosiloxanes based on alicyclic or adamantyl diamines

Mathews

Kim

2006

J. Polym. Sci. A Polym. Chem.

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A series of fully aliphatic polyimidosiloxanes (APISiO) were prepared by poly(addition/condensation) reaction of bicyclo [2,2,2] oct‐7‐ene‐2,3,5,6‐tetracarboxylic dianhydride or cyclobutane‐1,2,3,4‐tetracarboxylic dianhydride and varying compositions of 1,3‐bis (3‐amino propyl)‐tetra methyl disiloxane and rigid adamantyl diamines (1,3‐diaminoadamantane or 3,3′‐diamino‐1,1′‐diadamantane) or flexible alicyclic diamines (4,4′‐methylene bis(cyclohexylamine) or 4,4′‐methylene bis(2‐methylcyclohexylamine)). High temperature one‐step synthesis in m‐cresol was employed to obtain APISiOs with intrinsic viscosity in the range of 0.28–0.59 dL/g. The final materials were characterized by 1H and 13C NMR, 29Si‐MAS‐NMR and IR spectroscopic analysis, thermogravimetric and differential scanning calorimetric analysis, and wide angle X‐ray diffractometry. UV–visible spectra revealed the optical behavior of the polyimides. It was found that the APISiOs containing appropriate ratio of adamantyl moieties together with flexible aliphatic siloxane groups exhibit good thermal and mechanical stabilities, solubility, fair transparency, and low dielectric constant (2.4–2.7). © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 5254–5270, 2006

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Synthesis of Fluorine-Containing Wholly Alicyclic Polyimides by In Situ Silylation Method

Cited by 25 publications

References 8 publications

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

A novel positive‐type photosensitive polyimide based on soluble block copolyimide showing low dielectric constant with a low‐temperature curing process

Synthesis and characterization of novel fully aliphatic polyimidosiloxanes based on alicyclic or adamantyl diamines

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