Structure-property behaviour of soluble polyimide-polydimethylsiloxane segmented copolymers

Arnold, C.; Summers, J. D.; Chen, Y.P.; Bott, R. H.; Chen, D.; McGrath, James E.

doi:10.1016/0032-3861(89)90068-2

Cited by 146 publications

(91 citation statements)

References 4 publications

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“…Therefore, solvent soluble polyimides processed without difficulty are desired. The solubility of the polyimides has been successfully improved by the incorporation of fluorine moieties 2 -6 or, chlorine moieties 7 or, bulky side groups 8 or, pendant phenyl groups 9 or, polydimethylsiloxane segment, 10 or polyalicyclic structures 11 -13 into the polymer backbone. Because these modifications are generally carried out using relatively expensive special monomers, soluble polyimide copolymers which consist of common aromatic dianhydrides and diamines have been also investigated.…”

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confidence: 99%

Soluble Copolyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride and Conventional Aromatic Tetracarboxylic Dianhydrides

Tsuda¹,

Etou²,

Hiyoshi

et al. 1998

Polym J

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ABSTRACT:Soluble copolyimides based on 2,3,5-tricarboxycyclopentyl acetic dianhydride (TCA-AH)/aromatic tetracarboxilic dianhydrides/diamino diphenyl ether (DDE) were obtained. The maximum incorporation ratios of aromatic dianhydrides depend on flexibility of the dianhydrides. The ratios increase in the order of pyromellitic dianhydride (PMDA) (25 mo!%), 3,3' ,4,4' -biphenyltetracarboxylic dianhydride (BPDA) ( 50 mo!%) and 3,3' ,4,4' -benzophenonetetracarboxylic dianhydride (BTDA) (65 mo!%). The incorporation of conventional aromatic tetracarboxilic dianhydrides results in improvement of the thermal stability of soluble polyimides based on TCA-AH by the increment of aromatic components in polymer backbone, and the reduction of amount of a special monomer, that is TCA-AH.KEY WORDS Polyimide / Soluble Polyimide / Copolymerization / 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride / Soluble Copolyimide / Thermal Stability / Polyimides exhibit excellent thermal and mechanical properties, and have extensive engineering and microelectronics applications. 1 Aromatic polyimides such as pyromellitic polyimides are prepared from aromatic diamines and aromatic tetracarboxylic dianhydrides via poly(amic acid)s. Since conventional aromatic polyimides are insoluble, these polymers are usually processed as the corresponding soluble poly(amic acid) precursors, and then either thermally or chemically imidized. However, there are some problems owing to the unstability of poly(amic acid)s and the liberation of water in imidization process. Therefore, solvent soluble polyimides processed without difficulty are desired. The solubility of the polyimides has been successfully improved by the incorporation of fluorine moieties 2 -6 or, chlorine moieties 7 or, bulky side groups 8 or, pendant phenyl groups 9 or, polydimethylsiloxane segment, 10 or polyalicyclic structures 11 -13 into the polymer backbone. Because these modifications are generally carried out using relatively expensive special monomers, soluble polyimide copolymers which consist of common aromatic dianhydrides and diamines have been also investigated. 14 Recently the authors reported the synthesis and characterization of soluble polyimides prepared from an alicyclic tetracarboxylic dianhydride, 2,3,5-tricarboxycyclopentyl acetic dianhydride (TCA-AH), and aromatic diamines. 15 TCA-AH polyimides exhibited good thermal stability and 10% weight loss temperatures were in the range of 422--470°C in air and 457--494°C in nitrogen. These temperatures are about 100°C lower than the values of aromatic soluble polyimides based on fluorin containing monomers such as 4,4' -hexafluoroisopropylidenedi(phthalic anhydride) (6FDA). This paper reports the synthesis and characterization of soluble copolyimides based on TCA-AH and conven-222 tional aromatic tetracarboxylic dianhydrides such as pyromellitic dianhydride (PMDA), 3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA), 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA). The object of this study is to reduce the amounts ofTCA-AH ...

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confidence: 99%

Soluble Copolyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride and Conventional Aromatic Tetracarboxylic Dianhydrides

Tsuda¹,

Etou²,

Hiyoshi

et al. 1998

Polym J

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“…In particular, the graft polyimide of FPI-g-PDMS and MPI-g-PDMS were soluble in toluene, benzene and acetone. Therefore, FPI-g-PDMS and MPI-g-PDMS showed a relatively higher solubility compared to the other PDMS/polyimide polymers [13][14][15][16][17].…”

Section: Resultsmentioning

confidence: 99%

“…2. FT-IR spectra of all PDMS-grafted polyimide membranes shows the sharp absorption bands at about 1770 cm -1 (C=O symmetric stretching), 1710 cm -1 (C=O asymmetric stretching), 1378 cm -1 (C-N strethching) corresponding to the chracteristic imide bands [11][12][13][14][15][16][17]. In addition, the absorptions of the Si-O-Si are observed at 1080 and 1000 cm -1 .…”

Section: Syntheses and Characterizations Of Soluble Pdms-grafted Polymentioning

confidence: 99%

“…In order to improve the processability, the introduction of flexible linkages and bulky units into the aromatic groups were investigated [10][11][12]. Furthermore, several random or block copolymers have been prepared by incorporation of flexible polydimethylsiloxane (PDMS) components into the polyimide main chains [13][14][15][16][17]. These copolymers exhibited the higher solubility, the lower water adsorption and the lower dielectric constants, as compared with pure polyimide.…”

Section: Introductionmentioning

confidence: 99%

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Syntheses and Characterizations of Soluble PDMS-Grafted Polyimides

Yun

Abeta

Wirittichai

et al. 2010

Trans. Mat. Res. Soc. Japan

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Polydimethylsiloxane (PDMS) grafted polyimides with different backbone structures were prepared by polycondensation of 3,5-bis(4-aminophenoxy)benzyloxypropyl-terminated PDMS with 4,4'-oxydiphtalic dianhydride (ODPA) and 4,4'-hexafluoroisopropylidene diphthalic anhydride (6FDA) followed by chemical imidization to afford PI-g-PDMS and FPI-g-PDMS, respectively. Another PDMS-grafted polyimide, MPI-g-PDMS, was also prepared by similar procedure from 3,5-bis(4-amino-3-methylphenoxy)benzyloxypropyl-terminated PDMS and ODPA.1 H-NMR and FT-IR spectra clearly demonstrated that the desired PDMS-grafted polyimides were successfully synthesized. FPI-g-PDMS and MPI-g-PDMS exhibited the high solubility, which were soluble in chloroform, THF, DMF, NMP, toluene, benzene as well as acetone, while PI-g-PDMS was soluble only in chloroform. Therefore, the membranes could be prepared by solvent-casting method using chloroform. Interestingly, the obtained membranes became insoluble in any solvents after the thermal imidization at 200℃ in vacuo for 24 h.

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“…Extremely high thermoforming temperatures and insolubility in most solvents makes processing of polyimides very difficult. Recent papers [14][15][16] and a patent application l7 describe the synthesis of polyimides with flexible sequences in the polymer backbone. These efforts have led to materials that are soluble in some common solvents as well as being processible at lower temperatures.…”

Section: Introductionmentioning

confidence: 99%

Properties of polyamic acid ionomers

Grady

Reiner

et al. 1993

J of Applied Polymer Sci

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SYNOPSISPolymers containing amic acid units were produced by reacting an oligomer based on polytetramethylene oxide (PTMO) with 1,2,4,5-benzenetetracarboxylic dianhydride (BTDA) .Neutralization by a metal salt produced amic acid ionomers. Similar to other ionomer systems, neutralization from the acid to the ionomer led to the formation of a separate ionic phase as determined by dynamic mechanical analysis. Phase separation resulted in a substantial increase in mechanical properties. The effect of neutralization level, cation, soft-segment molecular weight, and soft-segment end group on mechanical and thermal properties was investigated. 0 1993 John Wiley & Sons, Inc.

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Structure-property behaviour of soluble polyimide-polydimethylsiloxane segmented copolymers

Cited by 146 publications

References 4 publications

Soluble Copolyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride and Conventional Aromatic Tetracarboxylic Dianhydrides

Soluble Copolyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride and Conventional Aromatic Tetracarboxylic Dianhydrides

Syntheses and Characterizations of Soluble PDMS-Grafted Polyimides

Properties of polyamic acid ionomers

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