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Development of High-performance Materials Using Polyisoimide as a Polyimide Precursor

Research Project

Project/Area Number 05453140
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionYamagata University

Principal Investigator

UEDA Mitsuru  Faculty of Engineering Yamagata Univ.Professor, 工学部, 教授 (20007199)

Co-Investigator(Kenkyū-buntansha) SUGIYAMA Junnichi  Faculty of Engineering Yamagata Univ.Associate Professor, 工学部, 助手 (10235905)
YONETAKE Kouichirou  Faculty of Engineering Yamagata Univ.Associate Professor, 工学部, 助教授 (30143085)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥5,600,000 (Direct Cost: ¥5,600,000)
Fiscal Year 1995: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1994: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1993: ¥3,400,000 (Direct Cost: ¥3,400,000)
KeywordsPolyisoimide / Polyimide / Isomerization / High-temperature adhesive / Photosesitive-polyimide / Chemical-amplification / Rigid-rod polymer / Molecular composite / アモルファス高分子 / ブレンド / ガラス転移温度 / ドメイン / 微細加工 / 溶解抑制剤 / 溶解促進剤 / 光塩基発生剤 / ポジ型レジスト / 2層フレキシブル基材 / 脱水剤 / 転位反応 / 剥離強度 / 接着性
Research Abstract

High-performance plastics are currently receiving considerable attention for their potential uses in aerospace, automotive, electronic and related industries. In particular, polyimide (PI) has been widely used as an insulation material for microelectronic devices because of their excellent properties, such as thermal and chemical stability, and low dielectric constants. However, the aromatic PI is usually intractable because of its insolubility to organic solvent and high melting temperature.
The PII as a PI precursor because PII would be expected to have some remarkable futures as describes follows ; 1) Thermally isomerized to the corresponding PI.2) Good solubility to wide range of organic solvent. 3) Lower glass transition temperature than that of corresponding PI.4) Isomerization reaction of PII to PI is catalyzed by acid or base. Therefore, in the stand point of PII as a PI-precursor, PII is expected to become a candidate of the new high-functional material that cannot be achieved … More with PAA or PI.
i) Synthesis and properties of PII
The reactions of N-phenylphthalamic acid with various dehydrating agents have been investigated and suitabel dehydrating agent was determined. On the basis of these studies, various PIIs were prepared and thermal properties were also investigated. These PIIs were relatively stable above their glass transition temperature (Tg), but easy to convert to corresponding PIs by high thermal treatment (>250゚C). Furthermore, there was a change of 20-100゚C in Tg due to isomeric conversion.
ii) Application of PII to the high temperature adhesives
The new high-temperature adhesives based on PII as one of the application of PII as a PI-precursor. Hexafluoroisopropiridene bisphthalic anhydride (6FDA) based PII were prepared and the adhesion properties to copper foil were investigated. PIIs showed stronger adhesions to copper foils. The results suggested that the good adhesion bond strength was produced by the favorable anchoring between PII and copper foil due to a good flow of PII.
(iii) Application of PII to the PSPI system
The new photosensitive polyimide precursor based on PII and various dissolution inhibitors such as nifedipine (DHP) or Diazonaphthoquinone sulfonic ester has been developed. Furthermore, a new amine photo-generator {[(4.5-dimethoxy-2-nitrobenzyl)oxy] carbonyl} -2,6-dimethyl piperidine was prepared from 2,6-dimethyl piperidine and 4,5-dimethoxy-2-nitrobenzyl-p-nitrophenylcarbonate. The chemically amplified resist system using this amine photo-generator catalyzed isomerization reaction of PII has been developed.
(iv) Application of PII to the Rigid-Rod molecular Composite
An approach to in-situ generated RRMC using PII as a rigid-rod polymer-precursor has been investigated, where polyethersulfone (PES) was used as matrix polymer. Transparent composite films were obtained by casting polymer solutions and the PII was isomerized to the corresponding PI during film formation. Tensile strength of composite films was improved in the composition of PII less the 10wt%. The diameters of PI domain for the PII/PES,4/96 were found to be 0.1 to 0.3mum observed in the TEM photograph and the formation of interpenetrating structure was confirmed by the elemental analysis on the domain parts. Less

Report

(4 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] A.Mochizuki: "Preparation and Properties of Polyisoimide as a Polyimide-Precursor" Polym.J.26. 315-323 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Preparation and Adhesion Properties of Polyisoimides as a High-Temperature Adhesive" Polymer. 35. 4022-4026 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Novel Photosensitive Polyimide Precursor Based on Polyisoimide Using Nifedipine as a Dissolution Inhibitor" ACS, Symposium Series. 579. 242-252 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Positive-Working Photosensitive Polyimide Precursor Based on Polyisoimide Using Nifedipine as a Dissolution Inhibitor" High Perform.Polym.6. 225-233 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Positive Working Alkaline Developable Photosensitive Polyimide-Precursor Based on Polyisoimide Using Diazonaphthoquinone as a Dissolution Inhibitor" Polymer. 36. 2153-2158 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Novel Photosensitive Polyimide Precursor Based on Polyisoimide Uisng Amine Photo-Generator" Macromolecules. 28. 365-369 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Photosensitive Polyimide: Polyisoimide and Diazonaphtoquinone System" J.Photopolymer Sci.& Technol. 8. 333-342 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Application of Polyisoimide as a Polyimide Precursor to Polymer Adhesives and Photosensitive Polymers" ACS, Symposium Series. 614. 413-424 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Compatability of Polyether sulfone and Polyimide Derived from Isomerization of Polyisoimide: An Approach to in-situ Generated Rigid-Rod Molecular Composites" High Perfrom.Polym.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A,Mochizuki, T.Teranishi, and M.Ueda: "Preparation and Properties of Polyisoimide as a Polymide-Precursor" Polym, J.26. 315-323 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, T.Teranishi, and M.Ueda: "Preparation and Adhesion Properties of Polyisoimides as a High-Temperature Adhesive" Polymer. 35. 4022-4026 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, T.Teranishi, M.Ueda, and T.Omote: "Novel Photosensitive Polymide Precursor Based on Polyisoimide Uisng Nifedipine as a Dissolution Inhibitor" ACS,Symposium Series. 579. 242-252 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, K.Yamada, T.Teranishi, K.Matsushita, and M.Ueda: "Positive-Working Photosensitive Polyimide Precursor based on Polyisosimide using Nifedipine as a Dissolution Inhibitor" High Perform. Polym. 6. 225-233 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, T.Teranishi, K.Matsushita, and M.Ueda: "Positive Working Alkaline Developable Photosensitive Polyimide-Precursor based on Polyisoimide using Diazonaphthoquinone as a Dissolution Inhibitor" Polymer. 36. 2153-2158 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, T.Teranishi, and M.Ueda: "Novel Photosensitive Polymide Precursor based on Polyisoimide using Amine Photo-Generator" Macronolecules. 28. 365-369 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, Y.Tamino, K.Yamada, and M.Ueda: "Photosensitive Polyimide : Polyisoimide and Diazonaphthoquinone System" J.Photopolymer Sci. & Tech.8. 333-342 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki and M.Ueda: "Application of Polyisoimide as a Polyimide Precursor to Polymer Adhesives and Photosensitive Polymers" ACS Symp. 614. 413-424 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki, K.Yamada, M.Ueda, and R.Yokota: "Compatability of Polyether sulfone and Polyimide derived from Isomerization of Polyisoimide : An Approach to in-situ generated Rigid-Rod Molecular Composite" High Perform. Polym. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Mochizuki: "Novel Photosensitive Polyimide Precursor Based on Polyisoimide using Nifedipine as Dissolution Inhibitor" ACS,Symposium Series. 579. 242-252 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Mochizuki: "Positive-Working Photosensitive Polyimide Precursor based on Polyisoimide using Nifedipine" High Perform.polym.6. 225-233 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Mochizuki: "Positive-Working Alkaline Developable Photosensitiv Polyimide Precursor based on Polyisoimide・・・・・・・・" Polymer.

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Mochizuki: "Novel Photosensitive Polyimide Precursor based on Polyisoimide using Amine Photo-Grnerator" Macromolecules. 28. 365-369 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Mochizuki: "Preparation and Properties of Polyisoimide as a Polyimide-Precursor" Polymer Journal. 26. 315-323 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] A.Mochizuki: "ポリイミド前駆体としてのポリイソイミドの合成とその機能性材料への展開" Japan Polyimide Conference '93. (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] A.Mochizuki: "Preparation an Adhesion Properties of Polyisoimide as a High-temperature adhesive" Polymer. 35. (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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