• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Photo-Initiated Formation of Amino Groups in Polymer Matrices and Its Applications to Functional Polymers

Research Project

Project/Area Number 63550690
Research Category

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

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionUniversity of Osaka Prefecture

Principal Investigator

TSUNOOKA Masahiro  University of Osaka Prefecture, College of Engineering, Associate Professor, 工学部, 助教授 (50081328)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1989: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1988: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsPhoto-Initiation / Acyloxyimino Groups / O-Acryloyl Acetophenone Oxime / Amino Groups / Dual-Tone Photoresist / O-Methacryloyl Acetophenone Oxime / Main-Chain Scission / Accelerated Photodegradation / O-アクリロイルアセトフェノンオキシム / O-メタクリロイルアセトフェノンオキシム / 極性変化型高分子 / フォトレジスト / 機能性高分子 / 親水化
Research Abstract

The photo-initiated formation of amino groups in polymer matrices and its applications to functional polymers were investigated. Copolymers bearing pendent acyloxyimino(AOI) groups used in this study were O-acryloyl acetophenone oxime(AAPO) or O-methacryloyl acetophenone oxime(HAAPO) with styrene(St) or methyl methacrylate(MMA). An yield of formation of amino groups in the photolysis of a AAPO(26.3)-St copolymer film was 69.9% and double bonds were also formed in a 28.0% yield. The yield of amino groups did not depend on comonomers, irradiation wavelengths, and irradiation atmosphere but depended on the amount of AOI groups in copolymers i.e., the yield for a homopolymer of AAPO decreased to 25%. In the case of MAAPO(28.3)-St copolymer films, the yield of amino groups under nitrogen was 21.5% but a total amount of double bonds was 62.7%, which consisted of double bonds in main-chains and vinylidene-type double bonds. Under air, the yield of amino groups did not changed but the yield of … More donds bondrdecreased to 30.2% and at the same time main-chain scissions occurred. Applications of the AAPO copolymers to functional polymers were also investigated. The treatment of irradiated AAPO copolymer films with an aqueous HC1 solution rendered the copolymer surface hydrophilic and the films dyed well with an acid dye. Before irradiation, the copolymers dissolved in non-polar solvents such as benzene and toluene but the films treated with HC1 after irradiation dissolved in polar solvents such as ethanol and methanol. On the basis of these results, the applications of AAPO copolymers to dual-tone photoresists were investigated and it was proved that these copolymers have excellent properties as a positive-type photoresist. In the case of MAAPO copolymers, although the yield of amino group formation was lower compared with that of AAPO copolymers, efficient main-chain scissions were observed and the rate of the main-chain scissions was found to be accelerated by an increase in the content of AOI groups and irradiation time. This result was explained by a lowering of glass transition temperature of irradiated copolymers. Less

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] Kyoung-Hun Song: "Crosslinking of 2,3-Epoxypropyl Methacrylate Copolymer Films by the Use of Photochemically Produced Pendent Amino groups." J.Polym.Sci.,Part C,Polym.Lett.,. 25. 417-421 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 角岡正弘: "アシルオキシイミノ基を有するポリマ-の固相光崩壊ー粘度法とGPC法の比較" 高分子論文集. 45. 303-307 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Photoinitiated Amino-Group Formation in a Polymer Matrix and Its Application to Polymer Surface Modification." J.Photochem.Photobiol.,A,. 44. 197-208 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoun-Hun Song: "Photochemical Reactions of Polymers Bearing O-Acryloxyimino Groups in the Solid Phase.Effects of Main-Chain Structure on the Formation of Pendent Amino Groups." Makromol.Chem.,Rapid Commun.,. 9. 519-524 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Changes of Chemical Structures in the Photodegradation of Polymer Films and Accelerated Photodegradation Behavior." J.Photopolym.Sci.Technol.,. 2. 249-252 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "A Positive-Type Photoresist Utilizing Photoinitiated Introduction of Pendent Amino Groups." J.Photochem.Photobiol.,A,. 49. 269-272 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Accelerated Photodegradation in the Solid Phase of Styrene Copolymers Bearing O-Acyloxyimino Groups." Polym.Degrad.Stab.,. 26. 255-267 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Photomodification of Polymer Surface by Utilizing Photoinitiated Amino Groups Formation-Effects of Comonomers on the Dyeing of Irradiated Polymer Surface." J.Appl.Polym.Sci.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photoinitiated Amino Groups Formation in a Polymer Matrix and Its Applications." Proc.MRS Int.Mtg.on Adv.Mats.,. 12. 357-361 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photochemical Reactions of Copolymers Bearing Acyloxyimino Groups in the Solid Phase and Applications." Chem.Func.Dyes(Proc.1st Int.Symp.on Chem.Func.Dyes). 194-197 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photo-initiated Introduction of Amino Groups and Image Formation in Thin Polymer Films." Proc.Int.Symp.on Polym.for Microelectronics.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] kyoung-Hun Song: "Crosslinking of 2, 3-Epoxypropyl Methacrylate Copolymer Films by the Use of Photochemically Produced Pendent Amino Groups." J. Polym.Sci., Part C, Polym.Lett., 25, 417 - 421 (1987).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photodegradation of the Copolymers Bearing Acyloxyimino Groups: Investigation by Viscometry and GPC." Kobunshi Ronbunshu, 45, 303 - 307 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Photo-initiated Amino Group Formation in a Polymer Matrix and Its Application to Polymer Surface Modification." J.Photochem.Photobiol., A. 44, 197 -208 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Photochemical Reactions of Polymers Bearing O-Acryloxyimino Groups in the Solid Phase. Effects of Main-Chain Structure on the Formation of Pendent Amino Groups." Makromol.Chem., Rapid Commun., 9, 519 - 524 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Changes of Chemical Structures in the Photodegradation of Polymer Films and Accelerated Photodegradation Behavior." J.Photopolym.Sci.Technol. 2, 249 - 252 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "A Positive-Type Photoresist Utilizing Photoinitiated Introduction of Pendent amino Groups." J.Photochem.Photobiol., A, 49, 269 - 272 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Accelerated Photodegradation in the Solid Phase of Styrene Copolymers Bearing O-Acyloxyimino Groups." Polym.Degrad.Stab., 26, 255 -267 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kyoung-Hun Song: "Photomodification of Polymer Surface by Utilizing Photoinitiated Amino Groups Formation - Effects of Comonomers on the Dyeing of Irradiated Polymer Surface." J.Appl.Polym.Sci.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photoinitiated Amino Groups Formation in a Polymer Matrix and Its Applications." Proc.MRS Int.Mtg. on Adv.Mats., 12, 357 - 361 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photochemical Reactions of Copolymers Bearing Acyloxyimino Groups in the Solid Phase and Applications." Chem.Func.Dyes (Proc.1st Int.Symp. on Chem.Func.Dyes) 194 -197 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Masahiro Tsunooka: "Photo-initiated Introduction of Amino Groups and Image Formation in Thin Polymer Films." Proc.Int.Symp. on Polym. for Microelectronics.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Tsunooka: "Changes of Chemical Structures in the Photodegradation of polymer Films and Accelerated Photodegradation Behavior." J.Photopolym.Sci.Technol.,. 2. 249-252 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] K.-H.Song: "A Positive-Type Photoresist Utilizing Photoinitiated Introduction of Pendent Amino Groups." J.Photochem.Photobilo., A,. 49. 269-272 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] K.-H.Song: "Accelerated Photodegradation in the Solid Phase of Styrene Copolymers Bearing O-Acyloxyimino Groups." Polym.Degrad.Stab.,. 26. 255-267 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] K.-H.Song: "Photomodification of Polymer Surface by Utilizing Photoinitiated Amino Groups Formation.-Effects of Comonomers on the Dyeing of Irradiated Polymer Surface." J.Appl.Polym.Sci.,.

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Tsunooka: "Photoinitiated Amino Groups Formation in a Polymer Matrix and Its Applications." Proc.MRS Int.Mtg.on Adv.Mats.12. 357-361 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Tsunooka: "Photochemical Reactions of Copolymers Bearing Acyloxyimino Groups in the Solid Phase and Applictions." Chem.of Func.Dyes(Proc.1st Int.Symp.on Chem.Func.Dyes). 194-197 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Tsunooka: "Photo-initiated Introduction of Amino Groups and Image Frmation in Polymer Films." Proc.Int.Symp.on Polym.for Microelectronics,in press.

    • Related Report
      1989 Annual Research Report
  • [Publications] K.-H.Song: J.Polym.Sci.25. 417-421 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.-H.Song: J.Photochem.Photobiol.,A:Chem.44. 197-208 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.-H.Song: Makromol.Chem.,Rapid Commun.9. 519-524 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.-H.Song: J.Appl.Polym.Sci.

    • Related Report
      1988 Annual Research Report
  • [Publications] K.-H.Song: Polym.Deg.Stab.

    • Related Report
      1988 Annual Research Report
  • [Publications] K.-H.Song: J.Photochem.Photobiol.

    • Related Report
      1988 Annual Research Report

URL: 

Published: 1988-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi