UV Curable Resins with Degradable Property and Their Application for Sacrificial Materials

• Project/Area Number: 21350128
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Polymer/Textile materials
• Research Institution: Osaka Prefecture University
• Principal Investigator: SHIRAI Masamitsu 大阪府立大学, 大学院・工学研究科, 教授 (00081331)
• Co-Investigator(Kenkyū-buntansha): OKAMURA Haruyuki 大阪府立大学, 大学院・工学研究科, 助教 (10316010)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥19,500,000 (Direct Cost: ¥15,000,000、Indirect Cost: ¥4,500,000); Fiscal Year 2011: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000); Fiscal Year 2010: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2009: ¥13,650,000 (Direct Cost: ¥10,500,000、Indirect Cost: ¥3,150,000)
• Keywords: 高分子材料合成 / 光硬化樹脂 / 架橋と分解 / 犠牲材料 / 光インプリント材料 / UV硬化樹脂 / 分解型硬化樹脂 / UVインプリント / 分解型光硬化樹脂 / リワーク樹脂 / 多官能モノマー / レプリカモールド / 低収縮性モノマー / 環境調和型硬化樹脂

Research Abstract

Novel resins which are curable on irradiation at365nm and are degradable on irradiation at254nm were designed and synthesized. The UV curable and degradable properties of the resins were studied. The resins were used as template resins for making the replicated resin mold for UV imprint lithography. It was shown that the degradable resins have a potential as sacrificial materials.

Research Products

• [Journal Article] Photo-cross-linking and De-cross-linking of modified Polystyrenes having Degradable Linkages (2011)
  • Author(s): H. Okamura, E. Yamaguchi, M. Shirai
  • Journal Title: React. Funct. Polym Volume: 71巻 Pages: 480-488
  • Peer Reviewed
• [Journal Article] Reworkable Dimethacrylates with Low Shrinkage and Their Application to UV Imprint Lithography (2011)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: J. Mater. Chem Volume: 21巻 Pages: 10407-10414
  • Peer Reviewed
• [Journal Article] Reworkable Resin Using Thiol-Ene System (2011)
  • Author(s): H. Okamura, M Shiai
  • Journal Title: J. Photopolym. Sci. Technol. Volume: 24巻 Pages: 561-564
  • Peer Reviewed
• [Journal Article] リワーク型低収縮ジメタクリラートとそのUVインプリント材料への応用 (2011)
  • Author(s): 岡村晴之、白井正充
  • Journal Title: ネットワークポリマー Volume: 33巻 Pages: 74-78
  • Peer Reviewed
• [Journal Article] Photo-cross-linking and De-cross-linking of modified Polystyrenes having Degradable Linkages (2011)
  • Author(s): H.Okamura, E.Yamaguchi, M.Shirai
  • Journal Title: React.Funct.Polym. Volume: 71 Pages: 480-488
  • Peer Reviewed
• [Journal Article] Reworkable Dimethacrylates with Low Shrinkage and Their Application to UV Imprint Lithography (2011)
  • Author(s): D.Matsukawa, H.Okamura, M.Shirai
  • Journal Title: J.Mater.Chem. Volume: 21 Pages: 10407-10414
  • Peer Reviewed
• [Journal Article] Reworkable Resin Using Thiol-Ene System (2011)
  • Author(s): H.Okamura, M Shiai
  • Journal Title: J.Photopolym.Sci.Technol. Volume: 24 Pages: 561-564
  • Peer Reviewed
• [Journal Article] Analysis of Chain Propagation in UV Curing Using Reworkable Resin (2010)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: J. Photopolym. Sci. Technol. Volume: 23巻 Pages: 125-128
  • NAID: 130004833323
  • Peer Reviewed
• [Journal Article] Novel Photo-Cross-Linkable Dendrimers Having Thermal De-Cross-linking Properties (2010)
  • Author(s): H. Okamura, M. Shirai
  • Journal Title: Polymer Volume: 51巻 Pages: 5087-5094
  • Peer Reviewed
• [Journal Article] Preparation of Replicated Resin Mold for UV Nanoimprint Using Reworkable Dimethacrylate (2010)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: J. Photopolym. Sci. Technol. Volume: 23巻 Pages: 781-787
  • NAID: 130004833379
  • Peer Reviewed
• [Journal Article] Analysis of Chain Propagation in UV Curing Using Reworkable Resin (2010)
  • Author(s): D.Matsukawa, H.Okamura, M.Shirai
  • Journal Title: J.Photopolym.Sci.Technol. Volume: 23 Pages: 125-128
  • NAID: 130004833323
  • Peer Reviewed
• [Journal Article] Novel Photo-Cross-Linkable Dendrimers Having Thermal De-Cross-linking Properties (2010)
  • Author(s): H.Okamura, M.Shirai
  • Journal Title: Polymer Volume: 51 Pages: 5087-5094
  • Peer Reviewed
• [Journal Article] Preparation of Replicated Resin Mold for UV Nanoimprint Using Reworkable Dimethacrylate (2010)
  • Author(s): D.Matsukawa, H.Okamura, M.SHirai
  • Journal Title: J.Photopolym.Sci.Technol. Volume: 23 Pages: 781-787
  • NAID: 130004833379
  • Peer Reviewed
• [Journal Article] Novel Reworkable Resins : Thermo- and Photo-Curable Di(meth)acrylates (2010)
  • Author(s): Daisaku Matsukawa
  • Journal Title: Polymer International 59 Pages: 263-268
  • Peer Reviewed
• [Journal Article] A UV Curable Resin with Reworkable Properties : Application to Imprint Lithography (2009)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: J. Mater. Chem. Volume: 19巻 Pages: 4085-4087
  • Peer Reviewed
• [Journal Article] Photocurable Oligo(hemiacetal ester) s Having Methacrylate Side Chains (2009)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: Eur. Polym. J. Volume: 45巻 Pages: 2087-2095
  • Peer Reviewed
• [Journal Article] Photo-and Thermal Curing of Trifunctional Methacrylate with Degradable Property (2009)
  • Author(s): H. Okamura, M. Shirai
  • Journal Title: Res. Chem. Intermediate Volume: 35巻 Pages: 865-878
  • Peer Reviewed
• [Journal Article] Novel Reworkable Resins : Thermo-and Photo-Curable Di(meth) acrylates (2009)
  • Author(s): D. Matsukawa, H. Okamura, M. Shirai
  • Journal Title: Polym. International Volume: 59巻 Pages: 263-268
  • Peer Reviewed
• [Journal Article] A UV Curable Resin with Reworkable Properties : Application to Imprint Lithography (2009)
  • Author(s): Daisaku Matsukawa
  • Journal Title: Journal of Materials Chemistry 19 Pages: 4085-4087
  • Peer Reviewed
• [Journal Article] Photocurable Oligo(hemiacetal ester)s Having Methacrylate Side Chains (2009)
  • Author(s): Daisaku Matsukawa
  • Journal Title: European Polymer Journal 45 Pages: 2087-2095
  • Peer Reviewed
• [Journal Article] Photo- and Thermal Curing of Trifunctional Methacrylate with Degradable Property (2009)
  • Author(s): Haruyuki Okamura
  • Journal Title: Research of Chemical Intermediate 35 Pages: 865-878
  • Peer Reviewed
• [Journal Article] アニオン硬化 (2009)
  • Author(s): 白井正充
  • Journal Title: 接着の技術 29 Pages: 8-14
• [Presentation] UV Imprint Lithography : Process, Materials and Applications (2011)
  • Author(s): M. Shirai
  • Organizer: Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: Seoul, Korea
  • Year and Date: 2011-10-29
• [Presentation] UV Imprint Lithography : Process, Materials and Applications (2011)
  • Author(s): M.Shirai
  • Organizer: Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: Seoul, Korea(招待講演)
  • Year and Date: 2011-10-29
• [Presentation] Novel Resin Mold for UV Nanoimprint : A Demolding Agent Free System (2011)
  • Author(s): M. Shirai
  • Organizer: 37th International Conference on Micro and Nano Engineering
  • Place of Presentation: Berlin, Germany
  • Year and Date: 2011-09-20
• [Presentation] Novel Monomers with Degradable Property and Their Applications to UV Imprint Lithography (2011)
  • Author(s): M. Shirai
  • Organizer: Photopolymerization Fundamentals 2011
  • Place of Presentation: Breckenridge, CO, USA
  • Year and Date: 2011-06-27
• [Presentation] Novel Monomers with Degradable Property and Their Applications to UV Imprint Lithography (2011)
  • Author(s): M.Shirai
  • Organizer: Photopolymerization Fundamentals2011
  • Place of Presentation: Breckenridge, Co, USA(招待講演)
  • Year and Date: 2011-06-27
• [Presentation] UV Curing and Degradation of Reworkable Methacrylates Having Hemiacetal Ester LInkage (2011)
  • Author(s): Y.Murakami, H.Okamura, M.Shirai
  • Organizer: Photopolymerization Fundamentals 2011
  • Place of Presentation: Breckenridge, Co, USA
  • Year and Date: 2011-06-27
• [Presentation] Reworkable Resin Using Thiol-Ene System (2011)
  • Author(s): H. Okamura
  • Organizer: The 28th International Conference of Photopolymer Science and Technology
  • Place of Presentation: Chiba, Japan
  • Year and Date: 2011-06-25
• [Presentation] UV Curing of Reworkable Dendrimers (2011)
  • Author(s): H. Okamura
  • Organizer: RadTech Asia 2011
  • Place of Presentation: Yokohama, Japan
  • Year and Date: 2011-06-23
• [Presentation] Duplication of Mold for UV Imprint Lithography Using UV Curable Resin with Reworkable Property (2011)
  • Author(s): S. Horii
  • Organizer: RadTech Asia 2011
  • Place of Presentation: Yokohama, Japan
  • Year and Date: 2011-06-23
• [Presentation] Reworkable Dimethacrylates Having Hemiacetal Ester U nits (2011)
  • Author(s): H. Okamura
  • Organizer: RadTech Asia 2011
  • Place of Presentation: Yokohama, Japan
  • Year and Date: 2011-06-23
• [Presentation] UV Curing of Reworkable Resin : Analysis of Chain Propagation (2011)
  • Author(s): D. Matsukawa
  • Organizer: RadTech Asia 2011
  • Place of Presentation: Yokohama, Japan
  • Year and Date: 2011-06-23
• [Presentation] Reworkable Dimethacrylates Having Hemiacetal Ester Units (2011)
  • Author(s): H.Okamura, T.Hatsuse, D.Matsukawa, M.Shirai
  • Organizer: RadTech Asia 2011
  • Place of Presentation: Yokohama, Japan
  • Year and Date: 2011-06-23
• [Presentation] リワーク型多官能メタクリラートのUVインプリント材料への応用 (2011)
  • Author(s): 松川大作
  • Organizer: 第60回高分子年次大会
  • Place of Presentation: 大阪
  • Year and Date: 2011-05-25
• [Presentation] 離型剤フリーなUVインプリント用モールドのための樹脂材料 (2011)
  • Author(s): 堀井俊哉
  • Organizer: 第60回高分子年次大会
  • Place of Presentation: 大阪
  • Year and Date: 2011-05-25
• [Presentation] UV Curable Monomers with Degradable Property-Molecular Design and Application to UV Imprint Lithography (2010)
  • Author(s): M. Shirai
  • Organizer: 1st European Symposium of Photopolymer Science
  • Place of Presentation: Mulhouse, France
  • Year and Date: 2010-12-01
• [Presentation] UV Curable Monomers with Degradable Property-Molecular Design and Application to UV Imprint Lithography- (2010)
  • Author(s): M.Shirai
  • Organizer: 1st European Symposium of Photopolymer Science
  • Place of Presentation: Mulhouse, France(招待講演)
  • Year and Date: 2010-12-01
• [Presentation] デンドリマー構造を有する再可溶化型光架橋樹脂 (2010)
  • Author(s): 岡村晴之
  • Organizer: 第60回ネットワークポリマー講演討論会
  • Place of Presentation: 東京
  • Year and Date: 2010-10-15
• [Presentation] リワーク型光硬化樹脂のUVインプリントへの応用および重合連鎖解析 (2010)
  • Author(s): 松川大作
  • Organizer: 第59回高分子討論会
  • Place of Presentation: 札幌
  • Year and Date: 2010-09-15
• [Presentation] 種々の熱分解部位を有するエポキシ基含有ポリマーの合成と光架橋および解架橋 (2010)
  • Author(s): 岡村晴之
  • Organizer: 第59回高分子討論会
  • Place of Presentation: 札幌
  • Year and Date: 2010-09-15
• [Presentation] Chain Propagation in UV Curing of Difunctional Mehtacrylates (2010)
  • Author(s): D. Matsukawa
  • Organizer: Coating Science International 2010
  • Place of Presentation: Noordwijk, Holland
  • Year and Date: 2010-06-30
• [Presentation] Analysis of Chain Propagation in UV Curing Using Reworkable Resin (2010)
  • Author(s): D. Matsukawa
  • Organizer: Photopolymer Conference
  • Place of Presentation: 千葉
  • Year and Date: 2010-06-23
• [Presentation] リワーク型多官能メタクリラートのUVインプリント材料への応用-インプリント条件下での重合連鎖解析 (2010)
  • Author(s): 松川大作
  • Organizer: 第59回高分子学会年次大会
  • Place of Presentation: 横浜
  • Year and Date: 2010-05-26
• [Presentation] UV Curable Monomers for Imprint Lithography (2010)
  • Author(s): M. Shirai
  • Organizer: RadTech UV & EB 2010 Technology Expo and Conference
  • Place of Presentation: Baltimore, MD, USA
  • Year and Date: 2010-05-23
• [Presentation] UV Curable Monomers for Imprint Lithography (2010)
  • Author(s): M.Shirai
  • Organizer: RadTech UV & EB 2010 Technology Expo and Conference
  • Place of Presentation: Baltimore, MD, USA(招待講演)
  • Year and Date: 2010-05-23
• [Presentation] UV Curable Resin with Degradable Property(Invited) (2009)
  • Author(s): M. Shirai
  • Organizer: 11th Pacific Polymer Conference 2009
  • Place of Presentation: Cairns, Australia
  • Year and Date: 2009-12-07
• [Presentation] UV Curable Resin with Degradable Property(Invited) (2009)
  • Author(s): Masamitsu Shirai
  • Organizer: 11th Pacific Polymer Conference 2009
  • Place of Presentation: オーストラリア, ケアンズ
  • Year and Date: 2009-12-07
• [Presentation] Degradable Resist for UV Nanoimprint Lithography (2009)
  • Author(s): M. Shirai
  • Organizer: The International Conference on Nanoimprint and Nanoprint Technology
  • Place of Presentation: San Jose, CA, USA
  • Year and Date: 2009-11-12
• [Presentation] Degradable Resist for UV Nanoimprint Lithography (2009)
  • Author(s): Masamitsu Shirai
  • Organizer: The International Conference on Nanoimprint and Nanoprint Technology
  • Place of Presentation: 米国, サンノゼ
  • Year and Date: 2009-11-12
• [Presentation] ヘミアセタールエステル部位を有する新規メタクリラートの合成とリワーク樹脂への応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第59回ネットワークポリマー講演討論会
  • Place of Presentation: 大阪
  • Year and Date: 2009-10-16
• [Presentation] エポキシ基を含むリワーク型モノマーのUVナノインプリントリソグラフィーへの応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子討論会
  • Place of Presentation: 熊本
  • Year and Date: 2009-09-16
• [Presentation] メタクリラートユニットを側鎖に有するヘミアセタールエステルオリゴマーの光架橋と解架橋 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子討論会
  • Place of Presentation: 熊本
  • Year and Date: 2009-09-16
• [Presentation] リワーク能を有する低収縮性UV硬化樹脂の合成とその応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子討論会
  • Place of Presentation: 熊本
  • Year and Date: 2009-09-16
• [Presentation] リワーク型エポキシ樹脂のUVナノインプリントリソグラフィーへの応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子学会年次大会
  • Place of Presentation: 神戸
  • Year and Date: 2009-05-27
• [Presentation] リワーク能を有する低収縮性UV硬化樹脂 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子学会年次大会
  • Place of Presentation: 神戸
  • Year and Date: 2009-05-27
• [Presentation] リワーク型光硬化樹脂のUVナノインプリントへの応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子学会年次大会
  • Place of Presentation: 神戸
  • Year and Date: 2009-05-27
• [Presentation] リワーク型UV架橋ポリマーの設計と応用 (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子学会年次大会
  • Place of Presentation: 神戸
  • Year and Date: 2009-05-27
• [Presentation] リワーク型UV架橋ポリマーの設計と応用(招待講演) (2009)
  • Author(s): 白井正充
  • Organizer: 第58回高分子学会年次大会
  • Place of Presentation: 神戸
  • Year and Date: 2009-05-27
• [Book] 高分子の架橋と分解III (2012)
  • Author(s): 白井正充(分担執筆)
  • Total Pages: 14
  • Publisher: シーエムシー
• [Book] 高機能アクリル樹脂の開発と応用 (2011)
  • Author(s): 白井正充
  • Publisher: シーエムシー
• [Book] 高分子の架橋と分解III (2011)
  • Author(s): 白井正充
  • Publisher: シーエムシー
• [Book] 高機能アクリル樹脂の開発と応用 (2011)
  • Author(s): 白井正充(分担執筆)
  • Total Pages: 10
  • Publisher: シーエムシー
• [Book] LED-UV硬化技術と硬化材料の現状と展望-発光ダイオードを用いた紫外線硬化技術 (2010)
  • Author(s): 白井正充
  • Publisher: シーエムシー
• [Book] 総説エポキシ樹枝最近の進歩I (2009)
  • Author(s): 白井正充
  • Publisher: エポキシ樹脂技術協会
• [Book] 高分子の架橋・分解技術-グリーンケミストリー (2009)
  • Author(s): 白井正充
  • Publisher: シーエムシー
• [Book] フォトレジスト材料開発の新展開 (2009)
  • Author(s): 白井正充
  • Publisher: シーエムシー
• [Book] 総説エポキシ樹枝 最近の進歩I (2009)
  • Author(s): 白井正充
  • Total Pages: 12
  • Publisher: エポキシ樹脂技術協会
• [Book] 高分子の架橋・分解技術-グリーンケミストリー (2009)
  • Author(s): 白井正充
  • Total Pages: 26
  • Publisher: シーエムシー出版
• [Book] フォトレジスト材料開発の新展開 (2009)
  • Author(s): 白井正充
  • Total Pages: 15
  • Publisher: シーエムシー出版
• [Book] Basics and Applications of Photopolymerization Reactions (2009)
  • Author(s): Masamitsu Shirai
  • Total Pages: 10
  • Publisher: Research Signpost, India
• [Remarks]
  • URL: http://www.chem.osakafu-u.ac.jp/ohka/ohka7/index/index.html
• [Remarks]
  • URL: http://www.chem.osakafu-u.ac.jp/ohka/ohka7/index/index.html