Development of dental resin adhesives using stimuli-responsively degradable and enamel-adhesive polyrotaxanes for orthodontics

• Project/Area Number: 24650274
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Biomedical engineering/Biological material science
• Research Institution: Tokyo Medical and Dental University
• Principal Investigator: NOBUHIKO Yui 東京医科歯科大学, 生体材料工学研究所, 教授 (70182665)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
• Keywords: 歯科材料 / ポリロタキサン / 刺激応答性

Outline of Final Research Achievements

Resin monomer-soluble polyrotaxane (PRX) crosslinkers with cleavable end-groups were designed to develop degradable resins for orthodontics. The PRX containing 50 α-cyclodextrins (α-CDs) with disulfide end-groups was modified with n-butyl groups per α-CD molecule was completely soluble in conventional resin monomers such as 2-hydroxyethyl methacrylate (HEMA) and urethane dimethacrylate (UDMA). The synthesized n-butyl-containing PRX was further modified with 2-aminoethyl methacrylate to provide crosslinkable acrylic groups onto PRX. The prepared resin monomer-soluble PRX crosslinker was successfully polymerized with a mixture of HEMA and UDMA to provide photosetting plastic. It was confirmed that the Vickers hardness of the prepared plastic was greatly decreased after treatment with dithiothreitol. This result indicates that the resin monomer-soluble PRX crosslinkers have much potential in applications for degradable photosetting plastics potentially used in orthodontics.

Research Products

• [Journal Article] Synthesis of a resin monomer-soluble polyrotaxane crosslinker containing cleavable end groups (2014)
  • Author(s): J.-H. Seo, S. Nakagawa, K. Hirata, N. Yui.
  • Journal Title: Beilstein J. Org. Chem. Volume: 10 Pages: 2623-2629
  • DOI: 10.3762/bjoc.10.274
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Presentation] 培養細胞を用いた歯科用レジン成分の感作性評価 (2012)
  • Author(s): 片岡いづみ、田村篤志、由井伸彦、松村光明、三浦宏之
  • Organizer: 日本補綴歯科学会東京支部総会
  • Place of Presentation: 東京（京成ホテル）
• [Patent(Industrial Property Rights)] 接着性組成物 (2014)
  • Inventor(s): 徐 知勲、由井伸彦、平田広一郎、中川史乃
  • Industrial Property Rights Holder: 徐 知勲、由井伸彦、平田広一郎、中川史乃
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2014-224016
  • Filing Date: 2014-11-04