Synthesis of a resin monomer soluble polyrotaxane crosslinker containing cleavable end groups for dental application

• Project/Area Number: 24700477
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Biomedical engineering/Biological material science
• Research Institution: Tokyo Medical and Dental University
• Principal Investigator: SEO JI-HUN 東京医科歯科大学, 生体材料工学研究所, 助教 (20611544)
• Research Collaborator: YUI Nobuhiko 東京医科歯科大学, 生体材料工学研究所, 教授 ; HIRATA Koichiro (株)トクヤマデンタル, 研究所所長 ; NAKAGAWA Shino (株)トクヤマデンタル, 研究所研究員
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 歯科用材料 / ポリロタキサン / 超分子化学 / 歯科材料

Outline of Final Research Achievements

A resin monomer-soluble polyrotaxane (PRX) crosslinker with cleavable end-groups was synthesized to develop degradable dental composite resins. The PRX containing 13 n-butyl group per CD molecule was completely soluble in conventional resin monomers such as 2-hydroxyethyl methacrylate (HEMA) and urethane dimethacrylate (UDMA). The synthesized n-butyl-introduced PRX was further modified with 2-aminoethyl methacrylate to provide crosslinkable acrylic groups onto PRX. The prepared resin monomer-soluble PRX crosslinker was successfully polymerised 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 indicates that the resin monomer-soluble PRX crosslinker can be applied to design degradable photosetting plastics potentially used in industrial or biomedical field.

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
• [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