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Development and application of water soluble surfactant which inhibit the adherence of plaque onto tooth surface.

Research Project

Project/Area Number 16390548
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Conservative dentistry
Research InstitutionKanagawa Dental College

Principal Investigator

TERANAKA Toshio  Kanagawa Dental College, Oral Medicine, Professor, 歯学部, 教授 (60104460)

Co-Investigator(Kenkyū-buntansha) YOSHINO Norio  Tokyo University of Science, Industrial Chemistry, Professor, 工学部, 教授 (50084380)
KURATA Shigeaki  Kanagawa Dental College, Biomaterials and Devises, Assistant Professor, 歯学部, 助教授 (20104333)
KONDO Yukishige  Tokyo University of Science, Industrial Chemistry, Assistant Professor, 工学部, 講師 (70277276)
二瓶 智太郎  神奈川歯科大学, 歯学部, 講師 (50237781)
Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥14,400,000 (Direct Cost: ¥14,400,000)
Fiscal Year 2006: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2005: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2004: ¥9,600,000 (Direct Cost: ¥9,600,000)
Keywordsplaque / dental caries / periodontal disease / bio-film / enamel / hydroxyapatite / surface free energy / fluorinated surface modifier / 歯周疾患予防 / バイオフィルム形成抑制 / リン酸エステル塩型フッ素系界面活性剤
Research Abstract

We have considered that decreasing the surface free energy of tooth surface may contribute to prevention of caries and periodontal disease. We have synthesized the novel hybrid surfactants named sodiuml-[(4hepta- decafluorooct1)-1-hexyl-phenyl phosphate (F8H5PPhNa), sodium1-[(4heptadecafluorooctyl)phenyl]-1-butylphenyl phosphate (F8H3PPhNa), 1H,1H,2H,2H-perfluorohexylphenylphosphoric acid (F4), 1H,1H,2H,2H-perfluorooctyl phenyl phosphoric acid (F6), and 1H,1H,2H,2H-perfluorodecyl phenyl phosphoric acid (F8) containing a fluorocarbon chain and hydrocarbon chain in a molecule. The aim of this study was to investigate the surface free energy and the acid resistance of the enamel surface treated with novel hybrid surfactants.
Smoothly finished bovine enamel surface was modified with F8H5PPhNa, F8H3PPhNa prepared to 1mmol/l with distilled water, and with a 20mmol/l of F4, F6 or F8/5% ethanol. The surface free energies were computed using the Drop Method. In order to evaluate water-proof of the modified surface, the enamel specimens were stored in water at 37℃ for 1, 3, 7, 14, 21, 28, 60, and 90 days. The specimens were immersed in a 0.1 mol/l of sodium acetate buffer of pH4.0 for 30min and the amounts of Ca^<2+> was measured by atomic absorption analysis.
The surfaces of specimens were observed by SEM.
The surface free energy of modified by these surfactants were significantly lower than the control (p<0.05). However, the surface free energies of all groups were increased after 3-day storage in water. The amounts of Ca^<2+> dissolved from modified groups were less than control (p<0.05). The F8 modified group was a quarter of that of the control and the lowest of the groups (p<0.01). The F8 modified enamel surface also showed less decalcification compared with that of the control by SEM observation.
From these results, it was suggested that the novel hybrid and aqueous surfactants i.e.F8 is promising to prevent plaque accumulation on the enamel surface.

Report

(4 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (48 results)

All 2007 2006 2005 2004

All Journal Article (45 results) Book (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Protein adsorption and stability of poly(ethylene oxide)-modified surfaces having hydrophobic layer between substrate and polymer.2007

    • Author(s)
      Tsukagoshi T, Kondo Y, Yoshino N
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 54

      Pages: 82-87

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Surface modification of poly(oligoethylene oxide methacrylate) for resisting protein adsorption.2007

    • Author(s)
      Tsukagoshi T, Kondo Y, Yoshino N
    • Journal Title

      Colloids and Surfaces B 54

      Pages: 94-100

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Protein adsorption on polymer-modified silica particle surface.2007

    • Author(s)
      Tsukagoshi T, Kondo Y, Yoshino N
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 54

      Pages: 101-107

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Preparation of thin polymer films with drug release and protein adsorption resistance.2007

    • Author(s)
      Tsukagoshi T, Kondo Y, Yoshino N
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 55

      Pages: 19-25

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Surface modification of poly(oligoethylene oxide methacrylate) for resisting protein adsorption.2007

    • Author(s)
      Tsukagoshi T, Kondo Y, Yoshino N
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 54

      Pages: 94-100

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Langmuir monolayer properties of the fluorinated-hydrogenated Hybrid amphiphiles with dipalmitoylphosphatidylcholine (DPPC)2006

    • Author(s)
      Hoda K, Nakahara H, Nakahara S, Nagadome S, Sugihara G, Yoshino N, Shibata O
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 47

      Pages: 165-175

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel highly heat-resistant fluorinated silane coupling agents.2006

    • Author(s)
      Yoshino N, Sato T, K, Furukawa M, Kondo Y
    • Journal Title

      J. Fluorine Chem. 127

      Pages: 1058-1065

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Mode of interaction of two fluorinated-hydrogenated hybrid amphiphiles with dipalmitoylphosphatidylcholine (DPPC) at the air-water interface.2006

    • Author(s)
      Hoda K, Kawasaki H, Yoshino N, Chang CH, Morikawa Y, Sugihara G, Shibata O
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 53

      Pages: 37-50

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Langmuir monolayer properties of the fluorinated-hydrogenated Hybrid amphiphiles with dipalmitoylphosphatidylcholine (DPPC).2006

    • Author(s)
      Hoda K, Nakahara H, Nakahara S, Nagadome S, Sugihara G, Yoshino N, Shibata O
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 47

      Pages: 165-175

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel highly heat-resistant fluorinated silane coupling agents.2006

    • Author(s)
      Yoshino N, Sato T, K, Furukawa M, Kondo Y
    • Journal Title

      Journal of Fluorine Chem. 127

      Pages: 1058-1065

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Mode of interaction of two fluorinated-hydrogenated hybrid amphiphiles with dipalmitoylphosphatidylcholine (DPPC) at the air-water interface.2006

    • Author(s)
      Hoda K, Kawasaki H, Yoshino N, Chang CH, Morikawa Y, Sugihara G, Shibata 0
    • Journal Title

      Colloids and Surfaces B : Biointerfaces 53

      Pages: 37-50

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel highly heat-resistant fluorinated silane coupling agents.2006

    • Author(s)
      Yoshino N, Sato T, Miyao K, Furukawa M, Kondo Y.
    • Journal Title

      J Fluorine Chem 127

      Pages: 1058-1065

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Micelle Formation of Phosphate-Type Hybrid Surfactants in Aqueous Solution.2005

    • Author(s)
      Inoue, T, Nakashima N, Sugihara G, Yoshino N
    • Journal Title

      J. Oleo Science 54・2

      Pages: 95-103

    • NAID

      130000055668

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Phase Behavior of Mixed Solutions of a Cationic Surfactant with a Ferrocenyl Group and an Anionic Surfactant : Surface Chemical and Electrochemical Approaches.2005

    • Author(s)
      Imamura H, Tsuchiya H, Kondo Y, Yoshino N, Ohkubo T, Sakai H, Abe M
    • Journal Title

      J. Oleo Science 54・3

      Pages: 125-134

    • NAID

      130000055655

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Solution Properties of Sulfate-Type Hybrid Surfactants with an Ethylene Spacer.2005

    • Author(s)
      Miyazawa H, Kondo Y, Yoshino N
    • Journal Title

      J. Oleo Science 54・3

      Pages: 167-178

    • NAID

      130000055660

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite.2005

    • Author(s)
      Miyazawa H, Yokokura H, Okubo Y, Kondo Y, Yoshino N
    • Journal Title

      J. Fluorine Chem. 126

      Pages: 301-306

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hybrid fluorocarbon/hydrocarbon surfactants.2005

    • Author(s)
      Kondo Y, Yoshino
    • Journal Title

      Current Opinion in Colloid & Interface Science 10・3, 4

      Pages: 88-93

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] リン酸エステル塩型ハイブリッド界面活性剤によるエナメル質表面の改質効果-ハイドロキシアパタイトプレートに対する改質効果-.2005

    • Author(s)
      尾本直大, 二瓶智太郎, 倉田茂昭, 近藤行成, 楳本貢三, 好野則夫, 寺中敏夫
    • Journal Title

      日本歯科保存学雑誌 48・1

      Pages: 128-136

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 重合性基を置換した新規芳香族系シランカップリング剤の耐水性.2005

    • Author(s)
      二瓶智太郎, 倉田茂昭, 大橋 桂, 近藤行成, 楳本貢三, 好野則夫, 寺中敏夫
    • Journal Title

      歯科材料・器械 24・1

      Pages: 1-8

    • NAID

      110002989929

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Micelle Formation of Phosphate-Type Hybrid Surfactants in Aqueous Solution.2005

    • Author(s)
      Inoue, T, Nakashima N, Sugihara G, Yoshino N
    • Journal Title

      Journal of Oleo Science 54-2

      Pages: 95-103

    • NAID

      130000055668

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Phase Behavior of Mixed Solutions of a Cationic Surfactant with a Ferrocenyl Group and an Anionic Surfactant.2005

    • Author(s)
      Imamura H, Tsuchiya H, Kondo Y, Yoshino N, Ohkubo T, Sakai H, Abe M
    • Journal Title

      Journal of Oleo Science 54-3

      Pages: 125-134

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Solution Properties of Sulfate-Type Hybrid Surfactants with an Ethylene Spacer2005

    • Author(s)
      Miyazawa H, Kondo Y, Yoshino N
    • Journal Title

      Journal of Oleo Science 54-3

      Pages: 167-178

    • NAID

      130000055660

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite.2005

    • Author(s)
      Miyazawa H, Yokokura H, Okubo Y, Kondo Y, Yoshino N
    • Journal Title

      Journal of Fluorine Chem. 126

      Pages: 301-306

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hybrid fluorocarbon/hydrocarbon surfactants.2005

    • Author(s)
      Kondo Y, Yoshino N
    • Journal Title

      Current Opinion in Colloid & Interface Science 10-3 and 4

      Pages: 88-93

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Modification effect of novel phosphate type hybrid surfactant-Modification effect of surfactants for hydroxyapatite plate-2005

    • Author(s)
      Omoto N, Nihei T, Kurata S, Kondo Y, Umemoto K, Yoshino N, Teranaka T
    • Journal Title

      The Japanese Journal of Conservative Dentistry 48-1

      Pages: 128-136

    • NAID

      10014496592

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Water resistance of novel silane coupling agents having aromatic group substituted a reactive double bond.2005

    • Author(s)
      Nihei T, Kurata S, Ohashi K, Kondo S, Umemoto K, Yoshino N, Teranaka T
    • Journal Title

      The Journal of the Japanese Society for Dental Materials and Devises 24-1

      Pages: 1-8

    • NAID

      110002989929

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 重合性基を置換した新芳香族系シランカップリング剤の耐水性.2005

    • Author(s)
      二瓶智太郎 他
    • Journal Title

      歯科材料・器械 24(1)

      Pages: 1-8

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis and solution properties of sulfate-type hybrid surfactants with an ethylene spacer.2005

    • Author(s)
      Miyazawa H.et al.
    • Journal Title

      J.Oleo Science 54(3)

      Pages: 167-178

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite.2005

    • Author(s)
      Miyazawa H.et al.
    • Journal Title

      J.Fluorine Chem. 54(6)

      Pages: 301-306

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Hybrid fluorocarbon/hydrocarbon surfactants.2005

    • Author(s)
      Kondo Y.et al.
    • Journal Title

      Opinion in Colloid & Interface 10(3-4)

      Pages: 88-93

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis and solution properties of nonionic hybrid surfactants With a benzene ring.2005

    • Author(s)
      Miyazawa H.et al.
    • Journal Title

      J.Oleo Science 54(6)

      Pages: 361-368

    • Related Report
      2005 Annual Research Report
  • [Journal Article] リン酸エステル塩型ハイブリッド界面活性剤の改質効果2005

    • Author(s)
      尾本直大ほか
    • Journal Title

      日歯保存誌 48(1)

      Pages: 128-136

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Solution Properties of Sulfate-Type Fluoro-Hybrid Anionic Surfactants with a Benzene Ring in Their Molecule.2004

    • Author(s)
      Sun C, Miyazawa H, Kondo Y, Yoshino N, Abe K, Sagisaka M, Kitiyanan B, Ohkubo T, Sakai H, Abe M
    • Journal Title

      J. Oleo Science 53・8

      Pages: 371-376

    • NAID

      10013338545

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Template-Directed Patterning Using Phase-Separated Langmuir-Blodgett Films.2004

    • Author(s)
      Matsumoto M, Tanaka K, Azumi R, Kondo Y, Yoshino N
    • Journal Title

      Langmuir 20・20

      Pages: 8728-8734

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] リン酸エステル塩型ハイブリッド界面活性剤によるエナメル質表面の改質効果 (第3報)改質溶液のpHの違いによる効果.2004

    • Author(s)
      尾本直大, 二瓶智太郎, 倉田茂昭, 近藤行成, 楳本貢三, 好野則夫, 寺中敏夫
    • Journal Title

      日本歯科保存学雑誌 47・4

      Pages: 562-575

    • NAID

      10013485006

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 再生すること,永らえること.2004

    • Author(s)
      寺中敏夫
    • Journal Title

      神奈川歯学 39・2, 3

      Pages: 115-117

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Solution Properties of Sulfate-Type Fluoro-Hybrid Anionic Surfactants with a Benzene Ring in Their Molecule.2004

    • Author(s)
      Sun C, Miyazawa H, Kondo Y, Yoshino N, Abe K, Sagisaka M, Kitiyanan B, Ohkubo T, Sakai H, Abe M
    • Journal Title

      Journal of Oleo Science 53-8

      Pages: 371-376

    • NAID

      10013338545

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Template-Directed Patterning Using Phase-Separated Langmuir-Blodgett Films.2004

    • Author(s)
      Matsumoto M, Tanaka K, Azumi R, Kondo Y, Yoshino N
    • Journal Title

      Langmuir 20-20

      Pages: 8728-8734

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enamel surface modification by nove phosphate type hybrid surfactant・Modification effect of surfactant at different pH-2004

    • Author(s)
      Omoto N, Nihei T, Kurata S, Kond Y, Umemoto K, Yoshinc N, Teranaka T
    • Journal Title

      The Japanese Journal of Conservative Dentistry 47-4

      Pages: 562-575

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Regeneration and long-lasting.2004

    • Author(s)
      Teranaka T
    • Journal Title

      Journal of Kanagawa Odontological Society 39-2 and 3

      Pages: 115-117

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of and Glass Surface Modification with Fluorinated Silane Coupling Agents with a Benzene Ring as a Spacer2004

    • Author(s)
      Kondo Y. et al.
    • Journal Title

      J.Oleo Science 53(3)

      Pages: 143-151

    • NAID

      10012104345

    • Related Report
      2004 Annual Research Report
  • [Journal Article] リン酸エステル塩型ハイブリッド界面活性剤によるエナメル質表面の改質効果(第2報)改質溶液濃度の違いによる効果2004

    • Author(s)
      尾本直大ら
    • Journal Title

      日歯保存誌 47(2)

      Pages: 242-252

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Solution Properties of Sulfate-Type Fluoro-Hybrid Anionic Surfactants with a benzene Ring in Their Molecule2004

    • Author(s)
      Chengxu Sun et al.
    • Journal Title

      J.Oleo Science 53(3)

      Pages: 371-376

    • Related Report
      2004 Annual Research Report
  • [Journal Article] リン酸エステル塩型ハイブリッド界面活性剤によるエナメル質表面の改質効果(第3報)改質溶液のpHの違いによる効果2004

    • Author(s)
      尾本直大ほか
    • Journal Title

      日歯保存誌 47(4)

      Pages: 562-575

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis and phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite2004

    • Author(s)
      Miyazawa H et al.
    • Journal Title

      J.Fluorine Chem. 125

      Pages: 1485-1490

    • Related Report
      2004 Annual Research Report
  • [Book] 初期う蝕のマネージメント2004

    • Author(s)
      寺中敏夫
    • Total Pages
      11
    • Publisher
      第3章 初期う蝕の予防と管理 3-4 プラークや汚れの付着を抑制する表面改質法
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] 初期う蝕のマネージメント-う蝕を進行させないために-(小松久憲 監修)2004

    • Author(s)
      寺中敏夫
    • Publisher
      クインテッセンス出版株式会社
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 学校法人東京理科大学科学技術交流センター2004

    • Inventor(s)
      好野則夫, 寺中敏夫他
    • Industrial Property Number
      2004-165988
    • Filing Date
      2004-06-03
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2004-04-01   Modified: 2016-04-21  

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