Synthesis and Coupling Effect of Novel Silane Coupling Agent with Fluoroalkyl Group and Phenyl Group Containing Double Bond

DOI 1 Citations 26 References
  • SHIMIZU Tota
    Division of Removal Prosthetics, Department of Oral and Maxillofacial Rehabilitation, Kanagawa Dental College
  • NIHEI Tomotaro
    Division of Restorative Dentistry, Department of Oral Medicine, Kanagawa Dental College
  • KURATA Shigeaki
    Department of Dental Materials and Devices, Kanagawa Dental College
  • OHASHI Katsura
    Division of Restorative Dentistry, Department of Oral Medicine, Kanagawa Dental College
  • KONDO Yukishige
    Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science
  • YOSHINO Norio
    Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science
  • TERANAKA Toshio
    Division of Restorative Dentistry, Department of Oral Medicine, Kanagawa Dental College

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  • 重合性基を有しフルオロアルキル基とベンゼン環を導入した新規シランカップリング剤の合成と接着耐水性効果

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Abstract

To improve the bond strength and durability against hydrolysis of the silica-resin interface, a novel silane coupling agent containing a hydrophobic fluoroalkyl and/or phenyl group, 3-{4-[di(trifluoromethyl)-4'-methacryloyloxyphenylmethyl]phenoxy}propyltrimethoxysilane (p-MBFBS), was synthesized. The silane coupling agents used in this study were 3-methacryloyloxypropyltrimethoxysilane (3-MPS), nonafluorohexyltrimethoxysilane (4F), 3-{4-[di(trifluoromethyl)-4'-methacryloyloxyphenylmethyl]phenoxy}propyltrimethoxysilane (p-MBS), and p-MBFBS. The concentration of each silane solution was adjusted to 2 mass% with ethanol, and then the contact angles of a resin monomer mixture (Bis-GMA:TEGDMA=50:50) to glass plates modified with each silane and the tensile bond strength of resin composite were measured. The glass surface modified with 4F/3-MPS showed significantly higher affinity than 3-MPS, p-MBS and p-MBFBS. The contact angle of the monomer mixture to the p-MBS or p-MBFBS modified glass plates was the same as that modified with 3-MPS. The tensile bond strength of the resin composites to glass plates modified with 4F/3-MPS, p-MBS or p-MBFBS was significantly higher compared with 3-MPS after water immersion for 360 days. Furthermore, the bond strength of 4F/3-MPS and p-MBS showed no significant difference after water immersion or thermal stress compared with those stored at room temperature in air for 1 day. These results suggest that the novel silane coupling agent containing both hydrophobic fluoroalkyl group and phenyl group has better water resistance than 3-MPS, however, the silane coupling agent containing only a hydrophobic group produces a coupling layer with the best water resistance over the long term.

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