Syntheses of o-methacryloyl-N-acyl tyrosines and their adhesiveness to un-etched human dentin.

J. Tanaka, K. Suzuki, H. Nakai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

O-Methacryloyl-N-acyl tyrosines (MAATY) having acyl groups with the various chain length were synthesized and the strength of bonding agents, consisting of MAATY as an adhesive monomer, to unetched human dentin was studied to elucidate the relationship between the molecular structure of MAATY and its adhesive characteristics. Increasing the flexibility of the carboxyl group of tyrosine favors the interaction with the tooth substrate, causing strict bonding. Also, the properties of the neighboring carboxyl group, i. e., steric hindrance and hydrophobicity, hydrophobic-hydrophilic balance in the monomer, and shrinkage of the monomer at copolymerization, are considered important. Especially, steric hindrance of the substituted group neighboring the carboxyl group of tyrosine would play an extremely important role in the adhesion of O-methacryloyl-N-octanoyl tyrosine. The maximum tensile bond strength was obtained with a bonding agent consisting of O-methacryloyl-N-hexanoyl tyrosine (15 mol%) and hydroxyethyl methacrylate (85 mol%), and the strength (4.75 MPa) was the maximum in all methacrylates with phenylalanine as a bone structure.

Original languageEnglish
Pages (from-to)55-65
Number of pages11
JournalDental Materials Journal
Volume13
Issue number1
Publication statusPublished - Jun 1994

Fingerprint

Adhesiveness
Dentin
Tyrosine
Monomers
Adhesives
Bond strength (materials)
Hydrophobicity
Chain length
Copolymerization
Molecular structure
Bone
Adhesion
Substrates
Methacrylates
Tensile Strength
Molecular Structure
Phenylalanine
Hydrophobic and Hydrophilic Interactions
Tooth
Bone and Bones

ASJC Scopus subject areas

  • Biomaterials
  • Dentistry(all)

Cite this

Syntheses of o-methacryloyl-N-acyl tyrosines and their adhesiveness to un-etched human dentin. / Tanaka, J.; Suzuki, K.; Nakai, H.

In: Dental Materials Journal, Vol. 13, No. 1, 06.1994, p. 55-65.

Research output: Contribution to journalArticle

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