Synthesis and antimicrobial activity of quaternary ammonium silane coupling agents.

Fourteen novel silane coupling agents with a quaternary ammonium group introduced into the molecule, [CH(2)=CHCH(2)N(+)(CH(3))(C(n)H(2n+1))(CH(2))(3)Si(OCH(3))(3)]X(-) (n-X, n=10-18, X=Cl, Br, or I), were synthesized with the aim of using these agents to make material surfaces antimicrobial for a long period of time. Measurements of the minimum inhibitory concentrations (MIC) against 12 kinds of fungi and bacteria revealed that the coupling agent with a C(10) alkyl chain and Cl- or Br- counter-ion (10-Cl or 10-Br) has the highest antimicrobial activity among the n-X agents synthesized, but 14-Cl and 14-Br showed the highest activity on a modified porcelain plate.