Method of fixing antibacterial agent and article obtained by the method

• US 8,859,009 B2
• Filed: 04/21/2009
• Issued: 10/14/2014
• Est. Priority Date: 05/09/2008
• Status: Active Grant

• Current Assignee: Hiroshima University
• Original Assignee: Hiroshima University
• Inventors: Nikawa, Hiroki
• Primary Examiner(s): Claytor, Renee
• Assistant Examiner(s): Kantamneni, Shobha
• Application Number:
  US12/736,794
• Publication Number:
  US 20110172183A1
• Time in Patent Office: 2,002 Days
• Field of Search: 424/613, 424/405, 427/452, 510/384
• US Class Current: 424/613
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/24 containing ingredients to enhance the sticking of the active ingredients
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: C11D 1/62 Quaternary ammonium compounds
• CPC Class Codes: C11D 3/162 containing Si
• CPC Class Codes: C11D 3/48 Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Abstract

An object of the present invention is to provide a method of fixing an antibacterial agent, by which method it is possible to impart articles of a wide range of materials with excellent antibacterial property and good persistence of antibacterial activity. Specifically, the method of fixing an antibacterial agent, comprises the steps of:

• • subjecting a surface of an article to a surface treatment of providing the surface with oxygen-containing functional groups; and then
  • subjecting the article to a treatment using an antibacterial agent composition including a silicon-containing compound (a) represented by general formula (1) below.

wherein R¹ represents a hydrocarbon group having 6 or more carbon atoms, R² and R³ represent lower hydrocarbon groups, respectively, which hydrocarbon groups may be the same or different from each other, R⁴ represents a divalent lower hydrocarbon group, R⁵, R⁶ and R⁷ represent lower alkyl groups or lower alkoxy groups, respectively, which may be the same or different from each other, and X represents a halogen ion or an organic carbonyloxy ion, or alternatively, first treating the article by using the antibacterial agent composition; and then subjecting the article to a 1-10 GHz microwave irradiation treatment in a state where the antibacterial agent composition remains on the surface of the article.

Claims

1. A method of fixing an antibacterial agent on an article, comprising the steps of:

subjecting a surface of an article to an ozone water treatment of providing the surface with oxygen-containing functional groups by treating the surface with ozone water; and

then

subjecting the article to a treatment using an antibacterial agent composition including a silicon-containing compound represented by the general formula below

2. The method of fixing an antibacterial agent of claim 1, wherein said ozone water treatment is one of immersing the article in ozone water, spraying ozone water onto the article, or coating the article with ozone water.

3. The method of fixing an antibacterial agent of claim 1, wherein R¹ of the silicon-containing compound represented by general formula represents C_10-25 alkyl group, R² and R³ represent C_1-6 alkyl groups, respectively, which alkyl groups may be the same or different from each other, R⁴ represents a C_1-6 alkylene group, R⁵, R⁶ and R⁷ represent C_1-6 alkoxy groups, respectively, which may be the same or different from each other, and X represents a halogen ion or an organic carbonyloxy ion.

4. The method of fixing an antibacterial agent of claim 1, wherein the silicon-containing compound represented by general formula is at least one type of silicon-containing compound selected from the group consisting of:

octadecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride,

octadecyldimethyl(3-triethoxysilylpropyl)ammonium chloride,

octadecyldiethyl(3-trimethoxysilylpropyl)ammonium chloride,

octadecyldipropyl(4-trimethoxysilylbutyl)ammonium acetate,

octadecyldimethyl(3-triisopropoxysilylpropyl)ammonium chloride,

heptadecyldimethyl(3-trimethoxylsilylpropyl)ammonium chloride,

heptadecyldiisopropyl(2-triethoxysilylethyl)ammonium chloride,

hexadecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride,

hexadecyldimethyl(3-trimethoxysilylpropyl)ammonium acetate, and

pentadecyldimethyl(3-triethoxysilylpropyl)ammonium chloride.

5. The method of fixing an antibacterial agent of claim 1, wherein the non-ionic surfactant is at least one type of non-ionic surfactant selected from the group consisting of alkyl ethers or esters of fatty acids derived from polyoxyalkylene glycol containing polyoxyethylene unit and/or polyoxypropylene unit, sorbitan esters of fatty acids, fatty acid monoglyceride, esters of fatty acids, fatty acid alkanolamides, fatty acid amides, alkyl ethers, alkyl amine oxides, polyoxyethylenealkyl ethers, and polyoxyethylene nonylphenyl ether.

6. The method of fixing an antibacterial agent of claim 5, wherein the non-ionic surfactant is polyoxyethylene sorbitan monolaurate.