N-halamine siloxanes for use in biocidal coatings and materials

一种烷基、化合物的技术，应用在用于杀生物涂层和材料的杂环卤胺硅氧烷领域，能够解决接触时间长等问题

Inactive Publication Date: 2005-09-28
AUBURN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sponges modified in this way can exhibit biocidal activity, but often the contact time required for action is long and some pathogens are not inactivated even after hours of contact time

Method used

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  • N-halamine siloxanes for use in biocidal coatings and materials
  • N-halamine siloxanes for use in biocidal coatings and materials
  • N-halamine siloxanes for use in biocidal coatings and materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Preparation of representative unhalogenated silane compounds

[0110] Two trialkoxysilylpropylhydantoin derivatives were prepared according to methods similar to those outlined in US Patent 4,412,078.

[0111]Equip a 1-liter three-necked round-bottom flask with a condenser, dropping funnel, and thermometer. A mixture of 500 mL of ethanol, 64.0 g (0.5 mol) of 5,5-dimethylhydantoin (Acros, Inc) and 28.0 g (0.5 mol) of potassium hydroxide was added to the flask. The mixture was heated to boiling point until the solution became clear. The solid potassium salt of 5,5-dimethylhydantoin was then isolated by evaporating the ethanol solvent and the water produced in the reaction under reduced pressure. The salt was dried under vacuum at 60°C for 4 days to form the anhydrous potassium salt. The dried salt was then returned to the one liter flask where it was mixed with 500 mL of anhydrous N,N-dimethylformamide (DMF) and the mixture was heated at 60° C. until a c...

Embodiment 2

[0114] Preparation and biocidal efficacy of representative chlorosilane compounds

[0115] A portion (6.11 g, 0.021 mol) of 3-trimethoxysilylpropylhydantoin prepared as described in Example 1 was dissolved in 30 mL of dichloromethane in a 125 mL Erlenmeyer flask. Then 2.30 g (0.021 mol) of tert-butyl hypochlorite prepared according to the method of Mintz et al. 3 hours and exclude all light. The tert-butanol produced in the reaction was removed by evaporation in vacuo. The product 1-chloro-3-trimethoxysilylpropyl-5,5-dimethylhydantoin was produced as a yellow oil in 89.7% yield. It was stored at 4 °C in the absence of light until use. The total chlorine content was determined by iodometry / thiosulfate titration to be 10.36%, whereas the theoretically possible value is 10.94%. 3-trimethoxysilylpropylhydantoin at δ7.07 1 The H NMR signal disappeared upon chlorination, indicating the presence of chlorine at the 1-position of the hydantoin moiety.

[0116] A 100.8 mg / L ...

Embodiment 3

[0118] Preparation of biocidal paper

[0119] Cut a handful of white and tan business office envelopes into small squares. A 2% aqueous base solution of 3-triethoxysilylpropyl-5,5-dimethylhydantoin (pH 3 due to NaOH addition) prepared as described in Example 1 was dissolved in a nebulizer bottle Spray onto both sides of the paper samples until they become saturated. The wet samples were then cured until dry at 60 °C for 15 min. Both sides of the cured sample were then sprayed with 10% CLOROX bleach until saturated, allowed to stand at room temperature for 10 minutes, rinsed 5 times with 50 mL of partially chlorine-free water, and dried at room temperature. Samples were stored in a vacuum desiccator until analysis and microbiological characterization.

[0120] Iodometric / thiosulfate titration was used to determine the chlorine loading on squares of both papers as a function of time after chlorination. The data are shown in Table 1.

[0121] sa...

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Abstract

Heterocyclic and acyclic silane monomers and siloxane polymers, and their halogenated derivatives, are provided for the purpose of functionalizing surfaces or materials so as to render them biocidal upon exposure to oxidative halogen solutions. The biocidal function can be imparted either before or after bonding or adhesion to the surface or material. The biocidal surfaces and materials can then be used to inactivate pathogenic microorganisms such as bacteria, fungi, and yeasts, as well as virus particles, which can cause infectious diseases, and those microorganisms which cause noxious odors and unpleasant coloring such as mildew. Examples of surfaces and materials which can be rendered biocidal in this invention include, but are not limited to, cellulose, chitin, chitosan, synthetic fibers, glass, ceramics, plastics, rubber, cement grout, latex caulk, porcelain, acrylic films, vinyl, polyurethanes, silicon tubing, marble, metals, metal oxides, and silica.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of pending U.S. Provisional Application 60 / 388,968, filed June 14, 2002, and is a continuation-in-part of U.S. Application 10 / 400,165, filed March 24, 2003, both of which are expressly written in full This article is incorporated by reference. field of invention [0003] The present invention relates to the synthesis and use of silanes and siloxane compounds for the purpose of structuring coatings and materials such that they become biocidal by contact with halogen solutions, either before or after curing. The biocidal coatings and materials can then be used to inactivate pathogenic microorganisms such as bacteria, fungi and yeast as well as virus particles that can cause infectious diseases and microorganisms that cause harmful odors and unpleasant stains such as mold. The coating is compatible with a variety of substrates including: cellulose, ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07F7/18
CPCC07F7/1836Y10T428/31663C07F7/1804
Inventor S·D·沃里陈永俊王佳万吴朗李阳君
Owner AUBURN UNIV
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