Biocidal N-halamine epoxides
Inventors
Worley, Shelby D. • Liang, Jie • Chen, Yongjun • Broughton, Royall M. • Wang, Jia-Wang • Wu, Rong • Cho, Unchin • Lee, Jaewoong • Barnes, Kevin
Assignees
Auburn University • Auburn University System
Publication Number
US-8821907-B2
Publication Date
2014-09-02
Expiration Date
2026-03-10
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Abstract
N-halaminehydantoinyl epoxide compounds which can be used for the construction of coatings and materials which can be rendered biocidal by exposure to halogen solutions either before or after curing the coating or material are disclosed. The biocidal coatings 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. The coatings are compatible with a variety of substrates including, but not limited to, cellulose, chitin, chitosan, synthetic fibers, cement grout, latex caulk, acrylic films, polyurethanes, plastics and paints.
Core Innovation
The invention provides methods for attaching biocides onto surfaces and/or incorporating them into materials by utilizing N-halamine hydantoinyl epoxide compounds. These compounds can be synthesized and used in the construction of biocidal coatings and materials. The N-halamine hydantoinyl epoxide compounds are preferably attached to surfaces or materials through a ring-opening mechanism of the epoxide portion, allowing for effective binding and subsequent halogenation to render the composition biocidal.
The resulting biocidal coatings and materials are capable of inactivating pathogenic microorganisms such as bacteria, fungi, and yeasts, as well as virus particles, which can cause infectious diseases and noxious odors or unpleasant coloring like mildew. The invention allows for compatibility with a wide variety of substrates, including cellulose, chitin, chitosan, synthetic fibers, cement grout, latex caulk, acrylic films, polyurethanes, plastics, and paints.
The problem addressed by this invention is that previous methods for imparting biocidal activity to materials and coatings, such as physical mixing or chemical binding of biocidal groups, have been inadequate, often requiring long contact times and using agents that are either weak, non-regenerable, or environmentally hazardous. Existing N-halamine-based biocides also had limited application for coating materials. Therefore, there is a continued need for more effective, versatile, and environmentally safer biocidal coatings and materials.
Claims Coverage
There are three independent claims in the patent, each introducing a different inventive feature relating to methods and compositions involving N-halamine hydantoinyl epoxides.
Method of rendering a material biocidal using N-halamine hydantoinyl epoxide
This inventive feature involves adding an N-halamine or a precursor of N-halamine, which comprises a hydantoinyl portion and an epoxide portion, to a material. The N-halamine or its precursor is specifically a hydantoinyl epoxide having a defined structure. The method enables the material to become biocidal after treatment.
Composition with hydantoinyl epoxide structures bound to a material
This feature covers a composition in which hydantoinyl epoxide structures are bound to a material via the oxygen atoms of the epoxide moieties. The hydantoinyl epoxide has a specific structural formula. The material can include substrates such as cellulose, chitin, chitosan, synthetic fibers, cement grout, latex caulk, acrylic film, polyurethane, plastics, and paint.
Halogenated composition with hydantoinyl epoxide structures bound to a material
This inventive feature is a composition comprising hydantoinyl epoxide structures bound to a material through oxygen atoms of the epoxide moieties, where the hydantoinyl structures are halogenated. The structure and the types of materials are as detailed for the previous composition claim.
The independent claims cover methods for making materials biocidal using hydantoinyl epoxides, compositions in which these structures are bound to materials, and compositions in which the bound hydantoinyl epoxides are halogenated for biocidal functionality.
Stated Advantages
The biocidal surfaces and materials of this invention are much more effective against pathogenic microorganisms encountered in medical applications than commercial biocides such as quaternary ammonium salts.
The invention enables inactivation of disease-causing pathogens and odor-causing microorganisms, allowing dual functionality in various settings.
Biocidal activity can be replenished by rechlorination or rebromination, enabling the coating to maintain efficacy throughout the lifetime of the material.
The coatings can be made compatible with a wide range of substrates and materials.
The invention addresses environmental hazards posed by tin-based biocidal materials, providing a potentially safer alternative.
Documented Applications
The invention can be used to make biocidal surfaces and materials such as envelopes, surgical gowns and gloves, sheets, bandages, sponges, synthetic fibers, wood, chitin, chitosan, cement grout, latex caulk, acrylic films, paints, and polyurethanes.
It is specifically noted to be useful in medical settings such as hospitals, nursing facilities, and research laboratories.
The invention can be applied for biocidal activity in a variety of industrial settings and in the home.
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