Compositions and methods for making and using acyclic N-halamine-based biocidal polymeric materials and articles

• US 8,486,428 B2
• Filed: 03/27/2006
• Issued: 07/16/2013
• Est. Priority Date: 03/27/2006
• Status: Active Grant

• Current Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Original Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Inventors: Sun, Yuyu, Luo, Jie
• Primary Examiner(s): DICKINSON, PAUL W
• Application Number:
  US11/389,968
• Publication Number:
  US 20070224161A1
• Time in Patent Office: 2,668 Days
• Field of Search: None
• US Class Current: 424/405
• CPC Class Codes: A01N 37/28 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: A61K 31/785 Polymers containing nitrogen
• CPC Class Codes: D06M 13/41 Amides derived from unsaturated carboxylic acids, e.g. acrylamide
• CPC Class Codes: D06M 14/04 of vegetal origin, e.g. cellulose or derivatives thereof
• CPC Class Codes: D06M 14/10 of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

Abstract

The present invention includes methods and compositions for providing rechargeable aliphatic N-halamine polymers, monomers, copolymers additives and coatings. The rechargeable aliphatic N-halamine includes an aliphatic N-halamine compound exchangeable associated with one or more halides.

Claims

1. A rechargeable aliphatic N-halamine polymer comprising:

a cotton substrate;

a rechargeable aliphatic N-halamine polymer grafted directly to the cotton substrate, wherein the rechargeable aliphatic N-halamine polymer is formed from the polymerization of one or more aliphatic N-halamine methacrylamide monomers selected from N-alkyl-monosubstituted, N-alkylamino-monosubstituted, and N,N-dialkyl-substituted, N,N-dialkylamino-disubstituted; and

one or more halides associated with the one or more aliphatic N-halamine methacrylamide monomers, whereby the one or more halides provide inactivation of bacteria cells, spores, fungus, yeasts, viruses or a combination thereof.

2. The composition of claim 1, wherein the rechargeable aliphatic N-halamine polymer is a random polymer, a segmented polymer, a block polymer, a multiblock polymer, a gradient polymer, a graft polymer, a star polymer, a branched polymer, a hyperbranched polymer or segments and combinations thereof.

3. The composition of claim 1, further comprising one or more second aliphatic N-halamine monomer copolymerized with the one or more aliphatic N-halamine methacrylamide monomers to form a random polymer, a segmented polymer, a block polymer, a multiblock polymer, a gradient polymer, a graft polymer, a star polymer, a branched polymer, a hyperbranched polymer or segments and combinations thereof, wherein the one or more second aliphatic N-halamine monomer are selected from an acrylic acid, a methacrylic acid, an ethylacrylic acid, a methyl acrylate, an ethyl acrylate, a propyl acrylate, an n-butyl acrylate, an isobutyl acrylate, an t-butyl acrylate, an 2-ethylhexyl acrylate, a decyl acrylate, a methyl methacrylate, an ethyl methacrylate, a propyl methacrylate, an n-butyl methacrylate isobutyl methacrylate, an t-butyl methacrylate, an 2-ethylhexyl methacrylate, a decyl methacrylate, and combinations thereof in the form of a random polymer, a segmented polymer, a block polymer, a multiblock polymer, a gradient polymer, a graft polymer, a star polymer, a branched polymer, a hyperbranched polymer or segments and combinations thereof.

4. The composition of claim 1, further comprising forming the cotton into a fabric.

5. The composition of claim 1, further comprising a halide source to recharge microbial activity.

6. A rechargeable biocidal organic polymer made by the process comprising the steps:

polymerizing one or more acyclic N-halamine methacrylamide monomers selected from N-alkyl-monosubstituted, N-alkylamino-monosubstituted, and N,N-dialkyl-substituted, N,N-dialkylamino-disubstituted;

grafting the rechargeable biocidal organic polymer directly to a cotton; and

contacting the one or more acyclic N-halamine methacrylamide monomers with a halide source to form an activated acyclic N-halamine organic polymer with biocidal activity against bacteria, spores, fungi, yeasts, virus or a combination thereof.

7. A rechargeable biocidal fabric made by the process comprising the steps:

forming an acyclic N-halamine methacrylamide polymer from one or more methacrylamide monomers having an acyclic N-halamine compound selected from N-alkyl-monosubstituted, N-alkylamino-monosubstituted, and N,N-dialkyl-substituted, N,N-dialkylamino-disubstituted;

forming an acyclic N-halamine fabric from the acyclic N-halamine methacrylamide polymer, wherein one or more articles or garments can be constructed from the acyclic N-halamine fabric; and

contacting the acyclic N-halamine fabric with a halide source to activate the biocidal activity against bacteria, spores, fungi, yeasts, virus or a combination thereof.

8. A method of making an biocidal methacrylamide polymer comprising the steps of:

polymerizing an acyclic N-halamine methacrylamide monomer selected from N-alkyl-monosubstituted, N-alkylamino-monosubstituted, and N,N-dialkyl-substituted, N,N-dialkylamino-disubstituted into an acyclic N-halamine methacrylamide polymer;

grafting the rechargeable biocidal organic polymer directly to a cotton; and

contacting the acyclic N-halamine methacrylamide polymer with a halide source to form an activated acyclic N-halamine methacrylamide polymer with biocidal activity against bacteria, spores, fungi, yeasts, virus or a combination thereof.

9. The method of claim 8, wherein the acyclic N-halamine methacrylamide polymer is a random polymer, a segmented polymer, a block polymer, a multiblock polymer, a gradient polymer, a graft polymer, a star polymer, a branched polymer, a hyperbranched polymer or segments and combinations thereof.

10. The method of claim 8, wherein the acyclic N-halamine acrylamide monomer is further modified by the addition of one or more alkyl groups, alkylene groups, alkenyl groups, alkynyl groups, aryl groups, alkoxy groups, alkylcarbonyl groups, alkylcarboxyl groups, amido groups, carboxyl groups, halogens, hydrogens or combinations thereof.

11. The method of claim 8, further comprising the step of forming the cotton into a fabric garment to have biocidal activity against bacteria, spores, fungi, yeasts, virus or a combination thereof.

12. The method of claim 8, further comprising the step of removing one or more halides from the activated acyclic N-halamine methacrylamide polymer and incubating the activated acyclic N-halamine methacrylamide polymer with a halide source to recharged the acyclic N-halamine methacrylamide monomer.

13. The method of claim 8, further comprising a halogenation regenerating step of renewing any removed halogens associated with the acyclic N-halamine methacrylamide monomer with a hypochlorite solution.