N-Halamine-Based Rechargeable Biofilm-Controlling Tubular Devices, Method of Making and Using

• US 20080268189A1
• Filed: 03/26/2008
• Published: 10/30/2008
• Est. Priority Date: 03/26/2007
• 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: Luo, Jie, Sun, Yuyu, Chen, Zhaobin
• Granted Patent: US 8,211,361 B2
• Time in Patent Office: Days
• US Class Current: 428/34.1
• 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 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/22 containing ingredients stabilising the active ingredients
• 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 37/28 containing the group; Thio analogues thereof
• CPC Class Codes: C08J 7/126 Halogenation
• CPC Class Codes: Y10T 428/13 Hollow or container type article [e.g., tube, vase, etc.]

Abstract

The present invention includes compositions, articles, methods controlling microbial contamination of a surface by functionalizing a surface of an object and binding one or more acyclic-amine structures to the surface. The one or more acyclic-amine structures are halogenated to form one or more acyclic N-halamine structures. The one or more acyclic N-halamine structures modulate the formation of a biofilm.

Claims

1. A method of controlling microbial contamination of a tubing surface comprising the steps of:

functionalizing at least a portion of an inner surface of a tube;

binding one or more methacrylamides to the inner surface; and

halogenating the one or more methacrylamides to form one or more acyclic N-halamines, wherein the one or more acyclic N-halamines modulate the growth of a biofilm on the inner surface of the tube.

2. The method of claim 1, wherein the acyclic N-halamine compound comprises 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.

3. The method of claim 1, wherein the acyclic N-halamine compound 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.

4. The method of claim 1, wherein the inner surface comprises polyethylene;

polypropylene;

polystyrene;

polyethylene terephthalate;

polyamide;

polyester Polyvinyl chloride;

polycarbonate;

acrylonitrile butadiene styrene;

polyvinylidene chloride;

polytetrafluoroethylene;

polymethyl methacrylate;

polylactic acid and combinations thereof.

5. A method of controlling microbial contamination of a surface comprising the steps of:

functionalizing a surface of an object;

binding one or more acyclic-amine structures to the surface; and

halogenating the one or more acyclic-amine structures to form one or more acyclic N-halamine structures, wherein the one or more acyclic N-halamine structures modulates the formation of a biofilm.

6. The method of claim 5, further comprising the step of recharging the one or more acyclic-amine structures with one or more halogens to form the one or more acyclic N-halamine structures.

7. The method of claim 5, wherein the object is a tube, a wall, a bottom, a heater, a chiller, a plate, a bath, a pipe, a conduit or a combination thereof.

8. The method of claim 5, wherein the one or more acyclic-amine structures comprise methacrylamide.

9. The method of claim 5, wherein the one or more acyclic N-halamines comprise and specific compounds.

10. The method of claim 5, wherein the acyclic N-halamine compound comprises 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 5, wherein the acyclic N-halamine compound 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.

12. The method of claim 5, wherein the surface comprises polyethylene;

polypropylene;

polystyrene;

polyethylene terephthalate;

polyamide;

polyester Polyvinyl chloride;

polycarbonate;

acrylonitrile butadiene styrene;

polyvinylidene chloride;

polytetrafluoroethylene;

polymethyl methacrylate;

polylactic acid and combinations thereof.

13. The method of claim 5, wherein the step of halogenating comprises the addition of a halide solution comprising fluorine, chlorine, bromine, iodine, astatine, or a combination thereof.

14. The method of claim 5, wherein the step of halogenating comprises the addition of a halide source comprises sodium di-X-isocyanurate, sodium hypohalite, N—

X-succinimide, or calcium hypohalite, wherein X is selected from Cl, I or Br.

15. A biofilm resistant surface comprising a surface and one or more acyclic-amines immobilized to the surface by a covalent bond to form a biofilm resistant surface.

16. The biofilm resistant surface of claim 15, wherein the acyclic N-halamine compound comprises 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.

17. The biofilm resistant surface of claim 15, wherein the acyclic N-halamine compound 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.

18. The biofilm resistant surface of claim 15, wherein the surface comprises at least a portion of a tube, a wall, a bottom, a heater, a chiller, a plate, a bath, a pipe, or a conduit.

19. A biofilm resistant conduit comprising one or more acyclic N-halamines immobilized to at lease a portion of an inner surface of at least a portion of a conduit, wherein the one or more acyclic N-halamines modulate the formation of a biofilm on the conduit.

20. The biofilm resistant conduit of claim 19, wherein the acyclic N-halamine compound comprises 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.

21. The biofilm resistant conduit of claim 19, wherein the acyclic N-halamine compound 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.

22. The biofilm resistant conduit of claim 19, wherein the conduit comprises at least a portion of a tube, a wall, a bottom, a heater, a chiller, a plate, a bath, a pipe, or a conduit.