COLORANTS BASED N-HALAMINES COMPOSITIONS AND METHOD OF MAKING AND USING

• US 20090074825A1
• Filed: 09/19/2008
• Published: 03/19/2009
• Est. Priority Date: 09/19/2007
• 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
• Granted Patent: US 8,367,823 B2
• Time in Patent Office: Days
• US Class Current: 424/402
• 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 43/38 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/42 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/52 condensed with carbocyclic rings, e.g. benzimidazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/66 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: A61L 15/46 Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• CPC Class Codes: A61L 2300/202 with halogen atoms, e.g. triclosan, povidone-iodine
• CPC Class Codes: A61L 2300/204 with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
• CPC Class Codes: A61L 2300/442 Colorants, dyes
• CPC Class Codes: C07D 209/56 Ring systems containing three or more rings
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 241/36 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 251/50 with a halogen atom attached to the third ring carbon atom
• CPC Class Codes: C07D 251/54 Three nitrogen atoms
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems
• CPC Class Codes: C07D 487/16 : Peri-condensed systems
• CPC Class Codes: C09B 43/16 : linking amino-azo or cyanuric acid residues
• CPC Class Codes: C09B 5/26 : Carbazoles of the anthracene series
• CPC Class Codes: C09B 56/12 : Anthraquinone-azo dyes from diazotised aminoanthracene C09B29/0022, azo dyes containing hydroxyl groups acylated with polyfunctional anthraquinone derivatives C09B43/26
• CPC Class Codes: C09B 7/00 : Indigoid dyes

Abstract

The present invention includes methods, articles, compositions and colorant dyes and pigments that include biocidal N-halamine dye composition having two or more heterocyclic ring structures attached to one or more N-halamine groups, wherein one or more halogens associate with the one or more one or more N-halamine groups to affect biocidal activity.

Claims

1. A biocidal N-halamine dye composition comprising:

two or more heterocyclic ring structures attached to one or more N-halamine groups, wherein one or more halogens associate with the one or more one or more N-halamine groups to affect biocidal activity.

2. The composition of claim 1, wherein the N-halamine biocidal dye composition comprises the formula

wherein A and C are independently ring structures having between 4 and 8 members, B may be an alkyl or a ring structures having between 4 and 8 members with one or more N-halamine groups.

3. The composition of claim 1, wherein the N-halamine biocidal dye composition comprises the formula:

wherein R is a halogen carbon or nitrogen, R1, R2, R3, R4, R5, R6, R7, R8, X and X2 are independently an alkyl group, an alkylene group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylcarbonyl group, an alkylcarboxyl group, an amido group, a carboxyl group or a halogen and may be an optionally substituted with one or more alkyl groups, alkylene groups, alkenyl groups, alkynyl groups, aryl groups, alkoxy groups, alkylcarbonyl groups, alkylcarboxyl groups, amido groups, carboxyl groups, a halogen or a hydrogen.

4. The composition of claim 1, wherein the N-halamine biocidal composition is integrated into a bead, a film, a tube, a sheet, a thread, a suture, a gauze, a bandage, an adhesive bandage, a vessel, a container, a cistern, a filter, a membrane, a coating, a paint, a solution, a polymer and combinations thereof.

5. The composition of claim 1, wherein the N-halamine biocidal composition comprises formula illustrated in FIGS. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16 wherein X, X¹, X², X³ and X⁴ are individually a hydrogen, a halogen, an alkyl, an alkylene, an amino, an alkynyl, an alkoxy;

R¹ to R¹⁰ are independently hydrogens, halogens, one or more C₁ to C₄₀ alkyl, C₁ to C₄₀ alkylene, C₁ to C₄₀ alkenyl, C₁ to C₄₀ alkynyl, C₁ to C₄₀ aryl, C₁ to C₄₀ alkoxy, C₁ to C₄₀ alkylcarbonyl, C₁ to C₄₀ alkylcarboxyl, C₁ to C₄₀ amido, C₁ to C₄₀ carboxyl, or combinations thereof.

6. A method of halogenating a biocidal N-halamine dye article comprising the steps of:

providing a N-halamine dye article comprising one or more N-halamine biocidal compounds comprising two or more heterocyclic ring structures attached to one or more N-halamine groups, wherein one or more halogens associate with the one or more one or more N-halamine groups to affect biocidal activity; and

exposing the N-halamine dye article to a halogen source.

7. The method of claim 6, wherein the one or more N-halamine biocidal compounds are added by solution blending, mechanical mixing, painting, coating, laminating, thermal mixing and combinations thereof.

8. The method of claim 6, wherein the one or more N-halamine biocidal compounds further comprise 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.

9. The method of claim 6, further comprising the step of recharging the one or more N-halamine groups by exposing to a halogen source.

10. The method of claim 6, wherein the N-halamine biocidal dye composition comprises:

Wherein X is a halogen R, R2, R3, R4, R5, R6, R7, and R8 are independently an alkyl group, an alkylene group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylcarbonyl group, an alkylcarboxyl group, an amido group, a carboxyl group or a halogen and may be an optionally substituted with one or more alkyl groups, alkylene groups, alkenyl groups, alkynyl groups, aryl groups, alkoxy groups, alkylcarbonyl groups, alkylcarboxyl groups, amido groups, carboxyl groups, a halogen or a hydrogen.

11. The method of claim 6, wherein the N-halamine biocidal composition comprises formula illustrated in FIGS. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16 wherein X, X¹, X², X³ and X⁴ are individually a hydrogen, a halogen, an alkyl, an alkylene, an amino, an alkynyl, an alkoxy;

R¹ to R¹⁰ are independently hydrogens, halogens, one or more C₁ to C₄₀ alkyl, C₁ to C₄₀ alkylene, C₁ to C₄₀ alkenyl, C₁ to C₄₀ alkynyl, C₁ to C₄₀ aryl, C₁ to C₄₀ alkoxy, C₁ to C₄₀ alkylcarbonyl, C₁ to C₄₀ alkylcarboxyl, C₁ to C₄₀ amido, C₁ to C₄₀ carboxyl, or combinations thereof.

12. The method of claim 6, wherein the N biocidal N-halamine dye article comprises a bead, a film, a tube, a sheet, a thread, a suture, a gauze, a bandage, an adhesive bandage, a vessel, a container, a cistern, a filter, a membrane, a coating, a paint, a solution, a polymer and combinations thereof.

13. A biofilm resistant surface comprising one or more N-halamine biocidal compounds immobilized to the surface to form a biofilm resistant surface, wherein the one or more N-halamine biocidal compounds comprise two or more heterocyclic ring structures attached to one or more N-halamine groups, wherein one or more halogens associate with the one or more one or more N-halamine groups to affect biocidal activity.

14. The biofilm resistant surface of claim 13, wherein the or more N-halamine biocidal compounds 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.

15. The biofilm resistant surface of claim 13, wherein the or more N-halamine biocidal compounds are 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.

16. The biofilm resistant surface of claim 13, wherein the surface comprises at least a portion of a fabric, a cloth, a material, a garment, synthetic fabric or a polymer.

17. The biofilm resistant surface of claim 13, wherein the or more N-halamine biocidal compounds comprises formula 1:

wherein X is a halogen R, R2, R3, R4, R5, R6, R7, and R8 are independently an alkyl group, an alkylene group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an alkylcarbonyl group, an alkylcarboxyl group, an amido group, a carboxyl group or a halogen and may be an optionally substituted with one or more alkyl groups, alkylene groups, alkenyl groups, alkynyl groups, aryl groups, alkoxy groups, alkylcarbonyl groups, alkylcarboxyl groups, amido groups, carboxyl groups, a halogen or a hydrogen.

18. The biofilm resistant surface of claim 13, wherein the or more N-halamine biocidal compounds comprises formula illustrated in FIGS. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16, wherein X, X¹, X², X³ and X⁴ are individually a hydrogen, a halogen, an alkyl, an alkylene, an amino, an alkynyl, an alkoxy;

R1 to R10 are independently hydrogens, halogens, one or more C1 to C40 alkyl, C1 to C40 alkylene, C1 to C40 alkenyl, C1 to C40 alkynyl, C1 to C40 aryl, C1 to C40 alkoxy, C1 to C40 alkylcarbonyl, C1 to C40 alkylcarboxyl, C1 to C40 amido, C1 to C40 carboxyl, or combinations thereof.

19. The biofilm resistant surface of claim 13, wherein the or more N-halamine biocidal compounds is integrated into a bead, a film, a tube, a sheet, a thread, a suture, a gauze, a bandage, an adhesive bandage, a vessel, a container, a cistern, a filter, a membrane, a coating, a paint, a solution, a polymer and combinations thereof.