N-halamines compounds as multifunctional additives

• US 10,138,379 B2
• Filed: 12/23/2014
• Issued: 11/27/2018
• Est. Priority Date: 08/11/2005
• 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, Chen, Zhaobin
• Primary Examiner(s): Tran, Susan T
• Assistant Examiner(s): Craigo, William
• Application Number:
  US14/580,540
• Publication Number:
  US 20150166796A1
• Time in Patent Office: 1,435 Days
• Field of Search: None
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• 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: C02F 1/50 by addition or application of a germicide or by oligodynamic treatment C02F1/4606, C02F1/467, C02F1/76 take precedence
• CPC Class Codes: C02F 1/76 with halogens or compounds of halogens C02F1/4674 takes precedence
• CPC Class Codes: C02F 2103/32 from the food or foodstuff industry, e.g. brewery waste waters
• CPC Class Codes: C02F 2303/16 Regeneration of sorbents, filters
• CPC Class Codes: C02F 2303/20 Prevention of biofouling
• CPC Class Codes: C09D 5/14 Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence

Abstract

The present invention is a composition and method for making and using a rechargeable multifunctional additive that reduce the formation of biofilms on a surface, the additive can also remain photo and thermally stable by synthesizing one or more N-halamine compounds and adding one or more N-halamine biocidal compounds to a target material prior, during or after the target material is made. The resultant material can be used directly to provide antimicrobial functions and control biofilm formation, or the material can be further processed into an article.

Claims

1. A method of making a rechargeable antimicrobial anti-biofilm article comprising the steps of:

adding one or more substituted hydantoins to a target material, wherein the one or more substituted hydantoins are selected from the group consisting of 1-chloro-3-ethyl-5,5-dimethylhydantoins, 1-chloro-3-dodecyl-5,5-dimethylhydantoin, 1-chloro-3-octadecyl-5,5-dimethylhydantoin, 1-chloro-3-docosyl-5,5-dimethylhydantoin, and mixtures thereof; and

forming a rechargeable antimicrobial anti-biofilm article from the target.

2. The method of claim 1, wherein the one or more substituted hydantoins are added by solution blending, mechanical mixing, painting, coating, laminating, thermal mixing and combinations thereof.

3. The method of claim 1, further comprising the step of recharging the antimicrobial anti-biofilm article by the addition of one or more halogens.

4. The method of claim 1, wherein the target material comprises a polymer, organic material, inorganic material or combinations and mixtures thereof.

5. The method of claim 1, wherein the rechargeable antimicrobial anti-biofilm article comprises plastics, rubbers, fibers, woods, paints, coatings, nanoparticles, glass, ceramics, resins, epoxies or combinations and mixtures thereof, wherein the antimicrobial anti-biofilm article is rechargeable.

6. A method of reducing the formation of biofilms on a surface comprising the steps of:

adding one or more substituted hydantoins to a target material, wherein the one or more substituted hydantoins comprise 1-chloro-3-ethyl-5,5-dimethylhydantoins, 1-chloro-3-dodecyl-5,5-dimethylhydantoin, 1-chloro-3-octadecyl-5,5-dimethylhydantoin, 1-chloro-3-docosyl-5,5-dimethylhydantoin and mixtures thereof; and

processing the target material into an article to reduce the formation of biofilms on a surface of the article.

7. The method of claim 6, further comprising the step of regenerating the activity of the one or more substituted hydantoins by exposing the one or more substituted hydantoins to a halogen source.

8. The method of claim 6, wherein the article comprises plastics, rubbers, fibers, woods, paints, coatings, nanoparticles, semiconductor materials, resins, epoxies paints, stains, inorganic materials or combinations thereof.