N-halamines compounds as multifunctional additives

• US 20070062884A1
• Filed: 08/11/2006
• Published: 03/22/2007
• Est. Priority Date: 08/11/2005
• Status: Abandoned Application

• 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: Chen, Zhaobin, Sun, Yuyu
• Application Number:
  US11/502,892
• Publication Number:
  US 20070062884A1
• Time in Patent Office: Days
• US Class Current: 210/764
• 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 biofilm-controlling and biocidal N-halamine composition comprising:

one or more 3 to 10 membered rings comprising one or more nitrogen heteroatoms, wherein one or more halogen associate with the one or more nitrogen heteroatoms and control biofilm growth.

2. The composition of claim 1, wherein the a N-halamine biocidal composition comprises formula 1, 2, 3, 4, 5, 6, 7, 8 or combinations thereof:

3. The composition of claim 1, wherein the N-halamine biocidal composition is mixed with a second material to produce an article.

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

adding one or more N-halamine biocidal compounds comprising one or more 3 to 10 membered rings and one or more nitrogen heteroatoms to a target material to be used directly or processed into a rechargeable antimicrobial anti-biofilm article.

6. The method of claim 5, wherein the one or more N-halamine biocidal compounds are added by solution blending, mechanical mixing, painting, coating, laminating, thermal mixing and combinations thereof.

7. The method of claim 5, wherein the one or more N-halamine biocidal compounds comprises 3-substituted-1-N-halo-5,5-disubstituted-hydantoin;

3,3′

-bissubstituted-1,1′

-N-halo-5,5,5′

5′

-substituted-2,2′

,4,4′

-imidazolidinedione;

1,3,8-Triaza-3-substituted-7,7,9,9-substituted-1,8-N-halo-2,4-dioxospiro[4.5]decane;

3,3′

-disubstitued-bis(7,7,9,9-substitued)-1,3,8-Triazaspiro[4.5]decane-1,1′

,8,8′

N-halo-2,4-dione;

8,8′

-disubstitued-bis(7,7,9,9-substitued)-1,3,8-Triazaspiro[4.5]decane-1,1′

,3,3′

N-halo-2,4-dione;

Vinyl chloride-co-3-vinyl-N-halo-5,5-disubstituted hydantoin;

Vinyl chloride-co-3-vinyl-1,3,8-Triaza-7,7,9,9-substituted-1,8-N-halo-2,4-dioxospiro[4.5]decane, 1,3-bis(hydroxylmethyl)-5,5-dimethylhydantoin, 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, 7,7,9,9-tetramethyl-3-hexyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-octadecyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-dodecyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-stearyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-octadecyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and mixtures thereof.

8. The method of claim 5, 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 5, wherein the one or more N-halamine biocidal compounds comprises the formula 1, 2, 3, 4, 5, 6, 7, 8 or combinations thereof:

10. The method of claim 5, further comprising the step of recharging antimicrobial article by the addition of one or more halogens.

11. The method of claim 5, wherein the target material comprise a polymer, organic material, inorganic material or combinations and mixtures thereof.

12. The method of claim 5, 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.

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

adding one or more N-halamine biocidal compounds to a target material; and

processing the target material into an article, wherein the one or more N-halamine biocidal compounds reduce the formation of biofilms on a surface of the article.

14. The method of claim 13, wherein the one or more N-halamine biocidal compounds comprises 3-substituted-1-N-halo-5,5-disubstituted-hydantoin;

3,3′

-bissubstituted-1,1′

-N-halo-5,5,5′

5′

-substituted-2,2′

,4,4′

-imidazolidinedione;

1,3,8-Triaza-3-substituted-7,7,9,9-substituted-1,8-N-halo-2,4-dioxospiro[4.5]decane;

3,3′

-disubstitued-bis(7,7,9,9-substitued)-1,3,8-Triazaspiro[4.5]decane-1,1′

,8,8′

N-halo-2,4-dione;

8,8′

-disubstitued-bis(7,7,9,9-substitued)-1,3,8-Triazaspiro[4.5]decane-1,1′

,3,3′

N-halo-2,4-dione;

Vinyl chloride-co-3-vinyl-N-halo-5,5-disubstituted hydantoin;

Vinyl chloride-co-3-vinyl-1,3,8-Triaza-7,7,9,9-substituted-1,8-N-halo-2,4-dioxospiro[4.5]decane, 1,3-bis(hydroxylmethyl)-5,5-dimethylhydantoin, 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, 7,7,9,9-tetramethyl-3-hexyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-octadecyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-dodecyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-stearyl-1,3,8-triazaspiro[4,5]decane-2,4-dione, 7,7,9,9-tetramethyl-3-octadecyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and mixtures thereof.

15. The method of claim 13, further comprising the step of regenerating the activity of the one or more N-halamine biocidal compounds by exposing the one or more N-halamine biocidal compounds to a halogen source.

16. The method of claim 13, wherein the article comprises plastics, rubbers, fibers, woods, paints, coatings, nanoparticles, semiconductor materials, resins, epoxies paints, stains, inorganic materials or combinations thereof.

17. The method of claim 13, wherein the one or more N-halamine biocidal precursors comprises one or more structures of the formula 1, 2, 3, 4, 5, 6, 7, 8 or combinations thereof:

18. A biofilm-controlling N-halamine biocidal composition that provides photo and thermal stability comprising:

one or more 3 to 10 membered rings comprising one or more nitrogen heteroatoms, wherein one or more halogen associate with the one or more nitrogen heteroatoms and control biofilm growth and provide photo and thermal stabilization effects.

19. A biofilm-controlling and photo and thermal stabilizing additive comprising:

a sterically hindered N-halo-amine with a molecular weight higher than 200 g/mol, wherein the composition provides anti-biofilm and thermal and photo stabilizing function.

20. The composition of claim 19, wherein the sterically hindered N-halo-amine comprises.

21. The composition of claim 19, wherein the sterically hindered N-halo-amine comprises Bis(N—

X-2,2,6,6-tetramethyl-4-piperidyl)sebacate;

2,2,6,6-tetramethyl-N-chloro-4-piperidinyl;

Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N—

X-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidylimino]];

N—

X-[(4-piperidyl)alkyl formate];

Poly[(6-morpholino-s-triazine-2,4-diyl)-N—

X-[2,2,6,6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]];

3-Dodecyl-N-chloro-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide;

2,2,4,4-Tetramethyl-N—

X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one;

D-Glucitol, 1,3;

2,4-bis-O-(N-chloro-2,2,6,6-tetramethyl-4-piperidinylidene);

1,1′

-ethylenebis(N—

X-3,3,5,5-tetramethyl-piperazinone);

N—

X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1.11.2]henicosan-21-one;

1,2,3,4-Butanetetracarboxylic acid, polymer with b,b,b′

,b′

-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, N—

X-2,2,6,6-tetramethyl-4-piperidinyl ester;

Poly[oxy[methyl[3-[N—

X—

(2,2,6,6-tetramethyl-4-piperidinyl)-oxy]propyl]silylene]];

1,1′

,1″

-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris(N-chloro-3,3,5,5-tetramethyl-piperazinone); and

mixtures and combinations thereof, wherein X is Cl, Br or a combination thereof.