Methods for making antimicrobial resins

• US 8,277,826 B2
• Filed: 06/25/2008
• Issued: 10/02/2012
• Est. Priority Date: 06/25/2008
• Status: Active Grant

• Current Assignee: Baxter Healthcare SA (Baxter International Inc.), Baxter International Inc.
• Original Assignee: Baxter Healthcare SA (Baxter International Inc.), Baxter International Inc.
• Inventors: Krongauz, Vadim V., Cawthon, Dustin C., Ling, Michael Tung-Kiung
• Primary Examiner(s): Schnizer, Richard
• Assistant Examiner(s): Buckley, Audrea
• Application Number:
  US12/145,548
• Publication Number:
  US 20090324666A1
• Time in Patent Office: 1,560 Days
• Field of Search: 424/409
• US Class Current: 424/409
• CPC Class Codes: A61L 2300/102 Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
• CPC Class Codes: A61L 2300/104 Silver, e.g. silver sulfadiazine
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 2300/624 Nanocapsules
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: A61L 29/10 Inorganic materials
• CPC Class Codes: A61L 29/14 Materials characterised by their function or physical properties , e.g. lubricating compositions
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Abstract

Methods for making antimicrobial resins and for forming coatings comprising antimicrobial resins on substrate surfaces are disclosed. The methods involve providing a mixture comprising about 15 weight % to about 80 weight % of a hydrophilic acrylic oligomer, about 10 weight % to about 80 weight % of a multifunctional acrylic monomer, about 5 weight % to about 40 weight % of an adhesion-promoting acrylic or vinyl monomer, and about 0.1 weight % to about 15 weight % of a metal salt; and exposing the mixture to a radiation source to cure at least a portion of the mixture, thereby forming an antimicrobial resin.

Claims

1. A method for forming an antimicrobial resin comprising:

providing a mixture comprising about 15 weight % to about 80 weight % of a hydrophilic acrylic oligomer, about 10 weight % to about 80 weight % of a multifunctional acrylic monomer, about 5 weight % to about 40 weight % of a monofunctional adhesion-promoting acrylic or vinyl monomer, and about 0.1 weight % to about 15 weight % of an antimicrobial metal salt; and

exposing the mixture to a radiation source to cure at least a portion of the mixture, thereby forming an antimicrobial resin.

2. The method of claim 1, further comprising forming a medical device or medical device component comprising the antimicrobial resin.

3. The method of claim 1, further comprising applying the antimicrobial resin to a substrate surface to form a coating on the substrate surface.

4. The method of claim 1, further comprising forming a coating comprising:

providing the mixture on a substrate surface before exposing the mixture to the radiation source.

5. The method of claim 4, wherein the substrate surface comprises at least one plastic, glass, metal, ceramic, elastomer, or mixtures or laminates thereof.

6. The method of claim 4, wherein the substrate surface comprises a plastic or elastomer selected from the group consisting of acrylonitrile butadiene styrenes, polyamides, polycarbonates, polyesters, polyetheretherketones, polyetherimides, polyethylenes, polyethylene terephthalates, polylactic acids, polymethyl methyacrylates, polypropylenes, polystyrenes, polyurethanes, poly(vinyl chlorides), polyvinylidene chlorides, polyethers, polysulfones, silicones, natural rubbers, synthetic rubbers, styrene butadiene rubbers, ethylene propylene diene monomer rubbers, polychloroprene rubbers, acrylonitrile butadiene rubbers, chlorosuphonated polyethylene rubbers, polyisoprene rubbers, isobutylene-isoprene copolymeric rubbers, chlorinated isobutylene-isoprene copolymeric rubbers, brominated isobutylene-isoprene copolymeric rubbers, and mixtures and copolymers thereof.

7. The method of claim 4, wherein the substrate surface comprises a surface of a medical device or medical device component.

8. The method of claim 4, wherein the substrate surface comprises a surface of a medical fluid container or medical fluid flow system.

9. The method of claim 4, wherein the substrate surface comprises a surface of an I.V. set.

10. The method of claim 4, wherein the substrate surface comprises a surface of a medical device or medical device component selected from the group consisting of:

I.V. tubing, I.V. fluid bags, access devices for I.V. sets, septa, stopcocks, I.V. set connectors, I.V. set adaptors, clamps, I.V. filters, catheters, needles, and cannulae.

11. The method of claim 4, wherein the substrate surface comprises a surface of a luer access device or a needleless luer access device.

12. The method of claim 4, wherein the radiation source comprises an ultraviolet (UV) light source, an electron beam source, a gamma radiation source, an X-ray source, an ion beam source, a microwave source, a heat source, or a combination of the foregoing.

13. The method of claim 4, wherein the hydrophilic acrylic oligomer comprises monofunctional oligomers, difunctional oligomers, trifunctional oligomers, tetrafunctional oligomers, pentafunctional oligomers, hexafunctional oligomers, or mixtures thereof.

14. The method of claim 4, wherein the hydrophilic acrylic oligomer comprises polyepoxy acrylates, polyurethane acrylates, polyester acrylates, polyether acrylates, amine-modified polyether acrylates, polyacrylic acrylates, polycarbonate acrylates, polyepoxy methacrylates, polyurethane methacrylates, polyester methacrylates, polyether methacrylates, amine-modified polyether methacrylates, polyacrylic methacrylates, polycarbonate methacrylates, polyepoxy acrylamides, polyurethane acrylamides, polyester acrylamides, polyether acrylamides, amine-modified polyether acrylamides, polyacrylic acrylamides, polycarbonate acrylamides, polyepoxy methacrylamides, polyurethane methacrylamides, polyester methacrylamides, polyether methacrylamides, amine-modified polyether methacrylamides, polyacrylic methacrylamides, polycarbonate methacrylamides, or mixtures thereof.

15. The method of claim 4, wherein the hydrophilic acrylic oligomer comprises ethoxylated bisphenol A diacrylates, polyethylene glycol diacrylates, or mixtures thereof.

16. The method of claim 4, wherein the multifunctional acrylic monomer comprises acrylate esters, methacrylate esters, acrylamides, methacrylamides, or mixtures thereof.

17. The method of claim 4, wherein the multifunctional acrylic monomer comprises difunctional monomers, trifunctional monomers, tetrafunctional monomers, pentafunctional monomers, hexafunctional monomers, or mixtures thereof.

18. The method of claim 4, wherein the multifunctional acrylic monomer comprises 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, or mixtures thereof.

19. The method of claim 4, wherein the monofunctional adhesion-promoting acrylic or vinyl monomer comprises acrylate esters, methacrylate esters, acrylamides, methacrylamides, or mixtures thereof.

20. The method of claim 4, wherein the monofunctional adhesion-promoting acrylic or vinyl monomer comprises acrylic acid, N,N-dimethyl acrylamide, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, tetrahydrofurfuryl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, N-vinyl pyrrolidone, or mixtures thereof.

21. The method of claim 4, wherein the metal salt comprises a metal selected from the group consisting of silver, copper, gold, zinc, cerium, and mixtures thereof.

22. The method of claim 4, wherein the metal salt comprises silver.

23. The method of claim 4, wherein the metal salt comprises silver sulfadiazine.

24. The method of claim 4, wherein the metal salt comprises particles having a diameter of about 1 nanometer to about 50 micrometers.

25. The method of claim 4, wherein the metal salt comprises silver sulfadiazine particles.

26. The method of claim 4, wherein the mixture further comprises about 0.1 weight % to about 15 weight % of an initiator.

27. The method of claim 26, wherein the initiator comprises α

-hydroxyketones, phenylglyoxylates, benzyldimethyl ketals, α

-aminoketones, mono acyl phosphines, bis acyl phosphines, phosphine oxides, metallocenes, iodonium salts, mercaptobenzothiazoles, mercaptobenzooxazoles, benzophenones, acetophenones, benzoin alkyl ethers, hexaarylbisimidazoles, and mixtures thereof.

28. The method of claim 26, wherein the initiator comprises 2,2-dimethoxy-1,2-diphenylethan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, or mixtures thereof.

29. The method of claim 4, wherein the mixture further comprises a saturated fatty acid, an unsaturated fatty acid, or a mixture thereof.

30. The method of claim 4, wherein the mixture further comprises a fatty acid selected from the group consisting of:

decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, eicosanoic acid, docsanoic acid, tetracosanoic acid, α

-linolenic acid, stearidonic acid, eicosapentaenoic acid, docosahexaenoic acid, linoleic acid, γ

-linolenic acid, dihomo-γ

-linolenic acid, arachidonic acid, oleic acid, erucic acid, nervonic acid, and mixtures thereof.

31. The method of claim 1, wherein hydrophilic acrylic oligomer is selected from the group consisting of difunctional oligomers, trifunctional oligomers, tetrafunctional oligomers, pentafunctional oligomers, hexafunctional oligomers, or mixtures thereof, and wherein the multifunctional acrylic monomer is selected from the group consisting of alkyl multifunctional monomers and alkenyl multifunctional monomers.