UV curable solventless antimicrobial compositions

• US 9,695,323 B2
• Filed: 02/13/2013
• Issued: 07/04/2017
• Est. Priority Date: 02/13/2013
• Status: Active Grant

• Current Assignee: Becton, Dickinson & Co
• Original Assignee: Becton, Dickinson & Co
• Inventors: Lin, Janice, Ma, Yiping
• Primary Examiner(s): MCCLENDON, SANZA L
• Application Number:
  US13/766,517
• Publication Number:
  US 20140228466A1
• Time in Patent Office: 1,602 Days
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 5/14 Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence

Abstract

Antimicrobial compositions and methods are disclosed. The antimicrobial compositions are particularly useful in providing antimicrobial capability to a wide-range of medical devices. In one aspect the invention relates a UV curable antimicrobial coating comprising a UV curable composition comprising an oligomer, a momoner, and a photoinitiator which are together capable of forming a UV curable polymer composition. The compositions also include insoluble antimicrobial agents, which may be selected from a wide array of agents. The insoluble antimicrobial agents include a particle size less than 15 μm. Representative insoluble antimicrobial agents include chlorhexidine diacetate, chlorhexidine base, alexidine(dihydrochloride), silver sulfadiazene, silver citrate, triclosan, octenidine(dihydrochloride), and rifampicin.

Claims

1. An antimicrobial;

ultraviolet (UV) curable spray comprising;

an adhesive comprising an oligomer, a monomer, and a photoinitiator; and

an insoluble non-metallic antimicrobial agent comprising a plurality of particles, each of the particles having a particle size less than 10 μ

m;

wherein the antimicrobial, ultraviolet (UV) curable spray does not comprise a rheology modifier, wherein a concentration of the antimicrobial agent is less than 8.9 parts by weight in 100 parts by weight of the coating, wherein the antimicrobial spray has a viscosity from approximately 5 centipose to approximately 500 centipose.

2. The antimicrobial UV curable spray of claim 1, wherein the insoluble antimicrobial agent is selected from a group consisting of chlorhexidine compounds, a polymer-bound antimicrobial peptide, alkylpyridinium iodide, sorbic acid, alexidine dihydrochloride, octenidine dihydrochloride, rifampicin, triclosan, and combinations thereof.

3. The antimicrobial UV curable spray of claim 1, wherein the insoluble antimicrobial agent is chlorhexidine diacetate.

4. The antimicrobial UV curable spray of claim 1, wherein the oligomer is selected from the group consisting of acrylated aliphatic urethanes, acrylated aromatic urethanes, acrylated polyesters, unsaturated polyesters, acrylated polyethers, and acrylated acrylics.

5. The antimicrobial UV curable spray of claim 4, wherein the acrylated functional group is selected from the group consisting of mono-functional, di-functional, tri-functional, tetra-functional, penta-functional, and hexa-functional acrylates.

6. The antimicrobial UV curable spray of claim 1, wherein the monomer is selected from the group consisting of 2-ethyl hexyl acrylate, isooctyl acrylate, isobornylacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, pentaerythritol tetra acrylate, penta erythritol tri acrylate, dimethoxy phenyl acetophenone hexyl methyl acrylate, and 1,6 hexanidiol methacrylate.

7. The antimicrobial UV curable spray of claim 1, wherein the photoinitiator is selected from the group consisting of benzoin ethers, acetophenones, benzoyl oximes, acyl phosphine oxide, and Michler'"'"'s ketone, thioxanthone, anthroguionone, benzophenone, methyl diethanol amine, and 2-N-butoxyethyl-4-(dimethylamino) benzoate.

8. The antimicrobial UV curable spray of claim 1 wherein the insoluble antimicrobial agent is selected from the group consisting of aldehydes, anilides, biguanides, bis-phenols, and quaternary ammonium compounds.

9. A UV curable coating composition comprising:

a) an adhesive, comprising;

an oligomer;

a monomer; and

a photoinitiator;

b) an insoluble antimicrobial agent comprising a plurality of particles, each of the particles having a particle size less than about 15 μ

m, and provided in a concentration from less than approximately 8.9 parts by weight in 100 parts UV curable coating composition;

wherein the UV curable coating comprises a viscosity from approximately 5 centipoise to approximately 500 centipoise, wherein the UV curable coating composition does not comprise a rheology modifier.

10. The UV curable coating composition of claim 9, wherein the particle size is less than 10 μ

m.

11. A method of facilitating gradual release of an antimicrobial agent from an antimicrobial, ultraviolet (UV) curable coating on a surface of a medical device, comprising:

providing an antimicrobial, UV curable coating composition, wherein the antimicrobial, UV curable coating composition comprises;

an adhesive comprising an oligomer, a monomer, and a photoinitiator; and

an insoluble non-metallic antimicrobial agent comprising a plurality of particles, each of the particles having a particle size less than 15 μ

m, wherein a concentration of the insoluble non-metallic antimicrobial agent is less than 8.9 parts by weight in 100 parts by weight of the coating,

wherein the antimicrobial, UV curable coating composition does not comprise a rheology modifier and has a viscosity from approximately 5 centipose to approximately 500 centipose; and

spraying the UV curable coating composition on the surface of the medical device.