Antimicrobial-coated medical articles

• US 9,809,717 B2
• Filed: 05/25/2011
• Issued: 11/07/2017
• Est. Priority Date: 05/25/2010
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Ali, Mahfuza B., Jing, Naiyong, Lirine, Valeri, Nagarkar, Pradnya V., Ylitalo, Caroline M., Lennhoff, Nancy S., Scholz, Matthew T., Parthasarathy, Ranjani V.
• Primary Examiner(s): Worsham, Jessica
• Application Number:
  US13/699,345
• Publication Number:
  US 20150024019A1
• Time in Patent Office: 2,358 Days
• Field of Search: None
• CPC Class Codes: A61L 2300/216 with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: B05D 3/02 by baking B05D3/04 takes precedence
• CPC Class Codes: B05D 3/06 by exposure to radiation B05D3/02 takes precedence ; plasma treatment B05D3/141
• CPC Class Codes: C03C 17/30 with silicon-containing compounds
• CPC Class Codes: C03C 17/42 at least one coating of an organic material and at least one non-metal coating
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/1808 C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
• CPC Class Codes: C08F 220/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C09D 183/10 Block or graft copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00
• CPC Class Codes: C09D 5/1637 Macromolecular compounds
• CPC Class Codes: C09D 5/1675 Polyorganosiloxane-containing compositions
• CPC Class Codes: C09D 5/1693 as part of a multilayer system
• CPC Class Codes: G06F 3/041 Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
• CPC Class Codes: G06F 3/047 using sets of wires, e.g. crossed wires
• CPC Class Codes: Y10T 428/31663 : As siloxane, silicone or silane

Abstract

The disclosure provides polymers having antimicrobial activity and articles with the polymers coated thereon. The polymers include a first pendant group comprising a first cationic component, a second pendant group comprising a nonpolar component, and a third pendant group comprising an organosilane component. The disclosure also includes methods of coating medical device articles and body fluid-receiving substrates with the antimicrobial polymers. The methods further include the use of adhesion-promoting components.

Claims

1. An article comprising:

a coating composition comprising a vinyl polymer having a plurality of pendant groups comprising

a first pendant group comprising a cationic component selected from the group consisting of a quaternary amine component, protonated tertiary amine component, and a protonated secondary amine component;

a second pendant group comprising a nonpolar component wherein the second pendant group is selected from the group consisting of linear or branched alkanes, alkaryl, aralkyl, aromatic groups, and combinations thereof; and

a third pendant group

a third pendant group comprising a first organosilicon component;

wherein the vinyl polymer does not comprise a pendant group that comprises a carboxylate group; and

a medical device comprising an elastomeric first substrate having a patient-contact first surface and a second surface;

wherein the vinyl polymer is durably adhered to the patient-contact first surface, wherein the composition is free of inorganic filler; and

wherein the coating composition was deposited and cured with an additional free silane present in the coating composition;

wherein the additional free silane is a quaternary ammonium silane or protonated tertiary amino silane having at least one straight or branched chain alkyl of 6-22 carbon atoms.

2. The article of claim 1, wherein the composition further comprises an adhesion-promoting component.

3. The article of claim 1, wherein the vinyl polymer does not comprise a pendant group that includes an alkoxylate chemical group.

4. The article of claim 1 wherein, in the vinyl polymer, the ratio of cationic amine molar equivalents to organosilicon molar equivalents is about 0.1:

1 to about 10;

1.

5. The article of claim 1, wherein at least one of the pendant groups comprises a fluorochemical.

6. The article of claim 1, wherein the first substrate further comprises a durable metal oxide layer on the first surface, wherein the metal oxide layer comprises an oxide of silicon, zirconium, aluminum, or a combination of any two or more of the foregoing metal oxides;

wherein the vinyl polymer is adhered to the metal oxide layer.

7. The article of claim 1, wherein the second surface of the first substrate is adhered to a second substrate.

17. The article of claim 1, wherein the second pendant group comprising the nonpolar component renders the vinyl polymer more hydrophobic than a polymer without the nonpolar component.

18. The article of claim 1, wherein the vinyl polymer is water insoluble.

8. An article comprising:

a coating composition comprising a vinyl polymer having a plurality of pendant groups comprising

a first pendant group comprising a cationic component selected from the group consisting of a quaternary amine component, protonated tertiary amine component, and a protonated secondary amine component;

a second pendant group comprising a nonpolar component wherein the second pendant group is selected from the group consisting of linear or branched alkanes, alkaryl, aralkyl, aromatic groups, and combinations thereof; and

a third pendant group comprising a first organosilicon component;

wherein the vinyl polymer does not comprise a pendant group that comprises a carboxylate group; and

an elastomeric body fluid-contacting first substrate having a body fluid-contacting first surface and a second surface;

wherein the vinyl polymer is durably adhered to the body fluid-contacting first surface, and

wherein the composition is free of inorganic filler.

9. The article of claim 8, wherein the coating was deposited and cured with an additional free antimicrobial silane component present in the composition.

10. The article of claim 8, wherein the composition further comprises an adhesion-promoting component.

11. The article of claim 8, wherein the vinyl polymer does not comprise a pendant group that includes an alkoxylate chemical group.

12. The article of claim 8 wherein, in the vinyl polymer, the ratio of cationic amine molar equivalents to organosilicon molar equivalents is about 0.1:

1 to about 10;

1.

13. The article of claim 8, wherein at least one of the pendant groups comprises a fluorochemical.

14. The article of claim 8, wherein the first substrate further comprises a durable metal oxide layer on the first surface, wherein the metal oxide layer comprises an oxide of silicon, zirconium, aluminum, or a combination of any two or more of the foregoing metal oxides;

wherein the vinyl polymer is adhered to the metal oxide layer.

15. A method of making a coated article, the method comprising:

forming a first coating composition comprising a vinyl polymer having a plurality of pendant groups comprising

a first pendant group comprising a first cationic component selected from the group consisting of a quaternary amine component, protonated tertiary amine component, and a protonated secondary amine component;

a second pendant group comprising a nonpolar component wherein the second pendant group is selected from the group consisting of linear or branched alkanes, alkaryl, aralkyl, aromatic groups, and combinations thereof; and

a third pendant group comprising a first organosilicon component;

wherein the vinyl polymer does not comprise a pendant group that comprises a carboxylate group; and

wherein the first coating composition is free of inorganic filler; and

contacting the first coating composition with a first surface of a first substrate to adhere the vinyl polymer to the first surface;

wherein the first substrate comprises an elastomeric component of a medical device or an elastomeric body fluid-contacting substrate.

16. A medical device article comprising a coating wherein the coating is derived from:

a composition comprising a free silane component and a vinyl polymer having a plurality of pendant groups comprising

a first pendant group comprising a first quaternary ammonium component;

a second pendant group comprising a nonpolar component wherein the second pendant group is selected from the group consisting of linear or branched alkanes, alkaryl, aralkyl, aromatic groups, and combinations thereof; and

a third pendant group comprising a first organosilicon component;

wherein the vinyl polymer does not comprise a pendant group that comprises a carboxylate group;

wherein the vinyl polymer is durably adhered to a surface of the article; and

wherein the composition is free of inorganic filler.