Coating agents and coated articles

• US 10,266,620 B2
• Filed: 12/06/2016
• Issued: 04/23/2019
• Est. Priority Date: 12/21/2009
• Status: Active Grant

• Current Assignee: Innovative Surface Technologies, Inc.
• Original Assignee: Innovative Surface Technologies, Inc.
• Inventors: Wen, Jie, Taton, Kristin, Lawin, Laurie, Knopke, William, Guire, Eric, Guire, Patrick
• Primary Examiner(s): Peng, Kuo Liang
• Application Number:
  US15/370,410
• Publication Number:
  US 20170081435A1
• Time in Patent Office: 868 Days
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 2300/42 Anti-thrombotic agents, anticoagulants, anti-platelet agents
• CPC Class Codes: A61L 2400/10 Materials for lubricating medical devices
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 2420/08 Coatings comprising two or more layers
• CPC Class Codes: A61L 29/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 29/085 Macromolecular 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: A61L 31/022 Metals or alloys
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/14 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: A61L 33/0005 Use of materials characterised by their function or physical properties
• CPC Class Codes: B05D 3/06 by exposure to radiation B05D3/02 takes precedence ; plasma treatment B05D3/141
• CPC Class Codes: C08F 222/06 Maleic anhydride
• CPC Class Codes: C08F 267/04 on to polymers of anhydrides
• CPC Class Codes: C08F 8/28 Condensation with aldehydes or ketones
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08F 8/42 : Introducing metal atoms or metal-containing groups
• CPC Class Codes: C09D 131/00 : Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid based on hydrolysed polymers C09D129/00; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 135/00 : Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
• CPC Class Codes: Y10T 428/31507 : Of polycarbonate
• CPC Class Codes: Y10T 428/31511 : Of epoxy ether
• CPC Class Codes: Y10T 428/31573 : Next to addition polymer of ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/31598 : Next to silicon-containing [silicone, cement, etc.] layer
• CPC Class Codes: Y10T 428/31663 : As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31667 : Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
• CPC Class Codes: Y10T 428/31721 : Of polyimide
• CPC Class Codes: Y10T 428/3175 : Next to addition polymer from unsaturated monomer[s]
• CPC Class Codes: Y10T 428/31797 : Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31855 : Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31884 : Regenerated or modified cellulose
• CPC Class Codes: Y10T 428/31909 : Next to second addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31913 : Monoolefin polymer
• CPC Class Codes: Y10T 428/31928 : Ester, halide or nitrile of addition polymer

Abstract

The invention describes novel coating agents that include a polymer, one or more latent reactive groups and one or more noncovalent linking groups, the noncovalent linking groups selected to interact with a substrate to which the coating agent is applied. The coating agents are useful for providing a coating that can be further functionalized (for example, by application of additional coating layers), or for providing desirable properties to a surface.

Claims

1. A method for forming a coated article, the method comprising steps of (a) applying a coating composition to a surface of the article, the coating composition comprising a polymer that includes a polymaleic acid derivative or a copolymer of a polymaleic acid derivative, one or more photoreactive groups that are pendent from the polymer, and one or more anionically charged moieties, wherein one or more of the anionically charged moieties is within the polymaleic acid derivative, and wherein the photoreactive groups are individually selected from acetophenone, benzophenone, anthrone, acridone, xanthone, thioxanthone, and anthraquinone;

and (b) exposing the coating composition to actinic energy, thereby activating at least some of the photoreactive groups and covalently coupling the coating composition on the surface.

2. The method according to claim 1 wherein the surface of the article is not pretreated by chemical, biological or physical pretreatments that generate reactive groups on the surface prior to applying the coating composition to the surface.

3. The method according to claim 1 wherein step (a) comprises applying a coating composition comprising a polymer that includes a polymaleic acid derivative or a copolymer of a polymaleic acid derivative, one or more photoreactive groups that are pendent from the polymer, and one or more anionically charged groups selected from carboxylate, tetrachlorophenol, phosphate, phosphonate, phosphinate, sulphate, sulphonate, thiocarboxylate and hydroxamic acid.

4. The method according to claim 1 further comprising a step of applying one or more overcoat layers onto the coating composition.

5. The method according to claim 1 further comprising a step of disposing an active agent coating layer on the coating composition.

6. The method according to claim 5 wherein the step of disposing an active agent coating layer is performed after step (b).

7. The method according to claim 1 further comprising a step of disposing a hydrophobic coating layer on the coating composition.

8. The method according to claim 7 wherein the hydrophobic coating layer comprises polyisobutylene, sulfobetaine methacrylate, polyethylene glycol, or a mixture of two or more of these.

9. The method according to claim 1 further comprising a step of disposing a lubricious coating layer on the coating composition.

10. The method according to claim 1 wherein the coating composition further comprises a C₄ to C₂₀ lipophilic alkyl group.

11. The method according to claim 1 wherein the polymaleic acid derivative is a derivatized poly(alkene-co-maleic anhydride).

12. A coated article comprising a medical device prepared by the method of claim 1.

13. The coated article according to claim 12 wherein the medical device is fabricated from a material selected from silicon;

silicone;

polyolefin;

polyethylene;

polypropylene;

vinyl polymer;

polystyrene;

polyacrylate;

polymethacrylate;

poly(methyl)methacrylate;

polyacrylonitrile;

poly(vinylacetate);

poly(vinyl alcohol);

chlorine-containing polymer;

polyoxymethylene;

polycarbonate;

polyamide;

polyimide;

polyurethane;

phenolics;

amino-epoxy resin;

polyester;

cellulose-based plastic;

rubber-like plastic;

aluminum, chromium, cobalt, iron, tantalum, titanium, and alloys thereof;

nitinol and other nickel-titanium alloys;

stainless steel;

noble metals; and

cobalt-chromium, and combinations of any two or more of these.

14. An article comprising a medical device and a multilayer coating on a surface of the medical device, the multilayer coating comprising:

(a) a coating layer comprising (i) a polymaleic acid derivative or a copolymer thereof;

(ii) one or more aryl ketones; and

(iii) one or more anionically charged moieties;

and

(b) a hydrophobic coating layer.

15. The article according to claim 14 wherein the anionically charged moiety is selected carboxylate, tetrachlorophenol, phosphate, phosphonate, phosphinate, sulphate, sulphonate, thiocarboxylate and hydroxamic acid.

16. The article according to claim 14 wherein the hydrophobic coating layer comprises polyisobutylene, sulfobetaine methacrylate, polyethylene glycol, or a mixture of two or more of these.

17. The article according to claim 14 wherein the medical device is fabricated from a material selected from silicon;

silicone;

polyolefin;

polyethylene;

polypropylene;

vinyl polymer;

polystyrene;

polyacrylate;

polymethacrylate;

poly(methyl)methacrylate;

polyacrylonitrile;

poly(vinylacetate);

poly(vinyl alcohol);

chlorine-containing polymer;

polyoxymethylene;

polycarbonate;

polyamide;

polyimide;

polyurethane;

phenolics;

amino-epoxy resin;

polyester;

cellulose-based plastic;

rubber-like plastic;

aluminum, chromium, cobalt, iron, tantalum, titanium, and alloys thereof;

nitinol and other nickel-titanium alloys;

stainless steel;

noble metals; and

cobalt-chromium, and combinations of any two or more of these.

18. The article according to claim 14 wherein the polymaleic acid derivative is a derivatized poly(alkene-co-maleic anhydride).

19. The article according to claim 14 further comprising an active agent selected from anti-microbial, anti-fouling, anti-angiogenic, angiogenic, antifibrotic, fibrotic, anti-thrombosis, and protein resistant agents, and combinations of any two or more of these.

20. The article according to claim 14 wherein the coating layer (a) further comprises a C₄ to C₂₀ lipophilic alkyl group.