Biomedical articles with ionically bonded polyelectrolyte coatings

• US 5,837,377 A
• Filed: 11/17/1995
• Issued: 11/17/1998
• Est. Priority Date: 12/16/1994
• Status: Expired due to Term

• Current Assignee: Surface Technology Limited Liability Company
• Original Assignee: Surface Technology Limited Liability Company
• Inventors: Sheu, Min-Shyan, Loh, Ih-Houng
• Primary Examiner(s): Thibodeau, Paul J.
• Assistant Examiner(s): TARAZANO, DONALD LAWRENCE
• Application Number:
  US08/560,023
• Time in Patent Office: 1,096 Days
• Field of Search: 428/411.1, 428/420, 428/413, 428/421, 428/515, 428/516, 428/474.4, 428/475.5, 428/412, 428/424.2, 428/473.5, 428/475.8, 428/483, 428/447, 428/500, 351/159, 351/160 R, 351/160 H, 351/166
• US Class Current: 428/412
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: B01D 67/0088 Physical treatment with compounds, e.g. swelling, coating or impregnation
• CPC Class Codes: B01D 67/0093 Chemical modification
• CPC Class Codes: C08J 2479/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: Y10T 428/249992 Linear or thermoplastic
• CPC Class Codes: Y10T 428/249993 Hydrocarbon polymer
• CPC Class Codes: Y10T 428/2991 Coated
• CPC Class Codes: Y10T 428/2998 including synthetic resin or polymer
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31536 Including interfacial reaction product of adjacent layers
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31573 Next to addition polymer of ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31721 Of polyimide
• CPC Class Codes: Y10T 428/31743 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 428/31909 : Next to second addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31913 : Monoolefin polymer

Abstract

A hydrophilic article for use in aqueous environments, including a substrate, an ionic polymeric layer on said substrate, and a disordered polyelectrolyte coating ionically bonded to said polymeric layer.

Claims

1. A hydrophilic biomedical article for use with aqueous environments, comprising

a biomedical substrate;

an ionic polymeric layer on said substrate; and

a disordered polyelectrolyte coating consisting of a polyelectrolyte polymer selected from the group consisting of polyethyleneimine, polyaminoalkyl methacrylate, polyvinylpyridine, polylysine, polyacrylic acid, polymethacrylic acid, polysulfonic acid, polyvinyl sulfate, polyacrylamido-2-methyl-1-propanesulfonic acid, and polystyrene sulfonic acid, and being attached via ionic bonding to said polymeric layer;

wherein the initial advancing water contact angle of said coating is less than 56°

.

2. An article of claim 1, wherein the advancing water contact angle of said coating is less than 60°

after said article is autoclaved at 125°

C. for 15 minutes, and then allowed to cool to room temperature.

3. An article of claim 1, wherein the advancing water contact angle of said coating is less than 60°

after said article is autoclaved at 125°

C. for 30 minutes, and then allowed to cool to room temperature.

4. The biomedical article of claim 2, wherein

said polymeric layer comprises a polymer selected from the group consisting of (A) polyethylene, polypropylene, polystyrene, polyester, polycarbonates, silicone polymers, polyurethane, polyamides, polyimides, polyalkylacrylates, polyalkylmethacrylates, and fluorocarbon polymers;

(B) poly- 2-hydroxylethylmethacrylate, polyhydroxylalkyl methacrylates, polyhydroxylalkyl acrylates, polyacrylic amides, polymethacrylic amides, polyvinyl alcohols, polyethylene oxide, and polyvinyl pyrrolidone;

(C) polylactic acid, polyglycolic acid, polyglycolide-co-lactides, polydioxanones, poly(glycolide-co-trimethylene carbonates), polyethylene carbonates, polyiminocarbonates, poly-β

-hydroxybutyrates, polyester-amides, polyorthoesters, polyanhydrides, and cyanoacrylates; and

(D) copolymers of members of (A), (B) and (C).

5. The biomedical article of claim 4, wherein said polymeric layer is a polymer or copolymer of silicone or a polymer or copolymer of poly-2-hydroxylethylmethacrylate, or copolymer of silicone and poly-2-hydroxylethylmethacrylate;

and said polyelectrolyte coating is polyethyleneimine.

6. The biomedical article of claim 5, wherein said biomedical substrate is an ophthalmic substrate.

7. The biomedical article of claim 1, wherein said coating has an advancing water contact angle less than 70°

after five ultrasonic wash cycles with deionized water.

8. The biomedical article of claim 1, wherein said coating has an advancing water contact angle less than 70°

after fifteen ultrasonic wash cycles with deionized water.

9. The biomedical article of claim 8, wherein

said polymeric layer comprises a polymer selected from the group consisting of (A) polyethylene, polypropylene, polystyrene, polyester, polycarbonates, silicone polymers, polyurethane, polyamides, polyimides, polyalkylacrylates, polyalkylmethacrylates, and fluorocarbon polymers;

(B) poly-2-hydroxylethylmethacrylate, polyhydroxylalkyl methacrylates, polyhydroxylalkyl acrylates, polyacrylic amides, polymethacrylic amides, polyvinyl alcohols, polyethylene oxide, and polyvinyl pyrrolidone;

(C) polylactic acid, polyglycolic acid, polyglycolide-co-lactides, polydioxanones, poly(glycolide-co-trimethylene carbonates), polyethylene carbonates, polyiminocarbonates, poly-β

-hydroxybutyrates, polyester-amides, polyorthoesters, polyanhydrides, and cyanoacrylates; and

(D) copolymers of members of (A) , (B) and (C).

10. The biomedical article of claim 9, wherein said polymeric layer is a polymer or copolymer of silicone or a polymer or copolymer of poly-2-hydroxylethylmethacrylate, or copolymer of silicone and poly-2-hydroxylethylmethacrylate;

and said polyelectrolyte coating is polyethyleneimine.

11. The biomedical article of claim 9, wherein said biomedical substrate is an ophthalmic substrate.

12. The biomedical article of claim 1, wherein the advancing water contact angle of said substrate is greater than 95°

.

13. The biomedical article of claim 1, wherein the advancing water contact angle of said substrate is greater than 110°

.

14. The biomedical article of claim 12, wherein

said polymeric layer comprises a polymer selected from the group consisting of (A) polyethylene, polypropylene, polystyrene, polyester, polycarbonates, silicone polymers, polyurethane, polyamides, polyimides, polyalkylacrylates, polyalkylmethacrylates, and fluorocarbon polymers;

(B) poly-2-hydroxylethylmethacrylate, polyhydroxylalkyl methacrylates, polyhydroxylalkyl acrylates, polyacrylic amides, polymethacrylic amides, polyvinyl alcohols, polyethylene oxide, and polyvinyl pyrrolidone;

(C) polylactic acid, polyglycolic acid, polyglycolide-co-lactides, polydioxanones, poly(glycolide-co-trimethylene carbonates), polyethylene carbonates, polyiminocarbonates, poly-β

-hydroxybutyrates, polyesteramides, polyorthoesters, polyanhydrides, and cyanoacrylates; and

(D) copolymers of members of (A), (B) and (C).

15. The biomedical article of claim 14, wherein said biomedical substrate is an ophthalmic substrate.