Lubricious medical device coating with low particulates

Patent metadata

Field	Value
Publication number	US-10905802-B2
Application number	US-201715643564-A
Country	US
Kind code	B2
Filing date	Jul 7, 2017
Priority date	Jan 18, 2012
Publication date	Feb 2, 2021
Grant date	Feb 2, 2021

Abstract

Embodiments of the invention include lubricious medical device coatings. In an embodiment the invention includes a coating for a medical device including a first layer comprising polyvinylpyrrolidone derivatized with a photoreactive group; and a first cross-linking agent comprising at least two photoreactive groups; a second layer disposed on the first layer comprising polyvinylpyrrolidone derivatized with a photoreactive group; a second cross-linking agent comprising at least two photoreactive groups; and a polymer comprising polyacrylamide, the polymer derivatized with at least one photoreactive group. Other embodiments are included herein.

First claim

The invention claimed is:

1. A coating for a medical device comprising:
a first layer comprising
a first polymer composition comprising a polyvinylpyrrolidone derivatized with a photoreactive group; and
a first ionic cross-linking agent comprising at least two photoreactive groups;

a second layer disposed on the first layer, the second layer distinct from the first layer, comprising
a second polymer composition comprising a polyvinylpyrrolidone derivatized with a photoreactive group, wherein the first polyvinylpyrrolidone derivatized with a photoreactive group and the second polyvinylpyrrolidone derivatized with a photoreactive group are the same; and
a second ionic cross-linking agent comprising at least two photoreactive groups;
wherein the first polymer composition of the first layer and the second polymer composition of the second layer are the same;
wherein the first ionic cross-linking agent is present in the first layer in a first concentration and the second ionic cross-linking agent is present in the second layer in a second concentration;
wherein the first concentration of the first ionic cross-linking agent present in the first layer is higher than the second concentration of the second ionic cross-linking agent present in the second layer such that the first concentration of the first ionic cross-linking agent comprises a higher concentration of photoreactive groups than the second concentration of the second ionic cross-linking agent in the second layer;
wherein the first ionic cross-linking agent and the second ionic cross-linking agent confer an ionic charge to both the first layer and the second layer, and wherein the ionic charge of the first and second layer are both anionic or both cationic; and
wherein the coating releases less than 10,000 particles greater than 10 microns in size when exposed to an aqueous environment.

2. The coating of claim 1 , wherein the first ionic cross-linking agent is different from the second ionic cross-linking agent.

3. The coating of claim 1 , the first layer and the second layer further comprising a polymer comprising polyacrylamide, 2-acrylamido-2-methylpropanesulfonate (AMPS), and polyethyleneglycol subunits.

4. The coating of claim 1 , the first layer and the second layer further comprising a polymer comprising N-Acetylated poly[acrylamide-co-sodium-2-acrylamido-2-methylpropanesulfonate-co-N-(3-(4-benzoylbenzamido)propyl)methacrylamide]-co-methoxy poly(ethylene glycol) monomethacrylate.

5. The coating of claim 1 , wherein the ratio of the first polyvinylpyrrolidone derivatized with a photo reactive group in the first layer to the first ionic cross-linking agent comprising at least two photoreactive groups is from about 8:1 to about 16:1 (wt./wt.).

6. The coating of claim 1 , wherein the ratio of the first polyvinylpyrrolidone derivatized with a photo reactive group in the first layer to the first ionic cross-linking agent comprising at least two photoreactive groups is about 13:1 (wt./wt.).

7. The coating of claim 1 , at least one of the first and second ionic cross-linking agents comprising a linking agent having formula Photo 1 -LG-Photo 2 , wherein Photo 1 and Photo 2 , independently represent at least one photoreactive group and LG represents a linking group comprising at least one silicon or at least one phosphorus atom, there is a covalent linkage between at least one photoreactive group and the linking group, wherein the covalent linkage between at least one photoreactive group and the linking group is interrupted by at least one heteroatom.

8. The coating of claim 1 , at least one of the first and second ionic cross-linking agents comprising a linking agent having a formula selected from:

wherein R1, R2, R8 and R9 are H; R3, R4, R6 and R7 are —CH3; R5 is —C 2 H 4 —; and each X is O; and

9. The coating of claim 1 , at least one of the first and second ionic cross-linking agents comprising sodium bis(4-benzoylphenyl) phosphate (BPP).

10. The coating of claim 1 , at least one of the first and second ionic cross-linking agents comprising ethylenebis (4-benzoylbenzyldimethylammonium) dibromide.

11. The coating of claim 1 , the first layer further comprising non-derivatized polyvinylpyrrolidone.

12. The coating of claim 11 , wherein the ratio of the first polyvinylpyrrolidone derivatized with a photoreactive group in the first layer to non-derivatized polyvinylpyrrolidone in the first layer to the first ionic cross-linking agent comprising at least two photoreactive groups is from about 13:0.1:1 to 13:8:1.

13. The coating of claim 1 , the coating exhibiting a lubricity when wetted of between 0 and 30 grams of force.

14. The coating of claim 1 , the coating exhibiting a lubricity when wetted of between 0 and 30 grams of force for at least 10 consecutive testing cycles.

15. The coating of claim 1 , the coating exhibiting a durability of lubricity such there is less than a 30 percent increase in measured friction between the average of cycles 1-5 of testing and cycles 10-15 of testing.

16. The coating of claim 1 , wherein the thickness of the first layer and second layer combined is between about 100 and 3000 nm when dry.

17. The coating of claim 1 , wherein the photoreactive groups are benzophenone.

18. A coating for a medical device comprising:
a first layer comprising
a first polymer composition comprising a polyvinylpyrrolidone derivatized with a photoreactive group; and
a first ionic cross-linking agent comprising at least two photoreactive groups; and

a second layer disposed on the first layer, the second layer distinct from the first layer, comprising
a second polymer composition comprising a polyvinylpyrrolidone derivatized with a photoreactive group, wherein the first polyvinylpyrrolidone derivatized with a photoreactive group and the second polyvinylpyrrolidone derivatized with a photoreactive group are the same; and
a second ionic cross-linking agent comprising at least two photoreactive groups;
wherein the first polymer composition of the first layer and the second polymer composition of the second layer are the same;
wherein the first ionic cross-linking agent is present in the first layer in a first concentration and the second ionic cross-linking agent is present in the second layer in a second concentration;
wherein the first concentration of the first ionic cross-linking agent present in the first layer is higher than the second concentration of the second ionic cross-linking agent present in the second layer such that the first concentration of the first ionic cross-linking agent comprises a higher concentration of photoreactive groups than the second concentration of the second ionic cross-linking agent in the second layer;
wherein the first ionic cross-linking agent and the second ionic cross-linking agent confer an ionic charge to both the first layer and the second layer, and wherein the ionic charge of the first and second layer are both anionic or both cationic; and
wherein the coating releases less than 1,592 particles greater than 10 microns in size per square centimeter of coating surface area when exposed to an aqueous environment.

19. The coating of claim 1 , wherein the first ionic cross linking agent and the second ionic cross-linking agent are both cationic.

20. The coating of claim 1 , wherein the

Assignees

• Surmodics Inc

Inventors

• Babcock David E

Classifications

• A61L31/10

  Macromolecular materials · CPC title

• A61L29/085 Primary

  Macromolecular materials · CPC title

• A61L27/34

  Macromolecular materials · CPC title

• A61L2400/10

  Materials for lubricating medical devices · CPC title

• A61L29/14

  Materials characterised by their function or physical properties {, e.g. lubricating compositions} · CPC title