Silane copolymer compositions containing active agents

• US 6,596,401 B1
• Filed: 05/10/2000
• Issued: 07/22/2003
• Est. Priority Date: 11/10/1998
• Status: Expired due to Term

• Current Assignee: C.R. Bard, Inc. (Becton, Dickinson & Co)
• Original Assignee: C.R. Bard, Inc. (Becton, Dickinson & Co)
• Inventors: Walsh, Kevin, Terry, Richard N.
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US09/568,770
• Time in Patent Office: 1,168 Days
• Field of Search: 524/17, 524/195, 524/434, 524/450, 524/588, 524/704, 524/714, 524/780, 524/789, 524/791, 524/858, 524/869, 424/280.1, 424/600, 424/617, 424/684, 427/2.28, 428/447, 428/448, 604/264
• US Class Current: 428/447
• CPC Class Codes: A61L 2400/10 Materials for lubricating medical devices
• CPC Class Codes: A61L 27/18 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 31/10 Macromolecular materials
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/3893 containing silicon
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08L 75/00 Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 175/08 from polyethers
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

The invention is drawn to silane copolymers prepared from the reaction of one or more polyisocyanates with one or more lubricious polymers having at least two functional groups, which may be the same or different, that are reactive with an isocyanate functional group and with one or more organo-functional silanes having at least two functional groups, which may be the same or different, that are reactive with an isocyanate functional group and at least one functional group reactive with a silicone rubber substrate. The silane copolymers of the invention can be used as coatings that are elastic when dry, lubricious when wet, and resist wet abrasion. These copolymers are useful as coatings for polysiloxane (rubber) and other difficult to coat substrates, especially for medical devices, such as catheters. These silane copolymers can contain active agents such as antimicrobials, pharmaceuticals, herbicides, insecticides, algaecides, antifoulants, and antifogging agents.

Claims

1. A composition comprising a silane copolymer and an active agent wherein the copolymer is the reaction product of molecules comprising:

an organo-functional silane having at least two functional groups that are reactive with an isocyanate group, and

an isocyanate-containing monomer or polymer.

2. A composition according to claim 1 wherein the silane copolymer is a polyurethane-urea-silane copolymer.

3. A composition according to claim 1 comprising:

(a) a silane copolymer that is the reaction product of molecules comprising one or more polyisocyanates, one or more organo-functional silanes, and one or more polyols; and

(b) an active agent.

4. A composition according to claim 1 wherein the active agent is selected from the group consisting of antimicrobial agents, antibacterial agents, antifungal agents, antiviral agents, antibiotics, chemotherapeutic drugs, anti-inflammatory drugs, growth factors, cytokines, immunoglobulins, pharmaceuticals, nutraceuticals, antithrombogenic agents, antitumoral agents, antiangiogenic agents, spermicides, anesthetics, analgesics, vasodilation substances, wound healing agents, diagnostic agents, antifoulants, insecticides, herbicides, algaecides, antifogging agents, screening agents, and mixtures thereof.

5. A composition according to claim 4 wherein the active agent is selected from the group consisting of oligodynamic metals and salts thereof, zeolites comprising ions of at least one oligodynamic metal, colloids of oligodynamic metal salts, biguanides, and mixtures thereof.

6. A composition according to claim 1 wherein the active agent is present in amounts from 0.1% to 50% based on the dry weight of the composition.

7. An article of manufacture comprising a substrate and a coating wherein the coating comprises a silane copolymer and an active agent and wherein the copolymer is the reaction product of molecules comprising:

an organo-functional silane having at least two functional groups that are reactive with an isocyanate group, and

an isocyanate-containing monomer or polymer.

8. The article according to claim 7 wherein the silane copolymer is a polyurethane-urea-silane copolymer.

9. The article according to claim 7 wherein the coating comprises:

(a) a silane copolymer that is the reaction product of molecules comprising one or more polyisocyanates, one or more organo-functional silanes, and one or more polyols; and

(b) an active agent.

10. An article according to claim 7 wherein the active agent is selected from the group consisting of antimicrobial agents, antibacterial agents, antifungal agents, antiviral agents, antibiotics, chemotherapeutic drugs, anti-inflammatory drugs, growth factors, cytokines, immunoglobulins, pharmaceuticals, nutraceuticals, antithrombogenic agents, antitumoral agents, antiangiogenic agents, spermicides, anesthetics, analgesics, vasodilation substances, wound healing agents, diagnostic agents, antifoulants, insecticides, herbicides, algaecides, antifogging agents, screening agents, and mixtures thereof.

11. An article according to claim 10 wherein the active agent is selected from the group consisting of oligodynamic metals and salts thereof, zeolites comprising ions of at least one oligodynamic metal, colloids of oligodynamic metal salts, biguanides, and mixtures thereof.

12. An article according to claim 7 wherein the active agent is present in amounts from 0.1% to 50% based on the dry weight of the composition.

13. An article according to claim 7 wherein the coating comprises multiple coating layers.

14. An article according to claim 13 wherein one or more of the coating layers comprises an agent that affects the release of the active agent from the coating.

15. An article according to claim 7 wherein the article comprises a layer of silver or a silver salt beneath the coating composition.

16. An article according to claim 7 wherein the active agent is retained in the coating.

17. An article according to claim 7 wherein the article is a medical device.

18. A medical device according to claim 17 which is selected from the group consisting of catheters, guidewires, implant devices, contact lenses, IUDs, peristaltic pump chambers, endotracheal tubes, gastroenteric feed tubes, arteriovenous shunts, condoms, and oxygenator and kidney membranes.

19. A medical device according to claim 18 which is a catheter.

20. A method for the manufacture of a coated article comprising dipping, spraying, or brushing a composition comprising a silane copolymer and at least one active agent onto the surface of the article and allowing the composition to dry wherein the copolymer is the reaction product of molecules comprising:

an organo-functional silane having at least two functional groups that are reactive with an isocyanate group, and

an isocyanate-containing monomer or polymer.