Amphiphilic block copolymers and their use

• US 7,847,025 B2
• Filed: 12/20/2005
• Issued: 12/07/2010
• Est. Priority Date: 12/20/2004
• Status: Active Grant

• Current Assignee: Amo Groningen B.V (Johnson & Johnson)
• Original Assignee: Amo Groningen B.V (Johnson & Johnson)
• Inventors: Norrby, Sverker, Haitjema, Hendrick Jan, Terwee, Thom, Hilborn, Jons Gunnar, Liu, Yan
• Primary Examiner(s): Choi; Ling-Siu
• Assistant Examiner(s): WANG, CHUN CHENG
• Application Number:
  US11/314,930
• Publication Number:
  US 20060134177A1
• Time in Patent Office: 1,813 Days
• Field of Search: 525/100, 424/427, 623/6.56, 623/4.1, 623/926, 514/63, 556/400
• US Class Current: 525/100
• CPC Class Codes: A61K 31/695 Silicon compounds
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: Y10S 623/926 Synthetic

Abstract

The present invention relates to amphiphilic block copolymers comprising at least one block of hydrophilic units and at least one block of hydrophobic units, wherein at least one hydrophobic block contains siloxane units. The present invention may be particularly useful as a tissue adhesive or as a coating for an intraocular lens (IOL). As an IOL coating, copolymers according to the invention may be used, for example, to promote tissue adhesion for the prevention of posterior capsule opacification.

Claims

1. A coating composition for adhering an implant to a biological tissue comprising an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units wherein said at least one hydrophobic block contains siloxane units, the siloxane units having the formula:

3. The composition according to claim 1, wherein said at least one block of hydrophilic units comprises a polymer selected from the group consisting of poly(vinyl alcohol), poly(ethylene glycol), poly(hydroxyethyl methacrylate), polyacrylamide, poly(N-vinyl-pyrrolidone), polyacrylic acid, poly(methacrylic acid), poly(maleic anhydride) and polymaleic acid.

4. The composition according to claim 3, wherein said at least one block of hydrophilic units are poly(ethylene glycol).

5. The composition according to claim 1, wherein said at least one hydrophilic block comprises terminal or lateral functional groups.

6. The composition according to claim 5 wherein said terminal or lateral groups are selected from functional groups which are water stable and which capable of reacting with nucleophilic groups.

7. The composition according to claim 5, wherein said terminal or lateral functional groups are selected from the group consisting of isocyanates, isothiocyanates, acrylates, maleinates, N-hydroxysuccimide esters and cyanoacrylates.

8. The composition according to claim 7, wherein said terminally functional groups are selected from isothiocyanates.

9. The composition according to claim 1, wherein said at least one hydrophilic block is formed from a precursor with the structure

11. The composition according to claim 1 wherein said composition is an ophthalmic composition.

12. The composition according to claim 1 wherein said composition is an aqueous emulsion.

2. A coating composition for adhering an implant to a biological tissue comprising an amphiphilic block copolymer having at least one block of hydrophilic units and at least one block of hydrophobic units wherein said at least one hydrophobic block contains siloxane units, the siloxane units having the formula:

13. The composition according to claim 2 wherein said terminal or lateral groups are selected from functional groups which are water stable and which capable of reacting with amino-groups.

14. The composition according to claim 2 wherein said at least one block of hydrophilic units comprises a polymer selected from the group consisting of poly(vinyl alcohol), poly(ethylene glycol), poly(hydroxyethyl methacrylate), polyacrylamide, poly(N-vinyl-pyrrolidone), polyacrylic acid, poly(methacrylic acid), poly(maleic anhydride) and polymaleic acid.

15. The composition according to claim 14, wherein said at least one block of hydrophilic units are poly(ethylene glycol).

16. The composition according to claim 2, wherein said at least one hydrophilic block comprises terminal or lateral functional groups.

17. The composition according to claim 16 wherein said terminal or lateral groups are selected from functional groups which are water stable and which capable of reacting with nucleophilic groups.

18. The composition according to claim 16, wherein said terminal or lateral functional groups are selected from the group consisting of isocyanates, isothiocyanates, acrylates, maleinates, N-hydroxysuccimide esters and cyanoacrylates.

19. The composition according to claim 18, wherein said terminally functional groups are selected from isothiocyanates.

20. The composition according to claim 2, wherein said at least one hydrophilic block is formed from a precursor with the structure

10. A coating composition for adhering an implant to a biological tissue comprising an amphiphilic block copolymer comprising an amphiphilic block copolymer comprising at least one block of hydrophilic units and at least one block of hydrophobic units, wherein said at least one hydrophobic block contains siloxane units, and wherein said amphiphilic block copolymer is an isothiocyanate terminated poly(ethylene glycol)-b-polysiloxane having the formula: