COATING SOLUTIONS COMPRISING SURFACE ACTIVE SEGMENTED BLOCK COPOLYMERS

• US 20090169716A1
• Filed: 12/16/2008
• Published: 07/02/2009
• Est. Priority Date: 12/27/2007
• Status: Abandoned Application

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay F., Linhardt, Jeffrey G., Shipp, Devon A.
• Application Number:
  US12/335,794
• Publication Number:
  US 20090169716A1
• Time in Patent Office: Days
• US Class Current: 427/2.250
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61M 25/0045 multi-layered, e.g. coated coating materials A61L29/08
• CPC Class Codes: C08F 130/08 containing silicon
• CPC Class Codes: C08F 230/00 Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal metal salts, e.g. phenolates or alcoholates, see the parent compounds
• CPC Class Codes: C08F 2438/03 Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
• CPC Class Codes: C08F 293/005 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
• CPC Class Codes: C08J 2343/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08J 2383/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31536 Including interfacial reaction product of adjacent layers
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

This invention is directed toward surface treatment of a device. The surface treatment comprises the placing of surface active segmented block copolymers to the surface of the substrate. The present invention is also directed to a surface modified medical device, examples of which include contact lenses, intraocular lenses, vascular stents, phakic intraocular lenses, aphakic intraocular lenses, corneal implants, catheters, implants, and the like, comprising a surface made by such a method.

Claims

1. A method of forming a surface modified medical device, the method comprising:

providing a medical device having at least one surface;

providing a surface modifying agent comprising a surface active segmented block copolymer; and

contacting the at least one surface of the medical device with the surface modifying agent to form a surface modified medical device.

2. The method of claim 1 wherein the medical device comprises a silicon containing monomer.

3. The method of claim 2 wherein the silicon containing monomer comprises a silicon containing monomer selected from the group consisting of silicon containing vinyl carbonates, silicon containing vinyl carbamates, polyurethane-polysiloxanes having one or more hard-soft-hard blocks and end-capped with a hydrophilic monomer, fumarate containing silicon containing monomers, poly(organosiloxanes) capped with an unsaturated group at two or more ends of the molecule, polyurethane-polysiloxane macromonomers and mixtures thereof.

4. The method of claim 1 wherein the medical device comprises hydrogel materials.

5. The method of claim 2 wherein the medical device comprises silicon containing hydrogel materials.

6. The method of claim 1 wherein the medical device comprises vinyl functionalized polydimethylsiloxanes copolymerized with hydrophilic monomers.

7. The method of claim 1 wherein the medical device comprises a fluorinated monomer.

8. The method of claim 7 wherein the fluorinated monomer is selected from the group consisting of methacrylate functionalized fluorinated polyethylene oxides, fluoroalkylmethacrylates, and mixtures thereof.

9. The method of claim 1 wherein the medical device is selected from the group consisting of heart valves, intraocular lenses, intraocular lens inserter, contact lenses, intrauterine devices, vessel substitutes, artificial ureters, vascular stents, phakic intraocular lenses, aphakic intraocular lenses, corneal implants, catheters, implants, endoscopic instruments, and artificial breast tissue.

10. The method of claim 9 wherein the medical device formed is a soft contact lens.

11. The method of claim 10 wherein the medical device is a silicon containing hydrogel contact lens material.

12. The method of claim 1 wherein the reactive segmented block copolymer has the following generic formula (I):

R1-[(A)m]p-[(B)n]q-X  

 

(I)

wherein R1 is a reactive residue of a moiety capable of acting as an initiator for Atom Transfer Radical Polymerization, A is a hydrophobic unit block, B is a hydrophilic unit block, m is 1 to 10,000, n is 1 to 10,000, p and q are natural numbers, and X is a halogen capping group of an initiator for Atom Transfer Radical Polymerization or a derivatized reaction product.

13. The method of claim 1 wherein the reactive segmented block copolymer has the following generic formula (II):

R1-[(A)m]p-[(B)n]q-R2  

 

(II)

wherein R1 is a radical forming residue of a RAFT agent or free radical initiator, A is a hydrophobic unit block, B is a hydrophilic unit block, m is 1 to 10,000, n is 1 to 10,000, p and q are natural numbers, and R2 is a thio carbonyl thio fragment of the chain transfer agent or a derivatized reaction product.

14. The method of claim 1 wherein the interactive segmented block copolymer has the following generic formula (III):

R1-[(B)n]q-[(A)m]p-R2-[(A)m]p-[(B)n]q-R1  

 

(III)

wherein R1 is a radical forming residue of a RAFT agent or free radical initiator, A is a hydrophobic unit block, B is a hydrophilic unit block, m is 1 to 10,000, n is 1 to 10,000, p and q are natural numbers, and R2 is a thio carbonyl thio group.

15. The method of claim 1, wherein the hydrophobic unit of the surface active segmented block copolymer comprises a monomer selected from the group consisting of alkyl acrylates, hexyl methacrylate, lauryl methacrylate, fluoroacrylates, octofluoropentamethacrylate, 3,3,4,4,5,5,6,6,7,7,8,8-tridecafluorooctyl methacrylate, polysiloxanylalkyl(meth)acrylic monomers, M1-MCR-C12, methacryloxypropyl tris(trimethyl-siloxy)silane, tris(trimethylsiloxy)silylpropyl methacrylate, 3-(trimethylsilyl)propyl vinyl carbonate;

3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane];

3-[tris(tri-methylsiloxy)silyl]propyl vinyl carbamate;

3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate;

3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, dodecyl methacrylate, hexyl vinyl carbamate, hexyl vinyl carbonate, octafluoropentamethacrylate, octafluoropenta vinyl carbamate, and mixtures thereof.

16. The method of claim 1, wherein the reactive segmented block copolymer comprises a hydrophilic unit monomer selected from the group consisting of 2-hydroxyethyl methacrylate, glycerol methacrylate, methacrylic acid, acrylic acid, methacrylamide, acrylamide, N,N′

-dimethylmethacrylamide, N,N′

-dimethylacrylamide;

ethylenically unsaturated poly(alkylene oxide)s, cyclic lactams, N-vinyl-2-pyrrolidone, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomers, 2-hydroxyethyl acrylate, 2-(2-ethoxyethoxy)ethyl(meth)acrylate, glyceryl(meth)acrylate, poly(ethylene glycol(meth)acrylate), tetrahydrofurfuryl(meth)acrylate, N-vinyl acetamide, copolymers, derivatives and combinations thereof.

17. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophobic unit comprises between 1 and about 1,000 units.

18. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophobic unit comprises between 1 and about 100 units.

19. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophobic unit comprising between 1 and about 30 units.

20. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophilic block comprising between 1 and about 10,000 units.

21. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophilic block comprising between about 10 and about 1,000 units.

22. The method of claim 1, wherein the surface active segmented block copolymer has a hydrophilic block comprising between about 20 and about 300 units.

27. The method of claim 12 wherein the hydrophobic unit block comprises vinylically unsaturated polymerizable monomers and the hydrophilic block comprises vinylically unsaturated polymerizable monomers.

28. The method of claim 13 wherein the hydrophobic unit block comprises vinylically unsaturated polymerizable monomers and the hydrophilic block comprises vinylically unsaturated polymerizable monomers.

29. The method of claim 14 wherein the hydrophobic unit block comprises vinylically unsaturated polymerizable monomers and the hydrophilic block comprises vinylically unsaturated polymerizable monomers.

23. A surface modified medical device comprising:

a medical device; and

a surface active segmented block copolymer comprising a hydrophobic unit block comprising vinylically unsaturated polymerizable monomers and a hydrophilic block comprising vinylically unsaturated polymerizable monomers applied to the surface of the medical device.

24. The surface modified medical device of claim 23 wherein the medical device is a contact lens.

25. The surface modified medical device of claim 24 wherein the medical device is a hydrophilic contact lens.

26. The surface modified medical device of claim 24 wherein the medical device is a hydrogel contact lens.