Material and process for controlled thin polymeric coatings on plastic surface

• US 7,247,387 B1
• Filed: 07/10/2004
• Issued: 07/24/2007
• Est. Priority Date: 07/24/2003
• Status: Active Grant

• Current Assignee: Sepax Technologies, Inc.
• Original Assignee: Sepax Technologies, Inc.
• Inventors: Huang, Xueying
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): TOSCANO, ALICIA
• Application Number:
  US10/887,672
• Time in Patent Office: 1,109 Days
• Field of Search: 428/447, 428/446, 526/81, 526/87, 526/91, 526/109, 526/118, 526/201
• US Class Current: 428/447
• CPC Class Codes: C08J 2383/10 Block- or graft-copolymers containing polysiloxane sequences
• CPC Class Codes: C08J 2433/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
• 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 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08J 7/16 with polymerisable compounds
• CPC Class Codes: C09D 133/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

This invention provides a chemically coated surface for the plastics surface such as contact lens. The chemical surface coating comprises of at least one addition polymer prepared from addition monomers selected from a group consisting of acrylates and its derivatives, metharylates and its derivatives, styrene and its derivatives, acrylamide, methacrylamide, dimethacrylamide, N-monosubstituted acrylamide, N-monosubstituted methacrylamide, N,N-bissubstituted acrylamide, N,N-bissubstituted methacrylamide, vinyl acetate, vinyl pyrolidone, vinyl ether, acrylic acid and methacrylic acid. This invention also provides a chemical process for making the chemically coated surface on the plastics surface. The process comprises:

• • (a) contacting the plastics surface with a coupling agent solution, then
  • (b) contacting the plastics surface with a first living radical polymerizing solution, and optionally
  • (c) contacting the plastics surface with a second living radical polymerizing solution.

Claims

1. A chemically coated surface comprising:

a) a plastics surface;

b) a coupling agent;

c) a chemical surface coating comprising at least one addition polymer;

wherein the chemical surface coating and the coupling agent are covalently bonded, and the coupling agent is a polymer or an oligomer comprising of;

(a) at least two functional groups capable of binding onto the plastics surface

(b) at least two functional groups capable of generating a living radical for initiating polymerization of addition monomers;

and wherein the coupling agent has a hydrocarbon backbone.

2. A chemically coated surface of claim 1, wherein the coupling agent is selected from the group consisting of:

3. A chemically coated surface of claim 2, wherein Y is:

4. A chemically coated surface of claim 3, wherein R₁═

R₂═

CH₃, X is Cl or Br.

5. A chemically coated surface of claim 2, wherein Y is:

6. A chemically coated surface of claim 5, wherein R₃═

R₄═

CH₃, X is Cl or Br.

7. A chemically coated surface of claim 1, wherein the polymer or oligomer is prepared from acrylic acid and the following molecule:

8. A chemically coated surface of claim 1, wherein the polymer or oligomer is prepared from

9. A chemically coated surface of claim 1, wherein the at least one addition polymer is prepared from addition monomers selected from a group consisting of acrylates and its derivatives, methacrylates and its derivatives, styrene and its derivatives, acrylamide, methacrylamide, N-monosubstituted acrylamide, N-monosubstituted methacrylamide, N,N-bissubstituted acrylamide, N,N-bissubstituted methacrylamide, vinyl acetate, vinyl pyrolidone, vinyl ether, acrylic acid, methacrylic acid.

10. A chemically coated surface of claim 9, wherein the addition monomers are selected from a group consisting of polyethylene glycol methacrylate with (CH₂CH₂O)_n, n=1-20, polyethylene glycol acrylate with (CH₂CH₂O)_n, n=1-20, glycidyl methacrylate, glycidyl acrylate, acrylamide, methacrylamide and vinyl pyrolidone.

11. A chemically coated surface of claim 10, wherein the addition monomers are selected from a group consisting of polyethylene glycol methacrylate with (CH₂CH₂O)_n, n=1-20, polyethylene glycol acrylate with (CH₂CH₂O)_n, n=1-20, acrylamide, methacrylamide.

12. A chemically coated surface of claim 1, wherein at least two addition polymers are crosslinked.

13. Contact lens made with the chemically coated surface of claim 1.

14. A method for making a chemically coated surface, comprising:

(a) contacting a plastics surface with a coupling agent solution, then

(b) contacting the plastics surface with a first living radical polymerization solution, and optionally

(c) contacting the plastics surface with a second living radical polymerization solution

wherein the coupling agent is a polymer or an oligomer comprising of;

(i) at least two functional groups capable of binding onto the plastics surface

(ii) at least two functional groups capable of generating a living radical for initiating polymerization of addition monomers;

and wherein the coupling agent has a hydrocarbon backbone.

15. A method for making a chemically coated surface of claim 14, wherein the polymer or oligomer is prepared from acrylic acid and the following molecule:

16. A method for making a chemically coated surface of claim 14, wherein the polymer or oligomer is prepared from

17. A method for making a chemically coated surface of claim 14, wherein the first and second living radical polymerizing solution independently comprises of at least one solvent, at least one catalyst and at least one addition monomer.

18. A method for making a chemically coated surface of claim 17, wherein the solvent is a mixture of water and water miscible organic solvent.

19. A method for making a chemically coated surface of claim 17, wherein the solvent is water.

20. A method for making a chemically coated surface of claim 17, wherein the at least one catalyst is selected from the group consisting of MX_nE_m, wherein M is Cu;

E is selected from bipyridine and its derivatives, n=1 or 2;

m=2;

X═

Cl or Br.

21. A method for making a chemically coated surface of claim 20, wherein the catalysts are CuCl(bipyridine)₂ and CuCl₂(bipyridine)₂.

22. A method for making a chemically coated surface of claim 17, wherein the at least one addition monomer is selected from the group consisting of acrylates and its derivatives, methacrylates and its derivatives, styrene and its derivatives, acrylamide, methacrylamide, N-monosubstituted acrylamide, N-monosubstituted methacrylamide, N,N-bissubstituted acrylamide, N,N-bissubstituted methacrylamide, vinyl acetate, vinyl pyrolidone, vinyl ether, acrylic acid, methacrylic acid, diolefins, triolefins and tetraolefins.

23. A method for making a chemically coated surface of claim 22, wherein the at least one addition monomer is selected from the group consisting of polyethylene glycol methacrylate with (CH₂CH₂O)_n, n=1-20, polyethylene glycol acrylate with (CH₂CH₂O)_n, n=1-20, glycidyl methacrylate, glycidyl acrylate, acrylamide, methacrylamide and vinyl pyrolidone.

24. A method for making a chemically coated surface of claim 23, wherein the at least one addition monomer is selected from the group consisting of polyethylene glycol methacrylate with (CH₂CH₂O)_n, n=1-20, polyethylene glycol acrylate with (CH₂CH₂O)_n, n=1-20, acrylamide, methacrylamide.

25. Contact lens made with the chemically coated surface prepared by the process of claim 14.