Process for surface modifying substrates and modified substrates resulting therefrom

• US 20020086160A1
• Filed: 08/24/2001
• Published: 07/04/2002
• Est. Priority Date: 08/24/2000
• Status: Active Grant

• Current Assignee: Alcon Incorporated, Commonwealth Scientific & Industrial Research Organisation (Commonwealth Of Australia As Represented By Department Of Industry, Innovation, Climate Change, Science, Research And Tertiary Education)
• Original Assignee: Commonwealth Scientific & Industrial Research Organisation (Commonwealth Of Australia As Represented By Department Of Industry, Innovation, Climate Change, Science, Research And Tertiary Education), Novartis Ag
• Inventors: Lally, John Martin, Winterton, Lynn Cook, Qiu, Yongxing, Chabrecek, Peter, Griesser, Hans, Pasic, Paul, Kambouris, Peter
• Granted Patent: US 6,893,685 B2
• Time in Patent Office: Days
• US Class Current: 428/413
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08J 7/16 with polymerisable compounds
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31667 Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31928 Ester, halide or nitrile of addition polymer

Abstract

The invention relates to a process for coating a material surface, comprising the steps of:

(a) applying to the material surface a tie layer comprising a polyionic material;

(b) covalently binding a bifunctional compound comprising an ethylenically unsaturated double bond to the tie layer; and

(c) graft polymerizing a hydrophilic monomer onto the compound comprising the ethylenically unsaturated double bond.

The coated articles that are obtainable by the process of the invention have desirable characteristics regarding adherence to the substrate, durability, hydrophilicity, wettability, biocompatibility and permeability and are thus useful for the manufacture of biomedical articles such as ophthalmic devices.

Claims

1. A process for coating a material surface, comprising the steps of:

(a) applying to the material surface a tie layer comprising a polyionic material;

(b) covalently binding a bifunctional compound comprising an ethylenically unsaturated double bond to the tie layer; and

(c) graft polymerizing a hydrophilic monomer onto the compound comprising the ethylenically unsaturated double bond.

2. A process according to claim 1, wherein the material surface is the surface of an organic bulk material, in particular the surface of a biomedical device comprising an organic bulk material.

3. A process according to claim 1 or 2, wherein the tie layer of step (a) consists of one single polyionic material.

4. A process according to claim 1 or 2, wherein the tie layer of step (a) includes at least one bilayer comprising a polycationic material and a polyanionic material.

5. A process according to any one of claims 1 to 4, wherein the polyionic material of the tie layer comprises one or more polymers selected from the group consisting of a poly(allylamine hydrochloride), a poly(ethyleneimine), a poly(acrylic acid), and a poly(methacrylic acid).

6. A process according to any one of the claims 1 to 5, wherein the covalent bonding between the tie layer and the bifunctional compound comprising an ethylenically unsaturated double bond occurs via reaction of a hydroxy, amino, alkylamine, thiol or carboxy group, of the tie layer with an isocyanato, azlactone, epoxy, carboxy anhydride, carboxy or hydroxy group, of the ethylenically unsaturated compound.

7. A process according to any one of claims 1 to 6, wherein the ethylenically unsaturated compound is of formula

8. A process according to claim 7, wherein, in step (b), the compound comprising an ethylenically unsaturated double bond is of formula (2a).

9. A process according to any one of the claims 1 to 8, wherein, in step c), the hydrophilic monomer is selected from the group consisting of acrylamide, acrylic acid, methacrylic acid, hydroxyethyl methacrylate, hydroxyethyl acrylate, methacrylamide, N,N-dimethylacrylamide, allylalcohol, N-vinylpyrrolidone and N,N-dimethylaminoethyl acrylate.

10. A process according to any one of claims 1 to 9, wherein in step (c), the monomer comprises one or more different monomers at least one of them comprising a reactive group.

11. A process according to any one of the claims 1 to 10, wherein in step (c), the monomer comprises a reactive group,

(i) said reactive groups are reacted with a further compound comprising an ethylenically unsaturated double bond,

(ii) a hydrophilic monomer and optionally a co-monomer having a crosslinkable group are graft-polymerized to said ethylenically unsaturated double bond, and

(iii) in case crosslinkable groups being present in step (ii), crosslinking of said groups is initiated.

12. A process according to claim 11, wherein, in step (i), the further compound comprising an ethylenically unsaturated double bond is a compound of formula (2a)-(2e) according to claim 7.

13. A process according to claims 11 or 12, wherein, in step (ii) the hydrophilic monomer is selected from the group consisting of acrylic acid, acrylamide, N,N-dimethylacrylamide and N-vinylpyrrolidone and no co-monomer having a crosslinking group is present.

14. A coated material that is obtainable by the process of any one of the claims 1 to 13.

15. A coated material according to claim 14, which is a biomedical device.

16. A coated material according to claim 15, which is an ophthalmic device.

17. A coated material according to claim 16, which is a contact lens, intraocular lens or artificial cornea.