Multilayer materials

• US 6,623,747 B1
• Filed: 02/14/1996
• Issued: 09/23/2003
• Est. Priority Date: 09/14/1992
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Dai, Liming, Li, Sheng, Lohmann, Dieter, Chabrecek, Peter, Zientek, Paul, Griesser, Hans Jörg, Chatelier, Ronald Christopher
• Primary Examiner(s): Kishore, Gollamudi S.
• Application Number:
  US08/601,420
• Time in Patent Office: 2,778 Days
• Field of Search: 424/400, 424/422-426, 424/427
• US Class Current: 424/422
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention is directed to a composite material, especially a biomedical device, e.g. an ophthalmic device, preferably a contact lens, with one or more wettable surfaces capable of holding a continous layer of aqueous fluid thereon which composite material comprises a bulk material and a hydrophilic coating characterized in that the hydrophilic coating consists of a carbohydrate attached covalently to reactive groups at the surface of the bulk material, either directly or via functional groups of an oligofunctional compound, said oligofunctional compound in turn having functional groups being capable of reacting with said reactive groups at the surface of the bulk material and with the carbohydrate, wherein said reactive groups are either inherently (a priori) present in the bulk material or wherein said reactive groups have been attached to the surface of the bulk material by a plasma surface preparation, as well as to a process of manufacture of such a composite material.

Claims

1. A composite materials having at least one wettable surface capable of holding a continuous layer of aqueous fluid therein, which material comprises:

(a) a bulk base material, and

(b) a hydrophilic coating, wherein the hydrophilic coating consists of a carbohydrate directly and covalently attached to amino groups at the surface of the bulk base material, wherein said amino groups are either inherently (a priori) present in the base material or have been attached to the surface of the bulk base material by plasma surface treatment.

2. A composite material according to claim 1 wherein the amino groups are inherently present in the base material.

3. A composite material according to claim 1 which is a biomedical device.

4. A composite material according to claim 1 which is an ophthalmic device.

5. A composite material according to claim 1 which is a contact lens.

6. A composite material according to claim 1 wherein the carbohydrate is selected from dextran, chitosan, hyaluronic acid, mucin, fucoidan, and glucosamine.

7. A composite material according to claim 1 wherein said amino groups have been directly and covalently attached to said surface by plasma surface treatment.

8. A composite material according to claim 1 wherein said amino groups have been directly and covalently attached to said surface by plasma surface treatment and the carbohydrate is a polysaccharide.

9. A composite material according to claim 8 wherin the carbohydrate is selected from dextran, chitosan, hyaluronic acid, mucin, fucoidan, and glucosamine.

10. A composite material according to claim 1 wherein amino groups are inherently present in the base material wherein the carbohydrate is a polysaccharide.

11. A composite material according to claim 10 wherin the carbohydrate is selected from dextran, chitosan, hyaluronic acid, mucin, fucoidan, and glucosamine.

12. A composite material according to claim 1 wherein amino groups are inherently present in the base material, wherein the carbohydrate is a non-polysaccharide carbohydrate with is directly attached to the amino groups.

13. A composite material according to claim 1 wherein amino groups are inherently present in the base material, wherein the carbohydrate is dextran.

15. A composite material according to claim 1, wherein the amino groups are covalently attached to the surface of preformed base material by subjecting the preformed base material to a low pressure plasma in a vapor of an alkylamine having up to eight carbon atoms under conditions whereby amino groups are formed on the desired surface of the base material.

16. A composite material according to claim 15 wherein the alkyl amine is heptylamine.

17. A composite material according to claim 15 wherein the alkyl amine is ethylamine.

18. A composite material according to claim 15 wherein the alkyl amine is methylamine.

14. A process for the manufacture of a wettable composite material with one or more wettable surface capable of holding a continuous layer of aqueous fluid thereon, wherein said composite material includes a bulk base material and a hydrophilic coating of a carbohydrate directly attached covalently to amino groups at the surface of the base materials, said process comprising the steps of:

(1) covalently attaching amino groups onto the surface of a preformed base material by subjecting the preformed base material to a gas plasma established in a vapor containing at least one amine compound;

(2) optionally treating the carbohydrate with a reagent which modifies said carbohydrate such that said carbohydrate is capable of reacting with the amino groups;

(3) reacting said amino groups on the surface with the carbohydrate to immobilize the carbohydrate onto the surface; and

(4) optionally treating the surface-immobilized carbohydrate with a reagent to stabilize the bond between the carbohydrate and the surface.

19. A process of claim 14 wherein the amine is an alkyl amine having up to eight carbon atoms.

20. A process of claim 14 wherein the alkyl amine is heptylamine.

21. A process of claim 14 wherein the alkyl amine is ethylamine.

22. A process of claim 14 wherein the alkyl amine is methylamine.