Polymeric materials for making contact lenses

• US 6,815,074 B2
• Filed: 05/22/2002
• Issued: 11/09/2004
• Est. Priority Date: 05/30/2001
• Status: Expired due to Term

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Aguado, Celeste, Lally, John Martin, Winterton, Lynn Cook, Qiu, Yongxing, Nicolson, Paul Clement, Schremmer, Jacalyn Mary
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US10/153,040
• Publication Number:
  US 20030008154A1
• Time in Patent Office: 902 Days
• Field of Search: 428/447, 528/32, 523/106, 523/107, 524/588, 526/279, 540/139, 540/140, 427/2.24, 427/162
• US Class Current: 428/447
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

An ophthalmic lens suited for extended-wear periods of at least one day on the eye without a clinically significant amount of corneal swelling and without substantial wearer discomfort. The lens has a balance of oxygen permeability and ion or water permeability, with the ion or water permeability being sufficient to provide good on-eye movement, such that a good tear exchange occurs between the lens and the eye. A preferred lens is a copolymerization product of a oxyperm macromer and an ionoperm monomer. The invention encompasses extended wear contact lenses, which include a core having oxygen transmission and ion transmission pathways extending from the inner surface to the outer surface.

Claims

1. An ophthalmic lens, comprising a core polymeric material and an ophthalmically compatible surface which is more hydrophilic than said core polymeric material, wherein the ophthalmic lens has a high oxygen permeability characterized by a D_k greater than 56 barrers and a high ion permeability characterized by an ionoflux diffusion coefficient of great than 4.0×

10<sup>−

4</sup> mm 2/min and comprises a water content of at least 25 weight percent when fully hydrated, wherein said ophthalmically compatible surface is an LbL coating comprisisg a plurality of bilayers and a capping layer of polyvinylpyrrolidone, wherein each bilayer comprises one layer of a first polyionic material and one layer of a second polyionic material having charges opposite of the charges of the first polyionic materials, wherein said core polymeric material is prepared by curing in a mold in an oxygen-containing or oxygen-free atmosphere a polymer composition including;

(i) about 5 to about 40 weight percent of a macromer, wherein said macromer is selected from the group consisting of Macromer A, Macromer B, Macromer C, and Macromer D;

(ii) about 10 to about 30 weight percent of a siloxane-containing monomer; and

(iii) about 30 to about 50 weight percent of a hydrophilic monomer,

wherein said weight percentages are based upon the dry weight of the polymer components,

wherein Macromer A is a polysiloxane macromer having a number-average molecular weight of 2000 to 10,000 and the the segment of the formula;

2. An ophthalmic lens of claim 1, wherein said ophthalmic lens is selected from the group consisting of contact lenses for vision correction, contact lenses for eye color modification, ophthalmic drug delivery devices, and ophthalmic wound healing devices.

3. An ophthalmic lens of claim 2, wherein said ophthalmic lens is a contact lens.

4. A contact lens of claim 3, wherein said contact lens further has:

(1) a tensile modulus of less than about 1.5 Mpa; and

/or (2) a short relaxation time constant (t₁) greater than about 3.5 seconds.

5. A contact lens of claim 3, wherein said contact lens further has a Hydrodell Water Permeability Coefficient of greater than about 0.2×

10<sup>−

6</sup> cm²/min.

6. A contact lens of claim 3, wherein said core polymeric material comprises at least a color additive.

7. A contact lens of claim 6, wherein said color additive is copper phthalocyanine.

8. A contact lens of claim 1, wherein said LbL coating comprises at least one lubricious bilayer which is composed of one layer of a lubricious coating material and one layer of a polyionic material having charges opposite of the charges of the lubricious coating material, wherein the lubricious coating material is selected from the group consisting of alginates, poly(allylamine hydrochloride) polymers comprising lactone as modifier units, hyaluronic acid and salts thereof, PAMAM dendrimers, PAAm-co-PAA, chondroitin sulfate, chitosan, proteoglycans, mimics, and mixtures thereof.

9. A contact lens of claim 1, wherein said LbL coating includes about 5 to 20 bilayers.

10. A contact lens of claim 9, wherein said first polyionic material is a polycationic material and said second polyionic material is a polyanionic material.

11. A contact lens of claim 10, wherein said polycationic material polycationic materials is selected from the group consisting of poly(allylamine hydrochloride) (PAH), poly(ethyleneimine) (PEI), poly(vinylbenzyltriamethylamine) (PVBT), polyaniline, sulphonated polyaniline, polypyrrole, and poly(pyridinium acetylene).

12. A contact lens of claim 10, wherein said polyanionic material is selected from the group consisting of polymethacrylic acid (PMA), polyacrylic acid (PAA), poly(thiophene-3-acetic acid) (PTAA), poly(4-styrenesulfonic acid) (PSS), sodium poly(styrene sulfonate) (SPS) and poly(sodium styrene sulfonate) (PSSS).

13. A method for making an ophthalmic lens, comprising the steps of:

(1) curing a polymer composition in a mold in an oxygen-containing or oxygen-free atmosphere to obtain a core of the ophthalmic lens, wherein the polymer composition includes;

(I) about 5 to about 40 weight percent of a macromer, wherein said macromer is selected from the group consisting of Macromer A, Macromer B, Macromer C, and Macromer D;

(II) about 10 to about 30 weight percent of a siloxane-containing monomer; and

(III) about 30 to about 50 weight percent of a hydrophilic monomer,

wherein said weight percentages are based upon the dry weight of the polymer components,

wherein Macromer A is a polysiloxane macromer having a number-average molecular weight of 2000 to 10,000 and the the segment of the formula;

14. A method of claim 13, wherein said hydrophilic monomer is selected from the group consisting of hydroxyl-substituted lower alkyl (C₁ to C₈) acrylates and methacrylates, acrylamide, methacrylamide, (lower allyl)aerylamides and -methacrylamides, ethoxylated acrylates and methaerylates, hydroxyl-substituted (lower alkyl)acrylamides and -methacrylamides, hydroxyl-substituted lower alkyl vinyl ethers, sodium vinylsulfonate, sodium styrenesulfonate, 2-acrylamido-2-methylpropanesulfonic acid, N-vinylpyrrole, N-vinyl-2-pyrrolidone, 2-vinyloxazoline, 2-vinyl-4,4′

-dialkyloxazolin-5-one, 2- and 4-vinylpyridine, vinylically unsaturated carboxylic acids having a total of 3 to 5 carbon atoms, amino(lower alkyl)-, mono(lower alkylamino)(lower alkyl) and di(lower alkylamino)(lower alkyl)acrylates and methaerylates, and allyl alcohol.

15. A method of claim 14, wherein said hydrophilic monomer is 2-hydroxyethylmethacrylate (HEMA), hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate (HPMA), trimethylammonium 2-hydroxy propylmethacrylate hydrochloride, dimethylaminoethyl methacrylate (DMAEMA), dimethylaminoethylmethacrylamide, aerylamide, methacrylamide, allyl alcohol, vinylpyridine, glycerol methacrylate, N-(1,1dimethyl-3-oxobutyl)acrylamide, N-vinyl-2-pyrrolidone (NVP), acrylic acid, methacrylic acid, or N,N-dimethyacrylamide (DMA).

16. A method of claim 15, wherein said siloxane-containing monomer is 3-methaeryloxypropyltris (trimethylsiloxy) silane (TRIS).

17. A method of claim 15, wherein the polymer composition further comprises an amount of less than about 3% weight percent of a photoinitiator.

18. A method of claim 17, wherein said photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone.

19. A method of claim 15, wherein the polymer composition further comprising an amount of less than about 10% weight percent of a crosslinking agent.

20. A method of claim 19, wherein said crosslinking agent is selected from the group consisting of allyl(meth)acrylate, lower alkylene glycol di(meth)acrylate, poly lower alkylene glycol di(meth)acrylate, lower alkylene di(meth)acrylate, divinyl ether, divinyl sulfone, di- or trivinylbenzene, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, bisphenol A di(meth)acrylate, methylenebis(meth)acrylamide, triallyl phthalate and diallyl phthalate.

21. A method of claim 20, wherein said crosslinking agent is ethylene glycol dimethacrylate (EGDMA).

22. A method of claim 15, wherein the polymer composition further comprises a solvent which is selected from the group consisting of water, C₁-C₄ alkanols, dimethylformamide, dimethyl sulfoxide, methyl ethyl ketone, acteone, cyclohexanone, toluene, ethers, THF, dimethoxyethane, dioxane, and trichloroethane, and mixtures thereof.

23. A method of claim 22, wherein said solvent is ethanol and present in an amount of from about 15 to about 40 weight percent.

24. A method of claim 15, wherein said siloxane-containing monomer is 3-methacryloxypropyltris (trimethylsiloxy) silane (TRIS), wherein said hydrophilic monomer is N,N-Dimetryl acrylamide.

25. A method of claim 15, wherein the polymer composition futher comprises a color additive.

26. A method of claim 25, wherein the color additive is copper phthalocyanine.

27. A method of claim 15, wherein the LbL coating comprises at least one lubricious bilayer which is composed of one layer of a lubricious coating material and one layer of a polyionic material having charges opposite of the charges of the lubricious coating material, wherein the lubricious coating material is selected from the group consisting of alginates, poly(allylamine hydrochloride) polymers comprising lactone as modifier units, hyaluronic acid and salts thereof, polyamidoamine dendrimers, chondroitin sulfate, chitosan, proteoglycans, and mixtures thereof.