METHODS FOR INCREASING THE ION PERMEABILITY OF CONTACT LENSES

• US 20110133350A1
• Filed: 12/06/2010
• Published: 06/09/2011
• Est. Priority Date: 12/07/2009
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing, Qian, Xinming
• Granted Patent: US 8,883,051 B2
• Time in Patent Office: Days
• US Class Current: 264/1.1
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Described herein are methods for increasing the ion permeability of a silicone hydrogel contact lens by adding a small amount of an ion-permeability-enhancing (“IP-enhancing”) hydrophilic vinylic monomer or macromer into a lens-forming material for cast-molding silicone hydrogel contact lenses, while not altering significantly the water content and/or the oxygen permeability of resultant lenses from the lens-forming material.

Claims

1. A method for increasing the ion permeability of a silicone hydrogel contact lens, the method comprising:

a. introducing into a mold a lens-forming material, wherein the lens-forming material comprises (i) at least one silicone-containing vinylic monomer or macromer, (ii) at least one hydrophilic vinylic monomer; and

(iii) at least one IP-enhancing vinylic monomer or macromer represented by formula I;

2. The method of claim 1, wherein the lens has an ion permeability that is at least 40% greater than the control lens.

3. The method of claim 1, wherein Y comprises a polyethylene glycol chain segment or a copolymer chain segment composed of ethylene oxide and propylene oxide units.

4. The method of claim 1, wherein Y comprises a polyalkylene oxide having a molecular weight of about 100 to 10,000.

5. The method of claim 1, wherein Y comprises a residue of polyethylene glycol having a molecular weight of 500 to 2,500, and Z is methyl.

6. The method of claim 1, wherein there are two different compounds having the formula I, wherein for each compound Y comprises a residue of polyethylene glycol having a molecular weight of 500 to 2,500, wherein the molecular weight of the polyethylene glycol residue for each compound is different.

7. The method of claim 1, wherein the silicon-containing vinylic monomer comprises N-[tris(trimethylsiloxy)silylpropyl]-(meth)acrylamide, N-[tris(dimethylpropylsiloxy)-silylpropyl]-(meth)acrylamide, N-[tris(dimethylphenylsiloxy)silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)silylpropyl](meth)acrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)-2-methyl acrylamide;

N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)acrylamide;

N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)-propyloxy)propyl]-2-methyl acrylamide;

N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy) methylsilyl)propyloxy)propyl]acrylamide;

N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)-silyl)propyloxy)propyl)-2-methyl acrylamide;

N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)acrylamide;

N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]-2-methyl acrylamide;

N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]acrylamide;

N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl acrylamide;

N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]acrylamide;

N,N-bis[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl acrylamide;

N,N-bis[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]acrylamide;

3-methacryloxy propylpentamethyldisiloxane, tris(trimethylsilyloxy)silylpropyl methacrylate (TRIS), (3-methacryloxy-2-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane), (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, 3-methacryloxy-2-(2-hydroxyethoxy)-propyloxy)propylbis(trimethylsiloxy)methylsilane, N-2-methacryloxyethyl-O-(methyl-bis-trimethylsiloxy-3-propyl)silyl carbamate, 3-(trimethylsilyl)propylvinyl carbonate, 3-(vinyloxycarbonylthio)propyl-tris(trimethyl-siloxy)silane, 3-[tris(trimethylsiloxy)silyl]propylvinyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, t-butyldimethyl-siloxyethyl vinyl carbonate;

trimethylsilylethyl vinyl carbonate, and trimethylsilylmethyl vinyl carbonate), or any combination thereof.

8. The method of claim 1, wherein the silicon-containing vinylic macromer comprises a monomethacrylated or monoacrylated polydimethylsiloxane;

a dimethacrylated or diacrylated polydimethylsiloxane;

a vinyl carbonate-terminated polydimethylsiloxane;

a vinyl carbamate-terminated polydimethylsiloxane;

a vinyl terminated polydimethylsiloxane;

a methacrylamide-terminated polydimethylsiloxane;

an acrylamide-terminated polydimethylsiloxane;

an acrylate-terminated polydimethylsiloxane;

a methacrylate-terminated polydimethylsiloxane;

bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane;

N,N,N′

,N′

-tetrakis(3-methacryloxy-2-hydroxypropyl)-alpha,omega-bis-3-aminopropyl-polydimethylsiloxane;

a polysiloxanylalkyl(meth)acrylic monomer, or any combination thereof.

9. The method of claim 1, wherein the hydrophilic vinylic monomer comprises a hydroxyl-substituted lower alkyl (C₁ to C₃) (meth)acrylate, a hydroxyl-substituted lower alkyl vinyl ether, a C₁ to C₃ alkyl(meth)acrylamide, a di-(C₁-C₃ alkyl)(meth)acrylamide, an N-vinylpyrrole, an N-vinyl-2-pyrrolidone, a 2-vinyloxazoline, a 2-vinyl-4,4′

-dialkyloxazolin-5-one, a 2- and 4-vinylpyridine, amino(lower alkyl), a mono(lower alkylamino)(lower alkyl) and di(lower alkylamino)(lower alkyl)(meth)acrylate, an allyl alcohol, an N-vinyl C₁ to C₃ alkylamide, an N-vinyl-N—

C₁ to C₃ alkylamide, or any combination thereof.

10. The method of claim 1, wherein the hydrophilic vinylic monomer comprises N,N-dimethylacrylamide (DMA), N,N-dimethylmethacrylamide (DMMA), 2-acrylamidoglycolic acid, 3-acryloylamino-1-propanol, N-hydroxyethyl acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, 2-hydroxyethylmethacrylate (HEMA), 2-hydroxyethyl acrylate (HEA), hydroxypropyl acrylate, hydroxypropyl methacrylate (HPMA), trimethylammonium 2-hydroxy propylmethacrylate hydrochloride, aminopropyl methacrylate hydrochloride, dimethylaminoethyl methacrylate (DMAEMA), glycerol methacrylate (GMA), N-vinyl-2-pyrrolidone (NVP), allyl alcohol, vinylpyridine, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, allyl alcohol, N-vinyl caprolactam, or any combination thereof.

11. The method of claim 1, wherein the lens-forming material further comprises a hydrophobic monomer.

12. The method of claim 11, wherein the hydrophobic monomer comprises methylacrylate, ethyl-acrylate, propylacrylate, isopropylacrylate, cyclohexylacrylate, 2-ethylhexylacrylate, methylmethacrylate, ethylmethacrylate, propylmethacrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoro-isopropyl methacrylate, hexafluorobutyl methacrylate, or any combination thereof.

13. The method of claim 1, wherein the lens-forming material further comprises a crosslinker.

14. The method of claim 13, wherein the crosslinker comprises tetraethyleneglycol diacrylate, triethyleneglycol diacrylate, ethyleneglycol diacylate, diethyleneglycol diacrylate, tetraethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, ethyleneglycol dimethacylate, diethyleneglycol dimethacrylate, trimethylopropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, vinyl methacrylate, ethylenediamine dimethyacrylamide, ethylenediamine diacrylamide, glycerol dimethacrylate, triallyl isocyanurate, triallyl cyanurate, allylmethacrylate, allylmethacrylate, 1,3-bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy) disiloxane, N,N′

-methylenebisacrylamide, N,N′

-methylenebismethacrylamide, N,N′

-ethylenebisacrylamide, N,N′

-ethylenebismethacrylamide,1,3-bis(N-methacrylamido-propyl)-1,1,3,3-tetrakis-(trimethylsiloxy)disiloxane, 1,3-bis(methacrylamidobutyl)-1,1,3,3-tetrakis(trimethylsiloxy)-disiloxane, 1,3-bis(acrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane, 1,3-bis(methacryloxyethylureidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane, and combinations thereof. A preferred cross-linking agent is tetra(ethyleneglycol)diacrylate, tri(ethyleneglycol)diacrylate, ethyleneglycol diacrylate, di(ethyleneglycol)diacrylate, methylenebisacrylamide, triallyl isocyanurate, triallyl cyanurate, or any combination thereof.

15. The method of claim 1, wherein the lens-forming material further comprises a polymerization initiator, a UV-absorber, a tinting agent, an antimicrobial agent, an inhibitor, a filler, or any combination thereof.