Methods for increasing the ion permeability of contact lenses

• US 8,883,051 B2
• Filed: 12/06/2010
• Issued: 11/11/2014
• Est. Priority Date: 12/07/2009
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing, Qian, Xinming
• Primary Examiner(s): ABRAHAM, AMJAD A
• Application Number:
  US12/960,612
• Publication Number:
  US 20110133350A1
• Time in Patent Office: 1,436 Days
• Field of Search: 264/1.1, 264/2.7
• US Class Current: 264/1.32
• 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, (iii) two ion-permeability-enhancing vinylic monomers or macromers which are two polyethylene glycol methacrylates which have a polyethylene glycol chain having a molecular weight of 500 to 2,500 and are different from each other in molecular weight, wherein each of the two polyethylene glycol methacrylates is obtained by reacting a monofunctional terminated polyethylene glycol having one first functional group selected from the group consisting of amino, hydroxyl, acid chloride, and epoxy group at one terminus and a methoxy or ethoxy group at the other terminus of the monofunctional terminated polyethylene glycol, with a vinylic monomer having a second functional group coreactive with the first functional group and selected from the group consisting of isocyanate, amino, epoxy, hydroxyl, acid chloride, azlactone, and thiol group; and

a crosslinking agent from about 0.05% to about 4% by weight

b. curing the lens-forming material to produce the lens; and

c. removing the lens from the mold, wherein the two polyethylene glycol methacrylates are present from about 0.5% to about 2.5% by weight and sufficient to provide the resultant lens with an increased ion permeability compared to a control lens while not significantly altering the water content

and the oxygen permeability of the resultant lens as characterized by having changes in water content and oxygen permeability being less than about 8% relative to the control lens, wherein the control lens is produced from a control formulation having identical concentrations of all polymerizable components but without any polyethylene glycol methacrylate, wherein the lens has an ion permeability that is at least 40% greater than the control lens.

2. 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.

3. 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.

4. 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.

5. 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.

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

7. The method of claim 6, 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.

8. The method of claim 1, 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.

9. 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.