Silicone hydrogel lenses with water-rich surfaces

Patent metadata

Field	Value
Publication number	US-10131815-B2
Application number	US-201715730773-A
Country	US
Kind code	B2
Filing date	Oct 12, 2017
Priority date	Jul 30, 2010
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The invention is related to a hydrated silicone hydrogel contact lens having a layered structural configuration: a lower water content silicone hydrogel core (or bulk material) completely covered with a layer of a higher water content hydrogel totally or substantially free of silicone. A hydrated silicone hydrogel contact lens of the invention possesses high oxygen permeability for maintaining the corneal health and a soft, water-rich, lubricious surface for wearing comfort.

First claim

What is claimed is:

1. A silicone hydrogel contact lens, comprising:
a silicone hydrogel bulk material covered with an outer surface hydrogel layer having a thickness of at least about 0.1 μm,
wherein the silicone hydrogel bulk material comprises (i) repeating units derived from a silicone-containing vinylic monomer, a silicone-containing vinylic macromer, a silicone-containing prepolymer, or combinations thereof, and (ii) repeating units derived from a hydrophilic vinylic monomer, and has a first water content, designated as WC siHy , of from about 10% to about 70% by weight when being fully hydrated,
wherein the outer surface hydrogel layer comprises poly(ethylene glycol) chains which are designated as PEG chains, and
wherein the outer surface hydrogel layer has a second water content higher than WC siHy and a water-swelling ratio of (a) at least about 150% if WC siHy ≤45% or (b) at least

130
·

WC
SiHy

1
-

WC
SiHy

⁢
%

if WC siHy >45% when being fully hydrated.

2. The silicone hydrogel contact lens of claim 1 , wherein the outer surface hydrogel layer has a water-swelling ratio of at least about 200%.

3. The silicone hydrogel contact lens of claim 2 , wherein the outer surface hydrogel layer has a thickness of from about 0.25 μm to about 15 μm.

4. The silicone hydrogel contact lens of claim 2 , wherein the outer surface hydrogel layer has a thickness of from about 0.25 μm to about 15 μm.

5. The silicone hydrogel contact lens of claim 1 , wherein the outer surface hydrogel layer has a thickness of from about 0.5 μm to about 12.5 μm.

6. The silicone hydrogel contact lens of claim 5 , wherein the outer surface hydrogel layer has a water-swelling ratio of at least about 200%.

7. The silicone hydrogel contact lens of claim 1 , wherein the outer surface hydrogel layer has a thickness of from about 1 μm to about 10 μm.

8. The silicone hydrogel contact lens of claim 7 , wherein the outer surface hydrogel layer has a water-swelling ratio of at least about 200%.

9. The silicone hydrogel contact lens of claim 1 , wherein the PEG chains which are derived from at least one member selected from the group consisting of: PEG-NH 2 ; PEG-SH; PEG-COOH; H 2 N-PEG-NH 2 ; HOOC-PEG-COOH; HS-PEG-SH; H 2 N-PEG-COOH; HOOC-PEG-SH; H 2 N-PEG-SH; a multi-arm PEG with one or more amino, carboxyl or thiol groups; a PEG dendrimer with one or more amino, carboxyl or thiol groups; and combinations thereof.

10. The silicone hydrogel contact lens of claim 9 wherein the silicone hydrogel bulk material comprises repeating units derived from a silicone-containing vinylic monomer selected from the group consisting of 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, trimethylsilylmethyl vinyl carbonate, and combinations thereof.

11. The silicone hydrogel contact lens of claim 9 , wherein the silicone hydrogel bulk material comprises: (i) repeating units derived from a polysiloxane vinylic monomer, a polysiloxane vinylic macromer, or combinations thereof; and (ii) repeating units derived from a hydrophilic vinylic monomer selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, 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, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, trimethylammonium 2-hydroxy propylmethacrylate hydrochloride, aminopropyl methacrylate hydrochloride, dimethylaminoethyl methacrylate, glycerol methacrylate, N-vinyl-2-pyrrolidone, allyl alcohol, vinylpyridine, a C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N-vinyl caprolactam, and mixtures thereof.

12. The silicone hydrogel contact lens of claim 11 , wherein the silicone hydrogel bulk material further comprises repeating units derived from a crosslinking agent.

13. The silicone hydrogel contact lens of claim 12 , wherein the crosslinking agent is selected from the group consisting of 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,

Assignees

• Novartis Ag

Inventors

• Qiu Yongxing
• Pruitt John Dallas
• Thekveli Sibichen J
• Tucker Robert Carey
• Nelson Jared

Classifications

• B29D11/00067 Primary

  Hydrating contact lenses · CPC title

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C08J7/042

  with two or more layers, where at least one layer of a composition contains a polymer binder · CPC title

• C09D133/02

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title