Silicone hydrogel contact lenses with convertible comfort agents

• US 8,357,760 B2
• Filed: 07/08/2009
• Issued: 01/22/2013
• Est. Priority Date: 07/21/2008
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WANG, CHUN CHENG
• Application Number:
  US12/499,113
• Publication Number:
  US 20100016514A1
• Time in Patent Office: 1,294 Days
• Field of Search: 525/327.4, 264/1.36
• US Class Current: 525/327.4
• CPC Class Codes: B29D 11/00 Producing optical elements, e.g. lenses or prisms grinding or polishing of optical elements B24B; constructional form of optical elements G02B; optical parts of spectacles G02C7/00
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: C08F 130/08 containing silicon
• CPC Class Codes: C08F 222/06 Maleic anhydride
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 236/06 Butadiene
• CPC Class Codes: C08F 2810/20 leading to a crosslinking, either explicitly or inherently
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/00 Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 290/14 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/148 Polysiloxanes
• CPC Class Codes: C08F 299/08 from polysiloxanes
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08F 8/42 Introducing metal atoms or metal-containing groups
• CPC Class Codes: C08J 3/28 Treatment by wave energy or particle radiation
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/043 : Contact lenses

Abstract

The invention provides a silicone hydrogel contact lens including a hydrolyzable polymer. The hydrolyzable polymer can be converted by hydrolysis into a hydrophilic polymer which is capable of imparting the silicone hydrogel contact lens a hydrophilic surface without post-curing surface treatment.

Claims

1. A silicone hydrogel contact lens, comprising:

a silicone hydrogel material, wherein the silicone hydrogel material is obtained by polymerizing a lens-forming material including (1) at least one silicone-containing monomer, at least one silicone-containing macromer, at least one silicone-containing prepolymer, or combination thereof and (2) a first hydrolyzable polymer without actinically-crosslinkable groups, a second hydrolyzable polymer with one sole actinically- crosslinkable group, or combination thereof; and

a first hydrophilic polymer and/or a second hydrophilic polymer, wherein the first and second hydrolyzable polymers are selected from the group consisting of hydroxylpropylmethylcellulose phthalate (HPMCP), cellulose acetate phthalate (CAP), poly(butadiene/maleic anhydride), and combination thereof, wherein the first and second hydrophilic polymers independent of each other are derived by converting the first or second hydrolyzable polymer in the obtained silicone hydrogel material to the hydrophilic polymer through hydrolysis, wherein the first or second hydrophilic polymer in the silicone hydrogel material is capable of imparting the silicone hydrogel contact lens a hydrophilic surface without post-curing surface treatment.

2. The silicone hydrogel contact lens of claim 1, wherein the first hydrolyzable polymer has a number-average molecular weight of from about 5,000 to about 1,000,000 daltons, wherein the second hydrolyzable polymer has a number-average molecular weight of from about 500 to about 20,000 daltons.

3. The silicone hydrogel contact lens of claim 2, wherein the first hydrolyzable polymer is poly(butadiene/maleic anhydride).

4. The silicone hydrogel contact lens of claim 2, wherein the first or second hydrolyzable polymer is hydrolyzed into the hydrophilic polymer in a primary package containing the silicone hydrogel contact lens during autoclave.

5. The silicone hydrogel contact lens of claim 2, wherein the silicone hydrogel contact lens has at least one property selected from the group consisting of an oxygen permeability of at least about 40 barrers, from about 0.3 MPa to about 1.5 MPa, an ion permeability characterized by an lonoflux Diffusion Coefficient, D, of at least about 1.5×

10<sup>−

6</sup> mm²/min, a water content of from about 15% to about 60%, a surface hydrophilicity characterized by having an averaged water contact angle of about 90 degrees or less, and combination thereof.

6. The silicone hydrogel contact lens of claim 2, wherein the lens-forming material comprises at least one hydrophilic vinylic monomer selected from the group consisting of N,N-dimethylacrylamide (DMA), 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), dimethylaminoethylmethacrylamide, acrylamide, methacrylamide, allyl alcohol, vinylpyridine, N-(1,1dimethyl-3-oxobutyl)acrylamide, acrylic acid, a C₁-C₄-alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of from 200 to 1500, methacrylic acid, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, and N-vinyl caprolactam.

7. The silicone hydrogel contact lens of claim 2, wherein the lens-forming material comprises at least one hydrophobic vinylic monomer selected from the group consisting of methylacrylate, ethyl-acrylate, propylacrylate, isopropylacrylate, cyclohexylacrylate, 2-ethylhexylacrylate, methylmethacrylate, ethyl methacrylate, 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, tris-trimethylsilyloxy-silyl-propyl methacrylate, 3-methacryloxypropyl-pentamethyl-disiloxane and bis(methacryloxypropy)-tetramethyl-disiloxane.

8. The silicone hydrogel contact lens of claim 2, wherein the lens-forming material comprises at least one member selected from the group consisting of an antimicrobial agent, a cross-linking agent, a chain transfer agent, an initiator, a UV-absorbers, a visibility tinting agent, and a mixture thereof.

9. The silicone hydrogel contact lens of claim 1, wherein the lens-forming material comprises a second hydrolyzable polymer with one sole crosslinkable group, wherein the second hydrophilic polymer is covalently anchored to the polymer matrix of the silicone hydrogel material, wherein the second hydrophilic polymer is derived from the second hydrolyzable polymer by converting the second hydrolyzable polymer in the obtained silicone hydrogel material to the second hydrophilic polymer through hydrolysis, wherein the second hydrophilic polymer in the silicone hydrogel material is capable of imparting the silicone hydrogel contact lens a hydrophilic surface without post-curing surface treatment.

10. The silicone hydrogel contact lens of claim 1, wherein the lens-forming material comprises a first hydrolyzable polymer with one sole crosslinkable group, wherein the first hydrophilic polymer is derived from the first hydrolyzable polymer by converting the first hydrolyzable polymer in the obtained silicone hydrogel material to the first hydrophilic polymer through hydrolysis, wherein the first hydrophilic polymer in the silicone hydrogel material is capable of imparting the silicone hydrogel contact lens a hydrophilic surface without post-curing surface treatment.