Silicone hydrogel soft contact lens having wettable surface

• US 10,241,234 B2
• Filed: 03/11/2013
• Issued: 03/26/2019
• Est. Priority Date: 04/18/2012
• Status: Active Grant

• Current Assignee: Hoya Corporation
• Original Assignee: Hoya Corporation
• Inventors: Imafuku, Suguru
• Primary Examiner(s): Pham, Thomas K
• Assistant Examiner(s): Diedhiou, Ibrahima
• Application Number:
  US14/361,195
• Publication Number:
  US 20140362339A1
• Time in Patent Office: 2,206 Days
• Field of Search: 35115933, 35115934, 351 26, 264 11, 264 22, 264 26, 525106-108, 5253294, 5253297, 526279, 526320, 523106-107, 524261, 524916, 424429, 206 51, 514915
• CPC Class Codes: B29C 39/006 Monomers or prepolymers by reaction injection moulding B29C67/246
• CPC Class Codes: B29C 39/02 for making articles of definite length, i.e. discrete articles
• CPC Class Codes: B29K 2083/00 Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
• CPC Class Codes: B29L 2011/0041 Contact lenses
• CPC Class Codes: C08F 220/282 and containing two or more oxygen atoms
• CPC Class Codes: C08F 220/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Provided is a silicone hydrogel soft contact lens obtained by curing in a double-sided casting mold, a liquid mixture including glycerol mono(meth)acrylate and at least one type of silicone monomer having at least one hydroxyl group or polyethylene glycol group in the molecular structure thereof, the silicone hydrogel soft contact lens having a wettable surface without a polymerized lens-shaped material being subjected to post-processing to improve the water wetting properties of a surface thereof.

Claims

1. A silicone hydrogel soft contact lens, which has a wettable surface and is obtained by a process comprising:

polymerizing a mixed solution of

a first silicone monomer comprising a hydroxyl group or a polyethylene glycol group and 4 or fewer silicon atoms and a molecular weight of less than 1,000 and

a glycerol mono(meth)acrylate,

wherein, once wetted, the lens surface is uniformly covered with a water film.

2. The silicone hydrogel soft contact lens according to claim 1, wherein the first silicone monomer is represented by formula (I):

3. The silicone hydrogel soft contact lens according to claim 1, wherein the mixed solution comprises 30-70 wt. % of the first silicone monomer and 15-60 wt. % of glycerol mono(meth)acrylate.

4. The silicone hydrogel soft contact lens according to claim 1, wherein the mixed solution comprises:

(a) 30-70 wt. % of the first silicone monomer,

(b) 15-60 wt. % of glycerol mono(meth)acrylate,

(c) 0-20 wt. % of a second silicone monomer not comprising a hydroxyl group or a polyethylene glycol group,

(d) 0-50 wt. % of a hydrophilic monomer, and

(e) 0.1-1 wt. % a cross-linkable monomer.

5. The silicone hydrogel soft contact lens according to claim 4, wherein the second silicone monomer (c) is present and is at least one selected from the group consisting of tris(trimethylsiloxy)-γ

-methacryloxypropylsilane and metacryloyloxyethylsuccinic acid 3-[tris(trimethylsiloxy) silyl] propyl.

6. The silicone hydrogel soft contact lens according to claim 4, wherein the hydrophilic monomer (d) is present and is at least one selected from the group consisting of 2-hydroxyethylmethacrylate, N-vinyl-2-pyrrolidone, and methacrylic acid.

7. The silicone hydrogel soft contact lens according to claim 1, wherein the both-face cast mold is composed of polypropylene.

8. The silicone hydrogel soft contact lens according to claim 1, which has a moisture content of 20% or more and less than 50%.

11. The silicone hydrogel soft contact lens according to claim 1, wherein the mixed solution does not include a high molecular weight hydrophilic polymer that enhances surface water wettability of the silicone hydrogel soft contact lens.

9. A process for manufacturing a silicone hydrogel soft contact lens, the process comprising:

preparing a mixed solution by mixing at least one silicone monomer that comprises a hydroxyl group or polyethylene glycol group and comprises 4 or fewer silicon atoms and a molecular weight of less than 1,000 and, and a glycerol mono(meth)acrylate;

filling the mixed solution into a both-face cast mold; and

polymerizing the mixed solution in the both-face cast mold,

whereby, once wetted, the lens surface of the resultant soft contact lens is uniformly covered with a water film.

10. A process according to claim 9, which does not require applying a treatment to improve surface water wettability to a lens-shaped material after said polymerizing.

12. A process according to claim 9, wherein the mixed solution does not include a high molecular weight hydrophilic polymer that enhances surface water wettability of the silicone hydrogel soft contact lens.