Low-tack ophthalmic and otorhinolaryngological device materials

• US 7,585,900 B2
• Filed: 07/20/2007
• Issued: 09/08/2009
• Est. Priority Date: 07/21/2006
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Alcon Incorporated
• Inventors: Schlueter, Douglas C., Karakelle, Mutlu, Weinschenk, Joseph I. III, Cordova, Diana M., Lehman, Chance
• Primary Examiner(s): Eashoo; Mark
• Assistant Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US11/780,649
• Publication Number:
  US 20080021129A1
• Time in Patent Office: 781 Days
• Field of Search: 523/106, 523/107, 526/259, 526/279, 526/319, 526/321, 526/326, 526/323.1, 526/323.2, 623/6.11, 623/6.59, 351/160.R
• US Class Current: 523/107
• CPC Class Codes: A61F 2/14 Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
• CPC Class Codes: A61F 2/142 Cornea, e.g. artificial corneae, keratoprostheses or corneal implants for repair of defective corneal tissue
• CPC Class Codes: A61F 2/16 Intraocular lenses
• CPC Class Codes: A61F 2/1616 Pseudo-accommodative, e.g. multifocal or enabling monovision
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/00 Materials for grafts or prostheses or for coating grafts or prostheses dental prostheses A61C13/00; shape or structure of prostheses A61F2/00; use of preparations for artificial teeth A61K6/80; artificial kidneys A61M1/14
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters

Abstract

Disclosed are soft, high refractive index, acrylic materials. These materials, especially useful as intraocular lens materials, contain an aryl acrylic hydrophobic monomer as the single principal device-forming monomer and a tack-reducing macromer additive. In addition to their use as intraocular lens materials, the present materials are also suitable for use in other ophthalmic or otorhinolaryngological devices, such as contact lenses, keratoprostheses, corneal inlays or rings; otological ventilation tubes and nasal implants.

Claims

1. A polymeric ophthalmic or otorhinolaryngological device material comprising

a) a principal device-forming monomer which is an aryl acrylic hydrophobic monomer of the formula

2. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein A is CH₃, B is (CH₂)_m, m is 2-5, Y is nothing or O, w is 0-1, and D is H.

3. The polymeric ophthalmic or otorhinolaryngological device material of claim 2 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of 4-phenylbutyl methacrylate;

5-phenylpentyl methacrylate;

2-benzyloxyethyl methacrylate; and

3-benzyloxypropyl methacrylate.

4. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 further comprising one or more components selected from the group consisting of reactive UV absorbers and reactive blue-light absorbers.

5. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the dimethylacryloxypropyl-terminated polydimethylsiloxane macromer is present in an amount from 0.5-2% (w/w).

6. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the dimethylacryloxypropyl-terminated polydimethylsiloxane macromer is present in an amount from 0.8-1.2% (w/w).

7. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein R₁═

R₂═

CH₃;

R₃ is H, CH₃, or CH₂CH₃;

z=3; and

x=0-22.

8. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein x =5-14.

9. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein x=2-5.

10. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material is an ophthalmic device material and has a refractive index of at least 1.50.

11. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material has a Tg less than about +15°

C.

12. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the material has an elongation of at least 90%.

13. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the cross-linking component comprises one or more cross-linking agents selected from the group consisting of ethylene glycol dimethacrylate;

diethylene glycol dimethacrylate;

allyl methacrylate;

1,3-propanediol dimethacrylate;

2,3-propanediol dimethacrylate;

1,6-hexanediol dimethacrylate;

1,4-butanediol dimethacrylate;

CH₂═

C(CH₃)C(═

O)O—

(CH₂CH₂O)_p—

C(═

O)C(CH₃)═

CH₂ where p=1-50;

CH₂═

C(CH₃)C(═

O)O(CH₂)_tOC(═

O)C(CH₃)═

CH₂ where t=3-20; and

their corresponding acrylates.

14. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the principal device-forming monomer is present in an amount of at least about 80% (w/w).

15. The polymeric ophthalmic or otorhinolaryngological device material of claim 1 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of 4-phenylbutyl methacrylate;

5-phenylpentyl methacrylate;

2-benzyloxyethyl methacrylate; and

3-benzyloxypropyl methacrylate; and

the cross-linking monomer is CH₂═

C(CH₃)C(═

O)O—

(CH₂CH₂O)_p—

C(═

O)C(CH₃)═

CH₂, where p is such that the number average molecular weight of the cross-linking monomer is about 1000.

16. An intraocular lens optic comprising the polymeric device material of claim 1

17. A device comprising the device material of claim 1 wherein the device is selected from the group consisting of a contact lens;

a keratoprosthesis, a corneal inlay or ring;

an otological ventilation tube; and

a nasal implant.