Low-tack, hydrophobic ophthalmic device materials

• US 8,969,429 B2
• Filed: 02/07/2012
• Issued: 03/03/2015
• Est. Priority Date: 02/08/2011
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Laredo, Walter R., Jiang, Xuwei
• Primary Examiner(s): Seidleck, James J
• Assistant Examiner(s): Salamon, Peter A
• Application Number:
  US13/367,914
• Publication Number:
  US 20120202916A1
• Time in Patent Office: 1,120 Days
• Field of Search: None
• US Class Current: 523/107
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Disclosed are low-tack, hydrophobic, high refractive index, acrylic materials. These materials, especially useful as intraocular lens materials, contain one or more aryl acrylic hydrophobic monomers as principal device-forming monomers, a tack-reducing block copolymer additive and a glistening-reducing additive. In addition to their use as intraocular lens materials, the present materials are also suitable for use in other implantable ophthalmic devices.

Claims

1. A copolymeric ophthalmic device material formed by polymerizing a mixture comprising

a) 70% (w/w) or more of an aryl acrylic hydrophobic monomer of the formula

2. The copolymeric ophthalmic device material of claim 1 wherein the copolymeric device material has an equilibrium water content at 35°

C. of less than 4%.

3. The copolymeric device material of claim 1 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of:

benzyl acrylate;

2-phenylethyl acrylate;

2-phenoxyethyl acrylate;

4-phenylbutyl acrylate;

5-phenylpentyl acrylate;

2-benzyloxyethyl acrylate;

3-benzyloxypropyl acrylate;

3-phenylpropyl acrylate;

3-phenoxypropyl acrylate;

2-(phenylthio)propyl acrylate; and

2-(phenylthio)ethyl acrylate.

4. The copolymeric device material of claim 3 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of:

2-phenylethyl acrylate;

2-phenoxyethyl acrylate;

benzyl acrylate; and

2-(phenylthio)ethyl acrylate.

5. The copolymeric device material of claim 1 wherein for the siloxane monomer of formula 2 R² is CH₃, G is nothing or OCH₂CH(OH)CH₂, J is (CH₂)₃, and K¹, K², and K³ independently are CH₃, C₆H₅, or OSi(CH₃)₃.

6. The copolymeric device material of claim 5 wherein the siloxane monomer of formula 2 is selected from the group consisting of:

3-[tris(trimethylsilyloxy)silyl]-propyl methacrylate;

3-(methacryloxy-2-hydroxypropoxy)propylmethylbis(trimethoxy)silane;

methacryloxypropylpentamethyldisiloxane;

3-methacryloxypropylbis(trimethylsiloxy)methylsilane;

methacryloxymethyltris(trimethylsiloxy)silane;

(methacryloxymethyl)phenyl-dimethylsilane; and

(methacryloxymethyl)bis(trimethylsiloxy)methylsilane.

7. The copolymeric device material of claim 1 wherein the mixture comprises 5-25% (w/w) of the siloxane monomer of formula 2.

8. The copolymeric device material of claim 7 wherein the mixture comprises 5-15% (w/w) of the siloxane monomer of formula 2.

9. The copolymeric device material of claim 1 wherein the hydrophilic monomer is a hydroxy(C₂-C₄ alkyl)methacrylate and the mixture comprises 5-15% (w/w) of the hydrophilic monomer.

10. The copolymeric device material of claim 9 wherein the hydrophilic monomer is 2-hydroxyethyl methacrylate and the mixture comprises 8-13% (w/w) of the hydrophilic monomer.

11. The copolymeric device material of claim 1 wherein the mixture comprises 0.5-10% (w/w) of the cross-linking agent.

12. The copolymeric device material of claim 11 wherein the mixture comprises 1-3% (w/w) of the cross-linking agent and the cross-linking agent is 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;

triethylene glycol dimethacrylate; and

their corresponding acrylates.

13. The copolymeric device material of claim 12 wherein the cross-linking agent is selected from the group consisting of 1,4-butanediol dimethacrylate and triethylene glycol dimethacrylate.

14. The copolymeric device material of claim 1 wherein the mixture further comprises a reactive blue-light absorbing compound.

15. An intraocular lens comprising the copolymeric device material of claim 1.