Method of preparing foldable high refractive index acrylic ophthalmic device materials

• US 5,891,931 A
• Filed: 08/07/1997
• Issued: 04/06/1999
• Est. Priority Date: 08/07/1997
• Status: Expired due to Term

• Current Assignee: Alcon Research Limited (Nestle SA)
• Original Assignee: Alcon Laboratories Incorporated (Alcon Incorporated)
• Inventors: Karakelle, Mutlu, Leboeuf, Albert R.
• Primary Examiner(s): Nutter, Nathan M.
• Application Number:
  US08/908,229
• Time in Patent Office: 607 Days
• Field of Search: 522/64, 522/26, 522/28, 522/182
• US Class Current: 522/64
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Foldable, acrylic, high refractive index ophthalmic device materials containing a UV absorbing chromophore are cured by exposure to blue light using a benzoylphosphine oxide photoinitiator.

Claims

1. A method of preparing a foldable, acrylic, high refractive index, copolymeric, ophthalmic device material comprising the steps of:

a) preparing a mixture comprising a benzoylphosphine oxide photoinitiator, a UV-absorbing chromophore and one or more monomers having the structure (I) ##STR2## where X is H or CH₃ ;

m is 0-10;

Y is a single bond, O, S, or NR wherein R is H, CH₃, C_n H_2n+1 (n=1-10) iso OC₃ H₇, C₆ H₅, or CH₂ C₆ H₅ ; and

Ar is any aromatic ring which can be unsubstituted or substituted with H, CH₃, C₂ H₅, n-C₃ H₇, iso-C₃ H₇, OCH₃, C₆ H₁₁, Cl, Br, C₆ H₅, or CH₂ C₆ H₅ ; and

b) exposing the mixture to a blue-light source for a period of time sufficient to cure the copolymeric material.

2. The method of claim 1 wherein the monomer of structure (I) is selected from the group consisting of:

2-phenoxyethyl acrylate;

2-phenylethylthio acrylate;

2-phenylethylamino acrylate;

phenyl acrylate;

benzyl acrylate;

2-phenylethyl acrylate;

3-phenylpropyl acrylate;

4-phenylbutyl acrylate;

4-methylphenyl acrylate;

4-methylbenzyl acrylate;

2-2-methylphenylethyl acrylate;

2-3-methylphenylethyl acrylate;

2-4-methylphenylethyl acrylate; and

their corresponding methacrylates.

3. The method of claim 1 wherein X is H;

m is 2-4;

Y is nothing or O; and

Ar is phenyl.

4. The method of claim 3 wherein the monomer of structure (I) is selected from he group consisting of:

2-phenylethyl acrylate;

2-phenoxyethyl acrylate;

3-phenylpropyl acrylate;

3-phenoxypropyl acrylate;

4-phenylbutyl acrylate; and

4-phenoxybutyl acrylate.

5. The method of claim 1 wherein the copolymeric material has a glass transition temperature no greater than 25°

C. and an elongation of at least 150%.

6. The method of claim 1 wherein the total amount of monomer of structure (I) present in the copolymeric material is at least 50% (w/w).

7. The method of claim 6 wherein the total amount of monomer of structure (I) present in the copolymeric material is at least 70% (w/w).

8. The method of claim 7 wherein the total amount of monomer of structure (I) present in the copolymeric material is at least 80% (w/w).

9. The method of claim 6 wherein the mixture further comprises one or more additional monomers selected from the group consisting of:

C₁ -C₈ alkylacrylates;

C₁ -C₈ cycloalkylacrylates;

N-alkylacrylamides (where alkyl=C₁ -C₄);

phenoxyalkylacrylates (where alkyl=C₁ -C₈);

glycerylacrylate;

polyethyleneoxide mono- and diacrylates;

2-hydroxyethylacrylate;

C₁ -C₈ alkylmethacrylates;

C₁ -C₈ cycloalkylmethacrylates;

N-alkylmethacrylamides (where alkyl=C₁ -C₄);

phenoxyalkylmethacrylates (where alkyl=C₁ -C₈);

glycerylmethacrylate;

polyethyleneoxide mono- and dimethacrylates;

2-hydroxyethylmethacrylate; and

N-vinylpyrrolidone.

11. The method of claim 1 wherein the benzoylphosphine oxide initiator is selected from the group consisting of:

2,4,6-trimethyl-benzoyidiphenylophosphine oxide;

bis-(2,6-dichlorobenzoyl)-4-N-propylphenyl-phosphine oxide; and

bis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide.

12. The method of claim 11 wherein the benzoylphosphine oxide initiator is 2,4,6-trimethyl-benzoyldiphenylophosphine oxide.

13. The method of claim 1 wherein the amount of benzoylphosphine oxide initiator is less than about 3% (w/w).

14. The method of claim 13 wherein the amount of benzoylphosphine oxide initiator is about 1% (w/w).

15. The method of claim 1 wherein the mixture further comprises one or more copolymerizable cross-linking monomers.

16. The method of claim 1 wherein the blue-light source has an intensity of from about 1 to about 40 mW/cm² and the period of time in which the mixture is exposed to the blue-light source is from about 5 minutes to about 4 hours.

17. The method of claim 1 wherein the blue-light source has an intensity of from about 10 to about 15 mW/cm².

18. The method of claim 1 wherein the mixture comprises 2-phenylethyl acrylate and 2-phenylethyl methacrylate.

19. The method of claim 1 wherein the mixture comprises 2-phenylethyl acrylate and 2-hydroxyethyl methacrylate.

20. The method of claim 1 wherein the mixture comprises phenoxyethyl acrylate and N-hexyl acrylate.

10. The method of claim 10 wherein the total amount of additional monomer is 45% (w/w) or less.