Intraocular lenses made from polymeric compositions and monomers useful in said compositions

a polymer composition and monomer technology, applied in the field of ophthalmic lenses, can solve the problems of deformation of acrylic materials that can be quite tacky, handling problems, disadvantageous decrease in the index of refraction of the final iol optic, etc., and achieve the effect of reducing surface tackiness, reducing surface tackiness, and reducing surface tackiness

Inactive Publication Date: 2006-01-10
JOHNSON & JOHNSON SURGICAL VISION INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017]New polymeric materials and ophthalmic lenses, for example, IOLs, produced from such polymeric materials have been discovered. The present polymeric materials are derived from 2-phenylpropyl acrylate and / or 2-phenylpropyl methacrylate monomers and provide very useful optical properties in terms of optical clarity and high index of refraction and can be formed into ophthalmic lenses, for example, optics of IOLs which are effectively deformable, preferably foldable, for insertion through small surgical incisions, preferably on the order of about 3 mm or less (in maximum transverse dimension). Importantly, the present compositions and ophthalmic lenses have reduced surface tackiness without requiring the presence of fluoroacrylates, hydrophilic components and without requiring plasma treatment. By selecting the monomeric components used to produce the present compositions and ophthalmic lenses in accordance with the present invention, reduced surface tackiness is achieved with little or no adverse impact on the optical clarity, refractive index, homogeneity, biocompatability, deformability, and cost of production of such compositions and ophthalmic lenses. The present compositions and lenses can be produced using conventional techniques, e.g., conventional polymerization techniques. Thus, the present invention is very effective and easy to practice and results in polymeric compositions and ophthalmic lenses which have outstanding properties.

Problems solved by technology

Deformable IOLs made of acrylic materials can be quite tacky in nature, which tackiness inhibits deforming to a sufficiently small size for insertion through a very small incision and / or may cause handling problems..
However, such hydrophilic constituent may cause a disadvantageous decrease in the index of refraction of the final IOL optic in that some water is included within the copolymer.
However, such plasma treatment does involve an additional manufacturing step.
Also, the non-homogeneous intraocular lens which results from the surface being treated with plasma has the potential of causing problems in the eye.

Method used

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  • Intraocular lenses made from polymeric compositions and monomers useful in said compositions
  • Intraocular lenses made from polymeric compositions and monomers useful in said compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0060]Synthesis of 2-phenylpropyl methacrylate

[0061]This monomer is prepared as follows:

[0062]A two-mouth one-liter round bottom flask containing a magnetic stir bar is lowered into an ice bath on top of a magnetic stirrer. 25 grams (0.18 mol) of 2-phenyl-1-propanol is added into the flask, followed by the addition of 30 ml (0.22 mol) of triethylamine to the flask. The now empty triethylamine addition flask is rinsed with about 10-ml of anhydrous diethyl ether and this is added to the round bottom flask. Another 200 ml of anhydrous diethyl ether is added to the round bottom flask, followed by 5 mg (0.0002 mol) of inhibitor (2,5-diphenyl-p-benzophenone). The magnetic stirrer stirs the resulting mixture at 555 rpm.

[0063]100 ml of anhydrous diethyl ether and 20-ml (0.21 mol) methacryloyl chloride are added, dropwise, while the contents of the flask are maintained at about 2° C. The methacryloyl chloride addition are adjusted so that the addition is completed in about 1½ hours. The reac...

example 2

Synthesis of 2-phenylpropyl acrylate

[0066]The above monomer is prepared as in Example 1 except that acryloyl chloride replaces methacryloyl chloride on an equal molar basis.

example 3

[0067]The following formulation is blended, purged with nitrogen for 3 minutes and then cured into a crosslinked copolymer.

[0068]

Quantity% Quantity2-phenylpropyl methacrylate15.0 g33.4%2-phenylpropyl acrylate21.5 g47.9%n-hexyl acrylate 6.5 g14.5%EGDMA ethylene glycol dimethacrylate 0.9 g 2.0%thermal initiator 0.1 g 0.2%(2,5-dimethyl-2,5bis(2-ethylhexanoylperoxy) hexaneUV absorber 0.9 g 2.0%

[0069]The resulting crosslinked copolymer has an index of refraction of 1.5396, hardness (Shore A) of 42, haze (after soaking) of 3, excellent optical transparency (clarity) and good mechanical properties, including low or reduced tackiness. A one cm diameter rod of this copolymer is folded 180° with no cracking and returns to its original shape within a few seconds.

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Abstract

Ophthalmic lenses, such as intraocular lenses, include crosslinked polymeric materials having a first constituent derived from a first monomeric component selected from the group consisting of 2-phenylpropyl acrylate or methacrylate and mixtures thereof, and a second constituent derived from a second component in an amount effective as a crosslinker in the crosslinked polymeric material. The crosslinked polymeric material has branched chain alkyl groups, in an amount effective to reduce the tackiness of the crosslinked polymeric material relative to a substantially identical crosslinked polymeric material without branched chain alkyl groups.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application is a continuation in part of and claims the benefit of U.S. patent application Ser. No. 60 / 106,381 filed Oct. 29, 1998, and entitled Intraocular Lenses Made From Polymeric Compositions.BACKGROUND OF THE INVENTION[0002](1) Field of the Invention[0003]The present invention relates to ophthalmic lenses made from polymeric compositions and novel monomers useful in said compositions. More particularly, the invention relates to ophthalmic lenses, preferably deformable intraocular lenses, having reduced surface tackiness made from 2-phenylpropylacrylate and / or methacrylate-based polymeric compositions.[0004](2) Description of Related Art[0005]Intraocular lenses (IOLs) have been known for a long time, since shortly after the end of World War II. Such a lens is surgically implanted into a mammalian eye, e.g., human eye, to replace a damaged or diseased natural lens of the eye and restore the patient's vision.[0006]Although IOLs are...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): A61F2/14A61L27/16G02B1/04
CPCA61L27/16A61L2430/16G02B1/043C08L33/06
Inventor MAKKER, HARISH C.LIAO, XIUGAOWEINSCHENK, III, JOSEPH I.
Owner JOHNSON & JOHNSON SURGICAL VISION INC
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