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  Process for making silicone intraocular lens with blue light absorption propertiesUSPTO Application #: 20060020338Title: Process for making silicone intraocular lens with blue light absorption properties Abstract: A process for producing silicone intraocular lenses (IOLs) capable of absorbing blue light. Intraocular lenses so produced block blue light from reaching the retina of an eye implanted with the IOL. By blocking blue light from reaching the retina, the IOL thereby prevents potential damage to the retina. (end of abstract) Agent: Bausch & Lomb Incorporated - Rochester, NY, US Inventors: Yu-Chin Lai, Dominic V. Ruscio USPTO Applicaton #: 20060020338 - Class: 623006110 (USPTO) Related Patent Categories: Prosthesis (i.e., Artificial Body Members), Parts Thereof, Or Aids And Accessories Therefor, Eye Prosthesis (e.g., Lens Or Corneal Implant, Or Artificial Eye, Etc.), Intraocular Lens The Patent Description & Claims data below is from USPTO Patent Application 20060020338. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS-REFERENCE OF RELATED APPLICATION [0001] This application is a divisional of Ser. No. 10/657,781 filed Sep. 8, 2003. FIELD OF THE INVENTION [0002] The present invention relates to a process for making silicone intraocular lenses with blue light absorption properties. More particularly, the present invention relates to a process for reacting a silicone intraocular lens with an ethyleneically unsaturated yellow dye to produce an intraocular lens capable of blocking blue light. BACKGROUND OF THE INVENTION [0003] Since the 1940's optical devices in the form of intraocular lens (IOL) implants have been utilized as replacements for diseased or damaged natural ocular lenses. In most cases, an intraocular lens is implanted within an eye at the time of surgically removing the diseased or damaged natural lens, such as for example, in the case of cataracts. For decades, the preferred material for fabricating such intraocular lens implants was poly(methyl methacrylate), which is a rigid, glassy polymer. [0004] Softer, more flexible IOL implants have gained in popularity in more recent years due to their ability to be compressed, folded, rolled or otherwise deformed. Such softer IOL implants may be deformed prior to insertion thereof through an incision in the cornea of an eye. Following insertion of the IOL in an eye, the IOL returns to its original pre-deformed shape due to the memory characteristics of the soft material. Softer, more flexible IOL implants as just described may be implanted into an eye through an incision that is much smaller, i.e., less than 4.0 mm, than that necessary for more rigid IOLs, i.e., 5.5 to 7.0 mm. A larger incision is necessary for more rigid IOL implants because the lens must be inserted through an incision in the cornea slightly larger than the diameter of the inflexible IOL optic portion. Accordingly, more rigid IOL implants have become less popular in the market since larger incisions have been found to be associated with an increased incidence of postoperative complications, such as induced astigmatism. [0005] With recent advances in small-incision cataract surgery, increased emphasis has been placed on developing soft, foldable materials suitable for use in artificial IOL implants. Mazzocco, U.S. Pat. No. 4,573,998, discloses a deformable intraocular lens that can be rolled, folded or stretched to fit through a relatively small incision. The deformable lens is inserted while it is held in its distorted configuration, then released inside the chamber of the eye, whereupon the elastic property of the lens causes it to resume its molded shape. As suitable materials for the deformable lens, Mazzocco discloses polyurethane elastomers, silicone elastomers, hydrogel polymer compounds, organic or synthetic gel compounds and combinations thereof. [0006] In recent years, blue light (400-500 nm) has been recognized as being potentially hazardous to the retina. Accordingly, yellow dyes to block blue light have been used in foldable intraocular lenses, in conjunction with ultraviolet light absorbers, to avoid potential damaging effects. Freeman et al., U.S. Pat. No. 6,353,069, disclose high refractive index copolymers comprising two or more acrylate and/or methacrylate monomers with aromatic groups. Ophthalmic devices made of the copolymers may also include colored dyes, such as the yellow dyes disclosed in U.S. Pat. No. 5,470,932. Such materials exhibit sufficient strength to allow devices made of them, such as intraocular lenses, to be folded or manipulated without fracturing. [0007] Because of shortcomings in the properties of many soft, flexible materials used in the manufacture of ophthalmic devices, such as the formation of water vacuoles or "glistenings", and low refractive index, which requires a lens to be relatively thick in order to provide a lens of proper refractive power, new materials and methods of manufacturing of ophthalmic devices are needed. SUMMARY OF THE INVENTION [0008] Soft, foldable, high refractive index, silicone intraocular lenses (IOLs) capable of absorbing blue light are prepared in accordance with the present invention through a coating process using a reactive yellow dye solution having blue light blocking properties. The blue light absorbing IOLs produced in accordance with the present invention protect an eye's retina from potentially damaging blue light and thereby possibly providing protection from macular degeneration. [0009] Blue light blocking silicone IOLs of the present invention are produced by exposing a semi-finished silicone IOL to an ethyleneically unsaturated yellow dye-containing solution and allowing the same to undergo a hydrosilation reaction. Such production process yields silicone IOLs with blue light absorbing properties. By absorbing blue light, the IOL serves to block blue light from reaching and potentially damaging the retina of an eye implanted with the IOL. Silicone IOLs so produced are transparent, relatively high in elongation and relatively high in refractive index. [0010] Accordingly, it is an object of the present invention to provide a process for the production of silicone IOLs capable of absorbing blue light. [0011] Another object of the present invention is to provide a process for the production of silicone IOLs having relatively high refractive indices and good clarity. [0012] Another object of the present invention is to provide a process for the production of silicone IOLs that are flexible. [0013] Still another object of the present invention is to provide biocompatible silicone IOLs capable of absorbing blue light. [0014] These and other objectives and advantages of the present invention, some of which are specifically described and others that are not, will become apparent from the detailed description and claims that follow. DETAILED DESCRIPTION OF THE INVENTION [0015] The present invention relates to a novel process for the production of high refractive index silicone IOLs capable of absorbing blue light and thereby blocking blue light from reaching the retina of an eye implanted with the IOL. Silicone IOLs of the present invention are produced by allowing a semi-finished silicone IOL to react with an ethyleneically unsaturated dye through a hydrosilation reaction. The subject process for treating silicone IOLs is relatively simple and produces biocompatible silicone IOLs capable of absorbing blue light. [0016] A "semi-finished" silicone IOL for purposes of the present invention, is a silicone IOL having free hydrosilyl groups. By dipping a semi-finished silicone IOL in a weak solvent, such as for example but not limited to methylene chloride, containing a one or more reactive dyes, such as a reactive yellow dye, and one or more platinum catalysts, followed by thermal treatment of the IOL in an oven at a low temperature, preferably less than approximately 100.degree. C. for a relatively short period of time, preferably less than several hours and more preferably less than approximately 30 minutes, a quantitative amount of dye can be incorporated into or coat the IOL. There are several platinum catalysts or catalyst systems suitable for the hydrosilation reaction of the present invention, depending on the reaction temperature and kinetics desired. For example, platinum (3 to 3.5%)-divinyltetramethyldisiloxane complex is suitable for use in a room temperature reaction. Platinum (3 to 3.5%)-cyclovinylmethylsiloxane complex is suitable for use in a reaction at a moderate temperature of 50 to 100.degree. C. The reaction kinetics can be regulated through the concentration of the catalyst and through the addition of various amounts of one or more inhibitors. Suitable inhibitors include for example but are not limited to 1,3-divinyltetramethyldisiloxane and 1,3,5,7-tetramethyl-1,3,5,7-tetravin- yl cyclosiloxane. Such inhibitors may be present in the catalyst complex. The chemical reaction that takes place as a result of this process is illustrated below in Reaction Scheme 1. As depicted above in Reaction Scheme 1, Si--H represents the free hydrosilyl groups of a "semi-finished" silicone IOL, and H.sub.2C.dbd.CR.sub.1R.sub.2 represents a reactive yellow dye. Here, R.sub.1 can be H or CH.sub.3 and R.sub.2 is a group containing other functional groups as well as functional groups responsible for yellow color. The reactive yellow dye can have for example, but is not limited to the following ethylenically unsaturated groups: vinyl, allyl, acrylate, methacrylate, acrylamide, methacrylamide, fumarate, maleate, itaconate, styrene, nitrile and the like. Depending on the particular solvent and the concentration of reactive yellow dyes in the solvent, the reactive yellow dye can penetrate into the polymer matrix of the lens body, as well as, partially or completely coat the lens surface. [0017] Reactive dyes useful in the manufacture of flexible, high refractive index silicone IOLs capable of absorbing blue light, may be prepared through a process of multiple chemical reaction steps. This process includes a step for forming a blue light absorbing functional group, i.e., a dye, such as for example but not limited to a diazo coupling for azo dye formation. The process also includes a step to incorporate the compound with a dye functional group and a reagent that is ethylenically unsaturated. For example, a reactive azo yellow dye having two ethylenically unsaturated groups can be prepared by reacting a yellow dye having two alcohol groups with an acid chloride or an isocyanate having an ethylenically unsaturated group. Such is depicted in Reaction Schemes 2 through 3 wherein a yellow dye, N,N-bis-(2-hydroxyethyl)-(4-phenylazo) aniline (Solvent Yellow 58), synthesized in accordance with the procedure of Example 1 below, is used as an example not intended to be limiting. [0018] Here, "Ph" represents either C.sub.6H.sub.5 or C.sub.6H.sub.4, as appropriate. Alternatively, a reactive yellow dye with one ethylenically unsaturated group useful in accordance with the present invention, such as for example but not limited to N-2-[3'-(2''-methylphen- ylazo)-4'-hydroxyphenyl]ethyl vinylacetamide, represented below in Formula 1, can be prepared by first reacting vinylacetyl chloride with 4-aminoethylphenol to give 4-vinylacetamidoethyl phenol, which is then coupled with the diazonium salt of toluidine as described in more detail below in Example 4. [0019] The process of the present invention for preparing flexible, high refractive index silicone IOLs with blue light absorption properties is described in still greater detail in the Examples provided below. Continue reading... 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