WO2012099555A2 - Cosmetic contact lenses having a sparkle effect - Google Patents
Cosmetic contact lenses having a sparkle effect Download PDFInfo
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- WO2012099555A2 WO2012099555A2 PCT/US2008/087876 US2008087876W WO2012099555A2 WO 2012099555 A2 WO2012099555 A2 WO 2012099555A2 US 2008087876 W US2008087876 W US 2008087876W WO 2012099555 A2 WO2012099555 A2 WO 2012099555A2
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- WIPO (PCT)
- Prior art keywords
- lens
- sparkle
- additive
- sparkle additive
- additive composition
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/046—Contact lenses having an iris pattern
Definitions
- the invention relates to contact lenses having a sparkle effect and sparkle additives useful in the production of cosmetic contact lenses.
- the invention is directed to sparkle additives that use interference particles to provide a sparkle effect to the lenses.
- cosmetic contact lenses to alter or augment the natural color of the iris is well known.
- Colorants used in cosmetic lenses generally are prepared with binding polymer to form a colorant mix.
- a variety of pigments are commercially available for use in the production of tinted contact lens.
- the cosmetic lenses use either or both opaque and translucent colors to change the color of an iris, as for example, from brown to blue.
- cosmetic lenses have been manufactured that attempt to enhance the eye to produce a more striking appearance so as to draw attention to the eye with or without changing the color of the iris.
- colorants that incorporate pigments capable of producing a pearl-type luster, phosphorescent pigments to produce a glow-effect, pigments with reflective material and the like are known.
- One aspect of the invention is a contact lens incorporating sparkle additives that produce a sparkle effect when the lens is viewed on-eye.
- the sparkle effect is produced while, at the same time, maintaining the natural appearance of the eye.
- contact lenses having sparkle effect exhibit a sparkle density value (p) that is greater than about 0.5 count/mm 2 .
- contact lenses having sparkle effect include sparkle particles that are randomly distributed within the area in the lens in which they are dispersed.
- contact lenses having a sparkle effect have a K sp greater than 0.25.
- contact lenses with sparkle effect have greater than about 0.5 to about 50 wt% cholesteric liquid crystal particles based on the total weight of sparkle additive composition (including binder, sparkle particle additive, and solvent).
- contact lenses with sparkle effect comprise cholesteric liquid crystal particles and one or more organic or inorganic pigments.
- a sparkle-effect may be obtained when the lens is observed on-eye.
- the additives useful in the invention are cholesteric liquid crystal particles, which are transparent platelets of an organic polymer network with a helical liquid crystal structure. Unlike interference systems, such as an interference stack, in which a cosmetic effect is obtained by light reflection through multiple layers, the cholesteric liquid crystal particles provide a cosmetic effect, sparkle effect and/or color change by transmission and reflection of light by a layer of material.
- Cholesteric liquid crystal particles useful in the invention are those that are suitable for incorporation into the lens material, can be used with the desired printing technology, such as pad-printing, ink-jet printing and the like, and are of a particle size for use in contact lenses.
- Examples of commercially available particles useful in the invention include, without limitation, HELICONE® additives available from LCP Technology GmbH, Burghausen, Germany.
- the sparkle effect observed in the practice of this invention can be subjectively observed when lenses that incorporate the sparkle additive compositions of this invention are worn on-eye or on devices used to simulate eyes.
- Lenses so made have an appearance described as glittery, twinkly, pixie dust, brightening/lightening, sparkly, luminescent, wet, moist, fresh, awake, energetic, lively, vivacious, and alert.
- the sparkle effect is quantified by reference to a number of sparkle factors including reflective properties and the randomness of the pattern of sparkle additive particles in the contact lens.
- the lenses of the invention exhibit greater than 35 points of reflection (or sparkle count) and most preferably they are greater than 45 when measured as described below.
- An additional sparkle effect factor is the area of the coverage of the particles. Indexing the number of reflective points (sparkle count) to the area in which the sparkle additive is applied is the most preferred component for assessing sparkle effect.
- Sparkle occurs when p > about 0.5 count/mm 2 , preferably it is greater than about 1 count/mm 2 , and most preferably it is greater than about 4 count/mm 2 .
- An additional sparkle effect factor is the degree of randomness of the pattern of particles in the lens.
- a random distribution of particles of the invention results in a natural sparkle effect whereas non-random distributions do not. Non-random distributions do not look natural. This is expressed as a k sp value (measured as described below) and is calculated with respect to the brightness or intensity of the main peak of a Fourier Transform of an illuminated lens, Ic and brightest secondary peak I s as follows:
- k sp it can be seen that if the secondary peak is as bright as the main peak, then k sp will be equal to zero. Conversely, if the secondary peak is zero, then k sp will be equal to one. Lenses having ksp values greater than 0.55 and preferably approaching 1 have sufficient randomness for exhibiting a natural sparkle effect.
- sparkle densities (p) of greater than about 0.5 count/mm 2 , preferably it is greater than about 1 count/mm 2 , and most preferably it is greater than about 4 count/mm 2 with randomness factor k sp values greater than 0.55 and preferably approaching 1.
- Sparkle effect can be observed by illuminating the lens, imaging the illuminated lens, and then analyzing the image to determine the sparkle effect factors. This is best done with a high resolution CCD camera affixed to a stabilized platform.
- the CCD camera is preferably at a distance of 97 +/-3 mm with the zoom on its lowest setting.
- the lenses are placed on a lens holder that is curved (with all air bubbles between the contact and the lens holder eliminated and all folds, wrinkles, or other features that may cause glare or shadows removed).
- the lenses are periodically moistened throughout the process, preferably with artificial tear solution (such as Prestige Brand Sterile Artifical Tears Lubricant Eye Drops) or saline solution (such as Target store brand Saline Solution for Sensitive Eyes). Ambient light is reduced as much as possible. Multiple images (preferably about ten) of the lens with light cast upon it are taken by rotating 30° +/- 5° between pictures and moistening with saline solution as needed. Exposure time is preferably about 600ms.
- the lens and lens holder is illuminated with a light source such as a DC-950 Fiber Lite (produced by Dolan-Jenner Industries of 159 Swanson Road, Boxborough, MA) together with a light collimating attachment and a polarizer (more preferably a right handed polarizer). These are preferably stabilized in a fixed position at an angle of twenty degrees to the lens so that light is cast on it with an intensity of 2,500-3,000 Lux.
- the light source is at a distance of about 135 mm from the lens in the lens holder. Sparkle count, or points of reflection, are counted in the images obtained from the camera.
- the sparkle count (or points of reflection) is preferably determined using ImagePro 8 software (commercially available from Media Cybernetics, Bethesda, MD, by: a) resizing the image to 10 or 15%, b) converting to 16-bit grayscale image twice, c) applying a "despeckle” filter to one gray image, d) selecting the remaining image and performing a background subtraction to subtract the despeckled image from the remaining gray image, e) engaging the "count” function (with the threshold set to "manual” with range "10,000-65,535"), f) removing any obvious bad points, such as glare in the pupil area or stray points outside of the printed contact, g) recording the number of counted objects.
- ImagePro 8 software commercially available from Media Cybernetics, Bethesda, MD, by: a) resizing the image to 10 or 15%, b) converting to 16-bit grayscale image twice, c) applying a "despeckle” filter to one gray image,
- Randomness is best distinguished using a Fourier Transform analysis approach.
- the Fourier Transform shows the component frequencies of the reflections of an image of the lenses.
- the Fourier Transform image is formulated to express the image's frequency domain as a symmetrically centered cloud of points wherein brightness represents the amplitude of the Fourier component and position represents its spatial frequency.
- Random or unordered images provide a diffuse Fourier transform with a central peak only. In cases in which the transform patterns show discernable sharp peaks outside the central peak it is because of periodicity (non- randomness or order) and the positions of the peaks are related inversely to spatial periodicities in the original image and lens.
- the most preferred method of obtaining these measurements is using the equipment, images and ImagePro 8 software described above with the FFT (Fast Fourier Transform) function. That is, after equipment set up, including but not limited to CCD camera, light source, lens and lens holder, a representative image is selected and (a) converted to 16-bit grayscale, (b) the FFT function was engaged (via pressing the icon, selecting "Amplitude” (floating pt), setting the spectrum gain to 15, and selecting "Forward”. This produces the Fourier Transform image from which randomness can be determined and the randomness factor (k sp ) is calculated (1 - (height of side peaks divided by height of central peak)).
- FFT Fast Fourier Transform
- the amount of the sparkle additive used is a sparkle effective amount meaning an amount that results in one or more areas of the lens having a sparkle effect when the lens is observed on-eye.
- an amount of about 0.5 to about 50 weight percent based on the total weight of the sparkle additive composition (including binder, cholesteric particle additive, and solvent) may be used.
- the particle size distribution range is approximately 4 to 70 um, preferably 4 to about 35 ⁇ and most preferably about 18 to about 35 ⁇ , in each case measuring the longest dimension of the particle. Those skilled in the art will realize that listed particle sizes refer to the average of the particle size and that a normal distribution around the average occurs.
- Pigments in addition to the cholesteric liquid crystal additives may be used in the sparkle additive composition.
- Such additional pigments may be those organic or inorganic pigments suitable for use in contact lenses, or combinations of such pigments.
- Illustrative organic pigments include, without limitation, pthalocyanine blue, pthalocyanine green, carbazole violet, vat orange # 1, and the like and combinations thereof.
- useful inorganic pigments include, without limitation, iron oxide black, iron oxide brown, iron oxide yellow, iron oxide red, titanium dioxide, and the like, and combinations thereof.
- soluble and non-soluble dyes may be used including, without limitation, dichlorotriazine and vinyl sulfone-based dyes. Useful dyes and pigments are commercially available.
- the sparkle additive compositions used in the lenses of the invention are composed of one or more sparkle additives with at least one of the sparkle additives being a cholesteric liquid crystal additive, one or more solvents, and a binding polymer.
- a binding polymer is used that is capable of forming an interpenetrating polymer network with the lens material.
- interpenetrating polymer network or “IPN” is defined as the combination of two or more independent polymers in which one polymer is synthesized and/or cross-linked in the presence of the other. Thus, some degree of interpenetration occurs within the network structures.
- the independent polymers used to form the IPN are in network form.
- IPN is composed of one or more polymers that are cross-linked and one or more polymers that are not substantially cross-linked as disclosed by "Interpenetrating Polymer Networks: An Overview" by Sperling,L.H. in Interpenetrating Polymer Network, Edited by Klempner, Sperling, and Utracki, pp 3-6(1994).
- the type of interpenetrating polymer network used is a semi-IPN.
- the semi-IPN is formed using a lens material, which is crosslinked and a binding polymer that is not substantially crosslinked.
- not substantially crosslinked means that the non-crosslinked material is not subjected to conventional crosslinking conditions prior to contact with the lens material.
- Semi-IPNs may be formed in one step, or in a series of steps, which are known as sequential semi-IPNs.
- cross-linking agents either through addition or as impurities, can create a reaction environment that favors the formation of a sequential interpenetrating polymer network.
- the binding polymers useful in the additive composition are made from a homopolymer or copolymer, or combinations thereof, having similar solubility parameters to each other and the binding polymer has similar solubility parameters to the lens material.
- These binding polymers may contain functional groups that render the polymers and copolymers of the binding polymer capable of interactions with each other.
- the functional groups must be such that the groups of one polymer or copolymer interact with that of another in a manner that increases the density of the interactions helping to inhibit the mobility of and/or entrap the additives and/or particles.
- the interactions between the functional groups may be polar, dispersive, or of a charge transfer complex nature.
- the functional groups may be located on the polymer or copolymer backbones or be pendant from the backbones.
- a monomer, or mixture of monomers, that form a polymer with a positive charge may be used in conjunction with a monomer or monomers that form a polymer with a negative charge to form the binding polymer.
- methacrylic acid (“MAA”) and 2-hydroxyethylmethacrylate (“HEMA”) may be used to provide a MAA/HEMA copolymer that is then mixed with a HEMA/3-(N, N-dimethyl) propyl acrylamide copolymer to form the binding polymer.
- the binding polymer may be composed of hydrophobically- modified monomers including, without limitation, amides and esters of the formula:
- CH 3 (CH 2 ) x -L-COCHR CH 2 wherein L may be -NH or oxygen, x may be a whole number from 2 to 24, R may be a Ci to Ce alkyl or hydrogen and preferably is methyl or hydrogen.
- amides and esters include, without limitation, lauryl methacrylamide, and hexyl methacrylate.
- polymers of aliphatic chain extended carbamates and ureas may be used to form the binding polymer.
- Preferred binding polymers will depend upon the lens material to be used.
- the preferred binding polymers are a random block copolymer of HEMA, and MAA or a homopolymer of HEMA.
- the weight percentages, based on the total weight of the binding polymer, of each component in these embodiments is about 93 to about 100 weight percent HEMA and about 0 to about 2 weight percent MAA.
- the preferred binding polymers are a random block copolymer of HEMA, OH-mPDMS, DMA, and, optionally, PVP.
- the molecular weight of the binding polymer must be such that it is somewhat soluble in the lens material and the lens material can diffuse into it.
- the molecular weight of the binding polymer cannot be so high as to impact the quality of the printed image.
- MW ranges can be significantly higher for binding polymers containing silicones including up to about 500,000 molecular weight.
- the molecular weight is determined using a gel permeation chromatograph with a 90° light scattering and refractive index detectors.
- Two columns of PW4000 and PW2500, a methanol-water eluent of 75/25 wt/wt adjusted to 50mM sodium chloride and a mixture of polyethylene glycol and polyethylene oxide molecules with well defined molecular weights ranging from 325,000 to 194 are used. This method is only for EtaA and binding polymers soluble in methanol-water eluent of 75/25 wt/wt. Binding polymers containing silicones may be soluble in alternate diluents.
- the desired binding polymer molecular weight may be obtained.
- a chain transfer agent is used in conjunction with an initiator, or more preferably with an initiator and one or more solvents to achieve the desired molecular weight.
- small amounts of very high molecular weight binding polymer may be used in conjunction with large amounts of solvent to maintain a desired viscosity for the binding polymer.
- the viscosity of the binding polymer will be about 4,000 to about 15,000 centipoise at 23° C.
- Chain transfer agents useful in forming the binding polymers have chain transfer constants values of greater than about 0.01, preferably greater than about 7, and more preferably greater than about 25,000.
- Suitable such chain transfer agents are known and include, without limitation, aliphatic thiols of the formula R-SH wherein R is a Ci to C aliphatic, a benzyl, a cyclicalipahtic or CH 3 (CH 2 ) X -SH wherein x is 1 to 24, benzene, n-butyl chloride, t-butyl chloride, n-butyl bromide, 2-mercapto ethanol, 1- dodecyl mercaptan, 2-chlorobutane, acetone, acetic acid, chloroform, butyl amine, triethylamine, di-n-butyl sulfide and disulfide, carbon tetrachloride and bromide, and the like, and combinations thereof.
- dodecanethiol, decanethiol, octanethiol, or combinations thereof is used as the chain transfer agent.
- any desirable initiators may be used including, without limitation, ultra-violet, visible light, thermal initiators and the like and combinations thereof.
- a thermal initiator is used, more preferably 2,2-azobis isobutyronitrile and 2,2-azobis 2-methylbutyronitrile.
- the amount of initiator used will be about 0.1 to about 5 weight percent based on the total weight of the formulation.
- 2,2-azobis 2-methylbutyronitrile is used with dodecanethiol.
- the binding polymers of the invention may be made by any convenient polymerization process including, without limitation, radical chain polymerization, step polymerization, emulsion polymerization, ionic chain polymerization, ring opening, group transfer polymerization, atom transfer polymerization, and the like.
- a thermal-initiated, free- radical polymerization is used. Conditions for carrying out the polymerization are within the knowledge of one ordinarily skilled in the art.
- Solvents useful in the production of the binding polymer are medium boiling solvents having boiling points between about 120 and 230 ° C. Selection of the solvent to be used will be based on the type of binding polymer to be produced and its molecular weight. Suitable solvents include, without limitation, diacetone alcohol, cyclohexanone, isopropyl lactate, 3-methoxy 1-butanol, l-ethoxy-2- propanol, ethanol, and the like.
- Coating, or wetting, of the cholesteric liquid crystal additives with binding polymer provides better dispersion of the additives in the bulk binding polymer.
- the coating may be achieved by use of dispersive, electrostatic, or hydrogen bonding forces to cover the additive's surface.
- the preferred sparkle additive composition of the invention may contain one or more solvents that aid in coating of the sparkle additive onto a surface. It may be desirableto control the sparkle additive composition's surface tension. This surface tension may be achieved by treatment of the surface, for example a mold surface, to which the sparkle additive composition will be applied. Surface treatments may be effected by methods known in the art, such as, but not limited to plasma and corona treatments. Alternatively, and preferably, the desired surface tension may be achieved by the choice of solvents used in the sparkle additive composition.
- the solvents useful in the sparkle additive composition of the invention are those solvents that are capable of increasing or decreasing the viscosity of the sparkle additive composition and aiding in controlling the surface tension.
- Suitable solvents include, without limitation, cyclopentanones, 4-methyl-2-pentanone, l-methoxy-2- propanol, 1 -ethoxy-2-propanol, isopropyl lactate, ethanol, and the like and combinations thereof.
- etafilcon A preferably, 1-ethoxy -2 -propanol and isopropyl lactate are used.
- narafilcon A preferably, l-ethoxy-2-propanol and ethanol are used.
- the specific amount of solvents used will depend on a number of factors.
- the amount of solvents used in forming the binding polymer will depend upon the molecular weight of the binding polymer desired and the constituents, such as the monomers and copolymers, used in the binding polymer.
- the amount of low boiling solvent used will depend upon the viscosity and surface tension desired for the sparkle additive composition.
- the amount of solvent used will depend upon the lens and mold materials used and whether the mold material has undergone any surface treatment to increase its wettability. Determination of the precise amount of solvent to be used is within the skill of one ordinarily skilled in the art. Generally, the total weight of the solvents used will be about 20 to about 75 weight percent of total additive composition will be used.
- each particle/additive used will have a critical particle/additive volume for the solvents selected.
- the critical particle/additive volume may be determined by any known means and, generally, is a volume based on the efficiency of a solvent and the binding polymer to suspend the pigment/additive particles for example, as disclosed in Patton, Temple C, Paint Flow and Pigment Dispersion, 2d ed., pp 126-300 (1993).
- a plasticizer may be added to the sparkle additive composition to reduce cracking during the drying of the colorant and optical mold parts, to enhance the final quality of the image produced using the sparkle additive composition, and to enhance the diffusion and swelling of the colorant by the lens material.
- plasticizer used will depend on the molecular weight of the binding polymer used and, for sparkle additive compositions placed onto molds that are stored prior to use, the shelf-life stability desired.
- Useful plasticizers include, without limitation, glycerol, propylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol 200, 400, or 600, and the like and combinations thereof.
- glycerol is used.
- Amounts of plasticizer used generally will be 0 to about 10 weight percent based on the weight of the sparkle additive composition.
- the opacity of the sparkle additive composition may be controlled by varying the sparkle additive concentration and the sparkle additive particle size used.
- an opacifying agent may be used. Suitable opacifying agents, such as for example titanium dioxide or zinc oxide, are commercially available.
- the intensity of the sparkle-effect may be controlled by varying the sparkle additive concentration and particle size or, in the case in which additional organic or inorganic pigments that are not cholesteric liquid crystal pigments are used in addition, the sparkle-effect may be controlled by varying the concentrations of these additional pigments as well.
- a preferred sparkle additive composition mixture of the invention about 0.5 to about 50 weight percent of cholesteric liquid crystal additive, about 10 to about 45 weight percent of binding polymer, about 20 to about 70 weight percent of solvents, and, optionally, about 0.2 to about 7 weight percent of plasticizer is used. The weight percentages are based on the total weight of the sparkle additive composition mixture.
- an amount of about 0 to about 25 weight percent based on the weight of the colorant for organic pigments and about 0 to about 50 weight percent for inorganic pigments may be used.
- high pigment concentrations of the additional pigments may impart a very dark hue. Therefore, preferably about 0 to about 7 weight percent of organic pigments and about 0 to about 20 weight percent of inorganic pigments may be used.
- Combinations of pigments may be used in ratios dependent upon the color, shade, and hue desired.
- additives other than those discussed also may be included in the sparkle additive composition of the invention.
- Suitable additives include, without limitation, additives that aid flow and leveling, additives for foam prevention, additives for rheology modification, and the like, and combinations thereof.
- the sparkle additive composition of the invention becomes embedded in the lens material upon curing of the material.
- the sparkle additive composition may embed closer to the front or back surface of the lens formed depending on the surface of the mold to which the lens the sparkle additive composition is applied.
- one or more layers of sparkle additive composition may be applied in any order.
- a clear binding polymer layer may be used in conjunction with the sparkle additive composition.
- a clear binding polymer layer may be applied to the molding surface of a mold half prior to application of the sparkle additive composition.
- the clear binding polymer may be the same or different from the binding polymer used for the sparkle additive composition layers. If the clear binding polymer is different from the binding polymer, it must be compatible with the binding polymer and lens material in terms of expansion factor and ability to swell and it must be capable of swelling into the lens material.
- the invention may be used to provide cosmetic hard or soft contact lenses made of any known lens material, or material suitable for manufacturing such lenses.
- the lenses of the invention are soft contact lenses having water contents of about 0 to about 90 percent.
- the lenses are made of monomers containing hydroxy groups, carboxyl groups, or both or be made from silicone- containing polymers, such as siloxanes, hydrogels, silicone hydrogels, and combinations thereof.
- Material useful for forming the lenses of the invention may be made by reacting blends of macromers, monomers, and combinations thereof along with additives such as polymerization initiators. Suitable materials include, without limitation, silicone hydrogels made from silicone macromers and hydrophilic monomers.
- silicone macromers include, without limitation, polydimethylsiloxane methacrylated with pendant hydrophilic groups as described in United States Patents Nos. 4,259,467; 4,260,725 and 4,261,875; polydimethylsiloxane macromers with polymerizable function described in U.S. Patents Nos.
- polysiloxane macromers incorporating hydrophilic monomers such as those described in U.S. Patents Nos. 5,010,141; 5,057,578; 5,314,960; 5,371,147 and 5,336,797; or macromers comprising polydimethylsiloxane blocks and polyether blocks such as those described in U.S. Patents Nos. 4,871,785 and 5,034,461. All of the cited patents are hereby incorporated in their entireties by reference.
- Suitable materials also may be made from combinations of oxyperm and ionoperm components such as is described in U.S. Patents Nos. 5,760,100; 5,776,999; 5,789,461; 5,807,944; 5,965,631 and 5,958,440.
- Hydrophilic monomers may be incorporated into such copolymers, including 2-hydroxyethyl methacrylate (“HEMA”), 2-hydroxyethyl acrylate, ⁇ , ⁇ -dimethylacrylamide (“DMA”), N- vinylpyrrolidone, 2-vinyl-4,4'-dimethyl-2-oxazolin-5-one, methacrylic acid, and 2- hydroxyethyl methacrylamide.
- HEMA 2-hydroxyethyl methacrylate
- DMA 2-hydroxyethyl acrylate
- DMA ⁇ , ⁇ -dimethylacrylamide
- N- vinylpyrrolidone 2-vinyl-4,4'-dimethyl-2-oxazolin-5-one
- siloxane monomers may be incorporated such as tris(trimethylsiloxy)silylpropyl methacrylate, or the siloxane monomers described in U.S. Patents Nos. 5,998,498; 3,808,178; 4,139,513; 5,070,215; 5,710,302; 5,714,557 and 5,908,906. They may also include various toughening agents, UV blockers, and wetting agents. They can be made using diluents such as primary alcohols, or the secondary or tertiary alcohols described in U.S. Patent No. 6,020,445. All of the cited patents are hereby incorporated in their entireties by reference.
- the materials for making the contact lenses are well known and commercially available.
- the material used is a HEMA based hydrogel, more preferably etafilcon A, and the binding polymer is formed from linear random block copolymers of MAA, and HEMA; linear random block copolymers of MAA and HEMA; linear random block copolymers of HEMA and LMA; or a HEMA homopolymer.
- Etafilcon A disclosed in U.S. Patent Nos.
- 4,680,336 and 4,495,313 incorporated herein in their entireties by reference generally is a formulation of 100 parts by weight (“pbw”) HEMA, about 1.5 to about 2.5 pbw MAA, approximately 0.3 to about 1.3 pbw ethylene glycol dimethacrylate, about 0.05 to about 1.5 pbw 1,1,1- trimethylolpropane trimethacrylate, and about 0.017 to about 0.024 pbw of a visibility tint.
- pbw 100 parts by weight
- etafilcon A is used with a linear random block copolymer of MAA and HEMA in a ratio of 0.47 MAA to 100 HEMA, or with a linear random block copolymer of HEMA and MAA in a ratio of 99.9 HEMA and 0.1 MAA to 99.5 HEMA and 0.5 MAA.
- a preferred method of manufacturing a cosmetic lens is carried out using pad printing as follows.
- a metal plate preferably made from steel and more preferably from stainless steel, is covered with a photo resist material that is capable of becoming water insoluble once cured.
- the pattern for the additive composition is selected or designed.
- the pattern may be a limbal ring pattern or a pattern that covers part or all of the iris but does not cover the portion of the eye effecting vision.
- the final overall pattern will then be reduced to the desired size using any of a number of techniques such as photographic techniques, placed over the metal plate, and the photo resist material is cured.
- the plate is subsequently washed with an aqueous solution and the resulting image is etched into the plate to a suitable depth, for example about 20 microns. Conditions for carrying out the pattern etching are within the knowledge of one ordinarily skilled in the art.
- the sparkle additive composition is then deposited onto the pattern to fill the depressions with sparkle additive composition.
- pattern or "design” in the above description refers to the layout of additive composition applied to the lens. However, wherever such a pattern or design will be used, the application of the additives in the additive composition to the pattern or design area will be random. That is, the pattern or design that is formed and used in printing onto the front curve of the lens is a random distribution of additives.
- a silicon pad of a suitable geometry and varying hardness, generally about 1 to about 10 Shore A durometer units, is pressed against the image on the plate to remove the sparkle additive composition and the sparkle additive composition may then dry slightly by evaporation of the solvent. The pad is then pressed against the molding surface of an optical mold and the sparkle additive composition is allowed to dry.
- the sparkle additive composition is applied to all or a portion of the molding surface of the mold.
- the sparkle additive composition is applied to that portion of the surface that will be used to mold the portion of the lens that will overlay the lens wearer's iris but not any portion of the eye affecting vision.
- the application may be carried out by any convenient means.
- the application is carried out by pad printing.
- molds containing printed patterns are stored for later use in the production of lenses said molds can be conditioned with heat and nitrogen to remove excess solvents and oxygen prior to their use in lens production. A lens-forming amount of a lens material then is dispensed into the mold.
- lens-forming amount is meant an amount sufficient to produce a lens of the size and thickness desired. Typically, about 10 to about 75, preferably about 50 to about 75 mg of lens material is used.
- lens material is meant the monomer or monomers that, when cured, form the lens.
- the lens material may include any of a wide variety of additives including, without limitation, initiators, ultraviolet absorbers, and the like and combinations thereof.
- the lens material and additive composition are cured under conditions suitable to form the tinted lens.
- the precise conditions for curing will depend upon the components of the additive composition and lens material selected and are within the skill of one of ordinary skill in the art to determine.
- a visible light cure is used at room air and at an elevated temperature of about 70 to about 85 0 C.
- curing takes from about 75 to about 240 seconds.
- binding polymer was made using 96 g of 1-dodecanethiol (“DODT”), 56.54 g lauryl methacrylate (“LMA”), 7.40 g methacrylic acid (“MAA”), 1367 g of hydroxyethylmethacrylate (“HEMA”), 68.5 g glycerol, 378 g l-ethoxy-2-propanol (“EP”), 1511 g isopropyl lactate (“IPL”) and 8.89g 2,2'-azobis(2- methylbutyronitrile) (“AMBN”).
- DODT 1-dodecanethiol
- LMA lauryl methacrylate
- MAA methacrylic acid
- HEMA hydroxyethylmethacrylate
- EP 378 g l-ethoxy-2-propanol
- IPL isopropyl lactate
- AMBN 8.89g 2,2'-azobis(2- methylbutyronitrile)
- Sparkle additive compositions containing 140 g of the binding polymer, HELICONE® jade colored cholesteric particles and 6 wt percent 1-propanol were prepared.
- the weight percent of the particle used for various compositions were 3.3, 6.1, and 8.9 wt percent based on the total weight of the additive composition (including binder, cholesteric particle additive, and solvent).
- Three formulations of each of the 3.3, 6.1 and 8.9 wt percent of sparkle additive formulations were prepared using particle size averages of 18, 24 and 35 ⁇ , respectively.
- a formulation using a particle size of > 35 ⁇ was prepared using a particle weight percent of 3.3.
- the front curve of a polystyrene optical mold was first printed with a 15 ⁇ clear layer, which was composed of the binding polymer described above.
- a random pattern using each of the additive compositions/formulations was pad printed onto the front curve molding surface of a polystyrene optical mold.
- Some lenses of each sparkle additive composition/formulation were single printed and some were double printed with a design.
- the mold was printed in a nitrogen enclosure having ⁇ 0.5 % oxygen after which the mold was filled with a lens-forming amount of etafilcon A.
- a complementary mold half was then used to complete the mold assembly.
- the mold assembly was placed onto a belt that then passed through a cure tunnel comprised of a dark zone and a curing zone that was equipped with lamps emitting a wavelength of 370 to 440 nm.having eele
- the mold assembly passed into the first stage of the tunnel, also referred to as the dark zone in which no bulbs were present, but in which heaters heated the air to between 55 and 75 0 C to maintain the mold temperature at or above the colorant sparkle additive Tg.
- the mold passed through the bulb and dark zone of the tunnel at a speed so that it remained in this zone for about 75 seconds during which time the Tg temperature was maintained by a continuous feedback system that monitored the mold environment temperature.
- the mold then exited the dark zone and entered the curing zone, which contained bulbs emitting a wavelength of 370 to 440 nm.
- the intensity output of each bulb was maintained by a microprocessor based temperature controller.
- the curing of the lens material was initiated and completed. Once curing was completed, the lens was removed from the mold and any uncured monomers or dilutes were leached from the lens. The lens was then was released from the mold and equilibrated in a buffered saline solution.
- the base curves for between 4 and 15 lenses made from each formulation were measured.
- the average base curve was measured using a Panametrics ultrasonic measurement system in which each lens is placed onto a pedestal and the return time is measured for an ultrasonic signal reflected from the lens base curve over a known diameter to measure the surface sag.
- the average base curves were found to be out of the specification of 8.50 mm ⁇ 0.2 mm.
- the highest concentrated lenses from each particle size were submitted for toxicity analysis for systemic toxicity, ocular irritation and cytotoxicity. The results showed that the lenses were non-toxic, non-irritating and non-cytotoxic.
- the lenses were then placed on prosthetic eyes, one having a light blue and a dark brown iris.
- Each eye was constructed from an acrylic substrate and had an average corneal radius of approximately 7.8 mm.
- the eye also had an artificial, painted iris about 3-4 mm from the surface.
- Visual observation by a single observer using a magnifier of approximately 3x power and at a distance of 40 cm or less under ambient lighting showed that, as concentrations and particle size increased, the resulting sparkle effect increased. Larger particles, increased concentration, or both were more visible on the light blue iris than smaller particles and lower concentrations.
- the 3.3 wt percent formulation of the >35um particle size distribution did not have an observable sparkle effect. It is believed that the sparkle effect was not observable due to the process - not the sparkle additive nor the sparkle additive composition.
- a sparkle additive composition containing 271.50 g of the binding polymer described in Example 1, 8.9 wt % HELICONE® jade colored pigment (based on the weight of the total sparkle additive composition) of a 24 ⁇ particle size distribution and 6 wt % of 1-propanol was prepared.
- the front curve of a polystyrene optical mold was first printed with a 15 ⁇ clear layer, which layer was composed of the binding polymer set forth hereinabove.
- a single or double layer of a 20 ⁇ thick pattern was pad printed onto the front curve molding surface of a polystyrene optical mold.
- the mold was degassed for at least 8 hours to remove excess solvents and oxygen after which the mold was placed onto a belt and filled with a lens-forming amount of etafilcon A.
- a complementary mold half was used to complete the mold assembly.
- the mold assembly was passed through a cure tunnel.
- the mold passed through the pre-cure, dark zone of the tunnel at a speed so that it remained in this zone for about 240 sees.
- the tunnel was equipped with heaters to heat the air to between 75 and 85 °C.
- the mold assembly then passed into a dark zone in which no bulbs were on, but in which heaters heated the air to between 75 and 85 0 C for an additional 240 sees.
- the mold then exited the dark zone and entered the curing zone, which contained bulbs emitting a wavelength of 370 to 440 nm and in which heaters heated the air to between 75 and 85 0 C.
- the mold was in this heated, lighted zone for 240 sec at which time the curing was completed.
- the lens was released from the mold, any uncured monomers and/or dilutes were leached from the lens, and the lens was then equilibrated in a buffered saline solution.
- a sparkle additive composition containing 149g of the binding polymer described in Example 1, 0.9 wt% Jade Helicone particles based on the weight of the total sparkle additive composition and 6 wt% 1-propanol was prepared for each of the three different particle size distributions 18, 24, and 35 um.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section). The lenses were placed on a dark brown prosthetic eye, as described in Example 1. Through visual observations, 0.9 wt% was determined to be the lowest concentration that resulted in a desired sparkle effect for 18 and 24 um particle size Helicones.
- the Jade 35um Helicone particles were remade at a concentration of 0.5 wt% relative to the total sparkle additive composition and manufactured as described above. Lenses were analyzed on a dark brown prosthetic eye.
- a concentration of 0.48 wt% relative to the total sparkle additive composition was the minimum concentration for the 35 um particle size Helicones to result in a desired sparkle effect.
- a sparkle additive composition containing up to 135, 120 and 105 g of the binding polymer described in Example 1; 9.4, 18.9, and 28.3 wt%, respectively, Jade Helicone particles based on the weight of the total sparkle additive composition and 6 wt% 1-propanol was prepared for each of the three different particle size distributions 18, 24, and 35 um, respectively.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section). Initial target weight percents were 40, 50 and 65 in clear (with 6, 20, 40 wt% 1-propanol respectively). Concentrations relative to the total of all components were 38, 42 and 46 wt %, respectively. The target 40 and 50wt% had flow while the target 65wt% had no flow but was wetted.
- a sparkle additive composition containing 135g of the binding polymer described in Example 1, 9.4 wt% Jade Helicone particles based on the weight of the total sparkle additive composition and 6 wt% 1-propanol was prepared for each of the three different particle size distributions 18, 24, and 35 um.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section) using cliches of 20 and 30 um depth. The lenses were placed on a dark brown prosthetic eye, as described in Example 1. Through visual observations, the 30 um depth cliche resulted in a lens whose printed region appeared more dense for each particle size. The lenses above were manufactured using a clear layer of 15 um depth.
- the 9.4 wt% Jade Helicone 24 um particles at 20 and 30 um depth were also manufactured using a 30 um depth clear layer. Through visual observations, there were no changes in appearance when increasing from a 15 to 30um clear layer.
- a sparkle additive composition containing 135g of the binding polymer described in Example 1, 9.4 wt% Jade Helicone particles based on the weight of the total sparkle additive composition and 6 wt% 1-propanol was prepared for each of the three different particle size distributions 18, 24, and 35 um.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section) but two different patterned cliches of 20 um depth each.
- One cliche design extended to but did not include the pupil region (donut-like in pattern) and the other included a limbal ring as (an annular band of color that, when the lens is on-eye and centered, partially or substantially completely overlies the lens wearer's limbal region, or the junction of the sclera with the cornea).
- the lenses were placed on a dark brown prosthetic eye, described in Example 1. Through visual observations, the effect was visible and similar in all printed regions.
- An additive composition in containing 120 g binding polymer described in Example 1, 18.9 wt% Jade 18 um distribution Helicone particles based on the weight of the total additive composition and 6 wt% 1-propanol was prepared.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section) but used three different cliches. Each cliche contained a single dot, a dot cluster of 5 and a dot cluster of 10 etched onto the surface. Each cliche differed in the size of the dot diameters. Size of the dot diameters were 200, 400 and 600 um, respectively, and all were at a 20um depth.
- the lenses were placed on a dark brown and light blue prosthetic eye, as described in Example 1. Through visual observations, the distinguish ability of the dots decreased as the size and number of dots in the cluster decreased. All dots were more visible on the dark brown prosthetic eye than on the light blue. Single dots were visible >200 um and all dot clusters > (and equal to) 200 um.
- Sparkle additive compositions were prepared by adding approximately 0.5 wt% 24 um distribution Jade Helicone particles to Etafilcon A, disclosed in U.S. Patent Nos. 4,680,336 and 4,495,313 and narafilcon A disclosed in U.S. Patent Nos. 6,270,218; 6,367,929; 6,822,016; 6,943,203; 5,697,495; and 6,054,090.
- the reactive monomer mixes containing cholesteric liquid crystal additives were left on a roller over night. Lenses were manufactured on a small scale using a glove box filled with nitrogen ( ⁇ 0.5wt% oxygen) and at a temperature of 50 to 65 degrees.
- Front curve plastic molds were dosed with approximately 100 uL of reactive monomer mix, back curve plastic molds were then placed on top of the front curves and a weight was added. The weights were removed and the assembly was then placed under UV lamps and allowed to cure for 10 or 25 minutes for etafilcon A and narafilcon A, respectively. The assembly was then placed in a saline packing solution at 90 degrees. Back curves were removed and lenses were released in aqueous solution. Through visual observations, the sparkle effect was visible and similar in both materials.
- An additive composition containing 105g of binding polymer described in example 1, 28.3wt% Jade 18um distribution Helicone particles based on the weight of the total sparkle additive composition and 6wt% 1-propanol was prepared.
- Lenses were fabricated as in Example 2 (Contact Lens Fabrication section) except that lenses were packaged in borate buffered saline containing 440 ppm PVP (K90 poly- N-vinylpyrrolidone).
- An additive composition containing 80 wt% (240.0g) of a silicone hydrogel binding polymer was combined to form a 20 wt % (60.0g) HELICONE® jade colored additive composition of a 24 mm particle size distribution.
- the silicone hydrogel is described in Example 3 of US Patent Application 61/040880 in the name of Johnson & Johnson Vision Care, Inc., the entire specification of which is incorporated herein by reference.
- a 50:50 solution of 1 -Ethoxy-2-Propanol and 200 proof Ethanol was added to the mixture until a viscosity of 1000 cP was achieved using a Brookfield digital viscometer, spindle 18 at 25 °C.
- the lens fabrication process was the same as that of Example 2 except that the dark zone pre-cure was 60 seconds and unheated and the cure was 544 seconds with temperatures between 60 and 70 °C.
- Example 1 An additive composition containing 135 or 120 g of binding polymer (described in Example 1), 10 or 20 wt%, respectively Jade, Maple, and Titanium Helicone particles based on the weight of binding polymer was prepared. Two different particle sizes (18 and 35 micron) for each formulation were fabricated. Lenses were fabricated as in Example 2 (Contact Lens Fabrication section) but two different patterned cliches for the sparkle additive composition transfer were used. These two cliches included one with a high and one with a low area coverage. Description of the contact lens parameters for each lot produced are listed in Table 1.
- Example 13 The lenses described in Example 13 were analyzed to determine the sparkle count, sparkle density (p), and sparkle randomness factor (k sp ). Particle sizes of 18, 24 and 35 microns with weight percents are listed in Table 1. Additionally, the lenses described in Examples 3 and 4 were analyzed to determine the sparkle count, sparkle density (p), and sparkle randomness factor (k sp ).
- a high resolution CCD camera was affixed to a stabilized platform.
- the CCD camera was at a distance of 97 +/-3 mm with the zoom on its lowest setting.
- the lenses were placed on a lens holder that is curved (with all air bubbles between the contact and the lens holder eliminated and all folds, wrinkles, or other features that may cause glare or shadows removed).
- the lenses were periodically moistened throughout the process with artificial tear solution (Prestige Brand Sterile Artifical Tears Lubricant Eye Drops). Ambient light was reduced as much as possible.
- Ten images of the lens with light cast upon it are taken by rotating 30° +/- 5° between pictures and moistening with artificial tears as needed. Exposure time was 600ms.
- the lens and lens holder was illuminated with a light source (DC-950 Fiber Lite, produced by Dolan-Jenner Industries of 159 Swanson Road, Boxborough, MA) together with a light collimating attachment and a right handed polarizer. These were stabilized in a fixed position at an angle of 20 degrees to the lens so that light is cast on it with an intensity of 2,500-3,000 Lux.
- the light source was at a distance of 135 mm from the lens in the lens holder. Sparkle count was counted in the images obtained from the camera.
- the sparkle count was determined using ImagePro 8 software (commercially available from Media Cybernetics, Bethesda, MD, by: a) resizing the image to 15%, b) converting to 16-bit grayscale image twice, c) applying a "despeckle” filter to one gray image, d) selecting the remaining image and performing a background subtraction to subtract the despeckled image from the remaining gray image, e) engaging the "count” function (with the threshold set to "manual” with range "10,000-65,535"), f) removing any obvious bad points, such as glare in the pupil area or stray points outside of the printed contact, g) recording the number of counted objects. This was repeated on the remaining 9 more images and the average sparkle count was obtained.
- the average sparkle count is listed in Table 1.
- the sparkle density (p) was obtained by dividing the sparkle count (obtained as above) by the total area count. Area count was determined with ImagePro 8 software (commercially available from Media Cybernetics, Bethesda, MD) by using the Manual Bright Objects and adjusting lower range value until pattern features are counted as one bright object and then using "Area" measurement in Measurement menu.
- the sparkle density (p) is listed in Table 1.
- the randomness factor (k sp ) was obtained as follows:
- Table 1 Average sparkle count, sparkle density (p) and randomness factor (k sp ) values.
Abstract
Description
Claims
Priority Applications (3)
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SG2012077129A SG185365A1 (en) | 2007-12-20 | 2008-12-20 | Cosmetic contact lenses having a sparkle effect |
AU2008366094A AU2008366094B2 (en) | 2007-12-20 | 2008-12-20 | Cosmetic contact lenses having a sparkle effect |
EA201291467A EA022159B1 (en) | 2007-12-20 | 2008-12-20 | Cosmetic contact lenses having a sparkle effect and method of making the same |
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US1521607P | 2007-12-20 | 2007-12-20 | |
US61/015,216 | 2007-12-20 | ||
US12/337,859 US7802883B2 (en) | 2007-12-20 | 2008-12-18 | Cosmetic contact lenses having a sparkle effect |
US12/337,859 | 2008-12-18 |
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US (1) | US7802883B2 (en) |
AR (1) | AR069941A1 (en) |
AU (1) | AU2008366094B2 (en) |
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WO2022208205A1 (en) * | 2021-03-29 | 2022-10-06 | Johnson & Johnson Vision Care, Inc. | Contact lens with improved cosmesis |
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WO2012177508A2 (en) * | 2011-06-20 | 2012-12-27 | E.I. Du Pont De Nemours And Company | Method for matching sparkle appearance of coatings |
US20130079660A1 (en) * | 2011-09-23 | 2013-03-28 | O Chang | Method utilizing thermograph of a tear film for generating a quantified index |
US20130083287A1 (en) | 2011-09-30 | 2013-04-04 | Johnson & Johnson Vision Care, Inc. | Method of creating a visible mark on lens using a leuco dye |
US20130083286A1 (en) | 2011-09-30 | 2013-04-04 | Johnson & Johnson Vision Care, Inc. | Method of creating a visible mark on lens using a leuco dye |
US8814350B2 (en) * | 2012-02-13 | 2014-08-26 | Johnson & Johnson Vision Care, Inc. | Dynamic stabilization zones for contact lenses |
US9046699B2 (en) * | 2012-03-13 | 2015-06-02 | Johnson & Johnson Vision Care, Inc. | Dynamic fluid zones in contact lenses |
US8911080B2 (en) * | 2012-08-27 | 2014-12-16 | Johnson & Johnson Vision Care, Inc. | Usage compliance indicator for contact lenses |
US9798162B2 (en) * | 2015-03-11 | 2017-10-24 | Johnson & Johnson Vision Care, Inc. | Annular shaped clear layer in cosmetic contact lenses |
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Also Published As
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TW200941028A (en) | 2009-10-01 |
TWI452324B (en) | 2014-09-11 |
US20090190091A1 (en) | 2009-07-30 |
EA022159B1 (en) | 2015-11-30 |
WO2012099555A3 (en) | 2012-09-13 |
SG185365A1 (en) | 2012-12-28 |
AU2008366094A1 (en) | 2013-02-07 |
AR069941A1 (en) | 2010-03-03 |
US7802883B2 (en) | 2010-09-28 |
EA201291467A1 (en) | 2013-04-30 |
AU2008366094B2 (en) | 2015-01-15 |
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