EP0177606A4 - COLORING CONTACT LENSES. - Google Patents

COLORING CONTACT LENSES.

Info

Publication number
EP0177606A4
EP0177606A4 EP19850902225 EP85902225A EP0177606A4 EP 0177606 A4 EP0177606 A4 EP 0177606A4 EP 19850902225 EP19850902225 EP 19850902225 EP 85902225 A EP85902225 A EP 85902225A EP 0177606 A4 EP0177606 A4 EP 0177606A4
Authority
EP
European Patent Office
Prior art keywords
lens
dye
colorant
pattern
vat
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19850902225
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0177606A1 (en
Inventor
Melvin E Kamen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Barnes Hind Inc
Original Assignee
Barnes Hind Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Barnes Hind Inc filed Critical Barnes Hind Inc
Publication of EP0177606A1 publication Critical patent/EP0177606A1/en
Publication of EP0177606A4 publication Critical patent/EP0177606A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00865—Applying coatings; tinting; colouring
    • B29D11/00894—Applying coatings; tinting; colouring colouring or tinting
    • B29D11/00903—Applying coatings; tinting; colouring colouring or tinting on the surface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M1/00—Inking and printing with a printer's forme
    • B41M1/26—Printing on other surfaces than ordinary paper
    • B41M1/30—Printing on other surfaces than ordinary paper on organic plastics, horn or similar materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M1/00—Inking and printing with a printer's forme
    • B41M1/40—Printing on bodies of particular shapes, e.g. golf balls, candles, wine corks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
    • B41M3/003—Printing processes to produce particular kinds of printed work, e.g. patterns on optical devices, e.g. lens elements; for the production of optical devices
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/001—Special chemical aspects of printing textile materials
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • 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
    • G02C7/021—Lenses; Lens systems ; Methods of designing lenses with pattern for identification or with cosmetic or therapeutic effects
    • 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 present invention relates to coloring lenses, such as ophthalmic lenses and particularly hard and soft contact lenses.
  • Coloring lenses such as ophthalmic lenses and particularly hard and soft contact lenses.
  • Past known attempts have included painting or printing a colored central portion onto a soft contact lens, fabricating the lens from two distinct pieces, the central one of which is colored (U.S. Patent No. 4,252,421) or masking selected areas of the lens and dipping it in its entirety into the coloring agent.
  • the present invention is a method for applying a dye to an ophthalmic, corneal contact, or intraocular lens, in a predetermined pattern, which comprises forming a colorant containing said dye into said pattern before applying it to the lens, then contacting the colorant with the lens while it is in said pattern, and then fixing the dye to said lens. No masking of portions of the lens, or equivalent expedients, are necessary.
  • the present invention provides colored lenses in a process which includes the steps of
  • the Figure depicts a normal human eye, to show the non-uniformity of the color pattern formed by the iris.
  • the preferred method for applying the colorant to the lens is indirect gravure.
  • the desired pattern is etched into a preferably horizontal metal plate, to one to two thousandths of an inch in depth.
  • Colorant is filled into the etched pattern, for instance, by washing the plate with the colorant and wiping off the plate with a doctor blade, thereby leaving colorant only in the etched area.
  • a printing pad is then pressed temporarily against the pattern, so that all the colorant is transferred to the pad.
  • the pad is then temporarily pressed against the surface of the lens sufficiently so that all the colorant in the desired pattern comes in contact with the lens and thereby transfers to the lens.
  • Preferred pads are elastomeric, more preferably silicone rubber, or neoprene (polychlorobutadiene), polybutadiene, polyisoprene, styrene-butadiene rubber, butyl rubber, nitrile rubber, ethylene-propylene
  • the elastomer should be chemically inert to the colorant.
  • the pad should be soft enough so that it can deform in shape as it is pressed against the metal plate, and against the entire curved surface being colored without fracturing the lens, but hard enough to retain its shape when at rest. Shore hardness values of about 1 to about 18 are satisfactory.
  • the end portion of the pad which transfers the colorant should approximate the shape of the lens being marked; thus, for a- contact lens the end of the pad should be a hemisphere or a paraboloid having a circular cross-section.
  • the pad is preferably a solid elastomeric body, but can be hollow.
  • the pad can be a cylinder which is rolled across the colorant on the etched plate, and then rolled across the lens to transfer the colorant to the lens.
  • the pad can also be made of harder material, such as hard rubber, provided that the printing surface matches the contour of the lens surface being colored so that when the pad is pressed against the lens surface all of the colorant contacts the lens.
  • the plate in which the pattern of colorant is initially formed is contoured to match the surface of the pad, so that all the colorant can be picked up by the pad when it is pressed against the plate.
  • Each lens can be mounted individually on a chuck or spindle, or a series of lenses on a conveyor can be passed through the printing station where they are colored.
  • a "negative" of the desired pattern is formed on the raised areas of a printing pad (in much the same manner as a conventional "rubber stamp", date stamp, and the like) by cutting away those portions of the pad which are not to form part of the pattern.
  • Colorant is then applied to the pattern only, for instance by rolling a colorant-loaded roller across the pad or by dipping the pad into a pan of colorant. The pad is then pressed against the lens surface.
  • the pad can be made of the same range of elastomeric materials as disclosed above for the indirect gravure method.
  • the flexographic pad can be made of stiffer material (e.g. hard rubber) if the pad is given a curve which closely approximates the surface of the lens being colored.
  • Another satisfactory, though less preferred, method is silk-screening, using conventional screen materials.
  • the desired pattern is formed on the screen, by combining numerous very small openings in the screen.
  • the colorant is forced through this pattern onto the lens using a wiper blade.
  • Jet-printing of the lens surface is also considered within the scope of this invention.
  • the colorant is sprayed through a number of closely spaced small-diameter orifices which are arrayed in the desired pattern and which are spaced just far enough from the lens surface so that after the colorant has been sprayed and is moving toward the lens surface, the individual sprays of colorant merge to form a continuous band defining the desired pattern (which then hits the lens surface).
  • the pad means a strip of paper or an equivalent carrier on which the pattern is formed, preferably by a thermosetting dye.
  • Lens materials The present invention is applicable to a wide range of lens materials. Particularly preferred are polymers which possess free hydroxyl groups, such as HEMA
  • Suitable lens materials are cellulosics, such as cellulose acetate butyrate, which like the hydroxyl-containing polymers, has a reactive bond or site with which a "reactive" dye (discussed below) can react.
  • lens materials which can be treated by this invention include poly(methylmethacrylate), which many hard contact lenses are made from, and copolymers thereof, and allyl diglycol carbonate (known under its trade name "CR-39”), silicones, silicone acrylates, and polycarbonates.
  • poly(methylmethacrylate) which many hard contact lenses are made from, and copolymers thereof, and allyl diglycol carbonate (known under its trade name "CR-39”), silicones, silicone acrylates, and polycarbonates.
  • the hydroxyl-bearing polymers and copolymers are generally hydrophilic, that is, they absorb water and are worn as "soft" contact lenses in the hydrated state, though they are manufactured in the hard, unhydrated state. Lenses made of these materials can be tinted by the present invention in either the hard or hydrated state, although if they are hydrated they should be blotted lightly so that the aqueous solution in which they have been hydrated is not dripping or running off the surface of the lens.
  • SUBSTITUTE SHEET Soft contact lenses are commercially available in the above polymers and copolymers.
  • the copolymers are generally cross-linked with a minor amount less than 1 wt. % of a cross-linking agent such as divinyl benzene, 1,1,1-trimethylolpropane trimethacrylate, ethylene glycol dimethacrylate, ethylene bis (oxyethylene)dimethacrylate, ethylene dimethacrylate, or 2-ethyl-2-hydroxymethyl-l,3- propanediol trimethacrylate.
  • a cross-linking agent such as divinyl benzene, 1,1,1-trimethylolpropane trimethacrylate, ethylene glycol dimethacrylate, ethylene bis (oxyethylene)dimethacrylate, ethylene dimethacrylate, or 2-ethyl-2-hydroxymethyl-l,3- propanediol trimethacrylate.
  • colorant is intended to mean a dye or pigment, that is, the agent which actually imparts color to the ' lens or combinations of dyes or pigments, plus the one or more solvents, vehicles, carriers, thickeners, and other auxiliary agents with which the dye or pigment is blended.
  • solvents, vehicles, carriers, thickeners, and other auxiliary agents with which the dye or pigment is blended.
  • the most preferred dyes are those known as "reactive" dyes.
  • a reactive dye is defined as one which reacts chemically with the substrate to which it is applied.
  • Such dyes generally include an easily displaced halogen atom, sulfone group, or sulfonyl group.
  • such dyes are the preferred ones to use with .lens materials which contain hydroxyl groups (such as hydroxyethylmethacrylate and copolymers thereof, and cellulosics such as cellulose acetate butyrate).
  • Reactive Black 5 4-amino-5-hydroxy-3,6-bis( (4-
  • Reactive Blue 21 copper-(29H,3lH-phthalocyaninato(2-)-
  • vat dyes Another class of"dyes which are highly suitable for use in this invention are the vat dyes. These dyes do not react with the lens but nonetheless penetrate into the lens and are retained therein, when the dye is dissolved in water under alkaline conditions. Examples of satisfactory vat dyes include:
  • thermosetting dyes Another class of dyes is the thermosetting dyes. These become fixed in the lens material by the application of heat. Examples include (numbers are references to the dye's entry in the Color Index): Yellow 54; Yellow 230; Red 60; Orange 25; Blue 95; and Blue 352. These are available from dye suppliers.
  • the dye is blended with other components to make up the colorant that is applied to the lens.
  • the reactive dye is mixed with water, an alkaline agent, and a thickener.
  • the alkaline agent can be sodium carbonate, sodium bicarbonate, or soda ash.
  • the amount must be effective to raise the pH ehough so that the dye and lens react together.
  • a satisfactory amount is about 15-30 grams of soda ash per kilogram of colorant, preferably 20-25 g/kg.
  • a highly satisfactory thickener is an alginate,- such as sodium alginate, or a finely divided montmorillonite clay. The amount should be effective to adjust the viscosity of the colorant to about 1000-3000 centipoise so that the colorant does not drip or run when it is on the printing pad or on the lens.
  • the viscosity should be high enough so that if a layer of the colorant is deposited on a smooth plate which is inclined at a 45° angle, the colorant does not flow down the plate.
  • the alginate can comprise 10-40 wt. % of the colorant.
  • Optional preferred additives to the colorant include a color-penetration improving agent such as thiodiethylene glycol; and a hygroscopic agent such as urea.
  • Colorants containing vat dyes or thermosetting dyes are formulated from water, thickener such as alginate, and an alkaline agent, with urea as an optional hygroscopic agent following the same criteria discussed above for reactive dyes.
  • Sodium hydroxide and sodium hydrosulfite are preferred vat dye alkaline reagents.
  • the amount of dye is not critical and can be adjusted in accordance with the intensity desired in the finished lens.
  • the dye can comprise about 1-15 wt. % of the colorant, and usually about 5-10 wt. %.
  • the lens is preferably hydrated with a solution which contains up to 1-2 wt. % of sodium bicarbonate or equivalent alkaline agent to promote the reaction of the dye and polymer.
  • Another class of dyes is oil-soluble dyes, which are formulated into the colorant by dissolving them in an organic or silicone oil. No alkaline agent is necessary; the colorant is otherwise thickened as taught above. Examples of such dyes are D&C Yellow No. 11, D&C Red No. 17, D&C Green No. 6, and 2-( (2,5-diethoxy-4- ( (methylphenyDthio)phenyl)azo)-l,3,5-benzenetrione. D. Fixing the colorant
  • the pattern which the colorant has assumed on the lens can be inspected.
  • An advantage of this invention is that if the pattern has a defect or is otherwise unsatisfactory for any reason, it can simply be washed off and the lens returned to be recolored.
  • the lens-colorant combination is treated to fix the dye into the lens.
  • the fixing is preferably accomplished by applying heat.
  • the object is to cause the dye to react with the polymer's -OH groups.
  • the combination is heated in a current of hot air at 150°C for 3 to 5 minutes, or at 190°C for about 1 minute; alternatively, the combination is heated in saturated or supersaturated steam for about 20-60 seconds at 100-110°C.
  • a vat dye the colorant is left on the lens for about 5 to about 30 minutes, at a temperature of 20°C to 100°C.
  • thermosetting dye or oil-soluble dye is heated to 125-150°C for about 2 to about 6 minutes.
  • the lens is then washed with water or a weak acid such as acetic or citric, and with solvents for the dye, thickener, and other agents (if any) of the colorant.
  • the object is to remove all material which remains on the surface of the lens.
  • the dyes discussed and applied as taught hereinabove actually penetrate into the lens, so the washing step will not remove the desired color.
  • the dye is a thermosetting dye which has been applied onto a paper strip or equivalent pad means
  • the dye can be transferred from the strip to the lens by pressing the strip against the lens and heating this combination to 100-250°C for 5 to 30 minutes, whereby the. dye sublimes into the lens material.
  • the preferred pattern on the contact lens is a ring of color, leaving the central region of the lens uncolored.
  • the uncolored central area can be about 3.85 to about 4.20 millimeters in diameter, to equal the size of the wearer's pupillary opening.
  • the colored area can have an outside diameter of about 9.60 to about 10.40 millimeters, to cover the wearer's iris. The portion of the lens outside the colored area remains clear.
  • the figure depicts a normal human eye and indicates the non-uniformity of the pattern of color in the iris.
  • the color of the general background areas 1 frequently differ slightly from the color that appears to be concentrated in filament-like areas 2 which radiate approximately radially from the pupil.
  • flecks or highlights 3 can appear randomly in the iris as well.
  • a pattern of this type can be readily reproduced by the process of this invention, by photographing a human eye and transforming the photographed image via conventional photoresist techniques into a detailed pattern in the etched plate of an indirect gravure, or onto the pad of a flexographic printer or a silk screen. Then, by successive applications of colorants containing dyes which have been selected and/or blended to match the desired colors for the various portions of the iris, the lens can be printed with a pattern which matches the actual patterns of the human iris.
  • the present invention can be employed to apply colorants which are coatings or films, and in which there is a pigment instead of a dye.
  • conventional film-forming agents such as nitrocellulose can be used in admixture with a desired dye or pigment.
  • the pigment must be reduced to an extremely fine sub-micron particle size, to avoid eye irritation.
  • Pigments include (phthalocyaninato(2-) )copper, red iron oxide, and ultramarine blue.
  • colorants which can be employed in this invention are (all amounts in grams):
  • This invention can also be utilized to tint the entire surface of a contact or ophthalmic lens.
  • functional coatings can be applied in the same manner such as photochromic and scratch-resistant compounds and ultraviolet absorbers.

Landscapes

  • Engineering & Computer Science (AREA)
  • Ophthalmology & Optometry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Textile Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mechanical Engineering (AREA)
  • Eyeglasses (AREA)
  • Coloring (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Non-Portable Lighting Devices Or Systems Thereof (AREA)
EP19850902225 1984-04-06 1985-04-03 COLORING CONTACT LENSES. Withdrawn EP0177606A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US59779184A 1984-04-06 1984-04-06
US597791 1990-10-15

Publications (2)

Publication Number Publication Date
EP0177606A1 EP0177606A1 (en) 1986-04-16
EP0177606A4 true EP0177606A4 (en) 1988-02-08

Family

ID=24392936

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19850902225 Withdrawn EP0177606A4 (en) 1984-04-06 1985-04-03 COLORING CONTACT LENSES.

Country Status (4)

Country Link
EP (1) EP0177606A4 (it)
AU (1) AU4219085A (it)
IT (1) IT1184407B (it)
WO (1) WO1985004679A1 (it)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL80039A0 (en) * 1986-09-16 1986-12-31 Saul Sterman Method and system for tinting contact lenses
IL82961A0 (en) * 1987-06-23 1987-12-20 Med Optics Corp Colored contact lens and methods for the production thereof
FR2622984A1 (fr) * 1987-11-09 1989-05-12 Charles Ayache Lentille de contact formant filtre solaire
US5034166A (en) * 1988-07-21 1991-07-23 Allergan, Inc. Method of molding a colored contact lens
US5120121A (en) * 1988-07-21 1992-06-09 Allergan, Inc. Colored lens
US4898695A (en) * 1988-11-01 1990-02-06 Pilkington Visioncare Holdings, Inc. Method for tinting hydrophilic plastic articles
ES2070340T3 (es) * 1989-11-01 1995-06-01 Schering Corp Lentes de contacto coloreadas que tienen una apariencia muy natural.
US5160463A (en) * 1990-10-30 1992-11-03 Pilkington Visioncare, Inc. Method of manufacturing a contact lens
GB2253919A (en) * 1991-03-22 1992-09-23 Tejprakash Singh Matharu Tinting soft hydrogel
US5266077A (en) * 1992-11-09 1993-11-30 Ciba-Geigy Corporation Method for tinting a hydrophilic contact lens
GB9411586D0 (en) * 1994-06-09 1994-08-03 Zeneca Ltd Coating process
US6149842A (en) * 1998-11-12 2000-11-21 Novartis Ag Methods and compositions for manufacturing tinted ophthalmic lenses
KR100463210B1 (ko) * 1998-11-26 2004-12-23 미쯔이카가쿠 가부시기가이샤 염색된 성형체
US6827440B2 (en) 2000-01-03 2004-12-07 Wesley Jessen Company Colored contact lens with a more natural appearance
DE102004047156A1 (de) * 2004-09-29 2006-03-30 Stefan Kloth Aufbewahrungs-, Reinigungs- und/oder Pflegelösung für Kontaktlinsen

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1583492A (en) * 1976-06-24 1981-01-28 Toppan Printing Co Ltd Method of dyeing or printing hydrogel resin
FR2406217A1 (fr) * 1977-10-14 1979-05-11 Essilor Int Procede pour le marquage d'une lentille ophtalmique en matiere organique, et une telle lentille ainsi marquee
JPS5458508A (en) * 1977-10-18 1979-05-11 Hoya Lens Co Ltd Method of printing on soft contact lens
US4238524A (en) * 1978-03-06 1980-12-09 American Optical Corporation Process for identification marking clear plastic articles
US4286957A (en) * 1979-01-10 1981-09-01 Essilor International "Cie Generale D'optique" Process of integrating a photochromic substance into an ophthalmic lens and a photochromic lens of organic material
US4468229A (en) * 1981-08-12 1984-08-28 Ciba-Geigy Corporation Tinted contact lenses and a method for their preparation with reactive dyes
JPS58104286A (ja) * 1981-12-16 1983-06-21 ジェイエスアール株式会社 着色された成形品の製造方法
US4447474A (en) * 1982-08-30 1984-05-08 Neefe Charles W Method of selectively tinting soft contact lenses
US4457761A (en) * 1983-02-16 1984-07-03 Precision Cosmet Co., Inc. Method and apparatus for marking contact lenses

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
No relevant documents have been disclosed. *

Also Published As

Publication number Publication date
IT1184407B (it) 1987-10-28
IT8520283A0 (it) 1985-04-09
EP0177606A1 (en) 1986-04-16
WO1985004679A1 (en) 1985-10-24
AU4219085A (en) 1985-11-01

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Inventor name: KAMEN, MELVIN, E.