Title of Invention

A METHOD FOR MANUFACTURING A CONTACT LENS

Abstract A method for manufacturing a contact lens, comprising the steps of: a) applying to at least a portion of a molding surface of a mold a tinting-effective amount of a colorant; b) dispensing a lens-forming amount of a lens material into the mold; c) heating rapidly the mold to at or above a glass transition temperature of the colorant; d) diffusing the lens material into the colorant while maintaining the mold temperature at or above a glass transition temperature of the colorant; and e) curing subsequently the lens material in the mold under conditions suitable to form the tinted contact lens.
Full Text METHODS FOR THE PRODUCTION OF TINTED CONTACT LENSES
Field of the Invention
The invention relates to methods useful in the production of tinted contact
lenses. In particular, the invention provides a method in which diffusion of monomer
into the colorant is aided by the heating of the molds used to produce the lenses.
Background of the Invention
The use of tinted contact lenses to alter the natural color of the iris is well
known. Colorants used to produce tinted lenses generally are composed of a binding
polymer and pigments. In one method of manufacturing tinted contact lenses, for
examples as described and claimed in Attorney Docket No. VTN-571, United States
Application Serial No. 10/027,579 incorporated in its entirety herein by reference,
the colorant is applied to uncured lens material, that is subsequently cured, by
transfer of the colorant from a mold surface to the lens material. A disadvantage of
this method for producing tinted lenses is that the lens material may not diffuse
adequately into the colorant prior to cure. This results in residual, unbound polymer
becoming attached to the lens surface during the hydration step of processing of the
cured lens
In order to overcome this disadvantage, it is has been attempted to increase
the cure time, thus allowing for a longer period for the diffusion to take place.
However, this method is problematic in that it results in an increase in edge defects
due to deformation of the lens mold. Thus, a need exits for a method to improve
diffusion that does not adversely affect the resulting lens.
Detailed Description of the Invention and Preferred Embodiments
The invention provides a method, and lenses produced by that method, that
reduces the residual, unbound polymer on the lens surface and lens surface
roughness. In one embodiment, the invention provides a method for manufacturing a

contact lens comprising, consisting essentially of, and consisting of the steps of: a.)
applying to at least a portion of a molding surface of a mold a tinting-effective
amount of a colorant; b.) dispensing a lens-forming amount of a lens material into the
mold; c.) heating rapidly the mold to at or above a glass transition temperature of the
colorant; d.) diffusing the lens material into the colorant while maintaining the mold
temperature at or above a glass transition temperature of the colorant; and e.) curing
subsequently the lens material in the mold under conditions suitable to form the
tinted contact lens. In another embodiment, the invention provides lenses produced
according to this process.
In a first step of the method of the invention, the colorant is applied to the
molding surface of a thermoplastic optical mold, made from any suitable material
including, without limitation, polypropylene resin, polystyrene resin, and the like and
combinations thereof. For purposes of the invention, by "molding surface" is meant
a mold surface used to form a surface of a lens.
A tinting-effective amount of the colorant is applied to all or a portion of the
molding surface of the mold. Typically, the colorant if 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. A "tinting-effective amount" of the colorant is an amount sufficient to
impart the desired level of color to the lens to be produced. Generally, about 0.5 mg
to about 4.0 mg of colorant is used per lens. The application may be carried out by
any convenient means. Preferably, the application is carried out by pad printing.
A lens-forming amount of a lens material then is dispensed into the mold. By
"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. By "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 mold is then heated rapidly to facilitate the diffusion of the lens material
into the colorant. It is a discovery of the invention that by rapidly heating the mold
to a temperature at or above the glass transition temperature ("Tg") of the colorant,
diffusion of the lens monomer mixture into the colorant is increased. However,
heating must be not be so rapid so as to cause the deformation of the lens molds,
which deformation will result in edge defects in the cured lens. Preferably, the mold
is heated from about room temperature to the Tg in about 28 seconds, more
preferably in about 10 seconds, and most preferably in about 4 seconds. The
temperature is then maintained for a period of time prior to the initiation of lens
material curing to permit diffusion to take place to the desired degree. Preferably,
the diffusion is carried out for a time sufficient to swell the colorant to about 1 to
about 4 times its dried thickness. The period of time during which the temperature of
the mold is maintained at or above the Tg will depend upon the composition of the
colorant and the lens material selected. Preferably, the period of time ranges from
about 45 to about 75 seconds, more preferably about 65 to about 75 seconds, and
most preferably about 65 to about 71 seconds.
Rapidly heating the mold may be carried out by any convenient method
including without limitation, infrared lamps, hot air, or any heating source capable of
heating the mold to the desired temperature, but which does not initiate
polymerization of the lens material. In a preferred method, a plurality of short wave
IR. lamps having peak wavelengths of about 1 to about 2 microns are used to rapidly
heat the molds. The lamps may be set at specific points along a tunnel through
which the mold moves. The mold temperature is maintained while diffusion takes
place. Maintenance of the mold temperature at or above the colorant Tg may be
carried out by any convenient heating means. In the preferred embodiment, mold
temperature is maintained by heating the air surrounding the mold. Thus, in the

above-described embodiment, after first rapidly being heated to the colorant Tg, the
molds move through a portion of the tunnel in which the air is heated, as for example
by heaters.
Subsequent to the diffusion of the lens material into the colorant, the lens
material and colorant are cured under conditions suitable to form the tinted lens. The
precise conditions for curing will depend upon the components of the colorant and
lens material selected and are within the skill of one of ordinary skill in the art to
determine. In a preferred embodiment, a visible light cure is used at room air and at
an elevated temperature of about 55 to about 70 ° C. In this embodiment, curing
takes from about 75 to about 150 seconds. Once curing is completed, the lens is
released from the mold and may be equilibrated in a buffered saline solution.
Typically, the colorant used is composed of one or more pigments, one or
more solvents, and a binding polymer. In a preferred embodiment of the invention, a
binding polymer is used that is capable of forming an interpenetrating polymer
network with the lens material. Thus, in another embodiment, the invention
provides a method for manufacturing a contact lens comprising, consisting
essentially of, and consisting of the steps of: a.) applying to at least a portion of a
molding surface of a mold a timing-effective amount of a colorant, the colorant
comprising, consisting essentially of, and consisting of: one or more pigments, one or
more solvents and a binding polymer; b.) dispensing a lens-forming amount of a lens
material into the mold; c.) heating rapidly the mold to a temperature that is at or
above a glass transition temperature of the colorant; d.) diffusing the lens material
into the colorant while maintaining the temperature; and e.) curing subsequently the
lens material in the mold under conditions suitable to form the tinted contact lens,
wherein the binding polymer and the lens material form an interpenetrating polymer
network.
i

For purposes of the invention, "interpenetrating polymer network" or "JPN"
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. Typically, the
independent polymers used to form the IPN are in network form. One type of IPN,
specifically a semi-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 Networks, Edited by Klempner, Sperling, and Utracki, pp
3-6(1994). For purposes of the invention, the type of interpenetrating polymer
network used is a semi-IPN. In one embodiment, the semi-IPN is formed using a
lens material, which is crosslinked and a binding polymer that is not substantially
crosslinked. For the purposes of this invention 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. One of
ordinarily skilled in the art will recognize that, the presence of 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 colorant 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 pigment 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.
For example, 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. As a more
specific example, 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.
As another example, the binding polymer may be composed of
hydrophobically-modified monomers including, without limitation, amides and esters
of the formula:

wherein L may be -NH or oxygen, x may be a whole number from 2 to 24, R may be
a Ci to C6 alkyl or hydrogen and preferably is methyl or hydrogen. Examples of
such amides and esters include, without limitation, lauryl methacrylamide, and hexyl
methacrylate As yet another example, polymers of aliphatic chain extended
carbamates and ureas may be used to form the binding polymer.
Preferred binding polymers are a random block copolymer of HEMA, MAA
and lauryl methacrylate ("LMA"), a random block copolymer of HEMA and MAA
or HEMA and LMA, 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, about 0 to about 2 weight percent
MAA, and about 0 to about 5 weight percent LMA.

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.
However, at the same time, the molecular weight of the binding polymer cannot be
so high as to impact the quality of the printed image. Preferably, the molecular
weight of the binding polymer is about 7,000 to about 100,000, more preferably
about 7,000 to about 40,000, most preferably about 17,000 to about 35,000 Mpeak
which corresponds to the molecular weight of the highest peak in the SEC analyses (

For purposes of the invention, 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.
One ordinarily skilled in the art will recognize that, by using chain transfer
agents in the production of the binding polymer, by using large amounts of initiator,
by using living polymerization, by selection of appropriate monomer and initiator
concentrations, by selection of amounts and types of solvent, or combinations
thereof, the desired binding polymer molecular weight may be obtained. Preferably,
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.
Alternatively, 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. Preferably, 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 C12 aliphatic, a benzyl, a cyclicalipahtic or CH3(CH2)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. Generally, about
0 to about 7 weight percent based on the total weight of polymer formulation will be
used. Preferably 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.
Preferably, 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. Preferably, 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.
Preferably, 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, and the like.
Pigments useful with the binding polymer are those organic or inorganic
pigments suitable for use in contact lenses, or combinations of such pigments. The
opacity may be controlled by varying the concentration of the pigment and
opacifying agent used, with higher amounts yielding greater opacity. Illustrative
organic pigments include, without limitation, pthalocyanine blue, pthalocyanine
green, carbazole violet, vat orange # 1, and the like and combinations thereof.
Examples of 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. In addition to these pigments, soluble and non-soluble
dyes may be used including, without limitation, dichlorotriazine and vinyl sulfone-
based dyes. Useful dyes and pigments are commercially available.
Coating, or wetting, of the pigment particles with binding polymer provides
better dispersion of the pigment particles in the bulk binding polymer. The coating
may be achieved by use of electrostatic, dispersive, or hydrogen bonding forces to
cover the pigment's surface. Preferably, a high shear force is used to disperse the
pigment into the binding polymer. The pigment may be added to the binding
polymer by dispensing the polymer and pigment into a suitable mixer, such as a
rotary shaft mixer and mixing until a homogeneous mixture results, typically for a
period of up to about 30 minutes. The mixture may be then fed into a high shear
mill, such as an Eiger mill to disperse the pigment into the binding polymer.
Repeated milling is carried out as necessary to achieve complete dispersion.
Generally, milling is carried out until the pigments are about 0.2 to about 3 microns
in size. Milling may be carried out using any suitable, commercially available device
including, without limitation, a high shear or ball milling device.

In addition to the pigment and binding polymer, the preferred colorant of the
invention contains one or more solvents that aid in coating of the colorant onto a
surface. It is desirable, and preferred, that the colorant has a surface tension below
about 27 mN/m. This surface tension may be achieved by treatment of the surface,
for example a mold surface, to which the colorant 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 colorant.
Thus, the solvents useful in the colorant of the invention are those solvents
that are capable of increasing or decreasing the viscosity of the colorant and aiding in
controlling the surface tension. Suitable solvents include, without limitation,
cyclopentanones, 4-methyl-2-pentanone, l-methoxy-2-propanol, l-ethoxy-2-
propanol, isopropyl lactate and the like and combinations thereof. Preferably, 1-
ethoxy-2-propanol and isopropyl lactate are used.
In a preferred embodiment, at least three different solvents are used in the
colorant of the invention. The first two of these solvents, both medium boiling point
solvents, are used in the production of the binding polymer. Although these solvents
may be stripped from the binding polymer after its formation, it is preferred that they
are retained. Preferably, the two solvents are l-ethoxy-2-propanol and isopropyl
lactate. An additional low boiling solvent, meaning a solvent the boiling point of
which is between about 75 and about 120° C, is used to decrease the viscosity of the
colorant as desired. Suitable low boiling solvents include, without limitation, 2-
propanol, l-methoxy-2-propanol, 1-propanol, and the like and combinations thereof.
Preferably, 1-propanol is used.
The specific amount of solvents used will depend on a number of factors. For
example, 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 colorant. Further, if the colorant is to be applied to a mold and cured with a lens
material, 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 40 to about 75 weight percent of solvent will be used.
One ordinarily skilled in the art will recognize that each pigment used will
have a critical pigment volume for the solvents selected. The critical pigment
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
particles for example, as disclosed in Patton, Temple C, Paint Flow and Pigment
Dispersion, 2d ed., pp 126-300 (1993).
In addition to the solvents, a plasticizer may be and, preferably is, added to
the colorant to reduce cracking during the drying of the colorant and optical mold
parts, to enhance the final quality of the image produced using the colorant, and to
enhance the diffusion and swelling of the colorant by the lens material. The type and
amount of plasticizer used will depend on the molecular weight of the binding
polymer used and, for colorants 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. Preferably, glycerol is used.
Amounts of plasticizer used generally will be 0 to about 10 weight percent based on
the weight of the colorant.
The opacity of the colorant may be controlled by varying the pigment
concentration and the pigment particle size used. Alternatively, an opacifying agent

may be used. Suitable opacifying agents, such as for example titanium dioxide or
zinc oxide, are commercially available.
In a preferred colorant mixture of the invention, about 0.2 to about 25 weight
percent of pigment, about 30 to about 45 weight percent of binding polymer, about
40 to about 70 weight percent of solvents, about 0 to about 25 weight percent of
titanium dioxide, and about 0.2 to about 7 weight percent of plasticizer is used. The
weight percentages are based on the total weight of the colorant mixture.
The binding polymer may be loaded with about 0.2 to about 25 weight
percent based on the weight of the colorant for organic pigments and about 0.2 to
about 50 weight percent for inorganic pigments. However, high pigment
concentrations may impart a very dark hue. Therefore, preferably about 0.2 to about
7 weight percent of organic pigments and about 0 to about 20 weight percent of
inorganic pigments are used. Combinations of pigments may be used in ratios
dependent upon the color, shade, and hue desired.
One ordinarily skilled in the art will recognize that additives other than those
discussed also may be included in the colorant 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 colorant of the invention becomes embedded in the lens material upon
curing of the material. Thus, the colorant 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
colorant is applied. Additionally, one or more layers of colorant may be applied in
any order. In yet another embodiment, a clear binding polymer layer may be used in
conjunction with the colorant. For example, in the method of the invention a clear
binding polymer layer may be applied to the molding surface of a mold half prior to

application of the colorant. The clear binding polymer may be the same or different
from the binding polymer used for the colorant 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 tinted hard or soft contact lenses made
of any known lens material, or material suitable for manufacturing such lenses.
Preferably, the lenses of the invention are soft contact lenses having water contents
of about 0 to about 90 percent. More preferably, 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. Examples of such silicone macromers include, without limitation,
polydimethylsiloxane methacrylated with pendant hydrophilic groups as described in
United States Patents Nos. 4,259,467; 4,760,725 and 4-,261,875;
polydimethylsiloxane macromers with polymerizable function described in U.S.
Patents Nos. 4,136,250; 4,153,641; 4,189,546; 4,182,822;

5,981,675; and 6,039,913; and combinations thereof. They may also be made using
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 03.4,461. 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; 5,807,94425,965,631 and 5,958,440. Hydrophilic monomers
may be incorporated into such copolymers, including 2-hydroxyethyl methacrylate
("HEMA"), 2-hydroxyethyl acrylate, N,N-dimethylacrylamide ("DMA"), N-
vinylpyrrolidone, 2-vinyl-4,4,-dimethyl-2-oxazolin-5-one, methacrylic acid, and 2-
hydroxyethyl methacrylamide. Additional 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. Preferably, 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, HEMA and lauryl methacrylate ("LMA"); 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. Preferably etafilcon A is used with a
linear random block copolymer of MAA, HEMA and LMA in a ratio of 0.47 MAA
to 100 HEMA to 4.14 LMA, 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 tinted 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 colorant is selected or
designed and then 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. Conditions for carrying out the pattern etching are within the
knowledge of one ordinarily skilled in the art.
Following the pattern, 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. The colorant is then deposited onto the pattern to fill the
depressions with colorant. 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 colorant and the colorant is then dried slightly
by evaporation of the solvent. The pad is then pressed against the molding surface of
an optical mold and the colorant s allowed to dry. The mold is degassed for a
minimum of about 8 hours to remove excess solvents and oxygen after which the
mold is filled with lens forming amount of a lens material. A complementary mold
half is then used to complete the mold assembly and, after a period of diffusion
during which the lens monomer diffuses into the printed image, the mold assembly is
exposed to conditions suitable to cure the lens material used.
The invention will be clarified further by consideration of the following, non-
limiting example.

A colorant composition containing a binding polymer (lauryl methacrylate, 2-
hydroxyethyl methacrylate and methacrylic acid), pigments and isopropyl lactate, 1-
ethoxy-2-propanol, and 1-propoanol, 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 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 passes through a cure tunnel,
the inside of which tunnel was mounted 4 sets of 2, side-by-side, short wave IR
lamps at the beginning of the tunnel. In this tunnel, the mold assembly passed under
the IR bulbs and was heated to the Tg of the colorant. Control of the intensity of
each bulb was maintained by a microprocessor-based temperature controller. The
mold assembly then passed into a dark zone in which no bulbs were present, but in
which heaters heated the air to between 55 and 75 o C to maintain the mold
temperature at or above the colorant Tg. The mold passed through the IR 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 temperature. The mold then exited this
zone and curing of the lens material was initiated and completed. Once curing was
completed, the lens was released from the mold and equilibrated in a buffered saline
solution.

WE CLAIM:
1. A method for manufacturing a contact lens, comprising the steps of:
a) applying to at least a portion of a molding surface of a moid a
tinting-effective amount of a colorant;
b) dispensing a lens-forming amount of a lens material into the mold;
c) heating rapidly the mold to at or above a glass transition
temperature of the colorant;
d) diffusing the lens material into the colorant while maintaining the
mold temperature at or above a glass transition temperature of the
colorant; and
e) curing subsequently the lens material in the mold under conditions
suitable to form the tinted contact lens.

2. The method as claimed in claim 1, wherein step c.) is carried out by
heating the mold from about room temperature to the glass transition
temperature in about 28 seconds.
3. The method as claimed in claim 1, wherein step c.) is carried out by
heating the mold from about room temperature to the glass transition
temperature in about 10 seconds.
4. The method as claimed in any one of claims 1 to 3, wherein heating of the
mold is carried out using a plurality of infra-red lamps.
5. The method as claimed in any of claims 1 to 3, wherein the heating is
carried out using hot air.
6. The method as claimed in any one of claims 1 to 5, wherein step d.) is
carried out for a time sufficient to swell the colorant to 1 to 4 times a
thickness of the colorant when it is dry.

The method as claimed in any of claims 1 to 6, wherein step d.) is carried
out for 45 to 75 seconds.
The method as claimed in any one of claims 1 to 7, wherein step e.) is
carried out using a visible light cure at a temperature of 55 to 70°C for 75
to 150 seconds.
The method as claimed in any one of claims 1 to 8, wherein the colorant
comprises one or more pigments, one or more solvents and a binding
polymer, wherein, in step e.), the binding polymer and the lens materials
form an interpenetrating polymer network.

A method for manufacturing a contact lens, comprising the steps of: a) applying
to at least a portion of a molding surface of a mold a tinting-effective amount of a
colorant; b) dispensing a lens-forming amount of a lens material into the mold; c)
heating rapidly the mold to at or above a glass transition temperature of the
colorant; d) diffusing the lens material into the colorant while maintaining the
mold temperature at or above a glass transition temperature of the colorant; and
e) curing subsequently the lens material in the mold under conditions suitable to
form the tinted contact lens.

Documents:

1956-KOLNP-2004-FORM-27.pdf

1956-kolnp-2004-granted-abstract.pdf

1956-kolnp-2004-granted-assignment.pdf

1956-kolnp-2004-granted-claims.pdf

1956-kolnp-2004-granted-correspondence.pdf

1956-kolnp-2004-granted-description (complete).pdf

1956-kolnp-2004-granted-examination report.pdf

1956-kolnp-2004-granted-form 1.pdf

1956-kolnp-2004-granted-form 18.pdf

1956-kolnp-2004-granted-form 2.pdf

1956-kolnp-2004-granted-form 26.pdf

1956-kolnp-2004-granted-form 3.pdf

1956-kolnp-2004-granted-form 5.pdf

1956-kolnp-2004-granted-reply to examination report.pdf

1956-kolnp-2004-granted-specification.pdf


Patent Number 231360
Indian Patent Application Number 1956/KOLNP/2004
PG Journal Number 10/2009
Publication Date 06-Mar-2009
Grant Date 04-Mar-2009
Date of Filing 20-Dec-2004
Name of Patentee JOHNSON & JOHNSON VISION CARE, INC.
Applicant Address 7500 CENTURION PARKWAY, SUITE 100, JACKSONVILLE, IL
Inventors:
# Inventor's Name Inventor's Address
1 HERRIN KEITH B 2068 SPOONBILL STREET, JACKSONVILLE, FL 32224
2 SPAULDING TERRY L 2015 WILLESDON DRIVE EAST, JACKSONVILLE, FL 32246
PCT International Classification Number B29D 11/00
PCT International Application Number PCT/US2003/18797
PCT International Filing date 2003-06-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10/180,587 2002-06-26 U.S.A.