Title of Invention

MOLDS FOR PRODUCING CONTACT LENSES.

Abstract This invention describes molds made from alicyclic co-polymers that are useful in the production of contact lenses and methods for their use. (FIG. - NIL)
Full Text MOLDS FOR PRODUCING CONTACT LENSES
This invention describes molds that are useful in the production of
contact lenses and methods for their use.
RELATED APPLICATIONS
This application is a continuation-in-part of U.S. Pat. App. Ser. No.
10/395,755, which is a continuation-in-part of U.S. Pat. App. Ser. No.
10/222,373.
BACKGROUND
Contact lenses have been used commercially to improve vision since the
1950s. The first contact lenses were made of hard materials. Although these
lenses are currently used, they are not suitable for all patients due to their poor
initial comfort and their relatively low permeability to oxygen. Later
developments in the field gave rise to soft contact lenses, based upon
hydrogels, which are extremely popular today. These lenses have higher
oxygen permeability and are often more comfortable to wear than contact
lenses made of hard materials. Unlike hard lenses that are manufactured by
lathing hard pieces of plastic, malleable soft contact lenses are often
manufactured by forming the lens using a two part mold where each half has
topography consistent with the desired final lens. Examples of such molds and
their methods of production may be found in U.S. Patent Nos. 4,565,348,
4,640,489,4,495,313, JP 08025378, and JP 0726644 which are hereby
incorporated by reference in their entirety.
These two part molds contain a male member whose convex surface
corresponds to the back curve of a finished lens and a female member whose
concave surface corresponds to the front curve of a finished lens. To prepare
lenses using these molds, an uncured lens formulation is placed between the
concave and convex surfaces of the mold halves and subsequently cured. The
cured lens and the mold are subsequently treated with a liquid medium in order
to release the cured lens from the surface of the mold. Although this is a
process is straightforward, there are a number requirements that must be
satisfied in order to produce a useable lens. First the material from which the
mold is made must have properties that are chemically compatible with the
uncured lens formulation. Second, the mold material must be able to withstand
the curing conditions and be compatible with such conditions. For example,
lenses may be cured by either or both heat and light. If a lens is cured by
transmitting light to the uncured polymer, it is important that the lens mold
permit the transmission of light at the appropriate wavelength. Third, the mold
material must not stick to the cured lens to a degree that prevents release of
the cured lens. Often the lenses are produced in a manufacturing environment
where it is important for the lenses to removably adhere to the same said of the
lens mold upon separation in a repeatable and predictable fashion. Therefore,
the selection of appropriate materials to make the molds continues to be a
subject of concern to those who produce soft contact lenses.
Others have used materials such as polypropylene, polystryene,
polyethylene, polymethyl methacrylates, and modified polyolefins containing an
alicyclic moiety in the main chain to prepare two part lens molds. Although
these materials are useful, with discovery of different lens formulations,
particularly silicone hydrogel lens formulations, other useful mold materials are
needed.
Further, new developments in the field have led to contact lenses made
from hydrogels and silicone hydrogels that are coated with polymers to improve
the comfort of the lenses. Often lenses are coated by treating the cured lenses
with a polymer. Recently polymer coated lenses have been produced by
coating the surfaces of a two part mold with a polymer, adding an uncured
formulation to the coated lens mold, curing the lens, and subsequently
releasing the cured lens from the mold where the surface of said cured lens is
coated with the polymer that was originally adhered to the surface of the mold.
This process is described in further detail in U.S. Patent Application No.
09/921,192, filed on August 8, 2001 and entitled "Method for Correcting Articles
by Mold Transfer," which is hereby incorporated by reference in its entirety.
When using this method of coating a lens, the choice of mold material is even
more critical than when one is producing an uncoated lens.
Therefore, there remains an unmet need to produce lens molds that may
be used to produce many different types of soft contact lenses. It is this need
that the following invention fills.
DETAILED DESCRIPTION OF THE INVENTION
This invention includes a mold for making a lens comprising, consisting
essentially of, or consisting of an alicyclic co-polymer wherein said alicyclic co-
polymer comprises, consists essentially of, or consists of at least two alicyclic
monomers of different chemical structures. As used herein "lens" refers to any
ophthalmic device that resides in or on the eye. These devices can provide
optical correction or may be cosmetic. The term lens includes but is not limited
to soft contact lenses, intraocular lenses, overlay lenses, ocular inserts, and
optical inserts. The preferred lenses of the invention are soft contact lenses
are made from silicone elastomers or hydrogels, which include but are not
limited to silicone hydrogels, and fluorohydrogels. Soft contact lens
formulations are disclosed in U.S. Patent No. 5,710,302, WO 9421698, EP
406161, JP 2000016905, U.S. Pat. No. 5,998,498, U.S. Pat. App. Ser. No.
09/957,299 filed on September 20,2001, U.S. Pat. App. No. 09/532,943, U.S.
Patent No. 6,087,415, U.S. Pat. No. 5,760,100, U.S. Pat. No.5,776,999, U.S.
Pat. No. 5,789,461, U.S. Pat. No. 5,849,811, and U.S. Pat. No. 5,965,631.
Further polymers that may be used to form soft contact lenses are disclosed in
the following U.S. Pat. Nos. 6,419,858; 6,308,314; and 6,416,690. The
foregoing references are hereby inc orporated by reference in their entirety.
The particularly preferred lenses of the inventions are etafilcon A, genfilcon A,
lenefilcon A, polymacon, acquafilcon A, balafilcon A, lotrafilcon A, galyfilcon A,
senofilcon A, silicone hydrogels as prepared in U.S. Pat. No. 5,998,498, US
Pat. App. No. 09/532,943, a continuation-in-part of US Pat App. No.
09/532,943, filed on August 30,2000, U.S. Pat. Ser. No. 09/957, 299 filed on
September 20, 2001, soft contact lenses as prepared in U.S. Pat. App. No.
60/318,536, entitled Biomedical Devices Containing Internal Wetting Agents,"
filed on September 10,2001 and its non-provisional counterpart of the same
title, filed on September 6,2002, U.S. Patent No. 6,087,415, U.S. Pat. No.
5,760,100, U.S. Pat. No.5,776.999, U.S. Pat. No. 5,789,461, U.S. Pat. No.
5,849,811, and U.S. Pat. No. 5,965,631. These patents (and applications) as
well as all other patent disclosed in this application are hereby incorporated by
reference in their entirety.
As used herein, the term "alicyclic monomers" refers to polymerizable
compounds having at least one saturated carbocyclic ring therein. The
saturated carbocyclic rings may be substituted with one or more members of
the group consisting of hydrogen, C1-10alkyl, halogen, hydroxyl,
C1-10 alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido, silyl, and substituted
C1-10alkyl where the substituents are selected from one or more members of
the group consisting of halogen, hydroxyl, C1-10alkoxycarbonyl, C1-10alkoxy,
cyano, amido, imido, and silyl. Examples of alicyclic monomers include but are
not limited to polymerizable cyclobutanes, cyclopentanes, cyclohexanes,
cycloheptanes, cyclooctanes, biscyclcbutanes, biscyclopentanes,
biscyclohexanes, biscycloheptanes, biscyclooctanes, and norbornanes. It is
preferred that the at least two alicyclic monomers be polymerized by ring
opening metathesis followed by hydrogenation. Since co-polymers are costly,
it is preferable that the molds made from these co-polymers may be used
several times to prepare lenses instead of once which is typical. For the
preferred molds of the invention, they may be used more than once to produce
lenses.
More particularly, examples of alicyclic monomer containing saturated
carbocyclic rings include but are not limited to the following structures
wherein R1-6 are independently selected from one or more members of
the group consisting of hydrogen, C1-10alkyl, halogen, hydroxyl,
C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido, silyl, and substituted
C1-10alkyl where the substituents selected from one or more members of the
group consisting of halogen, hydroxyl, C1-10aJkoxycarbonyl, C1-10a!koxy, cyano,
amido, imido and silyl. Further two or more of R1-6 may be taken together to
form an unsaturated bond, a carbocyclic ring, a carbocyclic ring containing one
or more unsaturated bonds, or an aromatic ring. The preferred R1-6 is selected
from the group consisting of C1-10alkyl and substituted C1-10alkyl where the
substituents are selected from the group consisting of halogen, hydroxyl,
C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido and sifyl.
The alicyclic co-polymers consist of at least two different alicyclic
monomers. The preferred alicyclic co-polymers contain two or three different
alicyclic monomers, selected from the group consisting of

Typically the surface energy of the alicyclic co-polymer is between 30
and 45 dynes/cm at 25 °C. The more particularly preferred alicyclic co-polymer
contains two different alicyclic monomers and is sold by Zeon Chemicals L.P.
under the tradename ZEONOR. There are several different grades of

ZEONOR, having of glass transition temperatures form 105-160°C. The
particularly preferred ZEONOR, is ZEONOR 1060R, which according the to the
manufacturer, ZEON Chemicals L.P. has an melt flow rate ("MFR") range of
11.0 grams/10 minutes to 18.0 grams/10 minutes (as tested JISK 6719
(230°C))F a specific gravity (H2O =1) of 1.01 and a glass transition temperature
of 105°C.
As used here, the term "mold" refers to a rigid object that may be used to
form lenses from uncured formulations. The preferred molds are two part
molds as described above, where either the front curve or the back curve of the
mold is made of the alicyclic co-polymers of the invention and the other curve is
made of polypropylene. Examples of polypropylene include but are not limited
to metallocene catalyzed polypropylene that is nucleated and darified, such as
but not limited to Achieve 1615 from Exxon and ATOFINA EOD 00-11. The
preferred method of making the molds of the invention is by injection molding
using known techniques, but the molds could be made by other techniques
lathing, diamond turning, or laser cutting.
Typically lenses are formed on at least one surface of both mold parts.
However, if need be one surface of the fenses may be formed from a moid and
the other surface could be formed using a lathing method, or other methods.
Aside from the alicyclic co-polymers, the molds of the invention may
contain additives that facilitate the separation of the lens forming surfaces,
reduce the adhesion of the cured lens to the molding surface, or both. For
example additives such as metal or ammonium salts of stearic acid, amide
waxes, polyethylene or polypropylene waxes, organic phosphate esters,
glycerol esters or alcohol esters may be added to alicyclic co-polymers prior to
curing said polymers to form a mold. Examples of such additives include but
are not limited to Dow Siloxane MB50-321 (a silicone dispersion), Nurcrel 535
& 932 (ethylene-methacrylic acid co-polymer resin Registry No. 25053-53-6),
Erucamide (fatty acid amide Registry No. 112-84-5), Oleamide (fatty acid
amide Registry No. 301-02-0), Mica (Registry No. 12001-26-2), Atmer 163
(fatty alkyl diethanolamine Registry No. 107043-84-5), Pluronic
(polyoxypropylene-polyoxyethylene block co-polymer Registry No. 106392-12-
5), Tetronic (alkyoxylated amine 110617-70-4), Flura (Registry No.7681-49-4),
calcium stearate, zinc stearate, Super-Floss anti block (slip/anti blocking agent,
Registry No. 61790-53-2), Zeospheres anti-block (slip/anti blocking agent);
Ampacet 40604 (fatty acid amide), Kemamide (fatty acid amide), Licowax fatty
acid amide, Hypermer B246SF, XNAP, polyethylene glycol monolaurate (anti-
stat) epoxidized soy bean oil, talc (hydrated Magnsium silicate), calcium
carbonate, behenic acid, pentaerythritol tetrastearate, succinic acid, epolene
E43-Wax, methyl cellulose, cocamide (anti-blocking agent Registry No. 61789-
19-3), poly vinyl pyrrolidinone (360,000 MW) and the additives disclosed in U.S.
Pat No. 5,690,865 which is hereby incorporated by reference in its entirety.
The preferred additives are polyvinyl pyrrolidinone, zinc stearate and glycerol
mono stearate, where a weight percentage of additives based upon the total
weight of the polymers is about 0.05 to about 10.0 weight percent, preferably
about 0.05 to about 3.0, most preferably about 2.0 weight percent.
In addition to additives, the separation of the lens forming surfaces may
be facilitated by applying surfactants to the lens forming surfaces. Examples of
suitable surfactants include Tween surfactants, particularly Tween 80 as
described in U.S. Pat. No. 5,837,314 which is hereby incorporated by reference
in its entirety. Other examples of surfactants are disclosed in U.S. Pat. No.
5,264,161 which is hereby incorporated by reference in its entirety.
Still further, in addition to the alicyclic co-polymers, the molds of the
invention may contain other polymers such as polypropylene, polyethylene,
polystyrene, polymethyl methacrylate, and modified polyolefins containing an
alicyclic moiety in the main chain. For example, a blend of the alicyclic co-
polymers and polypropylene (metallocene catalyst process with nucleation,
where ATOFINA EOD 00-11) may be used, where the ratio by weight
percentage of alicyclic co-polymer to polypropylene ranges from about 99:1, to
about 20:80 respectively. This blend can be used on either or both mold
halves, where it is preferred that this blend is used on the back curve and the
front curve consists of the alicyclic co-polymers.
Further this invention includes a method of making a lens comprising,
consisting essentially of, or consisting of 1) dispensing an uncured lens
formulation onto a mold surface comprising, consisting essentially of, or
consisting of, an alicyclic co-polymer wherein said alicyclic co-polymer
comprises, consists essentially of, or consists of at least two alicyclic
monomers of different chemical structures, and 2) curing said lens formulation
under suitable conditions. The terms lenses, alicyclic monomers, and molds
have their aforementioned meaning and preferred ranges.
As used herein, the term "uncured" refers to the physical state of a lens
formulation prior to final curing to form a lens. Some lens formulations contain
mixtures of monomers which are cured only once. Other lens formulations
contain monomers, partially cured monomers, macromers and other
components. F:or examples of such partially cured formulations are disclosed
in U.S. Pat. Nos. U.S. Pat. Nos. 6,419,858; 6,308,314; and 6,416,690. This
invention will be useful these formulations among others.
As used herein, the phrase "curing under suitable conditions" refers to
any of the known methods of curing lens formulations, such as using light, heat,
and the appropriate catalysts to produce a cured lens. Examples of such
curing conditions may be found in the soft lens formulation references listed
herein.
Still further, the invention includes a lens produced by a method
comprising, consisting essentially of, or consisting of 1) dispensing an uncured
lens formulation onto a surface of a mold comprising, consisting essentially of,
or consisting of, an alicyclic co-polymer wherein said alicyclic co-polymer
comprises, consists essentially of, or consists of at least two alicyclic
monomers of different chemical structures and 2) curing said lens formulation
under suitable conditions. The terms lens, alicyclic monomers, uncured, and
molds have their aforementioned meaning and preferred ranges.
Yet still further, the invention includes a mold comprising, consisting
essentially of, or consisting of, an alicyclic co-polymer and at least one lens
forming surface
wherein said alicyclic co-polymer comprises, consists essentially of, or
consists of at least two alicyclic monomers of different chemical
structures, and
wherein said at least one lens forming surface comprises, consists
essentially of, or consists of a coating effective amount of a high
molecular weight coating composition.
The terms lens, alicyclic monomers, uncured, and molds have their
aforementioned meaning and preferred ranges.
As used herein "lens forming surface" means the surface that is used to
mold the lens. Such surface has an optical quality surface finish, meaning that
it is sufficiently smooth so that a lens surface formed by the polymerization of a
lens forming material in contact with the molding surface Is optically acceptable.
Further said surface has a geometry that is necessary to impart to the lens
surface the desired optical characteristics, including without limitation, spherical
aspherical and cylinder power, wave front aberration correction, cornea!
topography correction and the like as well as combinations thereof.
The term "high molecular weight" means an average molecular weight
("MW") sufficiently high so as to avoid dissolution of the coating into the lens
formulation or the mold material. For purposes of the invention, preferably the
molecular weight is determined using gel permeation chromatography ("GPC")
with a light scattering detector and a high sensitivity refractive index detector,
for example model PL-RI available from Polymer Labs. The GPC is performed
using a phenogel 5 nm linear column equipped with a guard column of the
same components and a solution of 0.5 weight percent lithium bromide in
dimethyl formamide as the eluent. Flow rates are 0.5 mL per minute with
injection volumes from about 10 to about 20 µL. The precise MW used will
depend upon the coating selected and the monomer mixture used. In a
preferred embodiment, the MW of the coating is greater than about 300 kD.
"Coating compositions" useful in this invention include a wide variety of
known monomers and polymers. Preferred are poly(vinyl alcohol),
polyethylene oxide, poly(2-hydroxyethyl methacrylate), poly(methyl
methacrylate), po!y{acryJic acid), po!y(methacry!ic acid), poly(ma!eic acid),
poly(itaconic acid), poly(acrylamide), poly(methacrylamide),
poly(dimethylacrylamide), poly(glycerol methacrylate), polystyrene sulfonic
acid, polysulfonate polymers, poly(viny! pyrrofidone), carboxymethylated
polymers, such as carboxymethylcellulose, polysaccharides, glucose amino
glycans, polylactic acid, polyglycolic acid, block or random copolymers of the
aforementioned, and the like, and mixtures thereof. Preferably, po!y(2-
hydroxyethyl methacrylate), poly(vinyl pyrrolidone), poly(acrylic acid),
poly(methacrylic acid), poly(meth)acrylamide, or poly(acrylamide) is used.
More preferably, poly(2-hydroxyethyl methacrylate) is used.
Aside from the high molecular weight polymers, the coating composition
may include a low boiling point (less than about 100 °C) solvent and a high
boiling point, (greater than about 100 °C) solvent. Suitable low boiling solvents
include, without limitation, acetone, chloroform, and alcohols such as methanol,
ethanol, isopropanol, tert-butanol, and the like. Useful high boiling solvents
include, without limitation, methyl-, ethyl-, and isopropyl lactate, ethylene and
(poly)ethyfene giycol, propyiene glycol, n-methyl pyrrofidine, dimethyl
formamide, tetrahydrogeraniol, 1-butanol, 1-pentanol, 1-hexano|, 1-octanol, 3-
methyl-3-pentanol, dimethyl-3-octanol, 3-methoxy-1-butanol, 1,2 and 1,4-
butanediol, 1,3-hexanediol, water, and the (ike. Typically, the ratio of the low
to high boiling solvent will be about 10:90 to 90:10 when coating between 15
and 45 degrees C. When the coating composition is applied using spin coating
(discussed below), the coating composition contains either or both tow boiling
and high boiling solvents.
Additionally, the coating composition may include at least one surfactant.
Suitable surfactants include, without limitation, anionic surfactants, such as
carboxylic acid salts, sulfonic acid salts, sulfuric acid salts, phosphoric and
polyphosphoric acid esters, cationic surfactants, such as long chain amines
and their salts, diamines and polyamines and their salts, quarternary
ammonium salts, amine oxides, nonionic surfactants, such as
polyoxyethylenated alkylphenols, alkyl phenol ethoxylates, polyoxyethylenated
straight chain alcohols, polyethoxylated polyoxypropylene glycols,
polyethoxylated polydimethylsiloxane copolymers, fluorinated alkane ethoxyiate
copolymers, and long chain carboxylic acid esters, zwitterionic surfactants,
such as pH-sensitive and pH insensitive surfactants, and the like, and
combinations thereof. The specific type and amount of surfactants used will
depend upon the other components of the coating composition and the molding
surface used. Typically, greater than or equal to about 0.001 weight percent
and less than or equal to about 5 weight percent based on the total weight of
the coating composition will be used.
The coating composition may be applied to the molding surface by any
suitable method including, but not limited to, compression, swabbing, spray
coating, ink jet printing, aerosolization, nebulization, dip coating, spin coating,
and the like and combinations thereof. Preferably, spin coating is used. Also,
preferably, the coating is dried, or rendered non-tacky, prior to its use for
forming lenses. Drying may be carried out using any suitable method, but
preferably is carried out at temperatures up to about the glass transition
temperature (Tg") of the mold material in air or under vacuum followed by
equilibration under a blanket of nitrogen at any temperature up to about the Tg
of the mold material. During the vacuum exposure process, cold traps or other
filters preferably are used to prevent contamination of the mold.
In a spin coating method, the coating composition preferably has a lower
surface tension than that of the molding surface"s surface energy. More
preferably, the surface tension of the coating composition is greater than about
3 dynes/cm below that of the surface energy of the molding surface to which it
is applied when measured at the coating application temperature. Most
preferably, the surface tension of the coating composition is more than 8
dynes/cm below that of the surface energy of the molding surface.
In a preferred spin coating method for use in forming contact lenses,
spin coating is used to deposit a coating of a dry thickness of about 5 to about
70 nm onto a molding surface of a mold. If the surface tension of the coating
differs from the surface energy of the mold by greater than about 8 dynes/cm
when measured at the coating application temperature, a suitable spin profile of
at least about 6,000 and no more than about 8,000 RPM using at least about 2
and no more than about 20 µl of coating composition and spinning for at least
about 3 sec. If the surface tension difference is less than about 8 dynes/cm,
the mold is spun up to at least about 3,000 and no more than about 5,000 RPM
using at least about 2 and no more than about 10 µl of coating composition and
then the mold is spun up to at least about 7,000 and more than about 10,000
RPM for at least about 3 seconds prior to stopping.
Any excess coating accumulating at the mold edges must be removed
and removal may be carried out by any convenient method including, without
limitation, swabbing the excess, removing the excess using vacuum, solvent,
washing or pressurized air jet. Preferably, the excess is removed using an air
jet. in using the air-jet, it is critical that spinning is started prior to the jet being
turned on and, preferably, the air jet pressure is equal to or greater than about
3 psi.
The term "coating effective amount" refers to the thickness and the
roughness of the coating composition on the lens forming surface. For hydrated
contact lenses, preferably a peak-to-peak surface roughness of the hydrated
lens is less than about 500 nm is preferable. Thus, by coating effective amount
is meant an amount of the coating composition sufficient to provide a dry film
thickness of the coating composition on the lens forming surface that will result
in a hydrated article with an acceptable surface roughness and for contact
lenses preferably a hydrated lens peak-to-peak surface roughness of less than
about 500 nm. More preferably, the amount of coating composition used is an
amount sufficient to produce a dry film thickness of at least about 5 nm and no
more than about 70 nm, preferably at least about 5 nm and no more than about
50 nm, more preferably at least about 20 nm and no more than about 40 nm.
Still more preferably said coating effective amount covers the entire or
substantially the entire lens forming surface.
Coating additives may be added to the high molecular weight coating
compositions of the invention. Coating additives may include but are not
limited to tints, pigments, and antimicrobial compositions. Examples of
antimicrobial compositions that may be used in this manner are disclosed in the
following U.S. Patents and applications which are hereby incorporated by
reference in their entirety, U.S. Pat Nos. 6,218,492; 6,248,811; 6,160,056 and
U.S. Pat. App. Nos. 10/028,400 filed on December 20,2001, entitled
Antimicrobial Contact Lenses and Methods for Their Production; and
10/029,526, filed on December 21, 2001, entitled Antimicrobial Contact Lenses
and Methods of Use.
Still, yet further, the invention includes a method for making a coated
lenses comprising, consisting essentially of, or consisting of
(1) coating at least one lens forming surface of a lens mold with a coating
effective amount of a high molecular weight coating composition
wherein said lens mold comprises an alicyclic co-polymer and at least one lens
forming surface;
wherein said alicyclic co-polymer comprises, consists essentially of, or
consists of at least two alicyclic monomers of different chemical
structures;
(2) dispensing an uncured lens formulation onto said at least one lens forming
surface; and
(3) curing said lens formulation and said coating composition using a dwell time
of less than about 5 minutes and under conditions suitable to form a coated
lens.
The terms lens, alicyclic monomers, uncured, molds, high molecular weight,
coating composition, and coating effective amount all have their
aforementioned meaning and preferred ranges.
In order to illustrate the invention the following examples are included.
These examples dp not limit the invention. They are meant only to suggest a
method of practicing the invention. Those knowledgeable in the production of
lenses as well as other specialties may find other methods of practicing the
invention. However, those methods are deemed to be within the scope of this
invention.
EXAMPLES
In the examples, the following abbreviations are used:
BC back curve
Blue-HEMA product of the base-promoted displacement of one chloride
of Reactive Blue # 4 dye by hydroxyethyl methacrylate.
CIP Pre-Cure
CG11850 1:1 (wt) blend of 1-hydroxycyclohexyl phenyl ketone and
bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine
oxide
CGI 819 Bis (2,4,6-trimethylbenzolyl)phenyl phosphine oxide
D3O 3,7-dimethyl-3-octano|
Darocur 1173 UV photo initiator Ciba Speciality Chemicals
DMA N.N-dimethylacrylamide
FC front curve
ATOFINA EOD 00-11 A metallocene and isotactic polypropylene having a
melt flow of 14-18 g/10 minutes, ASTM D1238
HEMA 2-hydroxyethyl methacrylate
I PA isopropanol
Macromer 2 the reaction product of described in the examples of U.S.
Pat. App. Serial No. 10/028,400 filed on December 20,
2001 and entitled Antimicrobial Contact Lenses and
Methods for Their Production
mPDMS monomethacryloxypropyl terminated polydimethylsiloxane
m-PDMS-OH mono-(3-methacryloxy-2-hydroxypropyloxy)propyl
terminated, mono-butyl terminated polydimethylsiloxane
(MW1100)
Norbloc 2-(2"-hydroxy-5-methacrylyloxyethylphenyl)-2H-
benzotriazole
PVP poly(N-vinyl pyrrolidone)
poly-Hema poly hydroxy ethylmethacylate having a molecular weight
of greater than 1 MM Dalton
SIGMA 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-
tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl
ester
TEGDMA tetraethyleneglycol dimethacrylate
TrEGDMA triethyleneglycol dimethacrylate
TBACB tetrabutyl ammonium-m-chlorobenzoate
THF tetrahydrofuran
TMI 3-isopropenyl-a,a-dimethylbenzyl isocyanate
TRIS 3-methacryloxypropyltris (trimethylsiloxy) silane
Example 1
Preparation of Molds with Alicyclic Co-Polymers
Pellets of the alicyclic co-polymer ZEONOR® 1060R were placed in a
de-humidifying dryer at 90°C for approximately one to four (1-4) hours. The
material was subsequently heated and purged through an injection molding
machine using the techniques generally described in Injection Molding
Handbook, edited by Dominick &. Donaid Rosato, Published by Man Nosirand
Reinhold Company, 1986. Approximately three (3) pounds of material was
purged and molded within 10-15 minutes to give front curves and back curves
for lenses having a power of -1 00 D. Normal usable lens molds were
recovered and used to make lenses following the procedure of Example 2.
Example 2
The formulation listed in Table A was used to prepare sil/cone hydrogel
lenses. Further details on the precise mixing procedure is disclosed in U.S.
Pat App- Ser. No. OS/957,299 Wed on September 20, 2001,
The remainder of the formulation were additives and diluents. The nionomet to
diluent ratio was 100:20, the diluent being 3,7-dimethy"-3-octanol. Acetic acid,
1 % of the final mix. was used to stabilize the monomer
The front and hack curve mckis prepared by the method of Example 1
were coated with a high MW poly-HEMA coating. Approximately 6 microliters
of a 1.3% wt percent solution of po!y-HEMA in 70:30 ethanol:ethyl lactate was
applied onto the front curve mold surface (concave) by spin costing at 80W
rpm for B sec. A jet of air was applied to the edge of the spinning part during
the last two seconds of the spin cycle to remove the excess coating.
Approximately 8.5 microliters of a 1.1% solution of poly-HEMA in 70:30
ethanokethyl lactate was applied to the back curve mold surface (convex) by
spin coating at 6000 rpm for 2 sec followed by 6 sec at 8000 rpm. A jet of air
was applied to the edge of the spinning part during the last two seconds of the
spin cycle to remove the excess coating. Lenses were made by dispensing the
above lens fornnulation into the lens molds, closing the parts, precuring under
visible lights for 45 sec at 45°C followed by approximately 7 minutes of cure
under visible lights at 70cC. In all cases the precure was begun within 30 sec
of lens monomer dose into the mold.
The lenses were tested clinically and were found to be equivalent in on-
eye wettability, or tear break-up time, and deposition resistance to ACUVUE®
etafilcon A lenses demonstrating that application of the coating to the lens
results in a physiological compatible lens.
Example 3
Preparation of Polypropylene Lens Molds
The FC and BC of lens molds were prepared using the method of
Example 1 and substituting polypropylene (manufactured by Atofina EOD
00-11) for the alicyclic co-polymer of Example 1.
Example 4
Preparation of Lenses Using the Molds of Example 3
Lenses were made using the formulation and method of Example 2, but
substituting the molds of Example 3, for the molds of Example 1. The finished
lenses were examined for defects in the coating using a visual inspection
apparatus. Defects were discrete areas on the surface of the finished lens
where the coating was not applied. The percentage of defects was calculated
and recorded in Table B, below. This example demonstrates that molds made
from alicyclic co-polymers may be used to produce coated lenses with
significantly reduced coating defects.
Example 5
Lenses Prepared With Different Mold Materials for the FC and BC
FC and BC molds made by the method of Examples 1 and 3 were used
to prepare lenses by the method of Example 2. Dissimilar mold materials were
used to make some lenses as per Table C. The coating defect rate was
measured as well as the haze The haze values indicated were measured by
placing test lenses in saline in a clear cell above a black background,
illuminating from below with a fiber optic lamp at an angle 66° normal to the
lens cell, and capturing an image of the lens from above with a video camera.
The background-subtracted scattered light image was quantitatively analyzed,
by integrating over the central 10 mm of the lens, and then compared to a -1.00
diopter CSI Thin lens (commercial lens made by Wesley Jessen 33 East Tower
A, Des Planes, IL), which is arbitrarily set at a haze value of 100, with no lens
set as a haze value of zero. This data shows that the lowest number of defects
are produced when the FC and the BC molds were made from an alicyclic
co-polymer.
Example 6
Preparation of Lens Molds from Alicyclic Polymer
Pellets of the alicyclic polymer Zeonex® 480R were placed in a de-
humidifying dryer at 100°C for approximately four (4) hours. An attempt was
made to form molds using the method of Example 1. Usable lens molds could
not be formed with this material. Only tabs of cured materials were recovered
and the lens mold cavities were not formed. Increasing the temperature of the
molding machine (to the machine"s maximum safety level) and the temperature
of the mold material did not correct this problem. No usable molds were
formed. This example demonstrates the distinction between the successful
production of molds made from alicyclic co-polymers and the failure of molds
made from alicyclic polymers.
Example 7
Preparation of Blended Molds
An amount of polypropylene (ATOFINA EOD-0011, 50%) was blended
with Zeonor 1060 R (50%) in a mixing tumbler and processed for 15 minutes.
This mixture was processed in a extrusion or palletizing process to generate a
uniform material. The blended material was placed into an injection molding
machine and extruded into male and female halves of a lens mold and
subsequently cured. The cured molds were placed into a nitrogen environment
of 30 minutes before use.
Example 8
Preparation of Silicone Hydrogel Lenses B-
The reaction components and diluent (D30) listed in Table D were mixed
together with stirring or rolling for at least about 3 hours at about 23°C, until all
components were dissolved. The reactive components are reported as weight
percent of all reactive components and the diluent is weight percent of final
reaction mixture. The reaction mixture was placed into the lens molds of
Example 7 and irradiated using Philips TL 20W/03T fluorescent bulbs at 45°C
under N2. The cure conditions in a gJove box are at approx 0.2 mW/c2 for
about 6.5 minutes, followed by 2.5 mWw/c2 for about 12 min. The oxygen level
was determine if the cured lenses remained with the front curve or the back curve of
the mold. Table E lists the percentage of Zeonor and polypropylene (pp) in
each lens mold half and the number of lenses of Lens Type B which remained
with either the front curve or the back curve after they were separated.
We Claim:
1. A mold for making a lens comprising an alicylic co-polymer
characterized in that said alicylic co-polymer comprises at least
two alicyclic monomers of different chemical structures.
2. The mold of claim 1, wherein the alicyclic monomers comprise
polymerizable cyclobutanes, cyclopentanes, cyclohexanes,
cycloheptanes, cycloctanes, biscyclobutanes, biscyclopentanes,
biscyclohexanes, biscycloheptanes, biscyclooctanes, or
norbornanes.
3. The mold of claim 1 comprising two alicyclic monomers wherein
the alicyclic monomers comprise a saturated carbocydic ring.
4. The mold of claim 1 wherein the alicyclic monomers are selected
from the group consisting of

members of the group consisting of hydrogen, C1-10alkyl, halogen,
hydroxyl,
2)
C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido, silyl, and substituted
C1-10a!kyi where the substituents are selected from the group consisting of
halogen, hydroxy), C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido and
silyl.

wherein two or more of R1-6are taken together to form an unsaturated bond, a
carbocyclic ring, a carbocyclic ring containing one or mcore unsaturated bonds,
or an aromatic ring.
6. The mold of claim 1 wherein the alicyclic monomers are selected from
the group consisting of
wherein R1-6 are independently selected from one or more members of the
group consisting of hydrogen, C1-10alkyl, halogen, hydroxyl,
C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido, silyl, and substituted
C1-10alkyl where the substituents are selected from one or more members of
the group consisting of halogen, hydroxyl, C1-10alkoxycarbonyl, C1-10alkoxy,
cyano, amido, imido and silyl.
7. The mold of claim 1 where R1-6 C1-10alkyi, or substituted C1-10alkyl where
the substituents are selected from the group consisting of halogen, hydroxyl,
C1-10alkoxycarbonyl, C1-10alkoxy, cyano, amido, imido and silyl.
9. The mold of claim 1 wherein the alicyclic co-polymer has a MFR of about
11.0 grams/10 minutes to about 18.0 grams/10 minutes, a specific gravity of
1.01 and a glass transition temperature of 105°C.
10. The mold of claim 1 wherein the mold further comprises an additive.
11. The mold of claim 10 wherein the additive is about 2.0 weight percent
zinc sterate.
12. The mold of claim 10 wherein the additive is about 2.0 percent glycerol
monostearate.
13. The mold of claim 1 wherein the front curve and the back curve
comprise an alicyclic co-polymer having a MFR of about 11.0 grams/10
minutes to about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105°C.
14. The mold of claim 1 wherein the front curve comprises an alicyclic co-
polymer having a MFR of about 11.0 grams/10 minutes to about 18.0 grams/10
minutes, a specific gravity of 1.01 and a glass transition temperature of 105°C
and the back curve comprises polypropylene.
15. The mold of claim 1 wherein the back curve comprises an alicyclic co-
polymer having a MFR of about 11.0 grams/10 minutes to about 18.0 grams/10
minutes, a specific gravity of 1.01 and a glass transition temperature of 105°C
and the front curve comprises polypropylene.
16. The mold of claim 1 wherein the front curve comprises an alicyclic co-
polymer having a MFR of about 11.0 grams/10 minutes to about 18.0 grams/10
minutes, a specific gravity of 1.01 and a glass transition temperature of 105°C
and the back curve comprises polypropylene and an alicyclic co-polymer
having a melt flow of 14, a share rate of MFR=12.0g and 17.6g, a specific
gravity of 1.01, and a glass transition temperature of 105°.
17. The mold of claim 1 wherein the back curve comprises an alicyclic co-
polymer having a MFR of about 11.0 grams/10 minutes to about 18.0 grams/10
minutes, a specific gravity of 1.01 and a glass transition temperature of 105°C
and the front curve comprises polypropylene and an alicyclic co-polymer having
a MFR of about 11.0 grams/10 minutes to about 18.0 grams/10
minutes, a specific gravity of 1.01 and a glass transition
temperature of 105°C.
18. The mold of claim 16 wherein the ratio of alicyclic co-polymer to
polypropylene is about 5:95 to about 95:5.
19. The mod of claim 16 wherein the ratio of alicyclic co-polymer to
polypropylene is about 20:80 to about 80:20.
This invention describes molds made from alicyclic co-polymers that are useful in the
production of contact lenses and methods for their use.

Documents:

199-KOLNP-2005-FORM-27.pdf

199-kolnp-2005-granted-abstract.pdf

199-kolnp-2005-granted-claims.pdf

199-kolnp-2005-granted-correspondence.pdf

199-kolnp-2005-granted-description (complete).pdf

199-kolnp-2005-granted-examination report.pdf

199-kolnp-2005-granted-form 1.pdf

199-kolnp-2005-granted-form 18.pdf

199-kolnp-2005-granted-form 2.pdf

199-kolnp-2005-granted-form 26.pdf

199-kolnp-2005-granted-form 3.pdf

199-kolnp-2005-granted-form 5.pdf

199-kolnp-2005-granted-letter patent.pdf

199-kolnp-2005-granted-reply to examination report.pdf

199-kolnp-2005-granted-specification.pdf


Patent Number 213969
Indian Patent Application Number 199/KOLNP/2005
PG Journal Number 04/2008
Publication Date 25-Jan-2008
Grant Date 23-Jan-2008
Date of Filing 16-Feb-2005
Name of Patentee JOHNSON & JOHNSON VISION CARE INC.
Applicant Address 7500 CENTURION PARKWAY SUITE USA.
Inventors:
# Inventor's Name Inventor's Address
1 SCOTT F.ANSELL 1321 CRYSTAL ANDS DRIVE JACKSONVILLE USA
2 DOMINIC GOURD 4428 MILLSTONE COURT JACKSONVILLE USA.
3 THOMAS R. ROONEY 8664 REEDY BRABNCHDRIVE JACKSONVILLE USA
4 DHARMESH K DUBEY 9087 STAROASS DRIVE INDIA
5 DAVID C TRURNER 12359 TRAVERTINE TRAIL USA
6 LENORAL L. COPPER 12306 PEACH ORCHARD DRIVE JACKSONVILLE USA.
7 THOMAS A. MATIACIA 8167 WEKIVA WAY JACKSONVILLE USA
8 RICHARD W. ABRAMS 7816 SOUTHSIDE BLVD APT 161, JACKSONVILLE USA
9 KEVIN P. MCCABE 10550-205 BAYMEADOWS ROAD JACKSONVILLE USA.
10 RICHARD J. FOUGERE 109 PLANMTERS ROW EST PONTE VEDRE BEACH USA
11 XU SONG 4161 RIPKEN CIRCLE EAST JACKSONVILLE USA
PCT International Classification Number B 06
PCT International Application Number PCT/US03/025235
PCT International Filing date 2003-08-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10/222,373 2002-08-16 U.S.A.