Title of Invention

OPTHALMIC COMPOSITIONS COMPRISING POLYETHER SUBSTITUTED POLYMERS

Abstract A ophthalmic lens comprising at least one water soluble polymer having a molecular weight of at least 500,000 Daltons and comprising linear or branched polyether pendant groups having a molecular weight of at least 300.
Full Text

Ophthalmic Compositions comprising Polyether Substituted Polymers
Field of the Invention
The present invention relates to ophthalmic compositions comprising
polyether substituted polymers. More specifically, the present invention relates to
ophthalmic formulations, solutions and devices comprising polyether substituted
polymers.
Dry eye syndrome is an ocular surface disorder, which leads to severe
irritation, redness, and itchiness of the eye. The problem may arise from disruptions
in any one of the three major components of the tear film, namely the lipid, aqueous,
and mucous layers, or from abnormalities in the expression of their constituent
molecules.
Currently the majority of dry eye treatments involve the use of inorganic
salts, viscous solutions of hydrophilic polymers, and combinations of the two as
topical applications. It has been reported that an exponential loss of tear fluid occurs
via the puncta upon instillation of artificial tear substitutes. Accordingly, is not
limited to soft contact lenses, hard contact lenses, intraocular lenses, overlay lenses,
ocular inserts, and optical inserts.
The compositions of the present invention comprise, consist essentially and
consist of at least one lens forming component and at least one water soluble
polymer. As used herein the term water soluble, means both soluble in water at or
above room temperature as well as dispersible in water at or above room
temperature. Water soluble polymers of the present invention comprise linear or
branched polyether pendant groups having a molecular weight of at least about 300.
The water soluble polymers have a weight average molecular weight of at least
about 300,000 Daltons, preferably.greater than about 500,000; more preferably
greater than about 800,000 Daltons. The weight average molecular weight may be

measured via gel permeation chromatography against appropriate standards, such as
polymethyl methacrylate.
Suitable polyether pendant groups may be derived from monomers of the
Formula I

wherein n is greater than or equal to 7; m is 1 or 2; Z is a C1-C6 substituted or
unsubstituted alkyl group, q is 0,1 or 2 and p is 2-q, y is 2 to 4, A is any free radical
polymerizable group and X is a substituent independently selected from the group
consisting of H, hydroxyl, unsubstituted straight or branched alkyl groups,
substituted straight or branched alkyl groups, substituted and un substituted amines,
substituted and unsubstituted amides, mercaptans, ethers and esters.
Examples of free radical polymerizable groups include acrylates, styryls,
vinyls, vinyl ethers, C1-6alkylacrylates, acrylamides, C1-6alkylacrylamides, N-
vinyllactams, N-vinylamides, C2-12alkenyls, C2-12alkenylphenyls,
C2-12alkenylnaphthyls, or C2-6alkenylphenylC1-6alkyls. Preferred free radical
polymerizable groups include methacrylates, acryloxys, methacrylamides,
acrylamides, and mixtures thereof.
Preferably X is selected from substituted or unsubstituted straight
or branched C1-16 alkyl groups, and more preferably from substituted or
unsubstituted straight or branched C1-12 alkyl groups.
Substituents on the substituted alky groups for X include carboxylic acids,
esters, acyl halides, amines, amides, ketones, aldehydes, halides, sulfides,
mercaptans, quartenary ammonium salts combinations thereof and the like.
Substituents on the substituted alky groups for Z include hydroxyl,
carboxylic acids, esters, acyl halides, amines, amides, ketones, aldehydes, halides,
sulfides, mercaptans, quartenary ammonium salts combinations thereof and the like

Preferably n is 7 to 50 and more preferably 7 to 40.
Examples of monomers of Formula I include polymerizable ethoxylated
methanols having seven or more ether linkages, such as but not limited to mPEG
350, mPEG 475, mPEG1100, greater homologues thereof, combinations thereof and
the like. Preferred monomers of Formula I include mPEG 350, mPEG 475, mPEG
1100 combinations thereof and the like. Suitable monomers may be purchased from
various sources such as Aldrich, under the name polyethylene glycol methylether
methacrylate, with an average molecular weight within the ranges stated herein.
The water soluble polymer may further comprise pendant groups derived
from comonomers. Suitable comonomers may be hydrophilic or hydrophobic and
include polymerizable silicones, sugars, carbohydrates, polyethers, amides, lactams,
sulfonic acids, sulfonates, amines, hydroxyls, ethers, esters, aldehydes, ketones,
amino acids, methacrylated long chain hydrocarbons, polymerizable ionic
compounds, reactive latent compounds which may be converted to ionic groups after
the water soluble polymer is polymerized, combinations thereof and the like.
Preferably suitable comonomers include polymerizable amides, lactams,
polymerizable ionic compounds and glycosylated materials. Specific examples of
copolymers include lauryl methacrylate, butyl methacrylate, isopropyl methacrylate,
methyl methacrylate, phenyl methacrylate, hydroxyethyl methacrylate, methacrylic
acid, glycerol monomethacrylate, hydroxyethyl methacrylamide, 2-(-4-
morpholinyl)ethyl methacrylate, morpholinyl methacrylamide, 2-(N,N-
dimethylamino)ethyl methacrylate, dimethylacrylamide, N-vinyl polymerizable
materials including N-vinyl-N-methylacetamide and N-vinyl pyrrolidone, styrene
sulfonate, sodium 2- acrylamido-2-methyl-l-propanesulfonate,
sulfopropylacrylamide, combinations thereof and the like. Preferred comonomers
include dimethylacrylamide, N-vinyl pyrrolidone, combinations thereof and the like.
It is believed that the water soluble polymers of the present invention act as
artificial mucins, which help to retain the eyes natural tear film and lipid layer

integrity. The many polyether pendant groups provide a hydrophilic, brush or
comb-like structure to the water soluble polymers. Thus, in one embodiment, at
least about 20%, and preferably at least about 30 of backbone units of the water
soluble polymer have a pendant group bound thereto. In yet another embodiment at
least about 20%, preferably at least about 60% and more preferably at least about
75% of the pendant groups are polyether pendant groups of Formula I.
The water soluble polymers may be made by a variety of methods including
photopolymerization. The selected monomers of Formula I and comonomers are
mixed with a photoinitiator, with or without a solvent and polymerized using
radiation of the appropriate wavelength.
Suitable photoinitiator systems include aromatic alpha-hydroxy ketones,
alkoxyoxybenzoins, acetophenones, acylphosphine oxides, bisacylphosphine oxides,
and a tertiary amine plus a diketone, mixtures thereof and the like. Illustrative
examples of photoinitiators are 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-
methyl-1 -phenyl-propan-1 -one, bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentyl
phosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)-phenyl phosphineoxide
(Irgacure 819), 2,4,6-trimethylbenzyldiphenyl phosphine oxide and 2,4,6-
trimethylbenzoyl diphenylphosphine oxide, benzoin methyl ether and a combination
of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate. Commercially
available visible light initiator systems include Irgacure 819, Irgacure 1700, Irgacure
1800, Irgacure 819, Irgacure 1850 (all from Ciba Specialty Chemicals) and Lucirin
TPO initiator (available from BASF). Commercially available UV photoinitiators
include Darocur 1173 and Darocur 2959 (Ciba Specialty Chemicals). These and
other photoinitators which may be used are disclosed in Volume HI, Photoinitiators
for Free Radical Cationic & Anionic Photopolymerization, 2nd Edition by J.V.
Crivello & K. Dietliker; edited by G. Bradley; John Wiley and Sons; New York;
1998, which is incorporated herein by reference. The initiator is used in the reaction
mixture in effective amounts to initiate photopolymerization of the reaction mixture,

e.g., from about 0.1 to about 2 parts by weight per 100 parts of reactive monomer.
Polymerization of the reaction mixture can be initiated using the appropriate choice
of heat, visible or ultraviolet light or other means depending on the polymerization
initiator used. Alternatively, initiation can be conducted without a photoinitiator
using, for example, e-beam. However, when a photoinitiator is used, the preferred
initiators are bisacylphosphine oxides, such as bis(2,4,6-trimethylbenzoyl)-phenyl
phosphine oxide (Irgacure 819®) or a combination of 1-hydroxycyclohexyl phenyl
ketone and bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentyl phosphine oxide
(DMBAPO), CGI 1850and the preferred method of polymerization initiation is
visible light.
Suitable solvents include medium to high polarity systems such as toluene,
ethyl acetate, tertiary butyl alcohol, methyl sulfoxide, dimethylformamide,
methanol, combinations thereof and the like. Preferable solvents are those which are
readily miscible with hexanes while preparing a polar polymer, and water soluble
solvents while preparing a water immiscible polymer.
The solvent is used in amounts between about 10 and about 90 weight %,
based upon the amounts of all components in the reaction mixture (monomer,
comonomer, photoinitiator, solvent, etc.).
The reaction mixture is degassed prior to the reaction to remove dissolved
oxygen and the reaction is conducted under an inert atmosphere. Polymerization is
completed quickly, generally in times less than about 4 hours and preferably less
than about 2 hours.
The polymers may be isolated by known techniques, such as precipitation in
a non-polar solvent, followed by washing and or reprecipitation processes, and
evaporation of the residual solvent. These methods are well known in the art.
The water soluble polymers may be incorporated into a variety of ophthalmic
solutions and devices. For example, the water soluble polymers of the present

invention may be incorporated into eye drops, contact lens rewetting solutions,
contact lens packing and/or cleaning solutions or contact lenses themselves. When
the water soluble polymers are included in solutions, suitable amounts include
between about 50 ppm by weight and about 5 wt%, and preferably between about
100 ppm and about 3 wt%. When the water soluble polymers are included in
contact lenses they may be included in amounts up to about 15 weight % and
preferably in amounts between about 0.05 and about 10 weight %. The ophthalmic
solutions may include known additional components such as tonicity adjusting
agents (such as but not limited to buffers), viscosity adjusting agents, antimicrobial
agents, polyelectrolytes, stabilizers, chelants, antioxidants, combinations thereof and
the like.
The water soluble polymer may be incorporated into a contact lens in a
number of ways, including adding the water soluble polymer to the lens reaction
mixture and curing the mixture to form a lens, or soaking a preformed lens in a
solution comprising the water soluble polymer, coated onto a lens by any method,
including but not limited to grafting, mold transfer, dip coating, spin coating, etc,
combinations thereof and the like.
The water soluble polymer may be incorporated into any contact lens
formulation or used with any contact lens. A variety of formulations are known in
the art and include etafilcon A, galyfilcon A, lotrafilcon A and B, vifilcon,
balafilcon, omafilcon, genfilcon A, lenefilcon A, polymacon, acquafilcon A, and the
like. Other lens formulations using polymerizable components known in the art may
also be used.
The contact lenses may be hard or soft contact lenses. In one embodiment
the contact lenses are soft contact lenses. Soft contact lenses may be made from
conventional hydrophilic formulations or silicone hydrogel formulations.
In one embodiment, the water soluble polymers of the present invention are
incorporated into the hydrogel formulations without significant covalent bonding to

the hydrogel. The absence of significant covalent bonding means that while a minor
degree of covalent bonding may be present, it is incidental to the retention of the
wetting agent in the hydrogel matrix. Whatever incidental covalent bonding may be
present, it would not by itself be sufficient to retain the water soluble polymer in the
hydrogel matrix. Instead, the vastly predominating effect keeping the wetting agent
associated with the hydrogel is entrapment. The polymer is "entrapped", according
to this specification, when it is physically retained within a hydrogel matrix. This is
done via entanglement of the polymer chain of the water solublepolymer within the
hydrogel polymer matrix. However, van der Waals forces, dipole-dipole
interactions, electrostatic attraction and hydrogen bonding can also contribute to this
entrapment to a lesser extent.
The water soluble polymers may be incorporated into the hydrogel by a
variety of methods. For example, the water soluble polymers may be added to the
reaction mixture such that the hydrogel polymerizes "around" the water soluble
polymer, forming a semi-interpenetrating network. Alternatively, the water soluble
polymer may be included in the solution in which the lens is packaged. The water
soluble polymer permeates into the lens. The packaged lens may be heat treated to
increase the amount of water soluble polymer which permeates the lens. Suitable
heat treatments, include, but are not limited to conventional heat sterilization cycles,
which include temperatures of about 120°C for times of about 20 minutes. If heat
sterilization is not used, the packaged lens may be separately heat treated.
Alternatively, the water soluble polymers may be included in a coating
formulation and coated onto at least a portion of an ophthalmic device, and in one
embodiment a contact lens via suitable coating method, such as dip coating, mold
transfer, spin coating, grafting.
The non-limiting examples below further describe this invention.
The dynamic contact angle or DCA, was measured at 23°C, with borate
buffered saline, using a Wilhelmy balance. The wetting force between the lens

surface and borate buffered saline is measured using a Wilhelmy microbalance while
the sample strip cut from the center portion of the lens is being immersed into the
saline at a rate of 100 microns/sec . The following equation is used

where F is the wetting force, y is the surface tension of the probe liquid, p is the
perimeter of the sample at the meniscus and 9 is the contact angle. Typically, two
contact angles are obtained from a dynamic wetting experiment - advancing contact
angle and receding contact angle. Advancing contact angle is obtained from the
portion of the wetting experiment where the sample is being immersed into the
probe liquid, and these are the values reported herein. At least four lenses of each
composition are measured and the average is reported.
The water content was measured as follows: lenses to be tested were allowed
to sit in packing solution for 24 hours. Each of three test lens were removed from
packing solution using a sponge tipped swab and placed on blotting wipes which
have been dampened with packing solution. Both sides of the lens were contacted
with the wipe. Using tweezers, the test lens were placed in a weighing pan and
weighed. The two more sets of samples were prepared and weighed as above. The
pan was weighed three times and the average is the wet weight.
The dry weight was measured by placing the sample pans in a vacuum
oven which has been preheated to 60°C for 30 minutes. Vacuum was applied until
at least 0.4 inches Hg is attained. The vacuum valve and pump were turned off and
the lenses were dried for four hours. The purge valve was opened and the oven was
allowed reach atmospheric pressure. The pans were removed and weighed. The
water content was calculated as follows:
Wet weight = combined wet weight of pan and lenses - weight of weighing pan
Dry weight = combined dry weight of pan and lens - weight of weighing pan
% water content = (wet weight - dry weight) x 100
wet weight

The average and standard deviation of the water content are calculated for
the samples are reported.
Modulus and elongation were measured by using the crosshead of a constant
rate of movement type tensile testing machine equipped with a load cell that is
lowered to the initial gauge height. A suitable testing machine includes an Instron
model 1122. A dog-bone shaped sample having a 0.522 inch length, 0.276 inch
"ear" width and 0.213 inch "neck" width was loaded into the grips and elongated at
a constant rate of strain of 2 in/min. until it broke. The initial gauge length of the
sample (Lo) and sample length at break (Lf) were measured. Twelve specimens of
each composition were measured and the average is reported. Tensile modulus was
measured at the initial linear portion of the stress/strain curve.
The following abbreviations are used in the examples below:
HEMA 2-hydroxyethyl methacrylate
MAA methacrylic acid
EGDMA ethylene glycol dimethacrylate
mPEG350 polyethylene glycol methylether methacrylate, with a Mn of about
350
mPEG 475 polyethylene glycol methylether methacrylate, with a Mn of about 475
Norbloc 7966 2-(2,-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole
CGI 1850 1:1 (wgt) blend of 1 -hydroxycyclohexyl phenyl ketone and bis(2,6-
dimethoxybenzoyl)-2,4-4-trimethylpentyl phosphine oxide
CGI-819 bis(2,4,6-1ximethylbenzoyl)-phenylphosphineoxide
Blue HEMA the reaction product of Reactive Blue 4 and HEMA, as described in
Example 4 of U.S. Pat. no. 5,944,853

Examples
Example 1
The following compounds in the following amounts were mixed to form a
homogenous mixture.
mPEG350 59.66g
Norbloc 7966 340mg
CGI 1850 400mg
Isopropyl acetate 100mL
The homogeneous mixture was degassed under a vacuum of 80mm Hg over a period
of one hour. The vacuum was interrupted with a positive nitrogen flow on three to
four occasions during the degassing process. The material was moved to a glove
box, which was under a nitrogen environment. The mixture was transferred to a
crystallizing dish and covered with a watch glass. The system was then exposed to
visible light (Philips type T103 bulbs) for one hour at room temperature to form the
desired polymer.
The polymer was precipitated by the addition of 50mL of hexanes followed
by vigorous agitation. The solvent and any soluble material was decanted. Further
washes were performed using 300mL of hexanes followed by thorough mixing and
decantation of the liquids. The washing process was continued until the polymer
appeared tacky and very thick.
The product was dissolved in 50mL of ethyl acetate and reprecipitated by the
addition of hexanes to the system. The wash process described above was repeated
and the product was rid of all solvent in a rotary evaporator at 55°C. Yield of the
desired product was 39g. The material was obtained as a clear, thick paste whose
average molecular weight was determined to be 25000 by GPC.
Example 2
The following compounds in the following amounts were mixed to form a
homogenous mixture.

mPEG 475 45g
tertbutyl alcohol 70mL
Norbloc 75mg
CGI1850 300mg
The homogeneous mixture was degassed for 1 hour under a pressure of 100mm
Hg. The system was purged with nitrogen every 15 minutes during the degassing
process. The reaction mixture was transferred to a glove box under a nitrogen
atmosphere and into 110 ID x 175 OD x 70 mm height silvered crystallizing dish.
The dish was placed on a shelf approximately 115mm from the light source (visible
light bulbs, Philips - TL03). The vessel was covered with a 2mm thick filter cover
(Schott, VG-6, 339732) and the reactants were polymerized for one hour at room
temperature.
The polymer was precipitated in a beaker flask (Buchi - 450mL) with 100mL of
hexanes and vigorous agitation. The liquids were decanted and the polymer was
washed twice with 100mL of hexanes each time. The residual solid was then
dissolved in 50mL of ethyl acetate, reprecipitated and washed with hexanes as
described above. The ethyl acetate/hexanes sequence was repeated once more and
some of the crude product (2-4g) removed, dried under reduced pressure, and in a
vacuum oven at 50°C prior to obtaining molecular weight data by GPC.
An accurately weighed amount (W1) of 2-hydroxyethyl methacrylate (HEMA)
was added to the beaker flask (approximately 250g) and the system is gently mixed
on a rotary evaporator until the system is completely homogeneous. The bath was
then heated at 40°C under a vacuum of 10-15mbar. The evaporation was continued
for two hours after the point at which no solvent was being distilled over.
The weight of the beaker flask and solution was accurately measured (W2 =
weight of flask + polymer + HEMA). After transferring the solution to an
appropriate container, the beaker flask was thoroughly cleaned, dried, and accurately
weighed (W3 = weight of beaker flask).
W2-W3 - weight of HEMA + polymer = W4

W4 - W1 = total yield of polymer = W5 (typical yield = 45%)
Concentration of the polymer solution (weight percent) was determined as
W5/(W4). Molecular weights (Mn) were determined against polymethyl
methacrylate (PMMA) standards to be greater than about 300,000.
Example 3
One weight% of the polymer of Example 1 was added to Packing Solution.
5 ml of the Packing Solution polymer mixture was places in glass vials, and a 1-Day
ACUVUE brand contact lens (commercially available from Johnson & Johnson)
was placed in the vial. The vial was sealed and autoclaved at 121°C for 30 minutes.
The lenses were allowed to equilibrate after autoclaving for at least about 1 day at
ambient temperature.
Five subjects were recruited to wear the test lens in one eye and the control
lens in their other eye. The lenses were allowed to settle for 30-minutes prior to any
observations.
After 30 minutes, the non-invasive tear break-up time (NIBUT) and lipid
layer thickness were observed for both lenses using the Tearscope Plus™ (Keeler).
The test lens was found to have a longer NIBUT than the control lens (10.4 seconds
vs. 7.6 seconds). The test lens was also found to have a thicker lipid layer than the
control lens in 4 of the 5 of the subjects.



Example 4
The copolymer (MM-44) formed in Example 2 was used as a monomer
component in the formulation listed in Table 3, below. .

The components were mixed in a glass jar with 40 weight % boric acid
glyceryl ester, sealed and rolled on a jar roller until homogeneous.
The lenses were were made on a single cavity lens machine utilizing
polystyrene + 1% zinc front curve and back curve lens molds. Monomer was dosed
into the front curve, back curve was deposited, and parts were placed under pre-cure
lights for 10 seconds. Molds were cured for 4 minutes at approximately 4 mW/cm2
and 65°C. Lenses were demolded and placed into leach solution at 70±5°C for
180±30 minutes, followed by rinse at 45±5°C for 15 to 60 minutes and equilibration
at 45±5°C for a minimum of 3 hours. Lenses were visually inspected, packaged in
vials with packing solution and sterilized for 30 minutes at 121 °C. Physical
properties were measured for the lenses and are shown in Table 4, below.



Thirty myopic, current soft contact lens wearers were recruited to wear test
lenses and control lenses (1-DAY ACUVUE). Each lens type was worn daily wear
for 1-week and replaced on a daily disposable basis. The study design was a
randomized, bilateral cross-over design with investigator masking. Twenty-nine
subjects completed the study.
After wearing the lenses for 1-week, the subjects completed preference
questionnaires comparing their experiences with both lens types. The lenses from
this Example 4 were preferred 2:1 over 1-DAY ACUVUE® in the areas of overall
comfort, end of day comfort, dryness, wearing time, and moisture. Symptoms
reported by the subjects at the 1-week visit were reduced for the test lenses by 50%
compared to the control lens.

We claim:

1. A ophthalmic lens comprising at least one water soluble polymer having a molecular
weight of at least 500,000 Daltons and comprising linear or branched polyether pendant
groups having a molecular weight of at least 300.
2. The lens as claimed in claim 1 where said polyether pendant groups are derived from
monomers of the Formula I

wherein n is 7 or greater; Z is a C1-C6 substituted or unsubstituted alkyl group, q is 0,1 or
2 and p is 2-q, y is 2 to 4, m is 1 or 2; A is any free radical polymerizable group and X is
a substituent independently selected from the group consisting of H, hydroxyl,
unsubstituted straight or branched alkyl groups, substituted straight or branched alkyl
groups, substituted and un substituted amines, substituted and un substituted amides,
mercaptans, ethers and esters.
3. The lens as claimed in claim 2 wherein X is selected from substituted or unsubstituted
straight or branched C1 -16 alkyl groups.

4. The lens as claimed in claim 3 wherein X is selected from is selected from substituted
or unsubstituted straight or branched C1 -12 alkyl groups.
5. The lens as claimed in claim 3 wherein said alkyl group is substituted with a group
selected from the group consisting of carboxylic acids, esters, acyl halides, amines,
amides, ketones, aldehydes, halides, sulfides, mercaptans, quartenary ammonium salts
and combinations thereof.
6. The lens as claimed in claim 3 wherein n is an integer of between 7 to 50.
7. The lens as claimed in claim 3 wherein n is an integer of between 7 to 40.
8. The lens as claimed in claim 1 wherein said polymer comprises at least 20% of
backbone units have a pendant group bound thereto.
9. The lens as claimed in claim 1 wherein said polymer comprises at least 30% of
backbone units have a pendant group bound thereto.
10. The lens as claimed in claim 2 wherein at least 20% of said pendant groups are
polyether pendant groups of Formula I.

11. The lens as claimed in claim 2 wherein at least 60% of said pendant groups are
polyether pendant groups of Formula I.
12. The lens as claimed in claim 2 wherein at least 75% of said pendant groups are
polyether pendant groups of Formula I.
13. The lens as claimed in claim 1 wherein said pendant groups further comprise at least
one second pendant group selected from the group consisting of silicones, sugars,
carbohydrates, polyethers, amides, lactams, sulfonic acids, sulfonates, amines, hydroxyls,
ethers, esters, aldehydes, ketones, amino acids, methacrylated long chain hydrocarbons,
polymerizable ionic compounds, reactive latent compounds which may be converted to
ionic groups after the water soluble polymer is polymerized and combinations thereof.
14. The lens as claimed in claim 1 wherein said pendant groups further comprise at least
one second pendant group selected from the group consisting of amides, lactams,
glycosylated materials, polymerizable ionic compounds and combinations thereof.

15. The lens as claimed in claim 1 wherein said pendant groups further comprise at least
one second pendant group selected from the group consisting lauryl methacrylate, butyl
methacrylate, isopropyl methacrylate, methyl methacrylate, phenyl methacrylate,
hydroxyethyl methacrylate, methacrylic acid, glycerol monomethacrylate, hydroxyethyl
methacrylamide, 2-(-4-morpholinyl)ethyl methacrylate, morpholinyl methacrylamide, 2-
(N,N-dimethylamino)ethyl methacrylate, dimethylacrylamide, N-vinyl pyrrolidone, N-
vinyl-N-methylacetamide, styrene sulfonate, sodium 2- acrylamido-2-methyl-l-
propanesulfonate, sulfopropylacrylamide and combinations thereof.
16. An ophthalmic solution comprising at least one water soluble polymer having a
molecular weight of at least 500,000 Daltons and comprising linear or branched polyether
pendant groups having a molecular weight of at least 300.
17. The solution as claimed in claim 16 wherein said polyether pendant groups are
derived from monomers of the Formula I

wherein n is greater than 7; Z is a C1-C6 substituted or unsubstituted alkyl group, q is 0,1
or 2 and p is 2-q, y is 2 to 4, m is 1 or 2; A is any free radical polymerizable group and X
is a substituent independently selected from the group consisting of H, hydroxyl,
unsubstituted straight or branched alkyl groups, substituted straight or branched alkyl
groups, substituted and un substituted amines, substituted and un substituted amides,
mercaptans, ethers and esters.

18. The solution as claimed in claim 17 wherein X is selected from substituted or
unsubstituted straight or branched C1-16 alkyl groups.
19. The solution as claimed in claim 17 wherein X is selected from is selected from
substituted or unsubstituted straight or branched C1 -12 alkyl groups.
20. The solution as claimed in claim 18 wherein said alkyl group is substituted with a
group selected from the group consisting of carboxylic acids, esters, acyl halides, amines,
amides, ketones, aldehydes, halides, sulfides, mercaptans, quartenary ammonium salts
and combinations thereof.
21. The solution as claimed in claim 17 wherein n is an integer of between 7 to 50.
22. The solution as claimed in claim 16 wherein said polymer comprises at least 20% of
backbone units have a pendant group bound thereto.
21. The solution as claimed in claim 17 wherein at least 20% of said pendant groups are
polyether pendant groups of Formula I.

22. The solution as claimed in claim 16 wherein said pendant groups further comprise at
least one second pendant group selected from the group consisting of silicones, sugars,
carbohydrates, polyethers, amides, lactams, sulfonic acids, sulfonates, amines, hydroxyls,
ethers, esters, aldehydes, ketones, amino acids, methacrylated long chain hydrocarbons,
polymerizable ionic compounds, reactive latent compounds which may be converted to
ionic groups after the water soluble polymer is polymerized and combinations thereof.
23. The solution as claimed in claim 16 wherein said pendant groups further comprise at
least one second pendant group selected from the group consisting of amides, lactams,
glycosylated materials, polymerizable ionic compounds and combinations thereof.
24. The solution as claimed in claim 16 wherein said pendant groups further comprise at
least one second pendant group selected from the group consisting lauryl methacrylate,
butyl methacrylate, isopropyl methacrylate, methyl methacrylate, phenyl methacrylate,
hydroxyethyl methacrylate, methacrylic acid, glycerol monomethacrylate, hydroxyethyl
methacrylamide, 2-(-4-morpholinyl)ethyl methacrylate, morpholinyl methacrylamide, 2-
(N,N-dimethylamino)ethyl methacrylate, dimethylacrylamide, N-vinyl pyrrolidone, N-
vinyl-N-methylacetamide, styrene sulfonate, sodium 2- acrylamido-2-methyl-l-
propanesulfonate, sulfopropylacrylamide and combinations thereof.

25. The solution as claimed in claim 16, wherein said solution is a contact lens packing,
storing or cleaning solution.
26. The solution as claimed in claim 16, wherein said solution may be directly instilled
into the eye.
27. The solution as claimed in claim 18 further comprising additional components
selected from the group consisting of tonicity adjusting agents, viscosity adjusting agents,
antimicrobial agents, polyelectrolytes and mixtures thereof.


ABSTRACT

Title: Opthalmic compositions comprising polyether substituted polymers
A ophthalmic lens comprising at least one water soluble polymer having a molecular
weight of at least 500,000 Daltons and comprising linear or branched polyether pendant
groups having a molecular weight of at least 300.

Documents:

01815-kolnp-2007-abstract.pdf

01815-kolnp-2007-assignment.pdf

01815-kolnp-2007-claims.pdf

01815-kolnp-2007-correspondence others 1.1.pdf

01815-kolnp-2007-correspondence others 1.2.pdf

01815-kolnp-2007-correspondence others.pdf

01815-kolnp-2007-description complete.pdf

01815-kolnp-2007-form 1.pdf

01815-kolnp-2007-form 2.pdf

01815-kolnp-2007-form 3.pdf

01815-kolnp-2007-form 5.pdf

01815-kolnp-2007-gfa.pdf

01815-kolnp-2007-international publication.pdf

01815-kolnp-2007-international search report.pdf

01815-kolnp-2007-pct request form.pdf

1815-KOLNP-2007-(10-07-2012)-CORRESPONDENCE.pdf

1815-KOLNP-2007-(27-12-2011)-ABSTRACT.pdf

1815-KOLNP-2007-(27-12-2011)-CLAIMS.pdf

1815-KOLNP-2007-(27-12-2011)-CORRESPONDENCE.pdf

1815-KOLNP-2007-(27-12-2011)-DESCRIPTION (COMPLETE).pdf

1815-KOLNP-2007-(27-12-2011)-FORM-1.pdf

1815-KOLNP-2007-(27-12-2011)-FORM-2.pdf

1815-KOLNP-2007-(27-12-2011)-OTHERS.pdf

1815-KOLNP-2007-ASSIGNMENT.pdf

1815-KOLNP-2007-CORRESPONDENCE 1.1.pdf

1815-KOLNP-2007-CORRESPONDENCE.pdf

1815-KOLNP-2007-EXAMINATION REPORT.pdf

1815-KOLNP-2007-FORM 18 1.1.pdf

1815-kolnp-2007-form 18.pdf

1815-KOLNP-2007-FORM 3 1.1.pdf

1815-KOLNP-2007-FORM 3.pdf

1815-KOLNP-2007-FORM 5.pdf

1815-KOLNP-2007-GPA.pdf

1815-KOLNP-2007-GRANTED-ABSTRACT.pdf

1815-KOLNP-2007-GRANTED-CLAIMS.pdf

1815-KOLNP-2007-GRANTED-DESCRIPTION (COMPLETE).pdf

1815-KOLNP-2007-GRANTED-FORM 1.pdf

1815-KOLNP-2007-GRANTED-FORM 2.pdf

1815-KOLNP-2007-GRANTED-SPECIFICATION.pdf

1815-KOLNP-2007-INTERNATIONAL PUBLICATION.pdf

1815-KOLNP-2007-OTHERS 1.1.pdf

1815-KOLNP-2007-OTHERS.pdf

1815-kolnp-2007-pct search report.pdf

1815-KOLNP-2007-REPLY TO EXAMINATION REPORT.pdf


Patent Number 255651
Indian Patent Application Number 1815/KOLNP/2007
PG Journal Number 11/2013
Publication Date 15-Mar-2013
Grant Date 12-Mar-2013
Date of Filing 22-May-2007
Name of Patentee JOHNSON & JOHNSON VISION CARE, INC
Applicant Address 7500 CENTURION PARKWAY, SUITE 100JACKSONVILLE, FL 32256, U.S.A
Inventors:
# Inventor's Name Inventor's Address
1 FRANK MOLOCK 1543 WILD FERN DRIVE, ORANGE PARK, FL 32003
2 KATHRINE OSBORN LORENZ 3894 CRISWELL DRIVE, COLUMBUS, OHIO 43220
3 SHIVKUMAR MAHADEVAN 1905 WHITE DOGWOOD LANE, ORANGE PARK, FL 32003
PCT International Classification Number A61K 9/00, G02B 1/04
PCT International Application Number PCT/US2005/040836
PCT International Filing date 2005-11-10
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10/994,717 2004-11-22 U.S.A.