Ophthalmic Solutions
Disclosed are ophthalmic solutions such as packaging solutions for storing ophthalmic devices and lens care solutions for cleaning, disinfecting, rinsing and/or storing ophthalmic devices. The ophthalmic solutions contain at least a polymerization product obtained from a monomeric mixture comprising (a) a monomer bearing a center of permanent positive charge and (b) a non-ionic ethylenically unsaturated monomer, wherein the solution has an osmolality of at least about 200 mOsm/kg, and a pH of about 4 to about 9.
1 . A packaging system for the storage of an ophthalmic device comprising a sealed container containing one or more unused ophthalmic device immersed in an aqueous packaging solution comprising a polymerization product obtained from a monomer mixture comprising (a) a monomer bearing a center of permanent positive charge and (b) a non-ionic ethylenically unsaturated monomer, wherein the solution has an osmolality of at least about 200 mOsm/kg, a pH of about 4 to about 9 and is heat sterilized.
2 . The packaging system of claim 1 , wherein the monomer bearing a center of permanent positive charge is a cationic monomer.
3 . The packaging system of claim 1 , wherein the monomer bearing a center of permanent positive charge is a zwitterionic monomer.
4 . The packaging system of claim 1 , wherein the monomer bearing a center of permanent positive charge is of Formula I:
Y—B—X (I)
wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain; X is a group bearing a center of permanent positive charge and Y is an ethylenically unsaturated polymerizable group.
5 . The packaging system of claim 1 , wherein the monomer bearing a center of permanent positive charge is of general Formula III or IV:
wherein R 9 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or fluoroalkyl group; A is —O— or —NR 10 — wherein R 10 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or R 10 is —B—X wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain, X is a group bearing a center of permanent positive charge and K can be a group of the formulae —(CH 2 ) i CO(O)—, —(CH 2 ) i C(O)O—, —(CH 2 ) i COC(O)O—, —(CH 2 ) i CNR 11 —, —(CH 2 ) i NR 11 C(O)—, —(CH 2 ) i C(O)NR 11 —, (CH 2 ) i NR 11 C(O)O—, —(CH 2 ) i OC(O)NR 11 —, —(CH 2 ) i NR 11 C(O)NR 11 —, —(CH 2 ) i O—, —(CH 2 ) i SO 3 —, or, optionally in a combination with B, a valence bond, and i is from 1 to 12 and R 11 is the same or different and is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group.
6 . The packaging system of claim 2 , wherein the cationic monomer comprises a quaternary ammonium moiety.
7 . The packaging system of claim 3 , wherein the zwitterionic monomer comprises a quaternary ammonium moiety and a phosphate moiety.
8 . The packaging system of claim 1 , wherein the monomer bearing a center of permanent positive charge is selected from the group consisting of methacrylamidopropyltrimethyl ammonium chloride, acryloyloxyethyl trimethyl ammonium chloride, methacryloyloxyethyl trimethyl ammonium chloride, 2-methacryloxyethyl phosphorylcholine, 1-(4(4′-vinylbenzyloxy)butane)-2′(trimethylammonium)ethyl phosphate, [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl) ammonium hydroxide salt, dimethylaminoethyl methacrylate diethylsulfate and mixtures thereof.
9 . The packaging system of claim 1 , wherein the non-ionic ethylenically unsaturated monomer is selected from the group consisting of a hydroxyalkyl (alk)acrylate, a hydroxyalkyl acrylamide, a N-vinyl lactam, a polyhydroxyl (alk)acrylate, a polyhydroxyl acrylamide and mixtures thereof.
10 . The packaging system of claim 1 , wherein the polymerization product is present in the solution in an amount of about 0.005% w/w to about 1% w/w.
11 . The packaging system of claim 1 , wherein the solution further comprises a buffering agent.
12 . The packaging system of claim 11 , wherein the buffering agent comprises a borate or phosphate compound.
13 . The packaging system of claim 1 , wherein package is heat sterilized subsequent to sealing of the package.
14 . The packaging system of claim 1 , wherein the solution does not contain an effective disinfecting amount of a disinfecting agent.
15 . The packaging system of claim 1 , wherein the solution does not contain a germicide compound.
16 . The packaging system of claim 1 , wherein the ophthalmic device is a contact lens.
17 . The packaging system of claim 1 , wherein the ophthalmic device is an anionic contact lens.
18 . A method of treating a biomedical device, the method comprising:
contacting a biomedical device with a solution comprising a polymerization product obtained from a monomer mixture comprising (a) a monomer bearing a center of permanent positive charge and (b) a non-ionic ethylenically unsaturated monomer.
19 . The method of claim 18 , comprising:
immersing the biomedical device in the solution;
removing the device from the solution;
packaging the biomedical device in a packaging solution in a manner preventing contamination of the device by microorganisms; and
sterilizing the packaged solution and device.
20 . The method of claim 18 , comprising:
immersing the biomedical device in the solution;
packaging the solution containing the biomedical device in a packaging solution in a manner preventing contamination of the device by microorganisms; and
sterilizing the packaged solution and device.
21 . The method of claim 18 , comprising:
immersing the biomedical device in the solution;
packaging the solution and the device in a manner preventing contamination of the device by microorganisms; and
sterilizing the packaged solution and device.
22 . The method of claim 18 , comprising:
soaking the biomedical device in the solution;
removing the biomedical device from the solution; and
placing the biomedical device directly in the eye.
23 . The method of claim 18 , wherein the biomedical device is an ophthalmic lens.
24 . The method of claim 18 , wherein the biomedical device is a contact lens.
25 . The method of claim 18 , where in the monomeric mixture the monomer bearing a center of permanent positive charge is of the Formula I:
Y—B—X (I)
wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain; X is a group bearing a center of permanent positive charge and Y is an ethylenically unsaturated polymerizable group.
26 . The method of claim 18 , where in the monomeric mixture the monomer bearing a center of permanent positive charge is of general Formula III or IV:
wherein R 9 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or fluoroalkyl group; A is —O— or —NR 10 — wherein R 10 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or R 10 is —B—X wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain, X is a group bearing a center of permanent positive charge and K can be a group of the formulae —(CH 2 ) i CO(O)—, —(CH 2 ) i C(O)O—, —(CH 2 ) i COC(O)O—, —(CH 2 ) i CNR 11 —, —(CH 2 ) i NR 11 C(O)—, —(CH 2 ) i C(O)NR 11 —, (CH 2 ) i NR 11 C(O)O—, —(CH 2 ) i OC(O)NR 11 —, —(CH 2 ) i NR 11 C(O)NR 11 —, —(CH 2 ) i O—, —(CH 2 ) i SO 3 —, optionally in a combination with B, a valence bond, and i is from 1 to 12 and R 11 is the same or different and is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group.
27 . The method of claim 18 , where in the monomeric mixture the monomer bearing a center of permanent positive charge comprises a quaternary ammonium moiety.
28 . The method of claim 18 , where in the monomeric mixture the monomer bearing a center of permanent positive charge comprises a quaternary ammonium moiety and a phosphate moiety.
29 . The method of claim 18 , where in the monomeric mixture the monomer bearing a center of permanent positive charge is selected from the group consisting of methacrylamidopropyltrimethyl ammonium chloride, acryloyloxyethyl trimethyl ammonium chloride, methacryloyloxyethyl trimethyl ammonium chloride, 2-methacryloxyethyl phosphorylcholine, 1-(4(4′-vinylbenzyloxy)butane)-2′(trimethylammonium)ethyl phosphate, [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl) ammonium hydroxide salt, dimethylaminoethyl methacrylate diethylsulfate and mixtures thereof.
30 . The method of claim 18 , where in the monomeric mixture the non-ionic ethylenically unsaturated monomer is selected from the group consisting of a hydroxyalkyl (alk)acrylate, a hydroxyalkyl acrylamide, a N-vinyl lactam, a polyhydroxyl (alk)acrylate, a polyhydroxyl acrylamide and mixtures thereof.
31 . A multi-purpose ophthalmically acceptable solution comprising (a) a polymerization product obtained from a monomer mixture comprising (i) a monomer bearing a center of permanent positive charge and (ii) a non-ionic ethylenically unsaturated monomer; and (b) an ophthalmically acceptable carrier for the polymerization product.
32 . The multi-purpose ophthalmically acceptable solution of claim 31 , having an osmolality of at least about 200 mOsm/kg, and a pH of about 4 to about 9
33 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the monomer bearing a center of permanent positive charge is of the formula:
Y—B—X (I)
wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain; X is a group bearing a center of permanent positive charge and Y is an ethylenically unsaturated polymerizable group.
34 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the monomer bearing a center of permanent positive charge is of general Formula III or IV:
wherein R 9 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or fluoroalkyl group; A is —O— or —NR 10 — wherein R 10 is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group or R 10 is —B—X wherein B is a bond, a straight or branched, substituted or unsubstituted alkylene, substituted or unsubstituted oxaalkylene, or substituted or unsubstituted oligooxaalkylene chain, X is a group bearing a center of permanent positive charge and K can be a group of the formulae —(CH 2 ) i CO(O)—, —(CH 2 ) i C(O)O—, —(CH 2 ) i COC(O)O—, —(CH 2 ) i CNR 11 —, —(CH 2 ) i NR 11 C(O)—, —(CH 2 ) i C(O)NR 11 —, (CH 2 ) i NR 11 C(O)O—, —(CH 2 ) i OC(O)NR 11 —, —(CH 2 ) i NR 11 C(O)NR 11 —, —(CH 2 ) i O—, —(CH 2 ) i SO 3 —, or, optionally in a combination with B, a valence bond, and i is from 1 to 12 and R 11 is the same or different and is hydrogen or a substituted or unsubstituted C 1 -C 4 alkyl group.
35 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the monomer bearing a center of permanent positive charge comprises a quaternary ammonium moiety.
36 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the monomer bearing a center of permanent positive charge comprises a quaternary ammonium moiety and a phosphate moiety.
37 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the monomeric mixture the monomer bearing a center of permanent positive charge is selected from the group consisting of methacrylamidopropyltrimethyl ammonium chloride, acryloyloxyethyl trimethyl ammonium chloride, methacryloyloxyethyl trimethyl ammonium chloride, 2-methacryloxyethyl phosphorylcholine, 1-(4(4′-vinylbenzyloxy)butane)-2′(trimethylammonium)ethyl phosphate, [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl) ammonium hydroxide salt, dimethylaminoethyl methacrylate diethylsulfate and mixtures thereof.
38 . The multi-purpose ophthalmically acceptable solution of claim 31 , wherein the non-ionic ethylenically unsaturated monomer is selected from the group consisting of a hydroxyalkyl (alk)acrylate, a hydroxyalkyl acrylamide, a N-vinyl lactam, a polyhydroxyl (alk)acrylate, a polyhydroxyl acrylamide and mixtures thereof.
39 . The multi-purpose ophthalmically acceptable solution of claim 29 , wherein the polymerization product is present in the solution in an amount of about 0.005% w/w to about 1% w/w.
40 . The multi-purpose ophthalmically acceptable solution of claim 31 , further comprising one or more antimicrobial agents.
41 . A packaging system for the storage of an ophthalmic device comprising a sealed container containing one or more unused ophthalmic device immersed in an aqueous packaging solution comprising a copolymer comprising one or more first monomeric segments having a cationic charge and one or more second monomeric non-ionic segments, wherein the solution has an osmolality of at least about 200 mOsm/kg, a pH of about 4 to about 9 and is heat sterilized.
42 . A multi-purpose ophthalmically acceptable solution comprising (a) a copolymer comprising one or more first monomeric segments having a cationic charge and one or more second monomeric non-ionic segments; and (b) an ophthalmically acceptable carrier for the copolymer.