EP0216074A2
Expired / Lapsed
EP
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Polyvinyl alcohol derivatives and crosslinked hydrogel contact lenses made therefrom
Assignee: Novartis AG
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Filing: 1986-07-28
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Granted: —
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Expires: 2006-07-28
Abstract
Abstract Polymers which are derivatives of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of units of the formula wherein R' and R 2 are independently alkylene, arylene, a divalent cycloaliphatic group, arylenealkylene, alkylenearylene or arylenealkylenearylene, n is 0 or 1, A' is oxygen or NR', A is oxygen, NR" or a bivalent ureido group, R 3 is hydrogen or methyl, R 4 is hydrogen, methyl or COOR 5 , where R 5 is hydrogen or lower alkyl, with the proviso that if R 3 is methyl, R 4 is hydrogen, R' and R" are independently hydrogen or lower alkyl, these polymers being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I, and crosslinked hydrogel contact lenses made therefrom and their preparation.
Inventors
- 👤 Merrill Goldenberg
- 👤 Karl Friedrich Mueller
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-23 10:35
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08F; C08F261/00; C08F261/02; C08F261/04; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/62; C08G18/6212; C08G18/70; C08G18/81; C08G18/8108; C08G18/8116; C08G2210/00
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
157 words
A polymer which is a derivative of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of units of the formula wherein R 1 and R 2 are independently alkylene, arylene, a divalent cycloaliphatic group, arylenealkylene, alkylenearylene or arylenealkylenearylene, n is 0 or 1, A 1 is oxygen or NR', A is oxygen, NR" or a bivalent ureido group, R 3 is hydrogen or methyl, R 4 is hydrogen, methyl or COOR 5 , where R 5 is hydrogen or lower alkyl, with the proviso that if R 3 is methyl, R 4 is hydrogen, R' and R" are independently hydrogen or lower alkyl, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 2
Dependent Claim
157 words
A polymer which is a derivative of a polyvinyl alcohol, having a weight average molecular weight of at least about 2,000, and containing from about 0.5 to about 90 percent, based on the number of hydroxyl groups in said polyvinyl alcohol, of units of the formula wherein R 1 and R 2 are independently alkylene, arylene, a divalent cycloaliphatic group, arylenealkylene, alkylenearylene or arylenealkylenearylene, n is 0 or 1, A 1 is oxygen or NR', A is oxygen, NR" or a bivalent ureido group, R 3 is hydrogen or methyl, R 4 is hydrogen, methyl or COOR 5 , where R 5 is hydrogen or lower alkyl, with the proviso that if R 3 is methyl, R 4 is hydrogen, R' and R" are independently hydrogen or lower alkyl, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 3
Dependent Claim
197 words
A polymer according to claim 1 which is a derivative of a polyvinyl alcohol having a weight average molecular weight of at least about 2,000, and containing an effective amount between about 0.5 and 90 percent, based on the number of hydroxylgroups on said polyvinyl alcohol, of units of the formula I wherein R l and R 2 are independently alkylene of 2 to 8 carbon atoms, arylene of 6 to 12 carbon atoms, a saturated cycloaliphatic divalent group of 6 to 10 carbon atoms, arylenealkylene or alkylenearylene of 7 to 14 carbon atoms, or arylenealkylenearylene of 13 to 16 carbon atoms; n is 0 or 1; A 1 is oxygen or NR' where R' is hydrogen or lower alkyl; A is oxygen, NR" or NHCONR", where R" is hydrogen or lower alkyl; R 3 is hydrogen or methyl; R 4 is hydrogen, methyl or COOR 5 , where R 5 is hydrogen or lower alkyl with the proviso that if R 3 is methyl, R 4 is hydrogen, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 4
Dependent Claim
97 words
A polymer according to claim 2 wherein in formula I R 1 and R 2 are independently alkylene of 2 to 6 carbon atoms, phenylene, unsubstituted or substituted by lower alkyl, cyclohexylene, cyclohexylene lower alkylene, unsubstituted or substituted by lower alkyl, phenylene lower alkylene, lower alkylene phenylene or phenylene lower alkylene phenylene and n, A 1 , A, R 3 and R 4 are as defined in claim 2, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 5
Dependent Claim
63 words
A polymer according to claim 2 wherein in formula I A is oxygen, R 3 is methyl, R 4 is hydrogen, n is zero and R 1 is alkylene of 2 to 6 carbon atoms, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 6
Dependent Claim
77 words
A polymer according to claim 2 wherein in formula I A is oxygen, R 3 is methyl, R 4 is hydrogen, n is one, R 1 is lower alkyl phenylene or lower alkyl cyclohexylene lower alkylene, R 2 is lower alkylene, and A 1 is oxygen or N-lower alkyl, this polymer being an addition reaction product of units of formula I with from 0 to about 80 units of a vinylic monomer per unit of formula I.
Claim 7
Dependent Claim
20 words
A polymer according to claim 1 wherein said polyvinyl alcohol has a weight average molecular weight of at least 10,000.
Claim 8
Dependent Claim
20 words
A polymer according to claim 1 wherein said polyvinyl alcohol has a weight average molecular weight of up to 100,000.
Claim 9
Dependent Claim
15 words
A polymer according to claim 1 wherein no units of a vinylic monomer are used.
Claim 10
Dependent Claim
20 words
A polymer according to claim 8 containing from about 0.5 to about 35 percent of units of the formula I.
Claim 11
Dependent Claim
21 words
A polymer according to claim 9 wherein said polyvinyl alcohol has a weight average molecular weight of between 10,000 and 100,000.
Claim 12
Dependent Claim
10 words
A polymer according to claim 8 wherein n is zero.
Claim 13
Dependent Claim
15 words
A polymer according to claim 8 wherein n is 1 and A l is oxygen.
Claim 14
Dependent Claim
32 words
A polymer according to claim 8 wherein n is 0, R l is alkylene of 2 to 6 carbon atoms, A is oxygen, R 3 is methyl and R 4 is hydrogen.
Claim 15
Dependent Claim
11 words
A polymer according to claim 13 wherein R 1 is ethylene.
Claim 16
Dependent Claim
24 words
A polymer according to claim 1 wherein between about 0.01 and about 80 units of vinylic monomer are reacted per unit of formula I.
Claim 17
Dependent Claim
36 words
A polymer according to claim 15 wherein the polymer contains from at least about 1 percent to about 90 percent of units of formula I, based on the number of hydroxyl groups on the polyvinyl alcohol.
Claim 18
Dependent Claim
86 words
A polymer according to claim 16, wherein the polyvinyl alcohol contains at least about 1 up to about 20 percent units of formula I based upon the number of hydroxyl groups on said polyvinyl alcohol, which are reacted with about 0.5 to about 30 units of either a hydrophobic vinylic monomer or, a mixture of hydrophobic and hydrophilic vinylic monomers containing at least 50 percent by weight of hydrophobic monomer based upon the total weight of said vinylic monomers, based upon the units of formula I.
Claim 19
Dependent Claim
70 words
A polymer according to claim 16, wherein the polyvinyl alcohol contains from about 20 up to about 50 percent units of formula I based on the number of hydroxyl groups on said polyvinyl alcohol, which are reacted with about 0.01 to about 10 units of vinylic monomer, wherein u p to about 80 weight percent of the total vinylic monomer is hydrophilic, per unit of formula I in the polymer.
Claim 20
Dependent Claim
84 words
A polymer according to claim 16, wherein the polyvinyl alcohol contains from about 50 to about 90 percent units of formula I based on the number of hydroxyl groups on said polyvinyl alcohol, which are reacted with about 0.01 to about 10 units of either a hydrophilic vinylic monomer or, a mixture of hydrophilic and hydrophobic vinylic monomers containing at least 50 percent by weight of hydrophilic monomer based upon the total weight of said vinylic monomers, based upon the units of formula I.
Claim 21
Dependent Claim
19 words
A polymer according to any one of claims 17 to 19 wherein n is zero and A is oxygen.
Claim 22
Dependent Claim
37 words
A polymer according to any one of claims 17 to 19 wherein n is 0, R 1 is alkylene of 2 to 6 carbon atoms, A is oxygen, R 3 is methyl and R 4 is hydrogen.
Claim 23
Dependent Claim
11 words
A polymer according to claim 21 wherein R 1 is ethylene.
Claim 24
Dependent Claim
92 words
A polymer according to any one of claims 17 to 19 wherein a hydrophobic monomer is selected from C 1-18 -alkyl acrylates and methacrylates, C 3-18 -alkyl acrylamides and methacrylamides, acrylonitrile, methacrylonitrile, vinyl C 1-18 -alkanoates, C 2-18 -alkenes, C 2-18 -haloalkenes, styrene, C 1-6 -alkyl styrenes, vinyl alkyl ethers wherein the alkyl portion has 1 to 6 carbon atoms, C 3-12 -perfluoroalkyl ethyl thiocarbonylaminoethyl acrylates and methacrylates, C 3-12 -fluoroalkyl acrylates and methacrylates, acryloxy and methacryloxy alkyl siloxanes, N-vinyl carbazole, C 1-12 -alkyl esters of maleic, fumaric, itaconic, and mesaconic acids.
Claim 25
Dependent Claim
63 words
A polymer according to claim 23 wherein a hydrophobic monomer is selected from methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, vinyl ethyl ether, perfluorohexylethylthiocarbonylaminoethyl methacrylate, isobornyl methacrylate, hexafluorobutylmethacrylate, 3-methacryl- oxypropylpentamethyldisiloxane, and bis(methacryloxypropyl)tetramethyldisiloxane.
Claim 26
Dependent Claim
86 words
A polymer according to any one of claims 17 to 19 wherein a hydrophilic monomer is selected from hydroxy substituted lower alkyl acrylates and methacrylates, acrylamide, methacrylamide, C I-2 -lower alkyl acrylamide and methacrylamide, ethoxylated acrylates and methacrylates, hydroxy substituted lower alkyl acrylamide and methacrylamide, hydroxy substituted lower alkyl vinyl ethers, sodium ethylene sulfonate, sodium styrene sulfonate, 2-acrylamido-2-methylpropanesulfonic acid, N-vinylpyrrole, N-vinylsuccinimide, N-vinyl pyrrolidone, 2- and 4-vinyl pyridine, acrylic acid, methacrylic acid, amino (by amino including quaternary ammonium) -monolower-alkylamino- or diloweralkylamino-lower alkyl acrylates or methacrylates, allyl alcohol.
Claim 27
Dependent Claim
29 words
A polymer according to claim 25 wherein a hydrophilic monomer is selected from hydroxyethyl methacrylate, hydroxyethyl acrylate, acrylamide, methacrylamide, dimethylacrylamide, allyl alcohol, vinyl pyridine, vinyl pyrrolidone, glycerol methacrylate, N-(1,1-dimethyl-3-oxobutyl)acrylamide.
Claim 28
Dependent Claim
33 words
A polymer according to claim 17 wherein the hydrophobic vinylic monomer is selected from methyl methacrylate and vinyl acetate and the hydrophilic vinylic monomer is selected from 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone and acrylamide.
Claim 29
Dependent Claim
33 words
A polymer according to claim 18 wherein the hydrophobic vinylic monomer is selected from methyl methacrylate and vinyl acetate and the hydrophilic vinylic monomer is selected from 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone and acrylamide.
Claim 30
Dependent Claim
33 words
A polymer according to claim 19 wherein the hydrophobic vinylic monomer is selected from methyl methacrylate and vinyl acetate and the hydrophilic vinylic monomer is selected from 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone and acrylamide.
Claim 31
Dependent Claim
14 words
A crosslinked polymeric hydrogel material, prepared by crosslinking a polymer according to claim 1.
Claim 32
Dependent Claim
48 words
A hydrated contact lens prepared by crosslinking a polymer according to claim 1 in the presence of an organic solvent and a free radical initiator, in a contact lens mold, and equilibrating the resultant swollen crosslinked polymeric material in an aqueous medium to recover said hydrated contact lens.
Claim 33
Dependent Claim
33 words
Process for the manufacture of a crosslinked polymeric hydrogel material characterized in that a polymer according to claim 1 is crosslinked in the presence of an organic solvent and a free radical initiator.
Claim 34
Dependent Claim
12 words
Process according to claim 32 wherein a photoinitiator and UV-light are used.
Claim 35
Dependent Claim
27 words
Process according to claim 33 wherein the organic solvent is selected from ethanol, methanol, dimethylformamide, acetamide, acetonitrile, dimethylacetamide, dimethylsulfoxide or mixtures thereof, or mixtures thereof with water.
Claim 36
Dependent Claim
11 words
Process according to claim 33 wherein the organic solvent is dimethylsulfoxide.
Claim 37
Dependent Claim
55 words
Process for the manufacture of a hydrated contact Ions characterized in that a polymer according to claim 1 is crosslinked in the presence of an organic solvent and a free radical initiator, in a contact lens mold, and equilibrating the resultant swollen crosslinked polymeric material in an aqueous medium to recover said hydrated contact lens.
Claim 38
Dependent Claim
13 words
A process according to claim 36 wherein a photoinitiator and UV-light are used.
Claim 39
Dependent Claim
28 words
A process according to claim 36 wherein the organic solvent is selected from ethanol, methanol, dimethylformamide, acetamide, acetonitrile, dimethylacetamide, dimethylsulfoxide or mixtures thereof, or mixtures thereof with water.
Claim 40
Dependent Claim
12 words
A process according to claim 36 wherein the organic solvent is dimethylsulfoxide.
Claim 41
Dependent Claim
14 words
A crosslinked polymeric hydrogel according to claim 30 for use as a contact lens.
References Cited (Backward Citations)
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