US4536554A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydrophilic polymers and contact lenses made therefrom
Assignee: Barnes Hind Hydrocurve Inc
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Filing: 1984-02-22
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Granted: 1985-08-20
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Expires: 2004-02-22
Abstract
Abstract An interpenetrating network polymer is obtained by mixing hydrophilic monomer vinyl pyrrolidone and hydrophobic monomer (5-alkylene-m-dioxanyl) acrylic ester in the presence of at least two crosslinking agents and, optionally, hydroxyalkyl acrylic ester and catalysts and causing polymerization to occur. Contact lenses made from the polymer have high tensile strength and can absorb a high degree of water.
Inventors
- 👤 Drahoslav Lim
- 👤 Chidambar L. Kulkarni
- 👤 Dennis A. Repella
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:50
CPC Classifications
C; C08; C08L; C08L35/00; C08F; C08F226/00; C08F226/06; C08F226/10; C08L33/00; C08L33/04; C08L33/06; C08L33/10; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
169 words
A contact lens comprised of an interpenetrating network polymer comprising (a) hydrophilic vinyl pyrrolidone, 50-80% by weight; (b) a first crosslinking agent having an affinity for hydrophilic vinyl pyrrolidone, 0.1-1.0% by weight; said first crosslinking agent being 3,3'-ethylidine-bis (N-vinyl-2-pyrrolidone), diallyl itaconate, diallyl maleate, diallyl fumarate, dimethallyl fumarate, dimethallyl maleate, diallyl diglycollate, diethylene glycol bis (allyl carbonate), diallyl oxalate, diallyl adipate, diallyl succinate, diallyl azelate, divinyl benzene, divinyl adipate, or divinylethers; (c) (5-alkylene-m-dioxanyl)acrylic ester, 10-45% by weight, having the formula ##STR2## wherein R and R 1 are independently H or C 1 -C 4 alkyl, R 2 and R 3 are independently H, C 1 -C 4 alkyl, or phenyl, and n is an integer from 1-4; (d) hydroxyalkyl acrylic ester, 0-20% by weight; (e) a second crosslinking agent having an affinity for acrylic esters of (c) and (d), 0.1-2% by weight, said agent being neopentyl glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1,6-hexane diol dimethacrylate, glycerol trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, trimethylol propane trimethyacrylate, allylmethacrylate, or corresponding acrylates.
Claim 2
Dependent Claim
169 words
A contact lens comprised of an interpenetrating network polymer comprising (a) hydrophilic vinyl pyrrolidone, 50-80% by weight; (b) a first crosslinking agent having an affinity for hydrophilic vinyl pyrrolidone, 0.1-1.0% by weight; said first crosslinking agent being 3,3'-ethylidine-bis (N-vinyl-2-pyrrolidone), diallyl itaconate, diallyl maleate, diallyl fumarate, dimethallyl fumarate, dimethallyl maleate, diallyl diglycollate, diethylene glycol bis (allyl carbonate), diallyl oxalate, diallyl adipate, diallyl succinate, diallyl azelate, divinyl benzene, divinyl adipate, or divinylethers; (c) (5-alkylene-m-dioxanyl)acrylic ester, 10-45% by weight, having the formula ##STR2## wherein R and R 1 are independently H or C 1 -C 4 alkyl, R 2 and R 3 are independently H, C 1 -C 4 alkyl, or phenyl, and n is an integer from 1-4; (d) hydroxyalkyl acrylic ester, 0-20% by weight; (e) a second crosslinking agent having an affinity for acrylic esters of (c) and (d), 0.1-2% by weight, said agent being neopentyl glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1,6-hexane diol dimethacrylate, glycerol trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, trimethylol propane trimethyacrylate, allylmethacrylate, or corresponding acrylates.
Claim 3
Dependent Claim
40 words
A contact lens of claim 1 wherein (a) is N-vinyl-2-pyrrolidone; (c) has the formula wherein R is methyl, n is 1, R 1 is methyl, R 2 and R 3 are H, being (5-methyl-5-m-dioxanyl)methyl methacrylate; and (d) is 2-hydroxyethyl methacrylate.
Claim 4
Dependent Claim
17 words
A contact lens of claim 2 wherein (b) is 3,3'-ethylene-bis (N-vinyl-2-pyrrolidine) and (e) is neopentyl glycol dimethacrylate.
Claim 5
Dependent Claim
48 words
A contact lens comprised of an interpenetrating network polymer comprising (a) N-vinyl-2-pyrrolidone, 50-65%; (b) 3,3'-ethylene-bis (N-vinyl-2-pyrrolidine), 0.3-0.5%; (c) (5-methyl-5-m-dioxanyl)methyl methacylate, 30-33%; (d) 2-hydroxyethyl methacrylate, 5-8%; and (e) neopentyl glycol dimethacrylate 0.1-2.0%; wherein the percentages are by weight based on the total weight of monomer exclusive of crosslinking agents.
Claim 6
Dependent Claim
48 words
A contact lens comprised of an interpenetrating network polymer comprising (a) N-vinyl-2-pyrrolidone, 50-65%; (b) 3,3'-ethylene-bis (N-vinyl-2-pyrrolidine), 0.3-0.5%; (c) (5-methyl-5-m-dioxanyl)methyl methacylate, 30-33%; (d) 2-hydroxyethyl methacrylate, 5-8%; and (e) neopentyl glycol dimethacrylate 0.1-2.0%; wherein the percentages are by weight based on the total weight of monomer exclusive of crosslinking agents.
Claim 7
Dependent Claim
121 words
A contact lens comprised of an interpenetrating network polymer comprised of 50-80% of a first network comprised of N-vinyl-2-pyrrolidone crosslinked with 0.1-1.0% by weight, 3,3'-ethylidene-bis (N-vinyl-2-pyrrolidone), diallyl itaconate, diallyl maleate, diallyl fumarate, dimethallyl fumarate, dimethallyl maleate, diallyl diglycollate, diethylene glycol bis (allyl carbonate), diallyl oxalate, diallyl adipate, diallyl succinate, diallyl azelate, divinyl benzene, divinyl adipate, or divinylethers, and the balance a second network comprised of 2-hydroxyethyl methacrylate, 0-20% by weight and (5-methyl-5-m-dioxanyl)methyl methacrylate, 10-45% by weight, crosslinked with 0.1-2% neopentyl glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1,6-hexane diol dimethacrylate, glycerol trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, trimethylol propane trimethyacrylate, allylmethacrylate, or corresponding acrylates; wherein the percentages are by weight based on the total weight of monomer exclusive of crosslinking agents.
Claim 8
Dependent Claim
121 words
A contact lens comprised of an interpenetrating network polymer comprised of 50-80% of a first network comprised of N-vinyl-2-pyrrolidone crosslinked with 0.1-1.0% by weight, 3,3'-ethylidene-bis (N-vinyl-2-pyrrolidone), diallyl itaconate, diallyl maleate, diallyl fumarate, dimethallyl fumarate, dimethallyl maleate, diallyl diglycollate, diethylene glycol bis (allyl carbonate), diallyl oxalate, diallyl adipate, diallyl succinate, diallyl azelate, divinyl benzene, divinyl adipate, or divinylethers, and the balance a second network comprised of 2-hydroxyethyl methacrylate, 0-20% by weight and (5-methyl-5-m-dioxanyl)methyl methacrylate, 10-45% by weight, crosslinked with 0.1-2% neopentyl glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1,6-hexane diol dimethacrylate, glycerol trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, trimethylol propane trimethyacrylate, allylmethacrylate, or corresponding acrylates; wherein the percentages are by weight based on the total weight of monomer exclusive of crosslinking agents.
Claim 9
Dependent Claim
28 words
A contact lens of claim 5 wherein the first network has been crosslinked with 3,3'ethylidene bis (N-vinyl-2-pyrrolidone) and the second network has been crosslinked with neopentyl glycol dimethacylate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-19 | 1989-02-18 | 1989-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-19 | 1993-02-18 | 1993-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-19 | 1997-02-18 | 1997-08-20 | $7700.00 | Window Closed / Lapsed |