Patent US2459039A successfully refreshed from Google Patents.
US3957362A
Expired / Lapsed
US
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Hydrogels and articles made therefrom
Assignee: Corneal Sciences Inc
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Filing: 1974-03-18
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Granted: 1976-05-18
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Expires: 1994-03-18
Abstract
Abstract This invention relates to copolymers and hydrogels formed by copolymerization of a hydrophilic monomer from the group of dihydroxyalkyl acrylates and methacrylates and a substantially water insoluble monomer from the group of alkyl acrylates and methacrylates. The preferred copolymer of the invention is formed from methyl methacrylate and glyceryl methacrylate (2,3-dihydroxypropyl methacrylate). The hydrogels of the invention have unique physical and physiological properties which are particularly useful for the formation of contact lenses, particularly contact lenses having a relatively thin cross-section, though they may also be used for other purposes such as drug and pesticides delivery devices, dialysis, ultrafiltratiaon and reverse osmosis membranes, implants in surgery and dentistry and the like.
Inventors
- 👤 William L. Mancini
- 👤 Donald R. Korb
- 👤 Miguel F. Refojo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:08
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; A; A01; A01N; A01N25/00; A01N25/08; A01N25/10; A61; A61K; A61K9/00; A61K9/20; A61K9/2004; A61K9/2022; A61K9/2027; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/26; C08F220/28; C08F220/282
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
127 words
A contact lens of a copolymer formed by the free radical bulk polymerization of a mixture consisting essentially of two acrylic monomers in the substantial absence of water or other diluent, said first monomer being hydrophilic and conforming to the formula: ##EQU4## where R is hydrogen or methyl and n is a whole integer having a value of from 0 to 4, and said second monomer being substantially water insoluble and conforming to the formula: ##EQU5## where R is as above described and R' is alkyl having from 1 to 6 carbon atoms, the mole ratio of said first acrylate to said second acrylate varying between 1:1 and 10:1, said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 2
Dependent Claim
127 words
A contact lens of a copolymer formed by the free radical bulk polymerization of a mixture consisting essentially of two acrylic monomers in the substantial absence of water or other diluent, said first monomer being hydrophilic and conforming to the formula: ##EQU4## where R is hydrogen or methyl and n is a whole integer having a value of from 0 to 4, and said second monomer being substantially water insoluble and conforming to the formula: ##EQU5## where R is as above described and R' is alkyl having from 1 to 6 carbon atoms, the mole ratio of said first acrylate to said second acrylate varying between 1:1 and 10:1, said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 3
Dependent Claim
26 words
The contact lens of claim 1 where the mole ratio of said first acrylate of said copolymer to said second acrylate varies between 1.2:1 and 2:1.
Claim 4
Dependent Claim
17 words
The contact lens of claim 1 where the reaction temperature of the copolymerization reaction is about 40°C.
Claim 5
Dependent Claim
16 words
The contact lens of claim 1 where the R of each of said acrylates is methyl.
Claim 6
Dependent Claim
27 words
The contact lens of claim 1 where R of said first and said second acrylates and R' of said second acrylate are methyl and n is 1.
Claim 7
Dependent Claim
43 words
The contact lens of claim 1 where the copolymer is formed under conditions whereby a hydrated round button formed from said copolymer having a thickness of 3 mm and a diameter of 12 mm will appear slightly milky when viewed through its cross-section.
Claim 8
Dependent Claim
65 words
A contact lens of a copolymer formed by free radical bulk polymerization of a mixture consisting essentially of 2,3--dihydroxypropyl methacrylate and methyl methacrylate in the substantial absence of water or other diluent, the molar ratio of 2,3--dihydroxypropyl methacrylate to methyl methacrylate ranging between about 1:1 and 10:1 said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 9
Dependent Claim
65 words
A contact lens of a copolymer formed by free radical bulk polymerization of a mixture consisting essentially of 2,3--dihydroxypropyl methacrylate and methyl methacrylate in the substantial absence of water or other diluent, the molar ratio of 2,3--dihydroxypropyl methacrylate to methyl methacrylate ranging between about 1:1 and 10:1 said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 10
Dependent Claim
26 words
The contact lens of claim 7 where the mole ratio of 2,3--dihydroxypropyl methacrylate of said copolymer to the methyl methacrylate varies between about 1.2:1 and 3:1.
Claim 11
Dependent Claim
14 words
The contact lens of claim 8 where the ratio is about 1.5 to 1.
Claim 12
Dependent Claim
29 words
The contact lens of claim 8 where the copolymer is formed in the presence of 0.02 weight percent of a catalyst based upon the weight of the 2,3--dihydroxypropyl methacrylate.
Claim 13
Dependent Claim
43 words
The contact lens of claim 7 where the copolymer is formed under conditions whereby a hydrated round button formed from said copolymer having a thickness of 3 mm and a diameter of 12 mm will appear slightly milky when viewed through its cross-section.
Claim 14
Dependent Claim
10 words
The contact lens of claim 1 saturated with a drug.
Claim 15
Dependent Claim
9 words
The contact lens of claim 1 saturated with water.
Claim 16
Dependent Claim
17 words
The contact lens of claim 1 being saturated with an aqueous liquid containing a physiologically active solute.
Claim 17
Dependent Claim
11 words
The contact lens of claim 1 where said solute is bacteriostatic.
Claim 18
Dependent Claim
16 words
The contact lens of claim 1 having anterior or posterior peripheral curvature or multiple peripheral curvatures.
Claim 19
Dependent Claim
10 words
The contact lens of claim 7 saturated with a drug.
Claim 20
Dependent Claim
9 words
The contact lens of claim 7 hydrated with water.
Claim 21
Dependent Claim
16 words
The contact lens of claim 7 saturated with an aqueous liquid containing a physiologically active solute.
Claim 22
Dependent Claim
11 words
The contact lens of claim 7 where the solute is bacteriostatic.
Claim 23
Dependent Claim
16 words
The contact lens of claim 7 having anterior and/or posterior peripheral curvature or multiple peripheral curvatures.
Claim 24
Dependent Claim
151 words
A free radical, bulk polymerization process for preparing a copolymeric structure suitable for use as a contact lens comprising forming a mixture consisting essentially of two acrylates in the substantial absence of water or other diluent, said first acrylate being hydrophilic and conforming to the formula: ##EQU6## where R is hydrogen or methyl and n is a whole integer having a value of from 0 to 4, and said second acrylate being substantially water insoluble and conforming to the formula: ##EQU7## where R is as above described and R' is alkyl having from 1 to 6 carbon atoms, the molar ratio of said first acrylate to said second acrylate varying between 1:1 and 10:1 and causing said mixture to react so as to form a solid, shape-retaining body of copolymer of said two acrylates that is insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 25
Dependent Claim
151 words
A free radical, bulk polymerization process for preparing a copolymeric structure suitable for use as a contact lens comprising forming a mixture consisting essentially of two acrylates in the substantial absence of water or other diluent, said first acrylate being hydrophilic and conforming to the formula: ##EQU6## where R is hydrogen or methyl and n is a whole integer having a value of from 0 to 4, and said second acrylate being substantially water insoluble and conforming to the formula: ##EQU7## where R is as above described and R' is alkyl having from 1 to 6 carbon atoms, the molar ratio of said first acrylate to said second acrylate varying between 1:1 and 10:1 and causing said mixture to react so as to form a solid, shape-retaining body of copolymer of said two acrylates that is insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane.
Claim 26
Dependent Claim
16 words
The process of claim 22 including the step of hydrating the copolymer to form a hydrogel.
Claim 27
Dependent Claim
23 words
The process of claim 22 where the mole ratio of said first acrylate to said second acrylate varies between about 1.2:1 and 2:1.
Claim 28
Dependent Claim
15 words
The process of claim 22 where R and R' are methyl and n is 1.
Claim 29
Dependent Claim
12 words
The process of claim 22 where the reaction temperature is about 40°C.
Claim 30
Dependent Claim
22 words
The process of claim 22 where a catalyst is used in an amount of about 0.02% by weight of said first acrylate.
Claim 31
Dependent Claim
10 words
The process of claim 27 where the catalyst is isopropylpercarbonate.
Claim 32
Dependent Claim
86 words
A contact lens of a copolymer formed by free-radical bulk copolymerization of a mixture consisting essentially of 2,3--dihydroxypropyl methacrylate and methyl methacrylate, the mole ratio of said 2,3--dihydroxypropyl methacrylate to methyl methacrylate varying between 1:1 and 10:1, said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane, said lens being a hydrogel which when hydrated swells linearly between 17 and 19%, absorbs about 39 to 42% liquid and has a durometer hardness of between about 46 to 49.
Claim 33
Dependent Claim
86 words
A contact lens of a copolymer formed by free-radical bulk copolymerization of a mixture consisting essentially of 2,3--dihydroxypropyl methacrylate and methyl methacrylate, the mole ratio of said 2,3--dihydroxypropyl methacrylate to methyl methacrylate varying between 1:1 and 10:1, said copolymer being insoluble in a solvent system comprising 60% by volume acetone and 40% by volume dioxane, said lens being a hydrogel which when hydrated swells linearly between 17 and 19%, absorbs about 39 to 42% liquid and has a durometer hardness of between about 46 to 49.
Claim 34
Dependent Claim
15 words
The contact lens of claim 29 having a thickness varying between 0.05mm and 0.15 mm.
Claim 35
Dependent Claim
50 words
The contact lens of claim 1, further comprising from about 1% to about 3% by weight, based on said first monomer, of an epoxy compound conforming to the formula: ##EQU8## where R is hydrogen or methyl and n is a whole integer having a value of from 0 to 4.
Claim 36
Dependent Claim
28 words
The copolymer of claim 31, wherein the epoxy compound is present in an amount of from about 1.8% to about 2.2% by weight based on said first monomer.
References Cited (Backward Citations)
US2976576A
Cited
US3220960A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-18 | 1979-11-17 | 1980-05-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-18 | 1983-11-17 | 1984-05-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-18 | 1987-11-17 | 1988-05-18 | $7700.00 | Window Closed / Lapsed |