US4038264A
Expired / Lapsed
US
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Hema copolymers having high oxygen permeability
Assignee: NEATSIMPLE Ltd
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Filing: 1974-11-22
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Granted: 1977-07-26
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Expires: 1994-11-22
Abstract
Abstract Hydrophilic copolymers are prepared of compounds having the formulae: ##STR1## where R is hydrogen or methyl, R 2 is alkylene of 2 to 3 carbon atoms, R 1 is alkoxy of 1 to 6 carbon atoms, R 3 is alkylene of 2 to 3 carbon atoms and m is an integer of 2 to 6. The preferred copolymers are hydroxyethyl methacrylate-methoxytriethyleneglycol methacrylate copolymers. The products are characterized by having an unusually high oxygen permeability compared to other hydrophilic polymers and are particularly valuable in making contact lenses.
Inventors
- 👤 Martin Rostoker
- 👤 Leon Levine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 11:31
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/26; C08F220/28; C08F220/282
Claims Analysis
Total Claims: 56
Claim 1
Independent Claim
128 words
A hydrophilic, water insoluble copolymer which is (A) a copolymer of 25 to 97.5% of a compound having the formula (1) ##STR7## and 75 to 2.5% of a compound having the formula (2) ##STR8## where R is hydrogen or methyl, R 2 is alkylene of 2 to 3 carbon atoms, m is an integer of 2 to 6, R 3 is alkylene of 2 to 3 carbon atoms and R 1 is alkoxy of 1 to 6 carbon atoms or (B) a copolymer of at least 50% of (1), up to 40% of (2), and up to 40% of a modifier selected from the group consisting of vinylpyrrolidone, vinylacetate, glycerol methacrylate, trimethylolpropane methacrylate, vinyl propionate sodium salt of 2-acrylamide-2-methylpropane sulfonic acid, polyvinyl pyrrolidone, vinylpyrrolidonevinylacetate copolymer and polyvinyl alcohol.
Claim 2
Dependent Claim
128 words
A hydrophilic, water insoluble copolymer which is (A) a copolymer of 25 to 97.5% of a compound having the formula (1) ##STR7## and 75 to 2.5% of a compound having the formula (2) ##STR8## where R is hydrogen or methyl, R 2 is alkylene of 2 to 3 carbon atoms, m is an integer of 2 to 6, R 3 is alkylene of 2 to 3 carbon atoms and R 1 is alkoxy of 1 to 6 carbon atoms or (B) a copolymer of at least 50% of (1), up to 40% of (2), and up to 40% of a modifier selected from the group consisting of vinylpyrrolidone, vinylacetate, glycerol methacrylate, trimethylolpropane methacrylate, vinyl propionate sodium salt of 2-acrylamide-2-methylpropane sulfonic acid, polyvinyl pyrrolidone, vinylpyrrolidonevinylacetate copolymer and polyvinyl alcohol.
Claim 3
Dependent Claim
18 words
A copolymer according to claim 1 which has been prepared in the presence of a free radical initiator.
Claim 4
Dependent Claim
18 words
A copolymer according to claim 1 which is A and has a water uptake of 60 to 300%.
Claim 5
Dependent Claim
24 words
A copolymer according to claim 1 comprising at least 50% of (1), up to 40% of (2), and up to 40% of a modifier.
Claim 6
Dependent Claim
14 words
A copolymer according to claim 3 having a water uptake of 54.7 to 129.7%.
Claim 7
Dependent Claim
17 words
A copolymer according to claim 5 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 8
Dependent Claim
21 words
A copolymer according to claim 1 which is (A) and has been prepared in the presence of a free radical initiator.
Claim 9
Dependent Claim
21 words
A copolymer according to claim 1 which is (B) and has been prepared in the presence of a free radical initiator.
Claim 10
Dependent Claim
56 words
A hydrophilic, water insoluble copolymer of claim 1 which is (A) where R is hydrogen or methyl, R 2 is alkylene of 2 to 3 carbon atoms, m is an integer of 2 to 6, R 3 is alkylene of 2 to 4 carbon atoms and R 1 is alkoxy of 1 to 6 carbon atoms.
Claim 11
Dependent Claim
23 words
A copolymer according to claim 9 wherein m is 2 to 3 and R 1 is alkoxy of 1 to 2 carbon atoms.
Claim 12
Dependent Claim
28 words
A copolymer according to claim 10 wherein R is methyl, R 2 is alkylene of 2 carbon atoms, R 3 is alkylene of 2 to 3 carbon atoms.
Claim 13
Dependent Claim
17 words
A copolymer according to claim 11 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 14
Dependent Claim
22 words
A copolymer according to claim 12 wherein the methoxytriethylene glycol methacrylate is 5 to 65% of the total of (1) and (2).
Claim 15
Dependent Claim
22 words
A copolymer according to claim 13 wherein the methoxytriethylene glycol methacrylate is 10 to 65% of the total of (1) and (2).
Claim 16
Dependent Claim
22 words
A copolymer according to claim 14 wherein the methoxytriethylene glycol methacrylate is 40 to 60% of the total of (1) and (2).
Claim 17
Dependent Claim
21 words
A copolymer according to claim 12 which has the relationship of oxygen permeability to water uptake satisfied by the equation ##EQU1##
Claim 18
Dependent Claim
13 words
A copolymer according to claim 1 which is a sparingly cross-linked hydrophilic polymer.
Claim 19
Dependent Claim
26 words
A copolymer according to claim 17 wherein the cross-linking agent is a polymerizable diester of acrylic acid or methacrylic acid with a glycol or polyalkylene glycol.
Claim 20
Dependent Claim
27 words
A copolymer according to claim 17 wherein the cross-linking agent is present in an amount of 0.05 to 5% based on the total of (1) and (2).
Claim 21
Dependent Claim
25 words
A copolymer according to claim 19 wherein the cross-linking agent is present in an amount up to 2% of the total of (1) and (2).
Claim 22
Dependent Claim
27 words
A copolymer according to claim 20 wherein the cross-linking agent is present in an amount of 0.1 to 1% based on the total of (1) and (2).
Claim 23
Dependent Claim
23 words
A copolymer according to claim 17 wherein m is 2 to 3 and R 1 is alkoxy of 1 to 2 carbon atoms.
Claim 24
Dependent Claim
26 words
A copolymer according to claim 17 wherein R is methyl, R 2 is alkylene of 2 carbon atoms, R 3 is alkylene of 2 carbon atoms.
Claim 25
Dependent Claim
17 words
A copolymer according to claim 23 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 26
Dependent Claim
22 words
A copolymer according to claim 24 wherein the methoxytriethylene glycol methacrylate is 5 to 65% of the total of (1) and (2).
Claim 27
Dependent Claim
22 words
A copolymer according to claim 25 wherein the methoxytriethylene glycol methacrylate is 10 to 65% of the total of (1) and (2).
Claim 28
Dependent Claim
22 words
A copolymer according to claim 26 wherein the methoxytriethylene glycol methacrylate is 40 to 60% of the total of (1) and (2).
Claim 29
Dependent Claim
21 words
A copolymer according to claim 24 which has the relationship of oxygen permeability to water uptake satisfied by the equation ##EQU2##
Claim 30
Dependent Claim
15 words
A copolymer according to claim 24 wherein the cross linking agent is ethylene glycol dimethacrylate.
Claim 31
Dependent Claim
27 words
A copolymer according to claim 29 wherein the ethylene glycol dimethacrylate is present in an amount of 0.1 to 2% of the total of (1) and (2).
Claim 32
Dependent Claim
9 words
A copolymer according to claim 9 in dry form.
Claim 33
Dependent Claim
12 words
A copolymer according to claim 9 in the form of a hydrogel.
Claim 34
Dependent Claim
10 words
A contact lens made of the polymer of claim 9.
Claim 35
Dependent Claim
24 words
A contact lens according to claim 33 wherein m is 2 to 3 and R 1 is alkoxy of 1 to 2 carbon atoms.
Claim 36
Dependent Claim
28 words
A contact lens according to claim 33 wherein R is methyl, R 2 is alkylene of 2 carbon atoms, and R 3 is alkylene of 2 carbon atoms.
Claim 37
Dependent Claim
18 words
A contact lens according to claim 35 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 38
Dependent Claim
23 words
A contact lens according to claim 36 wherein the methoxytriethylene glycol methacrylate is 5 to 65% of the total of (1) and (2).
Claim 39
Dependent Claim
23 words
A contact lens according to claim 37 wherein the methoxytriethylene glycol methacrylate is 10 to 65% of the total of (1) and (2).
Claim 40
Dependent Claim
23 words
A contact lens according to claim 38 wherein the methoxytriethylene glycol methacrylate is 40 to 60% of the total of (1) and (2).
Claim 41
Dependent Claim
22 words
A contact lens according to claim 36 which has the relationship of oxygen permeability to water uptake satisfied by the equation ##EQU3##
Claim 42
Dependent Claim
27 words
A contact lens according to claim 33 wherein the cross-linking agent is a polymerizable diester of acrylic acid or methacrylic acid with a glycol or polyalkylene glycol.
Claim 43
Dependent Claim
28 words
A contact lens according to claim 33 wherein the cross-linking agent is present in an amount of 0.05 to 5% based on the total of (1) and (2).
Claim 44
Dependent Claim
26 words
A contact lens according to claim 42 wherein the cross-linking agent is present in an amount up to 2% of the total of (1) and (2).
Claim 45
Dependent Claim
28 words
A contact lens according to claim 43 wherein the cross-linking agent is present in an amount of 0.1 to 1% based on the total of (1) and (2).
Claim 46
Dependent Claim
24 words
A contact lens according to claim 33 wherein m is 2 to 3 and R 1 is alkoxy of 1 to 2 carbon atoms.
Claim 47
Dependent Claim
26 words
A copolymer according to claim 45 wherein R is methyl, R 2 is alkylene of 2 carbon atoms, R 3 is alkylene of 2 carbon atoms.
Claim 48
Dependent Claim
18 words
A contact lens according to claim 46 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 49
Dependent Claim
23 words
A contact lens according to claim 47 wherein the methoxytriethylene glycol methacrylate is 5 to 65% of the total of (1) and (2).
Claim 50
Dependent Claim
23 words
A contact lens according to claim 48 wherein the methoxytriethylene glycol methacrylate is 10 to 65% of the total of (1) and (2).
Claim 51
Dependent Claim
23 words
A contact lens according to claim 49 wherein the methoxytriethylene glycol methacrylate is 40 to 60% of the total of (1) and (2).
Claim 52
Dependent Claim
22 words
A contact lens according to claim 47 which has the relationship of oxygen permeability to water uptake satisfied by the equation ##EQU4##
Claim 53
Dependent Claim
7 words
A contact lens according to claim 4.
Claim 54
Dependent Claim
17 words
A copolymer according to claim 4 wherein (1) is hydroxyethyl methacrylate and (2) is methoxytriethylene glycol methacrylate.
Claim 55
Dependent Claim
34 words
A copolymer according to claim 4 comprising hydroxyethyl methacrylate as (1), methoxytriethylene glycol methacrylate as (2), and a mixture of the trimethylammonium chloride hydroxypropyl ester of methacrylic acid and the sodium 2-acrylamide-2-methylpropane sulfonic acid.
Claim 56
Dependent Claim
7 words
A contact lens according to claim 54.
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) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |