US4022754A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel copolymer having utility as contact lens
Assignee: AO Inc 14 MECHANIC ST A CORP OF
•
Filing: 1975-01-27
•
Granted: 1977-05-10
•
Expires: 1995-01-27
Abstract
Abstract Water-swellable lightly cross-linked copolymers, specifically terpolymers, between 3-methoxy-2-hydroxy-propyl methacrylate (G-MEMA), at least one N-vinyl lactam and at least one copolymerizable monomer to increase strength and stiffness, have utility as contact lenses. Preferred examples contain methyl methacrylate (MMA) and vinylpyrrolidone (VP) as comonomers, and up to 5% e.g. 2% of a cross-linking agent, preferably with non-equivalent functional groups such as allyl methacrylate. Preferably the water content is up to 65% based on total gel, e.g. 50-60% by weight; the VP:MMA ratio is from 50:50 to 70:30 and from 10-75% by weight G-MEMA units are present.
Inventors
- 👤 John Gordon Bernard Howes
- 👤 Rupert Aleck Selway
- 👤 Nicholas Mario DA Costa
- 👤 William Duncan Potter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 03:55
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; C08F226/00; C08F226/06
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
130 words
A lightly cross-linked hydrogel terpolymer formed from: 1. from 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate; 2. N-vinyl-2-pyrrolidone; 3. a further copolymerizable monomer selected from the group consisting of methacrylamide and methacrylate monomers which are more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable monomer ranging from 50:50 to 70:30; the terpolymer being cross-linked with up to 2%, by weight, of copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 2
Dependent Claim
130 words
A lightly cross-linked hydrogel terpolymer formed from: 1. from 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate; 2. N-vinyl-2-pyrrolidone; 3. a further copolymerizable monomer selected from the group consisting of methacrylamide and methacrylate monomers which are more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable monomer ranging from 50:50 to 70:30; the terpolymer being cross-linked with up to 2%, by weight, of copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 3
Dependent Claim
14 words
The terpolymer of claim 1 wherein the further copolymerizable monomer is a methacrylate monomer.
Claim 4
Dependent Claim
23 words
A terpolymer as claimed in claim 1 wherein the crosslinking agent is selected from the group consisting of diacrylyl and dimethacryl crosslinking agents.
Claim 5
Dependent Claim
25 words
A terpolymer as claimed in claim 2 wherein the said cross-linking agent is a cross-linking agent having two functional cross-linking groups which differ in reactivity.
Claim 6
Dependent Claim
33 words
A terpolymer as claimed in claim 2 wherein the cross-linking agent is selected from the group consisting of the unsaturated aliphatic monoesters of acrylic acid and the unsaturated aliphatic monoesters of methacrylic acid.
Claim 7
Dependent Claim
14 words
A terpolymer as claimed in claim 5 wherein the cross-linking agent is allyl methacrylate.
Claim 8
Dependent Claim
15 words
A terpolymer as claimed in claim 5 wherein the cross-linking agent is 3-allyloxy-2-hydroxy propyl methacrylate.
Claim 9
Dependent Claim
14 words
A terpolymer as claimed in claim 2 of water uptake from 50% to 60%.
Claim 10
Dependent Claim
32 words
A terpolymer as claimed in claim 1 wherein the further copolymerizable monomer (3) is selected from the group consisting of methyl methacrylate, 3-tert.-butoxy-2-hydroxy propyl methacrylate, phenoxyethyl methacrylamide, benzyl methacrylate and 2-phenylethyl methacrylate.
Claim 11
Dependent Claim
19 words
A terpolymer as claimed in claim 2 wherein the VP: monomer (3) weight ratio is from 55:45 to 65:35.
Claim 12
Dependent Claim
19 words
A terpolymer as claimed in claim 10 wherein the VP: monomer (3) weight ratio is from 58:42 to 62:38.
Claim 13
Dependent Claim
16 words
A terpolymer as claimed in claim 2 containing 25% to 75%, by weight, of component (1).
Claim 14
Dependent Claim
14 words
A terpolymer as claimed in claim 2 containing 30% to 60% of component (1).
Claim 15
Dependent Claim
14 words
A terpolymer as claimed in claim 2 containing 10% to 40% of component (1).
Claim 16
Dependent Claim
16 words
A terpolymer as claimed in claim 2 containing 25% to 35%, by weight, of component (1).
Claim 17
Dependent Claim
16 words
A terpolymer as claimed in claim 2 containing 50% to 75%, by weight, of component (1).
Claim 18
Dependent Claim
16 words
A terpolymer as claimed in claim 2 containing 55% to 65%, by weight, of component (1).
Claim 19
Dependent Claim
123 words
A lightly cross-linked hydrogel copolymer formed from (1) 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate, (2) N-vinyl-2-pyrrolidone and (3) at least one further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30, said copolymer being cross-linked with up to 2% of a copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 20
Dependent Claim
123 words
A lightly cross-linked hydrogel copolymer formed from (1) 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate, (2) N-vinyl-2-pyrrolidone and (3) at least one further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30, said copolymer being cross-linked with up to 2% of a copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 21
Dependent Claim
70 words
A lightly cross-linked hydrogen terpolymer between 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone and methyl methacrylate; said terpolymer having a water uptake of 50% to 60%, by weight, based on total eventual weight of gel, a ratio of N-vinyl-2-pyrrolidone to methyl methacrylate between 58:42 and 62:38, a content of 3-methoxy-2-hydroxy propyl methacrylate units from 50% to 75%, by weight, and said terpolymer being cross-linked by up to 2%, by weight, of allyl methacrylate.
Claim 22
Dependent Claim
70 words
A lightly cross-linked hydrogen terpolymer between 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone and methyl methacrylate; said terpolymer having a water uptake of 50% to 60%, by weight, based on total eventual weight of gel, a ratio of N-vinyl-2-pyrrolidone to methyl methacrylate between 58:42 and 62:38, a content of 3-methoxy-2-hydroxy propyl methacrylate units from 50% to 75%, by weight, and said terpolymer being cross-linked by up to 2%, by weight, of allyl methacrylate.
Claim 23
Dependent Claim
128 words
A contact lens made from a lightly cross-linked hydrogel terpolymer formed from: 1. from 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate; 2. N-vinyl-2-pyrrolidone; 3. a further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30; the terpolymer being cross-linked with (4) up to 2%, by weight, of copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 24
Dependent Claim
128 words
A contact lens made from a lightly cross-linked hydrogel terpolymer formed from: 1. from 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate; 2. N-vinyl-2-pyrrolidone; 3. a further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the swollen cross-linked N-vinyl-2-pyrrolidone, the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30; the terpolymer being cross-linked with (4) up to 2%, by weight, of copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents whereby it is in the form of a lightly cross-linked hydrogel, of water uptake up to 65% based on the total eventual weight of gel, suitable for use as a contact lens.
Claim 25
Dependent Claim
73 words
A contact lens made from a lightly cross-linked hydrogel terpolymer between 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone and methyl methacrylate; said terpolymer having a water uptake of 50% to 60%, by weight, based on total weight of gel, an N-vinyl-2-pyrrolidone to 3-methyl methacrylate ratio between 58:42 and 62:38, a content of 3-methoxy-2-hydroxy propyl methacrylate units from 50% to 75%, by weight, and said copolymer being cross-linked by up to 2%, by weight, of allyl methacrylate.
Claim 26
Dependent Claim
73 words
A contact lens made from a lightly cross-linked hydrogel terpolymer between 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone and methyl methacrylate; said terpolymer having a water uptake of 50% to 60%, by weight, based on total weight of gel, an N-vinyl-2-pyrrolidone to 3-methyl methacrylate ratio between 58:42 and 62:38, a content of 3-methoxy-2-hydroxy propyl methacrylate units from 50% to 75%, by weight, and said copolymer being cross-linked by up to 2%, by weight, of allyl methacrylate.
Claim 27
Independent Claim
178 words
A method of producing a terpolymer comprising the following steps: mixing together, in the presence of up to 2%, by weight, of a copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents; from (1) 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate, (2) N-vinyl-2-pyrrolidone and (3) a further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the eventual polymer the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30; heating the mixture at a temperature from 30° C to 55° C for a time from 4 to 24 hours to effect controlled isothermal polymerization, said polymerization being initiated in the presence of an initiator for free radical polymerization; heating the polymer formed at from 90° C to 120° C for up to 5 hours to effect a post-cure; and said terpolymer thereby formed as a lightly cross-linked hydrogel of water uptake up to 65% based on the total eventual weight of gel.
Claim 28
Independent Claim
178 words
A method of producing a terpolymer comprising the following steps: mixing together, in the presence of up to 2%, by weight, of a copolymerizable crosslinking agent selected from the group consisting of methacrylyl and acrylyl crosslinking agents; from (1) 10 to 75%, by weight, of 3-methoxy-2-hydroxy propyl methacrylate, (2) N-vinyl-2-pyrrolidone and (3) a further copolymerizable methacrylate monomer which is more hydrophobic than components (1) and (2) and which will increase the strength and stiffness of the eventual polymer the weight ratio of N-vinyl-2-pyrrolidone to the said further copolymerizable methacrylate monomer ranging from 50:50 to 70:30; heating the mixture at a temperature from 30° C to 55° C for a time from 4 to 24 hours to effect controlled isothermal polymerization, said polymerization being initiated in the presence of an initiator for free radical polymerization; heating the polymer formed at from 90° C to 120° C for up to 5 hours to effect a post-cure; and said terpolymer thereby formed as a lightly cross-linked hydrogel of water uptake up to 65% based on the total eventual weight of gel.
Claim 29
Independent Claim
148 words
A method of producing a terpolymer comprising the following steps: mixing together, in the presence of up to 2%, by weight, of allyl methacrylate as a crosslinking agent, 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone, and methyl methacrylate, the ratio of N-vinyl-2-pyrrolidone to methyl methacrylate being from 58:42 to 62:38 and the 3-methoxy-2-hydroxy propyl methacrylate content being 50% to 75%, by weight; heating the mixture at a temperature from 30° C to 55° C for a time from 4 to 24 hours to effect controlled isothermal polymerization, said polymerization being initiated in the presence of an initiator for free radical polymerization; heating the polymer formed at from 90° C to 120° C for up to 5 hours to effect a post-cure; and said terpolymer thereby being formed as a lightly cross-linked hydrogel with an uptake of physiological saline of up to 50% to 60% based on total eventual weight of gel.
Claim 30
Independent Claim
148 words
A method of producing a terpolymer comprising the following steps: mixing together, in the presence of up to 2%, by weight, of allyl methacrylate as a crosslinking agent, 3-methoxy-2-hydroxy propyl methacrylate, N-vinyl-2-pyrrolidone, and methyl methacrylate, the ratio of N-vinyl-2-pyrrolidone to methyl methacrylate being from 58:42 to 62:38 and the 3-methoxy-2-hydroxy propyl methacrylate content being 50% to 75%, by weight; heating the mixture at a temperature from 30° C to 55° C for a time from 4 to 24 hours to effect controlled isothermal polymerization, said polymerization being initiated in the presence of an initiator for free radical polymerization; heating the polymer formed at from 90° C to 120° C for up to 5 hours to effect a post-cure; and said terpolymer thereby being formed as a lightly cross-linked hydrogel with an uptake of physiological saline of up to 50% to 60% based on total eventual weight of gel.
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) | 1980-05-09 | 1980-11-08 | 1981-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-09 | 1984-11-08 | 1985-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-09 | 1988-11-08 | 1989-05-10 | $7700.00 | Window Closed / Lapsed |