Patent US4152508A successfully refreshed from Google Patents.
US4152508A
Expired / Lapsed
US
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Silicone-containing hard contact lens material
Assignee: B&L International Holdings Corp
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Filing: 1978-02-15
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Granted: 1979-05-01
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Expires: 1998-02-15
Abstract
Abstract An improved contact lens material is formed by a copolymer of a siloxanyl alkyl ester monomer, an itaconate ester and an ester of acrylic or methacrylic acid. The copolymer preferably includes a cross-linking agent and a hydrophilic monomer. Contact lenses made of the mterial can be readily machined and polished into hard contact lenses having excellent dimensional stability but also have extremely high permeability to oxygen.
Inventors
- 👤 Edward J. Ellis
- 👤 Joseph C. Salamone
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:26
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; C; C08; C08F; C08F230/00; C08F230/04; C08F230/08; G02B1/041; G02B1/043; Y; Y10; Y10S; Y10S526/00; Y10S526/923
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
203 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic, contact lens material of high transparency consisting essentially of a polymer formed by free radical polymerization from (a) 30-80% by weight of a siloxanyl alkyl ester monomer having the following formula: ##STR4## where R 1 is selected from the class of hydrogen or methyl groups, "a" is an integer from one to three, "b" and "c" are integers from zero to two, "d" is an integer from zero to one, A is selected from the class of methyl or phenyl groups, R 2 is selected from the class of methyl or phenyl groups, R 3 and R 4 represent either no group(cyclic ring from "c" to "d") or methyl or phenyl groups, (b) 5 to 60% by weight of an itaconate mono- or di-ester, (c) 1 to 60 parts by weight of an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid, (d) 0.1 to 10% by weight of a cross-linking agent, (e) 1 to 20% by weight of a hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material of this invention.
Claim 2
Dependent Claim
203 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic, contact lens material of high transparency consisting essentially of a polymer formed by free radical polymerization from (a) 30-80% by weight of a siloxanyl alkyl ester monomer having the following formula: ##STR4## where R 1 is selected from the class of hydrogen or methyl groups, "a" is an integer from one to three, "b" and "c" are integers from zero to two, "d" is an integer from zero to one, A is selected from the class of methyl or phenyl groups, R 2 is selected from the class of methyl or phenyl groups, R 3 and R 4 represent either no group(cyclic ring from "c" to "d") or methyl or phenyl groups, (b) 5 to 60% by weight of an itaconate mono- or di-ester, (c) 1 to 60 parts by weight of an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid, (d) 0.1 to 10% by weight of a cross-linking agent, (e) 1 to 20% by weight of a hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material of this invention.
Claim 3
Dependent Claim
94 words
A contact lens material in accordance with claim 1 wherein said siloxanyl alkyl ester monomer (a) is present in an amount of from 40 to 55% by weight, said itaconate ester (b) is present in an amount of from 20 to 40% by weight, said ester (c) is present in an amount of from 20 to 40% by weight, said cross-linking agent is present in an amount of from 0.1 to 10% by weight, and said hydrophilic monomer is present in an amount of from 1 to 20% by weight of the entire composition.
Claim 4
Dependent Claim
41 words
A contact lens material in accordance with claim 1 wherein said ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid is methyl methacrylate.
Claim 5
Dependent Claim
33 words
A contact lens material in accordance with claim 3 wherein said siloxanyl alkyl ester monomer is selected from the class consisting essentially of methacryloyloxymethyl pentamethyldisiloxane, methacryloyloxypropyl tris(trimethylsilyl) siloxane, methacryloyloxymethyl heptamethylcyclotetrasiloxane and methacryloyloxypropyl heptamethylcyclotetrasiloxane.
Claim 6
Dependent Claim
33 words
A contact lens material in accordance with claim 4 wherein said itaconate ester is selected from the class consisting essentially of methyl itaconate, dimethyl itaconate, phenyl itaconate, diphenyl itaconate and methyl phenyl itaconate.
Claim 7
Dependent Claim
41 words
A contact lens material in accordance with claim 5 wherein said material has an oxygen permeability in the range of from about 38 cm 3 mm/cm 2 sec cmHg×10 -10 to about 500 cm 3 mm/cm 2 sec cmHg×10 -10 .
Claim 8
Dependent Claim
41 words
A contact lens material in accordance with claim 1 wherein said material has an oxygen permeability in the range of from about 38 cm 3 mm/cm 2 sec cmHg×10 -10 to about 500 cm 3 mm/cm 2 sec cmHg×10 -10 .
Claim 9
Dependent Claim
41 words
A contact lens material in accordance with claim 2 wherein said material has an oxygen permeability in the range of from about 38 cm 3 mm/cm 2 sec cmHg×10 -10 to about 500 cm 3 mm/cm 2 sec cmHg×10 -10 .
Claim 10
Dependent Claim
199 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens consisting essentially of a polymer formed by free radical polymerization from (a) 30-80% by weight of a siloxanyl alkyl ester monomer having the following formula: ##STR5## where R 1 is selected from the class of hydrogen or methyl groups, "a" is an integer from one to three, "b" and "c" are integers from zero to two, "d" is an integer from zero to one, A is selected from the class of methyl or phenyl groups, R 2 is selected from the class of methyl or phenyl groups, R 3 and R 4 represent either no group(cyclic ring from "c" to "d") or methyl or phenyl groups, (b) 5 to 60% by weight of an itaconate mono- or di-ester, (c) 1 to 60 parts by weight of an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid, (d) 0.1 to 10% by weight of a cross-linking agent, (e) 1 to 20% by weight of a hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material of this invention.
Claim 11
Dependent Claim
199 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens consisting essentially of a polymer formed by free radical polymerization from (a) 30-80% by weight of a siloxanyl alkyl ester monomer having the following formula: ##STR5## where R 1 is selected from the class of hydrogen or methyl groups, "a" is an integer from one to three, "b" and "c" are integers from zero to two, "d" is an integer from zero to one, A is selected from the class of methyl or phenyl groups, R 2 is selected from the class of methyl or phenyl groups, R 3 and R 4 represent either no group(cyclic ring from "c" to "d") or methyl or phenyl groups, (b) 5 to 60% by weight of an itaconate mono- or di-ester, (c) 1 to 60 parts by weight of an ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid, (d) 0.1 to 10% by weight of a cross-linking agent, (e) 1 to 20% by weight of a hydrophilic monomer to impart hydrophilic properties to the surface of the contact lens material of this invention.
Claim 12
Dependent Claim
100 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens in accordance with claim 9 wherein said siloxanyl alkyl ester monomer (a) is present in an amount of from 40 to 55% by weight, said itaconate ester (b) is present in an amount of from 20 to 40% by weight, said ester (c) is present in an amount of from 20 to 40% by weight, said cross-linking agent is present in an amount of from 0.1 to 10% by weight, and said hydrophilic monomer is present in an amount of from 1 to 20% by weight of the entire composition.
Claim 13
Dependent Claim
47 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens in accordance with claim 9 wherein said ester of a C 1 -C 20 monohydric or polyhydric alkanol or phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid is methyl methacrylate.
Claim 14
Dependent Claim
39 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens in accordance with claim 11 wherein said siloxanyl alkyl ester monomer is selected from the class consisting essentially of methacryloyloxymethyl pentamethyldisiloxane, methacryloyloxypropyl tris(trimethylsilyl) siloxane, methacryloyloxymethyl heptamethylcyclotetrasiloxane and methacryloyloxypropyl heptamethylcyclotetrasiloxane.
Claim 15
Dependent Claim
39 words
An oxygen permeable, hard, machinable, dimensionally stable, hydrophilic contact lens in accordance with claim 12 wherein said itaconate ester is selected from the class consisting essentially of methyl itaconate, dimethyl itaconate, phenyl itaconate, diphenyl itaconate and methyl phenyl itaconate.
Claim 16
Dependent Claim
68 words
A hard, oxygen permeable contact lens having good dimensional stability, high transparency and formed by free radical copolymerization of dimethyl itaconate, methyl methacrylate, methacryloxyloxypropyl tris (trimethylsilyl) siloxane, methacrylic acid and tetraethylene glycol dimethacrylate, said lens having an oxygen permeability in the range of from 38 to 500 cm 3 mm/cm 2 sec cmHg×10 -10 and a Rockwell Hardness value of from 100 to 125 ASTM D-785 R scale.
Claim 17
Dependent Claim
68 words
A hard, oxygen permeable contact lens having good dimensional stability, high transparency and formed by free radical copolymerization of dimethyl itaconate, methyl methacrylate, methacryloxyloxypropyl tris (trimethylsilyl) siloxane, methacrylic acid and tetraethylene glycol dimethacrylate, said lens having an oxygen permeability in the range of from 38 to 500 cm 3 mm/cm 2 sec cmHg×10 -10 and a Rockwell Hardness value of from 100 to 125 ASTM D-785 R scale.
References Cited (Backward Citations)
US3808178A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-30 | 1982-10-30 | 1983-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-30 | 1986-10-30 | 1987-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-30 | 1990-10-30 | 1991-05-01 | $7700.00 | Window Closed / Lapsed |