WO1994011764B1 - Polymeric compositions and intraocular lenses made from same - Google Patents
Polymeric compositions and intraocular lenses made from sameInfo
- Publication number
- WO1994011764B1 WO1994011764B1 PCT/US1993/010657 US9310657W WO9411764B1 WO 1994011764 B1 WO1994011764 B1 WO 1994011764B1 US 9310657 W US9310657 W US 9310657W WO 9411764 B1 WO9411764 B1 WO 9411764B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- monomeric component
- constituent
- intraocular lens
- copolymer
- acrylate
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 21
- 239000000470 constituent Substances 0.000 claims abstract 24
- 229920001577 copolymer Polymers 0.000 claims abstract 20
- 229920001519 homopolymer Polymers 0.000 claims abstract 9
- 239000011521 glass Substances 0.000 claims abstract 4
- 238000004132 cross linking Methods 0.000 claims abstract 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 4
- -1 naphthyl acrylate Chemical compound 0.000 claims 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- BKKVYNMMVYEBGR-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(Br)=C1Br BKKVYNMMVYEBGR-UHFFFAOYSA-N 0.000 claims 2
- APQXWKHOGQFGTB-UHFFFAOYSA-N 1-ethenyl-9H-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C=C APQXWKHOGQFGTB-UHFFFAOYSA-N 0.000 claims 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims 2
- MUKJDVAYJDKPAG-UHFFFAOYSA-N 2,3-dibromopropyl prop-2-enoate Chemical compound BrCC(Br)COC(=O)C=C MUKJDVAYJDKPAG-UHFFFAOYSA-N 0.000 claims 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims 2
- 238000003780 insertion Methods 0.000 claims 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
Abstract
New high refractive index polymeric compositions and foldable intraocular lenses made from such compositions are disclosed. In one embodiment, the present compositions comprise a copolymer including a major amount of a first constituent derived from a first monomeric component the homopolymers of which have a refractive index of at least about 1.50, a minor amount of a second constituent derived from a second monomeric component other than the first monomeric component the homopolymers of which have a glass transition temperature of less than about 30 °C, preferably less than about 22 °C, and a third constituent derived from a cross-linking monomeric component in an amount effective to facilitate returning a deformed intraocular lens made of the composition to its original shape.
Claims
1. A composition comprising a copolymer including a first constituent derived from a first monomeric component the homopolymers of which have a refractive index of at least about 1.50, said first monomeric component including one or more aryl- containing groups, a second constituent derived from a second monomeric component other than said first monomeric component the homopolymers of which have a glass transition temperature of less than about 30°C, and a third constituent derived from a crosslin ing monomeric component in an amount effective to facilitate returning a deformed intraocular lens made of said composition to its original shape.
2. The composition of claim 1 wherein the homopolymers of said first monomeric component have a substantial degree of rigidity and the homopolymers of said second monomeric component have a glass transition temperature of less than about 22°C.
3. The composition of claim 1 wherein said copolymer is optically clear and has a refractive index of at least about 1.50.
4. The composition of claim 1 wherein said first constituent is a major amount of said copolymer, and said first constituent and said second constituent together are at least about 80% by weight of said copolymer.
5. The composition of claim 1 wherein neither said second monomeric component nor said third monomeric component include any aryl-containing groups.
6. The composition of claim 5 wherein said first constituent is a major amount by weight of said copolymer.
7. The composition of claim 1 wherein said copolymer further includes a fourth constituent derived from a hydrophilic monomeric component other than said first, second and third monomeric components, said fourth constituent being present in an amount effective to reduce the tackiness of said copolymer relative to a substantially identical copolymer without said fourth constituent.
8. The composition of claim 1 wherein each of said first, second and third monomeric components includes at least one functional group containing carbon-carbon unsaturation.
9. The composition of claim 1 wherein each of said first, second and third monomeric components includes at least one functional group containing a carbon-carbon double bond.
10. The composition of claim 1 wherein said first monomeric component is selected from the group consisting of styrene, vinyl carbazole, vinyl naphthalene, benzyl acrylate, phenyl acrylate, naphthyl acrylate, pentabromophenyl acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate and mixtures thereof, and said second monomeric component is selected from the group consisting of n-butyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, 2-ethoxyethyl acrylate, 2,3-dibromopropyl acrylate, n-1, 1- dihydroperfluorobutyl acrylate and mixtures thereof.
11. An intraocular lens sized and adapted to be inserted through an incision into a mammalian eye for use, said intraocular lens comprising a copolymer 24
including a first constituent derived from a first monomeric component the homopolymers of which have a refractive index of at least about 1.50, said first monomeric component including one or more aryl- containing groups, a second constituent derived from a second monomeric component other than said first monomeric component the homopolymers of which have a glass transition temperature of less than about 22°C, and a third constituent derived from a crosslinking monomeric component in an amount effective to facilitate returning a deformed intraocular lens made of said copolymer to its original shape.
12. The intraocular lens of claim 11 wherein the homopolymers of said first monomeric component have a substantial degree of rigidity.
13. The intraocular lens of claim 11 wherein said copolymer is optically clear and has a refractive index of at least about 1.50.
14. The intraocular lens of claim 11 which is sized and adapted to be deformed for insertion into a mammalian eye.
15. The intraocular lens of claim 11 which is sized and adapted to be deformed for insertion into a mammalian eye through an incision of about 3 mm.
16. The intraocular lens of claim 11 wherein said first constituent is a major amount by weight of said copolymer, and said first constituent and said second constituent together are at least about 80% by weight of said copolymer.
17. The intraocular lens of claim 11 wherein neither said second monomeric component nor said third 25
monomeric component include any aryl-containing groups.
18. The intraocular lens of claim 11 wherein said copolymer further includes a fourth constituent derived from a hydrophilic monomeric component other than said first, second and third monomeric components, said fourth constituent being present in an amount effective to reduce the tackiness of said copolymer relative to a substantially identical copolymer without said fourth constituent.
19. The intraocular lens of claim 11 wherein each of said first, second and third monomeric components includes at least one functional group containing carbon-carbon unsaturation.
20. The intraocular lens of claim 11 wherein each of said first, second and third monomeric components includes at least one functional group containing a carbon-carbon double bond.
21. The intraocular lens of claim 11 wherein said first monomeric component is selected from the group consisting of styrene, vinyl carbazole, vinyl naphthalene, benzyl acrylate, phenyl acrylate, naphthyl acrylate, pentabromophenyl acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate and mixtures thereof.
22. The intraocular lens of claim 18 wherein said second monomeric component is selected from the group consisting of n-butyl acrylate, n-hexyl acrylate, 2- ethylhexyl acrylate, 2-ethoxyethyl acrylate, 2,3- dibromopropyl acrylate and mixtures thereof.
23. The intraocular lens of claim 11 wherein said first constituent is a major amount by weight of said 26
copolymer.
24. The intraocular lens of claim 18 wherein said hydrophilic monomeric component is selected from the group consisting of N-vinyl pyrrolidone, hydroxyalkyl acrylates, hydroxyalkyl methacrylates, acrylamide, N- alkyl acrylamides and mixtures thereof.
25. The intraocular lens of claim 18 wherein said copolymer is optically clear and has a refractive index of at least about 1.50.
26. The intraocular lens of claim 18 wherein said first constituent is a major amount by weight of said copolymer.
27. The intraocular lens of claim 18 wherein neither said second monomeric component nor said third monomeric component include any aryl-containing groups.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU55497/94A AU5549794A (en) | 1992-11-09 | 1993-11-05 | Polymeric compositions and intraocular lenses made from same |
| AT94900553T ATE213338T1 (en) | 1992-11-09 | 1993-11-05 | POLYMERIC COMPOSITIONS AND INTRA-OCCULAR LENSES MADE THEREFROM |
| JP6512221A JPH08503506A (en) | 1992-11-09 | 1993-11-05 | Polymer composition and intraocular lens made therefrom |
| EP94900553A EP0667966B1 (en) | 1992-11-09 | 1993-11-05 | Polymeric compositions and intraocular lenses made from same |
| DE69331583T DE69331583T2 (en) | 1992-11-09 | 1993-11-05 | POLYMERIC COMPOSITIONS AND INTRA-OCULAR LENSES MADE THEREOF |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/973,470 US5331073A (en) | 1992-11-09 | 1992-11-09 | Polymeric compositions and intraocular lenses made from same |
| US07/973,470 | 1992-11-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1994011764A2 WO1994011764A2 (en) | 1994-05-26 |
| WO1994011764A3 WO1994011764A3 (en) | 1994-07-07 |
| WO1994011764B1 true WO1994011764B1 (en) | 1994-09-01 |
Family
ID=25520936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1993/010657 WO1994011764A2 (en) | 1992-11-09 | 1993-11-05 | Polymeric compositions and intraocular lenses made from same |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5331073A (en) |
| EP (1) | EP0667966B1 (en) |
| JP (1) | JPH08503506A (en) |
| AT (1) | ATE213338T1 (en) |
| AU (1) | AU5549794A (en) |
| DE (1) | DE69331583T2 (en) |
| ES (1) | ES2172526T3 (en) |
| WO (1) | WO1994011764A2 (en) |
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| CS264604B1 (en) * | 1986-12-19 | 1989-08-14 | Sulc Jiri | Syntetic,in hydrocare swelling,intraocular lens |
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| CS269158B1 (en) * | 1988-04-01 | 1990-04-11 | Sulc Jiri | Hard intraocular eyeglass with elastic memory |
| CS271433B1 (en) * | 1988-07-08 | 1990-09-12 | Vacik Jiri | Hydrophylic copolymer and method of its production |
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| US5217491A (en) * | 1990-12-27 | 1993-06-08 | American Cyanamid Company | Composite intraocular lens |
-
1992
- 1992-11-09 US US07/973,470 patent/US5331073A/en not_active Expired - Lifetime
-
1993
- 1993-09-16 US US08/123,016 patent/US5359021A/en not_active Expired - Lifetime
- 1993-11-05 EP EP94900553A patent/EP0667966B1/en not_active Expired - Lifetime
- 1993-11-05 AU AU55497/94A patent/AU5549794A/en not_active Abandoned
- 1993-11-05 WO PCT/US1993/010657 patent/WO1994011764A2/en active IP Right Grant
- 1993-11-05 DE DE69331583T patent/DE69331583T2/en not_active Expired - Fee Related
- 1993-11-05 ES ES94900553T patent/ES2172526T3/en not_active Expired - Lifetime
- 1993-11-05 JP JP6512221A patent/JPH08503506A/en active Pending
- 1993-11-05 AT AT94900553T patent/ATE213338T1/en not_active IP Right Cessation
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