Patent EA-001397-B1 (EA)
Title: Extnded wear ophthalmic lens
Inventor: NICOLSON PAUL CLEMENT
IPC: C08K3/00
Filed: 1996-03-22
Abstract: 1. An ophthalmic lens having ophthalmically compatible inner and outer surfaces, said lens being suited to extended periods of wear in continuous, intimate contact with ocular tissue and ocular fluids, said lens comprising a polymeric material which has a high oxygen permeability and a high ion permeability, said polymeric material being formed from polymerizable materials comprising: (a) at least one oxyperm polymerizable material and (b) at least one ionoperm polymerizable material, wherein said lens allows oxygen permeation in an amount sufficient to maintain corneal health and wearer comfort during a period of extended, continuous contact with ocular tissue and ocular fluids, and wherein said lens allows ion or water permeation in an amount sufficient to enable the lens to move on the eye such that corneal health is not substantially harmed and wearer comfort is acceptable during a period of extended, continuous contact with ocular tissue and ocular fluids, wherein said ophthalmic lens has an oxygen transmissibility of at least about 70 barrers/mm, and has an lonoton lon Permeability Coefficient of greater than about 0.2 x 10<-6> cm<2>/sec and has an lonoflux Diffusion Coefficient of greater than about 1.5 x 10<-6>mm<2>/min. 2. An ophthalmic lens of claim 1, wherein said ophthalmic lens is selected from the group consisting of contact lenses for vision correction, contact lenses for eye color modification, ophthalmic drug delivery devices, and ophthalmic wound healing devices. 3. An ophthalmic lens of claim 2, wherein said ophthalmic lens is a contact lens. 4. An ophthalmic lens of claim 1, wherein said ophthalmic lens has an oxygen transmissibility of at least about 75 barrers/mm. 5. An ophthalmic lens of claim 4, wherein said ophthalmic lens has an oxygen transmissibility of at least about 87 barrers/mm. 6. An ophthalmic lens of claim 1, wherein said polymeric material comprises an ionoperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens. 7. An ophthalmic lens of claim 1, wherein said polymeric material comprises an oxyperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens. 8. An ophthalmic lens of claim 1, wherein said polymeric material comprises a plurality of co-continuous phases, including at least one oxyperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens and at least one ionoperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens. 9. An ophthalmic lens of claim 1, wherein said polymeric material comprises at least one ion or water pathway which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens. 10. An ophthalmic lens of claim 1, wherein said polymeric material comprises at least one oxygen pathway which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens. 11. An ophthalmic lens of claim 1, wherein said polymeric material comprises a plurality of co-continuous pathways, at least one being an ion or water pathway and at least one other being an oxygen pathway, which pathways extend continuously from the inner surface of the lens to the outer surface of the lens. 12. An ophthalmic lens of claim 11, wherein said co-continuous pathways include a continuous phase of ionoperm polymeric material and a continuous phase of siloxanecontaining polymeric material. 13. An ophthalmic lens of claim 11, wherein said pathways have a domain size which is less than a size which undesirably distorts visible light in an amount which is visible to the eye of the wearer. 14. An ophthalmic lens of claim 1, wherein said lens has an lonoton lon Permeability Coefficient of greater than about 0.3 x 10<-6> cm<2>/s. 15. An ophthalmic lens of claim 14, wherein said lens has an lonoton lon Permeability Coefficient of greater than about 0.4 x 10<-6> cm<2>/s. 16. An ophthalmic lens of claim 1, wherein said lens has an lonoflux Diffusion Coefficient of greater than about 2.6 x 10<-6>mm<2>/min. 17. An ophthalmic lens of claim 16, wherein said lens has an lonoflux Diffusion Coefficient of greater than about 6.4 x 10<-6>mm<2>/min. 18. An ophthalmic lens of claim 1, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.2 x 10<-6> cm<2>/s. 19. An ophthalmic lens of claim 18, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.3 x 10<-6> cm<2>/s. 20. An ophthalmic lens of claim 19, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.4 x 10<-6> cm<2>/s. 21. An ophthalmic lens of claim 1, wherein when hydrated, said lens has an equilibrium water content of less than about 32 weight percent when tested in accordance with the Bulk Technique, described in details in the description. 22. An ophthalmic lens of claim 21, wherein when hydrated, said lens has an equilibrium water content of about 10 to about 30 weight percent when tested in accordance with the Bulk Technique, described in details in the description. 23. An ophthalmic lens of claim 22, wherein when hydrated, said lens has an equilibrium water content of about 15 to about 25 weight percent when tested in accordance with the Bulk Technique described in details in the description. 24. An ophthalmic lens of claim 1, wherein said lens comprises a core polymeric material and an ophthalmically compatible surface which is a hydrophilic surface, wherein said surface is more hydrophilic than said core. 25. An ophthalmic lens of claim 24, wherein said hydrophilic surface is a hydrophilic polymeric surface coating. 26. An ophthalmic lens of claim 25, wherein said hydrophilic surface coating is applied via a plasma coating process. 27. An ophthalmic lens of claim 26, wherein said plasma coating is generated in the presence of a mixture of (a) a C1-C6-alkane and (b) a gas selected from the group consisting of nitrogen, argon, oxygen, air and mixtures thereof. 28. An ophthalmic lens of claim 27, wherein said plasma coating is generated in the presence of a mixture of methane and air. 29. An ophthalmic lens of claim 1, wherein said oxyperm polymerizable material is a siloxane-containing macromer. 30. An ophthalmic lens of claim 29, wherein said siloxane-containing macromer is a poly(dimethyl siloxane) having a number average molecular weight of at least about 800 and a glass transition temperature less than about -115 degree C. 31. An ophthalmic lens of claim 30, wherein said siloxane-containing macromer has a number average molecular weight of at least about 1700. 32. An ophthalmic lens of claim 29, wherein said polymeric material is formed from a polymerizable mixture comprising about 1 to about 10 weight percent of a low molecular weight siloxane-containing monomer. 33. An ophthalmic lens of claim 32, wherein said low molecular weight siloxane-containing monomer is TRIS. 34. An ophthalmic lens of claim 1, wherein said polymeric material is formed from a polymerizable mixture comprising: (a) about 60 to about 85 weight percent oxyperm macromer; and (b) about 15 to about 40 weight percent ionoperm monomer. 35. An ophthalmic lens of claim 34, wherein said polymeric material is formed from a polymerizable mixture comprising: (a) about 70 to about 82 weight percent oxyperm macromer; and (b) about 18 to about 30 weight percent ionoperm monomer. 36. An ophthalmic lens of claim 1, wherein said polymeric material is formed from a polymerizable mixture comprising: (a) about 30 to 60 weight percent oxyperm macromer; (b) about 20 to 40 weight percent ionoperm polymerizable material; and (c) about 1 to 35 weight percent TRIS, based on the total lens weight. 37. An ophthalmic lens of claim 1, wherein said polymeric material includes a polymer composition having good optical clarity and high oxygen permeability, comprising: (a) about 5 to about 94 dry weight percent of a macromer having the formula   wherein: R1 and R2 are selected from C1-C6 alkyl, R3, R4, R5, and R6 are selected from C1-C6 alkylene, R7 and R8 are selected from linear or branched alkylene and bivalent cycloalkylene, R9, R10, R11, and R12 are selected from C1-C2 alkylene, R13 and R14 are selected from C1-C6 alkylene, R15 and R16 are selected from linear or branched lower alkenylene, m and p, independently of one another, are about 3 to about 44, and n is about 13 to about 80, wherein said macromer has a number-average molecular weight of 2000 to 10,000; (b) about 5 to about 60 weight percent of an acrylated or methacrylated siloxane monomer; (c) about 1 to about 30 weight percent of an acrylate or methacrylate monomer; and (d) 0 to 5 weight percent cross-linking agent; wherein said weight percentages are based upon the dry weight of the polymer components. 38. An ophthalmic lens of claim 37, wherein said lens is a contact lens. 39. An ophthalmic lens of claim 1, wherein said polymeric material comprises a polymer formed by polymerization of at least one macromer of formula (I): P1-(Y)m-(L-X1)p-Q-(X1-L)p-(Y)m-P1                (I) where each P1, independently of the others, is a free-radical-polymerizable group; each Y, independently of the others, is -CONHCOO-, -CONHCONH-, -OCONHCO-, -NHCONHCO-, -NHCO-, -CONH-, -NHCONH-, -COO-, -000-, -NHCOO- or -OCONH-; m and p, independently of one another, are 0 or 1; each L, independently of the others, is a divalent radical of an organic compound having up to 20 carbon atoms; each X1, independently of the others, is -NHCO-, -CONH-, -NHCONH-, -COO-, -OCO-, -NHCOO- or -OCONH-; and Q is a bivalent polymer fragment consisting of the segments: (a) - (E)k-Z-CF2-(OCF2)x-(OCF2CF2)y-OCF2-Z (E)k-, where x+y is a number in the range of from 10 to 30; each Z, independently of the others, is a divalent