Patent ID: 6815074
Filing Date: 2004-11-09
Classification: A61L,G02B,Y10T

Abstract:
An ophthalmic lens, comprising a core polymeric material and an ophthalmically compatible surface which is more hydrophilic than said core polymeric material, wherein the ophthalmic lens has a high oxygen permeability characterized by a Dk greater than 56 barrers and a high ion permeability characterized by an ionoflux diffusion coefficient of great than 4.0Ã—10âˆ’4 mm 2/min and comprises a water content of at least 25 weight percent when fully hydrated, wherein said ophthalmically compatible surface is an LbL coating comprisisg a plurality of bilayers and a capping layer of polyvinylpyrrolidone, wherein each bilayer comprises one layer of a first polyionic material and one layer of a second polyionic material having charges opposite of the charges of the first polyionic materials, wherein said core polymeric material is prepared by curing in a mold in an oxygen-containing or oxygen-free atmosphere a polymer composition including:(i) about 5 to about 40 weight percent of a macromer, wherein said macromer is selected from the group consisting of Macromer A, Macromer B, Macromer C, and Macromer D; (ii) about 10 to about 30 weight percent of a siloxane-containing monomer; and (iii) about 30 to about 50 weight percent of a hydrophilic monomer, wherein said weight percentages are based upon the dry weight of the polymer components, wherein Macromer A is a polysiloxane macromer having a number-average molecular weight of 2000 to 10,000 and the the segment of the formula: CP-PAO-DU-ALK-PDMS-ALK-DU-PAO-CP where PDMS is a divalent poly(disubstituted siloxane), ALK is an alkylene or alkylenoxy group having at least 3 carbon atoms, DU is a diurethane-containing group, PAO is a divalent polyoxyalkylene, and CP is selected from acrylates and methacrylates, wherein Macromer B is a polysiloxane-comprising perfluoroalkyl ether and has the formula: P1-(Y)m-(L-X1)p-Q-(X1-L)p-(Y)m-P1 where each P1, independently of the others, is a free-radical-polymerizable group; each Y, independently of the others, is â€”CONHCOOâ€”, â€”CONHCONHâ€”, â€”OCONHCOâ€”, â€”NHCONHCOâ€”, â€”NHCOâ€”, â€”CONHâ€”, â€”NHCONHâ€”, â€”COOâ€”, â€”OCOâ€”, â€”NHCOOâ€” or â€”OCONHâ€”; 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 â€”NHCOâ€”, â€”CONHâ€”, â€”NHCONHâ€”, â€”COOâ€”, â€”OCOâ€”, â€”NHCOOâ€” or â€”OCONHâ€”; and Q is a bivalent polymer fragment consisting of the segments: -(E)k-Z-CF2â€”(OCF2)xâ€”(OCF2CF2)yâ€”OCF2-Z-(E)k-,â€ƒâ€ƒ(a) where x+y is a number in the range of from 10 to 30; each Z, independently of the others, is a divalent radical having up to 12 carbon atoms or Z is a bond; each E, independently of the others, is â€”(OCH2CH2)qâ€”, where q has a value of from 0 to 2, and where the link -Z-E- represents the sequence -Z-(OCH2CH2)qâ€”; and k is 0 or 1; wherein is an integer from 5 to 100; Alk is alkylene having up to 20 carbon atoms; 80-100% of the radicals R1, R2, R3 and R4, independently of one another, are alkyl and 0-20% of the radicals R1, R2, R3 and R4, independently of one another, are alkenyl, aryl or cyanoalkyl; and (c) X2â€”Râ€”X2, where R is a divalent organic radical having up to 20 carbon atoms, and each X2, independently of the others, is â€”NHCOâ€”, â€”CONHâ€”, â€”NHCONHâ€”, â€”COOâ€”, â€”OCOâ€”, â€”NHCOOâ€” or OCONHâ€”; with the provisos that there must be at least one of each segment (a), (b), and (c) in Q, that each segment (a) or (b) has a segment (c) attached to it, and that each segment (c) has a segment (a) or (b) attached to it; wherein Macromer C has an average molecular weight of from about 300 to about 30,000 and comprises at least one segment of the formula (I), (IV), (V), (VI) or (VII): in which (a) is a polysiloxane segment; (b) is a polyol segment which contains at least 4 carbon atoms; Z is a segment (c) or a group X1; (c) is defined as X2â€”Râ€”X2, wherein R is a bivalent radical of an organic compound having up to 20 carbon atoms and each X2 independently of the other is a bivalent radical which contains at least one carbonyl group; X1 is defined as X2; x is 0, 1 or 2; q has an average numerical value of 1-20; and (d) is a radical of the formula (II): X3-L-(Y)k-P1â€ƒâ€ƒ(II) in which P1 is alkenyl, alkenylaryl or alkenylarylenealkyl having up to 20 carbon atoms; Y and X3 independently of one another are a bivalent radical which contains at least one carbonyl group; k is 0 or 1; and L is a bond or a divalent radical having up to 20 carbon atoms of an organic compound, wherein the polysiloxane segment (a) is derived from a compound containing at least one primary amino or hydroxyl group and being of the formula (III): in which n is an integer from 5 to 500; 99.8-25% of the radicals R1, R2, R3, R4, R5 and R6 independently of one another are alkyl and 0.2-75% of the radicals R1, R2, R3, R4, R5 and R6 independently of one another are partly fluorinated alkyl, aminoalkyl, alkenyl, aryl, cyanoalkyl, alk-NH-alk-NH2 or alk-(OCH2)mâ€”(OCH2)p-OR7, R7 is hydrogen or lower alkyl, alk is alkylene, and m and p independently of one another are an integer from 0 to 10, wherein the alkylenoxy groups â€”(OCH2CH2)m and â€”(OCH2)p in formula (III) are either distributed randomly in a ligand alk-(OCH2CH2)mâ€”(OCH2)p-OR7 or are distributed as blocks in a chain, wherein the polysiloxane segment (a) in formula (I) is linked a total of 1-50 times, via a group Z with the segment (b) or another segment (a), Z in an a-Z-a sequence always being a segment (c), wherein the segments (b) in Macromer C according to the formula (VI) are linked in total (per molecule) with up to 20 with up to 6 polymerizable segments (d), wherein the average number of segments (d) per molecule of the formula (VII) is in the range from 2 to 5, wherein macromer D has the formula: ACRYLATE-LINK-ALK-O-ALK-PDAS-ALK-O-ALK-LINK-ACRYLATE in which the ACRYLATE is selected from acrylates and methacrylates; LINK is selected from urethanes and dirurethane linkages; ALK-O-ALK is R1â€”Oâ€”R2 or R3â€”Oâ€”R4, R1, R2, R3, and R4, independently of one another, are lower alkylene; and PDAS is a poly(dialkylsiloxane) having a segment of the formula: in which n is an integer from about 5 to about 500; and R5, R6, R7, and R8 are, independently of one another, are lower alkyl.