Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing polyoxyalkylene backbone units, and use thereof

Claim 1

An optically clear, wettable, flexible, hydrolytically stable, biologically inert, substantially siloxane free, and oxygen permeable crosslinked polymer comprising a) units of formula I ##STR34## wherein each b, d, and f is independently 0-4; each q is a number of 1-1000; each x, y, and z is independently a number from 0 to a number such that (x+y+z) times q within each unit of formula I is 4-1000; each R 1 -R 18 is selected from the group consisting of (i) hydrogen, and (ii) aromatic or alicyclic containing radical, each of which uninterrupted or interrupted by a heteroatom provided no carbon atom in said unit is geminally singly-bound to oxygen atoms; or any 2 adjacent groups R 1 -R 18 , together with the atoms to which they are attached can form a 5-8 membered ring; or R 1 -R 18 may independently be additionally selected from, or any of the aforementioned R 1 -R 18 groups may have a substituent which is a cross-linkable moiety provided that no carbon atoms bearing geminally singly-bound oxygen atoms results; the terminal oxygen atom within any unit of formula I being replaceable by ##STR35## wherein R 19 is hydrogen, C 1-4 alkyl or phenyl; with the proviso that when b, d, and f are all zero, at least one of R 1 , R 2 , R 5 -R 8 , R 11 -R 14 , R 17 , and R 18 in at least a portion of the units of formula I is other than hydrogen; and further provided that R 1 -R 18 individually, or in the aggregate, is sufficiently hydrophobic such that in the absence of a hydrophilic modifier unit, the resulting polymer is substantially non-swellable in water; and b) a hydrophilic modifier unit in an amount sufficient to maintain the water content of said crosslinked polymer in excess of 10%; said cross-linked polymer having a receding contact angle with distilled water of less than 60° when measured at 20° C. and an oxygen permeability Dk greater than about 1-1.5 times that of polyhydroxyethyl methacrylate said hydrophilic modifier unit being the residue of a reactive monomer selected from N,N-dimethylacrylamide, or a) polyethylene glycols of the formula ##STR36## or b) pyrrolidones of the formula ##STR37## wherein R 20 is H or lower alkyl, n is 1-25, and R 21 is an ethylenically unsaturated group or c) of the formula (R.sub.21 -δ)Z'H' (C) wherein R 21 is a polymerizable moiety selected from the group consisting of ethylenically unsaturated radicals, epoxy groups, anhydrides, isocyanates, amines, acids, esters amides, ethers, acid halides, and hydroxy; 8 is selected from i) a divalent aliphatic group of up to 25 carbon atoms which may also be interrupted or terminated, or interrupted and terminated by oxy, carbonyloxy, amino, aminocarbonyl, oxycarbonyl, ureido, oxycarbonylamino, or carbonyl amino; ii) a divalent 5-7 membered cycloaliphatic and a 5-7 membered cycloaliphatic-C 1-20 aliphatic which may also be interrupted, terminated, or interrupted and terminated as in group i) above except that said interruptions cannot occur within the cycloaliphatic portions; iii) a divalent arylene having 6-25 carbon atoms which also is unsubstituted or substituted by at least one substituent selected from halogen, C 1-4 alkyl, and C 1-12 perhalo alkyl; iv) a divalent aralkyl or alkaryl having 7-25 carbon atoms which is uninterrupted or interrupted in the alkyl portion, or terminated, or interrupted in the alkyl portion and terminated with an interrupting or terminating group as mentioned in i) above, and each of said uninterrupted, interrupted, and terminated aralkyl and alkaryl groups is further unsubstituted or further substituted by a substituent selected from halogen, C 1-4 alkyl, and C 1-12 perhaloalkyl; and ##STR38## wherein na=8-100, each R a is CH 3 and each R b is H and nb is 0 or each R a is H and each R b is CH 3 and nb is zero or R a and R b are each H and nb is 1; and H' is a hydrophilic group selected from a) morpholino, cyclic amide radicals of 5-7 ring members; saturated and unsaturated cyclic N,N-diamides of 5-6 ring members, ##STR39## wherein nc and nd are each selected from 0-2; cyclic amines of 5-6 members; each unsubstituted or substituted by hydroxy-C 1-5 alkyl, carboxy, or lower alkyl b) tetrahydrofurfuryl c) mono, di, and poly saccharide radicals, whether straight chain or cyclic, and the corresponding sugar alcohol radicals, pentaerythritol radicals, polyvinyl alcohol radicals, and d) (poly hydroxy C 2 -C 7 alkyl) radicals and Z' is 1 up to the valency of said H' and when Z' is less than the valency of H', such excess valences are taken up by hydrogen; wherein the reactive group R 21 is capable of reacting with one or more non hydrophilic modifier sites in said polymer.