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US 4,740,533 AGranted
Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof
AssigneeCiba-Geigy Corporation
InventorsKai C. Su, J. Richard Robertson
Life of this patent
Estimating the term…
Abstract
Contact lenses which are optically clear, wettable, flexible, of high oxygen permeability and substantially non-swellable in the aqueous ocular environment of use, of a block copolymer containing polysiloxane and polyoxyalkylene oxide units are disclosed, as well as the preparation thereof and methods of treating vision defects therewith.
Claims54
An optically clear wettable, flexible, oxygen permeable, substantially non-swellable ophthalmic device fabricated from a polymer of a crosslinkable monomer having a segment S" of the formula
- --(D--S'--L--D--A--L)--.sub.b (I')
- wherein
- b is 1-10;
- each D is independently --O-- or --NR.sub.21 --;
- each L is independently --BRB'--, the terminal L group within any one monomer also being capable of being --BR--;
- each S' is independently of the formula ##STR24## each A is independently of the formula ##STR25## the terminal oxygen atom in formulae II or III being replaceable with --NR.sub.21 --;
- each R.sub.1 and R.sub.2 is independently lower alkyl or aryl;
- each R.sub.3, R.sub.4, R.sub.7 -R.sub.10, R.sub.13 -R.sub.16, R.sub.19 and R.sub.20 is independently selected from H, halogen, aliphatic, aromatic or heterocyclic containing radical selected from unsubstituted (C.sub.1 -C.sub.16) alkyl;
- substituted C.sub.1 -C.sub.16 alkyl;
- unsubstituted C.sub.2 -C.sub.16 alkenyl;
- and substituted C.sub.2 -C.sub.16 alkenyl;
- wherein the alkyl and alkenyl substituents are independently selected from C.sub.1 -C.sub.16 alkoxycarbonyl, C.sub.2 -C.sub.16 alkenyloxycarbonyl, fluoro, aryl of up to 10 carbon atoms, C.sub.1 -C.sub.16 alkoxy, C.sub.2 -C.sub.16 alkanoyloxy, aryloxy of up to 10 carbon atoms, C.sub.2 -C.sub.6 alkenoyloxy, aroyl of up to 10 carbon atoms, aroyloxy of up to 11 carbon atoms, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyloxy, C.sub.3 -C.sub.8 cycloalkyl-carbonyloxy, C.sub.3 -C.sub.8 cycloalkoxy-carbonyl, oxacycloalkyl of up to 7 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkoxy (up to 7 carbon atoms)-carbonyl, oxacycloalkyl (up to 7 carbon atoms)-carbonyloxy, and aryl (of up to 10 carbon atoms)-oxycarbonyl, each of said alkyl and alkenyl substituents being, in turn, optionally substituted by C.sub.1 -C.sub.6 alkyl, fluoro or a C.sub.1 -C.sub.6 alkoxy provided said last mentioned alkoxy is not bound to a carbon atom already singly bound to another oxygen atom;
- R.sub.3, R.sub.4, R.sub.7 -R.sub.10, R.sub.13 -R.sub.16, R.sub.19 and R.sub.20 being further independently selected from aryl of up to 10 carbon atoms, C.sub.3 -C.sub.8 cycloalkyl, and oxacycloalkyl of up to 7 carbon atoms, each of which may be unsubstituted or further substituted with a substituent selected from the group of substituents for said R.sub.3 alkyl set forth above;
- R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are selected from the same group set forth above for R.sub.3 ;
- and R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are further independently selected from C.sub.1 -C.sub.16 alkoxycarbonyl, C.sub.2 -C.sub.16 alkanoyloxy, C.sub.2 -C.sub.16 alkenoxycarbonyl, and C.sub.3 -C.sub.16 alkenoyloxy, each of which is unsubstituted or further substituted by fluoro, aryl of up to 10 carbon atoms, or C.sub.1 -C.sub.16 alkoxy;
- and R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are still further independently selected from aryloxy of up to 10 carbon atoms, cycloalkoxy of up to 8 carbon atoms, cycloalkyl (of up to 8 carbon atoms)-carbonyloxy, cycloalkoxy (of up to 8 carbon atoms)-carbonyl, aroyloxy of up to 11 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkenyloxy of up to 7 carbon atoms, oxacycloalkoxy (of up to 7 carbon atoms)-carbonyl, oxacycloalkyl (of up to 7 carbon atoms)-carbonyloxy, and aryloxy (of up to 10 carbon atoms)-carbonyl, each of which may be further substituted by fluoro, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, provided that any substituent having a singly bound oxygen atom thereof as its link to the rest of the molecule may not be a substituent on the same carbon atom which is singly bonded to another oxygen atom;
- and 2 adjacent groups selected from R.sub.3 -R.sub.20, together with the atoms to which they are attached may form a 5-8 membered cycloalkyl, oxacycloalkyl or bicycloalkyl ring;
- each f, g and h are independently 0-3;
- each w, x and z is independently 0-200;
- q is 1-100;
- (w+x+z) times q in any single group A is 4-1000;
- each n and m is independently 1-6;
- each y is independently 2-75;
- each R.sub.21 is independently H, C.sub.1 -C.sub.4 alkyl, or phenyl;
- each B and B' is independently ##STR26## with the carbony in each case being bound to A, S', or D;
- each R is independently
- (i) a divalent aliphatic group of up to 25 carbon atoms which may be interrupted by oxy, carbonyloxy, amino, aminocarbonyl, oxycarbonyl, ureido, oxycarbonylamino, or carbonylamino;
- (ii) a divalent 5-7 membered cycloaliphatic having 5-25 carbon atoms;
- (iii) a divalent arylene group have 6-25, preferably 7-15 carbon atoms;
- and
- (iv) a divalent aralkyl or alkaryl having 7 to 25;
- wherein groups b and d can be optionally interrupted by the same groups as in group i and wherein the aryl rings in groups iii and iv may be further substituted with one or more substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.12 perhalo alkyl;
- said device having a receding contact angle of less than 60%;
- being less than about 10% water in its swollen state;
- and having a Dk (x10.sup.-10 mm ccO.sub.2 /cm..sup.2 sec.mmHg) of at least about 7.
32 more elements
An optically clear wettable, flexible, oxygen permeable, substantially non-swellable polymer of a crosslinkable monomer having a segment S" of the formula
- --(D--S'--L--D--A--L)--.sub.b (I')
- wherein
- b is 1-10;
- each D is independently --O-- or --NR.sub.21 --;
- each L is independently --BRB'--, the terminal L group within any one monomer also being capable of being --BR--;
- each S' is independently of the formula ##STR39## each A is independently of the formula ##STR40## the terminal oxygen atom in formulae II or III being replaceable with --NR.sub.21 --;
- each R.sub.1 and R.sub.2 is independently lower alkyl or aryl;
- each R.sub.3, R.sub.4, R.sub.7 -R.sub.10, R.sub.13 -R.sub.16, R.sub.19 and R.sub.20 is independently selected from H, halogen, aliphatic, aromatic or heterocyclic containing radical selected from unsubstituted (C.sub.1 -C.sub.16) alkyl;
- substituted C.sub.1 -C.sub.16 alkyl;
- unsubstituted C.sub.2 -C.sub.16 alkenyl;
- and substituted C.sub.2 -C.sub.16 alkenyl;
- wherein the alkyl and alkenyl substituents are independently selected from C.sub.1 -C.sub.16 alkoxycarbonyl, C.sub.2 -C.sub.16 alkenyloxycarbonyl, fluoro, aryl of up to 10 carbon atoms, C.sub.1 -C.sub.16 alkoxy, C.sub.2 -C.sub.16 alkanoyloxy, aryloxy of up to 10 carbon atoms, C.sub.2 -C.sub.6 alkenoyloxy, aroyl of up to 10 carbon atoms, aroyloxy of up to 11 carbon atoms, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyloxy, C.sub.3 -C.sub.8 cycloalkyl-carbonyloxy, C.sub.3 -C.sub.8 cycloalkoxy-carbonyl, oxacycloalkyl of up to 7 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkoxy (up to 7 carbon atoms)-carbonyl, oxacycloalkyl (up to 7 carbon atoms)-carbonyloxy, and aryl (of up to 10 carbon atoms)-oxycarbonyl, each of said alkyl and alkenyl substituents being, in turn, optionally substituted by C.sub.1 -C.sub.6 alkyl, fluoro or a C.sub.1 -C.sub.6 alkoxy provided said last mentioned alkoxy is not bound to a carbon atom already singly bound to another oxygen atom;
- R.sub.3, R.sub.4, R.sub.7 -R.sub.10, R.sub.13 -R.sub.16, R.sub.19 and R.sub.20 being further independently selected from aryl of up to 10 carbon atoms, C.sub.3 -C.sub.8 cycloalkyl, and oxacycloalkyl of up to 7 carbon atoms, each of which may be unsubstituted or further substituted with a substituent selected from the group of substituents for said R.sub.3 alkyl set forth above;
- R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are selected from the same group set forth above for R.sub.3 ;
- and R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are further independently selected from C.sub.1 -C.sub.16 alkoxycarbonyl, C.sub.2 -C.sub.16 alkanoyloxy, C.sub.2 -C.sub.16 alkenoxycarbonyl, and C.sub.3 -C.sub.16 alkenoyloxy, each of which is unsubstituted or further substituted by fluoro, aryl of up to 10 carbon atoms, or C.sub.1 -C.sub.16 alkoxy;
- and R.sub.5, R.sub.6, R.sub.11, R.sub.12, R.sub.17 and R.sub.18 are still further independently selected from aryloxy of up to 10 carbon atoms, cycloalkoxy of up to 8 carbon atoms, cycloalkyl (of up to 8 carbon atoms)-carbonyloxy, cycloalkoxy (of up to 8 carbon atoms)-carbonyl, aroyloxy of up to 11 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkenyloxy of up to 7 carbon atoms, oxacycloalkoxy (of up to 7 carbon atoms)-carbonyl, oxacycloalkyl (of up to 7 carbon atoms)-carbonyloxy, and aryloxy (of up to 10 carbon atoms)-carbonyl, each of which may be further substituted by fluoro, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, provided that any substituent having a singly bound oxygen atom thereof as its link to the rest of the molecule may not be a substituent on the same carbon atom which is singly bonded to another oxygen atom;
- and 2 adjacent groups selected from R.sub.3 -R.sub.20, together with the atoms to which they are attached may form a 5-8 membered cycloalkyl, oxacycloalkyl or bicycloalkyl ring;
- each f, g and h are independently 0-3;
- each w, x and z is independently 0-200;
- q is 1-100;
- (w+x+z) times q in any single group A is 4-1000;
- each n and m is independently 1-6;
- each y is independently 2-75;
- each R.sub.21 is independently H, C.sub.1 -C.sub.4 alkyl, or phenyl;
- each B and B' is independently ##STR41## with the carbony in each case being bound to A, S', or D;
- each R is independently
- (i) a divalent aliphatic group of up to 25 carbon atoms which may be interrupted by oxy, carbonyloxy, amino, aminocarbonyl, oxycarbonyl, ureido, oxycarbonylamino, or carbonylamino;
- (ii) a divalent 5-7 membered cycloaliphatic having 5-25 carbon atoms;
- (iii) a divalent arylene group have 6-25, preferably 7-15 carbon atoms;
- and
- (iv) a divalent aralkyl or alkaryl having 7 to 25;
- wherein groups b and d can be optionally interrupted by the same groups as in group i and wherein the aryl rings in groups iii and iv may be further substituted with one or more substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.12 perhalo alkyl;
- said device having a receding contact angle of less than 60%;
- being less than about 10% water in its swollen state;
- and having a Dk (x10.sup.-10 mm ccO.sub.2 /cm..sup.2 sec.mmHg) of at least about 7.
32 more elements
Dependencies are inferred from the claim text.