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US 6,423,761 B1Granted
Contact lens material
AssigneeBiocompatibles Limited
InventorsRoderick William Jonathon Bowers, Peter William Stratford, Stephen Alister Jones
Life of this patent
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Abstract
Cross-linked copolymers which are obtainable by polymerising a neutral diluent monomer or monomers, a monomer or monomers bearing a center of permanent positive charge, and a bifunctional and/or trifunctional cross-linking agent, are suitable for use in contact lenses. Process for producing them by copolymerization, contact lens material comprising them, contact lenses made of them and processes for producing contact lenses from them.
Claims77
A cross-linked polymer obtained by polymerizing a mixture consisting essentially of:
- i) a zwitterionic monomer of the formula (V):
- wherein BB is a straight or branched C1-C6 alkylene chain optionally interrupted by one or more oxygen atoms:
- nn is from 1 to 12;
- R11 is H or a C1-C4 alkyl group;
- and
- YY is a zwitterionic group which is selected from the group consisting of:
- wherein mm is 1 to 4, nn is 1 to 12 and BB is a straight or branched C1-C6 alkylene chain optionally interrupted by one or more oxygen atoms;
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction.
7 more elements
A cross-linked polymer obtained by polymerizing a mixture consisting essentially of;
- i) a zwitterionic monomer of formula (I):
- Y—B—X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene chain or if X contains a carbon-carbon chain between B and the zwitterionic group or if K is joined to B via a carbon atom, a valence bond,
- Y is an ethylenically unsaturated polymerizable group selected from:
- wherein:
- R is hydrogen or a C1-C4 alkyl group;
- A is —O— or —NR1— where R1 is hydrogen or a C1-C4 alkyl group or R1 is —B—X where B and X are as defined above;
- and
- K is a group —(CH2)pOC(O)—, —(CH2)pC(O)O—, —(CH2)pOC(O)O—, —(CH2)pNR2—, —(CH2)pNR2C(O)—, —(CH2)pC(O)NR2—, —(CH2)pNR2C(O)O—, —(CH2)pNR2C(O)O—, —(CH2)pOC(O)NR2—, —(CH2)pNR2C(O)NR2— (in which the groups R2 are the same or different), —(CH2)pO—, —(CH2)pSO3—, or, optionally in a combination with B, a valence bond, and p is from 1 to 12 and R2 is hydrogen or a C1-C4 alkyl group and X is selected from the group consisting of groups of formula (IVC):
- wherein the groups R7 are the same or different and each is hydrogen or C1-4 alkyl, and e is 1, 3 or 4;
- groups of formula (IVD):
- wherein the groups R8 are the same or different and each is hydrogen or C1-4 alkyl, B1 is a valence bond or straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, f is from 1 to 4 and if B is other than a valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- groups of formula (IVE):
- wherein the groups R9 are the same or different and each is hydrogen or C1-4 alkyl, B2 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, g is from 1 to 4 and if B is other than a valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- and
- groups of formula (IVF):
- wherein the groups R10 are the same or different and each is hydrogen or C1-4 alkyl, B3 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, h is from 1 to 4 if B is other than a valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction.
17 more elements
A process for producing a cross-linked copolymer by copolymerizing a monomer solution consisting essentially of a non-ionic diluent monomer or monomers, a zwitterionic monomer or monomers and a cross-linking monomer, wherein said zwitterionic monomer or monomers has the formula (V):
- wherein BB is a straight or branched C1-C6 alkylene chain optionally interrupted by one or more oxygen atoms:
- nn is from 1 to 12;
- R11 is H or a C1-C4 alkyl group;
- and
- YY is a zwitterionic group which is selected from the group consisting of:
- wherein mm is 1 to 4, nn is 1 to 12 and BB is a straight or branched C1-C6 alkylene chain optionally interrupted by one or more oxygen atoms.
3 more elements
A process for producing a cross-linked copolymer by copolymerizing a monomer solution consisting essentially of a non-ionic diluent monomer or monomers, a zwitterionic monomer or monomers and a cross-linking monomer, wherein said zwitterionic monomer or monomers has the formula (I)
- Y—B—X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene chain or if X contains a carbon-carbon chain between B and the zwitterionic group or if K is joined to B via a carbon atom, a valence bond;
- Y is an ethylenically unsaturated polymerizable group selected from:
- wherein:
- R is hydrogen or a C1-C4 alkyl group;
- A is —O— or —NR1— wherein R1 is hydrogen or a C1-C4 alkyl group or R1 is —B—X where B and X are as defined above;
- and
- K is a group —(CH2)pOC(O)—, —(CH2)pC(O)O—, —(CH2)pOC(O)O—, —(CH2)pNR2—, —(CH2)pNR2C(O)—, —(CH2pC(O)NR2—, —(CH2)pNR2C(O)O—, —(CH2)pNR2C(O)O—, —(CH2)pOC(O)NR2—, —(CH2)pNR2C(O)NR2— (in which the groups R2 are the same or different), —(CH2)pO—, —(CH2)pSO3—, or, optionally in a combination with B, a valence bond, and p is from 1 to 12 and R2 is hydrogen or a C1-C4 alkyl group and X is selected from the group consisting of groups of formula (IVC):
- wherein the groups R7 are the same or different and each is hydrogen or C1-4 alkyl, and e is 1, 3 or 4:
- groups of formula (IVD):
- wherein the groups R8 are the same or different and each is hydrogen or C1-4 alkyl, B1 is a valence bond or straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, f is from 1 to 4 and if B is other than a valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- groups of formula (IVE):
- wherein the groups R9 are the same or different and each is hydrogen or C1-4 alkyl, B2 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, g is from 1 to 4 and if B is other than valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- and
- groups of formula (IVF):
- wherein the groups R10 are the same or different and each is hydrogen or C1-4 alkyl, B3 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, h is from 1 to 4 if B is other than a valence bond, z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1.
13 more elements
A contact lens material comprising a cross-linked polymer obtained by polymerizing a mixture consisting essentially of:
- i) a zwitterionic monomer of the formula (V):
- wherein BB is a straight or branched C1-C6 alkylene chain optionally interrupted by one or more oxygen atoms:
- nn is from 1 to 12;
- R11 is H or a C1-C4 alkyl group;
- and
- YY is a zwitterionic group VIB
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction selected from the group consisting of alkane diol di(alk)acrylates, alkane triol tri(alk)acrylates, alkylene di(alk)acrylamides, alkylene tri(alk)acrylamides, divinylbenzene, and trivinylbenzene.
6 more elements
A contact lens material comprising a cross-linked polymer obtained by polymerizing a mixture consisting essentially of:
- i) a zwitterionic monomer of formula (I):
- Y—B—X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligooxaalkylene chain or if X contains a carbon-carbon chain between B and the zwitterionic group or it Y contains a terminal carbon atom, a valence bond,
- Y is an ethylenically unsaturated polymerizable group selected from:
- wherein:
- R is hydrogen or a C1-C4 alkyl group;
- A is —O— or —NR1— where R1 is hydrogen or a C1-C4 alkyl group or R1 is —B—X where B and X are defined above;
- and
- K is a group —(CH2)pOC(O)—, —(CH2)pC(O)O—, —(CH2)FOC(O)O—, —(CH2)pNR2—, —(CH2)pNR2C(O)—, —(CH2)pC(O)NR2—, —(CH2)pNR2C(O)O—, —(CH2)pNR2C(O)O—, —(CH2)pOC(O)NR2—, —(CH2)pNR2C(O)NR2—, (in which the groups R2 are the same or different), —(CH2)pO—, —(CH2)pSO3—, or, optionally in a combination with B, a valence bond, and p is from 1 to 12 and R2 is hydrogen or a C1-C4 alkyl group and X is IVB
- wherein the groups R6 are the same or different and each is hydrogen or C104 alkyl and d is from 2 to 4, II
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction selected from the group consisting of alkane diol di(alk)acrylates, alkane triol tri(alk)acrylates, alkylene di(alk)acrylamides, alkylene tri(alk)acrylamides, divinylbenzene, and trivinylbenzene.
10 more elements
A crosslinked polymer obtained by polymerizing a mixture consisting essentially of:
- i) a zwitterionic monomer of formula (I):
- Y—B—X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene chain,
- Y is a group of formula
- CH2═C(R)—C(O)—A—
- wherein:
- R is hydrogen or a C1-C4 alkyl group;
- A is —O— or —NR1— where R1 is hydrogen or a C1-4-alkyl group or R1 is —B—X where B is defined above and X is as defined below;
- and
- X is selected from the group consisting of groups of formula (IVC):
- wherein the groups R7 are the same or different and each is hydrogen or C1-4 alkyl, and e is 1, 3 or 4;
- groups of formula (IVD):
- wherein the groups R8 are the same or different and each is hydrogen or C1-4 alkyl, B1 is a valence bond or straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, f is from 1 to 4 and z is 1;
- groups of formula (IVE):
- wherein the groups R9 are the same or different and each is hydrogen or C1-4 alkyl, B2 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, g is from 1 to 4 and z is 1;
- and
- groups of formula (IVF):
- wherein the groups R10 are the same or different and each is hydrogen or C1-4 alkyl, B3 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, h is from 1 to 4 and z is 1;
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction.
18 more elements
A process for producing a crosslinked copolymer by copolymerizing a solution containing mixture of monomers consisting essentially of a non-ionic diluent monomer or monomers, a zwitterionic monomer or monomers and a crosslinking monomer, wherein said zwitterionic monomer or monomers has the formula (I):
- Y—B—X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene chain,
- Y is a group of formula
- CH2═C(R)—C(O)—A—
- wherein:
- R is hydrogen or a C1-C4 alkyl group;
- A is —O— or —NR1— where R1 is hydrogen or a C1-4-alkyl group or R1 is —B—X where B is defined above and X is as defined below;
- and
- X is selected from the group consisting of groups of formula (IVC):
- wherein the groups R7 are the same or different and each is hydrogen or C1-4 alkyl, and e is 1, 3 or 4;
- groups of formula (IVD):
- wherein the groups R8 are the same or different and each is hydrogen or C1-4 alkyl, B1 is a valence bond or straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, f is from 1 to 4 and z is 1;
- groups of formula (IVE):
- wherein the groups R9 are the same or different and each is hydrogen or C1-4 alkyl, B2 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, g is from 1 to 4 and z is 1;
- and
- groups of formula (IVF):
- wherein the groups R10 are the same or different and each is hydrogen or C1-4 alkyl, B3 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, h is from 1 to 4 and z is 1;
- ii) a non-ionic diluent monomer;
- and
- iii) a cross-linking monomer which forms cross-links during the polymerization reaction.
17 more elements
Dependencies are inferred from the claim text.