Biomaterial
The present invention provides a triblock copolymer and a viscoelastic biostable foam comprising the same.
1. A triblock copolymer of formula I:
wherein:
each represents a point of attachment to a urethane or urea linkage and the triblock copolymer is chemically interspersed between the urethane or urea linkage;
each of X and Y is different and is independently an ether, an ester, a carbonate, or a flourohydrocarbon, or mixture thereof;
each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently selected from one or more of R, OR, —CO 2 R, a fluorinated hydrocarbon, a polyether, a polyester or a fluoropolymer;
each R is independently hydrogen, an optionally substituted C 1-20 aliphatic group, or an optionally substituted group selected from phenyl, 8-10 membered bicyclic aryl, a 4-8 membered monocyclic saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulphur, or 5-6 membered monocyclic or 8-10 membered bicyclic heteroaryl group having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
each of m n and p is independently 2 to 100; and
each of L 1 and L 2 is independently a bivalent C 1-20 hydrocarbon chain wherein 1-4 methylene units of the hydrocarbon chain are optionally and independently replaced by —O—, —S—, —N(R)—, —C(O)—, —C(O)N(R)—, —N(R)C(O)—, —SO 2 —, —SO 2 N(R)—, —N(R)SO 2 —, —OC(O)—, —C(O)O—, or a bivalent cycloalkylene, arylene, heterocyclene, or heteroarylene, provided that neither of L 1 nor L 2 comprises a urea or urethane moiety.
2. The copolymer according to claim 1 , wherein X and Y are both an ether.
3. The copolymer according to claim 1 , wherein m and p are each independently between 2 and 50 and n is between 2 and 20.
4. The copolymer according to claim 3 , wherein m and p are each independently between 2 and 30 and n is between 2 and 20.
5. The copolymer according to claim 3 , wherein each of m, n, and p are 8-16.
6. The copolymer according to claim 1 , wherein one or more of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently an optionally substituted C 1-6 alkyl.
7. The copolymer according to claim 6 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, or cyclobutyl.
8. The copolymer according to claim 7 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently mono-, di-, tri, or perfluorinated methyl, ethyl, propyl, butyl, or phenyl.
9. The copolymer according to claim 6 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently methyl, ethyl, propyl, trifluoromethyl, trifluoroethyl, or trifluoropropyl.
10. The copolymer according to claim 1 wherein each of L 1 and L 2 is independently a bivalent C 1-20 alkylene chain.
11. The copolymer according to claim 10 wherein each of L 1 and L 2 is independently a bivalent C 1-10 alkylene chain.
12. The copolymer according to claim 11 wherein each of L 1 and L 2 is independently a bivalent methylene, ethylene, propylene, or butylene chain.
13. The copolymer according to claim 1 wherein each of L 1 and L 2 is independently —OCH 2 —, —OCH 2 CH 2 —, —OCH 2 CH 2 CH 2 —, or —OCH 2 CH 2 CH 2 CH 2 —.
14. The copolymer according claim 1 wherein each of L 1 and L 2 is independently a bivalent C 1-6 alkylene chain wherein at least one methylene unit of the chain is replaced by —O— and at least one methylene unit of the chain is replaced by a bivalent arylene.
15. The copolymer according to claim 14 wherein each of L 1 and L 2 is independently —OCH 2 -phenylene-, —OCH 2 CH 2 --phenylene-, —OCH 2 CH 2 -phenylene-CH 2 —, or —OCH 2 CH 2 CH 2 CH 2 --phenylene-.
16. A triblock copolymer of formula II:
wherein:
each of R x and R y is independently —OH, —NH 2 , a protected hydroxyl or a protected amine;
each of X and Y is different and is independently an ether, an ester, a carbonate, or a flourohydrocarbon, or a mixture thereof;
each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently selected from one or more of R, OR, —CO 2 R, a fluorinated hydrocarbon, a polyether, a polyester or a fluoropolymer;
each R is independently hydrogen, an optionally substituted C 1-20 aliphatic group, or an optionally substituted group selected from phenyl, 8-10 membered bicyclic aryl, a 4-8 membered monocyclic saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulphur, or 5-6 membered monocyclic or 8-10 membered bicyclic heteroaryl group having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
each of m n and p is independently 2 to 100; and
each of L 1 and L 2 is independently a bivalent C 1-20 hydrocarbon chain wherein 1-4 methylene units of the hydrocarbon chain are optionally and independently replaced by —O—, —S—, —N(R)—, —C(O)—, —C(O)N(R)—, —N(R)C(O)—, —SO 2 —, —SO 2 N(R)—, —N(R)SO 2 —, —OC(O)—, —C(O)O—, or a bivalent cycloalkylene, arylene, heterocyclene, or heteroarylene, provided that neither of L 1 nor L 2 comprises a urea or urethane moiety.