Side-chain crystallizable polymers for medical applications
View Patent ↗Inherently radiopaque side-chain crystallizable polymers (IRSCCP's) are useful in various medical applications. An example of a IRSCCP is a polymer that comprises a main chain, a plurality of crystallizable side chains, and a plurality of heavy atoms attached to the polymer, the heavy atoms being present in an amount that is effective to render the polymer radiopaque. A polymeric material that includes a IRSCCP may be fabricated into a medical device useful for at least partially occluding a body cavity. For example, such a medical device may be an embolotherapy product.
1. A polymer comprising:
a main chain;
a plurality of crystallizable side chains; and
a plurality of heavy atoms attached to the polymer, the heavy atoms being present in an amount that is effective to render the polymer radiopaque.
2. The polymer of claim 1 having a melting point in the range of about 30° C. to about 80° C.
3. The polymer of claim 1 that is biocompatible.
4. The polymer of claim 1 that is bioresorbable.
5. The polymer of claim 1 in which the plurality of heavy atoms comprise an atom having an atomic number of at least 17.
6. The polymer of claim 5 in which the plurality of heavy atoms comprise an atom having an atomic number of at least 35.
7. The polymer of claim 1 in which the plurality of heavy atoms comprise an atom selected from the group consisting of bromine, iodine, bismuth, gold, platinum tantalum, tungsten, and barium.
8. The polymer of claim 1 in which the plurality of heavy atoms are covalently attached to the polymer.
9. The polymer of claim 1 in which the plurality of heavy atoms are ionically attached to the polymer.
10. The polymer of claim 1 that is a copolymer comprising at least two different recurring units.
11. The polymer of claim 10 that is a random copolymer.
12. The polymer of claim 10 that is a block copolymer.
13. The polymer of claim 1 in which the heavy atoms are attached to the polymer in a manner that minimizes disruption of side chain crystallinity.
14. The polymer of claim 1 that comprises a recurring unit of the formula (II):
wherein R 7 is H or CH 3 ; A 3 is a chemical group having a molecular weight of about 500 or less; and A 3 bears at least one of the heavy atoms attached to the polymer.
15. The polymer of claim 14 in which A 3 comprises a metal carboxylate or metal sulfonate.
16. The polymer of claim 15 in which A 3 comprises barium.
17. The polymer of claim 14 in which A 3 comprises an ester or amide linkage.
18. The polymer of claim 14 in which A 3 comprises an aromatic group bearing at least one halogen atom selected from the group consisting of bromine and iodine.
19. The polymer of claim 14 in which A 3 comprises a chemical group of the formula -L 1 -(CH 2 ) n2 -L 2 -Ar 1 , wherein L 1 and L 2 each independently represent a nullity, ester, ether or amide group; n2 is zero or an integer in the range of about 1 to about 30; and Ar 1 comprises a halogenated aromatic group containing from about 2 to about 20 carbon atoms.
20. The polymer of claim 14 that comprises a second recurring unit, the second recurring unit comprising at least one of the crystallizable side chains.
21. The polymer of claim 20 in which the second recurring unit is of the formula (III):
wherein R 8 is H or CH 3 ; L 3 is an ester or amide linkage; and R 9 comprises a C 6 to C 30 hydrocarbon group.
22. The polymer of claim 1 that comprises a recurring unit of the formula (IV):
wherein A 4 represents H or a chemical group containing from about 1 to about 30 carbons; A 3 is a chemical group having a molecular weight of about 500 or less; and A 3 bears at least one of the heavy atoms attached to the polymer.
23. The polymer of claim 22 in which A 3 comprises an aromatic group bearing at least one halogen atom selected from the group consisting of bromine and iodine.
24. The polymer of claim 22 that comprises a second recurring unit, the second recurring unit comprising at least one of the crystallizable side chains.
25. The polymer of claim 24 in which the second recurring unit is of the formula (V):
wherein R 10 comprises a C 6 to C 30 hydrocarbon group and R 11 represents H or a C 1 to C 30 hydrocarbon group.