Copolymers having polyisobutylene and biodegradable polymer segments
US-9631042-B2 · Apr 25, 2017 · US
US10882945B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10882945-B2 |
| Application number | US-201916359079-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 20, 2019 |
| Priority date | Mar 26, 2018 |
| Publication date | Jan 5, 2021 |
| Grant date | Jan 5, 2021 |
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A modified polyisobutylene-based polymer, method of making, and a medical device that includes such polymer, wherein the modified polyisobutylene-based polymer includes urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments include diisocyanate residues and optionally chain extender residues.
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The invention claimed is: 1. A modified polyisobutylene-based polymer comprising urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments comprise diisocyanate residues and optionally chain extender residues; wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene diol, diamine, or combination thereof. 2. The modified polyisobutylene-based polymer of claim 1 comprising urethane groups. 3. A modified polyisobutylene-based polymer comprising urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments comprise diisocyanate residues and chain extender residues. 4. A modified polyisobutylene-based polymer comprising urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments comprise diisocyanate residues and optionally chain extender residues; wherein the weight ratio of soft segments to hard segments is within a range of 90:10 to 10:90. 5. The modified polyisobutylene-based polymer of claim 1 further comprising additional soft segment residues. 6. The modified polyisobutylene-based polymer of claim 5 wherein the weight ratio of phenoxy-containing polyisobutylene residues to additional soft segment residues is within a range of 99:1 to 1:99. 7. The modified polyisobutylene-based polymer of claim 1 having a weight average molecular weight of 10,000 Daltons to 2,000,000 Daltons, as determined by gel permeation chromatography with multiangle laser light scattering detection. 8. A medical device comprising a polymeric region comprising a modified polyisobutylene-based polymer comprising urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments comprise diisocyanate residues and optionally chain extender residues. 9. The medical device of claim 8 comprising an implantable electrical lead, an implantable electrical pulse generator, or an implantable mechanical device. 10. The medical device of claim 9 comprising an implantable electrical lead. 11. The medical device of claim 8 wherein the polymeric region further comprises a therapeutic agent. 12. A method of making the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene residues of claim 1 , the method comprising combining reactants comprising a diisocyanate, an optional chain extender, a phenoxy-containing polyisobutylene diol, damine, or combination thereof, and an optional additional soft segment-containing diol, diamine, or combination thereof under conditions effective to form the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene residues. 13. A method of making the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene resides of claim 3 , the method comprising combining reactants comprising a diisocyanate, a chain extender, a phenoxy-containing polyisobutylene diol, diamine, or combination thereof, and an optional additional soft segment-containing diol, diamine, or combination thereof under conditions effective to form the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene residues. 14. A method of making the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene residues of claim 4 , the method comprising combining reactants comprising a diisocyanate, an optional chain extender, a phenoxy-containing polyisobutylene diol, damine, or combination thereof, and an optional additional soft segment-containing diol, diamine, or combination thereof under conditions effective to form the modified polyisobutylene-based polymer comprising phenoxy-containing polyisobutylene residues. 15. The modified polyisobutylene-based polymer of claim 1 wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene compound of the following formula: wherein R 1 is an initiator residue, each X is independently —OH, —NH 2 , or —NHR 2 , each r is independently 1-20, n=1-500, and m=1-500. 16. The modified polyisobutylene-based polymer of claim 1 wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene diol of the following formula: wherein R 1 is an initiator residue, each r is independently 1-20, n=1-500, and m=1-500. 17. The modified polyisobutylene-based polymer of claim 1 wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene diol of the following formula: wherein each r (independently)=1-20, n=1-500, and m=1-500. 18. The medical device of claim 8 , wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene diol, diamine, or combination thereof. 19. The medical device of claim 8 , wherein the phenoxy-containing polyisobutylene residues are derived from a phenoxy-containing polyisobutylene compound of the following formula: wherein R 1 is an initiator residue, each X is independently —OH, —NH 2 , or —NHR 2 , each r is independently 1-20, n=1-500, and m=1-500. 20. A modified polyisobutylene-based polymer comprising urethane, urea, or urethane-urea groups, hard segments, and soft segments, wherein the soft segments comprise phenoxy-containing polyisobutylene residues, and the hard segments comprise diisocyanate residues and optionally chain extender residues; wherein the phenoxy-containing polyisobutylene residues include oxygen atoms that are not part of a urethane or urethane-urea group, if present.
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