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US 10,590,218 B2Granted
Polymer compositions with enhanced radiopacity
AssigneeEndoshape, Inc.
InventorsStephen D. Goodrich, Jeffrey P. Castleberry
Life of this patent
Estimating the term…
Abstract
Radiopaque polymer compositions and methods for making the compositions are provided. These radiopaque polymer compositions include polymer compositions comprising a crosslinked polymer network, the network comprising a first repeating unit derived from a monofunctional monomer and a second repeating unit derived from a crosslinker monomer or oligomer having more than two polymerizable groups. Devices formed from radiopaque polymer compositions are also provided.
Claims16
A polymer composition comprising a crosslinked network, the network comprising
- a) a plurality of first repeating units derived from a first reagent, the first reagent comprising a monomer having the structure of Formula 1, Formula 1-A, Formula 1-B or Formula 1-C;
- wherein
- X is Br or I;
- m in Formula 1-C is 1-5;
- each R11 is independently a substituted or unsubstituted C2-C36 alkylene group;
- C3-C36 cycloalkylene group;
- C2-C36 alkenylene group;
- C3-C36 cycloalkenylene group;
- C2-C36 alkynylene group;
- C5-C36 arylene group;
- or C5-C36 heteroarylene group;
- each L11 is independently a single bond;
- —(CH2)q—;
- —(HCCH)q—;
- —O—;
- —S—;
- —SO—;
- —SO2—;
- —SO3—;
- —OSO2—;
- —NR12—;
- —CO—;
- —COO—;
- —OCO—;
- —OCOO—;
- —CONR13—;
- —NR14CO—;
- —OCONR15—, —NR16COO—, or —NR17CONR18—;
- each Ar11 is independently an iodine-, bromine or bismuth-containing C5-C36 aryl group containing one or more rings, or an iodine-, bromine or bismuth-containing C5-C36 heteroaryl group containing one or more rings;
- each of R12-R18 is independently hydrogen or a C1-C10 alkyl group;
- each q is independently an integer selected from the range of 1 to 10;
- b) a plurality of second repeating units derived from a second reagent, the second reagent comprising a branched monomer or oligomer comprising at least three terminal polymerizable groups but not comprising iodine, bromine or bismuth, wherein the branched monomer of the second reagent comprises a central portion R1 linked to at least two end portions, Y1 and Y2, at least one of the end portions being branched, wherein both Y1 and Y2 are represented by the structure of
- wherein
- R1 is C6 to C20 alkylene, and
- wherein the central portion R1 is linked to the end portions Y1 and Y2 through linker L1, wherein L1 is a single bond, —(CH2)n—, —(HCCH)n—, —O—, —S—, —SO—, —SO2—, —SO3—, —OSO2—, —NR3—, —CO—, —COO—, —OCO—, —OCOO—, —CONR4—, —NR5CO—, —OCONR6—, —NR7COO—, or —NR8CONR9 and each of R3-R9 is independently hydrogen or C1-C10 alkyl;
- and
- c) a plurality of third repeating units derived from a third reagent, the third reagent comprising a monomer having at least two terminal polymerizable groups.
34 more elements
A method of making a crosslinked polymer composition, the method comprising the steps of:
- a) forming a polymer precursor mixture comprising
- i) a first reagent comprising a monomer having the structure of Formula 1, Formula 1-A, Formula 1-B or Formula 1-C;
- wherein
- X is Br or I;
- m in Formula 1-C is 1-5;
- each R11 is independently a substituted or unsubstituted C2-C36 alkylene group;
- C3-C36 cycloalkylene group;
- C2-C36 alkenylene group;
- C3-C36 cycloalkenylene group;
- C2-C36 alkynylene group;
- C5-C36 arylene group;
- or C5-C36 heteroarylene group;
- each L11 is independently a single bond;
- —(CH2)q—;
- —(HCCH)q—;
- —O—;
- —S—;
- —SO—;
- —SO2—;
- —SO3—;
- —OSO2—;
- —NR12—;
- —CO—;
- —COO—;
- —OCO—;
- —OCOO—;
- —CONR13—;
- —NR14CO—;
- —OCONR15—, —NR16COO—, or —NR17CONR18—;
- each Ar11 is independently an iodine-, bromine or bismuth-containing C5-C36 aryl group containing one or more rings, or an iodine-, bromine or bismuth-containing C5-C36 heteroaryl group containing one or more rings;
- each of R12-R18 is independently hydrogen or a C1-C10 alkyl group;
- each q is independently an integer selected from the range of 1 to 10;
- ii) a second reagent comprising a branched monomer or oligomer comprising at least three terminal polymerizable groups but not comprising iodine, bromine or bismuth, wherein the branched monomer of the second reagent comprises a central portion R1 linked to at least two end portions, Y1 and Y2, at least one of the end portions being branched, wherein both Y1 and Y2 are represented by the structure of
- wherein
- R1 is C6 to C20 alkylene, and
- wherein the central portion R1 is linked to the end portions Y1 and Y2 through linker L1, wherein L1 is a single bond, —(CH2)n—, —(HCCH)n—, —O—, —S—, —SO—, —SO2—, —SO3—, —OSO2—, —NR3—, —CO—, —COO—, —OCO—, —OCOO—, —CONR4—, —NR5CO—, —OCONR6—, —NR7COO—, or —NR8CONR9 and each of R3-R9 is independently hydrogen or C1-C10 alkyl;
- and
- iii) a third reagent comprising a monomer having at least two terminal polymerizable groups, and
- b) polymerizing the polymer precursor mixture with an initiator.
36 more elements
Dependencies are inferred from the claim text.