Radiopaque polymers for medical devices
AssigneeEndoshape, Inc.
InventorStephen D. Goodrich
Life of this patent
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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 multifunctional non-iodinated monomer wherein neither of the two monomers is fluorinated. Devices formed from radiopaque polymer compositions are also provided.
Claims20
A polymer composition comprising a crosslinked network, the network comprising:
- a) a first repeating unit represented by one of Formula 1, 1-A, 1-B or 1-C:
- wherein X is Br or I;
- m is an integer from 3 to 5;
- R1 is substituted or unsubstituted C2-C36 alkylene, C2-C36 cycloalkylene, C2-C36 alkenylene, C2-C36 cycloalkenylene, C2-C36 alkynylene, C5-C36 arylene, or C5-C36 heteroarylene;
- L1 is a single bond, —(CH2)n—, —(HCCH)n—, —O—, —S—, —SO—, —SO2—, —SO3—, —OSO2—, —NR2—, —CO—, —COO—, —OCO—, —OCOO—, —CONR3—, —NR4CO—, —OCONR5—, —NR6COO—, or —NR7CONR8—;
- Ar1 is a C5-C30 aryl or C5-C30 heteroaryl that is substituted with three or more I, Br or Bi atoms;
- each of R2-R8 is independently hydrogen or C1-C10 alkyl;
- and
- n is an integer selected from the range of 1 to 16;
- wherein the amount of the first repeating unit in the polymer composition is from 15 to 35 wt %;
- and
- b) a second repeating unit represented by Formula 2:
- wherein R9 is
- wherein R11 is C6-C20 alkylene and n4 is an integer from 1 to 50;
- and
- wherein the amount of the second repeating unit in the polymer composition is from 65 to 85 wt %.
A polymer composition comprising a crosslinked network formed by polymerization of a monomer mixture comprising:
- a) a first monomer having the general structure of one of Formula 8, 8-A, 8-B or 8-C
- wherein X is Br or I;
- m is an integer from 3 to 5;
- wherein R1 is substituted or unsubstituted C2-C36 alkylene, C2-C36 cycloalkylene, C2-C36 alkenylene, C2-C36 cycloalkenylene, C2-C36 alkynylene, C5-C36 arylene, or C5-C36 heteroarylene;
- L1 is a single bond, —(CH2)n—, —(HCCH)n—, —O—, —S—, —SO—, —SO2—, —SO3—, —OSO2—, —NR2—, —CO—, —COO—, —OCO—, —OCOO—, —CONR3—, —NR4CO—, —OCONR5—, —NR6COO—, or —NR7CONR8—;
- Ar1 is a C5-C30 aryl or C5-C30 heteroaryl that is substituted with three or more I, Br or Bi atoms;
- and
- each of R2-R8 is independently hydrogen or C1-C10 alkyl;
- n is an integer selected from the range of 1 to 16;
- wherein the amount of the first monomer is from 15 to 35 wt % of the monomer mixture;
- and
- b) a second monomer having the general structure of Formula 9
- wherein R9 is
- wherein R11 is C6-C20 alkylene and n4 is an integer from 1 to 50;
- and
- wherein the amount of the second monomer is from 65 to 85 wt % of the monomer mixture.
A method for making a polymer composition comprising a crosslinked network, the method comprising the steps of:
- a) forming a monomer mixture comprising
- i) a first monomer having the general structure of one of Formula 8, 8-A, 8-B or 8-C
- wherein X is Br or I;
- m is an integer from 3 to 5;
- wherein R1 is substituted or unsubstituted C2-C36 alkylene, C2-C36 cycloalkylene, C2-C36 alkenylene, C2-C36 cycloalkenylene, C2-C36 alkynylene, C5-C36 arylene, or C5-C36 heteroarylene;
- L1 is a single bond, —(CH2)n—, —(HCCH)n—, —O—, —S—, —SO—, —SO2—, —SO3—, —OSO2—, —NR2—, —CO—, —COO—, —OCO—, —OCOO—, —CONR3, —NR4CO—, —OCONR5—, —NR6COO—, or —NR7CONR8—;
- Ar1 is a C5-C30 aryl or C5-C30 heteroaryl that is substituted with three or more I, Br or Bi atoms;
- and
- each of R2-R8 is independently hydrogen or C1-C10 alkyl;
- n is an integer selected from the range of 1 to 16;
- wherein the amount of the first monomer is from 15 to 35 wt % of the monomer mixture;
- and
- ii) a second monomer having the general structure of Formula 9
- wherein R9 is
- wherein R11 is C6-C20 alkylene and n4 is an integer from 1 to 50;
- and R14 is other than R9;
- and
- wherein the amount of the second monomer is from 65 to 85 wt % of the total amount of monomer in the monomer mixture;
- and
- iii) a free radical initiator;
- and
- b) polymerizing the monomer mixture.
Dependencies are inferred from the claim text.