Polyisobutylene urethane, urea and urethane/urea copolymers and medical devices containing the same

• US 8,501,831 B2
• Filed: 09/14/2012
• Issued: 08/06/2013
• Est. Priority Date: 06/27/2008
• Status: Active Grant

• Current Assignee: Cardiac Pacemakers Incorporated (Boston Scientific Corporation)
• Original Assignee: Cardiac Pacemakers Incorporated (Boston Scientific Corporation)
• Inventors: Desai, Shrojalkumar, Schwarz, Marlene C., Boden, Mark, Krishnan, Mohan, Smith, Michael C., Strickler, Frederick H., Cooke, Daniel J.
• Primary Examiner(s): ZIMMER, MARC S
• Application Number:
  US13/618,148
• Publication Number:
  US 20130013040A1
• Time in Patent Office: 326 Days
• Field of Search: None
• US Class Current: 523/105
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/4063 Mixtures of compounds of group C08G18/62 with other macromolecular compounds
• CPC Class Codes: C08G 18/4854 Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/4858 Polyethers containing oxyalkylene groups having more than four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/6204 Polymers of olefins unsaturated polymers of conjugated dienes C08G18/69
• CPC Class Codes: C08G 18/6511 compounds of group C08G18/3203
• CPC Class Codes: C08G 18/7657 containing two or more aromatic rings
• CPC Class Codes: C08L 75/00 Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers

Abstract

The present invention pertains to polyisobutylene urethane, urea and urethane/urea copolymers, to methods of making such copolymers and to medical devices that contain such polymers. According to certain aspects of the invention, polyisobutylene urethane, urea and urethane/urea copolymers are provided, which comprise a polyisobutylene segment, an additional polymeric segment that is not a polyisobutylene segment, and a segment comprising a residue of a diisocyanate. According to other aspects of the invention, polyisobutylene urethane, urea and urethane/urea copolymers are provided, which comprise a polyisobutylene segment and end groups that comprise alkyl-, alkenyl- or alkynyl-chain-containing end groups.

Claims

1. A method for making an implantable or insertable medical device including a polyisobutylene urethane, urea or urethane/urea copolymer, the method comprising:

reacting a diisocyanate, a polyisobutylene polyol or polyamine and a polyether diol to form a polyisobutylene urethane, urea or urethane/urea copolymer; and

forming at least a portion of an implantable or insertable medical device from the polyisobutylene urethane, urea or urethane/urea copolymer,

wherein the molar amount of the polyisobutylene reacted with the polyether diol is greater than or equal to the molar amount of polyether diol.

2. The method of claim 1, wherein the molar ratio of the polyisobutylene to the polyether diol is 1.5:

0.5 to 1;

1.

3. The method of claim 1, wherein the reacting step comprises:

reacting the diisocyanate with the polyisobutylene polyol or polyamine and the polyether diol to form an isocyante-end-capped prepolymer; and

reacting the isocyante-end-capped prepolymer with a chain extender.

4. The method of claim 3, wherein the chain extender includes at least one member selected from the group consisting of aliphatic diols, aromatic diols, aliphatic diamines, aromatic diamines.

5. The method of claim 3 wherein the molar ratio of the diisocyanate to polyisobutylene to chain extender is 2:

1.5;

0.5 to 2;

0.5;

1.5.

6. The method of claim 1, wherein the polyether diol includes at least one member selected from the group consisting of:

methylene oxide, dimethylene oxide (ethylene oxide), trimethylene oxide, propylene oxide, and tetramethylene oxide.

7. The method of claim 1, wherein the diisocyanate includes at least one member selected from the group consisting of an aromatic diisocyanate, an aliphatic diisocyanate and combinations thereof.

8. The method of claim 1, wherein the diisocyanate is selected from the group consisting of 4,4′

-methylenediphenyl diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, para-phenylene diisocyanate, 3,3′

-tolidene-4,4′

-diisocyanate, 3,3′

-dimethyl-diphenylmethane-4,4′

-diisocyanate, and combinations thereof.

9. An implantable or insertable medical device comprising:

a polyisobutylene urethane, urea or urethane/urea copolymer comprising;

a residue of a diisocyanate;

a residue of a polyisobutylene polyol or polyamine; and

a residue of a polyether diol, wherein a molar amount of the polyisobutylene is greater than the molar amount of polyether diol.

10. The implantable or insertable medical device of claim 9, wherein the molar ratio of the polyisobutylene to the polyether diol is 1.5:

0.5 to 1;

1.

11. The implantable or insertable medical device of claim 9, and further comprising a residue of a chain extender.

12. The implantable or insertable medical device of claim 11, wherein the chain extender includes at least one member selected from the group consisting of aliphatic diols, aromatic diols, aliphatic diamines, aromatic diamines.

13. The implantable or insertable medical device of claim 11, the molar ratio of the diisocyanate to polyisobutylene to chain extender is 2:

1.5;

0.5 to 2;

0.5;

1.5.

14. The implantable or insertable medical device of claim 9, wherein the polyether diol includes at least one member selected from the group consisting of:

methylene oxide, dimethylene oxide (ethylene oxide), trimethylene oxide, propylene oxide, and tetramethylene oxide.

15. The implantable or insertable medical device of claim 9, wherein the diisocyanate includes at least one member selected from the group consisting of an aromatic diisocyanate, an aliphatic diisocyanate and combinations thereof.

16. The implantable or insertable medical device of claim 9, wherein the diisocyanate includes at least one member selected from the group consisting of 4,4′

-methylenediphenyl diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, para-phenylene diisocyanate, 3,3′

-tolidene-4,4′

-diisocyanate, 3,3′

-dimethyl-diphenylmethane-4,4′

-diisocyanate, and combinations thereof.

17. The implantable or insertable medical device of claim 9, and further comprising at least one end group that comprise alkyl, alkenyl or alkynyl chains ranging from 1 to 17 carbons atoms in length.