Compositions and methods for copolymer solutions with high weight percent copolymer

Patent metadata

Field	Value
Publication number	US-2016311983-A1
Application number	US-201615097806-A
Country	US
Kind code	A1
Filing date	Apr 13, 2016
Priority date	Apr 23, 2015
Publication date	Oct 27, 2016
Grant date	—

Abstract

A method of making a solution including a block copolymer includes dissolving the block copolymer in a solvent mixture to form a solution, the solvent mixture including at least two solvent components. The solubility of the block copolymer in the solvent mixture is at least about 7 wt. % at about 64° C. The solvent mixture is non-reactive with the block copolymer. The solubility of the block copolymer in a single solvent solution consisting of any one of the at least two solvent components and the block copolymer is not greater than about 1 wt. % at about 64° C. The block copolymer includes polyisobutylene segments and polyurethane segments.

First claim

We claim:

1 . A method of making a solution including a block copolymer, the method comprising:
dissolving a block copolymer in a solvent mixture to form a solution, the solvent mixture including at least two solvent components, wherein the solubility of the block copolymer in the solvent mixture is at least about 7 wt. % at about 64° C., the solvent mixture is non-reactive with the block copolymer, and the solubility of the block copolymer in a single solvent solution consisting of any one of the at least two solvent components and the block copolymer is not greater than about 1 wt. % at about 64° C., wherein the block copolymer includes polyisobutylene segments and polyurethane segments.

2 . The method of claim 1 , wherein a Hansen Solubility Parameter Distance between the block copolymer and the solvent mixture is less than about 2 MPa 0.5 .

3 . The method of claim 1 , wherein the solvent mixture consists of two solvent components, a first solvent component selected from the group consisting of acetophenone, benzaldehyde, cyclohexanone, and ethyl cinnamate; and a second solvent component selected from the group consisting of aromatic hydrocarbons, cyclohexane, ethyl benzene, Solvesso™ 100, Solvesso™ 150, toluene, and xylene.

4 . The method of claim 3 , wherein the first solvent component is cyclohexanone, and the second solvent component is toluene.

5 . The method of claim 1 , wherein the solvent mixture consists of three solvent components, a first solvent component selected from the group consisting of toluene and Solvesso™ 150, a second solvent component selected from the group consisting of phenyl acetonitrile, caprolactone (epsilon), benzaldehyde, and butyl benzoate; and a third solvent component selected from the group consisting of benzyl acetate, tetrahydrofuran, 2,6-dimethylpyridine, benzyl benzoate, and safrole.

6 . The method of claim 1 , wherein the solvent mixture includes at least three solvent components, and at least one of the solvent components has a polar Hansen Solubility Parameter of at least about 5.6 MPa 0.5 and at least one of the solvent components has a hydrogen bonding Hansen Solubility Parameter of at least about 4.6 MPa 0.5 .

7 . The method of claim 1 , wherein the solubility of the block copolymer in the solvent mixture is at least about 20 wt. % at about 64° C.

8 . A composition comprising:
a first solvent; a second solvent; and a block copolymer including polyisobutylene segments and polyurethane segments in solution with the first solvent and the second solvent in an amount no less than about 7 wt. % at about 64° C., wherein a maximum solubility of the block copolymer in a solution consisting of the first solvent and the block copolymer is not greater than about 1 wt. % at about 64° C., and a maximum solubility of the block copolymer in a solution consisting of the second solvent and the block copolymer is not greater than about 1 wt. % at about 64° C.

9 . The composition of claim 8 , wherein the first solvent is selected from the group consisting of acetophenone, benzaldehyde, cyclohexanone, and ethyl cinnamate; and the second solvent is selected from the group consisting of aromatic hydrocarbons, cyclohexane, ethyl benzene, Solvesso™ 100, Solvesso™ 150, toluene, and xylene.

10 . The composition of claim 9 , wherein the first solvent is cyclohexanone, and the second solvent is toluene.

11 . The composition of claim 8 , further including a third solvent, wherein at least one of the solvents has a polar Hansen Solubility Parameter of at least about 5.6 MPa 0.5 and at least one of the solvents has a hydrogen bonding Hansen Solubility Parameter of at least about 4.6 MPa 0.5 , and a maximum solubility of the block copolymer in a solution consisting of the third solvent and the block copolymer is not greater than about 1 wt. % at about 64° C.

12 . The composition of claim 8 , further including a third solvent, wherein the first solvent is selected from the group consisting of toluene and Solvesso™ 150, the second solvent is selected from the group consisting of phenyl acetonitrile, caprolactone (epsilon), benzaldehyde, and butyl benzoate; and the third solvent is selected from the group consisting of benzyl acetate, tetrahydrofuran, 2,6-dimethylpyridine, benzyl benzoate, and safrole, wherein a maximum solubility of the block copolymer in a solution consisting of the third solvent and the block copolymer is not greater than about 1 wt. % at about 64° C.

13 . The composition of claim 8 , wherein the solubility of the block copolymer in the first solvent and the second solvent together is at least about 20 wt. % at about 64° C.

14 . A method for making an implantable medical device including a block copolymer layer, the method comprising:
formulating a block copolymer solution including a block copolymer including polyisobutylene segments and polyurethane segments, the block copolymer solution at a concentration of at least about 7 wt. % at about 64° C., wherein formulating includes:
dissolving a block copolymer in a solvent mixture to form the block copolymer solution, the solvent mixture including at least two solvent components, wherein the solubility of the block copolymer in the solvent mixture is at least about 7 wt. % at about 64° C., the solvent mixture is non-reactive with the block copolymer, and the solubility of the block copolymer in a single solvent solution consisting of any one of the at least two solvent components and the block copolymer is not greater than about 1 wt. % at about 64° C.
depositing the block copolymer solution onto the implantable medical device; and drying the implantable medical device and evaporating the solvent mixture to leave behind the block copolymer layer.

15 . The method of claim 14 , wherein the solvent mixture consists of two solvent components, a first solvent component selected from the group consisting of acetophenone, benzaldehyde, cyclohexanone, and ethyl cinnamate; and a second solvent component selected from the group consisting of aromatic hydrocarbons, cyclohexane, ethyl benzene, Solvesso™ 100, Solvesso™ 150, toluene, and xylene.

16 . The method of claim 15 , wherein the first solvent component is cyclohexanone, and the second solvent component is toluene.

17 . The method of claim 14 , wherein the solvent mixture consists of three solvent components, a first solvent component selected from the group consisting of toluene and Solvesso198 150, a second solvent component selected from the group consisting of phenyl acetonitrile, caprolactone (epsilon), benzaldehyde, and butyl benzoate; and a third solvent component selected from the group consisting of benzyl acetate, tetrahydrofuran, 2,6-dimethylpyridine, benzyl benzoate, and safrole.

18 . The method of claim 14 , wherein depositing includes at least one of solvent casting, spray coating, or dip coating the block copolymer solution onto the implantable medical device.

19 . The method of claim 14 , wherein the solvent mixture includes at least three solvent components, and at least one of the solvent components has a polar Hansen Solubility Parameter of at least about 5.6 MPa 0.5 and at least one of the solvent components has a hydrogen bonding Hansen Solubility Parameter of at least about 4.6 MPa 0.5 .

20 . The method of claim 19 , wherein depositing includes at least one of electrospinning and electrospraying the block copolymer solution onto the implantable medical device.

Assignees

• Cardiac Pacemakers Inc

Inventors

• Delaney Jr Joseph T
• Wulfman David R
• Aremu Adeniyi
• Adenusi Adegbola O

Classifications

• A61L31/10 Primary

  Macromolecular materials · CPC title

• A61L2420/06

  Coatings containing a mixture of two or more compounds · CPC title

• C08J2375/04

  Polyurethanes · CPC title

• C08J3/092

  Hydrocarbons · CPC title

• C08J3/095

  Oxygen containing compounds · CPC title