PET SOLUTIONS AND METHODS OF MAKING PET SOLUTIONS FOR MEDICAL DEVICES

• US 20170290957A1
• Filed: 04/12/2017
• Published: 10/12/2017
• Est. Priority Date: 04/12/2016
• Status: Active Grant

• Current Assignee: Cardiac Pacemakers Incorporated (Boston Scientific Corporation)
• Original Assignee: Cardiac Pacemakers Incorporated (Boston Scientific Corporation)
• Inventors: Delaney, JR., Joseph T., Wulfman, David R., Aremu, Adeniyi O., Adenusi, Adegbola O.
• Granted Patent: US 10,441,688 B2
• Time in Patent Office: Days
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: B05D 1/04 involving the use of an electrostatic field B05D1/025 and B05D1/14 take precedence
• CPC Class Codes: B05D 3/04 by exposure to gases
• CPC Class Codes: C08G 63/183 Terephthalic acids
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C09D 167/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C09D167/06 takes precedence
• CPC Class Codes: C09D 7/20 Diluents or solvents
• CPC Class Codes: D01D 1/02 Preparation of spinning solutions
• CPC Class Codes: D01D 5/003 the material being a polymer solution or dispersion D01D5/0053 takes precedence
• CPC Class Codes: D01D 5/0084 Coating by electro-spinning, i.e. the electro-spun fibres are not removed from the collecting device but remain integral with it, e.g. coating of prostheses
• CPC Class Codes: D01F 6/62 from polyesters

Abstract

A method of making a solution including poly(ethylene terephthalate). The method includes dissolving poly(ethylene terephthalate) in a solvent mixture to form a solution, the solvent mixture including two solvent components. A Hansen Solubility Parameter Distance between the solvent mixture and HSP coordinates having a dispersion HSP of 18.02 MPa^0.5, a polar HSP of 5.56 MPa^0.5, and a hydrogen bonding HSP of 14.27 MPa^0.5 is less than about 2 MPa^0.5.

Claims

1. A method of making a solution including poly(ethylene terephthalate), the method comprising:

dissolving poly(ethylene terephthalate) in a solvent mixture to form a solution, the solvent mixture including at least two solvent components, wherein a solubility of the poly(ethylene terephthalate) in the solvent mixture is at least about 2 wt. % at a temperature from about 20°

C. to about 25°

C., wherein a Hansen Solubility Parameter Distance between the solvent mixture and HSP coordinates having a dispersion HSP of 18.02 MPa^0.5, a polar HSP of 5.56 MPa^0.5, and a hydrogen bonding HSP of 14.27 MPa^0.5 is less than about 2 MPa^0.5.

2. The method of claim 1, wherein the solvent mixture consists of two solvent components, a first solvent component and a second solvent component, wherein the first solvent component is present in the solvent mixture in concentrations of greater than or equal to about 50 vol. % of the solvent mixture, with the balance being the second solvent component

3. The method of claim 2, wherein the second solvent component is dl-lactic acid and the first solvent component is one of (E)-cinnamyl alcohol, 2-allylphenol, 4-propylphenol, chavicol, dihydroeugenol, hawthorn carbinol, hawthorn ethanol, isopropenylphenol, n-butyl salicylate, peony alcohol, and trans anethole.

4. The method of claim 2, wherein the first solvent component is 2-phenoxy ethanol and the second solvent component is thymol;

or the first solvent component is n-butyl salicylate and the second solvent component is ethylene glycol.

5. The method of claim 2, wherein the first solvent component is benzyl alcohol and the second solvent component is one of 1-butanol, iso-butanol, and ethylene glycol.

6. The method of claim 2, wherein the first solvent component is thymol and the second solvent component is one of 2,3-butanediol, 2-hydroxy-2-methylpropanoic acid, and 2-methyl-1,3-butanediol.

7. The method of claim 2, wherein the first solvent component is cinnamyl alcohol and the second solvent component is one of 2-methyl-1,3-butanediol, 1-butanol, 2-propanol, or 3-methyl allyl alcohol.

8. The method of claim 1, wherein at least one of the first solvent component and the second solvent component has a Hansen polar solubility parameter of at least about 5.6 MPa^0.5, and a Hansen hydrogen bonding parameter of at least about 4.6 MPa^0.5.

9. The method of claim 1, wherein the solubility of the poly(ethylene terephthalate) in the solvent mixture is at least about 10 wt. % at a temperature from about 20°

C. to about 25°

C.

10. A method for making an implantable medical device including a poly(ethylene terephthalate) layer, the method comprising:

formulating a poly(ethylene terephthalate) solution by dissolving poly(ethylene terephthalate) in a solvent mixture to form a solution, the solvent mixture including at least two solvent components, wherein a solubility of the poly(ethylene terephthalate) in the solvent mixture is at least about 2 wt. % at a temperature from about 20°

C. to about 25°

C., wherein a Hansen Solubility Parameter Distance between the solvent mixture and HSP coordinates having a dispersion HSP of 18.02 MPa^0.5, a polar HSP of 5.56 MPa^0.5, and a hydrogen bonding HSP of 14.27 MPa^0.5 is less than about 2 MPa^0.5;

depositing the poly(ethylene terephthalate) solution onto the implantable medical device; and

drying the implantable medical device and evaporating the solvent mixture to leave behind the poly(ethylene terephthalate) layer.

11. The method of claim 10, wherein the solvent mixture consists of two solvent components, a first solvent component and a second solvent component, wherein the first solvent component is present in the solvent mixture in concentrations of greater than or equal to about 50 vol. % of the solvent mixture, with the balance being the second solvent component.

12. The method of claim 11, wherein the first solvent component of the composition is (E)-cinnamyl alcohol and the second solvent component is dl-lactic acid;

the first solvent component is 2-phenoxy ethanol and the second solvent component is thymol;

the first solvent component is 2-allylphenol and the second solvent component is dl-lactic acid;

the first solvent component cis 4-propylphenol and the second is dl-lactic acid;

the first solvent component is trans anethole and the second solvent component is dl-lactic acid;

the first solvent component is benzyl alcohol and the second solvent component is ethylene glycol, iso-butanol, or 1-butanol;

the first solvent component is chavicol and the second solvent component is dl-lactic acid;

the first solvent component is cinnamyl alcohol and the second solvent component is 2-methyl-1,3-butanediol, 1-butanol, 2-propanol, or 3-methyl allyl alcohol;

the first solvent component is dihydroeugenol and the second solvent component is dl-lactic acid;

the first solvent component is hawthorn carbinol, and the second solvent component is dl-lactic acid;

the first solvent component is hawthorn ethanol and the second solvent component is dl-lactic acid;

the first solvent component is isopropenylphenol and the second solvent component is dl-lactic acid;

the first solvent component is n-butyl salicylate and the second solvent component is dl-lactic acid or ethylene glycol;

the first solvent component is peony alcohol and the second solvent component is dl-lactic acid;

or the first solvent component is thymol and the second solvent component is 2,3-butanediol, 2-methyl-1,3-butanediol, or 2-hydroxy-2-methylpropanoic acid.

13. The method of claim 11, wherein at least one of the first solvent component and the second solvent component has a Hansen polar solubility parameter of at least about 5.6 MPa^0.5, and a Hansen hydrogen bonding parameter of at least about 4.6 MPa^0.5.

14. The method of claim 10, wherein the solubility of the poly(ethylene terephthalate) in the solvent mixture is at least about 10 wt. % at a temperature from about 20°

C. to about 25°

C.

15. The method of claim 10, wherein depositing includes at least one of electrospinning and electrospraying the poly(ethylene terephthalate) solution onto the implantable medical device.

16. A composition comprising:

a first solvent;

a second solvent; and

poly(ethylene terephthalate) in solution with the first solvent and the second solvent in an amount no less than about 2 wt. %,

wherein a Hansen Solubility Parameter Distance between the solvent mixture and HSP coordinates having a dispersion HSP of 18.02 MPa^0.5, a polar HSP of 5.56 MPa^0.5, and a hydrogen bonding HSP of 14.27 MPa^0.5 is less than about 2 MPa^0.5.

17. The composition of claim 16, wherein the first solvent of the composition is (E)-cinnamyl alcohol and the second solvent is dl-lactic acid;

the first solvent is 2-phenoxy ethanol and the second solvent is thymol;

the first solvent is 2-allylphenol and the second solvent is dl-lactic acid;

the first solvent cis 4-propylphenol and the second is dl-lactic acid;

the first solvent is trans anethole and the second solvent is dl-lactic acid;

the first solvent is benzyl alcohol and the second solvent is ethylene glycol, iso-butanol, or 1-butanol;

the first solvent is chavicol and the second solvent is dl-lactic acid;

the first solvent is cinnamyl alcohol and the second solvent is 2-methyl-1,3-butanediol, 1-butanol, 2-propanol, or 3-methyl allyl alcohol;

the first solvent is dihydroeugenol and the second solvent is dl-lactic acid;

the first solvent is hawthorn carbinol, and the second solvent is dl-lactic acid;

the first solvent is hawthorn ethanol and the second solvent is dl-lactic acid;

the first solvent is isopropenylphenol and the second solvent is dl-lactic acid;

the first solvent is n-butyl salicylate and the second solvent is dl-lactic acid or ethylene glycol;

the first solvent is peony alcohol and the second solvent is dl-lactic acid;

or the first solvent is thymol and the second solvent is 2,3-butanediol, 2-methyl-1,3-butanediol, or 2-hydroxy-2-methylpropanoic acid.

18. The composition of claim 17, wherein the second solvent is dl-lactic acid and the first solvent is one of (E)-cinnamyl alcohol, 2-allylphenol, 4-propylphenol, chavicol, dihydroeugenol, hawthorn carbinol, hawthorn ethanol, isopropenylphenol, n-butyl salicylate, peony alcohol, and trans anethole.

19. The composition of claim 16, wherein at least one of the first solvent and the second solvent has a Hansen polar solubility parameter of at least about 5.6 MPa^0.5, and a Hansen hydrogen bonding parameter of at least about 4.6 MPa^0.5.

20. The composition of claim 16, wherein poly(ethylene terephthalate) is in solution with the first solvent and the second solvent in an amount no less than about 10 wt. %.