# US 10,441,688 B2 · PET solutions and methods of making PET solutions for medical devices

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- Number: US 10,441,688 B2
- Document ID: US10441688B2
- Status: Granted
- Kind: B2
- Application number: 15/485,491
- Filed: 2017-04-12
- Published: 2017-10-12
- Granted: 2019-10-15
- Earliest claimed: 2016-04-12
- Assignees: Cardiac Pacemakers, Inc.
- Applicants: Cardiac Pacemakers, Inc.
- Inventors: Joseph T. Delaney, Jr.; David R. Wulfman; Adeniyi O. Aremu; Adegbola O. Adenusi
- Web page: https://patentgrep.com/patent/US10441688B2

## CPC

- A61L 31/10: Macromolecular materials
- A61L 27/34: Macromolecular materials
- B05D 1/04: involving the use of an electrostatic field {(B05D1/025 and B05D1/14 take precedence)}
- B05D 3/04: by exposure to gases
- C08G 63/183: Terephthalic acids
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C09D 7/20: Diluents or solvents
- C09D 167/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence)
- D01D 1/02: Preparation of spinning solutions
- D01D 5/003: {the material being a polymer solution or dispersion (D01D5/0053 takes precedence)}
- 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}
- D01F 6/62: from polyesters
- A61L 2420/02: Methods for coating medical devices
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- D01D: MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01F: CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS

## 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 MPa0.5, a polar HSP of 5.56 MPa0.5, and a hydrogen bonding HSP of 14.27 MPa0.5 is less than about 2 MPa0.5.

## Claims

### Claim 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 consisting of two solvent components, a first solvent component and a second solvent component 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 MPa0.5, a polar HSP of 5.56 MPa0.5, and a hydrogen bonding HSP of 14.27 MPa0.5 is less than about 2 MPa0.5, wherein:
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, or trans anethole and the second solvent component is dl-lactic acid;
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;
the first solvent component is benzyl alcohol and the second solvent component is one of 1-butanol, iso-butanol, and ethylene glycol;
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; or
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.

### Claim 2 (depends on 1)

The method of claim 1, 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.

### Claim 3 (depends on 1)

The method of claim 1, 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.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The method of claim 1, 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.

### Claim 6 (depends on 1)

The method of claim 1, 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.

### Claim 7 (depends on 1)

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 MPa0.5, and a Hansen hydrogen bonding parameter of at least about 4.6 MPa0.5.

### Claim 8 (depends on 1)

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.

### Claim 9

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 consisting of a first solvent component and a second solvent component, 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 MPa0.5, a polar HSP of 5.56 MPa0.5, and a hydrogen bonding HSP of 14.27 MPa0.5 is less than about 2 MPa0.5;
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, 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.

### Claim 10 (depends on 9)

The method of claim 9, 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 MPa0.5, and a Hansen hydrogen bonding parameter of at least about 4.6 MPa0.5.

### Claim 11 (depends on 9)

The method of claim 9, 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.

### Claim 12 (depends on 9)

The method of claim 9, wherein depositing includes at least one of electrospinning and electrospraying the poly(ethylene terephthalate) solution onto the implantable medical device.

### Claim 13 (depends on 9)

The method of claim 9, 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.

### Claim 14 (depends on 9)

The method of claim 9, wherein the first solvent component is benzyl alcohol and the second solvent component is one of 1-butanol, iso-butanol, and ethylene glycol.