Biodegradable terpolymers and terpolymer blends as pressure-sensitive adhesives

• US 9,416,221 B2
• Filed: 08/30/2011
• Issued: 08/16/2016
• Est. Priority Date: 08/30/2010
• Status: Active Grant

• Current Assignee: SurModics Pharmaceuticals, Inc (Rag-Stiftung)
• Original Assignee: Surmodics Incorporated
• Inventors: Morris, Philip, Bowman, Howard, Lucast, Don
• Primary Examiner(s): FERRE, ALEXANDRE F
• Application Number:
  US13/221,464
• Publication Number:
  US 20120078155A1
• Time in Patent Office: 1,813 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: A61L 2/0035 Gamma radiation
• CPC Class Codes: A61L 2/081 Gamma radiation
• CPC Class Codes: A61L 2202/24 Medical instruments, e.g. endoscopes, catheters, sharps
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C09J 167/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C09J167/06 takes precedence
• CPC Class Codes: C09J 2467/00 Presence of polyester
• CPC Class Codes: C09J 2467/006 in the substrate
• CPC Class Codes: C09J 7/255 Polyesters
• CPC Class Codes: C09J 7/38 Pressure-sensitive adhesives [PSA]
• CPC Class Codes: Y10T 428/1334 Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]
• CPC Class Codes: Y10T 428/1352 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/1476 Release layer
• CPC Class Codes: Y10T 428/21 : Circular sheet or circular blank
• CPC Class Codes: Y10T 428/24777 : Edge feature
• CPC Class Codes: Y10T 428/24942 : including components having same physical characteristic in differing degree
• CPC Class Codes: Y10T 428/249921 : Web or sheet containing structurally defined element or component
• CPC Class Codes: Y10T 428/2839 : with release or antistick coating
• CPC Class Codes: Y10T 428/2865 : including monomer or polymer of carbohydrate [e.g., starch, dextrin, etc.] Or protein [e.g., casein, animal protein, etc.] Or derivative thereof
• CPC Class Codes: Y10T 428/31681 : Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
• CPC Class Codes: Y10T 428/31786 : Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31855 : Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 442/172 : Coated or impregnated

Abstract

Disclosed herein are terpolymers and blends prepared from polyester terpolymers that can function as pressure-sensitive adhesives. The disclosed articles can comprise the terpolymer and terpolymer blends coated to a conformable backing member. The terpolymer and terpolymer blends can further comprise a bioactive agent.

Claims

1. An article comprising:

a conformable backing member comprising a sheet; and

a pressure-sensitive adhesive (PSA) comprising a poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) having a molecular weight (M_w) of from 60,000 to 130,000 Daltons and a polydispersity index (PDI) of less than 2.0;

wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) exhibits storage modulus (G′

) values of from about 1.5×

10⁵ Pa to about 5.5×

10⁵ Pa, over a frequency of from about 0.1 to about 1 Hz; and

exhibits storage modulus (G′

) values of from about 1.0×

10⁶ Pa to about 4.0×

10⁶ Pa, over a frequency of from about 10² to about 10⁴ Hz at 30°

C., and having a surface thereof coated to the conformable backing member;

wherein the PSA coats 0.1% to 100% of the surface area of the conformable backing member.

2. The article of claim 1, wherein the PSA further comprises a bioactive agent.

3. The article of claim 1, wherein the conformable backing member further comprises a bioactive layer.

4. The article of claim 1, wherein the PSA comprises an enzyme inhibitor to increase wound healing.

5. The article of claim 1, wherein the conformable backing member comprises gauze.

6. The article of claim 1, wherein the PSA is impregnated with chlorhexidine gluconate.

7. The article of claim 1, wherein the article is an anti-microbial carrier.

8. The article of claim 1, wherein the article is wrapped around an internal tissue or bone.

9. The article of claim 1, wherein the article is formed into a sealable package.

10. The article of claim 9, wherein the article formed is an envelope.

11. The article of claim 9, wherein the article formed contains a gel or liquid comprising a bioactive agent.

12. The article of claim 1, wherein the article is a diaper and the edges or seams of the diaper are adhered with the PSA.

13. The article of claim 1, wherein the article is compostable packing and the edges or seams of the compostable packing are adhered with the PSA.

14. The article of claim 1, wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) comprises from 10 to 60 mol % D,L-lactide, from 10 to 50 mol % D,L-glycolide, and from 10 to 80 mol % ε

-caprolactone.

15. The article of claim 1, wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) comprises from 20 to 40 mol % D,L-lactide, from 10 to 30 mol % D,L-glycolide, and from 40 to 60 mol % ε

-caprolactone.

16. The article of claim 1, wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) comprises 30 mol % D,L-lactide, 20 mol % D,L-glycolide, and 50 mol % ε

-caprolactone.

17. The article of claim 1, wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) has a polydispersity index (PDI) ranging from 1.5 to 1.8.

18. The article of claim 1, wherein the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) has a molecular weight (M_w) of from 100,000 to 130,000 Daltons.

19. An article, comprising:

a conformable backing member comprising a sheet; and

a pressure-sensitive adhesive (PSA) comprising a blend comprising;

(a) a first poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) having a molecular weight (M_w) of from 75,000 to 250,000 Daltons and a polydispersity index (PDI) of less than 2.0, and

(b) a second poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) having a molecular weight (M_w) of 130,000 Daltons or less and a polydispersity index (PDI) of less than 2.0;

wherein the second poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) has a molecular weight (M_w) that is less than the first poly(D,L-lactide-co-glycolide-co-ε

-caprolactone); and

wherein the weight ratio of the first poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) to the second poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) is from about 90;

10 to about 60;

40,

and having a surface of the PSA coated to the conformable backing member;

wherein the PSA coats 0.1% to 100% of the surface area of the conformable backing member.

20. An article, comprising:

a conformable backing member comprising a sheet; and

a pressure-sensitive adhesive (PSA) comprising a blend comprising

(a) a poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) having a molecular weight of from 75,000 to 250,000 Daltons and a polydispersity index (PDI) of less than 2.0, and

(b) a poly(D,L-lactide-co-glycolide-co-mPEG) having a molecular weight of less than 25,000 Daltons and a polydispersity index (PDI) of less than 2.0; and

wherein the weight ratio of the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone) to the poly(D,L-lactide-co-glycolide-co-mPEG) is from about 95;

5 to about 75;

25,

and having a surface of the PSA coated to the conformable backing member;

wherein the PSA coats 0.1% to 100% of the surface area of the conformable backing member.