Biodegradable terpolymers and terpolymer blends as pressure-sensitive adhesives

Patent metadata

Field	Value
Publication number	US-9416221-B2
Application number	US-201113221464-A
Country	US
Kind code	B2
Filing date	Aug 30, 2011
Priority date	Aug 30, 2010
Publication date	Aug 16, 2016
Grant date	Aug 16, 2016

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.

First claim

What is claimed is:

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 1.5×10 5 Pa to about 5.5×10 5 Pa, over a frequency of from about 0.1 to about 1 Hz; and exhibits storage modulus (G′) values of from about 1.0×10 6 Pa to about 4.0×10 6 Pa, over a frequency of from about 10 2 to about 10 4 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.

Assignees

• Bowman Howard
• Lucast Don
• Philip Morris
• Surmodics Inc

Inventors

• Bowman Howard
• Lucast Don
• Morris Philip

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P19/00

  Drugs for skeletal disorders · CPC title

• A61P17/02

  for treating wounds, ulcers, burns, scars, keloids, or the like · CPC title

• A61P1/00

  Drugs for disorders of the alimentary tract or the digestive system · CPC title

• Y10T428/31855

  Of addition polymer from unsaturated monomers · CPC title