Terpolymers as pressure-sensitive adhesives

• US 9,598,532 B2
• Filed: 08/30/2011
• Issued: 03/21/2017
• Est. Priority Date: 08/30/2010
• Status: Active Grant

• Current Assignee: SurModics Pharmaceuticals, Inc
• Original Assignee: Surmodics Incorporated
• Inventors: Bowman, Howard, Hudson, Bruce W.
• Primary Examiner(s): Parad, Dennis J
• Assistant Examiner(s): BECKHARDT, LYNDSEY MARIE
• Application Number:
  US13/221,389
• Publication Number:
  US 20120077887A1
• Time in Patent Office: 2,030 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 that can function as pressure-sensitive adhesives. The disclosed articles comprise the terpolymers adhered to a release liner. The disclosed implant devices comprise the pressure-sensitive adhesive terpolymer adhered to a surface thereof. The pressure-sensitive adhesive terpolymer can promote adhesion of the implant device to a location in a subject.

Claims

1. An article, comprising:

a pressure-sensitive adhesive (PSA) having a first adhesive surface and an opposing second adhesive surface,

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

-caprolactone) having a molecular weight (M_w) of from 100,000 to 140,000 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.;

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

-caprolactone) comprising from 50 to 60 mol % caprolactone; and

a bioactive agent selected from the group consisting of gentamicin, tobramycin, rifampin, and minocycline, or combinations thereof; and

a release liner, wherein the release liner fully covers the first adhesive surface and the second adhesive surface of the pressure-sensitive adhesive.

2. The article of claim 1, wherein the pressure-sensitive adhesive (PSA) consists of the poly(D,L-lactide-co-glycolide-co-ε

-caprolactone).

3. The article of claim 1, the pressure-sensitive adhesive comprising a planar film.

4. The article of claim 1, wherein the pressure-sensitive adhesive is divided into a plurality of discrete units separated from one another, the plurality of units held together by the release liner.