IP Library Granted Patent US 9,332,991
Granted Patent B2
US 9,332,991 · App. 14/092,015 · Granted May 10, 2016

Adhesive articles containing a combination of surface micropatterning and reactive chemistry and methods of making and using thereof

Inventors: Maria Jose M. N. Pereira (Lisbon, PT); Woo-Kyung Cho (Arlington, MA); Robert S. Langer (Newton, MA); Jeffrey M. Karp (Brookline, MA)
Assignees: Massachusetts Institute of Technology; The Brigham and Women's Hospital, Inc.
A61B17/11A61L15/26A61L15/42A61L15/44A61L15/58A61L15/62A61L15/64
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Quick Facts
Patent No.
US 9,332,991
App. No.
14/092,015
Granted
May 10, 2016
Kind
B2
Abstract

Adhesive articles containing microtopography, such as microprotrusions, and a coating of adhesive glue, such an adhesive having known toxicity and/or tissue reactive functional groups are described herein. The articles described herein contain a substrate, a plurality of microfeatures, and an adhesive, such as an adhesive glue. The articles described herein exhibit a 90° pull off adhesion of at least about 1.5 N/cm 2 . The articles described herein can contain less adhesive than when the adhesive is used alone without microtopography and yet exhibit equivalent adhesive strength with little or no toxicity or other adverse side effects (e.g., exothermic reaction).

Claims (32)

1. An adhesive article comprising a substrate comprising a surface, wherein the substrate surface comprises microprotrusions extending from the surface, wherein the improvement comprises:

the microprotrusions having an average height greater than about 10 microns;

at least a portion of the surface, microprotrusions, or combinations thereof coated with an adhesive glue,

wherein the adhesive glue coating has a thickness of less than 75% of the average height of the protrusions; and

wherein the 90° pull off adhesive strength of the article is at least about 1.0N/cm 2 .

2. The article of claim 1 , wherein the substrate comprises one or more biodegradable materials, one or more non-biodegradable materials, or combinations thereof.

3. The article of claim 2 , wherein the one or more biodegradable materials is selected from the group consisting of aliphatic polyesters, poly(amino acids), poly(ether-esters), polyalkylene oxalates, poly(carbonates), poly(iminocarbonates), poly(ortho esters), poly(oxaesters), poly(amidoesters), poly(anhydrides), polyphosphazenes, poly(lactic-co-glycolic acid) (PLGA), polycaprolactone (PCL), polyglycolide (PGA), polylactic acid (PLA), poly-3-hydroxybutyrate (PHB), star-poly-caprolactone-co-D,L-lactide, poly(tri-methyl carbonate-co-caprolactone), poly(ethylene glycol) (PEG), polyurethanes, parylene-C, poly(citric-diol), hyaluronic acid, collagen, elastin, laminin, gelatin, chondroitin sulfate, dextran, chitosan, alginate, keratin, agrose, or combinations thereof.

4. The article of claim 2 , wherein the one or more non-biodegradable materials is selected from the group consisting of acrylics, butyl rubber, ethyl vinyl acetate, poly(amide imides), poly(etherketones), polycarbonates, polyolefins, such as polyethylenes and polypropylenes, polybutylene terephthalates, polydimethylsiloxane (PDMS), polyethylene terephthalates, polyamides, polyvinylidene fluoride, polyacrylates, such as polymethylmethacrylate and polyhydroxyethylmethacrylate, polyacrylamides, such as poly(N-isopropylacrylamide), polyvinylalcohols, and combinations thereof.

5. The article of claim 2 , wherein the substrate is biodegradable in whole or in part.

6. The article of claim 5 , wherein the substrate comprises in whole or in part polycaprolactone.

7. The article of claim 1 , wherein the 90° pull off adhesive strength of the article is at least about 1.25 N/cm 2 .

8. The article of claim 1 , wherein the microprotrusions have a height between about 11 to about 20 microns.

9. The article of claim 8 , wherein the height of the microprotrusions is about 19 microns.

10. The article of claim 1 , wherein the microprotrusions have a base diameter between about 3 microns to about 7 microns.

11. The article of claim 10 , wherein the base diameter of the microprotrusions is about 5 microns.

12. The article of claim 1 , wherein the center-to-center distance between the microprotrusions is between about 5 microns to about 20 microns.

13. The article of claim 1 , wherein the aspect ratio of the microprotrusions is less than 7.

14. The article of claim 1 , wherein the adhesive glue is selected from the group consisting of cyanoacrylates, aldehyde adhesives, acrylate adhesives; urethane adhesives; hydroxysuccinimide adhesives, catechol-containing adhesives, and combinations thereof.

15. The article of claim 14 , wherein the adhesive glue comprises a cyanoacrylate.

16. The article of claim 1 , wherein the adhesive glue coating thickness at the base of the microprotrusions is between about 1 micron to about 5 microns.

17. The article of claim 16 , wherein the coating thickness is about 2.5 microns.

18. The article of claim 1 , wherein the 90° pull off adhesive strength is at least about 1.75 N/cm 2 .

19. The article of claim 1 , wherein the article is biocompatible.

20. The article of claim 1 , wherein the article is a tape or patch.

21. The article of claim 1 , wherein the article further comprises a sacrificial layer that is coated on top of the adhesive to protect the adhesive layer prior to application.

22. The articles of claim 1 , wherein the article further comprises one or more therapeutic agents, prophylactic agents, diagnostic agents, nutraceuticals, or combinations thereof.

23. A method comprising contacting the article of claim 1 to a tissue.

24. The method of claim 23 , wherein the tissue is contacted in viva.

25. A method comprising contacting the article of claim 1 to a medical device.

26. The article of claim 1 , wherein the thickness of the coating is less than 50% of the height of the protrusions.

27. The article of claim 1 , wherein the thickness of the coating is less than 25% of the height of the protrusions.

28. The article of claim 1 , wherein the 90° pull off adhesive strength of the article is at least about 1.5 N/cm 2 .

Assignments (3)
CONFIRMATORY LICENSE Recorded Aug 31, 2015
From: BRIGHAM AND WOMEN'S HOSPITAL
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 036509/0473 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2014
From: PEREIRA, MARIA JOSE M.N.; KARP, JEFFREY M.
To: THE BRIGHAM AND WOMEN'S HOSPITAL, INC.
Reel/Frame 034077/0478 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2014
From: CHO, WOO-KYUNG; LANGER, ROBERT S.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 034077/0493 →
Continuity (3)
Provisional Application 61731178 · Nov 29, 2012
Provisional Application 61731509 · Nov 30, 2012
Related Publication 20140148846A1 · May 29, 2014