IP Library Granted Patent US 11,904,067
Granted Patent B2
US 11,904,067 · App. 16/846,293 · Granted Feb 20, 2024

Dry double-sided material for adhesion of wet tissues and devices

Inventors: Xuanhe Zhao (Allston, MA); Hyunwoo Yuk (Cambridge, MA)
Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
A61L24/0031A61B5/1102A61B5/68335A61K9/7084A61L24/043B32B9/02B32B29/002A61B2562/0261A61F2013/00676B32B2307/7163B32B2307/748B32B2405/00B32B2535/00
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Quick Facts
Patent No.
US 11,904,067
App. No.
16/846,293
Granted
Feb 20, 2024
Kind
B2
Abstract

Dry adhesive materials, particularly in the form of a film or tape, for adhering one or more wet surfaces comprising: (i) one or more hydrophilic polymers; (ii) one or more amine coupling groups, and (iii) one or more cross linkers. The dry adhesive material, when placed in contact with the one or more wet surfaces, absorbs liquid from the one or more wet surfaces, swells to form temporary crosslinking with the wet surface, and forms covalent crosslinking with the one or more wet surfaces.

Claims (22)

1. A dry adhesive material for adhering one or more wet surfaces comprising:

(i) one or more hydrophilic polymers;

(ii) one or more amine coupling groups, and

(iii) one or more cross linkers,

wherein, the dry adhesive material is in the form of a film or tape having a top surface and a bottom surface, and

wherein the dry adhesive material has a liquid content such that placement of one or more of the top and/or bottom surfaces of the dry adhesive material in contact with the one or more wet surfaces causes the dry adhesive material to absorb liquid from the one or more wet surfaces, swell to form temporary crosslinking between the dry adhesive material and the wet surface, and form covalent crosslinking between the one or more amine coupling groups and the one or more wet surfaces,

wherein the dry adhesive material further comprises poly(acrylic acid) grafted with N-hydroxysuccinimide ester, crosslinked by biodegradable gelatin methacrylate, and further comprising one or more biodegradable biopolymers.

2. The dry adhesive material of claim 1 , wherein the (ii) one or more amine coupling groups are selected from N-hydroxysuccinimide ester, N-hydroxysulfosuccinimide ester, aldehyde, imidoester, epoxide, isocyanate, catechol, and combinations thereof.

3. The dry adhesive material of claim 1 , wherein the (iii) one or more crosslinkers are selected from gelatin methacrylate, hyaluronic acid methacrylate, oxidized methacrylic alginate, polycaprolactone diacrylate,N,N′-bis(acryloyl) cystamine, N,N′-methylenebis(acrylamide), polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, and combinations thereof.

4. The dry adhesive material of claim 1 , wherein the one or more biodegradable biopolymers are selected from gelatin, chitosan, and combination thereof.

5. The dry adhesive material of claim 1 , wherein negatively charged carboxylic acid groups in the poly(acrylic acid) grafted with N-hydroxysuccinimide ester facilitate absorption of liquid and swelling of the dry adhesive material and further form intermolecular bonds with the one or more wet tissue surfaces within less than 60 seconds after contact between the dry adhesive material and the one or more wet surfaces.

6. The dry adhesive material of claim 1 , wherein the N-hydroxysuccinimide ester grafted in the poly(acrylic acid) forms covalent coupling with primary amine groups present on the one or more wet surfaces.

7. The dry adhesive material of claim 1 , wherein after the covalent crosslinking is formed between the one or more amine coupling groups and the one or more wet surfaces, the swollen dry adhesive material transforms into a layer of a hydrogel.

8. The dry adhesive of claim 7 , wherein the hydrogel has a fracture toughness of at least 1,000 J m −2 .

9. The dry adhesive material of claim 1 in the form of a flat sheet, a perforated sheet, a double sided tape or film, and a perforated double sided tape or film.

10. The dry adhesive material of claim 9 , wherein the dry adhesive material comprises a top surface and a bottom surface, and wherein adhesive material further comprises one or more backing material layers disposed on at least one of the top surface and bottom surface.

11. The dry adhesive material of claim 10 , wherein the backing material is a removable backing material and is fabricated of polyethylene, a hydrophobic polymer-coated paper, poly(methyl methacrylate), a hydrophobic polymer film, or combinations thereof.

12. The dry adhesive material of claim 10 , wherein the backing material is a non-removable material layer and is fabricated of silicone elastomer, thermoplastic polyurethane, hydrogel, a biocompatible material that is non-adhesive to wet tissues, or combinations thereof.

13. The dry adhesive material of claim 1 , further comprising one or more engineering solids, and/or devices adhered to one or more surfaces of the dry adhesive material.

14. The dry adhesive material of claim 13 , wherein the one or more engineering solids are selected from hydrogel, silicon, titanium, polydimethylsiloxane, polyimide, polycarbonate, and combination thereof.

15. The dry adhesive material of claim 1 , wherein the dry adhesive material is biodegradable.

16. The dry adhesive material of claim 15 , wherein the (i) one or more polymers and/or the (iii) one or more crosslinkers are selected so as to modify biodegradability properties.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2020
From: ZHAO, XUANHE; YUK, HYUNWOO
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 052373/0680 →
Continuity (2)
Provisional Application 62845976 · May 10, 2019
Related Publication 20200353120A1 · Nov 12, 2020
Cited By (2)
US 12,343,443 US 12,485,202