IP Library › Granted Patent US 12,180,398
Granted Patent B2
US 12,180,398 · App. 17/838,835 · Granted Dec 31, 2024

One component (1K) curable adhesive composition

Inventors: Stefanie Stapf (Essen, DE); Alexandra Lieske (Duesseldorf, DE); Jordan Gutierrez Diaz (Duesseldorf, DE); Thomas Moeller (Duesseldorf, DE)
Assignee: Henkel AG & Co. KGaA
C09J9/02B32B7/12B32B15/20B32B43/006C09J5/00C09J11/04C09J11/06C09J11/08C09J163/00B32B2310/021B32B2311/24C09J2463/00
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Quick Facts
Patent No.
US 12,180,398
App. No.
17/838,835
Granted
Dec 31, 2024
Kind
B2
Abstract

The present invention is directed to a curable and one component (1K) debondable adhesive composition comprising: a) epoxy resin; b) a curing agent for said epoxy resin; c) an electrolyte; and, d) an electrically non-conductive filler; wherein said composition comprises at least one of: e) a combination of a solubilizer and a toughener; and, f) electrically conductive particles.

Claims (33)

1. A curable and one component (1K) debondable epoxy containing adhesive composition comprising:

a) epoxy resin;

b) a curing agent for said epoxy resin;

c) an electrolyte; and,

d) an electrically non-conductive filler;

wherein said composition comprises at least one of:

e) a combination of a solubilizer and a toughener; and

f) electrically conductive particles, and

wherein said electrolyte is selected from the group consisting of 1-ethyl-3-methylimidazolium methansulfonate, 1-ethyl-3-methylimidazolium methyl sulfate, 1-hexyl-3-methylimidazolium 2-(2-fluoroanilino)-pyridinate, 1-hexyl-3-methylimidazolium imide, 1-butyl-1-methyl-pyrrolidinium 2-(2-fluoroanilino)-pyridinate, 1-butyl-1-methyl-pyrrolidinium imide, trihexyl (tetradecyl) phospholium 2-(2-fluoroanilino)-pyridinate, cyclohexyltrimethylammonium bis (trifluormethylsulfonyl) imide, di (2-hydroxyethyl) ammonium trifluoroaetate, N,N-dimethyl (2-hydroxyethyl) ammonium octanoate, methyltrioctylammonium bis (trifluoromethylsulfonyl) imide, N-ethyl-N-N-N-N-tetramethylguanidinium trifluoromethanesulfonate, guanidinium trifluoromethanesulfonate, 1-butyl-4-methylpyridinium bromide, 1-buthyl-3-methylpyridinium tetrafluoroborate, 1-butyl-3-hydroxymethylpyridinium ethylsulfate, 1-butyl-1-methylpyrrolidinium bis (trifluoromethylsulfonyl) imide, 1-butyl-methylpyrrolidinium tris (pentafluoroethyl) trifluorophosphate, 3-methyl imidazolium ethylsulfate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-ethyl-methylimidazolium bromide, 1-butyl-3-methylimidazolium chloride, 1-hexyl-3-methylimidazolium chloride, 1-octyl-3-methylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-propyl-3-methylimidazolium iodide, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-2, 3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butylimidazol, 1-methylimidazolium tetrafluoroborate, tetrabutylphosphonium tris (pentafluoroethyl) trifluorophosphate, trihexyl (tetradecyl) phosphonium tetrafluoroborate and mixtures thereof.

2. A curable and debondable adhesive composition according to claim 1 , wherein said epoxy resin is selected from the group consisting of bis-phenol A epoxy resin, bis-phenol F epoxy resin, mixture of bis-phenol A epoxy resin and bis-phenol F epoxy resin and mixtures thereof.

3. A curable and debondable adhesive composition according to claim 1 , wherein said epoxy resin is present in an amount of from 15 to 75% by weight of the total weight of the composition.

4. A curable and debondable adhesive composition according to claim 1 , wherein said curing agent comprises a thiol-based curing agent selected from the group consisting of tris-(3-mercaptopropionate) (TMP), pentaerythritoltetra(3-mercaptopropionate), di-pentaerythritolhexa(3-mercaptopropionate), pentaerythritoltetra(3-mercaptopropionate), tris(2-(mercaptopropionyloxy)ethyl)isocyanate and mixtures thereof.

5. A curable and debondable adhesive composition according to claim 1 , wherein said curing agent comprises an amine-based curing agent, selected from the group consisting of cycloaliphatic amines, aliphatic amines, dicyanodiamides, polyether amines and mixtures thereof.

6. A curable and debondable adhesive composition according to claim 1 , wherein said curing agent is present in an amount of from 0.01 to 25% by weight of the total weight of the composition.

7. A curable and debondable composition according to claim 1 ,

wherein said electrolyte is selected from 1-ethyl-3-methylimidazolium methansulfonate, 1-ethyl-3-methylimidazolium methyl sulfate and mixtures thereof.

8. A curable and debondable adhesive composition according to claim 1 , wherein said electrolyte is present in an amount of from 2.0 to 25% by weight of the total weight of the composition.

9. A curable and debondable adhesive composition according to claim 1 , wherein said electrically non-conductive filler is selected from the group consisting of calcium carbonate, calcium oxide, talcum, fumed silica, silica, wollastonite, barium sulphate and mixtures thereof.

10. A curable and debondable adhesive composition according to claim 1 , wherein said electrically non-conductive filler is present in an amount of from 1 to 50% by weight of the total weight of the composition.

11. A curable and debondable adhesive composition according to claim 1 , wherein said solubilizer is selected from: polyoxyalkylene glycols; silicone surfactants; polpolyhydric alcohols; and, sugars.

12. A curable and debondable adhesive composition according to claim 1 , wherein said solubilizer is present in an amount of from 1 to 15% by weight of the total weight of the composition.

13. A curable and debondable adhesive composition according to claim 1 wherein toughener is present in an amount of from 5 to 40% by weight of the total weight of the composition.

14. A curable and debondable adhesive composition according to claim 1 comprising electrically conductive particles selected from the group consisting of silver, carbon black and mixtures thereof.

15. A curable and debondable adhesive composition according to claim 1 , wherein said electrically conductive particles are present in an amount of from 0.1 to 5% by weight of the total weight of the composition.

16. A bonded structure comprising

a first material layer having an electrically conductive surface; and

a second material layer having an electrically conductive surface;

wherein the curable and debondable adhesive composition according to claim 1 is disposed between the first and second material layers.

17. A method of debonding said bonded structure according to claim 16 , the method comprising the steps of:

1) applying a voltage across both surfaces to form an anodic interface and a cathodic interface; and

2) debonding the surfaces.

18. A method according to the claim 17 , wherein the voltage applied in step 1 is from 0.5 to 200 V.

19. A curable and debondable adhesive composition according to claim 1 , wherein said amine-based curing agent is selected from polyether amines, dicyanodiamides, and mixtures thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2022
From: STEFANIE STAPF; DIAZ, JORDAN GUTIERREZ; MOELLER, THOMAS; BRUNSTEDT, BENJAMIN
To: HENKEL AG & CO. KGAA
Reel/Frame 060900/0164 →
Priority Claims (1)
EP 19216097 · Dec 13, 2019 · regional
Continuity (2)
Continuation PCTEP2020083108 · Nov 24, 2020
Related Publication 20220411673A1 · Dec 29, 2022