One component (1K) curable adhesive composition

Patent metadata

Field	Value
Publication number	US-12180398-B2
Application number	US-202217838835-A
Country	US
Kind code	B2
Filing date	Jun 13, 2022
Priority date	Dec 13, 2019
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

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.

First claim

What is claimed is:

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.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Stapf Stefanie
• Lieske Alexandra
• Gutierrez Diaz Jordan
• Moeller Thomas

Classifications

• C09J2463/00

  Presence of epoxy resin · CPC title

• C09J163/00 Primary

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C09J11/08

  Macromolecular additives · CPC title

• C09J11/06

  organic · CPC title

• C09J11/04

  inorganic · CPC title