Two component (2K) curable adhesive composition

Patent metadata

Field	Value
Publication number	US-12398302-B2
Application number	US-202217838544-A
Country	US
Kind code	B2
Filing date	Jun 13, 2022
Priority date	Dec 13, 2019
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

The present invention is directed to a curable and debondable two-part (2K) adhesive composition comprising: i) a first part comprising: a) epoxy resin; b) an electrolyte; c) optionally, a solubilizer; and, ii) a second part comprising: a) a curing agent consisting of at least one compound possessing at least two epoxide reactive groups per molecule; and, b) an accelerator; wherein said composition further comprises an electrically non-conductive filler and, optionally a toughener.

First claim

What is claimed is:

1. A curable and debondable two-part adhesive composition comprising, based on the total weight of the composition:
a first part comprising:
a a) at least one epoxy resin present in an amount of from 50 to 70 wt %;
a b) at least one electrolyte present in an amount of from 15 to 25 wt %;
c) at least one solubilizer present in an amount of from 0.5 to about 15 wt %; and
d) at least one electrically non-conductive filler comprising fumed silica a present in an amount of from 0.5 to 5 wt %;

a second part comprising:
a) at least one curing agent comprising at least one compound having at least two epoxide reactive groups per molecule, the at a least one curing agent being present in an amount of from 5 to 10 wt %; and
b) at least one accelerator present in an amount of from 5 to 10 wt %; and

a toughener.

2. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one epoxy resin is selected from the group consisting of bis-phenol A epoxy resin, bis-phenol F epoxy resin, a mixture of bis-phenol A epoxy resin and bis-phenol F epoxy resin, cycloaliphatic epoxy resin, and mixtures thereof.

3. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one 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.

4. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one solubilizer is selected from the group consisting of polyphosphazenes, polymethylenesulfides, polyoxyalkylene glycols, polyethylene imines, silicone surfactants, fluorinated silicone surfactants, co-polymers of functionalized polyalkysiloxanes, epoxy resins, polyhydric alcohols, and sugars.

5. The curable and debondable two-part adhesive composition of claim 1 further comprising electrically conductive particles selected from the group consisting of carbon black, silver, and mixtures thereof.

6. The curable and debondable two-part adhesive composition of claim 1 , further comprising electrically conductive particles in an amount of from 0.05 to 10% wt %, based on the total weight of the composition.

7. The curable and debondable two-part adhesive composition of claim 1 , wherein the curing agent comprises at least one polyamine having at least two amine hydrogens reactive toward epoxide groups, primary and/or secondary amine groups, and an equivalent weight per primary or secondary amine group of not more than 150 g/eq.

8. The curable and debondable two-part adhesive composition of to claim 1 , wherein the accelerator is selected from the group consisting of tertiary amines, quaternary ammonium salts, amidines, guanidines, and mixtures thereof.

9. The curable and debondable two-part adhesive composition of claim 1 , wherein the accelerator is selected from the group consisting of imidazole, methylimidazole, benzyldimethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo(2,2,2) octane, and mixtures thereof.

10. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one electrolyte comprises a sulfonate.

11. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one electrolyte comprises a sulfite.

12. The curable and debondable two-part adhesive composition of claim 1 , wherein the at least one solubilizer comprises poly alkylene glycol.

13. The curable and debondable two-part adhesive composition of claim 1 , wherein the composition has an initial bond strength of at least 16.17 MPa.

14. The curable and debondable two-part adhesive composition of claim 1 , further comprising at least one additive.

15. The curable and debondable two-part adhesive composition of claim 1 , further comprising at least one adjuvant.

16. The curable and debondable two-part adhesive composition of claim 1 , further comprising polyethylene glycol.

17. The curable and debondable two-part adhesive composition of claim 1 , further comprising an elastomer epoxy resin.

18. A bonded structure comprising
a first material layer having an electrically conductive surface;
a second material layer having an electrically conductive surface; and
a cured debondable two-part adhesive composition of claim 1 disposed between the first and second material layers.

19. A method of debonding the bonded structure of claim 18 , the method comprising:
applying a voltage across the first and second material layers to form an anodic interface and a cathodic interface; and
debonding the first and second material layers,
wherein the applied voltage is from 0.5 to 200 V.

20. A curable and debondable two-part adhesive composition comprising, based on the total weight of the composition:
a first part comprising:
a) bisphenol A epoxy present in an amount of from 50 to 70 wt %;
b) 1-ethyl-3-methylimidazolium methansulfonate present in an amount of from 15 to 25 wt %;
c) 8-glycidooxyoctyl trimethoxysilane present in an amount of from 0.5 to 15 wt %; and
d) fumed silica present in an amount of from 0.5 to 5 wt %; and

a second part comprising:
a) 2-piperazin-1-ylethanamine present in an amount of from 5 to 10 wt %; and
b) an ether group-containing aliphatic primary polyamine present in an amount of from 5 to 0.10 wt %; and

a toughener.

Assignees

• Henkel Ag & Co Kgaa

Inventors

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

Classifications

• C09J2203/326

  for bonding electronic components such as wafers, chips or semiconductors · CPC title

• C09J9/02

  Electrically-conducting adhesives · CPC title

• C08K2201/001

  Conductive additives · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C09J2301/502

  process for debonding adherents · CPC title