# US 12,180,398 B2 · One component (1K) curable adhesive composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,398 B2 - Document ID: US12180398B2 - Status: Granted - Kind: B2 - Application number: 17/838,835 - Filed: 2022-06-13 - Published: 2022-12-29 - Granted: 2024-12-31 - Earliest claimed: 2019-12-13 - Assignees: Henkel AG & Co. KGaA - Applicants: Henkel AG & Co. KGaA - Inventors: Stefanie Stapf; Alexandra Lieske; Jordan Gutierrez Diaz; Thomas Moeller - Web page: https://patentgrep.com/patent/US12180398B2 ## CPC - C09J 9/02: Electrically-conducting adhesives - B32B 7/12: using interposed adhesives or interposed materials with bonding properties - B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} - B32B 43/006: {Delaminating} - C09J 5/00: Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers - C09J 11/04: inorganic - C09J 11/06: organic - C09J 11/08: Macromolecular additives - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - B32B 2310/021: using electrical effects (B32B2310/08 and B32B2310/12 take precedence) - B32B 2311/24: Aluminium - C09J 2301/502: process for debonding adherents - C09J 2463/00: Presence of epoxy resin - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM ## 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 ### Claim 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) 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. ### Claim 4 (depends on 1) 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. ### Claim 5 (depends on 1) 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. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 1) 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. ### Claim 8 (depends on 1) 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. ### Claim 9 (depends on 1) 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. ### Claim 10 (depends on 1) 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. ### Claim 11 (depends on 1) A curable and debondable adhesive composition according to claim 1, wherein said solubilizer is selected from: polyoxyalkylene glycols; silicone surfactants; polpolyhydric alcohols; and, sugars. ### Claim 12 (depends on 1) 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. ### Claim 13 (depends on 1) 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. ### Claim 14 (depends on 1) 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. ### Claim 15 (depends on 1) 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. ### Claim 16 (depends on 1) 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. ### Claim 17 (depends on 16) 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. ### Claim 18 (depends on 17) A method according to the claim 17, wherein the voltage applied in step 1 is from 0.5 to 200 V. ### Claim 19 (depends on 1) 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.