JP-2026075538-A - Two-component adhesive composition, method for curing a two-component adhesive composition, electropenetrating cured product, and method for removing an electropenetrating cured product.

JP2026075538AJP 2026075538 AJP2026075538 AJP 2026075538AJP-2026075538-A

Abstract

[Problem] To provide a two-component adhesive that has strong adhesive strength after curing and good peelability after applying voltage to the cured product. [Solution] The above problems are solved by using a two-component adhesive composition comprising: a first agent comprising at least one non-aromatic epoxy compound selected from aliphatic epoxy compounds having a hydroxyl group and two or more epoxy groups and cyclohexene oxide epoxy compounds, an aromatic epoxy compound, rubber particles and an ionic liquid; and a second agent comprising at least one curing agent selected from amine-based curing agents having two or more amino groups in the molecule, acid anhydride-based curing agents, phenol-based curing agents, mercaptan-based curing agents and polysulfide-based curing agents, wherein the ratio of the non-aromatic epoxy compound to the aromatic epoxy compound is within a certain range. [Selection Diagram] Figure 1A

Inventors

青木孝浩
森本要子
共田陸史
舘秀樹
中川雅美

Assignees

ビッグテクノス株式会社
地方独立行政法人大阪産業技術研究所

Dates

Publication Date: 20260508
Application Date: 20241022

Claims (14)

A first agent comprising at least one non-aromatic epoxy compound selected from aliphatic epoxy compounds having a hydroxyl group and two or more epoxy groups and cyclohexene oxide-based epoxy compounds, an aromatic epoxy compound, rubber particles and an ionic liquid, It comprises at least one curing agent selected from amine-based curing agents having two or more amino groups in the molecule, acid anhydride-based curing agents, phenol-based curing agents, mercaptan-based curing agents, and polysulfide-based curing agents, and a second agent. A two-component adhesive composition comprising 100% by weight of the total of the non-aromatic epoxy compound and the aromatic epoxy compound, wherein the non-aromatic epoxy compound is present in an amount of 60% to 95% by weight, and the aromatic epoxy compound is present in an amount of 5% to 40% by weight.
The adhesive composition according to claim 1, wherein the ionic liquid is represented by the following formula (1). (In the formula, R1 is a divalent or trivalent hydrocarbon group having 2 to 8 carbon atoms, which may contain a heteroatom, and together with N + in the formula, it forms a ring, and the hydrocarbon group may contain substituents, the substituent being an alkyl group or alkoxy group having 1 to 4 carbon atoms) R2 and R3 are the same or different hydrogen atoms or alkyl groups having 1 to 6 carbon atoms (however, if the nitrogen atom forms a double bond with an adjacent carbon atom, R3 does not exist). X- is an anion selected from Br- , AlCl4- , Al2Cl7- , NO3- , BF4- , PF6- , CH3COO- , CF3COO- , CF3SO3- , ( CF3SO2 ) 2N- , ( FSO2 ) 2N- , ( CF3SO2 ) 3C- , AsF6- , SbF6- , F ( HF ) n- , CF3 ( CF2 ) 3SO3- , ( CF3CF2SO2 ) 2N- , and CF3CF2COO- .
The adhesive composition according to claim 1, wherein the ionic liquid is 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide.
The adhesive composition according to claim 1, wherein the aliphatic epoxy compound is at least one selected from aliphatic polyol polyglycidyl ethers and hydroxyaliphatic carboxylic acid polyglycidyl esters.
The adhesive composition according to claim 1, wherein the aliphatic epoxy compound is sorbitol polyglycyl ether.
The adhesive composition according to claim 1, wherein the amine-based curing agent is triethyltetramine.
The adhesive composition according to claim 1, wherein the rubber particles are core-shell type rubber particles.
The adhesive composition according to claim 1, wherein the rubber particles are core-shell type rubber particles having a core portion made of cross-linked butadiene rubber and a shell portion made of an acrylic copolymer.
The adhesive composition according to claim 1, wherein the aromatic epoxy compound is at least one selected from bisphenol-type epoxy compounds, biphenyl-type epoxy compounds, phenol novolac-type epoxy compounds, cresol novolac-type epoxy compounds, bisphenol A novolac-type epoxy compounds, and glycidyl ether-type epoxy resins.
A method for curing a two-component adhesive composition, comprising mixing a first agent and a second agent according to any one of claims 1 to 9, and curing the resulting mixture by heating it at 40°C or higher but less than 150°C for 30 minutes or more and 24 hours or less, or by curing it at 10°C or higher but 40°C for 24 hours or more and 120 hours or less.
An electropeelable cured product obtained by curing the composition described in any one of claims 1 to 9.
A method for removing an electropeelable cured material, comprising applying a voltage to the electropeelable cured material in a second conductive object to which a first conductive object is bonded via the electropeelable cured material described in claim 11.
The method according to claim 12, wherein the voltage is 1V or more and 200V or less.
The method according to claim 12, wherein the voltage application time is 1 second or more and 1200 seconds or less.

Description

This invention relates to a two-component adhesive composition and a method for curing the same. This invention also relates to an electro-removable cured product and a method for removing the same. In the manufacturing of automobiles and electronic components, there is a growing demand for recycling, specifically the disassembly and recovery of parts after use. To meet this demand, adhesives that can bond components together during the manufacturing process of automobiles and electronic components, while also possessing a certain degree of release properties when the parts are disassembled, are sometimes used. As an adhesive that achieves the above-mentioned peelability, an adhesive that can be peeled off by applying a voltage to the adhesive layer (electro-peelable adhesive) is known. For example, Patent Document 1 describes an electro-peelable adhesive comprising a thermosetting resin precursor, a curing agent, an electrolyte, and a filler, wherein the thermal conductivity after curing is 1.0 W/m·K or higher. In the electro-peelable adhesive of Patent Document 1, the adhesive strength weakens when a voltage is applied, allowing it to be peeled off. Japanese Patent Publication No. 2024-80122 This is a schematic diagram of a composite structure, viewed from the horizontal, in which a first conductor and a second conductor are bonded together via a cured adhesive composition, and shows an example of a circuit in which electrode terminals are connected to the first conductor and the second conductor.This is a schematic diagram showing the state after applying a voltage to the composite in Figure 1A and electrically removing the cured material from the first conductor.Figure 1A shows an example of a circuit in which a first conductor is attached to a non-conductor as a conductive auxiliary material in the composite.This is a schematic diagram showing the state after applying a voltage to the composite in Figure 2A and electrically removing the cured material from the first conductor.Figure 1A shows an example of a circuit in which a second conductor is attached to a non-conductor as a conductive auxiliary material in the composite.This is a schematic diagram showing the state after applying a voltage to the composite in Figure 3A and electrically removing the cured material from the first conductor.Figure 1A shows an example of a circuit in the composite when the first and second conductors are attached to a non-conductive material as conductive auxiliary materials.This is a schematic diagram showing the state after applying a voltage to the composite in Figure 4A and electrically removing the cured material from the first conductor.This is a schematic diagram of the composite (test specimen) prepared for the adhesive strength test, viewed from the horizontal direction.This is a schematic diagram of a circuit in which electrode terminals are connected to a test piece prepared in an electropeelability test. <Two-component adhesive composition> The two-component adhesive composition of the present invention comprises at least one component comprising a first component containing at least one non-aromatic epoxy compound selected from aliphatic epoxy compounds having a hydroxyl group and two or more epoxy groups and cyclohexene oxide epoxy compounds, an aromatic epoxy compound, rubber particles, and an ionic liquid, and a second component containing at least one curing agent selected from amines having two or more amino groups in their molecule, acid anhydride curing agents, phenolic curing agents, mercaptan curing agents, and polysulfide curing agents. Polymerization is initiated and curing occurs when the first component and the second component are mixed. Hereinafter, the mixture obtained by mixing the first component and the second component before curing will also be referred to as the "adhesive". (Non-aromatic epoxy compounds) Aliphatic epoxy compounds having a hydroxyl group and two or more epoxy groups, and cyclohexene oxide-based epoxy compounds are collectively referred to as "non-aromatic epoxy compounds." Aliphatic epoxy compounds having a hydroxyl group and two or more epoxy groups (also called epoxy compounds having a hydroxyl group) include aliphatic polyol polyglycidyl ethers and hydroxyaliphatic carboxylic acid polyglycidyl esters. "Aliphatic polyol" is an aliphatic compound having two or more hydroxyl groups. The aliphatic portion may further have substituents other than hydroxyl groups. Examples of such substituents include alkoxy groups having 1 to 6 carbon atoms. Examples of aliphatic polyols include alkyl polyols. The alkyl in alkyl polyols is preferably alkyl having 3 to 30 carbon atoms, and more preferably alkyl having 3 to 16 carbon atoms. The alkyl may be linear or branched, and may have substituents other than hydroxyl groups, similar to the aliphatic compounds described above. In this specification, "polyglycidyl ether" means two or more glycidyl ethers, and examples include diglycidyl