Primer composition, method for manufacturing laminate, method for manufacturing laminated steel sheet, and adhesive composition kit

Abstract

According to the present invention, a method is provided that can suppress the performance degradation (decrease in lubrication performance over time) of a primer composition containing a curing accelerator and a lubricant (e.g., stamping oil) and can improve the curing speed and bond strength of an anaerobic curing adhesive. The present invention relates to a primer composition comprising component (A) and component (B), wherein component (A) comprises a (A-1) metal complex, and component (A) is 35 parts by weight or less relative to 100 parts by weight of component (B); component (A) is a curing accelerator for an anaerobic curing adhesive; and component (B) is a lubricant.

Description

Technical Field

[0001] This invention relates to a primer composition, a method for manufacturing a laminate, a method for manufacturing a laminated steel sheet, and a reagent package for adhesive composition. Background Technology

[0002] Currently, motors and stators are manufactured by stacking steel plates to obtain laminated steel plates. In assembling these laminated steel plates, methods such as laser welding and / or riveting are used. However, due to the increasing power output of motors, the laminated steel plates are being made thinner, leading to assembly methods based on adhesive bonding (Japanese Patent Application Publication No. 2006-334648). Furthermore, with the aim of improving quality and productivity, simplifying manufacturing processes, and / or miniaturizing manufacturing equipment, a method has been developed whereby a substance obtained by adding a curing accelerator to stamping oil is coated onto a steel plate, and this steel plate is then stacked with a steel plate coated with an adhesive for assembly (Japanese Patent Application Publication No. 2006-334648). Summary of the Invention

[0003] However, while conventional curing accelerators added to stamping oils increase the curing speed of the adhesive, there are concerns about reducing the properties (performance) of the stamping oil. In particular, conventional curing accelerators have the problem of increasing the coefficient of friction of the stamping oil over time (reducing lubrication performance), and there is also the problem of sintering sometimes occurring during the processing of metals, etc.

[0004] Therefore, the object of the present invention is to provide a method for suppressing the performance degradation (decrease in lubrication performance over time) of a primer composition containing a curing accelerator and a lubricant (e.g., stamping oil, etc.) and improving the curing speed and bond strength of an anaerobic curing adhesive.

[0005] In order to achieve the above-mentioned objective, the inventors conducted research and discovered the following method: even when a curing accelerator is added to the lubricating oil (e.g., stamping oil), the performance degradation (degradation of lubrication performance over time) of the primer composition containing the curing accelerator and the lubricating oil (e.g., stamping oil) is suppressed, and the curing speed and bond strength of the anaerobic curing adhesive are improved, thereby completing the present invention.

[0006] The main points of this invention are explained below.

[0007] One aspect of the present invention capable of achieving at least one of the above objectives relates to the following [1].

[0008] [1] A primer composition comprising component (A) and component (B), wherein component (A) comprises a (A-1) metal complex, and component (A) comprises 35 parts by weight or less relative to 100 parts by weight of component (B). (A) Ingredients: Curing accelerator for anaerobic curing adhesives. (B) Ingredients: Lubricating oil.

[0009] In addition, as a non-limiting example of a preferred embodiment, the present invention includes the embodiments described below [2] to [8].

[0010] [2] According to the primer composition of [1], wherein the component (A) is 0.1 to 35 parts by weight relative to 100 parts by weight of component (B).

[0011] [3] The primer composition according to [1] or [2], wherein the above-mentioned component (A) further comprises solvent (A-2).

[0012] [4] According to the primer composition of [3], wherein the above-mentioned component (A) is composed only of the above-mentioned (A-1) and (A-2).

[0013] [5] The primer composition according to [3] or [4], wherein (A-2) is a ketone solvent and / or an alcohol solvent.

[0014] [6] The primer composition according to any one of [1] to [5], wherein the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having an aromatic ring.

[0015] [7] The primer composition according to any one of [1] to [6] is used for the assembly of laminated steel sheets.

[0016] [8] The primer composition according to any one of [1] to [7], wherein the above-mentioned component (B) is a stamping oil.

[0017] Another aspect of the invention that can achieve at least one of the above objectives relates to [9].

[0018] [9] A primer composition comprising components (A-1), (A-2), and (B) below, wherein the total of components (A-1) and (A-2) is 35 parts by weight or less relative to 100 parts by weight of component (B). (A-1): Metal complex, (A-2): Solvent, (B) Ingredients: Lubricating oil.

[0019] In addition, as a non-limiting example of a preferred embodiment, the present invention includes the embodiments described below in

[10] to

[13] .

[0020]

[10] According to the primer composition of [9], the total of the above-mentioned components (A-1) and (A-2) is 0.1 to 35 parts by mass relative to 100 parts by mass of component (B).

[0021]

[11] The primer composition according to [9] or

[10] , wherein (A-2) is a ketone solvent and / or an alcohol solvent.

[0022]

[12] The primer composition according to any one of [9] to

[11] is used for the assembly of laminated steel sheets.

[0023]

[13] The primer composition according to any one of [9] to

[12] , wherein the above-mentioned component (B) is a stamping oil.

[0024] In addition, as a non-limiting example of a preferred embodiment, the present invention includes the embodiments described below

[14] to

[21] .

[0025]

[14] A method for manufacturing a laminate, comprising: Apply the primer composition described in any one of [1] to

[13] to the substrate; The anaerobic curing adhesive is applied to the substrate, the coating of the primer composition, or both; and After applying the primer composition and the anaerobic curing adhesive, the substrate is bonded to the substrate to be bonded, and then the anaerobic curing adhesive is cured.

[0026]

[15] According to the manufacturing method described in

[14] , the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having aromatic rings.

[0027]

[16] A method for manufacturing a laminated steel plate, comprising the following steps 1 to 4, Step 1: Apply the primer composition described in any one of [1] to

[13] to the strip steel plate; Step 2: The strip steel plate coated with the above primer composition is punched into a specified shape to obtain a steel sheet (steel sheet coated with the above primer composition). Step 3: Apply the anaerobic curing adhesive in a surface or dot pattern to the steel sheet coated with the above primer composition, and then laminate the steel sheet with other steel sheets (steel sheets to be bonded). Step 4: The above-mentioned anaerobic curing adhesive is cured under specified conditions to obtain laminated steel plates.

[0028]

[17] According to the manufacturing method described in

[16] , the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having aromatic rings.

[0029]

[18] An adhesive composition kit comprising an anaerobic curing adhesive and a primer composition as described in any one of [1] to

[13] .

[0030]

[19] According to the adhesive composition kit of

[18] , wherein the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having aromatic rings.

[0031]

[20] A method for promoting the curing of an anaerobic curing adhesive, comprising: curing the anaerobic curing adhesive while the coating of the primer composition described in any one of [1] to

[13] is in contact with the anaerobic curing adhesive.

[0032]

[21] According to the curing promotion method of

[20] , wherein the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having aromatic rings.

[0033] Another aspect of the invention capable of achieving at least one of the above objectives relates to the following

[22] .

[0034]

[22] A method for manufacturing a primer composition, comprising: mixing component (A) and component (B) in an amount of component (A) of 35 parts by mass or less relative to 100 parts by mass of component (B), (A) Ingredients: Curing accelerator for anaerobic curing adhesives. (B) Ingredients: Lubricating oil.

[0035] In addition, as a non-limiting example of a preferred embodiment, the present invention includes the embodiments described below in

[23] to

[24] .

[0036]

[23] The manufacturing method according to

[22] includes: mixing the above-mentioned component (A) with 0.1 to 35 parts by mass relative to 100 parts by mass of component (B).

[0037]

[24] According to the manufacturing method described in

[22] or

[23] , wherein the anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates and (meth)acrylates having aromatic rings. Detailed Implementation

[0038] Next, the details of the present invention will be described. It should be noted that the present invention is not limited to the following embodiments.

[0039] In this specification, "X~Y" refers to the range including the values ​​(X and Y) recorded before and after it as the lower and upper limits, meaning "above X and below Y".

[0040] Unless otherwise specified, the operation and physical property measurements shall be performed at 25°C and 55% RH.

[0041] In this specification, the term "(meth)acryloyl" includes both acryloyl and methacryloyl. Similarly, the term "(meth)acrylate" includes both acrylate and methacrylate, the term "(meth)acrylic acid" includes both acrylic acid and methacrylic acid, and the term "(meth)acrylamide" includes both acrylamide and methacrylamide. Therefore, for example, the term "(meth)acryloyl group" includes acryloyl group (H₂C=CH-C(=O)-). ) and methacryloyl (H2C=C(CH3)-C(=O)- These two. Here, This indicates the bonding site with an adjacent atom. The (meth)acryloyl group can also exist in the form of (meth)acryloyloxy. Therefore, compounds containing a (meth)acryloyl group can be, for example, (meth)acrylates.

[0042] <Primer Composition>

[0043] One aspect (first aspect) of the present invention relates to a primer composition comprising component (A) and component (B) below, wherein component (A) comprises a (A-1) metal complex, and component (A) is 35 parts by mass or less relative to 100 parts by mass of component (B). (A) Ingredients: Curing accelerator for anaerobic curing adhesives. (B) Ingredients: Lubricating oil.

[0044] The primer composition according to this method can suppress the performance degradation (degradation of lubrication performance over time) of the primer composition containing a curing accelerator and a lubricant (such as stamping oil) and can improve the curing speed and bond strength of the anaerobic curing adhesive.

[0045] The primer composition described herein will now be described in detail. However, the primer composition described herein is not limited to the embodiments described below.

[0046] [(A) Ingredient]

[0047] (A) is a curing accelerator for an anaerobic curing adhesive. (A) is a component that promotes the curing of an anaerobic curing adhesive (particularly preferably an anaerobic curing adhesive containing components (C) to (E) described below). Additionally, the primer composition described in this specification may be a composition containing a curing accelerator.

[0048] As a curing accelerator, it contains a metal complex (A-1), which is the main component that promotes the effect of the anaerobic curing adhesive described later. In addition to (A-1), it may also contain a solvent (A-2) as a curing accelerator. (A-2) dissolves (A-1), thereby enabling (A-1) to be uniformly dispersed in the primer composition, thus improving the curing accelerator effect. Component (A) may consist only of (A-1) or only of (A-1) and (A-2).

[0049] In addition to the curing accelerator described above, the primer composition of this method also contains component (B) described later. Therefore, the primer composition of this method can be used as a lubricant for metalworking, and by combining it with the anaerobic curing adhesive described later, it can promote the curing of the adhesive.

[0050] In one embodiment, the primer composition preferably does not contain curing components such as reactive resins. When the primer composition does not contain curing components such as reactive resins, the curing-promoting effect of component (A) is generally not produced when only the primer composition is used, and curing does not occur when only the primer composition is used.

[0051] (A-1) is a metal complex. (A-1) is the main component of a curing accelerator that promotes the curing of the anaerobic curing adhesive described later. The metal complex can be used alone or in combination of two or more.

[0052] (A-1): Examples of metal types in the metal complex are not particularly limited, and include Mg, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Al, Ag, etc. The metal type in the metal complex can be used alone, or two or more can be used together. Preferably, the metal type in the metal complex includes at least one metal type selected from the examples described above. From the viewpoint of further promoting the curing speed of the anaerobic curing adhesive, Cu is preferred. In one embodiment, (A-1) component: The metal type in the metal complex is preferably selected from at least one metal type selected from the examples described above, and more preferably Cu.

[0053] As a specific example of (A-1), there are no particular limitations, and examples include cobalt naphthenate, cobalt octanoate, copper naphthenate, copper neodecanoate, copper 2-ethylhexanoate, vanadium acetylacetonate, etc. These can be used alone or in combination of two or more. From the viewpoint of further promoting the curing speed of the anaerobic curing adhesive, copper naphthenate, copper neodecanoate, and copper 2-ethylhexanoate are preferred examples. (A-1): The metal complex preferably comprises at least one compound selected from the compounds exemplified above. In one embodiment, (A-1): the metal complex is preferably at least one compound selected from the compounds exemplified above, more preferably at least one compound selected from copper naphthenate, copper neodecanoate, and copper 2-ethylhexanoate, and even more preferably copper neodecanoate.

[0054] One embodiment of the curing accelerator may contain a solvent as (A-2). Various solvents may be used as (A-2).

[0055] There is no particular limitation on the boiling point of the solvent, but it is preferably less than 80°C. In one embodiment, (A-2) preferably contains a solvent with a boiling point less than 80°C, and more preferably a solvent with a boiling point less than 80°C. It should be noted that, in this specification, boiling point refers to the value at 1 standard atmosphere (760 mmHg, 1013.25 hPa).

[0056] Examples of solvents for (A-2) are not particularly limited, and include ketone solvents, alcohol solvents, hydrocarbon solvents, ester solvents, glycol solvents, glycol ether solvents, etc. Solvents can be used alone or in combination of two or more. From the viewpoint of solubility and dispersibility in (A-1), (A-2) the solvent is preferably selected from at least one of ketone solvents, alcohol solvents, hydrocarbon solvents, ester solvents, glycol solvents, and glycol ether solvents, more preferably ketone solvents and / or alcohol solvents, and even more preferably ketone solvents. Examples of ketone solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, diacetone alcohol, etc., but are not limited to these. They can be used alone or in combination of two or more. Examples of alcohol solvents include methanol, ethanol, modified ethanol, isopropanol, n-propanol, isobutanol, higher alcohols (alcohols with 6 or more carbon atoms), benzyl alcohol, etc., but are not limited to these. They can be used alone or in combination of two or more. Examples of hydrocarbon solvents include benzene, toluene, xylene, styrene, n-hexane, isohexane, cyclohexane, methylcyclohexane, n-heptane, and mineral oil, but are not limited to these. These solvents can be used alone or in mixtures of two or more. In this specification, mineral oil refers to a mixture of hydrocarbons containing 9 to 16 carbon atoms, specifically a mixture of aliphatic and aromatic hydrocarbons. Mineral oil is preferably a mixture of hydrocarbon compounds with boiling points in the range of 100 to 300°C. In one embodiment, (A-2): the solvent may contain at least one solvent selected from the solvents exemplified above, or at least one ketone solvent selected from the ketone solvents exemplified above. In one embodiment, (A-2): the solvent may be at least one ketone solvent selected from the ketone solvents exemplified above, or acetone.

[0057] When component (A) contains both (A-1) and (A-2), there is no particular limitation on the content ratio of (A-1) and (A-2). When component (A) contains both (A-1) and (A-2), it is preferable that (A-1) contains 0.1 to 200 parts by weight relative to 100 parts by weight of (A-2), more preferably 1 to 100 parts by weight of (A-1) relative to 100 parts by weight of (A-2), even more preferably 2 to 50 parts by weight of (A-1) relative to 100 parts by weight of (A-2), and even more preferably 2 to 20 parts by weight of (A-1) relative to 100 parts by weight of (A-2). It may contain 5 to 20 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 5 to 17 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 5 to 15 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 5 to 12 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 5 to 10 parts by mass of (A-1) relative to 100 parts by mass of (A-2). It may also contain 9 to 20 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 10 to 20 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 12 to 20 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or it may contain 15 to 20 parts by mass of (A-1) relative to 100 parts by mass of (A-2). It may contain 2 to 12 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or 5 to 12 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or 7 to 12 parts by mass of (A-1) relative to 100 parts by mass of (A-2). It may also contain 2 to 10 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or 5 to 10 parts by mass of (A-1) relative to 100 parts by mass of (A-2), or 7 to 10 parts by mass of (A-1) relative to 100 parts by mass of (A-2). By containing 0.1 to 200 parts by mass of (A-1) relative to 100 parts by mass of (A-2), the dispersibility in component (B) can be improved without reducing its properties as a curing accelerator. When two or more types of (A-1) are used in combination, the amount of (A-1) indicates their total amount. When two or more (A-2) are used in combination, the quantity of (A-2) represents their total quantity.

[0058] The content of (A-1) is not particularly limited, but is preferably 0.1 to 25% by mass relative to 100% by mass of the primer composition (relative to the total mass of the primer composition), more preferably 0.3 to 20% by mass, even more preferably 0.4 to 10% by mass, even more preferably 0.4 to 2.5% by mass, and even more preferably 0.4 to 1.5% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 0.4 to 2.1% by mass, 0.4 to 1% by mass, more than 0.4% by mass and less than 0.9% by mass, or 0.4 to 0.8% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 0.6 to 2.5% by mass, 0.6 to 2.2% by mass, or 0.6 to 2.1% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 0.8 to 2.5% by mass, 0.8 to 2.2% by mass, or 0.8 to 2.1% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 0.6~1.5% by mass, 0.7~1.5% by mass, 0.8~1.5% by mass, or 0.9~1.5% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 1~2.5% by mass, or 1.5~2.5% by mass. The content of (A-1) relative to 100% by mass of the primer composition can be 1~2.2% by mass, or 1.5~2.1% by mass. By using (A-1) at a content of 0.1~25% by mass relative to 100% by mass of the primer composition, the curing effect of the anaerobic curing adhesive is further improved without increasing the coefficient of friction. When two or more types of (A-1) are used in combination, the amount of (A-1) represents their total amount.

[0059] The content of (A-2) is not particularly limited, but is preferably 1 to 25% by mass relative to 100% by mass of the primer composition (relative to the total mass of the primer composition), more preferably 3 to 25% by mass, even more preferably 5 to 20% by mass, and even more preferably 5 to 15% by mass. The content of (A-2) relative to 100% by mass of the primer composition can be 7 to 25% by mass, 7 to 20% by mass, 7 to 15% by mass, or 7% by mass or more but less than 14% by mass. The content of (A-2) relative to 100% by mass of the primer composition can be 10% by mass to 25% by mass, 10% by mass to 20% by mass, 10% by mass to 15% by mass, or 10% by mass or more but less than 14% by mass. The content of (A-2) relative to 100% by mass of the primer composition can be 5 to 25% by mass, 10 to 25% by mass, 15 to 25% by mass, or 20 to 25% by mass. By using (A-2) at a content of 1 to 25% by mass relative to 100% by mass of the primer composition, the curing effect of the anaerobic curing adhesive is further improved without increasing the coefficient of friction. When two or more types of (A-2) are used in combination, the amount of (A-2) represents their total amount.

[0060] Regarding the content of component (A) (the total content of component (A)), relative to 100 parts by mass of component (B) described later, component (A) is 35 parts by mass or less. That is, the total content of component (A) is more than 0 parts by mass and less than 35 parts by mass relative to 100 parts by mass of component (B). More preferably, the content of component (A) (the total content of component (A)) is 25 parts by mass or less relative to 100 parts by mass of component (B), and even more preferably, 20 parts by mass or less (lower limit: more than 0 parts by mass). By making the content of component (A) less than 35 parts by mass relative to 100 parts by mass of component (B), there is no concern about increasing the coefficient of friction of the primer composition. There is no particular limitation on the lower limit value of the content of component (A). More preferably, the content of component (A) (the total content of component (A)) is 0.1 parts by mass or more relative to 100 parts by mass of component (B), and even more preferably, 5 parts by mass or more. By making the content of component (A) 0.1 parts by mass or more relative to 100 parts by mass of component (B), the curing of the anaerobic curing adhesive can be further promoted. Relative to 100 parts by mass of component (B), the adhesive may contain 0.1 to 35 parts by mass of component (A); relative to 100 parts by mass of component (B), the adhesive may contain 1 to 25 parts by mass of component (A); relative to 100 parts by mass of component (B), the adhesive may contain 5 to 20 parts by mass of component (A). Relative to 100 parts by mass of component (B), the adhesive may contain 1 to 35 parts by mass of component (A); relative to 100 parts by mass of component (B), the adhesive may contain 5 to 35 parts by mass of component (A); relative to 100 parts by mass of component (B), the adhesive may contain 15 to 35 parts by mass of component (A). It is permissible to contain 10-25 parts by mass of component (A) relative to 100 parts by mass of component (B), or 10-20 parts by mass of component (A) relative to 100 parts by mass of component (B), or more than 10 parts by mass but less than 20 parts by mass of component (A) relative to 100 parts by mass of component (B), or 10-18 parts by mass of component (A) relative to 100 parts by mass of component (B). It is permissible to contain 15-25 parts by mass of component (A) relative to 100 parts by mass of component (B), 15-20 parts by mass of component (A) relative to 100 parts by mass of component (B), more than 15 parts by mass but less than 20 parts by mass of component (A) relative to 100 parts by mass of component (B), or 15-18 parts by mass of component (A) relative to 100 parts by mass of component (B). When two or more components (A) are used in combination, the amount of component (A) indicates their total quantity. When two or more components (B) are used in combination, the amount of component (B) represents their total amount.

[0061] There is no particular limitation on the content of component (A) (the total content of component (A)). Preferably, it contains 0.1 to 26% by mass of component (A) relative to 100% by mass of the primer composition (relative to the total mass of the primer composition), more preferably 1 to 25% by mass of component (A) relative to 100% by mass of the primer composition, even more preferably 3 to 20% by mass of component (A) relative to 100% by mass of the primer composition, and even more preferably 5 to 17% by mass of component (A) relative to 100% by mass of the primer composition. The content of component (A) relative to 100% by mass of the primer composition can be 7% to 26% by mass, 7% to 25% by mass, 7% to 20% by mass, or 7% to 17% by mass. The content of component (A) relative to 100% by mass of the primer composition can be 9% to 26% by mass, 10% to 26% by mass, 10% to 25% by mass, 10% to 20% by mass, or 10% to 17% by mass. The content of component (A) relative to 100% by mass of the primer composition can be 12% to 26% by mass, 12% to 25% by mass, 12% to 20% by mass, or 12% to 17% by mass. When two or more components (A) are used in combination, the amount of component (A) indicates their total amount.

[0062] [(B) Component]

[0063] (B) Component is lubricating oil. In one embodiment, the primer composition preferably includes lubricating oil as component (B). Component (B) is preferably used to prevent sintering during the processing of metals, etc. The aforementioned component (A) does not significantly increase the coefficient of friction of component (B), thus enabling stable processing of metals, etc., using the primer composition described herein. When the primer composition of one embodiment includes the aforementioned component (A-2), component (A-2) is preferably a component other than component (B). Component (B) may not contain ketone solvents. Component (B) may not contain acetone. Component (B) may not contain either ketone solvents or alcohol solvents. Component (B) may not contain solvents with a boiling point less than 80°C.

[0064] (B) Composition: Examples of lubricating oils include mineral oil-based lubricating oils and chemically synthesized oils, but are not limited to these. Examples of mineral oil-based lubricating oils are not particularly limited; for example, hydrogenated petroleum fractions can be included. (B) Composition: Lubricating oils can be used alone or in combination with two or more types.

[0065] (B) The type of component is not particularly limited, but stamping oil is preferred. Stamping oil refers to an oil obtained by mixing one or more additives selected from ashless dispersants, antioxidants, anti-metal discoloration agents, extreme pressure agents, friction modifiers, viscosity index improvers, and / or defoamers into a base oil. Examples of base oils are not particularly limited, and examples include hydrogenated petroleum fractions that can be used as lubricants (oils that can function as general-purpose lubricants even when used alone). As a stamping oil, it is preferable to contain 50% by mass or more (50% by mass relative to 100% by mass of the stamping oil, or 50% by mass relative to the total mass of the stamping oil). The upper limit of the content of the aforementioned hydrogenated petroleum fraction in the stamping oil is less than 100% by mass relative to the total mass of the stamping oil. Stamping oil can be used alone or in combination with two or more types. In one embodiment, (B) component: the lubricant preferably contains stamping oil, more preferably stamping oil.

[0066] (B) Composition: Lubricating oils can be commercially available, synthetic, or a combination thereof. Examples of commercially available products are not particularly limited; for instance, G-6338F manufactured by Nippon Oil Co., Ltd., etc., can be cited.

[0067] The content of component (B) is not particularly limited. The content of component (B) relative to the total mass of the primer composition (relative to 100% by mass of the primer composition) is preferably 72% to 95% by mass, more preferably 75% to 95% by mass, even more preferably 80% to 95% by mass, and even more preferably 82% to 93% by mass. The content of component (B) relative to 100% by mass of the primer composition can be 72% or more and less than 90% by mass, or it can be 72% to 88% by mass. The content of component (B) relative to 100% by mass of the primer composition can be 82% or more and less than 90% by mass, or it can be 82% to 88% by mass. By setting the content of component (B) relative to 100% by mass of the primer composition to 72% to 95% by mass, the possibility of increasing the coefficient of friction of the primer composition becomes smaller. When two or more components (B) are used in combination, the amount of component (B) represents their total amount.

[0068] [Other components in the primer composition]

[0069] The primer composition described in one embodiment may further contain one or more other components, or may not contain any. There are no particular limitations on the other components in the primer composition described in one embodiment, as long as they are components other than (A) and (B). As mentioned above, the primer composition described in one embodiment preferably does not contain a curing component. Examples of curing components are not particularly limited and include reactive resins, etc.

[0070] [Anaerobic Curing Adhesives]

[0071] The primer composition described in one embodiment is preferably used for the purpose of promoting the curing of the anaerobic curing adhesive. The anaerobic curing adhesive is not particularly limited, but preferably contains a compound having one or more (meth)acryloyl groups as component (C), an organic peroxide as component (D), and an anaerobic curing catalyst as component (E).

[0072] (C) Ingredients

[0073] (C) is a compound having one or more (meth)acryloyl groups. (C) may be used alone or in combination of two or more.

[0074] (C) Component (C) can be a polymer having one or more (meth)acryloyl groups per molecule, a monomer having one or more (meth)acryloyl groups per molecule, or a combination thereof. The polymer can contain a portion of repeating monomer units, a portion derived therefrom, or both. Examples of component (C) are not particularly limited, and can include oligomers having one or more (meth)acryloyl groups per molecule and monomers having one or more (meth)acryloyl groups per molecule. Here, oligomers refer to polymers obtained by repeating monomer units (including monomer units other than (meth)acrylate monomers) approximately 2 to several tens of times (e.g., 2 to 10, 2 to 20, 2 to 30, 2 to 40, or 2 to 50 times). Oligomers can be polymers containing portions of repeating monomer units approximately 2 to several tens of times, portions derived therefrom, or both.

[0075] (C) Composition: The compound having one or more (meth)acryloyl groups preferably includes an oligomer having one or more (meth)acryloyl groups in one molecule, more preferably includes an oligomer having one or more (meth)acryloyl groups in one molecule and a monomer having one or more (meth)acryloyl groups in one molecule. (C) The mass ratio of oligomers having one or more (meth)acryloyl groups per molecule to monomers having one or more (meth)acryloyl groups per molecule is not particularly limited. Preferably, the ratio of oligomers having one or more (meth)acryloyl groups per molecule to monomers having one or more (meth)acryloyl groups per molecule is 1:99 to 99:1. More preferably, the ratio of oligomers having one or more (meth)acryloyl groups per molecule to monomers having one or more (meth)acryloyl groups per molecule is 20:80 to 80:20. Even more preferably, the ratio of oligomers having one or more (meth)acryloyl groups per molecule to monomers having one or more (meth)acryloyl groups per molecule is 50:50 to 75:25.

[0076] Examples of oligomers having one or more (meth)acryloyl groups in a molecule are not particularly limited, such as urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

[0077] From the viewpoint of the adhesive strength of the laminated steel sheets, (C) component: the compound having one or more (meth)acryloyl groups preferably includes one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings, more preferably including urethane-modified (meth)acrylates and / or epoxy-modified (meth)acrylates, and even more preferably including urethane-modified (meth)acrylates and epoxy-modified (meth)acrylates. In one embodiment, the anaerobic curing adhesive preferably includes one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

[0078] From the viewpoint of curing properties and adhesion strength to laminated steel sheets, (C) component: A compound having one or more (meth)acryloyl groups preferably includes a compound having two or more (meth)acryloyl groups, and more preferably includes an oligomer having two or more (meth)acryloyl groups per molecule. Examples of oligomers having two or more (meth)acryloyl groups are not particularly limited, and examples include urethane-modified (meth)acrylates having two or more (meth)acryloyl groups, epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and (meth)acrylates with aromatic rings having two or more (meth)acryloyl groups.

[0079] From the viewpoint of curing properties and adhesion strength to laminated steel sheets, (C) component: The compound having one or more (meth)acryloyl groups preferably includes one or more compounds selected from urethane-modified (meth)acrylates having two or more (meth)acryloyl groups, epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and (meth)acrylates having two or more (meth)acryloyl groups and having an aromatic ring. (C) component: The compound having one or more (meth)acryloyl groups more preferably includes urethane-modified (meth)acrylates having two or more (meth)acryloyl groups and / or epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and even more preferably includes urethane-modified (meth)acrylates having two or more (meth)acryloyl groups and epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups.

[0080] In one embodiment, the oligomer having one or more (meth)acryloyl groups in a molecule preferably comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having an aromatic ring, more preferably urethane-modified (meth)acrylates and / or epoxy-modified (meth)acrylates, and even more preferably urethane-modified (meth)acrylates and epoxy-modified (meth)acrylates.

[0081] When two or more compounds having one or more (meth)acryloyl groups are used as component (C), the content of urethane-modified (meth)acrylate is not particularly limited, but is preferably 1 to 90% by mass relative to the total mass of component (C), more preferably 5 to 90% by mass, further preferably 10 to 80% by mass, and particularly preferably 15 to 70% by mass. By containing 1% to 90% by mass of urethane-modified (meth)acrylate relative to the total mass of component (C), the bonding strength of the laminated steel sheets is superior.

[0082] When two or more of the above-mentioned compounds having one or more (meth)acryloyl groups are used as component (C), the content of epoxy-modified (meth)acrylate is not particularly limited, but is preferably 1 to 90% by mass relative to the total mass of component (C), more preferably 5 to 70% by mass, even more preferably 10 to 50% by mass, and particularly preferably 10 to 30% by mass. By containing 1 to 90% by mass of epoxy-modified (meth)acrylate relative to the total mass of component (C), the curing properties are superior.

[0083] When using urethane-modified (meth)acrylate and epoxy-modified (meth)acrylate ((C) Component: When a compound having one or more (meth)acryloyl groups comprises urethane-modified (meth)acrylate and epoxy-modified (meth)acrylate), the mass ratio of urethane-modified (meth)acrylate to epoxy-modified (meth)acrylate is not particularly limited. The preferred mass ratio of urethane-modified (meth)acrylate to epoxy-modified (meth)acrylate is urethane-modified (meth)acrylate:epoxy-modified (meth)acrylate = 90:10 to 10:90, more preferably urethane-modified (meth)acrylate:epoxy-modified (meth)acrylate = 85:15 to 30:70, and even more preferably urethane-modified (meth)acrylate:epoxy-modified (meth)acrylate = 80:20 to 50:50. If the mass ratio of urethane-modified (meth)acrylate to epoxy-modified (meth)acrylate is 90:10 to 10:90, the curing properties and adhesion strength to laminated steel sheets are superior.

[0084] A urethane-modified (meth)acrylate is a compound formed by reacting an isocyanate group with a hydroxyl group, having a urethane bond and a (meth)acryloyl group on its main chain. From the viewpoint of curability, the (meth)acryloyl group is preferably located at the end of the molecular chain. Examples of methods for manufacturing urethane-modified (meth)acrylates are not particularly limited, including methods of reacting a hydroxyl-containing polyol compound with an isocyanate-containing (meth)acrylate; methods of reacting a hydroxyl-containing polyol compound, a polyisocyanate compound, and a hydroxyl-containing (meth)acrylate, etc. In one embodiment, the urethane-modified (meth)acrylate preferably has a polyether backbone. The urethane-modified (meth)acrylate can be used alone or in combination of two or more types.

[0085] Examples of polyol compounds with hydroxyl groups used in the manufacture of urethane-modified (meth)acrylates are not particularly limited and include polyester polyols, polycarbonate polyols, polyether polyols, etc. They can be used alone or in combination of two or more.

[0086] Examples of isocyanate-containing (meth)acrylates used in the manufacture of urethane-modified (meth)acrylates are not particularly limited, and examples include 2-methacryloyloxyethyl isocyanate (also known as 2-isocyanate ethyl methacrylate) and 2-isocyanate ethyl acrylate. They can be used alone or in combination of two or more.

[0087] Examples of polyisocyanate compounds used in the manufacturing method of urethane-modified (meth)acrylates are not particularly limited, and examples include aromatic polyisocyanates, alicyclic polyisocyanates, and linear or branched aliphatic polyisocyanates. Examples of aromatic polyisocyanates are also not particularly limited, and examples include 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,3-phenylenedimethylene diisocyanate, 1,4-phenylenedimethylene diisocyanate, tetramethylphenylenedimethylene diisocyanate, diphenylmethane diisocyanate, naphthalene-1,5-diisocyanate, and triphenylmethane triisocyanate. Examples of alicyclic polyisocyanates are not particularly limited and include isophorone diisocyanate, bis(4-isocyanate-cyclohexyl)methane, 1,3-bis(isocyanate-methyl)cyclohexane, 1,4-bis(isocyanate-methyl)cyclohexane, norbornane diisocyanate, and dicycloheptane triisocyanate. Examples of straight-chain or branched aliphatic polyisocyanates are also not particularly limited and include hexamethylene diisocyanate, 1,3,6-hexamethylene triisocyanate, and 1,6,11-undecane triisocyanate. They can be used alone or in combination of two or more.

[0088] Examples of hydroxyl-containing (meth)acrylates used in the manufacturing method of urethane-modified (meth)acrylates are not particularly limited, and examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, 1,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, pentaerythritol tri(meth)acrylate, etc. They can be used alone or in combination of two or more.

[0089] Epoxy-modified (meth)acrylates can be compounds synthesized by ring-opening polymerization of acrylic acid and the glycidyl groups of glycidyl ether compounds. However, the method for synthesizing epoxy-modified (meth)acrylates is not limited to this method. Various backbones such as bisphenol A type, bisphenol F type, phenolic varnish type, hydrogenated bisphenol A type, and / or hydrogenated bisphenol F type can be used as the backbone of the glycidyl ether. They can be used alone or in combination of two or more. In one embodiment, the epoxy-modified (meth)acrylate preferably has a bisphenol A type backbone. Specific examples of epoxy-modified (meth)acrylates are not particularly limited, and examples include bisphenol A diglycidyl ether type epoxy diacrylates (such as Viscoat #540 manufactured by Osaka Organic Chemical Industry Co., Ltd.), ethoxylated bisphenol A diglycidyl ether type epoxy dimethacrylates, fatty acid modified epoxy (meth)acrylates, amine modified bisphenol epoxy (meth)acrylates, phenolic varnish epoxy (meth)acrylates, and epoxidized soybean oil (meth)acrylates. They can be used alone or in combination of two or more.

[0090] There are no particular limitations on (meth)acrylates having an aromatic ring, as long as they are compounds having one or more (meth)acryloyl groups and an aromatic ring within the molecule. However, compounds equivalent to urethane-modified (meth)acrylates are not treated as (meth)acrylates having an aromatic ring, but rather as urethane-modified (meth)acrylates. That is, if a compound equivalent to an urethane-modified (meth)acrylate has an aromatic ring, it is treated as an urethane (meth)acrylate, not an aromatic (meth)acrylate. Similarly, compounds equivalent to epoxy-modified (meth)acrylates are not treated as (meth)acrylates having an aromatic ring, but rather as epoxy-modified (meth)acrylates. That is, if a compound equivalent to an epoxy-modified (meth)acrylate has an aromatic ring, it is treated as an epoxy-modified (meth)acrylate, not an aromatic (meth)acrylate. Specific examples of (meth)acrylates having an aromatic ring are not particularly limited, such as phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, and ethoxylated nonylphenyl (meth)acrylate (also known as: nonylphenol EO modified acrylate), etc. They can be used alone or in combination of two or more.

[0091] In one embodiment, (C) component: The compound having one or more (meth)acryloyl groups preferably comprises one or more compounds selected from urethane-modified (meth)acrylates having two (meth)acryloyl groups at both ends, epoxy-modified (meth)acrylates having two (meth)acryloyl groups at both ends, and (meth)acrylates having two (meth)acryloyl groups at both ends and having an aromatic ring. More preferably, it comprises urethane-modified (meth)acrylates having two (meth)acryloyl groups at both ends and epoxy-modified (meth)acrylates having two (meth)acryloyl groups at both ends. More preferably, it comprises urethane-modified acrylates having two acryloyl groups at both ends and epoxy-modified acrylates having two acryloyl groups at both ends. Particularly preferred, it comprises urethane-modified acrylates having two acryloyl groups at both ends and having a polyether backbone, and epoxy-modified acrylates having two acryloyl groups at both ends and having a bisphenol A type backbone.

[0092] (C) Ingredients: The compound having one or more (meth)acryloyl groups preferably includes at least one compound selected from monofunctional (meth)acrylate compounds having one (meth)acryloyl group as a molecule, and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups as a molecule. (C) Ingredients: The compound having one or more (meth)acryloyl groups preferably includes a monomer having a (meth)acryloyl group. Examples of monomers having a (meth)acryloyl group include monofunctional (meth)acrylate monomers having one (meth)acryloyl group as a molecule, and polyfunctional (meth)acrylate monomers having two or more (meth)acryloyl groups as a molecule. They can be used alone or in combination of two or more. The monofunctional (meth)acrylate compound can be a monofunctional (meth)acrylate monomer. The polyfunctional (meth)acrylate compound can be a polyfunctional (meth)acrylate monomer.

[0093] (C) Composition: The compound having one or more (meth)acryloyl groups preferably includes one or more compounds selected from monofunctional (meth)acrylate monomers and polyfunctional (meth)acrylate monomers, more preferably includes monofunctional (meth)acrylate monomers, and even more preferably includes monofunctional methacrylate monomers.

[0094] Examples of monofunctional (meth)acrylate compounds are not particularly limited, and may be monofunctional (meth)acrylate compounds (I) that are not urethane-modified (meth)acrylates, not epoxy-modified (meth)acrylates, or not (meth)acrylates having an aromatic ring. Monofunctional (meth)acrylate compound (I) preferably does not contain any repeating monomer units or any units derived therefrom. That is, monofunctional (meth)acrylate compound (I) is preferably a monofunctional (meth)acrylate monomer.

[0095] Examples of monofunctional (meth)acrylate compounds (I) without particular limitation include ethyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, isobutyl methacrylate, 2-ethylhexyl (meth)acrylate, isodecanyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, and methpropylene. 4-Hydroxycyclohexyl acrylate, 1,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, isobornyl methacrylate, diethylene glycol mono(meth)acrylate, triethylene glycol mono(meth)acrylate, tetraethylene glycol mono(meth)acrylate, pentaethylene glycol mono(meth)acrylate, hexaethylene glycol mono(meth)acrylate, heptaethylene glycol mono(meth)acrylate, octaethylene glycol mono(meth)acrylate, nonaethylene glycol mono(meth)acrylate, decaethylene glycol mono(meth)acrylate, tripropylene glycol mono(meth)acrylate Acrylic esters, methoxytetrapropylene glycol mono(meth)acrylate, methoxypentapropylene glycol mono(meth)acrylate, methoxyhexapropylene glycol mono(meth)acrylate, methoxyheptapropylene glycol mono(meth)acrylate, methoxyoctapropylene glycol mono(meth)acrylate, methoxynonapropylene glycol mono(meth)acrylate, methoxydepropanediol mono(meth)acrylate, methoxytributylene glycol mono(meth)acrylate, methoxytetrabutylene glycol mono(meth)acrylate, methoxypentabutylene glycol mono(meth)acrylate, methoxyheptabutylene glycol mono(meth)acrylate, methoxyheptabutylene glycol mono(meth)acrylate, methoxyoctabutylene glycol mono(meth)acrylate, methoxynonabutylene glycol mono(meth)acrylate, methoxydebutanediol mono(meth)acrylate Ethoxydiethylene glycol mono(meth)acrylate, ethoxytriethylene glycol mono(meth)acrylate, ethoxytetraethylene glycol mono(meth)acrylate, ethoxypentaethylene glycol mono(meth)acrylate, ethoxyhexaethylene glycol mono(meth)acrylate, ethoxyheptaethylene glycol mono(meth)acrylate, ethoxyoctaneethylene glycol mono(meth)acrylate, ethoxynonethylene glycol mono(meth)acrylate, ethoxydeethylene glycol mono(meth)acrylate, ethoxytripropylene glycol mono(meth)acrylate, ethoxytetrapropylene glycol mono(meth)acrylate, ethoxypentapropylene glycol mono(meth)acrylate, ethoxyhexapropylene glycol mono(meth)acrylate, ethoxyheptapropylene glycol mono(meth)acrylate, ethoxyheptapropylene glycol mono(meth)acrylateEthoxyoctapropylene glycol mono(meth)acrylate, ethoxynonpropylene glycol mono(meth)acrylate, ethoxydecapropylene glycol mono(meth)acrylate, ethoxytributylene glycol mono(meth)acrylate, ethoxytetrabutylene glycol mono(meth)acrylate, ethoxypentabutylene glycol mono(meth)acrylate, ethoxyhexabutylene glycol mono(meth)acrylate, ethoxyheptabutylene glycol mono(meth)acrylate, ethoxyoctabutylene glycol mono(meth)acrylate, ethoxynonbutylene glycol mono(meth)acrylate, ethoxydecabutylene glycol mono(meth)acrylate, etc. They can be used alone or in combination of two or more. Preferred examples of monofunctional (meth)acrylate monomers include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, 1,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, ethylene glycol mono(meth)acrylate, and propylene glycol mono(meth)acrylate. These can be used alone or in combination of two or more.

[0096] Monofunctional (meth)acrylate compounds can be monofunctional (meth)acrylate monomers having an aromatic ring. Examples of monofunctional (meth)acrylate monomers having an aromatic ring are not particularly limited, and include 2-hydroxy-3-phenoxypropyl acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxyethyl (meth)acrylate, etc. Monomers having a monofunctional (meth)acryloyl group can be used alone or in combination of two or more.

[0097] Monofunctional (meth)acrylate compounds can be used alone or in combination of two or more.

[0098] In one embodiment, (C) component: the compound having one or more (meth)acryloyl groups preferably comprises a monofunctional (meth)acrylate compound, more preferably a monofunctional (meth)acrylate compound (I), and even more preferably at least one compound selected from the monofunctional (meth)acrylate compounds (I) exemplified above.

[0099] In one embodiment, (C) component: The compound having one or more (meth)acryloyl groups preferably comprises a monofunctional (meth)acrylate monomer, more preferably a monofunctional (meth)acrylate monomer as a monofunctional (meth)acrylate compound (I).

[0100] In one embodiment, (C) component: The compound having one or more (meth)acryloyl groups preferably comprises a monofunctional (meth)acrylate monomer having a hydroxyl group, more preferably comprises a monofunctional (meth)acrylate monomer having a hydroxyl group as a monofunctional (meth)acrylate compound (I).

[0101] In one embodiment, (C) component: the compound having one or more (meth)acryloyl groups further preferably contains 2-hydroxyethyl (meth)acrylate, and particularly preferably contains 2-hydroxyethyl methacrylate.

[0102] In one embodiment, the monofunctional (meth)acrylate compound may be a monomer having a monofunctional (meth)acryloyl group, or a monomer having a hydroxyl group and a monofunctional (meth)acryloyl group, or a monomer having a hydroxyl group and a monofunctional (meth)acryloyl group as the monofunctional (meth)acrylate compound (I), or 2-hydroxyethyl (meth)acrylate, or 2-hydroxyethyl methacrylate.

[0103] The polyfunctional (meth)acrylate compound is not particularly limited and can be any polyfunctional (meth)acrylate compound (II) that is not a urethane-modified (meth)acrylate, not an epoxy-modified (meth)acrylate, or not a (meth)acrylate with an aromatic ring. The polyfunctional (meth)acrylate compound can be a combination of at least one compound selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates with an aromatic ring with polyfunctional (meth)acrylate compound (II). Polyfunctional (meth)acrylate compound (II) preferably does not contain any repeating monomer units or any derivative thereof. That is, polyfunctional (meth)acrylate compound (II) is preferably a polyfunctional (meth)acrylate monomer. Examples of polyfunctional (meth)acrylate compounds are not particularly limited, and include difunctional (meth)acrylate compounds, trifunctional (meth)acrylate compounds, tetrafunctional (meth)acrylate compounds, pentafunctional (meth)acrylate compounds, hexafunctional (meth)acrylate compounds, etc. Examples of polyfunctional (meth)acrylate monomers are also not particularly limited, and include difunctional (meth)acrylate monomers, trifunctional (meth)acrylate monomers, tetrafunctional (meth)acrylate monomers, pentafunctional (meth)acrylate monomers, hexafunctional (meth)acrylate monomers, etc. Preferred examples of polyfunctional (meth)acrylate compounds, as described above, include urethane-modified (meth)acrylates having two or more (meth)acryloyl groups, epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and (meth)acrylates having two or more (meth)acryloyl groups and an aromatic ring, etc.

[0104] The polyfunctional (meth)acrylate compound (II) is not particularly limited. Examples of difunctional (meth)acrylate compounds that are polyfunctional (meth)acrylate compounds (II) are not particularly limited, and examples include ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, propylene glycol dimethacrylate, polypropylene glycol dimethacrylate, dihydroxymethyl-tricyclodecane dimethacrylate, tricyclodecyl dimethacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, neopentyl glycol dimethacrylate, 2-hydroxy-3-methacryl propylacrylate, etc. Preferred examples of difunctional (meth)acrylate monomers for polyfunctional (meth)acrylate compounds (II) are not particularly limited, and examples include ethylene glycol dimethacrylate, propylene glycol dimethacrylate, tricyclodecyl dimethacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, neopentyl glycol dimethacrylate, and 2-hydroxy-3-methacryloylpropyl acrylate. Examples of trifunctional (meth)acrylate monomers for polyfunctional (meth)acrylate compounds (II) are not particularly limited, and examples include trimethylolpropane trimethacrylate. Examples of tetrafunctional (meth)acrylate compounds for polyfunctional (meth)acrylate compounds (II) are not particularly limited, and examples include bis(trimethylolpropane)tetramethacrylate and pentaerythritol tetramethacrylate. Preferred examples of tetrafunctional (meth)acrylate monomers are not particularly limited, and examples include pentaerythritol tetra(meth)acrylate. Examples of pentafunctional (meth)acrylate compounds of polyfunctional (meth)acrylate compound (II) are not particularly limited, and examples include dipentaerythritol monohydroxy penta(meth)acrylate and alkyl-modified dipentaerythritol penta(meth)acrylate. Examples of hexafunctional (meth)acrylate compounds of polyfunctional (meth)acrylate compound (II) are not particularly limited, and examples include dipentaerythritol hexa(meth)acrylate. Polyfunctional (meth)acrylate compounds can be used alone or in combination of two or more.

[0105] The polyfunctional (meth)acrylate compound preferably comprises at least one compound selected from the compounds exemplified above. The polyfunctional (meth)acrylate compound may be at least one compound selected from the compounds exemplified above.

[0106] (C) The mass ratio of polyfunctional (meth)acrylate compounds to monofunctional (meth)acrylate compounds in component (C) is not particularly limited, but preferably polyfunctional (meth)acrylate compounds: monofunctional (meth)acrylate compounds = 1:99 to 99:1, more preferably polyfunctional (meth)acrylate compounds: monofunctional (meth)acrylate compounds = 20:80 to 80:20, and even more preferably polyfunctional (meth)acrylate compounds: monofunctional (meth)acrylate compounds = 50:50 to 75:25.

[0107] Compounds having one or more (meth)acryloyl groups can be used alone or in combination with two or more. (C) Component: The compound having one or more (meth)acryloyl groups preferably includes at least one compound selected from the above-mentioned compounds. (C) Component: The compound having one or more (meth)acryloyl groups more preferably includes, for example, urethane-modified (meth)acrylates having two or more (meth)acryloyl groups, epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and monofunctional (meth)acrylate compound (I). In this case, preferred examples of urethane-modified (meth)acrylates having two or more (meth)acryloyl groups, epoxy-modified (meth)acrylates having two or more (meth)acryloyl groups, and monofunctional (meth)acrylate compound (I) are as described above.

[0108] In one embodiment, component (C): a compound having one or more (meth)acryloyl groups may be, for example, a urethane-modified (meth)acrylate having two or more (meth)acryloyl groups, an epoxy-modified (meth)acrylate having two or more (meth)acryloyl groups, and a monofunctional (meth)acrylate compound (I). Alternatively, it may be a urethane-modified (meth)acrylate having two or more (meth)acryloyl groups, an epoxy-modified (meth)acrylate having two or more (meth)acryloyl groups, and a monofunctional (meth)acrylate as monofunctional (meth)acrylate compound (I). The monomer may also be a urethane-modified (meth)acrylate with two (meth)acryloyl groups at both ends, an epoxy-modified (meth)acrylate with two (meth)acryloyl groups at both ends, and a monofunctional (meth)acrylate monomer as a monofunctional (meth)acrylate compound (I).

[0109] In one embodiment, (C) component: a compound having one or more (meth)acryloyl groups can be, for example, a urethane-modified (meth)acrylate having two (meth)acryloyl groups at both ends, an epoxy-modified (meth)acrylate having two (meth)acryloyl groups at both ends, and 2-hydroxyethyl (meth)acrylate, or a urethane-modified acrylate having two acryloyl groups at both ends, an epoxy-modified acrylate having two acryloyl groups at both ends, and 2-hydroxyethyl methacrylate.

[0110] In one embodiment, (C) component: a compound having one or more (meth)acryloyl groups can be, for example, a urethane-modified (meth)acrylate having two (meth)acryloyl groups at both ends and having a polyether backbone, an epoxy-modified (meth)acrylate having two (meth)acryloyl groups at both ends and having a bisphenol A backbone, and 2-hydroxyethyl (meth)acrylate, or a urethane-modified acrylate having two acryloyl groups at both ends and having a polyether backbone, an epoxy-modified acrylate having two acryloyl groups at both ends and having a bisphenol A backbone, and 2-hydroxyethyl methacrylate.

[0111] There is no particular limitation on the content of component (C) in the anaerobic curing adhesive. The content of component (C) relative to 100% by mass (relative to the total mass of the anaerobic curing adhesive) is preferably 50% by mass or more and less than 100% by mass, more preferably 60% by mass or more and less than 100% by mass, further preferably 70% by mass or more and less than 100% by mass, more preferably 90% by mass or more and less than 100% by mass, and particularly preferably 95% by mass or more and less than 100% by mass. The content of component (C) relative to 100% by mass (relative to the total mass of the anaerobic curing adhesive) can be 60% by mass to 99% by mass, or 70% by mass to 99% by mass. When two or more components (C) are used in combination, the amount of component (C) represents their total amount.

[0112] (D) Ingredients

[0113] (D) is an organic peroxide. Component (D) is used in the purpose of curing component (C). Examples of component (D) are not particularly limited, and include hydroperoxides, ketone peroxides, diallyl peroxides, peroxide esters, etc. They can be used alone or in combination of two or more. Specific examples of component (D) are not particularly limited, and include cumene hydroperoxide, tert-butyl hydroperoxide, p-hydroxyl hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, diisopropylbenzene hydroperoxide, etc. They can be used alone or in combination of two or more. From the viewpoint of excellent anaerobic curing properties and the storage stability of the adhesive, hydroperoxides are preferred, and cumene hydroperoxide is more preferred. Organic peroxides can be used alone or in combination of two or more. Component (D): The organic peroxide preferably contains at least one compound selected from the compounds exemplified above. In one embodiment, component (D): the organic peroxide is preferably a compound selected from at least one of hydroperoxides, ketone peroxides, diallyl peroxides, and peroxide esters, more preferably a compound selected from at least one of cumene hydroperoxide, tert-butyl hydroperoxide, p-peroxylane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, and diisopropylbenzene hydroperoxide, and even more preferably cumene hydroperoxide. In one embodiment, component (D): the organic peroxide may be, for example, a hydroperoxide.

[0114] The content of component (D) in the anaerobic curing adhesive is not particularly limited. The content of component (D) is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of component (C), more preferably 0.3 to 15 parts by mass, and even more preferably 0.5 to 10 parts by mass. By setting the content of component (D) to 0.1 to 30 parts by mass relative to 100 parts by mass of component (C), both curing properties and storage stability can be achieved. The content of component (D) relative to 100 parts by mass of component (C) can be 0.1 to 20 parts by mass, 0.3 to 10 parts by mass, or 0.5 to 5 parts by mass. When two or more components (C) are used in combination, the amount of component (C) represents their total amount. When two or more components (D) are used in combination, the amount of component (D) represents their total amount.

[0115] There is no particular limitation on the content of component (D) in the anaerobic curing adhesive. The content of component (D) relative to 100 parts by weight of component (E) is preferably 1 to 300 parts by weight, more preferably 3 to 150 parts by weight, and even more preferably 5 to 100 parts by weight. When two or more components (D) are used in combination, the amount of component (D) represents their total amount. When two or more components (E) are used in combination, the amount of component (E) represents their total amount.

[0116] (E) Ingredients

[0117] (E) is an anaerobic curing catalyst. Component (E) decomposes component (D) in an anaerobic state without contact with oxygen to generate free radicals, promoting curing. Examples of component (E) are not particularly limited and include saccharin, amine compounds, azole compounds, thiols, hydrazine compounds, and their derivatives. They can be used alone or in combination. It should be noted that in this specification, the azole compound is used in a form where saccharin is not included. Component (C): The anaerobic curing catalyst preferably contains at least one compound selected from the compounds exemplified above. From the viewpoint of excellent curing properties, component (C): The anaerobic curing catalyst preferably contains one or more compounds selected from saccharin, azole compounds, thiols, and hydrazine compounds, more preferably at least one compound selected from saccharin and hydrazine compounds, further preferably saccharin, and particularly preferably a combination of saccharin and hydrazine compounds. In one embodiment, the compound corresponding to the curing accelerator of component (A): The anaerobic curing adhesive is preferably not treated as component (E). That is, in one embodiment, component (E) is preferably component (A): a compound other than the compound contained in the curing accelerator of the anaerobic curing adhesive.

[0118] Examples of amine compounds are not particularly limited and include heterocyclic secondary amines, heterocyclic tertiary amines, and aromatic tertiary amines. Examples of heterocyclic secondary amines are not particularly limited and include 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinazine. Examples of heterocyclic tertiary amines are not particularly limited and include quinoline, methylquinoline, quinazine, and quinoxaline phenazine. Examples of aromatic tertiary amines are not particularly limited and include N,N-dimethyl-anisidine and N,N-dimethylaniline. They can be used alone or in combination of two or more.

[0119] Examples of azole compounds are not particularly limited and may include thiazoles, isothiazoles, thiadiazoles, oxazoles, isoxazoles, oxadiazoles, diazoles, triazoles, etc. More specifically, examples of azole compounds may include benzothiazoles, 1,2,4-triazoles, benzotriazoles, hydroxybenzotriazoles, benzoxazoles, 1,2,3-benzothiadiazoles, 3-mercaptobenzotriazoles, etc., but are not limited to these. They can be used alone or in combination of two or more.

[0120] Examples of thiols are not particularly limited and include straight-chain thiols. Examples of straight-chain thiols include n-dodecyl thiols, ethyl thiols, and butyl thiols, but are not limited to these. They can be used alone or in combination of two or more.

[0121] Examples of hydrazine compounds include 1-acetyl-2-phenylhydrazine, 1-acetyl-2-(p-tolyl)hydrazine, 1-benzoyl-2-phenylhydrazine, 1-(1',1',1'-trifluoro)acetyl-2-phenylhydrazine, 1,5-diphenyl-carbonylhydrazine, 1-formyl-2-phenylhydrazine, 1-acetyl-2-(p-bromophenyl)hydrazine, 1-acetyl-2-(p-nitrophenyl)hydrazine, 1-acetyl-2-(2'-phenylethylhydrazine), ethyl hydrazine formate, p-nitrophenylhydrazine, and p-toluenesulfonylhydrazine, but are not limited thereto. They can be used alone or in combination of two or more. The hydrazine compound preferably contains at least one compound selected from the compounds exemplified above. From the viewpoint of excellent curability, hydrazine compounds having an acetyl group are preferred, and 1-acetyl-2-phenylhydrazine is more preferred.

[0122] In one embodiment, component (E): the anaerobic curing catalyst preferably comprises a hydrazine compound, more preferably at least one compound selected from the hydrazine compounds exemplified above, and even more preferably 1-acetyl-2-phenylhydrazine. In one embodiment, component (E): the anaerobic curing catalyst preferably comprises a hydrazine compound having an acetyl group. In one embodiment, the hydrazine compound may be, for example, a hydrazine compound having an acetyl group, or 1-acetyl-2-phenylhydrazine.

[0123] The anaerobic curing catalyst can be used alone or in combination with two or more. (E) Component: The anaerobic curing catalyst preferably contains at least one compound selected from the above-described compounds. In one embodiment, (E) component: The anaerobic curing catalyst is preferably saccharin and a hydrazine compound, more preferably saccharin and at least one compound selected from the hydrazine compounds exemplified above, and even more preferably saccharin and 1-acetyl-2-phenylhydrazine. In one embodiment, (E) component: The anaerobic curing catalyst is preferably saccharin and a hydrazine compound having an acetyl group.

[0124] There is no particular limitation on the content of component (E) in the anaerobic curing adhesive. From the viewpoint of curing properties, the content of component (E) is preferably 0.01 to 40 parts by weight relative to 100 parts by weight of component (C). The content of component (E) relative to 100 parts by weight of component (C) can be 0.5 to 30 parts by weight, or 1 to 25 parts by weight. For example, the content of component (E) relative to 100 parts by weight of component (C) can be 0.01 to 10 parts by weight, or 0.01 to 5 parts by weight. For example, the content of component (E) relative to 100 parts by weight of component (C) can be 0.1 to 10 parts by weight, or 0.1 to 5 parts by weight. For example, the content of component (E) relative to 100 parts by weight of component (C) can be 0.5 to 10 parts by weight, or 0.5 to 5 parts by weight. For example, the content of component (E) relative to 100 parts by weight of component (C) can be 1 to 10 parts by weight, or 1 to 5 parts by weight. When two or more (E) components are used in combination, the amount of (E) components represents their total amount. When two or more (C) components are used in combination, the amount of (C) components represents their total amount.

[0125] In the case of a combination of saccharin and hydrazine compounds, i.e., when component (E): the anaerobic curing catalyst contains saccharin and hydrazine compounds, the mass ratio of saccharin to hydrazine compounds in component (E) is not particularly limited. The preferred mass ratio of saccharin to hydrazine compounds in component (E) is 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 50:50 to 80:20, and particularly preferably 60:40 to 75:25. When two or more hydrazine compounds are used in combination, the amount of hydrazine compounds indicates their total amount.

[0126] Other components in anaerobic curing adhesives

[0127] The anaerobic curing adhesive may further contain one or more other components, or may not contain any. There are no particular restrictions on the other components in the anaerobic curing adhesive, as long as they are components (C) to (E). The anaerobic curing adhesive may further contain, to a suitable extent without impairing its properties, one or more additives selected from stabilizers, inorganic fillers, organic fillers, silane coupling agents, light stabilizers, photosensitizers, polymerization inhibitors, chelating agents, etc. (one or more other components). The anaerobic curing adhesive preferably further contains at least one additive selected from the additives exemplified above, and more preferably further contains a stabilizer.

[0128] Anaerobic curing adhesives may or may not contain stabilizers. Stabilizers may be used alone or in combination of two or more. Examples of stabilizers are not particularly limited and include 2,6-di-tert-butyl-p-cresol, hydroquinone, hydroquinone monomethyl ether, 4-tert-butylcatechol, etc. They may be used alone or in combination of two or more. From the viewpoint of the adhesive's storage stability, 2,6-di-tert-butyl-p-cresol is preferred as a stabilizer. The stabilizer preferably contains at least one compound selected from the compounds exemplified above. In one embodiment, the stabilizer is preferably at least one compound selected from the compounds exemplified above, more preferably 2,6-di-tert-butyl-p-cresol. In one embodiment, the content of the stabilizer is not particularly limited, but is preferably 0.01 to 0.5% by mass relative to the total mass of the anaerobic curing adhesive (relative to the total mass of the anaerobic curing adhesive; relative to 100% by mass of the anaerobic curing adhesive), more preferably 0.02 to 0.3% by mass, and even more preferably 0.05 to 0.15% by mass. When two or more stabilizers are used in combination, the amount of stabilizer represents their total amount.

[0129] Anaerobic curing adhesives may or may not contain inorganic fillers. Examples of inorganic fillers are not particularly limited and include glass, silica, talc, alumina, mica, ceramics, organosilicon particles, calcium carbonate, aluminum nitride, carbon powder, kaolin, dried clay minerals, and dried diatomaceous earth. They can be used alone or in combination of two or more.

[0130] Anaerobic curing adhesives may or may not contain organic fillers. Examples of organic fillers are not particularly limited, as long as they are powders of organic materials composed of rubber, elastomers, plastics, and / or polymers (homopolymers and / or copolymers). They can be used alone or in combination of two or more. Organic fillers can be multilayered organic fillers such as core-shell type. The average particle size of the organic filler is not particularly limited, but is preferably in the range of 0.05 to 50 μm.

[0131] Anaerobic curing adhesives may or may not contain silane coupling agents. Examples of silane coupling agents are not particularly limited and include glycidyl-containing silane coupling agents, vinyl-containing silane coupling agents, (meth)acryloyl-containing silane coupling agents, amino-containing silane coupling agents, γ-mercaptopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, etc. Examples of silane coupling agents containing glycidyl groups are not particularly limited, and include 3-acryloyloxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane, 3-epoxypropoxypropylmethyldipropoxysilane, 3-epoxypropoxypropyldimethylmonomethoxysilane, 3-epoxypropoxypropyldimethylmonoethoxysilane, 3-epoxypropoxypropyldimethylmonopropoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-epoxypropoxypropyltriethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane, etc. Examples of vinyl-containing silane coupling agents are not particularly limited, and include vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, vinyltrimethoxysilane, etc. Examples of silane coupling agents containing (meth)acrylyl groups are not particularly limited and include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropylmethyldipropoxysilane, 3-acryloxypropylmethyldiethoxysilane, 3-acryloxypropylmethyldipropoxysilane, 3-acryloxypropylmethyldipropoxysilane, 3-acryloxypropylmethyldimethoxysilane, 3-acryloxypropylmethyldipropoxysilane, 3-acryloxypropylmethyldimethoxysilane, 3-acryloxypropylmethyldipropoxysilane, γ-methacryloxypropyltrimethoxysilane, etc. Examples of amino-containing silane coupling agents are not particularly limited, and include N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, etc. In this specification, silane coupling agents containing (meth)acryloyl groups are not included in component (C). In one embodiment, component (C) preferably does not contain: compounds containing silicon (Si) atoms bonded with hydroxyl and / or hydrolyzable groups, and more preferably does not contain: compounds containing Si atoms. In this specification, amino-containing silane coupling agents are not included in component (E), and mercapto-containing silane coupling agents are not included in component (E).In one embodiment, component (E) preferably does not contain: compounds containing silicon (Si) atoms bonded with hydroxyl and / or hydrolyzable groups, more preferably does not contain: compounds containing Si atoms.

[0132] Anaerobic curing adhesives may further contain at least one additive selected from light stabilizers, photosensitizers, polymerization inhibitors, and chelating agents, or may not contain any of them. Anaerobic curing adhesives may not contain any of the light stabilizers, photosensitizers, polymerization inhibitors, and chelating agents.

[0133] From the viewpoint of maintaining stability, anaerobic curing adhesives preferably do not contain metals as components. In this specification, "anaerobic curing adhesive does not contain metals as components" means that none of the components constituting the anaerobic curing adhesive contain metal elements. In one embodiment, the anaerobic curing adhesive preferably does not contain metal elements. In this specification, "anaerobic curing adhesive does not contain metal elements" means that the anaerobic curing adhesive contains metal elements only in the form of unavoidable impurities, or does not contain any metal elements at all.

[0134] Another aspect (the second aspect) of the present invention also relates to a primer composition comprising the above-described (A-1), (A-2), and (B) components, wherein the total of (A-1) and (A-2) is 35 parts by mass or less relative to 100 parts by mass of component (B) (preferably, the total of (A-1) and (A-2) is 0.1 to 35 parts by mass relative to 100 parts by mass of component (B)). According to the primer composition of this aspect (the second aspect), it is possible to suppress the performance degradation (time-dependent reduction in lubrication performance) of primer compositions containing curing accelerators and lubricants (e.g., stamping oils, etc.) and to improve the curing speed and bond strength of anaerobic curing adhesives.

[0135] The total content of (A-1) and (A-2) in the primer composition described in this method (second method) is more than 0 parts by mass and less than 35 parts by mass relative to 100 parts by mass of component (B). As a preferred example of the total content of (A-1) and (A-2) in the primer composition described in this method (second method), there are no particular limitations. Examples of the total content relative to 100 parts by mass of component (B) include more than 0 parts by mass and less than 25 parts by mass, more than 0 parts by mass and less than 20 parts by mass, more than 0.1 parts by mass, more than 1 part by mass, more than 5 parts by mass, 0.1 to 35 parts by mass, 1 to 25 parts by mass, 5 to 20 parts by mass, 1 to 35 parts by mass, 5 to 35 parts by mass, 15 to 35 parts by mass, 10 to 25 parts by mass, 10 to 20 parts by mass, more than 10 parts by mass and less than 20 parts by mass, 10 to 18 parts by mass, 15 to 25 parts by mass, 15 to 20 parts by mass, more than 15 parts by mass and less than 20 parts by mass, and 15 to 18 parts by mass. When two or more types of (A-1) are used in combination, the amount of (A-1) represents their total amount. When two or more (A-2) components are used in combination, the quantity of (A-2) represents their total quantity. When two or more (B) components are used in combination, the quantity of (B) components represents their total quantity.

[0136] The embodiments of (A-1), (A-2), (B) and other components (other components in the primer composition) described in this method (second method) are the same as those described in the primer composition of the first method.

[0137] <Instructions for use of primer composition>

[0138] In this specification, the primer composition is pre-applied to the substrate before the adhesive is applied, thereby promoting the curing of the anaerobic curing adhesive and improving the curing time and bond strength. The primer composition described in the above embodiments may consist of component (A), component (B), and one or more other components as needed, preferably component (A) and component (B). Component (A) and component (B) may be mixed just before the application of the anaerobic curing adhesive or pre-mixed.

[0139] <Adhesive Composition Kit>

[0140] The primer composition described in the first embodiment is preferably used in an adhesive composition reagent kit comprising an anaerobic curing adhesive and the primer composition. The primer composition described in the second embodiment is preferably used in an adhesive composition reagent kit comprising an anaerobic curing adhesive and the primer composition. Therefore, another embodiment (the third embodiment) of the present invention may also relate to an adhesive composition reagent kit comprising an anaerobic curing adhesive and the primer composition described in the first or second embodiment above. According to the adhesive composition reagent kit of this embodiment, the performance degradation (degradation of lubrication performance over time) of the primer composition containing a curing accelerator and a lubricating oil (e.g., stamping oil) can be suppressed, and the curing speed and bond strength of the anaerobic curing adhesive can be improved. In the adhesive composition reagent kit of this embodiment, the primer composition and the anaerobic curing adhesive are present separately. The anaerobic curing adhesive in the adhesive composition reagent kit of this embodiment is the same as that described in the primer composition of the first embodiment. The preferred embodiment of the anaerobic curing adhesive in the adhesive composition reagent kit of this embodiment is also the same as that described in the primer composition of the first embodiment. The primer composition in the adhesive composition kit described in this embodiment is identical to that described in the primer composition of the first embodiment or the primer composition of the second embodiment. Preferred embodiments of the primer composition in the adhesive composition kit described in this embodiment are also identical to those described in the primer composition of the first embodiment or the primer composition of the second embodiment. In one embodiment, the anaerobic curing adhesive preferably comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

[0141] <Application>

[0142] The primer composition described in the first method, the primer composition described in the second method, and the adhesive composition kit described in the third method can be used, for example, in bonding and / or lamination when the adherends are metals. Examples of adherends are not particularly limited, including steel plates (e.g., electromagnetic steel plates), Welsh steel, etc. Examples of metals are not particularly limited, including SPCC (Steel Plate Cold Commercial), copper, etc.

[0143] Depending on the type of metal, there are often situations where anaerobic curing is not suitable. However, even for such metals, by applying the primer composition described in the first method, the primer composition described in the second method, or the primer composition in the adhesive composition reagent kit described in the third method, the primer composition and the anaerobic curing adhesive can sometimes be used together to promote curing and improve the bond strength based on the anaerobic curing adhesive.

[0144] As examples of more specific applications of the primer composition described in the first method, the primer composition described in the second method, and the adhesive composition reagent kit described in the third method, there are no particular limitations. Examples include the screwing in of spark plugs, the assembly of laminated steel plates and / or lamination molds for rotors of rotary motors, and the assembly of laminated steel plates and / or lamination molds for solenoids. Specifically, the primer composition described in the first method, the primer composition described in the second method, and the adhesive composition reagent kit described in the third method are each suitable for assembling laminated steel plates.

[0145] <Method for manufacturing laminates using primer compositions and laminates thereto>

[0146] The primer composition described in the first embodiment, the primer composition described in the second embodiment, and the adhesive composition reagent kit described in the third embodiment are preferably used in the method for manufacturing the laminate. In this case, the method for manufacturing the laminate preferably includes: applying the primer composition described in the first embodiment or the primer composition described in the second embodiment to a substrate; applying an anaerobic curing adhesive to the substrate, the primer composition film, or both; and after applying the primer composition and the anaerobic curing adhesive, bonding the substrate to the substrate to be bonded, and then curing the anaerobic curing adhesive. Therefore, another aspect (fourth aspect) of the present invention can also be said to relate to a method for manufacturing a laminate, comprising: applying a primer composition as described in the first aspect or the primer composition as described in the second aspect to an adherend; applying an anaerobic curing adhesive to the adherend, the primer composition film, or both; and after applying the primer composition and the anaerobic curing adhesive, bonding the adherend to the adherend as a bonding object, and then curing the anaerobic curing adhesive. According to the method for manufacturing a laminate described above, it is possible to suppress the performance degradation (time-dependent reduction in lubrication performance) of the primer composition containing a curing accelerator and a lubricant (e.g., stamping oil) and to improve the curing speed and bond strength of the anaerobic curing adhesive.

[0147] As an example of a laminate, there are no particular limitations, but a laminate comprising multiple steel plates is preferred, and a laminate comprising multiple electromagnetic steel plates is more preferred. One embodiment of the manufacturing method of the laminate is preferably a method for manufacturing laminated steel plates. In this case, the method for manufacturing laminated steel plates preferably includes: applying a primer composition as described in the first embodiment or a primer composition as described in the second embodiment to a steel plate (preferably an electromagnetic steel plate); applying an anaerobic curing adhesive to the substrate, the primer composition film, or both; and after applying the primer composition and the anaerobic curing adhesive, bonding the steel plate to the steel plate to be bonded (preferably an electromagnetic steel plate to be bonded), and then curing the anaerobic curing adhesive to obtain the laminate.

[0148] The primer composition coating can be partially or completely dried and / or cured. The primer composition coating can be dried and / or cured, for example, to a degree capable of laminating the anaerobic curing adhesive. The anaerobic curing adhesive can be applied to the surface (i.e., directly above) of the substrate (preferably a steel plate, particularly preferably an electromagnetic steel plate), the surface (i.e., directly above) of the primer composition coating, or both. The substrate (preferably a steel plate, particularly preferably an electromagnetic steel plate) to be bonded can be coated with the primer composition, the anaerobic curing adhesive, or both. When the substrate (preferably a steel plate, particularly preferably an electromagnetic steel plate) to be bonded is coated with both the primer composition and the anaerobic curing adhesive, the primer composition coating and the anaerobic curing adhesive coating can exist on different sides of the substrate, or they can be laminated and exist on the same side of the substrate.

[0149] The primer composition described in the first method, the primer composition described in the second method, and the adhesive composition reagent kit described in the third method are all particularly suitable for manufacturing methods of laminated steel sheets formed by stacking a specified number of thin steel sheets (preferably thin electromagnetic steel sheets) formed by punching strip steel sheets into a specified shape. There are no particular limitations on the manufacturing methods of laminates using the primer composition described in the first method, the primer composition described in the second method, or the adhesive composition reagent kit described in the third method. Examples of manufacturing methods of laminated steel sheets using the primer composition described in the first method, the primer composition described in the second method, or the adhesive composition reagent kit described in the third method are not particularly limited, and methods including steps 1 to 4 can be cited.

[0150] Step 1: Apply the primer composition described in the first method or the primer composition described in the second method to the strip steel plate;

[0151] Step 2: The strip steel plate coated with the above primer composition is punched into a specified shape to obtain the steel plate sheet coated with the above primer composition.

[0152] Step 3: Apply the anaerobic curing adhesive in a surface or dot pattern to the steel sheet coated with the above primer composition, so that the steel sheet is bonded and stacked with other steel sheets (steel sheets to be bonded).

[0153] Step 4: Under specified conditions, the above-mentioned anaerobic curing adhesive is cured to obtain laminated steel plates.

[0154] The steel sheet obtained in step 2 is a steel sheet coated with a primer composition. In step 3, the anaerobic curing adhesive can be applied to the surface of the object to be bonded (i.e., directly above), the surface of the applied primer composition (i.e., directly above), or both. The applied primer composition (the primer film) can be partially or completely dried and / or cured. The applied primer composition (the primer film) can, for example, be dried and / or cured to a degree that allows for the lamination of the anaerobic curing adhesive. In step 3, the steel sheet to be bonded can be coated with a primer composition, an anaerobic curing adhesive, or both. When the steel sheet to be bonded is a steel sheet coated with both a primer composition and an anaerobic curing adhesive, the primer composition coating and the anaerobic curing adhesive coating can exist separately on different sides of the steel sheet, or they can be laminated and exist on the same side of the steel sheet. Step 4 is a step set after step 3 in which the anaerobic curing adhesive is cured under specified conditions to obtain a laminated steel sheet. The curing of the anaerobic curing adhesive in step 4 takes place in a laminate containing the steel sheet coated with the primer composition, the anaerobic curing adhesive, and the steel sheet to be bonded.

[0155] In the above manufacturing method, when the primer composition described in the first aspect or the primer composition described in the second aspect includes (A-2), a drying step is preferably added between step 1 and step 2 and / or between step 2 and step 3. The drying temperature in the drying step is not particularly limited, but is preferably 10°C to 50°C, more preferably 15°C to 40°C, and even more preferably 20°C to 30°C. The total drying time in the drying step is not particularly limited, but is preferably 5 seconds to 5 hours, more preferably 5 seconds to 2 hours, and even more preferably 10 seconds to 1.5 hours.

[0156] In one embodiment of the method for manufacturing a laminate (preferably a method for manufacturing laminated steel plates), the anaerobic curing adhesive preferably comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

[0157] There are no particular restrictions on the materials constituting the two or more adhered objects, but it is preferred that at least a portion of them are the same, and particularly preferred that they are the same.

[0158] There are no particular limitations on the bonding of the adherends (preferably steel plates, and particularly preferably electromagnetic steel plates). For example, it is preferable to place the surface of the anaerobic adhesive layer (e.g., an anaerobic adhesive coating) on ​​the outermost surface of the adherends facing one surface of the adherends. The bonding of the adherends can be performed such that the surface of the anaerobic adhesive layer on the outermost surface of the adherends faces the surface of the primer composition layer on the outermost surface of the adherends. In adherends with an anaerobic adhesive layer on the outermost surface, it is preferable that the adherends are in contact with the primer composition layer, and that the primer composition layer is in contact with the anaerobic adhesive layer.

[0159] After two or more adherends are bonded together, the anaerobic curing adhesive is cured. The curing method is described below. One embodiment of the method for manufacturing a laminate may further include other operations and / or other steps.

[0160] The anaerobic curing adhesive used in the manufacturing method of the laminate described in the fourth embodiment is the same as that described in the primer composition described in the first embodiment. A preferred embodiment of the anaerobic curing adhesive used in the manufacturing method of the laminate described in the fourth embodiment is also the same as that described in the primer composition described in the first embodiment. The primer composition used in the manufacturing method of the laminate described in the fourth embodiment is the same as that described in the primer composition described in the first embodiment or the primer composition described in the second embodiment. A preferred embodiment of the primer composition used in the manufacturing method of the laminate described in the fourth embodiment is also the same as that described in the primer composition described in the first embodiment or the primer composition described in the second embodiment.

[0161] Another aspect (fifth aspect) of the present invention relates to a laminate manufactured using the primer composition described in the first aspect, the primer composition described in the second aspect, or the adhesive composition reagent package described in the third aspect, or by the laminate manufacturing method described in the fourth aspect. Examples of laminates are not particularly limited, but laminates comprising multiple steel plates are preferred, and laminates comprising multiple electromagnetic steel plates are more preferred. In one embodiment, the laminate is particularly preferably a laminate of steel plates.

[0162] The anaerobic curing adhesive used in the laminate of the fifth embodiment is the same as that described in the primer composition of the first embodiment. A preferred embodiment of the anaerobic curing adhesive used in the laminate of the fifth embodiment is also the same as that described in the primer composition of the first embodiment. The primer composition used in the laminate of the fifth embodiment is the same as that described in the primer composition of the first embodiment or the primer composition of the second embodiment. A preferred embodiment of the primer composition used in the laminate of the fifth embodiment is also the same as that described in the primer composition of the first embodiment or the primer composition of the second embodiment. The manufacturing method for obtaining the laminate of the fifth embodiment and its preferred embodiments are the same as those described in the manufacturing method of the laminate of the fourth embodiment.

[0163]

[0164] The primer composition described in the first embodiment, the primer composition described in the second embodiment, and the adhesive composition reagent package described in the third embodiment are preferably used in a curing promotion method for an anaerobic curing adhesive. In this case, the curing promotion method for the anaerobic curing adhesive preferably includes: curing the anaerobic curing adhesive while the coating film of the primer composition described in the first embodiment or the coating film of the primer composition described in the second embodiment is in contact with the anaerobic curing adhesive. Therefore, another embodiment of the present invention (the sixth embodiment) can also be said to relate to a curing promotion method for an anaerobic curing adhesive, which includes: curing the anaerobic curing adhesive while the coating film of the primer composition described in the first embodiment or the primer composition described in the second embodiment is in contact with the anaerobic curing adhesive. A preferred method for accelerating the curing of an anaerobic curing adhesive according to one embodiment includes: applying a primer composition as described in the first embodiment or the primer composition as described in the second embodiment; applying an anaerobic curing adhesive in contact with the film of the primer composition after applying the primer composition; and curing the anaerobic curing adhesive after applying the anaerobic curing adhesive. According to this method, the performance degradation (time-dependent reduction in lubrication performance) of the primer composition containing a curing accelerator and a lubricant (e.g., stamping oil) can be suppressed, and the curing speed and bond strength of the anaerobic curing adhesive can be improved. The film of the primer composition can be partially or completely dried and / or cured. The film of the primer composition can, for example, be dried and / or cured to a degree that allows for the lamination of the anaerobic curing adhesive. The curing method is described below. The method for accelerating the curing of an anaerobic curing adhesive according to one embodiment may also include other operations and / or other steps.

[0165] The anaerobic curing adhesive in the curing accelerator method described in this embodiment is the same as that described in the primer composition of the first embodiment. The preferred embodiment of the anaerobic curing adhesive in the curing accelerator method described in this embodiment is also the same as that described in the primer composition of the first embodiment. The primer composition in the curing accelerator method described in this embodiment is the same as that described in the primer composition of the first embodiment or the primer composition of the second embodiment. The preferred embodiment of the primer composition in the curing accelerator method described in this embodiment is also the same as that described in the primer composition of the first embodiment or the primer composition of the second embodiment. In one embodiment, the anaerobic curing adhesive preferably comprises components (C) to (E) described above. In one embodiment, the anaerobic curing adhesive preferably comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having an aromatic ring.

[0166] <Curing Method>

[0167] Examples of curing methods for anaerobic curing adhesives are not particularly limited, and include room temperature anaerobic curing, heated anaerobic curing, etc. By combining the primer composition described in the first method, the primer composition described in the second method, or the primer composition in the adhesive composition reagent kit described in the third method, the curing speed of the anaerobic curing adhesive can be significantly improved. Therefore, in a preferred embodiment, the anaerobic curing adhesive can sometimes be cured at room temperature. Here, the curing temperature is not particularly limited, for example, it can be a temperature in the range of 20°C to 25°C, or it can be 25°C. The curing time is not particularly limited. In a preferred embodiment, the anaerobic curing adhesive can sometimes be cured from 1 minute to 24 hours. The curing time can be, for example, 30 minutes to 2 hours.

[0168] <Method for manufacturing primer composition and method for manufacturing adhesive composition reagent package>

[0169] Another aspect (seventh aspect) of the present invention relates to a method for manufacturing a primer composition, comprising: mixing the above-described component (A) and component (B) in an amount of 35 parts by mass or less relative to 100 parts by mass of component (B). According to the primer composition manufactured by the method described in this aspect, it is possible to suppress the performance degradation (time-dependent reduction in lubrication performance) of the primer composition containing a curing accelerator and a lubricant (e.g., stamping oil) and to improve the curing speed and bond strength of the anaerobic curing adhesive. The method for manufacturing the primer composition according to one embodiment preferably comprises: mixing component (A) in an amount of 0.1 to 35 parts by mass relative to 100 parts by mass of component (B). In the method for manufacturing the primer composition according to one embodiment, the anaerobic curing adhesive preferably contains one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having an aromatic ring. One embodiment of the method for manufacturing the primer composition may further include, as needed, mixing one or more other components (one or more other components in the primer composition). Preferably, the primer composition described herein is manufactured using the method described in this embodiment.

[0170] Another aspect of the present invention (eighth aspect) relates to a method for manufacturing an adhesive composition reagent kit, the method comprising: manufacturing a primer composition by the method for manufacturing a primer composition as described above; and manufacturing an anaerobic curing adhesive. According to the adhesive composition reagent kit manufactured by the method described above, the performance degradation (degradation of lubrication performance over time) of the primer composition containing a curing accelerator and a lubricant (e.g., stamping oil) can be suppressed, and the curing speed and bond strength of the anaerobic curing adhesive can be improved. The method for manufacturing the anaerobic curing adhesive according to one embodiment may further include, as needed, mixing the components (C) to (E) above. The method for manufacturing the anaerobic curing adhesive according to one embodiment may further include, as needed, mixing one or more other components (one or more other components in the anaerobic curing adhesive). Preferably, the adhesive composition reagent kit described above is manufactured by the method for manufacturing the adhesive composition reagent kit described above.

[0171] The types and amounts of raw materials used in the anaerobic curing adhesive in the manufacturing methods described in these embodiments can be the same as those described in the description of the primer composition of the first embodiment, which specifies the types and amounts of each component. The types and amounts of raw materials used in the primer composition of the manufacturing methods described in these embodiments can be the same as those described in the description of the primer composition of the first embodiment or the primer composition of the second embodiment. Preferred embodiments of the types and amounts of raw materials used in the anaerobic curing adhesive in the manufacturing methods described in these embodiments can also be the same as those described in the description of the preferred embodiments of the types and amounts of each component of the anaerobic curing adhesive in the primer composition of the first embodiment. Preferred embodiments of the types and amounts of raw materials used in the primer composition of the manufacturing methods described in these embodiments can also be the same as those described in the description of the preferred embodiments of the types and amounts of each raw material in the primer composition of the first embodiment or the primer composition of the second embodiment.

[0172] Example

[0173] The present invention will now be described in more detail by way of examples, but the present invention is not limited to these examples.

[0174] [Examples 1-6, Comparative Examples 1-4]

[0175] <Preparation of Primer Composition>

[0176] Primer compositions of Examples 1-6 and Comparative Examples 1-3 were prepared respectively. Specifically, (A-2) was weighed in a glass container, (A-1) was added to (A-2), and the mixture was stirred for 30 minutes using a three-one motor from Shin-To Science Co., Ltd. to obtain component (A). Then, component (A) was added to component (B) and stirred for 30 minutes. It should be noted that, in the absence of (A-2), (A-1) was directly added to component (B) and stirred for 30 minutes. The detailed preparation amounts are shown in Table 1. It should be noted that in Table 1, all values ​​for the amounts of each material in the primer composition are expressed in parts by mass.

[0177] <Preparation of Anaerobic Curing Adhesives>

[0178] Components (C) to (E) and other components were weighed in a glass container and stirred for 60 minutes using a three-in-one electric motor from Shin-To Science Co., Ltd., to obtain an anaerobic curing adhesive. Specifically, components (C-1), (C-2), (C-3), (D), (E-1), (E-2), and other component (2,6-di-tert-butyl-p-cresol) were weighed and stirred for 60 minutes using a three-in-one electric motor from Shin-To Science Co., Ltd., thereby mixing these components to obtain an anaerobic curing adhesive.

[0179] It should be noted that the details of the materials used are as follows.

[0180] [Materials of the primer composition]

[0181] (A) Ingredient: Curing Accelerator

[0182] • (A-1): Copper neodecanoate (reagent)

[0183] • (A-2): Acetone (reagent)

[0184] (B) Ingredients: Lubricating oil

[0185] • Stamping fluid (manufactured by Nippon Oil Co., Ltd., G-6338F, hydrogenated petroleum fraction: 50% by mass or more)

[0186] Materials for anaerobic curing adhesives

[0187] (C) Ingredients: Compounds having one or more (meth)acryloyl groups

[0188] (Oligomers with one or more (meth)acryloyl groups in the molecule)

[0189] • (C-1): 45 parts by weight of urethane-modified acrylate with two acryloyl groups at both ends.

[0190] • (C-2): 20 parts by weight of epoxy-modified acrylate with two acryloyl groups at both ends.

[0191] (Monomers having one or more (meth)acryloyl groups in their molecules)

[0192] • (C-3): 35 parts by weight of 2-hydroxyethyl methacrylate.

[0193] Here, (C-1) is a urethane-modified acrylate with two acryloyl groups at both ends and a polyether backbone, and (C-2) is an epoxy-modified acrylate with two acryloyl groups at both ends and a bisphenol A type backbone.

[0194] (D) Ingredient: Organic peroxides

[0195] · cumene hydroperoxide, 1 part by weight

[0196] (E) Component: Anaerobic solidification catalyst

[0197] • (E-1): Saccharin, 1.5 parts by weight

[0198] • (E-2): 1-Acetyl-2-phenylhydrazine, 0.5 parts by weight

[0199] Other Ingredients

[0200] ·2,6-Di-tert-butyl-p-cresol, 0.1 parts by weight.

[0201] [Table 1]

[0202] <Evaluation of the primer composition>

[0203] The evaluations in Table 1 were conducted using the following methods.

[0204] [Maximum coefficient of friction (initial and after 30 minutes)]

[0205] 1g of each primer composition was applied to a SPCC-SD test piece measuring 25mm wide × 100mm long × 1.6mm thick, and spread with a cloth to form a test piece. A metal roller was pressed vertically onto the test piece with a load of 200N, and simultaneously rotated horizontally relative to the test piece 400 times over 30 minutes, measuring the coefficient of friction. The maximum coefficient of friction during the first 5 minutes (0-5 minutes) was taken as the initial maximum coefficient of friction, and the maximum coefficient of friction during the first 5 minutes (25-30 minutes) was taken as the maximum coefficient of friction after 30 minutes. The test was conducted using a vibration friction and wear testing machine manufactured by Shin-Tokyo Science Co., Ltd., and the test method was performed according to ASTM D6425. Preferably, the maximum coefficient of friction was 0.45 or less initially and after 30 minutes, more preferably 0.30 or less.

[0206] Shear bond strength

[0207] For SPCC-SD test pieces with a width of 25 mm × length of 100 mm × thickness of 1.6 mm, 0.1 g of each primer composition was applied, and the pieces were placed at 25°C for 1 hour to dry. Next, for the primer-treated test pieces, 0.1 g of the aforementioned anaerobic curing adhesive was applied, and the pieces were overlapped with another primer-treated test piece, with the long side end of the first piece being 10 mm long. The pieces were then fixed at 25°C for 1 hour to obtain the bonded test pieces. Next, the ends of the bonded test pieces were stretched using a universal tensile testing machine at a tensile speed of 50 mm / min, and the shear bond strength (unit: MPa) was determined according to JIS K6850 (1999). A shear bond strength of 15 MPa or higher is considered acceptable when using anaerobic curing adhesives and primer compositions. Additionally, "Not Measured" in Table 1 indicates that the maximum coefficient of friction exceeds 0.5 after 30 minutes, indicating a decrease in the performance of the stamping oil; therefore, the shear bond strength was not measured.

[0208] It should be noted that, for Comparative Example 4, the above-mentioned stamping oil was applied instead of the primer composition, and the shear bond strength was measured using the same method as described above.

[0209] In addition, without applying and drying the primer composition, an adhesion test piece was obtained using a test piece without primer treatment. Otherwise, the shear bond strength was determined using the same method as described above. In this case, the shear bond strength of the adhesion test piece was 2 MPa after being fixed at 25°C for 1 hour, and the shear bond strength of the adhesion test piece obtained after being fixed at 25°C for 24 hours was 17 MPa.

[0210] As shown in Table 1, for the primer compositions of Examples 1-6, where component (A) is 35 parts by mass or less than 100 parts by mass of component (B), the maximum coefficient of friction, a characteristic related to the properties of the stamping oil, is also good after 30 minutes, as is the shear bond strength. In particular, the primer compositions of Examples 1-4, where component (A) is 20 parts by mass or less than 100 parts by mass of component (B), show good results. On the other hand, for the primer compositions of Comparative Examples 1-3, which contain a large amount of component (A), it is shown that the maximum coefficient of friction increases significantly after 30 minutes, and the performance (lubricating properties) of the primer compositions containing curing accelerators and lubricants (such as stamping oil) decreases over time.

[0211] It should be noted that in Comparative Example 4, where only stamping oil was used without the use of a curing accelerator, no shear bond strength was observed within 1 hour of bonding with the anaerobic curing adhesive.

[0212] It has been confirmed from the above that by using the primer composition described in the first method or the primer composition described in the second method, the curing promotion and shear bond strength of the anaerobic curing adhesive are improved without causing the performance (lubricating properties) of the primer composition containing curing accelerator and lubricant (e.g., stamping oil) to decrease over time.

[0213] Industrial applicability

[0214] In this invention, the primer composition can suppress the increase in the coefficient of friction of the primer composition containing curing accelerator and lubricant (such as stamping oil) during the assembly of laminated steel sheets, and can improve the curing speed and bond strength of anaerobic curing adhesives. Therefore, it can produce laminated steel sheets more efficiently, which is very useful in industry.

[0215] This application is based on Japanese Patent Application No. 2023-213834, filed on December 19, 2023, the disclosure of which is referenced and incorporated herein by reference in its entirety.

Claims

1. A primer composition comprising component (A) and component (B), wherein component (A) comprises a (A-1) metal complex, and component (A) is 35 parts by weight or less relative to 100 parts by weight of component (B). (A) Ingredients: Curing accelerator for anaerobic curing adhesives. (B) Ingredients: Lubricating oil.

2. The primer composition according to claim 1, wherein, The amount of component (A) is 0.1 to 35 parts by mass relative to 100 parts by mass of component (B).

3. The primer composition according to claim 1, wherein, The component (A) also includes solvent (A-2).

4. The primer composition according to claim 3, wherein, The (A-2) is a ketone solvent and / or an alcohol solvent.

5. The primer composition according to any one of claims 1 to 4, wherein, The anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

6. The primer composition according to any one of claims 1 to 4, used for assembling laminated steel sheets.

7. The primer composition according to any one of claims 1 to 4, wherein, The component (B) is a stamping oil.

8. A method for manufacturing a laminate, comprising: Apply the primer composition according to any one of claims 1 to 4 to the substrate; Applying an anaerobic curing adhesive to the substrate, a coating of the primer composition, or both; and After the primer composition is applied and the anaerobic curing adhesive is applied, the substrate is bonded to the substrate to be bonded, and then the anaerobic curing adhesive is cured.

9. The manufacturing method according to claim 8, wherein, The anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

10. A method for manufacturing laminated steel plates, comprising the following steps 1 to 4, Step 1: Apply the primer composition according to any one of claims 1 to 4 to the strip steel plate; Step 2: The strip steel plate coated with the primer composition is punched into a specified shape to obtain a thin steel plate coated with the primer composition; Step 3: Apply the anaerobic curing adhesive in a surface or dot pattern to the steel sheet coated with the primer composition, and then laminate the steel sheet with the steel sheet to be bonded. Step 4: The anaerobic curing adhesive is cured under specified conditions to obtain laminated steel plates.

11. The manufacturing method according to claim 10, wherein, The anaerobic curing adhesive comprises one or more compounds selected from urethane-modified (meth)acrylates, epoxy-modified (meth)acrylates, and (meth)acrylates having aromatic rings.

12. An adhesive composition kit comprising an anaerobic curing adhesive and a primer composition according to any one of claims 1 to 4.

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