Deprecated: The each() function is deprecated. This message will be suppressed on further calls in /home/zhenxiangba/zhenxiangba.com/public_html/phproxy-improved-master/index.php on line 456
WO2025197894A1 - Procédé de production de stratifié de feuilles d'acier, stratifié de feuilles d'acier, et composition adhésive - Google Patents
[go: Go Back, main page]

WO2025197894A1 - Procédé de production de stratifié de feuilles d'acier, stratifié de feuilles d'acier, et composition adhésive - Google Patents

Procédé de production de stratifié de feuilles d'acier, stratifié de feuilles d'acier, et composition adhésive

Info

Publication number
WO2025197894A1
WO2025197894A1 PCT/JP2025/010394 JP2025010394W WO2025197894A1 WO 2025197894 A1 WO2025197894 A1 WO 2025197894A1 JP 2025010394 W JP2025010394 W JP 2025010394W WO 2025197894 A1 WO2025197894 A1 WO 2025197894A1
Authority
WO
WIPO (PCT)
Prior art keywords
steel sheet
meth
acrylate
mass
sheet laminate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/010394
Other languages
English (en)
Japanese (ja)
Inventor
智洋 緑川
拓馬 川島
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cemedine Co Ltd
Original Assignee
Cemedine Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cemedine Co Ltd filed Critical Cemedine Co Ltd
Priority to JP2025543247A priority Critical patent/JP7757573B1/ja
Publication of WO2025197894A1 publication Critical patent/WO2025197894A1/fr
Priority to JP2025170103A priority patent/JP2025182122A/ja
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined

Definitions

  • the present invention relates to a method for manufacturing a steel sheet laminate, a steel sheet laminate, and an adhesive composition.
  • Steel sheet laminates manufactured by laminating steel sheets, particularly electromagnetic steel sheets, are used in applications such as motor rotors and stators installed in various devices.
  • Steel sheet laminates are typically assembled by caulking or welding.
  • curable resins such as epoxy resin adhesives and curable acrylic adhesives are commonly used as adhesives.
  • curable acrylic adhesives are often used when room-temperature curing is desired.
  • Patent Document 1 describes the production of a steel sheet laminate using an anaerobic adhesive (a type of curing acrylic adhesive) and steel sheets whose surfaces are coated with press processing oil containing copper soap as a curing accelerator.
  • Patent Document 2 describes a method in which a pretreatment agent for accelerating the curing of an anaerobic adhesive containing a chelate compound of copper, vanadium, chromium, manganese, iron, titanium, nickel, or cobalt as an active ingredient is applied to a metal bolt/nut, and then an anaerobic adhesive containing a (meth)acrylate compound is applied to fix the bolt/nut, etc.
  • Patent Document 3 describes a method in which a curing accelerator for a (meth)acrylic curable composition containing a copper and/or vanadium chelate compound is applied to a metal bolt/nut, and then an anaerobic adhesive containing a (meth)acrylate compound is applied to fix the bolt/nut, etc.
  • Patent Document 4 describes a method in which an anaerobic adhesive composition containing an anaerobically polymerizable acrylic acid ester monomer, an organic peroxide, and a phosphoric acid compound having a (meth)acryloyl group is applied to the inner wall and/or shaft of a ring, and the shaft is inserted into the ring and fitted to be fixed.
  • Patent Document 5 describes the use of a polymerizable adhesive composition containing a polymerizable olefinically unsaturated monomer compound, a phosphoric acid compound having at least one olefinically unsaturated group, and an organic peroxide for bonding steel to steel and aluminum to aluminum.
  • Patent Document 6 describes a composition comprising: (A) component: a radical polymerizable compound; (B) component: a radical polymerization initiator; and (C) component: a compound represented by the following formula (1) or (2): -O-P(O)(OH)-O-...(1) -O-P(O)(OH) 2 ...(2)
  • the present invention discloses a radically polymerizable adhesive composition for bonding steel sheet laminates, which comprises a phosphoric acid ester compound having a group represented by the formula:
  • the adhesive compositions described in Patent Documents 1 to 6 are capable of producing steel sheet laminates with excellent adhesive strength, but they have insufficient curing speeds, and require a long time for completion of adhesion and formation of a steel sheet laminate, resulting in poor workability.
  • the problem to be solved by the present invention is to provide a method for producing a steel sheet laminate which can produce a steel sheet laminate having excellent adhesive strength, in which the adhesive has a sufficiently fast curing rate, the time required for completing bonding and forming the steel sheet laminate is short, and the method has good workability.
  • Another problem that the present invention aims to solve is to provide an adhesive composition for steel sheet laminates, which can produce steel sheet laminates with excellent adhesive strength, has a sufficiently fast curing rate, requires a short time for completion of bonding and construction of a steel sheet laminate, and has good workability.
  • the present inventors have found that the above-mentioned problems can be solved by a method for producing a steel sheet laminate using a specific adhesive composition, and by the steel sheet laminate and specific adhesive composition obtained thereby, and have thus completed the present invention.
  • [Item 1] A method for producing a steel sheet laminate, in which steel sheets coated with a primer containing a copper compound are bonded using a radical-polymerizable adhesive composition containing (A) a radical-polymerizable compound, (B) an organic peroxide, and (C) a phosphate ester compound having a radical-polymerizable group, wherein the amount of (C) the phosphate ester compound having a radical-polymerizable group is 0.055 parts by mass or more and less than 1 part by mass per 100 parts by mass of the (A) radical-polymerizable compound.
  • [Item 2] A steel sheet laminate produced by the method according to Item 1.
  • An adhesive composition for a steel sheet laminate that bonds steel sheets coated with a primer containing a copper compound comprising: (A) a radically polymerizable compound, (B) an organic peroxide, and (C) a phosphate ester compound having a radically polymerizable group,
  • the present invention provides a method for producing a steel sheet laminate that can produce a steel sheet laminate with excellent adhesive strength, has a sufficiently fast curing rate of the adhesive, requires a short time to complete bonding and form the steel sheet laminate, and is easy to work with.
  • the present invention also provides an adhesive composition for steel sheet laminates that can produce steel sheet laminates with excellent adhesive strength, has a sufficiently fast curing rate, requires a short time for completion of bonding and construction of a steel sheet laminate, and has good workability.
  • the method for producing a steel sheet laminate and the adhesive composition for a steel sheet laminate according to the present invention can simplify the manufacturing process of a steel sheet laminate, can reduce iron loss in the steel sheet laminate, and contribute to improving the performance and reliability of motor rotors and stators.
  • the adhesive composition for steel sheet laminates of the present invention exhibits excellent adhesive strength to steel sheets whose surfaces have been treated with punching oil, in particular to electrical steel sheets and cold-rolled steel sheets (SPCC-SD), and is capable of providing strong adhesion without removing the punching oil applied to the steel sheets in the process of producing the steel sheet laminate, making it extremely useful from an industrial perspective.
  • SPCC-SD electrical steel sheets and cold-rolled steel sheets
  • FIG. 1 is a schematic diagram of a manufacturing apparatus for a steel sheet stack according to an embodiment of the present invention.
  • (meth)acrylic means “acrylic” and “methacrylic
  • (meth)acrylate means “acrylate” and “methacrylate”
  • (meth)acryloyl means “acryloyl” and “methacryloyl”, respectively.
  • the method for producing a steel sheet laminate of the present invention involves bonding steel sheets coated with a primer containing a copper compound using a radical-polymerizable adhesive composition containing (A) a radical-polymerizable compound, (B) an organic peroxide, and (C) a phosphate ester compound having a radical-polymerizable group.
  • the radical-polymerizable adhesive composition contains (C) the phosphate ester compound having a radical-polymerizable group in an amount of 0.055 parts by mass or more and less than 1 part by mass per 100 parts by mass of the (A) radical-polymerizable compound.
  • the radically polymerizable compound (A) contained in the radically polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention is at least one selected from the group consisting of radically polymerizable monomers, radically polymerizable oligomers, and radically polymerizable polymers having a radically polymerizable functional group, particularly a radically polymerizable ethylenically unsaturated group.
  • the radically polymerizable compound (A) is a radically polymerizable compound other than the phosphate ester compound (C) having a radically polymerizable group, which will be described later.
  • the radically polymerizable functional group include a (meth)acryloyl group, a vinyl group, an allyl group, and a (meth)acrylamide group. Of these, a (meth)acryloyl group is preferred.
  • (A) From the viewpoint of adhesive strength to steel sheets, particularly electromagnetic steel sheets, having punching oil components applied to the surface, it is preferable to use one or more radically polymerizable oligomers and/or radically polymerizable polymers as the radically polymerizable compound. Furthermore, from the viewpoint of exhibiting better adhesive strength to steel sheets such as cold-rolled steel sheets and electromagnetic steel sheets, adjusting the viscosity of the adhesive composition to facilitate easy handling, and preventing adhesive from squeezing out when laminating steel sheets, it is preferable to use one or more radically polymerizable oligomers and/or radically polymerizable polymers in combination with one or more radically polymerizable monomers.
  • radically polymerizable oligomer and/or radical polymer examples include one or more selected from the group consisting of urethane (meth)acrylate, epoxy (meth)acrylate, bisphenol alkylene oxide adduct (meth)acrylate, ether (meth)acrylate, ester (meth)acrylate, isoprene-based (meth)acrylate, hydrogenated isoprene-based (meth)acrylate, (meth)acrylic group-containing acrylic polymer, (meth)acrylic group-containing polyisobutylene, etc.
  • urethane (meth)acrylate epoxy (meth)acrylate, bisphenol alkylene oxide adduct (meth)acrylate, ether (meth)acrylate, ester (meth)acrylate, isoprene-based (meth)acrylate, hydrogenated isoprene-based (meth)acrylate, (meth)acrylic group-containing acrylic polymer, (meth)acrylic group-containing polyisobut
  • urethane (meth)acrylate epoxy (meth)acrylate, bisphenol alkylene oxide adduct (meth)acrylate, and ether (meth)acrylate because of their excellent adhesive strength to cold-rolled steel sheets and/or electromagnetic steel sheets, and the high glass transition temperature of the cured product.
  • the urethane (meth)acrylate can be obtained by reacting at least a polyol component, a polyisocyanate component, and a compound having a (meth)acrylate group.
  • the polyol component may include, for example, one or more polymer polyols selected from the group consisting of (hydrogenated) butadiene polyols, polycarbonate polyols, polyether polyols, polyester polyols, polyacrylate polyols (acrylic polyols), polyurethane polyols, and the like.
  • polyisocyanate component for example, one or more selected from the group consisting of aliphatic polyisocyanates (hexamethylene diisocyanate, etc.), alicyclic polyisocyanates (dicyclohexylmethane diisocyanate, isobornyl diisocyanate, etc.), aromatic polyisocyanates (toluene diisocyanate, diphenylmethane diisocyanate, etc.), and araliphatic polyisocyanates (xylylene diisocyanate, etc.) can be used.
  • aliphatic polyisocyanates hexamethylene diisocyanate, etc.
  • alicyclic polyisocyanates dicyclohexylmethane diisocyanate, isobornyl diisocyanate, etc.
  • aromatic polyisocyanates toluene diisocyanate, diphenylmethane diisocyanate, etc.
  • the compound having a (meth)acrylate group for example, one or more compounds selected from the group consisting of (meth)acrylate group-containing compounds having a group reactive with an isocyanate group (hydroxyalkyl (meth)acrylate, acrylic acid, etc.) and isocyanate group-containing (meth)acrylate group-containing compounds can be used.
  • urethane (meth)acrylates include one or more selected from the group consisting of urethane (meth)acrylates having a (hydrogenated) polybutadiene skeleton, urethane (meth)acrylates having a polycarbonate skeleton, urethane (meth)acrylates having a polyether skeleton, urethane (meth)acrylates having a polyester skeleton, urethane (meth)acrylates having a polyacrylate skeleton, urethane (meth)acrylates having a polyurethane skeleton, and urethane (meth)acrylates having a castor oil skeleton.
  • Epoxy (meth)acrylate can be obtained by reacting an epoxy resin with a (meth)acrylate compound having a functional group reactive with an epoxy group.
  • the epoxy resin include at least one selected from the group consisting of bisphenol-type epoxy resins (bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, etc.), phenol novolac-type epoxy resins, and epoxy resins such as terminal glycidyl ethers of alkylene oxide adducts of bisphenol-type epoxy resins.
  • Examples of the (meth)acrylate compound having a functional group reactive with an epoxy group include one or more compounds selected from the group consisting of (meth)acrylate compounds having a carboxyl group such as (meth)acrylic acid, and (meth)acrylate compounds having a hydroxyl group such as hydroxyethyl (meth)acrylate.
  • epoxy (meth)acrylates can be used, including, for example, one or more selected from the group consisting of DICLITE (registered trademark) UE-8071-60BH, UE-8740, and UE-8410 (manufactured by DIC Corporation), Kayard R-115F (manufactured by Nippon Kayaku Co., Ltd.), HITAROID 7851 (manufactured by Showa Denko K.K.), Epoxy Ester 3000MK and 3000A (manufactured by Kyoeisha Chemical Co., Ltd.), Viscoat V#540 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), EBECRYL 600, and EBECRYL 3700 (manufactured by Daicel Allnex Corporation).
  • Examples of the bisphenol alkylene oxide adduct (meth)acrylate include those represented by the following formula (A): (In formula (A), R 11 is a hydrogen atom or a methyl group. R 12 is a hydrogen atom or a methyl group.
  • a 1 is an alkylene group having 1 to 6 carbon atoms, and when there are a plurality of A 1 s, they may be different from each other.
  • A2 is an alkylene group having 1 to 6 carbon atoms, and when there are a plurality of A2s, they may be different from each other.
  • X is any one of a direct bond, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —O—, —S—, —SO 2 —, —CO—, —CF 2 —, —C(CF 3 ) 2 —, —C(Ph) 2 —, and —CH(Ph)— (Ph is a phenyl group).
  • m is an integer of 0 or 1 or more.
  • n is an integer of 0 or 1 or more.
  • one or more compounds selected from the group consisting of (poly)ethoxy-modified bisphenol A di(meth)acrylate, (poly)propoxy-modified bisphenol A di(meth)acrylate, etc. may be used.
  • (poly)ethoxy-modified bisphenol A di(meth)acrylate is preferred, and particularly preferred is a compound represented by the above formula (A) in which R 11 is a hydrogen atom or a methyl group, R 12 is a hydrogen atom or a methyl group, A 1 and A 2 are alkylene groups having 2 carbon atoms, X is -C(CH 3 ) 2 -, and m+n (i.e., ethoxy equivalent) is 1 to 40 (preferably 2 to 10).
  • the radical polymerizable monomer is not particularly limited as long as it is a compound having one or more radical polymerizable groups in the molecule, is not an oligomer or a polymer, and is a radical polymerizable compound other than the (C) phosphate ester compound having a radical polymerizable group, and examples thereof include one or more types selected from the group consisting of monofunctional monomers, polyfunctional monomers, etc.
  • a monofunctional monomer having a functional group such as a hydroxyl group, a carboxyl group, an amino group, or a glycidyl group, since this allows the formation of a radical polymerizable adhesive composition for steel sheet laminates that has even better adhesion to steel sheets such as cold-rolled steel sheets and electromagnetic steel sheets and that forms a cured product with a high glass transition point.
  • monofunctional monomers examples include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, hexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, and benzyl (meth)acrylate.
  • one or more selected from the group consisting of dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, etc. are preferred.
  • polyfunctional monomers examples include 1,3-butylene glycol di(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, ethylene oxide-modified neopentyl glycol di(meth)acrylate, propylene oxide-modified neopentyl glycol di(meth)acrylate, hydroxypivalic acid ester neopentyl glycol diacrylate, caprolactone-modified hydroxypivalic acid ester neopentyl glycol diacrylate, neopentyl glycol-modified trimethylolpropane di(meth)acrylate, stearic acid-modified
  • dicyclopentenyl di(meth)acrylate ethylene oxide-modified dicyclopentenyl di(meth)acrylate, di(meth)acryloyl isocyanurate, dimethyloltricyclodecane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(acryloyloxyethyl)isocyanurate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol monohydroxypenta(meth)acrylate, etc.
  • the amount of (A) radically polymerizable compound blended is, for example, 90% by mass or more, preferably 95% by mass or more, and for example, 99% by mass or less, preferably 98% by mass or less, based on 100% by mass of the total amount of the radically polymerizable adhesive composition.
  • the (B) organic peroxide contained in the radical polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention is intended to impart anaerobic curability and/or heat curability to the radical polymerizable adhesive composition.
  • Examples of (B) organic peroxides include one or more selected from the group consisting of hydroperoxides such as cumene hydroperoxide, t-butyl hydroperoxide, p-menthane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, diisopropylbenzene hydroperoxide, and others, as well as ketone peroxides, diallyl peroxides, peroxy esters, etc.
  • hydroperoxides are preferably used from the viewpoint that the radically polymerizable adhesive composition for bonded steel sheet laminates will have even better reactivity and storage stability.
  • the (B) organic peroxide is preferably an organic peroxide having a one-hour half-life temperature of 80° C. or higher, preferably 100° C. or higher, and 300° C. or lower, preferably 200° C. or lower.
  • the one-hour half-life temperature is a value measured by thermal decomposition at a concentration of 0.1 mol/L of the organic peroxide in benzene.
  • Examples of organic peroxides having a one-hour half-life temperature in the range of 80° C. to 300° C. include hydroperoxides.
  • hydroperoxides include one or more selected from the group consisting of p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, and t-butyl hydroperoxide.
  • the amount of (B) organic peroxide blended is, for example, 0.05 parts by mass or more, preferably 0.1 parts by mass or more, and for example, 10 parts by mass or less, preferably 5 parts by mass or less, per 100 parts by mass of (A) radical polymerizable compound.
  • (B) organic peroxide in the range of 0.05 parts by mass or more and 10 parts by mass or less per 100 parts by mass of (A) radical polymerizable compound, the adhesive strength of the radical polymerizable adhesive composition can be improved.
  • the radically polymerizable adhesive composition (C) used in the method for producing a steel sheet laminate of the present invention contains a phosphate ester compound having a radically polymerizable group, which compound has a radically polymerizable functional group and a phosphate ester compound represented by the following formula (1) or (2): -O-P(O)(OH)-O-...(1) -O-P(O)(OH) 2 ...(2)
  • the use of (A) a radically polymerizable compound and (B) an organic peroxide in combination has the remarkable effect of providing a radically polymerizable adhesive composition for steel sheet laminates that exhibits adhesive strength to steel sheets the surfaces of which are covered with punching oil.
  • the phosphate ester compound having a radical polymerizable group is not particularly limited, but examples include one or more compounds selected from the group consisting of 2-hydroxymethyl (meth)acrylate acid phosphate, 2-hydroxyethyl (meth)acrylate acid phosphate, 2-hydroxypropyl (meth)acrylate acid phosphate, ethylene oxide-modified phosphate di(meth)acrylate, ethylene oxide-modified phosphate tri(meth)acrylate, and caprolactone-modified ethylene oxide-modified phosphate di(meth)acrylate.
  • the phosphate ester compound having a radical polymerizable group may be synthesized or a commercially available product.
  • commercially available products include one or more selected from the group consisting of Light Ester P-A, P-1M, and P-2M (all manufactured by Kyoeisha Chemical Co., Ltd.), Kayamar PM-1 (manufactured by Nippon Kayaku Co., Ltd.), and JPA-514 (manufactured by Johoku Chemical Industry Co., Ltd.).
  • the amount of the (C) phosphate ester compound having a radical polymerizable group is 0.055 parts by mass or more but less than 1 part by mass, preferably 0.06 parts by mass or more, more preferably 0.065 parts by mass or more, even more preferably 0.07 parts by mass or more, and preferably 0.8 parts by mass or less, more preferably 0.7 parts by mass or less, per 100 parts by mass of the (A) radical polymerizable compound.
  • the amount of the phosphate ester compound having a radical polymerizable group (C) is 1 part by mass or more, the tensile shear bond strength will be high and the adhesiveness will be excellent, but the setting time will be long and the curing rate will be slow. If the amount is less than 0.055 parts by mass, the setting time will be short and the curing rate will be fast, but the tensile shear bond strength will be low and the adhesiveness will be poor.
  • the radically polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention preferably further contains (D) an anaerobic curing catalyst.
  • the anaerobic curing catalyst (D) may be at least one selected from the group consisting of imide compounds, amine compounds, azole compounds, mercaptan compounds, hydrazine compounds, etc. Among these, imide compounds are preferred from the viewpoint of improving anaerobic curing properties.
  • the imide-based compound is represented by the following formula (3) or (4): -CONHCO-...(3) -CONHSO 2 -...(4) or a salt thereof.
  • the imide-based compound include one or more selected from the group consisting of o-benzoic acid sulfimide (saccharin), succinimide, phthalimide, and salts thereof (particularly alkali metal salts such as sodium and potassium).
  • Amine compounds include, for example, one or more compounds selected from the group consisting of heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine, heterocyclic tertiary amines such as quinoline, methylquinoline, quinaldine and quinoxalinephenazine, and aromatic tertiary amines such as N,N-dimethyl-anisidine and N,N-dimethylaniline.
  • heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine
  • heterocyclic tertiary amines such as quinoline, methylquinoline, quinaldine and quinoxalinephenazine
  • aromatic tertiary amines such as N,N-dimethyl-anisidine and N,N-dimethylaniline.
  • Azole compounds include, for example, one or more compounds selected from the group consisting of 1,2,4-triazole, oxazole, oxadiazole, thiadiazole, benzotriazole, hydroxybenzotriazole, benzoxazole, 1,2,3-benzothiadiazole, and 3-mercaptobenzotriazole.
  • mercaptan compounds include one or more compounds selected from the group consisting of linear mercaptans such as n-dodecyl mercaptan, ethyl mercaptan, and butyl mercaptan.
  • hydrazine compounds include one or more selected from the group consisting of 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-carbohydrazine, 1-formyl-2-phenylhydrazine, 1-acetyl-2-(p-bromophenyl)hydrazine, 1-acetyl-2-(p-nitrophenyl)hydrazine, 1-acetyl-2-(p-methoxyphenyl)hydrazine, 1-acetyl-2-(2'-phenylethylhydrazine), p-nitrophenylhydrazine, p-trisulfonylhydrazide, 1-acetyl-2-methylhydrazine, 1-pheny
  • the amount of (D) anaerobic curing catalyst is not particularly limited, as long as it does not impair the properties of the radical polymerizable adhesive composition, such as ease of handling, adhesive strength, rapid curing, or storage stability. It is, for example, 0.1 part by mass or more, preferably 0.5 part by mass or more, and for example, 5 parts by mass or less, preferably 3 parts by mass or less, per 100 parts by mass of (A) radical polymerizable compound.
  • the radical polymerizable adhesive composition can be made to have excellent anaerobic curing properties and storage stability.
  • the radically polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention preferably further contains (E) a storage stabilizer, such as one or more selected from the group consisting of polymerization inhibitors (radical scavengers, metal chelating agents), antioxidants, etc.
  • a storage stabilizer such as one or more selected from the group consisting of polymerization inhibitors (radical scavengers, metal chelating agents), antioxidants, etc.
  • polymerization inhibitors include one or more metal chelating agents selected from the group consisting of ethylenediaminetetraacetic acid, its di-sodium salt, its 4-sodium salt, oxalic acid, acetylacetone, o-aminophenol, etc.; one or more quinone compounds selected from the group consisting of hydroquinone, benzoquinone, hydroquinone monomethyl ether, ⁇ -naphthoquinone, 2-methoxy-1,4-naphthoquinone, methylhydroquinone, hydroquinone monomethyl ether, mono-tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, p-benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-di-tert-butyl-p-benzoquinone, etc.; pentaerythritol tetrakis(3
  • the amount of (E) storage stabilizer added is not particularly limited. It can be, for example, 7 parts by mass or less, and preferably 0.001 to 5 parts by mass, per 100 parts by mass of (A) (meth)acrylic polymerizable monomer.
  • the radically polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention may contain (F) other components in addition to (A) the radically polymerizable compound, (B) the organic peroxide, (C) the phosphate ester compound having a radically polymerizable group, (D) the anaerobic curing catalyst, and (E) the storage stabilizer, to the extent that the functions of the adhesive composition, such as curability and adhesiveness of the cured product, are not impaired.
  • Examples of the (F) other components include one or more selected from the group consisting of organic fillers (elastomers, thermoplastic resins, thermosetting resins, etc.), inorganic fillers, silane coupling agents, curing rate modifiers, plasticizers, antifoaming agents, heavy metal deactivators, adhesives and/or tackifiers, antioxidants, light stabilizers, reinforcing agents, colorants, flame retardants, rust inhibitors, dispersants, thixotropic agents, anti-precipitation agents, antioxidants, light stabilizers, ultraviolet absorbers, fragrances, and the like.
  • organic fillers elastomers, thermoplastic resins, thermosetting resins, etc.
  • silane coupling agents e.g., silane coupling agents, curing rate modifiers, plasticizers, antifoaming agents, heavy metal deactivators, adhesives and/or tackifiers
  • antioxidants light stabilizers, reinforcing agents, colorants, flame retardants, rust inhibitors, dis
  • organic fillers include one or more selected from the group consisting of polyethylene, polypropylene, polyamide, cross-linked acrylic, cross-linked polystyrene, polyester, polyvinyl alcohol, polyvinyl butyral, polycarbonate, epoxy resin, and various rubbers and elastomers (diene-based rubbers, olefin-based elastomers, urethane-based elastomers, silicone-based elastomers, etc.).
  • inorganic fillers include one or more selected from the group consisting of glass, silica, alumina, mica, ceramics, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, dried clay minerals, dried diatomaceous earth, etc.
  • Silane coupling agents are used as adhesion promoters.
  • the silane coupling agent include ⁇ -chloropropyltrimethoxysilane, octenyltrimethoxysilane, glycidoxyoctyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ -aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl- ⁇ -aminopropyltrimethoxysilane,
  • the tensile shear adhesive strength of the radically polymerizable adhesive composition of the present invention is, for example, 2.0 N/ mm2 or more, and preferably 3.0 N/mm2 or more .
  • the tensile shear adhesive strength can be obtained by the method described in the Examples below.
  • the setting time of the radically polymerizable adhesive composition of the present invention is, for example, less than 300 seconds, preferably less than 250 seconds, and more preferably less than 180 seconds.
  • the setting time can be obtained by the method described in the Examples below.
  • the glass transition point of the cured product of the radically polymerizable adhesive composition of the present invention is, for example, 60° C. or higher, preferably 70° C. or higher, from the viewpoint of the heat resistance of the steel sheet laminate.
  • the glass transition temperature can be determined, for example, by the following method.
  • a mixture of 100 parts by mass of a radically polymerizable adhesive composition and 0.3 parts by mass of the primer described below is poured between two PET films spaced 1 mm apart to produce a cured product.
  • a sample of 10 mm width x 40 mm length is cut out from the obtained cured product, and measurement is performed using a DMS6100 manufactured by Seiko Instruments Inc. in a tensile mode at a temperature range of 25°C to 350°C, a heating rate of 5°C/min, and a frequency of 1 Hz to determine the peak value of tan ⁇ , which is taken as the glass transition point.
  • the viscosity of the radical polymerizable adhesive composition used in the method for producing a steel sheet laminate of the present invention is not particularly limited. From the viewpoints of ease of handling and prevention of extrusion during adhesion, the viscosity may be, for example, 0.01 Pa s or more, preferably 0.05 Pa s or more, and more preferably 0.5 Pa s or more, and may be, for example, 50 Pa s or less, preferably 30 Pa s or less, and more preferably 15 Pa s or less.
  • the viscosity can be adjusted by a viscosity adjusting method known in the adhesive field, such as blending a viscosity adjuster (thixotropic agent).
  • the viscosity can be obtained, for example, by putting 100 g of the radically polymerizable adhesive composition into a bottle, discharging it into a measuring cup, and measuring the viscosity using a Brookfield viscometer (manufactured by Toki Sangyo Co., Ltd.) at 25°C and a rotation speed of 60 rpm.
  • a Brookfield viscometer manufactured by Toki Sangyo Co., Ltd.
  • the method for producing the radical polymerizable adhesive composition used in the method for producing the steel sheet laminate of the present invention is not particularly limited.
  • the composition can be produced by adding predetermined amounts of at least (A) the radical polymerizable compound, (B) the organic peroxide, and (C) the phosphate ester compound having a radical polymerizable group to a mixing vessel in any order and mixing them.
  • a mixing device such as a mixer (rotating/revolving mixer, planetary mixer, etc.), a tumbler, a stirrer, an agitator, a mechanical homogenizer, an ultrasonic homogenizer, a high-pressure homogenizer, a shaker, a V-type blender, or a Nauta mixer can be used, and it is preferable to use a mixer.
  • the mixing conditions are not particularly limited.
  • the temperature conditions can be, for example, 0° C. or higher, preferably 10° C. or higher, and for example, 100° C. or lower, more preferably 70° C. or lower.
  • the mixing time can be, for example, 1 minute or longer, preferably 5 minutes or longer, and for example, 10 hours or shorter, preferably 5 hours or shorter.
  • the primer used in the method for producing the steel sheet laminate of the present invention contains a copper compound.
  • the primer may contain, in addition to the copper compound, oil, solvent, rust inhibitor, preservative, and the like.
  • copper compounds include one or more selected from the group consisting of copper salts of carboxylic acids such as copper neodecanoate, copper 2-ethylhexanoate, copper naphthenate, copper octenoate, copper hexanoate, copper propionate, and copper 2,4-pentadionate (copper acetylacetonate); copper complexes such as copper ethylenediamine and copper propylenediamine; and others.
  • carboxylic acids such as copper neodecanoate, copper 2-ethylhexanoate, copper naphthenate, copper octenoate, copper hexanoate, copper propionate, and copper 2,4-pentadionate (copper acetylacetonate)
  • copper complexes such as copper ethylenediamine and copper propylenediamine; and others.
  • the oil that can be used includes punching oil, mineral oil, synthetic oil, animal and vegetable oil, etc.
  • the process of punching steel sheets into a desired shape and the process of stacking the punched steel sheets to form a steel sheet laminate are carried out consecutively, so it is preferable that the primer contains punching oil.
  • punching oil By including punching oil, it is possible to prevent galling, seizure, and other problems from occurring when the steel sheets are processed in various ways.
  • the solvent may be one or more organic solvents and/or water.
  • organic solvent examples include one or more selected from the group consisting of aliphatic hydrocarbon organic solvents having 5 to 40 carbon atoms (hexane, heptone, paraffin, etc.); alicyclic hydrocarbon solvents having 5 to 20 carbon atoms; aromatic hydrocarbon solvents having 6 to 20 carbon atoms (benzene, toluene, xylene, ethylbenzene, indene, etc.); alcohol solvents having 1 to 10 carbon atoms (methanol, ethanol, propanol, isopropanol, hexanol, etc.); ketone solvents having 3 to 20 carbon atoms (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.); ether solvents having 2 to 20 carbon atoms (tetrahydrofuran, diethyl ether, dioxan
  • the composition of the primer is not particularly limited.
  • the copper compound content is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and for example, 15.0% by mass or less, preferably 10.0% by mass or less, and more preferably 8.0% by mass or less, when the total amount of the primer is taken as 100% by mass.
  • the oil content is, for example, 20.0% by mass or more, preferably 25.0% by mass or more, more preferably 30.0% by mass or more, and for example, 80.0% by mass or less, preferably 70.0% by mass or less, and more preferably 60.0% by mass or less, when the total amount of the primer is taken as 100% by mass.
  • the solvent is used in an amount that makes the total amount 100% by mass.
  • the steel sheet used in the method for producing the steel sheet laminate of the present invention is not particularly limited. Various steel sheets can be used depending on the application, etc. In the present invention, steel sheets that are distributed in a rolled state can be used as they are without degreasing.
  • Steel sheets include, for example, various types of iron steel sheets. Of these, cold-rolled steel sheets, electromagnetic steel sheets, etc. are preferably used. In the present invention, electromagnetic steel sheets are preferably steel sheets that utilize the electromagnetic properties of steel sheets and are used primarily for components such as motor rotors and stators.
  • the thickness of the steel plate is not particularly limited and can be determined appropriately depending on the application, etc. For example, it is 0.01 mm or more, preferably 0.1 mm or more, and for example, 5 mm or less, preferably 3 mm or less, and more preferably 1 mm or less. Furthermore, there are no particular limitations on the thickness of the cured radical polymerizable adhesive composition layer in the steel plate laminate.
  • the shape of the steel sheets to be laminated is not particularly limited.
  • an electromagnetic steel sheet laminate can be formed by laminating, for example, two or more, preferably five or more, strip-shaped electromagnetic steel sheets punched into a predetermined shape.
  • FIG. 1 shows an embodiment of a steel sheet stack manufacturing apparatus used in the method for manufacturing a steel sheet stack according to the present invention.
  • a steel plate laminate manufacturing apparatus 1 in a steel plate laminate manufacturing apparatus 1, a steel strip 3 is unwound from a steel strip roll 2.
  • a primer containing punching oil is applied to one side of the steel strip 3 by a primer application device 4A, and an adhesive is applied to the other side of the steel strip 3 by an adhesive application device 4B. After that, the steel strip 3 is introduced into a press molding device 5.
  • the press molding device 5 by providing punching units 6A, 6B, 6C, 6D, and 6E for punching inner diameters/holes/slots, etc., as necessary, it is possible to perform one or more of punching processes for inner diameters, holes, slots, etc. on the steel strip 3. Note that the order of punching inner diameters, holes, slots, etc. is not particularly limited. After punching the inner diameters, holes, slots, etc., the steel strip 3 is punched into steel plate laminate forming members by an outer diameter punching punch unit 7 in the press molding device 5.
  • the punched steel plate laminate forming members are stored in a steel plate laminate forming member storage and holding section 8, and the primer layer and adhesive layer come into contact with each other to adhere the steel plate laminate forming members one by one, and a predetermined number of sheets are stacked and adhered together to produce a steel plate laminate 9.
  • the obtained steel plate laminate 9 is taken out from the steel plate laminate forming member storage and holding section 8.
  • a heat treatment may be carried out using a thermostatic bath, a far-infrared heater, or the like, for the purpose of heating to ensure curing of the adhesive.
  • the heating conditions at this time may be, for example, a temperature of 40° C. or higher and 300° C. or lower, and a time of 10 minutes to 5 hours.
  • a primer and an adhesive are simultaneously applied to the strip steel plate 3 by a primer application device 4A and an adhesive application device 4B, but the adhesive application device 4B can be provided upstream of the outer diameter punching section 7 (at any position before the outer diameter punching is performed).
  • the surfaces of each punch section 6A, 6B, 6C, 6D, 6E, 7 that punch out the strip steel plate 3 and the surfaces of the components that make up the conveying line for the strip steel plate 3 may be subjected to surface treatment (anti-adhesion treatment) to prevent the primer and/or radical polymerizable adhesive composition applied to the strip steel plate 3 from adhering.
  • a primer containing punching oil in order to improve the workability of the punching process and prevent galling, seizure, and the like.
  • punch units 6A, 6B, 6C, 6D, and 6E are provided as punch units for punching inner diameters/holes/slots, etc., but the number of punch units can be increased or decreased as needed. For example, the number of punch units can be increased to improve punching accuracy.
  • the positions of the primer applicator 4A and the adhesive applicator 4B are not particularly limited.
  • the primer applicator 4A may be provided below the steel strip 3.
  • the coating method in the primer coating device 4A and the adhesive coating device 4B is not particularly limited. For example, one or more coating methods including roller coating, dispensing coating, spray coating, inkjet coating, dipping, brush coating, etc. may be used.
  • the steel plate stack manufacturing apparatus 1 shown in Figure 1 instead of unwinding the strip steel plate 3 from the strip steel plate roll 2, it is also possible to continuously supply steel plates that have been pre-formed into a predetermined shape to manufacture a steel plate stack.
  • the steel sheet laminate of the present invention is obtained by the [Method for Producing a Steel Sheet Laminate].
  • the steel sheet laminate is preferably formed using electrical steel sheets coated with a primer containing a copper compound and a radically polymerizable adhesive composition, or the steel sheet laminate is preferably formed using electrical steel sheets punched into a predetermined shape from a strip steel sheet.
  • the thickness of the steel sheets used in the steel sheet laminate is not particularly limited, and is, from the viewpoint of the need for thinner steel sheet laminates in line with the miniaturization of motors and the like, in the range of, for example, 0.01 mm or more, preferably 0.1 mm or more, and for example, 3.0 mm or less, preferably 1.0 mm or less.
  • the thickness of the adhesive layer (cured product of the radically polymerizable adhesive composition) when the steel sheet laminate is formed is not particularly limited, and is, for example, 0.1 ⁇ m or more, preferably 0.5 ⁇ m or more, and is, for example, 1000 ⁇ m or less, preferably 500 ⁇ m or less.
  • the number of stacked steel sheets is not particularly limited, and is, for example, 2 or more, preferably 3 or more, and is, for example, 5000 or less, for example, 3000 or less, for example, 1000 or less, or for example, 800 or less.
  • the cured adhesive layer functions as an insulating layer and also as a buffer layer for the stress of the steel sheets.
  • the steel sheet laminate of the present invention is used in a rotor, stator, or the like of a motor, it is possible to reduce current loss, stress concentration, and stress distortion, thereby making it possible to form a motor with high efficiency, high performance, and high reliability.
  • Motors using the steel sheet laminate of the present invention as the core of a rotor and/or stator can be used as one or more motors selected from the group consisting of automobile drive motors, motors for adjusting the focus of cameras, drive motors for hard disks, and motors built into computers, mobile terminals, mobile phones, etc.
  • the adhesive composition according to the present invention is an adhesive composition for a steel sheet laminate for bonding steel sheets coated with a primer containing a copper compound, (A) a radically polymerizable compound, (B) an organic peroxide, and (C) a phosphate ester compound having a radically polymerizable group,
  • the adhesive composition comprises (C) a phosphoric acid ester compound having a radical polymerizable group, and the amount of the phosphoric acid ester compound is 0.055 parts by mass or more and less than 1 part by mass per 100 parts by mass of the radical polymerizable compound (A).
  • the adhesive composition, primer, and steel sheet are the same as those described in the ⁇ Radical polymerizable adhesive composition>, ⁇ Primer containing a copper compound>, and ⁇ Steel sheet> sections of the above [Method for producing a steel sheet laminate].
  • the adhesive composition of the present invention is useful for bonding various steel sheets, such as cold-rolled steel sheets and electrical steel sheets, to produce steel sheet laminates.
  • the adhesive composition can significantly shorten the set time (the time it takes for the bonded steel sheets to become fixed and immobile).
  • the set time can be measured by the method described in the Examples below, and can be, for example, less than 300 seconds, preferably less than 250 seconds, and more preferably less than 180 seconds.
  • the cured adhesive layer functions as an insulating layer and also as a buffer layer for the stress of the steel sheets. Therefore, when the steel sheet laminate is used in a rotor, stator, etc. of a motor, current loss, stress concentration, and stress distortion can be reduced, making it possible to form a highly efficient, high-performance, and highly reliable motor.
  • test steel plates A cold-rolled steel sheet having a thickness of 0.5 mm conforming to JIS G 3141 was cut into a size of 25 mm width x 100 mm length (W25mm x L100mm) to prepare a cold-rolled steel sheet for testing.
  • Test electrical steel sheets were prepared in the same manner as in the preparation of the test cold-rolled steel sheets, except that a 0.25 mm thick electrical steel sheet (thin Hi-X Core 25HX1500, manufactured by Nippon Steel Corporation) was used instead of the cold-rolled steel sheet.
  • the prepared test pieces were aged in an environment of 23°C for 24 hours and then pulled at a pulling rate of 0.5 mm/min using a universal tensile tester to obtain the tensile shear adhesive strength (N/mm 2 ) of the cold-rolled steel sheet in accordance with JIS K 6850 (1999).
  • the two bonded cold-rolled steel sheets for testing were pressed with an air press for a predetermined time and then removed to prepare a test piece (corresponding to a steel sheet laminate).
  • a test piece (corresponding to a steel sheet laminate).
  • one of the test cold-rolled steel plates was fixed, a 5 kg weight was hung from the other test cold-rolled steel plate, a tensile shear load was applied parallel to the adhesive surface, and it was visually confirmed whether the adhesive joint of the test specimens broke.
  • the time from when the test piece was pressed with the air press to when the pressure was released was defined as the air press time, and the air press time when the bonded surface of the test piece no longer broke was defined as the set time.
  • the weight was hung for 10 seconds.
  • test piece is compressed with an air press for 20 seconds, removed, and then a 5 kg weight is hung from it immediately after preparation, the bonded surface of the test piece will break; on the other hand, if the test piece is compressed with an air press for 30 seconds, removed, and then a 5 kg weight is hung from it immediately after preparation, the set time will be 30 seconds if the bonded surface of the test piece does not break.
  • ⁇ Tensile shear adhesive strength of electrical steel sheets> Two test magnetic steel sheets each measuring 25 mm wide and 100 mm long were prepared. 0.018 ml of primer was sprayed onto one end of one of the test electrical steel sheets in the longitudinal direction, and the sheet was left to dry at 25° C. for 3 hours. 0.03 ml of adhesive was applied with a spatula to one end of the other test electromagnetic steel sheet in the longitudinal direction. Immediately after applying the adhesive, the primer-coated surface and adhesive-coated surface of the test electromagnetic steel sheet were bonded together so that the bonding area was 25 mm wide x 12.5 mm long. Thereafter, the two bonded test magnetic steel sheet laminates were pressed with an air press for 200 seconds and then removed to prepare test specimens.
  • the prepared test pieces were aged in an environment of 23°C for 24 hours and then pulled in a direction parallel to the adhesive surface at a pulling rate of 0.5 mm/min using a universal tensile tester to obtain the tensile shear adhesive strength (N/ mm2 ) of the electrical steel sheet in accordance with JIS K 6850 (1999).
  • ⁇ Electromagnetic steel sheet setting time> Two test magnetic steel sheets each measuring 25 mm wide and 100 mm long were prepared. 0.018 ml of primer was sprayed onto one end of one of the cold-rolled steel sheets in the longitudinal direction, and the sheet was left to dry at 25° C. for 3 hours. 0.03 ml of adhesive was applied with a spatula to one end of the other cold-rolled steel sheet in the longitudinal direction. Immediately after applying the adhesive, the primer-coated surface and adhesive-coated surface of the test magnetic steel sheet were bonded together so that the bonding area was 25 mm wide x 12.5 mm long. Thereafter, the two bonded test magnetic steel sheet laminates were pressed with an air press for a predetermined time and then removed to prepare test specimens.
  • test cold-rolled steel plates Immediately after preparing the test specimens, one of the test cold-rolled steel plates was fixed, a 5 kg weight was hung from the other test cold-rolled steel plate, a tensile shear load was applied parallel to the adhesive surface, and it was visually confirmed whether the adhesive joint of the test specimens broke.
  • the time from when the test piece was pressed with the air press to when the pressure was released was defined as the air press time, and the air press time when the bonded surface of the test piece no longer broke was defined as the set time.
  • the weight was hung for 10 seconds.
  • test piece is compressed with an air press for 20 seconds, removed, and then a 5 kg weight is hung from it immediately after preparation, the bonded surface of the test piece will break; on the other hand, if a test piece is compressed with an air press for 30 seconds, removed, and then a 5 kg weight is hung from it immediately after preparation, the set time will be 30 seconds if the bonded surface of the test piece does not break.
  • Examples 1 to 5 Each component shown in Table 1 was taken in the amount (parts by mass) shown in Table 1 and mixed in a glass container to prepare an adhesive composition. The adhesive composition thus obtained was used to measure the tensile shear bond strength to cold-rolled steel sheets, the set time to cold-rolled steel sheets, and the tensile shear bond strength and set time to electrical steel sheets. The results are shown in Table 1.
  • Example 6 to 12 Each component shown in Table 2 was taken in the amount (parts by mass) shown in Table 2 and mixed in a glass container to prepare an adhesive composition. The adhesive composition thus obtained was used to measure the tensile shear adhesive strength and the set time of the cold-rolled steel sheet. The results are shown in Table 2.
  • Comparative Examples 1 to 7 in Table 3 show that when steel sheet laminates are constructed using steel sheets (cold-rolled steel sheets and electrical steel sheets) having punching oil on their surfaces, the steel sheet laminate manufacturing method and radically polymerizable adhesive composition of the present invention are not satisfactory in terms of tensile shear bond strength and/or fast curing properties (set time of less than 300 seconds) because the blending amount of (C) the phosphate ester compound having a radically polymerizable group is outside the range of the present invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention a pour premier objet de mettre à disposition un procédé de production de stratifié de feuilles d'acier permettant de produire un stratifié de feuilles d'acier ayant une excellente force adhésive, dans lequel la vitesse de durcissement d'un adhésif est suffisamment rapide et le temps nécessaire pour obtenir l'adhérence et former le stratifié de feuilles d'acier est court, et qui offre une bonne aptitude au façonnage ; et la présente invention a pour second objet de produire un stratifié de feuilles d'acier ayant une excellente force adhésive. À cet effet, la présente invention concerne un procédé de production de stratifié de feuilles d'acier qui consiste à faire adhérer des feuilles d'acier sur lesquelles est appliquée une amorce contenant un composé de cuivre, à l'aide d'une composition adhésive polymérisable par voie radicalaire contenant (A) un composé polymérisable par voie radicalaire, (B) un peroxyde organique, et (C) un composé d'ester de phosphate ayant un groupe polymérisable par voie radicalaire. Dans le procédé, la quantité du composé d'ester de phosphate (C) ayant un groupe polymérisable par voie radicalaire n'est pas inférieure à 0,055 partie en masse mais inférieure à 1 partie en masse par rapport à 100 parties en masse du composé polymérisable par voie radicalaire (A).
PCT/JP2025/010394 2024-03-18 2025-03-18 Procédé de production de stratifié de feuilles d'acier, stratifié de feuilles d'acier, et composition adhésive Pending WO2025197894A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2025543247A JP7757573B1 (ja) 2024-03-18 2025-03-18 鋼板積層体の製法、鋼板積層体及び接着剤組成物
JP2025170103A JP2025182122A (ja) 2024-03-18 2025-10-08 鋼板積層体の製法、鋼板積層体及び接着剤組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2024-041872 2024-03-18
JP2024041872 2024-03-18

Publications (1)

Publication Number Publication Date
WO2025197894A1 true WO2025197894A1 (fr) 2025-09-25

Family

ID=97139812

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2025/010394 Pending WO2025197894A1 (fr) 2024-03-18 2025-03-18 Procédé de production de stratifié de feuilles d'acier, stratifié de feuilles d'acier, et composition adhésive

Country Status (3)

Country Link
JP (2) JP7757573B1 (fr)
TW (1) TW202602673A (fr)
WO (1) WO2025197894A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51132234A (en) * 1975-04-21 1976-11-17 Suriibondo:Kk An anaerobic adhesive composition
JPS54141826A (en) * 1978-04-24 1979-11-05 Lord Corp Composition for bonding structure
US4433124A (en) * 1980-12-13 1984-02-21 Okura Kogyo Kabushiki Kaisha Adhesive compositions
JPH1060381A (ja) * 1996-08-21 1998-03-03 Denki Kagaku Kogyo Kk 嫌気性アクリル系接着剤用プライマー組成物
WO2019123885A1 (fr) * 2017-12-18 2019-06-27 株式会社スリーボンド Composition adhésive polymérisable par voie radicalaire pour feuille d'acier stratifiée adhésive, stratifié adhésif, moteur et procédé de production de stratifié adhésif
WO2023100906A1 (fr) * 2021-11-30 2023-06-08 東亞合成株式会社 Composition adhésive de durcissement anaérobie, stratifié lié, moteur et composition d'apprêt pour durcissement anaérobie
JP2023156179A (ja) * 2022-04-12 2023-10-24 セメダイン株式会社 二液型（メタ）アクリル系接着剤組成物を使用する接着工法
WO2023210718A1 (fr) * 2022-04-28 2023-11-02 東亞合成株式会社 Composition d'apprêt
JP2025069879A (ja) * 2023-10-18 2025-05-01 東亞合成株式会社 嫌気硬化型接着剤組成物、硬化物、及び積層体

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5780018B2 (ja) * 2011-06-30 2015-09-16 三菱レイヨン株式会社 シラップ組成物、シラップ配合組成物および積層体
JP6913273B2 (ja) * 2016-04-05 2021-08-04 株式会社スリーボンド ラジカル硬化性樹脂組成物、モータ用接着剤組成物
WO2018047597A1 (fr) * 2016-09-06 2018-03-15 株式会社スリーボンド Adhésif électroconducteur thermodurcissable
JP2018172565A (ja) * 2017-03-31 2018-11-08 コニシ株式会社 アクリル系硬化性樹脂組成物
US20240218216A1 (en) * 2021-05-25 2024-07-04 Cemedine Co., Ltd. Heat-resistant acrylic adhesive composition
WO2024043168A1 (fr) * 2022-08-25 2024-02-29 デンカ株式会社 Composition durcissable, produit durci et article

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51132234A (en) * 1975-04-21 1976-11-17 Suriibondo:Kk An anaerobic adhesive composition
JPS54141826A (en) * 1978-04-24 1979-11-05 Lord Corp Composition for bonding structure
US4433124A (en) * 1980-12-13 1984-02-21 Okura Kogyo Kabushiki Kaisha Adhesive compositions
JPH1060381A (ja) * 1996-08-21 1998-03-03 Denki Kagaku Kogyo Kk 嫌気性アクリル系接着剤用プライマー組成物
WO2019123885A1 (fr) * 2017-12-18 2019-06-27 株式会社スリーボンド Composition adhésive polymérisable par voie radicalaire pour feuille d'acier stratifiée adhésive, stratifié adhésif, moteur et procédé de production de stratifié adhésif
WO2023100906A1 (fr) * 2021-11-30 2023-06-08 東亞合成株式会社 Composition adhésive de durcissement anaérobie, stratifié lié, moteur et composition d'apprêt pour durcissement anaérobie
JP2023156179A (ja) * 2022-04-12 2023-10-24 セメダイン株式会社 二液型（メタ）アクリル系接着剤組成物を使用する接着工法
WO2023210718A1 (fr) * 2022-04-28 2023-11-02 東亞合成株式会社 Composition d'apprêt
JP2025069879A (ja) * 2023-10-18 2025-05-01 東亞合成株式会社 嫌気硬化型接着剤組成物、硬化物、及び積層体

Also Published As

Publication number Publication date
JP2025182122A (ja) 2025-12-11
TW202602673A (zh) 2026-01-16
JPWO2025197894A1 (fr) 2025-09-25
JP7757573B1 (ja) 2025-10-21

Similar Documents

Publication Publication Date Title
JP7244762B2 (ja) 接着積層鋼板用ラジカル重合性接着剤組成物、接着積層体、モータおよび接着積層体の製造方法
JP7809134B2 (ja) 嫌気硬化型接着剤組成物、接着積層体、モーター、及び、嫌気硬化用プライマー組成物
CA3131675A1 (fr) Noyau de stratification de colle pour stators et son procede de fabrication, et machine electrique tournante
JPH0621146B2 (ja) 構造接着剤組成物
WO2023210718A1 (fr) Composition d'apprêt
JP6949159B2 (ja) 一液型アクリル系接着剤
CN102300950A (zh) 含有马来酰亚胺封端的聚酰亚胺的结构粘合剂
JPH04275380A (ja) アクリル接着剤組成物
JP7757573B1 (ja) 鋼板積層体の製法、鋼板積層体及び接着剤組成物
WO2023100907A1 (fr) Composition adhésive de type à durcissement anaérobie, stratifié lié et moteur
JP2002088108A (ja) 硬化性樹脂組成物、硬化体、接着剤組成物及び接合体
JP7776047B2 (ja) ラジカル重合性接着剤
JP4117719B2 (ja) 硬化性樹脂組成物、硬化体、接着剤組成物、及び接合体
CN118401578A (zh) 可固化的两步两部分丙烯酸结构粘合剂组合物
JP2023156179A (ja) 二液型（メタ）アクリル系接着剤組成物を使用する接着工法
JP2022024753A (ja) プライマー付き基材及びその製造方法、並びに接合体
JP2025035169A (ja) 組成物、接着性組成物、接着構造体および接着構造体の製造方法
WO2025134838A1 (fr) Composition d'apprêt, procédé de production d'un stratifié, procédé de production d'une feuille d'acier stratifiée et kit de composition adhésive
WO2025142524A1 (fr) Composition adhésive en deux parties, stratifié lié, et moteur
WO2024135438A1 (fr) Composition adhésive de type à durcissement anaérobie, stratifié collé et moteur
WO2025022871A1 (fr) Adhésif anaérobie, produit durci, empilement lié et moteur
WO2025211230A1 (fr) Composition adhésive, structure adhésive, stratifié et moteur
JP2025035163A (ja) 接着性組成物、接着構造体および接着構造体の製造方法
JP7149956B2 (ja) ラジカル硬化型接着組成物、接着剤
WO2025134837A1 (fr) Composition d'apprêt, procédé de production de composition d'apprêt, procédé de production de stratifié, procédé de production de feuille d'acier stratifiée, trousse de composition adhésive et procédé d'accélération de durcissement pour agent adhésif anaérobie

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2025543247

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2025543247

Country of ref document: JP

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25773383

Country of ref document: EP

Kind code of ref document: A1