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WO2023210718A1 - Composition d'apprêt - Google Patents

Composition d'apprêt Download PDF

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Publication number
WO2023210718A1
WO2023210718A1 PCT/JP2023/016559 JP2023016559W WO2023210718A1 WO 2023210718 A1 WO2023210718 A1 WO 2023210718A1 JP 2023016559 W JP2023016559 W JP 2023016559W WO 2023210718 A1 WO2023210718 A1 WO 2023210718A1
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WO
WIPO (PCT)
Prior art keywords
meth
primer composition
adherend
acrylate
anaerobic
Prior art date
Application number
PCT/JP2023/016559
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English (en)
Japanese (ja)
Inventor
美香子 荒井
賢明 岩瀬
Original Assignee
東亞合成株式会社
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
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Publication of WO2023210718A1 publication Critical patent/WO2023210718A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • 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 primer composition and a method for producing an adhesive laminate.
  • the method of laminating steel plates using adhesives has been attracting attention when manufacturing motor cores for small motors.
  • the method of laminating steel plates with adhesive is expected to reduce distortion of the steel plates and improve energy efficiency.
  • Anaerobic adhesives are adhesives that bond metals together, but because a film is formed on the metal surface of the adherend through anti-corrosion or insulation treatment, it only comes into contact with the metal surface of the adherend. In some cases, the curing reaction may be difficult to proceed. For this reason, generally a primer containing a curing accelerator is applied to the surface of the metal to be adhered, and when joining the adherends, the primer and anaerobic adhesive are brought into contact and the anaerobic adhesive is applied. Let it harden.
  • Patent Document 1 discloses a radically polymerizable adhesive composition for adhesively laminated steel plates containing a phosphate ester compound, and also discloses a primer composition used together with the adhesive composition.
  • Patent Document 2 discloses a method for manufacturing a metal thin plate laminate using an anaerobic adhesive.
  • a hardening accelerator is added to the press working oil to use the press working oil as a primer.
  • Patent Document 3 describes a metal processing method containing (A) a solvent with a flash point of 20° C. or more and less than 70° C., (B) a metal soap represented by the general formula (1), and (C) an oily agent. Oil compositions are disclosed.
  • Patent Document 3 discloses a metal plate obtained by applying a metal working oil composition to one or both sides of a hoop-shaped metal, applying an anaerobic adhesive to one side of the hoop-shaped metal, and punching the hoop-shaped metal to its outer shape.
  • a method of manufacturing a metal laminate that laminates and adheres is disclosed, using a metalworking oil composition as a primer.
  • the primers described in Patent Documents 1 to 3 all consist of a solvent and a curing accelerator.
  • Patent Documents 2 and 3 new primers have been developed in which the primer functions as a press processing oil.
  • the composition itself consists of a solvent and a curing accelerator, and in terms of improving the adhesive strength of anaerobic adhesives, it was as effective as conventional primers.
  • primers have not been studied much. Therefore, the present inventors improved the composition of the primer and developed a primer capable of improving the adhesive strength of an anaerobic adhesive, thereby completing the present invention.
  • a first aspect of the present invention aims to provide a primer that can improve the adhesive strength of an anaerobic adhesive.
  • a second aspect of the present invention is to provide a method for manufacturing a laminate using a primer that can improve the adhesive strength of an anaerobic adhesive.
  • a primer composition containing an adhesion imparting agent and an anaerobic curing accelerator is a compound that forms a covalent bond or a hydrogen bond with a hydroxyl group, or a compound that corrodes the metal surface
  • the adhesion imparting agent is one or more selected from the group consisting of silane coupling agents, aluminum chelates, phosphate ester compounds, nitrogen atom-containing compounds, thiol-containing compounds, organic acids, and organic acid derivatives.
  • a method for producing an adhesive laminate comprising: [7] A step of preparing a plurality of adherend metals coated with the primer composition according to any one of [1] to [5] on one side and coated with an anaerobic adhesive on the other side.
  • a method for producing an adhesive laminate comprising: [8] Step (1) of preparing a plurality of first adherend metals having both surfaces coated with the primer composition according to any one of [1] to [5]; Step (2) of preparing a plurality of second adherend metals having both sides coated with an anaerobic adhesive; Step (3) of alternately overlapping the first adherend metal and the second adherend metal so that the surface of the body metal coated with the anaerobic adhesive comes into contact with the first adherend metal; A method for producing an adhesive laminate, comprising: [9] Step (1) of preparing a laminate in which at least two or more adherend metals are laminated, the method described in any one of [1] to [5] between the adherend metals of the laminate.
  • a method for producing an adhesive laminate comprising a step (2) of providing a primer
  • Primer compositions accelerate the curing of anaerobic adhesives and are used in combination with anaerobic adhesives.
  • the primer composition and the anaerobic adhesive are applied to separate adherends, and by bringing both coated surfaces together during adhesion, the primer composition and the anaerobic adhesive come into contact and the anaerobic adhesive is applied. The curing reaction of the adhesive begins, and the adherend can be firmly bonded.
  • the primer composition contains an adhesion promoter and an anaerobic curing accelerator.
  • the primer composition may further include a diluent.
  • the diluent is an optional component, and the primer composition does not need to contain a diluent. Note that the primer composition is different from an anaerobic adhesive, and preferably does not contain a radical polymerization initiator.
  • an adhesion imparting agent does not directly cure an anaerobic adhesive, but is a component that improves the adhesive strength of an anaerobic adhesive.
  • the adhesion-imparting agent is preferably one that dissolves in the diluent.
  • the adhesion imparting agent preferably contains a functional group or element that can chemically or physically interact with the metal contained in the adherend to which the primer composition is applied. Adhesion imparting agents containing such functional groups and elements can be highly effective in improving the adhesive strength of anaerobic adhesives.
  • the adhesion agent In order to impart adhesion, the adhesion agent must be a compound that partially corrodes the metal surface through chemical action, or a compound that forms covalent bonds or hydrogen bonds with the hydroxyl groups present on the surface of the adherend. is desirable.
  • the adhesion imparting agent may be added to the anaerobic adhesive, the effect of improving adhesive strength can be enhanced by adding it to the primer composition.
  • the concentration of the adhesion-imparting agent on the surface of the adherend can be increased. This allows the functional groups or elements contained in the adhesion imparting agent to interact efficiently with the adherend, thereby increasing the effect of improving adhesive strength.
  • the adhesion imparting agent may have a radically polymerizable group (a group having an ethylenically unsaturated bond).
  • the adhesion-imparting agent has a radically polymerizable group, the adhesive force of the adhesive to the adherend can be further improved.
  • adhesion-imparting agents include silane coupling agents, aluminum chelates, phosphate ester compounds, nitrogen atom-containing compounds, thiol-containing compounds, organic acids, and organic acid derivatives. These adhesion imparting agents may be used alone or in combination of two or more.
  • a silane coupling agent is a compound having one or more alkoxysilyl groups in one molecule.
  • Examples of the silane coupling agent include alkylalkoxysilanes, aminoalkoxysilanes, epoxyalkoxysilanes, vinylalkoxysilanes, and alkoxysilyl group-containing (meth)acrylates.
  • alkylalkoxysilanes include methyltrimethoxysilane, dimethyldimethoxysilane, trimethylmethoxysilane, triethoxysilane, and n-propyltrimethoxysilane.
  • aminoalkoxysilanes include N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, and 3-aminopropyltrimethoxysilane.
  • Examples include silane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, and N-phenyl-3-aminopropyltrimethoxysilane.
  • epoxyalkoxysilanes include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyltrimethoxysilane.
  • examples include propylmethyldiethoxysilane and 3-glycidoxypropyltriethoxysilane.
  • vinyl alkoxysilanes include vinyltrimethoxysilane, vinyltriethoxysilane, and vinylmethyldimethoxysilane.
  • alkoxysilyl group-containing (meth)acrylates include 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, and 3-(meth)acryloxypropylmethyldiethoxysilane. and 3-(meth)acryloxypropyltriethoxysilane.
  • the aluminum chelate a complex compound in which at least one ⁇ -ketoenolate anion is coordinated to aluminum is preferred.
  • the coordination number of the ⁇ -ketoenolate anion may be 1, 2 or 3.
  • the aluminum chelate further preferably has an alkoxy group.
  • the hydroxyl group on the metal surface and the alkoxy group of the aluminum chelate are bonded through a dealcoholization reaction, and the adhesion between the anaerobic adhesive and the metal surface can be improved.
  • the alkoxy group may have 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.
  • Typical aluminum chelate compounds include ethyl acetoacetate aluminum diisopropylate, aluminum tris (ethylacetoacetate), alkyl acetoacetate aluminum diisopropylate, aluminum monoacetylacetonate bis (ethylacetoacetate), and aluminum tris. (acetylacetate), aluminum monoacetylacetate bis(ethylacetoacetate), aluminum di-n-butoxide monomethylacetoacetate, aluminum diisobutoxide monomethylacetoacetate, aluminum di-sec-butoxide monomethylacetoacetate, and the like.
  • the phosphoric acid ester compound preferably has a group represented by the following general formula (1) or (2).
  • the phosphoric acid ester compound is a compound represented by the following general formula (3).
  • each R is independently an alkyl group having 1 to 5 carbon atoms, provided that the alkyl group may be substituted with a (meth)acryloxy group, a vinyl group or an allyl group, and a is 1 or 2.
  • Specific phosphoric acid ester compounds include monobutyl phosphate, dibutyl phosphate, tributyl phosphate, and 2-hydroxyethyl methacrylate acid phosphate.
  • the compound containing a nitrogen atom preferably contains a nitrogen-containing functional group (for example, an amino group, an amide group, an imide group, etc.) or a nitrogen-containing heterocyclic structure.
  • a nitrogen-containing functional group for example, an amino group, an amide group, an imide group, etc.
  • radically polymerizable monomers containing nitrogen atoms and aromatic amines are preferred.
  • radically polymerizable monomers containing a nitrogen atom include N-phenylmaleimide, N-(4-hydroxyphenyl)maleimide, N-(4-acetylphenyl)maleimide, and N-(4-methoxyphenyl).
  • examples include monomers having a maleimide skeleton such as maleimide, N-(4-ethoxyphenyl)maleimide, N-(4-chlorophenyl)maleimide, N-(4-bromophenyl)maleimide, and N-benzylmaleimide.
  • Other examples include compounds having an amide bond in which a (meth)acryloyl group is bonded to a nitrogen atom, such as acryloylmorpholine.
  • aromatic amines include, for example, toluidine, N,N-dimethylpara-toluidine, N,N-dimethylaniline, aniline, 4-methoxyaniline, aminophenol, and bis(4-aminophenyl)methane.
  • thiol-containing compounds examples include aliphatic thiols such as 1-dodecanethiol, 1-butanethiol, and 1,3-propanedithiol.
  • Silane coupling agents containing thiol, such as 3-(trimercaptopropyl)trimethoxysilane, can also be preferably used.
  • the organic acid is preferably a carboxylic acid
  • the organic acid derivative is preferably a carboxylic acid derivative.
  • organic acids and organic acid derivatives include compounds containing multiple acid functional groups in one molecule such as phthalic acid, trimellitic acid, and pyromellitic acid, and organic compounds having radically polymerizable groups such as (meth)acrylic acid.
  • examples include acids and organic acid derivatives having radically polymerizable groups such as (meth)acrylic acid esters. In addition to esters, acid anhydrides and the like can be used as organic acid derivatives. Among these, organic acids and organic acid derivatives having radically polymerizable groups are particularly preferred.
  • Examples of (meth)acrylic acid esters include monofunctional (meth)acrylates, specifically lauryl (meth)acrylate, stearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl ( meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate , phenoxytetraethylene glycol (meth)acrylate, nonylphenoxyethyl (meth)acrylate, nonylphenoxytetraethylene glycol (meth)acrylate, methoxydiethylene glycol (meth)acrylate, ethoxydiethylene glycol (meth)acryl
  • An oligomer having a (meth)acryloyl group at the end may be used as the (meth)acrylic ester.
  • Specific examples of the oligomer having a (meth)acryloyl group at the end include urethane (meth)acrylate, polyester (meth)acrylate, and epoxy (meth)acrylate. In detail, it may be the same as the oligomer having a (meth)acryloyl group at the end contained in the anaerobic adhesive described below.
  • an oligomer is a polymer with a weight average molecular weight of 500 or more and less than 5,000, and a polymer is a polymer with a weight average molecular weight of 5,000 or more.
  • the weight average molecular weight in this specification means the value calculated by converting the weight average molecular weight measured by GPC (gel permeation chromatography) using polystyrene as a standard substance.
  • adhesion agents can also be used as diluents.
  • Such an adhesion imparting agent is referred to as an "adhesion imparting agent having the function of a diluent.”
  • the adhesion imparting agent having the function of a diluent is preferably one that is liquid at room temperature and has low viscosity.
  • (meth)acrylic acid esters and oligomers having a (meth)acryloyl group at the end those with low viscosity (e.g., similar viscosity to the diluent described below) can be used as diluents.
  • the adhesion imparting agent having the function of a diluent is classified as an adhesion imparting agent, not a diluent.
  • the primer composition does not need to contain a diluent.
  • the amount of diluent used can be reduced, and in some cases, it may not be necessary to use the diluent.
  • the content of the adhesion-imparting agent in the primer composition may be increased. Therefore, the content of the adhesion-imparting agent in the primer composition needs to be considered separately for cases in which an adhesion-imparting agent having the function of a diluent is used as a diluent and in other cases.
  • the content of the adhesion imparting agent in the primer composition is preferably 0.01 to 30% by mass, more preferably 0.1 to 20% by mass, and particularly preferably 1 to 10% by mass.
  • the content of the adhesion-imparting agent in the primer composition is not particularly limited, and is, for example, 0.1 to 99.9% by mass. It may be within a range, preferably 1 to 99% by weight.
  • the adhesion imparting agent can impart especially high adhesive strength to the anaerobic adhesive when combined with a specific anaerobic curing accelerator.
  • preferred combinations include a combination of an anaerobic curing accelerator containing vanadium and a phosphate ester compound, a combination of an anaerobic curing accelerator containing manganese and a phosphate ester compound, and a combination of an anaerobic curing accelerator containing manganese and aluminum chelate. Can be mentioned.
  • Anaerobic curing accelerator is an accelerator that contributes to the initiation of anaerobic curing of an anaerobic adhesive.
  • Anaerobic hardening accelerators are metal compounds containing metals such as iron, cobalt, nickel, vanadium, copper, manganese, titanium, cerium, zirconium, zinc, tin, and bismuth.
  • the anaerobic curing accelerator is preferably an organometallic complex in which an organic group is bonded or coordinated to a metal atom.
  • anaerobic curing accelerators include copper ethylhexanoate, iron pentadione, cobalt pentadione, copper pentadione, copper propylene diamine, copper ethylene diamine, iron naphtate, nickel naphtate, cobalt naphtate, copper naphtate, copper octate, and iron.
  • organometallic complexes such as hexoate, iron propionate, and vanadium acetylacetonate.
  • the content of the anaerobic curing accelerator in the primer composition is preferably 0.01 to 30% by mass, more preferably 0.02 to 25% by mass, and particularly preferably 0.05 to 20% by mass. .
  • the adhesion imparting agent is a phosphoric acid ester compound
  • the anaerobic curing accelerator does not contain copper.
  • the content of copper in the primer composition is preferably 1% by mass or less, more preferably 0.1% by mass or less, and may be 0% by mass. . If the adhesion imparting agent is a phosphoric acid ester compound and the anaerobic curing accelerator contains copper, the effect of the adhesion imparting agent may be lower than that of other primer compositions depending on the composition of the anaerobic adhesive; Insoluble matter may be generated in the primer composition.
  • Diluent is not particularly limited as long as it is liquid at room temperature.
  • examples of diluents include press processing oils, organic solvents, and low-viscosity oligomers (excluding those used as adhesion imparting agents).
  • One type of diluent may be used alone, or two or more types of diluents may be used in combination.
  • the press working oil may be one that is commonly used when press working thin metal sheets such as steel plates. By applying press working oil during press working, foreign matter adhering to the surface of the steel plate can be removed and galling caused by the die during press working can be prevented.
  • the press processing oil may contain, for example, mineral oil or synthetic oil, which is commonly used as a base oil for rust preventive oil or metal processing oil, as a base oil, and one type of these mineral oils or synthetic oils may be used alone. or a combination of multiple types.
  • the mineral oil include paraffinic and naphthenic refined mineral oils obtained by refining the fraction obtained by distilling crude oil.
  • the synthetic oil include hydrocarbon synthetic oils such as paraffinic, naphthenic, and olefinic oils, and ester synthetic oils.
  • organic solvents examples include alcohols such as methyl alcohol, ethyl alcohol, and isopropyl alcohol, halogenated hydrocarbons such as dichloromethane, chloroform, 1.1.1-trichloroethane, and Freon, and hydrocarbons such as n-hexane and toluene. esters, ketones such as acetone and methyl ethyl ketone, and esters such as ethyl acetate and butyl acetate.
  • a highly soluble organic solvent such as N,N-dimethylformamide and dimethyl sulfoxide may be mixed and used as the diluent.
  • the viscosity of the primer composition can be adjusted to an appropriate range by adjusting the amount of diluent.
  • the viscosity of the diluent is preferably 0.1 mPa ⁇ s to 1,000 mPa ⁇ s, more preferably 0.15 mPa ⁇ s to 800 mPa ⁇ s, particularly preferably 0.2 mPa ⁇ s to 600 mPa ⁇ s. be.
  • viscosity is a value measured using a rotational viscometer described in JIS K 7117:1999 at a test temperature of 25°C.
  • the viscosity of the primer composition is preferably 0.1 mPa ⁇ s to 1,000 mPa ⁇ s, more preferably 0.2 mPa ⁇ s to 900 mPa ⁇ s, particularly preferably 0.3 mPa ⁇ s to 800 mPa ⁇ s. It is.
  • viscosity is a value measured using a rotational viscometer described in JIS K 7117:1999 at a test temperature of 25°C.
  • the application of the primer composition to the adherend may be carried out by a known method.
  • the primer composition may be applied by a known method such as roller, dispensing, spraying, inkjet, or dipping.
  • Anaerobic adhesives are adhesives that begin to harden when oxygen is blocked in the presence of metal ions.
  • the anaerobic adhesive used in this embodiment is not particularly limited, and any known adhesive may be used.
  • a commonly used anaerobic adhesive containing a radically polymerizable compound and a radical polymerization initiator can be used.
  • the anaerobic adhesive may further contain an anaerobic curing catalyst.
  • the radical polymerizable compound is a compound having a radical polymerizable group, and is particularly preferably a (meth)acrylic acid ester.
  • (meth)acrylic esters include acrylic monomers and acrylic oligomers such as monofunctional (meth)acrylates and polyfunctional (meth)acrylates.
  • Monofunctional (meth)acrylates include lauryl (meth)acrylate, stearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl ( meth)acrylate, isobornyl(meth)acrylate, benzyl(meth)acrylate, phenyl(meth)acrylate, phenoxyethyl(meth)acrylate, phenoxydiethylene glycol(meth)acrylate, phenoxytetraethyleneglycol(meth)acrylate, nonylphenoxyethyl(meth)acrylate ) acrylate, nonylphenoxytetraethylene glycol (meth)acrylate, methoxydiethylene glycol (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, butoxyethyl
  • polyfunctional (meth)acrylates examples include 1,3-butylene glycol di(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, and 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 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, stearin Acid-modified pentaerythritol di(meth)acrylate, dicyclopentenyl di(meth)acrylate, ethylene oxide-modified dicyclopentenyl di(meth)acrylate, di(meth)acryloyl isocyanurate, di
  • the anaerobic adhesive may include a polymer or oligomer having a (meth)acryloyl group at the end.
  • the polymer or oligomer having a (meth)acryloyl group at the end is not particularly limited, but from the viewpoint of anaerobic curability, urethane (meth)acrylate, epoxy (meth)acrylate, ester (meth)acrylate, isoprene-based (meth)acrylate, etc. ) acrylate, hydrogenated isoprene-based (meth)acrylate, and (meth)acrylic group-containing acrylic polymer, preferably at least one compound selected from the group consisting of urethane (meth)acrylate or epoxy (meth)acrylate. More preferably, urethane (meth)acrylate is particularly preferred.
  • Urethane (meth)acrylates include reactants of polyhydric alcohols, polyisocyanates, and hydroxy(meth)acrylate compounds, and products reacted with polyhydric isocyanates and hydroxy(meth)acrylate compounds without using polyhydric alcohols. It will be done.
  • polyhydric alcohols include polyether polyols such as polypropylene glycol and polytetramethylene glycol, polyester polyols obtained by the reaction of polyhydric alcohols and polybasic acids, and polyhydric alcohols, polybasic acids, and ⁇ -caprolactone. and polycarbonate polyols (for example, polycarbonate polyols obtained by the reaction of 1,6-hexanediol and diphenyl carbonate).
  • organic polyvalent isocyanates include isophorone diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, diphenylmethane-4,4'-diisocyanate, dicyclopentanyl diisocyanate, and the like.
  • urethane (meth)acrylate those manufactured from polyether polyol, polyester polyol, or polycarbonate polyol as the raw material polyol are preferable because they have excellent weather resistance, transparency, and adhesive strength.
  • the raw material organic polyisocyanate those manufactured from isophorone diisocyanate, hexamethylene diisocyanate, and xylene diisocyanate are preferable because they have excellent weather resistance.
  • examples of urethane (meth)acrylate include urethane (meth)acrylate having a polybutadiene skeleton, urethane (meth)acrylate having a hydrogenated polybutadiene skeleton, urethane (meth)acrylate having a polycarbonate skeleton, and urethane having a hydrogenated bisphenol A skeleton.
  • examples include (meth)acrylate, urethane (meth)acrylate having a polyether skeleton, urethane (meth)acrylate having a polyester skeleton, urethane (meth)acrylate having a castor oil skeleton, and the like.
  • epoxy (meth)acrylates examples include (meth)acrylates obtained by reacting epoxy resins such as conventionally known aromatic epoxy resins, alicyclic epoxy resins, and aliphatic epoxy resins with (meth)acrylic acid. can be mentioned.
  • radical polymerization initiator examples include organic peroxides and photoradical generators, but organic peroxides are preferred from the viewpoint of anaerobic curability.
  • organic peroxides examples include organic peroxides such as hydroperoxides, ketone peroxides, diallyl peroxides, and peroxy esters. Specifically, cumene hydroperoxide, t -butyl hydroperoxide, p-methane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, diisopropylbenzene hydroperoxide and the like. From the viewpoint of storage stability, hydroperoxides are preferably used.
  • organic peroxides with a 1-hour half-life temperature in the range of 80°C to 300°C are preferable, and organic peroxides with a 1-hour half-life temperature in the range of 100°C to 200°C are preferable. Peroxides are more preferred.
  • the 1-hour half-life temperature is a value measured by thermal decomposition in benzene at a peroxide concentration of 0.1 mol/L.
  • Organic peroxides with a 1-hour half-life temperature in the range of 80°C to 300°C include hydroperoxides.
  • hydroperoxides include p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-butyl hydroperoxide, etc. can be mentioned.
  • the photo-radical generator is not particularly limited, but includes, for example, an acetophenone-based radical photo-polymerization initiator, a benzoin-based radical photo-polymerization initiator, a benzophenone-based radical photo-polymerization initiator, a thioxanthone-based radical photo-polymerization initiator, and an acylphosphine oxide-based radical photopolymerization initiator.
  • examples include radical photopolymerization initiators, titanocene-based radical photopolymerization initiators, and the like.
  • acetophenone-based photoradical polymerization initiators include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, benzyl dimethyl ketal, and 4-(2-hydroxyethoxy)phenyl(2- hydroxy-2-propyl)ketone, 1-hydroxycyclohexylphenylketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)butanone, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone oligomer, and the like.
  • acetophenone photoradical polymerization initiators include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins), and ESACUREKIP-150 (manufactured by Lamberti S.P.A.). .
  • examples of the acylphosphine oxide-based photoradical polymerization initiator include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and the like.
  • acylphosphine oxide photoradical polymerization initiators include Omnirad TPO and Omnirad 819 (manufactured by IGM Resins B.V.).
  • the anaerobic adhesive may contain one type of radical polymerization initiator alone or may contain two or more types of radical polymerization initiators.
  • the content of the radical polymerization initiator is preferably 0.05% by mass to 20% by mass, and 0.1% by mass to 10% by mass, based on the total mass of the anaerobic adhesive. It is more preferable that the amount is 0.5% by mass to 5% by mass.
  • the anaerobic adhesive may further include an anaerobic curing catalyst. It is believed that the anaerobic curing catalyst reacts with the metal compound in the primer composition to generate active metal ions, and promotes radical generation through the reaction between these metal ions and the radical polymerization initiator, but this mechanism is speculative. However, this does not limit the present invention.
  • anaerobic curing catalyst examples include saccharin, amine compounds, azole compounds, mercaptan compounds, hydrazine compounds, and salts thereof.
  • Examples of the amine compound include heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine; heterocyclic compounds such as quinoline, methylquinoline, quinaldine, and quinoxaline phenazine; Examples include ring tertiary amines, aromatic tertiary amines such as N,N-dimethyl-anisidine, N,N-dimethylaniline, and N,N'-dimethyl-p-toluidine.
  • heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine
  • heterocyclic compounds such as quinoline, methylquinoline, quinaldine, and quinoxaline phenazine
  • Examples include ring tertiary amines, aromatic tertiary amines such as N,N-dimethyl-anisidine, N,N-dimethylani
  • azole compounds include 1,2,4-triazole, oxazole, oxadiazole, thiadiazole, benzotriazole, hydroxybenzotriazole, benzoxazole, 1,2,3-benzothiadiazole, 3-mercaptobenzotrizole, etc. can be mentioned.
  • Examples of the mercaptan compound include linear mercaptans such as n-dodecylmercaptan, ethylmercaptan, and butylmercaptan.
  • hydrazine compounds include 1-acetyl-2-phenylhydrazine, 1-acetyl-2(p-tolyl)hydrazine, 1-benzoyl-2-phenylhydrazine, 1-(1',1',1'-tri fluoro)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-(2'-phenylethylhydrazine), p-nitrophenylhydrazine, p-trisulfonylhydrazide, and the like.
  • examples of salts of hydrazine compounds include 4-methylsulfonylphenylhydrazine hydrochloride, hydrazine monohydrochloride, p-tolylhydrazine hydrochloride, and the like.
  • the anaerobic adhesive may contain only one type of anaerobic curing catalyst, or may contain two or more types of anaerobic curing catalysts.
  • the content of the anaerobic curing catalyst is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, based on the total mass of the anaerobic adhesive. It is particularly preferable that the content is 0.2% by mass or more. Further, the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less, and particularly preferably 10% by mass or less.
  • the anaerobic adhesive may include an adhesion-imparting agent contained in the primer composition.
  • radically polymerizable compounds such as (meth)acrylic acid esters can be a main component of the anaerobic adhesive, and are excluded as adhesion imparting agents contained in the anaerobic adhesive.
  • the anaerobic adhesive may include an adhesion agent selected from the group consisting of silane coupling agents, aluminum chelates, and phosphate ester compounds.
  • the adhesion imparting agent contained in the primer composition and the adhesion imparting agent contained in the anaerobic adhesive may be the same or different. It is also possible to improve the adhesive strength of an anaerobic adhesive by adding an adhesion agent only to the anaerobic adhesive, but if both the anaerobic adhesive and the primer composition or only the primer composition is added as an adhesion agent. By including, it may be possible to further enhance the effect of improving adhesive strength.
  • the content of the adhesion imparting agent (excluding radically polymerizable compounds) in the anaerobic adhesive is preferably 0.01 to 8% by mass, more preferably 0.05 to 5% by mass.
  • the total amount of adhesion imparting agent (excluding radically polymerizable compounds) is preferably 0.005 to 10% by mass, more preferably 0.01 to 5% by mass, particularly preferably is 0.02 to 1% by mass.
  • the anaerobic adhesive can exhibit high adhesive strength.
  • the mass ratio of the adhesion imparting agent contained in the primer composition to the adhesion imparting agent contained in the anaerobic adhesive (excluding radically polymerizable compounds) is preferably 0.005 to 100, more preferably is from 0.008 to 80, particularly preferably from 0.01 to 50.
  • the mass ratio of the adhesion imparting agent contained in the primer composition to the adhesion imparting agent contained in the anaerobic adhesive is expressed by the formula: It is a value calculated by (mass of adhesion imparting agent contained in the anaerobic adhesive)/(mass of adhesion imparting agent contained in the anaerobic adhesive).
  • the primer composition may be applied by known methods such as roller, dispensing, spraying, inkjet, or dipping.
  • a primer composition and an anaerobic adhesive can be used to bond at least two adherend metals to produce an adhesive laminate.
  • the adherend metal is preferably a thin metal plate, more preferably a steel plate such as an electromagnetic steel plate or a cold-rolled steel plate.
  • the surface of the adherend metal may be subjected to a surface treatment such as rust prevention treatment or insulation treatment depending on the purpose.
  • the use of the adhesive laminate is not particularly limited, and it can be used for various purposes, and is suitably used for motor cores, rotors, stators, etc. of motors.
  • the adhesive laminate may include a first metal layer, an adhesive layer containing a cured product of an anaerobic adhesive, and a second metal layer in this order.
  • the cured product of the anaerobic adhesive may contain the adhesion promoter and curing accelerator contained in the primer composition while maintaining their molecular structure.
  • the adhesion imparting agent contained in the primer composition may react with the anaerobic adhesive and become a part of the cured product of the anaerobic adhesive.
  • the manufacturing method shown below may be carried out by changing the order and conditions of the steps as appropriate depending on the adhesive laminate to be manufactured, and additional steps may be added.
  • the primer composition and the anaerobic adhesive may be applied in different ways, for example, the primer composition is applied by dipping and the anaerobic adhesive is applied by a roller.
  • the number of layers of the adhesive laminate obtained by the manufacturing method shown below is not particularly limited.
  • the adhesive laminate can be manufactured by sequentially laminating and bonding adherend metals.
  • layers containing adhesively laminated adherend metals have already been laminated.
  • Further adherend metals can be laminated and bonded to the topmost or bottommost layer of the unfinished adhesive laminate to complete the adhesive laminate.
  • adherend metals are successively laminated and bonded in this manner, the uppermost layer or the lowermost layer of the unfinished adhesive laminate can be considered one of the adherend metals.
  • the method for producing an adhesive laminate includes the step of: (1) providing a first adherend metal coated with a primer composition on at least one surface; Step (2) of preparing the coated second adherend metal, and applying the primer composition applied surface of the first adherend metal and the anaerobic adhesive of the second adherend metal. It includes a step (3) of overlapping the coated surfaces.
  • a method for manufacturing an adhesive laminate includes the steps (1) of providing a plurality of adherend metals coated with a primer composition on one side and coated with an anaerobic adhesive on the other side; The method includes a step (2) of stacking the plurality of adherend metals prepared in step (1) so that the surface coated with the primer composition and the surface coated with the anaerobic adhesive are in contact with each other.
  • the method for manufacturing an adhesive laminate includes the steps of: (1) preparing a plurality of first adherend metals coated with a primer composition on both sides; Step (2) of preparing a plurality of adherend metals, and a surface of the first adherend metal coated with a primer composition and a side of the second adherend metal coated with an anaerobic adhesive.
  • the method includes a step (3) of alternately overlapping the first adherend metal and the second adherend metal so that they are in contact with each other.
  • a laminate of the adherend metal is formed, and then the primer composition and the anaerobic adhesive that have not yet been applied are applied to the adherend metal.
  • the adherend metals forming the laminate may be bonded.
  • the adherend metals are simply laminated, there may be a gap large enough to allow the primer composition and anaerobic adhesive to penetrate. Therefore, by spraying the primer composition or anaerobic adhesive from the side of the laminate or by impregnating the laminate with the primer composition or anaerobic adhesive, the primer composition or anaerobic adhesive can be applied inside the laminate. Adhesive can be penetrated. It is also possible to insert an injection nozzle between the adherend metals and directly inject the primer composition or anaerobic adhesive between the adherend metals through the nozzle. When applying a primer composition or an anaerobic adhesive between adherend metals, it is desirable to physically fix the laminate from the outside.
  • the method for producing an adhesive laminate includes a step (1) of preparing a laminate in which at least two or more adherend metals are laminated, and providing a primer composition between the adherend metals of the laminate.
  • the method includes step (2) and step (3) of providing an anaerobic adhesive between the adherend metals of the laminate.
  • the method for producing an adhesive laminate includes a step (1) of preparing a laminate by laminating adherend metals coated with a primer composition on at least one surface; and step (2) of providing an anaerobic adhesive in between.
  • the method for producing an adhesive laminate includes a step (1) of preparing a laminate by laminating adherend metals coated with an anaerobic adhesive on at least one surface; The method includes a step (2) of providing a primer composition between the metals.
  • a step (1) of applying a primer composition to one side of a hoop material For example, a step (2) of applying an anaerobic adhesive to the side of the hoop material to which the primer composition is not applied, and a step of punching out the hoop material.
  • Manufacturing an adhesive laminate of electrical steel sheets by a method for manufacturing an adhesive laminate which includes a step (3) of manufacturing an adherend metal of a predetermined shape, and a step (4) of sequentially laminating the obtained adherend metals.
  • the step (5) of applying pressing oil to at least one surface of the hoop material may be performed before punching.
  • the diluent contained in the primer composition is a pressing oil
  • the primer composition as the pressing oil.
  • the step of applying press processing oil to the hoop material can be omitted. That is, the press processing oil application process and the primer composition application process can be performed in one process, making it possible to efficiently produce an adhesive laminate of electrical steel sheets.
  • the mass ratio of the pressing oil in the diluent is preferably 70% by mass or more, more preferably 90% by mass or more, and may be 100% by mass.
  • KBM-503 3-methacryloyloxypropyltrimethoxysilane
  • KBM-403 3-glycidyloxypropyltrimethoxysilane
  • P Tributyl phosphate
  • Al Aluminum ethyl acetoacetate diisopropylate
  • AA Acrylic acid
  • HEMA 2-hydroxyethyl methacrylate
  • ACMO acryloylmorpholine
  • DMpT N,N-dimethyl para-toluidine
  • Anaerobic adhesives A, B and C were used in the examples. Anaerobic adhesives A and B were prepared by mixing each component listed in Table 1 in a mixer at room temperature (25°C) for 60 minutes so that the content (mass%) was as listed in Table 1. It is. Anaerobic adhesive C is LOCTITE638 (manufactured by Henkel).
  • primer compositions were prepared as follows.
  • the anaerobic curing accelerator, adhesion imparting agent, and acetone as a diluent listed in Tables 2 to 7 were mixed in the mass ratios listed in parentheses in Tables 2 to 7 for 5 minutes with a mixer at room temperature (25°C).
  • a primer composition was obtained.
  • a primer composition was prepared without adding an adhesion imparting agent. Therefore, in the comparative example, a primer composition was prepared as follows.
  • the anaerobic curing accelerator and acetone as a diluent listed in Tables 2 to 7 were mixed in the mass ratios listed in parentheses in Tables 2 to 7 for 5 minutes with a mixer at room temperature (25°C) to form a primer composition. Obtained.
  • the primer composition was evaluated as follows. A set of two steel plates (35H300L or 35A300, 25 mm x 50 mm, manufactured by Nippon Steel Corporation) listed in Tables 2 to 7 was coated with 1 ⁇ L/cm 2 of the prepared primer composition on one tip. Subsequently, press processing oil was spread on it at 2 ⁇ L/cm 2 . Press processing oil was similarly spread on the steel plate to which the primer composition was not applied at 2 ⁇ L/cm 2 . Furthermore, 0.1 g of any of the anaerobic adhesives A to C listed in Tables 2 to 7 was dropped onto a steel plate coated with only press processing oil without applying a primer composition, and two sheets were immediately coated. The steel plates were pasted together and pressed together with two double clips. The above steps were carried out within 20 seconds, and the bonding area was 5 cm 2 to 6 cm 2 . The obtained test piece was left standing at 25°C for 12 to 24 hours.
  • Example 20 and Comparative Examples 6 to 9> In each example, the adhesion imparting agent listed in Table 8 was added to the anaerobic adhesive A so that the content became the mass ratio listed in parentheses in Table 8. The anaerobic adhesives used for each were prepared.
  • Example 20 a primer composition was prepared as follows. The anaerobic curing accelerator, adhesion imparting agent, and acetone as a diluent listed in Table 8 were mixed at room temperature (25°C) for 5 minutes in the mass ratio listed in parentheses in Table 8, and the primer composition was I got something. In Comparative Examples 6 to 9, no adhesion imparting agent was added. Therefore, in Comparative Examples 6 to 9, primer compositions were prepared as follows. The anaerobic curing accelerator and acetone as a diluent listed in Table 8 were mixed at room temperature (25° C.) for 5 minutes in a mixer at the mass ratios listed in parentheses in Table 8 to obtain a primer composition.

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Abstract

Une composition d'apprêt selon la présente invention contient un agent conférant de l'adhérence et un accélérateur de durcissement anaérobie, la composition d'apprêt étant caractérisée en ce que l'agent conférant de l'adhérence est un composé permettant de former une liaison covalente ou une liaison hydrogène avec des groupes hydroxyle ou d'éroder une surface métallique, et l'accélérateur de durcissement anaérobie est un composé métallique.
PCT/JP2023/016559 2022-04-28 2023-04-27 Composition d'apprêt WO2023210718A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024135438A1 (fr) * 2022-12-21 2024-06-27 東亞合成株式会社 Composition adhésive de type à durcissement anaérobie, stratifié collé et moteur

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JPS51143586A (en) * 1975-06-05 1976-12-09 Toagosei Chem Ind Co Ltd Polymerization accelerator for rapid hardening
JPS5227176B1 (fr) * 1968-03-04 1977-07-19
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JPH0288681A (ja) * 1988-09-27 1990-03-28 Toyo Ink Mfg Co Ltd プライマー
JPH05320584A (ja) * 1991-05-21 1993-12-03 Alps Electric Co Ltd 接着構造体
JPH0680937A (ja) * 1992-09-01 1994-03-22 Okura Ind Co Ltd 主剤−プライマー型アクリル系接着剤
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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
JPH10168398A (ja) * 1996-12-11 1998-06-23 Nippon Kayaku Co Ltd 接着体、及び高密度記録光ディスクの製造方法
JP2007169352A (ja) * 2005-12-20 2007-07-05 Denki Kagaku Kogyo Kk 接着性組成物、接着剤、接着方法及び家具
JP2008297399A (ja) * 2007-05-30 2008-12-11 Polymatech Co Ltd 熱伝導性接着剤組成物及び接着方法
JP2010031133A (ja) * 2008-07-28 2010-02-12 Three Bond Co Ltd 嫌気硬化性樹脂組成物
JP2012207116A (ja) * 2011-03-29 2012-10-25 Denki Kagaku Kogyo Kk 分子遮断性を有するシート状接着剤
JP2015076970A (ja) * 2013-10-08 2015-04-20 アイシン・エィ・ダブリュ株式会社 打抜き積層プレス機及び打抜き積層プレス方法
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
JP2019112475A (ja) * 2017-12-20 2019-07-11 出光興産株式会社 金属加工油組成物、及び金属板積層体の製造方法

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JPS5227176B1 (fr) * 1968-03-04 1977-07-19
JPS495215B1 (fr) * 1969-12-29 1974-02-06
JPS4921093B1 (fr) * 1970-08-07 1974-05-29
JPS51143586A (en) * 1975-06-05 1976-12-09 Toagosei Chem Ind Co Ltd Polymerization accelerator for rapid hardening
JPS594667A (ja) * 1982-06-09 1984-01-11 ロクタイト・コ−ポレ−シヨン 二液性無溶剤接着剤組成物ならびにこの組成物で表面を接着する方法
JPH0288681A (ja) * 1988-09-27 1990-03-28 Toyo Ink Mfg Co Ltd プライマー
JPH05320584A (ja) * 1991-05-21 1993-12-03 Alps Electric Co Ltd 接着構造体
JPH0680937A (ja) * 1992-09-01 1994-03-22 Okura Ind Co Ltd 主剤−プライマー型アクリル系接着剤
JPH07150113A (ja) * 1993-11-29 1995-06-13 Okura Ind Co Ltd 精密嵌め合い部品組立用二液型アクリル系接着剤およびそれを用いた精密嵌め合い部品の組立方法
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
JPH10168398A (ja) * 1996-12-11 1998-06-23 Nippon Kayaku Co Ltd 接着体、及び高密度記録光ディスクの製造方法
JP2007169352A (ja) * 2005-12-20 2007-07-05 Denki Kagaku Kogyo Kk 接着性組成物、接着剤、接着方法及び家具
JP2008297399A (ja) * 2007-05-30 2008-12-11 Polymatech Co Ltd 熱伝導性接着剤組成物及び接着方法
JP2010031133A (ja) * 2008-07-28 2010-02-12 Three Bond Co Ltd 嫌気硬化性樹脂組成物
JP2012207116A (ja) * 2011-03-29 2012-10-25 Denki Kagaku Kogyo Kk 分子遮断性を有するシート状接着剤
JP2015076970A (ja) * 2013-10-08 2015-04-20 アイシン・エィ・ダブリュ株式会社 打抜き積層プレス機及び打抜き積層プレス方法
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
JP2019112475A (ja) * 2017-12-20 2019-07-11 出光興産株式会社 金属加工油組成物、及び金属板積層体の製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024135438A1 (fr) * 2022-12-21 2024-06-27 東亞合成株式会社 Composition adhésive de type à durcissement anaérobie, stratifié collé et moteur

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