WO2017170957A1 - Composition - Google Patents

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Publication number
WO2017170957A1
WO2017170957A1 PCT/JP2017/013452 JP2017013452W WO2017170957A1 WO 2017170957 A1 WO2017170957 A1 WO 2017170957A1 JP 2017013452 W JP2017013452 W JP 2017013452W WO 2017170957 A1 WO2017170957 A1 WO 2017170957A1
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WO
WIPO (PCT)
Prior art keywords
meth
component
mass
parts
acrylate
Prior art date
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PCT/JP2017/013452
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English (en)
Japanese (ja)
Inventor
麻希子 佐々木
剛介 中島
Original Assignee
デンカ株式会社
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Priority to JP2018509481A priority Critical patent/JP6694057B2/ja
Publication of WO2017170957A1 publication Critical patent/WO2017170957A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/44Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F285/00Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08Macromolecular additives

Definitions

  • the present invention relates to, for example, a composition.
  • room-temperature fast-curing adhesive composition is used as an adhesive that bonds at room temperature in a short time.
  • room-temperature fast-curing adhesive compositions include two-part fast-curing epoxy adhesive compositions, anaerobic adhesive compositions, instantaneous adhesive compositions, and second-generation acrylic adhesive compositions (SGA). )It has been known.
  • the two-part type fast-curing epoxy adhesive is one in which a main agent and a curing agent are measured, mixed, applied to an adherend, and cured by a reaction between the main agent and the curing agent.
  • the two-part type fast-curing epoxy adhesive is required to have higher peel strength and impact strength.
  • the anaerobic adhesive is cured by pressure-bonding the adhesive composition between adherends to block air.
  • the anaerobic adhesive composition is required to have a property of curing even if the part of the adhesive composition comes out of the adherend when it is pressure-bonded, even if the part of the adhesive composition comes into contact with air. .
  • a property of curing even when the clearance between adherends is large is required.
  • SGA is a two-component (meth) acrylic adhesive, but it does not require accurate metering of the two components, and even if metering or mixing is incomplete, it can be done for several minutes to several tens of minutes at room temperature just by contacting the two components. Excellent workability due to curing. Furthermore, since the peel strength and impact strength are high and the hardened portion is well cured, it is widely used from the electrical / electronic parts field to the civil engineering / architecture field and the transportation vehicle field.
  • a steel plate or an aluminum alloy is often subjected to a baking coating treatment.
  • the steel plate In this baking coating processing step, the steel plate is exposed to a high temperature of, for example, 220 ° C. for one hour. Therefore, the adhesion of the transportation vehicle parts that pass through the baking coating treatment process must have heat resistance that can withstand the treatment at such a high temperature.
  • SGA retains its adhesiveness even after high-temperature baking treatment when it is bonded to a steel sheet, but if it is bonded to an adherend with a high coefficient of thermal expansion such as an aluminum alloy, the adhesive strength may be reduced. Was demanded.
  • Patent Documents 1 to 4 are disclosed.
  • Patent Document 1 discloses that the elastomer (A) is 1 to 30% by mass, the hydroxyl group-containing acrylic acid derivative (B) is 40 to 99% by mass, and a (meth) acrylic polymerizable monomer (C) other than the above (B). Describes an adhesive composition containing 0 to 59% by mass of a polymerization initiator (D) and a reducing agent (E). However, the structure (1-3) of the present invention is not described. Patent Document 1 has no report on the effect of improving heat resistance.
  • Patent Document 2 contains resin fine particles (a) having a core-shell structure and a photocurable resin (b), has a viscosity at 25 ° C. of 100 Pa ⁇ s or less as measured using an E-type viscometer, and has a viscosity after prebaking. Describes a liquid crystal sealant having a viscosity of 100 Pa ⁇ s to 400 Pa ⁇ s. However, the structure (1-3) of the present invention is not described. In Patent Document 2, although heat treatment is performed at 90 to 130 ° C. for thickening and curing the adhesive composition, there is no report on heat resistance under high-temperature baking conditions such as 220 ° C. as in the present invention. .
  • Patent Document 3 has a static viscosity at 20 rpm of 110,000 mPa or less, a thixotropic coefficient obtained by dividing the static viscosity at 2 rpm by the static viscosity at 20 rpm is 1.7 or more, and (1) a polymerizable vinyl monomer is The curable resin composition containing is described. However, there is no description about (2-1) of the present invention.
  • Patent Document 4 is an acrylic adhesive composition comprising (1) a (meth) acrylic acid derivative monomer, (2) a polymerization initiator, (3) a reducing agent, and (4) a diene core-shell polymer.
  • the diene-based core-shell polymer is swellable in the (meth) acrylic acid derivative monomer, and the swelling degree in toluene at 25 ° C. is 9.5 or more.
  • An acrylic adhesive composition is described. However, there is no description about (2-1) of the present invention.
  • an object of the present invention is to provide a composition having heat resistance, for example.
  • the present invention is as follows.
  • composition according to ⁇ 1> wherein in the component (2-1), the core portion is a silicone / acrylic composite rubber and the shell portion is a vinyl polymer.
  • ⁇ 8> In 100 parts by mass of component (1), 10 to 85 parts by mass of component (1-1), 5 to 60 parts by mass of component (1-2), and 1 to 60 parts by mass of component (1-3) ⁇ 1> to ⁇ 7>.
  • composition according to ⁇ 1> to ⁇ 8> which contains an acidic phosphoric acid compound.
  • composition described in ⁇ 1> to ⁇ 10> is divided into a first agent and a second agent, the first agent contains at least (3) a polymerization initiator, and the second agent is at least (4) A two-pack composition containing a reducing agent.
  • the present invention has, for example, heat resistance.
  • (Meth) acrylate refers to, for example, a monomer having a (meth) acryloyl group.
  • Monofunctional (meth) acrylate refers to a monomer having one (meth) acryloyl group.
  • the polyfunctional (meth) acrylate refers to a monomer having two or more (meth) acryloyl groups.
  • the amount used is preferably the amount used relative to the total of the first agent and the second agent.
  • the total content of (1) (meth) acrylate and (2) elastomer is preferably 70 parts by mass or more, preferably 85 parts by mass or more, and 90 parts by mass or more in 100 parts by mass of the composition. Most preferably.
  • (1) (Meth) acrylate includes (1-1) monofunctional (meth) acrylate having an aromatic group, (1-2) monofunctional (meth) acrylate having a hydroxyl group, and (1-3) general formula ( The polyfunctional (meth) acrylate represented by A) is preferably contained.
  • the (1) (meth) acrylate may or may not contain (meth) acrylates other than the above (1-1), (1-2), and (1-3).
  • the monofunctional (meth) acrylate having an aromatic group makes the adhesive composition rigid and improves the solubility of the elastomer component.
  • (1-1) preferably excludes (1-2).
  • (1-1) is by definition different from polyfunctional (1-3).
  • (1-1) preferably has no hydroxyl group.
  • Examples of such a monomer include (meth) acrylate of formula (B), phenoxydiethylene glycol (meth) acrylate, phenoxyethyl (meth) acrylate, and the like. In these, the (meth) acrylate of a formula (B) is preferable.
  • (meth) acrylate of the formula (B) benzyl (meth) acrylate, methylbenzyl (meth) acrylate, ethylbenzyl (meth) acrylate, propylbenzyl (meth) acrylate, methoxybenzyl (meth) acrylate, chlorobenzyl (meth) ) Acrylate and the like.
  • benzyl (meth) acrylate is preferred.
  • the amount of (1-1) used is preferably 10 to 85 parts by mass, more preferably 20 to 70 parts by mass, and most preferably 35 to 65 parts by mass in the total 100 parts by mass of (1).
  • the solubility of the elastomer component is improved, and workability and applicability are improved. If it is 85 parts by mass or less, the peel strength is improved.
  • a monofunctional (meth) acrylate having a hydroxyl group improves, for example, adhesion to an adherend.
  • (1-2) preferably excludes (1-1).
  • (1-2) is by definition different from polyfunctional (1-3).
  • (1-2) preferably has no aromatic ring.
  • Such monomers include hydroxyalkyl (meth) acrylate, glycerol mono (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, 4-hydroxycyclohexyl ( And meth) acrylate and 1,4-butanediol mono (meth) acrylate. Of these, hydroxyalkyl (meth) acrylate is preferred.
  • (meth) acrylates of formula (D) are preferred.
  • Formula (D) Z—O— (R 7 O) q —H (In the formula (D), Z represents a (meth) acryloyl group.
  • R 7 represents an alkylene group.
  • Q represents an integer of 1 to 10.
  • the alkylene group is preferably an alkylene group having 2 to 6 carbon atoms. q is preferably 1.
  • Examples of the (meth) acrylate of the formula (D) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate and the like. Among these, one or more members selected from the group consisting of 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate are preferable, and 2-hydroxypropyl (meth) acrylate is most preferable.
  • the amount of (1-2) used is preferably 5 to 60 parts by mass, more preferably 10 to 50 parts by mass, and most preferably 15 to 40 parts by mass in 100 parts by mass of (1). If it is 5 parts by mass or more, the adhesion is improved. When it is 60 parts by mass or less, the solubility of the elastomer component is improved, workability and applicability are improved, and heat resistance is improved.
  • the monomer of the general formula (A) has the following structure.
  • a monomer represented by formula (A) has the following structure.
  • R 1 and R 1 ′ are preferably an alkylene group having 2 to 6 carbon atoms, and more preferably an ethylene group having 2 carbon atoms.
  • R 2 and R 2 ′ are preferably a methyl group.
  • p and p ′ are preferably 0 to 8, more preferably 3 to 8, and most preferably 5.
  • Examples of such a monomer include 2,2-bis (4- (meth) acryloxyphenyl) propane, 2,2-bis (4- (meth) acryloxyethoxyphenyl) propane, 2,2- Bis (4- (meth) acryloxydiethoxyphenyl) propane, 2,2-bis (4- (meth) acryloxypropoxyphenyl) propane, 2,2-bis (4- (meth) acryloxytetraethoxyphenyl) Examples include propane and 2,2-bis (4- (meth) acryloxypolyethoxyphenyl) propane. Of these, 2,2-bis (4- (meth) acryloxypolyethoxyphenyl) propane is preferred.
  • the amount of (1-3) used is preferably 1 to 60 parts by mass, more preferably 10 to 45 parts by mass, and most preferably 15 to 30 parts by mass in the total 100 parts by mass of (1). When it is 1 part by mass or more, the heat resistance is improved. When it is 60 parts by mass or less, the solubility of the elastomer component is improved, and workability and applicability are improved.
  • the elastomer contains, for example, (2-1) a silicone-modified acrylic core-shell (co) polymer.
  • the silicone-modified acrylic core-shell (co) polymer refers to a core-shell type elastomer having silicone-acrylic rubber.
  • Co polymer means a polymer and a copolymer.
  • the core-shell type for example, the core means the nucleus, the shell means the shell, and the material of the nucleus and the shell is different for one particle.
  • silicone / acrylic rubber is preferably the core part.
  • the silicone / acrylic rubber is preferably a silicone / acrylic composite rubber in which an alkyl (meth) acrylate rubber polymer is combined with a silicone rubber polymer in terms of mechanical properties.
  • the complexing can be carried out, for example, by adding an alkyl (meth) acrylate component to a polyorganosiloxane latex and polymerizing in the presence of a radical polymerization initiator.
  • the silicone-acrylic composite rubber refers to a rubber having a structure in which, for example, polyorganosiloxane and polyalkyl (meth) acrylate are intertwined so that they cannot be separated from each other.
  • the shell portion examples include homopolymers and copolymers. Of these, homopolymers are preferred.
  • the homopolymer is preferably a vinyl polymer such as polystyrene, (meth) acrylonitrile, (meth) acrylic acid alkyl ester and the like.
  • vinyl polymers (meth) acrylic acid alkyl ester polymers are preferred.
  • alkyl (meth) acrylates methyl (meth) acrylate is preferred.
  • Copolymers include styrene- (meth) acrylonitrile copolymer, styrene- (meth) methacrylic acid alkyl ester copolymer, acrylic acid-methacrylic acid copolymer, styrene- (meth) acrylonitrile- (meth) acrylic acid alkyl ester.
  • a copolymer etc. are mentioned.
  • styrene- (meth) acrylonitrile copolymers are preferred.
  • a shell part is obtained as follows, for example.
  • a vinyl monomer is added and polymerization is carried out to obtain a graft copolymer latex.
  • the obtained graft copolymer latex is coagulated and solidified to obtain a shell portion, which becomes a core-shell (co) polymer.
  • the silicone-modified acrylic core-shell polymer is preferably used in an amount of 5 to 40 parts by mass, more preferably 15 to 30 parts by mass with respect to 100 parts by mass in total of (1) and (2). If it is 5 parts by mass or more, high-temperature bake heat resistance is sufficient. If it is 40 parts by mass or less, the viscosity will not be high, and there will be no inconvenience in work.
  • the elastomer preferably contains an elastomer other than (2-2) and (2-1).
  • (2-2) is preferably not a core-shell (co) polymer. Not being a core-shell (co) polymer means having no core-shell structure.
  • (2-2) is preferably an elastomer soluble in (meth) acrylate.
  • the (2) elastomer may contain an elastomer other than the above (2-1) and (2-2), but preferably does not contain it.
  • Examples of (2-2) include (meth) acrylonitrile-butadiene- (meth) acrylic acid copolymer, (meth) acrylonitrile-butadiene-methyl (meth) acrylate copolymer, and (meth) acrylonitrile-butadiene.
  • Examples include styrene-based thermoplastic elastomers such as copolymers, styrene-butadiene copolymers, chlorosulfonated polyethylene, and styrene-polybutadiene-styrene synthetic rubbers, as well as (butadiene) -modified polybutadienes and urethane elastomers. .
  • (meth) acrylonitrile-butadiene-methyl (meth) acrylate and acrylonitrile-butadiene copolymer are preferable, and (meth) acrylonitrile-butadiene copolymer is preferable. Is more preferable.
  • the amount of (2-2) used is preferably 5 to 30 parts by mass, more preferably 8 to 15 parts by mass with respect to 100 parts by mass in total of (1) and (2). If it is 5 parts by mass or more, the peel strength at low temperatures is improved. When it is 30 parts by mass or less, the adhesion is improved, the viscosity is not increased, and the handling property is improved.
  • the polymerization initiator is preferably an organic peroxide.
  • organic peroxides include cumene hydroperoxide, paramentane hydroperoxide, tertiary butyl hydroperoxide, diisopropylbenzene dihydroperoxide, methyl ethyl ketone peroxide, benzoyl peroxide, and tertiary butyl peroxybenzoate. Can be mentioned. Among these, cumene hydroperoxide is preferable from the viewpoint of stability.
  • the polymerization initiator is preferably used in an amount of 0.1 to 20 parts by weight, more preferably 0.5 to 10 parts by weight with respect to 100 parts by weight in total of (1) and (2). Most preferred is 8-5 parts by weight.
  • the curing speed is increased.
  • the storage stability is improved, and when it is 10 parts by mass or less, the storage stability is further improved.
  • the reducing agent may be any known reducing agent that reacts with the polymerization initiator to generate radicals.
  • Representative reducing agents include, for example, tertiary amines, thiourea derivatives and transition metal salts.
  • Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, and N, N-dimethylparatoluidine.
  • Examples of thiourea derivatives include 2-mercaptobenzimidazole, methylthiourea, dibutylthiourea, tetramethylthiourea, and ethylenethiourea.
  • Examples of the transition metal salt include cobalt naphthenate, copper naphthenate, and vanadyl acetylacetonate. Among these, transition metal salts are preferable in terms of reactivity. Of the transition metal salts, vanadyl acetylacetonate is preferred.
  • the amount of the reducing agent used is preferably 0.05 to 15 parts by mass, more preferably 0.1 to 5 parts by mass with respect to 100 parts by mass in total of (1) and (2). When it is 0.05 parts by mass or more, the curing speed is increased. When it is 15 parts by mass or less, the storage stability is improved.
  • the present invention preferably contains (5) an acidic phosphoric acid compound.
  • (5) is preferably an acidic phosphoric acid compound represented by the general formula (C).
  • component (5) examples include acid phosphooxyethyl (meth) acrylate, acid phosphooxypropyl (meth) acrylate and bis (2- (meth) acryloyloxyethyl) phosphate. (5) is preferably contained in the second agent.
  • the use amount of (5) is preferably 0.05 to 10 parts by mass, more preferably 0.1 to 7 parts by mass, with respect to 100 parts by mass of (1) and (2).
  • it is 0.05 parts by mass or more, the curing speed is increased and the adhesiveness is improved. Adhesiveness will improve if it is 10 mass parts or less.
  • the present invention preferably contains (6) paraffins.
  • (6) in the composition of the present invention speeds up the curing of the part in contact with air.
  • paraffins include paraffin, microcrystalline wax, carnauba wax, beeswax, lanolin, spermaceti, ceresin and candelilla wax. Of these, paraffin is preferred.
  • the amount of (6) used is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass in total of (1) and (2).
  • the amount is 0.1 parts by mass or more, the portion in contact with air is hardened.
  • it is 5 parts by mass or less, the adhesive strength is improved.
  • an antioxidant or the like can be used.
  • the present invention can be used as a curable resin composition.
  • the present invention can be used as an adhesive composition.
  • it is preferably used as a two-component adhesive composition.
  • all the essential components of the adhesive composition of the present invention are not mixed during storage, the adhesive composition is divided into a first agent and a second agent, and at least a polymerization initiator is added to the first agent.
  • the two-part type is preferable in that it has excellent storage stability. In this case, it can be used as a two-component adhesive composition by applying both agents simultaneously or separately to contact and cure.
  • the adherend is joined by the adhesive composition of the present invention to produce a joined body.
  • the various materials of the adherend are not limited, such as paper, wood, ceramic, glass, ceramics, rubber, plastic, mortar, concrete, and metal, but when the adherend is metal, it exhibits excellent adhesion.
  • Silicone / acrylic core shell rubber (shell: (meth) methyl acrylate polymer): Silicone-modified acrylic core-shell polymer silicone / acrylic core-shell rubber (shell: styrene acrylonitrile copolymer) whose core is silicone acrylic rubber and whose shell is methyl methacrylate polymer:
  • the core part is a silicone-acrylic rubber, and the shell part is a styrene-acrylonitrile copolymer silicone-modified acrylic core-shell polymer
  • NBR acrylonitrile-butadiene copolymer
  • MBS methyl methacrylate-butadiene-styrene copolymer
  • Paraffins Paraffinic acid phosphate compound: Phosphate ester, acid phosphooxyethyl methacrylate (Structural formula below) (CH 2 ⁇ C (CH 3 ) —COOC 2 H 4 O) n P (O) (OH) 3-n n is 1 or 2.
  • Epoxy acrylate Use PE210 (miwon). In the epoxy acrylate, R 1 and R ′ 1 in the general formula (A) do not correspond to (1-3) because they have OH groups, and are polyfunctional (1-1) and (1-2) Not applicable.
  • Test piece an aluminum alloy A5052 plate subjected to a 100 ⁇ 25 ⁇ 2.0 mm wiping treatment was used.
  • JISK-6850 1999 under an environment of a temperature of 23 ° C. and a humidity of 50%, an adhesive mixed with the first agent and the second agent is applied to one side of one test piece, and the test pieces are immediately overlapped with each other. Pasted together. After that, it was cured at room temperature for 24 hours, and this was used as a sample for measuring the tensile shear strength, and the tensile shear strength (unit: MPa) was measured to obtain the initial tensile shear strength.
  • the sample for measuring tensile shear strength was baked at 220 ° C. for 1 hour, cooled to a temperature of 23 ° C., measured for tensile shear strength (unit: MPa), and baked. Of tensile shear strength. All the measurements were performed at a tensile speed of 10 mm / min in an environment at a temperature of 23 ° C.
  • the workability of the two-part acrylic adhesive composition was determined as follows based on the value of 20 rotational viscosity as measured by a B-type viscometer. ⁇ : Workability is very good (viscosity less than 100,000 mPa ⁇ s). (Triangle
  • the unit of the amount used of each substance is shown in parts by mass.
  • Examples 1 to 6, Comparative Examples 1 to 4 Two-component acrylic adhesive compositions were prepared with the compositions of Examples and Comparative Examples shown in Table 1, and the initial and post-baking treatments were measured for tensile shear strength, peel strength, and workability.
  • a silicone-modified acrylic core-shell (co) polymer high adhesive strength was exhibited even after baking.
  • a silicone-modified acrylic core-shell polymer whose shell part is a methyl (meth) acrylate polymer high adhesive strength was exhibited even after baking.
  • MBS methyl methacrylate-butadiene-styrene copolymer
  • an acrylic core-shell polymer were applied, the tensile shear strength and peel strength after baking were low.
  • a butadiene-based core-shell polymer was applied, the core-shell rubber did not disperse well in the adhesive.
  • epoxy acrylate was used, the adhesive strength after baking treatment was low.
  • a two-component adhesive composition having heat resistance is obtained. Since the obtained two-component adhesive composition can withstand a high temperature baking process, the industrial advantage is great.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Graft Or Block Polymers (AREA)
  • Polymerisation Methods In General (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition présentant une résistance à la chaleur. La composition comprend (1) des (méth)acrylates comprenant (1-1) un (méth)acrylate monofonctionnel présentant un groupe aromatique, (1-2) un (méth)acrylate monofonctionnel présentant un groupe hydroxy et (1-3) un (méth)acrylate polyfonctionnel représenté par la formule générale (A), (2) des élastomères comprenant (2-1) un élastomère qui comprend un (co)polymère à noyau/enveloppe en acrylique modifié par silicone, (3) un initiateur de polymérisation et (4) un agent réducteur. Formule (A) (Dans la formule, Z et Z' peuvent être identiques ou différents et représentent chacun un groupe (méth)acryloyle ; R1 et R1' peuvent être identiques ou différents et représentent chacun un groupe alkylène ; R2 et R2' peuvent être identiques ou différents et représentent chacun un atome d'hydrogène ou un groupe alkyle en C1-4 ; et p et p' peuvent être identiques ou différents et représentent chacun un entier de 0 à 8.)
PCT/JP2017/013452 2016-03-31 2017-03-30 Composition WO2017170957A1 (fr)

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JP2018509481A JP6694057B2 (ja) 2016-03-31 2017-03-30 組成物

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JP2016-070071 2016-03-31
JP2016070071 2016-03-31

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WO2017170957A1 true WO2017170957A1 (fr) 2017-10-05

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JP2020026507A (ja) * 2018-08-16 2020-02-20 三菱ケミカル株式会社 二剤型アクリル系接着剤組成物、それにより接合された接合体
WO2020129946A1 (fr) * 2018-12-17 2020-06-25 日本製鉄株式会社 Noyau de stratification de colle pour stators et son procédé de fabrication, et machine électrique tournante
CN113196617A (zh) * 2018-12-17 2021-07-30 日本制铁株式会社 层叠芯、其制造方法、以及旋转电机
JPWO2022210166A1 (fr) * 2021-03-31 2022-10-06
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US12074476B2 (en) 2018-12-17 2024-08-27 Nippon Steel Corporation Adhesively-laminated core for stator and electric motor
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CN113196617A (zh) * 2018-12-17 2021-07-30 日本制铁株式会社 层叠芯、其制造方法、以及旋转电机
US11990795B2 (en) 2018-12-17 2024-05-21 Nippon Steel Corporation Adhesively-laminated core for stator, method of manufacturing same, and electric motor
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KR102693884B1 (ko) * 2018-12-17 2024-08-12 닛폰세이테츠 가부시키가이샤 스테이터용 접착 적층 코어, 그 제조 방법 및 회전 전기 기기
US12068097B2 (en) 2018-12-17 2024-08-20 Nippon Steel Corporation Laminated core, core block, electric motor and method of producing core block
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WO2022210166A1 (fr) * 2021-03-31 2022-10-06 デンカ株式会社 Composition adhésive, corps collé et procédé de production d'une composition adhésive
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