WO2004099284A1 - Composition de durcissement anaerobie - Google Patents

Composition de durcissement anaerobie Download PDF

Info

Publication number
WO2004099284A1
WO2004099284A1 PCT/JP2004/006131 JP2004006131W WO2004099284A1 WO 2004099284 A1 WO2004099284 A1 WO 2004099284A1 JP 2004006131 W JP2004006131 W JP 2004006131W WO 2004099284 A1 WO2004099284 A1 WO 2004099284A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
parts
component
compound
anaerobic
Prior art date
Application number
PCT/JP2004/006131
Other languages
English (en)
Japanese (ja)
Inventor
Aki Kusuyama
Original Assignee
Three Bond 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 Three Bond Co., Ltd. filed Critical Three Bond Co., Ltd.
Publication of WO2004099284A1 publication Critical patent/WO2004099284A1/fr

Links

Classifications

    • 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
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Definitions

  • the present invention relates to an anaerobic curable composition mainly used as an adhesive for electronic components, and more particularly to an anaerobic curable composition that generates less gas than conventional ones. Background technology>
  • the anaerobic curable composition contains a (meth) acrylate monomer as a main component and is kept in a liquid state without being gelled while in contact with oxygen in the air or the like. It has the property of hardening rapidly when it is removed, and by utilizing such properties, the composition can be used for bonding, fixing, fitting of components such as screws and bolts, bonding of components, bonding between flange surfaces, sealing, ⁇ Used for filling burrows generated in structural parts. When faster curing is required, it is used in combination with a curing accelerator such as a primer.
  • Anaerobic curable compositions have rapid curability at room temperature and have stable physical properties even after curing, so that their use in the electric field has increased significantly.
  • an anaerobic curable adhesive composition used in combination with a curing accelerator is used for adhesion between a bearing and its shaft, and for fitting and bonding around the shaft due to its productivity.
  • the magnetic recording plate magnetic disk
  • the distance between the magnetic head and the magnetic disk that reads the data has become extremely small. For this reason, if an art gas from the adhesive adheres to the magnetic disk or the magnetic head, a read / write failure occurs and the function of the HDD cannot be exhibited.
  • the present invention overcomes the above-mentioned conventional problems.For example, the generation of art gas at a high temperature after a baking process at about 90 ° C. for 1 hour after bonding of parts is compared with the case of using a conventional anaerobic curable composition.
  • An object of the present invention is to provide an anaerobic curable composition which is reduced to about one tenth in comparison with the present invention.
  • the present invention provides: (a) a compound having at least one or more radical polymerizable functional groups in a molecule: 100 parts by weight; (b) an organic peroxide: 0.1 to 5 parts by weight; ) Compound having at least one glycidyl group in the molecule: 30 to 200 parts by weight, (d) amine compound: 100 parts by weight based on the total amount of components (a) and (c) An anaerobic curable composition comprising 0.1 to 10 parts by weight.
  • the compound (a) having at least one or more radically polymerizable functional groups in the molecule used in the present invention is a compound having a butyl group such as acrylic acid or methacrylic acid in the molecule, preferably at the terminal of the molecule. Yes, monomer, oligomer, polymer Is mentioned.
  • the polymerizable monomer may be, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethyl hexylhexyl (meth) acrylate, phenyl (meth).
  • Monoesters such as acrylate and benzinole (meta) acrylate; hydroxyalkyl esters such as 2-hydroxyshethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; ethylene glycol dia Polyesters such as acrylate, polyethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropanetri (meth) acrylate, and pentaerythritol tetraacrylate, but are not limited to these. Not something to be done What is usually used in the field of anaerobic adhesives can be used. These polymerizable monomers can be used alone or as a mixture of two or more.
  • polymerizable oligomer examples include a curable resin having a malate group, a fumarate group, an aryl group, a (meth) acrylate group, an isocyanate-modified acryloligomer, an epoxy-modified acrylyl oligomer, a polyester acrylyl oligomer, and a polyether acrylate.
  • Clinole oligomers and the like, and these oligomers can be used alone or as a mixture of two or more.
  • polymerizable polymer a polymerizable unsaturated polymer such as an unsaturated polyester resin and an unsaturated acryl resin can be used.
  • These monomers, oligomers and polymers having polymerizability can be used together for the purpose of adjusting the viscosity of the anaerobic curable composition or adjusting the physical properties of the cured product.
  • the organic peroxide (b) used in the present invention is conventionally used in anaerobic curable compositions, and is not particularly limited.
  • cumenehide mouth baroxide t-pentinoleide mouth peroxide, ⁇ -menthanehydride dropoxide, methinoleethynoletone ketone peroxide, cyclohexane peroxide, dicumyl peroxide, diiso Hydroperoxides such as propylbenzene hydroperoxide, etc., ketone peroxides, diarylperoxide Organic peroxides such as oxides and peroxyesters, and the like can be mentioned.
  • the compounding amount of the component (b) is 0.1 to 5 parts by weight, preferably 0.5 to 4 parts by weight based on 100 parts by weight of the component (a). In this case, if it is less than 0.1 part by weight, it is insufficient to cause a polymerization reaction, and if it is more than 5 parts by weight, the storage stability of the thermosetting composition is reduced.
  • the component (c) used in the present invention is a compound having at least one glycidyl group in the molecule.
  • the glycidyl group is also called an oxysilane ring or ethylene oxide, and a compound having a glycidyl group is sometimes simply called an epoxy resin.
  • a typical example of the component (c) is an epoxy resin containing an average of two or more epoxy groups per molecule.
  • bisphenol A epoxy resin bisphenol F epoxy resin, bisphenol S epoxy resin , Glycidyl dimer ester type epoxy resin, polyalkylene ether type epoxy resin, phenol novolak type epoxy resin, orthocresol nopolak type epoxy resin, biphenyl type epoxy resin, dicyclopentadiene type epoxy resin, naphthol type epoxy resin Resin, naphthalene type epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, diglycidyl epoxy resin, glycidylamine type epoxy resin, etc., and these may be used alone or in combination of two or more. May be.
  • Epoxy resins containing only one glycidyl group in the molecule are usually low molecular weight compounds, and are called reactive diluents for epoxy resins, and are used to adjust viscosity, adjust physical properties of cured products, and adjust curing speed. To be added.
  • the component (c) is blended in an amount of 30 to 200 parts by weight, preferably 30 to 100 parts by weight, based on 100 parts by weight of the component (a). If the amount is less than 300 parts by weight, the amount of art gas generated during curing increases, and if it is more than 200 parts by weight, the anaerobic curability deteriorates.
  • the component (d) is an amine compound.
  • Component (d) acts as a curing agent for component (c).
  • examples of the amine compounds include heterocyclic compounds such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine.
  • the mixing ratio of the component (d) is 0.1 to 10 parts by weight with respect to 100 parts by weight of the total amount of the component (a) and the component (c). If the compounding ratio of the curing agent is less than 0.1 part by weight, there is no effect as a curing agent, and if it exceeds 10 parts by weight, the storage stability deteriorates. However, when it is desired to add more than 10 parts by weight, for example, to further improve the curability, the component (d) is not added to the present composition, but becomes two-part when mixed when used. It is also possible. In this case, the amount of the component (d) exceeding 10 parts by weight may be separately mixed, or the entire component (d) may be separately mixed.
  • a component that promotes polymerization of component (a), that is, anaerobic curability can be added to the present composition.
  • the polymerization accelerator include o-benzoxyl humide, a mercaptan compound, and a hydrazine compound.
  • the mercaptan compound include straight-chain mercaptans such as n-dodecyl mercaptan, ethyl mercaptan, and butyl mercaptan.
  • the hydrazine compound As the hydrazine compound,
  • the present invention can further use various additives.
  • a radical absorbent such as benzoquinone, hydroquinone, or hydroquinone monomethinoleate, ethylenediamine tetraacetic acid or its 2-sodium salt, oxalic acid, acetylaceton, o-- Metal chelating agents such as aminophenol may be added.
  • These additives for improving the storage stability are preferably 0 to 1 part by weight based on 100 parts by weight of the component (a).
  • a thickener a filler, a plasticizer, a colorant, and the like can be used as needed to adjust the properties of the anaerobic curable resin and the properties of the cured product.
  • a curing accelerator can be used to accelerate anaerobic curability.
  • the curing accelerator is obtained by dissolving a metal complex useful for improving anaerobic curability in an organic solvent, and is generally called a primer.
  • the solvent is volatilized by applying it to the adherend in advance, and the metal complex adheres to the surface of the adherend, which has the effect of accelerating the anaerobic curing of the anaerobic adhesive to be applied later.
  • various copper complexes typified by copper 2-ethylhexanoate and copper naphthenate, and vanadium are generally used, but any metal complex that improves anaerobic curability can be used. Can be used.
  • the composition of the present invention has anaerobic curability, air or oxygen is cut off by applying and bonding or fitting to an adherend, and the composition is cured and adhered. This is due to the fact that the components (a) and (b) harden and develop an adhesive force. (C) The component is not cured at this point, but is cured by heating in the baking step, and the entire composition is completely cured. Then, a cured product that hardly generates outgas can be obtained.
  • an acrylyl monomer mixture (1: 1 mixture of BP-2EM (Kyoeisha Chemical) and light ester HO (Kyoeisha Chemical) was used as the component (a).
  • BP-2EM Kinyoeisha Chemical
  • HO light ester HO
  • component (a) an acrylyl monomer mixture
  • 2 parts by weight of cumene hydroperoxide as a component (b)
  • 1 part by weight of o-benzoituxulamide as a polymerization accelerator
  • a component (c) the following Table 1
  • the amount of Epicot 828 (oiled shell epoxy) and Epicot 807 (oiled shell epoxy) shown in 11 were blended.
  • an adhesive was prepared using 5 parts by weight of 1-benzyl-1-methylimidazole with respect to 100 parts by weight of the component (a).
  • adhesives were prepared by changing the composition as shown in Tables 12 and 13 below.
  • the test piece used in the set time test and the adhesive strength test was made of SPCC_SD, 100 mm x 25 mm (JISG3141), and 0.5 parts of 2-ethylhexane was used as a primer in 100 parts of acetoneton. What melt
  • Comparative Example 1 Comparative Example 2 Comparative Example 3 Specific Acryl Monomer Mixture 100 100 100 Cumene Halo Dropperoxide 2 2 2 Polymerization Accelerator 1 1 1 Epicoat 828 0 20 0 Epicoat 807 0 0 10
  • the composition of the present invention shows a remarkable decrease in the amount of art gas generated as compared with Comparative Example 1 which is a conventional thermosetting adhesive to which the component (c) was not added. Can be Also, the set time and strength are satisfactory. As a matter of course, as in Comparative Example 4 and Comparative Example 6, the composition without the component (a) and the component Z or the component (b) did not result in curing.
  • the present invention has the quick curing property unique to the anaerobic curable composition and the easiness of the bonding step, and can drastically reduce the amount of outgas generated. Therefore, the present composition can be used in locations where art gas, such as HDD, is problematic when generated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne une composition de durcissement anaérobie constituée de (a) 100 parties en poids d'un composé ayant au moins un groupe fonctionnel polymérisable à radical dans la molécule, (b) entre 0,1 et 5 parties en poids d'un peroxyde organique, (c) entre 30 et 2 000 parties en poids d'un composé ayant au moins un groupe glycidyle dans la molécule, et (d) entre 0,1 et 10 parties en poids d'un composé d'amine pour 100 parties en poids de la quantité totale des composants (a) et (c). La composition de durcissement anaérobie retient les propriétés de durcissement rapide et de facilité d'adhésion présente une capacité de bulles réduites par rapport aux compositions de l'art antérieur.
PCT/JP2004/006131 2003-05-09 2004-04-28 Composition de durcissement anaerobie WO2004099284A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2003131837A JP2004331879A (ja) 2003-05-09 2003-05-09 嫌気硬化性組成物
JP2003-131837 2003-05-09

Publications (1)

Publication Number Publication Date
WO2004099284A1 true WO2004099284A1 (fr) 2004-11-18

Family

ID=33432147

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/006131 WO2004099284A1 (fr) 2003-05-09 2004-04-28 Composition de durcissement anaerobie

Country Status (2)

Country Link
JP (1) JP2004331879A (fr)
WO (1) WO2004099284A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114015397A (zh) * 2021-11-16 2022-02-08 Tcl华星光电技术有限公司 框胶和液晶显示面板

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5713170B2 (ja) 2010-03-18 2015-05-07 スリーボンドファインケミカル株式会社 硬化性組成物
CN103282402A (zh) * 2010-12-24 2013-09-04 三键株式会社 厌氧固化性组合物
WO2015125354A1 (fr) * 2014-02-20 2015-08-27 スリーボンドファインケミカル株式会社 Agent adhésif à durcissement anaérobie

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145781A (en) * 1978-03-29 1979-11-14 Loctite Corp Anaerobic composition and stabilizing method
JPS5765712A (en) * 1980-10-11 1982-04-21 Suriibondo:Kk Curable composition
JPS60235827A (ja) * 1984-04-28 1985-11-22 チバ‐ガイギー　アクチエンゲゼルシヤフト 硬化性組成物
JPH02502652A (ja) * 1987-12-22 1990-08-23 ソシエテ・ナシオナル・エルフ・アキテーヌ 化学的に安定な嫌気性アクリル系接着配合物
JPH03294329A (ja) * 1990-04-13 1991-12-25 Cemedine Co Ltd 樹脂組成物
JPH05105862A (ja) * 1991-10-14 1993-04-27 Three Bond Co Ltd 二液型接着剤
JP2004169912A (ja) * 2002-11-07 2004-06-17 Osaka Gas Co Ltd 配管用シール工法とシール剤

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145781A (en) * 1978-03-29 1979-11-14 Loctite Corp Anaerobic composition and stabilizing method
JPS5765712A (en) * 1980-10-11 1982-04-21 Suriibondo:Kk Curable composition
JPS60235827A (ja) * 1984-04-28 1985-11-22 チバ‐ガイギー　アクチエンゲゼルシヤフト 硬化性組成物
JPH02502652A (ja) * 1987-12-22 1990-08-23 ソシエテ・ナシオナル・エルフ・アキテーヌ 化学的に安定な嫌気性アクリル系接着配合物
JPH03294329A (ja) * 1990-04-13 1991-12-25 Cemedine Co Ltd 樹脂組成物
JPH05105862A (ja) * 1991-10-14 1993-04-27 Three Bond Co Ltd 二液型接着剤
JP2004169912A (ja) * 2002-11-07 2004-06-17 Osaka Gas Co Ltd 配管用シール工法とシール剤

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114015397A (zh) * 2021-11-16 2022-02-08 Tcl华星光电技术有限公司 框胶和液晶显示面板

Also Published As

Publication number Publication date
JP2004331879A (ja) 2004-11-25

Similar Documents

Publication Publication Date Title
TWI811288B (zh) 一液型樹脂組成物
JP5360359B2 (ja) エポキシ樹脂組成物
EP3596182B1 (fr) Adhésif hybride époxyde-acrylique
JP2009051954A (ja) 光および加熱硬化性組成物とその硬化物
JPWO2015060439A1 (ja) 柔軟性エポキシ樹脂組成物
JP2008001867A (ja) 硬化性樹脂組成物
WO2016143777A1 (fr) Composition de résine, agent adhésif, et agent d'étanchéité
JP2008297399A (ja) 熱伝導性接着剤組成物及び接着方法
KR20000023374A (ko) 열경화형 감압성 접착제 및 이의 접착시트
CA1128234A (fr) Colles
JP4745670B2 (ja) 二液主剤型アクリル系接着剤用ｂ剤
JPH01168777A (ja) 接着剤組成物
WO2004099284A1 (fr) Composition de durcissement anaerobie
JP4883264B2 (ja) 加熱硬化型一液性樹脂組成物
JPH05105862A (ja) 二液型接着剤
WO2014014045A1 (fr) Composition durcissable pour lecteur de disque dur
JP4645804B2 (ja) 液晶表示装置用硬化性組成物
KR20070103025A (ko) 가열 경화형 일액성 수지 조성물
JPH07216336A (ja) フレキシブル印刷配線板用接着剤組成物
JPH0680937A (ja) 主剤−プライマー型アクリル系接着剤
JP2009275160A (ja) 接着方法
WO2005010056A1 (fr) Composition a durcissement anaerobie
JPH05331447A (ja) 室温硬化型二液性組成物
JP2839348B2 (ja) アクリル系接着剤組成物
JP3661626B2 (ja) 嫌気硬化性組成物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase