JP5501241B2 - 耐熱性、嫌気硬化性組成物 - Google Patents
耐熱性、嫌気硬化性組成物 Download PDFInfo
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- JP5501241B2 JP5501241B2 JP2010532033A JP2010532033A JP5501241B2 JP 5501241 B2 JP5501241 B2 JP 5501241B2 JP 2010532033 A JP2010532033 A JP 2010532033A JP 2010532033 A JP2010532033 A JP 2010532033A JP 5501241 B2 JP5501241 B2 JP 5501241B2
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- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 19
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- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
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- 125000004429 atom Chemical group 0.000 claims 1
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
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- NQUSVAQGTYCOGL-UHFFFAOYSA-N cyclohexen-1-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CCCCC1 NQUSVAQGTYCOGL-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
- C08L2666/06—Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Description
本発明は、高い温度条件に対して耐性を示す嫌気硬化性組成物に関する。
一般に、嫌気接着剤組成物は周知である。例えば、R.D.Richによる、接着剤技術ハンドブック中の「嫌気接着剤」[Anaerobic Adhesives in Handbook of Adhesive Technology,29,467−79,A.Pizzi and K.L.Mittal,eds.,Maecel Dekker,Inc.,New York(1994)]およびそこに挙げられている参考文献を参照されたし。これらの組成物は多数利用され、新規の用途開発が続いている。
好ましくは、このハロゲン化ポリオレフィンのハロゲンはフッ素である。
R、R1、R2およびR3は、同じであっても、または異なっていてもよく、上で定義されたもの、および1から約30個の炭素原子有するシクロアルキル、シクロアルケニル、およびアリールであり、但しヘテロ原子、および複素環式構造によって置換されていても、または割り込まれていてもよく、または
R1およびR3は、共に結合して約20から約28個の環原子を有する環状構造を形成していてもよく、そして共にトリチアジアザペンタレン構造で置換または割り込まれていてもよいジアルキル置換ポリエーテル構造を表し、このトリチアジアザペンタレン構造はそれ自体、上で定義されたものと同じA1、R2、またはR3によって置換されていてもまたは置換されていなくてもよい。米国特許第6,583,289号(McArdle)公報を参照されたし。
下の表1には3つの試料を示しており、試料No.1は試料No.2およびNo.3に対するコントロールとしての役を果たし、試料No.2−4は、本発明の実施形態バージョンである。
ここで、2つの異なった高い温度(280℃および350℃)で3日間曝して相対的なシール性を決定するために、LOCTITE PST 567に対抗して試料No.3を評価した。LOCTITE PST 567は、ビスフェノールAフマレート樹脂(30−60重量%)、ポリグリコールジメタクリレート(10−30重量%)、ポリグリコールラウレート(10−30重量%)、ポリエチレングリコールモノココエート(10−30重量%)、ポリ(テトラフルオロエチレン)(5−10重量%)、二酸化チタン
(1−5重量%)、シリカ(1−5重量%)およびサッカリン(1−5重量%)を含む。
Claims (13)
- 嫌気硬化性組成物であって、
(a)(メタ)アクリレート成分;
(b)嫌気硬化システム;および
(c)IA族またはIIA族元素と、フッ素との化合物;および
(d)任意に、ポリオレフィン、ハロゲン化ポリオレフィンおよびこれらの組合せ;を含む、組成物。 - 前記(c)の化合物はIIA族元素と、フッ素との化合物である、請求項1に記載の組成物。
- 前記IIA族元素はカルシウムである、請求項2に記載の組成物。
- 前記(c)の化合物はCaF2である、請求項1に記載の組成物。
- 前記(メタ)アクリレート成分が、H2C=CGCO2R1で表され、ここでGは、H、ハロゲンおよび1から4個の炭素原子を有するアルキルからなる群より選択されるものであり、R1は、1から16個の炭素原子を有するアルキル、シクロアルキル、アルケニル、シクロアルケニル、アルカリール、およびアリール基からなる群より選択されるものである(但し、これらの基は、シラン、シリコン、酸素、ハロゲン、カルボニル、ヒドロキシル、エステル、カルボン酸、尿素、ウレタン、カルバメート、アミン、アミド、硫黄、スルホネートおよびスルホンからなる群より選択されるものによって置換されているかまたは割り込まれていても、または置換されていないかまたは割り込まれていなくてもよい。)、請求項1に記載の組成物。
- 前記(メタ)アクリレート成分が、シリコーン(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、ビスフェノール−A−(メタ)アクリレート、エトキシ化ビスフェノール−A−(メタ)アクリレート、ビスフェノール−F−(メタ)アクリレート、エトキシ化ビスフェノール−F−(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレートおよびジ(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、およびトリメチロールプロパントリ(メタ)アクリレートからなる群より選択される、請求項1に記載の組成物。
- 前記嫌気硬化システムが、下記:
A.サッカリン、トルイジン、アセチルフェニルヒドラジン、マレイン酸、およびキノンの組合せ;
B.以下の2種類の化合物の少なくともいずれか一方、
C.
D.
E.下記の構造:
AおよびA1は、各々独立して、OおよびNからなる群より選択され(ただし、AがOの場合、R1は存在せず、A1がOの場合、R3は存在しない。);
R、R1、R2およびR3は、同じであるかまたは異なっており、上で定義されたもの、または1から30個の炭素原子有するシクロアルキル、シクロアルケニル、またはアリールであり、但しヘテロ原子、または複素環式構造によって置換されていても、または割り込まれていてもよく、または
R1およびR3は、共に結合して20から28個の環原子を有する環状構造を形成していてもよく、そして共にトリチアジアザペンタレン構造で置換されていてもまたは割り込まれていてもよいジアルキル置換ポリエーテル構造を表し、このトリチアジアザペンタレン構造はそれ自体、上で定義されたものと同じA1、R2、またはR3によって置換されていてもまたは置換されていなくてもよく;および
F.トリアジンおよびチオールの組合せ、
の1種類以上を含む、請求項1に記載の組成物。 - 前記ポリオレフィンが、存在し、ポリエチレン、ポリプロピレン、ポリブチレンおよびこれらのコポリマーおよび組合せからなる群より選択される、請求項1に記載の組成物。
- 前記ハロゲン化ポリオレフィンが、存在し、ハロゲン化ポリエチレン、ハロゲン化ポリプロピレン、ハロゲン化ポリブチレンおよびこれらのコポリマーおよび組合せからなる群より選択される、請求項1に記載の組成物。
- 前記ハロゲン化ポリオレフィンのハロゲンが、フッ素である、請求項9に記載の組成物。
- 請求項1に記載の組成物の反応生成物。
- 嫌気硬化性組成物からの反応生成物を製造するための方法であって、以下のステップ:請求項1に記載の嫌気硬化性組成物を所望の基体表面に塗布するステップおよび組成物をそれが硬化するのに十分な時間嫌気環境に曝すステップを含む、方法。
- 請求項1に記載の組成物を硬化することで接着された2つの基体を含む複合体。
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PCT/US2008/012197 WO2009058250A2 (en) | 2007-10-29 | 2008-10-28 | Thermally resistant anaerobically curable compositions |
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JP2015525263A (ja) * | 2012-05-30 | 2015-09-03 | ヘンケル ユーエス アイピー エルエルシー | シール性能を改善する基材を被覆するための樹脂組成物 |
CN102703018B (zh) * | 2012-05-30 | 2014-06-25 | 朱立超 | 一种粘合剂及其制备方法 |
CN103342966B (zh) * | 2013-07-02 | 2015-03-18 | 广东恒大新材料科技有限公司 | 一种高强度耐高温型结构厌氧胶及其制备方法 |
CN104152086B (zh) * | 2014-08-08 | 2017-01-18 | 黑龙江省科学院石油化学研究院 | 一种改性丙烯酸酯耐高温厌氧胶粘剂及其制备方法 |
KR102198770B1 (ko) * | 2014-08-14 | 2021-01-05 | 덴카 주식회사 | 에너지선 경화성 접착제 |
CN104934550A (zh) * | 2015-05-07 | 2015-09-23 | 京东方科技集团股份有限公司 | Oled器件的封装结构、封装方法以及电子设备 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3218305A (en) | 1963-12-26 | 1965-11-16 | Loctite Corp | Accelerated anaerobic compositions and method of using same |
US3419512A (en) * | 1965-12-23 | 1968-12-31 | Borden Inc | Anaerobic curing composition |
US3851017A (en) | 1970-11-12 | 1974-11-26 | Loctite Corp | Thixotropic anaerobic composition |
US3988299A (en) * | 1974-10-10 | 1976-10-26 | Loctite Corporation | Anaerobic adhesive composition having improved strength at elevated temperature consisting of unsaturated diacrylate monomer and maleimide additive |
US4321349A (en) | 1975-05-23 | 1982-03-23 | Loctite Corporation | Accelerator for curable compositions |
US4287330A (en) * | 1975-05-23 | 1981-09-01 | Loctite Corporation | Accelerator for curable compositions |
IE43811B1 (en) | 1976-11-08 | 1981-06-03 | Loctite Ltd | Curable acrylate ester compositions containing hydrazine acelerators and acid co-accelerators |
CA1161586A (en) * | 1979-10-19 | 1984-01-31 | James P. Moran, Jr. | Anaerobically curing rubber adhesive compositions |
US4447588A (en) | 1980-11-03 | 1984-05-08 | Minnesota Mining & Manufacturing Company | Anaerobically-curing compositions |
US4500608A (en) | 1980-11-03 | 1985-02-19 | Minnesota Mining And Manufacturing Company | Anaerobically-curing compositions |
US4413108A (en) | 1980-11-03 | 1983-11-01 | Minnesota Mining & Manufacturing Company | Anaerobically-curing compositions |
US4528059A (en) | 1981-08-03 | 1985-07-09 | Minnesota Mining & Manufacturing Company | Anaerobically-cuting compositions |
LU85627A1 (fr) * | 1984-11-05 | 1986-06-04 | Trazollah Ouhadi | Procede de polymerisation de monomeres acryliques et eventuellement de co-monomeres non acryliques |
US4990281A (en) * | 1985-08-30 | 1991-02-05 | Loctite Corporation | Adhesion promoting primer activator for an anaerobic compositions |
AU646148B2 (en) * | 1991-03-06 | 1994-02-10 | Loctite (Ireland) Limited | Air-activatable polymerisable compositions |
US5605999A (en) | 1995-06-05 | 1997-02-25 | Loctite Corporation | Anaerobically curable silicones |
US5811473A (en) | 1996-04-02 | 1998-09-22 | Loctite Corporation | Primer activator composition for anaerobic adhesives |
DE69729378T2 (de) * | 1996-04-15 | 2005-06-02 | Lord Corp. | Frei radikalisch polymerisierbare zusammensetzungen, die parahalogenierte anilin derivate enthalten |
US6043327A (en) * | 1997-07-03 | 2000-03-28 | Loctite Corporation | Anaerobic adhesive compositions of acrylates coreactants and maleimides curable under ambient conditions |
CN1158314C (zh) * | 1997-07-03 | 2004-07-21 | 洛克泰特公司 | 室温固化的可控强度耐高温厌氧粘合剂组合物 |
US6150479A (en) * | 1998-11-23 | 2000-11-21 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
US6342545B1 (en) * | 1998-11-23 | 2002-01-29 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
WO2000040664A1 (en) | 1999-01-08 | 2000-07-13 | Loctite (R & D) Limited | Novel curative for anaerobic adhesive compositions |
CN1181152C (zh) * | 1999-06-11 | 2004-12-22 | 株式会社三键 | 厌氧可固化的组合物 |
WO2001051576A1 (en) * | 2000-01-11 | 2001-07-19 | Loctite (R & D) Limited | Acrylic adhesive compositions containing ketonyl (meth)acrylate |
US6800671B1 (en) * | 2000-04-21 | 2004-10-05 | Britesmile, Inc. | Low peak exotherm curable compositions |
AU2002211251A1 (en) * | 2000-09-25 | 2002-04-08 | Henkel Loctite Corporation | Rapid curing anaerobic compositions |
US6632908B1 (en) * | 2002-03-12 | 2003-10-14 | Henkel Loctite Corporation | Bonding system having adherence to low energy surfaces |
US6835762B1 (en) * | 2002-05-31 | 2004-12-28 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
US6958368B1 (en) * | 2002-05-31 | 2005-10-25 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
US6897277B1 (en) * | 2003-12-22 | 2005-05-24 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
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Publication number | Publication date |
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EP2207850A4 (en) | 2011-10-19 |
ES2426615T3 (es) | 2013-10-24 |
JP2011502199A (ja) | 2011-01-20 |
EP2207850B1 (en) | 2013-06-05 |
KR20100102596A (ko) | 2010-09-24 |
KR101603349B1 (ko) | 2016-03-14 |
WO2009058250A2 (en) | 2009-05-07 |
MX2010004765A (es) | 2010-07-02 |
WO2009058250A3 (en) | 2009-08-06 |
US20100086796A1 (en) | 2010-04-08 |
US8835533B2 (en) | 2014-09-16 |
CA2703865A1 (en) | 2009-05-07 |
CA2703865C (en) | 2016-01-05 |
EP2207850A2 (en) | 2010-07-21 |
CN101889057B (zh) | 2013-06-19 |
CN101889057A (zh) | 2010-11-17 |
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