JP6073131B2 - 嫌気硬化性組成物用の硬化促進剤 - Google Patents
嫌気硬化性組成物用の硬化促進剤 Download PDFInfo
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- JP6073131B2 JP6073131B2 JP2012508670A JP2012508670A JP6073131B2 JP 6073131 B2 JP6073131 B2 JP 6073131B2 JP 2012508670 A JP2012508670 A JP 2012508670A JP 2012508670 A JP2012508670 A JP 2012508670A JP 6073131 B2 JP6073131 B2 JP 6073131B2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08K5/14—Peroxides
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Indole Compounds (AREA)
Description
本発明は、嫌気硬化性組成物、例えば、接着剤およびシーラントのための有用な硬化促進剤に関し、その硬化促進剤は、下記の構造A:
嫌気接着組成物は一般に周知である。例えば、R.D.Rich「嫌気接着剤(Anaerobic Adhesives)」[接着剤技術ハンドブック(Handbook of Adhesive Technology)、第29章、467〜79頁、A.Pizzi、K.L.Mittal編、Marcel Dekker,Inc.、New York(1994年)]およびそこに引用されている参考文献を参照。それらは数多く使用され、新規の用途が引き続き開発されている。
上記のように本発明は、下記の構造A:
APHの代替品としてグリシドールとインドリンまたはTHQとの反応生成物(単数または複数)およびある種のアルキル化インドリンまたはTHQ付加物を、嫌気硬化性組成物、例えば、接着剤における硬化促進剤として評価するために研究を実施した。
下記の表にリストした成分を使用して、評価のための嫌気硬化性組成物を作製した。
接着剤配合物が82℃で3時間以上、液体のままである場合、その配合物は許容できる保存期間安定性を有すると判定する評価に従って、配合物の82℃での安定性を決定した。トルイジンパッケージ、THQ、インドリンの各々自体を含有する配合物の評価と同様に、N−メチルTHQまたはN−メチルインドリンのいずれかを含有する配合物について各々の3つの試験片を82℃で評価した。各配合物は、この温度で24時間を超えて液体のままであった。
破壊/優性接着力試験(break/prevail adhesion testing)をASTM D5649に従って行った。破壊トルクは、固定した組立品において軸力を減少または除去するのに必要な初期トルクである。優性/トルク(prevail/torque)は、接合の初期破壊の後、ナットの360°回転中の任意の点で測定される。優性トルクは通常、ナットの180°回転で決定される。解除接着力試験を、ナットとボルトの台座との間のスペーサーを用いて行った。スチール3/8×16ナットおよびボルトを1,1,1−トリクロロエチレンで脱グリースし、接着剤をボルトに塗布し、スペーサーとしてスチールカラーを備えたボルトにナットをねじ込んだ。
Claims (13)
- (1)(a)構造I:
(b)
(i)構造II:
(ii)アルキル化剤、アルケニル化剤またはアルカリル化剤、
のいずれかと、
を含む反応体から嫌気硬化性組成物の硬化を促進するための反応生成物を調製するステップと、
(2)前記反応生成物を(メタ)アクリレート成分および嫌気硬化システムと混合するステップと、
を含む、嫌気硬化性組成物の製造方法。 - 前記(a)において構造Iで表される化合物が、1,2,3,4−テトラヒドロキノリン、インドリンまたはインドールである、請求項1に記載の製造方法。
- 前記(b)において構造IIで表される化合物が、グリシドールである、請求項1または2に記載の製造方法。
- 前記(b)が(ii)アルキル化剤、アルケニル化剤またはアルカリル化剤であって、前記嫌気硬化性組成物の硬化を促進するための反応生成物が塩基の存在下で(a)および(b)を反応することによって調製される、請求項1〜3のいずれか1項に記載の製造方法。
- 前記(b)が、アルキルハライドである、請求項1〜4のいずれか1項に記載の製造方法。
- (1)(メタ)アクリレート成分と、
(2)嫌気硬化システムと、および
(3)構造A:
を含む、嫌気硬化性組成物。 - 前記嫌気硬化システムが、クメンヒドロペルオキシド、パラ−メンタンヒドロペルオキシド、t−ブチルヒドロペルオキシド、t−ブチルペルベンゾエート、ベンゾイルペルオキシド、ジベンゾイルペルオキシド、1,3−ビス(t−ブチルペルオキシイソプロピル)ベンゼン、ジアセチルペルオキシド、ブチル−4,4−ビス(t−ブチルパーオキシ)バリレート、p−クロロベンゾイルペルオキシド、t−ブチルクミルペルオキシド、t−ブチルペルベンゾエート、ジ−t−ブチルペルオキシド、ジクミルペルオキシド、2,5−ジメチル−2,5−ジ−t−ブチルペルオキシヘキサン、2,5−ジメチル−2,5−ジ−t−ブチル−ペルオキシヘキサ−3−イン、4−メチル−2,2−ジ−t−ブチルペルオキシペンタン、t−アミルヒドロペルオキシド、1,2,3,4−テトラメチルブチルヒドロペルオキシドおよびそれらの組合せからなる群より選択されるヒドロペルオキシドを含む、請求項6に記載の組成物。
- さらに、少なくとも1種の促進剤を含む、請求項6または7に記載の組成物。
- 前記促進剤が、アミン、アミンオキシド、スルホンアミド、金属および金属源、ならびにそれらの混合物からなる群より選択される、請求項8に記載の組成物。
- 前記促進剤が、トリアジン、エタノールアミン、ジエタノールアミン、トリエタノールアミン、N,N−ジメチルアニリン、ベンゼンスルホンイミド、シクロへキシルアミン、トリエチルアミン、ブチルアミン、サッカリン、N,N−ジエチル−p−トルイジン、N,N−ジメチル−o−トルイジン、アセチルフェニルヒドラジン、マレイン酸およびそれらの混合物からなる群より選択される、請求項8に記載の組成物。
- さらに、少なくとも1種の安定剤を含む、請求項6〜10のいずれか1項に記載の組成物。
- 前記安定剤が、ベンゾキノン、ナフトキノン、アントラキノン、ヒドロキノン、メトキシヒドロキノン、ブチル化ヒドロキシトルエン、エチレンジアミン四酢酸またはその塩、およびそれらの混合物からなる群より選択される、請求項11に記載の組成物。
- 嫌気硬化性組成物のための硬化促進剤として、構造A:
(a)(メタ)アクリレート成分および嫌気硬化誘導組成物を含む嫌気硬化性組成物を提供するステップ、
(b)嫌気硬化性組成物のための硬化促進剤として、構造A:
(c)前記嫌気硬化性組成物および前記硬化促進剤を、前記組成物を硬化するのに有利な条件に曝すステップ、
を含む、方法。
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US17461409P | 2009-05-01 | 2009-05-01 | |
US61/174,614 | 2009-05-01 | ||
PCT/US2010/032873 WO2010127055A2 (en) | 2009-05-01 | 2010-04-29 | Cure accelerators for anaerobic curable compositions |
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JP2012525417A JP2012525417A (ja) | 2012-10-22 |
JP6073131B2 true JP6073131B2 (ja) | 2017-02-01 |
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US (1) | US8481659B2 (ja) |
EP (1) | EP2424918A4 (ja) |
JP (1) | JP6073131B2 (ja) |
KR (1) | KR101514794B1 (ja) |
CN (1) | CN102686635B (ja) |
CA (1) | CA2760462C (ja) |
MX (1) | MX2011011029A (ja) |
WO (1) | WO2010127055A2 (ja) |
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GB2531052B (en) * | 2014-10-09 | 2017-04-26 | Henkel IP & Holding GmbH | Anaerobic curable compositions |
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JP2009046565A (ja) * | 2007-08-18 | 2009-03-05 | Konica Minolta Medical & Graphic Inc | 硬化性組成物 |
JP5428860B2 (ja) * | 2007-09-25 | 2014-02-26 | 株式会社スリーボンド | 嫌気硬化性組成物 |
CN101328395A (zh) * | 2008-07-31 | 2008-12-24 | 广东恒大新材料科技有限公司 | 一种厌氧胶组合物 |
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2010
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- 2010-04-29 CA CA2760462A patent/CA2760462C/en active Active
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- 2010-04-29 JP JP2012508670A patent/JP6073131B2/ja not_active Expired - Fee Related
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KR101514794B1 (ko) | 2015-04-24 |
MX2011011029A (es) | 2011-11-04 |
CA2760462C (en) | 2017-05-30 |
WO2010127055A3 (en) | 2011-03-31 |
CN102686635A (zh) | 2012-09-19 |
WO2010127055A2 (en) | 2010-11-04 |
EP2424918A2 (en) | 2012-03-07 |
KR20120028299A (ko) | 2012-03-22 |
CN102686635B (zh) | 2014-10-22 |
US8481659B2 (en) | 2013-07-09 |
US20120157641A1 (en) | 2012-06-21 |
EP2424918A4 (en) | 2013-03-27 |
JP2012525417A (ja) | 2012-10-22 |
CA2760462A1 (en) | 2010-11-04 |
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