JP6766035B2 - ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 - Google Patents
ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 Download PDFInfo
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- JP6766035B2 JP6766035B2 JP2017515173A JP2017515173A JP6766035B2 JP 6766035 B2 JP6766035 B2 JP 6766035B2 JP 2017515173 A JP2017515173 A JP 2017515173A JP 2017515173 A JP2017515173 A JP 2017515173A JP 6766035 B2 JP6766035 B2 JP 6766035B2
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
- C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/778—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur silicon
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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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)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
Description
a)イソシアネート基を含有する少なくとも1種のポリウレタンポリマー、
b)少なくとも1種のシラン接着促進剤、
c)少なくとも1種のアミン触媒、および
d)少なくとも1種のキレート錯化剤
を含んでなる湿気硬化接着剤組成物である。
−架橋剤、例えば、MDI、TDI、HDIまたはIPDIなどのジイソシアネートのオリゴマーおよび誘導体、特にイソシアヌレート、カルボジイミド、ウレトンイミド、ビウレット、アロファネートおよびイミノオキサジアジンジオン、あるいはMDIの混合物およびMDIホモログ(ポリマーMDIまたはPMDI);
−乾燥剤、例えば、p−トシルイソシアネートおよび他の反応性イソシアネート、酸化カルシウムまたはモレキュラーシーブ;
−レオロジー変性剤、例えば、国際公開第02/48228A2号パンフレットの第9〜11ページにチキソトロピー剤(「チキソトロピー付与剤」)として記載される種類の尿素化合物が例である増粘剤、ポリアミドワックス、ベントナイトまたはヒュームドシリカ;
−熱、光および紫外線に対する安定化剤;−燃焼抑制剤;
−界面活性物質、例えば、湿潤剤、流量調整剤、脱気剤または脱泡剤;
−殺生物剤、例えば、除藻剤または殺菌剤;
ならびに、例えば、ポリエチレンの繊維、染料、顔料または当業者に既知の他の補助剤などの1成分イソシアネート含有組成物で慣習的に使用されるさらなる物質。
a)20重量%〜50重量%の少なくとも1種のイソシアネート官能性ポリマー、
b)0.05重量%〜0.5重量%の少なくとも1種のシラン接着促進剤、好ましくは3−グリシジルオキシプロピルトリメトキシシラン、
c)0.15重量%〜0.6重量%の少なくとも1種のアミン触媒、好ましくはDMDEE、
d)0.005重量%〜0.1重量%の少なくとも1種の有機スズ(IV)化合物、
e)0.03重量%〜0.1重量%の少なくとも1種のキレート錯化剤、好ましくは8−ヒドロキシキノリンまたはジベンゾイルメタン、
f)30重量%〜50重量%の少なくとも1種の充てん剤、および
g)15重量%〜25重量%の少なくとも1種の可塑剤
を含んでなる。
引張強さおよび破断点伸びは、23℃(室温、「RT」)および50%の相対湿度において14日(d)間硬化された2mmの層厚を有するフィルム上でDIN EN ISO 527(引張速度:200mm/分)に従って決定した。
1=>95%の凝集破壊
2=75〜95%の凝集破壊
3=25〜75%の凝集破壊
4=<25%の凝集破壊
5=0%の凝集破壊(純粋に接着破壊)
1300gのポリオキシプロピレンジオール(Acclaim(登録商標)4200 N,Bayer MaterialScience AG,Germany;OH価28.5mg KOH/g)、2600gのポリオキシプロピレン−ポリオキシエチレントリオール(Caradol(登録商標)MD34−02,Shell Chemicals Ltd.,UK;OH価35.0mg KOH/g)、600gの4,4’−メチレンジフェニルジイソシアネート(4,4’−MDI;Desmodur(登録商標)44 MC L,Bayer MaterialScience AG,Germany)および500gのフタル酸ジイソデシル(DIDP;Palatinol(登録商標)Z,BASF SE,Germany)を80℃で既知の方法によって反応させ、2.05重量%の遊離イソシアネート基含有量を有するNCO末端ポリウレタンポリマーを形成した。
真空混合機中、表1で指定された成分を、指定され多量および指定された順序で添加し、そして混合して、そして混合物を、最後に20分間1000〜1200回転において減圧下で均質ペーストへと加工した。次いで、このペーストは、内部がコーティングされたアルミニウムガン適用カートリッジ中に分配された。
Claims (12)
- a)イソシアネート基を含有する少なくとも1種のポリウレタンポリマー、
b)少なくとも1種のシラン接着促進剤、
c)少なくとも1種のアミン触媒、
d)8−ヒドロキシキノリン、および
e)有機スズ(IV)化合物を含む金属触媒
を含んでなる湿気硬化接着剤組成物。 - 前記金属触媒が、全組成物に基づき、0.001重量%〜0.2重量%の範囲で存在する有機スズ(IV)化合物を含んでなることを特徴とする、請求項1に記載の湿気硬化接着剤組成物。
- 8−ヒドロキシキノリン対金属触媒のモル比が、2〜6の範囲であることを特徴とする、請求項1又は2に記載の湿気硬化接着剤組成物。
- 前記イソシアネート基含有ポリウレタンポリマーが、全組成物に基づき、10重量%〜70重量%の量で存在することを特徴とする、請求項1〜3のいずれか一項に記載の湿気硬化接着剤組成物。
- 前記シラン接着促進剤が、全組成物に基づき、0.01重量%〜1重量%の量で存在することを特徴とする、請求項1〜4のいずれか一項に記載の湿気硬化接着剤組成物。
- 前記アミン触媒が、全組成物に基づき、0.05重量%〜1重量%の量で存在することを特徴とする、請求項1〜5のいずれか一項に記載の湿気硬化接着剤組成物。
- 8−ヒドロキシキノリンが、全組成物に基づき、0.01重量%〜0.5重量%の量で存在することを特徴とする、請求項1〜6のいずれか一項に記載の湿気硬化接着剤組成物。
- 前記アミン触媒が、2,2’−ジモルホリノジエチルエーテルまたはその誘導体を含んでなることを特徴とする、請求項1〜7のいずれか一項に記載の湿気硬化接着剤組成物。
- 前記シラン接着促進剤が、3−グリシジルオキシプロピルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、3−メルカプトプロピルトリメトキシシランおよび3−メタクリルオキシオキシプロピルトリメトキシシランからなる群から選択されることを特徴とする、請求項1〜8のいずれか一項に記載の湿気硬化接着剤組成物。
- シラン接着促進剤と、アミン触媒と、有機スズ(IV)化合物を含む金属触媒とを含んでなるポリウレタンをベースとする湿気硬化接着剤組成物が、8−ヒドロキシキノリンと混合されることを特徴とする、前記湿気硬化接着剤組成物の安定化方法。
- 接着剤または封着剤としての請求項1〜9のいずれか一項に記載の湿気硬化接着剤組成物の使用。
- 請求項1〜9のいずれか一項に記載の湿気硬化接着剤組成物を水で硬化することにより得られうる硬化組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14185761.5 | 2014-09-22 | ||
EP14185761 | 2014-09-22 | ||
PCT/EP2015/070117 WO2016045927A1 (de) | 2014-09-22 | 2015-09-22 | Lagerstabiler, feuchtigkeitshärtender polyurethanklebstoff mit raschem haftungsaufbau auf glas |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020119431A Division JP2020180296A (ja) | 2014-09-22 | 2020-07-10 | ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017533299A JP2017533299A (ja) | 2017-11-09 |
JP2017533299A5 JP2017533299A5 (ja) | 2018-10-18 |
JP6766035B2 true JP6766035B2 (ja) | 2020-10-07 |
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ID=51582301
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Application Number | Title | Priority Date | Filing Date |
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JP2017515173A Active JP6766035B2 (ja) | 2014-09-22 | 2015-09-22 | ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 |
JP2020119431A Pending JP2020180296A (ja) | 2014-09-22 | 2020-07-10 | ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 |
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JP2020119431A Pending JP2020180296A (ja) | 2014-09-22 | 2020-07-10 | ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10494552B2 (ja) |
EP (1) | EP3197930B1 (ja) |
JP (2) | JP6766035B2 (ja) |
CN (1) | CN107075076B (ja) |
BR (1) | BR112017004058A2 (ja) |
ES (1) | ES2964777T3 (ja) |
WO (1) | WO2016045927A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109071749A (zh) * | 2016-11-14 | 2018-12-21 | 积水化学工业株式会社 | 湿气固化型树脂组合物和组装部件 |
CN111040707A (zh) * | 2018-10-12 | 2020-04-21 | 苏州美山子制衣有限公司 | 布料点胶机用胶水及其制备方法 |
US20230383156A1 (en) * | 2020-10-14 | 2023-11-30 | Ddp Specialty Electronic Materials Us, Llc | One-component polyurethane adhesive |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD108103A1 (ja) * | 1973-11-29 | 1974-09-05 | ||
US5290853A (en) * | 1990-06-15 | 1994-03-01 | Chemrex Inc. | Ambient moisture-curing polyurethane adhesive |
US6274674B1 (en) * | 1999-02-25 | 2001-08-14 | Ashland Inc. | Reactive hot melt adhesive |
JP4326181B2 (ja) | 2000-01-19 | 2009-09-02 | サンスター技研株式会社 | 湿気硬化性一液型ウレタン系接着剤組成物 |
JP2002179753A (ja) | 2000-12-13 | 2002-06-26 | Nippon Shiika Kk | 高耐候性ポリウレタン系一液型湿気硬化性組成物 |
RU2305079C2 (ru) * | 2001-11-29 | 2007-08-27 | Дау Глобал Текнолоджиз Инк. | Способ соединения стекла с субстратом без использования грунтовки |
EP1408062A1 (de) | 2002-10-08 | 2004-04-14 | Sika Technology AG | Bismutkatalysierte Polyurethanzusammensetzung |
US7834123B2 (en) * | 2006-05-19 | 2010-11-16 | Henkel Ag & Co. Kgaa | Two component polyurethane adhesive |
JP5765938B2 (ja) * | 2007-10-17 | 2015-08-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有機金属化合物を主成分とする光潜伏性触媒 |
US9309439B2 (en) * | 2010-07-22 | 2016-04-12 | Construction Research & Technology Gmbh | Sealant and adhesive using green prepolymer |
EP2604617A1 (de) * | 2011-12-12 | 2013-06-19 | Sika Technology AG | Eisen(III)-Komplexverbindungen als Katalysatoren für Polyurethan-Zusammensetzungen |
EP2604615A1 (de) * | 2011-12-12 | 2013-06-19 | Sika Technology AG | Bismuthaltiger Katalysator für Polyurethan-Zusammensetzungen |
EP2706075A1 (de) | 2012-09-11 | 2014-03-12 | Sika Technology AG | Struktureller Polyurethanklebstoff mit tiefer Glasübergangstemperatur |
-
2015
- 2015-09-22 WO PCT/EP2015/070117 patent/WO2016045927A1/de active Application Filing
- 2015-09-22 ES ES15791252T patent/ES2964777T3/es active Active
- 2015-09-22 BR BR112017004058-1A patent/BR112017004058A2/pt not_active Application Discontinuation
- 2015-09-22 EP EP15791252.8A patent/EP3197930B1/de active Active
- 2015-09-22 CN CN201580050725.4A patent/CN107075076B/zh active Active
- 2015-09-22 US US15/505,822 patent/US10494552B2/en active Active
- 2015-09-22 JP JP2017515173A patent/JP6766035B2/ja active Active
-
2020
- 2020-07-10 JP JP2020119431A patent/JP2020180296A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP2020180296A (ja) | 2020-11-05 |
EP3197930B1 (de) | 2023-11-08 |
WO2016045927A1 (de) | 2016-03-31 |
US20170275509A1 (en) | 2017-09-28 |
JP2017533299A (ja) | 2017-11-09 |
CN107075076A (zh) | 2017-08-18 |
CN107075076B (zh) | 2020-10-16 |
EP3197930A1 (de) | 2017-08-02 |
BR112017004058A2 (pt) | 2018-01-23 |
US10494552B2 (en) | 2019-12-03 |
ES2964777T3 (es) | 2024-04-09 |
EP3197930C0 (de) | 2023-11-08 |
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