JP2005513217A - 反応性ポリウレタン用接着性促進剤 - Google Patents
反応性ポリウレタン用接着性促進剤 Download PDFInfo
- Publication number
- JP2005513217A JP2005513217A JP2003554762A JP2003554762A JP2005513217A JP 2005513217 A JP2005513217 A JP 2005513217A JP 2003554762 A JP2003554762 A JP 2003554762A JP 2003554762 A JP2003554762 A JP 2003554762A JP 2005513217 A JP2005513217 A JP 2005513217A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- polyisocyanate
- polyurethane
- adhesives
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/809—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
イソシアヌレート化ヘキサメチレンジイソシアネート(分子量504.6g/mol、当量183g/mol、モノマー性HDIの残存量0.2%未満)59重量部をN−(n−ブチル)−3−アミノプロピルトリメトキシシラン41重量部と反応させた。反応はイソシアネート含有量が一定になるまでおこなった。反応生成物の粘度は1.7Pas/60℃であった。このシラン付加物は60℃で16時間にわたって溶融安定性を示し、また、室温においては優れた取扱い性を示した。
国際公開公報WO98/36007の教示内容に準拠して、IPDI 69重量部およびビス(3−トリエトキシシリルプロピル)アミン[ビス(3−トリエトキシシリルプロピル)アミン40%および3−アミノプロピルトリエトキシシラン60%を含有する]を基剤とする一般的な市販品であるアミノシラン31重量部を反応させた。反応はイソシアネート含有量が一定になるまでおこなった。高粘性のイソシアナト官能性シラン付加物(NCO含有量20%、粘度1Pa・s/20℃)が得られた。この調製物中のモノマー性IPDIの含有量は約35%であった。この通常の接着性促進剤は60℃においては十分な溶融安定性を示したが、7時間以内にその粘度は150mPasから200mPasへ約30%増加した。大過剰のモノマー性IPDIを含まない物質としては、このシラン付加物の溶融安定性は劣った。130℃においては、その粘度は6時間にわたって16Pasから91Pasへ約470%増加した。
未公開の独国特許出願DE10150722.4明細書の教示内容に従って、室温で液状、非晶質および結晶性のポリエステルの混合物(OH価:40.8)86.40部および2,4’−MDI(純度>97%)12.57部からホットメルト接着剤を調製した。実施例1で得られたシラン接着性促進剤1.03部をこのホットメルト接着剤へ添加した。130℃における粘度は6500mPas(サーモセルを備えたブルックフィールド粘度計を使用した測定値)であった。このホットメルト接着剤は良好な溶融安定性と加工性を示した。130℃で6時間の粘度増加率はわずかに約100%であった。
実施例2で得られたシラン接着性促進剤を使用する以外は実施例3の場合と同様の操作をおこなった。130℃で6時間の粘度増加率は約450%であった。
接着させた支持体を室温で7日間硬化させた後、試験体を、自動車工業において常用されている気候変化試験(VWP 1200規準による)に4日間付した。
V2A +
アルミニウム(未加工;99.5) +/−
鋼(未加工;ST37) +/−
PMMA +
PC +
PS +
硬質PVC +
PA6.6(未加工) +
Claims (6)
- 難揮発性脂肪族または脂環式ポリイソシアネートおよびツェレウィチノフ活性水素を含むNCO−反応性基を有する有機官能性シランから製造されるイソシアネート官能性シラン。
- ポリイソシアネートが5×10−5hPa/20℃未満の蒸気圧を有する請求項1記載のイソシアネート官能性シラン。
- 有機官能性シランが、ポリイソシアネートに対して1.3以下の官能価を有する請求項1または2記載のイソシアネート官能性シラン。
- ポリイソシアネートが、ヘキサメチレンジイソシアネート(HDI)のイソシアヌレート、イソホロンジイソシアネート(IPDI)のイソシアヌレート、および脂肪族もしくは脂環式ジイソシアネートと低分子量トリオールとの付加物から成る群から選択される請求項1〜3いずれかに記載のイソシアネート官能性シラン。
- 有機官能性シランが、NCO−反応性基としてヒドロキシ基、メルカプト基および/または第2アミノ基を有する請求項3または4記載のイソシアネート官能性シラン。
- ポリウレタン系の接着剤および封止剤、特にホットメルト接着剤または貼合せ接着剤における接着性促進剤としての請求項1〜5いずれかに記載のイソシアネート官能性シランの使用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10162642A DE10162642A1 (de) | 2001-12-20 | 2001-12-20 | Haftvermittler für reaktive Polyurethane |
PCT/EP2002/014057 WO2003054049A1 (de) | 2001-12-20 | 2002-12-11 | Haftvermittler für reaktive polyurethane |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005513217A true JP2005513217A (ja) | 2005-05-12 |
JP2005513217A5 JP2005513217A5 (ja) | 2006-01-05 |
JP4159472B2 JP4159472B2 (ja) | 2008-10-01 |
Family
ID=7709954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003554762A Expired - Fee Related JP4159472B2 (ja) | 2001-12-20 | 2002-12-11 | 反応性ポリウレタン用接着性促進剤 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20050032974A1 (ja) |
EP (1) | EP1456274B1 (ja) |
JP (1) | JP4159472B2 (ja) |
AT (1) | ATE444322T1 (ja) |
AU (1) | AU2002352240A1 (ja) |
DE (2) | DE10162642A1 (ja) |
ES (1) | ES2331235T3 (ja) |
WO (1) | WO2003054049A1 (ja) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10229519A1 (de) * | 2001-07-10 | 2003-01-30 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
EP1502927A1 (de) | 2003-07-31 | 2005-02-02 | Sika Technology AG | Isocyanatfreie Primerzusammensetzung für Glas und Glaskeramiken |
DE102004038274A1 (de) * | 2004-08-06 | 2006-03-16 | Henkel Kgaa | Bindemittel mit Barriere-Eigenschaften II |
EP1801138A1 (de) * | 2005-12-23 | 2007-06-27 | Sika Technology AG | Feuchtigkeitshärtende Heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles Polyurethanprepolymer |
EP1984417A2 (de) * | 2006-02-03 | 2008-10-29 | Basf Se | Durch energieeintrag reparable beschichtungen |
EP2113014A1 (en) * | 2007-02-23 | 2009-11-04 | NV Bekaert SA | A coupling agent to provide the coupling of a metal element to a material to be reinforced |
DE102007032666A1 (de) | 2007-07-13 | 2009-01-22 | Bayer Materialscience Ag | Allophanat- und Silangruppen enthaltende Polyisocyanate |
WO2009104161A2 (en) * | 2008-02-21 | 2009-08-27 | Sabmiller International Bv | A coating composition for strengthening glass |
DE102009016173A1 (de) | 2009-04-03 | 2010-10-14 | Bayer Materialscience Ag | Schutzlack |
DE102009019899A1 (de) | 2009-05-04 | 2010-11-11 | Fischerwerke Gmbh & Co. Kg | Klebstoffe auf Basis silanterminierter Isocyanate |
DE102009047964A1 (de) | 2009-10-01 | 2011-04-21 | Bayer Materialscience Ag | Hochfunktionelle Allophanat- und Silangruppen enthaltende Polyisocyanate |
DE102010060443A1 (de) | 2010-11-09 | 2012-05-10 | Fischerwerke Gmbh & Co. Kg | Harz für Kleb- und Beschichtungsstoffe auf Basis silanterminierter Harze mit mindestens zwei Edukten |
PL2638090T3 (pl) * | 2010-11-11 | 2015-07-31 | Dow Global Technologies Llc | Szczeliwo do szyb zespolonych na bazie poliuretanu |
WO2015140025A1 (de) * | 2014-03-17 | 2015-09-24 | Henkel Ag & Co. Kgaa | Polyurethan-klebstoff mit epoxidgruppen |
CN106414540B (zh) | 2014-06-13 | 2020-04-24 | 科思创德国股份有限公司 | 含硅烷基团的硫代脲基甲酸酯多异氰酸酯 |
KR20170129180A (ko) | 2015-03-17 | 2017-11-24 | 코베스트로 도이칠란트 아게 | 1,5-디이소시아네이토펜탄을 기재로 하는 실란 기 함유 폴리이소시아네이트 |
BR112020022227A2 (pt) | 2018-04-30 | 2021-02-02 | Dow Global Technologies Llc | composições adesivas de dois componentes com base em silanos terminados em isocianato e métodos para produzir as mesmas |
KR101932244B1 (ko) * | 2018-08-03 | 2019-03-20 | 성호정 | 폴리우레탄 도막 방수제, 그 제조방법 및 이를 이용한 방수공법 |
CA3136562A1 (en) | 2019-05-06 | 2020-11-12 | Basf Coatings Gmbh | Silane-based coating composition |
CA3157900A1 (en) | 2019-11-15 | 2021-05-20 | Jan Winsberg | Silane-based coating compositions comprising a metal alkoxide catalyst |
AU2021246184A1 (en) | 2020-04-02 | 2022-10-20 | Basf Coatings Gmbh | Silane-based coating compositions comprising a metal alkoxide catalyst and an acid-functional polymer |
JP2024516676A (ja) | 2021-04-28 | 2024-04-16 | ケメタル ゲゼルシャフト ミット ベシュレンクテル ハフツング | シーラント及びプライマー組成物における接着促進剤としてのイソシアネート官能化オルガノシラン |
Family Cites Families (18)
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CA1088696A (en) * | 1974-09-17 | 1980-10-28 | Nicholas J. Gervase | Isocyanto-functional organo silanes and adhesives therefrom |
US4031120A (en) * | 1974-09-17 | 1977-06-21 | Lord Corporation | Isocyanatosilane adducts |
US4052943A (en) * | 1976-09-16 | 1977-10-11 | The United States Of America As Represented By The Secretary Of The Navy | Coating composition and method for improving propellant tear strength |
DE3220865C2 (de) * | 1982-06-03 | 1984-08-02 | Dynamit Nobel Ag, 5210 Troisdorf | Haftkleber auf der Basis von hydroxylgruppenhaltigen Polymermischungen |
US4539345A (en) * | 1985-02-04 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Moisture-curable polyurethane composition |
US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
US4687533A (en) * | 1985-08-26 | 1987-08-18 | Essex Specialty Products, Inc. | Bonding method employing moisture curable polyurethane polymers |
DE3633777C2 (de) * | 1985-10-03 | 1996-08-22 | Mitsubishi Gas Chemical Co | Hot-melt-Kleberzusammensetzung |
US4640868A (en) * | 1986-02-10 | 1987-02-03 | Morton Thiokol Inc. | Clear, weather resistant adherent coating |
JP2772002B2 (ja) * | 1988-11-28 | 1998-07-02 | サンスター技研株式会社 | プライマー組成物 |
US5155201A (en) * | 1989-07-13 | 1992-10-13 | Akzo N.V. | Polyurethane polyols and high solids coatings therefrom |
DE4114220A1 (de) * | 1991-05-01 | 1992-11-05 | Bayer Ag | Durch feuchtigkeit haertbare, nco-polyurethan-schmelzklebstoff-zusammensetzung |
JP3466610B2 (ja) * | 1992-10-13 | 2003-11-17 | エセックス スペシャルティ プロダクツ インコーポレーテッド | ポリウレタンシーラント組成物 |
JPH10114813A (ja) * | 1997-09-01 | 1998-05-06 | Mitsui Chem Inc | 一液型ウレタン樹脂組成物 |
JP3263034B2 (ja) * | 1997-11-12 | 2002-03-04 | 横浜ゴム株式会社 | ポリウレタン組成物 |
DE19855999A1 (de) * | 1998-12-04 | 2000-06-15 | Bayer Ag | Alkoxysilanhaltige Lackzubereitung |
DE10013628A1 (de) * | 2000-03-18 | 2001-09-20 | Degussa | Stabile 1:1-Monoaddukte aus sekundären Aminoalkylalkoxysilanen und Diisocyanaten sowie ein Verfahren zu ihrer Herstellung |
DE10048615A1 (de) * | 2000-09-30 | 2002-04-11 | Degussa | Nichtwäßriges, wärmehärtendes Zweikomponenten-Beschichtungsmittel |
-
2001
- 2001-12-20 DE DE10162642A patent/DE10162642A1/de not_active Ceased
-
2002
- 2002-12-11 DE DE50213893T patent/DE50213893D1/de not_active Expired - Lifetime
- 2002-12-11 ES ES02787933T patent/ES2331235T3/es not_active Expired - Lifetime
- 2002-12-11 AT AT02787933T patent/ATE444322T1/de not_active IP Right Cessation
- 2002-12-11 JP JP2003554762A patent/JP4159472B2/ja not_active Expired - Fee Related
- 2002-12-11 WO PCT/EP2002/014057 patent/WO2003054049A1/de active Application Filing
- 2002-12-11 AU AU2002352240A patent/AU2002352240A1/en not_active Abandoned
- 2002-12-11 EP EP02787933A patent/EP1456274B1/de not_active Expired - Lifetime
-
2004
- 2004-06-17 US US10/870,344 patent/US20050032974A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
WO2003054049A1 (de) | 2003-07-03 |
ES2331235T3 (es) | 2009-12-28 |
EP1456274A1 (de) | 2004-09-15 |
EP1456274B1 (de) | 2009-09-30 |
AU2002352240A1 (en) | 2003-07-09 |
ATE444322T1 (de) | 2009-10-15 |
DE50213893D1 (de) | 2009-11-12 |
US20050032974A1 (en) | 2005-02-10 |
DE10162642A1 (de) | 2003-07-10 |
JP4159472B2 (ja) | 2008-10-01 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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LAPS | Cancellation because of no payment of annual fees |