JP5818890B2 - 二重反応性シラン官能基を含む硬化性組成物 - Google Patents
二重反応性シラン官能基を含む硬化性組成物 Download PDFInfo
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- JP5818890B2 JP5818890B2 JP2013518543A JP2013518543A JP5818890B2 JP 5818890 B2 JP5818890 B2 JP 5818890B2 JP 2013518543 A JP2013518543 A JP 2013518543A JP 2013518543 A JP2013518543 A JP 2013518543A JP 5818890 B2 JP5818890 B2 JP 5818890B2
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- triazabicyclo
- ene
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- fluorinated
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Classifications
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
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- C07F9/065—Phosphoranes containing the structure P=N-
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35998510P | 2010-06-30 | 2010-06-30 | |
| US36001910P | 2010-06-30 | 2010-06-30 | |
| US61/359,985 | 2010-06-30 | ||
| US61/360,019 | 2010-06-30 | ||
| US42311910P | 2010-12-15 | 2010-12-15 | |
| US61/423,119 | 2010-12-15 | ||
| PCT/US2011/042074 WO2012003160A1 (en) | 2010-06-30 | 2011-06-28 | Curable composition comprising dual reactive silane functionality |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013531113A JP2013531113A (ja) | 2013-08-01 |
| JP2013531113A5 JP2013531113A5 (enExample) | 2014-08-07 |
| JP5818890B2 true JP5818890B2 (ja) | 2015-11-18 |
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| JP2013518543A Expired - Fee Related JP5818890B2 (ja) | 2010-06-30 | 2011-06-28 | 二重反応性シラン官能基を含む硬化性組成物 |
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| US (1) | US8841399B2 (enExample) |
| EP (1) | EP2665788A1 (enExample) |
| JP (1) | JP5818890B2 (enExample) |
| CN (1) | CN102985503A (enExample) |
| WO (1) | WO2012003160A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2875007B2 (ja) | 1990-11-27 | 1999-03-24 | 積水化学工業株式会社 | プラスチックベンド管の製造方法 |
| KR20190131520A (ko) * | 2017-04-04 | 2019-11-26 | 메르크 파텐트 게엠베하 | 필름 형성 조성물 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| JP5818890B2 (ja) | 2010-06-30 | 2015-11-18 | スリーエム イノベイティブ プロパティズ カンパニー | 二重反応性シラン官能基を含む硬化性組成物 |
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Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2708289A (en) | 1951-10-03 | 1955-05-17 | Dow Corning | Method of preparing pressure sensitive organosiloxane sheet material |
| NL126303C (enExample) | 1965-01-08 | 1900-01-01 | ||
| NL129544C (enExample) | 1965-08-04 | |||
| US3628996A (en) | 1969-06-27 | 1971-12-21 | Dow Corning | Polydimethylsiloxane release agent |
| GB1451623A (en) | 1973-10-01 | 1976-10-06 | Mullard Ltd | Method of prov8ding a patterned layer of silicon-containing oxide on a substrate |
| US4181752A (en) | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| US4269963A (en) | 1979-12-03 | 1981-05-26 | Dow Corning Corporation | Mercaptoorganopolysiloxanes and curable compositions including same |
| US4489199A (en) | 1983-08-08 | 1984-12-18 | General Electric Company | Room temperature vulcanizable organopolysiloxane compositions |
| JPS6122094A (ja) | 1984-07-10 | 1986-01-30 | Toray Silicone Co Ltd | 有機けい素化合物の製造方法 |
| US4761443A (en) | 1987-06-04 | 1988-08-02 | Dow Corning Corporaton | Multiple release mold coating for high water, high resiliency polyurethane foam |
| JP3044048B2 (ja) | 1990-02-28 | 2000-05-22 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサン系エラストマー粉体およびその製造方法 |
| EP0448154A1 (en) | 1990-03-20 | 1991-09-25 | Akzo Nobel N.V. | Coating composition including a blocked basic catalyst |
| US5286815A (en) | 1992-02-07 | 1994-02-15 | Minnesota Mining And Manufacturing Company | Moisture curable polysiloxane release coating compositions |
| US5371162A (en) | 1992-07-09 | 1994-12-06 | Minnesota Mining And Manufacturing Company | Storage-stable silicone composition |
| US5403909A (en) | 1993-07-15 | 1995-04-04 | General Electric Company | Catalysts for polycondensation and redistribution of organosiloxane polymers |
| JP3499032B2 (ja) | 1995-02-02 | 2004-02-23 | ダウ コーニング アジア株式会社 | 放射線硬化性組成物、その硬化方法及びパターン形成方法 |
| US6136996A (en) | 1995-12-13 | 2000-10-24 | General Electric Company | Catalysts for polycondensation and redistribution of organosiloxane polymers |
| US6124371A (en) | 1996-02-22 | 2000-09-26 | Dsm N.V. | Anionic photocatalyst |
| JP3628098B2 (ja) | 1996-03-29 | 2005-03-09 | ダウ コーニング アジア株式会社 | 放射線硬化性組成物およびこれを用いた硬化物パターンの製造方法 |
| JPH09268228A (ja) | 1996-04-01 | 1997-10-14 | Dow Corning Asia Ltd | 紫外線硬化性組成物およびこれを用いた硬化物パターンの形成方法 |
| US5688888A (en) | 1996-04-08 | 1997-11-18 | General Electric Company | Peralkylated phosphazene base-catalyzed silanol condensation method |
| US6441118B2 (en) | 1996-04-25 | 2002-08-27 | 3M Innovative Properties Company | Polydiorganosiloxane oligourea segmented copolymers and a process for making same |
| ES2181162T3 (es) | 1997-01-22 | 2003-02-16 | Ciba Sc Holding Ag | Bases fotoactivables que contienen nitrogeno, basadas en alfa-amino-cetonas. |
| US6551761B1 (en) | 1997-02-26 | 2003-04-22 | Ciba Specialty Chemical Corporation | Photoactivatable nitrogen-containing bases based on α-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
| AU6461998A (en) | 1997-03-14 | 1998-09-29 | Minnesota Mining And Manufacturing Company | Cure-on-demand, moisture-curable compositions having reactive silane functionality |
| US5866222A (en) | 1997-07-18 | 1999-02-02 | Minnesota Mining And Manufacturing Co. | Silicone copolymer modified release tapes |
| DE19752935A1 (de) | 1997-11-28 | 1999-06-02 | Basf Ag | Verfahren zur Herstellung von bicyclischen Amidinen, Diazacycloalkene und ein Verfahren zu deren Herstellung |
| GB9818539D0 (en) * | 1998-08-26 | 1998-10-21 | Dow Corning | Process for producing a silicone polymer |
| US6235832B1 (en) * | 1998-12-21 | 2001-05-22 | Dow Corning Corporation | RTV silicone compositions with rapid development of green strength |
| US6780484B2 (en) | 2001-02-02 | 2004-08-24 | 3M Innovative Properties Company | Adhesive article and method of preparing |
| US6805933B2 (en) | 2001-07-31 | 2004-10-19 | 3M Innovative Properties Company | Articles comprising a release liner having a high coefficient of friction and good roll stability |
| EP1436297B1 (en) | 2001-10-17 | 2007-04-25 | Ciba Specialty Chemicals Holding Inc. | Photoactivable nitrogen bases |
| AU2003220460A1 (en) | 2002-04-05 | 2003-10-27 | Henkel Corporation | Curable foam elastomeric compositions |
| DE10237271A1 (de) | 2002-08-14 | 2004-03-04 | Consortium für elektrochemische Industrie GmbH | Polymermassen auf Basis alkoxysilanterminierter Polymere mit regulierbarer Härtungsgeschwindigkeit |
| US7064173B2 (en) | 2002-12-30 | 2006-06-20 | General Electric Company | Silicone condensation reaction |
| US6777512B1 (en) | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| DE602005002571T2 (de) | 2004-02-16 | 2008-01-31 | Mitsubishi Gas Chemical Co., Inc. | Photobasengenerator und härtbare Zusammensetzung |
| US7482391B1 (en) * | 2005-05-09 | 2009-01-27 | Henkel Corporation | Foaming RTV silicone compositions |
| US7148370B1 (en) | 2005-07-20 | 2006-12-12 | General Electric Company | Process for synthesis of diorganosilanes by disproportionation of hydridosiloxanes |
| EP1939257B1 (en) | 2005-09-30 | 2017-06-21 | Kaneka Corporation | Curable composition |
| JP5378684B2 (ja) | 2005-09-30 | 2013-12-25 | 株式会社カネカ | 硬化性組成物 |
| JP5281001B2 (ja) | 2006-06-20 | 2013-09-04 | ダウ・コーニング・コーポレーシヨン | 硬化可能な有機ケイ素組成物 |
| EP2088173B1 (en) | 2006-11-22 | 2012-02-22 | Kaneka Corporation | Curable composition and catalyst composition |
| FR2929286A1 (fr) | 2008-03-28 | 2009-10-02 | Bluestar Silicones France Soc | Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes |
| EP2270114B1 (en) | 2008-03-31 | 2014-07-09 | San-Apro Limited | Photobase generator |
| US8470899B2 (en) | 2009-06-19 | 2013-06-25 | Bluestar Silicones France Sas | Silicone composition which is cross-linkable by dehydrogenative condensation in the presence of a non-metal catalyst |
| WO2010149869A1 (fr) | 2009-06-19 | 2010-12-29 | Bluestar Silicones France | Composition silicone reticulable par deshydrogenocondensation en presence d'un catalyseur non metallique |
| US8840993B2 (en) | 2010-06-30 | 2014-09-23 | 3M Innovative Properties Company | Curable polysiloxane coating composition |
| CN102971380B (zh) | 2010-06-30 | 2015-08-19 | 3M创新有限公司 | 包含双反应性硅烷官能团的可按需固化组合物 |
| JP5818890B2 (ja) | 2010-06-30 | 2015-11-18 | スリーエム イノベイティブ プロパティズ カンパニー | 二重反応性シラン官能基を含む硬化性組成物 |
-
2011
- 2011-06-28 JP JP2013518543A patent/JP5818890B2/ja not_active Expired - Fee Related
- 2011-06-28 EP EP11733943.2A patent/EP2665788A1/en not_active Withdrawn
- 2011-06-28 WO PCT/US2011/042074 patent/WO2012003160A1/en not_active Ceased
- 2011-06-28 CN CN2011800329992A patent/CN102985503A/zh active Pending
- 2011-06-28 US US13/807,319 patent/US8841399B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2875007B2 (ja) | 1990-11-27 | 1999-03-24 | 積水化学工業株式会社 | プラスチックベンド管の製造方法 |
| KR20190131520A (ko) * | 2017-04-04 | 2019-11-26 | 메르크 파텐트 게엠베하 | 필름 형성 조성물 |
| KR102276502B1 (ko) | 2017-04-04 | 2021-07-12 | 메르크 파텐트 게엠베하 | 필름 형성 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20130102728A1 (en) | 2013-04-25 |
| CN102985503A (zh) | 2013-03-20 |
| US8841399B2 (en) | 2014-09-23 |
| EP2665788A1 (en) | 2013-11-27 |
| JP2013531113A (ja) | 2013-08-01 |
| WO2012003160A1 (en) | 2012-01-05 |
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