CN104024331B - 苯并噁嗪的胺/环氧树脂固化 - Google Patents
苯并噁嗪的胺/环氧树脂固化 Download PDFInfo
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- CN104024331B CN104024331B CN201280051619.4A CN201280051619A CN104024331B CN 104024331 B CN104024331 B CN 104024331B CN 201280051619 A CN201280051619 A CN 201280051619A CN 104024331 B CN104024331 B CN 104024331B
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- Prior art keywords
- oxazine
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- compound
- epoxy
- hydrocarbyl
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
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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
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- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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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
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- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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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
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| US201161552494P | 2011-10-28 | 2011-10-28 | |
| US61/552,494 | 2011-10-28 | ||
| PCT/US2012/061865 WO2013063236A1 (en) | 2011-10-28 | 2012-10-25 | Amine/epoxy curing of benzoxazines |
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| CN104024331A CN104024331A (zh) | 2014-09-03 |
| CN104024331B true CN104024331B (zh) | 2016-10-19 |
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| EP (1) | EP2771402B1 (oth) |
| JP (1) | JP2015502416A (oth) |
| KR (1) | KR101951266B1 (oth) |
| CN (1) | CN104024331B (oth) |
| IN (1) | IN2014CN03129A (oth) |
| SG (1) | SG11201401641WA (oth) |
| WO (1) | WO2013063236A1 (oth) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2691457B1 (en) * | 2011-03-28 | 2014-11-19 | 3M Innovative Properties Company | Curable composition, article, method of curing, and tack-free reaction product |
| EP3156450B1 (en) * | 2014-06-13 | 2019-10-09 | DIC Corporation | Curable resin composition, cured product thereof, semiconductor sealing material, semiconductor device, prepreg, circuit board, buildup film, buildup board, fiber-reinforced composite material, and fiber-reinforced resin molded article |
| JP2017538836A (ja) | 2014-12-18 | 2017-12-28 | スリーエム イノベイティブ プロパティズ カンパニー | 改善された熱安定性を有する硬化性ベンゾオキサジン組成物 |
| US20160297994A1 (en) * | 2015-04-10 | 2016-10-13 | Eastman Chemical Company | Curable benzoxazine-based phenolic resins and coating compositions thereof |
| WO2016200557A1 (en) | 2015-06-09 | 2016-12-15 | 3M Innovative Properties Company | Ammonium salt catalyzed benzoxazine polymerization |
| EP3498750A1 (de) | 2017-12-15 | 2019-06-19 | HILTI Aktiengesellschaft | Härterkomponente für mehrkomponenten-epoxidharzmasse und mehrkomponenten-epoxidharzmasse |
| KR20200139131A (ko) * | 2018-03-30 | 2020-12-11 | 도레이 카부시키가이샤 | 벤족사진 수지 조성물, 프리프레그 및 섬유 강화 복합 재료 |
| CN112673043B (zh) * | 2018-09-19 | 2024-03-29 | 喜利得股份公司 | 用于环氧树脂混合物的固化剂组合物、环氧树脂混合物和多组分环氧树脂体系 |
| US20230159705A1 (en) * | 2020-04-15 | 2023-05-25 | Kaneka Corporation | Synthesis, purification, and properties of ring-opened benzoxazine thermoplastic |
| WO2022069947A1 (en) * | 2020-09-29 | 2022-04-07 | Kaneka Corporation | Synthesis of self-healing benzoxazine polymers through melt polymerization |
| CN115232583A (zh) * | 2022-09-23 | 2022-10-25 | 武汉市三选科技有限公司 | 高储存性底部填充胶、其制备方法及芯片封装结构 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1381533A (zh) * | 2001-04-02 | 2002-11-27 | 日本油漆株式会社 | 含有苯并噁嗪化合物的涂料组合物 |
| WO2005000955A1 (en) * | 2003-06-27 | 2005-01-06 | Henkel Corporation | Heat curable compositions comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine terminal groups as a toughener |
| JP2009046590A (ja) * | 2007-08-20 | 2009-03-05 | Sekisui Chem Co Ltd | 熱硬化性樹脂組成物及びその製造方法 |
| JP2009227884A (ja) * | 2008-03-25 | 2009-10-08 | Showa Highpolymer Co Ltd | 熱硬化性樹脂組成物、それを用いた硬化物および積層板 |
| WO2010092723A1 (ja) * | 2009-02-12 | 2010-08-19 | 新日本石油株式会社 | ベンゾオキサジン樹脂組成物 |
| JP2010254895A (ja) * | 2009-04-28 | 2010-11-11 | Yokohama National Univ | エポキシ樹脂組成物及びその硬化物 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018262A (en) | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
| US3298998A (en) | 1961-03-07 | 1967-01-17 | Eastman Kodak Co | Bisglycidyl ethers of bisphenols |
| US3496250A (en) | 1967-02-21 | 1970-02-17 | Borg Warner | Blends of epoxy resins and acrylonitrile butadiene-styrene graft copolymers |
| US3890272A (en) | 1973-05-25 | 1975-06-17 | Univ Notre Dame Du Lac | Polymerizing bis-maleimides |
| US4501864A (en) | 1983-12-22 | 1985-02-26 | Monsanto Company | Polymerizable compositions comprising polyamines and poly(dihydrobenzoxazines) |
| US4503211A (en) | 1984-05-31 | 1985-03-05 | Minnesota Mining And Manufacturing Co. | Epoxy resin curing agent, process and composition |
| US4719253A (en) | 1986-08-01 | 1988-01-12 | The Glidden Company | Self-curable benzoxazine functional cathodic electrocoat resins and process |
| US5543516A (en) | 1994-05-18 | 1996-08-06 | Edison Polymer Innovation Corporation | Process for preparation of benzoxazine compounds in solventless systems |
| US20020006484A1 (en) | 1998-05-20 | 2002-01-17 | Balasubramaniam Ramalingam | Adhesive and coating formulations for flexible packaging |
| JP3965786B2 (ja) * | 1998-06-25 | 2007-08-29 | 日立化成工業株式会社 | 熱硬化性樹脂組成物及びプリプレグ、プリント配線板用積層板 |
| US6207586B1 (en) | 1998-10-28 | 2001-03-27 | Lucent Technologies Inc. | Oxide/nitride stacked gate dielectric and associated methods |
| WO2000026328A1 (en) * | 1998-11-03 | 2000-05-11 | The Lubrizol Corporation | Lubricants having overbased metal salts and organic phosphites |
| US6207786B1 (en) | 1998-11-10 | 2001-03-27 | Edison Polymer Innovation Corporation | Ternary systems of benzoxazine, epoxy, and phenolic resins |
| US6376080B1 (en) | 1999-06-07 | 2002-04-23 | Loctite Corporation | Method for preparing polybenzoxazine |
| JP2001288339A (ja) * | 2000-02-03 | 2001-10-16 | Nec Corp | エポキシ樹脂組成物の難燃化方法および難燃性エポキシ樹脂組成物 |
| US6437026B1 (en) | 2001-01-05 | 2002-08-20 | Cookson Singapore Pte Ltd. | Hardener for epoxy molding compounds |
| EA200300813A1 (ru) | 2001-01-22 | 2003-12-25 | Вантико Аг | Огнезащитные реагенты |
| MY138485A (en) | 2001-03-12 | 2009-06-30 | Hitachi Chemical Co Ltd | Process for producing benzoxazine resin |
| JP2003147165A (ja) * | 2001-08-29 | 2003-05-21 | Osaka City | 熱硬化性樹脂組成物 |
| US6743852B2 (en) | 2001-11-13 | 2004-06-01 | Henkel Corporation | Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof |
| CA2474694A1 (en) * | 2002-02-06 | 2003-08-14 | Sekisui Chemical Co., Ltd. | Resin composition_and products containing the same |
| US7157545B2 (en) * | 2002-08-27 | 2007-01-02 | Acushnet Company | Compositions for golf equipment |
| AU2003301550A1 (en) * | 2002-10-22 | 2004-05-13 | Henkel Corporation | Co-curable compositions |
| US6894133B2 (en) * | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US20050216075A1 (en) * | 2003-04-08 | 2005-09-29 | Xingwu Wang | Materials and devices of enhanced electromagnetic transparency |
| US20060102871A1 (en) * | 2003-04-08 | 2006-05-18 | Xingwu Wang | Novel composition |
| CN1890286B (zh) * | 2003-12-08 | 2010-05-26 | 积水化学工业株式会社 | 热固性树脂组合物、树脂片以及用于绝缘基板的树脂片 |
| US20070191555A1 (en) * | 2004-03-30 | 2007-08-16 | Hatsuo Ishida | Thermosetting resin composition and its article |
| US20060134901A1 (en) * | 2004-12-22 | 2006-06-22 | National Starch And Chemical Investment Holding Corporation | Hot-Melt Underfill Composition and Methos of Application |
| US7759435B2 (en) * | 2006-09-26 | 2010-07-20 | Loctite (R&D) Limited | Adducts and curable compositions using same |
| US20100007018A1 (en) * | 2006-12-08 | 2010-01-14 | Derek Wyatt | Process for coating a bumped semiconductor wafer |
| US7847034B2 (en) * | 2008-03-20 | 2010-12-07 | Loctite (R&D) Limited | Adducts and curable compositions using same |
| US7842401B2 (en) * | 2009-03-24 | 2010-11-30 | Iteq Corporation | Halogen-free varnish and prepreg thereof |
| US8383706B2 (en) | 2009-06-05 | 2013-02-26 | 3M Innovative Properties Company | Benzoxazine-thiol adducts |
| JP5813112B2 (ja) | 2010-08-04 | 2015-11-17 | スリーエム イノベイティブ プロパティズ カンパニー | ベンゾオキサジン−チオールポリマーフィルムの製造方法 |
| EP2691457B1 (en) | 2011-03-28 | 2014-11-19 | 3M Innovative Properties Company | Curable composition, article, method of curing, and tack-free reaction product |
| WO2012134731A1 (en) | 2011-03-28 | 2012-10-04 | 3M Innovative Properties Company | Curable composition, article, method of curing, and reaction product |
| JP2014528025A (ja) | 2011-09-28 | 2014-10-23 | スリーエム イノベイティブ プロパティズ カンパニー | ベンゾオキサジンのアミン／チオール硬化 |
-
2012
- 2012-10-25 CN CN201280051619.4A patent/CN104024331B/zh not_active Expired - Fee Related
- 2012-10-25 WO PCT/US2012/061865 patent/WO2013063236A1/en active Application Filing
- 2012-10-25 KR KR1020147013932A patent/KR101951266B1/ko not_active Expired - Fee Related
- 2012-10-25 US US14/345,258 patent/US9695273B2/en active Active
- 2012-10-25 SG SG11201401641WA patent/SG11201401641WA/en unknown
- 2012-10-25 EP EP12784828.1A patent/EP2771402B1/en not_active Not-in-force
- 2012-10-25 JP JP2014538996A patent/JP2015502416A/ja active Pending
- 2012-10-25 IN IN3129CHN2014 patent/IN2014CN03129A/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1381533A (zh) * | 2001-04-02 | 2002-11-27 | 日本油漆株式会社 | 含有苯并噁嗪化合物的涂料组合物 |
| WO2005000955A1 (en) * | 2003-06-27 | 2005-01-06 | Henkel Corporation | Heat curable compositions comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine terminal groups as a toughener |
| JP2009046590A (ja) * | 2007-08-20 | 2009-03-05 | Sekisui Chem Co Ltd | 熱硬化性樹脂組成物及びその製造方法 |
| JP2009227884A (ja) * | 2008-03-25 | 2009-10-08 | Showa Highpolymer Co Ltd | 熱硬化性樹脂組成物、それを用いた硬化物および積層板 |
| WO2010092723A1 (ja) * | 2009-02-12 | 2010-08-19 | 新日本石油株式会社 | ベンゾオキサジン樹脂組成物 |
| JP2010254895A (ja) * | 2009-04-28 | 2010-11-11 | Yokohama National Univ | エポキシ樹脂組成物及びその硬化物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015502416A (ja) | 2015-01-22 |
| IN2014CN03129A (oth) | 2015-07-03 |
| SG11201401641WA (en) | 2014-05-29 |
| KR101951266B1 (ko) | 2019-02-22 |
| CN104024331A (zh) | 2014-09-03 |
| EP2771402B1 (en) | 2018-06-27 |
| EP2771402A1 (en) | 2014-09-03 |
| KR20140084268A (ko) | 2014-07-04 |
| US20150045528A1 (en) | 2015-02-12 |
| US9695273B2 (en) | 2017-07-04 |
| WO2013063236A1 (en) | 2013-05-02 |
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