JP2003517009A - アミンオルガノボラン錯体重合開始剤および重合性組成物 - Google Patents
アミンオルガノボラン錯体重合開始剤および重合性組成物Info
- Publication number
- JP2003517009A JP2003517009A JP2001544798A JP2001544798A JP2003517009A JP 2003517009 A JP2003517009 A JP 2003517009A JP 2001544798 A JP2001544798 A JP 2001544798A JP 2001544798 A JP2001544798 A JP 2001544798A JP 2003517009 A JP2003517009 A JP 2003517009A
- Authority
- JP
- Japan
- Prior art keywords
- complex
- amine
- composition
- occurrence
- organoborane
- 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.)
- Pending
Links
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
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- 150000002466 imines Chemical class 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
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- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 9
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 5
- 230000009878 intermolecular interaction Effects 0.000 claims abstract description 4
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- -1 heterocyclic amine Chemical class 0.000 claims description 38
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
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- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 3
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- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
- Y10T428/31544—Addition polymer is perhalogenated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Dental Preparations (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/466,321 US6806330B1 (en) | 1999-12-17 | 1999-12-17 | Amine organoborane complex polymerization initiators and polymerizable compositions |
| US09/466,321 | 1999-12-17 | ||
| PCT/US2000/033806 WO2001044311A1 (en) | 1999-12-17 | 2000-12-14 | Amine organoborane complex polymerization initiators and polymerizable compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003517009A true JP2003517009A (ja) | 2003-05-20 |
| JP2003517009A5 JP2003517009A5 (enExample) | 2008-02-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2001544798A Pending JP2003517009A (ja) | 1999-12-17 | 2000-12-14 | アミンオルガノボラン錯体重合開始剤および重合性組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US6806330B1 (enExample) |
| EP (1) | EP1244710B1 (enExample) |
| JP (1) | JP2003517009A (enExample) |
| KR (1) | KR100746019B1 (enExample) |
| CN (1) | CN1174000C (enExample) |
| AT (1) | ATE527286T1 (enExample) |
| AU (1) | AU2096001A (enExample) |
| BR (1) | BR0016770B1 (enExample) |
| CA (1) | CA2396494A1 (enExample) |
| MX (1) | MXPA02005986A (enExample) |
| WO (1) | WO2001044311A1 (enExample) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007522332A (ja) * | 2004-02-17 | 2007-08-09 | ペン ステート リサーチ ファウンデイション | 官能性フルオロポリマーおよびその製法関連出願の相互参照本願は、米国特許出願第号、出願、発明の名称「官能性基を含有するテレケリックポリマー」、代理人整理番号５９５１６−０５４と類似の主題を含む。 |
| JP2007523248A (ja) * | 2004-02-23 | 2007-08-16 | ダウ グローバル テクノロジーズ インコーポレイティド | 低表面エネルギー基体接着用水性接着剤 |
| JP2008518082A (ja) * | 2004-10-28 | 2008-05-29 | ダウ・コーニング・コーポレイション | 硬化可能な伝導組成物 |
| JP2008527105A (ja) * | 2005-01-04 | 2008-07-24 | ダウ・コーニング・コーポレイション | 有機硅素官能基硼素アミン触媒錯体およびこれから調製された硬化可能な組成物 |
| JP2008544067A (ja) * | 2005-06-23 | 2008-12-04 | モーメンティブ・パフォーマンス・マテリアルズ・インク | 硬化触媒、組成物、電子機器及び関連する方法 |
| JP2009511502A (ja) * | 2005-10-07 | 2009-03-19 | ダウ グローバル テクノロジーズ インコーポレイティド | アミド有機ボラート開始剤系 |
| JP2009538367A (ja) * | 2006-05-23 | 2009-11-05 | ダウ・コーニング・コーポレイション | アミド官能性ポリマーとのボラン触媒錯体、およびその錯体から作られる硬化性組成物 |
| JP2012530601A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機ボラン−アミン錯体の解離方法 |
| JP2013520530A (ja) * | 2010-02-18 | 2013-06-06 | ダウ コーニング コーポレーション | 改質表面を有するヒドロゲルおよびヒドロゲル微小粒子 |
| WO2017138567A1 (ja) | 2016-02-09 | 2017-08-17 | サンメディカル株式会社 | 重合性組成物およびキット、ならびに重合開始剤 |
| WO2018043260A1 (ja) * | 2016-08-31 | 2018-03-08 | 富士フイルム株式会社 | 硬化性組成物、平版印刷版原版、及び、平版印刷版の作製方法 |
| WO2019064522A1 (ja) | 2017-09-29 | 2019-04-04 | サンメディカル株式会社 | 複合粒子、キット、材料および複合粒子の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1201722A1 (en) | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
| JP2002294101A (ja) * | 2001-03-28 | 2002-10-09 | Nippon Paint Co Ltd | 樹脂組成物、ボロン含有重合体の製造方法及び防汚塗料 |
| US6543404B2 (en) | 2001-04-04 | 2003-04-08 | Dow Global Technologies, Inc. | Adhesively bonded engine intake manifold assembly |
| GB0114684D0 (en) | 2001-06-15 | 2001-08-08 | Dow Chemical Co | Automobile assembly |
| BR0212192A (pt) | 2001-08-15 | 2004-10-05 | Dow Global Technologies Inc | Conjunto para interior veicular |
| US20030044553A1 (en) | 2001-08-23 | 2003-03-06 | Ravi Ramanathan | Fuel tanks |
| US20030047268A1 (en) * | 2001-08-23 | 2003-03-13 | Korchnak Gregory J. | Method for repairing fuel tanks |
| IE20020293A1 (en) | 2002-04-23 | 2003-10-29 | Loctite R & D Ltd | Initiator systems, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US6740716B2 (en) * | 2001-10-30 | 2004-05-25 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
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| AU2003225512A1 (en) | 2002-04-19 | 2003-11-03 | Loctite (R And D) Limited | Polymerisation initiators based on ammonium tetraalkyl boranes, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US6860010B2 (en) | 2002-05-15 | 2005-03-01 | Dow Global Technologies, Inc. | Method of forming an automotive valve cover with integral positive crankcase ventilation |
| US6867271B1 (en) | 2002-06-24 | 2005-03-15 | Henkel Corporation | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| US6988757B2 (en) * | 2002-08-28 | 2006-01-24 | Dow Global Technologies Inc. | Composite panel and method of forming the same |
| US7098279B2 (en) | 2002-10-22 | 2006-08-29 | Loctite (R&D) Limited | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| US7250091B2 (en) * | 2003-02-13 | 2007-07-31 | Dow Global Technologies Inc | Method of forming a seating system |
| CN100427336C (zh) * | 2003-02-13 | 2008-10-22 | 陶氏环球技术公司 | 座椅系统及其制作方法 |
| EP1597105A2 (en) * | 2003-02-13 | 2005-11-23 | Dow Global Technologies Inc. | Improved instrument panel assembly and method of forming same |
| US6777512B1 (en) * | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| US20040188885A1 (en) * | 2003-03-31 | 2004-09-30 | Luis Lorenzo | Instrument panel assembly and method of forming same |
| NZ544162A (en) * | 2003-05-29 | 2008-09-26 | Shire Llc | Abuse resistant amphetamine compounds |
| US20040238114A1 (en) | 2003-06-02 | 2004-12-02 | Dow Global Technologies Inc. | Air bag system and method of forming the same |
| GB2403329B (en) * | 2003-06-06 | 2006-05-31 | Igt Uk Ltd | Entertainment machines |
| EP1648944A1 (en) * | 2003-06-09 | 2006-04-26 | The Dow Global Technologies Inc. | Stabilized organoborane polymerization initiators and polymerizable compositions |
| US7360519B2 (en) * | 2003-07-10 | 2008-04-22 | Dow Global Technologies, Inc. | Engine intake manifold assembly |
| WO2005017005A1 (en) * | 2003-08-13 | 2005-02-24 | Dow Global Technologies Inc. | Method for joining substrates and objects |
| CN1835992B (zh) * | 2003-08-13 | 2010-10-06 | 陶氏环球技术公司 | 使基材与物体接合的方法 |
| GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
| US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
| WO2005063480A1 (en) * | 2003-12-22 | 2005-07-14 | Dow Global Technologies Inc. | Accelerated organoborane amine complex initiated polymerizable compositions |
| JP4959343B2 (ja) * | 2004-01-22 | 2012-06-20 | ヘンケル コーポレイション | 燃料電池用の低表面エネルギー基体を結合および封止するための重合性組成物 |
| EP1718710A1 (en) * | 2004-02-27 | 2006-11-08 | Akzo Nobel N.V. | Polymerization initiator systems containing aluminum compounds as curing inhibitors and polymerizable compositions made therewith |
| US7338038B2 (en) * | 2004-03-12 | 2008-03-04 | Dow Global Technologies, Inc. | Impact absorption structure |
| US7360552B2 (en) * | 2004-04-23 | 2008-04-22 | Dow Global Technologies Inc. | Injectable structural adhesive |
| US20050267261A1 (en) * | 2004-05-14 | 2005-12-01 | Dow Global Technologies, Inc. | Low gloss thermoplastic polyolefin composition |
| WO2006028924A1 (en) | 2004-09-01 | 2006-03-16 | Dow Global Technologies Inc. | Adhesion promoter |
| WO2006050242A1 (en) | 2004-10-28 | 2006-05-11 | Dow Global Technologies Inc. | Method of primerless bonding |
| US8202932B2 (en) | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| JP5090182B2 (ja) | 2005-01-04 | 2012-12-05 | ダウ・コーニング・コーポレイション | オルガノボランアミン錯体によって硬化されたシロキサンおよびシラン |
| JP5039567B2 (ja) * | 2005-02-16 | 2012-10-03 | ダウ・コーニング・コーポレイション | ポリマー粒子、および、有機ボランアミン錯体を用いた封入（ｅｎｃａｐｓｕｌａｔｅｄ）組成物 |
| ATE452742T1 (de) * | 2005-02-25 | 2010-01-15 | Dow Global Technologies Inc | Verfahren zur herstellung eines strukturs mit einer klebeverbindung |
| WO2006094042A1 (en) * | 2005-02-28 | 2006-09-08 | Dow Global Technologies, Inc. | Method of attaching components and article formed using same |
| US7408012B1 (en) | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| JP2009508190A (ja) * | 2005-08-12 | 2009-02-26 | シュガーシーアールエム インコーポレイテッド | 顧客関係管理システム及び方法 |
| CN101267949A (zh) | 2005-09-21 | 2008-09-17 | 陶氏康宁公司 | 使用有机基硼烷胺络合物的环境平版印刷方法 |
| US7682663B2 (en) * | 2006-02-23 | 2010-03-23 | Bowling Green State University | Remote curing of polymer coating by gaseous, vaporous or aerosol initiating agent |
| US20070236049A1 (en) * | 2006-03-31 | 2007-10-11 | Dow Global Technologies Inc. | Modular assembly for a vehicle |
| GB0607438D0 (en) * | 2006-04-13 | 2006-05-24 | Dow Corning | Water containing silicone rubber device, process to make the device and uses for it |
| ZA200807902B (en) * | 2006-04-19 | 2010-01-27 | Dow Global Technologies Inc | Method for blending materials in an extruder, the manufactured article and material pre-mix |
| US20070261224A1 (en) * | 2006-05-11 | 2007-11-15 | Dow Global Technologies Inc. | Methods and articles in having a fringed microprotrusion surface structure |
| US7926870B2 (en) * | 2006-05-26 | 2011-04-19 | Dow Global Technologies Llc | Modular assembly for a vehicle |
| CN101506308B (zh) * | 2006-06-20 | 2011-09-14 | 道康宁公司 | 可固化有机硅组合物 |
| MX2008016342A (es) | 2006-06-29 | 2009-01-19 | Dow Global Technologies Inc | Articulos termoplasticos y procesos para hacer los mismos usando un lote maestro mejorado. |
| US7887668B2 (en) * | 2006-08-30 | 2011-02-15 | Dow Global Technologies Inc. | Amine organoborane polymerizable compostion and uses therefor |
| US20080103274A1 (en) * | 2006-10-12 | 2008-05-01 | Jialanella Gary L | Accelerated organoborane initiated polymerizable compositions |
| US7524907B2 (en) | 2006-10-12 | 2009-04-28 | Dow Global Technologies, Inc. | Accelerated organoborane initiated polymerizable compositions |
| US7842146B2 (en) | 2007-01-26 | 2010-11-30 | Dow Global Technologies Inc. | Ultrasonic energy for adhesive bonding |
| ES2506096T3 (es) | 2007-07-16 | 2014-10-13 | Dow Global Technologies Llc | Polímeros funcionalizados y artículos preparados a partir de los mismos |
| US8377852B2 (en) * | 2007-10-26 | 2013-02-19 | Dow Corning Corporation | Method of preparing a substrate with a composition including an organoborane initiator |
| US8742050B2 (en) | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
| CN102137908B (zh) * | 2008-07-28 | 2013-10-30 | 陶氏康宁公司 | 复合制品 |
| WO2010014537A1 (en) * | 2008-07-28 | 2010-02-04 | Dow Corning Corporation | Radical polymerizable composition |
| US20110104508A1 (en) * | 2008-08-29 | 2011-05-05 | Dow Global Technologies Inc. | Adhesive for bonding to flexible polymer surfaces |
| BRPI0914446A2 (pt) * | 2008-10-23 | 2015-10-27 | Dow Global Technologies Llc | complexo de organoborano |
| WO2010088488A1 (en) | 2009-01-30 | 2010-08-05 | Dow Global Technologies Inc. | Polymeric compositions and filled tpo articles having improved aesthetics |
| EP2393855B1 (en) | 2009-02-04 | 2015-06-17 | Dow Corning Corporation | Method of forming a non-random copolymer |
| KR101867786B1 (ko) * | 2009-06-26 | 2018-06-15 | 바스프 코팅스 게엠베하 | 페인트 코팅계 및 다층 페인트 코팅의 제조 방법 |
| US9593209B2 (en) | 2009-10-22 | 2017-03-14 | Dow Corning Corporation | Process for preparing clustered functional polyorganosiloxanes, and methods for their use |
| TWI502004B (zh) | 2009-11-09 | 2015-10-01 | Dow Corning | 群集官能性聚有機矽氧烷之製法及其使用方法 |
| JP5740478B2 (ja) | 2010-11-01 | 2015-06-24 | ダウ ブラジル インダストリア エコメルシオ デ プロダトス クイミコス エルティーディーエイ | ポリイソシアネート官能性接着剤の接着性を改善するために修飾された１種以上の表面を有するポリオレフィン |
| US9045672B2 (en) | 2011-05-03 | 2015-06-02 | Dow GlobalTechnologies LLC | Dual cure adhesive useful for bonding to glass |
| KR20130143661A (ko) | 2011-05-03 | 2013-12-31 | 다우 글로벌 테크놀로지스 엘엘씨 | 아이소시아네이트 작용성 예비중합체를 함유하는 촉진된 경화 조성물 |
| GB2491170B (en) | 2011-05-26 | 2013-11-06 | Henkel Ireland Ltd | Two-part polymerisable compositions |
| WO2013059118A1 (en) * | 2011-10-19 | 2013-04-25 | The Trustees Of Columbia University In The City Of New York | Cyclopropenimine catalyst compositions and processes |
| US9018326B2 (en) | 2012-04-06 | 2015-04-28 | Ips Corporation | Adhesive composition for bonding low surface energy polyolefin substrates |
| WO2013156892A1 (en) * | 2012-04-20 | 2013-10-24 | Basf Se | Process for graft polymerization on polymer surfaces using organoborane-amine complexes as radical initiators |
| US9416301B2 (en) | 2012-11-08 | 2016-08-16 | Dow Global Technologies Llc | Ultrafast dual cure adhesive useful for bonding to glass |
| US9382452B2 (en) | 2013-02-07 | 2016-07-05 | Illinois Tool Works, Inc. | Low surface energy bonding adhesive formulation and process for the use thereof |
| CN105189685B (zh) | 2013-02-11 | 2017-08-08 | 道康宁公司 | 用于形成导热热自由基固化有机硅组合物的方法 |
| KR102170923B1 (ko) | 2013-02-11 | 2020-10-29 | 다우 실리콘즈 코포레이션 | 클러스터형 작용성 폴리오르가노실록산 및 실리콘 반응성 희석제를 포함하는 경화성 실리콘 조성물 |
| JP6370812B2 (ja) | 2013-02-11 | 2018-08-08 | ダウ シリコーンズ コーポレーション | クラスタ化官能性ポリオルガノシロキサン、これを生成するプロセス、及びこれを使用する方法 |
| US10370572B2 (en) | 2013-02-11 | 2019-08-06 | Dow Silicones Corporation | Moisture-curable hot melt silicone adhesive compositions including an alkoxy-functional siloxane reactive resin |
| US9670392B2 (en) | 2013-02-11 | 2017-06-06 | Dow Corning Corporation | Stable thermal radical curable silicone adhesive compositions |
| KR102186328B1 (ko) | 2013-02-11 | 2020-12-03 | 다우 실리콘즈 코포레이션 | 알콕시-작용성 유기폴리실록산 수지 및 중합체와 이의 관련된 형성 방법 |
| CN103483366B (zh) * | 2013-09-05 | 2017-02-08 | 润泽制药(苏州)有限公司 | 甲氧基二乙基硼烷的制备方法 |
| EP3080223B1 (de) * | 2013-12-11 | 2019-05-08 | Sika Technology AG | Vorbehandlung von substraten, die ungesättigte einheiten aufweisen |
| EP2963010B1 (en) * | 2014-07-04 | 2018-02-21 | Novaled GmbH | Electronic device and compound |
| EP3183311A1 (en) | 2014-08-18 | 2017-06-28 | LORD Corporation | Method for low temperature bonding of elastomers |
| EP3196229B1 (en) | 2015-11-05 | 2018-09-26 | Dow Silicones Corporation | Branched polyorganosiloxanes and related curable compositions, methods, uses and devices |
| EP3464495A4 (en) * | 2016-05-27 | 2020-03-04 | IPS Corporation | POLYMER-POLY (METH) ACRYLATE INTERPENETRATIVE POLYMER NETWORK ADHESIVE COMPOSITIONS AND METHOD OF USING THE SAME |
| CN106497440A (zh) * | 2016-11-11 | 2017-03-15 | 台州吉谷胶业股份有限公司 | 一种环保型常温固化双组分聚烯烃胶粘剂 |
| WO2018160373A1 (en) | 2017-02-28 | 2018-09-07 | Dow Silicones Corporation | Dual cure polyorganosiloxane composition and methods for its preparation and use |
| US11491461B2 (en) | 2017-03-14 | 2022-11-08 | Dow Silicones Corporation | Method of depleting an organosilicon component in a mixture using a sorbent copolymer and apparatus for practicing the method |
| EP3601414A1 (en) * | 2017-03-27 | 2020-02-05 | Dow Silicones Corporation | Method for adhering cured silicones to low energy plastics and composite prepared by the method |
| WO2019116201A1 (en) * | 2017-12-13 | 2019-06-20 | 3M Innovative Properties Company | Optically clear adhesives containing a trialkyl borane complex initiator and photoacid |
| WO2019209476A1 (en) | 2018-04-26 | 2019-10-31 | Dow Silicones Corporation | Method of depleting a volatile component in a mixture using a sorbent copolymer and apparatus for practicing the method |
| GB2580162B (en) | 2018-12-21 | 2022-07-13 | Henkel IP & Holding GmbH | One-part photocurable (meth) acrylate compositions |
| CN113950514B (zh) * | 2019-06-04 | 2023-01-24 | 美国陶氏有机硅公司 | 甲硅烷基氢化物与α-β不饱和酯之间的热引发酸催化反应 |
| US20210301183A1 (en) * | 2020-03-24 | 2021-09-30 | Illinois Tool Works Inc. | Low surface energy accelerated bonding adhesive formulation and process for the use thereof |
| CN114149527B (zh) * | 2021-12-10 | 2023-08-04 | 复旦大学 | 一种在空气氛围中实现可控自由基聚合的方法及其应用 |
| EP4410854A1 (en) | 2023-02-03 | 2024-08-07 | Arkema France | High strength urethane acrylate hybrid structure adhesives |
| CN117258838B (zh) * | 2023-02-28 | 2025-10-17 | 辽宁奥克化学股份有限公司 | 一种制备亚硫酸乙烯酯的催化剂、亚硫酸乙烯酯的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0598216A (ja) * | 1991-04-29 | 1993-04-20 | Natl Starch & Chem Investment Holding Corp | アクリル接着剤配合物 |
| US5539070A (en) * | 1994-02-22 | 1996-07-23 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
| US5935711A (en) * | 1996-10-23 | 1999-08-10 | 3M Innovative Properties Company | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275611A (en) | 1960-12-30 | 1966-09-27 | Monsanto Co | Process for polymerizing unsaturated monomers with a catalyst comprising an organoboron compound, a peroxygen compound and an amine |
| US3527737A (en) | 1967-09-15 | 1970-09-08 | G C Kagaku Kogyo Kk | Adhesive compositions |
| DE3041904C2 (de) | 1980-11-06 | 1984-11-22 | Henkel KGaA, 4000 Düsseldorf | Borverbindungen enthaltende lagerstabile Reaktionsklebstoffe |
| DE3207263A1 (de) | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Organo-borverbindungen enthaltende stoffgemische, verfahren zu ihrer herstellung und ihre verwendung |
| DE3207264A1 (de) | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Neue boralkylverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3518965A1 (de) | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
| CA1292591C (en) | 1986-10-30 | 1991-11-26 | Takeshi Sakashita | Curable composition |
| JPH075680B2 (ja) | 1987-07-03 | 1995-01-25 | 三井石油化学工業株式会社 | 硬化性組成物 |
| US5034464A (en) | 1989-07-19 | 1991-07-23 | E. I. Du Pont De Nemours And Company | Amine-borane adduct curing agents for epoxy/anhydride resins |
| US5143884A (en) | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5286821A (en) | 1992-03-17 | 1994-02-15 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5401805A (en) | 1992-04-06 | 1995-03-28 | The Penn State Research Foundation | Olefin graft copolymers prepared using borane-containing olefin backbone polymers |
| US5310835A (en) | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
| US5690780A (en) | 1995-02-22 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
| US5621143A (en) | 1995-04-14 | 1997-04-15 | Minnesota Mining And Manufacturing Company | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
| US5616796A (en) | 1995-04-14 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive composition made therewith |
| US5686544A (en) | 1995-08-11 | 1997-11-11 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
| JPH11512123A (ja) | 1995-08-11 | 1999-10-19 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 開始剤系および該開始剤を使用して製造された接着組成物 |
| CN1106411C (zh) | 1995-11-07 | 2003-04-23 | 美国3M公司 | 引发剂系统和由其制成的粘合剂组合物 |
| US5952409A (en) | 1996-01-31 | 1999-09-14 | 3M Innovative Properties Company | Compositions and methods for imparting stain resistance and stain resistant articles |
| US5912433A (en) | 1997-01-17 | 1999-06-15 | Minnesota Mining And Manufacturing Company | Cable closure injection sealed with low surface energy adhesive |
| US6252023B1 (en) | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
| US6410667B1 (en) * | 1999-11-04 | 2002-06-25 | 3M Innovative Properties Company | Initiator/amidine complexes, systems comprising the complexes, and polymerized compositions made therewith |
-
1999
- 1999-12-17 US US09/466,321 patent/US6806330B1/en not_active Expired - Fee Related
-
2000
- 2000-12-14 BR BRPI0016770-3A patent/BR0016770B1/pt not_active IP Right Cessation
- 2000-12-14 AU AU20960/01A patent/AU2096001A/en not_active Abandoned
- 2000-12-14 AT AT00984323T patent/ATE527286T1/de not_active IP Right Cessation
- 2000-12-14 KR KR1020027007666A patent/KR100746019B1/ko not_active Expired - Fee Related
- 2000-12-14 WO PCT/US2000/033806 patent/WO2001044311A1/en not_active Ceased
- 2000-12-14 JP JP2001544798A patent/JP2003517009A/ja active Pending
- 2000-12-14 CA CA002396494A patent/CA2396494A1/en not_active Abandoned
- 2000-12-14 CN CNB008170711A patent/CN1174000C/zh not_active Expired - Fee Related
- 2000-12-14 EP EP00984323A patent/EP1244710B1/en not_active Expired - Lifetime
- 2000-12-14 MX MXPA02005986A patent/MXPA02005986A/es active IP Right Grant
-
2001
- 2001-06-15 US US09/882,510 patent/US6713579B2/en not_active Expired - Fee Related
- 2001-06-15 US US09/881,980 patent/US6730759B2/en not_active Expired - Lifetime
- 2001-06-15 US US09/881,985 patent/US6713578B2/en not_active Expired - Fee Related
- 2001-06-15 US US09/881,984 patent/US6710145B2/en not_active Expired - Fee Related
- 2001-06-15 US US09/881,983 patent/US6706831B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0598216A (ja) * | 1991-04-29 | 1993-04-20 | Natl Starch & Chem Investment Holding Corp | アクリル接着剤配合物 |
| US5539070A (en) * | 1994-02-22 | 1996-07-23 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
| US5935711A (en) * | 1996-10-23 | 1999-08-10 | 3M Innovative Properties Company | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4885741B2 (ja) * | 2004-02-17 | 2012-02-29 | ザ・ペン・ステート・リサーチ・ファウンデイション | 官能性フルオロポリマーおよびその製法 |
| JP2007522332A (ja) * | 2004-02-17 | 2007-08-09 | ペン ステート リサーチ ファウンデイション | 官能性フルオロポリマーおよびその製法関連出願の相互参照本願は、米国特許出願第号、出願、発明の名称「官能性基を含有するテレケリックポリマー」、代理人整理番号５９５１６−０５４と類似の主題を含む。 |
| JP2007523248A (ja) * | 2004-02-23 | 2007-08-16 | ダウ グローバル テクノロジーズ インコーポレイティド | 低表面エネルギー基体接着用水性接着剤 |
| JP2008518082A (ja) * | 2004-10-28 | 2008-05-29 | ダウ・コーニング・コーポレイション | 硬化可能な伝導組成物 |
| JP2008527105A (ja) * | 2005-01-04 | 2008-07-24 | ダウ・コーニング・コーポレイション | 有機硅素官能基硼素アミン触媒錯体およびこれから調製された硬化可能な組成物 |
| JP2008544067A (ja) * | 2005-06-23 | 2008-12-04 | モーメンティブ・パフォーマンス・マテリアルズ・インク | 硬化触媒、組成物、電子機器及び関連する方法 |
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| JP2009511502A (ja) * | 2005-10-07 | 2009-03-19 | ダウ グローバル テクノロジーズ インコーポレイティド | アミド有機ボラート開始剤系 |
| JP2009538367A (ja) * | 2006-05-23 | 2009-11-05 | ダウ・コーニング・コーポレイション | アミド官能性ポリマーとのボラン触媒錯体、およびその錯体から作られる硬化性組成物 |
| JP2012530601A (ja) * | 2009-06-26 | 2012-12-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機ボラン−アミン錯体の解離方法 |
| JP2013520530A (ja) * | 2010-02-18 | 2013-06-06 | ダウ コーニング コーポレーション | 改質表面を有するヒドロゲルおよびヒドロゲル微小粒子 |
| US9574109B2 (en) | 2010-02-18 | 2017-02-21 | Dow Corning Corporation | Surface-modified hydrogels and hydrogel microparticles |
| KR101825607B1 (ko) | 2010-02-18 | 2018-02-05 | 다우 코닝 코포레이션 | 표면-개질된 하이드로겔 및 하이드로겔 미세입자 |
| WO2017138567A1 (ja) | 2016-02-09 | 2017-08-17 | サンメディカル株式会社 | 重合性組成物およびキット、ならびに重合開始剤 |
| WO2018043260A1 (ja) * | 2016-08-31 | 2018-03-08 | 富士フイルム株式会社 | 硬化性組成物、平版印刷版原版、及び、平版印刷版の作製方法 |
| JPWO2018043260A1 (ja) * | 2016-08-31 | 2019-02-21 | 富士フイルム株式会社 | 硬化性組成物、平版印刷版原版、及び、平版印刷版の作製方法 |
| CN109562634A (zh) * | 2016-08-31 | 2019-04-02 | 富士胶片株式会社 | 固化性组合物、平版印刷版原版及平版印刷版的制造方法 |
| WO2019064522A1 (ja) | 2017-09-29 | 2019-04-04 | サンメディカル株式会社 | 複合粒子、キット、材料および複合粒子の製造方法 |
| US11292905B2 (en) | 2017-09-29 | 2022-04-05 | Sun Medical Co., Ltd. | Composite particles, kit, material, and method for producing composite particles |
| US12173149B2 (en) | 2017-09-29 | 2024-12-24 | Sun Medical Co., Ltd. | Composite particles, kit, material, and method for producing composite particles |
Also Published As
| Publication number | Publication date |
|---|---|
| US20020058764A1 (en) | 2002-05-16 |
| ATE527286T1 (de) | 2011-10-15 |
| US20020028894A1 (en) | 2002-03-07 |
| US6713579B2 (en) | 2004-03-30 |
| US6806330B1 (en) | 2004-10-19 |
| US20020033227A1 (en) | 2002-03-21 |
| US20020031607A1 (en) | 2002-03-14 |
| US6730759B2 (en) | 2004-05-04 |
| MXPA02005986A (es) | 2004-08-12 |
| US6706831B2 (en) | 2004-03-16 |
| EP1244710B1 (en) | 2011-10-05 |
| KR20020072549A (ko) | 2002-09-16 |
| CA2396494A1 (en) | 2001-06-21 |
| WO2001044311A1 (en) | 2001-06-21 |
| CN1409728A (zh) | 2003-04-09 |
| US20020025381A1 (en) | 2002-02-28 |
| BR0016770A (pt) | 2002-09-03 |
| CN1174000C (zh) | 2004-11-03 |
| EP1244710A1 (en) | 2002-10-02 |
| KR100746019B1 (ko) | 2007-08-06 |
| US6713578B2 (en) | 2004-03-30 |
| AU2096001A (en) | 2001-06-25 |
| US6710145B2 (en) | 2004-03-23 |
| BR0016770B1 (pt) | 2011-01-25 |
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