RU2364605C2 - Полимеризуемые композиции, содержащие ускоритель и в качестве инициатора - комплекс органоборана и амина - Google Patents
Полимеризуемые композиции, содержащие ускоритель и в качестве инициатора - комплекс органоборана и амина Download PDFInfo
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- RU2364605C2 RU2364605C2 RU2006126672/04A RU2006126672A RU2364605C2 RU 2364605 C2 RU2364605 C2 RU 2364605C2 RU 2006126672/04 A RU2006126672/04 A RU 2006126672/04A RU 2006126672 A RU2006126672 A RU 2006126672A RU 2364605 C2 RU2364605 C2 RU 2364605C2
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- 239000013536 elastomeric material Substances 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- SWFMWXHHVGHUFO-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN.NCCCCCCN SWFMWXHHVGHUFO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- RNUUDKLGODSCNO-UHFFFAOYSA-N n-dodecylhydroxylamine Chemical compound CCCCCCCCCCCCNO RNUUDKLGODSCNO-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000012462 polypropylene substrate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000012722 thermally initiated polymerization Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- ZTKBVWUYLHTIBB-UHFFFAOYSA-N tri(propan-2-yl)borane Chemical compound CC(C)B(C(C)C)C(C)C ZTKBVWUYLHTIBB-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- 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
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)
- Polymerization Catalysts (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US53206603P | 2003-12-22 | 2003-12-22 | |
| US60/532,066 | 2003-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006126672A RU2006126672A (ru) | 2008-01-27 |
| RU2364605C2 true RU2364605C2 (ru) | 2009-08-20 |
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| RU2006126672/04A RU2364605C2 (ru) | 2003-12-22 | 2004-12-21 | Полимеризуемые композиции, содержащие ускоритель и в качестве инициатора - комплекс органоборана и амина |
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| JP (1) | JP2007515547A (enExample) |
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| BR (1) | BRPI0417298A (enExample) |
| CA (1) | CA2548109A1 (enExample) |
| DE (1) | DE602004015841D1 (enExample) |
| ES (1) | ES2309598T3 (enExample) |
| RU (1) | RU2364605C2 (enExample) |
| WO (1) | WO2005063480A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1720915B1 (en) * | 2004-02-17 | 2012-10-24 | The Penn State Research Foundation | Functional fluoropolymers and process therefor |
| JP2008531339A (ja) * | 2005-02-25 | 2008-08-14 | ダウ グローバル テクノロジーズ インコーポレイティド | 接着した混成構造物 |
| WO2006094042A1 (en) * | 2005-02-28 | 2006-09-08 | Dow Global Technologies, Inc. | Method of attaching components and article formed using same |
| BRPI0617975A2 (pt) * | 2005-10-07 | 2011-08-09 | Dow Global Tchnologies Inc | composto de amido-borato |
| CN101583476A (zh) * | 2006-04-19 | 2009-11-18 | 陶氏环球技术公司 | 在挤出机中共混材料的方法，制品和材料预混合 |
| 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 |
| BRPI0713204A8 (pt) | 2006-06-29 | 2017-12-12 | Dow Global Technologies Inc | Processo para fazer um artigo conformado, kit para uso em um processo para fazer um artigo conformado e artigo |
| US7887668B2 (en) * | 2006-08-30 | 2011-02-15 | Dow Global Technologies Inc. | Amine organoborane polymerizable compostion and uses therefor |
| US7524907B2 (en) * | 2006-10-12 | 2009-04-28 | Dow Global Technologies, Inc. | Accelerated organoborane initiated polymerizable compositions |
| US20080103274A1 (en) * | 2006-10-12 | 2008-05-01 | Jialanella Gary L | Accelerated organoborane initiated polymerizable compositions |
| US8742050B2 (en) | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
| US8529821B2 (en) | 2009-01-30 | 2013-09-10 | Dow Global Technologies Llc | Polymeric compositions and filled TPO articles having improved aesthetics |
| WO2010091001A1 (en) | 2009-02-04 | 2010-08-12 | Dow Corning Corporation | Method of forming a non-random copolymer |
| EP2695898A4 (en) * | 2011-04-07 | 2015-02-18 | Hitachi Ltd | DENSITY, MANUFACTURING PROCESS, METHOD FOR ITS REPAIR AND PARTS THEREFOR |
| CN103547606B (zh) | 2011-05-03 | 2016-01-20 | 陶氏环球技术有限责任公司 | 可用于粘合玻璃的双重固化粘合剂 |
| KR20130143661A (ko) | 2011-05-03 | 2013-12-31 | 다우 글로벌 테크놀로지스 엘엘씨 | 아이소시아네이트 작용성 예비중합체를 함유하는 촉진된 경화 조성물 |
| WO2014074140A1 (en) | 2012-11-08 | 2014-05-15 | Dow Global Technologies Llc | Ultrafast dual cure adhesive useful for bonding to glass |
| JP2014136706A (ja) * | 2013-01-15 | 2014-07-28 | Hitachi Chemical Co Ltd | 樹脂組成物、樹脂組成物の製造方法、樹脂組成物を含むレジスト組成物及びレジスト組成物を用いたパターン形成方法 |
| EP2945994B1 (en) | 2013-01-18 | 2018-07-11 | Basf Se | Acrylic dispersion-based coating compositions |
| WO2016028783A1 (en) | 2014-08-18 | 2016-02-25 | Lord Corporation | Method for low temperature bonding of elastomers |
| CN110088193B (zh) * | 2016-12-16 | 2022-02-25 | 电化株式会社 | 组合物 |
| WO2018182950A1 (en) | 2017-03-27 | 2018-10-04 | Dow Silicones Corporation | Method for adhering cured silicones to low energy plastics and composite prepared by the method |
| CN112262159A (zh) | 2018-06-15 | 2021-01-22 | 电化株式会社 | 组合物 |
| EP4141078A4 (en) | 2020-11-17 | 2023-08-09 | Resonac Corporation | Adhesive set, adhesive body, and manufacturing method therefor |
| WO2022107211A1 (ja) * | 2020-11-17 | 2022-05-27 | 昭和電工マテリアルズ株式会社 | 接着剤セット、並びに接着体及びその製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5684102A (en) * | 1995-04-14 | 1997-11-04 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive compositions made therewith |
| RU2171000C2 (ru) * | 1997-01-17 | 2001-07-20 | Миннесота Майнинг Энд Мэнюфекчуринг Компани | Кабельный кожух, уплотненный инжекцией клея с низкой поверхностной энергией |
Family Cites Families (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US530895A (en) * | 1894-12-11 | Incandescent electric lamp | ||
| BE599646A (enExample) * | 1960-02-02 | |||
| 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 |
| AT314710B (de) * | 1971-06-07 | 1974-04-25 | Reichhold Albert Chemie Ag | Verfahren zum Verkleben von festen Materialien und Schmelzhaftkleber hiefür |
| US3971751A (en) * | 1975-06-09 | 1976-07-27 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Vulcanizable silylether terminated polymer |
| GB1552046A (en) * | 1977-02-02 | 1979-09-05 | Ciba Geigy Ag | Film adhesives |
| DE2852621C4 (de) * | 1978-12-05 | 1995-11-30 | Siemens Ag | Isolierschicht-Feldeffekttransistor mit einer Drif tstrecke zwischen Gate-Elektrode und Drain-Zone |
| US4344800A (en) | 1980-06-03 | 1982-08-17 | Dow Corning Corporation | Method for producing hydrophobic reinforcing silica fillers and fillers obtained thereby |
| 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 |
| US4426243A (en) * | 1981-12-01 | 1984-01-17 | Illinois Tool Works Inc. | Room-temperature-curable, quick-setting acrylic/epoxy adhesives and methods of bonding |
| DE3207264A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Neue boralkylverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US4538920A (en) * | 1983-03-03 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Static mixing device |
| US4448927A (en) * | 1983-03-14 | 1984-05-15 | Dow Corning Corporation | Method of polymerizing oligomers of polydiorganosiloxane in the presence of filler |
| US5599856A (en) * | 1984-03-01 | 1997-02-04 | Amoco Corporation | Epoxy resin systems containing modifiers |
| DE3587828T2 (de) * | 1984-07-26 | 1994-09-29 | Kanegafuchi Chemical Ind | Vernetzbare Polymerzusammensetzung. |
| DE3518965A1 (de) * | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
| US4705838A (en) * | 1986-07-07 | 1987-11-10 | Ashland Oil, Inc. | Acceleration of rate of cure in boron trifluoride amine catalyzed cure of epoxy resins |
| KR950003688B1 (ko) * | 1986-10-30 | 1995-04-17 | 미쓰이세끼유 가가꾸 고오교오 가부시끼가이샤 | 경화성 조성물 |
| US4746725A (en) * | 1987-02-25 | 1988-05-24 | General Electric Company | Cyclic polycarbonate-polyepoxide reaction product and method for their preparation |
| 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 |
| US4823927A (en) * | 1987-08-24 | 1989-04-25 | Ancra Corporation | Retractable roller system for cargo handling |
| US5082147A (en) * | 1988-02-29 | 1992-01-21 | Richard Jacobs | Composition dispensing system |
| US5079098A (en) * | 1988-03-16 | 1992-01-07 | Loctite Corporation | Primer for bonding low surface energy plastics with cyanoacrylate adhesives and bonding method employing same |
| US4985477A (en) * | 1988-05-13 | 1991-01-15 | Dow Corning Corporation | Method of producing treated silica filler for silicone rubber |
| JPH0249088A (ja) * | 1988-08-11 | 1990-02-19 | Showa Denko Kk | 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 |
| US5409995A (en) * | 1989-05-29 | 1995-04-25 | Kanegafuchi Chemical Industry Co., Ltd. | Curing agent, preparation thereof and curable composition comprising the same |
| AU627316B2 (en) | 1989-06-05 | 1992-08-20 | Nippon Paint Co., Ltd. | Antimony, arsenic, boron and phosphorous halide salts of quaternary ammonium compounds |
| US5132377A (en) | 1989-06-05 | 1992-07-21 | Nippon Paint Company, Limited | Heat-latent, cationic polymerization initiator and resin compositions containing the same |
| US5126416A (en) * | 1990-03-26 | 1992-06-30 | Loctite Corporation | Peroxy cured (meth)acrylic ester compositions employing nitrite, borate, silicate or carbonate salt accelerators |
| ZA913801B (en) | 1990-05-21 | 1993-01-27 | Dow Chemical Co | Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| US5204386A (en) * | 1990-11-13 | 1993-04-20 | The Dow Chemical Company | Acrylic-modified epoxy resin adhesive compositions with improved rheological control |
| US5506326A (en) | 1991-03-06 | 1996-04-09 | Loctite (Ireland) Limited | Air-activatable polymerizable compositions containing onium salts |
| US5143884A (en) * | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| JP2995308B2 (ja) * | 1991-09-09 | 1999-12-27 | 鐘淵化学工業株式会社 | 硬化性組成物 |
| US5250228A (en) * | 1991-11-06 | 1993-10-05 | Raychem Corporation | Conductive polymer composition |
| JPH05132538A (ja) * | 1991-11-13 | 1993-05-28 | Nippon Paint Co Ltd | 新規常温硬化性樹脂組成物 |
| DE69315200T2 (de) * | 1992-01-24 | 1998-06-10 | Reilly Ind Inc | Neue härter und beschleuniger für epoxidharze und härtbare zusammensetzungen und verfahren |
| 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 |
| US5411998A (en) * | 1992-07-24 | 1995-05-02 | Loctite Limited | Curing anaerobic compositions through thick bondlines |
| JP3213424B2 (ja) * | 1993-02-15 | 2001-10-02 | 理想科学工業株式会社 | 孔版印刷装置の排紙装置 |
| CA2115607A1 (en) | 1993-02-18 | 1994-08-19 | Brendan Kneafsey | Air-activatable polymerisable compositions containing onium salts |
| KR100214288B1 (ko) * | 1993-04-16 | 1999-08-02 | 성재갑 | 안개서림 방지용 내마모성 피복조성물 및 이를 도포한 합성수지 성형품 |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| 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 |
| JP3335359B2 (ja) * | 1993-12-22 | 2002-10-15 | トレムコ、リミテッド | 湿気−硬化性改質アクリル重合体シーラント組成物 |
| JP3535167B2 (ja) * | 1994-02-22 | 2004-06-07 | 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 | 有機ホウ素アミン錯体に基づく重合開始剤システムを用いて製造される重合性組成物 |
| JPH07316525A (ja) * | 1994-05-24 | 1995-12-05 | Mitsui Petrochem Ind Ltd | フレキシブルプリント配線板用接着剤組成物 |
| BR9510062A (pt) | 1994-12-19 | 1998-06-02 | Dentsply Int Inc | Macromonômeto esterificado e composição |
| 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 |
| CN1089104C (zh) * | 1995-08-11 | 2002-08-14 | 美国3M公司 | 引发剂体系和由此制备的粘合剂组合物 |
| US5686544A (en) * | 1995-08-11 | 1997-11-11 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
| JP3084352B2 (ja) * | 1995-08-28 | 2000-09-04 | 太陽インキ製造株式会社 | 銅箔ラミネート方式ビルドアップ用絶縁樹脂組成物とこれを用いた多層プリント配線板の製造方法 |
| WO1997017383A1 (en) * | 1995-11-07 | 1997-05-15 | Minnesota Mining And Manufacturing Company | Initiator system and adhesive composition made therewith |
| US5952409A (en) * | 1996-01-31 | 1999-09-14 | 3M Innovative Properties Company | Compositions and methods for imparting stain resistance and stain resistant articles |
| US5817376A (en) * | 1996-03-26 | 1998-10-06 | Minnesota Mining And Manufacturing Company | Free-radically polymerizable compositions capable of being coated by electrostatic assistance |
| JP3920348B2 (ja) * | 1996-04-02 | 2007-05-30 | コグネックス コーポレイション | 平坦な鏡面基板の指標を観察する画像形成装置 |
| US5721281A (en) * | 1996-07-01 | 1998-02-24 | Blount; David H. | Flame retardant porous plastics |
| US5935711A (en) | 1996-10-23 | 1999-08-10 | 3M Innovative Properties Company | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
| US6090904A (en) * | 1996-12-19 | 2000-07-18 | Ara Werk Kramer Gmbh | Silicone compositions curable in presence of moisture |
| GB9703552D0 (en) * | 1997-02-20 | 1997-04-09 | Dow Corning | Polymerisation of cyclosiloxanes in the presence of fillers |
| US5807910A (en) * | 1997-06-23 | 1998-09-15 | Industrial Technology Research Institute | Preolymerizing epoxy resin, functionalized rubber with filler to form adhesive |
| US5948854A (en) * | 1997-09-25 | 1999-09-07 | Dow Corning S.A. | Alkoxy-functional RTV compositions with increased green strength and increased storage stability |
| US6008284A (en) * | 1997-12-23 | 1999-12-28 | Dow Corning Corporation | Fast curing alkoxy-functional RTV compositions |
| JP4286345B2 (ja) * | 1998-05-08 | 2009-06-24 | 株式会社リコー | 検索支援システム及びコンピュータ読み取り可能な記録媒体 |
| US6812308B2 (en) | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
| DE69823562T2 (de) | 1998-06-12 | 2005-04-21 | Minnesota Mining & Mfg | Initiatorsystem sowie damit hergestellte polymerisierbare zusammensetzungen |
| US6727320B2 (en) | 1998-11-02 | 2004-04-27 | Henkel Loctite Corporation | Polymerizable compositions in non-flowable forms |
| US6482868B1 (en) * | 1998-12-31 | 2002-11-19 | 3M Innovative Properties Company | Accelerators useful for energy polymerizable compositions |
| US6271377B1 (en) * | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| US6252023B1 (en) * | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
| US6207781B1 (en) * | 1999-08-20 | 2001-03-27 | Dow Corning Corporation | Polymerization of an organofunctional cocyclic siloxane |
| US6054548A (en) * | 1999-08-26 | 2000-04-25 | Dow Corning Limited | Process for producing a silicone polymer |
| US6410667B1 (en) * | 1999-11-04 | 2002-06-25 | 3M Innovative Properties Company | Initiator/amidine complexes, systems comprising the complexes, and polymerized compositions made therewith |
| US6806330B1 (en) | 1999-12-17 | 2004-10-19 | Dow Global Technologies Inc. | Amine organoborane complex polymerization initiators and polymerizable compositions |
| EP1201722A1 (en) * | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
| WO2003035703A1 (en) | 2001-10-23 | 2003-05-01 | Henkel Corporation | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| US6740716B2 (en) * | 2001-10-30 | 2004-05-25 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
| US6630555B2 (en) * | 2001-11-06 | 2003-10-07 | Lord Corporation | Internally blocked organoborate initiators and adhesives therefrom |
| US6762260B2 (en) * | 2002-03-05 | 2004-07-13 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
| 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 |
| JP2004203773A (ja) * | 2002-12-25 | 2004-07-22 | Tokuyama Corp | 硬化性組成物 |
| US6777512B1 (en) * | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| EP1648944A1 (en) * | 2003-06-09 | 2006-04-26 | The Dow Global Technologies Inc. | Stabilized organoborane polymerization initiators and polymerizable compositions |
| DE102004034645A1 (de) | 2004-07-16 | 2006-02-09 | Ewald Dörken Ag | Korrosionsschutz-Beschichtungsmittel für Metall und Verfahren zur Herstellung hierfür |
| BRPI0617975A2 (pt) | 2005-10-07 | 2011-08-09 | Dow Global Tchnologies Inc | composto de amido-borato |
-
2004
- 2004-12-21 DE DE602004015841T patent/DE602004015841D1/de not_active Expired - Lifetime
- 2004-12-21 US US11/019,056 patent/US7534843B2/en not_active Expired - Fee Related
- 2004-12-21 AT AT04815060T patent/ATE404359T1/de not_active IP Right Cessation
- 2004-12-21 KR KR1020067012306A patent/KR20060118559A/ko not_active Ceased
- 2004-12-21 CN CN200480038160XA patent/CN1898082B/zh not_active Expired - Fee Related
- 2004-12-21 JP JP2006547264A patent/JP2007515547A/ja active Pending
- 2004-12-21 ES ES04815060T patent/ES2309598T3/es not_active Expired - Lifetime
- 2004-12-21 RU RU2006126672/04A patent/RU2364605C2/ru not_active IP Right Cessation
- 2004-12-21 WO PCT/US2004/042939 patent/WO2005063480A1/en not_active Ceased
- 2004-12-21 BR BRPI0417298-1A patent/BRPI0417298A/pt not_active Application Discontinuation
- 2004-12-21 EP EP04815060A patent/EP1699625B1/en not_active Expired - Lifetime
- 2004-12-21 CA CA002548109A patent/CA2548109A1/en not_active Abandoned
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2007
- 2007-09-26 US US11/861,616 patent/US8114947B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5684102A (en) * | 1995-04-14 | 1997-11-04 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive compositions made therewith |
| RU2171000C2 (ru) * | 1997-01-17 | 2001-07-20 | Миннесота Майнинг Энд Мэнюфекчуринг Компани | Кабельный кожух, уплотненный инжекцией клея с низкой поверхностной энергией |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2309598T3 (es) | 2008-12-16 |
| EP1699625B1 (en) | 2008-08-13 |
| BRPI0417298A (pt) | 2007-03-13 |
| DE602004015841D1 (de) | 2008-09-25 |
| EP1699625A1 (en) | 2006-09-13 |
| CN1898082A (zh) | 2007-01-17 |
| ATE404359T1 (de) | 2008-08-15 |
| JP2007515547A (ja) | 2007-06-14 |
| CN1898082B (zh) | 2010-09-29 |
| US20080045681A1 (en) | 2008-02-21 |
| RU2006126672A (ru) | 2008-01-27 |
| US20050137370A1 (en) | 2005-06-23 |
| WO2005063480A1 (en) | 2005-07-14 |
| CA2548109A1 (en) | 2005-07-14 |
| US7534843B2 (en) | 2009-05-19 |
| US8114947B2 (en) | 2012-02-14 |
| KR20060118559A (ko) | 2006-11-23 |
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