JP6215317B2 - 硬化性ポリウレア形成組成物、製造方法、及び複合物品 - Google Patents
硬化性ポリウレア形成組成物、製造方法、及び複合物品 Download PDFInfo
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- JP6215317B2 JP6215317B2 JP2015517295A JP2015517295A JP6215317B2 JP 6215317 B2 JP6215317 B2 JP 6215317B2 JP 2015517295 A JP2015517295 A JP 2015517295A JP 2015517295 A JP2015517295 A JP 2015517295A JP 6215317 B2 JP6215317 B2 JP 6215317B2
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Images
Classifications
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/50—Compositions for coatings applied by spraying at least two streams of reaction components
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/90—Compositions for anticorrosive coatings
-
- 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261660245P | 2012-06-15 | 2012-06-15 | |
| US61/660,245 | 2012-06-15 | ||
| PCT/US2013/044111 WO2013188176A1 (en) | 2012-06-15 | 2013-06-04 | Curable polyurea forming composition, method of making, and composite article |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015525275A JP2015525275A (ja) | 2015-09-03 |
| JP2015525275A5 JP2015525275A5 (enExample) | 2016-06-30 |
| JP6215317B2 true JP6215317B2 (ja) | 2017-10-18 |
Family
ID=48626671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015517295A Expired - Fee Related JP6215317B2 (ja) | 2012-06-15 | 2013-06-04 | 硬化性ポリウレア形成組成物、製造方法、及び複合物品 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9587139B2 (enExample) |
| EP (1) | EP2861684B1 (enExample) |
| JP (1) | JP6215317B2 (enExample) |
| CN (1) | CN104520394B (enExample) |
| WO (1) | WO2013188176A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3116959T (pt) * | 2014-03-14 | 2019-01-11 | Akzo Nobel Coatings Int Bv | Composição de revestimento |
| EP3168246B1 (en) | 2014-07-08 | 2019-02-27 | Mitsui Chemicals, Inc. | Polymerizable composition for optical material, and application for same |
| EP3061779B2 (de) | 2015-02-27 | 2022-01-05 | Mipa Se | Beschichtungsmittel und deren Verwendung, insbesondere zur Ausbildung einer Schutzbeschichtung auf einer Oberfläche |
| WO2019038721A1 (en) * | 2017-08-25 | 2019-02-28 | 3M Innovative Properties Company | POLYUREA COMPOSITION COMPRISING A HYDROXYL COMPONENT AND METHODS |
| WO2019038722A1 (en) * | 2017-08-25 | 2019-02-28 | 3M Innovative Properties Company | POLYUREA COMPOSITION COMPRISING A WATER SENSOR AND A HYDROXYL COMPONENT AND METHOD |
| ES2972689T3 (es) | 2018-10-19 | 2024-06-14 | Momentive Performance Mat Gmbh | Polisiloxanos con funcionalidad éster de ácido aspártico, su preparación y uso de los mismos |
| CN109671869B (zh) * | 2018-12-12 | 2020-06-16 | 武汉华星光电半导体显示技术有限公司 | 复合膜层的制作方法及显示器件 |
| US20210039359A1 (en) * | 2019-08-08 | 2021-02-11 | Covestro Llc | Flexibilized polyurethanes for flexible packaging adhesive without aromatic amine migration |
| US11827788B2 (en) | 2019-10-07 | 2023-11-28 | Covestro Llc | Faster cure polyaspartic resins for faster physical property development in coatings |
| JP7324790B2 (ja) * | 2021-03-05 | 2023-08-10 | 日本ペイント・インダストリアルコーティングス株式会社 | 塗料組成物 |
| KR20240150469A (ko) | 2022-02-14 | 2024-10-15 | 모멘티브 퍼포먼스 머티리얼즈 게엠베하 | 아스파르트산 에스테르-관능 폴리실록산, 그 제조 및 용도 |
| KR102476592B1 (ko) * | 2022-02-21 | 2022-12-09 | 진유동 | 투명 폴리우레아 및 이를 이용한 방수공법 |
Family Cites Families (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB550022A (en) | 1940-06-14 | 1942-12-18 | Du Pont | Improved protein-containing materials and their applications |
| GB1073183A (en) | 1963-02-05 | 1967-06-21 | Ici Ltd | Leather-like materials |
| US3386942A (en) | 1964-06-29 | 1968-06-04 | Eastman Kodak Co | Stabilization of non-yellowing segmented polyurethane copolymers of polymeric diols, functionally aliphatic diisocyanates and functionally aliphatic diamines |
| US4036906A (en) | 1969-12-30 | 1977-07-19 | The Goodyear Tire & Rubber Company | Cured polyurethane compositions containing epoxy resins |
| US3931449A (en) | 1972-08-17 | 1976-01-06 | Toyo Seikan Kaisha Limited | Resinous laminates having improved gas permeation and resistance to delamination |
| DE2252280C3 (de) | 1972-10-25 | 1981-03-19 | Bayer Ag, 5090 Leverkusen | Textilbeschichtungen und Syntheseleder aus Polycarbonat-Polyharnstoff-Elastomeren |
| US3856749A (en) | 1973-04-17 | 1974-12-24 | Du Pont | Stabilization of polymers containing poly(alkylene oxide) units |
| US3900687A (en) | 1973-09-10 | 1975-08-19 | Chevron Res | Process for coating a surface and the coated surface |
| US4002598A (en) | 1975-03-06 | 1977-01-11 | Texaco Development Corporation | Polyether urea epoxy curing agent |
| US4178427A (en) | 1976-05-05 | 1979-12-11 | Texaco Development Corp. | Polyether urea epoxy curing agent |
| DE3018023A1 (de) | 1980-05-10 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyharnstoffen |
| DE3119151A1 (de) | 1981-05-14 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur splittersicheren beschichtung von glasoberflaechen |
| DE3520318A1 (de) | 1985-06-07 | 1986-12-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zum ummanteln von glasscheibenkanten mit einem elastischen polyisocyanat-polyadditionsprodukt unter verwendung eines epoxidharz-haertersystems als haftvermittler |
| US4881951A (en) | 1987-05-27 | 1989-11-21 | Minnesota Mining And Manufacturing Co. | Abrasive grits formed of ceramic containing oxides of aluminum and rare earth metal, method of making and products made therewith |
| DE3727128A1 (de) | 1987-08-14 | 1989-02-23 | Bayer Ag | Verfahren zur herstellung von in der waerme haertbaren einkomponenten-polyurethan-polyharnstoff-systemen |
| CA2057124A1 (en) | 1991-08-26 | 1993-02-27 | Dudley J. Ii Primeaux | Slow curing polyurea elastomers |
| DE4217023A1 (de) | 1992-05-22 | 1993-11-25 | Bayer Ag | Verwendung von alkylthiosubstituierten aromatischen Diaminen aus Härter für Polyisocyanate in Beschichtungsmitteln oder Fugenvergußmassen |
| US5352733A (en) | 1993-03-10 | 1994-10-04 | R. E. Hart Labs, Inc. | Water based, solvent free, two component aliphatic polyurethane coating |
| US6290614B1 (en) | 1998-03-18 | 2001-09-18 | Spalding Sports Worldwide, Inc. | Golf ball which includes fast-chemical-reaction-produced component and method of making same |
| DE4337236A1 (de) | 1993-10-30 | 1995-05-04 | Huels Chemische Werke Ag | Kalthärtende, lösungsmittelarme oder lösungsmittelfreie 2K-Polyurethan-Polyharnstoff-Massen |
| DE69637954D1 (de) | 1995-02-01 | 2009-07-30 | Boston Scient Scimed Inc | Medizinisches Gerät enthaltend ein chemisch behandeltes Metallsubstrat |
| US5919570A (en) | 1995-02-01 | 1999-07-06 | Schneider Inc. | Slippery, tenaciously adhering hydrogel coatings containing a polyurethane-urea polymer hydrogel commingled with a poly(N-vinylpyrrolidone) polymer hydrogel, coated polymer and metal substrate materials, and coated medical devices |
| US5814398A (en) | 1996-03-22 | 1998-09-29 | Fabick, Inc. | In situ vehicle bed liner and method of forming same |
| US6730150B1 (en) | 1996-06-28 | 2004-05-04 | Xerox Corporation | Phase change ink formulation containing a combination of a urethane resin, a mixed urethane/urearesin, a mono-amide and a polyethylene wax |
| JPH11130964A (ja) * | 1997-10-31 | 1999-05-18 | New Japan Chem Co Ltd | ロジン系ガラス化物及びポリオレフィン樹脂用核剤並びにポリオレフィン樹脂組成物とその成形体 |
| US6297320B1 (en) | 1998-11-20 | 2001-10-02 | The Sherwin-Williams Company | Curable compositions comprising acetoacetoxy and imine functionality |
| BR9915981B1 (pt) | 1998-12-07 | 2008-11-18 | processo para a coagulaÇço de dispersÕes aquosas pàs-reticulÁveis, dispersÕes assim obtidas e seu uso. | |
| EP1033440B1 (de) | 1999-03-04 | 2004-05-26 | Adisa Service und Entwicklungs AG | Flüssigkeitsdichter Bodenbelag und Verfahren zur Herstellung eines solchen |
| AU755902B2 (en) | 1999-03-29 | 2003-01-02 | Callaway Golf Company | Golf ball which includes fast-chemical-reaction-produced component and method of making same |
| DE19914882A1 (de) | 1999-04-01 | 2000-10-05 | Bayer Ag | Selbstvernetzende Polyurethan-, Polyurethan-Polyharnstoff- bzw. Polyharnstoff-Dispersionen für Schlichten |
| US6369189B1 (en) | 1999-12-07 | 2002-04-09 | Reichhold, Inc. | Hindered amine adducts for polyurea systems |
| DE10011277A1 (de) | 2000-03-08 | 2001-09-13 | Bayer Ag | Abziehlack |
| GB0019505D0 (en) | 2000-08-08 | 2000-09-27 | Wood Limited E | Coating for drinking water pipelines |
| BR0114368A (pt) | 2000-10-02 | 2003-12-09 | Huntsman Int Llc | Processo para preparar um elastÈmero de poliuréia, e, elastÈmero de poliuréia |
| US20030013835A1 (en) | 2001-04-25 | 2003-01-16 | Anastasios Zahariadis | 100% polyurea elastomeric system, process for producing and use thereof |
| US7001948B2 (en) | 2001-05-16 | 2006-02-21 | American Polymer Corporation | Polyurea coating compositions |
| CN1128850C (zh) | 2001-05-30 | 2003-11-26 | 海洋化工研究院 | 喷涂聚脲刚性材料及其施工方法 |
| US6632147B2 (en) | 2001-10-09 | 2003-10-14 | Acushnet Company | Golf ball with vapor barrier layer and method of making same |
| US6797789B2 (en) | 2001-10-19 | 2004-09-28 | Visuron Technologies, Inc. | Phenolic/polyurea coating co-polymer compositions and process |
| DE10201546A1 (de) | 2002-01-17 | 2003-07-31 | Bayer Ag | Stabilisierte wässrige Polyurethan-Polyharnstoff Dispersionen |
| JP2004027148A (ja) * | 2002-06-28 | 2004-01-29 | Canon Inc | ポリウレア樹脂組成物、ポリウレア樹脂用硬化剤及びポリウレア樹脂形成用の組成物セット |
| CN1179008C (zh) | 2002-08-31 | 2004-12-08 | 海洋化工研究院 | 用于固体浮力材料的喷涂聚脲包敷层 |
| GB0220462D0 (en) | 2002-09-03 | 2002-10-09 | Pipeline Polymers Ltd | Lining of pipes |
| US20070270240A1 (en) | 2002-09-09 | 2007-11-22 | Reactamine Technology, Llc | Pure polyurea and method for making same |
| US6774206B2 (en) | 2002-09-26 | 2004-08-10 | Bayer Polymers Llc | Polyaspartate resins with improved flexibility |
| US6774207B2 (en) | 2002-09-26 | 2004-08-10 | Bayer Polymers Llc | Polyaspartate resins with good hardness and flexibility |
| US6790925B2 (en) | 2002-12-05 | 2004-09-14 | Bayer Polymers Llc | In-situ preparation of polyaspartic ester mixtures |
| US20040197472A1 (en) | 2003-04-04 | 2004-10-07 | Scofield Harry J. | Process and apparatus for sealing freezer enclosures from moisture and contamination |
| GB0313275D0 (en) | 2003-06-09 | 2003-07-16 | Wood Ltd E | Renovating water pipelines |
| US20070043197A1 (en) * | 2003-07-07 | 2007-02-22 | Huntsman Petrochemical Corporation | Polyurea polymers from secondary polyether polyamines |
| DE10353663A1 (de) | 2003-11-17 | 2005-06-16 | Henkel Kgaa | Polyurethanzusammensetzungen mit NCO- und Silylreaktivität |
| US20050244628A1 (en) | 2004-04-28 | 2005-11-03 | Turek Robert L | Soft articles and method |
| CA2580582A1 (en) | 2004-10-15 | 2006-04-27 | Verena M. T. Thiede | An isocyanate-terminated prepolymer composition and a polyurethane or polyurea elastomer produced therefrom |
| JP2006183336A (ja) | 2004-12-28 | 2006-07-13 | Ntt Infranet Co Ltd | 歩道橋の床構造 |
| US20080200620A1 (en) | 2005-07-07 | 2008-08-21 | Huntsman International Llc | Spray Polyurea System, Process for Producing and Use Thereof |
| DE102005040130A1 (de) | 2005-08-25 | 2007-03-01 | Bayer Materialscience Ag | Polyurethanpolyharnstoff-Dispersionen |
| US20070066786A1 (en) | 2005-09-22 | 2007-03-22 | The Hanson Group, Llc | Methods of preparing and using polyurea elastomers |
| DE102005047562A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Materialscience Ag | Zweitkomponenten-Systeme für die Herstellung flexibler Beschichtungen |
| DE102005047560A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Materialscience Ag | Zusammensetzung zur Herstellung von Polyharnstoffbeschichtungen |
| EP1945724A2 (en) | 2005-11-08 | 2008-07-23 | Laxmi C. Gupta | Methods for applying fire retardant systems, compositions and uses |
| DE102006002156A1 (de) | 2006-01-17 | 2007-07-19 | Bayer Materialscience Ag | Polyurethan-Polyharnstoff-Dispersionen auf Basis von Polyether-Polycarbonat-Polyolen |
| CN100441648C (zh) | 2006-01-20 | 2008-12-10 | 广州秀珀化工有限公司 | 一种喷涂聚脲高强弹性防水涂料及其施工方法 |
| US8444758B2 (en) * | 2006-10-19 | 2013-05-21 | Eastman Chemical Company | Low voc additives for extending the wet edge and open time of aqueous coatings |
| JP4995282B2 (ja) * | 2006-10-27 | 2012-08-08 | ソシエテ ド テクノロジー ミシュラン | ポリ尿素接着剤 |
| BRPI0809049A2 (pt) | 2007-03-23 | 2014-09-02 | Innovatier Inc | Cartão eletrônico e respectivo método de fabrico |
| US20100252217A1 (en) | 2007-03-26 | 2010-10-07 | Robert Eberhardt | Paper machine clothing with edge reinforcement |
| US20090030161A1 (en) | 2007-07-27 | 2009-01-29 | Bayer Materialscience Llc | Allophanate modified diphenylmethane diisocyanates, prepolymers thereof, and their use in the preparation of polyureas and polyurethanes |
| US7980165B2 (en) | 2007-10-03 | 2011-07-19 | Martin Marietta Materials, Inc. | Modular blast-resistant panel system for reinforcing existing structures |
| US7781513B2 (en) | 2007-11-14 | 2010-08-24 | Momentive Performance Materials Inc. | Two-part moisture-curable resin composition and adhesive, sealant and coating compositions based thereon |
| US8378037B2 (en) | 2007-12-26 | 2013-02-19 | Momentive Performance Materials Inc. | Moisture-curable silylated polyurea and adhesive, sealant and coating compositions containing same |
| WO2009086256A1 (en) | 2007-12-27 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Adhesion-promoting agent for protective coatings |
| JP2009167281A (ja) * | 2008-01-15 | 2009-07-30 | Sekisui Chem Co Ltd | 両面粘着テープ及び液晶表示装置 |
| US8932497B2 (en) | 2008-03-13 | 2015-01-13 | Laxmi C. Gupta | Fire retardant coatings and bodies, and methods of use |
| WO2009131935A2 (en) | 2008-04-21 | 2009-10-29 | Ppg Industries Ohio, Inc. | Low temperature application coating composition comprising polyurea and a phosphorus-containing polyol and footwear comprising polyurea |
| JP4845220B2 (ja) | 2008-05-13 | 2011-12-28 | 日本特殊塗料株式会社 | ポリウレタン塗膜防水材組成物 |
| DE102008024352A1 (de) | 2008-05-20 | 2009-11-26 | Bayer Materialscience Ag | Polyharnstoffzusammensetzung |
| US20090293350A1 (en) | 2008-05-27 | 2009-12-03 | Fountainhead, Llc | Raised bed planter with biomimetic exoskeleton |
| JP5543439B2 (ja) | 2008-05-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | 複数の粘着付与剤を有する接着剤組成物 |
| CA2640098C (en) | 2008-09-26 | 2018-06-12 | Quantum Technical Services Ltd. | Flame retardant coating |
| WO2010034109A1 (en) | 2008-09-26 | 2010-04-01 | Quantum Technical Services Ltd. | Flame retardant coating |
| US20100080920A1 (en) | 2008-09-26 | 2010-04-01 | Tony Lagrange | Flame retardant coating |
| EP2221330A1 (de) | 2009-02-19 | 2010-08-25 | Bayer MaterialScience AG | Funktionalisierte Polyurethanpolyharnstoff-Dispersionen |
| WO2010120617A2 (en) | 2009-04-16 | 2010-10-21 | 3M Innovative Properties Company | Method and composition suitable for coating drinking water pipelines |
| US9944763B2 (en) | 2009-12-01 | 2018-04-17 | Gates Corporation | Polyurea-urethane cord treatment for power transmission belt and belt |
| WO2012010558A1 (en) | 2010-07-22 | 2012-01-26 | Construction Research & Technology Gmbh | Reduction in modulus of polyurethane sealants and adhesives |
| AU2012259420B2 (en) | 2011-03-30 | 2015-03-05 | 3M Innovative Properties Company | Composition comprising cyclic secondary amine and methods of coating drinking water pipelines |
-
2013
- 2013-06-04 US US14/399,254 patent/US9587139B2/en not_active Expired - Fee Related
- 2013-06-04 JP JP2015517295A patent/JP6215317B2/ja not_active Expired - Fee Related
- 2013-06-04 EP EP13729207.4A patent/EP2861684B1/en not_active Not-in-force
- 2013-06-04 CN CN201380031024.7A patent/CN104520394B/zh not_active Expired - Fee Related
- 2013-06-04 WO PCT/US2013/044111 patent/WO2013188176A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US9587139B2 (en) | 2017-03-07 |
| EP2861684B1 (en) | 2016-03-30 |
| CN104520394B (zh) | 2016-10-26 |
| JP2015525275A (ja) | 2015-09-03 |
| WO2013188176A1 (en) | 2013-12-19 |
| US20150104652A1 (en) | 2015-04-16 |
| CN104520394A (zh) | 2015-04-15 |
| EP2861684A1 (en) | 2015-04-22 |
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