JP2005534773A - ポリマー材料の変性方法および得られる組成物 - Google Patents
ポリマー材料の変性方法および得られる組成物 Download PDFInfo
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- JP2005534773A JP2005534773A JP2004526021A JP2004526021A JP2005534773A JP 2005534773 A JP2005534773 A JP 2005534773A JP 2004526021 A JP2004526021 A JP 2004526021A JP 2004526021 A JP2004526021 A JP 2004526021A JP 2005534773 A JP2005534773 A JP 2005534773A
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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
- C08F8/00—Chemical modification by after-treatment
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
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- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
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| US10/211,415 US7632916B2 (en) | 2002-08-02 | 2002-08-02 | Process to modify polymeric materials and resulting compositions |
| PCT/US2003/021051 WO2004013189A2 (en) | 2002-08-02 | 2003-07-03 | Process to modify polymeric materials and resulting compositions |
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| JP2011011742A Division JP5485920B2 (ja) | 2002-08-02 | 2011-01-24 | ポリマー材料の変性方法および得られる組成物 |
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| US (2) | US7632916B2 (enExample) |
| EP (1) | EP1551885B1 (enExample) |
| JP (2) | JP2005534773A (enExample) |
| KR (1) | KR20050033642A (enExample) |
| CN (1) | CN100387624C (enExample) |
| AU (1) | AU2003249701A1 (enExample) |
| BR (1) | BR0313156A (enExample) |
| CA (1) | CA2494238A1 (enExample) |
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Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US7157283B2 (en) * | 2002-08-02 | 2007-01-02 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of modified materials |
| US8236874B2 (en) * | 2003-06-11 | 2012-08-07 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| US7402625B2 (en) * | 2003-06-11 | 2008-07-22 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| FR2868782B1 (fr) * | 2004-04-13 | 2006-06-16 | Solvay Sa Sa Belge | Procede de recuperation d'un polymere en solution |
| US6969491B1 (en) | 2004-09-01 | 2005-11-29 | 3M Innovative Properties Company | Stirred tube reactor and method of using the same |
| US7495051B2 (en) * | 2004-09-27 | 2009-02-24 | 3M Innovative Properties Company | Nanocomposite and method of making the same |
| US7329702B2 (en) * | 2004-09-27 | 2008-02-12 | 3M Innovative Properties Company | Composition and method of making the same |
| US7691932B2 (en) * | 2004-09-27 | 2010-04-06 | 3M Innovative Properties Company | Method of making a composition and nanocomposites therefrom |
| US8193270B2 (en) * | 2004-12-14 | 2012-06-05 | 3M Innovative Properties Company | Method of making composites and nanocomposites |
| EP1861429B1 (en) | 2005-01-11 | 2013-03-13 | Basf Se | Process for the post-modification of homo and copolymers prepared by controlled free radical polymerization processes |
| BRPI0606959A2 (pt) * | 2005-02-23 | 2017-06-13 | 3M Innovative Properties Co | mescla polimérica |
| US20090306347A1 (en) * | 2005-08-29 | 2009-12-10 | Japan Science And Technology Agency | Antibody produced using ostrich and method for production thereof |
| US20070135577A1 (en) * | 2005-12-09 | 2007-06-14 | Shefelbine Terri A | Intermediate elastomer compositions |
| US7863381B2 (en) * | 2006-03-08 | 2011-01-04 | 3M Innovative Properties Company | Polymer composites |
| JP5425623B2 (ja) * | 2006-07-11 | 2014-02-26 | チバ ホールディング インコーポレーテッド | カラーフィルター組成物 |
| US20080139722A1 (en) * | 2006-12-08 | 2008-06-12 | 3M Innovative Properties Company | Vibration damping polymer composites |
| ATE506413T1 (de) * | 2007-03-01 | 2011-05-15 | Prs Mediterranean Ltd | Verfahren zur herstellung kompatibilisierter polymermischungen und artikeln |
| KR20100087158A (ko) * | 2007-10-09 | 2010-08-03 | 크레이튼 폴리머즈 유.에스. 엘엘씨 | 특정 블록 공중합체로 제조된 최종 용도 제품 |
| US9499642B2 (en) | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
| US9045575B2 (en) | 2011-11-11 | 2015-06-02 | Rohm And Haas Company | Polymethacrylic acid anhydride telomers |
| JP2014066650A (ja) * | 2012-09-26 | 2014-04-17 | Japan Polypropylene Corp | Ｄｏｓｙ法を用いるｎｍｒ測定方法 |
| EP2778183B1 (en) | 2013-03-15 | 2015-04-29 | Rohm and Haas Company | Polymethacrylic acid anhydride telomers |
| US9921207B2 (en) | 2015-10-27 | 2018-03-20 | International Business Machines Corporation | Method for determining wear of a connector contact using atom transfer radical polymerization |
| WO2019014662A1 (en) * | 2017-07-14 | 2019-01-17 | Arkema Inc. | HIGH-RESISTANCE VINYLIDENE POLYFLUORIDE SIZED FIBER DIMENSIONS |
| CN114075335B (zh) * | 2020-08-13 | 2023-03-07 | 台光电子材料(昆山)有限公司 | 一种聚苯醚树脂及含其的树脂组合物和制品 |
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| CN117777735A (zh) * | 2023-12-28 | 2024-03-29 | 江西蓝星星火有机硅有限公司 | 热硫化硅橡胶的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07268023A (ja) * | 1992-05-08 | 1995-10-17 | Shell Internatl Res Maatschappij Bv | 安定な酸無水物環を有するポリマー |
| JPH09277464A (ja) * | 1996-04-12 | 1997-10-28 | Sumitomo Chem Co Ltd | 耐熱性、ガスバリア性に優れたシートおよび成形体 |
| JP2002161110A (ja) * | 2000-11-28 | 2002-06-04 | Nippon Synthetic Chem Ind Co Ltd:The | ビニルアルコール−ビニルアミン共重合体の製造法 |
Family Cites Families (150)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3036997A (en) * | 1956-11-21 | 1962-05-29 | Du Pont | Diene-modified polymers and elastomers thereform |
| US2915554A (en) * | 1957-07-23 | 1959-12-01 | Minnesota Mining & Mfg | Non-ionic surfactant derivatives of perfluoro alkane-sulfonamides |
| US3252932A (en) * | 1959-08-10 | 1966-05-24 | Minnesota Mining & Mfg | Resin compositions comprising a segmented fluorine-containing copolymer and an aminoplast |
| US3356763A (en) | 1962-04-09 | 1967-12-05 | Phillips Petroleum Co | Continuous process for producing block copolymers of dienes and vinyl aromatic hydrocarbons |
| US3322857A (en) * | 1964-03-04 | 1967-05-30 | Monsanto Co | Polymeric blends containing a graft copolymer of vinyl chloride onto chlorinated or chlorosulfonated polyolefin |
| US3474081A (en) | 1966-03-14 | 1969-10-21 | Du Pont | Methyl methacrylate polymer and process for making same |
| CH506322A (de) | 1969-03-17 | 1971-04-30 | List Heinz | Mehrspindelige Misch- und Knetmaschine |
| US3565985A (en) * | 1969-04-10 | 1971-02-23 | Dow Chemical Co | Method of preparing multilayer plastic articles |
| US3647612A (en) * | 1969-06-06 | 1972-03-07 | Dow Chemical Co | Multilayer plastic articles |
| DE2003266A1 (de) * | 1970-01-26 | 1971-08-05 | Waldhof Zellstoff Fab | Verfahren zur Herstellung von Gelen |
| DE2123956C3 (de) | 1970-05-20 | 1979-09-20 | Heinz Dipl.-Ing. Pratteln List (Schweiz) | Misch- und Knetmaschine |
| US3787351A (en) | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
| US3804881A (en) * | 1972-06-20 | 1974-04-16 | Union Carbide Corp | Polymerization using varying monomer concentration |
| DE2250274A1 (de) | 1972-10-13 | 1974-04-25 | Manfred Dipl Ing Lapczyna | Verfahren und vorrichtung zur kontinuierlichen herstellung von faellungs- und traenkungskatalysatoren |
| CH583061A5 (enExample) | 1972-10-18 | 1976-12-31 | List Heinz | |
| US4039024A (en) | 1972-11-21 | 1977-08-02 | Heinz List | Heat exchanger |
| US4086151A (en) * | 1974-02-20 | 1978-04-25 | The Dow Chemical Company | Curable mixtures and cured resins made from linear polymers of glycidol |
| US3944527A (en) * | 1974-07-11 | 1976-03-16 | Minnesota Mining And Manufacturing Company | Fluoroaliphatic copolymers |
| US4172859A (en) | 1975-05-23 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Tough thermoplastic polyester compositions |
| US4346193A (en) * | 1981-05-04 | 1982-08-24 | Atlantic Richfield Company | Continuous process for making star-block copolymers |
| US4500687A (en) * | 1981-06-18 | 1985-02-19 | The Dow Chemical Company | Elastomeric polyether-containing impact polymer products |
| DD206387A1 (de) | 1981-08-03 | 1984-01-25 | Sprela Werke Spremberg Veb | Verfahren zur kontinuierlichen herstellung fluessiger resole |
| CA1231500A (en) * | 1981-10-07 | 1988-01-12 | Richard M. Kopchik | Thermoplastic, non-crosslinked anhydride polymers, imide polymers, and process for preparation |
| US4415615A (en) | 1982-01-15 | 1983-11-15 | Minnesota Mining And Manufacturing Co. | Cellular pressure-sensitive adhesive product and method of making |
| US4371661A (en) * | 1982-02-17 | 1983-02-01 | Atlantic Richfield Company | Semi-continuous process for making star-block copolymers |
| US4458064A (en) * | 1982-02-19 | 1984-07-03 | Celanese Corporation | Process and apparatus for continual melt hydrolysis of acetal copolymers |
| US4533482A (en) | 1982-12-30 | 1985-08-06 | Rohm And Haas Company | Hydrogenated diolefin-lower alkyl acrylate or methacrylate viscosity index improving copolymers for lubricating oils |
| US4485210A (en) | 1983-04-06 | 1984-11-27 | Atlantic Richfield Company | Process for the continuous production of star-block copolymers of a monovinyl aromatic monomer and a conjugated diene |
| US4442273A (en) * | 1983-04-06 | 1984-04-10 | Atlantic Richfield Company | Process and apparatus for continuous polymerization of a monovinyl aromatic monomer |
| IT1164238B (it) | 1983-05-25 | 1987-04-08 | Anic Spa | Procedimento per la polimerizzazione del butadiene |
| US4572819A (en) * | 1983-08-24 | 1986-02-25 | The Dow Chemical Company | Apparatus for anionic polymerization wherein the molecular weight of the polymer is closely controlled |
| US4540623A (en) * | 1983-10-14 | 1985-09-10 | The Dow Chemical Company | Coextruded multi-layered articles |
| FR2565350B1 (fr) | 1984-06-05 | 1986-10-10 | Paris Nord Universite | Moyens propres a permettre le support, le traitement, le stockage et l'analyse automatiques en continu d'echantillons biologiques |
| US4599437A (en) * | 1984-10-29 | 1986-07-08 | Wacker-Chemie Gmbh | Continuous process for varying molecular weight of organopolysiloxanes |
| DE3519411A1 (de) * | 1985-05-30 | 1986-12-04 | Wacker-Chemie GmbH, 8000 München | Kontinuierliches verfahren zur aenderung des molekulargewichts von organosiliciumverbindungen |
| CA1274936A (en) | 1986-12-25 | 1990-10-02 | Akihiro Watanabe | Random copolymer containing hexagonal imide units, a process for producing the same, and an optical disc substrate made of the random copolymer |
| JPH0689047B2 (ja) * | 1987-03-27 | 1994-11-09 | 新日鐵化学株式会社 | 重合反応装置 |
| US4857595A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound hindered amine light stabilizers |
| DE3741670A1 (de) | 1987-12-09 | 1989-06-22 | Basf Ag | Verstaerkte thermoplastische formmassen auf basis von polyphenylenether |
| DE3827668A1 (de) | 1988-08-16 | 1990-02-22 | Bayer Ag | Verstaerkte/gefuellte blends aus thermoplastischen interpolymeren und polyamiden, und ein verfahren |
| DE3832397A1 (de) | 1988-09-23 | 1990-03-29 | Bayer Ag | Formmassen aus polyamiden und tert.-butylacrylat-haltigen pfropfpolymerisaten |
| IT1230085B (it) | 1989-05-24 | 1991-10-05 | Montedipe Spa | Processo per la produzione in massa e in continuo di (co) polimeri vinil aromatici antiurto. |
| US5143854A (en) * | 1989-06-07 | 1992-09-01 | Affymax Technologies N.V. | Large scale photolithographic solid phase synthesis of polypeptides and receptor binding screening thereof |
| EP0406906A3 (en) | 1989-07-07 | 1991-11-27 | Toagosei Chemical Industry Co., Ltd. | Ethylene graft copolymer and molding resin composition containing the same |
| GB8919895D0 (en) | 1989-09-04 | 1989-10-18 | Du Pont Canada | Moisture cross-linking of polymers |
| US5047898A (en) | 1989-11-13 | 1991-09-10 | International Business Machines Corporation | Deflectable contact for providing positive surface contact for shielding electromagnetic interference |
| US5002676A (en) | 1989-12-06 | 1991-03-26 | Shell Oil Company | Block copolymers |
| US5093385A (en) | 1989-12-21 | 1992-03-03 | Minnesota Mining And Manufacturing Company | Method of accelerating photoiniferter polymerization, polymer produced thereby, and product produced therewith |
| JPH0714990B2 (ja) * | 1990-03-02 | 1995-02-22 | 新日鐵化学株式会社 | ゴム変性スチレン系樹脂の製造法 |
| JP2867642B2 (ja) | 1990-07-02 | 1999-03-08 | 日本油脂株式会社 | 不飽和基を含有する含フッ素ブロック共重合体及びその製造方法並びに活性エネルギー線硬化型樹脂用表面改質剤 |
| JPH0463802A (ja) | 1990-07-02 | 1992-02-28 | Takamatsu Yushi Kk | 撥水剤 |
| US5256489A (en) | 1990-08-03 | 1993-10-26 | Quantum Chemical Corporation | Flame retardant polymeric compositions |
| JPH04110315A (ja) | 1990-08-30 | 1992-04-10 | Nippon Oil & Fats Co Ltd | 不飽和基を含有する含フッ素ブロック共重合体及びその製造方法 |
| CA2070431C (en) * | 1990-10-05 | 1995-11-14 | Hirohisa Morishita | Polyoxymethylene copolymer and process for producing the copolymer |
| US5144069A (en) * | 1990-12-13 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Process for the preparation of fluoroaliphatic aminocarboxylate surfactants |
| US5314959A (en) * | 1991-03-06 | 1994-05-24 | Minnesota Mining And Manufacturing Company | Graft copolymers containing fluoroaliphatic groups |
| JP3176944B2 (ja) | 1991-03-11 | 2001-06-18 | 三菱レイヨン株式会社 | メタクリルイミド基含有重合体 |
| US6309752B1 (en) | 1991-04-02 | 2001-10-30 | 3M Innovative Properties Company | Substrate having high initial water repellency and a laundry durable water repellency |
| US5229472A (en) * | 1991-07-04 | 1993-07-20 | Shell Oil Company | Anionic extruder polymerization process |
| WO1993009668A1 (en) | 1991-11-22 | 1993-05-27 | Affymax Technology N.V. | Combinatorial strategies for polymer synthesis |
| US5705551A (en) * | 1991-12-06 | 1998-01-06 | Avery Dennison Corporation | Elastomeric pressure-sensitive adhesive compositions exhibiting good cutting performance |
| DE4142575A1 (de) | 1991-12-21 | 1993-06-24 | Basf Ag | Poly(meth)acrylimide |
| US5227460A (en) * | 1991-12-30 | 1993-07-13 | Xerox Corporation | Cross-linked toner resins |
| US5281651A (en) * | 1992-01-29 | 1994-01-25 | Exxon Chemical Patents Inc. | Compatibilization of dissimilar elastomer blends using ethylene/acrylate/acrylic acid terpolymers |
| FR2686886A1 (fr) | 1992-01-31 | 1993-08-06 | Atochem Elf Sa | Procede de fabrication en continu de copolymeres a bloc vinylaromatique. |
| US5521095A (en) * | 1992-02-10 | 1996-05-28 | Queen's University At Kingston | Temperature scanning reactor method |
| CA2106262C (en) * | 1992-10-01 | 2003-11-18 | Ralph H. Bland | Tear resistant multilayer films and articles incorporating such films |
| DE4234601A1 (de) * | 1992-10-14 | 1994-04-21 | Basf Ag | Verfahren zur Herstellung von Blockcopolymeren durch ionische Polymerisation |
| DE4235786A1 (de) | 1992-10-23 | 1994-04-28 | Basf Ag | Polystyrol-Formmasse und Verfahren zu ihrer Herstellung |
| DE4235980A1 (de) * | 1992-10-24 | 1994-04-28 | Basf Ag | Verfahren zur Herstellung einer vinylaromatischen Verbindung |
| US5356756A (en) | 1992-10-26 | 1994-10-18 | The United States Of America As Represented By The Secretary Of Commerce | Application of microsubstrates for materials processing |
| US5345213A (en) * | 1992-10-26 | 1994-09-06 | The United States Of America, As Represented By The Secretary Of Commerce | Temperature-controlled, micromachined arrays for chemical sensor fabrication and operation |
| US5338802A (en) | 1992-12-21 | 1994-08-16 | Shell Oil Company | Low temperature conversion of polymerized esters |
| DE4313008C1 (de) * | 1993-04-21 | 1994-11-10 | Beiersdorf Ag | Selbstklebemasse auf Acrylathotmelt-Basis, Verfahren zu deren Herstellung und deren Verwendung |
| DE4325352C1 (de) * | 1993-07-28 | 1994-09-01 | Rhodia Ag Rhone Poulenc | Plastifiziertes Celluloseacetat, Verfahren zu dessen Herstellung und seine Verwendung zur Herstellung von Filamenten |
| US5717040A (en) * | 1993-08-16 | 1998-02-10 | Basf Aktiengesellschaft | Continuous process for polymerizing anionically polymerizable vinyl compounds |
| US6160054A (en) | 1995-05-08 | 2000-12-12 | Fmc Corporation | Hetero-telechelic polymers and processes for making same |
| US6197891B1 (en) | 1994-05-13 | 2001-03-06 | Fmc Corporation | Functionalized chain extended initiators for anionic polymerization |
| DE69513526T2 (de) * | 1994-07-08 | 2000-05-04 | Minnesota Mining And Mfg. Co., Saint Paul | Superatmosphärische reaktion |
| US5952065A (en) * | 1994-08-31 | 1999-09-14 | Nike, Inc. | Cushioning device with improved flexible barrier membrane |
| EP0779853B1 (en) | 1994-09-09 | 1999-05-06 | Minnesota Mining And Manufacturing Company | Method of making a packaged hot melt adhesive |
| EP0779898B1 (en) | 1994-09-09 | 1998-08-05 | Minnesota Mining And Manufacturing Company | Process for the packaged polymerization of olefinic monomers |
| US5463564A (en) | 1994-09-16 | 1995-10-31 | 3-Dimensional Pharmaceuticals, Inc. | System and method of automatically generating chemical compounds with desired properties |
| US6004617A (en) | 1994-10-18 | 1999-12-21 | The Regents Of The University Of California | Combinatorial synthesis of novel materials |
| US5985356A (en) | 1994-10-18 | 1999-11-16 | The Regents Of The University Of California | Combinatorial synthesis of novel materials |
| GB2295152A (en) | 1994-11-18 | 1996-05-22 | Pfizer Ltd | Preparation of a library of compounds by solid-phase synthesis |
| JPH08193107A (ja) | 1995-01-17 | 1996-07-30 | Nippon Oil & Fats Co Ltd | 不飽和基含有型含フッ素ブロック共重合体組成物及びその製造方法 |
| US5478886A (en) | 1995-02-01 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Acrylic block copolymers |
| US5571655A (en) * | 1995-04-17 | 1996-11-05 | Xerox Corporation | Toner reactive melt mixing process |
| FR2735480B1 (fr) * | 1995-06-15 | 1997-07-18 | Atochem Elf Sa | Procede de polymerisation anionique en continu d'au moins un monomere (meth)acrylique pour l'obtention de polymeres a haut taux de solide |
| US5900464A (en) | 1995-07-25 | 1999-05-04 | Fmc Corporation | Processes for making methacrylate and acrylate polymers |
| US5814278A (en) | 1996-04-26 | 1998-09-29 | Minnesota Mining And Manufacturing Company | Shrouded reaction vessel |
| US5644007A (en) * | 1996-04-26 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Continuous process for the production of poly(1-alkenes) |
| US5804625A (en) * | 1996-05-21 | 1998-09-08 | Minnesota Mining And Manufacturing Company | Fluorochemical and hydrocarbon surfactant blends as hydrophilic additives to thermoplastic polymers |
| US6150498A (en) * | 1996-07-12 | 2000-11-21 | The Dow Chemical Company | Polymer recovery |
| DE59707512D1 (de) * | 1996-08-19 | 2002-07-18 | Basf Ag | Verfahren zur anionischen polymerisation |
| US6720186B1 (en) * | 1998-04-03 | 2004-04-13 | Symyx Technologies, Inc. | Method of research for creating and testing novel catalysts, reactions and polymers |
| JPH10130348A (ja) | 1996-10-25 | 1998-05-19 | Asahi Glass Co Ltd | ポリフルオロアルキル基を有するブロック共重合体およびその製造法 |
| WO1998020051A1 (en) * | 1996-11-07 | 1998-05-14 | The Penn State Research Foundation | Short-cycle removal of impurities from polymers |
| DE19648245A1 (de) | 1996-11-21 | 1998-05-28 | Basf Ag | Kontinuierliches Verfahren zur Herstellung thermoplastischer Formmassen |
| DE19652312A1 (de) | 1996-12-16 | 1998-06-18 | Basf Ag | Verfahren zur Herstellung von linearen Blockcopolymeren |
| US6277491B1 (en) * | 1997-01-20 | 2001-08-21 | Sekisui Kaseihin Kogyo Kabushikikaisha | Expandable thermoplastic resin beads and molded foam made from the same |
| DE19702988A1 (de) | 1997-01-28 | 1998-07-30 | Hoechst Ag | Isoxazol- und Crotonsäureamidderivate und deren Verwendung als Arzneimittel und Diagnostika |
| US5907017A (en) | 1997-01-31 | 1999-05-25 | Cornell Research Foundation, Inc. | Semifluorinated side chain-containing polymers |
| DE19715035A1 (de) | 1997-04-11 | 1998-10-15 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Blockcopolymeren |
| US6224832B1 (en) * | 1997-05-30 | 2001-05-01 | Smithkline Beecham Corporation | Multi-reactor synthesizer and method for combinatorial chemistry |
| US6184338B1 (en) | 1997-08-27 | 2001-02-06 | Fmc Corporation | Anionic polymerization initiators containing tertiary amine functionality, their chain extended analogues, and processes for using the same |
| US6013735A (en) | 1998-02-13 | 2000-01-11 | Ethyl Corporation | Process for the preparation of acrylate and methacrylate polymers |
| US6175409B1 (en) * | 1999-04-02 | 2001-01-16 | Symyx Technologies, Inc. | Flow-injection analysis and variable-flow light-scattering methods and apparatus for characterizing polymers |
| US6319881B1 (en) * | 1998-06-23 | 2001-11-20 | Exxonmobil Oil Corporation | Haze free oil additive compositions containing dispersants from selectively hydrogenated diene copolymers |
| US6160060A (en) | 1998-08-04 | 2000-12-12 | Eastman Chemical Company | Process for the synthesis of high molecular weight predominantly amorphous polymers with improved color and adhesive properties |
| US6306658B1 (en) | 1998-08-13 | 2001-10-23 | Symyx Technologies | Parallel reactor with internal sensing |
| DE69927839T2 (de) | 1998-09-03 | 2006-05-11 | Ciba Speciality Chemicals Holding Inc. | Propfung von äthylenisch ungesättigten monomeren auf polymeren |
| US6531704B2 (en) * | 1998-09-14 | 2003-03-11 | Nanoproducts Corporation | Nanotechnology for engineering the performance of substances |
| US6316112B1 (en) | 1998-11-24 | 2001-11-13 | Kraton Polymers Us Llc | Fluoro-functional polyethylene-polysiloxane block copolymers |
| US6485692B1 (en) * | 1998-12-04 | 2002-11-26 | Symyx Technologies, Inc. | Continuous feed parallel reactor |
| NO990119D0 (no) | 1999-01-12 | 1999-01-12 | Jotun As | Blokk-kopolymerer med blokker med perfluorerte sidekjeder, og fremgangsmÕte for fremstilling derav |
| US6749814B1 (en) * | 1999-03-03 | 2004-06-15 | Symyx Technologies, Inc. | Chemical processing microsystems comprising parallel flow microreactors and methods for using same |
| US20020010267A1 (en) * | 1999-03-09 | 2002-01-24 | Symyx Technologies, Inc., A Delaware Corporation | Block copolymers |
| DE19910811C2 (de) | 1999-03-11 | 2002-11-14 | Sunyx Surface Nanotechnologies | Hydrophilierbare Blockcopolymere |
| DE19910810C2 (de) | 1999-03-11 | 2001-06-28 | Bayer Ag | Hydrophilierbare Blockcopolymere, Verfahren zu ihrer Herstellung und deren Verwendung |
| US6693220B2 (en) * | 1999-05-07 | 2004-02-17 | General Electric Company | Method for screening multiple reactants and catalyst systems using incremental flow reactor methodology |
| EP1196458B1 (en) * | 1999-06-11 | 2004-05-19 | Dow Global Technologies Inc. | Hydrogenated block copolymers and optical media discs produced therefrom |
| EP1208150A4 (en) * | 1999-06-11 | 2005-01-26 | Sydney Hyman | IMAGE FORMING MATERIAL |
| AU1440901A (en) * | 1999-10-27 | 2001-05-08 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| US6586541B2 (en) * | 2000-02-02 | 2003-07-01 | E. I. Du Pont De Nemours And Company | Process for production of polyolefins |
| US6379791B1 (en) * | 2000-02-08 | 2002-04-30 | 3M Innovative Properties Company | Compatibilized pressure-sensitive adhesives |
| US6448353B1 (en) * | 2000-02-08 | 2002-09-10 | 3M Innovative Properties Company | Continuous process for the production of controlled architecture materials |
| DE10016652A1 (de) * | 2000-04-04 | 2001-10-18 | Basf Ag | Additivarme strahlenhärtbare Bindemittel |
| US6451287B1 (en) | 2000-05-26 | 2002-09-17 | Smithkline Beecham Corporation | Fluorinated copolymer surfactants and use thereof in aerosol compositions |
| US6268532B1 (en) * | 2000-06-05 | 2001-07-31 | 3M Innovative Properties Company | Sulfonated perfluorovinyl functional monomers |
| WO2002016517A2 (en) * | 2000-08-18 | 2002-02-28 | 3M Innovative Properties Company | Fluoroalkyl (meth)acrylate copolymer coating compositions |
| US6593436B2 (en) * | 2000-11-29 | 2003-07-15 | Crompton Corporation | Continuous manufacture of silicone copolymers via static mixing plug flow reactors |
| JP3714870B2 (ja) * | 2000-12-28 | 2005-11-09 | セントラル硝子株式会社 | 透明性含フッ素共重合体 |
| US6586483B2 (en) * | 2001-01-08 | 2003-07-01 | 3M Innovative Properties Company | Foam including surface-modified nanoparticles |
| US20020160527A1 (en) | 2001-02-26 | 2002-10-31 | 3M Innovative Properties Company | Combinatorial library comprising pouches as packages for library members and method therefor |
| US7118917B2 (en) * | 2001-03-07 | 2006-10-10 | Symyx Technologies, Inc. | Parallel flow reactor having improved thermal control |
| US7514263B2 (en) | 2001-04-02 | 2009-04-07 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of materials |
| US20030012700A1 (en) * | 2001-07-11 | 2003-01-16 | Carnahan James Claude | Systems and methods for parallel testing of catalyst performance |
| GB2378068B (en) * | 2001-07-27 | 2005-05-04 | Motorola Inc | Bipolar differential amplifier |
| JP4110315B2 (ja) | 2001-12-25 | 2008-07-02 | 株式会社昭和丸筒 | 逆止弁および逆流防止機能付き連結システム |
| US7619040B2 (en) * | 2002-02-15 | 2009-11-17 | Ppg Industries Ohio, Inc. | Compositions containing copolymers of olefinic monomers |
| US6753373B2 (en) * | 2002-06-20 | 2004-06-22 | Kris W. Winowiecki | Polyolefin compositions and method of use thereof in molded products |
| US7157283B2 (en) * | 2002-08-02 | 2007-01-02 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of modified materials |
| US6903173B2 (en) * | 2002-08-02 | 2005-06-07 | 3M Innovative Properties Co. | Fluorinated polymers |
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US6716935B1 (en) * | 2002-12-19 | 2004-04-06 | 3M Innovative Properties Company | Continuous process for the production of controlled architecture materials under high solids loading conditions |
| US6969490B2 (en) * | 2003-06-26 | 2005-11-29 | 3M Innovative Properties Company | Device for the continuous process for the production of controlled architecture materials |
| EP1881028B1 (en) * | 2005-05-02 | 2011-10-12 | Daikin Industries, Ltd. | Crosslinkable polytetrafluoroethylene composition, cross- linked polytetrafluoroethylene powder, polytetrafluoro- ethylene moldings, resin blend compositions, and resin blend moldings |
-
2002
- 2002-08-02 US US10/211,415 patent/US7632916B2/en not_active Expired - Fee Related
-
2003
- 2003-07-03 CA CA002494238A patent/CA2494238A1/en not_active Abandoned
- 2003-07-03 EP EP03766834.0A patent/EP1551885B1/en not_active Expired - Lifetime
- 2003-07-03 WO PCT/US2003/021051 patent/WO2004013189A2/en not_active Ceased
- 2003-07-03 KR KR1020057001849A patent/KR20050033642A/ko not_active Withdrawn
- 2003-07-03 BR BR0313156-4A patent/BR0313156A/pt not_active IP Right Cessation
- 2003-07-03 AU AU2003249701A patent/AU2003249701A1/en not_active Abandoned
- 2003-07-03 MX MXPA05001291A patent/MXPA05001291A/es unknown
- 2003-07-03 JP JP2004526021A patent/JP2005534773A/ja not_active Withdrawn
- 2003-07-03 CN CNB038184680A patent/CN100387624C/zh not_active Expired - Fee Related
-
2009
- 2009-10-26 US US12/605,496 patent/US8101711B2/en not_active Expired - Fee Related
-
2011
- 2011-01-24 JP JP2011011742A patent/JP5485920B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07268023A (ja) * | 1992-05-08 | 1995-10-17 | Shell Internatl Res Maatschappij Bv | 安定な酸無水物環を有するポリマー |
| JPH09277464A (ja) * | 1996-04-12 | 1997-10-28 | Sumitomo Chem Co Ltd | 耐熱性、ガスバリア性に優れたシートおよび成形体 |
| JP2002161110A (ja) * | 2000-11-28 | 2002-06-04 | Nippon Synthetic Chem Ind Co Ltd:The | ビニルアルコール−ビニルアミン共重合体の製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040024130A1 (en) | 2004-02-05 |
| WO2004013189A2 (en) | 2004-02-12 |
| KR20050033642A (ko) | 2005-04-12 |
| WO2004013189A3 (en) | 2004-06-10 |
| US8101711B2 (en) | 2012-01-24 |
| US7632916B2 (en) | 2009-12-15 |
| CN100387624C (zh) | 2008-05-14 |
| EP1551885A2 (en) | 2005-07-13 |
| JP5485920B2 (ja) | 2014-05-07 |
| CA2494238A1 (en) | 2004-02-12 |
| JP2011099112A (ja) | 2011-05-19 |
| BR0313156A (pt) | 2005-06-28 |
| CN1671752A (zh) | 2005-09-21 |
| AU2003249701A1 (en) | 2004-02-23 |
| US20100048819A1 (en) | 2010-02-25 |
| EP1551885B1 (en) | 2016-02-17 |
| MXPA05001291A (es) | 2005-04-28 |
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