KR20020043590A - 플루오로케미컬 소중합체 및 그것의 용도 - Google Patents
플루오로케미컬 소중합체 및 그것의 용도 Download PDFInfo
- Publication number
- KR20020043590A KR20020043590A KR1020027003837A KR20027003837A KR20020043590A KR 20020043590 A KR20020043590 A KR 20020043590A KR 1020027003837 A KR1020027003837 A KR 1020027003837A KR 20027003837 A KR20027003837 A KR 20027003837A KR 20020043590 A KR20020043590 A KR 20020043590A
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- South Korea
- Prior art keywords
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- oligomer
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- aliphatic
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RRLMGCBZYFFRED-UHFFFAOYSA-N undecyl prop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C=C RRLMGCBZYFFRED-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/435—Sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Filtering Materials (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/404,747 | 1999-09-24 | ||
| US09/404,747 US6174964B1 (en) | 1999-09-24 | 1999-09-24 | Fluorochemical oligomer and use thereof |
| PCT/US2000/002458 WO2001023351A1 (en) | 1999-09-24 | 2000-02-01 | Fluorochemical oligomer and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020043590A true KR20020043590A (ko) | 2002-06-10 |
Family
ID=23600864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027003837A Withdrawn KR20020043590A (ko) | 1999-09-24 | 2000-02-01 | 플루오로케미컬 소중합체 및 그것의 용도 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6174964B1 (enExample) |
| EP (1) | EP1214297B1 (enExample) |
| JP (1) | JP2003510305A (enExample) |
| KR (1) | KR20020043590A (enExample) |
| AU (1) | AU2748800A (enExample) |
| DE (1) | DE60032247T2 (enExample) |
| TW (1) | TWI268275B (enExample) |
| WO (1) | WO2001023351A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6476114B2 (en) * | 1997-11-19 | 2002-11-05 | 3M Innovative Properties Company | Thermoplastic polymer film comprising a fluorochemical compound |
| US7049379B2 (en) * | 1999-05-11 | 2006-05-23 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| US6525127B1 (en) | 1999-05-11 | 2003-02-25 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| JP4343354B2 (ja) * | 1999-11-02 | 2009-10-14 | Agcセイミケミカル株式会社 | 半田用フラックス這い上がり防止剤組成物とその用途 |
| US6753380B2 (en) * | 2001-03-09 | 2004-06-22 | 3M Innovative Properties Company | Water-and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| US20040231914A1 (en) * | 2003-01-02 | 2004-11-25 | 3M Innovative Properties Company | Low thickness sound absorptive multilayer composite |
| US20040131836A1 (en) * | 2003-01-02 | 2004-07-08 | 3M Innovative Properties Company | Acoustic web |
| US7320739B2 (en) * | 2003-01-02 | 2008-01-22 | 3M Innovative Properties Company | Sound absorptive multilayer composite |
| US7078456B2 (en) * | 2003-11-26 | 2006-07-18 | 3M Innovative Properties Company | Fluorochemical oligomeric composition and use thereof |
| US7399807B2 (en) * | 2004-07-09 | 2008-07-15 | Unitex Chemical Corporation | Hydrophobic, oleophobic and alcohol-resistant fluorochemical additive |
| US20060013983A1 (en) * | 2004-07-15 | 2006-01-19 | 3M Innovative Properties Company | Adhesive delivery of oil and water repellents |
| US7500541B2 (en) * | 2004-09-30 | 2009-03-10 | Kimberly-Clark Worldwide, Inc. | Acoustic material with liquid repellency |
| US20060194911A1 (en) * | 2005-02-25 | 2006-08-31 | Sterling Robert E | Thermoset polymers with dispersed fluorocarbon additives |
| US7651863B2 (en) * | 2005-07-14 | 2010-01-26 | 3M Innovative Properties Company | Surface-enhanced spectroscopic method, flexible structured substrate, and method of making the same |
| US20070014997A1 (en) * | 2005-07-14 | 2007-01-18 | 3M Innovative Properties Company | Tool and method of making and using the same |
| US7906057B2 (en) * | 2005-07-14 | 2011-03-15 | 3M Innovative Properties Company | Nanostructured article and method of making the same |
| US7390351B2 (en) * | 2006-02-09 | 2008-06-24 | 3M Innovative Properties Company | Electrets and compounds useful in electrets |
| WO2009076064A1 (en) * | 2007-12-06 | 2009-06-18 | 3M Innovative Properties Company | Electret webs with charge-enhancing additives |
| US8776367B2 (en) | 2008-03-10 | 2014-07-15 | National Taiwan University | Method of manufacturing an electret film |
| JP2011522101A (ja) * | 2008-06-02 | 2011-07-28 | スリーエム イノベイティブ プロパティズ カンパニー | エレクトレット用帯電促進添加剤 |
| CN102046871B (zh) * | 2008-06-02 | 2013-02-13 | 3M创新有限公司 | 驻极体料片、驻极体过滤介质和制备驻极体料片的方法 |
| US7765698B2 (en) * | 2008-06-02 | 2010-08-03 | 3M Innovative Properties Company | Method of making electret articles based on zeta potential |
| TWI462598B (zh) * | 2008-08-06 | 2014-11-21 | Univ Nat Taiwan | 駐極體薄膜之製造方法及包含該駐極體薄膜之揚聲器 |
| JP5527211B2 (ja) * | 2008-09-19 | 2014-06-18 | 旭硝子株式会社 | エレクトレット、静電誘導型変換素子、及びエレクトレットの製造方法 |
| US9682512B2 (en) | 2009-02-06 | 2017-06-20 | Nike, Inc. | Methods of joining textiles and other elements incorporating a thermoplastic polymer material |
| US20100199406A1 (en) | 2009-02-06 | 2010-08-12 | Nike, Inc. | Thermoplastic Non-Woven Textile Elements |
| US8906275B2 (en) | 2012-05-29 | 2014-12-09 | Nike, Inc. | Textured elements incorporating non-woven textile materials and methods for manufacturing the textured elements |
| US20100199520A1 (en) * | 2009-02-06 | 2010-08-12 | Nike, Inc. | Textured Thermoplastic Non-Woven Elements |
| US8850719B2 (en) | 2009-02-06 | 2014-10-07 | Nike, Inc. | Layered thermoplastic non-woven textile elements |
| US9296904B2 (en) | 2010-12-20 | 2016-03-29 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| US8742022B2 (en) | 2010-12-20 | 2014-06-03 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| US20130255103A1 (en) | 2012-04-03 | 2013-10-03 | Nike, Inc. | Apparel And Other Products Incorporating A Thermoplastic Polymer Material |
| EP2861677B1 (en) | 2012-06-19 | 2020-11-11 | 3M Innovative Properties Company | Additive comprising low surface energy group and hydroxyl groups and coating compositions |
| US9701850B2 (en) | 2012-06-19 | 2017-07-11 | 3M Innovative Properties Company | Coating compositions comprising polymerizable non-ionic surfactant exhibiting reduced fingerprint visibility |
| US20140102651A1 (en) * | 2012-10-12 | 2014-04-17 | Georgia-Pacific Chemicals Llc | Greaseproof paper with lower content of fluorochemicals |
| MX363157B (es) * | 2012-12-28 | 2019-03-13 | Cytec Ind Inc | Microgeles que inhiben la corrosión y composiciones de cebadores no cromados que los incorporan. |
| TWI555855B (zh) | 2015-12-18 | 2016-11-01 | 財團法人工業技術研究院 | 疏水性合金膜及其製造方法 |
| US10625196B2 (en) * | 2016-05-31 | 2020-04-21 | Hollingsworth & Vose Company | Coalescing filter media |
| US10543441B2 (en) | 2016-12-15 | 2020-01-28 | Hollingsworth & Vose Company | Filter media including adhesives and/or oleophobic properties |
| US10898838B2 (en) | 2016-12-15 | 2021-01-26 | Hollingsworth & Vose Company | Filter media including adhesives |
| WO2018169642A1 (en) | 2017-03-17 | 2018-09-20 | 3M Innovative Properties Company | Adhesive articles and methods of making the same |
| WO2018183481A1 (en) * | 2017-03-28 | 2018-10-04 | Hollingsworth & Vose Company | Filter media including adhesives and/or oleophobic properties |
| CN114075700B (zh) * | 2020-08-19 | 2022-11-29 | 中国科学院宁波材料技术与工程研究所 | 一种链式预调制熔喷方法、链式预调制熔喷头及熔喷装置 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2841573A (en) | 1955-12-29 | 1958-07-01 | Minnesota Mining & Mfg | Fluorocarbon vinyl-type esters and polymers |
| US2803656A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbonsulfonamidoalkanols and sulfates thereof |
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3886201A (en) | 1971-11-17 | 1975-05-27 | Ciba Geigy Corp | Perfluoroalkyl esters of mercapto- and thio-carboxylic acids |
| US3899563A (en) | 1971-12-06 | 1975-08-12 | Allied Chem | Synthetic fibers having improved soil and stain repellency |
| US3971373A (en) | 1974-01-21 | 1976-07-27 | Minnesota Mining And Manufacturing Company | Particle-loaded microfiber sheet product and respirators made therefrom |
| NL160303C (nl) | 1974-03-25 | 1979-10-15 | Verto Nv | Werkwijze voor het vervaardigen van een vezelfilter. |
| US4100324A (en) | 1974-03-26 | 1978-07-11 | Kimberly-Clark Corporation | Nonwoven fabric and method of producing same |
| NL181632C (nl) | 1976-12-23 | 1987-10-01 | Minnesota Mining & Mfg | Electreetfilter en werkwijze voor het vervaardigen daarvan. |
| FR2442861A1 (fr) | 1978-11-14 | 1980-06-27 | Ugine Kuhlmann | Nouveaux produits fluores destines aux traitements oleofuges et hydrofuges de substrats divers et plus particulierement de substrats fibreux |
| US4375718A (en) | 1981-03-12 | 1983-03-08 | Surgikos, Inc. | Method of making fibrous electrets |
| US4429001A (en) | 1982-03-04 | 1984-01-31 | Minnesota Mining And Manufacturing Company | Sheet product containing sorbent particulate material |
| WO1984003193A1 (en) | 1983-02-04 | 1984-08-16 | Minnesota Mining & Mfg | Method and apparatus for manufacturing an electret filter medium |
| JPS60168511A (ja) | 1984-02-10 | 1985-09-02 | Japan Vilene Co Ltd | エレクトレツトフイルタの製造方法 |
| US4843134A (en) | 1984-03-28 | 1989-06-27 | Minnesota Mining And Manufacturing Company | Acrylate pressure-sensitive adhesives containing insolubles |
| US4619976A (en) | 1984-11-30 | 1986-10-28 | Eastman Kodak Company | Blends of copolyesters and polycarbonate |
| US5025052A (en) | 1986-09-12 | 1991-06-18 | Minnesota Mining And Manufacturing Company | Fluorochemical oxazolidinones |
| JPH0341160A (ja) | 1989-07-07 | 1991-02-21 | Kao Corp | 撥液性のすぐれた熱可塑性樹脂組成物 |
| US5143963A (en) | 1989-12-06 | 1992-09-01 | Res Development Corp. | Thermoplastic polymers with dispersed fluorocarbon additives |
| IT1243747B (it) | 1990-10-24 | 1994-06-21 | Sviluppo Settori Impiego Srl | Composizioni polimeriche oleo-repellenti e loro impiego nella preparazione di corpi formati aventi superfici ad elevata resistenza ai solventi ed elevata repellenza allo sporco. |
| US5149576A (en) | 1990-11-26 | 1992-09-22 | Kimberly-Clark Corporation | Multilayer nonwoven laminiferous structure |
| US5145727A (en) | 1990-11-26 | 1992-09-08 | Kimberly-Clark Corporation | Multilayer nonwoven composite structure |
| US5536157A (en) | 1991-03-04 | 1996-07-16 | Ems-Inventa Ag.G. | Apparatus for cooling melt-spun filaments |
| US5314959A (en) | 1991-03-06 | 1994-05-24 | Minnesota Mining And Manufacturing Company | Graft copolymers containing fluoroaliphatic groups |
| US5147938A (en) * | 1991-04-02 | 1992-09-15 | Minnesota Mining And Manufacturing Company | Acrylate adhesives containing polymerizable fluorochemical surfactants |
| US5292796A (en) | 1991-04-02 | 1994-03-08 | Minnesota Mining And Manufacturing Company | Urea-aldehyde condensates and melamine derivatives comprising fluorochemical oligomers |
| US5276175A (en) * | 1991-04-02 | 1994-01-04 | Minnesota Mining And Manufacturing Company | Isocyanate derivatives comprising flourochemical oligomers |
| US5459188A (en) | 1991-04-11 | 1995-10-17 | Peach State Labs, Inc. | Soil resistant fibers |
| US5244951A (en) | 1991-05-02 | 1993-09-14 | Minnesota Mining And Manufacturing Company | Durably hydrophilic, thermoplastic fiber |
| US5451622A (en) | 1992-09-30 | 1995-09-19 | Minnesota Mining And Manufacturing Company | Composition comprising thermoplastic polymer and fluorochemical piperazine compound |
| US5380778A (en) | 1992-09-30 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Fluorochemical aminoalcohols |
| JP3612713B2 (ja) | 1992-11-13 | 2005-01-19 | ダイキン工業株式会社 | 非水乳化型表面処理剤組成物 |
| AU669420B2 (en) * | 1993-03-26 | 1996-06-06 | Minnesota Mining And Manufacturing Company | Oily mist resistant electret filter media |
| JP3041160B2 (ja) | 1993-05-14 | 2000-05-15 | 沖電気工業株式会社 | 読み取り方法および書き込み・読み取り制御回路 |
| RU2130521C1 (ru) | 1993-08-17 | 1999-05-20 | Миннесота Майнинг Энд Мэнюфекчуринг Компани | Способ электризации нетканого полотна, электретная фильтрующая среда, упругая фильтрующая маска и респираторная маска в сборе |
| US5508330A (en) | 1994-11-03 | 1996-04-16 | Ciba-Geigy Corporation | Barrier property enhancement of films and molded articles |
| US5908598A (en) | 1995-08-14 | 1999-06-01 | Minnesota Mining And Manufacturing Company | Fibrous webs having enhanced electret properties |
| DE19539940A1 (de) | 1995-10-26 | 1997-04-30 | Wacker Chemie Gmbh | Fluorsiloxanhaltige Pflegemittel |
| US5798402A (en) | 1995-12-21 | 1998-08-25 | E. I. Du Pont De Nemours And Company | Fluorinated sulfone melt additives for thermoplastic polymers |
| TW426712B (en) | 1995-12-21 | 2001-03-21 | Du Pont | Fluorinated diester melt additives for thermoplastic polymers and their uses |
| US5681963A (en) | 1995-12-21 | 1997-10-28 | E. I. Du Pont De Nemours And Company | Fluorinated melt additives for thermoplastic polymers |
| TW376397B (en) | 1995-12-21 | 1999-12-11 | Du Pont | Fluorinated ester melt additives for thermoplastic fibers |
| US5998549A (en) * | 1996-05-31 | 1999-12-07 | 3M Innovative Properties Company | Durable, low surface energy compounds and articles, apparatuses, and methods for using the same |
| JPH09323956A (ja) | 1996-05-31 | 1997-12-16 | Wako Pure Chem Ind Ltd | 新規なコハク酸誘導体 |
| JP3800672B2 (ja) * | 1996-06-11 | 2006-07-26 | 日本油脂株式会社 | 撥水撥油性組成物 |
| JPH108041A (ja) * | 1996-06-21 | 1998-01-13 | Daikin Ind Ltd | 水分散型フッ素系撥水撥油剤 |
| JP3779331B2 (ja) | 1996-10-09 | 2006-05-24 | ダイキン工業株式会社 | 撥水撥油性樹脂組成物 |
| JPH10176074A (ja) * | 1996-12-20 | 1998-06-30 | Kurabo Ind Ltd | 撥水性ポリウレタンフォーム |
| WO1998045345A1 (en) * | 1997-04-08 | 1998-10-15 | Minnesota Mining And Manufacturing Company | Mixed fluorochemical hydrocarbon condensates to impart oil and water repellency to a substrate |
| JP3864496B2 (ja) * | 1997-05-09 | 2006-12-27 | ユニマテック株式会社 | 撥水耐油剤 |
| EP0981567B1 (en) | 1997-05-14 | 2001-06-27 | Minnesota Mining And Manufacturing Company | Fluorochemical composition comprising a polymer derived from a fluorochemical urethane (meth)acrylate monomer for imparting stain release properties to a substrate |
| JP2001525872A (ja) | 1997-05-14 | 2001-12-11 | 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 | 基材に汚染放出性を与えるための、フルオロケミカルポリエーテルとポリイソシアネートとの縮合生成物を含有するフルオロケミカル組成物 |
| EP0981562B1 (en) | 1997-05-14 | 2002-09-04 | Minnesota Mining And Manufacturing Company | Fluorochemical composition comprising a polyurethane having a fluorochemical oligomer and a hydrophilic segment to impart stain release properties to a substrate |
| US6127485A (en) | 1997-07-28 | 2000-10-03 | 3M Innovative Properties Company | High temperature-stable fluorochemicals as hydrophobic and oleophobic additives to synthetic organic polymers |
| JPH11172126A (ja) * | 1997-12-12 | 1999-06-29 | Asahi Glass Co Ltd | 水分散型撥水撥油剤組成物及びその製造方法 |
| JP4510169B2 (ja) * | 1999-03-11 | 2010-07-21 | 石原薬品株式会社 | フルオロ飽和炭化水素基含有化合物、その製造方法、及び表面処理剤及び塗料添加剤 |
| WO2000061697A1 (fr) * | 1999-04-12 | 2000-10-19 | Daikin Industries, Ltd. | Repulsif en poudre pour eau-huile : procede de fabrication et utilisations |
| US6288157B1 (en) | 1999-05-11 | 2001-09-11 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof |
| US6235824B1 (en) | 1999-05-11 | 2001-05-22 | 3M Innovative Properties Company | Polish composition and method of use |
| US6193791B1 (en) * | 1999-09-24 | 2001-02-27 | 3M Innovative Properties Company | Polish composition and method of use |
-
1999
- 1999-09-24 US US09/404,747 patent/US6174964B1/en not_active Expired - Lifetime
-
2000
- 2000-02-01 WO PCT/US2000/002458 patent/WO2001023351A1/en not_active Ceased
- 2000-02-01 DE DE60032247T patent/DE60032247T2/de not_active Expired - Lifetime
- 2000-02-01 KR KR1020027003837A patent/KR20020043590A/ko not_active Withdrawn
- 2000-02-01 JP JP2001526505A patent/JP2003510305A/ja active Pending
- 2000-02-01 AU AU27488/00A patent/AU2748800A/en not_active Abandoned
- 2000-02-01 EP EP00905881A patent/EP1214297B1/en not_active Expired - Lifetime
- 2000-08-08 TW TW089115925A patent/TWI268275B/zh not_active IP Right Cessation
- 2000-09-29 US US09/677,396 patent/US6284843B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1214297A1 (en) | 2002-06-19 |
| DE60032247D1 (de) | 2007-01-18 |
| JP2003510305A (ja) | 2003-03-18 |
| DE60032247T2 (de) | 2007-06-28 |
| AU2748800A (en) | 2001-04-30 |
| TWI268275B (en) | 2006-12-11 |
| WO2001023351A1 (en) | 2001-04-05 |
| US6284843B1 (en) | 2001-09-04 |
| EP1214297B1 (en) | 2006-12-06 |
| US6174964B1 (en) | 2001-01-16 |
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| PA0105 | International application |
Patent event date: 20020323 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |