JP4271577B2 - 高耐久性、低黄変性の織物用の撥水および撥油剤 - Google Patents
高耐久性、低黄変性の織物用の撥水および撥油剤 Download PDFInfo
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- JP4271577B2 JP4271577B2 JP2003554977A JP2003554977A JP4271577B2 JP 4271577 B2 JP4271577 B2 JP 4271577B2 JP 2003554977 A JP2003554977 A JP 2003554977A JP 2003554977 A JP2003554977 A JP 2003554977A JP 4271577 B2 JP4271577 B2 JP 4271577B2
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- 230000000694 effects Effects 0.000 description 3
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- 229940051250 hexylene glycol Drugs 0.000 description 3
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- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
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- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
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- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
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- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85539501A | 2001-05-15 | 2001-05-15 | |
| US10/091,004 US6479605B1 (en) | 2001-05-15 | 2002-03-04 | High-durability, low-yellowing repellent for textiles |
| PCT/US2002/018395 WO2003054284A1 (en) | 2001-05-15 | 2002-05-14 | High-durability, low-yellowing water-and oil-repellent for textiles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005513245A JP2005513245A (ja) | 2005-05-12 |
| JP2005513245A5 JP2005513245A5 (OSRAM) | 2005-12-22 |
| JP4271577B2 true JP4271577B2 (ja) | 2009-06-03 |
Family
ID=26782903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554977A Expired - Fee Related JP4271577B2 (ja) | 2001-05-15 | 2002-05-14 | 高耐久性、低黄変性の織物用の撥水および撥油剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6479605B1 (OSRAM) |
| EP (1) | EP1399618B1 (OSRAM) |
| JP (1) | JP4271577B2 (OSRAM) |
| CN (1) | CN1239777C (OSRAM) |
| DE (1) | DE60216455T2 (OSRAM) |
| WO (1) | WO2003054284A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101339752B1 (ko) * | 2011-12-28 | 2014-01-03 | 주식회사 스노젠 | 가교제 역할을 하는 다관능 이소시아네이트가 도입된 내구성 불소 발수제 조성물 및 그 합성방법 |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4673962B2 (ja) * | 2000-08-25 | 2011-04-20 | 楠本化成株式会社 | クリアー型塗料塗膜の耐水白化性を有する消泡剤或いは平滑剤 |
| US20040198915A1 (en) * | 2000-08-25 | 2004-10-07 | Takao Uehara | Defoamers for top coat paints for motor vehicles |
| US7105270B2 (en) * | 2002-01-31 | 2006-09-12 | Fuji Photo Film Co., Ltd. | Fluoroaliphatic group-containing copolymer |
| CN100449055C (zh) * | 2003-07-11 | 2009-01-07 | 纳幕尔杜邦公司 | 用于油漆涂布器的氟化学品涂饰剂 |
| US7258925B2 (en) * | 2003-07-11 | 2007-08-21 | E.I. Du Pont De Nemours And Company | Fluorochemical finishes for paint applicators |
| US20050058779A1 (en) * | 2003-09-12 | 2005-03-17 | Goldbaum Richard H. | Suppression of repellency in polyolefins |
| CA2545001C (en) * | 2003-11-13 | 2010-07-06 | Newell Operating Company | Paint applicators including paint application element having non-stick coating |
| US6979711B2 (en) * | 2003-11-18 | 2005-12-27 | E. I. Du Pont De Nemours And Company | Fluorine efficient finishes for textiles |
| EP1571165B1 (en) * | 2004-03-01 | 2009-01-07 | Lorenzo Toffano | Compositions for the preparation of hydrophobic coatings |
| JP4752197B2 (ja) * | 2004-06-04 | 2011-08-17 | ユニマテック株式会社 | 撥水撥油剤の製造法 |
| WO2006001214A1 (ja) * | 2004-06-25 | 2006-01-05 | Daikin Industries, Ltd. | 含フッ素共重合体を含む汚れ脱離剤およびその製造方法 |
| US20060074188A1 (en) * | 2004-10-04 | 2006-04-06 | Franchina Justine G | Fluorine efficient finishes for textiles |
| US7652112B2 (en) | 2005-07-06 | 2010-01-26 | E.I. Du Pont De Nemours And Company | Polymeric extenders for surface effects |
| AU2006269600B2 (en) * | 2005-07-06 | 2011-11-24 | E. I. Du Pont De Nemours And Company | Polymeric extenders for surface effects |
| CN101356148A (zh) * | 2006-01-10 | 2009-01-28 | 克莱里安特财务(Bvi)有限公司 | 含氟调聚化合物和包含所述含氟调聚化合物的聚合物 |
| WO2007084952A2 (en) | 2006-01-18 | 2007-07-26 | Akrion Technologies, Inc. | Systems and methods for drying a rotating substrate |
| US8075556B2 (en) * | 2006-05-23 | 2011-12-13 | Andres Betts | High frequency epidural neuromodulation catheter for effectuating RF treatment in spinal canal and method of using same |
| RU2444534C2 (ru) * | 2006-08-25 | 2012-03-10 | Клариант Файненс (Бви) Лимитед | Масло-, водо- и грязеотталкивающие сополимеры перфторалкилэтилметакрилата |
| CN100368441C (zh) * | 2006-09-28 | 2008-02-13 | 东华大学 | 一种含氟碳链丙烯酸酯及其共聚物的制备方法和应用 |
| KR20090116774A (ko) * | 2007-02-02 | 2009-11-11 | 다이킨 고교 가부시키가이샤 | 세탁 내구성이 우수한 불소 함유 공중합체 및 오염 이탈제 |
| US8476385B2 (en) * | 2007-06-06 | 2013-07-02 | 3M Innovative Properties Company | Fluorinated ether compositions and methods of using the same |
| EP2009035A1 (de) * | 2007-06-27 | 2008-12-31 | Huntsman Textile Effects (Germany) GmbH | Copolymere mit Perfluoralkylgruppen und wässrige Dispersionen davon |
| WO2009014039A1 (ja) * | 2007-07-20 | 2009-01-29 | Daikin Industries, Ltd. | 撥アルコール性および汚れ脱離性を有する含フッ素繊維加工剤 |
| US20090030114A1 (en) * | 2007-07-25 | 2009-01-29 | Ying Wang | Fluoropolymer emulsions |
| ATE533800T1 (de) * | 2007-09-15 | 2011-12-15 | Huntsman Textile Effects Ger | Fluorhaltiges polymer und siloxan enthaltende zusammensetzungen |
| JP5439743B2 (ja) * | 2007-10-11 | 2014-03-12 | ユニマテック株式会社 | 撥水撥油剤 |
| US20110021099A1 (en) * | 2008-03-28 | 2011-01-27 | Hisako Nakamura | Fluorine-containing polymer and water-and oil-repellent agent |
| US10077327B2 (en) * | 2008-03-28 | 2018-09-18 | Daikin Industries, Ltd. | Fluorine-containing copolymer and water- and oil-repellent agent |
| CN102046673B (zh) * | 2008-06-02 | 2016-02-24 | 旭硝子株式会社 | 共聚物、其制造方法、斥油剂组合物及其处理物品 |
| KR101572296B1 (ko) * | 2008-08-28 | 2015-11-26 | 스미또모 가가꾸 가부시키가이샤 | 수지 조성물, 게이트 절연층 및 유기 박막 트랜지스터 |
| WO2010080473A1 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| US8329822B2 (en) * | 2009-11-09 | 2012-12-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
| US8507601B2 (en) * | 2009-11-09 | 2013-08-13 | E. I. Du Pont De Nemours And Company | Method using fluoropolymer emulsions |
| US20110178260A1 (en) * | 2010-01-20 | 2011-07-21 | Sheng Peng | Fluoropolymer compositions and method of use |
| US8975348B2 (en) * | 2010-02-12 | 2015-03-10 | E I Du Pont De Nemours And Company | Non-aqueous composition comprising partially fluorinated methacrylic polymers |
| CN102337677B (zh) * | 2010-07-14 | 2014-03-19 | 杜邦公司 | 表面涂覆过的聚酯纤维基质及其制备方法 |
| WO2012020735A1 (ja) * | 2010-08-11 | 2012-02-16 | 旭硝子株式会社 | 撥水剤組成物、その製造方法、疎水性基材処理剤組成物および物品 |
| CN102492087B (zh) * | 2011-12-02 | 2014-04-16 | 广东德美精细化工股份有限公司 | 一种含氟丙烯酸酯共聚物阳离子乳液及其制备方法和应用 |
| US9534343B2 (en) * | 2012-10-18 | 2017-01-03 | The Chemours Company Fc, Llc | Partially fluorinated copolymer emulsions containing fatty acids and esters |
| KR20170060124A (ko) | 2014-09-26 | 2017-05-31 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 비-플루오르화 및 부분 플루오르화 중합체 |
| CN105755808A (zh) * | 2016-03-14 | 2016-07-13 | 湖州新创丝织品有限公司 | 一种汉麻织物抗紫外线整理方法 |
| CN110485160B (zh) * | 2017-10-24 | 2022-02-15 | 广东德美精细化工集团股份有限公司 | 包含遥爪聚合物的高效防水防油剂的制备方法 |
| WO2019115392A1 (en) | 2017-12-13 | 2019-06-20 | Heiq Materials Ag | Soil release formulations for textile applications |
| US20210261706A1 (en) * | 2018-07-26 | 2021-08-26 | Showa Denko Materials Co., Ltd. | Resin composition, heat storage material, and article |
| CN112694569B (zh) * | 2020-12-23 | 2021-08-17 | 东莞泰岳光学镀膜材料有限公司 | 一种含氟接枝共聚物及其制备方法与应用 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3944527A (en) | 1974-07-11 | 1976-03-16 | Minnesota Mining And Manufacturing Company | Fluoroaliphatic copolymers |
| US4127711A (en) * | 1977-03-31 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Fluorine-containing terpolymers |
| JPS6040182A (ja) | 1983-08-16 | 1985-03-02 | Asahi Glass Co Ltd | 高引火点を有する撥水撥油剤 |
| JPS6119684A (ja) | 1984-07-06 | 1986-01-28 | Meisei Kagaku Kogyo Kk | 耐久性の改良された撥水撥油剤 |
| US4595518A (en) * | 1985-07-10 | 1986-06-17 | E. I. Du Pont De Nemours And Company | Coating fibrous substrates with fluoropolymer amphoteric polymer and surfactants |
| US4742140A (en) | 1986-01-23 | 1988-05-03 | E. I. Du Pont De Nemours And Company | Oil- and water-repellent copolymers |
| EP0294648B1 (en) | 1987-05-25 | 1993-01-07 | Daikin Industries, Limited | Novel copolymer and water- and oil-repellent comprising the same |
| JP2508760B2 (ja) | 1987-10-20 | 1996-06-19 | 旭硝子株式会社 | 汚れ離脱性を有する撥水撥油剤 |
| US5143991A (en) | 1989-06-21 | 1992-09-01 | Daikin Industries, Ltd. | Copolymer desoiling agent |
| DE3939341A1 (de) | 1989-11-29 | 1991-06-06 | Bayer Ag | Hydrophobierungs- und oleophobierungsmittel |
| JPH0453842A (ja) | 1990-06-20 | 1992-02-21 | Dainippon Ink & Chem Inc | 低吸水率多孔質シート状物質の製造方法 |
| DE4026097A1 (de) | 1990-08-17 | 1992-02-20 | Hoechst Ag | Waessrige dispersionen von fluorhaltigen polymeren |
| BR9205831A (pt) | 1991-04-02 | 1994-08-02 | Minnesota Mining & Mfg | Composição flúor-eficiente repelente ao óleo e à água, substrato com propriedade repelentes ao óleo e à água, disperso aquosa, processo para proporcionar a um material subtrato fibroso propriedades de repelência ao óleo e à água, e, processo para melhorar a flúor-eficiência de um agente fluoroquimico |
| DE4113893A1 (de) | 1991-04-27 | 1992-10-29 | Bayer Ag | Waessrige dispersionen mit perfluoralkylgruppen enthaltenden copolymerisaten, verfahren zu ihrer herstellung und ihre verwendung |
| US5387640A (en) | 1992-01-22 | 1995-02-07 | Bayer Aktiengesellschaft | Fluorine-containing copolymers and aqueous dispersions prepared therefrom |
| DE4201604A1 (de) | 1992-01-22 | 1993-07-29 | Bayer Ag | Fluorhaltige copolymerisate und daraus hergestellte waessrige dispersionen |
| JPH05263070A (ja) | 1992-03-17 | 1993-10-12 | Daikin Ind Ltd | 高引火点撥水撥油剤およびその製法 |
| JPH0617034A (ja) | 1992-07-03 | 1994-01-25 | Asahi Glass Co Ltd | 撥水撥油剤組成物およびその製造方法 |
| JPH06240239A (ja) | 1993-02-17 | 1994-08-30 | Asahi Glass Co Ltd | 撥水撥油剤組成物 |
| JP3320491B2 (ja) | 1993-03-24 | 2002-09-03 | 旭硝子株式会社 | 防汚加工剤 |
| US5344903A (en) * | 1993-04-14 | 1994-09-06 | E. I. Du Pont De Nemours And Company | Water- and oil-repellent fluoro(meth)acrylate copolymers |
| JP3279442B2 (ja) | 1994-09-08 | 2002-04-30 | 花王株式会社 | 撥水剤組成物及び撥水剤物品並びに撥水処理方法 |
| DE4441982A1 (de) | 1994-11-25 | 1996-05-30 | Bayer Ag | Öl-, wasser- und schmutzabweisend ausgerüstete Substrate und fluorhaltige Mittel hierzu |
| JPH08283654A (ja) | 1995-04-19 | 1996-10-29 | Dainippon Ink & Chem Inc | 防汚被膜の形成方法 |
| US5674961A (en) | 1996-04-12 | 1997-10-07 | E. I. Du Pont De Nemours And Company | Oil water and solvent resistant paper by treatment with fluorochemical copolymers |
| JPH10176002A (ja) | 1996-12-18 | 1998-06-30 | Kansai Paint Co Ltd | 非水系重合体分散液及び硬化性組成物 |
| JPH11279527A (ja) * | 1997-06-30 | 1999-10-12 | Asahi Glass Co Ltd | 防汚加工剤組成物、その製造方法およびそれを用いた被処理物 |
| CA2243772C (en) | 1997-07-23 | 2008-04-15 | Asahi Glass Company Ltd. | Water and oil repellent composition |
| US6180740B1 (en) | 1998-02-27 | 2001-01-30 | E. I. Du Pont De Nemours And Company | Stabilization of fluorochemical copolymer emulsions |
| JP3864610B2 (ja) | 1998-05-21 | 2007-01-10 | 旭硝子株式会社 | 水分散型撥水撥油剤組成物およびその製造方法 |
| JP2000136377A (ja) | 1998-08-24 | 2000-05-16 | Asahi Glass Co Ltd | 水分散型撥水撥油剤組成物 |
| US6353051B1 (en) * | 1999-03-10 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Top coating for synthetic leathers |
-
2002
- 2002-03-04 US US10/091,004 patent/US6479605B1/en not_active Expired - Fee Related
- 2002-05-14 EP EP02741966A patent/EP1399618B1/en not_active Expired - Lifetime
- 2002-05-14 CN CNB028101154A patent/CN1239777C/zh not_active Expired - Fee Related
- 2002-05-14 DE DE60216455T patent/DE60216455T2/de not_active Expired - Lifetime
- 2002-05-14 WO PCT/US2002/018395 patent/WO2003054284A1/en not_active Ceased
- 2002-05-14 JP JP2003554977A patent/JP4271577B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101339752B1 (ko) * | 2011-12-28 | 2014-01-03 | 주식회사 스노젠 | 가교제 역할을 하는 다관능 이소시아네이트가 도입된 내구성 불소 발수제 조성물 및 그 합성방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1509361A (zh) | 2004-06-30 |
| DE60216455D1 (de) | 2007-01-11 |
| CN1239777C (zh) | 2006-02-01 |
| EP1399618A1 (en) | 2004-03-24 |
| WO2003054284A1 (en) | 2003-07-03 |
| JP2005513245A (ja) | 2005-05-12 |
| EP1399618B1 (en) | 2006-11-29 |
| DE60216455T2 (de) | 2007-09-20 |
| US6479605B1 (en) | 2002-11-12 |
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