JP5548124B2 - ペルフルオロアルキル基を含有するコポリマーとその水性分散液 - Google Patents
ペルフルオロアルキル基を含有するコポリマーとその水性分散液 Download PDFInfo
- Publication number
- JP5548124B2 JP5548124B2 JP2010513692A JP2010513692A JP5548124B2 JP 5548124 B2 JP5548124 B2 JP 5548124B2 JP 2010513692 A JP2010513692 A JP 2010513692A JP 2010513692 A JP2010513692 A JP 2010513692A JP 5548124 B2 JP5548124 B2 JP 5548124B2
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- JP
- Japan
- Prior art keywords
- copolymer
- mol
- monomers
- units derived
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 54
- 239000006185 dispersion Substances 0.000 title claims description 22
- 125000005010 perfluoroalkyl group Chemical group 0.000 title abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 239000002657 fibrous material Substances 0.000 claims description 23
- 239000004745 nonwoven fabric Substances 0.000 claims description 7
- 239000004753 textile Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- -1 acrylate compound Chemical class 0.000 abstract description 14
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 230000001846 repelling effect Effects 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical class CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZAFBPXUQKNWAEZ-UHFFFAOYSA-N (3-chloro-3-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(O)Cl ZAFBPXUQKNWAEZ-UHFFFAOYSA-N 0.000 description 1
- OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2915—Rod, strand, filament or fiber including textile, cloth or fabric
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07012551.3 | 2007-06-27 | ||
| EP07012551A EP2009035A1 (de) | 2007-06-27 | 2007-06-27 | Copolymere mit Perfluoralkylgruppen und wässrige Dispersionen davon |
| PCT/EP2008/003845 WO2009000370A1 (en) | 2007-06-27 | 2008-05-14 | Copolymers containing perfluoroalkyl groups and aqueous dispersions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010531370A JP2010531370A (ja) | 2010-09-24 |
| JP2010531370A5 JP2010531370A5 (enExample) | 2011-04-21 |
| JP5548124B2 true JP5548124B2 (ja) | 2014-07-16 |
Family
ID=38476212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010513692A Active JP5548124B2 (ja) | 2007-06-27 | 2008-05-14 | ペルフルオロアルキル基を含有するコポリマーとその水性分散液 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8349976B2 (enExample) |
| EP (2) | EP2009035A1 (enExample) |
| JP (1) | JP5548124B2 (enExample) |
| KR (1) | KR101490137B1 (enExample) |
| CN (1) | CN101687955B (enExample) |
| AT (1) | ATE496950T1 (enExample) |
| BR (1) | BRPI0810643B1 (enExample) |
| DE (1) | DE602008004771D1 (enExample) |
| ES (1) | ES2358166T3 (enExample) |
| MX (1) | MX2009012017A (enExample) |
| WO (1) | WO2009000370A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008035906A1 (de) | 2008-08-02 | 2010-02-04 | Huntsman Textile Effects (Germany) Gmbh | Zusammensetzungen mit Fluor enthaltendem Polymeren und Siloxan |
| EP2264079B1 (en) * | 2008-03-12 | 2015-05-27 | Asahi Glass Company, Limited | Copolymer and method for producing the same |
| EP2233633A1 (de) * | 2009-03-28 | 2010-09-29 | Huntsman Textile Effects (Germany) GmbH | Fluorfreie wässrige Dispersion für die Behandlung von textilen Flächengebilden |
| EP2302130A1 (de) | 2009-09-26 | 2011-03-30 | Huntsman Textile Effects (Germany) GmbH | Zusammensetzung für die Öl- und/oder Wasserabweisende Ausrüstung von Fasermaterialien |
| EP3301220A1 (en) | 2016-09-30 | 2018-04-04 | Coöperatie Avebe U.A. | Greaseproof paper |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491169A (en) * | 1966-07-22 | 1970-01-20 | Du Pont | Oil and water repellent |
| DE1669046A1 (de) * | 1967-09-21 | 1971-06-03 | Schramm Lack & Farbenfab | Elektroisolierlack |
| JPS503438B1 (enExample) | 1969-01-17 | 1975-02-04 | ||
| US4060681A (en) | 1976-02-11 | 1977-11-29 | Ciba-Geigy Corporation | Unsaturated esters of polyfluoroalkylthioalcohols |
| JPS608068B2 (ja) * | 1978-09-28 | 1985-02-28 | ダイキン工業株式会社 | 撥水撥油剤 |
| US4742140A (en) | 1986-01-23 | 1988-05-03 | E. I. Du Pont De Nemours And Company | Oil- and water-repellent copolymers |
| DE4039193A1 (de) * | 1990-12-08 | 1992-06-11 | Bayer Ag | In wasser dispergierbare, elektrolytstabile polyetherester-modifizierte polyurethanionomere |
| US5387640A (en) * | 1992-01-22 | 1995-02-07 | Bayer Aktiengesellschaft | Fluorine-containing copolymers and aqueous dispersions prepared therefrom |
| US5344903A (en) * | 1993-04-14 | 1994-09-06 | E. I. Du Pont De Nemours And Company | Water- and oil-repellent fluoro(meth)acrylate copolymers |
| US6326447B1 (en) * | 1998-06-19 | 2001-12-04 | E. I. Du Pont De Nemours And Company | Polymeric compositions for soil release on fabrics |
| KR100682784B1 (ko) * | 1999-10-29 | 2007-02-16 | 아사히 가라스 가부시키가이샤 | 발수발유제용 수분산액 및 그 제조방법 |
| US7709563B2 (en) | 2001-01-30 | 2010-05-04 | Daikin Industries, Ltd. | Aqueous dispersion type fluorine-containing water- and-oil repellent composition having a polymer of a perfluoroalkyl group- containing etheylenically unsaturated monomer, a nonionic surfactant ana cationic surfactant, and preparation and use thereof |
| WO2002072727A1 (en) * | 2001-03-09 | 2002-09-19 | Daikin Industries, Ltd. | Water-and-oil repellant composition with improved suitability for cold cure |
| US6479605B1 (en) * | 2001-05-15 | 2002-11-12 | E. I. Du Pont De Nemours And Company | High-durability, low-yellowing repellent for textiles |
| CN100463931C (zh) * | 2003-11-03 | 2009-02-25 | 长春赛纳纳米服饰有限公司 | 一种纳米材料改性的织物整理剂及其制备方法 |
| JP2005146102A (ja) * | 2003-11-14 | 2005-06-09 | Daikin Ind Ltd | 撥水撥油剤組成物の製造方法 |
| RU2444534C2 (ru) * | 2006-08-25 | 2012-03-10 | Клариант Файненс (Бви) Лимитед | Масло-, водо- и грязеотталкивающие сополимеры перфторалкилэтилметакрилата |
| US8945712B2 (en) * | 2007-06-06 | 2015-02-03 | 3M Innovative Properties Company | Fluorinated compositions and surface treatments made therefrom |
| EP2172495A1 (en) * | 2008-10-03 | 2010-04-07 | Ineos Europe Limited | Method for the production of polymers |
-
2007
- 2007-06-27 EP EP07012551A patent/EP2009035A1/de not_active Withdrawn
-
2008
- 2008-05-14 KR KR1020097027107A patent/KR101490137B1/ko not_active Expired - Fee Related
- 2008-05-14 CN CN200880021729XA patent/CN101687955B/zh active Active
- 2008-05-14 JP JP2010513692A patent/JP5548124B2/ja active Active
- 2008-05-14 AT AT08758500T patent/ATE496950T1/de not_active IP Right Cessation
- 2008-05-14 EP EP08758500A patent/EP2160420B1/en active Active
- 2008-05-14 US US12/666,513 patent/US8349976B2/en active Active
- 2008-05-14 WO PCT/EP2008/003845 patent/WO2009000370A1/en not_active Ceased
- 2008-05-14 DE DE602008004771T patent/DE602008004771D1/de active Active
- 2008-05-14 MX MX2009012017A patent/MX2009012017A/es active IP Right Grant
- 2008-05-14 BR BRPI0810643-6A patent/BRPI0810643B1/pt active IP Right Grant
- 2008-05-14 ES ES08758500T patent/ES2358166T3/es active Active
-
2012
- 2012-12-11 US US13/710,567 patent/US8568875B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010531370A (ja) | 2010-09-24 |
| EP2160420B1 (en) | 2011-01-26 |
| EP2009035A1 (de) | 2008-12-31 |
| WO2009000370A1 (en) | 2008-12-31 |
| BRPI0810643B1 (pt) | 2018-04-10 |
| ES2358166T3 (es) | 2011-05-06 |
| CN101687955B (zh) | 2012-03-21 |
| EP2160420A1 (en) | 2010-03-10 |
| MX2009012017A (es) | 2010-03-26 |
| BRPI0810643A2 (pt) | 2014-11-04 |
| DE602008004771D1 (de) | 2011-03-10 |
| KR101490137B1 (ko) | 2015-02-05 |
| US8349976B2 (en) | 2013-01-08 |
| US8568875B2 (en) | 2013-10-29 |
| US20130102724A1 (en) | 2013-04-25 |
| KR20100036268A (ko) | 2010-04-07 |
| ATE496950T1 (de) | 2011-02-15 |
| CN101687955A (zh) | 2010-03-31 |
| US20100193724A1 (en) | 2010-08-05 |
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