DE69432228T2 - Fluorierte öl-in-wasser-emulsion zur oberflächenbehandlung - Google Patents
Fluorierte öl-in-wasser-emulsion zur oberflächenbehandlung Download PDFInfo
- Publication number
- DE69432228T2 DE69432228T2 DE69432228T DE69432228T DE69432228T2 DE 69432228 T2 DE69432228 T2 DE 69432228T2 DE 69432228 T DE69432228 T DE 69432228T DE 69432228 T DE69432228 T DE 69432228T DE 69432228 T2 DE69432228 T2 DE 69432228T2
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- oil
- group
- water
- surface treatment
- 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.)
- Expired - Fee Related
Links
- 238000004381 surface treatment Methods 0.000 title claims description 18
- 239000007764 o/w emulsion Substances 0.000 title claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 63
- 239000011737 fluorine Substances 0.000 claims description 63
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 62
- 239000003921 oil Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000000178 monomer Substances 0.000 claims description 35
- 229920001400 block copolymer Polymers 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000578 graft copolymer Polymers 0.000 claims description 25
- 239000010702 perfluoropolyether Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 12
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 230000001804 emulsifying effect Effects 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 description 32
- 239000004744 fabric Substances 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000005871 repellent Substances 0.000 description 13
- 230000002940 repellent Effects 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- -1 vinylidene halide Chemical class 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CHDVXKLFZBWKEN-UHFFFAOYSA-N C=C.F.F.F.Cl Chemical compound C=C.F.F.F.Cl CHDVXKLFZBWKEN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- HQBCITPSUTXPTN-UHFFFAOYSA-N n,n,1,1,2,2,3,3,3-nonafluoropropan-1-amine Chemical compound FN(F)C(F)(F)C(F)(F)C(F)(F)F HQBCITPSUTXPTN-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- IRAPFUAOCHNONS-UHFFFAOYSA-N potassium;phenylmethylbenzene Chemical compound [K+].C=1C=CC=CC=1[CH-]C1=CC=CC=C1 IRAPFUAOCHNONS-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
- 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
- C08L51/003—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 grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Colloid Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35103893 | 1993-12-29 | ||
| JP35103893 | 1993-12-29 | ||
| PCT/JP1994/002179 WO1995018194A1 (en) | 1993-12-29 | 1994-12-22 | Fluorinated oil/water emulsion and surface treatment composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69432228D1 DE69432228D1 (de) | 2003-04-10 |
| DE69432228T2 true DE69432228T2 (de) | 2004-01-22 |
Family
ID=18414626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69432228T Expired - Fee Related DE69432228T2 (de) | 1993-12-29 | 1994-12-22 | Fluorierte öl-in-wasser-emulsion zur oberflächenbehandlung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5965659A (enExample) |
| EP (1) | EP0743349B1 (enExample) |
| JP (1) | JP4006761B2 (enExample) |
| KR (1) | KR100332255B1 (enExample) |
| CN (1) | CN1082079C (enExample) |
| DE (1) | DE69432228T2 (enExample) |
| TW (1) | TW268902B (enExample) |
| WO (1) | WO1995018194A1 (enExample) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3502962B2 (ja) * | 1995-12-22 | 2004-03-02 | シキボウ株式会社 | ブロック共重合体オリゴマー、その製造法及び防汚加工剤及び繊維製品 |
| EP1000602B1 (en) * | 1997-06-04 | 2010-04-07 | Daikin Industries, Limited | Copolymers for cosmetics |
| US6143848A (en) * | 1997-10-23 | 2000-11-07 | The B.F.Goodrich Company | End-functionalized polymers by controlled free-radical polymerization process and polymers made therefrom |
| US6245854B1 (en) * | 1998-12-11 | 2001-06-12 | Visteon Global Technologies, Inc. | Fluorocarbon-containing hydrophilic polymer coating composition for heat exchangers |
| US6660828B2 (en) | 2001-05-14 | 2003-12-09 | Omnova Solutions Inc. | Fluorinated short carbon atom side chain and polar group containing polymer, and flow, or leveling, or wetting agents thereof |
| EP1389224B1 (en) | 2001-05-14 | 2010-01-13 | Omnova Soltions Inc | Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups |
| ITMI20011424A1 (it) * | 2001-07-05 | 2003-01-05 | Ausimont Spa | Dispersioni di polimeri fluorurati |
| JP2003129380A (ja) * | 2001-10-19 | 2003-05-08 | Daikin Ind Ltd | 蛋白質繊維の処理剤および処理方法 |
| US20050202997A1 (en) * | 2002-05-10 | 2005-09-15 | Makoto Hanazawa | Surfactant and dispersion aid each comprising graft fluoropolymer |
| BR0311260A (pt) * | 2002-05-24 | 2005-03-15 | 3M Innovative Properties Co | Composição fluoroquìmica, método de tratamento de um substrato fibroso, uso de uma composição fluoroquìmica e composto |
| DE60317663T2 (de) * | 2002-05-24 | 2008-10-30 | 3M Innovative Properties Co., St. Paul | Fluorchemische zusammensetzung enthaltend einen fluorierten polyether und dessen verwendung zur behandlung von fasermaterialien |
| US7425279B2 (en) * | 2002-05-24 | 2008-09-16 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| BR0311207A (pt) * | 2002-05-24 | 2005-03-15 | 3M Innovative Properies Compan | Composição fluoroquìmica, composição de revestimento, método de tratamento de um substrato fibroso, e , artigo |
| US20050005504A1 (en) * | 2003-06-30 | 2005-01-13 | Munagavalasa Murthy S. | Volatile insect control sheet and method of manufacture thereof |
| US20050064778A1 (en) * | 2003-09-19 | 2005-03-24 | Lam Robert C. | High coefficient friction material with symmetrical friction modifying particles |
| US20050075414A1 (en) * | 2003-10-03 | 2005-04-07 | Lam Robert C. | High performance, durable, deposit friction material |
| US7696261B2 (en) * | 2003-10-03 | 2010-04-13 | Borgwarner Inc. | Mixed deposit friction material |
| US20050074595A1 (en) | 2003-10-03 | 2005-04-07 | Lam Robert C. | Friction material containing partially carbonized carbon fibers |
| US20050075022A1 (en) * | 2003-10-03 | 2005-04-07 | Lam Robert C. | Elastic and porous friction material with high amount of fibers |
| JP4630955B2 (ja) * | 2004-05-19 | 2011-02-09 | 大原パラヂウム化学株式会社 | 親水・撥油加工剤で処理する繊維布帛の加工方法 |
| JP4996837B2 (ja) * | 2004-11-18 | 2012-08-08 | Ａｇｃセイミケミカル株式会社 | 潤滑オイルのバリア剤組成物およびその用途 |
| US20060216524A1 (en) | 2005-03-23 | 2006-09-28 | 3M Innovative Properties Company | Perfluoropolyether urethane additives having (meth)acryl groups and hard coats |
| GB2432836A (en) * | 2005-12-01 | 2007-06-06 | 3M Innovative Properties Co | Fluorinated surfactant |
| US8688161B2 (en) * | 2006-02-22 | 2014-04-01 | Qualcomm Incorporated | System and method for creating an ad hoc group in a push-to-talk system |
| US20070225176A1 (en) * | 2006-03-27 | 2007-09-27 | Pope Gary A | Use of fluorocarbon surfactants to improve the productivity of gas and gas condensate wells |
| US7772162B2 (en) | 2006-03-27 | 2010-08-10 | Board Of Regents, The University Of Texas System | Use of fluorocarbon surfactants to improve the productivity of gas and gas condensate wells |
| US8231973B2 (en) * | 2006-06-13 | 2012-07-31 | 3M Innovative Properties Company | Fluoro(meth)acrylate polymer composition suitable for low index layer of antireflective film |
| US7615283B2 (en) | 2006-06-13 | 2009-11-10 | 3M Innovative Properties Company | Fluoro(meth)acrylate polymer composition suitable for low index layer of antireflective film |
| US20080051300A1 (en) * | 2006-08-23 | 2008-02-28 | Pope Gary A | Compositions and method for improving the productivity of hydrocarbon producing wells |
| US20080047706A1 (en) * | 2006-08-23 | 2008-02-28 | Pope Gary A | Method of obtaining a treatment composition for improving the productivity of hydrocarbon producing wells |
| KR101249219B1 (ko) * | 2006-09-29 | 2013-04-03 | 삼성전자주식회사 | 공중합체, 뱅크 형성용 조성물 및 이를 이용한 뱅크 형성방법 |
| US20080124555A1 (en) | 2006-11-29 | 2008-05-29 | 3M Innovative Properties Company | Polymerizable composition comprising perfluoropolyether urethane having ethylene oxide repeat units |
| WO2008118240A1 (en) * | 2007-03-23 | 2008-10-02 | Board Of Regents, The University Of Texas System | Method and system for treating hydrocarbon formations |
| BRPI0721504B1 (pt) | 2007-03-23 | 2019-04-09 | Board Of Regents, The Unibersity Of Texas System | Método para tratamento com um fluido de uma formação portando hidrocarboneto |
| US8043998B2 (en) * | 2007-03-23 | 2011-10-25 | Board Of Regents, The University Of Texas System | Method for treating a fractured formation with a non-ionic fluorinated polymeric surfactant |
| WO2008118241A1 (en) * | 2007-03-23 | 2008-10-02 | Board Of Regents, The University Of Texas System | Compositions and methods for treating a water blocked well |
| WO2008118242A1 (en) * | 2007-03-23 | 2008-10-02 | Board Of Regents, The University Of Texas System | Compositions and methods for treating a water blocked well |
| US8403050B2 (en) * | 2007-03-23 | 2013-03-26 | 3M Innovative Properties Company | Method for treating a hydrocarbon-bearing formation with a fluid followed by a nonionic fluorinated polymeric surfactant |
| JP5453250B2 (ja) | 2007-06-06 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化エーテル組成物及びフッ素化エーテル組成物の使用方法 |
| KR101439538B1 (ko) | 2007-08-14 | 2014-09-12 | 삼성전자주식회사 | 보호막 형성용 조성물 및 이에 의한 보호막을 포함한유기박막 트랜지스터 |
| WO2009029438A1 (en) | 2007-08-31 | 2009-03-05 | 3M Innovative Properties Company | Hardcoats |
| JP5040583B2 (ja) * | 2007-10-19 | 2012-10-03 | ダイキン工業株式会社 | 含フッ素グラフト重合体および防汚剤 |
| EP2238312A4 (en) * | 2007-11-30 | 2011-08-17 | Univ Texas | METHOD FOR IMPROVING THE PRODUCTIVITY OF OIL EXTRACTION OILS |
| EP2222752B1 (en) * | 2007-12-12 | 2017-08-02 | 3M Innovative Properties Company | Hardcoats comprising perfluoropolyether polymers with poly(alkylene oxide) repeat units |
| CN101896515A (zh) * | 2007-12-13 | 2010-11-24 | 大金工业株式会社 | 含氟聚合物和水性处理剂 |
| WO2009087981A1 (ja) * | 2008-01-11 | 2009-07-16 | Kri Inc. | 重合性化合物及びこの製造方法 |
| EP2289484A4 (en) | 2008-05-21 | 2014-08-13 | Miyoshi Kasei Inc | SURFACE-TREATED POWDER AND COSMETICS THEREWITH |
| CN102317403A (zh) | 2008-12-18 | 2012-01-11 | 3M创新有限公司 | 使含烃地层与氟化醚组合物接触的方法 |
| JP2011088850A (ja) * | 2009-10-22 | 2011-05-06 | Miyoshi Kasei Inc | 表面処理粉体及びこれを配合した化粧料 |
| WO2011099540A1 (ja) * | 2010-02-12 | 2011-08-18 | ダイキン工業株式会社 | ブロック重合体の製造方法およびブロック重合体、ならびに表面処理剤 |
| 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 |
| US20130029151A1 (en) * | 2011-03-18 | 2013-01-31 | E. I. Du Pont De Nemours And Company | Flame-resistant finish for inherently flame resistant polymer yarns and process for making same |
| TWI503464B (zh) * | 2011-07-14 | 2015-10-11 | Du Pont | 表面經塗覆之聚酯基纖維基材 |
| JP5865648B2 (ja) * | 2011-09-29 | 2016-02-17 | ユニチカトレーディング株式会社 | 防汚性布帛の製造方法 |
| WO2013187432A1 (ja) * | 2012-06-13 | 2013-12-19 | ダイキン工業株式会社 | パーフルオロポリエーテル基含有シラン化合物および表面処理剤 |
| FR2998309B1 (fr) * | 2012-11-20 | 2015-04-10 | Snf Sas | Composition et procede d'encollage pour materiaux textile |
| WO2014097309A1 (en) | 2012-12-17 | 2014-06-26 | Asian Paints Ltd. | Stimuli responsive self cleaning coating |
| US9604918B2 (en) * | 2014-04-04 | 2017-03-28 | Unimatec Co., Ltd. | Carboxylic acid ester/carbamate compound with polymerizable functional group and fluorine atom group, and manufacturing method therefor |
| US10190051B2 (en) * | 2014-06-10 | 2019-01-29 | Alexium, Inc. | Emulsification of hydrophobic organophosphorous compounds |
| EP3070152B1 (fr) * | 2015-03-18 | 2018-02-28 | The Swatch Group Research and Development Ltd. | Substrat comprenant une surface recouverte d'un agent épilame et procédé d'épilamage d'un tel substrat |
| CN105155016B (zh) * | 2015-07-31 | 2018-01-05 | 江苏恒科新材料有限公司 | 一种超柔浓染型聚酯hoy纤维及其制备方法 |
| CN105002603B (zh) * | 2015-07-31 | 2018-01-05 | 江苏恒科新材料有限公司 | 一种超细旦聚酯纤维及其制备方法 |
| WO2017110698A1 (ja) * | 2015-12-25 | 2017-06-29 | ユニマテック株式会社 | 重合性官能基とフッ素原子団とを有するカルボン酸エステル化合物とその製造方法 |
| KR102170599B1 (ko) * | 2016-02-23 | 2020-10-27 | 다이킨 고교 가부시키가이샤 | 표면 처리제 |
| CN108286207A (zh) * | 2017-12-18 | 2018-07-17 | 巨化集团技术中心 | 一种纸制品用防水防油剂及其制备方法 |
| JP7779048B2 (ja) * | 2021-09-08 | 2025-12-03 | Ｔｏｐｐａｎホールディングス株式会社 | 撥液膜 |
| KR102551067B1 (ko) * | 2023-03-29 | 2023-07-04 | 국방과학연구소 | 화학작용제를 방어하기 위한 반응성 피부보호제 세정용 조성물 및 이를 이용한 세정 방법 |
| CN119462996A (zh) * | 2025-01-09 | 2025-02-18 | 衢州福聚电子材料有限公司 | 一种高强度pctfe树脂制备方法 |
| CN120817649B (zh) * | 2025-07-02 | 2025-12-30 | 上海柯珑清洁技术有限公司 | 一种隔油池用生物除油除味剂及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1215861A (en) * | 1967-02-09 | 1970-12-16 | Minnesota Mining & Mfg | Cleanable stain-resistant fabrics or fibers and polymers therefor |
| JPS52106386A (en) * | 1976-03-05 | 1977-09-06 | Dainippon Ink & Chem Inc | Nonaqueous emulsion |
| JPS6034730A (ja) * | 1983-08-05 | 1985-02-22 | Nippon Mektron Ltd | 繊維処理用撥水撥油剤エマルジョン |
| JPH0676303B2 (ja) * | 1986-06-10 | 1994-09-28 | 鐘紡株式会社 | 非水乳化型整髪化粧料 |
| JPS632916A (ja) * | 1986-06-23 | 1988-01-07 | Kanebo Ltd | 非水乳化型メイクアツプ化粧料 |
| JP2621206B2 (ja) * | 1987-08-21 | 1997-06-18 | 旭硝子株式会社 | 新規な含フツ素化合物及びその用途 |
| JPH02147601A (ja) * | 1988-08-08 | 1990-06-06 | Kao Corp | 自己分散型含フッ素樹脂水性エマルションの製造方法 |
| EP0593617B1 (en) * | 1991-07-10 | 1996-05-08 | Minnesota Mining And Manufacturing Company | Fluorochemical water- and oil- repellent treating compositions |
| JPH0778154B2 (ja) * | 1991-07-11 | 1995-08-23 | ヘキスト合成株式会社 | 含フッ素アクリル系共重合体水性エマルジョンの製造方法及びその組成物 |
-
1994
- 1994-12-22 EP EP95903930A patent/EP0743349B1/en not_active Expired - Lifetime
- 1994-12-22 US US08/669,288 patent/US5965659A/en not_active Expired - Fee Related
- 1994-12-22 CN CN94194737A patent/CN1082079C/zh not_active Expired - Fee Related
- 1994-12-22 WO PCT/JP1994/002179 patent/WO1995018194A1/ja not_active Ceased
- 1994-12-22 KR KR1019960703475A patent/KR100332255B1/ko not_active Expired - Fee Related
- 1994-12-22 DE DE69432228T patent/DE69432228T2/de not_active Expired - Fee Related
- 1994-12-22 JP JP51789295A patent/JP4006761B2/ja not_active Expired - Fee Related
-
1995
- 1995-01-27 TW TW084100777A patent/TW268902B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| CN1082079C (zh) | 2002-04-03 |
| CN1139950A (zh) | 1997-01-08 |
| KR970700747A (ko) | 1997-02-12 |
| EP0743349A4 (en) | 1998-06-03 |
| EP0743349A1 (en) | 1996-11-20 |
| JP4006761B2 (ja) | 2007-11-14 |
| EP0743349B1 (en) | 2003-03-05 |
| KR100332255B1 (ko) | 2002-10-25 |
| WO1995018194A1 (en) | 1995-07-06 |
| DE69432228D1 (de) | 2003-04-10 |
| US5965659A (en) | 1999-10-12 |
| TW268902B (enExample) | 1996-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69432228T2 (de) | Fluorierte öl-in-wasser-emulsion zur oberflächenbehandlung | |
| DE69400835T2 (de) | Verschmutzungsverhindernde Substanz | |
| DE60033924T2 (de) | Wasser- und ölabweisende zusammensetzung und verfahren zu deren herstellung | |
| DE60300949T2 (de) | Wässrige Dispersion | |
| DE69320362T2 (de) | Nicht-wässrige emulgierte oberflächenbehandlungszusammensetzung | |
| DE69210608T2 (de) | Fluorverbindung enthaltende wasser- und ölabweisende behandlungsmittel | |
| DE69405730T2 (de) | Wasser-und öl abweisende fluoro(meth)acrylat copolymere | |
| DE69914855T2 (de) | Wäßrige schmutzabweisende Zusammensetzung vom Dispersionstyp und damit behandelte Textilfasern | |
| DE69017557T2 (de) | Schmutzabweisendes Mittel. | |
| DE3787118T2 (de) | Fluor enthaltende, Wasser und Ölabweisende Zubereitung. | |
| DE69914267T2 (de) | Schmutzabweisende Fluorpolymer-Emulsion | |
| DE3856225T2 (de) | Wasser und Öl abweisende Verbindung mit reinigenden Eigenschaften | |
| DE2358647C3 (de) | Schmutz-, öl- und wasserabweisendes Copolymeres und dessen Verwendung | |
| DE69531993T2 (de) | Hydrophobierende und ölphobierende schmutzabweisungsmittel | |
| DE602004005498T2 (de) | Fluoreffiziente appreturen für textilien | |
| DE60018343T2 (de) | In wasser dispergierbare wasser- und ölabweisende zusammensetzung | |
| DE1745163B2 (de) | Impraegniermittel zum schmutz- und oelabweisenden impraegnieren von textilien | |
| DE69317300T2 (de) | Wässrige disperionszusammensetzung, verfahren zu ihrer herstellung, wasser und öl abstossendes mittel und trennmittel | |
| DE2104267C3 (de) | Verfahren zur Herstellung von Perfluoralkylgruppen enthaltenden Acryl säureesterpolymeren | |
| DE69211847T2 (de) | Fluoracrylatmonomere und polymere, verfahren zu ihrer herstellung und ihre verwendung | |
| DE69902345T2 (de) | In wasser dispergierte wasser- und ölabweisende zusammensetzung und verfahren zu ihrer herstellung | |
| US10513821B2 (en) | Water-based surface treatment agent | |
| DE60012804T2 (de) | Wasser- und ölabstossende Zusammensetzungen | |
| DE69429160T2 (de) | Behandlung von textilprodukt | |
| DE2749386A1 (de) | Dispersionen hydrophiler acrylharze |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |