CA2409504A1 - Water- and oil-repellent composition - Google Patents
Water- and oil-repellent composition Download PDFInfo
- Publication number
- CA2409504A1 CA2409504A1 CA002409504A CA2409504A CA2409504A1 CA 2409504 A1 CA2409504 A1 CA 2409504A1 CA 002409504 A CA002409504 A CA 002409504A CA 2409504 A CA2409504 A CA 2409504A CA 2409504 A1 CA2409504 A1 CA 2409504A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorine
- composition
- fluorochemical
- polyol
- dicarboxylic acid
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 353
- 239000005871 repellent Substances 0.000 title claims abstract description 31
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 91
- 239000011737 fluorine Substances 0.000 claims abstract description 91
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 90
- 229920005862 polyol Polymers 0.000 claims abstract description 76
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims abstract description 73
- 150000003077 polyols Chemical class 0.000 claims abstract description 72
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- -1 heteroaliphatic Chemical group 0.000 claims description 98
- 239000000835 fiber Substances 0.000 claims description 27
- 150000002009 diols Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 230000000699 topical effect Effects 0.000 claims description 17
- 229920001169 thermoplastic Polymers 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000155 melt Substances 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000010128 melt processing Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- 239000012713 reactive precursor Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000004416 thermosoftening plastic Substances 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 229920003232 aliphatic polyester Chemical group 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229920006294 polydialkylsiloxane Chemical group 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000004634 thermosetting polymer Substances 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 239000008135 aqueous vehicle Substances 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 229920000592 inorganic polymer Polymers 0.000 claims description 2
- 229920000620 organic polymer Polymers 0.000 claims description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 72
- 229920000728 polyester Polymers 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 239000003921 oil Substances 0.000 description 56
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
- HUFHNYZNTFSKCT-UHFFFAOYSA-N n-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-n-(2-hydroxyethyl)octane-1-sulfonamide Chemical compound OCCN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HUFHNYZNTFSKCT-UHFFFAOYSA-N 0.000 description 41
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000010998 test method Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000004745 nonwoven fabric Substances 0.000 description 20
- 239000000654 additive Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000004750 melt-blown nonwoven Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 16
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000004417 polycarbonate Substances 0.000 description 11
- 239000005020 polyethylene terephthalate Substances 0.000 description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- PLGACQRCZCVKGK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-n-(2-hydroxyethyl)-n-methyloctane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PLGACQRCZCVKGK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010276 construction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 150000002763 monocarboxylic acids Chemical class 0.000 description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 230000002940 repellent Effects 0.000 description 9
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- 238000001125 extrusion Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000008188 pellet Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 229920001610 polycaprolactone Polymers 0.000 description 7
- 239000004632 polycaprolactone Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000004205 dimethyl polysiloxane Chemical group 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Chemical group 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 229920001410 Microfiber Polymers 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 150000002221 fluorine Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000003658 microfiber Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 3
- 229920001643 poly(ether ketone) Polymers 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
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- 238000010926 purge Methods 0.000 description 3
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- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- DSRUAYIFDCHEEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(2-hydroxyethyl)-n-methylbutane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DSRUAYIFDCHEEV-UHFFFAOYSA-N 0.000 description 2
- SRMWNTGHXHOWBT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-n-methyloctane-1-sulfonamide Chemical compound CNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SRMWNTGHXHOWBT-UHFFFAOYSA-N 0.000 description 2
- NEOGGGHDLGYATP-UHFFFAOYSA-N 1,6-dimethylimidazo[4,5-b]pyridin-2-amine Chemical compound CC1=CN=C2N=C(N)N(C)C2=C1 NEOGGGHDLGYATP-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical class ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920002534 Polyethylene Glycol 1450 Polymers 0.000 description 2
- 229920002596 Polyethylene Glycol 900 Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 102100021669 Stromal cell-derived factor 1 Human genes 0.000 description 2
- 101710088580 Stromal cell-derived factor 1 Proteins 0.000 description 2
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- 239000008240 homogeneous mixture Substances 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
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- 238000012423 maintenance Methods 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- LOTWRKOXHCMWDB-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)benzamide Chemical compound OCCN(CCO)C(=O)C1=CC=CC=C1 LOTWRKOXHCMWDB-UHFFFAOYSA-N 0.000 description 1
- ZSBOIPHQFKYRMG-UHFFFAOYSA-N n-ethyl-1,1,2,2,3,3,4,4,4-nonafluoro-n-(2-hydroxyethyl)butane-1-sulfonamide Chemical compound OCCN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZSBOIPHQFKYRMG-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- LUUFSCNUZAYHAT-UHFFFAOYSA-N octadecane-1,18-diol Chemical compound OCCCCCCCCCCCCCCCCCCO LUUFSCNUZAYHAT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 239000000123 paper Substances 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- CXGONMQFMIYUJR-UHFFFAOYSA-N perfluorododecanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CXGONMQFMIYUJR-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003047 pimelic acids Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
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- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 230000003678 scratch resistant effect Effects 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
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- 150000003442 suberic acids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
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- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
- C03C17/324—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/236—Esters of carboxylic acids; Esters of carbonic acid 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
- 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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/438—Sulfonamides ; Sulfamic acids
-
- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/507—Polyesters
-
- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/507—Polyesters
- D06M15/5075—Polyesters containing sulfonic groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/592,105 US6586522B1 (en) | 2000-06-12 | 2000-06-12 | Water- and oil-repellent composition |
| US09/592,105 | 2000-06-12 | ||
| PCT/US2000/029420 WO2001096654A1 (en) | 2000-06-12 | 2000-10-25 | Water- and oil-repellent composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2409504A1 true CA2409504A1 (en) | 2001-12-20 |
Family
ID=24369302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002409504A Abandoned CA2409504A1 (en) | 2000-06-12 | 2000-10-25 | Water- and oil-repellent composition |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6586522B1 (enExample) |
| EP (1) | EP1290269A1 (enExample) |
| JP (1) | JP2004503690A (enExample) |
| KR (1) | KR100674050B1 (enExample) |
| AU (1) | AU2001212313A1 (enExample) |
| CA (1) | CA2409504A1 (enExample) |
| WO (1) | WO2001096654A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6762137B2 (en) * | 2000-12-21 | 2004-07-13 | Kimberly-Clark Worldwide, Inc. | Water repellant meltblown webs and laminates |
| US6753380B2 (en) * | 2001-03-09 | 2004-06-22 | 3M Innovative Properties Company | Water-and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| US20060100359A1 (en) * | 2002-06-19 | 2006-05-11 | Blackwood William R | Fire and stain resistant compositions |
| US20060003154A1 (en) * | 2004-06-30 | 2006-01-05 | Snowden Hue S | Extruded thermoplastic articles with enhanced surface segregation of internal melt additive |
| US7285595B2 (en) * | 2004-06-30 | 2007-10-23 | Kimberly-Clark Worldwide, Inc. | Synergistic fluorochemical treatment blend |
| US20060135673A1 (en) * | 2004-12-15 | 2006-06-22 | Temperante John A | Fluorochemical esters blends as repellent polymer melt additives |
| US7396866B2 (en) * | 2004-12-15 | 2008-07-08 | 3M Innovative Properties Company | Fluorochemical diesters as repellent polymer melt additives |
| 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 |
| 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 |
| US7820563B2 (en) | 2006-10-23 | 2010-10-26 | Hawaii Nanosciences, Llc | Compositions and methods for imparting oil repellency and/or water repellency |
| WO2008051221A2 (en) * | 2006-10-23 | 2008-05-02 | Nano-Structured Consumer Products, Llc | Compositions and methods for imparting oil repellency and/or water repellency |
| WO2008154414A2 (en) * | 2007-06-08 | 2008-12-18 | 3M Innovative Properties Company | Water- and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| CN101679705B (zh) | 2007-06-08 | 2013-12-11 | 3M创新有限公司 | 含氟烷基的酯低聚物与聚碳二亚胺的共混物 |
| ES2383047T3 (es) * | 2007-11-01 | 2012-06-15 | Asahi Glass Company, Limited | Copolímero fluorado, composición de agente impermeabilizante frente a agua y aceite y sus métodos de producción |
| CA2727701A1 (en) | 2008-06-12 | 2009-12-17 | 3M Innovative Properties Company | Biocompatible hydrophilic compositions |
| EP2291558B1 (en) * | 2008-06-12 | 2017-07-26 | 3M Innovative Properties Company | Melt blown fine fibers and methods of manufacture |
| US9487893B2 (en) | 2009-03-31 | 2016-11-08 | 3M Innovative Properties Company | Dimensionally stable nonwoven fibrous webs and methods of making and using the same |
| US8293928B2 (en) * | 2009-09-02 | 2012-10-23 | E I Du Pont De Nemours And Company | Fluorinated 4-oxo-chroman-7-carboxylates |
| US20110218319A1 (en) * | 2009-09-02 | 2011-09-08 | E. I. Du Pont De Nemours And Company | Polyaramid films comprising fluorovinylether functionalized aromatic moieties |
| BR112012004774A2 (pt) * | 2009-09-02 | 2017-05-30 | Du Pont | polímero e processo |
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| EP3368618B1 (en) | 2015-10-28 | 2020-11-25 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| CN108350289B (zh) * | 2015-10-28 | 2021-10-12 | 3M创新有限公司 | 基于溶剂的拒斥性涂料组合物和经涂覆的基材 |
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| JP7115718B2 (ja) * | 2017-06-13 | 2022-08-09 | スリーエム イノベイティブ プロパティズ カンパニー | 溶融添加剤化合物、その使用方法、並びにそれを含む物品及び組成物 |
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| US3255131A (en) * | 1961-05-10 | 1966-06-07 | Minnesota Mining & Mfg | Fluorochemical-containing varnishes |
| DE2024909B2 (de) | 1970-05-22 | 1977-09-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n-hydroxyalkyl-perfluoralkansulfonamiden und einige n,n-bis-(hydroxyalkyl)-perfluor-alkansulfonamide |
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| US5145727A (en) | 1990-11-26 | 1992-09-08 | Kimberly-Clark Corporation | Multilayer nonwoven composite structure |
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| IN186438B (enExample) | 1996-03-29 | 2001-09-01 | Daikin Ind Ltd | |
| KR20010012515A (ko) | 1997-05-14 | 2001-02-15 | 스프레이그 로버트 월터 | 기재에 오염 제거 특성을 부여하기 위한 플루오로케미칼폴리에테르와 폴리이소시아네이트의 축합 생성물을포함하는 플루오로케미칼 조성물 |
-
2000
- 2000-06-12 US US09/592,105 patent/US6586522B1/en not_active Expired - Fee Related
- 2000-10-25 WO PCT/US2000/029420 patent/WO2001096654A1/en not_active Ceased
- 2000-10-25 KR KR1020027016884A patent/KR100674050B1/ko not_active Expired - Fee Related
- 2000-10-25 EP EP00973848A patent/EP1290269A1/en not_active Withdrawn
- 2000-10-25 CA CA002409504A patent/CA2409504A1/en not_active Abandoned
- 2000-10-25 AU AU2001212313A patent/AU2001212313A1/en not_active Abandoned
- 2000-10-25 JP JP2002510757A patent/JP2004503690A/ja not_active Withdrawn
-
2003
- 2003-01-09 US US10/339,418 patent/US6960642B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| US20030199621A1 (en) | 2003-10-23 |
| WO2001096654A1 (en) | 2001-12-20 |
| KR100674050B1 (ko) | 2007-01-26 |
| US6586522B1 (en) | 2003-07-01 |
| JP2004503690A (ja) | 2004-02-05 |
| US6960642B2 (en) | 2005-11-01 |
| AU2001212313A1 (en) | 2001-12-24 |
| EP1290269A1 (en) | 2003-03-12 |
| KR20030011885A (ko) | 2003-02-11 |
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| EEER | Examination request | ||
| FZDE | Discontinued |