CA2487067A1 - Fluorochemical composition for treatment of a fibrous substrate - Google Patents
Fluorochemical composition for treatment of a fibrous substrate Download PDFInfo
- Publication number
- CA2487067A1 CA2487067A1 CA 2487067 CA2487067A CA2487067A1 CA 2487067 A1 CA2487067 A1 CA 2487067A1 CA 2487067 CA2487067 CA 2487067 CA 2487067 A CA2487067 A CA 2487067A CA 2487067 A1 CA2487067 A1 CA 2487067A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- groups
- fluorochemical
- compounds
- fluorinated
- 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 212
- 239000000758 substrate Substances 0.000 title claims abstract description 152
- 238000011282 treatment Methods 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 229920000570 polyether Polymers 0.000 claims abstract description 113
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 111
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000012948 isocyanate Substances 0.000 claims abstract description 67
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000005871 repellent Substances 0.000 claims abstract description 17
- 230000002940 repellent Effects 0.000 claims abstract description 17
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 96
- -1 isocyanate compounds Chemical class 0.000 claims description 96
- 150000002009 diols Chemical class 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 229920005862 polyol Polymers 0.000 claims description 50
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 31
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000006185 dispersion Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 125000005647 linker group Chemical group 0.000 claims description 14
- 239000000376 reactant Substances 0.000 claims description 14
- 150000004756 silanes Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000010702 perfluoropolyether Substances 0.000 claims description 7
- 230000003381 solubilizing effect Effects 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 125000005515 organic divalent group Chemical group 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000002689 soil Substances 0.000 abstract description 21
- 238000009877 rendering Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 52
- 150000003673 urethanes Chemical class 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000003921 oil Substances 0.000 description 44
- 235000019198 oils Nutrition 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 36
- 229920000742 Cotton Polymers 0.000 description 35
- 239000004744 fabric Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- XYQNMGJZDSSVRP-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n,n-bis(2-hydroxyethyl)butane-1-sulfonamide Chemical compound OCCN(CCO)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XYQNMGJZDSSVRP-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- 238000004900 laundering Methods 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 15
- 239000002981 blocking agent Substances 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 238000010409 ironing Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000539 dimer Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 150000002894 organic compounds Chemical class 0.000 description 11
- 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 10
- 229920001451 polypropylene glycol Polymers 0.000 description 10
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 125000000962 organic group Chemical group 0.000 description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960004592 isopropanol Drugs 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 150000001718 carbodiimides Chemical class 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 230000000149 penetrating effect Effects 0.000 description 5
- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 229920001400 block copolymer Polymers 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 4
- 150000004812 organic fluorine compounds Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
- 239000004632 polycaprolactone Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- FUVKFLJWBHVMHX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FUVKFLJWBHVMHX-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
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- 239000003599 detergent Substances 0.000 description 3
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229960003151 mercaptamine Drugs 0.000 description 3
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 229940117969 neopentyl glycol Drugs 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000002921 oxetanes Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 229940012831 stearyl alcohol Drugs 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- D06M15/53—Polyethers
-
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]
- Y10T442/102—Woven scrim
- Y10T442/172—Coated or impregnated
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]
- Y10T442/184—Nonwoven scrim
- Y10T442/198—Coated or impregnated
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2164—Coating or impregnation specified as water repellent
- Y10T442/2189—Fluorocarbon containing
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US38339202P | 2002-05-24 | 2002-05-24 | |
| US60/383,392 | 2002-05-24 | ||
| PCT/US2003/015088 WO2003100157A1 (en) | 2002-05-24 | 2003-05-13 | Fluorochemical composition for treatment of a fibrous substrate |
Publications (1)
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| CA2487067A1 true CA2487067A1 (en) | 2003-12-04 |
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| US7101618B2 (en) | 2004-05-07 | 2006-09-05 | 3M Innovative Properties Company | Article comprising fluorochemical surface layer |
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| US20060013983A1 (en) * | 2004-07-15 | 2006-01-19 | 3M Innovative Properties Company | Adhesive delivery of oil and water repellents |
| US20060029799A1 (en) * | 2004-08-03 | 2006-02-09 | 3M Innovative Properties Company | Adhesive delivery of fluoroether repellents |
| CA2593694A1 (en) * | 2004-12-30 | 2006-07-13 | 3M Innovative Properties Company | Articles comprising a fluorochemical surface layer and related methods |
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| EP2158264B1 (en) | 2007-06-08 | 2019-04-10 | 3M Innovative Properties Company | Blends of fluoroalkyl-containing ester oligomers with polydicarbodiimide(s) |
| JP2010529263A (ja) * | 2007-06-08 | 2010-08-26 | スリーエム イノベイティブ プロパティズ カンパニー | ペルフルオロアルキル部分を含む撥水性及び撥油性付与エステルオリゴマー |
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| CN102282191A (zh) * | 2008-11-25 | 2011-12-14 | 3M创新有限公司 | 氟化醚尿烷及其使用方法 |
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| US20140170917A1 (en) * | 2012-12-19 | 2014-06-19 | 3M Innovative Properties Company | Polyurethane polymer, synthetic leather, and method |
| CN104870106B (zh) * | 2012-12-19 | 2018-05-11 | 3M创新有限公司 | 用于易于清洁的表面的涂料组合物和多层膜 |
| CN104448278B (zh) * | 2014-12-12 | 2016-04-06 | 东华大学 | 一种防污阻燃防熔滴聚酯及其制备方法 |
| CN105603748A (zh) * | 2016-01-11 | 2016-05-25 | 苏州迈塔斯芯片科技有限公司 | 双疏整理剂及其制备方法 |
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| CA2303033A1 (en) * | 1997-09-29 | 1999-04-08 | The Dow Chemical Company | Liquid urethane compositions for textile coatings |
| IT1311977B1 (it) | 1999-03-25 | 2002-03-22 | Ausimont Spa | Composizioni idro-oleo repellenti. |
| IT1312344B1 (it) * | 1999-06-03 | 2002-04-15 | Ausimont Spa | Composizioni per film a basso indice di rifrazione. |
| JP4855616B2 (ja) | 1999-10-27 | 2012-01-18 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロケミカルスルホンアミド界面活性剤 |
| IT1317725B1 (it) | 2000-01-17 | 2003-07-15 | Ausimont Spa | Composizioni per coatings a base di (per)fluoropolieteri. |
| AU2001273428A1 (en) * | 2000-08-14 | 2002-02-25 | 3M Innovative Properties Company | Urethane-based stain-release coatings |
| US6646088B2 (en) * | 2000-08-16 | 2003-11-11 | 3M Innovative Properties Company | Urethane-based stain-release coatings |
| AU2003234544B2 (en) * | 2002-05-24 | 2008-04-03 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| US7425279B2 (en) * | 2002-05-24 | 2008-09-16 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| JP2005527677A (ja) | 2002-05-24 | 2005-09-15 | スリーエム イノベイティブ プロパティズ カンパニー | 弗素化ポリエーテルを含むフルオロケミカル組成物および該組成物による繊維基材の処理 |
-
2003
- 2003-05-13 AU AU2003234544A patent/AU2003234544B2/en not_active Ceased
- 2003-05-13 EP EP20030728884 patent/EP1507916A1/en not_active Withdrawn
- 2003-05-13 KR KR10-2004-7019000A patent/KR20050014832A/ko not_active Withdrawn
- 2003-05-13 CN CNB038119080A patent/CN1304683C/zh not_active Expired - Fee Related
- 2003-05-13 JP JP2004507593A patent/JP2005526924A/ja not_active Withdrawn
- 2003-05-13 BR BR0311207A patent/BR0311207A/pt not_active IP Right Cessation
- 2003-05-13 WO PCT/US2003/015088 patent/WO2003100157A1/en not_active Ceased
- 2003-05-13 CA CA 2487067 patent/CA2487067A1/en not_active Abandoned
- 2003-05-13 MX MXPA04011448A patent/MXPA04011448A/es not_active Application Discontinuation
- 2003-05-23 JP JP2004507594A patent/JP2005527674A/ja active Pending
- 2003-05-23 US US10/444,713 patent/US7214736B2/en not_active Expired - Lifetime
- 2003-05-23 CA CA2493857A patent/CA2493857C/en not_active Expired - Fee Related
- 2003-05-23 CN CNB038177153A patent/CN1316115C/zh not_active Expired - Fee Related
- 2003-05-23 AT AT03734154T patent/ATE448355T1/de not_active IP Right Cessation
- 2003-05-23 DE DE60330002T patent/DE60330002D1/de not_active Expired - Lifetime
- 2003-05-23 AU AU2003239603A patent/AU2003239603B2/en not_active Expired - Fee Related
- 2003-05-23 WO PCT/US2003/016341 patent/WO2003100158A1/en not_active Ceased
- 2003-05-23 KR KR10-2004-7018998A patent/KR20050014831A/ko not_active Ceased
- 2003-05-23 MX MXPA04011629A patent/MXPA04011629A/es active IP Right Grant
- 2003-05-23 BR BR0311249A patent/BR0311249A/pt not_active IP Right Cessation
- 2003-05-23 EP EP03734154A patent/EP1507917B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1671913A (zh) | 2005-09-21 |
| BR0311207A (pt) | 2005-03-15 |
| AU2003239603B2 (en) | 2008-08-28 |
| MXPA04011448A (es) | 2005-03-23 |
| EP1507917B1 (en) | 2009-11-11 |
| CN1304683C (zh) | 2007-03-14 |
| MXPA04011629A (es) | 2005-03-31 |
| WO2003100157A1 (en) | 2003-12-04 |
| EP1507916A1 (en) | 2005-02-23 |
| CA2493857A1 (en) | 2003-12-04 |
| AU2003239603A1 (en) | 2003-12-12 |
| US7214736B2 (en) | 2007-05-08 |
| AU2003234544A1 (en) | 2003-12-12 |
| ATE448355T1 (de) | 2009-11-15 |
| CN1656280A (zh) | 2005-08-17 |
| DE60330002D1 (de) | 2009-12-24 |
| BR0311249A (pt) | 2005-03-15 |
| KR20050014832A (ko) | 2005-02-07 |
| AU2003234544B2 (en) | 2008-04-03 |
| JP2005527674A (ja) | 2005-09-15 |
| WO2003100158A1 (en) | 2003-12-04 |
| CN1316115C (zh) | 2007-05-16 |
| EP1507917A1 (en) | 2005-02-23 |
| CA2493857C (en) | 2011-12-13 |
| JP2005526924A (ja) | 2005-09-08 |
| KR20050014831A (ko) | 2005-02-07 |
| US20040077238A1 (en) | 2004-04-22 |
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| EEER | Examination request | ||
| FZDE | Discontinued |