JP4025015B2 - 合成有機ポリマーに対する疎水性で疎油性の添加剤としての高温安定フルオロケミカル - Google Patents
合成有機ポリマーに対する疎水性で疎油性の添加剤としての高温安定フルオロケミカル Download PDFInfo
- Publication number
- JP4025015B2 JP4025015B2 JP2000504310A JP2000504310A JP4025015B2 JP 4025015 B2 JP4025015 B2 JP 4025015B2 JP 2000504310 A JP2000504310 A JP 2000504310A JP 2000504310 A JP2000504310 A JP 2000504310A JP 4025015 B2 JP4025015 B2 JP 4025015B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorochemical
- acid
- dimer
- alcohol
- alkyl group
- 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
- 229920005613 synthetic organic polymer Polymers 0.000 title claims description 14
- 230000002209 hydrophobic effect Effects 0.000 title claims description 11
- 239000000654 additive Substances 0.000 title description 12
- 239000002253 acid Substances 0.000 claims description 90
- 239000000539 dimer Substances 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 63
- 239000000835 fiber Substances 0.000 claims description 60
- 239000004744 fabric Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 2
- 239000003921 oil Substances 0.000 description 58
- 238000000034 method Methods 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 150000002148 esters Chemical class 0.000 description 48
- -1 extruded sheets Substances 0.000 description 39
- 239000010408 film Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 150000001412 amines Chemical class 0.000 description 30
- 238000012360 testing method Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 27
- 150000007513 acids Chemical class 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- 239000004743 Polypropylene Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 229920001155 polypropylene Polymers 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 16
- 238000001125 extrusion Methods 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 238000002411 thermogravimetry Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000000155 melt Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 12
- 150000002924 oxiranes Chemical class 0.000 description 12
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 11
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 11
- 239000005642 Oleic acid Substances 0.000 description 11
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 229910001651 emery Inorganic materials 0.000 description 11
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 229920001169 thermoplastic Polymers 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920005749 polyurethane resin Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- 229920001410 Microfiber Polymers 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003658 microfiber Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 229920001059 synthetic polymer Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000004049 embossing Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229920006097 Ultramide® Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000006162 fluoroaliphatic group Chemical group 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000011236 particulate material Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- OSIVISXRDMXJQR-UHFFFAOYSA-M potassium;2-[ethyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]acetate Chemical compound [K+].[O-]C(=O)CN(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 OSIVISXRDMXJQR-UHFFFAOYSA-M 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- GDCNXRJVBFTRMS-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)(=O)Cl.C(CCCCCCCCCCCCCCCCC)(=O)O Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)Cl.C(CCCCCCCCCCCCCCCCC)(=O)O GDCNXRJVBFTRMS-UHFFFAOYSA-N 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical class OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- BHFJBHMTEDLICO-UHFFFAOYSA-N Perfluorooctylsulfonyl fluoride 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)S(F)(=O)=O BHFJBHMTEDLICO-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- KBNBFLVBJDYEFE-UHFFFAOYSA-M butyl-hydroxy-oxotin;hydrate Chemical compound O.CCCC[Sn](O)=O KBNBFLVBJDYEFE-UHFFFAOYSA-M 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- UODXSCCNACAPCE-UHFFFAOYSA-N draft:flumetramide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1OCC(=O)NC1 UODXSCCNACAPCE-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000001192 hot extrusion Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HLWRUJAIJJEZDL-UHFFFAOYSA-M sodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC([O-])=O HLWRUJAIJJEZDL-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2915—Rod, strand, filament or fiber including textile, cloth or fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- 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
- Y10T442/183—Synthetic polymeric fiber
-
- 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
- Y10T442/2008—Fabric composed of a fiber or strand which is of specific structural definition
-
- 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
- Y10T442/2311—Coating or impregnation is a lubricant or a surface friction reducing agent other than specified as improving the "hand" of the fabric or increasing the softness thereof
- Y10T442/232—Fluorocarbon containing
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
- Nonwoven Fabrics (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/901,363 US6127485A (en) | 1997-07-28 | 1997-07-28 | High temperature-stable fluorochemicals as hydrophobic and oleophobic additives to synthetic organic polymers |
| US08/901,363 | 1997-07-28 | ||
| PCT/US1997/022227 WO1999005345A1 (en) | 1997-07-28 | 1997-12-05 | High temperature-stable fluorochemicals as hydrophobic and oleophobic additives to synthetic organic polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001511477A JP2001511477A (ja) | 2001-08-14 |
| JP2001511477A5 JP2001511477A5 (enExample) | 2005-12-22 |
| JP4025015B2 true JP4025015B2 (ja) | 2007-12-19 |
Family
ID=25414025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000504310A Expired - Fee Related JP4025015B2 (ja) | 1997-07-28 | 1997-12-05 | 合成有機ポリマーに対する疎水性で疎油性の添加剤としての高温安定フルオロケミカル |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6127485A (enExample) |
| EP (1) | EP1000184B1 (enExample) |
| JP (1) | JP4025015B2 (enExample) |
| KR (1) | KR100473674B1 (enExample) |
| AU (1) | AU5372798A (enExample) |
| CA (1) | CA2297145A1 (enExample) |
| DE (1) | DE69724287T2 (enExample) |
| WO (1) | WO1999005345A1 (enExample) |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6476114B2 (en) * | 1997-11-19 | 2002-11-05 | 3M Innovative Properties Company | Thermoplastic polymer film comprising a fluorochemical compound |
| US6342456B1 (en) * | 1999-02-01 | 2002-01-29 | Burlington Industries, Inc. | Polypropylene outdoor fabric |
| US6391807B1 (en) | 1999-09-24 | 2002-05-21 | 3M Innovative Properties Company | Polymer composition containing a fluorochemical oligomer |
| US6235824B1 (en) | 1999-05-11 | 2001-05-22 | 3M Innovative Properties Company | Polish composition and method of use |
| US6288157B1 (en) | 1999-05-11 | 2001-09-11 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof |
| US6525127B1 (en) | 1999-05-11 | 2003-02-25 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| US7049379B2 (en) | 1999-05-11 | 2006-05-23 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| US6193791B1 (en) | 1999-09-24 | 2001-02-27 | 3M Innovative Properties Company | Polish composition and method of use |
| US6174964B1 (en) | 1999-09-24 | 2001-01-16 | 3M Innovative Properties Company | Fluorochemical oligomer and use thereof |
| US6592988B1 (en) | 1999-12-29 | 2003-07-15 | 3M Innovative Properties Company | Water-and oil-repellent, antistatic composition |
| EP1174417B1 (en) * | 2000-02-29 | 2008-01-02 | Asahi Glass Company Ltd. | Fluorine compounds and water- and oil-repellant compositions |
| US6638610B1 (en) * | 2000-03-06 | 2003-10-28 | Porex Technologies Corp. | Water and oil repellent porous materials and processes for making the same |
| DE10101627B4 (de) * | 2001-01-16 | 2005-06-02 | C. Cramer, Weberei, Heek-Nienborg, Gmbh & Co. Kg | Textilfasermaterial mit permanenter Phobierwirkung |
| US6753380B2 (en) * | 2001-03-09 | 2004-06-22 | 3M Innovative Properties Company | Water-and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| DE10127362C2 (de) * | 2001-06-06 | 2003-05-15 | Siemens Ag | Zündanlage für eine Brennkraftmaschine |
| US6924329B2 (en) | 2001-11-05 | 2005-08-02 | 3M Innovative Properties Company | Water- and oil-repellent, antistatic compositions |
| KR100482671B1 (ko) * | 2002-02-05 | 2005-04-13 | 주식회사 태평양 | 디리놀레익산 유도체 및 이의 제조방법, 및 이를 함유하는복합체 |
| US20030220427A1 (en) * | 2002-05-09 | 2003-11-27 | Gary Wentworth | Adhesion promoter for cord-reinforced rubber and metal or polymer substrate/rubber composites |
| US7138450B2 (en) * | 2002-05-09 | 2006-11-21 | Cph Innovations Corp. | Vulcanized rubber composition with a liquid adhesion promoter containing an adhesive resin and ester |
| US7285588B2 (en) * | 2003-03-28 | 2007-10-23 | Hallstar Innovations Corp. | Low polarity dimerate and trimerate esters as plasticizers for thermoplastic compositions |
| US7144937B2 (en) * | 2002-05-09 | 2006-12-05 | Cph Innovations Corp. | Adhesion promoters for sealants |
| US7122592B2 (en) * | 2002-05-09 | 2006-10-17 | Cph Innovations Corp. | Adhesion promoters for cord-reinforced thermoplastic polymeric materials and substrate/thermoplastic polymeric material composites |
| US6884832B2 (en) * | 2002-05-09 | 2005-04-26 | The C.P. Hall Company | Adhesion promoter for cord-reinforced rubber and metal or polymer substrate/rubber composites |
| US6858290B2 (en) * | 2002-05-29 | 2005-02-22 | 3M Innovative Properties Company | Fluid repellent microporous materials |
| AU2003249191A1 (en) * | 2002-07-17 | 2004-02-09 | Cph Innovations Corporation | Low polarity dimerate and trimerate esters as plasticizers for elastomers |
| US7232855B2 (en) | 2002-07-17 | 2007-06-19 | Cph Innovations Corp. | Low polarity dimerate and trimerate esters as plasticizers for thermoplastic polymer/elastomer composites |
| JP2004106228A (ja) | 2002-09-13 | 2004-04-08 | Three M Innovative Properties Co | 保護フィルム付き撥水シート、着雪防止用シート、及び撥水性基板の製造方法 |
| US20050058779A1 (en) * | 2003-09-12 | 2005-03-17 | Goldbaum Richard H. | Suppression of repellency in polyolefins |
| CN1856522A (zh) * | 2003-09-25 | 2006-11-01 | 西巴特殊化学品控股有限公司 | 带有氟化基团的romp |
| US7422791B2 (en) * | 2003-11-19 | 2008-09-09 | Hallstar Innovations Corp. | Joint assemblies, methods for installing joint assemblies, and jointing compositions |
| US7931944B2 (en) | 2003-11-25 | 2011-04-26 | Kimberly-Clark Worldwide, Inc. | Method of treating substrates with ionic fluoropolymers |
| US7811949B2 (en) * | 2003-11-25 | 2010-10-12 | Kimberly-Clark Worldwide, Inc. | Method of treating nonwoven fabrics with non-ionic fluoropolymers |
| MY145571A (en) | 2003-12-19 | 2012-02-29 | Ciba Holding Inc | Fluorocarbon terminated oligo-and poly-carbonates as surface modifiers |
| US7521410B2 (en) * | 2004-03-26 | 2009-04-21 | Arrowstar, Llc | Compositions and methods for imparting odor resistance and articles thereof |
| US20080039558A1 (en) * | 2004-05-25 | 2008-02-14 | Dario Lazzari | Perfluorinated Esters, Polyester, Ethers and Carbonates |
| US7399807B2 (en) * | 2004-07-09 | 2008-07-15 | Unitex Chemical Corporation | Hydrophobic, oleophobic and alcohol-resistant fluorochemical additive |
| US20060013983A1 (en) | 2004-07-15 | 2006-01-19 | 3M Innovative Properties Company | Adhesive delivery of oil and water repellents |
| DE602005009549D1 (de) * | 2004-08-25 | 2008-10-16 | Ciba Holding Inc | Oberflächenmodifikatoren |
| US7230043B2 (en) | 2004-09-07 | 2007-06-12 | 3M Innovative Properties Company | Hydrophilic polymer composition |
| US20060110997A1 (en) * | 2004-11-24 | 2006-05-25 | Snowden Hue S | Treated nonwoven fabrics and method of treating nonwoven fabrics |
| US7396866B2 (en) * | 2004-12-15 | 2008-07-08 | 3M Innovative Properties Company | Fluorochemical diesters as repellent polymer melt additives |
| US20060135673A1 (en) * | 2004-12-15 | 2006-06-22 | Temperante John A | Fluorochemical esters blends as repellent polymer melt additives |
| MY145424A (en) * | 2005-02-07 | 2012-02-15 | Ciba Holding Inc | Functionalized esters, amides or urethanes of perfluorinated alcohols or amines as surface modifiers |
| EP1851270B1 (en) * | 2005-02-25 | 2009-12-23 | Basf Se | Fluorinated compounds |
| US7906057B2 (en) * | 2005-07-14 | 2011-03-15 | 3M Innovative Properties Company | Nanostructured article and method of making the same |
| US20070014997A1 (en) * | 2005-07-14 | 2007-01-18 | 3M Innovative Properties Company | Tool and method of making and using 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 |
| DE602007001975D1 (de) * | 2006-06-14 | 2009-09-24 | Basf Se | S-perfluoralkylsubstituierte hydroxybenzylthioether und derivate als oberflächenmodifizierungsmittel |
| US20080057019A1 (en) * | 2006-09-06 | 2008-03-06 | Collier Robert B | Compositions and methods for imparting odor resistance and articles thereof |
| WO2008028845A1 (en) * | 2006-09-07 | 2008-03-13 | Ciba Holding Inc. | Perfluoroalkyl substituted phenol derivatives as surface modifiers |
| US20140276470A1 (en) | 2006-11-07 | 2014-09-18 | Raymond Lareau | Dialysis Catheters with Fluoropolymer Additives |
| US8603070B1 (en) | 2013-03-15 | 2013-12-10 | Angiodynamics, Inc. | Catheters with high-purity fluoropolymer additives |
| JP5694768B2 (ja) * | 2007-09-14 | 2015-04-01 | スリーエム イノベイティブ プロパティズ カンパニー | 基材の撥水性を増加させる組成物及び方法 |
| US20090203276A1 (en) * | 2008-02-13 | 2009-08-13 | Goulston Technologies, Inc. | Polymer additive for providing an alcohol repellency for polypropylene nonwoven medical barrier fabrics |
| JP5670887B2 (ja) | 2008-06-12 | 2015-02-18 | スリーエム イノベイティブ プロパティズ カンパニー | 生体適合性親水性組成物 |
| JP5485988B2 (ja) * | 2008-06-12 | 2014-05-07 | スリーエム イノベイティブ プロパティズ カンパニー | メルトブローン微細繊維及び製造方法 |
| DK2321360T3 (da) * | 2008-08-28 | 2021-02-08 | Evonik Canada Inc | Termisk stabile biuret- og isocyanuratbaserede overflademodificerende makromolekyler og anvendelser deraf |
| US20100079055A1 (en) * | 2008-09-30 | 2010-04-01 | General Electric Company | Providing an improved thermal path to electronics by overmolding in a lighting source |
| BRPI1006777A2 (pt) | 2009-03-31 | 2019-09-24 | 3M Innovative Properties Co | "mantas, artigo, lençol cirúrgico, avental cirúrgico, invólucro de esterilização, material de contato para ferimentos e métodos para fabricação de uma manta" |
| WO2010112395A1 (en) | 2009-04-02 | 2010-10-07 | Basf Se | S-perfluoroalkyl substituted hydroxybenzylthioethers and derivatives as surface modifiers |
| EP2295132B8 (en) | 2009-05-15 | 2017-03-15 | Interface Biologics Inc. | Antithrombogenic hollow fiber membranes, potting material and blood tubing |
| CN105274733B (zh) * | 2009-12-17 | 2018-11-20 | 3M创新有限公司 | 尺寸稳定的非织造纤维幅材及其制造和使用方法 |
| EP2513365A4 (en) | 2009-12-17 | 2013-09-18 | 3M Innovative Properties Co | DIMENSION-STABLE FIBER-NETS, MELT-BLOWN FIBER-FIBERS, AND METHOD FOR THEIR PRODUCTION AND USE |
| WO2011106205A2 (en) | 2010-02-23 | 2011-09-01 | 3M Innovative Properties Company | Dimensionally stable nonwoven fibrous webs and methods of making and using the same |
| EP2542308A4 (en) | 2010-03-03 | 2016-09-14 | 3M Innovative Properties Co | DISTRIBUTABLE FACIAL MASK AND METHOD OF MANUFACTURING THE SAME |
| US8936111B2 (en) | 2010-03-06 | 2015-01-20 | Halliburton Energy Services, Inc. | Invert drilling fluids having enhanced rheology and methods of drilling boreholes |
| TW201221714A (en) | 2010-10-14 | 2012-06-01 | 3M Innovative Properties Co | Dimensionally stable nonwoven fibrous webs and methods of making and using the same |
| MX355184B (es) * | 2010-12-21 | 2018-04-09 | 3M Innovative Properties Co | Metodo para tratar formaciones que contienen hidrocarburos con amina fluorada. |
| US8784402B1 (en) | 2013-03-15 | 2014-07-22 | Angiodynamics, Inc. | Catheters with fluoropolymer additives |
| US9206283B1 (en) | 2013-03-15 | 2015-12-08 | Angiodynamics, Inc. | Thermoplastic polyurethane admixtures |
| US10166321B2 (en) | 2014-01-09 | 2019-01-01 | Angiodynamics, Inc. | High-flow port and infusion needle systems |
| US9447257B2 (en) | 2014-02-10 | 2016-09-20 | Eastman Chemical Company | Polymers combined with certain additives and devices made thererom |
| US9764884B2 (en) | 2014-10-06 | 2017-09-19 | Interface Biologics, Inc. | Packaging materials including a barrier film |
| BR112017008787A2 (pt) * | 2014-10-28 | 2017-12-26 | 3M Innovative Properties Co | componentes de um sistema de aplicação de aspersões que compreende uma superfície repelente & métodos |
| CN113145341A (zh) | 2015-10-28 | 2021-07-23 | 3M创新有限公司 | 包括拒液表面的喷雾施用系统部件和方法 |
| WO2017074708A1 (en) | 2015-10-28 | 2017-05-04 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| WO2017100045A1 (en) | 2015-12-11 | 2017-06-15 | 3M Innovative Properties Company | Fluorinated piperazine sulfonamides |
| CN109071992A (zh) | 2016-04-26 | 2018-12-21 | 3M创新有限公司 | 包括包含硅氧烷材料的排斥性表面的经受冰形成的制品 |
| US10662165B2 (en) | 2016-05-31 | 2020-05-26 | 3M Innovative Properties Company | Fluorochemical piperazine carboxamides |
| WO2018005040A1 (en) | 2016-06-27 | 2018-01-04 | 3M Innovative Properties Company | Fluorochemical piperazine carboxamides |
| US10590072B2 (en) * | 2016-09-09 | 2020-03-17 | 3M Innovative Properties Company | Partially fluorinated aromatic esters |
| WO2018075663A1 (en) | 2016-10-18 | 2018-04-26 | Interface Biologics, Inc. | Plasticized pvc admixtures with surface modifying macromolecules and articles made therefrom |
| US10961340B2 (en) | 2017-07-14 | 2021-03-30 | Fresenius Medical Care Holdings, Inc. | Method for providing surface modifying composition with improved byproduct removal |
| EP3724381B1 (en) * | 2017-12-13 | 2024-11-06 | Donaldson Company, Inc. | Oleophobic polyamide fine fibers, methods, filter media, and filter elements |
| CN108357783B (zh) * | 2018-03-16 | 2020-02-14 | 中塑新材料科技（杭州）有限公司 | 一种抗油污热封高阻隔膜 |
| DE102018110246B4 (de) | 2018-04-27 | 2020-12-31 | Johann Borgers GmbH | Faservliesformteil |
| CN109912468B (zh) * | 2019-02-26 | 2021-06-08 | 武汉松石科技股份有限公司 | 一种丙烯酸(1-氯甲基，2-n-甲基全氟己基磺酰胺基)乙酯的制备方法 |
| US11970595B2 (en) | 2020-12-30 | 2024-04-30 | 3M Innovative Properties Company | Partially fluorinated sulfonamide for use in PET films |
| CN112940396B (zh) * | 2021-02-03 | 2023-04-07 | 珠海格力新材料有限公司 | 一种具有双疏效果的熔喷聚丙烯及其制备方法和应用 |
| WO2022245657A1 (en) * | 2021-05-18 | 2022-11-24 | Edwards Lifesciences Corporation | Implantable fibers, yarns and textiles |
| EP4457279A1 (en) | 2021-12-30 | 2024-11-06 | 3M Innovative Properties Company | Additives for use in low surface-energy applications |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809990A (en) * | 1955-12-29 | 1957-10-15 | Minnesota Mining & Mfg | Fluorocarbon acids and derivatives |
| US2803656A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbonsulfonamidoalkanols and sulfates thereof |
| US3398182A (en) * | 1962-06-22 | 1968-08-20 | Minnesota Mining & Mfg | Fluorocarbon urethane compounds |
| US3923715A (en) * | 1973-07-26 | 1975-12-02 | Du Pont | Aqueous dispersions of perfluoroalkyl esters and vinyl polymers for treating textiles |
| US4001305A (en) * | 1974-02-04 | 1977-01-04 | Ciba-Geigy Corporation | Rf-glycols containing two perfluoroalkylthio groups and useful compositions therefrom |
| US4029585A (en) * | 1975-07-26 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Aqueous dispersions of perfluoroalkyl esters for treating textiles |
| US4215205A (en) * | 1977-01-12 | 1980-07-29 | Minnesota Mining And Manufacturing Company | Fluoroaliphatic radical and carbodiimide containing compositions for fabric treatment |
| US4264484A (en) * | 1979-01-24 | 1981-04-28 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| US4426466A (en) * | 1982-06-09 | 1984-01-17 | Minnesota Mining And Manufacturing Company | Paper treatment compositions containing fluorochemical carboxylic acid and epoxidic cationic resin |
| US4539006A (en) * | 1983-09-13 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Leather treatment |
| US4566981A (en) * | 1984-03-30 | 1986-01-28 | Minnesota Mining And Manufacturing Company | Fluorochemicals and fibrous substrates treated therewith: compositions of cationic and non-ionic fluorochemicals |
| US4668406A (en) * | 1984-04-02 | 1987-05-26 | Minnesota Mining And Manufacturing Company | Fluorochemical biuret compositions and fibrous substrates treated therewith |
| US4606737A (en) * | 1984-06-26 | 1986-08-19 | Minnesota Mining And Manufacturing Company | Fluorochemical allophanate compositions and fibrous substrates treated therewith |
| JP2502059B2 (ja) * | 1986-02-05 | 1996-05-29 | 旭硝子株式会社 | 汚れ除去性の高い撥水撥油剤 |
| GB8607803D0 (en) * | 1986-03-27 | 1986-04-30 | Kimberly Clark Ltd | Non-woven laminated material |
| US5025052A (en) * | 1986-09-12 | 1991-06-18 | Minnesota Mining And Manufacturing Company | Fluorochemical oxazolidinones |
| JPH0341160A (ja) * | 1989-07-07 | 1991-02-21 | Kao Corp | 撥液性のすぐれた熱可塑性樹脂組成物 |
| US5143963A (en) * | 1989-12-06 | 1992-09-01 | Res Development Corp. | Thermoplastic polymers with dispersed fluorocarbon additives |
| US5410073A (en) * | 1989-12-29 | 1995-04-25 | E. I. Du Pont De Nemours And Company | Manufacture of polyfluoro nitrogen containing organic compounds |
| IT1243747B (it) * | 1990-10-24 | 1994-06-21 | Sviluppo Settori Impiego Srl | Composizioni polimeriche oleo-repellenti e loro impiego nella preparazione di corpi formati aventi superfici ad elevata resistenza ai solventi ed elevata repellenza allo sporco. |
| US5145727A (en) * | 1990-11-26 | 1992-09-08 | Kimberly-Clark Corporation | Multilayer nonwoven composite structure |
| US5149576A (en) * | 1990-11-26 | 1992-09-22 | Kimberly-Clark Corporation | Multilayer nonwoven laminiferous structure |
| US5314959A (en) * | 1991-03-06 | 1994-05-24 | Minnesota Mining And Manufacturing Company | Graft copolymers containing fluoroaliphatic groups |
| US5459188A (en) * | 1991-04-11 | 1995-10-17 | Peach State Labs, Inc. | Soil resistant fibers |
| US5244951A (en) * | 1991-05-02 | 1993-09-14 | Minnesota Mining And Manufacturing Company | Durably hydrophilic, thermoplastic fiber |
| EP0613462B1 (en) * | 1991-11-12 | 1996-01-17 | Minnesota Mining And Manufacturing Company | Fluoroaliphatic dimer acid derivatives and use thereof |
| US5380778A (en) * | 1992-09-30 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Fluorochemical aminoalcohols |
| US5451622A (en) * | 1992-09-30 | 1995-09-19 | Minnesota Mining And Manufacturing Company | Composition comprising thermoplastic polymer and fluorochemical piperazine compound |
| AU669420B2 (en) * | 1993-03-26 | 1996-06-06 | Minnesota Mining And Manufacturing Company | Oily mist resistant electret filter media |
| SE9400437D0 (sv) * | 1994-02-10 | 1994-02-10 | Pharmacia Lkb Biotech | Filterbrunn och förfarande vid dess tillverkning |
| TW426712B (en) * | 1995-12-21 | 2001-03-21 | Du Pont | Fluorinated diester melt additives for thermoplastic polymers and their uses |
| US5798402A (en) * | 1995-12-21 | 1998-08-25 | E. I. Du Pont De Nemours And Company | Fluorinated sulfone melt additives for thermoplastic polymers |
| TW376397B (en) * | 1995-12-21 | 1999-12-11 | Du Pont | Fluorinated ester melt additives for thermoplastic fibers |
| JPH09323956A (ja) * | 1996-05-31 | 1997-12-16 | Wako Pure Chem Ind Ltd | 新規なコハク酸誘導体 |
| US5981614A (en) * | 1996-09-13 | 1999-11-09 | Adiletta; Joseph G. | Hydrophobic-oleophobic fluoropolymer compositions |
-
1997
- 1997-07-28 US US08/901,363 patent/US6127485A/en not_active Expired - Lifetime
- 1997-12-05 JP JP2000504310A patent/JP4025015B2/ja not_active Expired - Fee Related
- 1997-12-05 KR KR10-2000-7000901A patent/KR100473674B1/ko not_active Expired - Fee Related
- 1997-12-05 WO PCT/US1997/022227 patent/WO1999005345A1/en not_active Ceased
- 1997-12-05 DE DE1997624287 patent/DE69724287T2/de not_active Expired - Fee Related
- 1997-12-05 CA CA 2297145 patent/CA2297145A1/en not_active Abandoned
- 1997-12-05 EP EP19970950832 patent/EP1000184B1/en not_active Expired - Lifetime
- 1997-12-05 AU AU53727/98A patent/AU5372798A/en not_active Abandoned
-
2000
- 2000-06-30 US US09/609,191 patent/US6262180B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1028796A1 (en) | 2001-03-02 |
| JP2001511477A (ja) | 2001-08-14 |
| US6127485A (en) | 2000-10-03 |
| DE69724287D1 (de) | 2003-09-25 |
| CA2297145A1 (en) | 1999-02-04 |
| EP1000184B1 (en) | 2003-08-20 |
| WO1999005345A1 (en) | 1999-02-04 |
| EP1000184A1 (en) | 2000-05-17 |
| AU5372798A (en) | 1999-02-16 |
| KR20010022322A (ko) | 2001-03-15 |
| DE69724287T2 (de) | 2004-05-27 |
| US6262180B1 (en) | 2001-07-17 |
| KR100473674B1 (ko) | 2005-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4025015B2 (ja) | 合成有機ポリマーに対する疎水性で疎油性の添加剤としての高温安定フルオロケミカル | |
| US5451622A (en) | Composition comprising thermoplastic polymer and fluorochemical piperazine compound | |
| US20030162903A1 (en) | High temperature stable fluorochemical graft polymers as hydrophobic, oleophobic and alcohol-resistant additives to synthetic organic polymers | |
| US7399807B2 (en) | Hydrophobic, oleophobic and alcohol-resistant fluorochemical additive | |
| US5099026A (en) | Fluorochemical oxazolidinones | |
| EP0876342B1 (en) | Fluorinated melt additives for thermoplastic polymers | |
| US7396866B2 (en) | Fluorochemical diesters as repellent polymer melt additives | |
| JP2003519281A (ja) | 撥水撥油性帯電防止組成物 | |
| AU603604B2 (en) | Fluorochemical oxazolidinones | |
| US20190241510A1 (en) | Partially fluorinated aromatic esters | |
| US20060135673A1 (en) | Fluorochemical esters blends as repellent polymer melt additives | |
| HK1028796B (en) | High temperature-stable fluorochemicals as hydrophobic and oleophobic additives for synthetic organic polymers | |
| CN1205692A (zh) | 热塑性聚合物的氟化熔体添加剂 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20041203 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20041203 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070420 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070522 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070809 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20070904 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20071004 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101012 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |