JP5412629B2 - 帯電防止組成物 - Google Patents
帯電防止組成物 Download PDFInfo
- Publication number
- JP5412629B2 JP5412629B2 JP2001528488A JP2001528488A JP5412629B2 JP 5412629 B2 JP5412629 B2 JP 5412629B2 JP 2001528488 A JP2001528488 A JP 2001528488A JP 2001528488 A JP2001528488 A JP 2001528488A JP 5412629 B2 JP5412629 B2 JP 5412629B2
- Authority
- JP
- Japan
- Prior art keywords
- antistatic
- bis
- test method
- imide
- compound
- 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
- 239000000203 mixture Substances 0.000 title claims description 72
- 150000003839 salts Chemical class 0.000 claims description 73
- 238000002844 melting Methods 0.000 claims description 37
- 230000008018 melting Effects 0.000 claims description 36
- 229920000642 polymer Polymers 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 239000000835 fiber Substances 0.000 claims description 24
- 150000001450 anions Chemical class 0.000 claims description 22
- 239000011810 insulating material Substances 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 150000001768 cations Chemical class 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 150000002891 organic anions Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000003949 imides Chemical class 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003930 superacid Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000010998 test method Methods 0.000 description 63
- -1 polyoxyethylene Chemical class 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000005979 thermal decomposition reaction Methods 0.000 description 30
- 239000002216 antistatic agent Substances 0.000 description 28
- 239000010408 film Substances 0.000 description 28
- 230000003068 static effect Effects 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- 239000004744 fabric Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 17
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 16
- 239000004743 Polypropylene Substances 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 229920000515 polycarbonate Polymers 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 239000004417 polycarbonate Substances 0.000 description 13
- 238000001125 extrusion Methods 0.000 description 12
- 239000004745 nonwoven fabric Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 239000002608 ionic liquid Substances 0.000 description 8
- 238000010128 melt processing Methods 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 238000009825 accumulation Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229920001410 Microfiber Polymers 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000003658 microfiber Substances 0.000 description 5
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 102100021669 Stromal cell-derived factor 1 Human genes 0.000 description 4
- 101710088580 Stromal cell-derived factor 1 Proteins 0.000 description 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
- 238000000137 annealing Methods 0.000 description 4
- 238000000071 blow moulding Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- PUZYNDBTWXJXKN-UHFFFAOYSA-M tetraethylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC[N+](CC)(CC)CC PUZYNDBTWXJXKN-UHFFFAOYSA-M 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- KZJUHXVCAHXJLR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KZJUHXVCAHXJLR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910013528 LiN(SO2 CF3)2 Inorganic materials 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- GHAVIAOYNKGAPG-UHFFFAOYSA-N [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.C[N+](C)(C)C Chemical compound [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.C[N+](C)(C)C GHAVIAOYNKGAPG-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- CFAPFDTWIGBCQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;tetrabutylazanium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC CFAPFDTWIGBCQK-UHFFFAOYSA-N 0.000 description 3
- PBVQLVFWBBDZNU-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F PBVQLVFWBBDZNU-UHFFFAOYSA-N 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920001643 poly(ether ketone) Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]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 YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 2
- POKOASTYJWUQJG-UHFFFAOYSA-M 1-butylpyridin-1-ium;chloride Chemical compound [Cl-].CCCC[N+]1=CC=CC=C1 POKOASTYJWUQJG-UHFFFAOYSA-M 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- CHJYKNDQMVDBKS-UHFFFAOYSA-N 4,4,4-trifluorobutane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCC(F)(F)F CHJYKNDQMVDBKS-UHFFFAOYSA-N 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000004425 Makrolon Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JUGOREOARAHOCO-UHFFFAOYSA-M acetylcholine chloride Chemical compound [Cl-].CC(=O)OCC[N+](C)(C)C JUGOREOARAHOCO-UHFFFAOYSA-M 0.000 description 2
- 229960004266 acetylcholine chloride Drugs 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UQWLFOMXECTXNQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F UQWLFOMXECTXNQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 239000004750 melt-blown nonwoven Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920005615 natural polymer Polymers 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000011087 paperboard Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- NLDFCSJIMQJDGQ-UHFFFAOYSA-M 1-butyl-2-ethylpyrazol-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+]1=CC=CN1CC NLDFCSJIMQJDGQ-UHFFFAOYSA-M 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- BOFPDEISADDIGX-UHFFFAOYSA-N 1-ethyl-2-methylpyrazol-2-ium Chemical compound CCN1C=CC=[N+]1C BOFPDEISADDIGX-UHFFFAOYSA-N 0.000 description 1
- ZPTRYWVRCNOTAS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;trifluoromethanesulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)F ZPTRYWVRCNOTAS-UHFFFAOYSA-M 0.000 description 1
- MVUOWNJFAFRIJV-UHFFFAOYSA-N 1-ethyl-3-methylimidazol-3-ium;trifluoromethylsulfonyliminomethylideneazanide Chemical compound CC[N+]=1C=CN(C)C=1.FC(F)(F)S(=O)(=O)[N-]C#N MVUOWNJFAFRIJV-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- BUAUZIKFYHTSRC-UHFFFAOYSA-M 1-hexadecylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 BUAUZIKFYHTSRC-UHFFFAOYSA-M 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 1
- TYTPXMXMCVKLPR-UHFFFAOYSA-N 1H-imidazol-1-ium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound FC(C(C(C(S(=O)(=O)[O-])(F)F)(F)F)(F)F)(F)F.[NH2+]1C=NC=C1 TYTPXMXMCVKLPR-UHFFFAOYSA-N 0.000 description 1
- JNJFONBBNLVENC-UHFFFAOYSA-N 1h-imidazole;trifluoromethanesulfonic acid Chemical compound C1=CNC=N1.OS(=O)(=O)C(F)(F)F JNJFONBBNLVENC-UHFFFAOYSA-N 0.000 description 1
- UDFNGYSINJNFCO-UHFFFAOYSA-N 2,4,5-trifluoro-1-(1,1,2,2,2-pentafluoroethyl)-3-(trifluoromethyl)imidazol-3-ium Chemical compound FC1=C(F)[N+](C(F)(F)F)=C(F)N1C(F)(F)C(F)(F)F UDFNGYSINJNFCO-UHFFFAOYSA-N 0.000 description 1
- UINDRJHZBAGQFD-UHFFFAOYSA-O 2-ethyl-3-methyl-1h-imidazol-3-ium Chemical compound CCC1=[NH+]C=CN1C UINDRJHZBAGQFD-UHFFFAOYSA-O 0.000 description 1
- CGBIQADMUFXPTP-UHFFFAOYSA-N 2-ethyl-3-methyl-1h-imidazol-3-ium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound CCC=1NC=C[N+]=1C.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CGBIQADMUFXPTP-UHFFFAOYSA-N 0.000 description 1
- ZLMDEDTUVUQBMM-UHFFFAOYSA-N 2-ethyl-3-methyl-1h-imidazol-3-ium;trifluoromethanesulfonate Chemical compound CCC=1NC=C[N+]=1C.[O-]S(=O)(=O)C(F)(F)F ZLMDEDTUVUQBMM-UHFFFAOYSA-N 0.000 description 1
- OCAPHIRVDIMADR-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-octylazanium Chemical compound CCCCCCCC[N+](C)(C)CCO OCAPHIRVDIMADR-UHFFFAOYSA-N 0.000 description 1
- DVSPHWCZXKPJEQ-UHFFFAOYSA-N 2-methoxyethyl(trimethyl)azanium Chemical compound COCC[N+](C)(C)C DVSPHWCZXKPJEQ-UHFFFAOYSA-N 0.000 description 1
- OKTPHJDYPJYNCI-UHFFFAOYSA-N 3-ethyl-1,3-oxazol-3-ium Chemical compound CC[N+]=1C=COC=1 OKTPHJDYPJYNCI-UHFFFAOYSA-N 0.000 description 1
- XDSCQDZFYBUCQY-UHFFFAOYSA-N 3-ethyl-1,3-thiazol-3-ium Chemical compound CC[N+]=1C=CSC=1 XDSCQDZFYBUCQY-UHFFFAOYSA-N 0.000 description 1
- NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- 229920002574 CR-39 Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PJZCDIDROVMMKV-UHFFFAOYSA-M FC(CCCS(=O)(=O)[O-])(F)F.C(C)OCC[N+](C)(C)C Chemical compound FC(CCCS(=O)(=O)[O-])(F)F.C(C)OCC[N+](C)(C)C PJZCDIDROVMMKV-UHFFFAOYSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229920001079 Thiokol (polymer) Polymers 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- XOZHIVUWCICHSQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XOZHIVUWCICHSQ-UHFFFAOYSA-N 0.000 description 1
- LUWJQOLQUXTUGM-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane;1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C.FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F LUWJQOLQUXTUGM-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- WXCZUWHSJWOTRV-UHFFFAOYSA-N but-1-ene;ethene Chemical compound C=C.CCC=C WXCZUWHSJWOTRV-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- FITUNPSTVBUGAH-UHFFFAOYSA-N chloroform;heptane Chemical compound ClC(Cl)Cl.CCCCCCC FITUNPSTVBUGAH-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VWYHCWVXCWCOPV-UHFFFAOYSA-L dilithium trifluoromethanesulfonate Chemical compound [Li+].[Li+].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F VWYHCWVXCWCOPV-UHFFFAOYSA-L 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000011521 glass Substances 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
- 229920006258 high performance thermoplastic Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- XVCUGNWRDDNCRD-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [Li+].[O-]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 XVCUGNWRDDNCRD-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005525 methide group Chemical group 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229950003332 perflubutane Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-O propan-1-aminium Chemical compound CCC[NH3+] WGYKZJWCGVVSQN-UHFFFAOYSA-O 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0075—Antistatics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/412,850 | 1999-10-06 | ||
| US09/412,850 US6372829B1 (en) | 1999-10-06 | 1999-10-06 | Antistatic composition |
| PCT/US2000/006597 WO2001025326A1 (en) | 1999-10-06 | 2000-03-14 | Antistatic composition |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012270411A Division JP5395248B2 (ja) | 1999-10-06 | 2012-12-11 | イオン性塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003511505A JP2003511505A (ja) | 2003-03-25 |
| JP2003511505A5 JP2003511505A5 (enExample) | 2007-05-10 |
| JP5412629B2 true JP5412629B2 (ja) | 2014-02-12 |
Family
ID=23634751
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001528488A Expired - Fee Related JP5412629B2 (ja) | 1999-10-06 | 2000-03-14 | 帯電防止組成物 |
| JP2012270411A Expired - Fee Related JP5395248B2 (ja) | 1999-10-06 | 2012-12-11 | イオン性塩 |
| JP2013171136A Expired - Fee Related JP5643401B2 (ja) | 1999-10-06 | 2013-08-21 | 帯電防止組成物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012270411A Expired - Fee Related JP5395248B2 (ja) | 1999-10-06 | 2012-12-11 | イオン性塩 |
| JP2013171136A Expired - Fee Related JP5643401B2 (ja) | 1999-10-06 | 2013-08-21 | 帯電防止組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6372829B1 (enExample) |
| EP (1) | EP1232206B1 (enExample) |
| JP (3) | JP5412629B2 (enExample) |
| KR (1) | KR100755813B1 (enExample) |
| AU (1) | AU3743500A (enExample) |
| CA (1) | CA2385476C (enExample) |
| DE (1) | DE60018597T2 (enExample) |
| TW (1) | TWI230176B (enExample) |
| WO (1) | WO2001025326A1 (enExample) |
Families Citing this family (131)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6372829B1 (en) * | 1999-10-06 | 2002-04-16 | 3M Innovative Properties Company | Antistatic composition |
| GB9928290D0 (en) * | 1999-12-01 | 2000-01-26 | Univ Belfast | Process for preparing ambient temperature ionic liquids |
| US6592988B1 (en) * | 1999-12-29 | 2003-07-15 | 3M Innovative Properties Company | Water-and oil-repellent, antistatic composition |
| AU2001262242A1 (en) * | 2000-05-12 | 2001-11-20 | Bayer Aktiengesellschaft | Antistatic agent |
| JP2002124108A (ja) * | 2000-10-17 | 2002-04-26 | Koito Mfg Co Ltd | 車両用灯具 |
| US20030054172A1 (en) * | 2001-05-10 | 2003-03-20 | 3M Innovative Properties Company | Polyoxyalkylene ammonium salts and their use as antistatic agents |
| US6436619B1 (en) * | 2001-05-11 | 2002-08-20 | Eastman Kodak Company | Conductive and roughening layer |
| JP4677134B2 (ja) * | 2001-07-27 | 2011-04-27 | 株式会社イノアックコーポレーション | 帯電防止シート |
| CN100351294C (zh) * | 2001-08-02 | 2007-11-28 | 3M创新有限公司 | 光学透明和抗静电的压敏粘合剂 |
| US6740413B2 (en) * | 2001-11-05 | 2004-05-25 | 3M Innovative Properties Company | Antistatic compositions |
| US6924329B2 (en) * | 2001-11-05 | 2005-08-02 | 3M Innovative Properties Company | Water- and oil-repellent, antistatic compositions |
| US6531270B1 (en) * | 2001-11-21 | 2003-03-11 | Eastman Kodak Company | Ionic liquids as coupler solvents in photothermographic systems |
| US6531273B1 (en) * | 2001-11-21 | 2003-03-11 | Eastman Kodak Company | Dispersions of ionic liquids for photothermographic systems and methods of making such systems |
| US6586166B1 (en) | 2001-11-21 | 2003-07-01 | Eastman Kodak Company | Ionic liquids as addenda in photothermographic systems |
| AU2003237797B2 (en) | 2002-04-05 | 2009-02-26 | University Of South Alabama | Functionalized ionic liquids, and methods of use thereof |
| US6580006B1 (en) | 2002-05-02 | 2003-06-17 | 3M Innovative Properties Company | Catalytic process for preparing perfluoroethanesulfonyl fluoride and/or perfluorodiethylsulfone |
| US20040077519A1 (en) * | 2002-06-28 | 2004-04-22 | The Procter & Gamble Co. | Ionic liquid based products and method of using the same |
| US6900257B2 (en) * | 2002-08-06 | 2005-05-31 | General Electric Company | Antistatic agents and polymer compositions derived therefrom |
| US6841598B2 (en) * | 2002-08-16 | 2005-01-11 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
| US7320947B2 (en) * | 2002-09-16 | 2008-01-22 | Milliken & Company | Static dissipative textile and method for producing the same |
| AU2003287507B2 (en) * | 2002-11-04 | 2008-05-01 | Solutia Inc. | Functional fluid compositions containing erosion inhibitors |
| JP4625255B2 (ja) * | 2002-12-27 | 2011-02-02 | 三洋化成工業株式会社 | 帯電防止剤および帯電防止性樹脂組成物 |
| JP4615855B2 (ja) * | 2003-01-15 | 2011-01-19 | 住友ゴム工業株式会社 | 制電性ポリマー組成物からなる成形品 |
| WO2004078898A1 (ja) * | 2003-03-06 | 2004-09-16 | Tokuyama Corporation | 帯電防止性洗浄剤 |
| JP4519487B2 (ja) * | 2003-03-06 | 2010-08-04 | 株式会社トクヤマ | 洗浄用組成物 |
| US6765112B1 (en) * | 2003-03-25 | 2004-07-20 | E. I. Du Pont De Nemours And Company | Fluorinated onium salts |
| WO2005040458A1 (en) * | 2003-10-23 | 2005-05-06 | Transfert Plus, S.E.C. | Electrode having a cos layer thereon, process of preparation, and uses thereof |
| US7220792B2 (en) | 2003-12-30 | 2007-05-22 | General Electric Company | Water resistant permanent antistatic thermoplastic composition |
| US7731881B2 (en) | 2003-12-30 | 2010-06-08 | Sabic Innovative Plastics Ip B.V. | Method for making fog resistant thermoplastic articles and articles made therefrom |
| US7094861B2 (en) | 2003-12-30 | 2006-08-22 | General Electric Company | Thermoplastic composition containing polymeric anti-static salt, method of making, and use thereof |
| JP5384279B2 (ja) * | 2004-03-08 | 2014-01-08 | 日東電工株式会社 | 粘着剤組成物、粘着シート類及び表面保護フィルム |
| JP5019552B2 (ja) * | 2004-05-26 | 2012-09-05 | 日東電工株式会社 | 粘着型光学部材 |
| ATE484559T1 (de) * | 2004-03-08 | 2010-10-15 | Nitto Denko Corp | Druckemfindliche klebstoffzusammensetzung, druckempfindliche klebefolie und oberflächenschutzfolie |
| JP5437192B2 (ja) * | 2004-05-26 | 2014-03-12 | 日東電工株式会社 | 粘着型光学部材 |
| TWI388640B (zh) * | 2004-06-01 | 2013-03-11 | Nitto Denko Corp | 壓敏黏合劑組成物、壓敏黏合片及表面保護膜 |
| TWI387629B (zh) | 2004-07-26 | 2013-03-01 | Nitto Denko Corp | 壓感黏合劑組成物、壓感黏合片及表面保護膜 |
| JP4559800B2 (ja) * | 2004-08-30 | 2010-10-13 | 株式会社トクヤマ | 電気・電子部品用の洗浄剤 |
| US7776810B2 (en) * | 2004-11-01 | 2010-08-17 | The Procter & Gamble Company | Compositions containing ionic liquid actives |
| US20060094616A1 (en) * | 2004-11-01 | 2006-05-04 | Hecht Stacie E | Ionic liquids derived from surfactants |
| US20060090271A1 (en) * | 2004-11-01 | 2006-05-04 | Price Kenneth N | Processes for modifying textiles using ionic liquids |
| US20060090777A1 (en) * | 2004-11-01 | 2006-05-04 | Hecht Stacie E | Multiphase cleaning compositions having ionic liquid phase |
| US7737102B2 (en) | 2004-11-01 | 2010-06-15 | The Procter & Gamble Company | Ionic liquids derived from functionalized anionic surfactants |
| US7939485B2 (en) * | 2004-11-01 | 2011-05-10 | The Procter & Gamble Company | Benefit agent delivery system comprising ionic liquid |
| JP2006137106A (ja) * | 2004-11-12 | 2006-06-01 | Nitto Denko Corp | 溶剤含有物除去用粘着シート |
| JP4888680B2 (ja) * | 2004-11-15 | 2012-02-29 | パイオトレック株式会社 | 帯電防止剤およびその使用方法 |
| JP4767561B2 (ja) * | 2004-12-13 | 2011-09-07 | 広栄化学工業株式会社 | 樹脂組成物用帯電防止剤 |
| US7786065B2 (en) * | 2005-02-18 | 2010-08-31 | The Procter & Gamble Company | Ionic liquids derived from peracid anions |
| JP2006232882A (ja) * | 2005-02-22 | 2006-09-07 | Nitto Denko Corp | 粘着剤組成物、粘着シート類および両面粘着テープ |
| JP4358190B2 (ja) * | 2005-03-16 | 2009-11-04 | 日東電工株式会社 | 粘着剤組成物、粘着シート類および表面保護フィルム |
| WO2006123638A1 (ja) * | 2005-05-20 | 2006-11-23 | Nitto Denko Corporation | 粘着剤組成物、粘着シートおよび表面保護フィルム |
| KR100812507B1 (ko) * | 2005-08-19 | 2008-03-11 | 주식회사 엘지화학 | 아크릴계 점착제 조성물 |
| JP2007063298A (ja) * | 2005-08-29 | 2007-03-15 | Nippon Carbide Ind Co Inc | 粘着剤溶液組成物及び表面保護フィルム |
| EP1939263B1 (en) * | 2005-09-05 | 2012-08-01 | Nitto Denko Corporation | Adhesive composition, adhesive sheet, and surface protective film |
| JP4851753B2 (ja) * | 2005-09-05 | 2012-01-11 | 日東電工株式会社 | 粘着剤組成物および粘着シート類 |
| US20090110849A1 (en) * | 2005-09-20 | 2009-04-30 | Soken Chemical & Engineering Co., Ltd. | Adhesive Composition for Polarizing Plate and Polarizing Plate with Adhesive Layer |
| DE102006000651A1 (de) * | 2006-01-03 | 2007-07-12 | Degussa Gmbh | Präparation aus Ionischen Flüssigkeiten und Harzen |
| KR100753959B1 (ko) * | 2006-01-12 | 2007-08-31 | 에이펫(주) | 기판 건조장치를 이용한 기판 건조방법 |
| PT1984438E (pt) * | 2006-02-07 | 2010-05-17 | Basf Se | Poliuretano antiestático |
| EP1985661B1 (en) * | 2006-02-13 | 2012-08-01 | Toray Industries, Inc. | Antistatic thermoplastic resin composition and molded article made from same |
| KR100845687B1 (ko) * | 2006-08-22 | 2008-07-11 | 임성혁 | 코팅용 대전방지 조성물, 내첨용 대전 방지 조성물 및 이를이용한 기능성 대전방지 제품 |
| US20080070030A1 (en) * | 2006-09-15 | 2008-03-20 | 3M Innovative Properties Company | Static dissipative articles |
| US20080069887A1 (en) * | 2006-09-15 | 2008-03-20 | 3M Innovative Properties Company | Method for nanoparticle surface modification |
| JP5224693B2 (ja) * | 2007-01-30 | 2013-07-03 | 伊藤光学工業株式会社 | ハードコーティング組成物 |
| TW200909549A (en) * | 2007-04-13 | 2009-03-01 | 3M Innovative Properties Co | Antistatic optically clear pressure sensitive adhesive |
| JP2008297432A (ja) * | 2007-05-31 | 2008-12-11 | Asahi Glass Co Ltd | 含フッ素重合体組成物 |
| JP5769353B2 (ja) * | 2007-07-13 | 2015-08-26 | チェイル インダストリーズ インコーポレイテッド | 粘着剤組成物及び光学部材 |
| KR100946157B1 (ko) * | 2007-11-15 | 2010-03-05 | 광 석 서 | 이온성 액체를 포함한 자외선 경화형 대전방지 코팅 조성물 |
| EP2254962B1 (en) * | 2008-03-07 | 2016-04-27 | 3M Innovative Properties Company | Antistatic block copolymer pressure sensitive adhesives and articles |
| WO2009126532A2 (en) * | 2008-04-11 | 2009-10-15 | 3M Innovative Properties Company | Transparent adhesive sheet and image display device including the same |
| WO2009130873A1 (ja) * | 2008-04-21 | 2009-10-29 | 日本カーリット株式会社 | ハイドロアルカンスルホネートおよびその用途 |
| DE102008021271A1 (de) * | 2008-04-29 | 2010-01-28 | Merck Patent Gmbh | Reaktive ionische Flüssigkeiten |
| JP5126840B2 (ja) * | 2008-05-22 | 2013-01-23 | 大和製罐株式会社 | 帯電防止性樹脂組成物およびそれからなるフィルム |
| KR20110028600A (ko) * | 2008-06-03 | 2011-03-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리알킬 질소 또는 인 오늄 플루오로알킬 설포닐 염을 포함하는 미세구조체 |
| US20100028564A1 (en) * | 2008-07-29 | 2010-02-04 | Ming Cheng | Antistatic optical constructions having optically-transmissive adhesives |
| EP2157133A1 (de) | 2008-08-19 | 2010-02-24 | Bayer MaterialScience AG | Folien mit verbesserten Eigenschaften |
| EP2168783A1 (de) | 2008-09-24 | 2010-03-31 | Bayer MaterialScience AG | Verwendung einer Kunststoff-Folie im Farblaserdruck |
| EP2172336A1 (de) * | 2008-09-24 | 2010-04-07 | Bayer MaterialScience AG | Fälschungssichere Sicherheitsmerkmale in Sicherheits- oder Wertdokumenten |
| SG172204A1 (en) | 2008-12-30 | 2011-07-28 | 3M Innovative Properties Co | Antireflective articles and methods of making the same |
| JP5940809B2 (ja) | 2008-12-30 | 2016-06-29 | スリーエム イノベイティブ プロパティズ カンパニー | ナノ構造化物品及びナノ構造化物品の作製方法 |
| FR2941700B1 (fr) * | 2009-02-02 | 2012-03-16 | Arkema France | Procede de synthese d'un alliage de copolymere a blocs presentant des proprietes antistatiques ameliorees. |
| TW201103885A (en) * | 2009-07-22 | 2011-02-01 | Daxon Technology Inc | Antistatic ionic compound, oligomer thereof, copolymer thereof, and pressure-sensitive adhesive composition |
| EP2470929B1 (en) * | 2009-08-28 | 2018-06-27 | 3M Innovative Properties Company | Optical device with antistatic coating |
| EP2470509A2 (en) | 2009-08-28 | 2012-07-04 | 3M Innovative Properties Company | Compositions and articles comprising polymerizable ionic liquid mixture, and methods of curing |
| KR101783062B1 (ko) | 2009-08-28 | 2017-09-28 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 다작용성 양이온을 포함하는 중합성 이온성 액체 및 정전기 방지 코팅 |
| EP2493941B1 (en) | 2009-10-30 | 2017-09-20 | 3M Innovative Properties Company | Optical device with antistatic property |
| KR101257144B1 (ko) | 2009-12-08 | 2013-04-22 | 코오롱인더스트리 주식회사 | 광확산판,이의 제조방법,이를 구비한 백라이트 장치 및 액정표시장치 |
| RU2012131166A (ru) | 2009-12-22 | 2014-01-27 | 3М Инновейтив Пропертиз Компани | Отверждаемые стоматологические композиции и изделия, содержащие полимеризуемые ионные жидкости |
| JP2013521534A (ja) | 2010-03-03 | 2013-06-10 | スリーエム イノベイティブ プロパティズ カンパニー | ナノ構造化表面を有するコーティングされた偏光子、及びこれを作製する方法 |
| KR20130037668A (ko) | 2010-03-03 | 2013-04-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 나노구조 표면을 갖는 복합 다층 구조체 |
| JP5607442B2 (ja) * | 2010-07-09 | 2014-10-15 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー系粘接着性組成物 |
| CN103563155B (zh) | 2011-06-07 | 2017-07-21 | 3M创新有限公司 | 包含碳氟化合物电解质添加剂的锂离子电化学电池 |
| JP5882667B2 (ja) * | 2011-10-19 | 2016-03-09 | 日東電工株式会社 | 水分散型アクリル系粘着剤組成物、及び粘着シート |
| US20150068635A1 (en) * | 2012-01-27 | 2015-03-12 | Titeflex Corporation | Energy dissipative tubes |
| CN102660103B (zh) * | 2012-03-13 | 2014-09-03 | 大连路阳科技开发有限公司 | 一种抗静电聚醚醚酮复合材料及其制备方法 |
| CN102602080B (zh) * | 2012-03-13 | 2015-04-08 | 大连路阳科技开发有限公司 | 一种钢基聚醚醚酮复合板及其制备方法 |
| JP2013226806A (ja) * | 2012-03-30 | 2013-11-07 | Dainippon Printing Co Ltd | 熱転写シート |
| WO2013191762A1 (en) | 2012-06-21 | 2013-12-27 | 3M Innovative Properties Company | A static dissipating laser engravable film |
| WO2014062536A1 (en) * | 2012-10-16 | 2014-04-24 | Ticona Llc | Antistatic liquid crystalline polymer composition |
| JP2014098053A (ja) * | 2012-11-13 | 2014-05-29 | Nippon Synthetic Chem Ind Co Ltd:The | 合成潤滑剤 |
| JP2014143415A (ja) | 2012-12-31 | 2014-08-07 | Rohm & Haas Electronic Materials Llc | イオン注入法 |
| JP6328931B2 (ja) | 2012-12-31 | 2018-05-23 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | フォトレジストパターントリミング方法 |
| CN105189641B (zh) | 2013-05-02 | 2018-02-23 | 3M创新有限公司 | 部分氟化的弹性体及其制备和使用方法 |
| JP5457596B1 (ja) * | 2013-07-19 | 2014-04-02 | 日本乳化剤株式会社 | Abs樹脂組成物用帯電防止剤およびabs樹脂組成物 |
| EP2853560A1 (de) | 2013-09-27 | 2015-04-01 | Bayer MaterialScience AG | Polycarbonatzusammensetzung mit verbesserten elektrischen Eigenschaften enthaltend Kohlenstoffnanoröhrchen |
| EP2853559A1 (de) | 2013-09-27 | 2015-04-01 | Bayer MaterialScience AG | Polycarbonatzusammensetzung mit verbesserten elektrischen Eigenschaften enthaltend Ruß |
| KR102346806B1 (ko) | 2013-12-30 | 2022-01-04 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 포토레지스트 패턴 트리밍 조성물 및 방법 |
| JP6327704B2 (ja) * | 2014-05-20 | 2018-05-23 | 日東電工株式会社 | 表面保護フィルムの製造方法 |
| JP6327703B2 (ja) * | 2014-05-20 | 2018-05-23 | 日東電工株式会社 | 表面保護フィルム |
| EP3233947A1 (en) | 2014-12-16 | 2017-10-25 | 3M Innovative Properties Company | Antistatic polymers and methods of making the same |
| CN107001252B (zh) * | 2014-12-16 | 2019-04-26 | 3M创新有限公司 | 离子型二醇抗静电聚氨酯及其制备方法 |
| WO2016099948A1 (en) | 2014-12-16 | 2016-06-23 | 3M Innovative Properties Company | Antistatic polymers and methods of making the same |
| CN105985277A (zh) * | 2015-02-05 | 2016-10-05 | 江苏国泰超威新材料有限公司 | 一种离子液体的制备方法及其应用 |
| JP2018081942A (ja) * | 2015-03-20 | 2018-05-24 | 株式会社ブリヂストン | 太陽電池用封止材及びこれを用いた太陽電池モジュール |
| JP6529120B6 (ja) * | 2015-05-07 | 2019-07-17 | 大和製罐株式会社 | 帯電防止性樹脂組成物およびそれからなるフィルム |
| JP6797346B2 (ja) * | 2015-12-22 | 2020-12-09 | Dic株式会社 | ポリアリーレンスルフィド樹脂組成物、成形品および製造方法 |
| JP6816431B2 (ja) * | 2016-09-29 | 2021-01-20 | 東レ株式会社 | イオン塩、それを含有する熱可塑性樹脂組成物およびその製造方法 |
| JP2018165315A (ja) * | 2017-03-28 | 2018-10-25 | 三菱エンジニアリングプラスチックス株式会社 | 芳香族ポリカーボネート樹脂組成物及びその成形品 |
| JP6952497B2 (ja) * | 2017-05-31 | 2021-10-20 | 日東電工株式会社 | 粘着剤組成物、表面保護シート、及び、光学部材 |
| KR102164253B1 (ko) * | 2017-10-18 | 2020-10-12 | 주식회사 엘지화학 | 그래프트 공중합체 복합체의 제조방법, 그래프트 공중합체 복합체 및 이를 포함하는 열가소성 수지 조성물 |
| WO2019147261A1 (en) | 2018-01-26 | 2019-08-01 | Hewlett-Packard Development Company, L.P. | Three-dimensional printing |
| US11667766B2 (en) | 2018-01-26 | 2023-06-06 | Hewlett-Packard Development Company, L.P. | Three-dimensional printing |
| WO2020122055A1 (ja) * | 2018-12-14 | 2020-06-18 | 三菱瓦斯化学株式会社 | 樹脂組成物、樹脂シート、セキュリティカードおよび樹脂組成物の製造方法 |
| KR102190762B1 (ko) * | 2019-01-18 | 2020-12-16 | 율촌화학 주식회사 | 대전방지 조성물 및 이를 포함하는 이형필름 |
| CN114746488A (zh) | 2019-12-12 | 2022-07-12 | 科思创知识产权两合公司 | 具有特殊性质的膜 |
| JP7440306B2 (ja) * | 2020-03-10 | 2024-02-28 | 帝人株式会社 | ポリカーボネート樹脂組成物及びその成形体 |
| JP6871450B2 (ja) * | 2020-03-12 | 2021-05-12 | 藤森工業株式会社 | 粘着剤組成物、及び表面保護フィルム |
| JP2022128971A (ja) * | 2021-02-24 | 2022-09-05 | 帝人株式会社 | 樹脂組成物およびその成形品 |
| CN113980171B (zh) * | 2021-12-01 | 2022-10-11 | 香港中文大学(深圳) | 遇湿变硬的高分子材料及其制备方法和用途 |
| KR102806427B1 (ko) * | 2022-01-26 | 2025-05-21 | 대흥하이텍 주식회사 | 대전 방지용 조성물 및 이를 이용한 대전 방지막 형성 방법 |
| CN115141480A (zh) * | 2022-06-29 | 2022-10-04 | 上海朗亿功能材料有限公司 | 一种抗静电热塑性聚氨酯及其制备方法和应用 |
| WO2025133762A1 (en) | 2023-12-21 | 2025-06-26 | 3M Innovative Properties Company | Retroreflective article comprising a retroreflective layer and an antireflective layer, kits, and methods thereof |
Family Cites Families (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2732398A (en) | 1953-01-29 | 1956-01-24 | cafiicfzsojk | |
| US3476753A (en) | 1965-05-03 | 1969-11-04 | Minnesota Mining & Mfg | Tertiaryamino perfluoro alkylene sulfonic acid fluorides |
| SU406849A1 (ru) | 1972-02-15 | 1973-11-21 | О П ЙПГЖ W4t ИЗОБРЕТЕНИЯ | |
| SU427962A1 (ru) | 1972-06-09 | 1974-05-15 | Способ уменьшения электризуемости термопластичных полимеров | |
| SU448199A1 (ru) | 1973-03-16 | 1974-10-30 | Предприятие П/Я В-2913 | Способ понижени электризуемости термопластичных полимеров |
| SU446522A1 (ru) | 1973-03-16 | 1974-10-15 | Предприятие П/Я В-2913 | Способ антистатической обработки термопластичных полимеров |
| JPS5315747B2 (enExample) | 1973-08-28 | 1978-05-26 | ||
| DE2506726C2 (de) | 1975-02-18 | 1982-06-16 | Bayer Ag, 5090 Leverkusen | Verwendung von Perfluoralkansulfonamiden und/oder Ammoniumsalzen von Perfluoralkansulfonsäuren und/oder Cyclimmoniumsalzen von Perfluoralkansulfonsäuren als Entformungsmittel |
| CA1078107A (en) | 1975-08-04 | 1980-05-27 | Kimberly-Clark Corporation | Anti-static composition |
| JPS5315747A (en) | 1976-07-28 | 1978-02-14 | Toshiba Corp | Electonic gun |
| US4144367A (en) | 1977-05-09 | 1979-03-13 | Minnesota Mining And Manufacturing Company | Carpet-treating compositions |
| US4266015A (en) | 1977-09-13 | 1981-05-05 | Minnesota Mining And Manufacturing Company | Light sensitive materials with fluorinated polymer antistats |
| US4328280A (en) | 1978-05-15 | 1982-05-04 | Minnesota Mining And Manufacturing Company | Suppression of spark discharges from negatively triboelectrically charged surfaces |
| US4313978A (en) | 1978-12-20 | 1982-02-02 | Minnesota Mining And Manufacturing Company | Antistatic compositions and treatment |
| SU749081A1 (ru) | 1979-01-09 | 1983-12-15 | Предприятие П/Я В-2913 | Способ антистатической обработки термопластичных полимеров |
| SU749084A1 (ru) | 1979-01-09 | 1983-12-15 | Предприятие П/Я В-2913 | Способ антистатической обработки термопластичных полимеров |
| SU854949A1 (ru) | 1979-01-09 | 1981-08-15 | Предприятие П/Я В-2913 | Способ обработки термопластичных полимеров |
| JPS55149938A (en) | 1979-05-11 | 1980-11-21 | Konishiroku Photo Ind Co Ltd | Photographic coating fluid |
| DE3034988A1 (de) | 1980-09-17 | 1982-04-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung elektrisch leitfaehiger polyaromaten und deren verwendung in der elektrotechnik und zur antistatischen ausruestung von kunststoffen |
| US4335201A (en) | 1980-11-24 | 1982-06-15 | Eastman Kodak Company | Antistatic compositions and elements containing same |
| US4472286A (en) | 1981-01-09 | 1984-09-18 | Ciba-Geigy Corporation | Perfluoroalkyl anion/perfluoroalkyl cation ion pair complexes |
| US4387222A (en) | 1981-01-30 | 1983-06-07 | Minnesota Mining And Manufacturing Company | Cyclic perfluoroaliphaticdisulfonimides |
| US4393159A (en) | 1981-12-04 | 1983-07-12 | Bengal, Inc. | Anti-static material and method of making the material |
| US4439505A (en) | 1982-01-21 | 1984-03-27 | Eastman Kodak Company | Electrical conductive compositions |
| US4478922A (en) | 1982-01-21 | 1984-10-23 | Eastman Kodak Company | Electrically conductive compositions |
| FR2527602A1 (fr) | 1982-06-01 | 1983-12-02 | Anvar | Bis perhalogenoacyl- ou sulfonyl- imidures de metaux alcalins, leurs solutions solides avec des matieres plastiques et leur application a la constitution d'elements conducteurs pour des generateurs electrochimiques |
| US4570197A (en) | 1983-01-03 | 1986-02-11 | Minnesota Mining & Manufacturing Company | Static reduction in magnetic recording cassettes |
| JPS60221442A (ja) | 1984-04-18 | 1985-11-06 | Kao Corp | 帯電防止剤 |
| US4582781A (en) | 1984-08-01 | 1986-04-15 | Eastman Kodak Company | Antistatic compositions comprising polymerized oxyalkylene monomers and an inorganic tetrafluoroborate, perfluoroalkyl carboxylate, hexafluorophosphate or perfluoroalkylsulfonate salt |
| JPH0618863B2 (ja) | 1986-03-28 | 1994-03-16 | 三菱化成株式会社 | 有機半導体 |
| US4687222A (en) * | 1986-04-28 | 1987-08-18 | Chalmers Wallace G | Tandem axle air suspension |
| JPH0689323B2 (ja) | 1986-06-13 | 1994-11-09 | 第一工業製薬株式会社 | 制電加工剤 |
| US5025052A (en) | 1986-09-12 | 1991-06-18 | Minnesota Mining And Manufacturing Company | Fluorochemical oxazolidinones |
| JPH0690447B2 (ja) | 1986-09-12 | 1994-11-14 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
| US5099026A (en) | 1986-09-12 | 1992-03-24 | Crater Davis H | Fluorochemical oxazolidinones |
| JPS6371923A (ja) | 1986-09-13 | 1988-04-01 | Sony Corp | 磁気記録媒体 |
| US4939204A (en) | 1986-12-05 | 1990-07-03 | The Dow Chemical Company | Process for preparing static dissipative linear segmented polyurethanes |
| JPS63295667A (ja) | 1987-05-27 | 1988-12-02 | Showa Electric Wire & Cable Co Ltd | 透明導電性樹脂組成物 |
| JPH07103228B2 (ja) | 1987-06-09 | 1995-11-08 | 日立電線株式会社 | 導電性フィルムの製造方法 |
| JPS6475534A (en) | 1987-09-17 | 1989-03-22 | Nissha Printing | Production of electrically conductive composite material |
| US4812381A (en) * | 1987-12-17 | 1989-03-14 | Eastman Kodak Company | Electrostatographic toners and developers containing new charge-control agents |
| US4834921A (en) * | 1987-12-17 | 1989-05-30 | Eastman Kodak Company | Quaternary ammonium salts |
| US4873020A (en) | 1988-10-04 | 1989-10-10 | Minnesota Mining And Manufacturing Company | Fluorochemical surfactants and process for preparing same |
| US5043195A (en) | 1988-10-28 | 1991-08-27 | Minnesota Mining & Manufacturing Company | Static shielding film |
| US4904825A (en) | 1988-11-08 | 1990-02-27 | Ppg Industries, Inc. | Quaternary ammonium antistatic compounds |
| IT1227930B (it) | 1988-11-25 | 1991-05-14 | Minnesota Mining & Mfg | Materiali fotografici agli alogenuri d'argento sensibili alla luce. |
| FR2645533B1 (fr) | 1989-04-06 | 1991-07-12 | Centre Nat Rech Scient | Procede de synthese de sulfonylimidures |
| FR2645534B1 (fr) | 1989-04-06 | 1991-07-12 | Centre Nat Rech Scient | Procede de preparation de sulfonylmethanes et de leurs derives |
| CA2022205A1 (en) | 1989-08-24 | 1991-02-25 | Charles G. Koethe | Antistatic coating for brush elements |
| JPH03192186A (ja) * | 1989-12-21 | 1991-08-22 | Toho Chem Ind Co Ltd | 高性能表面塗布型帯電防止剤 |
| US5273840A (en) | 1990-08-01 | 1993-12-28 | Covalent Associates Incorporated | Methide salts, formulations, electrolytes and batteries formed therefrom |
| US5149576A (en) | 1990-11-26 | 1992-09-22 | Kimberly-Clark Corporation | Multilayer nonwoven laminiferous structure |
| US5145727A (en) | 1990-11-26 | 1992-09-08 | Kimberly-Clark Corporation | Multilayer nonwoven composite structure |
| US5244951A (en) | 1991-05-02 | 1993-09-14 | Minnesota Mining And Manufacturing Company | Durably hydrophilic, thermoplastic fiber |
| CA2071124A1 (en) * | 1991-06-19 | 1992-12-20 | Utami Yonemura | Resin article having anti-static property |
| US5176943A (en) | 1991-07-09 | 1993-01-05 | Minnesota Mining And Manufacturing Company | Optical recording medium with antistatic hard coating |
| US5348799A (en) | 1991-09-03 | 1994-09-20 | Minnesota Mining And Manufacturing Company | Antistatic coatings comprising chitosan acid salt and metal oxide particles |
| JP3242683B2 (ja) | 1991-11-27 | 2001-12-25 | 有限会社ユーエムエス | プラスチック表面処理剤及び処理方法 |
| US5220106A (en) | 1992-03-27 | 1993-06-15 | Exxon Research And Engineering Company | Organic non-quaternary clathrate salts for petroleum separation |
| JPH05289224A (ja) | 1992-04-10 | 1993-11-05 | Konica Corp | ハロゲン化銀写真感光材料 |
| DE4217366A1 (de) | 1992-05-26 | 1993-12-02 | Bayer Ag | Imide und deren Salze sowie deren Verwendung |
| JPH0618863A (ja) | 1992-07-06 | 1994-01-28 | Toshiba Corp | 液晶表示器 |
| JPH06103228A (ja) | 1992-09-18 | 1994-04-15 | Fujitsu Ltd | 処理システム |
| JP3299598B2 (ja) | 1993-02-17 | 2002-07-08 | 株式会社イノアックコーポレーション | 導電性ポリウレタンフォーム及びその製造方法 |
| EP0633496B1 (en) | 1993-07-09 | 1999-09-15 | Imation Corp. | Silver halide photographic material having improved antistatic properties |
| US6171707B1 (en) | 1994-01-18 | 2001-01-09 | 3M Innovative Properties Company | Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent |
| GB9402612D0 (en) | 1994-02-10 | 1994-04-06 | British Petroleum Co Plc | Ionic liquids |
| DE69413020T2 (de) | 1994-07-12 | 1999-02-18 | Imation Corp., Oakdale, Minn. | Antistatischer Röntgenstrahlenverstärkungsschirm mit Sulfonylmethid- und Sulfonylimidlithiumsalzen |
| JP3117369B2 (ja) | 1994-09-12 | 2000-12-11 | セントラル硝子株式会社 | スルホンイミドの製造方法 |
| JPH0892450A (ja) | 1994-09-22 | 1996-04-09 | Sekisui Chem Co Ltd | 塩化ビニル系樹脂組成物 |
| JPH08100169A (ja) * | 1994-09-30 | 1996-04-16 | Daikin Ind Ltd | 帯電防止剤 |
| US5518788A (en) | 1994-11-14 | 1996-05-21 | Minnesota Mining And Manufacturing Company | Antistatic hard coat incorporating a polymer comprising pendant fluorinated groups |
| DE69534293T2 (de) | 1994-12-21 | 2006-05-18 | Centre National De La Recherche Scientifique (C.N.R.S.) | Flüssige, hydrophobe Salze, ihre Herstellung und ihre Verwendung in der Elektrochemie |
| JPH08208889A (ja) | 1995-02-02 | 1996-08-13 | Sekisui Chem Co Ltd | 帯電防止性樹脂組成物 |
| DE69600572T2 (de) | 1995-02-08 | 1999-04-29 | Imation Corp (N.D.Ges.D. Staates Delaware), Oakdale, Minn. | Antistatikhartschicht |
| US5874616A (en) | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
| US5514493A (en) | 1995-03-06 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them |
| US5554664A (en) | 1995-03-06 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Energy-activatable salts with fluorocarbon anions |
| US5827602A (en) | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
| DE69512645T2 (de) | 1995-07-07 | 2000-06-08 | Minnesota Mining And Mfg. Co., Saint Paul | Antistatischer Verstärkungsschirm für Röntgenstrahlen mit Fluoroalkylsulfonat-Salzen |
| JPH09255939A (ja) | 1996-03-26 | 1997-09-30 | Arakawa Chem Ind Co Ltd | 耐熱性帯電防止剤およびその製造方法 |
| GB9616264D0 (en) | 1996-08-02 | 1996-09-11 | British Nuclear Fuels Plc | Reprocessing irradiated fuel |
| JPH10265674A (ja) | 1997-03-25 | 1998-10-06 | Mitsubishi Chem Corp | 高分子化合物複合体及びその製造方法 |
| JPH10298539A (ja) | 1997-04-22 | 1998-11-10 | Arutetsuku Kk | 静電防止剤及びこの静電防止剤を用いて成る塗布及び接着剤 |
| JPH1111675A (ja) | 1997-06-27 | 1999-01-19 | Kawasaki Steel Corp | H形鋼のパイリング姿の判別方法および判別装置 |
| US6358601B1 (en) | 1997-07-11 | 2002-03-19 | 3M Innovative Properties Company | Antistatic ceramer hardcoat composition with improved antistatic characteristics |
| US6194497B1 (en) | 1997-07-23 | 2001-02-27 | General Electric Company | Anti-static resin composition containing fluorinated phosphonium sulfonates |
| JP2909735B2 (ja) | 1997-07-25 | 1999-06-23 | 三洋化成工業株式会社 | 耐熱性に優れる樹脂用帯電防止剤および帯電防止性樹脂組成物 |
| US5965054A (en) * | 1997-08-12 | 1999-10-12 | Covalent Associates, Inc. | Nonaqueous electrolyte for electrical storage devices |
| JPH11116752A (ja) | 1997-10-17 | 1999-04-27 | Sekisui Chem Co Ltd | 抗菌・防黴性樹脂組成物 |
| WO1999030381A1 (en) * | 1997-12-10 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Bis(perfluoroalkylsulfonyl)imide surfactant salts in electrochemical systems |
| JP3060107B2 (ja) * | 1998-01-28 | 2000-07-10 | 三洋化成工業株式会社 | 難燃性非水電解液およびそれを用いた二次電池 |
| JP3702645B2 (ja) * | 1998-05-12 | 2005-10-05 | 三菱化学株式会社 | 有機オニウム塩の製造方法 |
| JP2001035253A (ja) * | 1999-07-19 | 2001-02-09 | Fuji Photo Film Co Ltd | 電解質組成物、光電変換素子および光電気化学電池 |
| CA2388621A1 (en) * | 1999-08-16 | 2001-02-22 | Bayer Aktiengesellschaft | Antistatic agent |
| US6372829B1 (en) * | 1999-10-06 | 2002-04-16 | 3M Innovative Properties Company | Antistatic composition |
-
1999
- 1999-10-06 US US09/412,850 patent/US6372829B1/en not_active Expired - Lifetime
-
2000
- 2000-03-14 DE DE60018597T patent/DE60018597T2/de not_active Expired - Lifetime
- 2000-03-14 KR KR1020027004360A patent/KR100755813B1/ko not_active Expired - Fee Related
- 2000-03-14 JP JP2001528488A patent/JP5412629B2/ja not_active Expired - Fee Related
- 2000-03-14 CA CA002385476A patent/CA2385476C/en not_active Expired - Lifetime
- 2000-03-14 WO PCT/US2000/006597 patent/WO2001025326A1/en not_active Ceased
- 2000-03-14 AU AU37435/00A patent/AU3743500A/en not_active Abandoned
- 2000-03-14 EP EP00916312A patent/EP1232206B1/en not_active Expired - Lifetime
- 2000-09-21 TW TW089119475A patent/TWI230176B/zh not_active IP Right Cessation
-
2001
- 2001-12-28 US US10/032,916 patent/US6706920B2/en not_active Expired - Lifetime
-
2012
- 2012-12-11 JP JP2012270411A patent/JP5395248B2/ja not_active Expired - Fee Related
-
2013
- 2013-08-21 JP JP2013171136A patent/JP5643401B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013076081A (ja) | 2013-04-25 |
| CA2385476A1 (en) | 2001-04-12 |
| DE60018597T2 (de) | 2005-12-29 |
| DE60018597D1 (de) | 2005-04-14 |
| JP2013253254A (ja) | 2013-12-19 |
| WO2001025326A8 (en) | 2001-08-30 |
| US6706920B2 (en) | 2004-03-16 |
| US6372829B1 (en) | 2002-04-16 |
| EP1232206B1 (en) | 2005-03-09 |
| CA2385476C (en) | 2009-08-04 |
| EP1232206A1 (en) | 2002-08-21 |
| US20020137825A1 (en) | 2002-09-26 |
| KR20020042857A (ko) | 2002-06-07 |
| WO2001025326A1 (en) | 2001-04-12 |
| JP5643401B2 (ja) | 2014-12-17 |
| JP2003511505A (ja) | 2003-03-25 |
| TWI230176B (en) | 2005-04-01 |
| AU3743500A (en) | 2001-05-10 |
| KR100755813B1 (ko) | 2007-09-07 |
| JP5395248B2 (ja) | 2014-01-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5412629B2 (ja) | 帯電防止組成物 | |
| US6592988B1 (en) | Water-and oil-repellent, antistatic composition | |
| US6740413B2 (en) | Antistatic compositions | |
| US7678941B2 (en) | Polyoxyalkylene ammonium salts and their use as antistatic agents | |
| KR100943549B1 (ko) | 물- 및 오일-반발성 정전기 방지 조성물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070314 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070314 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20091216 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100622 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100922 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110906 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111205 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20111212 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120305 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120911 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121211 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20130521 |
|
| 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: 20130917 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131017 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5412629 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |