JP5502060B2 - 帯電防止剤の製造方法 - Google Patents
帯電防止剤の製造方法 Download PDFInfo
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- JP5502060B2 JP5502060B2 JP2011270290A JP2011270290A JP5502060B2 JP 5502060 B2 JP5502060 B2 JP 5502060B2 JP 2011270290 A JP2011270290 A JP 2011270290A JP 2011270290 A JP2011270290 A JP 2011270290A JP 5502060 B2 JP5502060 B2 JP 5502060B2
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- Prior art keywords
- acid
- phosphonium
- formula
- carbon atoms
- aqueous medium
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 239000002216 antistatic agent Substances 0.000 title description 52
- -1 phosphonium sulfonate salt Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000012736 aqueous medium Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical group 0.000 claims abstract description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims abstract description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 11
- 229910052739 hydrogen Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000006184 cosolvent Substances 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
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- 239000011737 fluorine Substances 0.000 claims description 4
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 4
- OYGQVDSRYXATEL-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OYGQVDSRYXATEL-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- QZHDEAJFRJCDMF-UHFFFAOYSA-N perfluorohexanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 claims description 2
- XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 claims description 2
- ACEKLXZRZOWKRY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ACEKLXZRZOWKRY-UHFFFAOYSA-N 0.000 claims description 2
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 claims description 2
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 claims description 2
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical group C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 claims description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims description 2
- HOMONHWYLOPSLL-UHFFFAOYSA-N tributyl(ethyl)phosphanium Chemical compound CCCC[P+](CC)(CCCC)CCCC HOMONHWYLOPSLL-UHFFFAOYSA-N 0.000 claims description 2
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 claims description 2
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 claims description 2
- NVQBNLRCSAEYHZ-UHFFFAOYSA-N trimethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](C)(C)C NVQBNLRCSAEYHZ-UHFFFAOYSA-N 0.000 claims description 2
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=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-N 0.000 claims 2
- IKNWWJMESJSJDP-UHFFFAOYSA-N benzyl(tributyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CC1=CC=CC=C1 IKNWWJMESJSJDP-UHFFFAOYSA-N 0.000 claims 1
- YQPAAVMEUPILEE-UHFFFAOYSA-N butyl(trimethyl)phosphanium Chemical compound CCCC[P+](C)(C)C YQPAAVMEUPILEE-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- IKANSXQHJXBNIN-UHFFFAOYSA-N trimethyl(octadecyl)phosphanium Chemical compound CCCCCCCCCCCCCCCCCC[P+](C)(C)C IKANSXQHJXBNIN-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000047 product Substances 0.000 description 43
- 239000000203 mixture Substances 0.000 description 36
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical class O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 21
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- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000012535 impurity Substances 0.000 description 13
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- 239000000376 reactant Substances 0.000 description 13
- 239000011342 resin composition Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
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- 239000000654 additive Substances 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
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- 238000002411 thermogravimetry Methods 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
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- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- JFWJJBXZSJXYCT-UHFFFAOYSA-N 18,18-dimethylnonadecylphosphane Chemical compound CC(C)(C)CCCCCCCCCCCCCCCCCP JFWJJBXZSJXYCT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 239000004697 Polyetherimide Substances 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- FEDFHMISXKDOJI-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FEDFHMISXKDOJI-UHFFFAOYSA-M 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical class [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
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- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
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- QBJDFZSOZNDVDE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QBJDFZSOZNDVDE-UHFFFAOYSA-M 0.000 description 1
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- 150000008054 sulfonate salts Chemical class 0.000 description 1
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- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
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- QCLVFLIIJODTJU-UHFFFAOYSA-N triethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](CC)(CC)CC QCLVFLIIJODTJU-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
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- 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
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
別の実施形態では、熱可塑性ポリマーと、上述の方法のいずれかで製造される帯電防止剤とを含んでなる熱可塑性樹脂組成物が提供される。
まず、100mL二口丸底フラスコに5.00g(MW302、16.55mmol)のペルフルオロブタンスルホニルフルオライド(「A」)を秤量して仕込み、磁気攪拌子で攪拌し、85℃の油浴中で還流する。
まず、54.8g(180.837mmol)のペルフルオロブタンスルホン酸リチウム(「Li Rimar」)を300mLの室温のMQ水に添加して溶解し、60.8g(179.062mmol)のTBPBrを200mLの室温のMQ水に添加して溶解する。TBPBr溶液を濾過し、次いでプロペラ攪拌機で攪拌しながらLi Rimar塩溶液中に徐々に注ぎ込むと、帯電防止剤生成物が生じる。すべてのTBPBrを添加した後、反応混合物をさらに15分間攪拌する。反応終了後、帯電防止剤生成物を濾過によって単離し、50mLのMQ水でフラッシュして大部分の不純物を除去する。さらに、帯電防止剤生成物をMQ水中に懸濁し、それを80℃まで加熱し、数分間攪拌し、混合物を冷却して帯電防止剤生成物を再び晶出させて追加の精製を行う。次いで、帯電防止剤生成物を濾過によって単離し、50℃の真空乾燥炉内で乾燥することができる。理論収量は帯電防止剤100.0gであり、87.1gが得られた。
まず、100mL二口丸底フラスコに5.00g(MW302、16.55mmol)のペルフルオロブタンスルホニルフルオライド(「A」)を秤量して仕込み、磁気攪拌子で攪拌し、85℃の油浴中で還流する。
まず、5.77g(18.083mmol)のペルフルオロブタンスルホン酸ナトリウム(「Na Rimar」)を50mLの室温のMQ水に添加して溶解し、6.08g(17.906mmol)のTBPBrを20mLの室温のMQ水に添加して溶解する。TBPBr溶液を濾過し、次いで強力な磁気攪拌子で攪拌しながらNa Rimar塩溶液中に徐々に注ぎ込むと、帯電防止剤生成物が生じる。すべてのTBPBrを添加した後、反応混合物をさらに15分間攪拌する。反応終了後、帯電防止剤生成物を濾過によって単離し、50mLのMQ水でフラッシュして大部分の不純物を除去する。さらに、帯電防止剤生成物をMQ水中で攪拌し、それを80℃に加熱し、数分間攪拌し、混合物を冷却して帯電防止剤生成物を晶出させて追加の精製を行う。次いで、帯電防止剤生成物を濾過によって単離し、50℃の真空乾燥炉内で乾燥する。理論収量は帯電防止剤10.0gであり、
8.10gが得られた。
まず、100mL二口丸底フラスコに5.00g(MW302、16.55mmol)のペルフルオロブタンスルホニルフルオライド(「A」)を秤量して仕込み、磁気攪拌子で攪拌し、85℃の油浴中で還流する。次に、4.46gの50wt%KOH溶液をゆっくりと添加して2.4当量のKOH(2.23g、39.72mmol)(4.46gの50wt%溶液)を供給する。混合物を1時間還流させ、それから75mLのエタノール/MQ水(体積比3/4)を添加し、すべてのものが溶解するまで攪拌する。次に、5.56g(16.38mmol)のTBPBrを25mLのMQ水に溶解し、この溶液にゆっくりと添加すると、帯電防止剤生成物が生じる。すべての溶解TBPBrを添加した後、混合物をさらに15分間攪拌してから、混合物を室温に冷却する。分液漏斗内で帯電防止剤生成物を75mLのジクロロメタンで抽出し、50mLのMQ水で3回洗う。有機層を減圧下で除去する(50℃、Pstart=475mbar及びPend=125mbar)。さらに、帯電防止剤生成物をMQ水中で攪拌し、それを80℃に加熱し、数分間攪拌し、混合物を冷却して帯電防止剤生成物を晶出させて追加の精製を行うことができる。次いで、帯電防止剤生成物を濾過によって単離し、50℃の真空乾燥炉内で乾燥する。理論収量は帯電防止剤9.24gであり、6.04gが得られた。
まず、6.06g(17.9mmol)のペルフルオロブタンスルホン酸カリウム(「K Rimar」)を75mLのエタノール/MQ水溶液(体積比3/4)に添加して溶解し、6.01g(17.7mmol)のTBPBrを25mLの室温のMQ水に添加して溶解する。攪拌しながらTBPBr溶液をK Rimar塩溶液中に徐々に注ぎ込むと、帯電防止剤生成物が生じる。すべてのTBPBrを添加した後、反応混合物をさらに15分間攪拌する。分液漏斗内で帯電防止剤生成物を75mLのジクロロメタンで抽出し、50mLのMQ水で3回洗う。有機層を減圧下で除去する(50℃、Pstart=475mbar及びPend=125mbar)。さらに、帯電防止剤生成物をMQ水中で攪拌し、それを80℃に加熱し、数分間攪拌し、混合物を冷却して帯電防止剤生成物を晶出させて追加の精製を行うことができる。次いで、帯電防止剤生成物を濾過によって単離し、50℃の真空乾燥炉内で乾燥する。理論収量は帯電防止剤10.0gであり、8.91gが得られた。
まず、100mL二口丸底フラスコに5.00g(MW302、16.55mmol)のAを秤量して仕込み、磁気攪拌子で攪拌し、85℃の油浴中で還流する。次に、10.98g(39.72mmol)の40%水酸化テトラブチルホスホニウムを添加する。次いで、混合物を1時間還流する。次いで、50mLのMQ水を添加し、さらに15分間攪拌する。次いで、混合物を(好ましくは氷/水浴中で)冷却し、それから水をデカントする。次いで、100mLのMQ水を添加し、85℃の油浴中で加熱しながら15分間攪拌する。続いて、混合物を室温に冷却し、帯電防止剤生成物を濾過によって単離し、25mLのMQ水でフラッシュする。次に、帯電防止剤生成物を50℃の真空乾燥炉内で乾燥する。理論収量は帯電防止剤9.24gであり、7.4gが得られた。
1323406754736_0
に示すように、臭素の存在量が増すと、130℃で936時間の熱老化後にポリカーボネートの黄変の増加をもたらすことがある。表3はさらに、標記の量のイオン夾雑物を含むポリカーボネートの熱老化後のYIの変化(ΔYI)を示す。熱老化したポリカーボネートにはスポットが認められたが、これは恐らくカリウム及びナトリウム汚染に由来するものである。
Claims (7)
- 以下の一般式(1)のスルホン酸ホスホニウム塩の製造方法であって、
水性媒質中で以下の一般式(2)の化合物を化学量論的過剰量の一般式(3)の化合物と混合する段階、及び
水性媒質から式(1)のスルホン酸ホスホニウムを分離する段階
を含んでなり、
水性媒質が、1体積%未満の共溶媒を含む、水の溶液、分散液、または懸濁液である、方法。
- Xがフッ素であり、Zが臭素又は塩素であり、3つのR基が炭素原子数1〜8の同一の脂肪族炭化水素基又は炭素原子数6〜12の同一の芳香族炭化水素基であり、4番目のR基が炭素原子数1〜18の炭化水素基である、請求項1記載の方法。
- pが0である、請求項2記載の方法。
- スルホン酸がペルフルオロメタンスルホン酸、ペルフルオロエタンスルホン酸、ペルフルオロプロパンスルホン酸、ペルフルオロブタンスルホン酸、ペルフルオロペンタンスルホン酸、ペルフルオロヘキサンスルホン酸、ペルフルオロヘプタンスルホン酸、ペルフルオロオクタンスルホン酸又はこれらのスルホン酸の1種以上を含む組合せであり、ホスホニウムがテトラメチルホスホニウム、テトラエチルホスホニウム、テトラブチルホスホニウム、トリエチルメチルホスホニウム、トリブチルメチルホスホニウム、トリブチルエチルホスホニウム、トリオクチルメチルホスホニウム、トリメチルブチルホスホニウム、トリメチルオクチルホスホニウム、トリメチルラウリルホスホニウム、トリメチルステアリルホスホニウム、トリエチルオクチルホスホニウム、テトラフェニルホスホニウム、トリフェニルメチルホスホニウム、トリフェニルベンジルホスホニウム、トリブチルベンジルホスホニウム、或いはこれらのホスホニウムの1種以上を含む組合せである、請求項1記載の方法。
- スルホン酸がペルフルオロメタンスルホン酸、ペルフルオロブタンスルホン酸、ペルフルオロヘキサンスルホン酸、ペルフルオロヘプタンスルホン酸、ペルフルオロオクタンスルホン酸又はこれらの有機スルホン酸陰イオンの1種以上を含む組合せであり、ホスホニウムがテトラブチルホスホニウムである、請求項4記載の方法。
- 式(2)の化合物と式(3)の化合物とのモル比が1:1.002〜1:1.1である、請求項1記載の方法。
- 各Rが、炭素原子数1〜8の同一又は異なる直鎖又は枝分れ脂肪族炭化水素基である、請求項1記載の方法。
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KR (1) | KR101176669B1 (ja) |
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US20060100327A1 (en) * | 2004-11-08 | 2006-05-11 | Hoeks Theodorus L | Methods of making an antistatic agent |
JP5821582B2 (ja) * | 2011-01-31 | 2015-11-24 | 住友化学株式会社 | 製造方法 |
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2004
- 2004-10-15 US US10/966,774 patent/US7211690B2/en active Active
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- 2005-04-07 DE DE602005021768T patent/DE602005021768D1/de active Active
- 2005-04-07 AT AT07110825T patent/ATE519735T1/de not_active IP Right Cessation
- 2005-04-07 EP EP07110825A patent/EP1832574B1/en not_active Not-in-force
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- 2005-04-07 KR KR1020067021182A patent/KR101176669B1/ko active IP Right Grant
- 2005-04-07 AT AT05735086T patent/ATE470658T1/de not_active IP Right Cessation
- 2005-04-07 EP EP05735086A patent/EP1737814B1/en not_active Not-in-force
- 2005-04-13 TW TW094111716A patent/TW200606138A/zh unknown
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2007
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- 2007-10-09 US US11/869,338 patent/US7429628B2/en not_active Expired - Fee Related
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2011
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Also Published As
Publication number | Publication date |
---|---|
ATE519735T1 (de) | 2011-08-15 |
KR101176669B1 (ko) | 2012-08-23 |
EP1737814A2 (en) | 2007-01-03 |
JP2011201900A (ja) | 2011-10-13 |
JP2007532647A (ja) | 2007-11-15 |
DE602005021768D1 (de) | 2010-07-22 |
EP1832574A3 (en) | 2010-03-17 |
JP5377570B2 (ja) | 2013-12-25 |
TW200606138A (en) | 2006-02-16 |
JP2012092122A (ja) | 2012-05-17 |
EP1832574B1 (en) | 2011-08-10 |
US20070129472A1 (en) | 2007-06-07 |
US20050228194A1 (en) | 2005-10-13 |
KR20060135879A (ko) | 2006-12-29 |
US7309735B2 (en) | 2007-12-18 |
EP1832574A2 (en) | 2007-09-12 |
JP4932702B2 (ja) | 2012-05-16 |
US7211690B2 (en) | 2007-05-01 |
WO2005100307A3 (en) | 2005-12-15 |
US7429628B2 (en) | 2008-09-30 |
US20080081857A1 (en) | 2008-04-03 |
WO2005100307A2 (en) | 2005-10-27 |
EP1737814B1 (en) | 2010-06-09 |
ATE470658T1 (de) | 2010-06-15 |
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