JP5254123B2 - リチウムイオン選択性電極 - Google Patents
リチウムイオン選択性電極 Download PDFInfo
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- JP5254123B2 JP5254123B2 JP2009110895A JP2009110895A JP5254123B2 JP 5254123 B2 JP5254123 B2 JP 5254123B2 JP 2009110895 A JP2009110895 A JP 2009110895A JP 2009110895 A JP2009110895 A JP 2009110895A JP 5254123 B2 JP5254123 B2 JP 5254123B2
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims description 90
- 229910001416 lithium ion Inorganic materials 0.000 title claims description 90
- 150000002500 ions Chemical class 0.000 claims description 48
- 239000012528 membrane Substances 0.000 claims description 22
- -1 diphenyl ether compound Chemical class 0.000 claims description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 12
- VNHGETRQQSYUGZ-UHFFFAOYSA-N 1-nitro-2-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1 VNHGETRQQSYUGZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ZRERPOUKPQCAQG-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[3-(2-fluorophenyl)-2-nitrophenoxy]-2-nitrobenzene Chemical compound C1=CC=C(C=2C(=CC=CC=2)F)C([N+](=O)[O-])=C1OC(C=1[N+]([O-])=O)=CC=CC=1C1=CC=CC=C1F ZRERPOUKPQCAQG-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 229910001415 sodium ion Inorganic materials 0.000 description 17
- 238000005259 measurement Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000012488 sample solution Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000007717 exclusion Effects 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- CXVOIIMJZFREMM-UHFFFAOYSA-N 1-(2-nitrophenoxy)octane Chemical compound CCCCCCCCOC1=CC=CC=C1[N+]([O-])=O CXVOIIMJZFREMM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- XVZDYNSMGNIZSS-UHFFFAOYSA-N 1-(2-fluorophenoxy)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1F XVZDYNSMGNIZSS-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000013060 biological fluid Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000008235 industrial water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CFPFMAGBHTVLCZ-UHFFFAOYSA-N (4-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(Cl)C=C1 CFPFMAGBHTVLCZ-UHFFFAOYSA-N 0.000 description 2
- AGCBIBHANSJWDX-UHFFFAOYSA-N 2,2,3,3-tetramethyl-9-tetradecyl-1,4,8,11-tetraoxacyclotetradecane Chemical compound CCCCCCCCCCCCCCC1COCCCOC(C)(C)C(C)(C)OCCCO1 AGCBIBHANSJWDX-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 2
- GTKRFUAGOKINCA-UHFFFAOYSA-M chlorosilver;silver Chemical compound [Ag].[Ag]Cl GTKRFUAGOKINCA-UHFFFAOYSA-M 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000000700 radioactive tracer Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 1
- DDUJCCRSCBUHMI-UHFFFAOYSA-N 2-dodecoxybenzonitrile Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1C#N DDUJCCRSCBUHMI-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- DWDDCROEBRKXIF-UHFFFAOYSA-N O.O.O.B(O)(O)O Chemical compound O.O.O.B(O)(O)O DWDDCROEBRKXIF-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000002555 ionophore Substances 0.000 description 1
- 230000000236 ionophoric effect Effects 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- KAVKNHPXAMTURG-UHFFFAOYSA-N n-(4-bromonaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=C(Br)C2=C1 KAVKNHPXAMTURG-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Images
Description
(1)
(式(1)において、R1およびR2はそれぞれ独立して、水素原子、アルキル基、ベンジル基、ベンジルオキシメチル基、フェニル基、シクロヘキシル基から選択されるいずれか1種であり、R3〜R6はそれぞれ独立して炭化水素基である。)
[リチウムイオン選択性電極の作製]
感応膜は、所定量のイオン選択性配位分子、アニオン排除剤、可塑剤、高分子マトリクスとしてポリ塩化ビニルを、テトラヒドロフランに加えて室温下で溶解させ、10分間撹拌した後にガラスシャーレ上に展開して一昼夜風乾させた。その後、直径6mmの膜を切り出し、ポリ塩化ビニルの50mg/mLテトラヒドロフラン溶液を接着剤として用いて、外筒に取り付けた。内部液として、0.01mol/LのLiCl溶液を入れ、内部電極を挿入し、リチウムイオン選択性電極を完成させた。外筒は市販のイオン電極キット(東亜ディーケーケー製)、内部電極は銀線に塩化銀を電着させたものを用いた。
応答電位の測定は、参照電極として銀−塩化銀電極(東亜ディーケーケー製、HS−205C)、直流電位差計としてイオンメータ(東亜ディーケーケー製、IM−55G)を用いて行った。
イオン選択性電極の選択性は一般に選択係数によって表される。選択係数は、測定対象イオンに対して妨害イオンがどれだけ応答電位に影響を与えるかを示す数値であり、この値の大きさによってイオン選択性電極の性能が評価される。測定方法に関する詳細は、参考文献(JIS K−0122(イオン電極測定方法通則))に記載されている。
(1)0.1M NaCl溶液にリチウムイオン電極を浸漬させて、応答電位の測定を開始
(2)リチウムイオン電極を浸漬した溶液にLiCl溶液を順次添加し、応答電位を測定
製作したリチウムイオン選択性電極は測定を行わない間、相模原市水を5倍濃縮した水にリチウムイオンを1mg/Lとなるよう添加した溶液に常時浸漬させておいた。このリチウムイオン選択性電極について、製作直後、および製作から60日後、80日後、130日後にリチウムイオンのナトリウムイオンに対する選択性を測定した結果を図4に示す。リチウムイオンのナトリウムイオンに対する選択係数は、上記参考文献に記載の方法に従って算出した。図4から明らかな通り、比較例1,2のNPOE、DOSや、参考例1,2のCPDDE、DBPに比べて、実施例1,2のNPPE、FPNPEを可塑剤として用いたリチウムイオン選択性電極の方が、より長期間にわたり、高いリチウムイオンのナトリウムイオンに対する選択性を維持できることがわかる。
液性の異なる試料溶液にリチウムイオン選択性電極を漬け替えた際の応答速度を比較した。測定手順は以下の通りである。
(1)相模原市水を5倍濃縮して全溶解成分の濃度を高めた水に、リチウムイオンを1mg/Lとなるように添加した溶液を準備
(2)上記の溶液にリチウムイオン電極を浸漬させて一晩放置
(3)リチウムイオン電極を、リチウム濃度1mg/Lを含む0.01mol/L 塩化アンモニア溶液に漬け替えて測定開始
Claims (2)
- 請求項1に記載のリチウムイオン選択性電極であって、
前記式(2)で示されるジフェニルエーテル化合物が、2−ニトロフェニルフェニルエーテル、2−フルオロフェニル−2−ニトロフェニルエーテルから選択されるいずれか1種であることを特徴とするリチウムイオン選択性電極。
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JP2009110895A JP5254123B2 (ja) | 2009-04-30 | 2009-04-30 | リチウムイオン選択性電極 |
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JP2009110895A JP5254123B2 (ja) | 2009-04-30 | 2009-04-30 | リチウムイオン選択性電極 |
Publications (2)
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JP2010261745A JP2010261745A (ja) | 2010-11-18 |
JP5254123B2 true JP5254123B2 (ja) | 2013-08-07 |
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Cited By (1)
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WO2021067770A1 (en) * | 2019-10-03 | 2021-04-08 | President And Fellows Of Harvard College | Chelator-in-ionic liquid electrolytes |
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CN112285183A (zh) * | 2020-10-10 | 2021-01-29 | 广州大学 | 一种无膜全固态离子选择性电极及其制备方法和应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0227252A (ja) * | 1988-07-18 | 1990-01-30 | Hitachi Ltd | イオン選択性電極 |
US5286365A (en) * | 1992-01-15 | 1994-02-15 | Beckman Instruments, Inc. | Graphite-based solid state polymeric membrane ion-selective electrodes |
JP3307687B2 (ja) * | 1992-08-31 | 2002-07-24 | 鈴木 孝治 | イオン選択性配位分子およびイオンセンサ |
JP4292380B2 (ja) * | 2002-04-23 | 2009-07-08 | オルガノ株式会社 | 水処理用薬品の濃度管理方法及び濃度管理装置 |
JP4111742B2 (ja) * | 2002-05-09 | 2008-07-02 | 独立行政法人科学技術振興機構 | アザアヌーレン誘導体からなるイオノフォア、感応膜、およびそれを用いたイオンセンサ |
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WO2021067770A1 (en) * | 2019-10-03 | 2021-04-08 | President And Fellows Of Harvard College | Chelator-in-ionic liquid electrolytes |
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