JP5017801B2 - キレート樹脂 - Google Patents
キレート樹脂 Download PDFInfo
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- JP5017801B2 JP5017801B2 JP2005153111A JP2005153111A JP5017801B2 JP 5017801 B2 JP5017801 B2 JP 5017801B2 JP 2005153111 A JP2005153111 A JP 2005153111A JP 2005153111 A JP2005153111 A JP 2005153111A JP 5017801 B2 JP5017801 B2 JP 5017801B2
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- Prior art keywords
- group
- chelate
- resin
- amino group
- carrier
- Prior art date
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- 229920001429 chelating resin Polymers 0.000 title description 6
- 239000013522 chelant Substances 0.000 claims description 64
- 229920005989 resin Polymers 0.000 claims description 64
- 239000011347 resin Substances 0.000 claims description 64
- 125000003277 amino group Chemical group 0.000 claims description 30
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical group OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 4
- 229920006037 cross link polymer Polymers 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical group OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical group OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- DMQQXDPCRUGSQB-UHFFFAOYSA-N 2-[3-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical group OC(=O)CN(CC(O)=O)CCCN(CC(O)=O)CC(O)=O DMQQXDPCRUGSQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 239000003513 alkali Substances 0.000 description 11
- 229910001385 heavy metal Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000010949 copper Substances 0.000 description 9
- 239000011575 calcium Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical group N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- TXPKUUXHNFRBPS-UHFFFAOYSA-N 3-(2-carboxyethylamino)propanoic acid Chemical compound OC(=O)CCNCCC(O)=O TXPKUUXHNFRBPS-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- -1 CH 3 ) 2 (C 2 H 5 ) Chemical class 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatment Of Water By Ion Exchange (AREA)
Description
で示される構造である上記(1)記載のキレート樹脂。
で示されるものであれば、特に限定されないが、上記式中の置換基(R1、R2、R3)となりうるアルキル基およびアルキルアルコール基の炭素数は3以下であることが好ましい。本発明におけるアミノ基として、具体的には、例えば、−N+H3、−N+(CH3)3、−N+(CH3)2(C2H5)、−N(C2H5OH)2、−HN+−NH2、−N(CH3)2、−HN(C2H5)などを挙げることができ、好ましくは−N+(CH3)3、−N+(CH3)2(C2H5)、−N(CH3)2等の、樹脂担体に結合後、窒素原子に水素原子が結合した1級や2級のアミンが残らないものである。上記キレート基と同様、1級や2級のアミンが残っていると、試料中のクロルやエポキシ含有の有機物等と反応し、選択性や再現性が損ねられる場合がある。
(a)樹脂担体の製造
グリシジルメタクリレート100g、テトラメチロールメタントリメタクリレート100g、酢酸ブチル180g、イソアミルアルコール120g及びアゾビスイソブチロニトリル0.7gの混合物にイオン交換水1000ml、1%ポリビニルアルコール水溶液200mlを加え、攪拌しながら水酸化ナトリウム水溶液を用いてpH7〜8に調整した。その後、70℃で6時間重合反応を行った。反応物を冷却した後、生成した共重合体粒子を濾取し、メタノール及び水で順次洗浄した。次いで、得られた共重合体粒子を一日風乾し、さらに80℃の真空乾燥機に入れて6時間乾燥した。さらに、乾燥した共重合体粒子を分級することで、平均粒径40〜50μmの多孔性架橋重合体粒子(樹脂担体)30gを得た。
上記(a)で作製した樹脂担体10gとイミノジ酢酸ナトリウム10gを15%水酸化ナトリウム水溶液100mlに入れ、60℃で5時間反応させた。反応物を濾過しイオン交換水で洗浄し、キレート基導入樹脂担体を得た。
上記(b)で得たキレート基導入樹脂担体を30%トリメチルアミン100mlに全量入れ、30℃で5時間反応させ、反応物を濾過しイオン交換水、メタノールで洗浄し、キレート樹脂を得た。
(1)カートリッジに、上記で作製したキレート樹脂0.25gを充填し、アセトニトリル、10mM硝酸、0.05M酢酸アンモニウム、イオン交換水でコンディショニング後、これに0.5M硫酸銅4mLを負荷し、余剰分の硫酸銅を10mM硝酸、イオン交換水で洗い、1M硝酸6mLで溶出し、吸光光度計でキレート樹脂のCu捕捉量を測定した(測定波長:805nm、参照セル:水)。その結果、キレート樹脂のCu捕捉量は、240μmol/gであった。
キレート基導入樹脂担体を50%ジメチルアミン水溶液100mlに入れ、30℃で5時間反応させることで、残存エポキシ基にアミノ基を導入した以外は、実施例1と同様にしてキレート樹脂を作製した。このキレート樹脂について、実施例1と同様にして、Cu及びCa捕捉量を求めたところ、Cu捕捉量は250μmol/g、Ca捕捉量は0μmol/gであった。
実施例1の(a)と(b)と同様にして作製したキレート基導入樹脂担体を0.01N硫酸水溶液100mlに入れ、40℃で5時間反応させ、残存エポキシ基を開環させた。その後、反応物を濾過し、イオン交換水で洗浄して、イミノジ酢酸型キレート樹脂を得た。このキレート樹脂について、実施例1と同様にして、Cu及びCa捕捉量を求めたところ、Cu捕捉量は200μmol/g、Ca捕捉量は300μmol/gであった。
Claims (6)
- 前記アミノ基が−N(CH3)2または−N+(CH3)3である請求項1記載のキレート樹脂。
- 前記キレート基がイミノジ酢酸基である請求項1又は2に記載のキレート樹脂。
- 前記樹脂担体が架橋重合体である請求項1〜3のいずれか1項記載のキレート樹脂。
- 前記樹脂担体中、架橋剤が10〜90重量%含まれている請求項1〜4のいずれか1項記載のキレート樹脂。
- 前記樹脂担体に導入、結合した前記アミノ基量が前記キレート基に対し、0.1〜1.0当量(モル)の範囲である請求項1〜5のいずれか1項記載のキレート樹脂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005153111A JP5017801B2 (ja) | 2005-05-25 | 2005-05-25 | キレート樹脂 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005153111A JP5017801B2 (ja) | 2005-05-25 | 2005-05-25 | キレート樹脂 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006328203A JP2006328203A (ja) | 2006-12-07 |
JP5017801B2 true JP5017801B2 (ja) | 2012-09-05 |
Family
ID=37550236
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005153111A Active JP5017801B2 (ja) | 2005-05-25 | 2005-05-25 | キレート樹脂 |
Country Status (1)
Country | Link |
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JP (1) | JP5017801B2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3406637B1 (en) | 2016-01-20 | 2021-03-31 | Hymo Corporation | Iminodiacetic acid type chelate resin and method for producing same |
CN111517546B (zh) * | 2020-04-07 | 2022-03-01 | 江苏南大华兴环保科技股份公司 | 一种含铜废水中回收镁盐的处理方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57177012A (en) * | 1981-04-23 | 1982-10-30 | Sumitomo Chem Co Ltd | Preparation of chelate resin |
JPS6088008A (ja) * | 1983-10-20 | 1985-05-17 | Asahi Chem Ind Co Ltd | キレ−ト樹脂の製法 |
JPS60123508A (ja) * | 1984-05-19 | 1985-07-02 | Agency Of Ind Science & Technol | ピリジルアルキルアミノポリカルボン酸型キレ−ト樹脂の製造方法 |
JPH074537B2 (ja) * | 1985-11-26 | 1995-01-25 | ミヨシ油脂株式会社 | キレ−ト樹脂 |
-
2005
- 2005-05-25 JP JP2005153111A patent/JP5017801B2/ja active Active
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