JP2002356464A - 高純度アミノポリカルボン酸及びその塩と製造方法 - Google Patents
高純度アミノポリカルボン酸及びその塩と製造方法Info
- Publication number
- JP2002356464A JP2002356464A JP2001161528A JP2001161528A JP2002356464A JP 2002356464 A JP2002356464 A JP 2002356464A JP 2001161528 A JP2001161528 A JP 2001161528A JP 2001161528 A JP2001161528 A JP 2001161528A JP 2002356464 A JP2002356464 A JP 2002356464A
- Authority
- JP
- Japan
- Prior art keywords
- purity
- aminopolycarboxylic acid
- ppm
- salt
- acid
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims abstract description 185
- 150000003839 salts Chemical class 0.000 title claims abstract description 90
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 31
- 229910052751 metal Inorganic materials 0.000 claims abstract description 114
- 239000002184 metal Substances 0.000 claims abstract description 114
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 55
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 51
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 47
- 239000011734 sodium Substances 0.000 claims description 43
- 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 claims description 38
- 229910052708 sodium Inorganic materials 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 27
- 239000011575 calcium Substances 0.000 claims description 26
- 239000011651 chromium Substances 0.000 claims description 26
- 229910052742 iron Inorganic materials 0.000 claims description 25
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 24
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052791 calcium Inorganic materials 0.000 claims description 24
- 229910052804 chromium Inorganic materials 0.000 claims description 24
- 229910052759 nickel Inorganic materials 0.000 claims description 24
- 150000002739 metals Chemical class 0.000 claims description 20
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 19
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 18
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002736 metal compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000011591 potassium Substances 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003637 basic solution Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 8
- 229960003330 pentetic acid Drugs 0.000 claims description 8
- DMQQXDPCRUGSQB-UHFFFAOYSA-N 2-[3-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCCN(CC(O)=O)CC(O)=O DMQQXDPCRUGSQB-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- UWRBFYBQPCJRRL-UHFFFAOYSA-N 3-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)CCN(CC(O)=O)CC(O)=O UWRBFYBQPCJRRL-UHFFFAOYSA-N 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 description 65
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
- -1 amine salt Chemical class 0.000 description 21
- 239000007787 solid Substances 0.000 description 12
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
- 229910021642 ultra pure water Inorganic materials 0.000 description 7
- 239000012498 ultrapure water Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- DCCWEYXHEXDZQW-BYPYZUCNSA-N (2s)-2-[bis(carboxymethyl)amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)N(CC(O)=O)CC(O)=O DCCWEYXHEXDZQW-BYPYZUCNSA-N 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VKZRWSNIWNFCIQ-UHFFFAOYSA-N 2-[2-(1,2-dicarboxyethylamino)ethylamino]butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NCCNC(C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-UHFFFAOYSA-N 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- LESFYQKBUCDEQP-UHFFFAOYSA-N tetraazanium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound N.N.N.N.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O LESFYQKBUCDEQP-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002002 slurry Substances 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
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 1
- YXSJRZBKSLLIOM-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O YXSJRZBKSLLIOM-UHFFFAOYSA-N 0.000 description 1
- PKEHCDMPTPHNCT-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;n,n-diethylethanamine Chemical compound CCN(CC)CC.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O PKEHCDMPTPHNCT-UHFFFAOYSA-N 0.000 description 1
- 101710192523 30S ribosomal protein S9 Proteins 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 101100345345 Arabidopsis thaliana MGD1 gene Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- TXFNJUJUNSLXBA-UHFFFAOYSA-N acetic acid 2-[bis(2-hydroxyethyl)amino]ethanol Chemical compound C(C)(=O)O.C(C)(=O)O.N(CCO)(CCO)CCO TXFNJUJUNSLXBA-UHFFFAOYSA-N 0.000 description 1
- HNNSBCLHPSBHEV-UHFFFAOYSA-N acetic acid;n,n-diethylethanamine Chemical compound CC(O)=O.CC(O)=O.CCN(CC)CC HNNSBCLHPSBHEV-UHFFFAOYSA-N 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- PUASVKQNSZWGLI-XRIGFGBMSA-L dipotassium;(2s)-2-[carboxylatomethyl(carboxymethyl)amino]-5-hydroxy-5-oxopentanoate Chemical compound [K+].[K+].OC(=O)CC[C@@H](C([O-])=O)N(CC(O)=O)CC([O-])=O PUASVKQNSZWGLI-XRIGFGBMSA-L 0.000 description 1
- YKZPPPNXRZHVGX-PXYKVGKMSA-L dipotassium;(2s)-2-aminobutanedioate;hydron;hydrate Chemical compound [H+].[H+].O.[K+].[K+].[O-]C(=O)[C@@H](N)CC([O-])=O.[O-]C(=O)[C@@H](N)CC([O-])=O YKZPPPNXRZHVGX-PXYKVGKMSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940068988 potassium aspartate Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 description 1
- VWNRYDSLHLCGLG-NDNWHDOQSA-J tetrasodium;(2s)-2-[bis(carboxylatomethyl)amino]butanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)C[C@@H](C([O-])=O)N(CC([O-])=O)CC([O-])=O VWNRYDSLHLCGLG-NDNWHDOQSA-J 0.000 description 1
- OHOTVSOGTVKXEL-UHFFFAOYSA-K trisodium;2-[bis(carboxylatomethyl)amino]propanoate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C(C)N(CC([O-])=O)CC([O-])=O OHOTVSOGTVKXEL-UHFFFAOYSA-K 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001161528A JP2002356464A (ja) | 2001-05-30 | 2001-05-30 | 高純度アミノポリカルボン酸及びその塩と製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001161528A JP2002356464A (ja) | 2001-05-30 | 2001-05-30 | 高純度アミノポリカルボン酸及びその塩と製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002356464A true JP2002356464A (ja) | 2002-12-13 |
| JP2002356464A5 JP2002356464A5 (https=) | 2008-06-26 |
Family
ID=19004787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001161528A Pending JP2002356464A (ja) | 2001-05-30 | 2001-05-30 | 高純度アミノポリカルボン酸及びその塩と製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002356464A (https=) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012080299A1 (en) | 2010-12-17 | 2012-06-21 | Akzo Nobel Chemicals International B.V. | Ammonium salts of chelating agents and their use in oil and gas field applications |
| US8399705B2 (en) | 2007-08-17 | 2013-03-19 | Akzo Nobel N.V. | Alkali metal salt of glutamic acid N,N-diacetic acid, a process to prepare such salt, and the use thereof |
| CN103058878A (zh) * | 2013-01-14 | 2013-04-24 | 聂世保 | 1，3丙烯基二胺四乙酸及其制备方法和应用 |
| WO2014090943A1 (en) * | 2012-12-14 | 2014-06-19 | Akzo Nobel Chemicals International B.V. | Crystalline particles of salts of glutamic acid n,n-diacetic acid |
| WO2014090942A1 (en) | 2012-12-14 | 2014-06-19 | Akzo Nobel Chemicals International B.V. | Crystalline particles of glutamic acid n,n-diacetic acid |
| US9150780B2 (en) | 2010-12-17 | 2015-10-06 | Akzo Nobel Chemicals International B.V. | Environmentally friendly stimulation fluids, processes to create wormholes in carbonate reservoirs, and processes to remove wellbore damage in carbonate reservoirs |
| US9676706B2 (en) | 2014-10-17 | 2017-06-13 | Halliburton Energy Services, Inc. | Low pH metal-free preparation of aminated organic acid |
| WO2018060212A1 (en) * | 2016-09-27 | 2018-04-05 | Camurus Ab | Mixtures and formulations comprising an alkyl ammonium edta salt |
| US10745612B2 (en) | 2016-06-30 | 2020-08-18 | Halliburton Energy Services, Inc. | Sulfonated iminodialkanoic acids formed from an iminodialkylnitrile and a sultone and methods for use thereof |
| RU2775780C2 (ru) * | 2016-09-27 | 2022-07-11 | Камурус Аб | Смеси и составы, содержащие алкиламмониевую соль эдта |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1017533A (ja) * | 1996-07-04 | 1998-01-20 | Mitsubishi Chem Corp | 高純度エチレンジアミンジオルトヒドロキシフェニル酢酸及びそれを用いた表面処理組成物 |
| JPH10265798A (ja) * | 1997-01-27 | 1998-10-06 | Mitsubishi Chem Corp | 表面処理組成物及びそれを用いた基体の表面処理方法 |
-
2001
- 2001-05-30 JP JP2001161528A patent/JP2002356464A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1017533A (ja) * | 1996-07-04 | 1998-01-20 | Mitsubishi Chem Corp | 高純度エチレンジアミンジオルトヒドロキシフェニル酢酸及びそれを用いた表面処理組成物 |
| JPH10265798A (ja) * | 1997-01-27 | 1998-10-06 | Mitsubishi Chem Corp | 表面処理組成物及びそれを用いた基体の表面処理方法 |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9080133B2 (en) | 2007-08-17 | 2015-07-14 | Akzo Nobel N.V. | Glutamic acid N,N-diacetic amide, glutamic acid N-acetic amide N-acetonitrile, alkali metal salts thereof, process to prepare them and their use |
| US8399705B2 (en) | 2007-08-17 | 2013-03-19 | Akzo Nobel N.V. | Alkali metal salt of glutamic acid N,N-diacetic acid, a process to prepare such salt, and the use thereof |
| WO2012080299A1 (en) | 2010-12-17 | 2012-06-21 | Akzo Nobel Chemicals International B.V. | Ammonium salts of chelating agents and their use in oil and gas field applications |
| US9587171B2 (en) | 2010-12-17 | 2017-03-07 | Akzo Nobel Chemicals International B.V. | Ammonium salts of chelating agents and their use in oil and gas field applications |
| US9150780B2 (en) | 2010-12-17 | 2015-10-06 | Akzo Nobel Chemicals International B.V. | Environmentally friendly stimulation fluids, processes to create wormholes in carbonate reservoirs, and processes to remove wellbore damage in carbonate reservoirs |
| WO2014090943A1 (en) * | 2012-12-14 | 2014-06-19 | Akzo Nobel Chemicals International B.V. | Crystalline particles of salts of glutamic acid n,n-diacetic acid |
| WO2014090942A1 (en) | 2012-12-14 | 2014-06-19 | Akzo Nobel Chemicals International B.V. | Crystalline particles of glutamic acid n,n-diacetic acid |
| US9738594B2 (en) | 2012-12-14 | 2017-08-22 | Akzo Nobel Chemicals International B.V. | Crystalline particles of salts of glutamic acid N,N-diacetic acid |
| US9815773B2 (en) | 2012-12-14 | 2017-11-14 | Akzo Nobel Chemicals International B.V. | Crystalline particles of glutamic acid N,N-diacetic acid |
| CN103058878B (zh) * | 2013-01-14 | 2014-08-13 | 聂世保 | 1.3丙烯基二胺四乙酸的制备方法和应用 |
| CN103058878A (zh) * | 2013-01-14 | 2013-04-24 | 聂世保 | 1，3丙烯基二胺四乙酸及其制备方法和应用 |
| US9676706B2 (en) | 2014-10-17 | 2017-06-13 | Halliburton Energy Services, Inc. | Low pH metal-free preparation of aminated organic acid |
| US10745612B2 (en) | 2016-06-30 | 2020-08-18 | Halliburton Energy Services, Inc. | Sulfonated iminodialkanoic acids formed from an iminodialkylnitrile and a sultone and methods for use thereof |
| US11248165B2 (en) | 2016-06-30 | 2022-02-15 | Halliburton Energy Services, Inc. | Sulfonated iminodialkanoic acids formed from an iminodialkylnitrile and a sultone and methods for use thereof |
| WO2018060212A1 (en) * | 2016-09-27 | 2018-04-05 | Camurus Ab | Mixtures and formulations comprising an alkyl ammonium edta salt |
| US10688148B2 (en) | 2016-09-27 | 2020-06-23 | Camurus Ab | Formulations containing a somatostatin receptor agonist |
| AU2017336199B2 (en) * | 2016-09-27 | 2020-08-20 | Camurus Ab | Mixtures and formulations comprising an alkyl ammonium EDTA salt |
| US11135264B2 (en) | 2016-09-27 | 2021-10-05 | Camurus Ab | Formulations containing a somatostatin receptor agonist |
| US11241476B2 (en) | 2016-09-27 | 2022-02-08 | Camurus Ab | Mixtures and formulations comprising an alkyl ammonium EDTA salt |
| CN109789214A (zh) * | 2016-09-27 | 2019-05-21 | 卡姆拉斯公司 | 包含edta烷基铵盐的混合物和制剂 |
| CN109789214B (zh) * | 2016-09-27 | 2022-06-28 | 卡姆拉斯公司 | 包含edta烷基铵盐的混合物和制剂 |
| RU2775780C2 (ru) * | 2016-09-27 | 2022-07-11 | Камурус Аб | Смеси и составы, содержащие алкиламмониевую соль эдта |
| US11564968B2 (en) | 2016-09-27 | 2023-01-31 | Camurus Ab | Formulations containing a somatostatin receptor agonist |
| US12257282B2 (en) | 2016-09-27 | 2025-03-25 | Camarus Ab | Mixtures and formulations |
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