FI112075B - N-bis- eller N-tris[(1,2-dikarboxyl-etoxi)-etyl]aminderivat, framställning och användning av dem - Google Patents
N-bis- eller N-tris[(1,2-dikarboxyl-etoxi)-etyl]aminderivat, framställning och användning av dem Download PDFInfo
- Publication number
- FI112075B FI112075B FI962261A FI962261A FI112075B FI 112075 B FI112075 B FI 112075B FI 962261 A FI962261 A FI 962261A FI 962261 A FI962261 A FI 962261A FI 112075 B FI112075 B FI 112075B
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- FI
- Finland
- Prior art keywords
- compounds
- formula
- ethyl
- acid
- alkaline earth
- Prior art date
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- -1 1,2-dicarboxyl-ethoxy Chemical group 0.000 title claims abstract description 12
- 239000007983 Tris buffer Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 title claims description 3
- 239000002738 chelating agent Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 24
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 19
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000011976 maleic acid Substances 0.000 claims description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000002601 lanthanoid compounds Chemical class 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000002386 leaching Methods 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 239000011541 reaction mixture Substances 0.000 description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 16
- 238000004061 bleaching Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910001385 heavy metal Inorganic materials 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000009920 chelation Effects 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000001630 malic acid Substances 0.000 description 4
- 235000011090 malic acid Nutrition 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 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 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010934 O-alkylation reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229960001484 edetic acid Drugs 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229960005261 aspartic acid Drugs 0.000 description 2
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 159000000011 group IA salts Chemical class 0.000 description 2
- 150000002604 lanthanum compounds Chemical class 0.000 description 2
- CZMAIROVPAYCMU-UHFFFAOYSA-N lanthanum(3+) Chemical class [La+3] CZMAIROVPAYCMU-UHFFFAOYSA-N 0.000 description 2
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 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 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- NFGMTENHSQDVJW-UHFFFAOYSA-K lanthanum(3+);octanoate Chemical compound [La+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NFGMTENHSQDVJW-UHFFFAOYSA-K 0.000 description 1
- OXHNIMPTBAKYRS-UHFFFAOYSA-H lanthanum(3+);oxalate Chemical compound [La+3].[La+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O OXHNIMPTBAKYRS-UHFFFAOYSA-H 0.000 description 1
- VQEHIYWBGOJJDM-UHFFFAOYSA-H lanthanum(3+);trisulfate Chemical compound [La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VQEHIYWBGOJJDM-UHFFFAOYSA-H 0.000 description 1
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 238000004076 pulp bleaching Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/037—Stabilisation by additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/10—Bleaching ; Apparatus therefor
- D21C9/1026—Other features in bleaching processes
- D21C9/1042—Use of chelating agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paper (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Claims (13)
1. N-bis- eller N-tris-[(1,2-dikarboxi-etoxi)-etyl]-amin- derivat med formeln 5 R-.OOC--- R‘ ^-COORj R2OOC ° COOR2 10 (I) cHrCOOR2 cHrCOOR^ I där R,är H, I eller CH2-CH2 /CH\ CH_ / COOR2 / ^~COOR2 / ° 15 och R2 är väte, en alkalimetall eller en alkalisk jordartsmetall.
2. Förening enligt krav 1, kännetecknad av att 20 den är N-bis-[(1,2-dikarboxi-etoxi)-etyl]-amin eller ett Na+, K+, Ca2+ eller Mg2+ -salt därav. • ·
3. Förening enligt krav 1, kännetecknad av att • · den är N-bis-[(1,2-dikarboxi-etoxi)-etyl]-asparagin-syra : :*: 25 eller ett Na+, K+, Ca2+ eller Mg2+ -salt därav.
4. Förening enligt krav 1, kännetecknad av att den är N-tris-[ (1,2-dikarboxi-etoxi) -etyl] -amin eller ett Na+,K+, Ca2+ eller Mg2+ -salt därav. 30
5. Förfarande för framställning av föreningar med formel I I ! enligt krav 1, vilket förfarande är i och för sig kännat, kännetecknat av att di- eller trietanolamin , bringas att reagera med ett alkalimetall- eller ’ ' 35 jordalkalimetallsalt av maleinsyra för bildning av en förening med formel I, varvid man säsom katalysator använder 112075 lantanidföreningar, blandningar av lantanid-föreningar eller föreningar av alkaliska jordartsmetaller.
6. Förfarande enligt krav 5, kännetecknat av att 5 di- eller trietanolamin bringas att reagera med ett alka-limetall- eller jordalkalimetallsalt av malein-syra i närvaro av en La3+-katalysator tili bildning av en förening med formel I. 10
7. Förfarande enligt krav 5, kännetecknat av att alkalimetall- eller jordalkalimetallsaltet av malein-syra framställes genom en reaktion mellan maleinsyraan-hydrid och en hydroxid eller ett karbonat av en alkalimetall eller en alkalisk jordartsmetall. 15
8. Förfarande enligt krav 5, kännetecknat av att reaktionen genomföres vid en temperatur av 75-95°C.
9. Användning av föreningar med formel I enligt krav 1 säsom 20 kelatbildare för metaller. i » ·
10. Användning av föreningar med formel I enligt krav 1 säsom kelatbildare för metaller i samband med massablekning.
11. Användning av föreningar med formel I enligt krav 1 ;.· i alkaliska vattenlösningar som innehäller väteperoxid eller ,· · peroxiföreningar.
12. Användning av föreningar med formel I enligt krav 1 30 säsom kelatbildare i detergenter, rengöringsmedel och desinfektionsmedel. * * * * • »
13. Användning av föreningar med formel I enligt krav 1 säsom kelatbildare i fotokemikalier. • I < · > * > » » ·
Priority Applications (24)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI962261A FI112075B (sv) | 1996-05-30 | 1996-05-30 | N-bis- eller N-tris[(1,2-dikarboxyl-etoxi)-etyl]aminderivat, framställning och användning av dem |
FI970304A FI105932B (sv) | 1996-05-30 | 1997-01-24 | Förfarande för blekning av högbytes- eller returfibermassa |
FI970303A FI104572B (sv) | 1996-05-30 | 1997-01-24 | Förfarande för blekning av kemisk massa |
PT97924047T PT904263E (pt) | 1996-05-30 | 1997-05-30 | Derivados de n-bis- ou n-tris-¬(1,2-dicarboxi-etoxi)-etil|-amina e preparacao e utilizacao dos mesmos |
AU29643/97A AU2964397A (en) | 1996-05-30 | 1997-05-30 | N-bis- or n-tris-{(1,2-dicarboxy-ethoxy)-ethyl}-amine derivatives and preparation and use of the same |
JP54169397A JP3901735B2 (ja) | 1996-05-30 | 1997-05-30 | N―ビス―またはn―トリス〔(1,2―ジカルボキシエトキシ)エチル〕アミン誘導体およびそれらの製造および用途 |
BR9709393A BR9709393A (pt) | 1996-05-30 | 1997-05-30 | Derivados de n-bis ou n-tris-[(1,2-dicarbóxietóxi)etil] amina e preparação e uso dos mesmos |
AT97924047T ATE198316T1 (de) | 1996-05-30 | 1997-05-30 | N-bis- oder n-tris-((1,2-dicarboxy-ethoxy)-ethyl)-amin-deri ate und herstellung und anwendung derselben |
PCT/FI1997/000332 WO1997045396A1 (en) | 1996-05-30 | 1997-05-30 | N-bis- or n-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivatives and preparation and use of the same |
CNB971951357A CN1158243C (zh) | 1996-05-30 | 1997-05-30 | N-双-或n-三-[(1,2-二羟基-乙氧基)-乙基]胺衍生物以及它们的制备和用途 |
PCT/FI1997/000334 WO1997045585A1 (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of high yield pulp or recycled paper pulp |
CA002256559A CA2256559C (en) | 1996-05-30 | 1997-05-30 | N-bis- or n-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivatives and preparation and use of the same |
CA002256579A CA2256579C (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of chemical pulp |
DE69703796T DE69703796T2 (de) | 1996-05-30 | 1997-05-30 | N-bis- oder n-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amin-derivate und herstellung und anwendung derselben |
EP97924047A EP0904263B1 (en) | 1996-05-30 | 1997-05-30 | N-bis- or n-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivatives and preparation and use of the same |
ES97924047T ES2154902T3 (es) | 1996-05-30 | 1997-05-30 | Derivados de la n-bis o n-tris-((1,2-dicarboxi-etoxi)-etil)-amina y a la preparacion y empleo de los mismos. |
AU29644/97A AU2964497A (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of chemical pulp |
US09/194,349 US6264790B1 (en) | 1996-05-30 | 1997-05-30 | Process for the peracid bleaching of chelated chemical pulp |
AT97924048T ATE252178T1 (de) | 1996-05-30 | 1997-05-30 | Verfahren zum bleichen von zellstoff |
EP97924048A EP0907788B1 (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of chemical pulp |
PCT/FI1997/000333 WO1997045586A1 (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of chemical pulp |
US09/194,310 US6093849A (en) | 1996-05-30 | 1997-05-30 | N-bis- or N-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivatives and preparation and use of the same |
AU29645/97A AU2964597A (en) | 1996-05-30 | 1997-05-30 | Process for the bleaching of high yield pulp or recycled paper pulp |
DE69725573T DE69725573T2 (de) | 1996-05-30 | 1997-05-30 | Verfahren zum bleichen von zellstoff |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI962261A FI112075B (sv) | 1996-05-30 | 1996-05-30 | N-bis- eller N-tris[(1,2-dikarboxyl-etoxi)-etyl]aminderivat, framställning och användning av dem |
FI962261 | 1996-05-30 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI962261A0 FI962261A0 (sv) | 1996-05-30 |
FI962261A FI962261A (sv) | 1997-12-01 |
FI112075B true FI112075B (sv) | 2003-10-31 |
Family
ID=8546117
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI962261A FI112075B (sv) | 1996-05-30 | 1996-05-30 | N-bis- eller N-tris[(1,2-dikarboxyl-etoxi)-etyl]aminderivat, framställning och användning av dem |
Country Status (13)
Country | Link |
---|---|
US (1) | US6093849A (sv) |
EP (1) | EP0904263B1 (sv) |
JP (1) | JP3901735B2 (sv) |
CN (1) | CN1158243C (sv) |
AT (1) | ATE198316T1 (sv) |
AU (1) | AU2964397A (sv) |
BR (1) | BR9709393A (sv) |
CA (1) | CA2256559C (sv) |
DE (1) | DE69703796T2 (sv) |
ES (1) | ES2154902T3 (sv) |
FI (1) | FI112075B (sv) |
PT (1) | PT904263E (sv) |
WO (1) | WO1997045396A1 (sv) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI105214B (sv) * | 1997-11-13 | 2000-06-30 | Kemira Chemicals Oy | Effektiverat förfarande för blekning av en kemisk massa |
FI106258B (sv) | 1998-03-09 | 2000-12-29 | Kemira Chemicals Oy | Förfaranden för framställning av ett N-bis-[2-(1,2-dikarboxi-etoxi)-etyl]aminderivat samt produkter som erhålls genom förfarandena och användningar därav |
DE60020318T2 (de) | 1999-09-03 | 2006-05-18 | Nippon Shokubai Co., Ltd. | Zusammensetzung von Aminosäure-Derivaten und Verfahren zur Herstellung von einem Aminosäure-Derivat |
JP4632500B2 (ja) * | 1999-09-03 | 2011-02-16 | 株式会社日本触媒 | アミノ酸誘導体組成物及びアミノ酸誘導体の製造方法 |
FI122828B (sv) | 2010-06-02 | 2012-07-31 | Kemira Oyj | Förfarande för återvinning av en katalysator |
FI122829B (sv) | 2010-06-02 | 2012-07-31 | Kemira Oyj | Förfarande för framställning av en blandning av kelaterande ämnen |
US9745504B2 (en) | 2013-03-21 | 2017-08-29 | Halliburton Energy Services, Inc. | Wellbore servicing compositions and methods of making and using same |
US9512348B2 (en) | 2013-03-28 | 2016-12-06 | Halliburton Energy Services, Inc. | Removal of inorganic deposition from high temperature formations with non-corrosive acidic pH fluids |
SI2902544T1 (sl) * | 2014-01-30 | 2017-09-29 | Archroma France Sas | Vodni sestavek, ki obsega polivalentno kovino, ki tvori komplekse s kabonatnimi ligandi in ligandi karboksilne kisline, ter njegova uporaba |
CN106905171B (zh) * | 2017-03-31 | 2018-12-11 | 浙江大学 | 2-[2-叔丁氧基乙氧基]-乙胺的制备方法 |
BR112019027294A2 (pt) * | 2017-06-30 | 2020-07-21 | Kemira Oyj | processo para preparação de mistura de agentes quelantes, mistura de agentes quelantes e métodos de uso |
CN110891931B (zh) | 2017-06-30 | 2022-11-08 | 凯米拉公司 | 制备螯合剂混合物的方法、螯合剂混合物及其使用方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4044034A (en) * | 1975-07-22 | 1977-08-23 | The Miranol Chemical Company, Inc. | Nitrogenous condensation products |
JP2896541B2 (ja) * | 1991-09-11 | 1999-05-31 | コニカ株式会社 | ハロゲン化銀写真感光材料用処理液 |
JPH06282044A (ja) * | 1993-03-26 | 1994-10-07 | Konica Corp | ハロゲン化銀写真感光材料用固形処理剤包装体 |
JPH07120894A (ja) * | 1993-10-21 | 1995-05-12 | Fuji Photo Film Co Ltd | 写真用処理組成物及び処理方法 |
JPH07120899A (ja) * | 1993-10-27 | 1995-05-12 | Fuji Photo Film Co Ltd | 写真用処理組成物及び処理方法 |
JPH07261355A (ja) * | 1994-03-17 | 1995-10-13 | Fuji Photo Film Co Ltd | カラー写真用処理装置および処理方法 |
-
1996
- 1996-05-30 FI FI962261A patent/FI112075B/sv not_active IP Right Cessation
-
1997
- 1997-05-30 PT PT97924047T patent/PT904263E/pt unknown
- 1997-05-30 AU AU29643/97A patent/AU2964397A/en not_active Abandoned
- 1997-05-30 DE DE69703796T patent/DE69703796T2/de not_active Expired - Lifetime
- 1997-05-30 WO PCT/FI1997/000332 patent/WO1997045396A1/en active IP Right Grant
- 1997-05-30 ES ES97924047T patent/ES2154902T3/es not_active Expired - Lifetime
- 1997-05-30 JP JP54169397A patent/JP3901735B2/ja not_active Expired - Fee Related
- 1997-05-30 AT AT97924047T patent/ATE198316T1/de active
- 1997-05-30 BR BR9709393A patent/BR9709393A/pt not_active IP Right Cessation
- 1997-05-30 CA CA002256559A patent/CA2256559C/en not_active Expired - Fee Related
- 1997-05-30 US US09/194,310 patent/US6093849A/en not_active Expired - Lifetime
- 1997-05-30 CN CNB971951357A patent/CN1158243C/zh not_active Expired - Fee Related
- 1997-05-30 EP EP97924047A patent/EP0904263B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1158243C (zh) | 2004-07-21 |
PT904263E (pt) | 2001-04-30 |
AU2964397A (en) | 1998-01-05 |
US6093849A (en) | 2000-07-25 |
WO1997045396A1 (en) | 1997-12-04 |
JP2000515121A (ja) | 2000-11-14 |
DE69703796D1 (de) | 2001-02-01 |
CN1220659A (zh) | 1999-06-23 |
FI962261A (sv) | 1997-12-01 |
BR9709393A (pt) | 1999-08-10 |
CA2256559A1 (en) | 1997-12-04 |
EP0904263B1 (en) | 2000-12-27 |
FI962261A0 (sv) | 1996-05-30 |
DE69703796T2 (de) | 2001-04-19 |
CA2256559C (en) | 2006-05-02 |
ATE198316T1 (de) | 2001-01-15 |
EP0904263A1 (en) | 1999-03-31 |
ES2154902T3 (es) | 2001-04-16 |
JP3901735B2 (ja) | 2007-04-04 |
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