CA2285308C - Preparation and use of iminodisuccinic acid salts - Google Patents
Preparation and use of iminodisuccinic acid salts Download PDFInfo
- Publication number
- CA2285308C CA2285308C CA002285308A CA2285308A CA2285308C CA 2285308 C CA2285308 C CA 2285308C CA 002285308 A CA002285308 A CA 002285308A CA 2285308 A CA2285308 A CA 2285308A CA 2285308 C CA2285308 C CA 2285308C
- Authority
- CA
- Canada
- Prior art keywords
- water
- ammonia
- mol
- solution
- alkali metal
- 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.)
- Expired - Fee Related
Links
- PQHYOGIRXOKOEJ-UHFFFAOYSA-N 2-(1,2-dicarboxyethylamino)butanedioic acid Chemical class OC(=O)CC(C(O)=O)NC(C(O)=O)CC(O)=O PQHYOGIRXOKOEJ-UHFFFAOYSA-N 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 109
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000007787 solid Substances 0.000 claims abstract description 37
- -1 Iminodisuccinic acid alkaline salts Chemical class 0.000 claims abstract description 21
- 239000011541 reaction mixture Substances 0.000 claims abstract description 15
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 198
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 187
- 239000000243 solution Substances 0.000 claims description 72
- 229910021529 ammonia Inorganic materials 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 35
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 229920001131 Pulp (paper) Polymers 0.000 claims description 13
- 238000004061 bleaching Methods 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- 239000012266 salt solution Substances 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000009895 reductive bleaching Methods 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 238000009896 oxidative bleaching Methods 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 51
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 51
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 42
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 30
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 30
- 239000011976 maleic acid Substances 0.000 description 30
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 21
- 235000003704 aspartic acid Nutrition 0.000 description 21
- 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 21
- 239000001530 fumaric acid Substances 0.000 description 21
- 239000008139 complexing agent Substances 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 6
- 229910001385 heavy metal Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000001630 malic acid Substances 0.000 description 6
- 235000011090 malic acid Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229910004878 Na2S2O4 Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002352 surface water Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 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 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241001484259 Lacuna Species 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- CKKXWJDFFQPBQL-UAIGNFCESA-N diazanium;(z)-but-2-enedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)\C=C/C([O-])=O CKKXWJDFFQPBQL-UAIGNFCESA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000012851 eutrophication Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 150000002689 maleic acids Chemical class 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
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910001453 nickel ion Inorganic materials 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- D21C9/1084—Bleaching ; Apparatus therefor with reducing compounds
- D21C9/1089—Bleaching ; Apparatus therefor with reducing compounds with dithionites
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the 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
-
- 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
- D21C9/16—Bleaching ; Apparatus therefor with per compounds
- D21C9/163—Bleaching ; Apparatus therefor with per compounds with peroxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19713911A DE19713911A1 (de) | 1997-04-04 | 1997-04-04 | Herstellung und Verfahren von Iminodibernsteinsäuresalzen |
| DE19713911.6 | 1997-04-04 | ||
| PCT/EP1998/001670 WO1998045251A1 (de) | 1997-04-04 | 1998-03-23 | Herstellung und verwendung von iminodibernsteinsäuresalzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285308A1 CA2285308A1 (en) | 1998-10-15 |
| CA2285308C true CA2285308C (en) | 2007-07-24 |
Family
ID=7825432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285308A Expired - Fee Related CA2285308C (en) | 1997-04-04 | 1998-03-23 | Preparation and use of iminodisuccinic acid salts |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6107518A (enExample) |
| EP (2) | EP0975582B1 (enExample) |
| JP (2) | JP4027992B2 (enExample) |
| KR (2) | KR100592446B1 (enExample) |
| AT (2) | ATE227260T1 (enExample) |
| AU (1) | AU7039998A (enExample) |
| BR (1) | BR9809063A (enExample) |
| CA (1) | CA2285308C (enExample) |
| DE (3) | DE19713911A1 (enExample) |
| DK (1) | DK0975582T3 (enExample) |
| ES (1) | ES2183345T3 (enExample) |
| PT (1) | PT975582E (enExample) |
| WO (1) | WO1998045251A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6870026B1 (en) | 1999-09-17 | 2005-03-22 | Lidochem, Inc. | Chelation compositions |
| US6444614B2 (en) | 2000-04-12 | 2002-09-03 | Lidochem Inc. | Aspartic acid derivative-containing compositions and use thereof in stimulating and/or regulating plant and plant precursor growth |
| US7166688B1 (en) * | 2000-07-08 | 2007-01-23 | Lidochem, Inc. | Chelation compositions |
| DE10034102A1 (de) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen in Form von Gelen, enthaltend Iminodibernsteinsäure |
| DE10034101A1 (de) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen in Form von Emulsionen, enthaltend Iminodibernsteinsäure |
| DE10100720A1 (de) * | 2001-01-10 | 2002-07-11 | Beiersdorf Ag | Kosmetische und dermatologische waschaktive Zubereitungen, enthaltend eine wirksame Menge an Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140540A1 (de) * | 2001-08-17 | 2003-03-06 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an wasserlöslichen UV-Filtersubstanzen und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140537A1 (de) * | 2001-08-17 | 2003-02-27 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinen und/oder Triazinderivaten und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140546A1 (de) * | 2001-08-17 | 2003-03-06 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an öllöslichen UV-Filtersubstanzen und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140547A1 (de) * | 2001-08-17 | 2003-02-27 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an bei Raumtemperatur flüssigen UV-Filtersubstanzen und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140548A1 (de) * | 2001-08-17 | 2003-02-27 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Dibenzoylmethanderivaten und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10140536A1 (de) * | 2001-08-17 | 2003-02-27 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Benzotriazolen und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10142927A1 (de) * | 2001-09-01 | 2003-03-20 | Beiersdorf Ag | Erhöhung der Stabilität von kosmetischen Zubereitungen durch Zusatz von Iminodibernsteinsäure |
| DE10142931A1 (de) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Erhöhung der hautbefeuchtenden Eigenschaften von Polyolen |
| DE10142932A1 (de) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Erhöhung der Stabilität von lecithin-und chitosanhaltigen Formulierungen durch Zusatz von Iminodibernsteinsäure |
| DE10155965A1 (de) * | 2001-11-09 | 2003-05-22 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Hydroxybenzophenonen und Iminodibernsteinsäure und/oder ihren Salzen |
| DE10219037A1 (de) * | 2002-04-29 | 2003-11-06 | Bayer Ag | Herstellung und Verwendung von Iminodibernsteinsäureammoniummetallsalzen |
| DE10248022B4 (de) * | 2002-10-15 | 2008-11-13 | Lanxess Deutschland Gmbh | Verwendung chelatisierter Pflanzenspurennährstoffe |
| DE10301535A1 (de) * | 2003-01-17 | 2004-07-29 | Cht R. Beitlich Gmbh | Verfahren zur Veredlung von textilem Fasermaterial |
| DE102004012873A1 (de) * | 2004-03-16 | 2005-10-06 | Bayer Chemicals Ag | Lagerstabile Iminodisuccinatlösungen |
| CN100341847C (zh) * | 2005-02-07 | 2007-10-10 | 刘启民 | 一种可降解螯合型表面活性剂及生产方法 |
| EP1811080A1 (en) * | 2006-01-24 | 2007-07-25 | Solvay SA | Process for the bleaching of mechanical paper pulp |
| DE102006008689B4 (de) | 2006-02-24 | 2012-01-26 | Lanxess Deutschland Gmbh | Poliermittel und dessen Verwendung |
| EP2113044A1 (en) * | 2007-02-21 | 2009-11-04 | SOLVAY (Société Anonyme) | Process for the bleaching of paper pulp |
| GB0721587D0 (en) * | 2007-11-02 | 2007-12-12 | Innospec Ltd | Process for bleaching pulp |
| US20140202646A1 (en) * | 2013-01-23 | 2014-07-24 | Buckman Laboratories International, Inc. | Bleach Stabilizer Compositions And Methods |
| CN103320139B (zh) * | 2013-06-09 | 2016-06-15 | 沈阳大学 | 一种用于治理重金属污染土壤的环保型淋洗液 |
| CN105461579B (zh) * | 2015-12-24 | 2019-04-02 | 石家庄铁道大学 | 一种亚氨基二琥珀酸及其盐的制备方法 |
| CA3082580A1 (en) | 2017-12-14 | 2019-06-20 | Colgate-Palmolive Company | Antiperspirant/deodorant compositions including biodegradable amino carboxylates and methods for the same |
| CN108997170B (zh) * | 2018-08-07 | 2021-04-06 | 贾国苓 | 一种易碱解多羧基螯合物及其制备工艺 |
| DE102019124958B4 (de) | 2019-09-17 | 2023-03-23 | Zschimmer & Schwarz Mohsdorf GmbH & Co. KG. | Phosphonsäurederivate und Verfahren zu deren Herstellung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1306331A (enExample) * | 1970-12-07 | 1973-02-07 | ||
| US5362412A (en) * | 1991-04-17 | 1994-11-08 | Hampshire Chemical Corp. | Biodegradable bleach stabilizers for detergents |
| JPH06329606A (ja) * | 1993-05-24 | 1994-11-29 | Nippon Shokubai Co Ltd | イミノジコハク酸金属塩の製造方法 |
| DE4340043A1 (de) * | 1993-11-24 | 1995-06-01 | Henkel Kgaa | Verwendung Stickstoff-haltiger Komplexbildner bei der Holzstoffbleiche |
| JPH0812631A (ja) * | 1994-06-24 | 1996-01-16 | Nitto Chem Ind Co Ltd | イミノジコハク酸とそのアルカリ金属塩の製造法およびそれらを含む生分解性キレート剤 |
| JPH0841490A (ja) * | 1995-06-23 | 1996-02-13 | Nippon Shokubai Co Ltd | 生分解性の改良された洗剤用ビルダーおよび洗浄剤組成物 |
| DE19638569A1 (de) * | 1996-09-20 | 1998-04-02 | Bayer Ag | Bleichregulatoren und Bleichverfahren damit |
-
1997
- 1997-04-04 DE DE19713911A patent/DE19713911A1/de not_active Withdrawn
-
1998
- 1998-03-23 DK DK98917048T patent/DK0975582T3/da active
- 1998-03-23 EP EP98917048A patent/EP0975582B1/de not_active Expired - Lifetime
- 1998-03-23 WO PCT/EP1998/001670 patent/WO1998045251A1/de not_active Ceased
- 1998-03-23 EP EP02010124A patent/EP1247800B1/de not_active Expired - Lifetime
- 1998-03-23 KR KR1020057017741A patent/KR100592446B1/ko not_active Expired - Fee Related
- 1998-03-23 DE DE59813446T patent/DE59813446D1/de not_active Expired - Lifetime
- 1998-03-23 JP JP54230498A patent/JP4027992B2/ja not_active Expired - Lifetime
- 1998-03-23 AU AU70399/98A patent/AU7039998A/en not_active Abandoned
- 1998-03-23 ES ES98917048T patent/ES2183345T3/es not_active Expired - Lifetime
- 1998-03-23 CA CA002285308A patent/CA2285308C/en not_active Expired - Fee Related
- 1998-03-23 DE DE59806191T patent/DE59806191D1/de not_active Expired - Lifetime
- 1998-03-23 BR BR9809063-1A patent/BR9809063A/pt not_active Application Discontinuation
- 1998-03-23 AT AT98917048T patent/ATE227260T1/de active
- 1998-03-23 AT AT02010124T patent/ATE321020T1/de not_active IP Right Cessation
- 1998-03-23 KR KR10-1999-7009039A patent/KR100539643B1/ko not_active Expired - Fee Related
- 1998-03-23 US US09/381,792 patent/US6107518A/en not_active Expired - Lifetime
- 1998-03-23 PT PT98917048T patent/PT975582E/pt unknown
-
2000
- 2000-06-01 US US09/585,224 patent/US6207010B1/en not_active Expired - Lifetime
-
2007
- 2007-08-15 JP JP2007211739A patent/JP2007327168A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1247800B1 (de) | 2006-03-22 |
| KR20010005962A (ko) | 2001-01-15 |
| ES2183345T3 (es) | 2003-03-16 |
| CA2285308A1 (en) | 1998-10-15 |
| ATE321020T1 (de) | 2006-04-15 |
| AU7039998A (en) | 1998-10-30 |
| US6107518A (en) | 2000-08-22 |
| KR20050100709A (ko) | 2005-10-19 |
| KR100539643B1 (ko) | 2005-12-29 |
| EP1247800A1 (de) | 2002-10-09 |
| KR100592446B1 (ko) | 2006-06-22 |
| US6207010B1 (en) | 2001-03-27 |
| BR9809063A (pt) | 2000-08-01 |
| JP4027992B2 (ja) | 2007-12-26 |
| WO1998045251A1 (de) | 1998-10-15 |
| DE59806191D1 (de) | 2002-12-12 |
| EP0975582A1 (de) | 2000-02-02 |
| DE19713911A1 (de) | 1998-10-08 |
| EP0975582B1 (de) | 2002-11-06 |
| PT975582E (pt) | 2003-03-31 |
| JP2001519792A (ja) | 2001-10-23 |
| ATE227260T1 (de) | 2002-11-15 |
| JP2007327168A (ja) | 2007-12-20 |
| DK0975582T3 (da) | 2003-02-24 |
| DE59813446D1 (de) | 2006-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2285308C (en) | Preparation and use of iminodisuccinic acid salts | |
| DE69227479T2 (de) | Bioabbaubare Bleichstabilisatoren für Waschmittel | |
| US6569286B1 (en) | Method for the alkaline bleaching of pulp with a peroxyacid based oxygen bleaching species using an agglomerated bleach activator | |
| CA2321543C (en) | Methods for the preparation of an n-bis-[2-(1,2-dicarboxy-ethoxy)-ethyl]amine derivative and products of the methods and their uses | |
| CN104471146B (zh) | 漂白纸浆的方法 | |
| EP0740015B1 (en) | Ethylenediaminetriacetic acid and salts thereof as chelating agents in pulp bleaching | |
| EP1127153A1 (de) | Verfahren zur herstellung von asparaginsäurederivaten | |
| Kuwabara et al. | Impact on the filtrate from bleached pulp treated with peroxymonosulfuric acid for effective removal of hexenuronic acid | |
| EP1607519B1 (en) | Activator for pulp bleaching | |
| KR100874635B1 (ko) | 반도체 제조 부산 인산액으로부터 비료를 합성하는 방법 | |
| US4950787A (en) | Chemical process | |
| JP3804091B2 (ja) | アントラハイドロキノンのアルカリ塩溶液の製造方法 | |
| RU2200155C2 (ru) | Способ получения раствора пероксокислот для делигнификации и отбеливания | |
| KR100482289B1 (ko) | 과산화물 표백에 사용되는 안정제 조성물 및 과산화물 표백제의 안정화 방법 | |
| JP3444306B2 (ja) | 二酸化チオ尿素の製造法および同製造法による二酸化チオ尿素を用いた製紙用パルプの漂白方法 | |
| CN113735724B (zh) | 天冬氨酸二乙酸钠及其制备方法 | |
| JPH02229146A (ja) | グリセリンアミノカルボキシレート、その製法及びそれより成る重金属イオン及びアルカリ土類金属イオンに対する錯化剤 | |
| CA1312623C (en) | Process for preparing 1-hydroxy-3-oxa-1,2,4,5-pentane tetracarboxylic acid and 3,6-dioxa-1,2,4,5,7,8-octane hexacarboxylic acid | |
| JPH0710832A (ja) | 二酸化チオ尿素の製造法および同製造法による二酸化チオ尿素を用いた製紙用パルプの漂白方法 | |
| RU2113422C1 (ru) | Способ переработки продуктов биохимического окисления сульфитных щелоков | |
| CN113214098A (zh) | 一种二乙烯三胺五乙酸五钠的制备方法 | |
| CA2743838A1 (en) | Composition and process for bleaching of mechanical wood pulp | |
| CA3067494A1 (en) | Process for the preparation of a mixture of chelating agents, mixture of chelating agents and methods of using them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |