DE1045373B - Use of phosphonic acids - Google Patents
Use of phosphonic acidsInfo
- Publication number
- DE1045373B DE1045373B DEF22912A DEF0022912A DE1045373B DE 1045373 B DE1045373 B DE 1045373B DE F22912 A DEF22912 A DE F22912A DE F0022912 A DEF0022912 A DE F0022912A DE 1045373 B DE1045373 B DE 1045373B
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic acids
- acid
- ions
- phosphonates
- dyes
- 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
- 150000003009 phosphonic acids Chemical class 0.000 title claims description 7
- 239000008139 complexing agent Substances 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- -1 Halogen esters Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910001424 calcium ion Inorganic materials 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
- 239000008233 hard water Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 102000005701 Calcium-Binding Proteins Human genes 0.000 description 2
- 108010045403 Calcium-Binding Proteins Proteins 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- PUVMVPFLXCHEOY-UHFFFAOYSA-N 3-phosphonopropylphosphonic acid Chemical compound OP(O)(=O)CCCP(O)(O)=O PUVMVPFLXCHEOY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- RXSYPQBNTPQOTQ-UHFFFAOYSA-L disodium;hydroxy-[[hydroxy(oxido)phosphoryl]methyl]phosphinate Chemical compound [Na+].[Na+].OP([O-])(=O)CP(O)([O-])=O RXSYPQBNTPQOTQ-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/08—Preparations for bleaching the hair
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3843—Polyphosphonic acids containing no further substituents than -PO3H2 groups
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/361—Phosphonates, phosphinates or phosphonites
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/365—Organic compounds containing phosphorus containing carboxyl groups
-
- 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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3937—Stabilising agents
- C11D3/394—Organic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
- G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/51—Chelating agents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- General Chemical & Material Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
Description
Verwendung von Phosphonsäuren Es ist bereits bekannt, daß sich Pyro- und Polvphosphate als Komplexbildnngsmittel für mdrwertige Metalle eignen. Diese Phosphate haben jedoch den Nachteil, daß sie bei steigenden p-Werten und Temperaturen zu unwirksamer o-Phospho,rsäure hydrolysiert werden. Sie sind deshalb nur sehr beschränkt anwendbar.Use of phosphonic acids It is already known that pyro- and poly phosphates are suitable as complexing agents for low-grade metals. These However, phosphates have the disadvantage that with increasing p-values and temperatures hydrolyzed to ineffective o-phosphorous acid. They are therefore only very limited applicable.
Es ist fernerbekannt, Poiyphosphonate - hergestellt aus z. B. Äthulendiamin oder seinen N-Alkylverbindungen oder seiner N-,N'-Diessigsäure und 2 Mol Chlormetltylphosphonsäure - als Komplexbildner zu verwenden. Entscheidend für die Wirksamkeit dieser Verbindungen ist die Kombination einer Phosphonatmit einer Aminogruppe. Erst die Einführung dieser Aminogruppe mit den freien Elektronenpaaren ermöglicht die Komplexbildung. It is also known to use polyphosphonates - made from e.g. B. Ethulene diamine or its N-alkyl compounds or its N-, N'-diacetic acid and 2 moles of chloromethylphosphonic acid - to be used as a complexing agent. Critical to the effectiveness of these compounds is the combination of a phosphonate with an amino group. Only the introduction of this Amino group with the free electron pairs enables complex formation.
Demgegenfiber sind stickstofffreie Polyphosphonate in der Regel keine Komplexbildner, wie beispielsweise die Verbindungen lithan-1,2-diphosphonsäure und Propan-1,3-diphosphonsäure zeigen. In contrast, nitrogen-free polyphosphonates are usually not Complexing agents, such as, for example, the compounds lithane-1,2-diphosphonic acid and Show propane-1,3-diphosphonic acid.
Es wurde gefunden, daß Diphosphonsäuren und Phosphoncarbonsäuren, deren funktionelle Gruppen nur durch eine C H2-Gruppe verbunden sind. bzw. ihre Alkalisalze sich vorzüglich als Komplexbildner eignen. It has been found that diphosphonic acids and phosphonic carboxylic acids, whose functional groups are only linked by a C H2 group. or their Alkali salts are particularly suitable as complexing agents.
Die Phosphonsäuren lassen sich nach verschiedenen, an sich bekannten Verfahren herstellen. Beispielsweise kann man aus Chloressigsäurealkylestern durch Umsatz mit Trialkylphosphiten den Phosphonessigsäure-trialkylester erhalten, der bei der Verseifung in glatter Reaktion die Phosphonessigsäure gibt. Man kann ferner Halogenester, wie z. B. Chlofmethylphosphonsäure-dialkylester, mit Alkali-dialkylphosphiten zu Diphosphon- bzw. Phosphoncarhonsäureestern kondensieren und diese in üblicher Weise zu den Säuren verseifen. The phosphonic acids can be classified according to various known per se Process. For example, you can from chloroacetic acid alkyl esters by Sales with trialkyl phosphites obtained the trialkyl phosphonoacetate, the in the saponification the phosphonoacetic acid gives in a smooth reaction. One can also Halogen esters, such as. B. Chlofmethylphosphonsäure dialkyl ester, with alkali dialkyl phosphites Condense to diphosphonic or phosphonic acid esters and these in the usual way Way to saponify the acids.
Die stickstoffhaltigen Polyphospbonate haben gegenüber den erfindungsgemäßen Phosphonsäuren den Nachteil, daß sie schwerer zugänglich sind. Nachteilig für die stickstoffhaltigen Phosphonate ist es auch, daß sie z. B. in Gegenwart von Säuren bei etwa Pn 2 ausfallen und völlig unwirksam werden. The nitrogen-containing polyphosphonates have compared to the invention Phosphonic acids have the disadvantage that they are more difficult to access. Detrimental to the nitrogen-containing phosphonates, it is also that they z. B. in the presence of acids fail at about Pn 2 and become completely ineffective.
Die vorliegenden Phosphonsäuren, insbesondere die Methylen-diphosphonsäure, vermögen als solche oder in Form ihrer Alkalisalze Kationen außer denen der Alkalimetalle hervorragend komplex zu binden. Die Ionen sind in den Komplexen so stark maskiert, daß sie zahlreiche chemische Reaktionen nicht mehr geben. The phosphonic acids present, in particular methylene-diphosphonic acid, as such or in the form of their alkali metal salts, they have cations other than those of the alkali metals excellent to bind complex. The ions are so strongly masked in the complexes, that they no longer give numerous chemical reactions.
Zum Beispiel gibt der Fe3+-Komplex der Methylendiphosphonsäure mit Rhodanid keine Rotfärbung, der entsprechende Caldumkomplex mit Ammoninmoxalat keine Fällung. Von besonderer Bedeutung ist, daß die erfindungsgemäß genannten Phosphonsäuren in wäßriger Lösung vollkommen temperatur- und p-be- ständig sind, also in dieser Beziehung keinen Einschränkungen in ihrer Anwendung unterliegen wie Pyro- oder Polyphosphate. Gegenüber letzteren besitzen sie außerdem noch den großen Vorteil des stärkeren Komplexbildungsvermögens. weshalb man in der Praxis viel weniger Phosphonate als Phosphate einzusetzen braucht. Das Calciumbindevermögen wurde in der Weise bestimmt, daß 10 g Komplexbildner in wäßriger Lösung mit 0,5 n Calciumchlorid lösung titriert wurden unter Verwendung von Ammon-oxalat als Indikator bis zum Auftreten einer Trübung durch Calcium-oxalat.For example, the Fe3 + complex gives the methylenediphosphonic acid with Rhodanide no red color, the corresponding Caldum complex with ammonine moxalate none Precipitation. It is of particular importance that the phosphonic acids mentioned according to the invention in aqueous solution completely temperature and p-loading are constantly, so in this one Relationship are not subject to any restrictions in their application such as pyro- or polyphosphates. Compared to the latter, they also have the great advantage of being stronger Complexing ability. which is why in practice much less phosphonates than Needs to use phosphates. The calcium binding capacity was determined in the way that 10 g of complexing agent in aqueous solution is titrated with 0.5 N calcium chloride solution were using ammonium oxalate as an indicator until turbidity appeared by calcium oxalate.
1 g Na-pyrophosphat bindet 18,6 mg Calciumionen; 1 g Na-tripolyphosphat bindet 61,0 mg Calciumionen; 1 g Dinatrium-methylen-diphosphonat bindet 99 mg Calciumionen. 1 g Na pyrophosphate binds 18.6 mg calcium ions; 1 g sodium tripolyphosphate binds 61.0 mg calcium ions; 1 g of disodium methylene diphosphonate binds 99 mg of calcium ions.
Man kommt im allgemeinen mit Konzentrationen von etwa 0,01 bis 1 ovo aus. Die Diphosphon und Phosphoncarbonsäuren bzw. ihre Salze können überall bei industriellen Prozessen in wäßrigem Medium mit Vorteil verwendet werden, wo durch Fremdionen Störungen verursacht werden. Sie können als temperatur- und p-beständige Wasserenthärter verwendet werden. Als Zusatz zu festen und flüssigen Seifen, Waschmitteln, kosmetischen Artikeln, Haar-Shampoos und anderen Reinigungsmitteln unterbinden sie in genügender Konzentration die Bildung schwerlöslicher Metallseifen, Verfärbungen und Ranzigwerden und wirken gleichzeitig als Antioxydans und Stabilisatoren des Schaumes. In der photographischen Praxis können alle durch Verwendung von hartem Wasser bedingten Störungen beseitigt werden, z. B. können Entwicklerlösungen stabilisiert werden. Auf Grund ihrer Fähigkeit, Schwermetailsalze zu binden, eignen sich die erfindungsgemäß genannten Diphosphonate und Phosphoncarboxylate zum Stabilisieren von Peroxyverbindungen, wie sie für Reinigungs- und Bleichzwecke gebraucht werden, zum Stabilisieren von Latices aus natürlichem Kautschuk oder auch synthetischer Produkte aus Polystyrol, Butadien u. a. Aus demselben Grund vermögen sie Autoxydationen zu hemmen, wie z. B. von Sulfit (Haarbleichen), Fetten, Ölen, Proteinen, Gummen, Kunststoffen u. a. Bei der Darstellung und zur Stabilisierung von Antibiotika, wie Penicillin, lassen sie sich vorteilhaft anwenden. In der Lederindustrie lassen sich mit ihrer Hilfe Lederverfärbungen (z. B. durch Eisen) und Fäulnis der Häute vermeiden. Bei der Hydrazindarstellung wirken sie wie Leimzusatz ausbeuteverbessernd. Bei der elektrolytischen Reindarstellung von Metallen wifit sich der Zusatz der genannten Phosphonate wegen ihrer Fäligkeit, Fremdionen zu binden, günstig aus. Bei Galvanisierprozessen zeigen sie sich den Alkalicyaniden überlegen, weil sie physiologisch unbedenklich sind und nicht die Verwendung destillierten Wassers erfordern. Als Zusatz zu alkalischen Bädern beim »Finish« von Metallgegenständen sowie beim Polieren von Metallteilen lassen sich mit ihrer Hilfe gute Glanzeffekte erzielen, da sie die Entstehung schwerlöslicher Salze und Seifen verhindern. Auch für agrikulturchemische Zwecke lassen sie sich in zahlreichen Fällen mit Vorteil anwenden. So können dem Boden fehlende Spurenelemente besonders wirksam als Phosphonatkomplexe zugeführt werden. Wuchsstoffiösungen und Unkrautvertilgungsmittel, wie a-Naphthylessigsäure und Dichlorphenoxyessigsäure, die durch hartes Wasser ausgefällt werden, können durch die genannten Phosphonate in Lösung gehalten werden. Auf Grund ihres Calciumbindungsvermögens vermögen sie wie Zitronensäure die Blutgerinnung zu hemmen. Bei der Papierherstellung lassen sich mit ihrer Hilfe leicht sehr weiße und leicht zu bleichende Papiere herstellen. In der Färberei und bei der Farbstoffdarstellung können die Phosphonate mit Vorteil verwendet werden, um Calcium-, Magnesium- und Schwermetallionen zu binden. Das hat bei all den Farbstoffen, z. B. Küpenfarbstoffen, Eisfarben und Azofarbstoffen mit zur Azogruppe oder Carboxylgruppe orthoständigen Oxygruppen, Bedeutung, die mit den genannten Ionen meist schwerlösliche Salze bilden, wodurch Ausbeuteverminderung und Echtheitsverluste, z. B. der Reib- und Waschechtheit, eintreten können. Auch die katalytische Zersetzung diazotierter Amine durch Spuren von Eisen- und Kupferionen läßt sich mit den genannten Phosphonaten unterbinden. Bei der Darstellung von Chromierungsfarbstoffen können sie dazu dienen, um Spuren störender Schwermetallionen, wie vor allem Kupfer-und Eisenionen, zu binden. Auch beim Abziehen mancher Farbstoffe, wie z. B. einiger Schwefelfarbstoffe, und zum Entkupfern von Kupferfarbstoffen können sie mit Erfolg verwendet werden. Bei der Stärkedarstellung verhindern sie das Stockigwerden, soweit es durch hartes Wasser oder Metalle bedingt ist. Bei der Rayondarstellung lassen sich die durch Blejionen bedingten Störungen mit den genannten Phosphonaten beheben. Bei der Tieftemperaturpolymerisation von Kunststoffen eignen sich die FeS+-Komplexe der erfindungsgemäß genannten Phosphonate in Kombination mit Fe2l+-Salzen vorzüglich zur Polymerisationsauslösung. In general, concentrations of about 0.01 to 1 are used ovo off. The diphosphonic and phosphonic carboxylic acids or their salts can be used anywhere be used with advantage in industrial processes in aqueous medium, where interference is caused by foreign ions. They can be used as temperature and p-resistant Water softeners can be used. As an additive to solid and liquid soaps, detergents, Cosmetic items, hair shampoos and other cleaning products stop them in sufficient concentration, the formation of sparingly soluble metal soaps, discoloration and becoming rancid and at the same time act as antioxidants and stabilizers of the Foam. In photographic practice, all can be achieved by using hard Water related disturbances are eliminated, e.g. B. developer solutions can be stabilized will. on Because of their ability to bind heavy metal salts, the diphosphonates and phosphonic carboxylates mentioned according to the invention are suitable for stabilizing peroxy compounds such as those used for cleaning and bleaching purposes are used to stabilize latices made of natural rubber or also synthetic products made from polystyrene, butadiene and others Ability for the same reason to inhibit autoxidation, such as B. of sulfite (hair bleaching), fats, oils, Proteins, gums, plastics, etc. In the display and for stabilization antibiotics such as penicillin can be used to advantage. In the leather industry With their help, leather discolouration (e.g. due to iron) and decay of the Avoid skins. In the hydrazine preparation, they have the effect of improving the yield like an additive of glue. In the electrolytic preparation of metals, the addition of called phosphonates because of their ability to bind foreign ions, favorable. In electroplating processes, they are superior to alkali cyanides because they are physiologically harmless and do not require the use of distilled water. As an additive to alkaline baths for the »finish« of metal objects as well as for Polishing of metal parts can be used to achieve good gloss effects, as they prevent the formation of sparingly soluble salts and soaps. Also for agricultural chemicals They can be used to advantage in numerous cases. So can that Soil missing trace elements particularly effectively supplied as phosphonate complexes will. Growth solutions and weedkillers, such as a-naphthylacetic acid and dichlorophenoxyacetic acid, which can be precipitated by hard water are kept in solution by the phosphonates mentioned. Because of their calcium binding capacity Like citric acid, they can inhibit blood clotting. In papermaking With their help, very white and easy-to-bleach papers can easily be produced. The phosphonates can be used to advantage in dyeing and in the preparation of dyes used to bind calcium, magnesium and heavy metal ions. That has with all the dyes, e.g. B. vat dyes, ice colors and azo dyes with the azo group or carboxyl group ortho-position oxy groups, meaning those with the ones mentioned Ions usually form poorly soluble salts, which leads to a reduction in yield and loss of authenticity, z. B. the rub and wash fastness can occur. Catalytic decomposition too Diazotized amines by traces of iron and copper ions can be with the mentioned Stop phosphonates. In the representation of chromating dyes they serve to remove traces of disruptive heavy metal ions, such as especially copper and Iron ions, to bind. Even when peeling off some dyes, such as. B. some You can use sulfur dyes and copper dyes to decopper with success be used. With the representation of strength, they prevent the foxing, so far it is caused by hard water or metals. Leave at the rayon display the disorders caused by lead ions can be remedied with the above-mentioned phosphonates. The FeS + complexes are suitable for the low-temperature polymerisation of plastics of the phosphonates mentioned according to the invention in combination with Fe2l + salts are excellent to initiate polymerization.
Claims (1)
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DEF22912A DE1045373B (en) | 1957-04-26 | 1957-04-26 | Use of phosphonic acids |
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Cited By (24)
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DE1163114B (en) * | 1962-02-13 | 1964-02-13 | Dehydag Gmbh | Galvanic metal baths |
DE1192021B (en) * | 1963-01-12 | 1965-04-29 | Dehydag Gmbh | Galvanic baths |
US3201246A (en) * | 1961-04-10 | 1965-08-17 | Eastman Kodak Co | Photographic developers containing calcium precipitation inhibitors |
US3213030A (en) * | 1963-03-18 | 1965-10-19 | Procter & Gamble | Cleansing and laundering compositions |
DE1217928B (en) * | 1962-10-18 | 1966-06-02 | Monsanto Co | Process for preventing the separation of heavy metal ions from an aqueous solution |
US3271306A (en) * | 1963-11-06 | 1966-09-06 | Monsanto Co | Method for preventing the formation of insoluble iron compounds |
US3297578A (en) * | 1963-07-26 | 1967-01-10 | Monsanto Co | Bleaching, sterilizing, disinfecting, and deterging compositions |
US3348613A (en) * | 1965-05-19 | 1967-10-24 | Monsanto Co | Novel acidizing composition and method |
US3368978A (en) * | 1964-12-28 | 1968-02-13 | Monsanto Co | Builder compositions and detergent compositions using same |
US3422021A (en) * | 1963-03-18 | 1969-01-14 | Procter & Gamble | Detergent composition |
US3488707A (en) * | 1964-07-02 | 1970-01-06 | Agfa Gevaert Nv | Light-sensitive silver halide elements containing phosphonic acids |
US4083723A (en) * | 1976-02-24 | 1978-04-11 | Fuji Photo Film Co., Ltd. | Process for color photographic processing |
US4146397A (en) * | 1976-08-06 | 1979-03-27 | Fuji Photo Film Co., Ltd. | Method of forming a photographic image |
US4162161A (en) * | 1976-08-06 | 1979-07-24 | Fuji Photo Film Co., Ltd. | Reversal color photographic process |
USRE30064E (en) * | 1976-02-24 | 1979-08-07 | Fuji Photo Film Co., Ltd. | Process for color photographic processing |
EP0008640A1 (en) * | 1978-07-21 | 1980-03-19 | Ciba-Geigy Ag | Method for the removal of hydrogen sulfide from gases or liquid hydrocarbons and gases or liquid hydrocarbons thus purified |
US4277556A (en) * | 1976-08-18 | 1981-07-07 | Konishiroku Photo Industry Co., Ltd. | Process for treating light-sensitive silver halide color photographic materials |
US4689200A (en) * | 1981-09-04 | 1987-08-25 | Ciba-Geigy Corporation | Systems inhibited against corrosion and/or scale deposition |
EP0375615A2 (en) * | 1988-12-21 | 1990-06-27 | Ciba-Geigy Ag | Method of treating water containing fertilisers |
WO1997011148A1 (en) * | 1995-09-19 | 1997-03-27 | Colgate-Palmolive Company | Personal cleansing composition |
EP1974945A2 (en) | 2007-03-28 | 2008-10-01 | FUJIFILM Corporation | Heat-sensitive transfer image-receiving sheet |
EP1974950A1 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Thermal transfer image-receiving sheet and method for producing it |
EP1974949A1 (en) | 2007-03-28 | 2008-10-01 | FUJIFILM Corporation | Heat-sensitive transfer image-receiving sheet and production method thereof |
EP1982839A1 (en) | 2007-03-27 | 2008-10-22 | FUJIFILM Corporation | Heat-sensitive transfer image-forming method |
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Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3201246A (en) * | 1961-04-10 | 1965-08-17 | Eastman Kodak Co | Photographic developers containing calcium precipitation inhibitors |
DE1168208B (en) * | 1962-02-13 | 1964-04-16 | Dehydag Gmbh | Galvanic metal baths |
DE1163114B (en) * | 1962-02-13 | 1964-02-13 | Dehydag Gmbh | Galvanic metal baths |
DE1217928B (en) * | 1962-10-18 | 1966-06-02 | Monsanto Co | Process for preventing the separation of heavy metal ions from an aqueous solution |
DE1192021B (en) * | 1963-01-12 | 1965-04-29 | Dehydag Gmbh | Galvanic baths |
DE1196464B (en) * | 1963-01-12 | 1965-07-08 | Dehydag Gmbh | Galvanic baths |
DE1201152B (en) * | 1963-01-12 | 1965-09-16 | Dehydag Gmbh | Galvanic baths |
US3422021A (en) * | 1963-03-18 | 1969-01-14 | Procter & Gamble | Detergent composition |
US3213030A (en) * | 1963-03-18 | 1965-10-19 | Procter & Gamble | Cleansing and laundering compositions |
US3297578A (en) * | 1963-07-26 | 1967-01-10 | Monsanto Co | Bleaching, sterilizing, disinfecting, and deterging compositions |
US3271306A (en) * | 1963-11-06 | 1966-09-06 | Monsanto Co | Method for preventing the formation of insoluble iron compounds |
US3488707A (en) * | 1964-07-02 | 1970-01-06 | Agfa Gevaert Nv | Light-sensitive silver halide elements containing phosphonic acids |
US3368978A (en) * | 1964-12-28 | 1968-02-13 | Monsanto Co | Builder compositions and detergent compositions using same |
US3348613A (en) * | 1965-05-19 | 1967-10-24 | Monsanto Co | Novel acidizing composition and method |
US4083723A (en) * | 1976-02-24 | 1978-04-11 | Fuji Photo Film Co., Ltd. | Process for color photographic processing |
USRE30064E (en) * | 1976-02-24 | 1979-08-07 | Fuji Photo Film Co., Ltd. | Process for color photographic processing |
US4162161A (en) * | 1976-08-06 | 1979-07-24 | Fuji Photo Film Co., Ltd. | Reversal color photographic process |
US4146397A (en) * | 1976-08-06 | 1979-03-27 | Fuji Photo Film Co., Ltd. | Method of forming a photographic image |
US4277556A (en) * | 1976-08-18 | 1981-07-07 | Konishiroku Photo Industry Co., Ltd. | Process for treating light-sensitive silver halide color photographic materials |
US4251492A (en) | 1978-06-07 | 1981-02-17 | Ciba-Geigy Corporation | Purification process |
EP0008640A1 (en) * | 1978-07-21 | 1980-03-19 | Ciba-Geigy Ag | Method for the removal of hydrogen sulfide from gases or liquid hydrocarbons and gases or liquid hydrocarbons thus purified |
US4689200A (en) * | 1981-09-04 | 1987-08-25 | Ciba-Geigy Corporation | Systems inhibited against corrosion and/or scale deposition |
US4828795A (en) * | 1981-09-04 | 1989-05-09 | Ciba-Geigy Corporation | Systems inhibited against corrosion and/or scale deposition |
EP0375615A2 (en) * | 1988-12-21 | 1990-06-27 | Ciba-Geigy Ag | Method of treating water containing fertilisers |
EP0375615A3 (en) * | 1988-12-21 | 1990-09-12 | Ciba-Geigy Ag | Method of treating water containing fertilisers |
AU630396B2 (en) * | 1988-12-21 | 1992-10-29 | Ciba-Geigy Ag | Method of treating water containing fertilisers |
WO1997011148A1 (en) * | 1995-09-19 | 1997-03-27 | Colgate-Palmolive Company | Personal cleansing composition |
US5891834A (en) * | 1995-09-19 | 1999-04-06 | Colgate Palmolive Company | Composition |
EP1982839A1 (en) | 2007-03-27 | 2008-10-22 | FUJIFILM Corporation | Heat-sensitive transfer image-forming method |
EP1974945A2 (en) | 2007-03-28 | 2008-10-01 | FUJIFILM Corporation | Heat-sensitive transfer image-receiving sheet |
EP1974949A1 (en) | 2007-03-28 | 2008-10-01 | FUJIFILM Corporation | Heat-sensitive transfer image-receiving sheet and production method thereof |
EP1974950A1 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Thermal transfer image-receiving sheet and method for producing it |
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