ES2595180T3 - Stabilization of phthalimido percarboxylic acids with lithium salts - Google Patents
Stabilization of phthalimido percarboxylic acids with lithium salts Download PDFInfo
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- ES2595180T3 ES2595180T3 ES12725048.8T ES12725048T ES2595180T3 ES 2595180 T3 ES2595180 T3 ES 2595180T3 ES 12725048 T ES12725048 T ES 12725048T ES 2595180 T3 ES2595180 T3 ES 2595180T3
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- lithium
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- weight
- phthalimido
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- 229910003002 lithium salt Inorganic materials 0.000 title claims abstract description 27
- 159000000002 lithium salts Chemical class 0.000 title claims abstract description 27
- 239000002253 acid Substances 0.000 title claims description 39
- 125000005544 phthalimido group Chemical group 0.000 title claims description 30
- 150000007513 acids Chemical class 0.000 title description 16
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 62
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 25
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007844 bleaching agent Substances 0.000 claims abstract description 12
- 239000003599 detergent Substances 0.000 claims description 21
- -1 lithium hexafluorosilicate Chemical compound 0.000 claims description 15
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 11
- 239000004327 boric acid Substances 0.000 claims description 11
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 claims description 11
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 claims description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000004645 aluminates Chemical class 0.000 claims description 5
- FSBGUSGSQKUNCC-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)hexaneperoxoic acid Chemical compound C1=CC=C2C(=O)N(C(CCCC)C(=O)OO)C(=O)C2=C1 FSBGUSGSQKUNCC-UHFFFAOYSA-N 0.000 claims description 4
- NQUPKCJGWCPODR-UHFFFAOYSA-N hexaneperoxoic acid Chemical compound CCCCCC(=O)OO NQUPKCJGWCPODR-UHFFFAOYSA-N 0.000 claims description 4
- 229910001386 lithium phosphate Inorganic materials 0.000 claims description 4
- SNKMVYBWZDHJHE-UHFFFAOYSA-M lithium;dihydrogen phosphate Chemical compound [Li+].OP(O)([O-])=O SNKMVYBWZDHJHE-UHFFFAOYSA-M 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- REKWWOFUJAJBCL-UHFFFAOYSA-L dilithium;hydrogen phosphate Chemical compound [Li+].[Li+].OP([O-])([O-])=O REKWWOFUJAJBCL-UHFFFAOYSA-L 0.000 claims description 2
- BBLSYMNDKUHQAG-UHFFFAOYSA-L dilithium;sulfite Chemical compound [Li+].[Li+].[O-]S([O-])=O BBLSYMNDKUHQAG-UHFFFAOYSA-L 0.000 claims description 2
- SUPUVLWGKPVHBQ-UHFFFAOYSA-M lithium sulfite Chemical compound [Li+].OS([O-])=O SUPUVLWGKPVHBQ-UHFFFAOYSA-M 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- HPCCWDVOHHFCKM-UHFFFAOYSA-M lithium;hydrogen sulfate Chemical compound [Li+].OS([O-])(=O)=O HPCCWDVOHHFCKM-UHFFFAOYSA-M 0.000 claims description 2
- 229910001290 LiPF6 Inorganic materials 0.000 claims 1
- GCPNLDYWHHIXMX-UHFFFAOYSA-H hexalithium;hexachloride Chemical compound [Li+].[Li+].[Li+].[Li+].[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] GCPNLDYWHHIXMX-UHFFFAOYSA-H 0.000 claims 1
- 150000001450 anions Chemical class 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- WTQMRYVXRLESSC-UHFFFAOYSA-N 2-(6-hydroxyhexan-3-yl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(CCCO)CC)C(=O)C2=C1 WTQMRYVXRLESSC-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229910012219 LiPFa Inorganic materials 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- JSEYWLJWQKMDSA-UHFFFAOYSA-N [O-]B(O)O.[Li+].Cl.Cl.Cl.Cl Chemical compound [O-]B(O)O.[Li+].Cl.Cl.Cl.Cl JSEYWLJWQKMDSA-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010412 laundry washing Methods 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/046—Salts
-
- 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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/06—Phosphates, including polyphosphates
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
Abstract
Mezcla para su uso con un agente blanqueador que comprende al menos un ácido ftalimido percarboxílico y al menos una sal de litio inorgánica.Mixture for use with a bleaching agent comprising at least one phthalimide percarboxylic acid and at least one inorganic lithium salt.
Description
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DESCRIPCIONDESCRIPTION
Estabilizacion de acidos ftalimido percarbox^licos con sales de litio Campo de la invencionStabilization of phthalimide percarboxylic acids with lithium salts Field of the invention
La presente invencion se refiere a una mezcla para su uso como un agente blanqueador que comprende al menos un acido ftalimido percarbox^lico y al menos una sal de litio inorganica, a una composicion detergente que comprende dicha mezcla y al uso de al menos una sal de litio para estabilizar un acido ftalimido percarboxflico en una composicion detergente.The present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimide percarboxylic acid and at least one inorganic lithium salt, a detergent composition comprising said mixture and the use of at least one salt. of lithium to stabilize a phthalimide percarboxylic acid in a detergent composition.
Antecedentes de la invencionBackground of the invention
En el pasado, los peracidos organicos han encontrado un interes creciente en el campo industrial, entre otras cuestiones debido a sus excelentes propiedades como agentes blanqueadores en formulaciones detergentes. Por lo tanto, un gran numero de publicaciones estan relacionadas con compuestos de peracido organicos dotados de la propiedad requerida de actividad blanqueadora suficiente, siendo esencial dicha caractenstica para una aplicacion industrial y un uso extendido de tales compuestos. De esta manera, se conocen y usan muchos acidos organicos mono- o di-percarboxflicos, de cadena lineal o dclicos, por ejemplo en composiciones detergentes.In the past, organic perazides have found a growing interest in the industrial field, among other issues due to their excellent properties as bleaching agents in detergent formulations. Therefore, a large number of publications are related to organic perazide compounds endowed with the required property of sufficient bleaching activity, said feature being essential for an industrial application and extended use of such compounds. In this way, many mono- or di-percarboxylic, straight chain or dical organic acids are known and used, for example in detergent compositions.
Un problema con el uso extendido de peracidos organicos surge a partir de su baja estabilidad termica, que hace necesario estabilizar ffsica o qmmicamente estos compuestos. Los peracidos organicos conocidos hasta ahora muestran una disminucion significativa del oxfgeno activo, incluso en condiciones de almacenamiento convencionales. Este tambien es el caso con los acidos imido percarboxflicos, como ya se ha descrito en Chem. Soc. 1962, 3821 y Chem. Ind. 1961,469. Entre los acidos imido percarboxflicos, los acidos ftalimido percarboxflicos han conseguido un uso extendido en la industria, especialmente como agentes blanqueadores en composiciones detergentes. Sin embargo, la adiccion de acido borico a los acidos ftalimido percarboxflicos se considera necesaria para garantizar una estabilidad a largo plazo suficiente.A problem with the widespread use of organic peraids arises from their low thermal stability, which makes it necessary to physically or chemically stabilize these compounds. The organic peraids known so far show a significant decrease in active oxygen, even under conventional storage conditions. This is also the case with the imido percarboxylic acids, as already described in Chem. Soc. 1962, 3821 and Chem. Ind. 1961,469. Among the imido percarboxylic acids, phthalimido percarboxylic acids have achieved widespread use in industry, especially as bleaching agents in detergent compositions. However, the addition of boric acid to phthalimide percarboxylic acids is considered necessary to ensure sufficient long-term stability.
Puesto que el acido borico se ha convertido en una sustancia qmmica de gran preocupacion, cabe esperar que se prohfba el uso de acido borico en aplicaciones domesticas en el futuro proximo. En consecuencia, hay necesidad de maneras alternativas de estabilizar los acidos ftalimido percarboxflicos en composiciones detergentes sin usar acido borico.Since boric acid has become a chemical of great concern, it is expected that the use of boric acid in domestic applications will be banned in the near future. Consequently, there is a need for alternative ways of stabilizing phthalimido percarboxylic acids in detergent compositions without using boric acid.
Sumario de la invencionSummary of the invention
La presente invencion satisface esta necesidad proporcionando una mezcla para su uso como un agente blanqueador que comprende al menos un acido ftalimido percarboxflico y al menos una sal de litio inorganica. Con la presente invencion, es posible estabilizar acidos ftalimido percarboxflicos para minimizar una disminucion del oxfgeno en condiciones de almacenamiento convencionales, para evitar el uso de acido borico. De esta manera, pueden obtenerse composiciones detergentes que muestran una actividad blanqueadora suficiente con el tiempo.The present invention satisfies this need by providing a mixture for use as a bleaching agent comprising at least one phthalimide percarboxylic acid and at least one inorganic lithium salt. With the present invention, it is possible to stabilize phthalimide percarboxylic acids to minimize a decrease in oxygen under conventional storage conditions, to avoid the use of boric acid. In this way, detergent compositions can be obtained that show sufficient bleaching activity over time.
Descripcion detallada de la invencionDetailed description of the invention
Despues de estudios extensivos, los inventores han encontrado que los acidos ftalimido percarboxflicos pueden estabilizarse mediante sales inorganicas de litio. Esto es bastante sorprendente, puesto que la tecnica anterior sugena que, si no se estabilizaban, los acidos ftalimido percarboxflicos se degradaban siguiendo una ruta de reaccion por radicales.After extensive studies, the inventors have found that phthalimide percarboxylic acids can be stabilized by inorganic lithium salts. This is quite surprising, since the prior art suggests that, if they were not stabilized, phthalimide percarboxylic acids were degraded following a radical reaction path.
Sin desear quedar ligado a teona alguna, se supone que los acidos ftalimido percarboxflicos, de hecho, se degradan por el ataque de nucleofilos. En la figura 1 se muestra un esquema de degradacion plausible del acido ftalimido peroxihexanoico (acido ftalimido percaproico, PAP) en condiciones alcalinas. De acuerdo con la figura 1, el PAP se degrada a 4-ftalimido-1-hexanol y dioxido de carbono por reaccion electrodclica. En consecuencia, la presencia de al menos una sal de litio evitana que los nucleofilos degradaran el PAP, ya sea excluyendo los nuecleofilos reactivos, bloqueando sitios de reaccion nucleofilos en el PAP y/o captando nucleofilos con electrofilos distintos de PAP.Without wishing to be bound to any theone, it is assumed that phthalimide percarboxylic acids, in fact, are degraded by the attack of nucleophiles. A plausible degradation scheme of peroxyhexanoic phthalimido acid (percaproic phthalimido acid, PAP) in alkaline conditions is shown in Figure 1. According to Figure 1, the PAP is degraded to 4-phthalimido-1-hexanol and carbon dioxide by electrodic reaction. Consequently, the presence of at least one lithium salt will prevent the nucleophiles from degrading the PAP, either by excluding the reactive nucleophiles, blocking nucleophilic reaction sites in the PAP and / or capturing nucleophiles with electrophiles other than PAP.
Por lo tanto, la presente invencion se refiere a una mezcla para su uso como un agente blanqueador que comprende al menos un acido ftalimido percarboxflico y al menos una sal de litio inorganica.Therefore, the present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimide percarboxylic acid and at least one inorganic lithium salt.
No hay restriccion respecto a la naturaleza qmmica de la al menos una sal de litio. De esta manera, la al menos una sal de litios es inorganica. Aparte, la al menos una sal de litio puede ser hfdrica o anhidra.There is no restriction regarding the chemical nature of the at least one lithium salt. In this way, the at least one lithium salt is inorganic. In addition, the at least one lithium salt can be water or anhydrous.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que comprende al menos una sal de litio inorganica.Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one inorganic lithium salt.
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De acuerdo con la presente invencion, se prefiere que el anion de la al menos una sal de litio sea bastante no nucleofilo. Si el anion en cuestion es demasiado nucleofilo, se supone que compite contra el cation litio para interaccionar con el acido ftalimido percarbox^lico. Los aniones no nucleofilos adecuados para su uso de acuerdo con la presente invencion son hexafluorosilicato (SiF62-), sulfito (SO32-), hidrogenosulfito (HSO3-), sulfato (SO42-), hidrogenosulfato (HSO42-), fosfato (PO43-), hidrogenofosfato (HPO42-), dihidrogenofosfato (H2PO4-), tetrafluoro borato (BF4-), tetracloro borato (BCI4-), tetrabromo borato (BBr4-), tetrayodo borato (BU-), tetrafenil borato (B[C6H5]4-), tetra(pentafluoro)fenilborato (B[C6F5]4-), hexafluorofosfato (PF6-), hexacloro aluminato (AICI63-), hexabromo aluminato (AIBr63-) y combinaciones de los mismos, en las que el anion sulfato representa el anion mas preferido.In accordance with the present invention, it is preferred that the anion of the at least one lithium salt is quite non-nucleophilic. If the anion in question is too nucleophilic, it is supposed to compete against the lithium cation to interact with the phthalimide percarboxylic acid. Non-nucleophilic anions suitable for use in accordance with the present invention are hexafluorosilicate (SiF62-), sulphite (SO32-), hydrogen sulphite (HSO3-), sulfate (SO42-), hydrogen sulfate (HSO42-), phosphate (PO43-) , hydrogen phosphate (HPO42-), dihydrogen phosphate (H2PO4-), tetrafluoro borate (BF4-), tetrachloro borate (BCI4-), tetrabromo borate (BBr4-), tetraiodine borate (BU-), tetraphenyl borate (B [C6H5] 4- ), tetra (pentafluoro) phenylborate (B [C6F5] 4-), hexafluorophosphate (PF6-), hexachloro aluminate (AICI63-), hexabromo aluminate (AIBr63-) and combinations thereof, in which the anion sulfate represents the anion more preferred
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que comprende al menos una sal de litio seleccionada del grupo que consiste en hexafluorosilicato de litio (Li2SiF@), sulfito de litio (U2SO3), hidrogenosulfito de litio (LiHSO3), sulfato de litio (Li2SO4), hidrogenosulfato de litio (LiHSO4), fosfato de litio (Li3PO4), hidrogenofosfato de litio (Li2HPO4), dihidrogenofosfato de litio (LH2PO4), tetrafluoro borato de litio (UBF4), tetracloro borato de litio (LiBCU), tetrabromo borato de litio (LiBBu), tetrayodo borato de litio (LiBU), tetrafenil borato de litio (LiB[C6H5]4), tetra(pentafluoro)fenil borato de litio (LiB[C6F5]4), hexafluorofosfato de litio (LiPFa), hexacloro aluminato de litio (Li3AICl6), hexabromo aluminato de litio (Li3AIBr6). La presente invencion se refiere ademas a la mezcla que se ha descrito anteriormente, caracterizada por que comprende sulfato de litio.Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one lithium salt selected from the group consisting of lithium hexafluorosilicate (Li2SiF @), lithium sulphite (U2SO3), lithium hydrogen sulphite (LiHSO3), lithium sulfate (Li2SO4), lithium hydrogen sulfate (LiHSO4), lithium phosphate (Li3PO4), lithium hydrogen phosphate (Li2HPO4), lithium dihydrogen phosphate (LH2PO4), lithium tetrafluoro borate (UBF4), tetrachloride borate lithium (LiBCU), lithium tetrabromo borate (LiBBu), lithium tetraiodine borate (LiBU), lithium tetraphenyl borate (LiB [C6H5] 4), tetra (pentafluoro) phenyl borate lithium (LiB [C6F5] 4), hexafluorophosphate lithium (LiPFa), lithium hexachloro aluminate (Li3AICl6), lithium hexabromo aluminate (Li3AIBr6). The present invention also relates to the mixture described above, characterized in that it comprises lithium sulfate.
Asimismo, no hay restriccion respecto a la naturaleza qmmica de el al menos un acido ftalimido percarboxflico. Los acidos ftalimido percarboxflicos adecuados para su uso de acuerdo con la presente invencion pueden seleccionarse del grupo de los acidos ftalimido percarboxilicos de formula general (I), donde n es un numero entero de 1 a 5:Likewise, there is no restriction regarding the chemical nature of the at least one phthalimide percarboxylic acid. Phthalimido percarboxylic acids suitable for use in accordance with the present invention can be selected from the group of phthalimido percarboxylic acids of general formula (I), where n is an integer from 1 to 5:
De esta manera, los acidos ftalimido percarboxilicos adecuados para su uso de acuerdo con la presente invencion pueden seleccionarse del grupo que consiste en acido ftalimido peracetico (n=1), acido ftalimido perpropionico (n=2), acido ftalimido perbutmco (n=3), acido ftalimido perairnlico (n=4) y acido ftalimido percaproico (n=5), en el que el acido ftalimido percaproico (acido ftalimido peroxihexanoico, PAP) representa el acido ftalimido percarboxflico mas preferido.Thus, percarboxylic phthalimido acids suitable for use in accordance with the present invention can be selected from the group consisting of peracetic phthalimide acid (n = 1), perpropionic phthalimido acid (n = 2), perbutmco phthalimido acid (n = 3 ), perairnlico phthalimido acid (n = 4) and percaproic phthalimido acid (n = 5), in which the percaproic phthalimido acid (peroxyhexanoic phthalimido acid, PAP) represents the most preferred percarboxylic phthalimido acid.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que esta comprende al menos un acido ftalimido percarboxflico seleccionado de los acidos ftalimido percarboxilicos de la formula general (I) anterior, donde n es un numero entero de 1 a 5. La presente invencion se refiere ademas a la mezcla descrita anteriormente, caracterizada por que comprende acido ftalimido percaproico (acido ftalimido peroxihexanoico, PAP).Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one percarboxylic phthalimido acid selected from the percarboxylic phthalimido acids of the general formula (I) above, where n is an integer of 1 a 5. The present invention also relates to the mixture described above, characterized in that it comprises percaproic phthalimido acid (peroxyhexanoic phthalimido acid, PAP).
Los acidos ftalimido percarboxilicos y, especialmente, acido ftalimido peroxicaproico, pueden prepararse como se describe en los documentos EP 0 325 288 A1 y EP 0 349 940 B1, respectivamente. De esta manera, un sustrato seleccionado de acidos ftalimido percarboxilicos y anfudridos de los mismos, que tiene una estructura correspondiente al acido percarboxflico deseado, por ejemplo, de formula general (I), puede hacerse reaccionar con H2O2 concentrado en un medio de reaccion seleccionado de H2SO4 concentrado y CH3SO3H o en un medio alcalino, y el acido percarboxflico se separa despues de la mezcla de reaccion por tecnicas convencionales y conocidas.Phthalimido percarboxylic acids and, especially, peroxycaproic phthalimido acid, can be prepared as described in EP 0 325 288 A1 and EP 0 349 940 B1, respectively. In this way, a substrate selected from phthalimido-percarboxylic acids and amphudiated thereof, having a structure corresponding to the desired percarboxylic acid, for example, of general formula (I), can be reacted with concentrated H2O2 in a reaction medium selected from Concentrated H2SO4 and CH3SO3H or in an alkaline medium, and the percarboxylic acid is separated after the reaction mixture by conventional and known techniques.
Para obtener una estabilizacion optima de el al menos un acido ftalimido percarboxflico, el contenido de sal de litio en la mezcla debe variar entre el 1 y el 50 % en peso, preferentemente entre el 1 y el 25 % en peso, mas preferentemente entre el 1 y el 10 % en peso, lo mas preferentemente entre el 2 y el 5 % en peso, basado en el peso total de la mezcla.To obtain an optimal stabilization of the at least one phthalimide percarboxylic acid, the content of lithium salt in the mixture should vary between 1 and 50% by weight, preferably between 1 and 25% by weight, more preferably between 1 and 10% by weight, most preferably between 2 and 5% by weight, based on the total weight of the mixture.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que el contenido de sal de litio es entre el 1 y el 50 % en peso, preferentemente entre el 1 y el 25 % en peso, mas preferentemente entre el 1 y el 10 % en peso, lo mas preferentemente entre 2 y el 5 % en peso, basado en el peso total de la mezcla.Therefore, the present invention also relates to the mixture described above, characterized in that the content of lithium salt is between 1 and 50% by weight, preferably between 1 and 25% by weight, more preferably between 1 and 10% by weight, most preferably between 2 and 5% by weight, based on the total weight of the mixture.
Ventajosamente, la proporcion en peso de acido ftalimido percarboxflico a sal de litio es entre 20:1 y 1:1, preferentemente entre 10:1 y 1:1, mas preferentemente entre 5:1 y 1:1, lo mas preferentemente entre 2:1 y 1:1.Advantageously, the weight ratio of phthalimido percarboxylic acid to lithium salt is between 20: 1 and 1: 1, preferably between 10: 1 and 1: 1, more preferably between 5: 1 and 1: 1, most preferably between 2 : 1 and 1: 1.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que la proporcion en peso de acido ftalimido percarboxflico a sal de litio es entre 20:1 y 1:1, preferentemente entre 10:1 y 1:1, mas preferentemente entre 5:1 y 1:1, lo mas preferentemente entre 2:1 y 1:1.Therefore, the present invention also relates to the mixture described above, characterized in that the weight ratio of phthalimide percarboxylic acid to lithium salt is between 20: 1 and 1: 1, preferably between 10: 1 and 1: 1 , more preferably between 5: 1 and 1: 1, most preferably between 2: 1 and 1: 1.
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Una mezcla especialmente conveniente para su uso como un agente blanqueador comprende entre el 10 y el 25 % en peso de acido ftalimido peroxihexanoico (acido ftalimido percaproico, PAP) y entre el 2 y el 5 % en peso de sulfato de litio, basado en el peso total de la mezcla.A mixture especially suitable for use as a bleaching agent comprises between 10 and 25% by weight of phthalimido peroxyhexanoic acid (phthalimide percaproic acid, PAP) and between 2 and 5% by weight of lithium sulfate, based on the total weight of the mixture.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que compre entre el 10 y el 25 % en peso de acido ftalimido peroxihexanoico (acido ftalimido percaproico, PAP) y entre el 2 y el 5 % en peso de sulfato de litio, basado en el peso total de la mezcla.Therefore, the present invention also relates to the mixture described above, characterized in that it purchases between 10 and 25% by weight of phthalimido peroxyhexanoic acid (phthalimide percaproic acid, PAP) and between 2 and 5% by weight of lithium sulfate, based on the total weight of the mixture.
La mezcla que comprende el al menos un acido ftalimido percarboxflico y la al menos una sal de litio de acuerdo con la presente invencion puede fabricarse en forma de una solucion acuosa, gel, emulsion, pasta, dispersion, polvo, copos, granulos, escamas, perlas, comprimidos, una forma de bloque solido, extruidos y otras formas conocidas en la tecnica, aunque preferentemente representa un polvo o un copo.The mixture comprising the at least one phthalimide percarboxylic acid and the at least one lithium salt according to the present invention can be manufactured in the form of an aqueous solution, gel, emulsion, paste, dispersion, powder, flakes, granules, flakes, beads, tablets, a solid block form, extrudates and other forms known in the art, although preferably it represents a powder or a flake.
Por lo tanto, la presente invencion se refiere tambien a la mezcla descrita anteriormente, caracterizada por que la mezcla esta en forma de un polvo o un copo.Therefore, the present invention also relates to the mixture described above, characterized in that the mixture is in the form of a powder or a flake.
La mezcla de acuerdo con la presente invencion es particularmente adecuada como agente blanqueador eficaz en formulaciones detergentes.The mixture according to the present invention is particularly suitable as an effective bleaching agent in detergent formulations.
Por lo tanto, la presente invencion se refiere tambien al uso de una mezcla descrita anteriormente como un agente blanqueador.Therefore, the present invention also relates to the use of a mixture described above as a bleaching agent.
La presente invencion se refiere ademas a una composicion detergente que comprende una mezcla descrita anteriormente. La composicion detergente puede contener cualquier aditivo o ingrediente activo usado habitualmente en los correspondientes agentes de lavado, limpieza y/o desinfeccion, tales como aditivos, tensioactivos, jabones, zeolitas, agentes hidrotropicos, inhibidores de la corrosion, enzimas, abrillantadores opticos, estabilizadores, abrasivos, perfumes, agentes colorantes.The present invention further relates to a detergent composition comprising a mixture described above. The detergent composition may contain any additive or active ingredient commonly used in the corresponding washing, cleaning and / or disinfecting agents, such as additives, surfactants, soaps, zeolites, hydrotropic agents, corrosion inhibitors, enzymes, optical brighteners, stabilizers, abrasives, perfumes, coloring agents.
La mezcla inventiva puede incorporarse en la composicion detergente ya sea tal cual o en combinacion con otros aditivos, por ejemplo, fosfatos, carbonatos, zeolitas, carboximetilcelulosa o agentes filminogenos como acidos grasos, amidas o esteres de acido graso, etc., en las formas mencionadas anteriormente para la mezcla.The inventive mixture can be incorporated into the detergent composition either as it is or in combination with other additives, for example, phosphates, carbonates, zeolites, carboxymethyl cellulose or filminogen agents such as fatty acids, amides or fatty acid esters, etc., in the forms mentioned above for mixing.
Se prefiere que la composicion detergente este sustancialmente libre de acido borico, es decir, que comprenda menos de 10 ppm, preferentemente menos de 5 ppm, aun mas preferentemente menos de 1 ppm y, lo mas preferentemente, menos de 0,1 ppm de acido borico.It is preferred that the detergent composition be substantially free of boric acid, that is, that it comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm and, most preferably, less than 0.1 ppm acid. boric.
Por lo tanto, la presente invencion se refiere tambien a la composicion detergente descrita anteriormente, caracterizada por que comprende menos de 10 ppm, preferentemente menos de 5 ppm, incluso mas preferentemente menos de 1 ppm y, lo mas preferentemente, menos de 0,1ppm de acido borico.Therefore, the present invention also relates to the detergent composition described above, characterized in that it comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm and, most preferably, less than 0.1 ppm. of boric acid.
La composicion detergente puede usarse como un detergente para lavado de ropa, preferentemente como un detergente para telas, y no solo es adecuado para un lavado general de la colada, sino tambien para desinfectar.The detergent composition can be used as a laundry detergent, preferably as a fabric detergent, and is not only suitable for general laundry washing, but also for disinfecting.
Aparte, el detergente de acuerdo con la presente invencion puede usarse como limpiador y/o desinfectante para limpiar y desinfectar diversas clases de superficies duras como, por ejemplo, en el campo medico o institucional, en la preparacion de alimentos, en la industria del procesamiento y/o venta, en agricultura, en el negocio hotelero, en el negocio de catering y/o en edificios y/o instituciones publicas. Puede ser util tambien en otras aplicaciones en las cuales se requiere o se desea una superficie desinfectada, y que no se mencionan explfcitamente en ese documento. La superficie que se supone queda desinfectada puede estar fabricada de los materiales comunes mencionados en el estado de tecnica como, por ejemplo, metal, vidrio, ceramica, plastico, madera (revestida).In addition, the detergent according to the present invention can be used as a cleaner and / or disinfectant to clean and disinfect various kinds of hard surfaces such as, for example, in the medical or institutional field, in food preparation, in the processing industry and / or sale, in agriculture, in the hotel business, in the catering business and / or in buildings and / or public institutions. It may also be useful in other applications in which a disinfected surface is required or desired, and which is not explicitly mentioned in that document. The surface that is supposed to be disinfected can be made of the common materials mentioned in the state of the art such as, for example, metal, glass, ceramic, plastic, wood (coated).
Finalmente, la presente invencion se refiere al uso de al menos una sal de litio para estabilizar un acido ftalimido percarboxflico en una composicion detergente.Finally, the present invention relates to the use of at least one lithium salt to stabilize a phthalimide percarboxylic acid in a detergent composition.
A continuacion, la estabilizacion de los acidos ftalimido peroxicarboxflicos con sales de litio se demostrara sin restringirse a estos ejemplos.Next, the stabilization of the phthalimido peroxycarboxylic acids with lithium salts will be demonstrated without being restricted to these examples.
EjemplosExamples
Ejemplo 1:Example 1:
Una mezcla para su uso como un agente blanqueador que comprende 86 % en peso de acido ftalimido peroxihexanoico (acido ftalimido percaproico, PAP) y 14% en peso de un agente estabilizador (ejemplo 1a: acido borico (comparativo); ejemplo 1b: sulfato sodico (comparativo); ejemplo 1c: sulfato de litio) se ensayo para su estabilidad a largo plazo. Por lo tanto, la cantidad de PAP qmmicamente activo en la mezcla respectiva se determino despues del almacenamiento a 40 °C a los 1, 3, 7, 14, 21,28, 49, 84, 119, 161 y 210 dfas, respectivamente.A mixture for use as a bleaching agent comprising 86% by weight of phthalimido peroxyhexanoic acid (phthalimide percaproic acid, PAP) and 14% by weight of a stabilizing agent (example 1a: boric acid (comparative); example 1b: sodium sulfate (comparative); example 1c: lithium sulfate) was tested for long-term stability. Therefore, the amount of chemically active PAP in the respective mixture was determined after storage at 40 ° C at 1, 3, 7, 14, 21,28, 49, 84, 119, 161 and 210 days, respectively.
Como puede verse en la tabla 1, una mezcla que comprende sulfato de litio (ejemplo 1c) muestra una estabilidad a largo plazo significativamente mayor del acido ftalimido peroxihexanoico (acido ftalimido percaproico PAP) que una mezcla que comprende sulfato sodico (ejemplo 1b).As can be seen in Table 1, a mixture comprising lithium sulfate (example 1c) shows significantly greater long-term stability of the peroxyhexanoic phthalimido acid (PAP percaproic phthalimido acid) than a mixture comprising sodium sulfate (example 1b).
5 Tabla 1:5 Table 1:
Actividad de PAP %PAP% activity
- Dias Days
- 0 1 3 7 14 21 28 49 84 119 161 210 0 1 3 7 14 21 28 49 84 119 161 210
- PAP a 40 °C con acido borico al 14 % PAP at 40 ° C with 14% boric acid
- 84,4 84,3 82,2 84,0 81,4 83,3 79,7 81,2 77,2 73,3 73,6 74,0 84.4 84.3 82.2 84.0 81.4 83.3 79.7 81.2 77.2 73.3 73.6 74.0
- PAP a 40 °C con sulfato sodico al 14 % PAP at 40 ° C with 14% sodium sulfate
- 84,5 80,2 78,7 75,5 78,2 77,3 77,3 75,3 73,6 72,8 72,0 70,8 84.5 80.2 78.7 75.5 78.2 77.3 77.3 75.3 73.6 72.8 72.0 70.8
- PAP a 40 °C con sulfato de litio al 14 % PAP at 40 ° C with 14% lithium sulfate
- 84,6 78,3 81,1 83,9 76,9 83,8 82,0 80,8 79,8 79,8 77,7 77,3 84.6 78.3 81.1 83.9 76.9 83.8 82.0 80.8 79.8 79.8 77.7 77.3
Ademas, como puede verse en la figura 2, el acido ftalimido peroxihexanoico (acido ftalimido percaproico, PAP) puede estabilizarse aun mas eficazmente mediante una sal de litio de acuerdo con la presente invencion (ejemplo 10 1c) que mediante el acido borico usado convencionalmente (ejemplo 1a).In addition, as can be seen in Figure 2, peroxyhexanoic phthalimido acid (percaproic phthalimido acid, PAP) can be stabilized even more efficiently by a lithium salt according to the present invention (example 10 1c) than by conventionally used boric acid ( example 1a).
Claims (13)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2012/060448 WO2013178289A1 (en) | 2012-06-01 | 2012-06-01 | Stabilization of phthalimido percarboxylic with lithium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2595180T3 true ES2595180T3 (en) | 2016-12-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12725048.8T Active ES2595180T3 (en) | 2012-06-01 | 2012-06-01 | Stabilization of phthalimido percarboxylic acids with lithium salts |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2855653B8 (en) |
| ES (1) | ES2595180T3 (en) |
| WO (1) | WO2013178289A1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1233846B (en) | 1988-01-20 | 1992-04-21 | Ausimont Spa | IMMEDIATE AROMATIC PEROXIDES |
| DE3823172C2 (en) | 1988-07-08 | 1998-01-22 | Hoechst Ag | Omega-phthalimidoperoxihexanoic acid, process for its preparation and its use |
| EP1586628A1 (en) * | 2004-04-05 | 2005-10-19 | The Procter & Gamble Company | Particulate bleaching compositions |
| DE102004030900A1 (en) * | 2004-06-25 | 2006-01-26 | Henkel Kgaa | Preparation of particulate peroxycarboxylic acid compositions |
| GB0509377D0 (en) * | 2005-05-09 | 2005-06-15 | Reckitt Benckiser Nv | Detergent composition |
| JP2010138268A (en) * | 2008-12-11 | 2010-06-24 | Kao Corp | Liquid bleaching detergent composition |
-
2012
- 2012-06-01 ES ES12725048.8T patent/ES2595180T3/en active Active
- 2012-06-01 EP EP12725048.8A patent/EP2855653B8/en active Active
- 2012-06-01 WO PCT/EP2012/060448 patent/WO2013178289A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2855653A1 (en) | 2015-04-08 |
| EP2855653B8 (en) | 2016-12-07 |
| WO2013178289A1 (en) | 2013-12-05 |
| EP2855653B1 (en) | 2016-07-20 |
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