EP2049643A1 - Utilisation d'aminoscétones et de leur sels en tant qu'amplificateurs d'aptitude au blanchiment pour composés peracide - Google Patents

Utilisation d'aminoscétones et de leur sels en tant qu'amplificateurs d'aptitude au blanchiment pour composés peracide

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Publication number
EP2049643A1
EP2049643A1 EP07801473A EP07801473A EP2049643A1 EP 2049643 A1 EP2049643 A1 EP 2049643A1 EP 07801473 A EP07801473 A EP 07801473A EP 07801473 A EP07801473 A EP 07801473A EP 2049643 A1 EP2049643 A1 EP 2049643A1
Authority
EP
European Patent Office
Prior art keywords
bleaching
salts
sub
aminoacetones
sup
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.)
Withdrawn
Application number
EP07801473A
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German (de)
English (en)
Inventor
Gerd Reinhardt
Georg Borchers
Michael Seebach
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Finance BVI Ltd
Original Assignee
Clariant Finance BVI Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2049643A1 publication Critical patent/EP2049643A1/fr
Withdrawn legal-status Critical Current

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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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0034—Fixed on a solid conventional detergent ingredient
    • 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
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • 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
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/3927—Quarternary ammonium compounds

Definitions

  • the present invention relates to the use of certain aminoacetones and their salts for enhancing the bleaching effect of peroxygen compounds in the bleaching of dyed soils on textiles as well as on hard surfaces, as well as solid and liquid detergents and cleaners containing such aminoacetones or their salts.
  • inorganic peroxygen compounds have been used as oxidizing agents for disinfecting and bleaching purposes.
  • Typical examples include hydrogen peroxide and solid peroxygen compounds such as sodium perborate and sodium carbonate perhydrate which dissolve in water to release hydrogen peroxide.
  • the oxidation effect of the peroxygen compounds is strongly temperature-dependent, a sufficiently fast bleaching is achieved only at temperatures above 80 0 C.
  • the oxidation effect of inorganic peroxygen compounds can be improved by addition of so-called bleach activators, so that even at temperatures around 60 0 C substantially the same bleaching result is achieved as with the peroxide solution alone at 95 ° C.
  • bleach activators are compounds from the group of N- and O-acyl compounds, such as polyacylated alkylenediamines, in particular tetraacetylethylenediamine (TAED), tetraacetylglucouril (TAGU), N-acylated hydantoins, hydrazides, triazoles, hydrotriazines, urazoles, diketopiperazines, sulfurylamides and Cyanurate, as well Carboxylic anhydrides, in particular phthalic anhydride and substituted maleic anhydrides, carboxylic acid esters, in particular sodium nonanoyloxybenzenesulfonate (NOBS), sodium isononanoyloxybenzenesulfonate (ISONOBS) and acylated sugar derivatives, such as pentaacetylglucose (PAG).
  • N- and O-acyl compounds such as polyacylated alkylenediamines, in particular tetraace
  • bleach activators At washing temperatures below 60 0 C, especially below 45 ° C up to the cold water temperature, the effect of the previously known bleach activators often decreases.
  • Another significant disadvantage of said bleach activators is their limited effectiveness in the pH range ⁇ 9. Since their activation requires a high concentration of perhydroxyl anions, known activators preferably work best between pH 9 and 11. However, this results in deficits in certain fields of application, for example in liquid detergents or neutral or low-alkaline detergents and cleanser formulations.
  • No. 3,822,114 describes metal-free bleaching agents which, in addition to an organic or inorganic peroxygen compound, contain cyclic and open-chain aldehydes and ketones as bleach boosters. These systems allow a good oxidation effect at temperatures above 25 ° C.
  • Other bleaching enhancers are i.a. in WO 95/31527 (bicyclic and tricyclic ketones such as decalin-1, 5-dione, methyldecalin-1, 6-dione and tricycloundecanedione) and in EP 1 209 221 (sugar ketones).
  • US 5,785,887 protects the use of cyclic and open chain monoketals of diketones, e.g. Cyclohexanedione as
  • the object of the invention is to improve the oxidizing and bleaching action of inorganic peroxygen compounds, in particular in the temperature range from 10 0 C to 45 ° C and pH values in the range 7 to 9
  • the invention relates to the use of aminoacetones or their salts of the general formulas (I) and (II)
  • R 1 and R 2 independently of one another are hydrogen, C 1 -C 22 -alkyl, C 2 -C 22 -alkenyl-phenyl or C 5 -C 8 -cycloalkyl or R 1 and R 2 together with the nitrogen atom are a 5, 6 or 7-membered one X "is an anion, preferably chloride, bromide, iodide, toluenesulfonate, benzenesulfonate, cumene sulfonate, mesityl sulfonate, sulfate, hydrogensulfate, acetate, a fatty acid anion or an anion of polycarboxylates, especially fatty acids
  • Anions of C 8 -C 22 - Anions of polycarboxylates are preferably anions of polyacrylic acid or of copolymers of maleic anhydride and acrylic acid.
  • aminoacetones in particular those which are liquid with short-chain radicals R 1 and R 2 , are highly volatile compounds, they are preferably in the form of their salts are used, for better handling, they are adsorbed in a particular embodiment on a solid support material.
  • Salts are formed by reacting the aminoacetone with an inorganic or organic acid.
  • Preferred acids are hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, acetic acid, lauric acid, benzoic acid or polymeric carboxylic acids such as acidic or partially neutralized polyacrylic acids and copolymers of acrylic acid and maleic acid.
  • Aminoacetone or their salts are: N, N-dimethylaminoacetone, N 1 N- diethylaminoacetone, NN-Dipropylaminoaceton, N, Nn-Dibutylaminoaceton and N, N-Diisobutylaminoaceton, Piperidylaceton, 1-morpholin-4-yl-acetone, and N, N-dimethylaminoacetone hydrochloride, N, N-diethylaminoacetone hydrochloride, N, N-diethylaminoacetone hydrogensulfate, N, N-diethylaminoacetone acetate, N, N-diethylaminoacetone polycarboxylate, N, N-dipropylaminoacetone hydrochloride, N, N- Di-n-butylaminoacetone hydrochloride, N, N-diisobutylaminoacetone hydrochloride, piperidylacetone
  • aminoacetones or their salts can be used either individually or in a mixture.
  • the aminoacetones and their salts can be used both with and without the use of a carrier for use in detergents and cleaners.
  • suitable carrier materials include clays, silicates, carbonates, phosphates, sulfates and citrates.
  • Clays are naturally occurring crystalline or amorphous silicates of aluminum, iron, magnesium, calcium, potassium and sodium, for example kaolin, talc, pyrophyllite, attapulgite, sepiolite, saponites, hectorites, smectites such as montmorillonite, in particular bentonites, bauxite and zeolites.
  • bentonites such as are commercially available under the name Copisil® S 401, Copisil® N 401, Laundrosil® DGA, Laundrosil® EX 0242, Copisil® S 401, Copisil® N 401 or Ikomont® CA.
  • Sheet silicates can also be used in acid-modified form, as are available in the commercial products Tonsil® EX 519, Tonsil Optimum 210 FF, Tonsil Standard 310 FF and 314 FF, and Opazil® SO from the company Südchemie.
  • Amorphous polysilicic acids whose internal surface is preferably in the range from 10 m 2 / g to 500 m 2 / g, in particular 100 m 2 / g to 450 m 2 / g, may furthermore be suitable as the carrier material.
  • Suitable silicas are those which have been produced after the thermal process (flame hydrolysis of SiCl 4 ) (so-called pyrogenic silicic acids) and silicas produced by wet processes (so-called precipitated silicas). They can also be prepared by the action of mineral acids on water glass.
  • support materials are sodium or potassium sulfates, sodium carbonates and sodium bicarbonates and alkali metal phosphates, which may be in the form of their alkaline, neutral or acidic sodium or potassium salts. Examples of these are trisodium phosphate, tetrasodium diphosphate, disodium dihydrogen diphosphate,
  • Pentasodium triphosphate so-called sodium hexameta phosphate, oligomeric trisodium phosphate with degrees of oligomerization of 5 to 1000, in particular 5 to 50, and mixtures of sodium and potassium salts.
  • Useful organic support materials are, for example, the carboxylic acids preferably used in the form of their sodium salts, such as citric acid, nitriloacetate (NTA) and ethylenediaminetetraacetic acid.
  • NTA nitriloacetate
  • polymeric carboxylates and their salts include, for example, the salts of homopolymeric or copolymeric polyacrylates,
  • Polymethacrylates and in particular copolymers of acrylic acid with maleic acid preferably those of 50% to 10% of maleic acid, polyaspartic acid and also polyvinylpyrrolidone and urethanes.
  • the molecular weight of the homopolymers is generally between 1000 and 100,000, that of the copolymers between 2000 and 200,000, preferably 50,000 to 120,000, based on the free acid.
  • water-soluble polyacrylates which are crosslinked, for example, with about 1% of a polyallyl ether of sucrose and which have a molecular weight of more than one million are also suitable. Examples of these are the polymers available under the name Carbopol 940 and 941.
  • the salts of the aminoacetones according to the invention can be prepared in situ, e.g. by spraying the aminoacetone on an acidic or partially neutralized support (e.g., polyacrylic acid).
  • an acidic or partially neutralized support e.g., polyacrylic acid
  • the compounds according to the invention consist of 20 to 98 wt .-%, preferably 30 to 95 wt .-%, particularly preferably 40 to 90 wt .-% of carrier material, the remainder is the aminoacetone or its salt, optionally also further aids.
  • these powdery compounds may be in granulated form.
  • Suitable binders for the granulation may include cellulose and starch and their ethers or esters, for example carboxymethylcellulose (CMC), methylcellulose (MC) or
  • Hydroxyethyl cellulose and the corresponding starch derivatives, but also film-forming polymers, for example polyacrylic acids and copolymers of maleic anhydride and acrylic acid, and the salts of these polymer acids.
  • film-forming polymers for example polyacrylic acids and copolymers of maleic anhydride and acrylic acid, and the salts of these polymer acids.
  • Commercially available products are, for example, Sokalan® CP 5 or 45, Sokalan® CP 12 S or CP 13 S.
  • binders and granulating agents and surfactants in particular anionic and nonionic surfactants, surfactant compounds, di- and
  • saturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, hydrogenated Erucic acid and behenic acid
  • natural fatty acids eg Coconut, palm kernel or Taigfett720 derived mixtures
  • soaps in particular saturated fatty acid soaps and waxes are used.
  • the amount of auxiliaries, likewise based on the finished bleach compound, can be from 0 to 45% by weight, preferably from 2 to 20% by weight.
  • the mixture is initially introduced into the pulverulent carrier material in a mixer, preferably a plowshare mixer or intensive mixer, and charged with an aqueous aminoacetone or aminoacetone salt solution.
  • the moist product is dried, preferably fluidized bed or fluidized bed dryers are used. After drying, granules are obtained which typically have an active content of 10-60% aminoacetone or aminoacetone salt. From the granules produced by segregating the coarse grain and the fine grain fraction are separated. The coarse grain fraction is crushed by grinding and just like the
  • the grain size of the granules produced in this way is generally in the range of 50 to 2000 microns, preferably 150 to 1800 microns, more preferably from 300 to 1500 microns.
  • the carrier material is to be selected and the loading concentration adjusted so that the mixture has a sufficient plastic deformability.
  • the extrudates obtained from the process may be rounded in a raking apparatus. Finally, the granules are dried and worked up in an analogous manner as described above.
  • the aminoacetone or aminoacetone salt solution is sprayed onto the carrier material in a fluidized-bed granulation process and granulated. Since the process offers the advantage of simultaneous granulation and drying, higher loadings can usually be achieved compared to a sequential process of carrier in the mixer with subsequent drying. The loading limit is then determined by the physical properties of the individual components or of the mixture.
  • the granules obtained according to the invention are suitable directly for use in detergents and cleaners.
  • they can be provided with a coating shell according to methods known per se.
  • the granules are coated in an additional step with a film-forming substance, whereby the product properties can be significantly influenced.
  • Suitable coating agents are all film-forming substances, such as waxes, silicones, fatty acids, fatty alcohols, soaps, anionic surfactants, nonionic surfactants, cationic surfactants, anionic and cationic polymers, and polyalkylene glycols. Preference is given to coating substances with a Melting point of 30 - 100 0 C used.
  • C 8 -C 31 fatty acids for example lauric, myristic, stearic acid
  • C ⁇ -CarFettalkohole Polyethylene glycols having a molecular weight of 1000 to 50,000 g / mol
  • Fatty alcohol polyalkoxylates with 1 to 100 moles EO Alkanesulfonates, alkylbenzenesulfonates, ⁇ -olefinsulfonates, alkyl sulfates, alkyl ether sulfates having C 8 -C 31 -hydrocarbon radicals
  • polymers for example polyvinyl alcohols, waxes, for example montan waxes, paraffin waxes, ester waxes, polyolefin waxes, silicones.
  • further substances which do not soften or melt in this area can be present in dissolved or suspended form, for example homopolymers, copolymers or graft copolymers of unsaturated carboxylic acids and / or sulfonic acids and their derivatives Alkali salts, cellulose ethers, starch, starch ethers, polyvinylpyrrolidone; mono- and polyvalent carboxylic acids,
  • Hydroxycarboxylic acids or ether carboxylic acids having 3 to 8 C atoms and their salts Silicates, carbonates, bicarbonates, sulfates, phosphates, phosphonates.
  • the content of coating substance can be from 1 to 30% by weight, preferably from 5 to 15% by weight, based on the coated granules.
  • mixers mechanically induced fluidized bed
  • fluidized bed apparatuses pneumatically induced fluidized bed
  • mixers for example, plowshare mixers (continuous and batchwise), ring layer mixers or even Schugi mixers are possible.
  • the tempering can be carried out using a mixer in a granule preheater and / or in the mixer directly and / or in a fluidized bed downstream of the mixer.
  • Granulated coolers or fluid bed coolers can be used to cool the coated granules.
  • the heat treatment takes place via the hot gas used for fluidization.
  • the granules coated by the fluidized-bed method can be cooled by a granulate cooler or a fluidized-bed cooler, similar to the mixing method. Both in the mixing process and in the fluidized bed process can the coating substance be sprayed on a single-material or a Zweistoffdüsvorraum.
  • the optional tempering consists in a heat treatment at a temperature of 30 to 100 0 C, but equal to or below the melting or softening temperature of the respective shell substance. Preference is given to working at a temperature which is just below the melting or softening temperature.
  • the bleaching compounds according to the invention are distinguished by very good storage stability in pulverulent washing, cleaning and disinfecting agent formulations. They are ideal for use in heavy-duty detergents, stain salts, machine dishwashing detergents and powdery all-purpose cleaners.
  • aminoacetones or their salts are used in the detergents and cleaners according to the invention which additionally also contain organic or inorganic peroxygen compounds in concentrations of from 0.01 to 10%, preferably from 0.1 to 8% and in particular from 0.5 to 5%.
  • alkali metal or ammonium peroxosulfates are primarily considered, e.g. potassium peroxymonosulfate
  • potassium peroxomonosulfate (usually in the form of the triple salt) in the form of granules such as e.g. in DE 196 46 225 are described in order to increase their storage stability.
  • alkali perborate monohydrate or tetrahydrate and / or alkali metal percarbonate with sodium being the preferred alkali metal.
  • concentration of the inorganic oxidizing agents on the total formulation of the cleaning agents is 1 to 90%, but preferably 5 to 25%.
  • the cleaning agents according to the invention may contain organic-based oxidizing agents in the concentration range from 1 to 20%.
  • organic-based oxidizing agents include all known peroxycarboxylic acids, such as Monoperoxyphthalic acid, dodecanediperoxyacid or phthalimidoperoxycarboxylic acids such as PAP.
  • bleaching is understood here to mean both the bleaching of dirt located on the textile surface and the bleaching of dirt located in the wash liquor and detached from the textile surface. The same applies analogously to the bleaching of stains on hard surfaces. Other potential applications are in the personal care field, e.g. to improve the effectiveness of denture cleaners. Furthermore, find the complexes of the invention
  • the invention relates to a washing and cleaning agent such as detergents and bleaches for textile materials, cleaning agents for hard surfaces such as dishwashers or denture cleaners containing the aminoacetones or their salts as defined above and peroxygen compounds.
  • a washing and cleaning agent such as detergents and bleaches for textile materials, cleaning agents for hard surfaces such as dishwashers or denture cleaners containing the aminoacetones or their salts as defined above and peroxygen compounds.
  • Such conditions are especially present when the reactants meet in aqueous solution. This can be done by separately adding the peroxygen compound and the aminoacetone or its salt to a washing or detergent-containing solution. From the beginning, the cleaning or washing agent particularly advantageously contains the aminoacetone or a
  • the peroxygen compound may also be used separately in bulk or as preferably aqueous solution or suspension may be added to the solution when a non-oxygen detergent or cleaning agent is used.
  • the detergents and cleaning agents according to the invention which may be in the form of granules, powdered or tablet-like solids, other shaped articles, homogeneous solutions or suspensions, may in principle contain all known and conventional ingredients in addition to the aminoacetones and their salts mentioned.
  • the detergents and cleaners according to the invention may contain, in particular, builder substances, surface-active surfactants, sequestering agents, enzymes and also special additives with a dye-protecting or fiber-sparing action.
  • builder substances surface-active surfactants
  • sequestering agents enzymes
  • enzymes enzymes
  • special additives with a dye-protecting or fiber-sparing action.
  • Other adjuvants such as electrolytes, foam regulators and dyes and fragrances are possible.
  • the compositions according to the invention may contain system and environmentally acceptable acids, in particular citric acid, acetic acid, tartaric acid, malic acid, lactic acid, glycolic acid, succinic acid, glutaric acid and / or adipic acid, but also mineral acids, in particular sulfuric acid or alkali metal hydrogensulfates, or bases, in particular ammonium or alkali metal hydroxides.
  • Such pH regulators are preferably not more than 10% by weight, in particular from 0.5 to 6% by weight, in the compositions according to the invention. contain.
  • Recrystallized diethylamino hydrochloride was filtered off with suction and washed with a small amount of cold diethyl ether.
  • the ethereal solution of diethylaminoacetone was completely concentrated in vacuo and the remaining brown oil fractionally distilled in vacuo. Boiling point 67 to 70 ° C (49 mbar).
  • Example 12 pH dependence of the bleach (comparison of diethylaminoacetone, diethylaminoacetone hydrochloride and diethylmethylammonium acetone tosylate)
  • the whiteness of the test soiling was determined by means of an Elrepho measuring instrument.
  • the whiteness (dE) was represented as a function of the pH:
  • Example 13 Bleaching performance of dialkylaminoacetones and their salts

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  • 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)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne l'utilisation d'aminoacétones ou de leurs sels de formules générales (I) et (II), dans lesquelles R<SUP>1</SUP> et R<SUP>2</SUP> représentent indépendamment l'hydrogène, un alkyle en C<SUB>1</SUB>-C<SUB>22</SUB>, un alcényle en C<SUB>2</SUB>-C<SUB>22</SUB>, un phényle ou un cycloalkyle en C<SUB>5</SUB>-C<SUB>8</SUB> ou R<SUP>1</SUP> et R<SUP>2</SUP> forment avec l'atome d'azote un système cyclique à 5, 6 ou 7 éléments, X<SUP>-</SUP> représente un anion, par exemple chlorure, bromure, iodure, toluènesulfonate, benzènesulfonate, cumènesulfonate, mésitylsulfonate, sulfate, hydrogénosulfate, acétate, anion d'acide gras ou anion de polycarboxylats, en tant qu'amplificateur d'aptitude au blanchiment pour composés peracides inorganiques dans une gamme de pH de 7 à 9.
EP07801473A 2006-08-04 2007-07-31 Utilisation d'aminoscétones et de leur sels en tant qu'amplificateurs d'aptitude au blanchiment pour composés peracide Withdrawn EP2049643A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006036889A DE102006036889A1 (de) 2006-08-04 2006-08-04 Verwendung von Aminoacetonen und deren Salzen als Bleichkraftverstärker für Persauerstoffverbindungen
PCT/EP2007/006742 WO2008014965A1 (fr) 2006-08-04 2007-07-31 Utilisation d'aminoscétones et de leur sels en tant qu'amplificateurs d'aptitude au blanchiment pour composés peracide

Publications (1)

Publication Number Publication Date
EP2049643A1 true EP2049643A1 (fr) 2009-04-22

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EP07801473A Withdrawn EP2049643A1 (fr) 2006-08-04 2007-07-31 Utilisation d'aminoscétones et de leur sels en tant qu'amplificateurs d'aptitude au blanchiment pour composés peracide

Country Status (5)

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US (1) US20090289221A1 (fr)
EP (1) EP2049643A1 (fr)
JP (1) JP2010526156A (fr)
DE (1) DE102006036889A1 (fr)
WO (1) WO2008014965A1 (fr)

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JP2010526156A (ja) 2010-07-29
WO2008014965A1 (fr) 2008-02-07
US20090289221A1 (en) 2009-11-26

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