EP0909810B1 - Utilisation des aminonitrile-N-oxides comme activateurs de blanchiment - Google Patents

Utilisation des aminonitrile-N-oxides comme activateurs de blanchiment Download PDF

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Publication number
EP0909810B1
EP0909810B1 EP98117813A EP98117813A EP0909810B1 EP 0909810 B1 EP0909810 B1 EP 0909810B1 EP 98117813 A EP98117813 A EP 98117813A EP 98117813 A EP98117813 A EP 98117813A EP 0909810 B1 EP0909810 B1 EP 0909810B1
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EP
European Patent Office
Prior art keywords
aminonitrile
formula
oxide
alkyl
detergent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP98117813A
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German (de)
English (en)
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EP0909810A1 (fr
Inventor
Bernd Dr. Nestler
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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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
    • C11D3/3925—Nitriles; Isocyanates or quarternary ammonium nitriles
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/32—Bleaching agents

Definitions

  • peroxidic bleaching agents such as perborates, Percarbonates, persilicates and perphosphates
  • Bleach activators are called.
  • nitrile bleach activators and their use as bleach activators in Bleaching agents are described, for example, in EP 303 520, GB 802 035, US 4,883,917, US 5 478 356, US 5 591 378, WO 9 606 912 and WO 9 640 661.
  • aminonitrile N-oxides or thereof derived salts have a better bleaching effect than bleach activators according to the state of the art.
  • Aminonitrile N-oxides or their salts of the formula 1 are preferred, in which R 1 and R 2 are C 1 -C 4 -alkyl, in particular methyl, and A is phenylene.
  • the aminonitrile N-oxides or the salts derived therefrom are easily accessible by reacting aminonitriles with oxidizing agents; Such reactions are described, for example, in J. Backes "Amine", Methods of Organic Chemistry (Houben-Weyl), D. Klamann (ed.) Vol. E 16d (1992), pp. 1235-1329 and the literature cited therein.
  • the invention also relates to the use of these bleach activators in bleaching detergents and cleaning agents as well as in paper and textile bleaching.
  • the detergents and cleaning agents contain a peroxide compound and the bleach activator usually also surface-active compounds and other known ingredients.
  • Bleach activators and other suitable bleach activators e.g. TAED, Tetraacetylglycoluril, glucose pentaacetate, sodium nonanoyloxybenzenesulfonate, Benzoylcaprolactam or nitrile activators may be included.
  • TAED Tetraacetylglycoluril
  • glucose pentaacetate glucose pentaacetate
  • sodium nonanoyloxybenzenesulfonate Benzoylcaprolactam or nitrile activators
  • Benzoylcaprolactam or nitrile activators may be included.
  • These additional Bleach activators can be present in an amount of 1 to 10% by weight.
  • the surfactant can be derived from natural products such as Soap, or is a synthetic compound from the group of anionic, non-ionic, amphoteric, zwitterionic or cationic surface-active Substances, or mixtures of these.
  • suitable substances commercially available, and are described in the literature, for example in "Surface active agents and detergents", Vol. 1 and 2, by Schwartz, Perry and Berch.
  • the total proportion of surface-active compounds can be up to 50 % By weight, preferably 1% by weight to 40% by weight, in particular 4% by weight up to 25% by weight.
  • Synthetic anionic surfactants are common water-soluble alkali metal salts of organic sulfates and sulfonates with alkyl radicals from about 8 to 22 carbon atoms, the term "alkyl” being the Includes alkyl substituents of higher aryl groups.
  • Examples include sodium and ammonium alkyl sulfates, especially the sulfates obtained by sulfating higher (C 8 -C 18 ) alcohols; Sodium and ammonium alkylbenzenesulfonates with an alkyl radical from C 9 to C 20 , in particular linear secondary sodium alkylbenzenesulfonates with an alkyl radical from C 10 to C 15 ; Sodium alkyl glycerol ether sulfates, especially the esters of the higher alcohols derived from tallow and coconut oil; the sodium sulfates and sulfonates of the coconut fatty acid monoglycerides; Sodium and ammonium salts of the sulfuric acid esters of higher (C 9 to C 18 ) oxalkylated, especially the fatty alcohols alkoxylated with ethylene oxide; the reaction products of the esterification of fatty acids with isethionic acid and subsequent neutralization with sodium hydroxide; Sodium and ammonium salts of the
  • nonionic surface-active compounds which are preferably used together with anionic surface-active compounds, are in particular the reaction products of alkylene oxides (usually ethylene oxide) with alkylphenols (alkyl radicals from C 5 to C 22 ), the reaction products generally 5 to 25 ethylene oxide (EO ) Units contained in the molecule; the reaction products of aliphatic (C 8 to C 18 ) primary or secondary, linear or branched alcohols with ethylene oxide, generally with 6 to 30 EO, and the addition products of ethylene oxide with reaction products of propylene oxide and ethylenediamine.
  • Other nonionic surface active compounds are alkyl polyglycosides, long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulfoxides.
  • Amphoteric or zwitterionic surfactants can also be used can be used in the compositions according to the invention, but what is usually not desired because of its high cost. If amphoteric or zwitterionic compounds are used, so this usually happens in small amounts in compositions that are mainly anionic and contain nonionic surfactants.
  • the detergents and cleaning agents generally also contain a builder.
  • Builders come into consideration: calcium binding substances, precipitants, calcium-specific Ion exchangers and their mixtures.
  • calcium binders include alkali metal polyphosphates such as sodium tripolyphosphate; Nitrilotriacetic acid and its water-soluble salts; the alkali metal salts of Carboxymethyloxy succinic acid, ethylenediaminetetraacetic acid, Oxydisuccinic acid, mellitic acid, benzene polycarboxylic acids, citric acid and Polyacetal carboxylates as described in U.S. Pat. 4,144,226 and 4,146,495.
  • precipitants are sodium orthophosphate, sodium carbonate and Long chain fatty acid soaps.
  • ion exchangers specific for calcium are various types of water-insoluble, crystalline or amorphous Aluminum silicates, of which the zeolites are the best known representatives.
  • the washing and Detergents contain each of the conventional additives in amounts that one usually finds in such means.
  • additives are Foaming agents, such as alkanolamides, especially the monoethanolamides Palm kernel oil fatty acids and coconut fatty acids; foam-preventing substances such as alkyl phosphates and silicones; Graying inhibitors and the like Auxiliaries such as sodium carboxymethyl cellulose and alkyl or substituted alkyl cellulose ethers; Stabilizers such as ethylenediaminetetraacetic acid; softener for textiles; inorganic salts such as sodium sulfate; and, usually small Quantities, fluorescent substances, perfumes, enzymes such as proteases, cellulases, Lipases and amylases, disinfectants and dyes.
  • the bleach activators of this invention can be used in a variety of laundry and Detergents are used. These include laundry detergents, Textile bleach, surface cleaners, toilet cleaners, Dishwasher cleaner, and also denture cleaner.
  • the detergents can be in solid or liquid form. It is for the sake of stability and Manageability advantageous to the bleach activators in the form of granules use that contain a binder in addition to the bleaching catalyst.
  • Various methods for producing such granules are in the patent literature described, for example, in Canada Pat. No.
  • the granules containing the bleach activators are generally the Detergent composition along with the other dry Components such as enzymes, inorganic peroxide bleach added.
  • the detergent composition to which the catalyst granules are added can be obtained in several ways, such as Dry mixing, extruding, spray drying.
  • the bleach activators according to the invention are Particularly suitable for non-aqueous, liquid detergents, together with a bleaching peroxide compound, such as sodium perborate, around the detergent great cleaning ability for fabrics and textiles.
  • aqueous, liquid detergents, pasty and gelatinous Including detergent compositions are well known in the art are known, and are described, for example, in US 2,864,770, US 2,940,938, US 4,772,412, US 3 368 977, GB-A-1 205 711 GB-A-1 370 377, GB-A-1 270 040, GB-A-1 292 352, GB-A-2 194 536, DE-A-2 233 771, EP-A-0 028 849.
  • compositions in the form of a non-aqueous, liquid medium in which a solid phase can be dispersed can be a liquid, surface-active substance, preferably a nonionic surfactant; a non polar liquid medium such as liquid paraffin; a polar solvent such as Polyols, for example glycerin, sorbitol, ethylene glycol, possibly in combination with low molecular weight monohydric alcohols such as ethanol or isopropanol; or Mixtures of these.
  • the solid phase can consist of builder substances, alkalis, abrasive substances, Polymers and other solid ionic surfactants, bleaches fluorescent substances and other common solid ingredients.
  • a lead composition was prepared by combining 200 ml of an aqueous solution of reference detergent WMP (laundry research Krefeld, 5 g / l in water with 15 ° dH) solution, 150 mg of sodium perborate monohydrate and 50 mg of the respective activator.
  • WMP laundry research Krefeld, 5 g / l in water with 15 ° dH
  • tissue pieces soiled with the standard soiling BC-1 tea were subjected to a treatment at a temperature of 40 ° C. under isothermal washing conditions in a Linitest device (Heraeus).
  • Connections 1-5 are: 1 2 3 4 5 ⁇ R 1.0 0.7 1.2 0.3 0.1 mCBA: meta-chlorobenzoic acid salt
  • the washing experiments show that the aminonitrile N-oxides according to the invention have good bleaching performance. Further advantageous properties of the complexes described are low color damage and low fiber damage.

Claims (8)

  1. Utilisation d'aminonitriles N-oxydes de formule générale (1)
    Figure 00160001
    dans laquelle
    R1, R2
    représentent indépendamment l'un de l'autre des groupes alkyle en C1 à C15, cycloalkyle ou aryle, substitués ou non substitués, qui peuvent être substitués par un fluor, chlore, brome, alcoxy en C1 à C5, alcoxy en C1 à C5-carbonyle, amino, ammonium, carboxyle, cyano ou cyanamino, ou forment ensemble avec l'atome d'azote auquel ils sont liés un cycle ayant de 4 à 6 atomes de carbone, qui peut être substitué par un alkyle en C1 à C5, alcoxy en C1 à C5, alcanoyle en C1 à C5, phényle, amino, ammonium, cyano, cyanamino, chlore ou brome et ce cycle pouvant contenir en plus de l'atome d'azote, à la place de groupes -CH2- un ou plusieurs atomes d'oxygène ou un groupe
    Figure 00160002
    dans lequel R3 est un hydrogène, alkyle en C1 à C7 ou cycloalkyle, phényle ou alkylaryle en C7 à C9,
    A
    représente un groupe alkylène en C1 à C5, un cycloalkylène en C5 à C10 ou un groupe arylène,
    comme activateurs de blanchiment dans des lessives et détergents ainsi que dans le blanchiment des papiers et des textiles.
  2. Utilisation d'aminonitriles N-oxydes ou de leurs sels de formule (1) selon la revendication 1, caractérisée en ce qu'on utilise un composé de formule (1), dans laquelle R1 et R2 représentent un alkyle en C1 à C4, en particulier un méthyle et A un phénylène.
  3. Lessives et détergents contenant un composé peroxydique et un aminonitrile N-oxyde de formule (1) selon la revendication 1.
  4. Lessives et détergents contenant un composé peroxydique et de 0,05 à 20 % en poids d'un aminonitrile N-oxyde de formule 1 selon la revendication 1.
  5. Lessives et détergents contenant de 1 à 60 % en poids d'un composé peroxydique et un aminonitrile N-oxyde de formule 1 selon la revendication 1.
  6. Lessives et détergents contenant un aminonitrile N-oxyde de formule (1) selon la revendication 1 et un perborate, percarbonate, perphosphate, persilicate, monopersulfate, peroxyde d'urée, hydroperoxyde de cumène ou hydroperoxyde de tert.-butyle.
  7. Lessives et détergents contenant un composé peroxydique, un aminonitrile N-oxyde de formule (1) selon la revendication 1 ainsi qu'un activateur de blanchiment, qui n'est pas un aminonitrile N-oxyde.
  8. Lessives et détergents contenant un composé peroxydique, un aminonitrile N-oxyde de formule (1) selon la revendication 1 et des composés tensioactifs.
EP98117813A 1997-10-20 1998-09-19 Utilisation des aminonitrile-N-oxides comme activateurs de blanchiment Expired - Lifetime EP0909810B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19746290A DE19746290A1 (de) 1997-10-20 1997-10-20 Verwendung von Aminonitril-N-oxiden als Bleichaktivatoren
DE19746290 1997-10-20

Publications (2)

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EP0909810A1 EP0909810A1 (fr) 1999-04-21
EP0909810B1 true EP0909810B1 (fr) 2004-12-22

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US (2) US6007583A (fr)
EP (1) EP0909810B1 (fr)
JP (1) JP4021075B2 (fr)
BR (1) BR9804057A (fr)
DE (2) DE19746290A1 (fr)

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US6825160B1 (en) 1999-08-27 2004-11-30 Procter & Gamble Company Color safe laundry methods employing cationic formulation components
US6818607B1 (en) * 1999-08-27 2004-11-16 Procter & Gamble Company Bleach boosting components, compositions and laundry methods
US6903060B1 (en) 1999-08-27 2005-06-07 Procter & Gamble Company Stable formulation components, compositions and laundry methods employing same
ATE311432T1 (de) * 1999-08-27 2005-12-15 Procter & Gamble Stabile substanzen, zusammensetzungen und waschverfahren zu deren verwendung
AU6935800A (en) * 1999-08-27 2001-03-26 Procter & Gamble Company, The Controlled availability of formulation components, compositions and laundry methods employing same
US6821935B1 (en) 1999-08-27 2004-11-23 Procter & Gamble Company Color safe laundry methods employing zwitterionic formulation components
BR0013610A (pt) * 1999-08-27 2002-07-16 Procter & Gamble Componentes de formulções de ação rápida,composições e métodos para lavar roupa empregando os mesmos
US7109156B1 (en) 1999-08-27 2006-09-19 Procter & Gamble Company Controlled availability of formulation components, compositions and laundry methods employing same
CN1384867A (zh) 1999-08-27 2002-12-11 宝洁公司 稳定性提高的配制组分、使用该组分的组合物和洗衣方法
DE10064636A1 (de) * 2000-12-22 2002-07-04 Henkel Kgaa Flüssiges Wasch-und/oder Reinigungsmittel
US7169744B2 (en) * 2002-06-06 2007-01-30 Procter & Gamble Company Organic catalyst with enhanced solubility
US7557076B2 (en) * 2002-06-06 2009-07-07 The Procter & Gamble Company Organic catalyst with enhanced enzyme compatibility
US20050113246A1 (en) * 2003-11-06 2005-05-26 The Procter & Gamble Company Process of producing an organic catalyst
AR051659A1 (es) * 2005-06-17 2007-01-31 Procter & Gamble Una composicion que comprende un catalizador organico con compatibilidada enzimatica mejorada

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Publication number Publication date
DE59812405D1 (de) 2005-01-27
JP4021075B2 (ja) 2007-12-12
JPH11199894A (ja) 1999-07-27
BR9804057A (pt) 1999-12-07
DE19746290A1 (de) 1999-04-22
US6120557A (en) 2000-09-19
EP0909810A1 (fr) 1999-04-21
US6007583A (en) 1999-12-28

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