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EP0909810A1 - 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
EP0909810A1
EP0909810A1 EP98117813A EP98117813A EP0909810A1 EP 0909810 A1 EP0909810 A1 EP 0909810A1 EP 98117813 A EP98117813 A EP 98117813A EP 98117813 A EP98117813 A EP 98117813A EP 0909810 A1 EP0909810 A1 EP 0909810A1
Authority
EP
European Patent Office
Prior art keywords
aminonitrile
detergents
formula
alkyl
oxide
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.)
Granted
Application number
EP98117813A
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German (de)
English (en)
Other versions
EP0909810B1 (fr
Inventor
Bernd Dr. Nestler
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 Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
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 GmbH filed Critical Clariant GmbH
Publication of EP0909810A1 publication Critical patent/EP0909810A1/fr
Application granted granted Critical
Publication of EP0909810B1 publication Critical patent/EP0909810B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C11D3/3925—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
  • Bleaching activators are called.
  • bleach activators Many substances are known in the art as bleach activators. Usually these are reactive organic compounds with a O-acyl or N-acyl group in alkaline solution together with a source form the corresponding peroxyacids for hydrogen peroxide.
  • bleach activators are, for example N, N, N ', N'-tetraacetylethylenediamine (TAED), glucose pentaacetate (GPA), Xylose tetraacetate (TAX), sodium 4-benzoyloxybenzenesulfonate (SBOBS), Sodium trimethylhexanoyloxybenzenesulfonate (STHOBS), tetraacetylglucoluril (TAGU), tetraacetylcyanoic acid (TACA), di-N-acetyldimethylglyoxin (ADMG) and 1-phenyl-3-acetylhydantoin (PAH).
  • TAED N, N, N ', N'-tetraacetylethylenediamine
  • GPA glucose pentaacetate
  • TAX glucose pentaacetate
  • TAX Xylose tetraacetate
  • SBOBS sodium 4-benzoyloxybenzenesulfon
  • nitrile bleach activators have become more important because they are turn out to be extraordinarily bleaching active. These are probably connections in perhydrolysis a peroxyimidic acid, which is the bleaching agent.
  • 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.
  • the aminonitrile-N-oxides to be used according to the invention also include their salts, for example those salts which are obtained, for example, by reacting the corresponding aminonitrile-N-oxide with acids such as, in particular, HCl, HBr, HF, H 2 SO 4 , H 3 PO 4 and others acidic phosphates, pyro-, meta- and poly-phosphoric acid, HBF 4 , HPF 6 , H 2 CO 3 , HNO 3 -, citric acid, formic acid, R 4 SO 4 H, R 4 SO 3 H, R 4 COOH, where R 4 represents a substituted or unsubstituted C 1 -C 21 alkyl or aryl radical can be obtained.
  • acids such as, in particular, HCl, HBr, HF, H 2 SO 4 , H 3 PO 4 and others acidic phosphates, pyro-, meta- and poly-phosphoric acid, HBF 4 , HPF 6 , H 2 CO 3 , HNO
  • 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.
  • Suitable peroxidic bleaching agents are alkali peroxides, organic peroxides such as Urea peroxide, and inorganic persalts, such as the alkali perborates, -percarbonates, -perphosphates, -persilicates and -persulfate. Mixtures of two or more of these compounds are also suitable. Particularly preferred are sodium perborate tetrahydrate and especially sodium perborate monohydrate. Sodium perborate monohydrate is because of its good shelf life and its good solubility in water preferred. Sodium percarbonate can be made Environmental reasons may be preferred. Alkyl hydroperoxides are another suitable group of peroxide compounds. Examples of these substances are Cumene hydroperoxide and tert-butyl hydroperoxide.
  • the nitrile agent according to the invention can be used in detergents and cleaning agents Bleach activator with a weight fraction of about 0.05% to 20%, preferably from 0.5% to 10%, especially 1% to 7.5%, may be present together with a peroxide compound.
  • the proportion by weight of these peroxide compounds is usually from 1% to 60%, preferably from 4% to 30%, in particular from 10% up to 25%.
  • 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 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, with generally 6 to 30 EO, and the addition products of ethylene oxide with reaction products of propylene oxide and ethylenediamine.
  • Other nonionic surfactants 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 non-ionic surfactants.
  • Soaps can also be used in the compositions according to the invention, preferably in a proportion of less than 25% by weight. They are particularly suitable in small amounts in binary (soap / anionic surfactant) or in ternary mixtures together with nonionic or mixed synthetic anionic and nonionic surfactants.
  • the soaps used are preferably the sodium salts, and less preferably the potassium salts of saturated or unsaturated C 10 -C 24 fatty acids, or mixtures thereof.
  • the proportions of such soaps can be from 0.5% by weight to 25% by weight, smaller amounts from 0.5% by weight to 5% by weight are generally sufficient for foam control. Soap contents between about 2% and about 20%, especially between about 5% and about 10%, have a positive effect. This is particularly the case in hard water, where the soap serves as an additional builder.
  • 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.
  • These builder substances can be present from 5% by weight to 80% by weight, a proportion of 10% by weight to 60% by weight is preferred.
  • the washing and Detergents contain each of the conventional additives in amounts that one usually finds in such means.
  • Foaming agents such as alkanolamides, especially the monoethanolamides Palm kernel oil fatty acids and coconut fatty acids; anti-foam substances such as alkyl phosphates and silicones; Graying inhibitors and the like Auxiliaries such as sodium carboxymethyl cellulose and alkyl or substituted Alkyl cellulose ether; Stabilizers such as ethylenediaminetetraacetic acid; Plasticizers 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 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 connection 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 2nd 3rd 4th 5 ⁇ R 1.0 0.7 1.2 0.3 0.1
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Paper (AREA)
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)

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

Family

ID=7846054

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98117813A Expired - Lifetime EP0909810B1 (fr) 1997-10-20 1998-09-19 Utilisation des aminonitrile-N-oxides comme activateurs de blanchiment

Country Status (5)

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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001016276A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulation ameliorant la stabilite, et compositions et procedes de blanchissage les utilisant
WO2001016275A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulation a action rapide, compositions et procedes de nettoyage utilisant ces composants
WO2001016274A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulations stables, compositions et procedes de nettoyage ces composants
WO2001016263A3 (fr) * 1999-08-27 2001-06-07 Procter & Gamble Disponibilite controlee de composants de formulation, compositions et procede de blanchissage utilisant ces produits
WO2002051973A1 (fr) * 2000-12-22 2002-07-04 Henkel Kommanditgesellschaft Auf Aktien Detergent et/ou nettoyant liquide

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US6821935B1 (en) 1999-08-27 2004-11-23 Procter & Gamble Company Color safe laundry methods employing zwitterionic formulation components
US6903060B1 (en) 1999-08-27 2005-06-07 Procter & Gamble Company Stable formulation components, compositions and laundry methods employing same
US7109156B1 (en) 1999-08-27 2006-09-19 Procter & Gamble Company Controlled availability of formulation components, compositions and laundry methods employing same
US7557076B2 (en) * 2002-06-06 2009-07-07 The Procter & Gamble Company Organic catalyst with enhanced enzyme compatibility
US7169744B2 (en) * 2002-06-06 2007-01-30 Procter & Gamble Company Organic catalyst with enhanced solubility
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996040661A1 (fr) * 1995-06-07 1996-12-19 The Clorox Company Activateur de blanchiment a l'acetonitrile d'ammonium n-alkyle
US5591378A (en) * 1994-07-06 1997-01-07 The Clorox Company Substituted benzonitriles and compositions useful for bleaching
EP0790244A1 (fr) * 1996-02-15 1997-08-20 Hoechst Aktiengesellschaft Activateurs de blanchiment à de nitriles d'ammonium
WO1997042295A1 (fr) * 1996-05-06 1997-11-13 S.C. Johnson & Son, Inc. Activateurs de blanchiment a base de n-oxyde peroxyde de cyanopyridine

Family Cites Families (7)

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NL208181A (fr) * 1955-07-08
DE2346504A1 (de) * 1973-09-15 1975-04-24 Hoechst Ag Verfahren zum faerben von textilmaterial aus polyesterfaser-/cellulose-mischungen
US4883917A (en) * 1985-10-01 1989-11-28 Ethyl Corporation Quaternary ammonium compounds
US4915863A (en) * 1987-08-14 1990-04-10 Kao Corporation Bleaching composition
GB9011618D0 (en) * 1990-05-24 1990-07-11 Unilever Plc Bleaching composition
US5478356B1 (en) * 1994-05-10 1997-11-18 Clorox Co Cyanoimides and compositions useful for bleaching
JP3811508B2 (ja) * 1994-08-31 2006-08-23 ジョンソン株式会社 過酸化物の活性化方法およびその組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5591378A (en) * 1994-07-06 1997-01-07 The Clorox Company Substituted benzonitriles and compositions useful for bleaching
WO1996040661A1 (fr) * 1995-06-07 1996-12-19 The Clorox Company Activateur de blanchiment a l'acetonitrile d'ammonium n-alkyle
EP0790244A1 (fr) * 1996-02-15 1997-08-20 Hoechst Aktiengesellschaft Activateurs de blanchiment à de nitriles d'ammonium
WO1997042295A1 (fr) * 1996-05-06 1997-11-13 S.C. Johnson & Son, Inc. Activateurs de blanchiment a base de n-oxyde peroxyde de cyanopyridine

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001016276A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulation ameliorant la stabilite, et compositions et procedes de blanchissage les utilisant
WO2001016275A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulation a action rapide, compositions et procedes de nettoyage utilisant ces composants
WO2001016274A1 (fr) * 1999-08-27 2001-03-08 The Procter & Gamble Company Composants de formulations stables, compositions et procedes de nettoyage ces composants
WO2001016263A3 (fr) * 1999-08-27 2001-06-07 Procter & Gamble Disponibilite controlee de composants de formulation, compositions et procede de blanchissage utilisant ces produits
WO2002051973A1 (fr) * 2000-12-22 2002-07-04 Henkel Kommanditgesellschaft Auf Aktien Detergent et/ou nettoyant liquide

Also Published As

Publication number Publication date
JP4021075B2 (ja) 2007-12-12
BR9804057A (pt) 1999-12-07
JPH11199894A (ja) 1999-07-27
EP0909810B1 (fr) 2004-12-22
DE19746290A1 (de) 1999-04-22
US6007583A (en) 1999-12-28
US6120557A (en) 2000-09-19
DE59812405D1 (de) 2005-01-27

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