EP0825251A2 - L'utilisation de dérivés de sulphonylimin comme catalyseurs de blanchiment - Google Patents

L'utilisation de dérivés de sulphonylimin comme catalyseurs de blanchiment Download PDF

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Publication number
EP0825251A2
EP0825251A2 EP97113940A EP97113940A EP0825251A2 EP 0825251 A2 EP0825251 A2 EP 0825251A2 EP 97113940 A EP97113940 A EP 97113940A EP 97113940 A EP97113940 A EP 97113940A EP 0825251 A2 EP0825251 A2 EP 0825251A2
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EP
European Patent Office
Prior art keywords
alkyl
cleaning agent
washing
agent according
contain
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Withdrawn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
EP97113940A
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German (de)
English (en)
Inventor
Matthias Dr. Löffler
Gerd Dr. Reinhardt
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
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Clariant GmbH
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Filing date
Publication date
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Publication of EP0825251A2 publication Critical patent/EP0825251A2/fr
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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

Definitions

  • This invention relates to the use of sulphonylimine derivatives as novel ones Bleaching catalysts, as well as detergent compositions, these Contain compounds as bleaching catalysts.
  • 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
  • bleach activators are not catalytic are effective. As soon as the peroxyacid precursor, for example an ester or Imide that has been perhydrolized cannot be regenerated again. Hence relatively large amounts of bleach activator are required. In Detergent compositions are up to 8% by weight.
  • Oxidation catalysts Inspired by work in the field of oxidation of organic substances compounds with activated CN double bonds have been shown to be effective Oxidation catalysts detected. Building on the results of Hanquet et al. became, for example, quaternary imines and their corresponding ones Oxaziridinium salts for use as bleaching catalysts in textile washing used (Hanquet, Lusinchi, Milliet, Tetrahedron Lett. 1988, 3941; Hanquet, Lusinchi, Milliet, Acad.Sci. Paris. 1991 Series II, 625; Hanquet, Lusinchi, Milliet, Tetrahedron Lett.
  • Sulphonylimines of the formula form a special class of metal-free bleaching catalysts because they are highly effective.
  • Such bleaching catalysts and their derivatives are described for example in EP-446 982, EP-A-446 981 and US-5 429 768.
  • sulphonylimines are those of 3-substituted benzoisothiazole-1,1-dioxides are derived, a better one Have bleaching performance than the catalysts according to the prior art.
  • R 1 is preferably C 1 to C 4 alkyl, C 2 to C 4 alkenyl or phenyl.
  • the invention also relates to bleaching detergents and cleaning agents which contain the bleaching catalysts according to the invention.
  • This washing and Cleaning agents contain a peroxy compound and the Bleaching catalyst usually also surface-active compounds and others Ingredients.
  • Suitable peroxy compounds 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 peroxy compounds. Examples of these substances are cumene hydroperoxide and t-butyl hydroperoxide.
  • the detergent according to the invention can be used in such washing and cleaning agents Bleaching catalyst with a weight fraction of about 0.05% to 10%, preferred from 0.2% to 5%, along with a peroxy compound.
  • a weight fraction of about 0.05% to 10%, preferred from 0.2% to 5% along with a peroxy compound.
  • the proportion by weight of these peroxy compounds is usually from 2% to 40%, preferably from 4% to 30%, in particular from 10% to 25%.
  • Bleach catalysts and other suitable bleach activators such as TAED, tetraacetylglycoluril, glucose pentaacetate, Sodium nonanoyloxybenzenesulfonate, benzoylcaprolactam or nitrile activators be included.
  • TAED tetraacetylglycoluril
  • glucose pentaacetate e.g., glucose pentaacetate
  • Sodium nonanoyloxybenzenesulfonate enzoylcaprolactam or nitrile activators
  • benzoylcaprolactam or nitrile activators e.glycerin activators
  • the surfactant can be derived from natural products such as Soap, or can be 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.
  • Suitable anionic detergents are sodium and ammonium alkyl sulfates, especially the sulfates obtained by sulfating higher (C 8 to 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 salt
  • 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 preferred 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 up to 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 to 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.
  • Possible builders are: calcium-binding substances, precipitants, calcium-specific substances Ion exchangers and their mixtures.
  • Examples of calcium binding Fabrics 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 disclosed in U.S. 4,144,226 and U.S. 4,146,495.
  • precipitants are sodium orthophosphate, sodium carbonate and soaps from long chain fatty acids.
  • ion exchangers specific for calcium are the 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.
  • these additives include foaming agents such as alkanolamides, especially those Monoethanolamides from palm kernel oil fatty acids and coconut fatty acids; anti-foaming agents such as alkyl phosphates and silicones; Graying inhibitors and similar aids such as Sodium carboxymethyl cellulose and alkyl or substituted alkyl cellulose ethers; Stabilizers such as ethylenediaminetetraacetic acid; Softeners for textiles; inorganic salts such as sodium sulfate; and, usually in small amounts, fluorescent substances, perfumes, enzymes such as proteases, cellulases, lipases and Amylases, disinfectants and dyes.
  • the bleaching catalysts of this Invention can be used in a variety of products. This include textile detergents, textile bleaches, surface cleaners, Toilet cleaner, dishwasher cleaner, and also denture cleaner.
  • the Detergents can be in
  • bleaching catalysts in the form of granules, in addition to the Bleach catalyst contain a binder.
  • Different methods such Producing granules are described in the patent literature, for example in CA-1 102 966, GB-1 561 333, US-4 087 369, EP-A-0 240 057, EP-A-0 241 962, EP-A-0 101 634 and EP-A-0 062 523. Each of these methods is for the Bleach catalysts of the invention applicable.
  • the granules containing the bleaching catalysts are generally the Detergent composition along with the other, dry Ingredients such as enzymes and inorganic peroxide bleaches added.
  • the detergent composition to which the catalyst granules added can be obtained in various ways, such as Dry blending, extrusion or spray drying.
  • the bleaching catalysts 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-1205,711 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, and 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, other solid ionic surfactants, bleaches, fluorescent substances and other common solid ingredients.
  • Bleaching compositions with bleaching catalysts 1 to 4 were prepared. Their effectiveness was determined by measuring the remissions of the fabric before and after the bleaching process and comparing them with the remission differences when using the reference detergent. The corresponding ⁇ R values are given in Table 1.
  • ⁇ R SULF ⁇ R (SULF) - ⁇ R (WMP)
  • Example 2 The preparation of compound 1 is described in Example 2, the preparation of compounds 2 and 3 was carried out analogously to Examples 1 and 3 Catalyst No. ⁇ R (SULF-WMP) on tea ⁇ R (SULF-WMP) on red wine 1 8.9 14.0 2nd 7.6 11.8 3rd 8.0 13.5

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (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)
  • Detergent Compositions (AREA)
EP97113940A 1996-08-19 1997-08-13 L'utilisation de dérivés de sulphonylimin comme catalyseurs de blanchiment Withdrawn EP0825251A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19633305 1996-08-19
DE19633305A DE19633305A1 (de) 1996-08-19 1996-08-19 Sulphonylimin-Derivate als Bleichkatalysatoren

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EP0825251A2 true EP0825251A2 (fr) 1998-02-25

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US (1) US5952282A (fr)
EP (1) EP0825251A2 (fr)
JP (1) JPH10130692A (fr)
DE (1) DE19633305A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2001016263A3 (fr) * 1999-08-27 2001-06-07 Procter & Gamble Disponibilite controlee de composants de formulation, compositions et procede de blanchissage utilisant ces produits

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410214B1 (en) * 1998-10-01 2002-06-25 Lg Electronics Inc. Method for manufacturing black matrix of plasma display panel
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
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
US6821935B1 (en) 1999-08-27 2004-11-23 Procter & Gamble Company Color safe laundry methods employing zwitterionic formulation components
US6825160B1 (en) 1999-08-27 2004-11-30 Procter & Gamble Company Color safe laundry methods employing cationic formulation components
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
ATE465230T1 (de) * 2006-01-23 2010-05-15 Procter & Gamble Zusammensetzung enthaltend vorgeformte persäure und einen bleichmittelkatalysator
JP2009523904A (ja) 2006-01-23 2009-06-25 ザ プロクター アンド ギャンブル カンパニー リパーゼと漂白剤触媒を含む組成物
CA2635927A1 (fr) * 2006-01-23 2007-08-02 The Procter And Gamble Company Composition comprenant une lipase et un catalyseur de blanchiment
IN2014DN03452A (fr) 2006-07-07 2015-07-10 Procter & Gamble
DE102010043497A1 (de) 2010-11-05 2011-09-22 Henkel Ag & Co. Kgaa Saccharin-Derivate als Bleichaktivatoren
DE102017208585A1 (de) * 2017-05-22 2018-11-22 Henkel Ag & Co. Kgaa Bleichendes Wasch- oder Reinigungsmittel mit Oxaziridin-Vorläufer

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
DE1074187B (de) * 1956-10-03 1960-01-28 The Procter ·&. Gamble Company, Cincinnati, Ohio (V. St. A.) Thixotropes, flüssiges Reinigungsmittel
US2940938A (en) * 1956-10-05 1960-06-14 Procter & Gamble Process of making a colloidal suspension of phosphates
US3368977A (en) * 1965-03-23 1968-02-13 Monsanto Co Built liquid detergent compositions
US5041232A (en) * 1990-03-16 1991-08-20 Lever Brothers Company, Division Of Conopco, Inc. Sulfonimines as bleach catalysts
US5047163A (en) * 1990-03-16 1991-09-10 Lever Brothers Company, Division Of Conopco, Inc. Activation of bleach precursors with sulfonimines
US5413733A (en) * 1993-07-26 1995-05-09 Lever Brothers Company, Division Of Conopco, Inc. Amidooxy peroxycarboxylic acids and sulfonimine complex catalysts

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2001016263A3 (fr) * 1999-08-27 2001-06-07 Procter & Gamble Disponibilite controlee de composants de formulation, compositions et procede de blanchissage utilisant ces produits

Also Published As

Publication number Publication date
US5952282A (en) 1999-09-14
JPH10130692A (ja) 1998-05-19
DE19633305A1 (de) 1998-02-26

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