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WO1995014075A1 - Activateurs pour composes peroxydes inorganiques - Google Patents

Activateurs pour composes peroxydes inorganiques Download PDF

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Publication number
WO1995014075A1
WO1995014075A1 PCT/EP1994/002569 EP9402569W WO9514075A1 WO 1995014075 A1 WO1995014075 A1 WO 1995014075A1 EP 9402569 W EP9402569 W EP 9402569W WO 9514075 A1 WO9514075 A1 WO 9514075A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
alkyl
activators
activator
phenyl
Prior art date
Application number
PCT/EP1994/002569
Other languages
German (de)
English (en)
Inventor
Georg Thiele
Michael Del Grosso
Original Assignee
Degussa Aktiengesellschaft
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 Degussa Aktiengesellschaft filed Critical Degussa Aktiengesellschaft
Priority to EP94926143A priority Critical patent/EP0729503A1/fr
Publication of WO1995014075A1 publication Critical patent/WO1995014075A1/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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/18—Liquid substances or solutions comprising solids or dissolved gases

Definitions

  • the invention is directed to the use of N-acylated pyroglutamic acid derivatives as activators for inorganic peroxygen compounds, such as, in particular, hydrogen peroxide and compounds releasing hydrogen peroxide.
  • the invention is also directed to bleaching, washing, cleaning and disinfecting agents which contain these activators.
  • Inorganic peroxygen compounds are used as oxidizing agents in bleaching, washing, cleaning and disinfecting agents in order to improve the action of such agents.
  • hydrogen peroxide and those substances which release hydrogen peroxide in aqueous solution, such as perborates and percarbonates, are used as peroxygen compounds.
  • the effect of the inorganic peroxygen compounds depends not only on the pH value, but also on the temperature. While at
  • the use of so-called activators is required when using the inorganic peroxygen compounds mentioned at lower temperatures, in particular at 60 ° C or 40 ° C or below.
  • the activators are predominantly N-acyl or O-acyl compounds.
  • the inorganic peroxygen compounds and the activators form percarboxylic acids, which have a higher oxidation potential than H2O2 and these releasing compounds and therefore also have a good washing, cleaning, bleaching and disinfecting effect in the low temperature range.
  • N-acyl compounds Numerous classes of substances have been proposed as activators among the N-acyl compounds, including: N, N, N ', N'-tetraacetylethylene diamine in (TAED), N, N, N', N'-tetraacetylglycoluril (TAGU), N, N'-di (alkoxycarbonyl) hydantoins (US 3,928,223), N-mono- and N, N * -Di (-C * - to C ⁇ alkanoyl-hydantoins (DE-A 14 67 582 and DE-C 19 49 561), N- (C ⁇ ⁇ to C4) alkyloxycarbonylsucciniird.de (US 3,928,223) and N, N'-diacyl-2,5-diketopiperazines (DE-A 20 38 106) -Acyl compounds essentially only enforce TAED Both in the TAED and in several other N-acyl compounds not all
  • activators based on N-acyl compounds which essentially approach the property profile of the TAED and / or exceed it in one or the other point. If possible, the activators should be accessible from readily available and biodegradable raw materials.
  • R 1 is hydrogen, C 1 -C 4 -alkyl, alkali metal or ammonium
  • R 2 is a linear or branched saturated or olefinically unsaturated hydrocarbon radical having 1 to 11 C atoms, the longest chain of which can be interrupted by one or more ether bridges and one or two in addition Substituents from the series carboxy, C ⁇ ⁇ to C ß -alkoxy, -N ((Ci-C ⁇ ) alkyl) 3 + Cl ⁇ ,
  • R 1 has the abovementioned meaning and n represents an integer between 2 and 12,
  • the preferred compound of the formula (I), which can be in the form of its diastereomers, is cyclo- [pyroglutamyl-pyroglutamyl], which is also known as tetrahydro-dipyrrolo [1,2-a; 1 ', 2'-d] pyrazine-3, 5, 8, 10-tetraon.
  • the compound of formula (I) is known - GB 1 068 814 and J. Amer. Chem. Soc. (1952), Vol. 74, 2859-2864 - but was not previously known as an activator.
  • the compound (I) which can be obtained in a simple manner from racemic or optically active pyroglutamic acid and acetic anhydride, can be regarded both as N-acylated pyrrolidone and as N-acylated diketopiperazine.
  • the optically active starting compound L-pyroglutamic acid is easily accessible from L-glutamic acid obtained by fermentation.
  • N-acylated pyroglutamic acid derivative of the formula (I) proved to be a very effective activator: on average over six test stains on cotton (stained with tea, coffee, red wine, curry, tomato ketchup and clay), the bleaching effectiveness of this activator comes close to that of the TAED and clearly exceeds this for soiling like tomato.
  • N-acylated racemic or optically active pyroglutamic acid derivatives of the general formulas (II) and (III) which can be used as activators can be obtained in a manner known per se by acylation of DL-, L- or D-pyroglutamic acid with an acyl halide or carboxylic anhydride.
  • Activators according to formula (II) have proven to be surprisingly effective, although only one mole of peracid can be formed per mole: when used at the same weight, the bleaching effect of these activators when washing at 60 ° C. is comparable to that of TAED.
  • the radical R 1 is H, methyl, ethyl, propyl or butyl or in the form of the cation Li, Na, K or NH4. Substances with R 1 equal to H or alkali metal, in particular Na, are preferred. In principle, R * - * - can also stand for an equivalent of an alkaline earth metal, but such substances are not preferred because of the undesirable content of
  • Alkaline earth ions in the washing and bleaching liquors should not be increased.
  • substances with the preferred meaning for R 1 are obtained directly.
  • the solubility of compounds of the formula (II) can be increased by converting R * * * - H to R 1 to Na, which is particularly expedient if R 2 is a longer hydrocarbon radical, benzyl or phenyl.
  • R 2 is particularly advantageously a linear alkyl group having 1 to 11 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, undecyl.
  • Olefinic hydrocarbon residues such as vinyl, allyl, propen-2-yl are possible, but are less preferred.
  • the number and size of the substituents on the hydrocarbon residue is generally kept low to limit the molecular weight of the resulting percarboxylic acid.
  • the aromatic radical R 2 is substituted phenyl with preferably one or two carboxy or sulfo groups is preferred.
  • N is particularly advantageously 2, 3, 4 and 10.
  • the dicarboxylic acids required for the preparation of these compounds namely succinic acid, glutaric acid, adipic acid and dodecanedioic acid, their dichlorides with 2 mol
  • R * - * - is also preferably hydrogen or sodium in the case of the substances of the formula (III).
  • the use according to the invention relates to the activation of inorganic peroxygen compounds, in particular H2O2, and those compounds which release hydrogen peroxide in the aqueous phase.
  • inorganic peroxygen compounds in particular H2O2
  • perborates especially sodium perborate monohydrate, sodium perborate tetrahydrate, super-oxidized sodium perborate, and sodium percarbonate (2 Na2CO3-3 H2O2).
  • Perphosphates, persilicates and persulfates can also be used.
  • Several inorganic per-compounds can also be present during activation.
  • inorganic peroxygen compounds and activators are used in a ratio of 1 mol of active oxygen to 0.05 to 1 mol, preferably 1 to 0.1 to 0.5 mol, of activator.
  • the activators to be used according to the invention can be used for activation in pure form or with auxiliaries, such as granulation aids, stabilizers, pH-regulating substances; Suitable forms of addition are powders, pastes, tablets, granules or coated granules.
  • the activators and inorganic peroxygen compounds can also be used in the aqueous-organic phase in addition to the purely aqueous phase come.
  • the usual washing, bleaching and cleaning liquors have a purely aqueous environment.
  • An aqueous-organic environment can be useful in disinfection applications and in technical oxidation processes.
  • the pH of the reaction medium can be between about 4 and 13, but is preferably carried out in the alkaline range, usually at pH 8 to 11, since in this range both the in situ formation of the organic peracid proceeds well and the stability of the Perconnections is satisfactory.
  • Another object of the invention is directed to bleaching, washing, cleaning and disinfecting agents which contain an inorganic peroxygen compound and an activator from the series of the N-acylated compounds which can be used according to the invention and described above
  • the agent can contain one or more inorganic peroxygen compounds and one or more activators, including at least one activator according to the invention and, if required, commercially available or other known activators.
  • Activators and inorganic peroxygen compounds to be used according to the invention can be combined with all the usual constituents of detergents and bleaches in order to obtain detergents and bleaches which are used for textile treatment in low and high temperatures
  • the main constituents of such detergents and bleaches are, in addition to the per-compounds and activators mentioned, builders and surfactants.
  • builders are in particular sodium aluminum silicates (zeolites), condensed phosphates, alkali silicates, alkali carbonates, complexing aminocarboxylic acids, polyphosphonic acids, polyvalent hydroxycarboxylic acids and polycarboxylic acids and salts of the acids mentioned.
  • non-ionic surfactants such as fatty alcohol and alkylphenol polyethylene glycol ethers and long-chain alkyl glycosides
  • anionic surfactants such as alkyl benzene sulfonates and sulfates of fatty alcohols and polyethylene glycol monoethers
  • Other substances in the detergents and bleaches are electrolytes, pH regulators, stabilizers, foam regulators, graying inhibitors, optical brighteners, enzymes, softeners.
  • the substances and amounts to be used in such agents are known to the person skilled in the art - an overview, together with literature, is provided by HG Hauthal in "Chemistry in Our Time” 26 (1992) No. 6, 293-303).
  • the detergents and bleaches according to the invention are usually composed as follows:
  • Surfactants 5 to 60% by weight, preferably 20 to 40% by weight
  • Builders from the group sodium aluminum silicates, condensed phosphates, alkali silicates,
  • Alkali carbonates, and mixtures thereof 0 to 20% by weight, preferably 1 to 8% by weight
  • Polyphosphonic acids, polycarboxylic acids or their salts and their mixtures 2 to 35% by weight, preferably 10 to 25% by weight, of inorganic peroxygen compounds from the group sodium perborates and
  • Pure bleaching agents as they can be used as additives for bleach-free detergents, are generally composed as follows:
  • inorganic peroxygen compounds in particular Na perborate onohydrate or tetrahydrate or / and
  • N-acylated pyroglutamic acid derivatives to be used as activators
  • peroxide stabilizers such as
  • Cleaning agents according to the invention generally contain surfactants, builders, peroxygen compounds and activators to be used according to the invention; Abrasives also contain abrasive components.
  • Disinfectants according to the invention are generally based on a combination of inorganic per-compounds and activators to be used according to the invention and auxiliaries from the series of stabilizers, surfactants, pH-regulating substances and, if desired, organic solvents and others microbiocidal substances as the peracids resulting from the activators and per-compounds.
  • the aqueous phase was washed with acetic ester, adjusted to pH 2, extracted with ethyl acetate, dried (MgSC> 4) and the solvent was removed on a rotary evaporator. 26.3 g were obtained as a colorless solid.
  • the * - * - H NMR spectroscopic data are consistent with the structure.
  • N-Nonanoyl-2-pyrrolidone-5-carboxylic acid sodium salt The product prepared according to Example 3 was dissolved in 100 ml of ethanol, and the solution was mixed with an amount of ethanolic NaOH (1 molar) equivalent to the carboxylic acid; then the solvent was removed.
  • Example 6 From the course of the peracid formation and its degradation it can be seen that the activator according to Example 1 is readily soluble under the test conditions and after a short time about 62% of the theoretically possible amount of peracid is available.
  • the activators of Examples 2 to 4 show a higher stability of the formed Peracid. Peracid formation is accelerated by using an activator in the salt form over that in the acid form.
  • Example 6
  • the test is carried out in a launderometer (type Atlas) using a bleach and activator-free commercial detergent from the US market (TIDE-Ultra®).
  • the bleaching action of the activator according to Example 4 was tested on six test soils on cotton (bandy black clay; WFK-BW: tea, curry, red wine, coffee, tomato ketchup) in comparison with TAED in the launderometer (Atlas).
  • Washing time 15 minutes (laboratory washing machine)

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne l'utilisation de dérivés N-acylés de l'acide pyroglutamique de formule (I ou II), dans lesquelles R1 désigne de préférence H ou Na et R2 un reste hydrocarbure aliphatique ou aromatique, éventuellement substitué, de préférence un rest alkyle linéaire, comme activateurs pour des composés peroxydés inorganiques dans des systems aqueux, en particulier pour les produits de blanchiment à basse température. L'invention concerne également des produits de blanchiment, de lavage, de nettoyage et de désinfection contenant ces activateurs. Les composés reconnus comme activateurs atteignent un pouvoir de blanchiment du niveau du TAED et le dépassent dans certains cas.
PCT/EP1994/002569 1993-11-15 1994-08-03 Activateurs pour composes peroxydes inorganiques WO1995014075A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP94926143A EP0729503A1 (fr) 1993-11-15 1994-08-03 Activateurs pour composes peroxydes inorganiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4338922.8 1993-11-15
DE19934338922 DE4338922A1 (de) 1993-11-15 1993-11-15 Aktivatoren für anorganische Persauerstoffverbindungen

Publications (1)

Publication Number Publication Date
WO1995014075A1 true WO1995014075A1 (fr) 1995-05-26

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ID=6502600

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Application Number Title Priority Date Filing Date
PCT/EP1994/002569 WO1995014075A1 (fr) 1993-11-15 1994-08-03 Activateurs pour composes peroxydes inorganiques

Country Status (3)

Country Link
EP (1) EP0729503A1 (fr)
DE (1) DE4338922A1 (fr)
WO (1) WO1995014075A1 (fr)

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997041202A1 (fr) * 1996-04-26 1997-11-06 Henkel Kommanditgesellschaft Auf Aktien Acyllactames s'utilisant comme activateurs de blanchiment pour detergents et nettoyants
EP0730631B1 (fr) * 1993-11-25 1999-07-07 WARWICK INTERNATIONAL GROUP LIMITED (Company No. 2982784) Compositions de blanchiment
US6221824B1 (en) 1999-02-25 2001-04-24 Henkel Kommanditgesellschaft Auf Aktien Process for the production of compounded acetonitrile derivatives
US6221820B1 (en) 1997-12-31 2001-04-24 Henkel Kommanditgesellschaft Auf Aktien Granular component containing alkylaminotriazole for use in machine dishwashing detergents
US6225274B1 (en) 1996-11-29 2001-05-01 Henkel Kommandigesellschaft Auf Aktien Acetonitrile derivatives as bleaching activators in detergents
US6225276B1 (en) 1997-02-07 2001-05-01 Henkel Kommanditgesellschaft Auf Aktien pH-controlled release of detergent components
US6329335B1 (en) 1997-03-07 2001-12-11 Henkel Kommanditgesellschaft Auf Aktien Detergent tablets
US6380147B1 (en) 1998-06-03 2002-04-30 Henkel Kommanditgesellschaft Auf Aktien Detergents containing amylase and protease
US6410500B1 (en) 1997-12-30 2002-06-25 Henkel Kommanditgesellschaft Auf Aktien Moulded body dishwasher detergents with soil release polymers
US6417152B1 (en) 1997-07-30 2002-07-09 Henkel Kommanditgesellshaft Auf Aktien Detergent containing glucanase
US6462006B1 (en) * 1998-04-30 2002-10-08 Henkel Kommanditgesellschaft Auf Aktien Solid machine dishwashing detergent with phosphate and crystalline lamellar silicates
US6541233B1 (en) 1997-07-30 2003-04-01 Henkel Kommanditgesellschaft Auf Aktien β-glucanase from a bacillus
US6686327B1 (en) 1999-10-09 2004-02-03 Cognis Deutschland Gmbh & Co. Kg Shaped bodies with improved solubility in water
US6703357B1 (en) 1997-07-30 2004-03-09 Henkel Kommanditgesellschaft Auf Aktien Cleaning agent for hard surfaces, containing glucanase
US6881359B2 (en) 2000-01-26 2005-04-19 Cognis Deutschland Gmbh & Co. Kg Processes for the preparation of low dust, limited particle size distribution, surfactant granules
US6897193B2 (en) 2001-12-22 2005-05-24 Cognis Deutschland Gmbh & Co., Kg Hydroxy mixed ethers and polymers in the form of solid preparations as a starting compound for laundry detergents, dishwashing detergents and cleaning compositions
US6936581B2 (en) 2000-04-19 2005-08-30 Cognis Deutschland Gmbh & Co. Kg Processes for preparing anhydrous detergent granules
US6951838B1 (en) 1999-09-15 2005-10-04 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US6977239B1 (en) 1999-11-25 2005-12-20 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US6992056B1 (en) 1997-12-30 2006-01-31 Henkel Kgaa Process for preparing detergent tablets having two or more regions
US7049279B1 (en) 1999-11-25 2006-05-23 Cognis Deutschland Gmbh & Co. Kg Process for preparing detergent granules with an improved dissolution rate
US7087570B2 (en) 1999-12-24 2006-08-08 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US7091168B2 (en) 2000-06-29 2006-08-15 Cognis Deutschland Gmbh & Co. Kg Liquid detergents
US7153818B2 (en) 2000-07-28 2006-12-26 Henkel Kgaa Amylolytic enzyme extracted from bacillus sp. A 7-7 (DSM 12368) and washing and cleaning agents containing this novel amylolytic enzyme
US7186678B2 (en) 1999-12-24 2007-03-06 Cognis Deutschland Gmbh & Co. Kg Tenside granules with improved disintegration rate
US7199096B1 (en) 1999-11-09 2007-04-03 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
WO2007054203A2 (fr) 2005-11-08 2007-05-18 Henkel Ag & Co. Kgaa Systeme pour produire du peroxyde d'hydrogene par voie enzymatique
US7262042B2 (en) 2001-12-20 2007-08-28 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus gibsonii (DSM 14393) and washing and cleaning products comprising said alkaline protease
US7300782B2 (en) 2001-12-21 2007-11-27 B.R.A.I.N. Biotechnology Research And Information Network Ag Glycosyl hydrolases
US7320887B2 (en) 2001-10-31 2008-01-22 Henkel Kommanditgesellschaft Auf Aktien Alkaline protease variants
DE102007003143A1 (de) 2007-01-16 2008-07-17 Henkel Kgaa Neue Alkalische Protease aus Bacillus gibsonii und Wasch- und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE102007003885A1 (de) 2007-01-19 2008-07-24 Lanxess Deutschland Gmbh Geschirrreinigungsmittel
DE102007016391A1 (de) 2007-04-03 2008-10-09 Henkel Ag & Co. Kgaa Farbschützendes Wasch- oder Reinigungsmittel
EP1980237A1 (fr) * 2006-01-06 2008-10-15 Ajinomoto Co., Inc. Agent gelifiant
US7449187B2 (en) 2001-12-20 2008-11-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus gibsonii (DSM 14391) and washing and cleaning products comprising said alkaline protease
US7510859B2 (en) 2002-12-20 2009-03-31 Henkel Kommanditgesellschaft Auf Aktien Subtilisin variants with improved perhydrolase activity
DE102007049830A1 (de) 2007-10-16 2009-04-23 Henkel Ag & Co. Kgaa Neue Proteinvarianten durch zirkulare Permutation
DE102007051092A1 (de) 2007-10-24 2009-04-30 Henkel Ag & Co. Kgaa Subtilisin aus Becillus pumilus und Wasch- und Reinigungsmittel enthaltend dieses neue Subtilisin
DE102008000029A1 (de) 2008-01-10 2009-07-16 Lanxess Deutschland Gmbh Geschirrreinigungsmittel
US7569226B2 (en) 2001-12-22 2009-08-04 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus sp. (DSM 14392) and washing and cleaning products comprising said alkaline protease
US7601678B2 (en) 2001-02-07 2009-10-13 Henkel Ag & Co. Kgaa Washing and cleaning agents comprising fine microparticles with cleaning agent components
US7691618B2 (en) 2004-04-23 2010-04-06 Henkel Ag & Co. Kgaa Alkaline proteases and detergents and cleaners comprising these alkaline proteases
US7811076B2 (en) 2003-12-23 2010-10-12 Henkel Ag & Co. Kgaa Alkaline protease and washing and cleaning products containing said novel alkaline protease
US7888104B2 (en) 2000-11-28 2011-02-15 Henkel Ag & Co. Kgaa Cyclodextrin glucanotransferase (CGTase), obtained from<I>Bacillus agaradherens<λ>(DSM 9948) and detergents and cleaning agents containing said novel cyclodextrin glucanotransferase
US8262804B2 (en) 2007-10-12 2012-09-11 Basf Se Dishwasher detergent formulations comprising a mixture of hydrophobically modified polycarboxylates and hydrophilically modified polycarboxylates
US8263541B2 (en) 2005-08-19 2012-09-11 Henkel Ag & Co. Kgaa Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor
DE102015002877A1 (de) 2015-03-09 2016-09-15 Henkel Ag & Co. Kgaa Granulares Wasch- oder Reinigungsmittel mit verbesserter Lösegeschwindigkeit
DE102004047777B4 (de) 2004-10-01 2018-05-09 Basf Se Alpha-Amylase-Varianten mit erhöhter Lösungsmittelstabilität, Verfahren zu deren Herstellung sowie deren Verwendung
DE102004047776B4 (de) 2004-10-01 2018-05-09 Basf Se Gegen Di- und/oder Multimerisierung stabilisierte Alpha-Amylase-Varianten, Verfahren zu deren Herstellung sowie deren Verwendung

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2226456A1 (fr) * 1995-07-07 1997-01-30 Durham Pharmaceuticals, Llc. Amides cycliques et derives desdits amides
US6175374B1 (en) * 1995-10-13 2001-01-16 Agfa-Gevaert Method for stable electro (stato) graphic reproduction of a continuous tone image
FR2827175B1 (fr) * 2001-07-10 2003-11-14 Rival De Services D Etudes De Composition a base de compose peroxyde et de compose n-acyle et procede de desinfection

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135444A1 (fr) * 1983-09-12 1985-03-27 Laboratoires Serobiologiques S.A. Dérivés pyroglutamiques, procédé de préparation, intermédiaires de synthèse de préparation de ceux-ci et compositions antibactérien ou antifongiques, cosmetiques ou pharmaceutiques
EP0399584A2 (fr) * 1989-05-10 1990-11-28 Unilever N.V. Activation du blanchiment et compositions à cet effet
EP0427224A1 (fr) * 1989-11-08 1991-05-15 Kao Corporation Composés polycationiques et compositions de blanchiment les contenant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135444A1 (fr) * 1983-09-12 1985-03-27 Laboratoires Serobiologiques S.A. Dérivés pyroglutamiques, procédé de préparation, intermédiaires de synthèse de préparation de ceux-ci et compositions antibactérien ou antifongiques, cosmetiques ou pharmaceutiques
EP0399584A2 (fr) * 1989-05-10 1990-11-28 Unilever N.V. Activation du blanchiment et compositions à cet effet
EP0427224A1 (fr) * 1989-11-08 1991-05-15 Kao Corporation Composés polycationiques et compositions de blanchiment les contenant

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. A. KING ET. AL.: "The Reaction of Glutamic Acid with Acetic Anhydride and Pyridine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 74, no. 10, 24 May 1952 (1952-05-24), WASHINGTON, DC US, pages 2859 - 2864 *
See also references of EP0729503A1 *

Cited By (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0730631B1 (fr) * 1993-11-25 1999-07-07 WARWICK INTERNATIONAL GROUP LIMITED (Company No. 2982784) Compositions de blanchiment
WO1997041202A1 (fr) * 1996-04-26 1997-11-06 Henkel Kommanditgesellschaft Auf Aktien Acyllactames s'utilisant comme activateurs de blanchiment pour detergents et nettoyants
US6225274B1 (en) 1996-11-29 2001-05-01 Henkel Kommandigesellschaft Auf Aktien Acetonitrile derivatives as bleaching activators in detergents
US6407052B2 (en) 1997-02-07 2002-06-18 Henkel Kommanditgesellschaft Auf Aktien pH-controlled release of detergent components
US6225276B1 (en) 1997-02-07 2001-05-01 Henkel Kommanditgesellschaft Auf Aktien pH-controlled release of detergent components
US6329335B1 (en) 1997-03-07 2001-12-11 Henkel Kommanditgesellschaft Auf Aktien Detergent tablets
US6417152B1 (en) 1997-07-30 2002-07-09 Henkel Kommanditgesellshaft Auf Aktien Detergent containing glucanase
US6703357B1 (en) 1997-07-30 2004-03-09 Henkel Kommanditgesellschaft Auf Aktien Cleaning agent for hard surfaces, containing glucanase
US6541233B1 (en) 1997-07-30 2003-04-01 Henkel Kommanditgesellschaft Auf Aktien β-glucanase from a bacillus
US6410500B1 (en) 1997-12-30 2002-06-25 Henkel Kommanditgesellschaft Auf Aktien Moulded body dishwasher detergents with soil release polymers
US6992056B1 (en) 1997-12-30 2006-01-31 Henkel Kgaa Process for preparing detergent tablets having two or more regions
US6221820B1 (en) 1997-12-31 2001-04-24 Henkel Kommanditgesellschaft Auf Aktien Granular component containing alkylaminotriazole for use in machine dishwashing detergents
US6462006B1 (en) * 1998-04-30 2002-10-08 Henkel Kommanditgesellschaft Auf Aktien Solid machine dishwashing detergent with phosphate and crystalline lamellar silicates
US6380147B1 (en) 1998-06-03 2002-04-30 Henkel Kommanditgesellschaft Auf Aktien Detergents containing amylase and protease
US6221824B1 (en) 1999-02-25 2001-04-24 Henkel Kommanditgesellschaft Auf Aktien Process for the production of compounded acetonitrile derivatives
US6951838B1 (en) 1999-09-15 2005-10-04 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US6686327B1 (en) 1999-10-09 2004-02-03 Cognis Deutschland Gmbh & Co. Kg Shaped bodies with improved solubility in water
US7199096B1 (en) 1999-11-09 2007-04-03 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US7049279B1 (en) 1999-11-25 2006-05-23 Cognis Deutschland Gmbh & Co. Kg Process for preparing detergent granules with an improved dissolution rate
US6977239B1 (en) 1999-11-25 2005-12-20 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US7186678B2 (en) 1999-12-24 2007-03-06 Cognis Deutschland Gmbh & Co. Kg Tenside granules with improved disintegration rate
US7087570B2 (en) 1999-12-24 2006-08-08 Cognis Deutschland Gmbh & Co. Kg Detergent tablets
US6881359B2 (en) 2000-01-26 2005-04-19 Cognis Deutschland Gmbh & Co. Kg Processes for the preparation of low dust, limited particle size distribution, surfactant granules
US6936581B2 (en) 2000-04-19 2005-08-30 Cognis Deutschland Gmbh & Co. Kg Processes for preparing anhydrous detergent granules
US7091168B2 (en) 2000-06-29 2006-08-15 Cognis Deutschland Gmbh & Co. Kg Liquid detergents
US7153818B2 (en) 2000-07-28 2006-12-26 Henkel Kgaa Amylolytic enzyme extracted from bacillus sp. A 7-7 (DSM 12368) and washing and cleaning agents containing this novel amylolytic enzyme
US7803604B2 (en) 2000-07-28 2010-09-28 Henkel Ag & Co. Kgaa Amylolytic enzyme extracted from Bacillus sp. A 7-7 (DSM 12368) and washing and cleaning agents containing this novel amylolytic enzyme
US7888104B2 (en) 2000-11-28 2011-02-15 Henkel Ag & Co. Kgaa Cyclodextrin glucanotransferase (CGTase), obtained from<I>Bacillus agaradherens<λ>(DSM 9948) and detergents and cleaning agents containing said novel cyclodextrin glucanotransferase
US7601678B2 (en) 2001-02-07 2009-10-13 Henkel Ag & Co. Kgaa Washing and cleaning agents comprising fine microparticles with cleaning agent components
US7320887B2 (en) 2001-10-31 2008-01-22 Henkel Kommanditgesellschaft Auf Aktien Alkaline protease variants
US7449187B2 (en) 2001-12-20 2008-11-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus gibsonii (DSM 14391) and washing and cleaning products comprising said alkaline protease
US7262042B2 (en) 2001-12-20 2007-08-28 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus gibsonii (DSM 14393) and washing and cleaning products comprising said alkaline protease
US7300782B2 (en) 2001-12-21 2007-11-27 B.R.A.I.N. Biotechnology Research And Information Network Ag Glycosyl hydrolases
US6897193B2 (en) 2001-12-22 2005-05-24 Cognis Deutschland Gmbh & Co., Kg Hydroxy mixed ethers and polymers in the form of solid preparations as a starting compound for laundry detergents, dishwashing detergents and cleaning compositions
US7569226B2 (en) 2001-12-22 2009-08-04 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Alkaline protease from Bacillus sp. (DSM 14392) and washing and cleaning products comprising said alkaline protease
US7510859B2 (en) 2002-12-20 2009-03-31 Henkel Kommanditgesellschaft Auf Aktien Subtilisin variants with improved perhydrolase activity
US7811076B2 (en) 2003-12-23 2010-10-12 Henkel Ag & Co. Kgaa Alkaline protease and washing and cleaning products containing said novel alkaline protease
US7691618B2 (en) 2004-04-23 2010-04-06 Henkel Ag & Co. Kgaa Alkaline proteases and detergents and cleaners comprising these alkaline proteases
DE102004047776B4 (de) 2004-10-01 2018-05-09 Basf Se Gegen Di- und/oder Multimerisierung stabilisierte Alpha-Amylase-Varianten, Verfahren zu deren Herstellung sowie deren Verwendung
DE102004047777B4 (de) 2004-10-01 2018-05-09 Basf Se Alpha-Amylase-Varianten mit erhöhter Lösungsmittelstabilität, Verfahren zu deren Herstellung sowie deren Verwendung
US8263541B2 (en) 2005-08-19 2012-09-11 Henkel Ag & Co. Kgaa Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor
WO2007054203A2 (fr) 2005-11-08 2007-05-18 Henkel Ag & Co. Kgaa Systeme pour produire du peroxyde d'hydrogene par voie enzymatique
EP1980237A4 (fr) * 2006-01-06 2012-01-18 Ajinomoto Kk Agent gelifiant
EP1980237A1 (fr) * 2006-01-06 2008-10-15 Ajinomoto Co., Inc. Agent gelifiant
DE102007003143A1 (de) 2007-01-16 2008-07-17 Henkel Kgaa Neue Alkalische Protease aus Bacillus gibsonii und Wasch- und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE102007003885A1 (de) 2007-01-19 2008-07-24 Lanxess Deutschland Gmbh Geschirrreinigungsmittel
DE102007016391A1 (de) 2007-04-03 2008-10-09 Henkel Ag & Co. Kgaa Farbschützendes Wasch- oder Reinigungsmittel
US8262804B2 (en) 2007-10-12 2012-09-11 Basf Se Dishwasher detergent formulations comprising a mixture of hydrophobically modified polycarboxylates and hydrophilically modified polycarboxylates
DE102007049830A1 (de) 2007-10-16 2009-04-23 Henkel Ag & Co. Kgaa Neue Proteinvarianten durch zirkulare Permutation
DE102007051092A1 (de) 2007-10-24 2009-04-30 Henkel Ag & Co. Kgaa Subtilisin aus Becillus pumilus und Wasch- und Reinigungsmittel enthaltend dieses neue Subtilisin
DE102008000029A1 (de) 2008-01-10 2009-07-16 Lanxess Deutschland Gmbh Geschirrreinigungsmittel
DE102015002877A1 (de) 2015-03-09 2016-09-15 Henkel Ag & Co. Kgaa Granulares Wasch- oder Reinigungsmittel mit verbesserter Lösegeschwindigkeit
DE102015002877B4 (de) 2015-03-09 2024-09-12 Henkel Ag & Co. Kgaa Wasch- oder reinigungsaktive Extrudate, deren Herstellung und Verwendung in granularen Wasch- oder Reinigungsmitteln

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DE4338922A1 (de) 1995-05-18

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