EP0882117B1 - Agent antisalissure et procede de traitement des articles a base de coton tisse - Google Patents

Agent antisalissure et procede de traitement des articles a base de coton tisse Download PDF

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Publication number
EP0882117B1
EP0882117B1 EP97906221A EP97906221A EP0882117B1 EP 0882117 B1 EP0882117 B1 EP 0882117B1 EP 97906221 A EP97906221 A EP 97906221A EP 97906221 A EP97906221 A EP 97906221A EP 0882117 B1 EP0882117 B1 EP 0882117B1
Authority
EP
European Patent Office
Prior art keywords
agent
antisoiling
cationic
les
process according
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
EP97906221A
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German (de)
English (en)
French (fr)
Other versions
EP0882117A1 (fr
Inventor
Emmanuelle Chilou
Claire David
Etienne Fleury
Jean-Pierre Marchand
Kenneth Wong
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.)
Rhodia Chimie SAS
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Rhodia Chimie SAS
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Filing date
Publication date
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Publication of EP0882117A1 publication Critical patent/EP0882117A1/fr
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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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3753—Polyvinylalcohol; Ethers or esters thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/60—Sulfonium or phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707—Polyethers, e.g. polyalkyleneoxides
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3715—Polyesters or polycarbonates
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3776—Heterocyclic compounds, e.g. lactam

Definitions

  • the subject of the present invention is a method of anti-fouling treatment of articles based on woven cotton, by depositing an anti-fouling agent on said article during one or more washing, rinsing and / or softening or drying operations and an anti-fouling agent for woven cotton articles.
  • said method makes it possible to treat articles of woven cotton fibers against soiling; it is also suitable for the treatment of articles made from a mixture of cotton fibers and other fibers, natural, artificial or synthetic, such as viscose, polyesters, polyacrylic fibers ... , the fibers other than cotton being able to represent up to 65% of the mixture of fibers.
  • cationic function means any function which is either cationic as such is having an electrophilic atom.
  • ammonium phosphonium groups, groups derived from primary, secondary or tertiary amines, betaines, sultaines, glycinates ...
  • MH hydrophobic in nature
  • These hydrophobic patterns make it possible to increase, at least locally, the thickness of the surface layer of electrostatic charges on the cotton.
  • these hydrophobic character patterns are also capable of interacting with soil components.
  • the counterions capable of forming a salt with said cationic functions can be of any nature. Mention may be made of the halide ions (Cl - , Br - , ... ), acetate, sulfate, sulfonate, phosphate ...
  • alkyl alkenyl, linear, branched or cyclic, aryl groups, ... containing at least 4 carbon atoms, preferably from 8 to 20 carbon atoms. Mention may very particularly be made of C 4 -C 20 alkyl groups.
  • the quantities of units carrying cationic (MC) functions are such that they ensure, during treatment, sufficient adhesion of the molecule of antifouling agent to the surface of the cotton article. Amounts of 0.1 to 40 parts by weight of cationic functions per 100 parts by weight of anti-fouling agent are generally satisfactory. In the case of the ammonium functions, these can represent from 0.01 to 4 gram (s) of nitrogen per 100 grams of antifouling agent.
  • the quantities of units of hydrophobic character are such as to ensure during treatment, with the anti-fouling molecule a hydrophite / hydrophobic balance (HLB) greater than 15 allowing it to be divided between water and the surface of the article based woven cotton.
  • HLB hydrophite / hydrophobic balance
  • the hydrophilicity of the anti-fouling molecule is such that it can remove in the next wash at the same time as the soiling.
  • anti-fouling agents there may be mentioned in particular cationic alkyl guars, cationic alkyl hydroxypropylguars.
  • MH hydrophobic nature
  • alkyl radicals preferably linear, containing from 8 to 20 carbon atoms, these being possibly chemically linked to the oligomer, polymer or copolymer chain of the polyvinyl alcohol directly by CC bond or indirectly via a bivalent or polyvalent hydrocarbon group containing at least one heteroatom.
  • bivalent or polyvalent hydrocarbon groups containing at least one heteroatom mention may be made of ethers, esters, urethanes, acetals and amides bridges.
  • said agent contains of the order of 0.1 to 10, preferably from 1 to 6 units carrying a cationic function (MC) per 100 monomer units of the oligomer.
  • polyvinyl alcohol polymer or copolymer and from 0.01 to 10, preferably from 0.1 to 5 units of hydrophobic nature (MH) per 100 monomer units of the polymer or copolymer of polyvinyl alcohol.
  • oligomers polymers and copolymers of vinyl alcohol constituting the hydrophilic chain, mention may be made of those of molecular weight from 500 to 500,000, preferably of the order of 1000 to 100,000; said copolymers can contain up to 5 mol% of units derived from at least one comonomer such as vinyl acetate, ethylene, maleic anhydride ...
  • Said anti-fouling agent which is the subject of the invention can be obtained for example by modification of a homopolymer or of a copolymer of vinyl acetate, at least partially hydrolyzed to (co) polyvinyl alcohol (i.e. - say hydrolyzed up to at least 80%) using precursor compounds of the units carrying cationic function (MC) and hydrophobic units (MH); this modification involves substitution reactions (for example esterification, acetalization, etherification ... ) well known to those skilled in the art and described in particular in "Polyvinyl Alcohol Developments" - Ed. CA Finch (Wiley) - pages 183 and following and 84 and following.
  • a particular antifouling agent can be obtained by modification of a polyvinyl alcohol using (2,3-epoxypropyl) trimethylammonium chloride followed by a modification using an alkylisocyanate.
  • anti-fouling agent that can be used according to the treatment method of the invention, depend on the nature of the molecule used. These can be from 0.05 to 5 gram (s) per liter of treatment medium.
  • the anti-fouling agent can be used during a washing operation by means of a washing powder or liquid formulation (detergent composition), the treatment medium being constituted by the bath. of washing.
  • the powder or liquid detergent compositions may contain from 0.02 to 20% of their weight of said anti-fouling agent.
  • the anti-fouling agent can also be used for rinsing and / or softening by means of a liquid formulation for rinsing and / or softening of articles, the treatment medium consisting of the rinsing bath and / or softening.
  • the liquid rinsing and / or softening compositions may contain on the order of 0.02 to 20% of their weight of said anti-fouling agent.
  • the anti-fouling agent can also be introduced on drying into the wet laundry to be dried, by means of a support constituted for example by a strip of nonwoven fabric impregnated with said anti-fouling agent, support which may contain about 20% of its weight of antifouling agent.
  • test tubes size 10x12 cm, are used.
  • Two already washed test pieces are introduced into a TERGOTOMETER; powdered antifouling agent is added, then 1 liter of water (30 ° TH).
  • the rinsing pretreatment is carried out at 100 cycles / minute for 20 minutes at 40 ° C.
  • the two other test pieces are used as a reference and pretreated with water alone (30 ° TH).
  • Washing is carried out at 40 ° C. for 20 minutes, using 5 g of the detergent described above for 1 liter of water at 30 ° TH, then 3 rinses of 5 minutes in cold water and 2 drying under ice.
  • the reflectance of the fabrics before and after washing is measured using the DR colorimeter.
  • the antifouling agent tested is a cationic alkylguar (AGC), having a viscosity at 1% in water of 1000 mPa.s., containing 1.7% by weight of nitrogen derived from hydroxypropyltrimethylammonium chloride and having groups alkyl epoxy derivatives of formula
  • 40 g of polyvinyl alcohol with a molar mass of 15,000 and having a hydrolysis rate of 88% are introduced into a three-necked flask.
  • the polymer is then dissolved under an inert atmosphere, at 40 ° C in 200g of water.
  • introduced 5.2 g of sodium hydroxide tablet, then 97.6 g of an aqueous solution of (2,3-epoxypropyl) trimethylammonium chloride at 70% (0.45 moles) are slowly injected into the reaction medium.
  • the medium is maintained for 8 h at 40 ° C., then cooled and neutralized with acetic acid.
  • the polymer is then separated from the reaction medium by precipitation in ethanol then filtration.
  • the proportion of grafted ammonium groups is then obtained by comparing the integral of the CH 2 protons of polyvinyl alcohol (between 1, 2 and 1.5 ppm) with that of the ammonium protons [(CH 3 ) 3 N + ] at 3.1 ppm.
  • the molar ratio (CH 3 ) 3 N + / PVOH is 1/26.
  • the proportion of grafted hydrophobic units is then obtained by comparing the integral of the CH 2 protons of polyvinyl alcohol (between 1.2 and 1.5 ppm) with that of methyl at the end of the alkyl chain (at 0, 8ppm) or with that of the methylene group of the alkyl chain in alpha of the carbamate group (at 2.9ppm).
  • the content of alkyl units relative to 100 vinyl units (monomer units) is 1%.
  • Example 2 -4- The performances of the anti-fouling agent prepared in Example 2 -4- are evaluated at 0.2 g / l of water, vis-à-vis the drain oil and a purple pigmentary stain (oil of olive colored by a purple organic pigment).
  • the results observed on the pretreated test pieces, compared to those observed on the reference test pieces, are as follows: Test pieces tested E in% motor oil E in% purple pigment Reference ones 44 79 Those processed 58 88

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
  • Woven Fabrics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatment Of Fiber Materials (AREA)
EP97906221A 1996-02-20 1997-02-19 Agent antisalissure et procede de traitement des articles a base de coton tisse Expired - Lifetime EP0882117B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9602181A FR2745014B1 (fr) 1996-02-20 1996-02-20 Procede de traitement antisalissure des articles a base de coton tisse
FR9602181 1996-02-20
PCT/FR1997/000304 WO1997031085A1 (fr) 1996-02-20 1997-02-19 Agent antisalissure et procede de traitement des articles a base de coton tisse

Publications (2)

Publication Number Publication Date
EP0882117A1 EP0882117A1 (fr) 1998-12-09
EP0882117B1 true EP0882117B1 (fr) 2002-11-13

Family

ID=9489465

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97906221A Expired - Lifetime EP0882117B1 (fr) 1996-02-20 1997-02-19 Agent antisalissure et procede de traitement des articles a base de coton tisse

Country Status (11)

Country Link
US (1) US6379394B1 (es)
EP (1) EP0882117B1 (es)
JP (1) JP3253972B2 (es)
AT (1) ATE227765T1 (es)
AU (1) AU2098397A (es)
BR (1) BR9707650A (es)
CA (1) CA2246381A1 (es)
DE (1) DE69717079T2 (es)
ES (1) ES2187757T3 (es)
FR (1) FR2745014B1 (es)
WO (1) WO1997031085A1 (es)

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WO2002044350A2 (de) 2000-11-28 2002-06-06 Henkel Kommanditgesellschaft Auf Aktien Cyclodextrin-glucanotransferase (cg tase) aus bicillus agaradherens (dsm 9948) sowie wasch- und reinigungsmittel mit dieser neuen cyclodextrin-glucanotransferase
DE10121463A1 (de) * 2001-05-02 2003-02-27 Henkel Kgaa Neue Alkalische Protease-Varianten und Wasch- und Reinigungsmittel enthaltend diese neuen Alkalischen Protease-Varianten
DE10153792A1 (de) * 2001-10-31 2003-05-22 Henkel Kgaa Neue Alkalische Protease-Varianten und Wasch- und Reinigungsmittel enthaltend diese neuen Alkalischen Protease-Varianten
DE10162728A1 (de) * 2001-12-20 2003-07-10 Henkel Kgaa Neue Alkalische Protease aus Bacillus gibsonii (DSM 14393) und Wasch-und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE10162727A1 (de) * 2001-12-20 2003-07-10 Henkel Kgaa Neue Alkalische Protease aus Bacillus gibsonii (DSM 14391) und Wasch-und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE10163748A1 (de) 2001-12-21 2003-07-17 Henkel Kgaa Neue Glykosylhydrolasen
DE10163884A1 (de) * 2001-12-22 2003-07-10 Henkel Kgaa Neue Alkalische Protease aus Bacillus sp. (DSM 14392) und Wasch- und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE10163883A1 (de) * 2001-12-22 2003-07-10 Henkel Kgaa Neue Alkalische Protease aus Bacillus sp. (DSM 14390) und Wasch- und Reinigungsmittel enthaltend diese neue Alkalische Protease
DE10202390A1 (de) * 2002-01-23 2003-09-25 Henkel Kgaa Kombination von Cellulasen und spezieller Cellulose in Waschmitteln
DE10260930A1 (de) * 2002-12-20 2004-07-15 Henkel Kgaa Neue Cholinoxidasen
DE10260903A1 (de) * 2002-12-20 2004-07-08 Henkel Kgaa Neue Perhydrolasen
DE10360805A1 (de) * 2003-12-23 2005-07-28 Henkel Kgaa Neue Alkalische Protease und Wasch- und Reinigungsmittel, enthaltend diese neue Alkalische Protease
DE102004019751A1 (de) * 2004-04-23 2005-11-17 Henkel Kgaa Neue Alkalische Proteasen und Wasch- und Reinigungsmittel, enthaltend diese neuen Alkalischen Proteasen
DE102004029475A1 (de) * 2004-06-18 2006-01-26 Henkel Kgaa Neues enzymatisches Bleichsystem
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
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GB0504536D0 (en) * 2005-03-04 2005-04-13 Unilever Plc Fabric softening composition
US20070096052A1 (en) * 2005-10-28 2007-05-03 Shuey Steven W Poly(hydroxystyrene) stain resist
US7553985B2 (en) * 2005-11-02 2009-06-30 E.I. Du Pont De Nemours And Company Fluorinated surfactants
DE102005053529A1 (de) 2005-11-08 2007-06-21 Henkel Kgaa System zur enzymatischen Generierung von Wasserstoffperoxid
DE102006022224A1 (de) * 2006-05-11 2007-11-15 Henkel Kgaa Subtilisin aus Bacillus pumilus und Wasch- und Reinigungsmittel enthaltend dieses neue Subtilisin
CN101627139A (zh) * 2006-12-11 2010-01-13 六号元素（产品）（控股）公司 立方氮化硼压块
US8426351B2 (en) 2006-12-12 2013-04-23 Kao Corporation Liquid softener composition or transparent or semitransparent liquid softener composition
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
DE102007008655A1 (de) 2007-02-20 2008-08-21 Henkel Ag & Co. Kgaa Siderophor-Metall-Komplexe als Bleichkatalysatoren
DE102007008656A1 (de) 2007-02-20 2008-09-04 Henkel Ag & Co. Kgaa Verwendung von Harnstoff-Derivaten in Wasch- und Reinigungsmitteln
DE102007008868A1 (de) 2007-02-21 2008-08-28 Henkel Ag & Co. Kgaa Verwendung von N-Zuckersäureamiden zur Entfernung hartnäckiger Anschmutzungen
DE102007010785A1 (de) 2007-03-02 2008-09-04 Henkel Ag & Co. Kgaa Verwendung von Superoxid-Dismutasen in Wasch- und Reinigungsmitteln
DE102007017655A1 (de) 2007-04-12 2008-10-16 Henkel Ag & Co. Kgaa Verwendung von Acylharnstoffen in Wasch- und Reinigungsmittlen
DE102007017656A1 (de) 2007-04-12 2008-10-16 Henkel Ag & Co. Kgaa Biheteroaryl-Metallkomplexe als Bleichkatalysatoren
DE102007017657A1 (de) 2007-04-12 2008-10-16 Henkel Ag & Co. Kgaa Tris/heterocyclyl)-Metallkomplexe als Bleichkatalysatoren
DE102007017654A1 (de) 2007-04-12 2008-10-16 Henkel Ag & Co. Kgaa Bis(hydroxychinolin)-Metallkomplexe als Bleichkatalysatoren
DE102007036392A1 (de) 2007-07-31 2009-02-05 Henkel Ag & Co. Kgaa Zusammensetzungen enthaltend Perhydrolasen und Alkylenglykoldiacetate
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
DE102008053519A1 (de) 2008-02-20 2009-09-03 Henkel Ag & Co. Kgaa Ester von oligomeren oder polymeren Kieselsäuren mit Alkoxygruppen umfassenden Tensiden
DE102008014759A1 (de) 2008-03-18 2009-09-24 Henkel Ag & Co. Kgaa Verwendung von Imidazolium-Salzen in Wasch- und Reinigungsmitteln
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Also Published As

Publication number Publication date
WO1997031085A1 (fr) 1997-08-28
JP3253972B2 (ja) 2002-02-04
ES2187757T3 (es) 2003-06-16
ATE227765T1 (de) 2002-11-15
FR2745014B1 (fr) 1998-04-03
CA2246381A1 (fr) 1997-08-28
DE69717079T2 (de) 2003-07-24
EP0882117A1 (fr) 1998-12-09
BR9707650A (pt) 1999-07-27
DE69717079D1 (de) 2002-12-19
AU2098397A (en) 1997-09-10
JPH11505568A (ja) 1999-05-21
US6379394B1 (en) 2002-04-30
FR2745014A1 (fr) 1997-08-22

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