WO1997031085A1 - 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 PDFInfo
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- WO1997031085A1 WO1997031085A1 PCT/FR1997/000304 FR9700304W WO9731085A1 WO 1997031085 A1 WO1997031085 A1 WO 1997031085A1 FR 9700304 W FR9700304 W FR 9700304W WO 9731085 A1 WO9731085 A1 WO 9731085A1
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- WIPO (PCT)
- Prior art keywords
- agent
- cationic
- function
- cotton
- carrying
- Prior art date
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Classifications
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- 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
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- 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
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- 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-soiling treatment of articles based on woven cotton, by depositing an anti-soiling agent on said article during one or more washing, rinsing and / or softening or drying and an anti-fouling agent for woven cotton articles
- a first object of the invention consists of a process for the anti-fouling treatment of articles based on woven cotton, by deposition on said article, during one or more washing, rinsing and / or softening or drying operations. , an amphiphilic anti-fouling agent soluble or dispersible in the treatment medium, said anti-fouling agent having
- said method makes it possible to treat articles of woven cotton fibers against soiling, the latter also suitable for the treatment of articles consisting of a mixture of cotton fibers and other fibers, natural, artificial or synthetic, such as viscose, polyesters, polyacryhchic fibers ..., fibers other than cotton can represent up to 65% of the fiber mixture.
- said motif carrying a function Is a cationic function (MC) capable of being adsorbed on the surface of the cotton and its counterion.
- an anti-fouling treatment process for articles based on woven cotton by deposition on said article, during one or more washing, rinsing and / or softening or drying, of an amphiphilic anti-fouling agent soluble or dispersible in the treatment medium, said anti-fouling agent having
- MC cationic function
- MH unit of hydrophobic character
- hydrophobic character unit capable of configuring the anti-fouling agent at the cotton / water interface, any pattern which, in the treatment medium, promotes the sharing of the anti-fouling molecule between water and the surface of the cotton-based article woven.
- 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 halide ions (CI “ , Br “ , ...), acetate, sulfate, sulfonate, phosphate ... Among the counter preferential ions, there may be mentioned in particular the Br “and Cl " ions. Among the units of hydrophobic nature (MH), mention may be made of hydrocarbon groups, such as alkyls, alkenyls, linear, branched or cyclic, aryls, etc. containing at least 4 carbon atoms, preferably from 8 to 20 carbon atoms . Mention may very particularly be made of C4-C20- alkyl groups.
- Said motif with hydrophobic character can itself be one of the substituents of the heteroatom of the motif carrying a function with cationic character (MC), or be chemically linked to said motif (MC) via a hydrophilic chain.
- hydrophilic chains mention may be made of hydrophilic oligomer or polymer chains consisting of oligomer units or similar or different polymers such as those derived from
- polysaccha ⁇ des guar, cellulose derivatives, alginates, starch derivatives .
- polyoxyalkylene glycols polyoxyethylene glycols
- copolyesters in particular terephthalic (ethylene terephthalate / poly (oxyethylene) terephthalate copolymers, etc.)
- sulfone copolyesters terephthalic in particular (copolymers derived from terephthalic, isophthalic, sulfoisophthalic and diol acids, anhydrides or diesters ). polyvinyl alcohols and their copolymers. acrylic polymers and copolymers
- hydrophilic functions such as sulfonate, carboxylate, phosphate, etc.
- hydrophilic functions such as sulfonate, carboxylate, phosphate, etc.
- MC cationic
- Amounts in the range of 0.1 to 40 parts by weight of cationic functions per 100 parts by weight of antifouling agent are generally satisfactory.
- these can represent on the order of 0.01 to
- HLB hydrophilic / hydrophobic balance
- the hydrophyll of the anti-fouling molecule is such that the latter can be removed in the next wash at the same time as the soiling
- amphiphilic anti-fouling agents which can be used, there may be mentioned in particular cationic surfactants and oligomers or polymers formed from an oligomeric trunk or hydrophilic hydrocarbon polymer having in its chain or in branching units carrying a function cationic in nature (MC) with its counterion and hydrophobic in nature (MH).
- MC function cationic in nature
- MH hydrophobic in nature
- R ⁇ R ⁇ and R ⁇ are similar or different and represent H or an alkyl radical containing less than 4 carbon atoms, preferably 1 or 2 carbon atom (s) represents an alkyl radical containing more than 4 carbon atoms, preferably of the order of 8 to 20 carbon atoms.
- X " is a halide ion, preferably bromide, acetate, sulfate ...
- oligomeric or polymeric antifouling agents Mention may very particularly be made of dodecylt ⁇ methylammonium bromides, tetradecylt ⁇ methylammonium bromides, cetylt ⁇ methylammonium bromides.
- At least one motif carrying a cationic (MC) function capable of adsorbing on the surface of the cotton and its counterion
- MH hydrophobic character
- MC cationic function
- the functions of cationic nature are ammonium functions of formula R 1 R 2 R 3 N + - O ⁇
- . are similar or different and represent H or an alkyl radical containing less than 4 carbon atoms, preferably 1 or 2 carbon atom (s), optionally substituted, in particular by one or more hydroxyl function (s),. or else form together, with the nitrogen atom N + , at least one aromatic or non-aromatic ring, said functions of cationic nature (MC) being chemically linked to the oligomer, polymer or copolymer chain of polyvinyl alcohol directly by CC bond or indirectly via a bivalent or polyvalent hydrocarbon group containing at least one heteroatom.
- cationic (MC) functions mention may in particular be made of those derived from glycidylt ⁇ methylammonium chloride or bromide, chloro-1 chloride, 2-hydroxypropyl trimethylammonium
- bivalent or polyvalent hydrocarbon groups containing at least one heteroatom mention may be made those with a free bond ether, ester, urethane, acetal, amide ...
- halide ions CI “ , Br “ , 7), acetate, sulfate, sulfonate, phosphate ... hydrophobic (MH)
- linear or branched alkyl radicals preferably linear, containing from 8 to 20 carbon atoms, these being able to be chemically linked to the oligomer, polymer or copolymer chain of polyvinyl alcohol directly by CC link or indirectly by through 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 those having a free ether, ester, urethane, acetal, amide bond, etc.
- 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, of the polymer or of the polyvinyl alcohol 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
- MC cationic function
- MH hydrophobic nature
- oligomers polymers and copolymers of vinyl alcohol constituting the hydrophilic chain
- 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 (that is to say -display hydrolysis up to at least 80%) by grafting using precursor compounds of the units carrying cationic function (MC) and hydrophobic units (HD), this modification by grafting involves substitution reactions (for example ester ication, acetalisatio ⁇ , Merkeléffication ..) 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 II can also be prepared by radical copolymerization of vinyl acetate and of precursor comonomers of units carrying cationic function (MC) and hydrophobic units (MH) followed by hydrolysis (deacetalization). This type of process is also well known to those skilled in the art and described in "Polyvinyl Alcohol Developments” - Ed. C. A Finch (Wiley).
- a particular antifouling agent can be obtained by modification of a polyvinyl alcohol using (2,3-epoxypropyl) tmethylammonium chloride followed by a modification using an alkylisocyanate.
- the amounts of soiling agent that can be used according to the treatment method of the invention depend on the nature of the molecule used. These can be of the order of 0.05 to 5 grams (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. 97/31085 PC17FR97 / 00304
- the powder or liquid detergent compositions may contain on the order of 0.02 to 20% of their weight of said anti-fouling agent.
- additives of the type described below may be present - SURFACTANT AGENTS, in amounts corresponding to approximately 3-40% by weight relative to the detergent composition, surfactants such as anionic surfactants
- alkyl sulfonate esters of formula R-CH (S ⁇ 3M) -COOR ' where R represents a C-8-20 alkyl radical. preferably C10-C16 'R' an alkyl radical C6 alkyl, preferably C1 -C3, and M an alkali metal cation (sodium, potassium, lithium), substituted or unsubstituted ammonium (methyl-, dimethyl-, t ⁇ méthyl- , tetramethylammonium, dimethylpipe ⁇ dinium) or derivative of an alkanolamine (monoethanolamine, diethanolamine, triethanolamine) Mention may very particularly be made of methyl ester sulfonates whose radicals R is C - ⁇ ⁇ -C] Q, the alkyl sulfates of formula ROSO3M, or R represents a C5-C24 alkyl or hydroxyalkyl radical, preferably Cj o-Cl ⁇ 'M representing a hydrogen
- the alkylamide sulfates of formula RCONHROSO3M or R represents an alkyl radical in C2-C22. preferably in C5-C20.
- R 'a C2-C3 alkyl radical, M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylene derivatives (OE) and / or propoxylenes (OP), having an average of 0, 5 to 60 OE and / or OP patterns,.
- the salts of saturated or unsaturated C8-C24 fatty acids preferably C14-C20.
- 'C9-C20 alkylbenzenesulfonates primary or secondary C 6 -C 22 alkyl sulfonates.
- alkylglycerol sulfonates sulfonated polycarboxylic acids described in GB-A-1 082 179, paraffin sulfonates, N-acyl N-alkyltaurates, alkylphosphates, isethionates, alkylsuccmamates alkylsulfosuccinates, monoesters or diesters of sulfosuccinates, N-acyl sarcosinates, alkyl glycoside sulfates, polyethoxycarboxylates, the cation being an alkali metal (sodium, potassium, lithium), a substituted or unsubstituted ammonium residue (methyl-, dimethyl-, t ⁇ methyl-, tetramethylammonium, dimethylpipe ⁇ dinium) or derivative of an alkanolamine (monoethanolamine, diethanolamine, triethanolamine), nonionic surfactants polyoxyalkylene alkylphenols (polylphenols
- polyoxyalkylenated Cg-C22 aliphatic alcohols containing from 1 to 25 oxyalkylene units oxyethylene, oxypropylene
- ethoxylated amines amphoteric and zwitterionic surfactants alkyldimethylbetaines, alkylamidopropyldimethylbetaines, alkyltrimethylsulfobetaines, Islands of condensation products of fatty acids and protein hydrolysates
- builders agents such as adjuvants (“builders”) inorganic polyphosphates (t ⁇ polyphosphates, pyrophosphates, orthophosphates, hexametaphosphates) of alkali metals, ammonium or alkanolamines
- silicates in particular those having a Si ⁇ 2 / Na2 ⁇ ratio of the order of 1.6 / 1 to
- alkali or alkaline earth carbonates (bicarbonates, sesquicarbonates).
- alkali metal silicates and alkali metal carbonates (sodium or potassium) rich in silicon atoms in Q2 or Q3 form, described in EP-A-488 868.
- crystalline or amorphous aminosilicates of alkali metals (sodium, potassium) or ammonium such as zeolites A, P, X, zeolite A with a particle size of the order of 0.1-10 micrometers is preferred as adjuvants ( organic "builders"
- water-soluble polyphosphonates ethane 1-hydroxy-1, 1 -phosphonates, methylene salts diphosphonates
- polycarboxylate ethers (oxidisuccinic acid and its salts, monosuccinic tartrate acid and its salts, distrustic tartrate acid and its salts.
- hydroxypolycarboxylate ethers (oxidisuccinic acid and its salts, monosuccinic tartrate acid and its salts, distrustic tartrate acid and its salts.
- citric acid and its salts citric acid and its salts, mellitic acid, succinic acid and their salts.
- the salts of polyacetic acids ethylenediaminetetraacetates, nitnlot ⁇ acetates, N- (2 hydroxyethyD-nit ⁇ lodiacetates) C5-C20 alkyl succinic acids and their salts (2-dodecenylsucc ⁇ nates, lauryl succinates,)
- polyacetal carboxylic esters polyaspartic acid, polyglutamic acid and their salts, polyimides derived from the polycondensation of aspartic acid and / or glutamic acid. polycarboxymethyl derivatives of I glutamic acid or other amino acids
- BLEACHING AGENTS in amounts of about 0.1-20%, preferably about 1 -10% by weight, optionally combined with BLEACHING ACTIVATORS, in amounts of about 0.1 -60%, preferably d '' about 0.5-40% by weight, agents and activators such as bleaches
- perborates such as sodium perborate monohydrate or tetrahydrate peroxygen compounds such as sodium carbonate peroxyhydrate, pyrophosphate peroxyhydrate, urea peroxyhydrate, sodium peroxide, sodium persulfate preferably associated with a whitening activator generating in located in the washing medium, a peroxyacidic carboxylic acid, among these activators, one can mention, tetraacetylethylene diamine, tetraacetyl methylene diamine, tetraacetyl glycoluryl, p-acetoxybenzene sulfonate sodium, pentaacetyl glucose, octaacetyl lactose. .
- percarboxylic acids and their salts such as magnesium monoperoxyphthalate hexahydrate, magnesium metachloroperbenzoate, 4-nonylam ⁇ no-4-oxoperoxybutyr ⁇ que acid, 6-nonylamino-6-oxoperoxycaproic acid, diperoxydodecanedioic acid, nonoxamide peroxysuccinic acid, decyldiperoxysuccinic acid.
- These agents can be combined with at least one of the anti-fouling or anti-redeposition agents mentioned below.
- non-oxygenated bleaching agents acting by photoactivation in the presence of oxygen, agents such as sulfonated aluminum and / or zinc phthalocyanms
- agents such as. cellulose derivatives such as cellulose hydroxyethers, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose polyvinylesters grafted on polyalkylene trunks such as polyvinylacetates grafted on polyoxyethylene trunks (EP-A-219 048) .
- polyvinyl alcohols such as cellulose hydroxyethers, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose
- polyvinylesters grafted on polyalkylene trunks such as polyvinylacetates grafted on polyoxyethylene trunks (EP-A-219 048) .
- polyester copolymers based on ethylene terephthalate and / or propylene terephthalate and polyoxyethylene terephthalate units with a molar ratio (number of units) ethylene terephthalate and / or propylene terephalate / (number of units) polyoxyethylene terephthalate of the order of 1/10 at 10/1, preferably of the order of 1/1 to 9/1, the polyoxyethylene terephthalates having polyoxyethylene units having a molecular weight of the order of 300 to 5000, preferably of the order of 600 to 5000 (US-A-3,959,230, US-A-3,893,929, US-A-4,116,896, US-A-4,702,857, US-A-4,770,666); .
- sulfonated polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethylterephthalate and 1,2 propylene diol, having from 1 to 4 sulfone groups (US Pat. No. 4,968,451)
- polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated with ethyl or methyl units (US-A-4 71 1 730) or polyester oligomers terminated with alkylpolyethoxy groups (US-A-4 702 857) or sulfopolyethoxy anionic groups (US-A-4,721,580), sulfoaroyl groups (US-A-4,877,896)
- sulphonated polyester copolymers derived from terephthalic, isophthalic and sulphoisophthalic acid, anhydride or diester and a diol FR-A-2 720 399) - ANTI-REDEPOSITION AGENTS, in amounts of about 0.01 -10% by weight for a powder detergent composition from about 0.01 -5% by weight for a liquid detergent composition, agents such as . ethoxylated monoamines or polyamines, polymers of ethoxylated amines (US-A-4,597,898, EP-A-1 1,984).
- polyester sulfonated oligomers obtained by condensation of isophthalic acid, dimethyl sulfosuccinate and diethylene glycol (FR-A-2 236 926).
- polyvinylpyrollidones obtained by condensation of isophthalic acid, dimethyl sulfosuccinate and diethylene glycol (FR-A-2 236 926).
- aminocarboxylates such as ethylenediaminetetraacetates, hydroxyethyl ethylenediaminet ⁇ acetates, nit ⁇ lot ⁇ acetates
- aminophosphonates such as neutrillates (methylene phosphonates)
- polyfunctional aromatic compounds such as dihydroxydisulfobenzenes
- agents such as. the water-soluble salts of polycarboxylic acids of molecular mass of the order of 2000 to 100,000, obtained by polymerization or copolymerization of ethylenically unsaturated carboxylic acids such as acrylic acid, maleic acid or anhydride, fumaic acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid, and in particular polyacrylates of molecular mass of the order of 2,000 to 10,000 (US-A-3,308,067), copolymers of arylic acid and maleic anhydride of mass molecular of the order of 5,000 to 75,000 (EP-A-66,915).
- agents such as
- Q "24 C-OR 'ors is's alkali, ammonium or alkanolamine, of fatty acid triglycerides
- saturated or aliphatic, alicyclic, aromatic or heterocyclic unsaturated hydrocarbons such as paraffins, waxes, N-alkylaminot ⁇ azines
- monostearylphosphates monostearyl alcohol phosphates oils or polyorganosiloxane resins optionally combined with silica particles - SOFTENING AGENTS, in amounts of about 0.5-10% by weight, agents such as clays
- - ENZYMES in quantities up to 5 mg by weight, preferably of the order of 0.05-3 mg of active enzyme / g of detergent composition, enzymes such as. proteases, amylases, lipases, cellulases, peroxidases (US-A-3 553 139, US-A-4 101 457, US-A-4 507 219, US-A-4 261 868
- alcohols methanol, ethanol, propanol, isopropanol, propanediol, ethylene glycol, glycerin. buffering agents
- 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.
- liquid rinsing and / or softening compositions may contain of the order of
- additives of the type may be present - associations of anionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-ionic surfactants (lauryl ether sulfate, etc.), non-
- the anti-fouling agent can also be introduced on drying in the damp linen 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 can contain approximately 20% of its weight of antifouling agent.
- composition of detergent parts by weight Composition of detergent parts by weight
- the rinse pretreatment is carried out at 100 cycles / minute for 20 minutes at
- test pieces are used as a reference and pretreated with water alone (30 ° TH).
- the washing is carried out at 40 ° C for 20 minutes, using 5g of the detergent described above for 1 liter of water of 30 ° TH, then 3 rinses of 5 minutes in cold water and 2 dryings under ice
- test pieces The results observed on the pretreated test pieces, compared to those observed on the reference test pieces, are the following test pieces tested in% those of reference 57 those treated CTAB 68 those treated TTAB 72
- 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 hydroxypropylt ⁇ methylammonium chloride and having derived alkyl groups.
- AAC cationic alkylguar
- PVQH polyvinyl alcohol
- the proportion of grafted ammonium groups is then obtained by comparing the integral of the CHp protons of polyvinyl alcohol (between 1.2 and 1.5 ppm) with that of the ammonium protons l (CH3) 3N + J to 3 , 1 ppm
- the mixture is heated to 90 ° C. to dissolve the polymer
- reaction medium is maintained at 90 ° C for 8 hours, then the polymer is separated by precipitation with ethyl acetate
- the proportion of grafted hydrophobic units is then obtained by comparing the integral of the CH2 protons of polyvinyl alcohol (between 1.2 and 1.5 ppm) with that of methyl at the end of the alkyl chain (at 0.8 ppm). ) or with that of the methylene group of the alkyl chain in alpha of the carbamate group (at 2.9 ppm)
- the performances of the antifouling agent prepared in Example 4 are evaluated at 0.2 g / l of water, vis-à-vis the drain oil and a purple pigmentary stain (olive oil 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
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatment Of Fiber Materials (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
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Abstract
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69717079T DE69717079T2 (de) | 1996-02-20 | 1997-02-19 | Schmutzabweisendes mittel und verfahren zur behandlung von gewebten baumwollartikeln |
BR9707650A BR9707650A (pt) | 1996-02-20 | 1997-02-19 | Processo para tratamento repelente de sujeira para artigos à base de algodão tecido e agente repelente de sujeira para artigos à base de algodão tecido |
EP97906221A EP0882117B1 (fr) | 1996-02-20 | 1997-02-19 | Agent antisalissure et procede de traitement des articles a base de coton tisse |
AU20983/97A AU2098397A (en) | 1996-02-20 | 1997-02-19 | Soil-repellent agent and method for treating articles based on woven cotton |
JP52984897A JP3253972B2 (ja) | 1996-02-20 | 1997-02-19 | 汚れ剥離剤及び綿織物製品の処理方法 |
AT97906221T ATE227765T1 (de) | 1996-02-20 | 1997-02-19 | Schmutzabweisendes mittel und verfahren zur behandlung von gewebten baumwollartikeln |
Applications Claiming Priority (2)
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 |
FR96/02181 | 1996-02-20 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/631,657 Continuation US6379394B1 (en) | 1996-02-20 | 2000-08-03 | Soil-repellent agent and process for the treatment of articles based on woven cotton |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997031085A1 true WO1997031085A1 (fr) | 1997-08-28 |
Family
ID=9489465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1997/000304 WO1997031085A1 (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 (fr) |
EP (1) | EP0882117B1 (fr) |
JP (1) | JP3253972B2 (fr) |
AT (1) | ATE227765T1 (fr) |
AU (1) | AU2098397A (fr) |
BR (1) | BR9707650A (fr) |
CA (1) | CA2246381A1 (fr) |
DE (1) | DE69717079T2 (fr) |
ES (1) | ES2187757T3 (fr) |
FR (1) | FR2745014B1 (fr) |
WO (1) | WO1997031085A1 (fr) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001059053A1 (fr) * | 2000-02-09 | 2001-08-16 | Unilever Plc | Composition d'entretien de tissus |
US6566516B1 (en) * | 1998-08-31 | 2003-05-20 | Nof Corporation | High purity polysaccharide containing a hydrophobic group and process for producing it |
WO2007054203A2 (fr) | 2005-11-08 | 2007-05-18 | Henkel Ag & Co. Kgaa | Systeme pour produire du peroxyde d'hydrogene par voie enzymatique |
US7300782B2 (en) | 2001-12-21 | 2007-11-27 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Glycosyl hydrolases |
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 |
DE102007008868A1 (de) | 2007-02-21 | 2008-08-28 | Henkel Ag & Co. Kgaa | Verwendung von N-Zuckersäureamiden zur Entfernung hartnäckiger Anschmutzungen |
DE102007008656A1 (de) | 2007-02-20 | 2008-09-04 | Henkel Ag & Co. Kgaa | Verwendung von Harnstoff-Derivaten in Wasch- und Reinigungsmitteln |
DE102007010785A1 (de) | 2007-03-02 | 2008-09-04 | Henkel Ag & Co. Kgaa | Verwendung von Superoxid-Dismutasen in Wasch- und Reinigungsmitteln |
DE102007017657A1 (de) | 2007-04-12 | 2008-10-16 | Henkel Ag & Co. Kgaa | Tris/heterocyclyl)-Metallkomplexe als Bleichkatalysatoren |
DE102007017656A1 (de) | 2007-04-12 | 2008-10-16 | Henkel Ag & Co. Kgaa | Biheteroaryl-Metallkomplexe als Bleichkatalysatoren |
DE102007017655A1 (de) | 2007-04-12 | 2008-10-16 | Henkel Ag & Co. Kgaa | Verwendung von Acylharnstoffen in Wasch- und Reinigungsmittlen |
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 |
DE102008027375A1 (de) | 2008-06-09 | 2009-12-10 | Henkel Ag & Co. Kgaa | Bacitracin-Metall-Komplexe als Bleichkatalysatoren |
DE102009033248A1 (de) | 2009-07-14 | 2010-05-06 | Henkel Ag & Co. Kgaa | Waschmittel für die Niedrigtemperaturwäsche von hochfunktionellen Materialien |
DE102009001693A1 (de) | 2009-03-20 | 2010-09-23 | Henkel Ag & Co. Kgaa | 4-Aminopyridin-Derivate als Katalysatoren für die Spaltung organischer Ester |
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 |
US8426351B2 (en) | 2006-12-12 | 2013-04-23 | Kao Corporation | Liquid softener composition or transparent or semitransparent liquid softener composition |
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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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 |
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 |
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 |
DE10202390A1 (de) * | 2002-01-23 | 2003-09-25 | Henkel Kgaa | Kombination von Cellulasen und spezieller Cellulose in Waschmitteln |
DE10260903A1 (de) * | 2002-12-20 | 2004-07-08 | Henkel Kgaa | Neue Perhydrolasen |
DE10260930A1 (de) * | 2002-12-20 | 2004-07-15 | Henkel Kgaa | Neue Cholinoxidasen |
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 |
GB0504535D0 (en) * | 2005-03-04 | 2005-04-13 | Unilever Plc | Fabric softening composition |
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 |
DE102006022224A1 (de) * | 2006-05-11 | 2007-11-15 | Henkel Kgaa | Subtilisin aus Bacillus pumilus und Wasch- und Reinigungsmittel enthaltend dieses neue Subtilisin |
KR101518190B1 (ko) * | 2006-12-11 | 2015-05-07 | 엘리먼트 씩스 (프로덕션) (피티와이) 리미티드 | 입방정계 질화붕소 콤팩트 |
EP4400570A1 (fr) * | 2023-01-13 | 2024-07-17 | The Procter & Gamble Company | Composition détergente liquide pour le lavage de la vaisselle à la main |
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US3597416A (en) * | 1968-05-31 | 1971-08-03 | Procter & Gamble | Soil anti-redeposition agents,their use and detergent compositions containing same |
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1996
- 1996-02-20 FR FR9602181A patent/FR2745014B1/fr not_active Expired - Fee Related
-
1997
- 1997-02-19 JP JP52984897A patent/JP3253972B2/ja not_active Expired - Fee Related
- 1997-02-19 AU AU20983/97A patent/AU2098397A/en not_active Abandoned
- 1997-02-19 BR BR9707650A patent/BR9707650A/pt not_active Application Discontinuation
- 1997-02-19 ES ES97906221T patent/ES2187757T3/es not_active Expired - Lifetime
- 1997-02-19 CA CA002246381A patent/CA2246381A1/fr not_active Abandoned
- 1997-02-19 EP EP97906221A patent/EP0882117B1/fr not_active Expired - Lifetime
- 1997-02-19 AT AT97906221T patent/ATE227765T1/de not_active IP Right Cessation
- 1997-02-19 DE DE69717079T patent/DE69717079T2/de not_active Expired - Fee Related
- 1997-02-19 WO PCT/FR1997/000304 patent/WO1997031085A1/fr active IP Right Grant
-
2000
- 2000-08-03 US US09/631,657 patent/US6379394B1/en not_active Expired - Fee Related
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GB916555A (en) * | 1960-05-28 | 1963-01-23 | British Nylon Spinners Ltd | Detergent compositions |
US3597416A (en) * | 1968-05-31 | 1971-08-03 | Procter & Gamble | Soil anti-redeposition agents,their use and detergent compositions containing same |
US4214997A (en) * | 1977-10-26 | 1980-07-29 | Lever Brothers Company | Soil-release compositions |
US4179382A (en) * | 1977-11-21 | 1979-12-18 | The Procter & Gamble Company | Textile conditioning compositions containing polymeric cationic materials |
US4576729A (en) * | 1983-08-10 | 1986-03-18 | Sterling Drug Inc. | Liquid disinfectant laundry detergents |
US4741842A (en) * | 1986-01-27 | 1988-05-03 | Colgate-Palmolive Company | Particulate detergent softener compositions comprising a mixture of cationic softener and ethoxylated amine |
US4830784A (en) * | 1986-03-01 | 1989-05-16 | Henkel Kommanditgesellschaft Auf Aktien | Laundry detergents and cleaners with reduced requirement for conventional chemicals |
US4873003A (en) * | 1987-05-26 | 1989-10-10 | Gaf Corporation | Cationic soil release polymers |
EP0398137A2 (fr) * | 1989-05-19 | 1990-11-22 | The Procter & Gamble Company | Compositions de conditionnement de tissu, additionnées lors du rinçage contenant des agents d'assouplissement de tissu et des polyesters cationiques comme agents polymères antisalissures |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6566516B1 (en) * | 1998-08-31 | 2003-05-20 | Nof Corporation | High purity polysaccharide containing a hydrophobic group and process for producing it |
WO2001059053A1 (fr) * | 2000-02-09 | 2001-08-16 | Unilever Plc | Composition d'entretien de tissus |
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 |
US7300782B2 (en) | 2001-12-21 | 2007-11-27 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Glycosyl hydrolases |
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 |
WO2007054203A2 (fr) | 2005-11-08 | 2007-05-18 | Henkel Ag & Co. Kgaa | Systeme pour produire du peroxyde d'hydrogene par voie enzymatique |
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 |
DE102007008656A1 (de) | 2007-02-20 | 2008-09-04 | Henkel Ag & Co. Kgaa | Verwendung von Harnstoff-Derivaten in Wasch- und Reinigungsmitteln |
DE102007008655A1 (de) | 2007-02-20 | 2008-08-21 | Henkel Ag & Co. Kgaa | Siderophor-Metall-Komplexe als Bleichkatalysatoren |
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 |
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 |
DE102007017655A1 (de) | 2007-04-12 | 2008-10-16 | Henkel Ag & Co. Kgaa | Verwendung von Acylharnstoffen in Wasch- und Reinigungsmittlen |
US8361951B2 (en) | 2007-04-12 | 2013-01-29 | Henkel Ag & Co. Kgaa | Tris(heterocyclyl) metal complexes, washing and cleaning agents containing the same, and use as bleach catalysts |
US8318651B2 (en) | 2007-04-12 | 2012-11-27 | Henkel Ag & Co. Kgaa | Biheteroaryl metal complexes as bleach catalysts |
DE102007017656A1 (de) | 2007-04-12 | 2008-10-16 | Henkel Ag & Co. Kgaa | Biheteroaryl-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 |
DE102008027375A1 (de) | 2008-06-09 | 2009-12-10 | Henkel Ag & Co. Kgaa | Bacitracin-Metall-Komplexe als Bleichkatalysatoren |
DE102009001693A1 (de) | 2009-03-20 | 2010-09-23 | Henkel Ag & Co. Kgaa | 4-Aminopyridin-Derivate als Katalysatoren für die Spaltung organischer Ester |
DE102009033248A1 (de) | 2009-07-14 | 2010-05-06 | Henkel Ag & Co. Kgaa | Waschmittel für die Niedrigtemperaturwäsche von hochfunktionellen Materialien |
Also Published As
Publication number | Publication date |
---|---|
DE69717079T2 (de) | 2003-07-24 |
AU2098397A (en) | 1997-09-10 |
ATE227765T1 (de) | 2002-11-15 |
EP0882117A1 (fr) | 1998-12-09 |
CA2246381A1 (fr) | 1997-08-28 |
FR2745014A1 (fr) | 1997-08-22 |
JPH11505568A (ja) | 1999-05-21 |
FR2745014B1 (fr) | 1998-04-03 |
BR9707650A (pt) | 1999-07-27 |
JP3253972B2 (ja) | 2002-02-04 |
EP0882117B1 (fr) | 2002-11-13 |
ES2187757T3 (es) | 2003-06-16 |
DE69717079D1 (de) | 2002-12-19 |
US6379394B1 (en) | 2002-04-30 |
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