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WO1994024250A1 - Composition et procede d'inhibition du transfert de couleur - Google Patents

Composition et procede d'inhibition du transfert de couleur Download PDF

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Publication number
WO1994024250A1
WO1994024250A1 PCT/US1994/003727 US9403727W WO9424250A1 WO 1994024250 A1 WO1994024250 A1 WO 1994024250A1 US 9403727 W US9403727 W US 9403727W WO 9424250 A1 WO9424250 A1 WO 9424250A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen peroxide
catalyst
composition
water
bleaching
Prior art date
Application number
PCT/US1994/003727
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English (en)
Inventor
Kakumanu Pramod
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to CA002160230A priority Critical patent/CA2160230A1/fr
Priority to DE69407776T priority patent/DE69407776T2/de
Priority to EP94912957A priority patent/EP0693116B1/fr
Priority to JP6523281A priority patent/JPH08508781A/ja
Publication of WO1994024250A1 publication Critical patent/WO1994024250A1/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
    • C11D3/3932—Inorganic compounds or complexes
    • 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
    • C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
    • 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
    • C11D3/3947—Liquid compositions

Definitions

  • the invention pertains to prevention of dye transfer among fabrics when said fabrics are treated in an aqueous medium, such as in laundering.
  • This invention relates to a process for prevention of dye transfer among fabrics in an aqueous bath (particularly a washing solution) by decolorizing dyes which bleed from fabrics into the solution, and to compositions for use in carrying out the process.
  • detergent compositions have contained bleaching agents to decolorize stains such as tea, coffee, wine and fruit stains on household laundry.
  • bleaching agents to decolorize stains such as tea, coffee, wine and fruit stains on household laundry.
  • Persul fates e.g., Oxone (Trade Name) although sometimes deemed low temperature bleaches, in fact have little effect at low temperatures in washing conditions and may be included in this class.
  • Hydrogen-peroxide-releasing bleaching agents can be made more effective at lower temperatures by adding "activators," which are usually organic acid anhydrides, esters or imides. These activators have to be present in about the same molar proportion as the perhydrate bleaching agent and are not regenerated in use. Thus they are not catalysts. Furthermore the activated bleaching agents attack intentional colors (dyes) as well as unintentional colors (stains) on fabrics, and yet, perhaps because their action upon dispersed or dissolved dyes is too slow, they are not very effective as dye transfer inhibitors.
  • activators are usually organic acid anhydrides, esters or imides. These activators have to be present in about the same molar proportion as the perhydrate bleaching agent and are not regenerated in use. Thus they are not catalysts. Furthermore the activated bleaching agents attack intentional colors (dyes) as well as unintentional colors (stains) on fabrics, and yet, perhaps because their action upon dispersed or dissolved dyes is too slow, they are not very effective as dye transfer inhibitors.
  • low-temperature bleaching can be effected using more aggressive oxidizing agents, such as percarboxyl ic acid bleaches. These may cause color damage and even damage to some- fibers, and yet are not very effective dye transfer inhibitors.
  • Chlorine bleaches are reasonably effective dye transfer inhibitors, but are generally very harmful to colored fabrics.
  • the solid source should be coated with a material (e.g., tallow alcohol) to insure that the hydrogen peroxide will be released into the solution at a controlled rate so the hydrogen peroxide is used up in the bleaching process at substantially the same rate it is being released from the solid source.
  • a material e.g., tallow alcohol
  • the present invention is a process for treating fabrics, which process comprises contacting said fabrics in an aqueous solution comprising:
  • a bleaching catalyst selected from the group consisting of metalloporphin and metallo porphyrins and their water-soluble and water-dispersible derivatives, and
  • the concentration of a) being from about 0.02 to about 10 (preferably about 1 to about 10) micromoles ( ⁇ M) per liter and the initial concentration of hydrogen peroxide in solution being such that the molar ratio of said hydrogen peroxide to said catalyst is from about 20:1 to about 40:1, the said solution having a pH of from about 9 to about 10.
  • the process herein is preferably carried out at 5oC to about 75oC, especially from about 20oC to 60oC, but the catalysts are effective at up to about 95°C.
  • the process is typically carried out in the process of laundering fabrics.
  • materials which may contain color bodies typically at least some of the fabrics in a load of laundry are colored, i.e., contain dyes which may bleed into the laundering solution and onto other fabrics.
  • compositions suitable for use in carrying out the process comprise:
  • a bleaching catalyst selected from the group consisting of metalloporphins and metallo porphyrins and their water-soluble and water-dispersible derivatives, and
  • a bleaching agent selected from the group consisting of hydrogen peroxide, and water-soluble sources of hydrogen peroxide wherein the water solubility of the said source is such that substantially all of the hydrogen peroxide in said source is released quickly into solution when the composition is added to water, the molar ratio of hydrogen peroxide to catalyst in said composition being from about 20:1 to about 40:1.
  • the said composition should have a pH of from about 9 to about 10 when dissolved in water at a concentration sufficient to provide from about 0.02 to about 10 ⁇ M per liter of said bleaching catalyst.
  • the bleaching catalysts of the present invention are selected from metalloporphins, metalloporphyrins, and their water-soluble or water-dispersible derivatives.
  • the metalloporphin structure may be visualized as indicated in Formula I below.
  • Formula I the atom positions of the porphin structure are numbered conventionally and the double bonds are put in conventionally.
  • Formula II the double bonds have been omitted in the drawing of the structure, but are actually present as in I.
  • Preferred metalloporphin structures are those substituted at one or more of the 5, 10, 15 and 20 carbon positions of Formula I (meso positions), with a phenyl or pyridyl substituent selected from the group consisting of
  • n and m may be 0 or 1; A may be sulfate, sulfonate, phosphate or carboxylate groups; and B is C 1 -C 10 alkyl, polyethoxy alkyl or hydroxy alkyl.
  • Preferred molecules are those in which the substituents on the phenyl or pyridyl groups are selected from the group consisting of
  • a particularly preferred metalloporphin is one in which the molecule s substituted at the 5, 10, 15, and 20 carbon positions with the substituent.
  • This preferred compound is known as metal lo tetrasulfonated tetraphenylporphin.
  • the symbol X 1 is (-CY-) wherein each Y, independently, is hydrogen, chlorine, bromine or meso substituted alkyl, cycloalkyl, aralkyl, aryl, alkaryl or heteroaryl.
  • M is hydrogen or a neutralizing metal ion, preferably sodium.
  • X 2 of Formula I represents an anion, preferably OH- or Cl-.
  • the compound of Formula I may be substituted at one or more of the remaining carbon positions with C 1 -C 10 alkyl, hydroxyalkyl or oxyalkyl groups.
  • Porphin derivatives also include chlorophyls, chlorines, i.e., isobacterio chlorines and bacteriochlorines.
  • Metal loporphyrin and water-soluble or water-dispersible derivatives thereof have a structure given in Formula II.
  • Xi can be alkyl, alkylcarboxy, alkylhydroxyl, vinyl, alkenyl. alkyl sulfate, alkyl sulfonate, sulfate, sulfonate.
  • X 2 of Formula II represents an anion, preferably OH- or Cl-.
  • the bleaching agents for the method and compositions of the invention are hydrogen peroxide itself (when practicable) or solid sources of hydrogen peroxide, e.g., persalts such as sodium or potassium perborate, percarbonate and perpolyphosphates, or addition products such as the addition product of hydrogen peroxide, and urea.
  • persalts such as sodium or potassium perborate, percarbonate and perpolyphosphates
  • addition products such as the addition product of hydrogen peroxide, and urea.
  • the lithium, calcium or magnesium persalts can also be used.
  • hydrogen peroxide becomes a very effective dye transfer inhibitor, and yet causes practically no attack on dyes actually on fabrics.
  • the fabric treatment process of the invention is conveniently carried out in the course of a washing process, and the treatment bath as well as the compositions of the invention can contain the usual components of detergent compositions in the usual amounts.
  • detergent compositions of the invention typically contain from 1% to 60% (preferably 5 to 30%) of a detergent surfactant.
  • the detergent compositions herein are in the form of granules or solids, and the source of hydrogen peroxide is an addition compound of hydrogen peroxide.
  • the bleaching catalyst is usually present in an amount of from about- 0.01% to about 1%, preferably from about 0.05% to about 0.5%.
  • the source of hydrogen peroxide is present in an amount so as to provide a molar ratio of hydrogen peroxide to catalyst of from about 20:1 to about 40:1.
  • a detergent composition intended for use at 0.10% concentration using sodium perborate monohydrate as the source of hydrogen peroxide and iron tetrasulfonated tetraphenyl porphin (FeTPPS) as the catalyst the amount of sodium perborate monohydrate will be present in the composition at from about 0.1% to about 2% and the FeTPPS will be present at about 0.05 to about 0.5%.
  • the hydrogen peroxide source dissolve quickly to achieve the desired solution ratio of hydrogen peroxide to catalyst.
  • the product should therefore be formulated, so the hydrogen peroxide source will be completely dissolved, i.e., will release all of its hydrogen peroxide into the solution, within two minutes at the intended wash temperature. This can be achieved by choice of a hydrogen peroxide source having inherently quick dissolving properties at the desired fabric treatment temperature, and/or using small particle size to enhance rate of solution.
  • Particularly preferred hydrogen peroxide sources because of their high solubility over a wide temperature range are sodium perborate monohydrate and sodium percarbonate.
  • the surfactant can be selected from anionics, non-ionics, zwitterionics, amphoterics, cationics and mixtures thereof.
  • Water-soluble salts of the higher fatty acids are useful anionic surfactants in the compositions herein.
  • Soaps can be made by direct saponification of fats and oils or by the neutralization of free fatty acids.
  • Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
  • Useful anionic surfactants also include the water-soluble slats, preferably the alkali metal, ammonium and alkylol ammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl group " containing from about 10 to about 20 carbon atoms and a sulfonic acid or sulfuric acid ester group.
  • alkyl is the alkyl portion of acyl groups.
  • this group of synthetic surfactants are the sodium and potassium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C 12 -C 18 carbon atoms) such as those produced by reducing the glycerides to tallow or coconut oil; and the sodium and potassium alkyl benzene sulfonates in which the alkyl group contains from about 10 to about 16 carbon atoms, in straight chain or branched chain configuration, i.e., see U.S. Patents 2,220,099 and 2,477,383.
  • Especially valuable are linear straight chain alkylbenzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 to 14, abbreviated C 11-14 LAS.
  • anionic surfactants herein are the sodium alkyl glyceryl ether sulfonates, especially those ethers of higher alcohols derived from tallow and coconut oil; sodium coconut oil fatty acid monoglyceride sulfonates and sulfates; sodium or potassium salts of alkyl phenol ethylene oxide ether sulfates containing from about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl groups contain from about 8 to about 12 carbon atoms; and sodium or potassium salts of alkyl ethylene oxide ether sulfates containing about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl group contains from about 10 to about 20 carbon atoms.
  • Other useful anionic surfactants herein include the water-soluble salts of esters of alpha-sulfonated fatty acids containing from about 6 to 20 carbon atoms in the fatty acid group and from about 1 to 10 carbon atoms in the ester group; water-soluble salts of 2-acyloxyalkane-1- sulfonic acids containing from about 2 to 9 carbon atoms in the acyl group and from about 9 to about 23 carbon atoms in the alkane moiety; water-soluble salts of olefin and paraffin sulfonates containing from about 12 to 20 carbon atoms; and beta-alkyloxy alkane sulfonates containing from about 1 to 3 carbon atoms in the alkyl group and from about 8 to 20 carbon atoms in the alkane moiety.
  • Water-soluble nonionic surfactants are also useful in the instant compositions, such nonionic materials include compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • the length of the polyoxyalkylene group which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Suitable nonionic surfactants include the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 15 carbon atoms, in either a straight chain or branched chain configuration, with from about 3 to 80 moles of ethylene oxide per mole of alkyl phenol.
  • water-soluble and water-dispersible condensation products of aliphatic alcohols containing from 8 to 22 carbon atoms, in either straight chain or branched configuration, with from 3 to 12 moles of ethylene oxide per mole of alcohol .
  • nonionic surfactants useful herein are polyhydroxy fatty acid amides of the formula wherein R is C 9 -C 17 alkyl or alkenyl, R 1 is methyl and Z is glycityl derived from a reduced sugar or alkoxylated derivative thereof. Examples are N-Methyl N-1-deoxyglucityl cocoamide and N-Methyl N-1-deoxyglucityl oleamide. Processes for making polyhydroxy fatty acid amides are known, e.g., see U.S. Pat. 2,965,576, Wilson, issued December 20, 1960 and U.S. Pat. 2,703,798, Schwartz, issued March 8, 1955.
  • Semi-polar nonionic surfactants include water-soluble amine oxides containing one alkyl moiety of from about 10 to 18 carbon atoms and two moieties selected from the group of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and two moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
  • Preferred nonionic surfactants are of the formula R 1 (OC 2 H 4 ) n OH, wherein R 1 is a C 10 -C 16 alkyl group or a C 8 -C 12 alkyl phenyl group, and n is from 3 to about 80.
  • Amphoteric surfactants include derivatives of aliphatic or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic moiety can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one aliphatic substituent contains an anionic water-solubilizing group.
  • Zwitterionic surfactants include derivatives of aliphatic, quaternary, ammonium, phosphonium, and sulfonium compounds in which one of the aliphatic substituents contains from about 8 to 18 carbon atoms. See U.S. Pat. 3,929,678, Laugh! in et al., issued December 30, 1975. Zwitterionic surfactants are sometimes classified as a type of amphoteric surfactants.
  • Cationic surfactants can also be included in the present detergent compositions.
  • Cationic surfactants comprise a wide variety of compounds characterized by one or more organic hydrophobic groups in the cation and generally by a quaternary nitrogen associated with an acid radical. Pentavalent nitrogen ring compounds are also considered quaternary nitrogen compounds. Halides, methyl sulfate and hydroxide are suitable balancing anions for such compounds.
  • Tertiary amines can have characteristics similar to cationic surfactants at washing solution pH values less than about 8.5. A more complete disclosure of these and other cationic surfactants useful herein can be found in U.S. Patent 4,228,044, Cambre, issued October 14, 1980, incorporated herein by reference.
  • Cationic surfactants are often used in detergent compositions to provide fabric softening and/or antistatic benefits.
  • Antistatic agents which provide some softening benefit and which are preferred herein are the quaternary ammonium salts describe din U.S. Patent 3,936,537, Baskerville, Jr., et al., issued February 3, 1976, which is incorporated herein by reference.
  • Useful cationic surfactants also include those described in U.S. Patent 4,222,905, Cockrell, issued September 16, 1980, and in U.S. Patent 4,239,659, Murphy, issued,- December 16, 1980, both incorporated herein by reference.
  • compositions herein can also contain a variety of other components which are useful in the employment of said compositions.
  • Inorganic detergency builders useful in the compositions herein include, but are not limited to, the alkali metal, ammonium and alkanol ammonium salts of polyphosphates (exemplified by the tripolyphosphates, pyrophosphates, and glassy polymeric meta-phosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulphates, and aluminosilicates (i.e., zeolites).
  • Borate builders, as well as builders containing borate-forming materials that can produce borate under detergent storage or wash conditions hereinafter, collectively “borate builders"
  • non-borate builders are used in the compositions of the invention intended for use at wash conditions less than about 50oC, especially less than about 40oC.
  • silicate builders are the alkali metal silicates, particularly those having a SiO 2 :Na 2 O ratio in the range 1.6:1 to 3.2:1 and layered silicates, such as the layered sodium silicates described in U.S. Patent ' 4,664,839, issued May 12, 1987 to H. P. Rieck, incorporated herein by reference.
  • Organic detergency builders preferred for the purposes of the present invention include a wide variety of polycarboxylate compounds.
  • polycarboxylate refers to compounds having a plurality of carboxylate groups, preferably at least two carboxylates.
  • citric acid is a useful organic builder.
  • Polycarboxylate builders can generally be added to the composition in acid form, but can also be added in the form of a neutralized salt. When utilized in salt form, alkali metals, such as sodium, potassium, and lithium or alkanol ammonium salts are preferred. Included among the polycarboxylate builders are a variety of categories of useful materials. One important category of polycarboxylate builders encompasses the ether polycarboxylates. A number of ether polycarboxylates have been disclosed for use as detergent builders. Examples of useful ether polycarboxylates include oxydisuccinate, as disclosed in Berg, U.S. Patent 3,128,287, issued April 7, 1965 and Lamberti et al., U.S. Patent 3,635,830, issued January 18, 1972, both of which are incorporated herein by reference.
  • Organic polycarboxylate builders also include the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids. Examples include the sodium, potassium, lithium, ammonium and substituted ammonium salts of ethylenediamine tetraacetic acid, and ni tri l otri acetic acid .
  • Detergency builders are useful for precipitating or chelating hardness ions (i.e., Ca 2+ and Mg 2+ ) in water used in formulating the compositions herein and in wash solutions made with the compositions. Typically, builders are used at levels of from about 1% to about 40%, preferably from about 5% to about 30% in the compositions herein.
  • pH adjustment agents such as alkali metal hydroxides and organic and inorganic acids can be used to adjust the compositions to the pH desired.
  • the composition should be formulated so as to produce a pH of from about 9 to about 11 when diluted for use in laundering.
  • Enzymes which attack soils and stains such as lipases, alkaline proteases and cellulases can be used, and enzyme stabilizers such as diethylaminoethanol can be used.
  • Soil release polymers such as block copolymers of ethylene terephthalate with polyethylene oxide or polypropylene oxide (see U.S. Pat. 3,959,230, Hayes, issued May 25, 1976 and incorporated by reference herein) can be used in the present compositions at levels of from about
  • Materials which stabilize the bleaching catalyst e.g., imidizole can be included in the compositions at levels of from about 0.005 to about 5%.
  • Non-bleach types of dye transfer inhibition agents e.g., polyvinylpyrrolidone and polyvinylpyridine-N-oxide can be used in combination with the dye transfer inhibition agents of the present invention.
  • Phenolic compounds such as sodium salt of phenol sulfonate can be used to accelerate the rate of dye bleaching by the compositions herein.
  • compositions herein include soil dispersing agents such as polyacrylic acid and polyaspartic acid and their salts
  • Optical brighteners e.g., sodium or potassium salts
  • tetraethylene-pentaamine ethoxylate 15-18 EO units
  • Optical brighteners, perfumes, and suds suppressants e.g., fatty acids or silicones
  • suds suppressants e.g., fatty acids or silicones
  • This example illustrates the dye bleaching performance of tetrasulfonated tetraphenyl porphin (FeTPPS) at various pH's and ratios of hydrogen peroxide to catalyst.
  • FeTPPS tetrasulfonated tetraphenyl porphin
  • the multifibre pickup swatches are dried at room temperature overnight and measured for the amount of dye transferred on to the cotton portion of the swatches from the bleeding fabric during the wash process. Amount of the dye transferred on to the pickup swatches is measured in L, a, b units using a Hunter Color Meter and the results are expressed in delta C units vs. the original unwashed cotton.
  • the granular detergent used -in these experiments is substantially the same formula as that shown in Example II, except that it does not contain perborate and FeTPPS.
  • a granular laundry detergent of the present invention has the following formula: Na linear C 12.3 alkylbenzene sulfonate 12.71

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Abstract

L'invention se rapporte à un procédé et une composition de traitement des tissus dans un bain aqueux dans lequel le transfert de couleur sur les tissus est inhibé en présence, dans le bain, de peroxyde d'hydrogène et d'un catalyseur de blanchiment de métalloporphine ou métalloporphyrine, à un niveau de pH compris entre 9 et 10 et à un rapport spécifié du peroxyde d'hydrogène et du catalyseur.
PCT/US1994/003727 1993-04-08 1994-04-05 Composition et procede d'inhibition du transfert de couleur WO1994024250A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002160230A CA2160230A1 (fr) 1993-04-08 1994-04-05 Composition et methode pour empecher le transfert de colorant
DE69407776T DE69407776T2 (de) 1993-04-08 1994-04-05 Zusammensetzung und verfahren zur verbinderung der farbstoffübertragung
EP94912957A EP0693116B1 (fr) 1993-04-08 1994-04-05 Composition et procede d'inhibition du transfert de couleur
JP6523281A JPH08508781A (ja) 1993-04-08 1994-04-05 染料移動を防止するための組成物および方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4574293A 1993-04-08 1993-04-08
US08/045,742 1993-04-08

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WO1994024250A1 true WO1994024250A1 (fr) 1994-10-27

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JP (1) JPH08508781A (fr)
CA (1) CA2160230A1 (fr)
DE (1) DE69407776T2 (fr)
ES (1) ES2111924T3 (fr)
WO (1) WO1994024250A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995031526A1 (fr) * 1994-05-11 1995-11-23 The Procter & Gamble Company Compositions pour inhiber le transfert des couleurs, contenant des catalyseurs constitues de complexes metalliques speciaux
WO1995034629A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions detergentes comprenant des catalyseurs redox a pores larges
WO1996006155A1 (fr) * 1994-08-24 1996-02-29 The Procter & Gamble Company Compositions de blanchiment comprenant des catalyseurs de blanchiment metalliferes et des sels d'ammonium
WO1998008926A1 (fr) * 1996-08-26 1998-03-05 The Procter & Gamble Company Regulation de l'activite de la cellulase par un terminateur
EP0832969A2 (fr) * 1996-09-26 1998-04-01 Henkel Kommanditgesellschaft auf Aktien Composé catalytique actif pour améliorer l'efficacité de blanchiment
US5908821A (en) * 1994-05-11 1999-06-01 Procter & Gamble Company Dye transfer inhibiting compositions with specifically selected metallo catalysts
CN101922111A (zh) * 2010-09-14 2010-12-22 东华大学 一种使用水溶性金属卟啉的低温活化漂白的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
EP0306089A2 (fr) * 1987-09-04 1989-03-08 Unilever N.V. Porphirines de métaux comme catalyseur de blanchiment et procédé de nettoyage du linge
EP0384503A1 (fr) * 1989-02-22 1990-08-29 Unilever N.V. Métalloporphyrines pour l'utilisation comme catalyseur de blanchiment

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
EP0306089A2 (fr) * 1987-09-04 1989-03-08 Unilever N.V. Porphirines de métaux comme catalyseur de blanchiment et procédé de nettoyage du linge
EP0384503A1 (fr) * 1989-02-22 1990-08-29 Unilever N.V. Métalloporphyrines pour l'utilisation comme catalyseur de blanchiment

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995031526A1 (fr) * 1994-05-11 1995-11-23 The Procter & Gamble Company Compositions pour inhiber le transfert des couleurs, contenant des catalyseurs constitues de complexes metalliques speciaux
US5908821A (en) * 1994-05-11 1999-06-01 Procter & Gamble Company Dye transfer inhibiting compositions with specifically selected metallo catalysts
WO1995034629A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions detergentes comprenant des catalyseurs redox a pores larges
US5560748A (en) * 1994-06-10 1996-10-01 The Procter & Gamble Company Detergent compositions comprising large pore size redox catalysts
WO1996006155A1 (fr) * 1994-08-24 1996-02-29 The Procter & Gamble Company Compositions de blanchiment comprenant des catalyseurs de blanchiment metalliferes et des sels d'ammonium
WO1998008926A1 (fr) * 1996-08-26 1998-03-05 The Procter & Gamble Company Regulation de l'activite de la cellulase par un terminateur
EP0832969A2 (fr) * 1996-09-26 1998-04-01 Henkel Kommanditgesellschaft auf Aktien Composé catalytique actif pour améliorer l'efficacité de blanchiment
EP0832969A3 (fr) * 1996-09-26 1998-09-02 Henkel Kommanditgesellschaft auf Aktien Composé catalytique actif pour améliorer l'efficacité de blanchiment
CN101922111A (zh) * 2010-09-14 2010-12-22 东华大学 一种使用水溶性金属卟啉的低温活化漂白的方法

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EP0693116B1 (fr) 1998-01-07
DE69407776T2 (de) 1998-08-06
DE69407776D1 (de) 1998-02-12
EP0693116A1 (fr) 1996-01-24
JPH08508781A (ja) 1996-09-17
ES2111924T3 (es) 1998-03-16
CA2160230A1 (fr) 1994-10-27

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