WO1994011479A1 - Detergents renfermant un metallocatalyseur non ferreux et un agent de blanchiment pour empecher le transfert des couleurs au lavage - Google Patents

Detergents renfermant un metallocatalyseur non ferreux et un agent de blanchiment pour empecher le transfert des couleurs au lavage Download PDF

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Publication number
WO1994011479A1
WO1994011479A1 PCT/US1993/010548 US9310548W WO9411479A1 WO 1994011479 A1 WO1994011479 A1 WO 1994011479A1 US 9310548 W US9310548 W US 9310548W WO 9411479 A1 WO9411479 A1 WO 9411479A1
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WO
WIPO (PCT)
Prior art keywords
water
dye transfer
transfer inhibiting
composition according
iron
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Application number
PCT/US1993/010548
Other languages
English (en)
Inventor
Abdennaceur Fredj
Alfred Busch
Andre Christian Convents
James Pyott Johnston
Regine Labeque
Christiaan Arthur J. K. Thoen
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 AU55908/94A priority Critical patent/AU5590894A/en
Priority to JP6512177A priority patent/JPH08503248A/ja
Publication of WO1994011479A1 publication Critical patent/WO1994011479A1/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

Definitions

  • the present invention relates to a composition and a process for inhibiting dye transfer between fabrics during washing.
  • U.S. Patent 4,077,768 describes a process for inhibiting dye transfer by the use of an oxidizing bleaching agent together with a catalytic compound such as iron porphins.
  • Copending EP Patent Application 91202655.6 filed October 9, 1991, relates to dye transfer inhibiting compositions comprising an enzymatic system capable of generating hydrogen peroxide and porphin catalysts.
  • a dye transfer inhibiting composition which exhibits optimum dye transfer inhibiting properties.
  • the invention provides an efficient process for laundering operations involving colored fabrics.
  • the present invention relates to inhibiting dye transfer compositions comprising :
  • a process is also provided for laundering operations involving colored fabrics.
  • the present invention provides a dye transfer inhibiting composition comprising :
  • the preferred usage range of the catalyst in the wash is 10 -8 molar to 10 ⁇ 3 molar, more preferred 10 ⁇ - 10 ⁇ 4 molar.
  • the essential metallo porphin structure may be visualized as indicated in Formula I in the accompanying drawings.
  • the atom positions of the porphin structure are numbered conventionally and the double bonds are put in conventionally. In other formula, the double bonds have been omitted in the drawings, but are actually present as in I.
  • Preferred metallo porphin 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 is selected from water- solubilizing group, e.g. sulfate, sulfonate, phosphate, and carboxylate groups; and B is selected from the group consisting of _-C]_o alkyl, polyethoxy alkyl or C]_-CIQ 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 metallo phorphin is one in which the molecule is substituted at the 5, 10, 15, and 20 carbon positions with the substituent
  • This preferred compound is known as metallo tetrasulfonated tetraphenylporphin.
  • 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 ⁇ C o alkyl, hydroxyalkyl or oxyalkyl groups.
  • Porphin derivatives also include chlorophyls, chlorines, i.e. isobacterio chlorines and bacteriochlorines.
  • Metallo porphyrin and water-soluble or water-dispersable derivatives thereof ha ⁇ a structure given in formula II.
  • X can be alkyl, ⁇ ⁇ yi carboxy, alkyl hydroxyl, vinyl, alkenyl, alkyl sulfate, alkylsulfonate, sulfate, sulfonate, aryl.
  • X 2 of Formula II represents an anion, preferably OH- or Cl-.
  • the symbol X_ can be alkyl, alkylcarboxy, alkylhydroxyl, vinyl, alkenyl, alkylsulfate, alkylsulfonate, sulfate, sulfonate.
  • Metallo phthalocyanine and derivatives have the structure indicated in Formula III, wherein the atom positions of the phthalocyanine structure are numbered conventionally.
  • the anionic groups in the above structures contain cations selected from the group consisting of sodium and potassium cations or other non-interfering cations which leave the structures water-soluble.
  • Preferred phthalocyanine derivatives are metallo phthalocyanine trisulfonate and metallo phthalocyanine tetrasulfonate.
  • the choice of the substituent groups can be used to control the solubility of the catalyst in water or in detergent solutions. Yet again, especially where it is desired to avoid attacking dyes attached to solid surfaces, the substituents can control the affinity of the catalyst compound for the surface.
  • strongly negatively charged substituted compounds for instance the tetrasulfonated porphin, may be repelled by negatively charged stains or stained surfaces and are therefore most likely not to cause attack on fixed dyes, whereas the cationic or zwitterionic compounds may be attracted to, or at least not repelled by such stained surfaces.
  • the bleach used in the different examples should be such that at least 70%, preferably all of the oxygen active species is available after 5 min at 40°C.
  • the available oxygen species can be determined very easily by titration by the man skilled in the art.
  • a 1% solution of detergent is prepared in 0°C water. 5 min later, the solution is centrifuged to precipitate all non- dissolving substances. From the supernatant the available oxygen is measured as follows: a known weight of the supernatant solution to be measured is sampled and the reaction is stopped using glacial acetic acid. Excess potassium iodide (KI) is added to the solution:
  • the liberated iodine (according to eq 1) is then titrated with sodium thiosulfate (Na2S2U3) . Starch which gives a purple/blue complex with I- is used as an indicator.
  • a quick releasing bleach should have at least 70%, preferably all the available oxygen in solution after 5 minutes at 40°C.
  • the quick releasing bleaches suitable for the present invention include peroxygen bleaches.
  • suitable water-soluble solid peroxygen bleaches include hydrogen peroxide releasing agents such as hydrogen peroxide, perborates, e.g. perborate monohydrate, perborate tetrahydrate, persulfates, percarbonates, peroxydisulfates, perphosphates and peroxyhydrates.
  • Preferred bleaches are percarbonates and perborates.
  • the hydrogen peroxide releasing agents can be used in combination with bleach activators such as tetraacetylethylenediamine (TAED) , monanoyloxybenzenesulfonate (NOBS, described in US 4, 412, 934) , 3, 5, 5- trimethylhexanoloxybenzenesulfonate (ISONOBS, described in EP 120,591), or pentaacetylglucose (PAG), which are perhydrolyzed to form a peracid as the active bleaching species, leading to improved bleaching effect.
  • bleach activators such as tetraacetylethylenediamine (TAED) , monanoyloxybenzenesulfonate (NOBS, described in US 4, 412, 934) , 3, 5, 5- trimethylhexanoloxybenzenesulfonate (ISONOBS, described in EP 120,591), or pentaacetylglucose (PAG), which are perhydro
  • peroxygen bleaches suitable for the present invention include organic peroxyacids such as percarboxylic acids.
  • an efficient amount of bleach is by definition the necessary amount of bleach which combined with a bleach catalyst leads to a level of dye oxidation which is between 40% to 100%, preferably 40% to 60%, more preferred 60% to 80%, most preferred 80%-100% of the maximum (Z) per cent of dye oxidation that can be achieved under the most optimal conditions determined by those skilled in the art.
  • a washing machine or launderometer add a known bleeding fabric and a known uncolored pick-up tracer (e.g. cotton) to the wash load. After simulating a wash cycle, determine the amount of dye that has been picked up by the tracer according to methods known to those skilled in the art. Now to separate washing machines, add the same amount of bleeding fabric and pick-up tracer, a fixed amount of catalyst and vary the bleach level. Determine the level of dye transfer onto the pick tracers and vary the amount of bleach as to minimize dye transfer according to standard optimization method known to those skilled in the art. In this way the most optimal bleach concentration can be determined.
  • a known bleeding fabric and a known uncolored pick-up tracer e.g. cotton
  • compositions are conveniently used as additives to conventional detergent compositions for use in laundry operations.
  • the present invention also encompasses dye transfer inhibiting compositions which will contain detergent ingredients and thus serve as detergent compositions.
  • a wide range of surfactants can be used in the detergent compositions.
  • anionic surfactants are particularly suitable herein, especially mixtures of sulphonate and sulphate surfactants in a weight ratio of from 5:1 to 1:2, preferably from 3:1 to 2:3, more preferably from 3:1 to 1:1.
  • Preferred sulphonates include alkyl benzene sulphonates having from 9 to 15, especially 11 to 13 carbon atoms in the alkyl radical, and alpha-sulphonated methyl fatty acid esters in which the fatty acid is derived from a C ⁇ -C ⁇ g fatty source preferably from a Cl6 -C 18 fatty source.
  • the cation is an alkali metal, preferably sodium.
  • Preferred sulphate surfactants are alkyl sulphates having from 12 to 18 carbon atoms in the alkyl radical, optionally in admixture with ethoxy sulphates having from 10 to 20, preferably 10 to 16 carbon atoms in the alkyl radical and an average degree of ethoxylation of 1 to 6.
  • alkyl sulphates herein are tallow alkyl sulphate, coconut alkyl sulphate, and c 14-15 alkyl sulphates.
  • the cation in each instance is again an alkali metal cation, preferably sodium.
  • One class of nonionic surfactants useful in the present invention are condensates of ethylene oxide with a hydrophobic moiety to provide a surfactant having an average hydrophilic- lipophilic balance (HLB) in the range from 8 to 17, preferably from 9.5 to 13.5, more preferably from 10 to 12.5.
  • HLB hydrophilic- lipophilic balance
  • the hydrophobic (lipophilic) moiety may be aliphatic or aromatic in nature and the length of the polyoxyethylene 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.
  • Especially preferred nonionic surfactants of this type are the C9-C15 primary alcohol ethoxylates containing 3-8 moles of ethylene oxide per mole of alcohol, particularly the C1 -C15 primary alcohols containing 6-8 moles of ethylene oxide per mole of alcohol and the C12-C14 primary alcohols containing 3- 5 moles of ethylene oxide per mole of alcohol.
  • Another class of nonionic surfactants comprises alkyl polyglucoside compounds of general formula
  • Z is a moiety derived from glucose; R is a saturated hydrophobic alkyl group that contains from 12 to 18 carbon atoms; t is from 0 to 10 and n is 2 or 3; x is from 1.3 to 4, the compounds including less than 10% unreacted fatty alcohol and less than 50% short chain alkyl polyglucosides.
  • Compounds of this type and their use in detergent are disclosed in EP-B 0 070 077, 0 075 996 and 0 094 118.
  • nonionic surfactants are polyhydroxy fatty acid amide surfactants of the formula
  • R 1 is H, or R 1 is C ⁇ _4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or a mixture thereof
  • R 2 is 05-31 hydrocarbyl
  • Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative thereof.
  • R 1 is methyl
  • R 2 is a straight Cn_i5 alkyl or alkenyl chain such as coconut alkyl or mixtures thereof
  • Z is derived from a reducing sugar such as glucose, fructose, maltose, lactose, in a reductive amination reaction.
  • compositions according to the present invention may further comprise a builder system.
  • a builder system Any conventional builder system is suitable for use herein including aluminosilicate materials, silicates, polycarboxylates and fatty acids, materials such as ethylenediamine tetraacetate, metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid.
  • phosphate builders can also be used herein.
  • Suitable builders can be an inorganic ion exchange material, commonly an inorganic hydrated aluminosilicate material, more particularly a hydrated synthetic zeolite such as hydrated zeolite A, X, B or HS.
  • SKS-6 is a crystalline layered silicate consisting of sodium silicate (Na2Si2 ⁇ 5) .
  • Suitable polycarboxylates builders for use herein include citric acid, preferably in the form of a water-soluble salt, derivatives of succinic acid of the formula R- CH(C00H)CH2 (COOH) wherein R is C10-20 alkyl or alkenyl, preferably C12-16, or wherein R can be substituted with hydroxyl, sulfo sulfoxyl or sulfone substituents.
  • lauryl succinate yristyl succinate, palmityl succinate2-dodecenylsuccinate, 2-tetradecenyl succinate.
  • Succinate builders are preferably used in the form of their water-soluble salts, including sodium, potassium, ammonium and alkanolammonium salts.
  • polycarboxylates are oxodisuccinates and mixtures of tartrate monosuccinic and tartrate disuccinic acid such as described in US 4,663,071.
  • suitable fatty acid builders for use herein are saturated or unsaturated C10- 18 fatty acids, as well as the corresponding soaps.
  • Preferred saturated species have from 12 to 16 carbon atoms in the alkyl chain.
  • the preferred unsaturated fatty acid is oleic acid.
  • Another preferred builder system for liquid compositions is based on dodecenyl succinic acid.
  • Preferred builder systems for use in granular compositions include a mixture of a water-insoluble aluminosilicate builder such as zeolite A, and a watersoluble carboxylate chelating agent such as citric acid.
  • builder materials that can form part of the builder system for use in granular compositions for the purposes of this invention include inorganic materials such as alkali metal carbonates, bicarbonates, silicates, and organic materials such as the organic phosphonates, amino polyalkylene phosphonates and amino polycarboxylates.
  • Suitable water-soluble organic salts are the homo- or co-polymeric acids or their salts, in which the polycarboxylic acid comprises at least two carboxyl radicals separated from each other by not more than two carbon atoms.
  • Polymers of this type are disclosed in GB-A-1, 596, 756.
  • Examples of such salts are polyacrylates of MW 2000-5000 and their copolymers with maleic anhydride, such copolymers having a molecular weight of from 20,000 to 70,000, especially about 40,000.
  • Detergency builder salts are normally included in amounts of from 10% to 80% by weight of the composition preferably from 20% to 70% and most usually from 30% to 60% by weight.
  • detergent compositions may be employed, such as suds boosting or depressing agents, enzymes and stabilizers or activators therefore, soil-suspending agents soil-release agents, optical brighteners, abrasives, bactericides, tarnish inhibitors, coloring agents, and perfumes.
  • enzyme technologies which also provide a type of color care benefit. Examples are cellulase for color maintenance/ rejuvenation.
  • These components should preferably be chosen such that they are compatible with the bleach component of the composition.
  • the detergent compositions according to the invention can be in liquid, paste or granular forms.
  • Granular compositions according to the present invention can also be in "compact form", i.e. they may have a relatively higher density than conventional granular detergents, i.e. from 550 to 950 g/1; in such case, the granular detergent compositions according to the present invention will contain a lower amount of "inorganic filler salt", compared to conventional granular detergents; typical filler salts are alkaline earth metal salts of sulphates and chlorides, typically sodium sulphate; "compact" detergents typically comprise not more than 10% filler salt.
  • the present invention also relates to a process for inhibiting dye transfer from one fabric to another of solubilized and suspended dyes encountered during fabric laundering operations involving colored fabrics.
  • the process comprises contacting fabrics with a laundering solution as hereinbefore described.
  • the process of the invention is conveniently carried out in the course of the washing process.
  • the washing process is preferably carried out at 5°C to 90°C, especially 20 to 60, but the catalysts are effective at up to 95°C.
  • the pH of the treatment solution is preferably from 7 to 11, especially from 7.0 to 9.0.
  • the process and compositions of the invention can also be used as additive during laundry operations.
  • the extent of dye oxidation was measured by two different methods: (i) in solution dye bleaching and (2) measurement of the reduction of dye transfer from textile to textile.
  • a detergent solution (100 mL) containing dyes (40 ppm final concentration) and the catalyst (1 x 10-5 M) was prepared and its pH value adjusted to 8.0 or 10.
  • the absorbance spectrum was recorded from 350-800 nm. This region should encompasses the wavelength maximum of the dyes (as noted for some example in the table below) and the maximum absorbance of the catalyst (Soret band and Q band for porphyrins and phthalocyanines, respectively) .
  • the oxidant H2O2, perborate, percarbonate, activated bleach or oxone
  • the level of oxidant should be optimum as defined in test method A. After 30 min the absorbance spectrum was recorded and the decrease in absorbance of the dyes noted.
  • MnTPPS Mangano tetrasulfonated phenylporphyrin
  • MnTDPP8S Mangano octasulfonated dichlorophenylporphyrin
  • Cr-TPPS Chromium-tetrasulfonated phenylporphyrin
  • MnPC Mangano-tetrasulfonated phenylporphyrin
  • ⁇ a and ⁇ b represents the difference in the intensity of reflected light between the test multifibres and a multifibre reference that was not on contact with the dyed fabrics.
  • b represents the intensity of reflected yellow light (positive b value) or the intensity of reflected blue light (negative blue value)
  • a is the measure of the intensity of the reflected red light (positive a value) or the reflected green light (negative a value) .
  • the higher ⁇ . C the more dye transfer has transferred onto the multifibre.
  • a liquid dye transfer inhibiting composition according to the present invention is prepared, having the following compositions :
  • Ci4_i5 alkyl 2.5 times ethoxylated sulfate 0
  • Catalyst 1 Mn-tetrasulfonated tetraphenylporphine 0.05 0.0
  • Catalyst 2 Cr-tetrasulfonated tetraphenylporphine 0.100
  • Catalyst 3 Fe-Phthalocyanine tetrasulfonated
  • a compact granular dye transfer inhibiting composition according to the present invention is prepared, having the following formulation:
  • Catalyst 1 Mn-tetrasulfonated tetraphenylporphine 0.1 0.0
  • Catalyst 2 Cr-tetrasulfonated tetraphenylporphine
  • Catalyst 3 Fe-Phthalocyanine tetrasulfonated

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Un métallocatalyseur non ferreux choisi parmi: a) une métalloporphine non ferreuse et des dérivés de cette substance solubles dans l'eau ou dispersables dans l'eau; b) une métalloporphyrine non ferreuse et des dérivés de cette substance solubles dans l'eau ou dispersables dans l'eau; c) une métallophtalocyanine non ferreuse et des dérivés de cette substance solubles dans l'eau ou dispersables dans l'eau; une dose efficace d'un agent de blanchiment à libération rapide, cet agent de blanchiment se présentant sous une forme se prétant à une libération dans la solution de lavage dans les cinq premières minutes après que la composition s'est dissoute ou dispersée dans l'eau.
PCT/US1993/010548 1992-11-06 1993-11-03 Detergents renfermant un metallocatalyseur non ferreux et un agent de blanchiment pour empecher le transfert des couleurs au lavage WO1994011479A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU55908/94A AU5590894A (en) 1992-11-06 1993-11-03 Detergents containing non-iron metallocatalyst and bleach to inhibit dye transfer in washing
JP6512177A JPH08503248A (ja) 1992-11-06 1993-11-03 洗浄中における染料移動を抑制するための非鉄金属触媒と漂白剤とを含有する洗剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92870183.8 1992-11-06
EP92870183A EP0596186A1 (fr) 1992-11-06 1992-11-06 Compositions détergentes avec additifs pour empêcher le transfert de colorant

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WO1994011479A1 true WO1994011479A1 (fr) 1994-05-26

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EP (1) EP0596186A1 (fr)
JP (1) JPH08503248A (fr)
CN (1) CN1088255A (fr)
AU (1) AU5590894A (fr)
CA (1) CA2148809A1 (fr)
MX (1) MX9306970A (fr)
WO (1) WO1994011479A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8993504B2 (en) 2007-12-19 2015-03-31 Lion Corporation Oxidation catalyst for bleaching, and bleaching composition using the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998008926A1 (fr) * 1996-08-26 1998-03-05 The Procter & Gamble Company Regulation de l'activite de la cellulase par un terminateur
CN113338061A (zh) * 2021-05-27 2021-09-03 广州骏亚纺织科技有限公司 双氧水催化剂的组合物及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927967A (en) * 1972-06-02 1975-12-23 Procter & Gamble Photoactivated bleaching process and composition
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
US4240920A (en) * 1978-02-28 1980-12-23 The Procter & Gamble Company Detergent bleach composition and process

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE12254T1 (de) * 1980-12-22 1985-04-15 Unilever Nv Einen photoaktivator enthaltende zusammensetzung mit verbesserter bleichwirkung.
US4399049A (en) * 1981-04-08 1983-08-16 The Procter & Gamble Company Detergent additive compositions
CH657864A5 (de) * 1984-02-17 1986-09-30 Ciba Geigy Ag Wasserloesliche phthalocyaninverbindungen und deren verwendung als photoaktivatoren.
ES2075132T3 (es) * 1989-02-22 1995-10-01 Unilever Nv Uso de metalo-porfirinas como catalizadores de blanqueo.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927967A (en) * 1972-06-02 1975-12-23 Procter & Gamble Photoactivated bleaching process and composition
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
US4240920A (en) * 1978-02-28 1980-12-23 The Procter & Gamble Company Detergent bleach composition and process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8993504B2 (en) 2007-12-19 2015-03-31 Lion Corporation Oxidation catalyst for bleaching, and bleaching composition using the same

Also Published As

Publication number Publication date
MX9306970A (es) 1995-01-31
CA2148809A1 (fr) 1994-05-26
EP0596186A1 (fr) 1994-05-11
JPH08503248A (ja) 1996-04-09
AU5590894A (en) 1994-06-08
CN1088255A (zh) 1994-06-22

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