EP0068547A1 - Gemischte Peroxysäure-Bleichmittel mit verbesserter Bleichkraft - Google Patents

Gemischte Peroxysäure-Bleichmittel mit verbesserter Bleichkraft Download PDF

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Publication number
EP0068547A1
EP0068547A1 EP82200707A EP82200707A EP0068547A1 EP 0068547 A1 EP0068547 A1 EP 0068547A1 EP 82200707 A EP82200707 A EP 82200707A EP 82200707 A EP82200707 A EP 82200707A EP 0068547 A1 EP0068547 A1 EP 0068547A1
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EP
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Prior art keywords
acid
bleach
peroxyacid
hydrophobic
bleaching
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Granted
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EP82200707A
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English (en)
French (fr)
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EP0068547B1 (de
Inventor
Frank Paul Bossu
Mark Leslie Kacher
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Procter and Gamble Co
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Procter and Gamble Co
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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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3945—Organic per-compounds

Definitions

  • This invention relates broadly to bleaching com- positions. More particularly, this invention relates to bleaching compositions which derive their bleaching activity from a compound having an active oxygen content. Still more particularly, this.invention relates to peroxyacid bleaching compositions.
  • Peroxygen bleaching agents in general and peroxyacid compounds in particular have long been recognized as effective bleaching agents for use when the adverse color and fabric damage effects of harsh active halogen bleaching agents cannot be tolerated. See, for example, Canadian Pat. No. 635,620, issued January 30, 1962, to McCune. U.S. Pat. No. 3,414,593, issued December 3, 1968, to Robson, discloses alpha-sulfo peroxy fatty acid compounds as detergents and bleaching agents.
  • Peroxyacid bleach compositions having increased solubility are also disclosed in U.S. Pat. No. 4,126,573, November 21, 1978, to Johnston.
  • 1,687,804 discloses that inorganic and organic peroxide which has a high proportion of available oxygen but an ordinarily low efficacy as a bleach may be activated by the addition of 1-20% of an organic peroxide which is a more active bleach.
  • the preferred activating organic peroxyacids are the fatty acids.
  • hydrophilic peroxyacid bleaches are effective bleaches for hydrophilic soils, but ineffective for bleaching hydrophobic soils, and vice versa, hydrophobic peroxyacid bleaches are more effective on hydrophobic soils.
  • hydrotropic are somewhere in between the hydrophilic and hydrophobic bleaches in effectiveness on a particular type of soil. Bleaching ineffectiveness on a particular type of soil equates with poorer overall bleaching. This problem has not been recognized and addressed in modern peroxyacid bleach art.
  • the present invention is directed to a laundry bleach comprising a mixture of peroxyacid bleaches selected from the group consisting of:
  • the two essential components of the present invention are at least two peroxyacid compounds selected from different classes of peroxyacids. These will be described in turn below.
  • the peroxyacid bleach-composition of the instant invention comprises a mixture of at least two peroxyacid compounds.
  • the preferred peroxyacid compounds are "normally solid", i.e., dry or solid at room temperature.
  • the peroxyacid compounds of the present invention in general, are the organic peroxyacids, water-soluble salts thereof which yield a species containing a -0-0 moiety in aqueous solu- tion, and adducts of the organic peroxyacids and urea.
  • R1 and R2 are alkylene groups containing from 1 to about 20 carbon atoms or phenylene groups
  • X and Y are hydrogen, halogen, alkyl, aryl or any group which provides an anionic moiety in aqueous solution.
  • Such X and Y groups can include, for example, wherein M is H or a water-soluble, salt-forming cation. It is preferred that the acids used in the present invention be dried to a moisture level lower than 1.0%, and preferably lower than 0.5%.
  • peroxyacids are classified as either (1) hydrophilic, (2) hydrophobic, or (3) hydrotropic. These classifications are based on their different levels of effectiveness on real world soils.
  • Real world soils contain hydrophilic and/or hydrophobic components.
  • a hydrophilic bleach is most effective on a hydrophilic bleachable soil, such as tea (tannic acid based), fruit juices, and the like.
  • hydrophobic bleaches are most effective on hydrophobic bleachable soils, such as body soils (fatty acid/triglyceride based).
  • Hydrotropic bleaches find utility on both types of soils, but are less effective on hydrophilic soils than hydrophilic bleaches and less effective on hydrophobic soils than hydrophobic bleaches. Combinations of peroxyacids of the different classes result in better overall bleaching than is achieved with a single peroxyacid.
  • hydrophilic bleach is defined as a peroxyacid whose parent carboxylic acid (or the salts thereof):
  • hydrophobic bleach is defined as a peroxyacid whose parent carboxylic acid (or salts thereof) has a CMC of less than 0.5M.
  • the "hydrotropic bleach” is defined as a peroxyacid whose parent carboxylic acid (or salts thereof) has no measurable CMC below 0.5M and has a chromatographic retention time of greater than 5.0 minutes under the HPLC conditions described above.
  • the CMC is measured in aqueous solution at 20°-50°C.
  • Class a - Hydrophilic peroxyacid bleaches can include:
  • Aromatic monoperoxyacids X substitution in 2-6 position
  • Class b - Hydrotropic peroxyacid-bleaches can include:
  • Class c - Hydrophobic peroxyacid bleaches can include:
  • hydrophobic peroxyacid bleaches there been found that those which have a long hydrocarbon chain with the percarboxylate group at one end (e.g., perlauric acid) tend to be more effective (on an equal available oxygen basis) in the bleaching of hydrophobic stains from fabrics than those which are not constructed in this way, e.g., peroxybenzoic acid and diperoxydodecanedioic acid.
  • the long chain peroxyacids with the percarboxylate groups at one end have a structure similar to surface active agents (surfactants). It is believed that in a washing solution, their hydrophobic "tail” tends to be attached to the hydrophobic stains on the fabrics, thereby causing a localized increase in bleach concentration around the stain and thus resulting in increased efficiency in bleaching for a given concentration of active oxygen in the bleaching solution.
  • surface active agents surfactants
  • surfactants be present in the bleaching solutions in which the peroxyacids are used.
  • Surfactants should generally be present in the bleaching solution at a level of at least 150 ppm. It is the usual practice to bleach fabrics in a laundering solution which contains a laundry detergent. Such detergents contain surfactants and are generally used at solution concentrations which provide more than 200 ppm surfactant to the solution. Thus, if the bleach compositions herein are to be used with a laundry detergent there is no need to incorporate a surfactant into the bleach composition.
  • surfactants are incorporated into the bleach compositions herein they will generally be present at levels of from 0.5% to 60%, preferably from 20% to 30% of the compositiop. Examples of suitable surfactants are given below.
  • Water-soluble salts of the higher fatty acids are useful as the anionic surfactant herein.
  • This class of surfactants includes ordinary alkali metal soaps such as the sodium, potassium, ammonium and alkanolammonium salts of higher fatty acids containing from 8 to 24 carbon atoms and preferably from 10 to 20 carbon atoms. 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 soaps.
  • anionic surfactants includes water-soluble salts, particularly the alkali metal, ammonium and alkanolammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl group containing from 8 to 22 carbon atoms and a sulfonic acid or sulfuric acid ester group.
  • alkyl is the alkyl portion of acylgroups.
  • this group of synthetic surfactants which can be used in the present bleaching compositions are the sodium and potassium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C 8 -C 18 carbon atoms) produced by reducing the glycerides of tallow or coconut oil; and sodium and potassium alkyl benzene sulfonates, in which the alkyl group contains from 9 to 15 carbon atoms in straight chain or branched chain configuration, e.g., those of the type described in U.S. Pat. Nos. 2,220,099, Guenther et al., issued November 5, 1940; and 2,477,383, Lewis, issued . July 26, 1949.
  • anionic surfactant compounds useful herein include 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; and sodium or potassium salts of alkyl phenol ethylene oxide ether sulfates containing 1 to 10 units of ethylene oxide per molecule and wherein the alkyl groups contain 8 to 12 carbon atoms.
  • Other useful anionic surfactants herein include the water-soluble salts of esters of a-sulfonated fatty acids containing from 6 to 20 carbon atoms in the ester group; water-soluble salts of 2-acyloxy-alkane-1-sulfonic acids containing from 2 to 9 carbon atoms in the acyl group and from 9 to 23 carbon atoms in the alkane moiety; alkyl ether sulfates containing from 10 to 20 carbon atoms in the alkyl group and from 1 to 30 moles of ethylene oxide; water-soluble salts of olefin sulfonates containing from 12 to 24 carbon atoms; and ⁇ -alkyloxy alkane sulfonates containing from 1 to 3 carbon atoms in the alkyl group and from 8 to 20 carbon atoms in the alkane moiety.
  • Preferred water-soluble anionic organic surfactants herein include linear alkyl benzene sulfonates containing from 11 to 14 carbon atoms in the alkyl group; the tallow range alkyl sulfates; the coconut range alkyl glyceryl sulfonates; and alkyl ether sulfates wherein the alkyl moiety contains from 14 to 18 carbon atoms and wherein the average degree of ethoxylation varies between 1 and 6.
  • Specific preferred anionic surfactants for use herein include: sodium linear C 10 -C 12 alkyl benzene sulfonate; triethanolamine C 10 -C 12 alkyl benzene sulfonate; sodium tallow alkyl sulfate; sodium coconut alkyl glyceryl ether sulfonate; and the sodium salt of a sulfated condensation product of tallow alcohol with from 3 to 10 moles of ethylene oxide.
  • anionic surfactants can be used separately herein or as mixtures.
  • Nonionic surfactants include the water-soluble ethoxylates of C 10 -C 20 aliphatic alcohols and C 6 -C 12 alkyl phenols. Many nonionic surfactants are especially suitable for use as suds controlling agents in combination with anionic surfactants of the type disclosed herein.
  • Semi-polar surfactants useful herein include water-soluble amine oxides containing one alkyl moiety of from 10 to 28 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxylalkyl groups containing from 1 to 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of 10 to . 28 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from 1 to 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from 10 to 28 carbon atoms and a moiety selected.from the group consisting of alkyl and hydroxyalkyl moieties of from 1 to 3 carbon atoms.
  • Ampholytic surfactants include derivatives of aliphatic amines 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 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 the aliphatic moieties can be straight or branched chain, and wherein one of the aliphatic substituents contains from 8 to 18 carbon atoms and one contains an anionic water-solubilizing group.
  • compositions can also comprise those detergency builders commonly taught for use in laundry compositions.
  • Useful builders herein include any of the conventional inorganic and organic water-soluble builder salts, as well as various water-insoluble and so-called "seeded" builders.
  • Inorganic detergency builders useful herein include, for example, water-soluble salts of phosphates, pyrophosphates, orthophosphates, polyphosphates, carbonates, bicarbonates, borates and silicates.
  • Specific examples of inorganic phosphate builders include sodium and potassium tripolyphosphates, phosphates, and hexametaphosphates.
  • Sodium tripolyphosphate is an especially preferred, water-soluble inorganic builder herein.
  • Nonphosphorus-containing sequestrants can also be selected for use herein as detergency builders.
  • Specific examples of nonphosphorus, inorganic builder ingredients include water-soluble inorganic carbonate, bicarbonate, borate and silicate salts.
  • the alkali metal, e.g., sodium and potassium, carbonates, bicarbonates, borates (Borax) and silicates are particularly useful herein.
  • Water-soluble, organic builders are also useful herein.
  • the alkali metal, ammonium and substituted ammonium polyacetates, carboxylates, polycarboxylates, succinates, and polyhydroxysulfonates are useful builders in the present compositions and processes.
  • Specific examples of the polyacetate and polycarboxylate builder salts include sodium, potassium, lithium, ammonium and substituted ammonium salts of ethylene diamine tetraacetic acid, nitrilotriacetic-acid, oxydisuccinic acid, mellitic acid, benzene polycarboxylic acids, and citric acid.
  • Highly preferred nonphsophorous builder materials include sodium carbonate sodium bicarbonate, sodium silicate, sodium citrate, sodium oxydisuccinate, sodium mellitate, sodium nitrilotriacetate, and sodium ethylenediaminetetraacetate, and mixtures thereof.
  • materials capable of forming the water-insoluble reaction product include the water-soluble salts of carbonates, bicarbonates, sesquicarbonates, silicates, aluminates and oxalates.
  • the alkali metal, especially sodium, salts of the foregoing materials are preferred for convenience and ecomony.
  • Another type of builder useful herein includes various substantially water-insoluble materials which are capable of reducing the hardness content of laundering liquors, e.g., by ion-exchange processes.
  • Examples of such builder materials include the phosphorylated cloths disclosed in U.S. Pat. No.,3,424,545, Bauman, issued January 28,'1969.
  • the complex aliminosilicates i.e., zeolite-type' materials
  • zeolite-type' materials are useful detergency builders herein in that these materials soften water, i.e., remove hardness ions.
  • zeolites especially zeolite A and hydrated zeolite A materials, are useful for this purpose.
  • a description of zeolite materials and a method of preparation appear in U.S. Pat. No. 2,882,243, Milton, issued April 14, 1959.
  • aminophosphonate stabilizers which are commercially available compounds sold under the names Dequest 2000, Dequest 2041 and Dequest 2060, by The Monsanto Company, St. Louis, Missouri.
  • the.aminophosphonate compounds can be used in their acid form, represented by the above formulas, or one or more of the acidic hydrogens can be replaced by an alkali metal ion, e.g., sodium or potassium..
  • Additional stabilizers can also be used, primarily to protect the peroxyacids against decomposition which is catalyzed by heavy metals such as iron and copper. Such additional stabilizing agents are preferably present at levels of from 0.005% to 1.0% of the composition. These additional stabilizers can be any of the well-known chelating agents, but certain ones are preferred.
  • U.S. Pat. No. 3,442,937, Sennewald et al., issued May 6, 1969 discloses a chelating system comprising quinoline or a salt thereof, an alkali metal polyphosphate, and optionally, a synergistic amount of urea.
  • a . preferred auxilliary chelating system for the present invention is a mixture of 8-hydroxyquinoline or dipicolinic acid and an acid polyphosphate, preferably acid sodium pyrophosphate.
  • the latter may be a mixture of phosphoric acid and sodium pyrophosphate wherein the ratio of the former to the latter is from 0.2:1 to . 2:1 and the ratio of the mixture of 8-hydroxyquinoline or dipicolinic acid is from 1:1 to 5:1.
  • the dry granular compositions can be coated with coating materials in order to protect them against moisture and other environmental factors which may tend to cause deterioration of the compositions when stored for long periods of time.
  • coating materials may be in general, acids, esters, ethers, surfactants and hydrocarbons and include such a wide variety of materials as fatty acids, derivatives of fatty alcohols such as esters and ethers, poly functional carboxylic acids and amides, alkyl benzene sulfonates, alkyl sulfates and hydrocarbon oils and waxes. These materials aid in preventing moisture from reaching the peroxyacid compound.
  • the coating may be used to segregate the peroxyacid compound from other agents which may be present in the composition and which could adversely affect the peroxyacid's stability.
  • the amount of the coating material used is generally from
  • Agents which improve the solubility of the peroxyacid product such as sodium sulfate, starch, cellulose. derivatives, surfactants, etc., are also advantageously used herein. (See U.S. Pat. No. 4, 126, 573, Johnson, issued November 21, 1978) These agents can be called solubilizers and are generally used in an amount of from 10% to 200% based on the weight of the peroxyacid.
  • organic peroxyacids When subjected to excessive heat, organic peroxyacids can undergo a self-accelerating decomposition which can generate sufficient heat to ignite the peroxyacid. For this reason, it is desirable to include an exotherm control agent in peroxyacid bleaching compositions. Suitable materials include urea, hydrates of potassium aluminum sulfate and aluminum sulfate. A preferred exotherm agent is boric acid (See U.S. Pat. No. 4,100,095, Hutchins, issued July 11, 1978). The exotherm agent is preferably used in the composition at a level of from 50% to 400% of the amount of peroxyacid.
  • compositions herein may also be used in the compositions herein at the levels conventionally present in detergent and bleaching compositions.
  • the Hunter. Whiteness values set froth are a measure of the bleaching activity of the bleaching agents tested. The larger Hunter Whiteness value represents greater cleaning and whitening.
  • hydrophobic peroxyacid, peroxylauric acid was prepared by the oxidation of the parent carboxylic acid, lauric acid, with hydrogen peroxide in the presence of water and sulfuric acid.
  • the CMC of sodium laurate equals 2 x J.0 -2 molar. Reaction conditions were typical of those cited in the literature (e.g., Parker et al., J. Am. Chem. Soc., 77, ⁇ 4037 (1955).
  • the resulting 70/30 peroxylauric acid-water mixture was blended with finely ground urea (3 parts urea to 1 part peroxylauric acid) and dried to form the peroxyacid adduct. The adduct was analyzed and determined to contain 1.7% AvO.
  • the hydrotropic peroxyacid, diperoxydodecanedioic acid was prepared by the oxidation.of dodecanedioic acid with hydrogen peroxide in the'presence of sulfuric acid. Reaction conditions were typical of those cited in the literature (e.g., McCune Can. 635, 620). Neither the mono- or disodium salts of dodecanedioic acid has a measurable CMC below 0.5M and the parent acid has a retention time of 23.3 minutes under the chromatographic conditions ⁇ previously cited.
  • the diperoxyacid-water mixture resulting from the synthesis contained 34% peroxyacid. This mixture was blended with finely ground urea (3 parts urea to 1 part peroxyacid) and dried. The resulting chemical was partially adducted and was analyzed to contain 2.7% AvO.
  • Example 2 The preparation and properties of the hydrophilic bleach, diperoxyadipic acid, are described in Example 2, paragraph 2.
  • the preparation and description of the hydrophobic peroxyacid, peroxylauric acid, are described in Example 1, paragraph 1.
  • the preparation of the bleach solution and bleachable stains are as described in Example 1.
  • the three bleach compositions are listed in Table III. The results show an increase in hydrophilic stain removal for the mixture over the individual components, and an increase in hydrophobic stain removal for the mixture over DPAA. When the composite of results on both stains is considered the mixture has an overall advantage over the individual components.

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  • Life Sciences & Earth Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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EP19820200707 1981-06-22 1982-06-09 Gemischte Peroxysäure-Bleichmittel mit verbesserter Bleichkraft Expired EP0068547B1 (de)

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US27556881A 1981-06-22 1981-06-22
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Cited By (26)

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DE3240505A1 (de) * 1981-10-29 1983-06-30 Colgate-Palmolive Co., 10022 New York, N.Y. Bleichmittel- und waschmittelzusammensetzung
EP0167375A2 (de) * 1984-07-02 1986-01-08 The Clorox Company Stabile Bleichmittelzusammensetzungen
EP0168204A2 (de) * 1984-07-02 1986-01-15 The Clorox Company Alkylmonoperoxybernsteinsäure-Bleichmittel sowie deren Herstellung und Verwendung
EP0185522A2 (de) * 1984-12-14 1986-06-25 The Clorox Company Gemischte Phenylendiester als Persäurevorläufer
US4671891A (en) * 1983-09-16 1987-06-09 The Procter & Gamble Company Bleaching compositions
US4772290A (en) * 1986-03-10 1988-09-20 Clorox Company Liquid hydrogen peroxide/peracid precursor bleach: acidic aqueous medium containing solid peracid precursor activator
US4853143A (en) * 1987-03-17 1989-08-01 The Procter & Gamble Company Bleach activator compositions containing an antioxidant
EP0399584A2 (de) * 1989-05-10 1990-11-28 Unilever N.V. Bleichaktivierung und Bleichmittel-Zusammensetzungen
US5130045A (en) * 1987-10-30 1992-07-14 The Clorox Company Delayed onset active oxygen bleach composition
US5234616A (en) * 1987-10-30 1993-08-10 The Clorox Company Method of laundering clothes using a delayed onset active oxygen bleach composition
EP0588622A1 (de) * 1992-09-16 1994-03-23 Unilever Plc Bleichmittel
US5405412A (en) * 1994-04-13 1995-04-11 The Procter & Gamble Company Bleaching compounds comprising N-acyl caprolactam and alkanoyloxybenzene sulfonate bleach activators
US5409633A (en) * 1992-09-16 1995-04-25 Lever Brothers Company, Division Of Conopco, Inc. Bleach composition
US5520835A (en) * 1994-08-31 1996-05-28 The Procter & Gamble Company Automatic dishwashing compositions comprising multiquaternary bleach activators
US5534180A (en) * 1995-02-03 1996-07-09 Miracle; Gregory S. Automatic dishwashing compositions comprising multiperacid-forming bleach activators
US5595967A (en) * 1995-02-03 1997-01-21 The Procter & Gamble Company Detergent compositions comprising multiperacid-forming bleach activators
US5688757A (en) * 1990-01-22 1997-11-18 Novo Nordisk A/S The Procter & Gamble Co. Sugar derivatives containing both long and short chain acyl groups as bleach activators
US8822719B1 (en) 2013-03-05 2014-09-02 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
US9242879B2 (en) 2012-03-30 2016-01-26 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
EP3266762A1 (de) 2016-07-06 2018-01-10 3V SIGMA S.p.A Aktivatoren für persauerstoffverbindungen
US9902627B2 (en) 2011-12-20 2018-02-27 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US10165774B2 (en) 2013-03-05 2019-01-01 Ecolab Usa Inc. Defoamer useful in a peracid composition with anionic surfactants
US10323218B2 (en) 2008-03-28 2019-06-18 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10893674B2 (en) 2013-03-05 2021-01-19 Ecolab Usa Inc. Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids
US12058999B2 (en) 2018-08-22 2024-08-13 Ecolab Usa Inc. Hydrogen peroxide and peracid stabilization with molecules based on a pyridine carboxylic acid
US12096768B2 (en) 2019-08-07 2024-09-24 Ecolab Usa Inc. Polymeric and solid-supported chelators for stabilization of peracid-containing compositions

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DE3681973D1 (de) * 1985-06-14 1991-11-21 Procter & Gamble Dipercarbonsaeuren und bleichmittel.
DE3630818A1 (de) * 1986-09-10 1988-03-24 Stoll & Co H Einrichtung zur versatzsteuerung der nadelbetten einer flachstrickmaschine
US4686063A (en) * 1986-09-12 1987-08-11 The Procter & Gamble Company Fatty peroxyacids or salts thereof having amide moieties in the fatty chain and low levels of exotherm control agents
US8871807B2 (en) 2008-03-28 2014-10-28 Ecolab Usa Inc. Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids
WO2009118714A2 (en) 2008-03-28 2009-10-01 Ecolab Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10626350B2 (en) 2015-12-08 2020-04-21 Ecolab Usa Inc. Pressed manual dish detergent

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US4013581A (en) * 1975-07-10 1977-03-22 The Procter & Gamble Company Bleach tablet composition
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US4126573A (en) * 1976-08-27 1978-11-21 The Procter & Gamble Company Peroxyacid bleach compositions having increased solubility

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DE2612587A1 (de) * 1975-03-27 1976-10-14 Procter & Gamble Bleichmittel
US4013581A (en) * 1975-07-10 1977-03-22 The Procter & Gamble Company Bleach tablet composition
US4100095A (en) * 1976-08-27 1978-07-11 The Procter & Gamble Company Peroxyacid bleach composition having improved exotherm control
US4126573A (en) * 1976-08-27 1978-11-21 The Procter & Gamble Company Peroxyacid bleach compositions having increased solubility

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3240505A1 (de) * 1981-10-29 1983-06-30 Colgate-Palmolive Co., 10022 New York, N.Y. Bleichmittel- und waschmittelzusammensetzung
US4671891A (en) * 1983-09-16 1987-06-09 The Procter & Gamble Company Bleaching compositions
AU592758B2 (en) * 1984-07-02 1990-01-25 Clorox Company, The Process for synthesising alkyl monoperoxysuccinic acid
EP0168204A3 (en) * 1984-07-02 1986-08-27 The Clorox Company Alkyl monoperoxysuccinic acid bleaching compositions and synthesis and use thereof
US4655781A (en) * 1984-07-02 1987-04-07 The Clorox Company Stable bleaching compositions
US4659519A (en) * 1984-07-02 1987-04-21 The Clorox Company Process for synthesizing alkyl monoperoxysuccinic acid bleaching compositions
EP0168204A2 (de) * 1984-07-02 1986-01-15 The Clorox Company Alkylmonoperoxybernsteinsäure-Bleichmittel sowie deren Herstellung und Verwendung
EP0167375A2 (de) * 1984-07-02 1986-01-08 The Clorox Company Stabile Bleichmittelzusammensetzungen
EP0167375B1 (de) * 1984-07-02 1991-02-27 The Clorox Company Stabile Bleichmittelzusammensetzungen
EP0185522B1 (de) * 1984-12-14 1990-11-07 The Clorox Company Gemischte Phenylendiester als Persäurevorläufer
EP0185522A2 (de) * 1984-12-14 1986-06-25 The Clorox Company Gemischte Phenylendiester als Persäurevorläufer
US4772290A (en) * 1986-03-10 1988-09-20 Clorox Company Liquid hydrogen peroxide/peracid precursor bleach: acidic aqueous medium containing solid peracid precursor activator
US4853143A (en) * 1987-03-17 1989-08-01 The Procter & Gamble Company Bleach activator compositions containing an antioxidant
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EP0068547B1 (de) 1985-09-18
DE3266352D1 (en) 1985-10-24
JPS5840400A (ja) 1983-03-09
AU8506682A (en) 1983-01-06

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