US3630921A - Scouring agents with a bleaching and disinfecting action - Google Patents

Scouring agents with a bleaching and disinfecting action Download PDF

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US3630921A
US3630921A US787623A US3630921DA US3630921A US 3630921 A US3630921 A US 3630921A US 787623 A US787623 A US 787623A US 3630921D A US3630921D A US 3630921DA US 3630921 A US3630921 A US 3630921A
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acid
carbon atoms
scouring
glycoluril
acids
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Karlheinz Disch
Dieter Kuhling
Peter Krings
Horst Bellinger
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/14—Fillers; Abrasives ; Abrasive compositions; Suspending or absorbing agents not provided for in one single group of C11D3/12; Specific features concerning abrasives, e.g. granulometry or mixtures
    • 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
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames

Definitions

  • An object of the present invention is the obtention of scouring agents having a bleaching and disinfecting action comprising a major amount of water-insoluble scouring components and a minor amount of essentially watersoluble components including a solid water-soluble percompound and an eifective amount of acylated glycol compound and an effective amount of acylated glycoluril activators having the formula DESCRIPTION OF THE INVENTION
  • the present invention provides scouring agents having a bleaching and disinfecting action comprising a major amount of water-insoluble scouring components and a minor amount of essentially water-soluble components including a solid water-soluble per-compound and an effective amount of acylated glycoluril activators having the formula wherein at least two of the residues R to R represent acyls of organic carboxylic acids having from 2 to 8 carbon atoms, while the other residues represent hydrogen atoms and/or alkyland/or aryl-
  • alkanoic acids having 2 to 4 carbon atoms, are used.
  • acylated glycoluril activators having the formula R5 is 1i H g C:0
  • R R R and R are acyls of carboxylic acids selected from the group consisting of alkanoic acids having from 2 to 4 carbon atoms and benzoic acid and the remainder of R R R and R are members selected from the group consisting of hydrogen, alkyl having from 1 to 8 carbon atoms, phenyl,
  • phenyalkyl having from 7 to 8 carbon atoms, alkanoyl having from 2 to 4 carbon atoms, and benzoyl.
  • Suitable acyl residues of organic carboxylic acids havfrom 2 to 8 carbon atoms are, for example, alkanoyls, such as acetyl, propionyl, butyryl, etc.: haloalkanoyls, such as monochloroacetyl, dichloroacetyl. trichloroacetyl, etc.; benzoyl and toluyl which may be substituted with nitro groups or halogen atoms; methoxybenzoyls; and nitrilobenzoyls.
  • Suitable alkyls having 1 to 8 carbon atoms are, for example, methyl, ethyl, etc.
  • Tetraacetyl-glycoluril and its preparation are known. It is obtained by acetylating glycoluril with acetic acid anhydride.
  • the other acylated glycolurils can be prepared in a similar way by reacting glycoluril with acetic acid anhydride.
  • the other acylated glycolurils can be prepared in a similar way by reacting glycoluril with carboxylic acid anhydrides, carboxylic acid chlorides or carboxylic acid esters.
  • the activators employed in the washing agents of the present invention are new chemical components, and are the subject of copending commonly-assigned U.S. application No. 787,597 filed concurrently herewith and entitled Acylated Glycolurils as Activators for Per-Compounds.
  • acylated glycolurils can be mentioned the following: tetraacetyl-glycoluril, tetrapropionyI-glycoluril, tetrabutyryl glycoluril, 1.3 dimethyl- 4,6 diacetyl glycoluril, l methyl 3.4.6 triacetylglycoluril, diacetyl dipropionyl glycoluril. 1.3 dimethyl 4 acetyl 6 propionyl glycoluril. diacetyldibenzoyl-glycoluril.
  • the alkyl and aryl substituted glycolurils may be produced by condensation of glyoxal with the alkyl or aryl substituted ureas.
  • any of the above acylated glycolurils may be substituted for the tetraacetyl-glycoluril and tetrapropionyl-glycoluril utilized in the examples with comparable activation of the active oxygen. taking into account the fact that a larger amount of a diacylated or triacylated glycoluril must be utilized in replacement of a tetraacylated glycoluril.
  • the quantitative ratio between the acylated glycoluril activator and the per-compound should be selected so that from 10 to 0.1 particularly from 4 to 0,2 N-acyl groups are available per molecule of organically or inorganically bound H Particularly advantageous is the usage of tetraacylated glycolurils.
  • composition of the scouring agents of the invention preferably lie within the scope of the following general recipe.
  • nonionic and/or amphoteric surface active agents are nonionic and/or amphoteric surface active agents.
  • water-insoluble scouring components are mineral finely-ground materials such as quartz. feldspar, marble or fiuor-spar powder, kaolin and pumice stone.
  • mineral ground materials finely-ground synthetic resin granulates or their mixtures with mineral scouring components may be used.
  • mineral ground materials coated with a synthetic resin film may be used.
  • the per-compounds used in the scouring agents of the invention may be of an organic or inorganic nature. Suitable are. for instance, per-compounds such as urea and malamine perhydrate and in particular inorganic per salts Cal such as, for instance, alkali metal perborates, percarbonates, perpyrophosphates and persilicates. Among those preferably inorganic per salts to be used, sodium perborate tetrahydrate is of specific practical importance. Instead may as well be used partially or completely dehydrated perborates.
  • the perborates may be wholly or partly replaced by the above-identified inorganic per-compounds.
  • These peroxyhydrates are preferably soluble in water and are ordinarily utilized in the form of their alkali metal salts, such as their sodium salts.
  • the anionic. amphoteric or non-ionic surface-active compounds contain in the molecule at least one hydrophobic residue containing 8 to 26, preferably 10 to 20 and in particular 12 to 18 carbon atoms and at least one anionic or non-ionic or amphoteric water-solubilizing group.
  • the advantageously hydrophobic residue may be of aliphatic or alicyclic nature, and be combined with the water-solubilizing groups directly or through intermediate members. Suitable intermediate members are, for example, benzene rings, carboxylic acid ester or carbonamide groups ether or ester-like bound residues of polyvalent alcohols, such as ethylene glycol or propylene glycol, glycerine or corresponding polyether residues.
  • the hydrophobic residue is preferably an aliphatic hydrocarbon residue with 10 to 18 carbon atoms, but deviations from this preferred carbon range are possible depending on the nature of the surface-active compound in question.
  • Soaps are useful as anionic detergents which are derived from natural or synthetic fatty acids, and possibly also from resin or naphthenic acids, particularly, if these acids have iodine numbers of 30 at the most and preferably of less than 10.
  • the sulfonates and sulfates are of special practical importance.
  • the sulfonates include, for example, the alkylaryl sulfonates, especially the alkyl benzene sulfonates, which are obtained among others from preferably straight-chain aliphatic hydrocarbons with 9 to 15, preferably 10 to 14 carbon atoms by chlorination with alkylation of benzene or from corresponding olefins with terminal or non-terminal double bonds by alkylation of benzene and sulfonation of the alkylbenzenes obtained.
  • the alkylaryl sulfonates especially the alkyl benzene sulfonates, which are obtained among others from preferably straight-chain aliphatic hydrocarbons with 9 to 15, preferably 10 to 14 carbon atoms by chlorination with alkylation of benzene or from corresponding olefins with terminal or non-terminal double bonds by alkylation of benzene and sulfonation of the alkylbenzenes obtained.
  • aliphatic sulfonates are of interest, such as, for example, are obtainable from preferably saturated hydrocarbons containing 8 to 18 and preferably 12 to 18 carbon atoms in the molecule by sulfochlorination with sulfur dioxide and chlorine or sulfoxidation with sulfur dioxide and oxygen and conversion of the products thereby obtained into the sulfonates. Furthermore, mixtures of alkenesulfonates, hydroxyalkenesulfonates and disulfonates, such as are obtained.
  • terminal or central C C and preferably C C C olefins by sulfonation with sulfur trioxide and acid or alkaline hydrolysis of the sulfonate products are utilizable as aliphatic sulfonates.
  • the sulfonate group is often found on a secondary carbon atom, but by reacting terminal olefins with bisulfite, sulfonates with terminal sultonate groups, may be prepared.
  • Salts preferably dialkali salt of a-sulfo-fatty acids as well as salts of esters of these acids with alcohols containing l to 4 and preferably 1 or 2 carbon atoms also belong to the sulfonates to be used according to the inventiOn.
  • sulfonates are the fatty acid esters of hydroxyethanesulfonic acid and dihydroxypropanesulfonic acid, the salts of fatty alcohol esters of lower aliphatic or aromatic sulfo-monoand di-carboxylic acids containing 1 to 8 carbon atoms, the alkylglycerylethersulfonates, aswe ll as the salts of the amide-like condensation products of fatty acids or sulfonic acids with aminoethanesulfonic acid.
  • Suitable surface-active compounds of the sulfate type are fatty alcohol sulfates, especially those derived from coconut fatty alcohols, tallow fatty alcohols or oleyl alcohol.
  • Useful sulfonation products of the sulfate type can also be prepared from C to C olefins with terminal or nonterminal double bonds.
  • this group of surface-active compounds includes sulfated fatty acid alkylolamides, sulfated monoglycerides and sulfated products of ethoxylated and/or propoxylated fatty alcohols, alkylphenols with 8 to 15 carbon atoms in the alkyl residue, fatty acid amides, fatty acid alkylolamides and so on, where 0.5 to 20, preferably 1 to 8, and especially 2 to 4 mols of ethylene oxide and/or propylene oxide are added on to one mol of the said compounds to be ethoxylated and/or propoxylated.
  • Suitable as anionic surface-active agents of the carboxylate type are, for example, the fatty acid esters or fatty alcohol ethers of hydroxy carboxylic acids as well as the amide-like condensation products of fatty acids or sulfonic acid with amino carboxylic acids, for example, with glycocol, sarcosine or albumin hydrolysates.
  • Non-ionic surface-active agents useful in the scouring agents are the so-called Non-ionics which are products which owe their water solubility to the presence of polyether chains, amineoxide, sulfoxide or phosphineoxide groups, alkylolamide groupings as well as in general to a large number of hydroxyl groups.
  • Nonionics may contain from 2 to 100, preferably 6 to 40 and especially 8 to 20 ether radicals, and above all ethyleneglycolether radicals per molecule.
  • these polyether radicals may contain central or terminal propyleneor butyleneglycolether radicals or polyether chains.
  • Watersoluble addition products of ethyleneoxide to water-insoluble propyleneglycols which are known commercially under the name of Pluronics, Tetronics or Ucon Fluid," as well as addition products of propyleneoxide to alkylenediamines or to lower aliphatic alcohols containing from 1 to 8 and preferably 3 to 6 carbon atoms are also classed as Non-ionics.
  • These water-insoluble propyleneoxide derivatives represent the hydrophobic residue.
  • Non-ionics are fatty acid or sulfonic acid alkylolamides which are derived, for instance, from monoor diethanolamine, from dihydroxypropylamine or other polyhydroxyalkylamines, e.g., the glycamines. They may be replaced by amides from higher primary or sec. alkylarnines and polyhydroxycarboxylic acids.
  • capillary active amineoxides belong, for instance, those products which are derived from higher tert. amines which possess a hydrophobic alkyl radical and two shorter alkyl and/ or alkylol radicals 'with up to 4 carbon atoms each.
  • Amphoteric surface-active agents contain both acid and basic hydrophile groups in the molecule.
  • the acid groups are carboxylic acid groups, sulfonic acid groups, sulfuric acid half ester groups, phosphonic acid groups and phosphoric acid partial ester groups.
  • the basic groups are primary, secondary, tertiary and quaternary ammonium groupings.
  • carboxy, sulfate and sulfonate betaines are of special practical interest.
  • Suitable sulfobetaines are obtained, for instance, through reaction of tert. amines, containing at least one hydrophobic alkyl radical, with sultones, for instance, propane or butane sultone.
  • Corresponding carboxybetaines are obtained through reaction of the above-identified tert. amines with chloroacetic acid, its salts or with chloroacetic acid esters and cleavage of the ester bond.
  • the foaming properties of the surface-active agents may be increased or decreased by means of combination of suitable surface-active agent types as well as being modified by addition of non-surface-active organic substances.
  • suitable surface-active agent types as well as being modified by addition of non-surface-active organic substances.
  • foam stabilizers for surface-active agents of the sulfonate or sulfate type are capillary active carboxy or sulfobetaines as well as the above-identified non-ionics of the alkylolamide type.
  • Equally well suited for this purpose are fatty alcohols or higher terminal alkanediols.
  • Suitable alkaline-reacting builders are, for instance, the bicarbonates, carbonates, borates or silicates of the alkali metals, mono-, dior trialkali orthophosphates dior tetra alkali pyrophosphates, alkali metal tripolyphosphates as well as the alkali metal metaphosphates known as complex-forming compounds.
  • Usable organic complexforming compounds are, for example, the alkali metal salts of hydroxy'car'boxylic acids such as the salts of lactic acid, citric acid and tartaric acid.
  • organic complex-forming compounds are the alkali metal salts of nitr-ilotriacetic acid, ethylenediaminetetraacetic acid, N- hydroxyethylethylenediaminetriacetic acid, polyalkylenepolyamine-N-polycanboxylic acids as well as other known organic complex-forming compounds. Combinations of several complex-forming compounds may be employed as well. Diand poly-phosphonic acids of the following constitutions also belong to the other known complex-forming compounds:
  • R represents alkyl and R represents alkylene residues with l to 8, preferably 1 to 4, carbon atoms
  • X and Y represent hydrogen atoms or alkyl with 1 to 4 carbon atoms.
  • Carboxy-methylenephosphonic acid is also useful as a complex-forming compound according to the invention. All these complex-forming compounds may be present as free acids, but it is preferred to use them as their alkali metal salts.
  • alkaline-reacting inorganic builders and organic complex-forming compounds may partly be replaced by neutrally-reacting diluents, for example, sodium sulfate or sodium chloride.
  • dirt-dispersing colloids such as watersoluble cellulose derivatives or water soluble salts of higher molecular weight polycarboxylic acids, particularly polymerizates of maleic acid, acrylic acid, itaconic acid, mesaconic acid, fumaric acid, aconitic acid, methylenemalonic acid and citraconic acid.
  • Usable as dirt-dispersing colloids as well are mixed polymerizates of these latter acids among themselves or with other polymerizable substances such as, for instance. with ethylene. propylene, acrylic acid, methacrylic acid. crotonic acid. 3-butenecarboxylic acid. 3 methyl-3-butenecarboxylic acid as well as vinylmethylether, vinyl acetate.
  • compositions of some of the prepa ations of the present invention will be further described by way of reference to the following examples. These are. however, not to be deemed limitative in any respect.
  • salt components salt of surface-active agents. other organic salts as well as inorganic salts which are contained therein, are sodium salts.
  • the terms used in the examples are as follows:
  • Alkylbenzenesulfonate represents the sodium salt of an alkylbenzenesulfonic acid with from to 15. preferably ll to 13 carbon atoms in the alkyl chain which is obtained by condensation of straight-chain olefins with benzene and sulfonation of the thus obtained alkylbenzene.
  • Fatty alcohol-t-EO represents the addition products of ethylene oxide (E0) to technical oleyl alcohol.
  • Olefinsulfonate represents a sulfonate obtained from olefin mixtures with from 12 to 18 carbon atoms through sulfonation with 50; and hydrolyzation of the sulfonation product with sodium hydroxide solution.
  • This sulfonate mainly consists of alkenesulfonates and hydroxyalkanesulfonates as well as small amounts of disulfonates.
  • Each of the olefinsulfonate containing preparations was prepared from two different olefinsulfonate types: one of these had been prepared from a mixture of straight-chain terminal olefins, the other from a mixture of non-terminal olefins.
  • Fatty alcohol-ZEO-sulfate represents a sulfated addition product of 2 mols of ethyleneoxide to 1 mol of coconut fatty alcohol.
  • Fatty alcohol sulfate represents a sulfated coconut fatty alcohol.
  • Fatty acid diethanol amide represents the amide from coconut fatty acid and diethanolamine.
  • Alkanesulfonate represents a sulfonate obtained from parafiins with from 12 to 16 carbon atoms by means of sulfoxidation.
  • Soap represents the sodium salts of a fatty acid mixture of the following composition:
  • Example 1 Percent by wt. Alkylbenzenesulfonate Fatty alcohol-H0 EO Pyrophosphate 1 Sodium carbonate Perborate Tetraacetyl-glycoluril Quartz powder 88.
  • Example 2 Percent by wt. Olefinsulfonate 4 ⁇ onylphenol ltl EO 0.5 Tripolyphosphate 2 Perborate 2 l .3-dimethyl-4.6-diacetyl-glycoluril 2 Quartz powder 89.5
  • Example 3 Percent by wt. 1- ⁇ lltylbenzencsulfonate 2.5 Fatty alcohol sulfate 2 Borax 2 Perborate 2.5
  • Example 4 Percent by wt. Alkylbenzenesulfonate 3 Fatty alcohol-2 EO-sulfate 1 Fatty acid diethanolamide 0.5 Nitrilotriacetate 0.5
  • Example 7 Percent by wt. Alkylbenzenesulfonate 2 Fatty alcohol sulfate 1 Sodium carbonate 3 Orthophosphate 2 Tripolyphosphate 2 Perborate 3 Diacetybdipropionyl'glycoluril 2 Quartz powder
  • Example 8 Percent by wt.
  • Example 9 Percent by wt. Alkylbenzenesulfonate 3 Fatty acid monoethanolamide+8 EO 1 Ethylenediaminetetraacetate 0.5 Sodium carbonate 2 lerborate 2 Tetraacetyl-glycoluril 2 Quartz powder 89.5
  • Example 13 Percent by wt. ()l fin lfonate 3 Scouring agents were prepared which in addition to 4% Fatty 1-4 Bo lfat 15 by weight of alkylbenzenesulfonate; 1% by weight of T ipolyphosphate 2 fatty alcohol-2 EO-sulfate; 2% by welght of tripolyphos- Perborate 2, 5 phate; 85% by weight of quartz powder contained i 2 gh f i gm f fifi ffiI 89 (a) 4% by weight of perborate; 4% by weight of tetraacetyl-glycoluril Example 11 (b) 2% by weight of perborate; 2% by weight of tetra- Percent by acetyl-glycoluril; 4% by weight of sodium sulfate Alkylbenzenesulfonate 5 (c) 1% by weight of perborate; 1% by weight of tetra-
  • BLE I (c) A scouring agent with 0.5% by weight of per- Bleachin borate, 0.5% by weight of tetraacetylglycoluril, 6% by welght of sodlum sulfate; otherwise the composition of Stain g fi f jglg the scouring agent of Example 11.
  • Scouring agents having a bleaching and disinfecting action consisting essentially of:
  • R R R and R are acyls of carboxylic acids selected from the group consisting of alkanoic acids having from 2 to 4 carbon atoms and benzoic acid, and the remainder of R R R and R are members selected from the group consisting of alkyl having from 1 to 8 carbon atoms, alkanoyl having from 2 to 4 carbon atoms and benzoyl, said acylated glycoluril activators being present in said combination in an amount sufiicient to supply from 4 to 0.2 N-acyl groups per molecule of said bound H 0 (2) from 10% to 60% by weight of surface-active agents selected from the group consisting of anionic surface-active agents, non-ionic surfaceactive agents and amphoteric surface-active agents,
  • alkaline-reacting inorganic builders selected from the group consisting of alkali metal bicarbonates, carbonates, borates, silicates, orthophosphates, pyrophosphates and metaphosphates and organic complex-forming compounds selected from the group consisting of alkali metal salts of hydroxycarboxylic acids, nitrilotriacetic acid, ethylenediaminetetraacetic acid, N hydroxyethyethylenediaminetriacetic acid, polyalkylene-polyamine N polycarboxylic acids, diphosphonic acids, polyphosphonic acids and carboxy-methylenephosphonic acid, and
  • Scouring agents having a bleaching and disinfecting action consisting essentially of:
  • R R R and R are acyls of organic carboxylic acids having from 2 to 8 carbon atoms, selected from the group consisting of alkanoic acids, haloalkanoic acids, benzoic acid, nitrobenzoic acid, toluic acid, nitrotoluic acid, methoxybenzoic and nitrilobenzoic acid, and the remainder of R R R and R are members selected from the group consisting of alkyl having from 1 to 8 carbon atoms and acyls of organic carboxylic acids having from 2 to 8 carbon atoms, selected from the group consisting of alkanoic acids, halo-alkanoic acids, benzoic acid, nitrobenzoic acid, toluic acid, nitrotoluic acid, methoxybenzoic acid and nitrilobenzoic acid, said acylated glycoluril activators being present in said combination in an amount sufiicient to supply from 10 to 0.1 N-acyl groups per molecule of said inorganic
  • alkaline-reacting inorganic builders selected from the group consisting of alkali metal bicarbonates, carbonates, borates, silicates, orthophosphates, pyrophosphates and metaphosphates and organic complex-forming compounds selected from the group consisting of alkali metal salts of hydroxycarboxylic acids, nitrilotriacetic acid, ethylenediaminetetraacetic acid, N-hydroxyethylethylenediaminetriacetic acid, polyalkylene-polyamine-N- polycarboxylic acids, diphosphonic acids, polyphosphonic acids and carboxy-methylenephosphonic acid, and
  • R R R and R are acyls of alkanoic acids having from 2 to 4 carbon atoms.
  • the scouring agents as defined in claim 2 activators are selected from the group consisting of tetraacetylglycoluril and tetrapropionyl-glycoluril.

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US787623A 1968-12-03 1968-12-27 Scouring agents with a bleaching and disinfecting action Expired - Lifetime US3630921A (en)

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AT (1) AT288904B (enrdf_load_stackoverflow)
BE (1) BE742304A (enrdf_load_stackoverflow)
CH (1) CH496088A (enrdf_load_stackoverflow)
DE (1) DE1812382A1 (enrdf_load_stackoverflow)
ES (1) ES374141A1 (enrdf_load_stackoverflow)
FR (1) FR1600258A (enrdf_load_stackoverflow)
GB (1) GB1247425A (enrdf_load_stackoverflow)
IE (1) IE33867B1 (enrdf_load_stackoverflow)
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3740187A (en) * 1971-06-03 1973-06-19 Monsanto Co Processes for bleaching textiles
US3779931A (en) * 1970-12-10 1973-12-18 Henkel & Cie Gmbh Compositions useful in the aqueous cold-bleaching of textiles including optical brighteners
US3919102A (en) * 1971-03-16 1975-11-11 Henkel & Cie Gmbh Composition and method for activating oxygen utilizing N-acylated tetraaza-bicyclo-nonandiones
US3956156A (en) * 1971-04-28 1976-05-11 Colgate-Palmolive Company Cleansing of fabrics
US4003700A (en) * 1970-05-01 1977-01-18 Colgate-Palmolive Company Cleaning fabrics
US5021187A (en) * 1989-04-04 1991-06-04 Lever Brothers Company, Division Of Conopco, Inc. Copper diamine complexes and their use as bleach activating catalysts
US6540960B2 (en) * 1996-12-11 2003-04-01 Henkel-Ecolab Gmbh & Co. Ohg (Henkel-Ecolab) Process for disinfecting instruments
WO2011005830A1 (en) * 2009-07-09 2011-01-13 The Procter & Gamble Company Laundry detergent composition comprising low level of sulphate
US20110005001A1 (en) * 2009-07-09 2011-01-13 Eric San Jose Robles Detergent Composition
WO2011005623A1 (en) * 2009-07-09 2011-01-13 The Procter & Gamble Company Laundry detergent composition comprising low level of bleach

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1355795A (en) * 1970-05-01 1974-06-05 Colgate Palmolive Co Process and composition for cleaning fabrics
NL173919C (nl) * 1970-05-29 1984-04-02 Henkel Kgaa Werkwijze voor het desinfecteren van medische apparaten en instrumenten.

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4003700A (en) * 1970-05-01 1977-01-18 Colgate-Palmolive Company Cleaning fabrics
US3779931A (en) * 1970-12-10 1973-12-18 Henkel & Cie Gmbh Compositions useful in the aqueous cold-bleaching of textiles including optical brighteners
US3919102A (en) * 1971-03-16 1975-11-11 Henkel & Cie Gmbh Composition and method for activating oxygen utilizing N-acylated tetraaza-bicyclo-nonandiones
US3956156A (en) * 1971-04-28 1976-05-11 Colgate-Palmolive Company Cleansing of fabrics
US3740187A (en) * 1971-06-03 1973-06-19 Monsanto Co Processes for bleaching textiles
US5021187A (en) * 1989-04-04 1991-06-04 Lever Brothers Company, Division Of Conopco, Inc. Copper diamine complexes and their use as bleach activating catalysts
US6540960B2 (en) * 1996-12-11 2003-04-01 Henkel-Ecolab Gmbh & Co. Ohg (Henkel-Ecolab) Process for disinfecting instruments
WO2011005830A1 (en) * 2009-07-09 2011-01-13 The Procter & Gamble Company Laundry detergent composition comprising low level of sulphate
US20110009307A1 (en) * 2009-07-09 2011-01-13 Alan Thomas Brooker Laundry Detergent Composition Comprising Low Level of Sulphate
US20110005001A1 (en) * 2009-07-09 2011-01-13 Eric San Jose Robles Detergent Composition
WO2011005623A1 (en) * 2009-07-09 2011-01-13 The Procter & Gamble Company Laundry detergent composition comprising low level of bleach

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IE33867L (en) 1970-06-03
GB1247425A (en) 1971-09-22
NL6818746A (enrdf_load_stackoverflow) 1970-06-05
AT288904B (de) 1971-03-25
ES374141A1 (es) 1972-03-01
FR1600258A (enrdf_load_stackoverflow) 1970-07-20
CH496088A (de) 1970-09-15
DE1812382A1 (de) 1970-12-10
IE33867B1 (en) 1974-11-27
BE742304A (enrdf_load_stackoverflow) 1970-05-27

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