US3650962A - Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines - Google Patents

Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines Download PDF

Info

Publication number
US3650962A
US3650962A US881264A US3650962DA US3650962A US 3650962 A US3650962 A US 3650962A US 881264 A US881264 A US 881264A US 3650962D A US3650962D A US 3650962DA US 3650962 A US3650962 A US 3650962A
Authority
US
United States
Prior art keywords
washing
alkali metal
bleaching
agents
acid
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
US881264A
Other languages
English (en)
Inventor
Achim Werdehausen
Arnold Heins
Manfred Dohr
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Application granted granted Critical
Publication of US3650962A publication Critical patent/US3650962A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0206—Polyalkylene(poly)amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • 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
    • C11D3/3937—Stabilising agents
    • C11D3/394—Organic compounds

Definitions

  • NTA can protect the optical brighteners only insufiiciently from an oxidizing attack, while EDTA and DTPA are not completely stable against oxidizing agents and are oxidized to inactive compounds.
  • An object of the present invention is the obtaining of washing, bleaching and cleansing agents which have incorporated therein complexing aminopolycarboxylic acids or their salts which increase the stability and cleaning properties of the washing agents and stabilize the optical brighteners present.
  • Another object of the invention is the obtaining of a washing, bleaching and cleansing agent having a content of from 50% to 99.9%, by weight, of customary components of washing, bleaching and cleansing agents and from 0.1% to 50%, by weight, of a polyethyleneimine selected from the group consisting of (1) branched poly- (N-acetic acid)-polyethyleneimines having an average molecular weight of from 2,000 to 200,000 wherein from about 50% to of the primary and secondary amine groups in the polyethyleneimine molecule are carboxymethylated and (2) their alkali metal, ammonium and organic ammonium salts.
  • V 7 branched poly- (N-acetic acid)-polyethyleneimines having an average molecular weight of from 2,000 to 200,000 wherein from about 50% to of the primary and secondary amine groups in the polyethyleneimine molecule are carboxymethylated and (2) their alkali metal, ammonium and organic ammonium salts.
  • the invention therefore comprises a washing, bleaching and cleansing agent having a content of from 50% to 99.9%, by weight, of customary components of wash ing, bleaching and cleansing agents and from 0.1% to 50%, by weight, of a polyethyleneimine selected from the group consisting of (1) branched poly-(N-acetic acid)- polyethyleneimines having an average molecular weight of from 2,000 to 200,000 wherein from about 50% to 100% of the primary and secondary amine groups in the polyethyleneimine molecule are carboxymethylated and (2) their alkali metal, ammonium and organic ammonium salts.
  • a polyethyleneimine selected from the group consisting of (1) branched poly-(N-acetic acid)- polyethyleneimines having an average molecular weight of from 2,000 to 200,000 wherein from about 50% to 100% of the primary and secondary amine groups in the polyethyleneimine molecule are carboxymethylated and (2) their alkali metal, ammonium and organic ammonium salts.
  • the preparation of the branched polymeric-N-acetic acid-ethyleneimines is executed according to known procedures, for example, by reacting branched polyethyleneimines of an average molecular weight of 1200 to 120,000 in an aqueous alkaline medium with alkali metal salts of chloroacetic or bromoacetic acid. By treatment with ionexchange resins, the alkali metal salts obtained are converted to the free acids or, by subsequent neutralization with ammonia or organic ammonia bases, such as mono-, di-, and triethanolamine, morpholine and N-methylmorpholine, to the corresponding ammonium salts.
  • ammonia or organic ammonia bases such as mono-, di-, and triethanolamine, morpholine and N-methylmorpholine
  • A represents the CH COOH radical.
  • the polymers can also contain unsubstituted primary or secondary amine groups. In products with a high degree of alkylation also quaternary ammonium groups can be present.
  • the primary and secondary amine groups contained in the starting material are carboxymethylated to from about 50% to 100%, preferably from 60% to 98%.
  • the cleaning properties of the polymers increase with increasing molecular weight and, therefore, such polymers are preferably used which have an average molecular weight of at least 4000, for example, 4000* to 150,000.
  • the polymeric N-acetic-acid-ethyleneimines can be added to the washing, bleaching, and cleansing agents in forms of salts or the free acid, if in the latter case, the substrate contains suflicient amounts of alkaline reacting compounds so that on dissolving the agents in water a neutralization of the free acid groups takes place.
  • the agents according to the invention contain at least one other cleaning or bleaching component, such as nonionic, anionic and amphoteric surface-active materials, iorganic or organic builders, oxygen-containing bleaching agents, as well as other conventional washing and cleansing ingredients.
  • other cleaning or bleaching component such as nonionic, anionic and amphoteric surface-active materials, iorganic or organic builders, oxygen-containing bleaching agents, as well as other conventional washing and cleansing ingredients.
  • nonionic compounds such as the polyalkyleneglycolether derivatives of alcohols, fatty acids and alkylphenols which contain 3 to 30 alkyleneglycolether groups and 8 to 20 carbon atoms in the hydrocarbon radical.
  • polyalkyleneglycolether derivatives in which the number of oxyethylene groups is from 5 to 15 and whose hydrocarbon radicals are derived from straight-chain primary alcohols with 12 to 18 carbon atoms, or from alkylph'enols with a straight-chain alkyl chain of 6 to 14 carbon atoms.
  • nonionic basic washing components are the water soluble polyethylene oxide adducts, adducted to polypropyleneglycol, ethylenediaminc-polypropyleneglycol and alkylpolypropyleneglycol with l to 10 carbon atoms in the alkyl chain.
  • these adducts contain from 20 to 250 oxyethylene groups and 1-0 to 100 oxypropylene groups in the molecule.
  • the named compounds contain usually 1 t oxyethylene units per oxypropylene unit.
  • nonionic compounds of the type of aminooxides and sulfoxides which, if necessary, can also be ethoxylated, are usable.
  • the washing and cleansing agents can also contain anionic basic washing components of the sulfonate or sulfate type.
  • alkylbenzene sulfonates such as dodecylbenzene sulfonate are suitable.
  • olefin sulfonates such as, are obtained by sulfonation of primary and secondary aliphatic monoolefins with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis, as well as alkylsulfonates obtainable from n-alkanes by sulfochlorination or sulfoxidation and subsequent hydrolysis, or neutralization, or by addition of bisultite to olefins are also suitable.
  • u-sulfo fatty acid esters, primary and secondary alkyl sulfates and the sulfates of ethoxylated or propoxylated higher alcohols are suitable.
  • Other compounds of this class which can be occasionally present in the detergents are the higher molecular weight sulfated partial ethers and partial esters of polyhydric alcohols, such as, the alkali metal salts of the monoalkyl ethers, or mono-fatty acid esters of the glycerine monosulfuric acid esters, or, of 1,2 dihydroxypropane-sulfonic acid.
  • sulfates of ethoxylated or propoxylated fatty acid amides and alkyl phenols as well as fatty acid taurides and fatty acid isethionates are suitable.
  • alkylbetaines and, particularly, alkylsulfobetaines are suitable, for example, 3-(N,N-dimethyl-N-alkylammonium)- propane-l-sulfonate and 3-(N,N-dimethyl-N-alkyl-ammonium)-2-hydroxypropane-l-sulfonate, preferably where alkyl is a lower alkyl such as methyl or ethyl.
  • the anionic basic washing components can be present in the form of the alkali metal salts such as the sodium and potassium salts as well as the ammonium salt, or as salts of organic bases, such as mono, di, and triethanolamine.
  • the named surface-active nonionic, anionic and amphoteric compounds have a long-chain aliphatic hydrocarbon radical, the latter should preferably be straight-chained and should have from 8 to 22 carbon atoms.
  • the preferred straight alkyl chains contain an average of from 6 to 16 carbon atoms.
  • inorganic builders particularly condensed phosphates, such as, pyrophosphates, triphosphates, tetraphosphates, trimetaphosphates, tetrametaphosphates as well as more highly condensed phopshates in the form of the neutral or acidic alkali metal salts such as the sodium and potassium salts as well as the ammonium salt.
  • condensed phosphates can also be partly or completely substituted by organic complexing agents containing phosphorus or nitrogen atoms.
  • Such compounds are the alkali metal or ammonium salts of aminopolyphosphonic acids, particuuarly aminotri- (methylenephosphonic acid), l-hydroxyethanel,1-diphosphonic acid, methylene diphosphonic acid, ethylene diphosphonic acid as well as the higher homologs of the named polyphosphonic acids, as well as the alkali metal or ammonium salts of loW-molecular-weight aminopolycarboxylic acids, such as NTA and EDTA.
  • alkali metal silicates are suitable, particularly sodium silicate in which the ratio Na O:SiO is 1:3.5 to 1:1.
  • mixture ingredients are neutral salts, such as, sodium sulfate and sodium chloride, as well as compounds for adjustment of the pH, such as bicarbonates, carbonates, borates and hydroxides of sodium and potassium and acids, such as, lactic and citric acid.
  • the amount of the alkaline reacting substances should be calculated so that the pH of a serviceable washing liquor for coarse laundry is 9 to 12 and for fine laundry 6 to 9.
  • the washing agents of the invention can contain oxygen-releasing bleaching compounds, such as, hydrogen peroxide, alkali metal perborates, alkali metal percarbonates, alkali metal perphosphates, urea hydrogen peroxide and alkali metal persulfates or active-chlorine compounds, such as, alkali metal hypochlorites, chlorinated trisodium phosphate and chlorinated cyanuric acid, or its alkali metal salts.
  • the peroxide compounds can be present in a mixture with bleaching activators and stabilizers, such as, magnesium silicate.
  • Optical brighteners suitable for cellulosic fibers used in the Washing agents of the invention are those of the diaminostilbene disulfonic acid type of the formula:
  • Ar and Ar are aryl radicals, such as,
  • phenyl, diphenyl, or naphthyl which can have further substituents, such as, hydroxy, alkoxy, hydroxyalkyl, amino, alkylamino, acylamino, carboxyl, sulfonic acid, and sulfonamide groups, or halogen atoms.
  • Preferred is a 1,3-diarylpyrazoline derivative in which the radical Ar is a p-sulfonamidophenyl group and the radical Ar is a p-chlorophenyl group.
  • greying-inhibiting compounds such as, sodium celluloseglycolate, as well as the water soluble sodium salts of synthetic polymers which contain free carboxylic groups.
  • these latter include the polyesters or the polyamides of triand tetracarboxylic acids and dihydric alcohols or diamines, and also polymeric acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and aconitic acid as well as the mixed polymerizates of the named unsaturated carboxylic acids, or their mixed polymerizates with olefins and vinylethers.
  • Washing agents intended for the use in drum-washing machines contain appropriately known foam-suppressing substances such as saturated fatty acids with to 24 carbon atoms, or their alkali metal soaps, or triazine derivatives which can be obtained by reacting one mol cyanuric chloride with 2 to 3 mols of aliphatic, straightchained, branched-chained or cyclic primary monoamines or by propoxylating, or, butoxylating melamine.
  • foam-suppressing substances such as saturated fatty acids with to 24 carbon atoms, or their alkali metal soaps, or triazine derivatives which can be obtained by reacting one mol cyanuric chloride with 2 to 3 mols of aliphatic, straightchained, branched-chained or cyclic primary monoamines or by propoxylating, or, butoxylating melamine.
  • the washing agents can also contain enzymes from the class of proteases, lipases( or amylases.
  • These enzymes can be of animal or plant origin, for example, those obtained from digestive ferments or yeasts, such as pepsin, pancreatin, trypsin, papin, catalase and diastase.
  • enzymatic active substances obtained from bacterial strains or molds, such as, Bacillus subtilis and Streptomyces griseus which are relatively stable against alkalis, peroxide compounds and anionic detergents and essentially not inactivated even at temperatures between 45 C. and 70 C.
  • the washing and cleansing agents can be present in liquid, pasty or solid form, as powder, granules or lumps.
  • Liquid preparations may contain water-miscible solvents, particularly lower alkanols such as ethanol and isopropanol, as well as dissolving aids, such as, the alkali metal salts of benzene, toluene, xylene, or ethylbenzene sulfonic acids.
  • the skin compatibility alkylolamides such as, fatty acid mono, or diethanolamides may, if necessary, be added.
  • the mixture can also contain dyes or odorizing substances, bactericidally-active materials, activators as well as fillers, for example, urea.
  • the preparation of the agents according to the invention can be done in customary manner by mixing, granulating or spray-drying.
  • enzymes it is recommended to mix them with the nonionic basic washing components and, if necessary, odorizing substances, or to disperse them in the melt of a salt containing water of crystallization, such as Glaubers salt, and to combine these premixtures with the other powdery ingredients.
  • the enzymes are cemented with the other powder particles so that the mixtures do not tend to dust or separate.
  • the content of the washing, bleaching and cleansing agents of poly-(Nacetic acid)-ethyleneimine or its alkali metal salts amounts from about 0.1% to 50% preferably 0.2% to by weight, depending, upon their use. , The difference to 100% is taken up by the previously named detergent and bleaching active substances as well as, if necessary, the additional builders to improve the cleaning power.
  • the qualitative and quantitative composition of these additional ingredients depend widely upon the special use of these agents. It corresponds in the case of the technically particular important washing and cleansing agents to the following recipe: (Data in percent by weight) 1% to of at least one compound from the class of the anionic, nonionic, and amphoteric detergents.
  • a per-compound especially sodium perborate, with or without water of crystallization, as well as their mixtures with stabilizers and activators.
  • the detergent substances can consist of up to 100% preferably from 5% to of compounds of the sulfonate and/or the sulfate type, up to 100%, preferably from 5% to 40% of the nonionic polyglycolether type, and up to 100%, preferably from 10% to 50% of soaps.
  • the builders can consist of up to 100%, preferably from 25% to of alkali metal triphosphates and their mixtures with alkali metal pyrophosphates, up to preferably from 5% to 50%, of an alkali salt of a complexing agent from the class of polyphosphonic acids, nitrilotriacetic acid, ethylenediaminetetraacetic acid, and up to 100%, preferably from 5% to 75% of at least one compound of the class of alkali metal silicates, alkali metal carbonates and alkali metal borates.
  • the foam inhibitors which can be present in the agents according to the invention in an amount of up to 5%, preferably from 0.2% to 3%; also the enzymes which can be present in an amount up to 5%, preferably from 0.2% to 3%; and the greying-inhibitors which can be present in an amount up to 5%, preferably from 0.2% to 3%.
  • poly-(N-acetic acid)-ethyleneimine or its alkali metal salt 1% to 5% of sodium silicate 10% to 35% of sodium perborate tetrahydrate to of enzymes 0.05% to 1% of at least one optical brightener from the class of diaminostilbenedisulfonic acid or diarylpyrazoline derivatives 0.1% to 30% of an inorganic alkali metal salt from the class of the carbonates, bicarbonates, borates, sulfates and chlorides.
  • Liquid washing agent 0.5% to 10% of a sul-fonate basic washing component (potassium salt) 0 to 10% of alkylpolyglycolether sulfate (alkyl C to C 1 to 5 oxyethylene groups) 0.2% to 25% of poly-(N-acetic acid)-ethyleneimine or its alkali metal salts 0.1% to 5% of fatty amide-glycolether condensate (alkyl C to C 1 to 10 oxyethylene groups) 1% to 10% of solution aids from the class of the alkali metal salts of benzene, toluene, or Xylene sulfonic acids.
  • a sul-fonate basic washing component potassium salt
  • alkylpolyglycolether sulfate alkyl C to C 1 to 5 oxyethylene groups
  • poly-(N-acetic acid)-ethyleneimine or its alkali metal salts 0.1% to 5% of fatty amide-glycolether condensate
  • bleaching activators O to 5% of anionic and/or nonionic detergents 0 to 10% of other ingredients, such as, corrosion inhibitors, optical brighteners, neutral salts, magnesium salicate.
  • branched poly-(N-acetic acid)- ethyleneimine For the preparation of the branched poly-(N-acetic acid)- ethyleneimine, branched polya'mines of average molecular weights of 2,500, 5,000 and 70,000 were heated to 80 to 90 C. in a 20% aqueous solution each time with 80% of TABLE I Average Percent molecular Bright- Example Builders weight ening 1 Sodium salts of branched poly-(N- 5, 000 7s.
  • Example 9-foam-suppressing heavy washing agent Example l0--cold-washing agent
  • Example 1l-liquid washing agent Example 12wool-washing agent
  • Example 13-steeping agent Example 14bleaching agent
  • Example 15liquid dish-rinsing agent Example 16-cleanser for heavy soiling
  • Example 17scouring agent The ingredients a to d and f to i were present as the sodium salts, the pyrophosphate (ingredient k) was used 1 1 in Example 9 as the potassium salt, and in all other examples as sodium salt.
  • enzyme As enzyme (ingredient q), a preparation Maxatase (registered trademark), made from Bacillus subtilis, with an activity of 100,000 LVA/ gm. was utilized.
  • the foam suppressor (ingredient v) is a reaction product of 1 mol cyanuric chloride with 2.7 mols of a primary n-alkylamine with a C to C chain length.
  • a washing, bleaching and cleansing agent having a content of from 50% to 99.9%, by weight, of customary components of washing, bleaching and cleansing agents and from 0.1% to 50%, by weight, of a polyethyleneimine selected from the group consisting of (1) branched poly-(N-acetic acid)-polyethyleneimines having an average molecular weight of from 2,000 to 200,000 wherein from about 50% to 100% of the primary and secondary amine groups in the polyethyleneimine molecule are carboxymethylated and (2) their alkali metal, ammonium and organic ammonium salts with bases selected from the group consisting of mono-, diand triethanolamine, morpholine and N-methyl morpholine, said customary components of washing, bleaching and cleansing agents consisting essentially of from 1% to by weight of at least one compound selected from the group consisting of anionic, non-ionic and amphoteric surface-active basic washing components, from 0% to 80% by weight of at least one builder selected from the group consisting of condensed inorganic phosphate builders

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Detergent Compositions (AREA)
US881264A 1968-12-21 1969-12-01 Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines Expired - Lifetime US3650962A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19681816348 DE1816348A1 (de) 1968-12-21 1968-12-21 Wasch-,Bleich- und Reinigungsmittel

Publications (1)

Publication Number Publication Date
US3650962A true US3650962A (en) 1972-03-21

Family

ID=5717064

Family Applications (1)

Application Number Title Priority Date Filing Date
US881264A Expired - Lifetime US3650962A (en) 1968-12-21 1969-12-01 Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines

Country Status (8)

Country Link
US (1) US3650962A (de)
AT (1) AT295709B (de)
BE (1) BE743349A (de)
CH (1) CH511279A (de)
DE (1) DE1816348A1 (de)
FR (1) FR2026793B1 (de)
NL (1) NL6913788A (de)
SE (1) SE364724B (de)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779931A (en) * 1970-12-10 1973-12-18 Henkel & Cie Gmbh Compositions useful in the aqueous cold-bleaching of textiles including optical brighteners
US3901819A (en) * 1972-09-14 1975-08-26 Kao Corp Compositions for activating an inorganic peroxide bleaching agent
US4551506A (en) * 1982-12-23 1985-11-05 The Procter & Gamble Company Cationic polymers having clay soil removal/anti-redeposition properties useful in detergent compositions
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4659802A (en) * 1982-12-23 1987-04-21 The Procter & Gamble Company Cationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
US4661288A (en) * 1982-12-23 1987-04-28 The Procter & Gamble Company Zwitterionic compounds having clay soil removal/anti/redeposition properties useful in detergent compositions
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US5747440A (en) * 1996-01-30 1998-05-05 Procter & Gamble Company Laundry detergents comprising heavy metal ion chelants
WO2015187757A1 (en) * 2014-06-06 2015-12-10 The Procter & Gamble Company Detergent composition comprising polyalkyleneimine polymers
KR20160014672A (ko) * 2013-05-27 2016-02-11 바스프 에스이 고농도의 착물화제를 함유하는 수용액
US20160145544A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20160145543A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20160145545A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20160145546A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20180216031A1 (en) * 2017-01-27 2018-08-02 The Procter & Gamble Company Concentrated surfactant composition
US20180312782A1 (en) * 2015-11-11 2018-11-01 Basf Se Aqueous formulations with good storage capabilities
WO2020103997A1 (en) * 2018-11-23 2020-05-28 ACT.Global A/S Eco-friendly long-term protection compositions and uses
WO2022043042A1 (en) * 2020-08-28 2022-03-03 Unilever Ip Holdings B.V. Detergent composition
US12545856B2 (en) 2020-08-28 2026-02-10 Conopco, Inc. Detergent compositions comprising secondary alkane sultanate, a second anionic surfactant, and alkyl hydroxysultaine cosurfactant

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2082249A5 (de) * 1970-03-09 1971-12-10 Colgate Palmolive Co
US3726814A (en) * 1971-03-15 1973-04-10 Colgate Palmolive Co Liquid laundry detergents and a process for preparing same
DE2703998C3 (de) * 1977-02-01 1981-10-01 Henkel KGaA, 4000 Düsseldorf Flüssiges Waschmittelkonzentrat mit geringem Schaumvermögen
EP2650352A1 (de) * 2012-04-11 2013-10-16 Basf Se Reinigungszusammensetzung für harte Oberflächen

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779931A (en) * 1970-12-10 1973-12-18 Henkel & Cie Gmbh Compositions useful in the aqueous cold-bleaching of textiles including optical brighteners
US3901819A (en) * 1972-09-14 1975-08-26 Kao Corp Compositions for activating an inorganic peroxide bleaching agent
US4551506A (en) * 1982-12-23 1985-11-05 The Procter & Gamble Company Cationic polymers having clay soil removal/anti-redeposition properties useful in detergent compositions
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4659802A (en) * 1982-12-23 1987-04-21 The Procter & Gamble Company Cationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
US4661288A (en) * 1982-12-23 1987-04-28 The Procter & Gamble Company Zwitterionic compounds having clay soil removal/anti/redeposition properties useful in detergent compositions
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US5747440A (en) * 1996-01-30 1998-05-05 Procter & Gamble Company Laundry detergents comprising heavy metal ion chelants
US5929010A (en) * 1996-01-30 1999-07-27 Procter & Gamble Company Laundry detergents comprising heavy metal ion chelants
RU2656211C2 (ru) * 2013-05-27 2018-06-01 Басф Се Водные растворы, содержащие комплексообразующий агент в высокой концентрации
KR20160014672A (ko) * 2013-05-27 2016-02-11 바스프 에스이 고농도의 착물화제를 함유하는 수용액
US20160097020A1 (en) * 2013-05-27 2016-04-07 Basf Se Aqueous solutions containing a complexing agent in high concentration
JP2016525585A (ja) * 2013-05-27 2016-08-25 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 高濃度で錯化剤を含有する水溶液
WO2015187757A1 (en) * 2014-06-06 2015-12-10 The Procter & Gamble Company Detergent composition comprising polyalkyleneimine polymers
US20160145545A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20160145546A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
US20160145543A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
JP2017536306A (ja) * 2014-11-26 2017-12-07 ザ プロクター アンド ギャンブル カンパニー 洗浄用パウチ
US20160145544A1 (en) * 2014-11-26 2016-05-26 The Procter & Gamble Company Cleaning pouch
JP2019116320A (ja) * 2014-11-26 2019-07-18 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 洗浄用パウチ
US20180312782A1 (en) * 2015-11-11 2018-11-01 Basf Se Aqueous formulations with good storage capabilities
US10961485B2 (en) * 2015-11-11 2021-03-30 Basf Se Aqueous formulations with good storage capabilities
US20180216031A1 (en) * 2017-01-27 2018-08-02 The Procter & Gamble Company Concentrated surfactant composition
WO2020103997A1 (en) * 2018-11-23 2020-05-28 ACT.Global A/S Eco-friendly long-term protection compositions and uses
WO2022043042A1 (en) * 2020-08-28 2022-03-03 Unilever Ip Holdings B.V. Detergent composition
US12545856B2 (en) 2020-08-28 2026-02-10 Conopco, Inc. Detergent compositions comprising secondary alkane sultanate, a second anionic surfactant, and alkyl hydroxysultaine cosurfactant

Also Published As

Publication number Publication date
SE364724B (de) 1974-03-04
DE1816348A1 (de) 1970-06-25
FR2026793B1 (de) 1976-02-20
NL6913788A (de) 1970-06-23
AT295709B (de) 1972-01-10
BE743349A (de) 1970-06-18
CH511279A (de) 1971-08-15
FR2026793A1 (de) 1970-09-18

Similar Documents

Publication Publication Date Title
US3650962A (en) Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines
US3676340A (en) Combinations of detergents with controlled foaming properties and washing agents containing them
US3965024A (en) Washing agent compositions and washing assistant composition containing phosphonopolycarboxylate sequestering agents
US3726797A (en) Detergent compositions and processes incorporating n-(2-hydroxy hydrocarbyl)iminodicarboxylates
US3637339A (en) Stain removal
US3775332A (en) Method of activating per-compounds and solid activated per-compound compositions
US3663444A (en) Washing and cleansing agents with polyamides having improved dirtcarrying capacity
US3850832A (en) Washing, rinsing and cleansing agent compositions containing furan-maleic anhydride copolymer sequestering agents
JPS6183299A (ja) 洗剤組成物
US3686128A (en) Washing,bleaching and cleansing agents containing poly - (n-tricarballylic acid)-alkyleneimines
CA1105658A (en) Activated bleaching process and compositions therefor
US3746646A (en) Detergent washing composition
US3650963A (en) Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines
US3897347A (en) Washing agents containing a textile softener and process of washing and softening textiles
CA1217403A (en) Stabilized bleaching and laundering composition
US3718597A (en) Washing, bleaching and cleansing agents containing copolymeric n-alkylcarboxylic acid alkyleneimines
US3640874A (en) Bleaching and detergent compositions
US3708427A (en) Washing and cleansing compositions
US3751370A (en) Low-foaming rinsing washing and cleaning compositions
US4115309A (en) Compositions and method for activating oxygen utilizing cyclic ester-anhydrides of α-hydroxycarboxylic acids
US3691082A (en) Low-foaming rinsing,washing and cleaning compositions
CA1207956A (en) Peroxyacid bleaching and laundering composition
US3753914A (en) Synergistic bleaching textile treating compositions with an antimicrobial action
US3816378A (en) Polyester salts containing quaternary ammonium groups
US3844959A (en) Detergent composition with an amido-amine fabric softening agent