US3920564A - Softener-detergent composition - Google Patents

Softener-detergent composition Download PDF

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Publication number
US3920564A
US3920564A US290720A US29072072A US3920564A US 3920564 A US3920564 A US 3920564A US 290720 A US290720 A US 290720A US 29072072 A US29072072 A US 29072072A US 3920564 A US3920564 A US 3920564A
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Prior art keywords
detergent
composition
detergent composition
group
carbon atoms
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US290720A
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John Jerome Grecsek
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Colgate Palmolive Co
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Colgate Palmolive Co
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Priority to US290720A priority Critical patent/US3920564A/en
Priority to AU59781/73A priority patent/AU5978173A/en
Priority to DE19732343636 priority patent/DE2343636A1/de
Priority to IT52583/73A priority patent/IT1008041B/it
Priority to CA181,462A priority patent/CA1011506A/en
Priority to FR7333710A priority patent/FR2200353B1/fr
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Publication of US3920564A publication Critical patent/US3920564A/en
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines

Definitions

  • the formulations conventionally employed generally comprise synthetic detergent surfac. tants and certain alkaline so-called builder materials" which function to enhance the cleaning levels of synthetic materials.
  • Someinorganic-builder materials present in detergent formulations have been known to have a tendency to react with the metal ions present in the washing solution precipitating out insoluble salts which deposit on the textile material being laundered. Such deposited mineral salts weaken the laundered fabrics, particularly at those areas of, the fabric which are exposed to frictional and creasing effects such as collars and cuffs.
  • compositions commonly employed inhome laundering processes for the treatment of fabrics to improve softness or hand normally are liquid fabric softener compositions which contain in a water vehicle a quaternary ammonium active component wherein all the hydrogen atoms of an ammonium radical are re-.
  • cationic softener compounds have an affinity for nagatively-charged fibers and normally have at least one long chain alkyl radical of from l6-t0 carbon atoms.
  • Other fabric softeners generally employed are .of the N-higher alkyl been formulated based upon, linear alkyl benzene sulfonates, compounds thought to possess the best detergency characteristics. While such anionic detergents do possess excellent detergency characteristics. theuse of linear alkyl benzene sulfonatesand other anionic detergents based upon the alkyl aryl sulfonates has certain distinct shortcomings.
  • the alkyl aryl sulfonates or linear alkyl benzene sulfonates do not possess any fabric-softening characteristics, it is necessary to employ an additional fabric softener when using such anionic detergents. Since, however, the preferred fabric softeners are of the cationic quaternary ammonium type, such fabric softeners cannot be formulated in the same detergent composition with the anionic detergent. Thus, the conjoint employmentof the anionic detergent and the cationic fabric softener is precluded, since such fabric-softeners and detergents complex and precipitate when employed conjointly, thereby eliminating the'functional characteristics of each of the materials.
  • anionic detergents based upon linear alkyl benzene sulfonates or alkyl aryl sulfonates in general possess the undesirable characteristics of phase incompatibility with various water-soluble alkaline detergent builders in aqueous systems.
  • the anionic detergents are incompatible with various phosphate builders generally employedin detergent compositions, thereby eliminating the all-purpose functionality of.the detergents. Accordingly, a clear single-phase liquid detergent composition cannot be prepared from the conventional phosphate builders and the linear alkyl benzene sulfonate detergents such a separation of phases usually results.
  • cationic and amine fabric softeners can successfully be incorporated into anionic and nonionic detergent compositions where the builder is a water-soluble salt of an aminopolycarboxylate or a water-soluble salt of citric acid, rather than the usual sodium or potassium tripolyphosphate.
  • the substitution of an aminopolycarboxylate salt or a citric acid salt for tripolyphosphate as a builder increases the functionality of cationic and amine type fabric soften ers in a softergent.
  • the anionic detergents to be used in the present invention may generally be designated as water-soluble salts of organic reaction products having in their molecular structure an anionic solubilizing group such as SO H, SO H, P0 and COOI-l, and an alkyl or aralkyl radical having about 8 to 22 carbon atoms, such as: water-soluble sulfated and sulfonated anionic alkali metal and alkaline earth metal detergent salts containing a hydrophobic higher alkyl moiety, such as salts of higher alkyl-mono-or polynuclear arylsulfonates hav ing from about,8 to 18 carbon atoms in the alkyl group which may have a straight or branched structure, e.g.
  • alkali metal salts of sulfated condensation products of ethylene oxide e.g., 3 to 20 and preferably 3l0 mols of ethylene oxide per mol or other compound
  • ethylene oxide e.g., 3 to 20 and preferably 3l0 mols of ethylene oxide per mol or other compound
  • alkali metal salts of sulfated condensation products of ethylene oxide e.g., 3 to 20 and preferably 3l0 mols of ethylene oxide per mol or other compound
  • alkyl phenols having alkyl groups containing 6 to 18 carbon atoms
  • alkali metal salts of sulfated alcohols containing from about 8 to 18 carbon atoms e.g. sodium lauryl sulfate and sodium stearyl sulfate
  • alkali metal salts of higher fatty acid esters of low molecular weight alkylol sulfonic acid e.g. fatty acid esters of the sodium salt of isethionic acid
  • fatty cthanolamide sulfates fatty acid amides of amino alkyl sulfonic acids, e.g.
  • lauric acid amide of taurine alkali metal salts of hydroxy alkane sulfonic acid having 8 to 18 carbon atoms in the alkyl group, e.g. hexadecyl al- 3 phahydroxy sodium sulfonate.
  • these organic surface active agents are employed in the form of their alkali metal salts or alkaline earth metal salts because such salts possess the requisite stability, water solubility, and low cost essential to practical utility.
  • Suitable water-soluble, higher fatty acid salts which are used in conjunction with the foregoing anionic detergents include alkali metal salts of saturated, unsaturated, or mixtures of unsaturated and saturated.
  • fatty acids containing from about 8 to 18 carbon atoms in the moleculesuch as: sodium caprate, sodium laurate, sodium myristate, sodium palmitate, potassium oleate, sodium stearate, sodium and potassium salts of tallow fatty acids, sodium and potassium salts of coconut oil fatty acids, and the like.
  • a water-soluble higher fatty acid salt will be added to compositions of the invention as a salt.
  • a water-soluble higher fatty acid salt can also be formed in situ by adding stoichiometric amounts of the desired fatty acid and the desired alkaline hydroxide directly to a composition; or, alternatively, by adding a desired fatty acid or fatty acid mixture directly to a heavy-duty detergent composition where the normal alkalinity desirable in such compositions is sufficient to form the water-soluble, higher fatty acid salt.
  • the anionic detergent may be present in the formulation in amounts ranging from -357r, with a range of 5-15% preferred.
  • the anionic detergent may be mixed with a nonionic detergent, as the mixtures appear to have greater washing power than'the individual components and, in some instances, have greater wetting powder and physical stability.
  • nonionic wetting agent or detergent it is preferred to use the low-foaming ethylene oxide condensate type of nonionic detergents.
  • nonionic wetting agent or detergent it is preferred to use the low-foaming ethylene oxide condensate type of nonionic detergents.
  • examples thereof are the reaction products of benzyl chlorideand ethoxylated alkyl phenol having the formula where R is an alkyl chain having from 6 to 12 carbon atoms and X is a whole number from 12 to polyof the formula (ClC,H,),CH-C0,(CH,CH,O).,CH
  • alkyl phenol such as the polyglycol ethers of alkyl phenols having an alkyl group of at least about 6 and usually about 8 to 20 carbon atoms and an ethylene oxide ratio (number of ethenoxy groups per mole of condensate) of about 7.5, 8.5, l 1.5, 20.5, 30, and the like.
  • the alkyl substituent on the aromatic nucleus may be di-isobutylene, diamyl, polymerized propylene, isooctyl, nonyl, dimerized C C -olefm, and the like.
  • condensates with phenols is an alkylated B-naphthol condensed with 8 moles of ethylene oxide, the alkyl group having 6 to 8 carbon atoms.
  • detergents are the polyoxyalkylene esters of organic acids, such as the higher fatty acids, rosin acids, tall oil, or acids from the oxidation of petroleum, and the like.
  • the polyglycol esters will usually contain from about 8 to about 30 moles of ethylene oxide or its equivalent and about 8 to 22 carbon atoms in the acyl group.
  • Suitable products are refinedtall oil condensed with l6 or 20 ethylene oxide groups, or similar polyglycol esters of laurie, stearic, oleic and like acids.
  • Non-ionic detergents are the polyalkylene oxide condensates with higher fatty acid amides, such as the higher fatty acid primary amides and higher fatty acid mono and di-cthanol-amides.
  • Suitable agents are coconut fatty acid amide condensed with about 10 to 30 moles of ethylene oxide.
  • the fatty acyl group will similarly have about 8 to 22 carbon atoms, and usually about 10 to 18 carbon atoms in such products.
  • the corresponding sulphonamides may also be used if desired.
  • polyether non-ionic detergents are the polyalkylene oxide ethers of higher aliphatic alcohols.
  • Suitable alcohols are those having a hydrophobic character, and preferably 8 to 22 carbon atoms. Examples thereof are iso-octyl, nonyl. decyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl and oleyl alcohols which may be condensed with an appropriate amount of ethylene oxide, such as at least about 6, and preferably about l0-30 moles.
  • a typical product is tridecyl alcohol, produced by the 0x0 process, condensed with about l2, 15 or 20 moles of ethylene oxide.
  • the corresponding higher alkyl mercaptans or thioalcohols condensed with ethylene oxide are also suitable for use in compositions of the present invention.
  • the water soluble polyoxyethylene condensates with polyoxypropylene polymers may likewise be employed in compositions of the present invention.
  • the polyoxypropylene polymer which is prepared by condensing propylene oxide with an organic compound containing at least one reactive hydrogen, represents the hydrophobic portion of the molecule, exhibiting sufficient water insolubility per se, at a molecular weight of at least about 900, such as about 900 to 2,400, and preferbly about 1,200 to 1,800.
  • the increasing addition or condensation of ethylene oxide on a given water insolubie polyoxypropylene polymer tends to increase its water solubility and raise the melting point such that the products may be water soluble, and normally liquid, paste or solid in physical form.
  • the quantity of ethylene oxide varies with the molecular weight of the hydrophobic unit but will usually be at least about 20% and preferably at least about 40% by weight of the product. With an ethylene oxide content of about 40 up to 50%, there are usually obtained normally liquid products, above 50% soft waxlike products. and from about -90% normally solid products may be obtained which can be prepared in flake form if desired.
  • These condensates may be designated by the following structure:
  • Y is the residue of an organic compound which contained x active hydrogen atoms.
  • n is an integer
  • x is an integer, the value of n and x being such that the molecular weight of the compound, exclusive of E, is at least 900, as determined by hydroxy number,
  • E is a polyoxyethylene chain and constitutes 2090%
  • H is hydrogen
  • Alt is preferred to use products of the type just described having a total molecular weight within the range 2,000 and 10,000 and preferably about 4,000 to 8,000.
  • a suitable material is a condensate having a typical average molecular weight of about 7,500 the hydrophobic polypropylene glycol being condensed with sufficient ethylene oxide until a normally 'solid watersoluble product is obtained which has an ethylene oxide content of about 80-90% and a melting point usually of about 515 4 C.
  • Another material is a liquid condensate having an ethylene oxide content of 40-50% anda molecular weight of about 4,500.
  • the nonionic detergents may be present in the for,- mulations of the present invention in. amounts ranging from )35%,. and preferably from about 5 to Preferred fabric softeners for use in the compositions of the present invention are the N-higher alkyl alkylene diamines, where the alkyl chain ranges from about 8 to about carbon atoms and the alkylene chain ranges from about 2 to about 6 carbon atoms.
  • An example is N-tallow propylene diamine.
  • Cationic fabric softeners may also be used in detergentformulations according to the present invention.
  • Preferred quaternary ammonium fabric softeners include dialkyl dimethyl ammonium chloride wherein the alkyl" groups are derived from tallow or contain from about 12 to about 2 4 carbon atoms.
  • the anion may be selected from thegroup consisting of bromide, chloride, fluoride, methosulfate and ethosulfate.
  • the fabric softener for use in the present invention may be an amine-type fabric softener or a quaternary ammonium fabric softener, or a mixture of both types of fabric softener.
  • the amount of fabric softener may range from about 1% to about 10% preferably 2 to 7%.
  • the builder salts used in the present invention include water-soluble salts (e.g. sodium, potassium, am monium and amine) of ammonium carboxylic acids, such as nitrilo triacetic (NTA), ethylene diamine-tetraacetic (EDTA), N(2-hydroxyethyl) iminodiacetic, diethylene triamine pentaacetic, N(2 -hydroxyethyl) (EDTA 1,2-diamino cyclohexane diacetic, nitrilo ethylene diamine triacetic and the like, and water-soluble salts of citric acid.
  • NTA nitrilo triacetic
  • EDTA ethylene diamine-tetraacetic
  • EDTA N(2-hydroxyethyl) iminodiacetic
  • diethylene triamine pentaacetic N(2 -hydroxyethyl)
  • EDTA 1,2-diamino cyclohexane diacetic, nitrilo
  • compositions herein can include other substances generally employed in detergent compositions, provided that the use of any such materials does not substantially adversely affect thedesired properties of the .compositions.
  • suitable materials are hydrotropic solubilizing agents such as sodium xyleneand toluene sulfonates; sodium carboxymethyl-v cellulose and polyvinylalcohol anti-redeposition agents; optical or fluorescent brightener materials of the triazole or benzidinesulfone type; germicides; coloring agents; perfumes; and the like
  • the detergent compositions of the present invention are, excellent compositions for allv types of cleaning operations, they are extremely effective for the cleaning of textiles in a conventional laundry or washing machine.
  • the detergentcompositions of the present invention can be effectively used for laundering fabrics in water having a teperature from about 60 to about 212 F., the detergent compositions of the present invention exhibiting unusually effective detergency and fabric softening characteristics in both cold and hot water'Preferably, the step of the present invention is followed by rinsing and drying of the fabric.
  • detergent composition concentrated in the wash solution should range from about 0.05 percent to about 0.5 percent" by total weight.
  • the addition of the fabrics and the detergent composition can be conducted in-any suitable conventional manner.
  • the fabrics can be added to the container or washer either before or after the washing solution is added.'The fabrics are then agitated in the detergent solution for varied periods of time, a wash cycle of from 8 to 15 minutes being generally used in the washing cycle of an automatic agitator type washer.
  • the detergent composition is drained off and the fabrics are rinsed in substantially pure water.
  • thc fabrics can be rinsed as many times as desired. After the fabrics are rinsed they are dried, first by spinning, and
  • the organic detergent and-fabric-softening component as well as the builders and any minor ingredients are incorporated into the composition prior to its conversion into the final product form, e.g., detergent granules, flakes, bar, etc.
  • the individual components of the novel detergent compositions of the present invention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
  • the softener-builder interaction was then examined in the presence of a variety of builders with and without a nonionic'detergent for turbidity of the solutions.
  • the turbidity of a material is defined by the expression:
  • I is.the intensity of the incident light beam l, is the intensity of the transmitted light beam 1 is-the length of the sample tis the turbidity of the material
  • Turbidity measurements were made on a Lumetron colorimeter using a green filter and a 3cm-cell and by eye. All solutions were made with tap water of 100 ppm hardness.
  • the softener used was N-tallow propylenediamine; the nonionic used was Neodol 45-11, an ethoxylated fatty alcohol manufactured by Shell Chemical Corporation. The results are shown in 5% Softener, l0% nonionic. 40% sodium Table ll-continued It can thus be seen that even at high concentrations of sodium nitrilotriacetate or sodium citrate builders. the softener-detergent solutions remain relatively clear and do not break down.
  • softergent solutions were formulated using 10% nonionic detergent (ethoxylated fatty alcohol). 5% N-tallow propylene diamine softener, and 040% of a builder salt in tap water of I00 ppm hardness. Towel swatches weighing 15 grams each were treated with dilute solutions (0.15%) of the softergent solutions for 10 minutes in a Tergotometer set at rpm. The swatches were then rinsed with tap water for ten minutes. The initial and final yellowness values were recorded to show a final change in yellow color. The results are shown in Table III.
  • results show that sodium nitrilotriacetic acid does not inhibit yellow color development and thus promotes softness.
  • the results also show a negative solution interaction between softener and sodium tripolyphosphate.
  • a detergent composition essentially free of phosphate comprising:
  • a a synthetic organic detergent selected from the group consisting of nonionic and anionic detergents and mixtures thereof;
  • a builder salt selected from the group consisting of water-soluble salts of aminocarboxylic acids, sodium citrate, and mixtures thereof.
  • the synthetic organic detergent comprises from about 0.5 to about by weight of .the composition
  • the fabric softener comprises from about 1 to about by weight of the composition.
  • the builder salt comprises from about 5 to about- 80% by weight of the composition.
  • composition of claim 5 wherein the builder salt is sodium citrate.
  • the builder salt is sodium nitrilotriacetate.
  • R is an alkyl chain having from 6 to 12 carbon atoms and .r is a whole number from 12 to 20, and polyether esters of the formula (CIC HJ CHCOACH CH 0),R
  • x is an integer from 4 to 20 and R is a lower alkyl group of not over four carbon atoms.
  • nonionic detergent is a polyethylene oxide condensate of an alkyl phenol, said alkyl containing from about 6 to 20 carbons, said detergent containing from about 8 to 30 moles of ethylene oxide.
  • a detergent composition essentially free of phosphate comprising: 7
  • a fabric softener selected from the group consisting of N-higher alkyl alkylene diamines wherein the higher alkyl group contains from about 8 to 20 carbon atoms and the alkylene group contains from about 2 to 6 carbon atoms; and
  • a builder salt selected from the group consisting of water-soluble salts of aminocarboxylic acids. sodium citrate, and mixtures thereof.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US290720A 1972-09-20 1972-09-20 Softener-detergent composition Expired - Lifetime US3920564A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US290720A US3920564A (en) 1972-09-20 1972-09-20 Softener-detergent composition
AU59781/73A AU5978173A (en) 1972-09-20 1973-08-29 Softener-detergent composition
DE19732343636 DE2343636A1 (de) 1972-09-20 1973-08-30 Weichspuelendes waschmittel
IT52583/73A IT1008041B (it) 1972-09-20 1973-09-18 Perfezionamento nelle composizioni detergenti
CA181,462A CA1011506A (en) 1972-09-20 1973-09-19 Softener-detergent composition
FR7333710A FR2200353B1 (enrdf_load_stackoverflow) 1972-09-20 1973-09-20

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US290720A US3920564A (en) 1972-09-20 1972-09-20 Softener-detergent composition

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AU (1) AU5978173A (enrdf_load_stackoverflow)
CA (1) CA1011506A (enrdf_load_stackoverflow)
DE (1) DE2343636A1 (enrdf_load_stackoverflow)
FR (1) FR2200353B1 (enrdf_load_stackoverflow)
IT (1) IT1008041B (enrdf_load_stackoverflow)

Cited By (21)

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US4045361A (en) * 1975-05-21 1977-08-30 The Procter & Gamble Company Fabric conditioning compositions
US4261869A (en) * 1977-07-01 1981-04-14 Lever Brothers Company Detergent compositions
US4560492A (en) * 1984-11-02 1985-12-24 The Procter & Gamble Company Laundry detergent composition with enhanced stain removal
US4698181A (en) * 1986-06-30 1987-10-06 The Procter & Gamble Company Detergent compositions containing triethylenetetraminehexaacetic acid
US4704233A (en) * 1986-11-10 1987-11-03 The Procter & Gamble Company Detergent compositions containing ethylenediamine-N,N'-disuccinic acid
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US4983315A (en) * 1989-08-10 1991-01-08 The Procter & Gamble Company N,N'-(1-oxo-1,2-ethanediyl)-bis(aspartic acid), salts and use in detergent compositions
US5252246A (en) * 1992-01-10 1993-10-12 Allergan, Inc. Nonirritating nonionic surfactant compositions
US5472642A (en) * 1994-12-22 1995-12-05 Lever Brothers Company, Division Of Conopco Inc. Diaminoalkyl di(sulfosuccinates) and their use as builders
US5488146A (en) * 1994-12-22 1996-01-30 Lever Brothers Company, Division Of Conopco, Inc. Process for the preparation of sulfo carboxymethyloxysuccinic acid and its salts
US5531915A (en) * 1993-03-05 1996-07-02 The Procter & Gamble Company Detergent compositions containing ethylenediamine-N,N'-diglutaric acid or 2-hydroxypropylenediamine-N,N'-disuccinic acid
WO1997003172A1 (en) * 1995-07-11 1997-01-30 The Procter & Gamble Company Concentrated, stable fabric softening compositions including chelants
US5663427A (en) * 1995-12-21 1997-09-02 Lever Brothers Company, Division Of Conopco, Inc. Cysteic monosuccinic acid and its salts
US5668098A (en) * 1996-03-19 1997-09-16 Lever Brothers Company, Division Of Conopco, Inc. Detergent compositions containing ethylene aspartate cysteate (EAC) sequestrants
US5686402A (en) * 1995-12-27 1997-11-11 Lever Brothers Company, Division Of Conopco, Inc. Detergent compositions containing ethylene dicysteate (EDC) sequestrants
US5693854A (en) * 1995-12-27 1997-12-02 Lever Brothers Company, Division Of Conopco, Inc. Ethylene dicysteate sequestrants and methods for preparation
US5714455A (en) * 1994-12-02 1998-02-03 Lever Brothers Company, Division Of Conopco, Inc. Intimate admixtures of salts of sulfo carboxymethyloxy succinate (SCOMS) with selected glycolipid based surfactants to improve the flow and handling
US20030195134A1 (en) * 2002-04-11 2003-10-16 The Procter & Gamble Company Detergent granule comprising a nonionic surfactant and a hydrotrope
WO2004011590A1 (en) * 2002-07-31 2004-02-05 Colgate-Palmolive Company Unit dose nonaqueous softener disposed in water soluble container
WO2004011582A1 (en) * 2002-07-31 2004-02-05 Colgate-Palmolive Company Fabric conditioning compositions containing an amine acid softening compound
US20050113278A1 (en) * 2003-11-20 2005-05-26 Ecolab, Inc. Binding agent for solidification matrix

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57183471A (en) * 1981-04-30 1982-11-11 Takemoto Oil & Fat Co Ltd Synthetic fiber treating oil agent
FR2602955B1 (fr) * 1986-08-19 1991-04-05 Henkel France Composition pour le nettoyage et la desinfection du materiel de traite

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US4045361A (en) * 1975-05-21 1977-08-30 The Procter & Gamble Company Fabric conditioning compositions
US4261869A (en) * 1977-07-01 1981-04-14 Lever Brothers Company Detergent compositions
US4560492A (en) * 1984-11-02 1985-12-24 The Procter & Gamble Company Laundry detergent composition with enhanced stain removal
EP0181025A3 (en) * 1984-11-02 1989-12-13 The Procter & Gamble Company Laundry detergent composition with enhanced stain removal
US4698181A (en) * 1986-06-30 1987-10-06 The Procter & Gamble Company Detergent compositions containing triethylenetetraminehexaacetic acid
US4704233A (en) * 1986-11-10 1987-11-03 The Procter & Gamble Company Detergent compositions containing ethylenediamine-N,N'-disuccinic acid
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US4983315A (en) * 1989-08-10 1991-01-08 The Procter & Gamble Company N,N'-(1-oxo-1,2-ethanediyl)-bis(aspartic acid), salts and use in detergent compositions
US5252246A (en) * 1992-01-10 1993-10-12 Allergan, Inc. Nonirritating nonionic surfactant compositions
US5531915A (en) * 1993-03-05 1996-07-02 The Procter & Gamble Company Detergent compositions containing ethylenediamine-N,N'-diglutaric acid or 2-hydroxypropylenediamine-N,N'-disuccinic acid
US5714455A (en) * 1994-12-02 1998-02-03 Lever Brothers Company, Division Of Conopco, Inc. Intimate admixtures of salts of sulfo carboxymethyloxy succinate (SCOMS) with selected glycolipid based surfactants to improve the flow and handling
US5472642A (en) * 1994-12-22 1995-12-05 Lever Brothers Company, Division Of Conopco Inc. Diaminoalkyl di(sulfosuccinates) and their use as builders
US5488146A (en) * 1994-12-22 1996-01-30 Lever Brothers Company, Division Of Conopco, Inc. Process for the preparation of sulfo carboxymethyloxysuccinic acid and its salts
WO1997003172A1 (en) * 1995-07-11 1997-01-30 The Procter & Gamble Company Concentrated, stable fabric softening compositions including chelants
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US5693854A (en) * 1995-12-27 1997-12-02 Lever Brothers Company, Division Of Conopco, Inc. Ethylene dicysteate sequestrants and methods for preparation
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US20030195134A1 (en) * 2002-04-11 2003-10-16 The Procter & Gamble Company Detergent granule comprising a nonionic surfactant and a hydrotrope
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US20050113278A1 (en) * 2003-11-20 2005-05-26 Ecolab, Inc. Binding agent for solidification matrix
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Also Published As

Publication number Publication date
AU5978173A (en) 1975-03-06
CA1011506A (en) 1977-06-07
FR2200353B1 (enrdf_load_stackoverflow) 1977-03-11
DE2343636A1 (de) 1974-03-28
IT1008041B (it) 1976-11-10
FR2200353A1 (enrdf_load_stackoverflow) 1974-04-19

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