EP0199765B1 - Monoglykoside als viskositätsregler in detergenzien - Google Patents

Monoglykoside als viskositätsregler in detergenzien Download PDF

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Publication number
EP0199765B1
EP0199765B1 EP85905299A EP85905299A EP0199765B1 EP 0199765 B1 EP0199765 B1 EP 0199765B1 EP 85905299 A EP85905299 A EP 85905299A EP 85905299 A EP85905299 A EP 85905299A EP 0199765 B1 EP0199765 B1 EP 0199765B1
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EP
European Patent Office
Prior art keywords
composition
weight
monoglycoside
alkyl
saccharide
Prior art date
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Expired - Lifetime
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EP85905299A
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English (en)
French (fr)
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EP0199765A1 (de
EP0199765A4 (de
Inventor
Allen D. Urfer
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • This invention deals with liquid detergent products.
  • liquid detergents usually contain a substantial amount of water in the product.
  • Liquid detergent products are considerably easier to manufacture than are granular detergent products. The latter materials require a substantial amount of capital investment for spray-drying towers.
  • a consumer preference has emerged for the liquid products due to their more concentrated form.
  • Most liquid detergent products do not contain the inert inorganic material which is required to give spray-dried granules their crisp, non-caking structure. Accordingly, the liquid detergent products are used in much smaller amounts while giving approximately the same level of active ingredients in the wash water.
  • a second consumer preference is for a product having a desirable viscosity.
  • Products which are water- thin are not desirable.
  • products which are too thin are more likely to be spilled by the consumer when attemping to handle the approximately four-liter bottles in which liquid detergents are commonly packaged.
  • Another advantage of liquid detergent products is that they can be applied directly to a heavily soiled portion of a garment. In such cases, raising the viscosity of a normally thin liquid detergent product allows the detergent to stay on the soiled area longer.
  • a market also exists for shampoo, liquid hand soaps, body soaps, dishwashing liquids, cosmetics and personal care products having a relatively high viscosity.
  • Mao in European Patent Application No. 0092875 published on November 2,1983 discloses a process for the production of alkyl glycosides involving a wiped-film evaparator. Mao further teaches that the fatty portion of the glycoside may be a primary or secondary alcohol having straight or branched chains which may be either saturated or unsaturated and may contain either linkages as well. Substantially similar teachings to European Patent Application No. 0092875 are also found in United States Patent 4,393,203 issued July 12, 1983 to the same inventor.
  • European Patent Application No. 0096917 (laid open December 12, 1983), to Farris describes the production of glycosides containing from 8 to 25 carbon atoms in the alcohol residue of the glycoside.
  • the alcohol residue may be primary or secondary, straight or branched and obtained from a saturated or unsaturated material.
  • Europan Patent Application No. 0105556 to Jones et al made public April 18, 1984 describes detergent products containing glycosides, nonionics, and anionics.
  • Canadian Patent 919,424 to Culver et al issued January 23, 1973 describes alkaline drain cleaning compositions containing phosphate esters, and a glycoside or an anionic surfactant.
  • This invention describes a liquid detergent comprising:
  • R is the hydrophobic moiety (fatty organic portion) of the molecule containing from 10 to 24 carbon atoms
  • O is an oxygen, preferably in the 1 position of the saccharide
  • G represents the saccharide
  • glycosides which have been found useful in increasing the viscosity of aqueous detergent products containing an anionic surfactant are monoglycosides.
  • monoglycoside as used herein includes such substituted monosaccharides as fructosides, glucosides, mannosides, galactosides, talosides, allosides, altrosides, idosides, arabinosides, xylosides, lyxosides, ribosides, and mixtures thereof.
  • R is the hydrophobic moiety (fatty organic portion) of the molecule containing from 10 to 24 carbon atoms
  • 0 is an oxygen, preferably in the 1 position of the saccharide
  • G represents the saccharide. While more than one R group may be on each saccharide molecule (attached as an ether linkage), the difficulty and expense outweigh the benefit of introducing more than the initial hydrophobic moiety.
  • the benefits of the invention in the order of importance are that the glycoside first be a monoglycoside, and second that the glycoside contain from 10 to 24, and preferably from 12 to 18 carbon atoms in the hydrophobic moiety of the molecule.
  • a third condition is that the hydrophobic moiety on the monoglycoside be branched either by using a secondary alcohol or by branching within the hydrophobic moiety.
  • branching is desirably multiple branched, e.g. several groups. The oxo alcohols having multiple methyl branching are particularly desirable.
  • the monoglycoside is preferably a glucoside and may be obtained as is described in United States Patent 3,219,656 to Boettner issued November 23, 1965 or the article entitled "Preparation and Properties of Pure Alkyl Glucosides, Maltosides, and Maltotriosides by Koeltzow and Urfer, JAOCS, V. 61, No. 10, p. 1651 (1984).
  • the amount of monoglycoside obtained can be maximized by utilizing an excess of alcohol to promote the acetal formation over the polymerization reaction.
  • Particular alcohols which may be utilized herein are n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-octadecyl, n-decyl, tetramethyl 1-nonanol, and trimethyl-nonanol.
  • Secondary alcohols which may be used to obtain the monoglycoside include 2-decanol, 2-undecanol, 2-dodecanol and 2-tridecanol.
  • Additional alcohols which may be employed in forming the monoglycoside include guerbet alcohols such as are described in United States Patent 4,425,458 to Lindner issued January 10, 1984.
  • anionic surfactants which are useful herein are alkyl ether sulfates, alkyl benzene sulfonates, alkyl sulfates, olefin sulfonates, paraffin sulfonates and soap (carboxylate). Particularly valuable are those anionic surfactants containing from 10 to 20 carbon atoms in the hydrophobic portion of the molecule.
  • a preferred surfactant group is the alpha-olefin sulfonates.
  • a second preferred surfactant is an alkyl ether sulfate which contains an average of from 1 to 3 ethoxy groups in the molecule.
  • the preferred cation for the anionic surfactants is sodium or potassium or mixtures thereof. Further anionic surfactants which may be employed are those described in United States Patent 4,476,045 to O'Lenick issued October 9, 1984.
  • Alkoxylated nonionic surfactants are to be minimized as an ingredient in the compositions of this invention. It has been found that nonionics such as ethoxylated alcohols reduce the viscosity thereby negating the advantages of the monoglycosides described herein. Typically the alkoxylated nonionic should not be present at greater than 10%, preferably less than 5% by weight. It has also been observed that higher glycosides (DP 2 and greater) reduce the viscosity as the DP increases and the hydrophobic moiety decreases. Therefore higher (DP 2 and greater) glycosides are minimized such that the average DP is less than 1.4, preferably less than 1.3.
  • the amount of glycoside as monoglycoside in the product is preferably from 0.5% to 10%, most preferably from 1 % to 5% by weight.
  • the amount of anionic surfactant in the formula is preferably from 5% to 30%, most preferably from 8% to 25% by weight.
  • the level of water in the product is conveniently set at from 35% to 92%, preferably from 40% to 90% by weight. It is also desirable that the amount of monoglycoside as used herein be in a weight ratio to the anionic surfactant of from 4:1 to 1:60, preferably from 2:1 to 1:10.
  • ingredients of the present invention may be combined in any convenient manner.
  • a preferred order of addition of the components involves obtaining the monoglycoside in its solid state, and adding thereto a mixture of the anionic surfactant and water.
  • the anionic surfactant is usually a fairly concentrated material, it is often necessary to add further water to the end mixture to obtain the desired product.
  • the viscosity will increase substantially as the monoglycoside is added, adequate mixing and pumping capabilities should be utilized to ensure that the product may be efficiently transferred.
  • the product herein will have a viscosity of from 50 to 100,000 preferably from 150 to 10,000 mPa - s at 25°C as determined by a Brookfield cone-plate viscometer having a cone angle of 1.57°.
  • compositions of the present invention may also include all manner of materials normally found in aqueous liquid detergent products including, compatible hydrotropes, optical brighteners and dyes, perfumes, enzymes and the like. Additional ingredients which may be included in the composition of the present invention include builders such as tripolyphosphate, nitrilotriacetate, pyrophosphate and any of the organic builders as discussed in European Patent Application No. 0150930 published 07.08.85.
  • the products of the invention when utilized as laundry detergent products are normally employed at from 0.05% to 1% by weight of the active ingredients in the wash water. It is recommended that the laundry be washed at from 37°C to 60°C.
  • the products herein may also be formulated as liquid dishwashing or hard surface cleaning products in a similar fashion. As dishwashing products are typically of a lower viscosity than is desired for a laundry detergent product, smaller quantities of the monoglycoside may be used.
  • the products described herein are also useful in cosmetics, handcleaners, body soaps, shower gels, shaving creams or gels and hair shampoos.
  • the pH of the products described in the Summary should be from 5 to 8 when diluted on a dry solids basis at 0.1% by weight when no other pH influencing ingredients are present.
  • the products are conveniently adjusted to a pH of from 2.5 to 7.8, preferably 3 to 7.5, most preferably 3 to 7.2 to give maximum thickening. Any convenient buffer or pH adjusting material such as citric acid and its salts may be employed therein.
  • glycosides are prepared. These glycosides are obtained from substantially pure compounds according to Koeltzow and Urfer, supra. These compounds are referenced in the syle of R x DPy wherein R indicates the starting alcohol used to prepare the glycoside, x indicates the chain length of the alcohol, and DP indicates that the material is a saccharide having a degree of polymerization as indicated by y, e.g., DPi is glucose.
  • a base formulation of an anionic surfactant is prepared containing:
  • the pH of the base formula is adjusted and maintained from 5 to 5.5 with citric acid.
  • cocoamide monoethanolamine which is a commonly accepted viscosity control agent for liquid detergent products. Like all amines the cocoamide monoethanolamine has a slightly objectionable odor. The products of this invention are free of objectionable odors.
  • a base formula is prepared as indicated in Example II with the exception that the additive is increased to 4% and the water in the formulation is decreased in a corresponding amount.
  • the oxo alcohol product * gives a viscosity measurement of 3049.
  • a control sample utilizes an equal amount of Glucamate DOE-120 which is a methyl glucoside dioleate with 120 moles ethylene oxide. The control gives a viscosity of 835.
  • Glucamate DOE-120 is a Registered Trademark of Amerchol Corporation, Edison N.J. USA.
  • Example II Substantially similar results are obtained in Example II when a similar amount of a C 14 triethoxysulfate sodium salt is employed. Further, substitution for the olefin sulfonate with a C 12 linear alkyl benzene sulfonate potassium salt gives substantially similar results.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Detergent Compositions (AREA)

Claims (10)

1. Flüssigwaschmittel enthaltend:
(a) 3 bis 45 Gew.-% eines anionischen Tensids,
(b) 0,3 bis 20 Gew.-% eines Monoglykosids der Formel ROG, in der R den hydrophoben Teil des Moleküls (Fettalkylrest) mit 10 bis 24 Kohlenstoffatomen, O ein Sauerstoffatom, vorzugsweise in 1-Stellung des Saccharids, und G das Saccharid bedeuten, und
(c) 30 bis 95 Gew.-% Wasser,
und wobei in diesem Mittel der Gehalt an Glykosidverbindungen mit einem Polymerisationsgrad (D.P.) von 2 oder höher so gewählt ist, daß der Durchschnitts-D.P.-Wert aller Glkosidverbindungen weniger als 1,4 beträgt.
2. Mittel nach Anspruch 1, in dem das anionische Tensid aus der Gruppe bestehend aus Alkylsulfaten, Olefinsulfonaten, Paraffinsulfonaten, Alkylbenzolsulfonaten, Alkylethersulfaten, Alkylcarboxylaten und Mischungen davon ausgewählt ist.
3. Mittel nach Anspruch 1, in dem das Monoglykosid ein Monoglucosid ist.
4. Mittel nach Anspruch 1, das zusätzlich eine Waschmittel-Buildersubstanz enthält.
5. Mittel nach Anspruch 4, in dem die Waschmittel-Buildersubstanz ein Nitrilotriacetat- oder Phosphat-Salz ist.
6. Mittel nach Anspruch 1 oder 3, in dem der hydrophobe Teil des Monoglykosids von einem verzweigten Alkohol abgeleitet ist.
7. Mittel nach Anspruch 1, das zusätzlich bis zu 10 Gew.-% eines alkoxylierten nichtionischen Tensids enthält.
8. Mittel nach einem der Ansprüche 1, 3 and 6, in dem der hydrophobe Teil des Monoglykosids von einer Oxoalkohol-Struktur abgeleitet ist.
9. Mittel nach einem der Ansprüche 1 bis 8, das, nach Verdünnung mit Wasser auf einen Gehalt von 0,1 Gew.-%, bezogen auf eine trockene Feststoffbasis, einem pH-Wert von 5 bis 8 aufweist.
10. Verfahren zur Erhöhung der Viskosität eines wäßrigen Flüssigwaschmittels, das ein anionisches Tensid enthält, durch Einarbeiten von 0,3 bis 20 Gew.-% eines Alkylmonoglykosids der Formel ROG, in der R den hydrophoben Teil des Moleküls (Fettalkylrest) mit 10 bis 24 Kohlenstoffatomen, 0 ein Sauerstoffatom, vorzugsweise in 1-Stellung des Saccharids, und G das Saccharid bedeuten, zum Verdicken des wäßrigen Flüssigwaschmittels, wobei man den Anteil der Glykosidverbindungen mit einem Polymerisationsgrad (D.P.) von 2 oder mehr so einstellt, daß der Durchschnitts-D.P.-Wert aller Glykosidverbindungen weniger als 1,4 beträgt.
EP85905299A 1984-11-06 1985-10-15 Monoglykoside als viskositätsregler in detergenzien Expired - Lifetime EP0199765B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66876284A 1984-11-06 1984-11-06
US668762 1984-11-06

Publications (3)

Publication Number Publication Date
EP0199765A1 EP0199765A1 (de) 1986-11-05
EP0199765A4 EP0199765A4 (de) 1987-03-30
EP0199765B1 true EP0199765B1 (de) 1990-05-23

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ID=24683625

Family Applications (1)

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EP85905299A Expired - Lifetime EP0199765B1 (de) 1984-11-06 1985-10-15 Monoglykoside als viskositätsregler in detergenzien

Country Status (5)

Country Link
EP (1) EP0199765B1 (de)
JP (1) JPH0676595B2 (de)
CA (1) CA1247492A (de)
DE (1) DE3577878D1 (de)
WO (1) WO1986002943A1 (de)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL81354A (en) * 1986-01-30 1990-11-05 Colgate Palmolive Co Liquid detergent having improved softening properties
WO1987006949A1 (en) * 1986-05-06 1987-11-19 A. E. Staley Manufacturing Company Built liquid laundry detergent containing alkyl glycoside surfactant
MY103951A (en) * 1988-01-12 1993-10-30 Kao Corp Detergent composition
DE3822997A1 (de) * 1988-07-07 1990-01-18 Henkel Kgaa Detergensmischung aus nichtionischen und anionischen tensiden und deren verwendung
JP2526105B2 (ja) * 1988-09-20 1996-08-21 花王株式会社 洗浄剤組成物
DE3838808A1 (de) * 1988-11-17 1990-05-23 Henkel Kgaa Wasch- und reinigungsmittel, enthaltend ein tensidgemisch aus alkylglykosiden und aniontensiden
AU5709090A (en) * 1989-06-30 1991-01-03 Amway Corporation Built liquid detergent compositions
US5972628A (en) * 1989-11-17 1999-10-26 Schebo Tech Medizinisch-Biologische Forschungsgesellschaft M.B.H. Pyruvatekinase-iosenzyme typ-M2 (Tumor-M2-PK)-specific antibody/process for the preparation and use thereof
DE4017922A1 (de) * 1990-06-05 1991-12-12 Henkel Kgaa Fluessige alkylglykosidhaltige tensidmischung
DE4036663A1 (de) * 1990-11-17 1992-05-21 Huels Chemische Werke Ag Fluessiges, schaeumendes reinigungsmittel mit erhoehter viskositaet
DE4102744A1 (de) * 1991-01-30 1992-08-06 Henkel Kgaa Schwachschaeumendes scheuerpulver
DE4105851A1 (de) * 1991-02-25 1992-08-27 Henkel Kgaa Verfahren zur herstellung von alkyl- und/oder alkenylsulfat-pasten mit verbesserter fliessfaehigkeit
DE4117689A1 (de) * 1991-05-29 1992-12-03 Henkel Kgaa Fluessige, giess- und pumpfaehige tensidzubereitung
DE4121612A1 (de) * 1991-06-29 1993-01-07 Henkel Kgaa Waessrige tensidzubereitungen
DE4134077A1 (de) * 1991-10-15 1993-04-22 Henkel Kgaa Viskose waessrige tensidzubereitungen
DE4210365C2 (de) * 1992-03-30 1995-06-08 Henkel Kgaa Verwendung von Reinigungsmitteln für harte Oberflächen
SE502525C2 (sv) * 1993-03-23 1995-11-06 Berol Nobel Ab Användning av alkylglykosid som tensid vid rengöring av hårda ytor samt komposition för detta ändamål
DE4320119A1 (de) * 1993-06-18 1994-12-22 Henkel Kgaa Flüssigkristalline wäßrige Tensidzubereitung
DE4404199A1 (de) * 1994-02-10 1995-08-17 Henkel Kgaa Reinigungsmittel für harte Oberflächen
AU702743B2 (en) * 1994-04-07 1999-03-04 Unilever Plc Fabric softening composition
GB9406824D0 (en) * 1994-04-07 1994-06-01 Unilever Plc Fabric softening composition
AU6306594A (en) * 1994-05-12 1995-11-23 R & C Products Pty Limited Liquid dishwashing composition
GB9509452D0 (en) * 1995-05-10 1995-07-05 Unilever Plc Light duty cleaning composititon
US6555515B1 (en) 1995-12-06 2003-04-29 Henkel Kommanitgesellschaft Auf Aktien Formulations for cleaning hard surfaces based on at least partly branched-chain alkyl oligoglucosides
DE19933404A1 (de) * 1999-07-21 2001-01-25 Henkel Kgaa Reinigungsmittel für harte Oberflächen
AR088676A1 (es) 2011-11-11 2014-06-25 Procter & Gamble Composiciones para tratar superficies incluyendo sales protectoras
BR112014014976A2 (pt) 2011-12-19 2017-06-13 Firmenich & Cie composição de limpeza corporal sem sulfato e sem peg
US20150210964A1 (en) 2014-01-24 2015-07-30 The Procter & Gamble Company Consumer Product Compositions
EP3266859A1 (de) * 2016-07-05 2018-01-10 Basf Se Zusammensetzung zur verwendung als entfettungsmittel zum entfernen von fett- und/oder ölartigen ablagerungen
EP3932988A4 (de) * 2019-03-01 2022-11-23 Sumitomo Seika Chemicals Co., Ltd. Viskose zusammensetzung
JP6641068B1 (ja) * 2019-03-01 2020-02-05 住友精化株式会社 粘性組成物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0136844A2 (de) * 1983-09-06 1985-04-10 Henkel Kommanditgesellschaft auf Aktien Glykoside enthaltende Reinigungsmittel

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Publication number Priority date Publication date Assignee Title
US3721633A (en) * 1969-10-06 1973-03-20 Atlas Chem Ind Aqueous built liquid detergents containing alkyl glycosides
EP0105556A1 (de) * 1982-09-30 1984-04-18 THE PROCTER & GAMBLE COMPANY Nichtionische und ionische Tenside enthaltende flüssige Detergenszusammensetzung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0136844A2 (de) * 1983-09-06 1985-04-10 Henkel Kommanditgesellschaft auf Aktien Glykoside enthaltende Reinigungsmittel

Also Published As

Publication number Publication date
CA1247492A (en) 1988-12-28
JPS62500725A (ja) 1987-03-26
EP0199765A1 (de) 1986-11-05
JPH0676595B2 (ja) 1994-09-28
EP0199765A4 (de) 1987-03-30
WO1986002943A1 (en) 1986-05-22
DE3577878D1 (de) 1990-06-28

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