EP0500819B1 - Composition liquide de lavage de vaisselle - Google Patents

Composition liquide de lavage de vaisselle Download PDF

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Publication number
EP0500819B1
EP0500819B1 EP91910074A EP91910074A EP0500819B1 EP 0500819 B1 EP0500819 B1 EP 0500819B1 EP 91910074 A EP91910074 A EP 91910074A EP 91910074 A EP91910074 A EP 91910074A EP 0500819 B1 EP0500819 B1 EP 0500819B1
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Prior art keywords
amphoteric
group
formula
compounds
surface active
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EP91910074A
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German (de)
English (en)
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EP0500819A1 (fr
Inventor
Jadwiga Palicka
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Nouryon Surface Chemistry AB
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Akzo Nobel Surface Chemistry AB
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic 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
    • C11D1/75—Amino oxides

Definitions

  • the present invention relates to liquid dishwashing compositions and more particularly to such compositions which contain an anionic tenside, a mixture of amphoteric surface active compounds and at least one foam boosting compound.
  • the most common commercial liquid dishwashing compositions are primarily intended for hand dishwashing and are as a rule aqueous solutions containing anionic tensides, such as alkyl sulfonates and alkyl ether sulfates, as essential component. These dishwashing agents are entirely satisfactory with regard to cleaning effect, foam forming effect and foam stability. However, the dishwashing compositions based on this type of anionic surface active agents are not satisfactory from an environmental point of view nor with regard to mildness to skin, since they have a certain irritating and allergy causing effect. For environmental reasons it has during the last few years been desired to decrease the total amount of anionic tensides, such as for example paraffin sulfonates, used in different cleaning purposes.
  • anionic tensides such as alkyl sulfonates and alkyl ether sulfates
  • anionic tensides in dishwashing compositions can be replaced by a mixture of amphoteric surface active compounds and at least one foam boasting compound which is an amine oxide, an amido betaine or an amide to give a dishwashing composition which is mild and kind to the skin, has a good foam stability and gives a low biological load and is more efficient than a dishwashing composition based solely on anionic tensides.
  • Dishwashing compositions according to the present invention are particularly suitable for manual washing, of glass, china, kitchen utensils etc, thanks to their mildness.
  • the amphoteric surface active compounds present in the dishwashing compositions of the invention can be characterized by the general formula (I) wherein R is a hydrocarbon group having from 7 to 22 carbon atoms, A is the group (C(O)), n is 0 or 1, R1 is hydrogen or a lower alkyl group, x is 2 or 3, y is an integer of 0 to 4, Q is the group -R2COOM wherein R2 is an alkylene group having from 1 to 6 carbon atoms and M is hydrogen or an ion from the groups alkali metals, alkaline earth metals, ammonium and substituted ammonium and B is hydrogen or a group Q as defined.
  • R is a hydrocarbon group having from 7 to 22 carbon atoms
  • A is the group (C(O))
  • n is 0 or 1
  • R1 is hydrogen or a lower alkyl group
  • x is 2 or 3
  • y is an integer of 0 to 4
  • Q is the group -R2CO
  • Amphoteric compounds encompassed by the above given formula are per se known and used in cleaning compositions and shampoo compositions. They are for example described in the European patent applications 160507, 162600 and 214868. According to the European patent application 160507 a combination of two different amphoteric compounds encompassed by the above given formula is used in mild shampoo compositions.
  • R is a hydrocarbon group having from 7 to 22 carbon atoms and suitably from 11 to 22 carbon atoms.
  • the hydrocarbon group R can be straight or branched, saturated or unsaturated and optionally contain substituents such as hydroxyl groups.
  • the group R can also contain one or several, up to about 20, ethylene oxide groups.
  • the group R can also be a cycloalkyl-alkyl group, an aralkyl or aralkenyl group where the alkyl or alkenyl group contains at least 6 carbon atoms.
  • R is preferably an alkyl or alkenyl group and it is particularly preferred that R is a hydrocarbon group originating from coco, tallow or oleic fatty acid.
  • R1 in the given formula is hydrogen or a lower alkyl group, suitably with 1 to 6 carbon atoms and is preferably hydrogen or a methyl group.
  • x is 2 or 3 and y is suitably 2, 3 or 4 and preferably 2 or 3.
  • the group R2 is suitably a methylene or an ethylene group, preferably a methylene group.
  • M is hydrogen or an ion from the groups alkali metals, alkaline earth metals, ammonium or substituted ammonium such as for example mono-, di- or tri-hydroxyethylammonium.
  • M is preferably a sodium ion.
  • Preferred compounds of the formula (I) have the formula (II): wherein Q is CH2-COOM or CH2CH2COOM, y is 1, 2 or 3 and wherein M, R, x, A, n and B have the above given meanings.
  • R in these compounds suitably originates from tallow, oleic or coco fatty acid.
  • the present dishwashing composition may contain a combination of two amphoteric compounds encompassed by the formulae (I) and (II) whereby one compound contains a carbonyl group (below termed type 1) and the other does not contain such a group (below termed type 2), ie an amphoteric compound wherein n is 1 and, respectively, an amphoteric compound wherein n is 0.
  • the amphoteric compound of type 1 acts primarily as a tenside and suds former and the amphoteric compound of type 2 acts primarily as a detoxifying tenside.
  • Suitable weight ratios between compounds of type 1 and type 2 is within the range of from 1:10 to 10:1 and preferably within the range of from 1:5 to 5:1.
  • For amphoteric compounds of type 1 x in the above given formulae is suitably 2 and the groups B are hydrogen or groups Q.
  • For amphoteric compounds of type 2 x in the above given formulae is suitably 3 and all groups B are groups Q.
  • the mixture of amphoteric compounds contains a carbonyl group containing compound having the general formula (III) wherein R, A, y, Q and B have the same meaning as given for compounds of formula (I), whereby, however, one group B is the group -CH2CHR'OH, wherein R' is H or CH3, in combination with the amphoteric compound having the formula I or II, in which n is 0.
  • R, A, y, Q and B have the same meaning as given for compounds of formula (I), whereby, however, one group B is the group -CH2CHR'OH, wherein R' is H or CH3, in combination with the amphoteric compound having the formula I or II, in which n is 0.
  • R and for M in the group Q are as given for compounds of formula (I).
  • Most suitable are compounds of formula (III) wherein y is 1 and Q is the group -CH2COOM.
  • Amphoteric compounds of formulae IIIa and IIIb are commercially available as mixtures and usually with a weight ratio of compounds of formula IIIa to compounds of formula IIIb within the range of 1:10 to 10:1. Like the amphoteric compounds of formula I and II which contain a carbonyl group the compounds of formula III, IIIa and IIIb act primarily as tensides and suds formers. Suitable weight ratios between compounds of formula III or IIIa and/or IIIb and amphoteric compounds of formula I or II which do not contain a carbonyl group is within the range of from 1:10 to 10:1 and preferably within the range of from 1:5 to 5:1.
  • Amphoteric compounds of the above given formulae are commercially available and sold under the trade name Ampholak (R) by Berol Nobel AB, Sweden.
  • amphoteric compounds can partly replace anionic tensides in liquid dishwashing compositions.
  • the amphoteric compounds are combined with an amide, an amido betaine or an amine oxide having this effect.
  • Amides, amido betaines and amine oxides with this effect for dishwashing agents and other products are per se known and can generally be characterized as amides, amido betaines and amine oxides respectively containing at least one longer hydrophobic hydrocarbon group, ie a fatty acid residue having at least 7 carbon atoms and suitably up to 22 carbon atoms.
  • suitable amides can be mentioned ammonium and ethanol amides, such as mono- and diethanol amides of fatty acids containing at least one longer hydrophobic group having at least 7 carbon atoms.
  • the amides can be characterized by the general formula (IV) R - CO - N(H) p (R 1 OH) 2-p wherein R is the longer hydrophobic hydrocarbon group, which suitably is a saturated or unsaturated, straight or branched, aliphatic hydrocarbon group with 7 to 21 carbon atoms and preferably is an alkyl or alkenyl group with from 11 to 17 carbon atoms.
  • R1 is a methylene or ethylene group and p is 1 or 2.
  • suitable amides can be mentioned mono- and diethanol amides of natural or synthetic fatty acids having 12 to 18 carbon atoms, for example dodecyl carboxylic acid and coco fatty acid.
  • amido betaines which can be used can be characterized bv the general formula (V) wherein R is the longer hydrophobic hydrocarbon group, which suitably is a saturated or unsaturated, straight or branched, aliphatic hydrocarbon group with 7 to 21 carbon atoms and preferably is an alkyl or alkenyl group with from 11 to 17 carbon atoms, n is 1 or 2 and M is preferably hydrogen or a sodium ion.
  • R is the longer hydrophobic hydrocarbon group, which suitably is a saturated or unsaturated, straight or branched, aliphatic hydrocarbon group with 7 to 21 carbon atoms and preferably is an alkyl or alkenyl group with from 11 to 17 carbon atoms, n is 1 or 2 and M is preferably hydrogen or a sodium ion.
  • the amine oxides which can be used can be characterized by the formula (VI) R(R1)2N ⁇ O wherein R is the longer hydrophobic hydrocarbon group, suitably a saturated or unsaturated, straight or branched aliphatic hydrocarbon group having at least 8 carbon atoms. R is especially a group having from 8 to 22 carbon atoms, and suitably it is an alkyl group which can be substituted by a hydroxyl group and also contain one or several, up to about 10, alkoxy groups, preferably ethylene oxide groups.
  • the groups R1 are, independent of each other, lower alkyl or hydroxy alkyl groups with from 1 to 4 carbon atoms. Of the mentioned foam boosting compounds the amine oxides are preferred.
  • the group R is preferable a coconut alkyl group.
  • the weight ratio of the foam boosting compounds, ie the amide, amidobetaine or amine oxide or mixture of two or more of these, to the amphoteric compound or compounds should suitably be at least 1:10 and the ratio is suitably within the range of from 1:10 to 10:1 and preferably within the range from 1:5 to 5:1.
  • an amidobetaine or an amine oxide having foam boosting and foam stabilizing effect anionic tensides which normally are water soluble salts of organic sulfonated acid or sulfated alcohols
  • anionic tensides which normally are water soluble salts of organic sulfonated acid or sulfated alcohols
  • liquid dishwashing compositions can be replaced to a certain extent and hereby a dishwashing composition is obtained which is advantageous from a biological point of view and advantageous with regard to mildness at use.
  • the improved mildness which is obtained is dependent on an efficient detoxification of anionic tensides through formation of mixed micelles of the anionic surface active compounds and the amphoteric surface active compounds.
  • the very low critical micelle concentration of the specific amphoteric compounds is hereby utilized.
  • the desired effect is thus obtained with very small amounts of amphoteric compound, particularly of those of type 2.
  • Dishwashing compositions according to the present invention have also been found to be as effective as such based on solely anionic
  • anionic tensides of the above mentioned types are also present, but in lower amounts than usual.
  • the amount of anionic tenside is suitably within the range of from 90 to 20 per cent by weight, based on the total amount of amphoteric surface active compounds and anionic surface active compounds, preferably within the range 85 to 60 per cent and most preferably within the range of from 80 to 60 per cent by weight.
  • the anionic tensides are, as indicated above, water soluble salts of organic sulfonated acids or sulfated alcohols, and then particularly alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkyl aryl sulfonates, wherein the alkyl group usually contains from 8 to 22 carbon atoms.
  • alkyl group usually contains from 8 to 22 carbon atoms.
  • anionic tensides containing ether groups these are usually ethylene oxide groups and the compounds normally contain between 1 and 10 such groups per molecule.
  • the cations of these salts are alkali metals, alkaline earth metals, ammonium or amines such as mono-, di- and triethanol amine cations.
  • anionic tensides can be mentioned sodium lauryl sulfonate, sodium lauryl ether sulfate with two or three ethylene oxide groups, the corresponding ammonium or ethanol amine salts, sodium or other salts of dodecyl benzene sulfonic acid and alkyl benzene sulfonic acid wherein the alkyl group contains an average of from 11 to 13 carbon atoms.
  • the present dishwashing compositions are liquid and the main component for this is of course preferably water.
  • Water used in liquid dishwashing compositions is often deionized but other types of water can also be used.
  • Other liquid solvents can of course be included, such as for example lower alcohols and glycols and lower alkyl ethers of the glycols. These types of solvents are normally present, if at all present, in minor amounts. As some specific examples can be mentioned ethanol, isopropanol, ethylene glycol etc.. Solvents are sometimes included mainly for preservation.
  • One advantage of the present compositions is, however, that since they contain amphoteric compounds of the type according to formula (I) no solvent is required in order to obtain preservative effect.
  • the present dishwashing compositions can be prepared in per se conventional manner by simple mixing of the components and they can of course also be used in conventional manner. Normal dosage is about 0.2 g/l dish liquor of a dishwashing composition with a total dry content of from about 10 to about 45 per cent by weight.
  • the dishwashing compositions can of course also contain other conventionally used additives for improvement of different properties such as thickeners, antibacterial agents, colorants, pigments, perfumes etc.
  • Other amphoteric compounds can also be present if desired, such as betaines, and also nonionic tensides such as glycosides.
  • Dishwashing compositions were prepared from the following components (all amounts given are as 100% active substance): Composition I: 12 g of linear alkyl benzene sulfonate with C12 to C18 alkyl groups, 7 g of sodium lauryl ether sulfate with 3 ethylene oxide groups, 2 g of C12-C18 alkane sulfonate, 2 g of ethanol and 77 g of water. This composition is a standard dishwashing composition.
  • Composition II 1.68 g of sodium lauryl ether sulfate with 3 ethylene oxide groups, 10.8 g of C12-C18 alkane sulfonate, 2.22 g of amphoteric compounds, a 1:1 mixture of amphoteric compounds sold under the trade marks Ampholak (R) XCO-30 and Ampholak (R) 7TX, respectively, 1.11 g of alkyl dimethyl amine oxide wherein the alkyl group had 14 carbon atoms and 84.19 g of water.
  • the first mentioned amphoteric compound can chemically be characterized as cocoamphocarboxyglycinate and contains a carbonyl group and comprises a mixture of compounds defined in formulae IIIa and IIIb) and the other one can chemically be described as tallowampho polycarboxyglycinate, corresponds to formulae II and does not contain a carbonyl group.
  • composition II The efficiency of composition II according to the invention was set in relation to this and found to be 2.4.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Claims (7)

  1. Composition liquide pour le lavage de la vaisselle, caractérisée en ce qu'elle comprend :
    a) un mélange d'au moins un composé amphotère de formule :
    Figure imgb0019
     dans laquelle R est un groupe hydrocarboné ayant de 7 à 22 atomes de carbone, A est le groupe (C(O)), n vaut 0 ou 1, R₁ est l'hydrogène ou un groupe alkyle ayant de 1 à 6 atomes de carbone, x vaut 2 ou 3, y est un entier compris entre 0 et 4, Q est le groupe -R₂COOM où R₂ est un groupe alkylène ayant de 1 à 6 atomes de carbone et M est l'hydrogène ou un ion de métal alcalin, de métal alcalino-terreux, ammonium ou ammonium substitué, et B est l'hydrogène ou un groupe Q tel que défini ;
    ou de formule :
    Figure imgb0020
     dans laquelle y vaut 1, 2 ou 3, R est un groupe hydrocarboné ayant de 7 à 22 atomes de carbone, A est le groupe (C(O)), n vaut 0 ou 1, x vaut 2 ou 3, y vaut 1, 2 ou 3, Q est -CH₂-COOM ou CH₂CH₂-COOM, M est l'hydrogène ou un ion de métal alcalin, de métal alcalino-terreux, ammonium ou ammonium substitué, et B est l'hydrogène ou un groupe Q tel que défini ;
    dans lequel n vaut 1,
    et d'au moins un composé amphotère de formule I ou II dans lequel n vaut 0,
    ou un mélange d'au moins un composé amphotère de formule :
    Figure imgb0021
     dans laquelle R, A, y, Q et B ont les mêmes significations que celles indiquées à propos des composés de formule (I), un groupe B étant toutefois le groupe -CH₂CHR'OH où R' est H ou CH₃,
    en combinaison avec le composé amphotère de formule I ou II dans lequel n vaut 0,
    et d'au moins un composé amphotère de formule I ou II dans lequel n vaut 0,
    selon un rapport en poids compris entre 1/10 et 10/1,
    b) un renforçateur de mousse qui est un amide, une amido-bétaïne ou un oxyde d'amine, contenant au moins un groupe hydrocarboné hydrophobe à longue chaîne ayant 7 à 22 atomes de carbone,
    c) un tensioactif anionique,
    le rapport du renforçateur de mousse aux composés amphotères étant compris entre 1/10 et 10/1 et la quantité du tensioactif anionique étant comprise entre 20 et 90 % en poids par rapport à la quantité totale des composés amphotères et du tensioactif anionique.
  2. Composition pour le lavage de la vaisselle selon la revendication 1, caractérisée en ce qu'elle contient au moins un composé amphotère de formules :
    Figure imgb0022
     et/ou
    Figure imgb0023
     dans lesquelles R, A et M ont les mêmes significations que celles indiquées ci-dessus à propos des composés amphotères de formules (I) et (II), et au moins un composé amphotère de formule I ou II, dans lequel n vaut 0 ; selon un rapport en poids compris entre 1/5 et 5/1.
  3. Composition pour le lavage de la vaisselle selon l'une quelconque des revendications précédentes, caractérisée en ce que R, dans les composés amphotères, est un groupe alkyle ou alcényle ayant de 12 à 22 atomes de carbone.
  4. Composition pour le lavage de la vaisselle selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle comprend des composés amphotères de formule I ou II dans lesquels n vaut 0 et tous les groupes B sont des groupes Q.
  5. Composition pour le lavage de la vaisselle selon la revendication 1, caractérisée en ce que le renforçateur de mousse est un oxyde d'amine.
  6. Composition pour le lavage de la vaisselle selon la revendication 1, caractérisée en ce que le tensioactif anionique est un sel soluble dans l'eau d'un alcool sulfaté ou d'un acide sulfoné organique.
  7. Utilisation d'un mélange de composés amphotères et d'un renforçateur de mousse conformes à la revendication 1, 2, 3, 4 ou 5, dans une composition liquide pour le lavage de la vaisselle contenant un tensioactif anionique, pour remplacer une partie du tensioactif anionique, le mélange de composés amphotères étant utilisé en une quantité telle que le tensioactif anionique représente 20 à 90 % en poids de la quantité totale du tensioactif anionique et du mélange de composés amphotères.
EP91910074A 1990-09-19 1991-04-09 Composition liquide de lavage de vaisselle Expired - Lifetime EP0500819B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE9002986 1990-09-19
SE9002986A SE9002986D0 (sv) 1990-09-19 1990-09-19 Flytande diskmedelskomposition
PCT/SE1991/000257 WO1992005236A1 (fr) 1990-09-19 1991-04-09 Composition liquide de lavage de vaisselle

Publications (2)

Publication Number Publication Date
EP0500819A1 EP0500819A1 (fr) 1992-09-02
EP0500819B1 true EP0500819B1 (fr) 1996-03-06

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EP91910074A Expired - Lifetime EP0500819B1 (fr) 1990-09-19 1991-04-09 Composition liquide de lavage de vaisselle

Country Status (11)

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EP (1) EP0500819B1 (fr)
JP (1) JPH05502265A (fr)
AT (1) ATE135038T1 (fr)
AU (1) AU7903291A (fr)
DE (1) DE69117726T2 (fr)
DK (1) DK0500819T3 (fr)
ES (1) ES2084165T3 (fr)
FI (1) FI922184A (fr)
NO (1) NO179952C (fr)
SE (1) SE9002986D0 (fr)
WO (1) WO1992005236A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2121888B1 (fr) 2007-03-08 2015-04-22 Rhodia Operations Utilisation d'une betaïne a titre d'agent de reduction du drainage de la mousse

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE469428B (sv) * 1991-11-21 1993-07-05 Berol Nobel Ab Flytande diskmedelskomposition innehaallande anjonisk tensid och en kombination av tre typer av amfotaera foereningar
US5269974A (en) * 1992-09-01 1993-12-14 The Procter & Gamble Company Liquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions
SE9203373L (sv) * 1992-11-11 1994-05-12 Berol Nobel Ab Flytande diskmedelskomposition
SE502482C2 (sv) * 1993-06-30 1995-10-30 Berol Nobel Ab Schampokompositioner innefattande en amfoter förening av alkylaminopolyamfokarboxiglycinattypen, en blandning av två monoetanolamider och ett anjoniskt ytaktivt medel
US5801139A (en) * 1997-06-05 1998-09-01 Lever Brothers Company, Division Of Conopco, Inc. Process for making bar compositions comprising novel chelating surfactants
US5869441A (en) * 1997-06-05 1999-02-09 Lever Brothers Company, Division Of Conopco, Inc. Bar compositions comprising novel chelating surfactants

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8522413D0 (en) * 1985-09-10 1985-10-16 Amphoterics International Ltd Surfactants
US4876034A (en) * 1986-11-18 1989-10-24 Kao Corporation Secondary amidoamino acid based detergent composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2121888B1 (fr) 2007-03-08 2015-04-22 Rhodia Operations Utilisation d'une betaïne a titre d'agent de reduction du drainage de la mousse

Also Published As

Publication number Publication date
ES2084165T3 (es) 1996-05-01
DE69117726T2 (de) 1996-07-18
AU7903291A (en) 1992-04-15
NO179952B (no) 1996-10-07
EP0500819A1 (fr) 1992-09-02
NO179952C (no) 1997-01-15
DE69117726D1 (de) 1996-04-11
SE9002986D0 (sv) 1990-09-19
DK0500819T3 (da) 1996-06-24
FI922184A0 (fi) 1992-05-13
FI922184A (fi) 1992-05-13
NO921960L (no) 1992-07-20
NO921960D0 (no) 1992-05-18
ATE135038T1 (de) 1996-03-15
WO1992005236A1 (fr) 1992-04-02
JPH05502265A (ja) 1993-04-22

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