WO1999010463A1 - Detergents aqueux pour laver la vaisselle a la main - Google Patents

Detergents aqueux pour laver la vaisselle a la main Download PDF

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Publication number
WO1999010463A1
WO1999010463A1 PCT/EP1998/005201 EP9805201W WO9910463A1 WO 1999010463 A1 WO1999010463 A1 WO 1999010463A1 EP 9805201 W EP9805201 W EP 9805201W WO 9910463 A1 WO9910463 A1 WO 9910463A1
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Prior art keywords
alkyl
carbon atoms
composition according
fatty acid
contain
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PCT/EP1998/005201
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German (de)
English (en)
Inventor
Hermann Hensen
Bernd Fabry
Karl Heinz Schmid
Michael Elsner
Hans-Christian Raths
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Cognis Deutschland Gmbh
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Priority claimed from DE19736906A external-priority patent/DE19736906A1/de
Priority claimed from DE19741911A external-priority patent/DE19741911C1/de
Priority claimed from DE1998113045 external-priority patent/DE19813045A1/de
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Publication of WO1999010463A1 publication Critical patent/WO1999010463A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2669—Non-metals or compounds thereof
    • C08G65/2672—Nitrogen or compounds 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/65—Mixtures of anionic with cationic 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
    • C11D1/83—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
    • C11D1/86—Mixtures of anionic, cationic, and 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
    • C11D1/88—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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
    • 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
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • 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
    • C11D1/90—Betaines

Definitions

  • the invention relates to aqueous hand dishwashing detergents containing fatty acid polyglycol ester sulfates and other surfactants, and to the use of these mixtures for producing manual hand dishwashing detergents.
  • Concentrated surfactant solutions are usually used for manual cleaning of soiled dishes, to which a whole series of very different requirements are made today. The funds should
  • the invention relates to aqueous dishwashing detergents containing
  • the agents according to the invention are also highly concentrated, flowable, have a low cloud point, largely irrespective of the concentration, are not irritating to the skin and at the same time still have a voluminous foam which is stable even under high fat loads and an excellent dishwashing capacity.
  • the invention includes the finding that mixtures of fatty acid polyglycol ester sulfates with alkyl sulfates, alkyl ether sulfates, monoglyceride sulfates, sulfosuccinates, alkyl oligoglucosides and / or betaines leads to a further improvement in the desired properties.
  • Fatty acid polyglycol ester sulfates which may be present as component (a) preferably follow the formula (I),
  • R 1 CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, x for numbers from 1 to 3 on average and AO for a CH2CH2O-, CH2CH (CH3) 0- and / or CH (CH3) CH 2 0 radical and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, and are usually prepared by sulfation of the corresponding fatty acid polyglycol ester. These in turn can be obtained using the relevant preparative processes in organic chemistry.
  • ethylene oxide, propylene oxide or a mixture thereof - in random or block distribution - is added to the corresponding fatty acids, this reaction being acid-catalyzed, but preferably in the presence of bases, such as, for example, sodium methylate or calcined hydrotalcite.
  • bases such as, for example, sodium methylate or calcined hydrotalcite.
  • the intermediates can also be prepared by esterifying the fatty acids with an appropriate alkylene glycol.
  • the sulfation of the fatty acid polyglycol esters can be carried out in a manner known per se with chlorosulfonic acid or preferably gaseous sulfur trioxide, the molar ratio between fatty acid polyglycol ester and sulfating agent being in the range from 1: 0.95 to 1: 1, 2, preferably 1: 1 to 1: 1 , 1 and the reaction temperature can be 30 to 80 and preferably 50 to 60 ° C. It is also possible to undersulfate the fatty acid polyglycol esters, ie to use significantly fewer sulfating agents than would be stoichiometrically required for complete conversion.
  • Typical examples of suitable starting materials are the addition products of 1 to 3 moles of ethylene oxide and / or propylene oxide, but preferably the adducts with 1 mole of ethylene oxide or 1 mole of propylene oxide with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, Palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, which are then sulfated and neutralized as described above.
  • Fatty acid polyglycol ester sulfates of the formula (I) are preferably used in which R 1 CO stands for an acyl radical having 12 to 18 carbon atoms, x for an average of 1 or 2, AO for a CH2CH2 ⁇ group and X for sodium or ammonium, such as lauric acid + 1 EO sulfate sodium salt, lauric acid + 1 EO sulfate ammonium salt, coconut fatty acid + 1 EO sulfate sodium salt, coconut fatty acid + 1 EO sulfate ammonium salt, tallow fatty acid + 1 EO sulfate sodium salt, tallow fatty acid + 1 EO sulfate Ammonium salt and mixtures thereof.
  • R 1 CO stands for an acyl radical having 12 to 18 carbon atoms
  • x for an average of 1 or 2
  • AO for a CH2CH2 ⁇ group
  • X for sodium or ammonium, such as lauric acid + 1 EO s
  • anionic surfactants which can be considered as component (b) are soaps, alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, alkyl ether sulfates, glycerol ether sulfate, mono ether sulfate, monoglyme sulfate, monoglyme sulfate , fatty acid amide (ether) sulfates, mono- and Dialkylsulfo- succinate, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid taurides, N-acylamino acids
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution. Alkyl sulfates, alkyl ether sulfates and / or sulfosuccinates are preferably used.
  • the agents according to the invention can contain components (a) and (b) in a weight ratio of 90:10 to 10:90, preferably 75:25 to 15:85 and in particular 60:40 to 25:75.
  • nonionic surfactants which can be considered as component (c) are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxyated triglycerides, alk (en) yl oligoglycosides, especially fatty acid-N-alkyl-vegetable protein gluamides, fatty acid-N-vegetable-alkyl-fatty acids Wheat-based products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • Fatty alcohol polyglycol ethers, alkyl oligoglucosides, fatty acid N-alkyl glucamides and / or betaines are preferably used.
  • the agents according to the invention can contain components (a) and (c) in a weight ratio of 90:10 to 10:90, preferably 75:25 to 25:75 and in particular 60:40 to 40:60 and components (a), (b) and (c) in the weight ratio (10 to 90): (5 to 85): (5 to 85) and in particular (20 to 80): (10 to 50): (10 to 50), with the proviso that add the weight information to 100% by weight.
  • nonionic surfactants used are alkyl and alkenyl oligoglycosides which follow the formula (II)
  • R 2 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglycosides.
  • the index number p in the general formula (II) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • alkyl oligo glycoside is an analytically calculated value that usually represents a fractional number.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization -p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 1.7 and is in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 2 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms.
  • Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyial alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, and the technical mixtures described above. Alkyl oligoglucosides based on hardened Ci2 are preferred. .4 coconut alcohol with a DP of 1 to 3.
  • component (c) Another group of preferred nonionic surfactants which can form component (c) are fatty acid N-alkylpolyhydroxyalkylamides which follow the formula (III)
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • H.Kelkenberg An overview of this topic by H.Kelkenberg can be found in Tens.Surf.Deterg. 25, 8 (1988).
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (IV):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (IV) in which R 4 is an alkyl group and R 3 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • R 4 is an alkyl group and R 3 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, Oleic acid, elaidic acid, petroselinic acid, lino
  • Fatty acid N-alkylglucamides of the formula (IV) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C12 / 14-coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • surfactants of the betaine type can form component (c).
  • Betaines are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation, of aminic compounds.
  • the starting materials are preferably condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, one mol of salt being formed per mole of betaine.
  • unsaturated carboxylic acids such as acrylic acid, is also possible.
  • R 5 represents alkyl and / or alkenyl radicals having 6 to 22 carbon atoms
  • R 6 represents hydrogen or alkyl radicals having 1 to 4 carbon atoms
  • R 7 represents alkyl radicals having 1 to 4 carbon atoms
  • n represents numbers from 1 to 6 and X for a alkali and / or alkaline earth metal or ammonium
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, Removal cyldimethylamin, dodecylmethylamine, dodecyldimethylamine, Dodecylethylmethylamin, Ci2 / i4-Kokosal- kyldimethylamin, My ⁇ styldimethylamin, cetyldimethylamine, Stearyidimethylamin, Stearylethylmethyl- amine, Oleyldimethylamm , Ci6 / 18
  • R 8 CO represents an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
  • m represents numbers from 1 to 3
  • R 6 , R 7 , n and X have the meanings given above.
  • Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, including caproic, caprylic acid, Cap ⁇ nsaure, lauric acid, My ⁇ stmsaure, palmitic tinsaure, Palmoleinsaure, stearic acid, Isosteannsaure, oleic acid, Elaidmsaure, Petroselmsaure linoleic acid, linolenic acid, Elaeosteannsaure, Arachmsaure, Gadoleinsaure, behenic acid and erucic acid and their Technical mixtures with NN-dimethylaminoethylamine, N, N-dimethylamino-
  • R 9 is an alkyl radical having 5 to 21 carbon atoms
  • R 10 is a hydroxyl group
  • an OCOR 9 or NHCOR 9 radical and m is 2 or 3.
  • These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines, such as, for example, aminoethylethanoiamine (AEEA) or diethylenetriamine.
  • AEEA aminoethylethanoiamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the above-mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again Ci2 / 14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • the invention further relates to the use of the surfactant mixtures according to the invention for the production of hand dishwashing detergents.
  • the mixtures may contain minor amounts of other customary auxiliaries and additives, such as foam boosters, fragrances, etc.
  • the agents usually have an active substance or surfactant content - based on components (a), (b) and (c) - of 10 to 50 and preferably 15 to 35% by weight.
  • the foaming power was determined by the Ross Miles method using 1% by weight surfactant solutions at 20 ° C. in the presence of 1 g / l of dispersed olive oil. The base foam and the foam height are given after 5 minutes.
  • the determination of the dishwashing capacity was carried out with the help of the dish test [Fette, Seifen, Anstrichmitt., 74, 163 (1972)]. For this purpose, plates with a diameter of 14 cm were soiled with 2 cm 3 of beef tallow (acid number 9-10) and stored for 24 hours at room temperature. The plates were then rinsed at 50 ° C. with 5 liters of tap water with a hardness of 16 ° d.
  • test mixtures were used at a dosage of 0.15 g active substance / l. The rinsing attempt was stopped as soon as the foam had completely disappeared.
  • skin tolerance of the comparison formulation V1 was selected as the standard according to the zeintest and all the information related to it.
  • Formulations 1 to 8 are according to the invention, formulations V1 and V2 are used for comparison. The results are summarized in Table 1.

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Abstract

L'invention concerne de nouveaux détergents aqueux pour laver la vaisselle à la main, qui contiennent (a) des sulfates d'ester de polyglycol d'acide gras, (b) des tensioactifs anioniques et (c) des tensioactifs non ioniques et/ou amphotères ou zwitterioniques. Ces agents se caractérisent non seulement en ce qu'ils présentent un excellent pouvoir de lavage au niveau des assiettes, mais également en ce que leur tenue de mousse est remarquable, même lorsque l'eau de vaisselle est chargée en graisses. En outre, sur le plan cosmétique, ils sont parfaitement bien tolérés par la peau.
PCT/EP1998/005201 1997-08-25 1998-08-17 Detergents aqueux pour laver la vaisselle a la main WO1999010463A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE19736906.5 1997-08-25
DE19736906A DE19736906A1 (de) 1997-08-25 1997-08-25 Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
DE19741911.9 1997-09-25
DE19741911A DE19741911C1 (de) 1997-09-25 1997-09-25 Stark schäumende Detergensgemische
DE19813045.7 1998-03-25
DE1998113045 DE19813045A1 (de) 1998-03-25 1998-03-25 Wäßrige Handgeschirrspülmittel

Publications (1)

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WO1999010463A1 true WO1999010463A1 (fr) 1999-03-04

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999049007A1 (fr) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Produit vaisselle comprenant des sulfates d'ester d'oligoalkylenglycol d'acide gras
KR100697813B1 (ko) * 2004-07-21 2007-03-20 삼성에스디아이 주식회사 연료전지용 전해질, 이를 이용한 막전극 접합체, 연료전지 스택, 연료전지 및 상기 연료전지용 전해질의 제조 방법
WO2015178902A1 (fr) * 2014-05-21 2015-11-26 Colgate-Palmolive Company Composition aqueuse de liquide vaisselle

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010208A1 (fr) * 1991-11-18 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents aqueux
DE4236506A1 (de) * 1992-10-29 1994-05-05 Henkel Kgaa Verfahren zur Herstellung wäßriger Lösungen anionischer Tenside mit verbesserter Kältestabilität
DE19527596A1 (de) * 1995-07-28 1997-01-30 Henkel Kgaa Wäßrige Tensidmischung
EP0763591A1 (fr) * 1995-09-15 1997-03-19 Henkel Kommanditgesellschaft auf Aktien Produit pour laver la vaiselle à la main

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010208A1 (fr) * 1991-11-18 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents aqueux
DE4236506A1 (de) * 1992-10-29 1994-05-05 Henkel Kgaa Verfahren zur Herstellung wäßriger Lösungen anionischer Tenside mit verbesserter Kältestabilität
DE19527596A1 (de) * 1995-07-28 1997-01-30 Henkel Kgaa Wäßrige Tensidmischung
EP0763591A1 (fr) * 1995-09-15 1997-03-19 Henkel Kommanditgesellschaft auf Aktien Produit pour laver la vaiselle à la main

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999049007A1 (fr) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Produit vaisselle comprenant des sulfates d'ester d'oligoalkylenglycol d'acide gras
WO1999049006A1 (fr) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Sulfates d'ester d'oligoalkylenglycol d'acide gras dans des solutions aqueuses
KR100697813B1 (ko) * 2004-07-21 2007-03-20 삼성에스디아이 주식회사 연료전지용 전해질, 이를 이용한 막전극 접합체, 연료전지 스택, 연료전지 및 상기 연료전지용 전해질의 제조 방법
WO2015178902A1 (fr) * 2014-05-21 2015-11-26 Colgate-Palmolive Company Composition aqueuse de liquide vaisselle
US10329521B2 (en) 2014-05-21 2019-06-25 Colgate-Palmolive Company Aqueous liquid dishwashing composition comprising an ammonium alkyl ether sulfate and alkylamidopropyl betaine

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