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WO1999049006A1 - Sulfates d'ester d'oligoalkylenglycol d'acide gras dans des solutions aqueuses - Google Patents

Sulfates d'ester d'oligoalkylenglycol d'acide gras dans des solutions aqueuses Download PDF

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Publication number
WO1999049006A1
WO1999049006A1 PCT/EP1999/001698 EP9901698W WO9949006A1 WO 1999049006 A1 WO1999049006 A1 WO 1999049006A1 EP 9901698 W EP9901698 W EP 9901698W WO 9949006 A1 WO9949006 A1 WO 9949006A1
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Prior art keywords
mpa
fatty acid
sulfates
formula
weight
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PCT/EP1999/001698
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German (de)
English (en)
Inventor
Christian Block
Berthold Schreck
Hans-Christian Raths
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority claimed from DE1998113042 external-priority patent/DE19813042A1/de
Priority claimed from DE19813043A external-priority patent/DE19813043A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1999049006A1 publication Critical patent/WO1999049006A1/fr
Anticipated expiration legal-status Critical
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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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
    • 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
    • C11D1/88—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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D1/29—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
    • C11D1/66—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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the present invention relates to the use of fatty acid oligoalkylene glycol ester sulfates in aqueous surfactant solutions for adjusting the viscosity and aqueous surfactant solutions of defined viscosity with fatty acid oligoalkylene glycol ester sulfates and alkyl ether sulfates.
  • Aqueous surfactant solutions especially those used in the field of cleaning agents used as all-purpose cleaners, dishwashing detergents or carpet care products and in the field of body care as hair shampoos, bubble baths, shower baths, hand washing pastes and the like, usually contain anionic surfactants, for example alkyl ether sulfates.
  • anionic surfactants for example alkyl ether sulfates.
  • thickening agents are usually added to these surfactant solutions.
  • Figure 9 on page 24 shows that the input Setting a viscosity of 10,000 mPa-s in the case of the solution of the C 12 / i 4 fatty alcohol 3EO ether sulfate 5% by weight NaCl and in the case of the solution of the C 2 / i4 fatty acid 4EO ester sulfate even 8%. -% NaCl required.
  • organic thickeners are fatty acid alkanolamides, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • organic thickeners In most cases it is at most possible to use large amounts to adjust the desired viscosity of the surfactant solution by using only inorganic electrolyte salts. It is therefore generally the way to use organic thickeners in addition to the inorganic salts, but some of them have a number of disadvantages.
  • the surfactant solutions thickened with polyethylene glycol fatty acid diesters often have inadequate viscosity stability during storage, while water-soluble polymers have an undesirable slimy flow behavior with a tendency to become stringy in the thickened surfactant solutions.
  • This object was achieved according to the invention by using fatty acid oligoalkylene glycol ester sulfates, in particular in combination with alkyl ether sulfates.
  • the present invention therefore relates to the use of fatty acid oligoalkylene glycol ester sulfates of the formula I for adjusting the viscosity of aqueous surfactant solutions,
  • IM stands for a cation, in particular an ammonium ion
  • R 1 CO for a linear or branched, aliphatic, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
  • Another object of the present invention are aqueous surfactant solutions, the fatty acid oligoalkylene glycol ester sulfates of the formula I, R 1 COO (R 2 0) n S0 3 M (I)
  • R 2 0) is an alkylene radical, in particular CH 2 CH 2 or CH (CH 3 ) CH 2 or CH 2 CH (CH 3 ), where n is then a Number from 0.5 to 5, preferably 0.7 to 3, in particular 0.9 to 2, stands or represents (R 2 0) "a unit of the type (EO) u (PO)" (EO) ", where E is CH 2 CH 2 and P is CH (CH 3 ) CH 2 and CH 2 CH (CH 3 ) as well as 0 ⁇ u ⁇ 5, 0.1 ⁇ v ⁇ 5, 0 ⁇ w ⁇ 5 and u + w> 0 and the sum u + v + w assumes a value of 0.5 to 5, preferably 0.7 to 3, in particular 0.9 to 2, contain and at room temperature a vis
  • these surfactant solutions additionally contain alkyl ether sulfates of the formula II,
  • R 3 stands for a saturated or unsaturated C 8 -C 22 alkyl group, m for numbers from 1 to 10 and M 'for an alkali or an alkaline earth metal cation or an ammonium ion, in a weight ratio of fatty acid oligoalkylene glycol ester sulfates to alkyl ether sulfates in the range from 1 to 4 to 2 to 1, preferably 1 to 3.5 to 1.5 to 1, in particular 1 to 3 to 1 to 1, or in a ratio in the range from 5 to 1 to 100 to 1, preferably at least 8 to 1, especially at least 10 to 1.
  • the present invention also relates to aqueous surfactant solutions which contain fatty acid oligoalkylene glycol ester sulfates of the formula I,
  • these surfactant solutions additionally contain alkyl ether sulfates of the formula II,
  • R 3 stands for a saturated or unsaturated C 8 -C 22 alkyl group, m for numbers from 1 to 10 and M 'for an alkali or an alkaline earth metal cation or an ammonium ion, in a weight ratio of fatty acid oligoalkylene glycol ester sulfates to alkyl ether sulfates in the range from 1 to 1.2 to 12 to 1, preferably 1.3 to 1 to 8 to 1, in particular 2 to 1 to 5 to 1, or in a ratio in the range from 1 to 20 to 1 to 1.9 , preferably 1 to 10 to 1 to 2.1, in particular 1 to 7 to 1 to 2.3.
  • An essential advantage of the invention is to achieve a desired effect, ie a certain viscosity, without using a component that is only useful for this purpose, but moreover is more harmful than useful and therefore undesirable per se, usually a thickener, but through the skilful use of the properties or the interaction of the core components of a surfactant solution, namely the surfactant.
  • the invention thus makes surfactant solutions of defined viscos also accessible without the use of a thickener.
  • aqueous surfactant solutions according to the invention are notable for their skin-friendliness and are suitable as cleaning agents.
  • Preferred surfactant solutions according to the invention are, for example, high-performance hand dishwashing detergents whose viscosity can be adjusted in a wide range in a targeted manner solely by metering the fatty acid oligoalkylene glycol ester sulfates or the weight ratio of fatty acid oligoalkylene glycol ester sulfate to alkyl ether sulfate, without appreciably impairing the cleaning action and without adding an additional thickening agent (see examples).
  • Another advantage of the surfactant solutions according to the invention is their good emulsifying power.
  • An increasing proportion of fatty acid oligoalkylene glycol ester sulfate (A) results in an increasing stability of the emulsion, whereby in combination with alkyl ether sulfate (B) a surprisingly high increase in stability can be found even with a weight ratio A to B of 1 to 1 (see examples).
  • the fatty acid oligoalkylene glycol ester sulfates (FSES) of the formula I according to the invention are known compounds which are distinguished by excellent skin compatibility and by sulfating fatty acid oligoalkylene glycol esters of the formula R 1 C00 (R 2 0) n H, in which R 1 , R 2 and n or . (R 2 0) n have the same meaning as in formula I, are accessible (cf. K. Engel, W. Ruback Fette, Seifen und Anstrichstoff 1986, 88, 20-25).
  • the sulfation is preferably carried out with sulfur trioxide in a molar ratio of 1 to 1 to 1 to 1.3, in particular 1 to 1.05 to 1 to 1.1, on a continuously working falling film reactor preferably at temperatures of at least 5 to 10 ° C.
  • the melting point of the fatty acid oligoalkylene glycol esters followed by neutralization of the acidic ester obtained with alkali metal hydroxides, alkaline earth metal hydroxides, ammonia and / or water-soluble organic amines, preferably NaOH, KOH and / or NH 3 , in the form of their 20 to 50% by weight aqueous solutions, the pH in a range from 5 to 9, preferably 6 to 8, and the temperature preferably between 10 and 40 ° C., in particular 20 and 35 ° C. , is held.
  • alkali metal hydroxides alkaline earth metal hydroxides, ammonia and / or water-soluble organic amines, preferably NaOH, KOH and / or NH 3
  • the fatty acid oligoalkylene glycol esters used in the sulfation can be prepared, for example, according to application P 19736906.5 above by basic homogeneously catalyzed addition of ethylene oxide and / or propylene oxide to fatty acids.
  • amines such as alkanolamines, preferably monoethanolamine or diethanolamine, in particular triethanolamine, in amounts, based on the amount of fatty acids, of 0.1 to 5% by weight, preferably 0.5 to 1.5% by weight, described there. %, as a catalyst it is now also possible to obtain selectively low-alkoxylated, in particular low-ethoxylated, products with a narrow homolog distribution and a low proportion of by-products.
  • the alkoxylation of the fatty acids with 0.5 to 5, preferably 1 to 2 equivalents, based on the amounts of material, ethylene oxide, propylene oxide or an ethylene oxide / propylene oxide mixture can be carried out in a known manner at temperatures from 80 to 180 ° C., preferably 100 to 120 ° C, under autogenous pressure of 1 to 5 bar, preferably 2 to 3 bar.
  • FSES with conventional as well as preferably with narrowed homolog distribution are suitable according to the invention.
  • the FSES according to the invention can - if necessary for production reasons - to a lesser extent glycol mono- and glycol disulfa- te, fatty acid soaps, unsulfated parts and / or inorganic sulfates.
  • the FSES are sulfates of alkoxylated aliphatic carboxylic acids of the formula R ⁇ -COOH, in which R x CO is an aliphatic, linear or branched acyl radical having 6 to 22, preferably 12 to 18, carbon atoms and 0, 1, 2 or 3 double bonds.
  • Typical examples are the oligoalkyl ester sulfates of caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, linoleic acid, linoleic acid, linoleic acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, lauric acid, elauric acid, Gadolic acid, behenic acid and erucic acid as well as their technical mixtures, which occur, for example, in the pressure splitting of natural fats and oils.
  • the sulfates of the formula I with an average degree of alkoxylation n or (u + v + w) of 0.7 to 3, preferably 0.9 to 2 are preferred.
  • Further cations M according to the invention are alkali and alkaline earth metal cations, in particular Mg 2+ .
  • the fatty acid oligoalkylene glycol ester sulfates are used to adjust the viscosity of aqueous surfactant solutions in which C 8 -C 22 -alkyl ether sulfates according to formula II are used as a further surfactant component.
  • the aqueous surfactant solution contains 1 to 70% by weight, in particular 3 to 50% by weight, extremely preferably 6 to 30% by weight, of fatty acid oligoalkylene glycol ester sulfates.
  • aqueous surfactant solutions according to the invention necessarily contain C 8 -C 22 -alkyl ether sulfates according to formula II in amounts, based on the composition, of usually 0.1 to 40% by weight, preferably 0.1 to 20% by weight, in particular 1 to 13% by weight, most preferably 2 to 9% by weight.
  • Typical examples are the sulfation products of adducts of 0.5 to 10 mol ethylene oxide (conventional or restricted homolog distribution) with 1 mol capryl alcohol, caprinal alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol , Arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol as well as their technical mixtures or also with 1 mole of a petrochemical alcohol such as the commercially available C ⁇ 2 / ⁇ 3 oxo alcohols Neodol 23 ® or Lial 123 ® .
  • a petrochemical alcohol such as the commercially available C ⁇ 2 / ⁇ 3 oxo alcohols Neodol 23 ® or Lial 123 ® .
  • Sulfates of adducts of 1 to 7 moles of ethylene oxide with saturated coconut oil alcohols in the form of their sodium, potassium and / or magnesium salts and ammonium salts, such as monoisopropanolammonium salts, are preferred.
  • alkyl ether sulfates can be used, which are derived from corresponding fatty alcohol polyglycol ethers, which in turn are present in the presence of calcined or, in particular, hydrogenated phobicized hydrocalcite have been produced and therefore have a particularly advantageous narrow homolog distribution.
  • the surfactant solutions according to the invention can be C 8 -C 22 carboxamide amide sulfates of the formula R-CO-NH (CH 2 CH 2 0) j -S0 3 X, in which R represents a saturated or unsaturated C 8 -C 22 - Alkyl group, j are numbers from 1 to 10 and X is an alkali metal, alkaline earth metal or quaternary ammonium ion.
  • C 8 -C 22 carboxylic acid amide ether sulfates are known anionic surfactants which have a pronounced foaming capacity and low sensitivity to hardness (cf. A. Reng Parf. And Kosmetik 1980, 61, 87-97). They can be produced by methods known from the prior art (cf. J. Falbe Surfactants in Consumer Products 1987, Springer Verlag, p. 93 ff.).
  • C 8 -C 22 carboxylic acid amide ether sulfates are the sulfated adducts of 1 to 10 moles of ethylene oxide (conventional or narrowed homolog distribution) with 1 mole of carboxylic acid real alkanolamide, such as, for example, the amide of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitolemic acid , Stearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, lmoleic acid, arachic acid, gadoleic acid, behenic acid and erucic acid.
  • carboxylic acid real alkanolamide such as, for example, the amide of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitolemic acid , Stearic acid, oleic acid, elaidic acid, petroselinic acid, l
  • the fatty acid component of the amides can also be derived from technical fatty acid cuts, such as those that occur in the pressure splitting of natural fats and oils, for example palmol, palm kernel oil, coconut oil, rubol or beef tallow.
  • Preferred feedstocks are the carboxylic acid amide ether sulfates of coconut fatty acid.
  • the C 8 -C 22 -carboxylic acid amide ether sulfates can be used in the surfactant solutions according to the invention in amounts of 0.01 to 60% by weight, based on the finished solution, preferably 0.1 to 40% by weight, in particular 0.2 to 25% by weight, most preferably 0.5 to 15% by weight, can be contained.
  • anionic surfactants for example, alkyl sulfates with 8 to 22 carbon atoms in the alkyl radical, n-alkylbenzenesulfonates with 9 to 16 carbon atoms in the alkyl radical, alkanesulfonates with 10 to 20 carbon atoms in the alkyl radical and / or olefin sulfonates with 12 to 16 carbon atoms in the alkyl radical can be present in the surfactant solutions according to the invention .
  • Soaps ie alkali or ammonium salts of saturated or unsaturated C 8 -C 22 fatty acids, are preferably not contained in the surfactant combinations according to the invention because of their foam-suppressing properties.
  • the feature "preferably not included” is intended to mean that very small amounts of soap of up to 2% by weight, based on the total solution, can still be tolerated in the sense of the invention.
  • the preferred nonionic surfactants are alkyl polyglycosides (APG) of the formula III,
  • R 4 is a linear or branched, saturated or unsaturated alkyl radical having 8 to 22 carbon atoms
  • [G] is a glycosidically linked sugar radical and x is a number from 1 to 10.
  • APG are non-ionic surfactants and are known substances that can be obtained using the relevant methods of preparative organic chemistry.
  • the surfactant solutions according to the invention preferably contain APG in amounts of 0.1 to 20% by weight, in particular 0.5 to 10% by weight, extremely preferably 1 to 5% by weight, and / or in a ratio to the total amount of anionic surfactant from 1: 8 to 1: 4, in particular 1: 7 to 1: 5.
  • the alkyl or alkenyl radical R 4 (formula III) can be derived from primary alcohols having 8 to 18, preferably 8 to 14, carbon atoms. Typical examples are capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as those obtained in the course of the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from RoELEN's oxo synthesis.
  • the alkyl or alkenyl radical R 4 is preferably derived from lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol or oleyl alcohol.
  • Elaidyl alcohol, petroselinyl alcohol, arachidyl alcohol, gadolinyl alcohol, behenyl alcohol, erucyl alcohol and their technical mixtures are also to be mentioned.
  • Nonionic surfactants are C 8 -C 18 alcohol alkoxylates of the formula R'O- (CH 2 CH 2 0), -H are used, wherein R 'is a saturated or unsaturated C 8 -C ⁇ 8 alkyl group, and i for Numbers from 1 to 20 stands.
  • the fatty alcohol alkoxylates are known compounds which can be obtained by alkoxylating the fatty alcohols.
  • Alcohol alkoxylates ⁇ The fat may be present in an amount of 0.1 to 15 wt .-% in the surfactant solution according to the invention.
  • nonionic surfactants that can be used are fatty acid alkanolamides, for example CIO / 22 fatty acid monoethanolamide or addition products of 4 to 20, preferably 4 to 10, moles of C 2 -C 3 -alkylene oxide, preferably ethylene oxide to C 0 -C 20 , preferably C 2 -C 2 8 -alkanols, as well as the adducts of ethylene oxide and propylene glycols, which are known under the name Pluronics ®, as well as addition products of 1 to 7 moles of ethylene oxide with 1 to 5 moles of propylene oxide converted C suitable 12 -C 18 alkanols.
  • Fatty alkyl amine oxides are also suitable.
  • Fatty acid N-alkylpolyhydroxyalkylamides can also be used as nonionic surfactants, which are also known substances which are usually obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, one Fatty acid alkyl esters or a fatty acid chloride can be obtained.
  • nonionic surfactants which are also known substances which are usually obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, one Fatty acid alkyl esters or a fatty acid chloride can be obtained.
  • Preferred fatty acid N-alkylpolyhydroxyalkylamides are the fatty acid N-alkylglycamides derived from reducing sugars with 5 or 6 carbon atoms, in particular glucose.
  • R 5 optionally by heteroatoms or hetero- alkyl groups interrupted by atomic groups and having 8 to 25, preferably 10 to 21 carbon atoms and R 6 and R 7 are identical or different alkyl radicals having 1 to 3 carbon atoms.
  • R 6 and R 7 are identical or different alkyl radicals having 1 to 3 carbon atoms.
  • Preferred are -C 0 -C 8 -alkyl-dimethylcarboxymethyl-betaine and Cn--C- 7 -Alkylamidopropyl-dimethylcarboxymethyl-betaine.
  • the betaine compounds of the formula IV are preferably present in an amount of 0.1 to 14% by weight, in particular 1 to 8% by weight, of the surfactant solutions according to the invention.
  • the total surfactant content in the surfactant solutions according to the invention is preferably above 15% by weight, based on the total solution, but not above 75% by weight, in particular not above 50% by weight.
  • the solvents to be added if necessary are preferably low molecular weight alkanols having 1 to 4 carbon atoms in the molecule, in particular ethanol and isopropanol.
  • Other solution mediators for example for dyes and perfumes, can optionally be, for example, alkanolamines, polyols such as ethylene glycol, propylene glycol, glycerol and alkylbenzenesulfonates having 1 to 3 carbon atoms in the alkyl radical, in particular cumene, toluene and xylene sulfonates.
  • the pH of the surfactant solutions according to the invention is preferably between 5 and 9, in particular between 6 and 8, most preferably between 6 and 7.
  • the pH is optionally adjusted by means of conventional pH regulators such as citric acid or sodium hydroxide.
  • antimicrobial agents or pH buffers can be added in amounts of up to 10% by weight based on the active substance content of fatty acid oligoalkylene glycol ester sulfate (s).
  • Substances such as gelatin or casein can also be used to adjust the viscosity of the surfactant solution.
  • the additional use of a conventional thickening agent is dispensed with.
  • preservatives examples include sodium benzoate, formaldehyde and sodium sulfite.
  • the surfactant solutions according to the invention can also contain conventional disinfectants.
  • surfactant solutions according to the invention can contain, as further constituents, perfume, dyes and opacifiers, as well as skin protection components, such as those e.g. are known from the document EP 0 522 756.
  • the agents E1 to E33 according to the invention and the comparison agents V0 to V3 were produced (composition in% by weight according to Tables 1 to 3).
  • the pH was adjusted between 6.2 and 6.6 with citric acid.
  • Water in Tables 1 to 3 means water and pH regulator (s).
  • the following surfactant components were used: A lauric acid + IEO estersulfate NH 4 salt (FSES), B lauryl ether sulfate Na salt (AES), CC 8 14 alkyl polyglucoside (APG) and D coconut fatty acid amidopropyl betaine.
  • the viscosity of the surfactant solutions E1 to E5 and V0 and VI was determined. The measurements were carried out using a Broc / cfield LV viscometer of the type LVDV-II + in a Brookfield Small Sample Adapter (measuring tube for sample volumes from 2 to 16 ml) at 20 ° C. and a measuring time of 2 minutes, with spindle and Speed was chosen so that the measured viscosity was in the recommended measuring range.
  • the type numbers of the spindles used and the vicissosites obtained are given in Table 1. The rotation frequency was 30 revolutions per minute.
  • the viscosity can be set in a very wide range from 160 to 6016 mPa • s. Viscosities that are significantly lower than those of solution VI without fatty acid oligoalkylene glycol ester sulfate (E1 to E4, table 1) and one that is significantly greater than that of solution V0 without alkyl ether sulfate (E5, table 1) can be set here.
  • an FSES: AES ratio of 1: 2.5 (E9) to 1.8: 1 (E14) is a marked increase in viscosity with a maximum of 1: 1 , 3 (rush) to watch (Table 2).
  • FSES proportion of FSES in this case results in an exceptionally high thickening of the aqueous surfactant systems, without the need to add further thickeners, such as, for example, inorganic salts. But even beyond the maximum viscosity in terms of increasing FSES content, very low viscosities of less than 100 mPa-s can be set (E16, Table 2; E30, E31, Table 3).
  • the percentage cleaning power obtained with respect to the VI standard is shown in Table 4.
  • the viscosity can be set in a very wide range from 160 to 6016 mPa-s.
  • the rinse power of the compositions E1 to E5 which contain components A and B, is synergistically superior to that of the comparative solutions V0 and VI containing only one of these two components.

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  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des sulfates d'ester d'oligoalkylènglycol d'acide gras de la formule (I) R<1>COO(R<2>O)nSO3M où M représente un cation, notamment un ion d'ammonium, et R<1>CO représente un reste acyle avec 6 à 22 atomes de carbone, linéaire ou ramifié, aliphatique, saturé ou non saturé et R<2>, dans (R<2>O)n, représente un reste alkylène, notamment CH2CH2, CH(CH3)CH2 ou CH2CH(CH3), n valant alors un nombre de 0,5 à 5, de préférence, de 0,7 à 3, notamment de 0,9 à 2 ou (R<2>O)n représente une unité du type (EO)u(PO)v(EO)w, E représentant CH2CH2 et P représentant CH(CH3)CH2 ou CH2CH(CH3) et 0</=u</=5, 0,1</=v</=5 et 0</=w</= 5 ainsi que u + w > 0 et la somme u + v + w représente une valeur de 0,5 à 5, de préférence de 0,7 à 3, notamment de 0,9 à 2. L'utilisation de ces sulfates d'ester d'oligoalkylènglycol d'acide gras, notamment associés à des sulfates d'éther d'alkyle, permet de régler de façon ciblée la viscosité de solutions tensio-actives aqueuses - même sans les épaississants usuels -. Des solutions tensio-actives aqueuses contenant des sulfates d'ester d'oligoalkylènglycol d'acide gras de la formule (I) ont, à température ambiante, des viscosités supérieures à 1000 à 10<5> mPa.s, de préférence au moins de 5000 mPa.s, notamment au moins de 10000 mPa.s, à savoir au moins de 20000 mPa.s, ou encore des viscosités comprises entre 0,01 et 1000 mPa.s, de préférence entre 0,1 et 600 mPa.s, notamment entre 0,5 et 300 mPa.s, de préférence entre 1 et 100 mPa.s.
PCT/EP1999/001698 1998-03-25 1999-03-16 Sulfates d'ester d'oligoalkylenglycol d'acide gras dans des solutions aqueuses Ceased WO1999049006A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE1998113042 DE19813042A1 (de) 1998-03-25 1998-03-25 Handgeschirrspülmittel mit Fettsäureoligoalkylenglykolestersulfaten
DE19813043.0 1998-03-25
DE19813042.2 1998-03-25
DE19813043A DE19813043A1 (de) 1998-03-25 1998-03-25 Fettsäureoligoalkylenglykolestersulfate in wäßrigen Tensidlösungen

Publications (1)

Publication Number Publication Date
WO1999049006A1 true WO1999049006A1 (fr) 1999-09-30

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Application Number Title Priority Date Filing Date
PCT/EP1999/001698 Ceased WO1999049006A1 (fr) 1998-03-25 1999-03-16 Sulfates d'ester d'oligoalkylenglycol d'acide gras dans des solutions aqueuses
PCT/EP1999/001697 Ceased WO1999049007A1 (fr) 1998-03-25 1999-03-16 Produit vaisselle comprenant des sulfates d'ester d'oligoalkylenglycol d'acide gras

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001697 Ceased WO1999049007A1 (fr) 1998-03-25 1999-03-16 Produit vaisselle comprenant des sulfates d'ester d'oligoalkylenglycol d'acide gras

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WO (2) WO1999049006A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2757145B1 (fr) 2013-01-21 2018-01-10 The Procter & Gamble Company Détergent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19741911C1 (de) * 1997-09-25 1999-01-14 Henkel Kgaa Stark schäumende Detergensgemische
WO1999010460A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Preparations tensioactives coulantes contenant des sulfates d'ester de polyglycol d'acide gras
WO1999010319A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Procede de preparation de sulfates d'ester de polyglycol d'acide gras
WO1999010463A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Detergents aqueux pour laver la vaisselle a la main
WO1999010461A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999010460A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Preparations tensioactives coulantes contenant des sulfates d'ester de polyglycol d'acide gras
WO1999010319A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Procede de preparation de sulfates d'ester de polyglycol d'acide gras
WO1999010463A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Detergents aqueux pour laver la vaisselle a la main
WO1999010461A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras
DE19741911C1 (de) * 1997-09-25 1999-01-14 Henkel Kgaa Stark schäumende Detergensgemische

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2757145B1 (fr) 2013-01-21 2018-01-10 The Procter & Gamble Company Détergent
EP2757145B2 (fr) † 2013-01-21 2024-02-07 The Procter & Gamble Company Détergent

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