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WO2001072947A1 - Savons au detergent synthetique - Google Patents

Savons au detergent synthetique Download PDF

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Publication number
WO2001072947A1
WO2001072947A1 PCT/EP2001/003020 EP0103020W WO0172947A1 WO 2001072947 A1 WO2001072947 A1 WO 2001072947A1 EP 0103020 W EP0103020 W EP 0103020W WO 0172947 A1 WO0172947 A1 WO 0172947A1
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Prior art keywords
acid
alkyl
fatty acid
carbon atoms
fatty
Prior art date
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PCT/EP2001/003020
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German (de)
English (en)
Inventor
Werner Seipel
Anke Eggers
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BASF Personal Care and Nutrition GmbH
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Cognis Deutschland GmbH and Co KG
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Publication of WO2001072947A1 publication Critical patent/WO2001072947A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—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
    • C11D1/38—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
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • 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
    • C11D3/2093—Esters; Carbonates
    • 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

Definitions

  • the invention relates to fatty acid-free syndet soaps containing selected sugar surfactants and partial glycerides as well as starch or cellulose.
  • bar soaps not only have to clean the skin, they also have to take care of it, i.e. Prevent drying out, regreasing and protecting against external influences.
  • the soap is particularly well tolerated by the skin, but in use it should not only result in as much and creamy foam as possible but also have a particularly high stability and allow the incorporation of new oil bodies.
  • bar soap manufacturers are constantly looking for new ingredients that meet this increased requirement profile.
  • the soap bars obtainable according to the teaching of the prior art do not always develop a sufficient amount of foam, and also foam consistency and in particular the feeling on the skin leave something to be desired. If free fatty acids are used as refatting agents, there can also be corrosion problems in the manufacturing plants. Furthermore, cracks often occur, so that the stability of the soaps is in need of improvement.
  • the object of the invention was therefore to provide syndet soaps which are free from the disadvantages described and have an increased stability and consistency.
  • particular attention had to be paid to the fact that new bar soap compositions must also be able to be produced on an industrial scale, ie that the compositions have, for example, sufficient but not too high deformability and do not tend to crack during drying.
  • the invention proposes new syndet soaps containing
  • sugar surfactants selected from the group formed by (a1) alkyl and / or alkenyl oligoglycosides and / or (a2) fatty acid N-alkyl polyhydroxyalkyl amides,
  • bar soaps can be produced in the absence of fatty acids or fatty acid salts by adding selected sugar surfactants in combination with partial glycerides and starch as builders, which are stable over a longer period of time. It is particularly surprising that there is no hydrolysis of the partial glyceride, for example glycerol monooleate, at an alkaline pH or that the hydrolysis has no influence on the stability of the bar soap. Such formulations furthermore have a higher consistency or elasticity, good foaming power and an optimal skin feel.
  • the invention includes the knowledge that the mixtures are also outstandingly suitable for the large-scale production of syndet soaps. In addition to their high stability, they are not very hygrospcopic, deformable, but not too hard, and show little or no crack formation when dried.
  • Alkyl and alkenyl oligoglycosides which make up the sugar surfactant component (a1) are known nonionic surfactants which follow the formula (I)
  • R 1 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 oligoglucosides.
  • the index number p in the general formula (I) gives the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • alkyl oligoglycoside is an analytically determined arithmetic parameter, which 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, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronalcohol, 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, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred.
  • the preparations according to the invention can contain the alkyl and / or alkenyl oligoglycosides in amounts of 0.5 to 40, preferably 1 to 30 and in particular 2 to 20% by weight, based on the total composition.
  • Fatty acid N-alkylpolyhydroxyalkylamides which make up sugar surfactant component (a2) are nonionic surfactants which follow the formula (II),
  • 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 (III):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (III) in which R 3 is an alkyl group and R 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 3 is an alkyl group and R 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
  • Fatty acid N-alkylglucamides of the formula (III) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or Ci2 / i4 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • fatty acid N-alkylpolyhydroxyalkylamides are also the subject of a large number of publications. Their use as a thickener is known, for example, from European patent application EP 0285768 A1 (Hüls). French published patent application FR 1580491 A (Henkel) describes aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and, if appropriate, soaps, which contain fatty acid N-alkylglucamides as foam regulators. Mixtures of short- and longer-chain glucamides are described in German patent DE 4400632 C1 (Henkel).
  • German Offenlegungsschriften DE 4326959 A1 and DE 4309567 A1 also report on the use of glucamides with longer alkyl residues than pseudoceramides in skin care products and on combinations of glucamides with protein hydrolysates and cationic surfactants in hair care products.
  • WO 92/06153, WO 92/06156, WO 92/06157, WO 92/06158, WO 92/06159 and WO 92/06160 are mixtures of fatty acid N-alkylglucamides with anionic surfactants, surfactants with a sulfate and / or sulfonate structure, ether carboxylic acids, ether sulfates, methyl ester sulfonates and nonionic surfactants.
  • the preparations according to the invention can contain the fatty acid N-alkylpolyhydroxyalkylamides in amounts of 0.5 to 40, preferably 1 to 30 and in particular 2 to 10% by weight, based on the total composition.
  • Partial glycides which form component (b), that is to say monoglycerides, diglycerides and their technical mixtures, may still contain small amounts of triglycerides due to the production process.
  • the partial glycerides preferably follow the formula (VI)
  • R 4 CO for a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18 carbon atoms, R 5 and R 6 independently of one another for R4CO or OH and the sum (m + n + p) for 0 or numbers from 1 to 100, preferably 5 to 25, with the proviso that at least one of the two radicals R 5 and R 6 is OH.
  • Typical examples are mono- and / or diglycerides based on 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, linoleic acid, linostolic acid acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • the preparations according to the invention can contain the fatty acid partial glycerides in amounts of 0.5 to 40, preferably 1 to 30 and in particular 2 to 10% by weight, based on the total composition.
  • component (c) is the use of wheat and / or maize starch which is untreated or in an open, i.e. partially hydrolyzed or acid-built form can be used.
  • Untreated starch has the advantage that it is present in the bar soaps in the form of small, solid grains which, when used, have a gentle abrasive effect and improve the skin feel.
  • Hydrolyzed starch leads to products with better deformability and homogeneity.
  • compounds are prepared from alkoxylated carboxylic acids and starch by subjecting aqueous slurries of the two components to drying with superheated steam.
  • the preparations according to the invention can contain the starch and / or cellulose in amounts of 5 to 40 preferably 15 to 30 wt .-% - based on the total composition - contain.
  • Monoglyceride sulfates and monoglyceride ether sulfates which may be included as further anionic surfactants, are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • the usual starting point for their preparation is triglycerides, which, if appropriate, are transesterified to the monoglycerides after ethoxylation and subsequently sulfated and neutralized. It is also possible to react the partial glycerides with suitable sulfating agents, preferably gaseous sulfur trioxide or chlorosulfonic acid [cf. EP 0561825 B1, EP 0561999 B1 (Henkel)].
  • the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE 4204700 A1 (Henkel)].
  • Overviews on the chemistry of monoglyceride sulfates are available, for example, from A.K. Biswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and F.U. Ahmed J.Am.Oil.Chem. Soc. 67, 8 (1990).
  • the monoglyceride (ether) sulfates to be used in accordance with the invention follow the formula (V),
  • R 7 CO stands for a linear or branched acyl radical with 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and X stands for an alkali or alkaline earth metal.
  • Typical examples of monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride as well as their ethylene oxide adducts with sulfur trioxide or chlorosulfonic acid in the form of their sodium salts.
  • Monoglyceride sulfates of the formula (V) are preferably used, in which R 7 CO stands for a linear acyl radical having 8 to 18 carbon atoms.
  • the monoglyceride (ether) sulfates are preferably used as dry granules or powders, which can be obtained, for example, by drying aqueous pastes in a flash dryer.
  • Betaines which can also be used as representatives of the amphoteric or zwitterionic surfactants, are known substances which are predominantly prepared 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
  • R 10 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms
  • R 8 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 9 for alkyl radicals with 1 to 4 carbon atoms
  • q for numbers from 1 to 6 and X. represents an alkali and / or alkaline earth metal or ammonium.
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, Decyldi- methylamine, dodecylmethylamine, dodecyldimethylamine, Dodecylethylmethylamin, Ci ⁇ -Kokosalkyldi- methylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearyl, oleyl, Ci6 / 18 tallow alkyl dimethyl amine and technical mixtures thereof.
  • Carboxyalkylation products of amidoamines which follow the formula (VII) are also suitable, I
  • R 11 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 8 , R 9 , q and X have the meanings given above.
  • Typical examples are reaction products of fatty acids with 6 to 22 carbon atoms, namely 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, elaeostearic acid, galenic acid, arachene acid and erucic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-dieth
  • Fatty acid polyglycol ester sulfates which may be present as an optional component, preferably follow the formula (VIII),
  • R 12 CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, w for numbers of 1 to 3 on average and AO for a CH2CH2O-, CH CH (CH 3 ) 0- and / or CH (CH 3 ) CH 0 radical and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, are known anionic surfactants and are prepared by sulfating 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.
  • molar amounts of fatty acid polyglycol ester to sulfating agent from 1: 0.5 to 1: 0.95, mixtures of fatty acid polyglycol ester sulfates and fatty acid polyglycol esters are obtained, which are also advantageous for a whole range of applications.
  • 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 (VIII) are preferably used in which R 12 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 12 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
  • the bar soaps according to the invention can contain, as an optional component, olefin sulfonates, which are usually obtained by addition of SO 3 to olefins of the formula (IX)
  • R 14 and R 13 independently of one another represent H or alkyl radicals having 1 to 20 carbon atoms, with the proviso that R 14 and R 13 together have at least 6 and preferably 10 to 16 carbon atoms.
  • olefin sulfonates can be used which result when R 14 or R 13 are hydrogen.
  • Typical examples of olefin sulfonates used are the sulfonation products which are obtained by treating SO 3 with 1-, 2-butene, 1-, 2-, 3-hexene, 1-, 2-, 3-, 4-octene, 1- , 2-, 3-, 4-, 5-decene, 1-, 2-, 3-, 4-, 5-, 6- dodecene, 1-, 2-, 3-, 4-, 5-, 6- , 7-tetradecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-hexadecene, 1-, 2-, 3-, 4-, 5-, 6-, 7- , 8-, 9-octadecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-octadecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-eicosen and
  • olefin sulfonate as alkali metal, alkaline earth metal, ammonium nium, alkylammonium, alkanolammonium, glucammonium, preferably sodium salt is present in the mixture.
  • olefin sulfonates in aqueous paste preferably at a pH of 7 to 10
  • anhydrous products preferably as granules
  • Alkoxylated carboxylic acid esters which form component (a) are known from the prior art.
  • such alkoxylated carboxylic acid esters can be obtained by reacting alkoxylated carboxylic acids with alcohols.
  • the compounds are preferably prepared by reacting carboxylic acid esters with alkylene oxides using catalysts, in particular using calcined hydrotalcite according to German Offenlegungsschhft DE 3914131 A, which provide compounds with a restricted homolog distribution.
  • Both carboxylic acid esters of monohydric alcohols and polyhydric alcohols can be alkoxylated by this process. According to the present invention, preference is given to using alkoxylated carboxylic acid esters of the formula (X)
  • R 1 CO stands for an aliphatic acyl radical with 6 to 30 C atoms
  • AlkO for alkylene oxide
  • n for numbers from 1 to 30
  • R 16 for an aliphatic alkyl radical with 1 to 8 carbon atoms.
  • AlkO stands for the alkylene oxides which are reacted with the carboxylic acid esters and include ethylene oxide, propylene oxide and / or butylene oxide, preferably ethylene oxide and / or propylene oxide, in particular ethylene oxide alone.
  • Alkoxylated carboxylic acid esters of the formula (X) are particularly suitable, in which R 15 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 and in particular 10 to 18 carbon atoms, AlkO for ethylene oxide and / or propylene oxide, n on average for numbers 5 to 20 and R 16 is an aliphatic alkyl radical having 1 to 8, preferably 1 to 4 carbon atoms and in particular methyl.
  • Preferred acyl radicals are derived from carboxylic acids having 6 to 22 carbon atoms of natural or synthetic origin, in particular from linear, saturated and / or unsaturated fatty acids, including technical mixtures thereof, as are obtainable by fat cleavage from animal and / or vegetable fats and oils, for example from coconut oil, palm kernel oil, palm oil, soybean oil, sunflower oil, rape oil, cottonseed oil, fish oil, beef tallow and lard.
  • carboxylic acids examples include 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 / or erucic acid.
  • R 15 CO is a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 10 to 18 carbon atoms
  • n for numbers from 5 to 20
  • R 16 represents a methyl radical.
  • examples of such compounds are methyl lauric acid, methyl coconut fatty acid and methyl tallow fatty acid alkoxylated with an average of 5, 7, 9 or 11 moles of ethylene oxide.
  • the preparations according to the invention can contain the preferred further surfactants in amounts of 0 to 50, preferably 25 to 45% by weight, based on the total composition.
  • the syndet soaps according to the invention can contain non-ionic, anionic, cationic and / or amphoteric or amphoteric surfactants as further optional surfactant additives.
  • anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerin ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monosuccinate sulfates, fatty acid sulfate monates, fatty acid sulfonates, fatty acid sulfate monates, fatty acid sulfate monates, fatty acid sulfate monates, fatty acid
  • anionic surfactants contain polyglycol ether chains, these can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally glucoronic acid derivatives, protein hydrolysates (in particular vegetable polyol fatty acid esters), amine sugar polyesters or sorbate esters, amine vegetable polyols or ester oxides, and amine sugar products, in particular, vegetable polyol orbic acid esters, amine orbital polyesters, and sugar-based ester-based polyols.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • cationic surfactants are quaternary ammonium compounds, such as, for example, dimethyldistearylammonium chloride, and esterquats, in particular quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • n alkyl sulfates, mono and dialkyl sulfosuccinates, alkyl sulfoacetates and / or isothionates are preferably used.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example, J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, Tenside und Mineralöladditive ", Thieme Verlag, Stuttgart, 1978, pp. 123-217.
  • the preparations according to the invention can contain the further surfactants in amounts of 0 to 50, preferably 25 to 45% by weight, based on the overall composition.
  • Syndet soaps with a particularly beneficial skin feel and creamy foam contain the ingredients in the following amounts:
  • sugar surfactants selected from the group formed by (a1) alkyl and / or alkenyl oligoglycosides and / or (a2) fatty acid-N -alkylpoly-hydroxyalkylamides,
  • Alkyl and / or alkenyl oligoglycosides fatty acid N-alkyl glucamides, monoglyceride (ether) sulfates, preferably coconut fatty acid monoglyceride sulfate, betaines, alkoxylated carboxylic acid esters, fatty acid polyglycol ester sulfates and olefin sulfonates, preferably ⁇ -olefin sulfonates, are used as surfactants.
  • syndet soaps according to the invention are fatty alcohols and polyethylene glycol ethers.
  • suitable fatty alcohols are lauryl alcohol, myristyl alcohol, cetearyl alcohol, stearyl alcohol and isostearyl alcohol.
  • Suitable polyethylene glycol ethers are those which have an average molecular weight in the range from 5,000 to 20,000 daltons.
  • component (a) and / or (b) and, if appropriate, further surfactants are used in anhydrous, granular form, as is the case after Drying in a so-called “Flash dryer” receives.
  • flash dryer a so-called "Flash dryer” receives.
  • the syndet soaps according to the invention are practically free of free fatty acids or fatty acid salts, i.e. the content of these substances is below 0.5% by weight. Nevertheless, when used, the soaps provide a surprisingly high amount of a particularly creamy foam and also convey a very pleasant feeling on the skin.
  • syndet soaps can also be used as additional auxiliaries and additives, mild surfactants (cf. above), oil bodies, superfatting agents, consistency enhancers, thickeners, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, stabilizers, biogenic agents, film formers, swelling agents, UV - Contain sun protection factors, antioxidants, hydrotropes, insect repellents, solubilizers, perfume oils, dyes and the like.
  • Suitable oil bodies are, for example, Guerbet alcohols preferably containing 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear C6-C22-fatty alcohols, esters of branched C6-C ⁇ come based on fatty alcohols having 6 to 18: 3 carboxylic acids with linear C ⁇ C22 fatty alcohols, for example myristyl myristate, myristyl palmitate, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, My- ristylerucat, cetyl myristate, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cety- lerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylisostearat, stearyl oleate, stearyl behen
  • esters of linear C6-C22 fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of hydroxycarboxylic acids with linear or branched C ⁇ -C ⁇ fatty alcohols in particular dioctyl malates
  • esters of linear and / or branched fatty acids are also suitable polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglyce de based on C6-C ⁇ 0 fatty acids, liquid mono- / di- / triglyceride mixtures based on C6-Ci8 fatty acids, esters of C6- C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C2-Ci2-dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons such as squalane, squalene or dialkylcyclohexanes into consideration.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable consistency agents are primarily fatty alcohols or hydroxyfatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty acids. A combination of these substances with fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates , (eg Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyylpyrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with restricted homolog distribution and electrolytes such as Cooking salt and ammonium chloride.
  • Aerosil types hydrophilic silicas
  • polysaccharides in particular xanthan gum, guar gu
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as, for example, Luviquat® (BASF) , Condensation products of polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as, for example, amidomethicones, copolymers of adipic acid and dimethyldiethylaminohydroxypropylaminohydroxyaminohydroxyaminohydroxin
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, non-injured acrylamide and with polyesters, non-injured acrylamide acrylamide and polyacrylamide acrylamide / non-injected acrylamide and with polyesters, non-injured polyacrylamide and untreated polyamide acrylamide and non-injured acrylamide and with polyethers, acrylate and non-injured polyacrylamide Copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxyproyl methacrylate copolymers, polyvinylpyrrol
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Simethicones which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are also suitable.
  • a detailed overview of suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
  • fats are glycerides
  • waxes include natural waxes, e.g. Candelilla wax, carnauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes; chemically modified waxes (hard waxes), e.g.
  • natural waxes e.g. Candelilla wax, carnauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum,
  • R typically represents linear aliphatic hydrocarbon radicals with 15 to 17 carbon atoms and up to 4 cis double bonds.
  • lecithins are the cephalins, which are also referred to as phosphatidic acids and are derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood to be mono- and preferably diesters of phosphoric acid with glycine (glycerol phosphates), which are generally classed as fats.
  • sphingosines or sphingolipids are also suitable.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmorillonites, clay minerals, pemules and alkyl-modified carbopol types can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).
  • UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 3-benzylidene camphor or 3-benzylidene norcampher and its derivatives for example 3- (4-methylbenzylidene) camphor as described in EP 0693471 B1; 4-aminobenzoic acid derivatives, preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate; Esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, propyl 4-methoxycinnamate, isoamyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3,3-phenylcinnamate (octocrylene); > Esters of salicylic acid, preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomethyl
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1 '-hexyloxy) -1, 3,5-triazine and octyl triazone as described in EP 0818450 A1 or dioctyl butamido triazone (Uvasorb ® HEB);
  • UV-A filters -4'-methoxydibenzoyl-methane (Parsol 1789), 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione and enamine compounds, as described in DE 19712033 A1 (BASF).
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • insoluble light protection pigments namely finely dispersed metal oxides or salts
  • suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
  • Silicates (talc), barium sulfate or zinc stearate can be used as salts.
  • the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobicized.
  • Typical examples are coated titanium dioxides such as titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck). Silicones, and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used. Further Suitable UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
  • Typical examples include amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as DL-carnosine, D-camosine, L-carnosine and their derivatives (e.g. anserine), carotenoids , Carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives,
  • Chlorogenic acid and its derivatives, lipoic acid and its derivatives eg dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl) -, Amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, Nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximine, Butioninsulfone, penta-, hexa-, heptathioninsulfoximine) in very low tolerable dosages (e.g. pmol to ⁇ mol / kg), also (metal) chelators (e.g. ⁇ - Hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their D derivatives, unsaturated fatty acids and their derivatives (e.g. ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and
  • metal chelators e.g. ⁇ - Hydroxy fatty acids, palmitic acid, phytic acid
  • vitamin C and derivatives e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g. vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • Ferulic acid furfurylidene glucitol, camosin, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguajak resin acid, nordihydroguajaretic acid, trihydroxybutyrophenon, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, zinc and its derivatives (e.g. Zn and its derivatives (e.g.
  • Zn and its derivatives eg Selenium-methionine
  • stilbenes and their derivatives eg stilbene oxide, trans-stilbene oxide
  • derivatives salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • Hydrotropes such as ethanol, isopropyl alcohol, or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are >Glycerin;
  • Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Dialcohol amines such as diethanolamine or 2-amino-1, 3-propanediol.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenylglycinate, allylcyclohexyl benzylatepylpropionate, allyl cyclohexyl propyl pionate.
  • the ethers include, for example, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the jonones, ⁇ -isomethyl ionone and methyl cedryl ketone the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol
  • the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • soap bars were pressed and examined for their application properties.
  • the composition of the soap bars and the results of the tests are summarized in Table 1. The stability, crack formation after drying and skin feel were assessed on a scale from - poor, + sufficient, ++ satisfactory to +++ very good.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
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  • Detergent Compositions (AREA)
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Abstract

L'invention concerne de nouveaux savons au détergent synthétique contenant (a) des tensioactifs de sucre sélectionnés dans le groupe constitué de (a1) oligoglycosides d'alkyle et/ou d'alcényle et /ou de (a2) N-alkylpoly-hydroxyalkylamides d'acides gras, (b) de glycérides partiels d'acides gras et (c) d'amidon et/ou de cellulose.
PCT/EP2001/003020 2000-03-25 2001-03-16 Savons au detergent synthetique Ceased WO2001072947A1 (fr)

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DE10015000.4 2000-03-25
DE2000115000 DE10015000A1 (de) 2000-03-25 2000-03-25 Syndetseifen

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1829956A1 (fr) 2006-03-03 2007-09-05 Sebapharma GmBH & Co. Pièce à laver à l'aide de détergents synthétiques
EP1829955A1 (fr) * 2006-03-03 2007-09-05 Sebapharma GmBH & Co. Pièce à laver à l'aide de détergents synthétiques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6544938B1 (en) * 2001-10-02 2003-04-08 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Soap bar comprising high levels of specific alkoxylated triglycerides which provide enhanced sensory properties and process well

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3011813A1 (de) * 1980-03-27 1981-10-22 Zschimmer & Schwarz Gmbh & Co Chemische Fabriken, 5420 Lahnstein Verfahren zur verbesserung der gebrauchseigenschaften von stueckfoermigen reinigungsmitteln
WO1998015606A2 (fr) * 1996-10-07 1998-04-16 Henkel Kommanditgesellschaft Auf Aktien Savons detersifs synthetiques
DE19703745A1 (de) * 1997-02-03 1998-08-06 Henkel Kgaa Stückseifen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3011813A1 (de) * 1980-03-27 1981-10-22 Zschimmer & Schwarz Gmbh & Co Chemische Fabriken, 5420 Lahnstein Verfahren zur verbesserung der gebrauchseigenschaften von stueckfoermigen reinigungsmitteln
WO1998015606A2 (fr) * 1996-10-07 1998-04-16 Henkel Kommanditgesellschaft Auf Aktien Savons detersifs synthetiques
DE19703745A1 (de) * 1997-02-03 1998-08-06 Henkel Kgaa Stückseifen

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1829956A1 (fr) 2006-03-03 2007-09-05 Sebapharma GmBH & Co. Pièce à laver à l'aide de détergents synthétiques
EP1829955A1 (fr) * 2006-03-03 2007-09-05 Sebapharma GmBH & Co. Pièce à laver à l'aide de détergents synthétiques

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