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EP1007508A1 - Procede de preparation de sulfates d'ester de polyglycol d'acide gras - Google Patents

Procede de preparation de sulfates d'ester de polyglycol d'acide gras

Info

Publication number
EP1007508A1
EP1007508A1 EP98947432A EP98947432A EP1007508A1 EP 1007508 A1 EP1007508 A1 EP 1007508A1 EP 98947432 A EP98947432 A EP 98947432A EP 98947432 A EP98947432 A EP 98947432A EP 1007508 A1 EP1007508 A1 EP 1007508A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
acid polyglycol
formula
sulfation
neutralization
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98947432A
Other languages
German (de)
English (en)
Inventor
Hans-Christian Raths
Thomas Engels
Rainer Rüben
Jörg KAHRE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1007508A1 publication Critical patent/EP1007508A1/fr
Withdrawn legal-status Critical Current

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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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
    • C11D17/065—High-density particulate detergent compositions
    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
    • 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
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    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246—Silicates, e.g. diatomaceous earth
    • C11D3/128—Aluminium silicates, e.g. zeolites
    • 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
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2082—Polycarboxylic acids-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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-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
    • 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
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    • 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
    • C11D1/04—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
    • C11D1/14—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
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    • 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
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    • 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
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    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the application relates to a process for the preparation of fatty acid polyglycol ester sulfates by sulfating fatty acid polyglycol esters and subsequent neutralization, and the use thereof of foam boosters especially for nonionic surfactant mixtures.
  • Fatty acid polyethylene glycol esters in particular low ethoxylated fatty acids such as fatty acid + 1 E0 adducts, have been described in the literature for some time as an interesting precursor for the synthesis of ether sulfate surfactants with an isethionate-like structure. Initially, however, it was already difficult to produce the fatty acid polyethylene glycol esters to be used as starting compounds in satisfactory selectivities. In addition to the undesirable proportion of higher ethoxylated homologues, significant amounts of polyethylene glycol and diesters were also formed by the older processes known to date.
  • the object of the present invention was to provide an improved process for the sulfation of especially low alkoxylated fatty acids, which can be used on an industrial scale to supply fatty acid polyglycol ester sulfates without further work-up.
  • the present invention relates to a process for the preparation of fatty acid polyglycol ester sulfates of the formula (I),
  • R 1 CO is a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms
  • AO is CH2CH2O, CHCH3CH2O and / or CH2CHCH3O
  • n is a number from 0.5 to 5
  • M is a cation , by sulfation of fatty acid polyglycol esters and subsequent neutralization, which is characterized in that the entire neutralization process is carried out at a pH of 5 to 9.
  • R 1 CO is a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms
  • AO is CH2CH2O, CHCH3CH2O and / or CH2CHCH3O
  • n is a number from 0.5 to 5.
  • the esters can be prepared by known methods of preparative organic chemistry, for example by basic homogeneously catalyzed addition of ethylene oxide and / or propylene oxide to fatty acids.
  • Fatty acids are to be understood as aliphatic carboxylic acids of the formula R 1 COOH, in which R 1 CO is an aliphatic, linear or branched acyl radical having 6 to 22, preferably 12 to 18 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples are, ristin Textre caproic acid caprylic acid 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristyl, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petrochemical Selin acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, Gadoieinklare, behenic acid and erucic acid and their technical mixtures, which are obtained, for example, in the pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or as a monomer fraction in the dimerization of unsaturated fatty acids.
  • R 1 CO in formula (I) or (II) is preferably an acyl radical having 12 to 18 carbon atoms.
  • Suitable basic catalysts for the alkoxylation are both alkanolamines such as monoethanolamine, diethanolamine and preferably triethanolamine and also the amines described in DE 2024050 AS such as mono-, di- and trimethylamine, mono-, di-, triethylamine, mono-, di - and tri-n-butylamine, tert.
  • the alkanolamines described are particularly preferred as catalysts.
  • the alkanolamines are usually used in amounts of 0.1 to 5, preferably 0.5 to 1.5,% by weight, based on the fatty acids.
  • the alkoxylation can be carried out in a manner known per se.
  • the fatty acid and the catalyst are placed in a stirred autoclave, which is freed of traces of water by alternately evacuating and flushing with nitrogen before the reaction.
  • the fatty acid is then reacted with ethylene oxide and / or propylene oxide in a molar ratio of 1: 0.5 to 1: 5, preferably 1: 1 to 1: 2, which, after heating, can be metered in portions into the pressure vessel using a siphon.
  • n stands for a number from 0.5 to 5, preferably for a number from 1 to 2.
  • the alkoxylation can be carried out at temperatures in the range from 80 to 180, preferably 100 to 120 ° C. and autogenous pressures in the range from 1 to 5, preferably 2 to 3, bar. After the end of the reaction, it is advisable to stir at the reaction temperature for a certain time to complete the conversion (15 to 90 min). The autoclave is then cooled, decompressed and, if desired, acids such as lactic acid or phosphoric acid are added to the product in order to neutralize the basic catalyst.
  • either exclusively or exclusively propoxylated or also ethoxylated and propoxylated fatty acids are used as starting compounds. If ethoxylated and propoxylated fatty acids are used, they can be random or block compounds.
  • the ratio of ethylene oxide and propylene oxide to be used can be set within a wide range, as long as the degree of alkoxylation n is in the above range.
  • the consistency of the alkoxylated fatty acid can be influenced via the proportion of propylene oxide. As the degree of propylation increases, the softening temperature of the alkoxylated fatty acids becomes lower. If the fatty acids are exclusively propoxylated, even liquid products are obtained, while the exclusively ethoxylated fatty acids are solid compounds.
  • the sulfation of the fatty acid alkylene glycol esters can be carried out using gaseous sulfur trioxide in the manner known for fatty acid lower alkyl esters, preference being given to continuously operating reactors which operate on the falling film principle.
  • the sulfur trioxide is diluted with an inert gas, preferably air or nitrogen, and used in the form of a gas mixture which contains the sulfur trioxide in a concentration of 1 to 8, in particular 2 to 5,% by volume.
  • the molar ratio of fatty acid alkylene glycol ester to sulfur trioxide is generally 1: 1 to 1: 1.3, preferably 1: 1.05 to 1: 1.1.
  • the sulfation is preferably carried out in a continuous falling film reactor at temperatures which are at least 5 to 10 ° C. above the melting point of the fatty acid alkylene glycol esters. As a rule, the sulfation temperatures are up to a maximum of 30 ° C above the melting point of the fatty acid alkylene glycol esters.
  • the sulfation is carried out with a sulfation reagent, in particular with chlorosulfonic acid. The reaction takes place under conditions known to the person skilled in the art, for example in a continuously operating process with approximately stoichiometric amounts of chlorosulfonic acid.
  • the acid esters of the formula (I) obtained after the sulfation are neutralized with bases in such a way that the pH is in the range from 5 and 9, preferably from 6 and 8, during the entire neutralization process. It has proven advantageous to carry out the neutralization in such a way that the acid ester is run into an aqueous solution, the pH of the aqueous solution always being adjusted to pH values between 5 and 9 by metering in the alkaline solution intended for neutralization is held. On an industrial scale, this can be done by simultaneously dosing the liquid acid ester and of the alkaline solution intended for neutralization into the neutralization cycle.
  • An example of such a suitable neutralization circuit can be found in German published patent application DE 4017463 A1.
  • neutralization it has proven to be advantageous to carry out the neutralization at temperatures from 10 ° C. to 40 ° C., preferably at 20 ° C. to 35 ° C.
  • any other neutralization method known to the person skilled in the art such as, for example, spray neutralization, as long as the above pH value for neutralization is maintained.
  • hydroxides such as alkali metal, alkaline earth metal hydroxide or also ammonia can be used and / or also water-soluble organic amines such as mono-, di- and tri-C2-alkanolamines, for example mono-, di- and triethanolamine as well as primary, secondary or tertiary C ⁇ -4-alkylamines.
  • the neutralization bases are preferably used in the form of 20 to 50% by weight aqueous solutions.
  • Aqueous solutions of ammonia or sodium and / or potassium hydroxide are particularly preferably used for the neutralization, so that in formula (I) M preferably represents a sodium, potassium or ammonium ion. M stands in particular for an ammonium ion, since such compounds of the formula (I) have particularly good solubility behavior.
  • the aqueous solutions of the sulfation products are preferably adjusted to pH values between 6 and 7. Such solutions are stable even when stored for months at room temperature.
  • the fatty acid polyglycol ester sulfates can subsequently be bleached in the manner known to the person skilled in the art, the bleaching also being carried out here at the above-mentioned pH values.
  • Antimicrobial agents or pH buffers can also be added in amounts of up to 10% by weight, based on the active substance content of the sulfation products, to stabilize the storage of the aqueous preparations.
  • the sulfation products - based on the non-aqueous fraction - have the following composition:
  • the aqueous fraction is not critical and can typically be in the range from 50 to 95% by weight.
  • the fatty acid polyglycol ester sulfates of the formula (I), alone or as a mixture with one or more of the compounds described under (b) to (e), are excellent foam boosters for low-foaming surfactant mixtures;
  • Mixtures of the fatty acid polyglycol ester sulfates with unsulfated starting materials are also particularly suitable.
  • These preparations can be prepared by mixing or also generated in situ, for example by only partially carrying out the sulfation.
  • the low-foaming surfactant mixtures preferably contain nonionic surfactants.
  • "weak foaming” refers to those surfactant mixtures which, according to the rotor test described in Example 2, have a foam volume of less than 500 ml after 3 minutes.
  • Nonionic surfactants that can be contained in the surfactant mixtures are fatty alcohol polyglycol ethers, alkyl phenol polyglycol ethers, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, polyol fatty acid esters, fatty acid polyethyleneglycol esters, fatty acid methyl ester ethoxylates, acyl ester glucosorbides, sugar esters, glyceryl sorbides, sugar esters, glucosorbides, sorbyl glucosorbides, sugar esters, glucosorbides, sorbyl glucosorbides, sugar esters, sorbyl glucosorbides, sugar esters, sorbyl glycides, sorbylsorbyl glycides, sorbylsorbylsorbides, sugar esters, sorbylsorbides, sorbylsorbylsorbides,
  • surfactant mixtures containing alkyl polyglycosides no longer have these disadvantages if sulfated fatty acid alkylene glycol esters are added alone or in a mixture with one or more of the compounds described under (b) to (e).
  • Another object of the present invention therefore relates to the use of sulfated fatty acid polyalkylene glycol esters of the formula (I) as foam boosters for low-foaming surfactant mixtures.
  • the compounds described are preferably used as foam boosters for surfactant mixtures containing nonionic surfactants, in particular for surfactant mixtures containing alkyl polyglycosides.
  • the amount of fatty acid polyglycol ester sulfates added can be in the range from 0.1 to 5% by weight, based on the amount of solids in the preparations.
  • alkyl polyglycosides is understood to mean alkyl and alkenyl oligoglycosides which follow the formula (III) R0- [G] p fill)
  • R stands for an alkyl and / or alkenyl residue with 4 to 22 carbon atoms
  • G stands for a sugar residue with 5 or 6 carbon atoms
  • p stands for numbers from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry.
  • the alkyl and / or aikenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or aikenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • alkyl and / or aikenyl 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 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic 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 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 C, 2/14 coconut alcohol with a DP of 1 to 3 are preferred.
  • the surfactant mixtures can of course contain further surfactants, for example anionic, cationic and / or amphoteric surfactants.
  • anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxy mixed ether sulfates, fatty (ether) sulfate ethers, monoglyl ether sulfates, monoglyl ether sulfate and dialkyl sulfo succinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, amide
  • cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid triaikanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • Example 1 200 g (1 mol) of technical lauric acid were placed in a 1 liter stirred autoclave and 2 g of triethanolamine (corresponding to 1% by weight, based on lauric acid) were added.
  • the autoclave was alternately evacuated and pressurized with nitrogen three times to remove traces of water that could lead to the formation of polyethylene glycol.
  • the autoclave was closed and heated to 100 ° C. and 44 g (1 mol) of ethylene oxide were added in portions at a maximum pressure of 5 bar. After completion of the reaction, recognizable by the fact that the pressure dropped again to a value of 1.2 bar and then remained constant, stirring was continued for 30 minutes and the reaction mixture was then cooled and let down.
  • the basic catalyst was neutralized by adding an appropriate amount of lactic acid.
  • the lauric acid + 1 EO adduct obtained was melted at 40 ° C. and sulfated in a falling film reactor with gaseous sulfur trioxide (dilution 3 to 5% in dried air) in a molar ratio of 1: 1.1 at 40 ° C.
  • the acidic ester obtained was neutralized with an aqueous ammonia solution which contained 1% by weight of triethanolamine, based on ammonia, at a temperature below 40 ° C. by allowing both solutions to run in together.
  • the pH was always kept at 6 to 8.
  • the solution was then adjusted to a pH of 6.5.
  • the dried salt had the following composition:
  • Fatty acid polyglycol ester sulfate (anionic substance) 56.0% by weight
  • Ethylene glycol mono- and diesters 22.0% by weight
  • Example 2 1 liter test solutions were prepared in 15 ° dH water (see Table 1). 200 ml of the test solutions were foamed at 40 ° C for 3 minutes in a rotor test (1300 rpm). With the help of a special stirring head, air is stirred into the test solution to be tested, which causes foaming. To measure the foaming kinetics, ie the foam behavior in the beginning, the stirrer is switched off at intervals of 10 seconds during the first 90 seconds in order to read the foam height and liquid level on the scale. The agitator is then switched on again. To determine the foam stability, the foam and liquid height is recorded for a further 5 minutes after the total stirring time of 3 minutes. The foaming kinetics are calculated from the linear part of the gradient line of the average foam volume determined within the first minute at intervals of 10 seconds. It is given in ml / s. The results are summarized in Table 1. Table 1
  • fatty acid polyglycol ester sulfates for alkyl polyglycosides produce better foaming kinetics than ether sulfates (sodium laureth sulfates) and also ensure better foaming behavior in the long term.

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Abstract

L'invention concerne un procédé de préparation de sulfates d'ester de polyglycol d'acide gras de la formule (I) R1COO(AO)¿n?SO3M dans laquelle R?1¿CO désigne un reste acyle linéaire ou ramifié, aliphatique, saturé et/ou non saturé ayant entre 6 et 22 atomes de carbone, AO désigne CH¿2?CH2O,CHCH3CH2O et/ou CH2CH3O, n désigne des nombres compris entre 0,5 et 5 et M désigne un cation, par sulfatation d'esters de polyglycol d'acide gras et par neutralisation subséquente. Ce procédé se caractérise en ce que l'ensemble du processus de neutralisation s'effectue à un pH compris entre 5 et 9.
EP98947432A 1997-08-25 1998-08-17 Procede de preparation de sulfates d'ester de polyglycol d'acide gras Withdrawn EP1007508A1 (fr)

Applications Claiming Priority (3)

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DE19736906 1997-08-25
DE19736906A DE19736906A1 (de) 1997-08-25 1997-08-25 Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
PCT/EP1998/005209 WO1999010319A1 (fr) 1997-08-25 1998-08-17 Procede de preparation de sulfates d'ester de polyglycol d'acide gras

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Families Citing this family (151)

* 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
DE19904847A1 (de) 1999-02-08 2000-08-10 Rwe Dea Ag Öl-in-Wasser-Mikroemulsion enthaltend Alkanolammonium-Salze der Alkylsulfate und/oder Alkylpolyalkylenglykolethersulfate
NO311041B1 (no) * 1999-12-22 2001-10-01 Norsk Hydro As Stabilisering av pigmenter og flerumettede oljer og oljekonsentrater
WO2002012179A1 (fr) * 2000-08-07 2002-02-14 The Procter & Gamble Company Procede de sulfatation
DE10233330B4 (de) * 2002-07-22 2007-04-26 Sasol Germany Gmbh Mikroemulsion enthaltend UV-Lichtschutzfilter und/oder Antischuppenmittel
DE10338883A1 (de) * 2003-08-23 2005-03-24 Hans Schwarzkopf & Henkel Gmbh & Co. Kg Verfahren zur Glättung keratinhaltiger Fasern
US20060150344A1 (en) * 2003-08-13 2006-07-13 Burkhard Muller Method for smoothing fibers containing keratin
DE102004032734A1 (de) * 2004-03-18 2005-10-06 Henkel Kgaa Präbiotisch wirksame Substanzen für Deodorantien
US20070267035A1 (en) 2004-09-07 2007-11-22 Henkel Kommanditgesellschaft Auf Aktien Composition and Method for the Smoothing of Fibres Containing Keratin
DE102005002486A1 (de) * 2005-01-18 2006-07-27 Henkel Kgaa Tensidhaltiges Reinigungsmittel mit speziellen Proteinen
DE102005014687A1 (de) * 2005-03-29 2006-10-12 Henkel Kgaa Zusammensetzung enthaltend ß-Defensin 2
DE102005028985A1 (de) 2005-06-21 2006-12-28 Henkel Kgaa Mikroemulsionen und ihr Gebrauch
DE102005038359A1 (de) 2005-08-11 2007-02-15 Henkel Kgaa Amaranthsamenöl in Haarbehandlungsmitteln
DE102005060181B4 (de) * 2005-12-14 2008-09-18 Henkel Ag & Co. Kgaa Behälter mit Überkopfschaumapplikator
DE102005062268A1 (de) * 2005-12-24 2007-08-02 Henkel Kgaa Pulverförmige Stylingmittel und deren Spendersysteme
DE102007024377A1 (de) 2007-05-23 2008-11-27 Henkel Ag & Co. Kgaa Desinfizierendes Hautbehandlungsmittel
DE102006032505A1 (de) * 2006-07-12 2008-01-17 Henkel Kgaa Anti-Schuppen-Shampoo
DE102006039283A1 (de) 2006-08-22 2008-02-28 Henkel Kgaa Formfixierung faserhaltiger Materialien durch Polymere
DE102006045965A1 (de) 2006-09-27 2008-04-03 Henkel Kgaa Stylingmittel mit hohem Haltegrad
JP5204390B2 (ja) * 2006-09-27 2013-06-05 ユシロ化学工業株式会社 水溶性金属加工剤、クーラント及びその調製方法、水溶性金属加工剤の微生物劣化防止方法、並びに金属加工
DE102006051729A1 (de) 2006-10-30 2008-05-08 Henkel Kgaa Kosmetisches Mittel
DE102006061863A1 (de) * 2006-12-21 2008-06-26 Henkel Kgaa Haarkonditionierende Mittel mit ausgewählten kationischen Polymeren und wasserlöslichen Silikonen
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DE102009009004A1 (de) 2008-02-18 2009-09-17 Seaquist Perfect Dispensing Gmbh Abgabevorrichtung mit einem kosmetischen Fluid
DE102008002707A1 (de) 2008-06-27 2009-12-31 Evonik Goldschmidt Gmbh Haarbehandlungsmittel und Haarnachbehandlungsmittel zum Schutz vor Schäden durch chemische Behandlung und zur Reparatur bereits geschädigter Haare enthaltend als Wirksubstanzen Etherguanidine
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DE102008038109A1 (de) 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein weiteres zusätzliches filmbildendes kationisches und/oder festigendes Polymer
DE102008059479A1 (de) 2008-11-28 2010-06-10 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens zwei weitere zusätzliche filmbildende kationische und/oder festigende kationische Polymere
DE102008038105A1 (de) * 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles, kationisches Polymer und mindestens ein spezielles amphiphiles, anionisches Polymer
DE102008038110A1 (de) * 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein spezielles, zusätzliches filmbildendes nichtionisches und/oder festigendes nichtionisches Polymer
DE102008038106A1 (de) 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein spezielles, zusätzliches filmbildendes anionisches und/oder festigendes anionisches Polymer
DE102008059480A1 (de) 2008-11-28 2010-06-02 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer, mindestens ein davon verschiedenes kationisches Stylingpolymer und mindestens ein filmbildendes nichtionisches und/oder festigendes nichtionisches Polymer
DE102008038112A1 (de) 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles, kationisches Polymer und mindestens ein Polyol
DE102008038107A1 (de) * 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein zusätzliches filmbildendes und/oder festigendes Polymer ausgewählt aus Chitosan und dessen Derivaten
WO2010020500A2 (fr) 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Préparation pour fibres kératiniques contenant au moins un polymère cationique amphiphile spécial et au moins un polymère cationique additionnel filmogène et/ou fixant
DE102008038104A1 (de) * 2008-08-18 2010-02-25 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein Polymer mit silikonhaltigen Seitenketten und anionischen Gruppen
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DE102009027925A1 (de) 2009-07-22 2011-01-27 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein Acrylat/Glycerylacrylat-Copolymer, mindestens ein filmbildendes und/oder festigendes Polymer und mindestens ein Esteröl
DE102009028054A1 (de) 2009-07-28 2011-02-10 Henkel Ag & Co. Kgaa Kosmetisches Mittel
DE102009028052A1 (de) 2009-07-28 2011-02-03 Henkel Ag & Co. Kgaa Kosmetisches Reinigungsmittel mit neuer Wirkstoffmischung
DE102009028209A1 (de) 2009-08-04 2011-02-10 Henkel Ag & Co. Kgaa Haarbehandlungsmittel mit Polyether-modifizierten organischen Verbindungen und haarfestigenden Polymeren
DE102009028206A1 (de) 2009-08-04 2011-02-10 Henkel Ag & Co. Kgaa Haarbehandlungsmittel mit speziellen Polyethern und haarfestigenden Polymeren
DE102009028207A1 (de) 2009-08-04 2011-02-17 Henkel Ag & Co. Kgaa Haarbehandlungsmittel mit Polyether-modifizierten Feststoffpartikeln und haarfestigenden Polymeren
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DE102009029183A1 (de) 2009-09-03 2011-03-10 Henkel Ag & Co. Kgaa Dauerwellsystem
DE102009045605A1 (de) 2009-10-13 2011-04-14 Henkel Ag & Co. Kgaa Versprühbares Haarreinigungsmittel
DE102009045856A1 (de) 2009-10-20 2010-07-29 Henkel Ag & Co. Kgaa Verwendung kationischer Polymere in Haut- und Haarreinigungsmitteln
DE102009045925A1 (de) 2009-10-22 2011-04-28 Henkel Ag & Co. Kgaa Zusammensetzungen zur Formgebung keratinischer Fasern
WO2011048176A1 (fr) 2009-10-22 2011-04-28 Henkel Ag & Co. Kgaa Produits pour le traitement de fibres kératiniques, contenant un amidon non ionique, modifié par de l'oxyde de propylène, et un autre polymère non ionique filmogène et/ou fixateur
DE102009045933A1 (de) 2009-10-22 2011-04-28 Henkel Ag & Co. Kgaa Zusammensetzung zur Formgebung keratinischer Fasern
DE102009047528A1 (de) 2009-12-04 2011-06-09 Henkel Ag & Co. Kgaa Verwendung von Esteröl in Verfahren zur permanenten Haarumformung
DE102009055281A1 (de) 2009-12-23 2011-06-30 Henkel AG & Co. KGaA, 40589 Emulsion für keratinhaltige Fasern, enthaltend mindestens ein anionisches verdickend wirkendes Polymer, mindestens ein nichtionisches haarfestigendes Polymer, mindestens ein Esteröl, mindestens ein Wachs und Wasser
DE102009055357A1 (de) 2009-12-29 2011-06-30 Henkel AG & Co. KGaA, 40589 Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein spezielles kationisches Polymer mit Vinylimidazolstruktureinheiten
DE102010000746A1 (de) 2010-01-08 2011-01-27 Henkel Ag & Co. Kgaa Verwendung von 1,2-Alkandiolen zur Behandlung von Körpergeruch
DE102010012628A1 (de) 2010-03-24 2011-09-29 Holger Bartels Dauerwell-Fixiermittel mit Indikator
DE102010043016A1 (de) 2010-10-27 2012-05-03 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern
DE102010043018A1 (de) 2010-10-27 2012-05-03 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern
DE102010055817A1 (de) 2010-12-23 2012-06-28 Henkel Ag & Co. Kgaa Treibmittelhaltige verschäumbare kosmetische Zusammensetzung zur Haut- und Körperpflege
DE102010055816A1 (de) 2010-12-23 2012-06-28 Henkel Ag & Co. Kgaa Deodorant- und Antitranspirant-Zusammensetzungen Zusammensetzungen zur Verhinderung von Körpergeruch
DE102011077233A1 (de) 2011-06-08 2012-12-13 Henkel Ag & Co. Kgaa nicht beschwerendes Stylingmittel
DE102011077365A1 (de) 2011-06-10 2012-12-13 Henkel Ag & Co. Kgaa Stylingmittel mit interessanter Textur
DE102011077364A1 (de) 2011-06-10 2012-12-13 Henkel Ag & Co. Kgaa Stylingmittel mit höchstem Halt
DE102011081108A1 (de) 2011-08-17 2013-02-21 Henkel Ag & Co. Kgaa Verwendung eines Mittels für keratinhaltige Fasern, enthaltend mindestens eine nichtionische, mittels Propylenoxid modifizierte Stärke und mindestens ein zusätzliches filmbildendes und/oder festigendes zur Verbesserung des Farberhalts oxidativer Haarcolorationen
DE102011087893A1 (de) 2011-12-07 2013-06-13 Henkel Ag & Co. Kgaa Haarpflegemittel mit interessanter Textur
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DE102011089040A1 (de) 2011-12-19 2013-06-20 Henkel Ag & Co. Kgaa Kosmetikum mit alkoxysilylfunktionalisierten, wasserlöslichen Polymeren und speziellen polaren Alkoxysilanen
DE102011089430A1 (de) 2011-12-21 2012-08-23 Henkel Ag & Co. Kgaa Treibmittelhaltige Zusammensetzungen mit verbesserter Umweltverträglichkeit
DE102011089562A1 (de) 2011-12-22 2013-06-27 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein spezielles Copolymer
DE102011089627A1 (de) 2011-12-22 2013-06-27 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens eine Cellulose mit kationischer Struktureinheit und mindestens ein spezielles Copolymer
DE102011089628A1 (de) 2011-12-22 2013-06-27 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles Copolymer des N-Vinylpyrrolidons und mindestens ein Polymer mit Struktureinheiten abgeleitet vom Maleinsäureester
DE102011089564A1 (de) 2011-12-22 2013-06-27 Henkel Ag & Co. Kgaa Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein Polymer mit Struktureinheiten abgeleitet vom Maleinsäureester
DE102012216671A1 (de) 2012-09-18 2013-06-06 Henkel Ag & Co. Kgaa Ressourcenschonendes Haut- und Haarreinigungsverfahren
DE102012218021A1 (de) 2012-10-02 2014-04-03 Henkel Ag & Co. Kgaa Leistungsgesteigerte Wasch- oder Reinigungsmittel mit Komplexbildnern II
DE102012218020A1 (de) 2012-10-02 2014-04-03 Henkel Ag & Co. Kgaa Leistungsstarke Tensidmischung und Wasch- oder Reinigungsmittel enthaltend diese
DE102012218019A1 (de) 2012-10-02 2014-04-03 Henkel Ag & Co. Kgaa Leistungsgesteigerte Wasch- oder Reinigungsmittel mit Komplexbildnern I
DE102012223975A1 (de) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Schaumaerosol zur Volumensteigerung
DE102012224051A1 (de) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Verwendung eines Mittels für keratinhaltige Fasern, enthaltend mindestens eine spezielle Polymerkombination zur Verbesserung des Farberhalts oxidativer Haarcolorationen
DE102012223971A1 (de) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Schaumaerosol zur Volumensteigerung
DE102012223978A1 (de) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Schaumaerosol zur Volumensteigerung
DE102012224298A1 (de) 2012-12-21 2014-06-26 Henkel Ag & Co. Kgaa Spray für elastischen und dauerhaften Halt
DE102013212873A1 (de) 2013-07-02 2015-01-08 Henkel Ag & Co. Kgaa Reinigungszusammensetzung mit hohem Fettsäuregehalt
DE102013219980A1 (de) 2013-10-02 2014-04-10 Henkel Ag & Co. Kgaa Rasiermittel für die empfindliche Haut
DE102013225609A1 (de) 2013-12-11 2014-06-12 Henkel Ag & Co. Kgaa Haarreinigungsmittel mit interessanter Textur
DE102013225761A1 (de) 2013-12-12 2014-07-03 Henkel Ag & Co. Kgaa Wirkstoffkombination und Haarbehandlungsmittel
DE102013226048A1 (de) 2013-12-16 2015-06-18 Henkel Ag & Co. Kgaa Stylingspray mit Volumeneffekt
DE102014215486A1 (de) 2014-08-06 2016-02-11 Henkel Ag & Co. Kgaa "Glättungsmittel, enthaltend eine Polymerkombination aus Polyurethanen und Amodimethiconen"
DE102014221367A1 (de) 2014-10-21 2016-04-21 Henkel Ag & Co. Kgaa Stylingmittel mit verbesserter Applizierbarkeit
JP6822961B2 (ja) 2014-12-19 2021-01-27 ロレアル 固体無水化粧用組成物、調製方法、美容処置方法及び関連キット
DE102015213478A1 (de) 2015-07-17 2017-01-19 Henkel Ag & Co. Kgaa Stabilisierungsgemisch
DE102015222976A1 (de) 2015-11-20 2017-05-24 Henkel Ag & Co. Kgaa Haarpflegemittel enthaltend Caseinhydrolysat zur Verbesserung der Haarstruktur
DE102015223196A1 (de) 2015-11-24 2017-05-24 Henkel Ag & Co. Kgaa Mittel und Verfahren zur Reinigung und/oder zur Pflege geschädigter keratinischer Fasern
DE102016207570A1 (de) 2016-05-03 2017-11-09 Henkel Ag & Co. Kgaa Feststoffstabilisierte Oxidationsmittelzubereitung, Produkt und Kit zur oxidativen Färbveränderung von Haaren
DE102016207569A1 (de) 2016-05-03 2017-11-09 Henkel Ag & Co. Kgaa Feststoffstabilisierte Farbcremes und Kit zur Färbung von Haaren
DE102021209511A1 (de) 2021-08-31 2023-03-02 Henkel Ag & Co. Kgaa Kosmetisches Reinigungsmittel
DE102021214287A1 (de) 2021-12-14 2023-06-15 Henkel Ag & Co. Kgaa "Haarbehandlungsmittel mit verbesserter Pflegewirkung"
DE102022203486A1 (de) 2022-04-07 2023-10-12 Henkel Ag & Co. Kgaa Verwendung verzweigter mittelkettiger Glycerinether als Antischuppenwirkstoffe
EP4382090A1 (fr) 2022-12-08 2024-06-12 Evonik Operations GmbH Compositions cosmétiques et pharmaceutiques contenant des souches de bacillus ou des bouillons de fermentation de celles-ci

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884946A (en) 1970-05-16 1975-05-20 Henkel & Cie Gmbh Process for the production of alkylene glycol monoesters
DE2024050B2 (de) 1970-05-16 1979-03-29 Henkel Kgaa, 4000 Duesseldorf Verfahren zur Herstellung von Alkylenglykolmonoestern
DE3836447C2 (de) 1988-10-26 1994-02-03 Stockhausen Chem Fab Gmbh Verfahren zur Gewinnung hochsulfatierter Fettsäuren, Hydroxifettsäuren oder oxalkylierter Hydroxifettsäuren
DE4017463A1 (de) 1990-05-30 1991-12-05 Henkel Kgaa Verfahren zur herstellung hochkonzentrierter pasten von alpha-sulfofettsaeure- alkylester-alkalimetallsalzen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9910319A1 *

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US6235913B1 (en) 2001-05-22
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JP2001514166A (ja) 2001-09-11
WO1999010319A1 (fr) 1999-03-04

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