EP1007508A1 - Verfahren zur herstellung von fettsäurepolyglycolestersulfaten - Google Patents

Verfahren zur herstellung von fettsäurepolyglycolestersulfaten

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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Withdrawn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)
French (fr)
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/de
Withdrawn legal-status Critical Current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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • 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
    • C11D3/02—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
    • 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
    • C11D1/04—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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • C—CHEMISTRY; METALLURGY
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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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the 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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EP98947432A 1997-08-25 1998-08-17 Verfahren zur herstellung von fettsäurepolyglycolestersulfaten Withdrawn EP1007508A1 (de)

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DE102014215486A1 (de) 2014-08-06 2016-02-11 Henkel Ag & Co. Kgaa "Glättungsmittel, enthaltend eine Polymerkombination aus Polyurethanen und Amodimethiconen"
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AU9435498A (en) 1999-03-16
DE19736906A1 (de) 1999-03-04

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