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DE19741911C1 - Fatty acid polyglycol ester sulphate as foam booster for surfactants - Google Patents

Fatty acid polyglycol ester sulphate as foam booster for surfactants

Info

Publication number
DE19741911C1
DE19741911C1 DE19741911A DE19741911A DE19741911C1 DE 19741911 C1 DE19741911 C1 DE 19741911C1 DE 19741911 A DE19741911 A DE 19741911A DE 19741911 A DE19741911 A DE 19741911A DE 19741911 C1 DE19741911 C1 DE 19741911C1
Authority
DE
Germany
Prior art keywords
fatty acid
ether
sulfates
alkyl
surfactants
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.)
Expired - Fee Related
Application number
DE19741911A
Other languages
German (de)
Inventor
Hermann Dr Hensen
Ullrich Dr Bernecker
Joerg Dr Kahre
Werner Seipel
Holger Dr Tesmann
Thomas Dr Engels
Hans-Christian Dr Raths
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
Henkel AG and Co KGaA
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
Priority to DE19741911A priority Critical patent/DE19741911C1/en
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to PCT/EP1998/005202 priority patent/WO1999010458A1/en
Priority to EP98943891A priority patent/EP1007613A1/en
Priority to EP98945253A priority patent/EP1007614A1/en
Priority to US09/486,401 priority patent/US6498268B1/en
Priority to EP98948836A priority patent/EP1007620A1/en
Priority to PCT/EP1998/005213 priority patent/WO1999009942A1/en
Priority to DE59803990T priority patent/DE59803990D1/en
Priority to PCT/EP1998/005212 priority patent/WO1999010459A1/en
Priority to AU92631/98A priority patent/AU9263198A/en
Priority to PCT/EP1998/005207 priority patent/WO1999010470A1/en
Priority to ES98946355T priority patent/ES2186229T3/en
Priority to EP98946355A priority patent/EP1007500B1/en
Priority to AT98946355T priority patent/ATE227702T1/en
Priority to US09/486,340 priority patent/US6235696B1/en
Priority to PCT/EP1998/005208 priority patent/WO1999009938A1/en
Priority to PCT/EP1998/005206 priority patent/WO1999010471A1/en
Priority to JP2000507777A priority patent/JP2001514306A/en
Priority to PCT/EP1998/005186 priority patent/WO1999009943A1/en
Priority to PCT/EP1998/005200 priority patent/WO1999009940A1/en
Priority to JP2000507334A priority patent/JP2001513535A/en
Priority to EP98945252A priority patent/EP1007619A1/en
Priority to EP98946359A priority patent/EP1006992B1/en
Priority to PCT/EP1998/005210 priority patent/WO1999010461A1/en
Priority to PCT/EP1998/005204 priority patent/WO1999010309A1/en
Priority to CA002301507A priority patent/CA2301507A1/en
Priority to DE59806292T priority patent/DE59806292D1/en
Priority to PCT/EP1998/005205 priority patent/WO1999010469A1/en
Priority to PCT/EP1998/005201 priority patent/WO1999010463A1/en
Priority to JP2000507778A priority patent/JP2001514307A/en
Priority to PCT/EP1998/005211 priority patent/WO1999009935A2/en
Priority to PCT/EP1998/005189 priority patent/WO1999010468A1/en
Priority to PCT/EP1998/005187 priority patent/WO1999009944A1/en
Priority to JP2000507640A priority patent/JP2001514160A/en
Priority to US09/486,138 priority patent/US6300297B1/en
Priority to PCT/EP1998/005199 priority patent/WO1999010457A1/en
Priority to PCT/EP1998/005203 priority patent/WO1999010460A1/en
Priority to JP2000507770A priority patent/JP2001514302A/en
Application granted granted Critical
Publication of DE19741911C1 publication Critical patent/DE19741911C1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular 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
    • C08G65/2642Macromolecular 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
    • C08G65/2669Non-metals or compounds thereof
    • C08G65/2672Nitrogen or compounds thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular 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
    • C08G65/2603Macromolecular 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
    • C08G65/2615Macromolecular 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
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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    • C11D1/38Cationic compounds
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/94Mixtures with anionic, cationic or non-ionic compounds
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    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/042Compositions 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
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02Inorganic compounds ; Elemental compounds
    • C11D3/12Water-insoluble compounds
    • C11D3/124Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246Silicates, e.g. diatomaceous earth
    • C11D3/128Aluminium silicates, e.g. zeolites
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
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    • C11D3/2082Polycarboxylic acids-salts thereof
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/22Carbohydrates or derivatives thereof
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    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
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Abstract

A strongly-foaming detergent comprises (A) 10-90 wt. parts foam booster comprising a fatty acid polyglycol ester sulphate of formula R<1>COO(AO)xSO3X (I) where R<1>CO = optionally unsaturated 6-22C acyl group; x = on average 1-3; AO = an oxyethylene and/or oxypropylene group; and X = alkali(ne earth), ammonium, alkylammonium, alkanolammonium or glucammonium; and (B) 90-10 wt. parts anionic, nonionic, cationic, amphoteric and/or zwitterionic surfactant.

Description

Gebiet der ErfindungField of the Invention

Die Erfindung betrifft stark schäumende Detergensgemische mit einem Gehalt an niedrigalkoxylierten Fettsäurepolyglycolestersulfaten sowie die Verwendung dieser Stoffe als Schaumbooster für Tensid­ mischungen.The invention relates to strongly foaming detergent mixtures containing low alkoxylated Fatty acid polyglycol ester sulfates and the use of these substances as foam boosters for surfactants blends.

Stand der TechnikState of the art

In einer Vielzahl von Tensidanwendungen wird vom Verbraucher ein ausgeprägtes Schaumvermögen gewünscht. Ein Haarwaschmittel beispielsweise, das beim Shampoonieren eine nicht ausreichende Menge möglichst cremigen und beständigen Schaums produziert, hat kaum Aussicht im Markt zu be­ stehen; gleiches gilt für manuelle Geschirrspülmittel, auch wenn ein direkter Zusammenhang zwischen Schaumvermögen und Reinigungsleistung in vielen Fällen gar nicht nachweisbar ist. Ein Hersteller der­ artiger Produkte wird zwar in erster Linie bemüht sein, Formulierungen zu entwickeln, die den anwen­ dungstechnischen Anforderungen beispielsweise an Reinigungsleistung und Hautverträglichkeit ent­ sprechen, nichtsdestotrotz muß er aber auch den Schaumeigenschaften Rechnung tragen. Nun zeich­ nen sich nicht alle Tensidmischungen, die aus anwendungstechnischer Sicht zufriedenstellend und auch unter ökonomischer Betrachtung vertretbar sind, durch zufriedenstellendes Schaumvermögen aus. In dem einen Fall ist der Basisschaum zwar hoch, zerfällt jedoch rasch, im anderen Fall ist es genau umgekehrt, d. h. das Anschäumverhalten ist zwar eher durchschnittlich, der Schaum bleibt je­ doch lange Zeit stabil. Wenn diese Eigenschaften sich dann doch einmal vorteilhaft miteinander ver­ binden lassen, stellt man fest, daß die Mischungen entweder keine Wasserhärte oder Ölbelastung ver­ tragen. Demzufolge ist die Zahl der Tensidkombinationen, die dieses komplexe Anforderungsprofil er­ füllen, eher gering, weswegen im Markt stets die gleichen Formulierungen gefunden werden. Eine Mög­ lichkeit dieses Problem zu umgehen, besteht darin, Tensidformulierungen mit Additiven zu versehen, sogenannten Schaumboostern, die die Schaumeigenschaften der Mischungen günstig beeinflussen. Eine typische Gruppe von Verbindungen, die hierzu herangezogen werden können, sind die Fett­ säurealkanolamide, die jedoch den Nachteil aufweisen, daß sie selbst keine Tensideigenschaften aufweisen, also beispielsweise keinen Beitrag zum Reinigungsvermögen liefern, und zudem noch im Verdacht stehen, Spuren an Nitrosaminen enthalten zu können, was für Anwendungen, bei denen die Zubereitungen mit der menschlichen Haut in Kontakt kommen, absolut unerwünscht ist.In a variety of surfactant applications, the consumer has a pronounced foaming power wanted. For example, a shampoo that is not sufficient when shampooing Producing as much creamy and stable foam as possible has little prospect in the market stand; The same applies to manual dishwashing detergents, even if there is a direct connection between Foaming capacity and cleaning performance is in many cases not detectable. A manufacturer of the like products will primarily endeavor to develop formulations that the user technical requirements for cleaning performance and skin compatibility speak, but nevertheless he must also take the foam properties into account. Now draw not all surfactant mixtures that are satisfactory from an application point of view are also acceptable from an economic point of view, due to satisfactory foaming power out. In one case, the base foam is high, but disintegrates quickly, in the other it is exactly the opposite, d. H. the foaming behavior is rather average, the foam remains but stable for a long time. If these properties are mutually beneficial can bind, it is found that the mixtures either no water hardness or oil pollution ver carry. Accordingly, the number of surfactant combinations that meet this complex profile of requirements fill, rather low, which is why the same formulations are always found in the market. A possibility to avoid this problem is to add additives to surfactant formulations, So-called foam boosters, which have a favorable influence on the foam properties of the mixtures. A typical group of compounds that can be used for this are the fats Acid alkanolamides, which, however, have the disadvantage that they themselves have no surfactant properties  have, so for example make no contribution to the cleaning ability, and also in Are suspected of being able to contain traces of nitrosamines, which is for applications in which the Preparations come into contact with human skin, which is absolutely undesirable.

In diesem Zusammenhang sei auf die Patentschrift US 4,412,944 (Alcolac) verwiesen, aus der stark schäumende Reinigungsmittel bekannt sind, die neben anderen Tensiden Fettsäurepolyglycolester­ sulfate mit 6 bis 100 Alkylenoxideinheiten enthalten. Gegenstand der GB-PS 1498692 (Ciba-Geigy) sind Detegensgemische mit einem Gehalt an sulfatierten Ölsäureethoxylaten.In this connection, reference is made to US Pat. No. 4,412,944 (Alcolac), from which stark foaming cleaning agents are known which, in addition to other surfactants, include fatty acid polyglycol esters contain sulfates with 6 to 100 alkylene oxide units. Subject of GB-PS 1498692 (Ciba-Geigy) are detergent mixtures containing sulfated oleic acid ethoxylates.

Die komplexe Aufgabe der Erfindung hat somit darin bestanden, oberflächenaktive Zubereitungen zur Verfügung zu stellen, die frei von den oben geschilderten Nachteilen sind. Speziell galt es Schaum­ booster zu finden, die sowohl den Basisschaum als auch die Schaumbeständigkeit einer möglichst großen Zahl von Tensiden verbessern, und dies auch in Gegenwart von Wasserhärte und Ölbelastung.The complex object of the invention was therefore to prepare surface-active preparations To be available that are free from the disadvantages described above. Foam was especially important to find boosters that have both the base foam and the foam resistance of one Improve large number of surfactants, even in the presence of water hardness and oil pollution.

Beschreibung der ErfindungDescription of the invention

Gegenstand der Erfindung sind stark schäumende Detergensgemische, enthaltend
The invention relates to strongly foaming detergent mixtures containing

  • a) Fettsäurepolyglycolestersulfate der Formel (I),
    R1COO(AO)XSO3X (I)
    in der R1CO für einen linearen oder verzweigten, gesättigten oder ungesättigten Acylrest mit 6 bis 22 Kohlenstoffatomen, x für Zahlen von durchschnittlich 1 bis 3 und AO für einen CH2CH2O-, CH2CH(CH3)O- und/oder CH(CH3)CH2O-Rest und X für ein Alkali- und/oder Erdalkalimetall, Am­ monium, Alkylammonium, Alkanolammonium oder Glucammonium steht, und
    a) fatty acid polyglycol ester sulfates of the formula (I),
    R 1 COO (AO) X SO 3 X (I)
    in the R 1 CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, x for numbers from 1 to 3 on average and AO for a CH 2 CH 2 O-, CH 2 CH (CH 3 ) O- and / or CH (CH 3 ) CH 2 O radical and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, and
  • b) weitere anionische, nichtionische, kationische, amphotere und/oder zwitterionische Tenside,b) further anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants,

mit der Maßgabe, daß das Gewichtsverhältnis der Komponenten (a) und (b) 90 : 10 bis 10 : 90 beträgt.with the proviso that the weight ratio of components (a) and (b) is 90:10 to 10:90.

Überraschenderweise wurde gefunden, daß niedrigalkoxylierte Fettsäurepolyglycolestersulfate, die selbst über keine ausgeprägten Schaumeigenschaften verfügen, Schaumbooster darstellen, also so­ wohl den Basisschaum als auch die Schaumstabilität anderer Tenside in synergistischer Weise verbes­ sern. Die Erfindung schließt die Erkenntnis mit ein, daß diese synergistischen Effekte auch in hartem Wasser und in Gegenwart von Ölbelastung (Sebum) erhalten werden und für ein breites Spektrum von Tensiden gelten. Ein weiterer Vorteil der Erfindung besteht darin, daß die Fettsäurepolyglycolester solu­ bilisierende Eigenschaften besitzen und so die Formulierung von ansonsten in kaltem Wasser eher schwerlöslichen Tensiden verbessern. Zudem besitzen die Schaumbooster hinreichende Detergens­ eigenschaften, so daß sie im Gegensatz beispielsweise zu Alkanolamiden einen Beitrag zum Reini­ gungsvermögen liefern. Schließlich sind die Stoffe aus hautkosmetischer Sicht unbedenklich, biologisch leicht abbaubar und natürlich frei von Nitrosaminen.Surprisingly, it was found that low alkoxylated fatty acid polyglycol ester sulfates, the themselves have no pronounced foam properties, are foam boosters, so like this probably the base foam as well as the foam stability of other surfactants in a synergistic way ser. The invention includes the knowledge that these synergistic effects also in hard Water and in the presence of oil pollution (sebum) can be obtained and for a wide range of Surfactants apply. Another advantage of the invention is that the fatty acid polyglycol ester solu possess bilizing properties and thus the formulation of otherwise in cold water  improve poorly soluble surfactants. The foam boosters also have sufficient detergent properties, so that, in contrast to, for example, alkanolamides, they contribute to the cleaning deliver ability. After all, the substances are harmless from the skin cosmetic point of view, organic easily degradable and of course free of nitrosamines.

FettsäurepolyglycolestersulfateFatty acid polyglycol ester sulfates

Fettsäurepolyglycolestersulfate werden durch Sulfatierung der entsprechenden Fettsäurepolyglycol­ ester hergestellt. Diese wiederum sind nach den einschlägigen präparativen Verfahren der organischen Chemie erhältlich. Hierzu wird Ethylenoxid, Propylenoxid oder deren Gemisch - in random- oder Block­ verteilung - an die entsprechenden Fettsäuren angelagert, wobei diese Reaktion säurekatalysiert, vor­ zugsweise aber in Gegenwart von Basen, wie z. B. Natriummethylat oder calciniertem Hydrotalcit er­ folgt. Wird ein Alkoxylierungsgrad von 1 gewünscht, können die Zwischenprodukte auch durch Vereste­ rung der Fettsäuren mit einem entsprechenden Alkylenglycol hergestellt werden. Die Sulfatierung der Fettsäurepolyglycolester kann in an sich bekannter Weise mit Chlorsulfonsäure oder vorzugsweise gasförmigem Schwefeltrioxid durchgeführt werden, wobei das molare Einsatzverhältnis zwischen Fett­ säurepolyglycolester und Sulfatierungsmittel im Bereich von 1 : 0,95 bis 1 : 1,2, vorzugsweise 1 : 1 bis 1 : 1,1 und die Reaktionstemperatur 30 bis 80 und vorzugsweise 50 bis 60°C betragen kann. Es ist ferner möglich, die Fettsäurepolyglycolester zu untersulfatieren, d. h. deutlich weniger Sulfatierungs­ mittel einzusetzen, als dies für eine vollständige Umsetzung stöchiometrisch erforderlich wäre. Wählt man beispielsweise molare Einsatzmengen von Fettsäurepolyglycolester zu Sulfatierungsmittel von 1 : 0,5 bis 1 : 0,95 werden Mischungen von Fettsäurepolyglycolestersulfaten und Fettsäurepolyglycol­ estern erhalten, die für eine ganze Reihe von Anwendungen ebenfalls vorteilhaft sind. Um eine Hydrolyse zu vermeiden ist es dabei sehr wichtig, die Neutralisation bei einem pH-Wert im Bereich von 5 bis 9, vorzugsweise 7 bis 8 durchzuführen. Typische Beispiele für geeignete Ausgangsstoffe sind die Anlagerungsprodukte von 1 bis 3 Mol Ethylenoxid und/oder Propylenoxid, vorzugsweise aber die Addukte mit 1 Mol Ethylenoxid oder 1 Mol Propylenoxid an Capronsäure, Caprylsäure, 2-Ethyl­ hexansäure, Caprinsäure, Laurinsäure, Isotridecansäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Elaeo­ stearinsäure, Arachinsäure, Gadoleinsäure, Behensäure und Erucasäure sowie deren technische Mischungen, die dann wie oben beschrieben sulfatiert und neutralisiert werden. Vorzugsweise werden Fettsäurepolyglycolestersulfate der Formel (I) eingesetzt, in der R1CO für einen Acylrest mit 12 bis 18 Kohlenstoffatomen, x für durchschnittlich 1 oder 2, AO für eine CH2CH2O-Gruppe und X für Natrium oder Ammonium steht, wie beispielsweise Laurinsäure+1EO-sulfat-Natriumsalz, Laurinsäure+1EO- sulfat-Ammoniumsalz, Kokos-fettsäure+1EO-sulfat-Natriumsalz, Kokosfettsäure+1EO-sulfat-Ammo­ niumsalz, Talgfettsäure+1EO-sulfat-Natriumsalz, Talgfettsäure+1EO-sulfat-Ammoniumsalz sowie de­ ren Mischungen. Fatty acid polyglycol ester sulfates are produced by sulfating the corresponding fatty acid polyglycol esters. These in turn can be obtained using the relevant preparative processes in organic chemistry. For this purpose, 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. B. sodium methylate or calcined hydrotalcite it follows. If a degree of alkoxylation of 1 is desired, 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 using 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 less sulfating agents than would be required stoichiometrically for a complete reaction. For example, if one chooses 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. In order to avoid hydrolysis, it is very important to carry out the neutralization at a pH in the range from 5 to 9, preferably 7 to 8. 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, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, which are then sulfated and neutralized as described above. Fatty acid polyglycol ester sulfates of the formula (I) are preferably used in which R 1 CO stands for an acyl radical having 12 to 18 carbon atoms, x for an average of 1 or 2, AO for a CH 2 CH 2 O group and X for sodium or ammonium, such as for example lauric acid + 1EO sulfate sodium salt, lauric acid + 1EO sulfate ammonium salt, coconut fatty acid + 1EO sulfate sodium salt, coconut fatty acid + 1EO sulfate ammonium salt, tallow fatty acid + 1EO sulfate sodium salt, tallow fatty acid + 1EO sulfate Ammonium salt and their mixtures.

TensideSurfactants

Als oberflächenaktive Stoffe können nichtionische, anionische, kationische und/oder amphotere bzw. amphotere Tenside enthalten sein. Typische Beispiele für anionische Tenside sind Seifen, Alkylben­ zolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, α-Methyl­ estersulfonate, Sulfofettsäuren, Alkylsulfate, Fettalkoholethersulfate, Glycerinethersulfate, Hydroxy­ mischethersulfate, Monoglycerid(ether)sulfate, Fettsäureamid(ether)sulfate, Mono- und Dialkylsulfo­ succinate, Mono- und Dialkylsulfosuccinamate, Sulfotriglyceride, Amidseifen, Ethercarbonsäuren und deren Salze, Amidethercarbonsäuren und deren Salzen, Fettsäureisethionate, Fettsäuresarcosinate, Fettsäuretauride, N-Acylaminosäuren wie beispielsweise Acyllactylate, Acyltartrate, Acylglutamate und Acylaspartate, Alkyloligoglucosidsulfate, Proteinfettsäurekondensate (insbesondere pflanzliche Pro­ dukte auf Weizenbasis) und Alkyl(ether)phosphate. Sofern die anionischen Tenside Polyglycolether­ ketten enthalten, können diese eine konventionelle, vorzugsweise jedoch eine eingeengte Homologen­ verteilung aufweisen. Typische Beispiele für nichtionische Tenside sind Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolyglycolether, Fettaminpolygly­ colether, alkoxylierte Triglyceride, Mischether bzw. Mischformale, gegebenenfalls partiell oxidierte Alk(en)yloligoglykoside bzw. Glucoronsäurederivate, Fettsäure-N-alkylglucamide, Proteinhydrolysate (insbesondere pflanzliche Produkte auf Weizenbasis), Polyolfettsäureester, Zuckerester, Sorbitanester, Polysorbate und Aminoxide. Sofern die nichtionischen Tenside Polyglycoletherketten enthalten, können diese eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen. Typische Beispiele für kationische Tenside sind quartäre Tetraalkylammoniumverbindungen und Esterquats, insbesondere quaternierte Difettsäuretrialkanolamin- oder Difettsäuremethyldiethanolamin­ estersalze. Typische Beispiele für amphotere bzw. zwitterionische Tenside sind Alkylbetaine, Alkyl­ amidobetaine, Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine. Bei den ge­ nannten Tensiden handelt es sich ausschließlich um bekannte Verbindungen. Hinsichtlich Struktur und Herstellung dieser Stoffe sei auf einschlägige Übersichtsarbeiten beispielsweise J. Falbe (ed.), "Sur­ factants in Consumer Products", Springer Verlag, Berlin, 1987, S. 54-124 oder J. Falbe (ed.), "Katalysatoren, Tenside und Mineralöladditive", Thieme Verlag, Stuttgart, 1978, S. 123-217 ver­ wiesen. Die Detergensmischungen können die Komponenten (a) und (b) vorzugsweise im Gewichtsverhältnis 75 : 25 bis 25 : 75 und insbesondere im Verhältnis 60 : 40 bis 40 : 60 enthalten. Bevorzugte binäre bzw. ternäre Kombinationen sind die von Laurinsäure- bzw. Kokosfettsäure+1EO- sulfat-Natrium- bzw. -Ammoniumsalz mit Alkylethersulfaten, Fettsäuremonoglyceridsulfaten, Alkyloligo­ glucosiden und/oder Betainen. Nonionic, anionic, cationic and / or amphoteric or amphoteric surfactants may be included. Typical examples of anionic surfactants are soaps, alkylbenes benzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, α-methyl estersulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfo succinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, amide ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, Fatty acid taurides, N-acylamino acids such as acyl lactylates, acyl tartrates, acyl glutamates and Acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable pro wheat-based products) and alkyl (ether) phosphates. If the anionic surfactants polyglycol ether chains contain, these can be a conventional, but preferably a narrowed homolog have distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, Alkylphenol polyglycol ether, fatty acid polyglycol ester, fatty acid amide polyglycol ether, fatty amine polygly colethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized Alk (en) yl oligoglycosides or glucoronic acid derivatives, fatty acid N-alkyl glucamides, protein hydrolyzates (especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, Polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these have a conventional, but preferably a narrowed homolog distribution. Typical examples of cationic surfactants are quaternary tetraalkylammonium compounds and Ester quats, especially quaternized difatty acid trialkanolamine or difatty acid methyl diethanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. With the ge named surfactants are only known compounds. Regarding structure and The production of these substances is based on relevant reviews, for example J. Falbe (ed.), "Sur factants in Consumer Products ", Springer Verlag, Berlin, 1987, pp. 54-124 or J. Falbe (ed.), "Catalysts, surfactants and mineral oil additives", Thieme Verlag, Stuttgart, 1978, pp. 123-217 ver grasslands. The components (a) and (b) can preferably be used in the detergent mixtures Weight ratio 75:25 to 25:75 and in particular in a ratio of 60:40 to 40:60. Preferred binary or ternary combinations are those of lauric acid or coconut fatty acid + 1EO- sulfate sodium or ammonium salt with alkyl ether sulfates, fatty acid monoglyceride sulfates, alkyl oligo glucosides and / or betaines.  

Gewerbliche AnwendbarkeitIndustrial applicability

Die Fettsäurepolyglycolestersulfate der Formel (I) verbessern das Anschäumverhalten und die Schaumbeständigkeit einer großen Zahl von Tensiden auch dann noch in synergistischer Weise, wenn Wasserhärte und Ölbelastung zugegen sind. Ein weiterer Gegenstand der Erfindung betrifft daher ihre Verwendung als Schaumbooster zur Verbesserung der Schaumeigenschaften anionischer, nichtioni­ scher, kationischer und/oder amphoterer bzw. zwitterionischer Tenside.The fatty acid polyglycol ester sulfates of the formula (I) improve the foaming behavior and Foam resistance of a large number of surfactants even in a synergistic manner if Water hardness and oil pollution are present. Another object of the invention therefore relates to their Use as a foam booster to improve the foam properties of anionic, non-ionic shear, cationic and / or amphoteric or zwitterionic surfactants.

BeispieleExamples

Zur Untersuchung des Schaumverhaltens wurden 10 Gew.-%ige wäßrige Tensidlösungen (21°dH, + 1 Gew.-% Sebum) hergestellt und das Schaumvolumen gemäß DIN-Norm 53 902, Teil 1 bestimmt. Bei dieser Methode wird der Schaum durch 30 Sekunden langes Schlagen der flüssigen Probe in einem Standzylinder mit einer an einem Stiel befestigten, waagerecht ausgerichteten gelochten Platte er­ zeugt. Das entstandene Schaumvolumen wird unmittelbar nach dem Beendigen des Schlagens, sowie nach 1, 5 und 20 min gemessen. Die Ergebnisse sind in den Tabellen 1 bis 3 zusammengefaßt. Folgende Tenside wurden eingesetzt (Mengenangaben als Gew.-%).
To investigate the foam behavior, 10% by weight aqueous surfactant solutions (21 ° dH, + 1% by weight sebum) were prepared and the foam volume was determined in accordance with DIN standard 53 902, part 1. In this method, the foam is generated by beating the liquid sample in a standing cylinder for 30 seconds with a horizontally aligned perforated plate attached to a handle. The resulting foam volume is measured immediately after stopping, as well as after 1, 5 and 20 minutes. The results are summarized in Tables 1 to 3. The following surfactants were used (quantitative data as% by weight).

  • 1. Sodium Laureth Sulfate (Texapon® NSO, Henkel KGaA)1. Sodium Laureth Sulfate (Texapon® NSO, Henkel KGaA)
  • 2. Cocosmonoglyceridsulfat-Natriumsalz (Plantapon® CMGS, Henkel KGaA)2. Coconut monoglyceride sulfate sodium salt (Plantapon® CMGS, Henkel KGaA)
  • 3. Laureth-7 Ethercarbonsäure-Natriumsalz3. Laureth-7 ether carboxylic acid sodium salt
  • 4. Coco Glucosides (Plantacare® APG 1200, Henkel KGaA)4. Coco Glucosides (Plantacare® APG 1200, Henkel KGaA)
  • 5. Laurinsäure-N-methylglucamid5. Lauric acid N-methylglucamide
  • 6. Cocamidopropyl Betaine (Dehyton® PK, Henkel KGaA)6. Cocamidopropyl betaine (Dehyton® PK, Henkel KGaA)
  • 7. Laurinsäure+1EO-sulfat-Natriumsalz7. Lauric acid + 1EO sulfate sodium salt
  • 8. Kokosfettsäure+1EO-sulfat-Ammoniumsalz8. Coconut fatty acid + 1EO sulfate ammonium salt

Tabelle 1 Table 1

Schaummessungen - Binäre Tensidmischungen (erfindungsgemäß) Foam measurements - binary surfactant mixtures (according to the invention)

Tabelle 1 Table 1

Schaummessungen - Binäre Tensidmischungen (erfindungsgemäß) - Fortsetzung Foam measurements - binary surfactant mixtures (according to the invention) - continued

Tabelle 2 Table 2

Schaummessungen - Ternäre Tensidmischungen (erfindungsgemäß) Foam measurements - ternary surfactant mixtures (according to the invention)

Tabelle 3 Table 3

Schaummessungen (Vergleichsversuche) Foam measurements (comparative tests)

Claims (7)

1. Stark schäumende Detergensgemische, enthaltend
  • a) Fettsäurepolyglycolestersulfate der Formel (I),
    R1COO(AO)XSO3X (1)
    in der R1CO für einen linearen oder verzweigten, gesättigten oder ungesättigten Acylrest mit 6 bis 22 Kohlenstoffatomen, x für Zahlen von durchschnittlich 1 bis 3 und AO für einen CH2CH2O-, CH2CH(CH3)O- und/oder CH(CH3)CH2O-Rest und X für ein Alkali- und/oder Erd­ alkalimetall, Ammonium, Alkylammonium, Alkanolammonium oder Glucammonium steht, und
  • b) weitere anionische, nichtionische, kationische, amphotere und/oder zwitterionische Tenside,
mit der Maßgabe, daß das Gewichtsverhältnis der Komponenten (a) und (b) 90 : 10 bis 10 : 90 be­ trägt.
1. Highly foaming detergent mixtures containing
  • a) fatty acid polyglycol ester sulfates of the formula (I),
    R 1 COO (AO) X SO 3 X (1)
    in the R 1 CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, x for numbers from 1 to 3 on average and AO for a CH 2 CH 2 O-, CH 2 CH (CH 3 ) O- and / or CH (CH 3 ) CH 2 O radical and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, and
  • b) further anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants,
with the proviso that the weight ratio of components (a) and (b) be 90:10 to 10:90 be.
2. Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie Fettsäurepolyglycol­ estersulfate der Formel (I) enthalten, in der R1CO für einen Acylrest mit 12 bis 18 Kohlenstoff­ atomen, x für durchschnittlich 1 oder 2, AO für eine CH2CH2O-Gruppe und X für Natrium oder Ammonium steht.2. Detergent mixtures according to claim 1, characterized in that they contain fatty acid polyglycol ester sulfates of the formula (I) in which R 1 CO for an acyl radical having 12 to 18 carbon atoms, x for an average of 1 or 2, AO for a CH 2 CH 2 O group and X represents sodium or ammonium. 3. Detergensgemische nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, daß sie anionische Tenside enthalten, die ausgewählt sind aus der Gruppe, die gebildet wird von Seifen, Alkylbenzol­ sulfonaten, Alkansulfonaten, Olefinsulfonaten, Alkylethersulfonaten, Glycerinethersulfonaten, α- Methylestersulfonaten, Sulfofettsäuren, Alkylsulfaten, Fettalkoholethersulfaten, Glycerinethersul­ faten, Hydroxymischethersulfaten, Monoglycerid(ether)sulfaten, Fettsäureamid(ether)sulfaten, Mono- und Dialkylsulfosuccinaten, Mono- und Dialkylsulfosuccinamaten, Sulfotriglyceriden, Amid­ seifen, Ethercarbonsäuren und deren Salze, Amidethercarbonsäuren und deren Salzen, Fett­ säureisethionaten, Fettsäuresarcosinaten, Fettsäuretauriden, N-Acylaminosäuren, Alkyloligogluco­ sidsulfaten, Proteinfettsäurekondensatn und Alkyl(ether)phosphaten.3. Detergent mixtures according to claims 1 and 2, characterized in that they are anionic Contain surfactants selected from the group consisting of soaps, alkylbenzene sulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, α- Methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulf faten, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, Mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, amide ether carboxylic acids and their salts, fat Acid isethionates, fatty acid sarcosinates, fatty acid aurides, N-acylamino acids, alkyl oligogluco sulfides, protein fatty acid condensates and alkyl (ether) phosphates. 4. Detergensgemische nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß sie nicht­ ionische Tenside enthalten, die ausgewählt sind aus der Gruppe, die gebildet wird von Fettalkohol­ polyglycolethern, Fettsäurepolyglycolester, Alkylphenolpolyglycolethern, Fettsäureamidpolyglycol­ ethern, Fettaminpolyglycolethern, alkoxylierten Triglyceriden, Mischethern bzw. Mischformalen, gegebenenfalls partiell oxidierten Alk(en)yloligoglykosiden bzw. Glucoronsäurederivaten, Fettsäu­ re-N-alkylglucamiden, Proteinhydrolysaten, Polyolfettsäureestern, Zuckerestern, Sorbitanestern, Polysorbaten und Aminoxiden.4. Detergent mixtures according to claims 1 to 3, characterized in that they are not contain ionic surfactants selected from the group consisting of fatty alcohol polyglycol ethers, fatty acid polyglycol esters, alkylphenol polyglycol ethers, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk (en) yl oligoglycosides or glucoronic acid derivatives, fatty acid  re-N-alkyl glucamides, protein hydrolyzates, polyol fatty acid esters, sugar esters, sorbitan esters, Polysorbates and amine oxides. 5. Detergensgemische nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß sie kationische Tenside enthalten, die ausgewählt sind aus der Gruppe, die gebildet wird von quartären Tetra­ alkylammoniumverbindungen und Esterquats.5. Detergent mixtures according to claims 1 to 4, characterized in that they are cationic Contain surfactants that are selected from the group that is formed by quaternary tetra alkyl ammonium compounds and ester quats. 6. Detergensgemische nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß sie amphotere bzw. zwitterionische Tenside enthalten, die ausgewählt sind aus der Gruppe, die gebildet wird von Alkylbetainen, Alkylamidobetainen, Aminopropionaten, Aminoglycinaten, Imidazoliniumbetainen und Sulfobetainen.6. Detergent mixtures according to claims 1 to 5, characterized in that they are amphoteric or zwitterionic surfactants which are selected from the group formed by Alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. 7. Verwendung von Fettsäurepolyglycolestersulfaten der Formel (I) als Schaumbooster zur Verbes­ serung der Schaumeigenschaften von anionischen, nichtionischen, kationischen und/oder ampho­ teren bzw. zwitterionischen Tensiden.7. Use of fatty acid polyglycol ester sulfates of the formula (I) as foam boosters for verbs improvement of the foam properties of anionic, nonionic, cationic and / or ampho teren or zwitterionic surfactants.
DE19741911A 1997-08-25 1997-09-25 Fatty acid polyglycol ester sulphate as foam booster for surfactants Expired - Fee Related DE19741911C1 (en)

Priority Applications (38)

Application Number Priority Date Filing Date Title
DE19741911A DE19741911C1 (en) 1997-09-25 1997-09-25 Fatty acid polyglycol ester sulphate as foam booster for surfactants
EP98945252A EP1007619A1 (en) 1997-08-25 1998-08-17 Hard soap containing fatty acid polyglycol ester sulphates
EP98945253A EP1007614A1 (en) 1997-08-25 1998-08-17 Heavily foaming detergent mixtures containing fatty acid polyglycol ester sulphates
US09/486,401 US6498268B1 (en) 1997-08-25 1998-08-17 Method for producing alkylene glycol esters with limited homologue distribution
EP98948836A EP1007620A1 (en) 1997-08-25 1998-08-17 Syndet soaps containing fatty acid polyglycol ester sulfate
PCT/EP1998/005213 WO1999009942A1 (en) 1997-08-25 1998-08-17 Use of fatty acid polyglycol ester sulphates
DE59803990T DE59803990D1 (en) 1997-08-25 1998-08-17 USE OF FATTY ACID POLYGLYCOLESTER SULFATES
PCT/EP1998/005212 WO1999010459A1 (en) 1997-08-25 1998-08-17 Method for producing water- and dust-free anion tenside granules
AU92631/98A AU9263198A (en) 1997-08-25 1998-08-17 Heavily foaming detergent mixtures containing fatty acid polyglycol ester sulphates
PCT/EP1998/005207 WO1999010470A1 (en) 1997-08-25 1998-08-17 Use of fatty acid polyglycol ester sulphates
ES98946355T ES2186229T3 (en) 1997-08-25 1998-08-17 PROCEDURE FOR THE OBTAINING OF ALKYL CHOLESTERS WITH LIMITED DISTRIBUTION OF HOMOLOGIES.
EP98946355A EP1007500B1 (en) 1997-08-25 1998-08-17 Method for producing alkylene glycol esters with limited homologue distribution
AT98946355T ATE227702T1 (en) 1997-08-25 1998-08-17 METHOD FOR PRODUCING ALKYLENE GLYCOL ESTERS WITH RESTRICTED HOMOLOGEN DISTRIBUTION
US09/486,340 US6235696B1 (en) 1997-08-25 1998-08-17 Heavily foaming detergent mixtures containing fatty acid polyglycol ester sulphates
PCT/EP1998/005208 WO1999009938A1 (en) 1997-08-25 1998-08-17 Cosmetic agents containing fatty acid polyglycol ester sulphates
PCT/EP1998/005206 WO1999010471A1 (en) 1997-08-25 1998-08-17 Solid detergents containing fatty acid polyglycol ester sulphates and solid builders
JP2000507777A JP2001514306A (en) 1997-08-25 1998-08-17 Synthetic makeup soap containing fatty acid polyglycol ester sulfate
PCT/EP1998/005186 WO1999009943A1 (en) 1997-08-25 1998-08-17 Sunscreening agent containing fatty acid polyglycol ester sulphates
PCT/EP1998/005202 WO1999010458A1 (en) 1997-08-25 1998-08-17 Aqueous agents for cleaning hard surfaces
JP2000507334A JP2001513535A (en) 1997-08-25 1998-08-17 Use of fatty acid polyglycol ester sulfate
PCT/EP1998/005210 WO1999010461A1 (en) 1997-08-25 1998-08-17 Heavily foaming detergent mixtures containing fatty acid polyglycol ester sulphates
EP98943891A EP1007613A1 (en) 1997-08-25 1998-08-17 Method for producing water- and dust-free anion tenside granules
EP98946359A EP1006992B1 (en) 1997-08-25 1998-08-17 Use of fatty acid polyglycol ester sulphates
PCT/EP1998/005204 WO1999010309A1 (en) 1997-08-25 1998-08-17 Method for producing alkylene glycol esters with limited homologue distribution
CA002301507A CA2301507A1 (en) 1997-08-25 1998-08-17 Method for producing alkylene glycol esters with limited homologue distribution
DE59806292T DE59806292D1 (en) 1997-08-25 1998-08-17 METHOD FOR PRODUCING ALKYLENE GLYCOLESTERS WITH RESTRICTED HOMOLOGOUS DISTRIBUTION
PCT/EP1998/005205 WO1999010469A1 (en) 1997-08-25 1998-08-17 Hard soap containing fatty acid polyglycol ester sulphates
PCT/EP1998/005201 WO1999010463A1 (en) 1997-08-25 1998-08-17 Aqueous agents for washing dishes by hand
JP2000507778A JP2001514307A (en) 1997-08-25 1998-08-17 Hard soap containing fatty acid polyglycol ester sulfate
PCT/EP1998/005211 WO1999009935A2 (en) 1997-08-25 1998-08-17 Cosmetic preparations containing fatty acid polyglycol ester sulphates and polymers
PCT/EP1998/005189 WO1999010468A1 (en) 1997-08-25 1998-08-17 Syndet soaps containing fatty acid polyglycol ester sulfate
PCT/EP1998/005187 WO1999009944A1 (en) 1997-08-25 1998-08-17 Aqueous nacreous lustre dispersions
JP2000507640A JP2001514160A (en) 1997-08-25 1998-08-17 Preparation of alkylene glycol esters with narrow homolog distribution
US09/486,138 US6300297B1 (en) 1997-08-25 1998-08-17 Hard soap containing fatty acid polyglycol ester sulphates
PCT/EP1998/005199 WO1999010457A1 (en) 1997-08-25 1998-08-17 Method for stabilising aqueous ester sulphate tensides
PCT/EP1998/005203 WO1999010460A1 (en) 1997-08-25 1998-08-17 Flowable tenside preparations containing fatty acid polyglycol ester sulphates
JP2000507770A JP2001514302A (en) 1997-08-25 1998-08-17 Highly foamable detergent mixtures containing fatty acid polyglycol ester sulfate
PCT/EP1998/005200 WO1999009940A1 (en) 1997-08-25 1998-08-17 Method for permanently deforming keratin fibres

Applications Claiming Priority (1)

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DE19741911A DE19741911C1 (en) 1997-09-25 1997-09-25 Fatty acid polyglycol ester sulphate as foam booster for surfactants

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Publication number Priority date Publication date Assignee Title
WO1999049006A1 (en) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Fatty acid oligo-alkylene glycol ester sulfates in aqueous tenside solutions
CN104672113A (en) * 2015-03-12 2015-06-03 中国科学院广州能源研究所 Preparation method of fatty ester sulphonate

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GB1498692A (en) * 1975-01-29 1978-01-25 Ciba Geigy Ag Detergent composition
US4412944A (en) * 1980-02-12 1983-11-01 Alcolac, Inc. High foaming, low eye irritation cleaning compositions containing ethoxylated anionic (C13-C30) sulphates

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Publication number Priority date Publication date Assignee Title
GB1498692A (en) * 1975-01-29 1978-01-25 Ciba Geigy Ag Detergent composition
US4412944A (en) * 1980-02-12 1983-11-01 Alcolac, Inc. High foaming, low eye irritation cleaning compositions containing ethoxylated anionic (C13-C30) sulphates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999049006A1 (en) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Fatty acid oligo-alkylene glycol ester sulfates in aqueous tenside solutions
CN104672113A (en) * 2015-03-12 2015-06-03 中国科学院广州能源研究所 Preparation method of fatty ester sulphonate
CN104672113B (en) * 2015-03-12 2016-06-08 中国科学院广州能源研究所 A kind of preparation method of fatty acid ester sulfonate

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