WO1993020171A1 - Low foaming aqueous detergent mixtures - Google Patents

Low foaming aqueous detergent mixtures Download PDF

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Publication number
WO1993020171A1
WO1993020171A1 PCT/EP1993/000724 EP9300724W WO9320171A1 WO 1993020171 A1 WO1993020171 A1 WO 1993020171A1 EP 9300724 W EP9300724 W EP 9300724W WO 9320171 A1 WO9320171 A1 WO 9320171A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
detergent mixtures
aqueous detergent
low
carbon atoms
Prior art date
Application number
PCT/EP1993/000724
Other languages
German (de)
French (fr)
Inventor
Wolfgang Poly
Christian Nitsch
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1993020171A1 publication Critical patent/WO1993020171A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D1/88—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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—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
    • C11D1/66—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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to low-foaming aqueous detergent mixtures comprising alkyl and / or alkenyl oligoglycoside ethers and anionic, nonionic and / or amphoteric or zwitterionic surfactants, and to the use of alkyl and / or alkylene oligoglycoside ethers as defoamers for producing low-foam aqueous detergent mixtures and the products containing them.
  • foam brakes which are also often referred to as "foam brakes".
  • foam brakes include the salts of long-chain fatty acids [DE-PS-10 56 316, DE-PS-10 80 250, Procter & Gamble Co.] as well as end-capped fatty alcohol polyglycol ethers, so-called “mixed ethers” [DE-Al- 33 45 349, EP-B1-0 303 928, Henkel KGaA].
  • the object of the invention was therefore to schaumregu ⁇ profiled detergent mixtures based on anionic, nonionic to provide "shear and / or amphoteric or zwitterionic surfactants are available which are free from the share Nach ⁇ .
  • the invention relates to low-foam aqueous detergent mixtures containing
  • Rl is a linear or branched aliphatic hydrocarbon radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds
  • R2 represents a linear or branched alkyl radical having 1 to 8 carbon atoms or a benzyl radical
  • alkyl and / or alkenyl oligoglycoside ethers reduces the foaming power of a large number of anionic surfactants in a synergistic manner.
  • the detergent mixtures according to the invention have low foaming and a constantly high performance over a wide temperature range.
  • Alkyl oligoglucoside benzyl ethers have proven to be particularly effective foam brakes.
  • Alkyl and / or alkenyl oligoglycoside ethers are known low-foaming substances which are known, for example, from DE-Al-38 35 199 (BASF AG). For their preparation, one can start from alkyl and / or alkenyl oligoglycosides which are etherified with alkyl or alkyl aryl halides in the presence of alkali metal hydroxides.
  • Alkyl and / or Alkenyloligoglykosidether which can be used in the context of the invention preferably provide Um ⁇ reduction products of Cg-C22 ⁇ A lkyl- and / or Alkenyloligogly ⁇ kosiden with Ci-Cg-alkyl halides or benzyl halides.
  • Typical examples are reaction products of Ci2 / 14 ⁇ cocoalkyl oligoglucoside, Cg i Q -Ko ⁇ os- ⁇ lkyloligoglucosid or Ci6 / ⁇ g-tallow alkyl oligoglucoside with methyl chloride, butyl chloride, octyl chloride or benzyl chloride.
  • Preferred alkyl and / or alkenyl oligoglycoside ethers are the alkyl and / or alkenyl oligoglycoside ethers of the formula (I) in which R! for an alkyl radical with 12 to 18 carbon atoms.
  • R2 fo r * a benzyl radical, p is a number from 1 to 3 and n is a number from 0.7 to 1.3.
  • Suitable anionic surfactants which can make up the mixture component b) are soaps, alkylbenzenesulfonates, olefin sulfonates, alkanesulfonates, alkyl ether sulfonates, alpha sulfo fatty acids, internal sulfo fatty acids, alpha ester sulfonates, glycerol ether sulfonates, alkyl sulfates, alkyl ether sulfates with conventional narrow homolog distribution, glycerol ether sulfates, monoglyceride (ether) sulfates, hydroxy mixed ether sulfates, alkyl oligoglucoside sulfates, isethionates,
  • Taurides sarcosinates, ether carboxylic acids, sulfosuccinates, sulfotriglycerides, protein fatty acid condensates and / or alkyl (ether) phosphates.
  • Detergent mixtures in the sense of the invention. Processes are preferred because of their particularly effective foam regulation and contain, as component b), alkylbenzenesulfonates, alkyl sulfates, alkyl ether sulfates and / or alpha-ester sulfonates.
  • Suitable nonionic surfactants which can constitute mixture component b) are alkyl and / or alkenyl oligoglycosides, sugar esters, sorbitan esters and polysorbates.
  • Detergent mixtures which are preferred in the sense of the process according to the invention because of their particularly effective foam regulation contain as component b) alkyl oligoglucosides.
  • alkyl betaines, alkylaminopropionates, imidazolinium betaines and sulfobetaines are suitable as amphoteric or zwitterionic surfactants, which can also be used as mixture component b).
  • the low-foam aqueous detergent mixtures according to the invention can the alkyl and / or alkenyl oligoglycoside ethers and the anionic, nonionic and / or amphoteric or zwitterionic surfactants in a weight ratio of 10: 1 to 1:10, preferably 5: 1 to 1: 5 and in particular 1: 1 to 1: 4 included.
  • the detergent mixtures according to the invention are low-foaming and are distinguished by excellent surface-active properties. They are therefore suitable for the production of detergents, dishwashing detergents and cleaning products and products for hair and body care, in which they can be present in concentrations of 1 to 50, preferably 5 to 25% by weight, based on the composition.
  • Another object of the invention further relates to the use of alkyl and / or alkenyl oligoglycoside ethers as defoamers for the preparation of low-foam aqueous detergent mixtures and agents containing them.
  • test solutions 250 ml of the test solutions were first transferred to a 500 ml standing cylinder.
  • the foam was produced with the aid of a perforated disk attached to a stamp, which was immersed in the solutions and was moved up and down there at a high frequency over a short period of time.
  • the foam height was read off immediately, ie after the end of foam generation, and the foam disintegration was monitored over a period of 20 minutes.
  • Anionic surfactants AI) Ci2 / 14 coconut alcohol sulfate r Na salt
  • AT anionic surfactant
  • NT nonionic surfactant
  • E weight ratio of anionic / nonionic surfactant

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Low foaming aqueous detergent mixtures contain: (a) alkyl- and/or alkenyloligoglycoside ethers having the formula (I): (R1-0-[G]¿p)(R?2)n, in which R1 stands for a linear or branched aliphatic hydrocarbon residue with 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds; R2 stands for a linear or branched alkyl residue with 1 to 8 carbon atoms or a benzyl residue, [G] stands for a sugar residue with 5 to 6 carbon atoms, p stands for numbers from 1 to 10 and n for numbers from 0.1 p to 2 p; and (b) anionic, non-ionic and/or amphoteric or zwitterionic surface-active agents.

Description

Schaumarme wäßrige Petergensgemisehe Low-foaming aqueous petroleum mixture
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft schaumarme wäßrige Detergensgemische enthaltend Alkyl- und/oder Alkenyloligoglykosidether und an¬ ionische, nichtionische und/oder amphotere bzw. zwitterioni¬ sche Tenside sowie die Verwendung der Alkyl- und/oder Alke¬ nyloligoglykosidether als Entschäumer zur Herstellung schaumarmer wäßriger Detergensgemische und die sie enthal¬ tenden Produkte.The invention relates to low-foaming aqueous detergent mixtures comprising alkyl and / or alkenyl oligoglycoside ethers and anionic, nonionic and / or amphoteric or zwitterionic surfactants, and to the use of alkyl and / or alkylene oligoglycoside ethers as defoamers for producing low-foam aqueous detergent mixtures and the products containing them.
Stand der TechnikState of the art
Die wirksame und gleichmäßige Steuerung der Schaummenge, die während des Waschens, Spülens und Reinigens gebildet wird, ist ein althergebrachter und wohlbekannter Aspekt der Pro¬ duktformulierung, dessen zusätzliche Verbesserung erwünscht ist. Eine übermäßige Schaumbildung kann die gesamten Vorteile moderner Detergensmischungen beeinträchtigen, beispielsweise dann, wenn eine Waschbehandlung in einer Trommelwaschmaschine durchgeführt wird. Zu starkes Schäumen in der Waschmaschine ist unerwünscht, weil es nicht nur die Wirkung der Wasch¬ flotte auf die Textilien mindert, sondern auch restlicher Schaum in der Waschmaschine auf den Spülzyklus übertragen werden kann. Dadurch werden nicht nur die Schaummengen beim" Spülen und die dabei verbundenen Schwierigkeiten der Unter¬ drückung derselben vermehrt, sondern es können auch die bei der Spülstufe zugesetzten Wirkstoffe, beispielsweise Weich¬ macher, nachteilig beeinflußt werden [SÖFW, 117. 177 (1991)].The effective and uniform control of the amount of foam that is formed during washing, rinsing and cleaning is a traditional and well-known aspect of the product formulation, the additional improvement of which is desired. Excessive foaming can adversely affect the overall benefits of modern detergent mixtures, for example when washing is performed in a drum type washing machine. Excessive foaming in the washing machine is undesirable because it not only reduces the effect of the washing liquor on the textiles, but also less Foam in the washing machine can be transferred to the rinse cycle. This not only amounts of foam at the "Rinse and thereby associated difficulties are the Unter¬ suppression same increases, but it is also the added during the rinsing agents, for example Weich¬ maker, adversely affecting [SFW, 117. 177 (1991)] .
In der Vergangenheit hat es nicht an Versuchen gemangelt, das Problem einer übermäßigen Schaumentwicklung insbesondere an¬ ionischer Tenside durch den Zusatz geeigneter Schaumregulie¬ rungsmittel, die auch häufig als "Schaumbremsen" bezeichnet werden, zu lösen. Zu den wichtigsten gehören die Salze lang- kettiger Fettsäuren [DE-PS-10 56 316, DE-PS-10 80 250, Proc¬ ter & Gamble Co.] sowie endgruppenverschlossene Fettalkohol- polyglycolether, sogenannte "Mischether" [DE-Al-33 45 349, EP-B1-0 303 928, Henkel KGaA].In the past there has been no lack of attempts to solve the problem of excessive foam development, in particular anionic surfactants, by adding suitable foam regulating agents, which are also often referred to as "foam brakes". The most important include the salts of long-chain fatty acids [DE-PS-10 56 316, DE-PS-10 80 250, Procter & Gamble Co.] as well as end-capped fatty alcohol polyglycol ethers, so-called "mixed ethers" [DE-Al- 33 45 349, EP-B1-0 303 928, Henkel KGaA].
Nachteile bei der Verwendung der genannten Schaumregulie¬ rungsmittel sind darin begründet, daßDisadvantages when using the foam regulating agents mentioned are due to the fact that
o sie nicht auf alle anionischen Tensidsysteme angewendet werden können, o eine verminderte Regulieraktivität bei Temperaturen im Bereich von 60 bis 90°C aufweisen, o eine verminderte Aktivität in weichem Wasser besitzen, o eine ungleichmäßige Regelung über den praktischen An¬ wendungsbereich zeigen und o zu einer negativen Beeinflussung der anwendungstechni¬ schen Eigenschaften der von ihnen schaumregulierten Produkten führen können. Die Aufgabe der Erfindung bestand somit darin, schaumregu¬ lierte Detergensgemische auf Basis anionischer, nichtioni-" scher und/oder amphoterer bzw. zwitterionischer Tenside zur Verfügung zu stellen, die frei von den geschilderten Nach¬ teilen sind.o they cannot be applied to all anionic surfactant systems, o have a reduced regulating activity at temperatures in the range from 60 to 90 ° C, o have a reduced activity in soft water, o show uneven regulation over the practical application range and o zu can have a negative influence on the application properties of the foam-regulated products. The object of the invention was therefore to schaumregu¬ profiled detergent mixtures based on anionic, nonionic to provide "shear and / or amphoteric or zwitterionic surfactants are available which are free from the share Nach¬.
Beschreibung der ErfindungDescription of the invention
Gegenstand der Erfindung sind schaumarme wäßrige Detergens¬ gemische enthaltendThe invention relates to low-foam aqueous detergent mixtures containing
a) Alkyl- und/ oder Alkenyloligoglykosidether der Formel (I)a) alkyl and / or alkenyl oligoglycoside ethers of the formula (I)
(Rl-0-[G]p)(R2)n (I)(Rl-0- [G] p ) (R2) n (I)
in derin the
Rl für einen linearen oder verzweigten aliphatisehen Kohlenwasserstoffrest mit 6 bis 22 Kohlenstoffatomen und 0, 1, 2 oder 3 Doppelbindungen,Rl is a linear or branched aliphatic hydrocarbon radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds,
R2 für einen linearen oder verzweigten Alkylrest mit 1 bis 8 Kohlenstoffatomen oder einen Benzylrest,R2 represents a linear or branched alkyl radical having 1 to 8 carbon atoms or a benzyl radical,
[G] für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen, p für Zahlen von 1 bis 10 und n für Zahlen von 0,1 p bis 2 p[G] for a sugar residue with 5 or 6 carbon atoms, p for numbers from 1 to 10 and n for numbers from 0.1 p to 2 p
steht, und b) anionische, nichtionische und/oder amphotere bzw. zwit¬ terionische Tenside.stands, and b) anionic, nonionic and / or amphoteric or zwitterionic surfactants.
Überraschenderweise wurde gefunden, daß der Zusatz von Alkyl- und/oder Alkenyloligoglykosidethern das Schaumvermögen einer Vielzahl von anionischen Tensiden in synergistischer Weise herabsetzt. Die erfindungsgemäßen Detergensgemische weisen über einen weiten Temperaturbereich eine geringe Schaument¬ wicklung und ein konstant hohes Leistungsvermögen auf. Als besonders effektive Schaumbremsen haben sich Alkyloligoglu- cosidbenzylether erwiesen.Surprisingly, it has been found that the addition of alkyl and / or alkenyl oligoglycoside ethers reduces the foaming power of a large number of anionic surfactants in a synergistic manner. The detergent mixtures according to the invention have low foaming and a constantly high performance over a wide temperature range. Alkyl oligoglucoside benzyl ethers have proven to be particularly effective foam brakes.
Alkyl- und/oder Alkenyloligoglykosidether stellen bekannte schaumarme Substanzen dar, die beispielsweise aus der DE- Al-38 35 199 (BASF AG) bekannt sind. Zu ihrer Herstellung kann man von Alkyl- und/oder Alkenyloligoglykosiden ausgehen, die in Gegenwart von Alkalihydroxiden mit Alkyl- oder Alkyl- arylhalogeniden verethert werden.Alkyl and / or alkenyl oligoglycoside ethers are known low-foaming substances which are known, for example, from DE-Al-38 35 199 (BASF AG). For their preparation, one can start from alkyl and / or alkenyl oligoglycosides which are etherified with alkyl or alkyl aryl halides in the presence of alkali metal hydroxides.
Alkyl- und/oder Alkenyloligoglykosidether, die im Sinne der Erfindung Verwendung finden können, stellen vorzugsweise Um¬ setzungsprodukte von Cg-C22~Alkyl- und/oder Alkenyloligogly¬ kosiden mit Ci-Cg-Alkylhalogeniden oder Benzylhalogeniden dar. Typische Beispiele sind Umsetzungsprodukte von Ci2/14~ Kokosalkyloligoglucosid, Cg iQ-Ko^os-^lkyloligoglucosid oder Ci6/ιg-Talgalkyloligoglucosid mit Methylchlorid, Butylchlo- rid, Octylchlorid oder Benzylchlorid.Alkyl and / or Alkenyloligoglykosidether, which can be used in the context of the invention preferably provide Um¬ reduction products of Cg-C22 ~ A lkyl- and / or Alkenyloligogly¬ kosiden with Ci-Cg-alkyl halides or benzyl halides. Typical examples are reaction products of Ci2 / 14 ~ cocoalkyl oligoglucoside, Cg i Q -Ko ^ os- ^ lkyloligoglucosid or Ci6 / ιg-tallow alkyl oligoglucoside with methyl chloride, butyl chloride, octyl chloride or benzyl chloride.
Bevorzugte Alkyl- und/oder Alkenyloligoglykosidether sind die Alkyl- und/oder Alkenyloligoglykosidether der Formel (I), in der R! für einen Alkylrest mit 12 bis 18 Kohlenstoffatomen. R2 für einen Benzylrest*, p für Zahlen von 1 bis 3 und n für Zahlen von 0,7 bis 1,3 steht.Preferred alkyl and / or alkenyl oligoglycoside ethers are the alkyl and / or alkenyl oligoglycoside ethers of the formula (I) in which R! for an alkyl radical with 12 to 18 carbon atoms. R2 fo r * a benzyl radical, p is a number from 1 to 3 and n is a number from 0.7 to 1.3.
Als anionische Tenside, die die Mischungskomponente b) aus¬ machen können, kommen Seifen, Alkylbenzolsulfonate, Olefin- sulfonate, Alkansulfonate, Alkylethersulfonate, alpha-Sulfo- fettsäuren, innenständige Sulfofettsäuren, alpha-Estersulfo- nate, Glycerinethersulfonate, Alkylsulfate, Alkylethersulfate mit konventioneller oder eingeengter Homologenverteilung, Glycerinethersulfate, Monoglycerid(ether)sulfate, Hydroxy- mischethersulfate, Alkyloligoglucosidsulfate, Isethionate,Suitable anionic surfactants which can make up the mixture component b) are soaps, alkylbenzenesulfonates, olefin sulfonates, alkanesulfonates, alkyl ether sulfonates, alpha sulfo fatty acids, internal sulfo fatty acids, alpha ester sulfonates, glycerol ether sulfonates, alkyl sulfates, alkyl ether sulfates with conventional narrow homolog distribution, glycerol ether sulfates, monoglyceride (ether) sulfates, hydroxy mixed ether sulfates, alkyl oligoglucoside sulfates, isethionates,
Tauride, Sarcosinate, Ethercarbonsäure, Sulfosuccinate, Sulfotriglyceride, Eiweißfettsäurekondensate und/oder Alkyl- (ether)phosphate in Betracht. Detergensgemische, die im Sinne des erfindungsgemäßen. Verfahrens wegen ihrer besonders ef¬ fektiven Schaumregulierung bevorzugt sind, enthalten als Komponente b) Alkylbenzolsulfonate, Alkylsulfate, Alkyl¬ ethersulfate und/oder alpha-Estersulfonate.Taurides, sarcosinates, ether carboxylic acids, sulfosuccinates, sulfotriglycerides, protein fatty acid condensates and / or alkyl (ether) phosphates. Detergent mixtures in the sense of the invention. Processes are preferred because of their particularly effective foam regulation and contain, as component b), alkylbenzenesulfonates, alkyl sulfates, alkyl ether sulfates and / or alpha-ester sulfonates.
Als nichtionische Tenside, die die Mischungskomponente b) ausmachen können, kommen Alkyl- und/oder Alkenyloligogly- koside, Zuckerester, Sorbitanester und Polysorbate in Frage. Detergensgemische, die im Sinne des erfindungsgemäßen Verfah¬ rens wegen ihrer besonders effektiven Schaumregulierung be¬ vorzugt sind, enthalten als Komponente b) Alkyloligogluco- side.Suitable nonionic surfactants which can constitute mixture component b) are alkyl and / or alkenyl oligoglycosides, sugar esters, sorbitan esters and polysorbates. Detergent mixtures which are preferred in the sense of the process according to the invention because of their particularly effective foam regulation contain as component b) alkyl oligoglucosides.
Als amphotere bzw. zwitterionische Tenside, die die ebenfalls als Mischungskomponente b) eingesetzt werden können, kommen schließlich Alkylbetaine, Alkylaminopropionate, Imidazolini- umbetaine und Sulfobetaine in Betracht. Die erfindungsgemäßen schaumarmen wäßrigen Detergensgemische -können die Alkyl- und/oder Alkenyloligoglykosidether und die anionischen, - nichtionischen und/oder amphoteren bzw. zwitterionischen Tenside im Gewichtsverhältnis 10 : 1 bis 1 : 10, vorzugsweise 5 : 1 bis 1 : 5 und insbesondere 1 : 1 bis 1 : 4 enthalten.Finally, alkyl betaines, alkylaminopropionates, imidazolinium betaines and sulfobetaines are suitable as amphoteric or zwitterionic surfactants, which can also be used as mixture component b). The low-foam aqueous detergent mixtures according to the invention can the alkyl and / or alkenyl oligoglycoside ethers and the anionic, nonionic and / or amphoteric or zwitterionic surfactants in a weight ratio of 10: 1 to 1:10, preferably 5: 1 to 1: 5 and in particular 1: 1 to 1: 4 included.
Zur Herstellung der erfindungsgemäßen Detergensgemische ist es ausreichend, die einzelnen Komponenten gegebenenfalls bei einer erhöhten Temperatur von 40 bis 50°C unter Rühren zu¬ sammenzugeben. Die Vermischung erfolgt auf rein mechanischem Wege,- eine chemische Reaktion findet nicht statt.To prepare the detergent mixtures according to the invention, it is sufficient to combine the individual components, if appropriate at an elevated temperature of 40 to 50 ° C., with stirring. The mixing takes place in a purely mechanical way - there is no chemical reaction.
Gewerbliche AnwendbarkeitIndustrial applicability
Die erfindungsgemäßen Detergensgemische sind schaumarm und zeichnen sich durch ausgezeichnete oberflächenaktive Eigen¬ schaften aus. Sie eignen sich daher zur Herstellung von Wasch-, Spül- und Reinigungsmitteln sowie Produkten der Haar- und Körperpflege, in denen sie in Konzentrationen von 1 bis 50, vorzugsweise 5 bis 25 Gew.-% - bezogen auf die Mittel - enthalten sein können.The detergent mixtures according to the invention are low-foaming and are distinguished by excellent surface-active properties. They are therefore suitable for the production of detergents, dishwashing detergents and cleaning products and products for hair and body care, in which they can be present in concentrations of 1 to 50, preferably 5 to 25% by weight, based on the composition.
Ein weiterer Gegenstand der Erfindung betrifft ferner die Verwendung von Alkyl- und/oder Alkenyloligoglykosidethern als Entschäumer zur Herstellung von schaumarmen wäßrigen Deter¬ gensmischungen und diese enthaltende Mittel.Another object of the invention further relates to the use of alkyl and / or alkenyl oligoglycoside ethers as defoamers for the preparation of low-foam aqueous detergent mixtures and agents containing them.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken. BeispieleThe following examples are intended to explain the subject matter of the invention in more detail without restricting it. Examples
I. Herstellung von C-\7/14-KokosalkyloligoglucosidbenzyletherI. Preparation of C- \ 7/14-Kokosalkyloligoglucosidbenzylether
In einem 1-1-Dreihalskolben mit Rührer und Innenthermometer wurdenIn a 1-1 three-necked flask equipped with a stirrer and internal thermometer
434 g (1 Mol) Ci2/14-K°kosalkylglucosid,434 g (1 mol) Ci2 / 14 -K ° kosalkylglucoside,
Durchschnittlicher Oligomerisierungsgrad: 1,4 Hydroxylzahl : 635,5 undAverage degree of oligomerization: 1.4 hydroxyl number: 635.5 and
126 g (1 Mol) Benzylchlorid126 g (1 mole) of benzyl chloride
vorgelegt und über einen Zeitraum von 1 h bei einer Tempera¬ tur von 90°C gerührt. Anschließend wurde 44 g (1 Mol) Natri¬ umhydroxid zugegeben und die Reaktionsmischung 8 h bei 80°C gerührt. Nach dem Abkühlen wurde der rohe Benzylether mit Wasser verdünnt und mit 50 gew.-%iger Schwefelsäure neutra¬ lisiert. Die organische Phase wurde mit Hilfe eines Scheide¬ trichters abgetrennt und anschließend im Wasserstrahlvakuum bei 200°C von letzten Wasserspuren befreit. Schließlich wurde das Produkt in Gegenwart eines Filterhilfsmittels (Celite(R)) filtriert. Der wasserfreie Alkylglucosidbenzylether wurde als klare, gelb gefärbte Flüssigkeit erhalten. Das Produkt zeigte die folgenden Kennzahlen:submitted and stirred over a period of 1 h at a temperature of 90 ° C. Then 44 g (1 mol) of sodium hydroxide were added and the reaction mixture was stirred at 80 ° C. for 8 h. After cooling, the crude benzyl ether was diluted with water and neutralized with 50% by weight sulfuric acid. The organic phase was separated off using a separating funnel and then freed from any traces of water in a water jet vacuum at 200 ° C. Finally, the product was filtered in the presence of a filter aid (Celite (R )). The anhydrous alkyl glucoside benzyl ether was obtained as a clear, yellow colored liquid. The product showed the following key figures:
Hydroxylzahl : 437Hydroxyl number: 437
Mittlerer. Veretherungsgrad : 1 II. Anwendungstechnische BeispieleMiddle. Degree of etherification: 1 II. Examples of application technology
Die anwendungstechnischen Untersuchungen des Schaumvermögens wurden gemäß DIM 53 902,2 unter folgenden Bedingungen durch¬ geführt:The application tests of the foaming power were carried out in accordance with DIM 53 902.2 under the following conditions:
Konzentration : 0,5 g/1 (bezogen auf Aktivsubstanz) Wasserhärte : 16°d Temperatur : 40°C.Concentration: 0.5 g / 1 (based on active substance) Water hardness: 16 ° d Temperature: 40 ° C.
Für die Messungen wurden zunächst jeweils 250 ml der Testlö- sungen in einen 500 ml-Standzylinder überführt. Die Schaum¬ erzeugung erfolgte mit Hilfe einer an einem Stempel befe¬ stigten Lochscheibe, die in die Lösungen eintauchte und dort über einen kurzen Zeitraum mit hoher Frequenz auf- und abbe¬ wegt wurde. Die Schaumhöhe wurde unmittelbar, d. h. nach Be¬ endigung der Schaumerzeugung, abgelesen und der Schaumzerfall über einen Zeitraum von 20 min verfolgt. For the measurements, 250 ml of the test solutions were first transferred to a 500 ml standing cylinder. The foam was produced with the aid of a perforated disk attached to a stamp, which was immersed in the solutions and was moved up and down there at a high frequency over a short period of time. The foam height was read off immediately, ie after the end of foam generation, and the foam disintegration was monitored over a period of 20 minutes.
Eingesfe >τ.e Stoffe;Mixed> τ.e substances;
Aniontenside : AI) Ci2/14-Kokosfettalkoholsulfatr-Na-SalzAnionic surfactants: AI) Ci2 / 14 coconut alcohol sulfate r Na salt
Texapon(R) LS 35, Fa.Henkel KGaA A2) Dodecylbenzolsulfonat-Na-SalzTexapon ( R ) LS 35, from Henkel KGaA A2) dodecylbenzenesulfonate Na salt
Maranil(R) A55, Fa.Henkel KGaA A3) Cig/ig-Talgmethylestersulfonat-Na-SalzMaranil ( R ) A55, Henkel KGaA A 3) Cig / ig tallow methyl ester sulfonate Na salt
Texin(R) ES 68, Fa.Henkel KGaA A4) Cis/ig-Talgalkoholsulfat-Na-SalzTexin ( R ) ES 68, Henkel KGaA A4) Cis / ig tallow alcohol sulfate Na salt
Sulfopon(R) T 55, Fa.Henkel KGaASulfopon ( R ) T 55, Henkel KGaA
Niotenside B1) Ci2/χ4-Kokosalkyloligoglucosidbenzylether gemäß I) B2) Ci2/14"K°kosalkyloligoglucosidNonionic surfactants B1 ) Ci2 / χ4-Kokosalkyloligoglucosidbenzylether according to I) B2) Ci2 / 14 "K ° kosalkyloligoglucosid
Plantaren(R) APG 600, Fa.Henkel KGaAPlantaren ( R ) APG 600, Fa. Henkel KGaA
B3) Ci2/18-Kokosalk 1~10 EO-butylether Dehypon(R) LT 104, Fa.Henkel KGaA B3 ) Ci2 / 18 coconut lime 1 ~ 10 EO-butyl ether Dehypon ( R ) LT 104, from Henkel KGaA
Die Ergebnisse der Schaummessungen sind in Tab.l zusammenge¬ faßt. Detergensmischungen mit Bl sind erfindungsgemäß, die Mischungen mit B2 und B3 dienen dem Vergleich. The results of the foam measurements are summarized in Tab. 1. Detergent mixtures with B1 are according to the invention, the mixtures with B2 and B3 are used for comparison.
Tab.1: SchaummessungenTab. 1: Foam measurements
Figure imgf000012_0001
Figure imgf000012_0001
Legende: AT = Aniontensid NT = Niotensid AT:E = Gewichtsverhältnis Anion-/Niotensid Legend: AT = anionic surfactant NT = nonionic surfactant AT: E = weight ratio of anionic / nonionic surfactant

Claims

Patentansprüche Claims
1. Schaumarme wäßrige Detergensgemische enthaltend1. Containing low-foam aqueous detergent mixtures
a) Alkyl- und/ oder Alkenyloligoglykosidether der For¬ mel (I)a) alkyl and / or alkenyl oligoglycoside ethers of the formula (I)
Figure imgf000013_0001
Figure imgf000013_0001
in derin the
Rl für einen linearen oder verzweigten aliphati- schen Kohlenwasserstoffrest mit 6 bis 22 Koh¬ lenstoffatomen und 0, 1, 2 oder 3 Doppelbin¬ dungen,R1 for a linear or branched aliphatic hydrocarbon radical with 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds,
R2 für einen linearen oder verzweigten Alkylrest mit 1 bis 8 Kohlenstoffatomen oder einen Ben¬ zylrest,R2 represents a linear or branched alkyl radical having 1 to 8 carbon atoms or a benzyl radical,
[G] für einen Zuckerrest mit 5 oder 6 Kohlenstoff¬ atomen, p für Zahlen von 1 bis 10 und n für Zahlen von 0,1 p bis 2 p[G] for a sugar residue with 5 or 6 carbon atoms, p for numbers from 1 to 10 and n for numbers from 0.1 p to 2 p
steht, undstands, and
b) anionische, nichtionische und/oder amphotere bzw. zwitterionische Tenside.b) anionic, nonionic and / or amphoteric or zwitterionic surfactants.
2. Schaumarme wäßrige Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie Alkyl- und/oder Alke- nyloligoglucosidether der Formel (I) enthalten, in der R1 für einen Alkylreεt mit 12 bis 18 Kohlenstoffatomen, R2 fü einen Benzylrest, p für Zahlen von 1 bis 3 und n" für Zahlen von 0,7 bis 1,3 steht.2. Low-foam aqueous detergent mixtures according to claim 1, characterized in that they contain alkyl and / or alkylene oligoglucoside ethers of the formula (I) in which R 1 stands for an alkyl radical with 12 to 18 carbon atoms, R2 for a benzyl radical, p for numbers from 1 to 3 and n " for numbers from 0.7 to 1.3.
3. Schaumarme wäßrige Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie anionische Tenside aus¬ gewählt aus der Gruppe, die gebildet wird von Seifen, Alkylbenzolsulfonaten, Olefinsulfonaten, Alkansulfona- ten, Alkylethersulfonaten, alpha-Sulfofettsäuren, in¬ nenständigen Sulfofettsäuren, alpha-Estersulfonaten, Glycerinethersulfonaten, Alkylsulfaten, Alkylethersul- faten mit konventioneller oder eingeengter Homologen¬ verteilung, Glycerinethersulfaten, Monoglycerid(ether)- sulfaten, Hydroxymischethersulfaten, Alkyloligoglucosid- sulfaten, Isethionaten, Tauriden, Sarcosinaten, Ether- carbonsäuren, Sulfosuccinaten, Sulfotriglyceriden, Ei¬ weißfettsäurekondensaten und Alkyl(ether)phosphaten, gebildet wird, enthalten.3. Low-foam aqueous detergent mixtures according to claim 1, characterized in that they selected anionic surfactants from the group formed by soaps, alkylbenzenesulfonates, olefin sulfonates, alkanesulfonates, alkyl ether sulfonates, alpha-sulfofatty acids, internal sulfofatty acids, alpha Ester sulfonates, glycerol ether sulfonates, alkyl sulfates, alkyl ether sulfates with conventional or narrow homolog distribution, glycerol ether sulfates, monoglyceride (ether) sulfates, hydroxymixed ether sulfates, alkyl oligoglucoside sulfates, isethionates, taurides, sarcosinates, sulfosuccinate acid, sulfonate carboxylates Alkyl (ether) phosphates formed.
4. Schaumarme wäßrige Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie nichtionische Tenside ausgewählt aus der Gruppe, die von Alkyl- und/oder Al- kenyloligoglykosiden, Zuckerestern, Sorbitanestern und Polysorbaten gebildet wird, enthalten.4. Low-foam aqueous detergent mixtures according to claim 1, characterized in that they contain nonionic surfactants selected from the group consisting of alkyl and / or alkenyl oligoglycosides, sugar esters, sorbitan esters and polysorbates.
5. Schaumarme wäßrige Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie amphotere bzw. zwitter¬ ionische Tenside ausgewählt aus der Gruppe, die von Alkylbetainen, Alkylaminopropionaten, Imidazoliniuπibe- tainen und Sulfobetainen gebildet wird, enthalten. 5. Low-foam aqueous detergent mixtures according to claim 1, characterized in that they contain amphoteric or zwitter¬ ionic surfactants selected from the group consisting of alkyl betaines, alkylaminopropionates, imidazoliniuπibe- taines and sulfobetaines.
6. Schaumarme wäßrige Detergensgemische nach Anspruch 1, dadurch gekennzeichnet, daß sie die Alkyl- und/oder Al¬ kenyloligoglykosidether und die anionischen, nichtio¬ nischen und/oder amphoteren bzw. zwitterionischen Ten¬ side im Gewichtsverhältnis 10 : 1 bis 1 : 10 enthalten.6. Low-foam aqueous detergent mixtures according to claim 1, characterized in that they contain the alkyl and / or Al¬ kenyloligoglycosidether and the anionic, non-ionic and / or amphoteric or zwitterionic Ten¬ side in a weight ratio of 10: 1 to 1:10 .
7. Verwendung von Alkyl- und/oder Alkenyloligoglykosid¬ ethern als Entschäumer zur Herstellung von schaumarmen wäßrigen Detergensmischungen und diese enthaltenden Mittel. 7. Use of alkyl and / or alkenyl oligoglycoside ethers as defoamers for the preparation of low-foam aqueous detergent mixtures and agents containing them.
PCT/EP1993/000724 1992-04-02 1993-03-25 Low foaming aqueous detergent mixtures WO1993020171A1 (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996007473A1 (en) * 1994-09-09 1996-03-14 Henkel Kommanditgesellschaft Auf Aktien Mild detergent mixtures
US5562848A (en) * 1992-09-21 1996-10-08 Wofford; James A. Viscosity-stabilized amide composition, methods of preparing and using same
WO1996034078A1 (en) * 1995-04-28 1996-10-31 Akzo Nobel N.V. Aqueous composition, and the use of a wetting-improving agent
US5576284A (en) * 1994-09-26 1996-11-19 Henkel Kommanditgesellschaft Auf Aktien Disinfecting cleanser for hard surfaces
US5585472A (en) * 1992-08-21 1996-12-17 Basf Aktiengesellschaft Preparation of alkyl glycosides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0136844A2 (en) * 1983-09-06 1985-04-10 Henkel Kommanditgesellschaft auf Aktien Glycoside-containing detergents
EP0364852A2 (en) * 1988-10-15 1990-04-25 BASF Aktiengesellschaft Substituted glucosides
WO1992001772A1 (en) * 1990-07-23 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Pumpable fluid surfactant concentrate
DE4131281A1 (en) * 1991-09-20 1993-03-25 Henkel Kgaa PROCESS FOR THE PREPARATION OF ALKYL AND / OR ALKENYL POLYGLYCOSID ETHER

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0136844A2 (en) * 1983-09-06 1985-04-10 Henkel Kommanditgesellschaft auf Aktien Glycoside-containing detergents
EP0364852A2 (en) * 1988-10-15 1990-04-25 BASF Aktiengesellschaft Substituted glucosides
WO1992001772A1 (en) * 1990-07-23 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Pumpable fluid surfactant concentrate
DE4131281A1 (en) * 1991-09-20 1993-03-25 Henkel Kgaa PROCESS FOR THE PREPARATION OF ALKYL AND / OR ALKENYL POLYGLYCOSID ETHER

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5585472A (en) * 1992-08-21 1996-12-17 Basf Aktiengesellschaft Preparation of alkyl glycosides
US5562848A (en) * 1992-09-21 1996-10-08 Wofford; James A. Viscosity-stabilized amide composition, methods of preparing and using same
WO1996007473A1 (en) * 1994-09-09 1996-03-14 Henkel Kommanditgesellschaft Auf Aktien Mild detergent mixtures
US5952279A (en) * 1994-09-09 1999-09-14 Henkel Kommanditgesellschaft Auf Aktien Mild detergent mixtures
US5576284A (en) * 1994-09-26 1996-11-19 Henkel Kommanditgesellschaft Auf Aktien Disinfecting cleanser for hard surfaces
WO1996034078A1 (en) * 1995-04-28 1996-10-31 Akzo Nobel N.V. Aqueous composition, and the use of a wetting-improving agent
US5928993A (en) * 1995-04-28 1999-07-27 Akzo Nobel Nv Aqueous composition, and the use of a wetting-improving agent

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