EP0750034A2 - Storage stable, concentrated surfactant composition based on alkylglycosides - Google Patents

Storage stable, concentrated surfactant composition based on alkylglycosides Download PDF

Info

Publication number
EP0750034A2
EP0750034A2 EP96109168A EP96109168A EP0750034A2 EP 0750034 A2 EP0750034 A2 EP 0750034A2 EP 96109168 A EP96109168 A EP 96109168A EP 96109168 A EP96109168 A EP 96109168A EP 0750034 A2 EP0750034 A2 EP 0750034A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
surfactant composition
carbon atoms
storage
alkylglycosides
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.)
Granted
Application number
EP96109168A
Other languages
German (de)
French (fr)
Other versions
EP0750034B1 (en
EP0750034A3 (en
Inventor
Burghard Dr. Grüning
Christian Dr. Weitemeyer
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.)
Evonik Operations GmbH
Original Assignee
TH Goldschmidt AG
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7764710&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0750034(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by TH Goldschmidt AG filed Critical TH Goldschmidt AG
Publication of EP0750034A2 publication Critical patent/EP0750034A2/en
Publication of EP0750034A3 publication Critical patent/EP0750034A3/en
Application granted granted Critical
Publication of EP0750034B1 publication Critical patent/EP0750034B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • 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
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • CCHEMISTRY; METALLURGY
    • 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
    • C11D1/04Carboxylic acids or salts thereof
    • CCHEMISTRY; METALLURGY
    • 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
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/917The agent contains organic compound containing oxygen
    • Y10S516/919The compound contains -C[=O]OH or salt thereof

Landscapes

  • 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)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Storage-stable, conc. aq. surfactant compsn. comprises 40 - 75 wt.% alkyl glucosides of formula R<1>O-(G)p (I); 1 - 15 wt.% fatty acid; 0 - 5 wt.% alkali or alkaline earth halide as electrolyte; and 5 - 59 wt.% water. R<1> = 6-22C (pref. 12 - 18)C alkyl; G = glucoside residue; and p = 1 - 3.

Description

Die Erfindung betrifft eine lagerstabile, konzentrierte Tensidzusammensetzung auf der Basis von Alkylglucosiden mit einem Zusatz von Fettsäuren als stabilisierendes Mittel.The invention relates to a storage-stable, concentrated surfactant composition based on alkyl glucosides with the addition of fatty acids as a stabilizing agent.

Alkylglucoside sind bekannte Stoffe. Sie entsprechen der allgemeinen Formel

        R-O-[G]p

in der R von einem Fettalkoholrest abgeleitet ist und G für den Glucoserest steht. An einem Fettalkoholrest können ein oder mehrere Glucosereste gebunden sein, wodurch sich ein mittlerem Oligomerisierungsgrad p über die Glucoseeinheiten ergibt. In der Literatur werden daher auch die Bezeichnungen Alkylpolyglucosid und Alkyloligoglucosid für diese Produktgruppe gebraucht.
Alkyl glucosides are known substances. They correspond to the general formula

RO- [G] p

in which R is derived from a fatty alcohol residue and G stands for the glucose residue. One or more glucose residues can be bound to a fatty alcohol residue, which results in an average degree of oligomerization p via the glucose units. In the literature, the terms alkyl polyglucoside and alkyl oligoglucoside are therefore used for this product group.

Alkylglucoside sind wichtige nichtionische Tenside, die infolge ihrer guten Detergenseigenschaften und hohen Umweltverträglichkeit in immer stärkerem Maße Eingang in Wasch-, Spül- und Reinigungsmittel gefunden haben.Alkyl glucosides are important non-ionic surfactants, which have found their way into detergents, dishwashing detergents and cleaning agents due to their good detergent properties and high environmental compatibility.

Für diesen Zweck ist es erforderlich, Alkylglucoside über bestimmte Zeiträume beispielsweise als wäßrige Lösungen oder Pasten zur Verfügung zu halten und zu lagern, bis eine Endverarbeitung stattfindet. Da wäßrige Alkylglucoside jedoch eine starke Neigung zur Kristallisation zeigen, bilden sich bei Lagerung unter Umgebungsbedingungen im Laufe der Zeit kristallwasserhaltige Agglomerate, die die Pumpfähigkeit der Produkte stark herabsetzen.For this purpose it is necessary to keep alkyl glucosides available for a certain period of time, for example as aqueous solutions or pastes, until they are finished. However, since aqueous alkyl glucosides show a strong tendency to crystallize, water containing crystals form over time when stored under ambient conditions Agglomerates that greatly reduce the pumpability of the products.

Diese Probleme treten insbesondere bei Alkylglucosiden auf, bei denen der Alkylrest 12 oder mehr C-Atome aufweist bzw. bei handelsüblichen Alkylglucosid-Gemischen, bei denen der höherkettige Anteil entsprechend hoch liegt und zu mehr als 50 % Alkylreste mit 12 und mehr C-Atomen aufweist.These problems occur in particular in the case of alkyl glucosides in which the alkyl radical has 12 or more carbon atoms or in commercially available alkyl glucoside mixtures in which the higher-chain fraction is correspondingly high and has more than 50% alkyl radicals with 12 and more carbon atoms .

Üblicherweise erfolgt die Lagerung von Alkylglucosiden daher nicht bei Raumtemperatur, sondern bei Temperaturen von mindestens 35 °C. Auf diese Weise kann zwar eine Kristallisation der Zübereitungen weitgehend verhindert werden, die Lagerung bei erhöhter Temperatur ist jedoch mit zusätzlichem Aufwand verbunden und kann zudem die Farbqualität der Produkte stark beeinträchtigen.Usually, alkyl glucosides are therefore not stored at room temperature, but at temperatures of at least 35 ° C. In this way, crystallization of the preparation can largely be prevented, but storage at elevated temperature is associated with additional effort and can also severely impair the color quality of the products.

Gemäß DE-A-42 25 224 wird zur Verbesserung der Kristallisationsbeständigkeit der Zusatz einer Reihe von

Figure imgb0001
Figure imgb0001
Kristallisationsmoderatoren" vorgeschlagen, wie beispielsweise Alkyloligoglykoside auf Basis kurzkettiger Alkohole, Polyethylenglykol oder Eisen-(III)-Ionen, die aber den Nachteil aufweisen, daß sie die Tensideigenschaften bzw. die Farbe beeinträchtigen.According to DE-A-42 25 224, the addition of a number of to improve the crystallization resistance
Figure imgb0001
Figure imgb0001
Crystallization moderators "proposed, such as alkyl oligoglycosides based on short-chain alcohols, polyethylene glycol or iron (III) ions, but which have the disadvantage that they impair the surfactant properties or the color.

Die Aufgabe der Erfindung bestand somit darin, eine konzentrierte Tensidzusammensetzung auf der Basis von Alkylglucosiden zu finden, bei der eine Lagerung der Glucoside bei Temperaturen unterhalb von 35 °C möglich ist, ohne daß die Pumpfähigkeit der Produkte durch Bildung von kristallinen Agglomeraten beeinträchtigt wird.The object of the invention was therefore to find a concentrated surfactant composition based on alkyl glucosides, in which the glucosides can be stored at temperatures below 35 ° C. without the pumpability of the products being impaired by the formation of crystalline agglomerates.

Gegenstand der Erfindung ist somit eine lagerstabile, konzentrierte, wäßrige Tensidzusammensetzung, enthaltend

  • a) 40 bis 75 Gew.-% Alkylglucoside der Formel

            R1O-[G]p     (I)

    wobei
    R1
    einen Alkylrest mit 6 bis 22 C-Atomen, insbesondere 12 bis 18 C-Atomen, bedeutet,
    G
    der Glucosid-Rest und
    p
    eine Zahl von 1 bis 3 ist,
  • b) 1 bis 15 Gew.-% Fettsäure,
  • c) 0 bis 5 Gew.-% Elektrolyt aus Alkali- oder Erdalkalihalogeniden sowie
  • d) 5 bis 59 Gew.-% Wasser.
The invention thus relates to a storage-stable, concentrated, aqueous surfactant composition containing
  • a) 40 to 75 wt .-% alkyl glucosides of the formula

    R 1 O- [G] p (I)

    in which
    R 1
    is an alkyl radical having 6 to 22 carbon atoms, in particular 12 to 18 carbon atoms,
    G
    the glucoside residue and
    p
    is a number from 1 to 3,
  • b) 1 to 15% by weight of fatty acid,
  • c) 0 to 5 wt .-% electrolyte from alkali or alkaline earth metal halides and
  • d) 5 to 59 wt .-% water.

In einer besonders bevorzugten Ausführungsform gilt, daß mindestens 50 % der Reste R1 12 oder mehr C-Atome aufweisen.In a particularly preferred embodiment, at least 50% of the radicals R 1 have 12 or more carbon atoms.

Eine bevorzugte Alkylrest-Verteilung im Alkylglucosid ist C8 < 3 % C10 < 3 % C12 50 bis 100 % C14 10 bis 40 % C16 0 bis 15 % C18 0 bis 10 % A preferred alkyl residue distribution in the alkyl glucoside is C 8 <3% C 10 <3% C 12 50 to 100% C 14 10 to 40% C 16 0 to 15% C 18 0 to 10%

Es wurde nun überraschend gefunden, daß in den erfindungsgemäßen konzentrierten Tensidzusammensetzungen die Kristallisationsneigung der längerkettigen Alkylglucoside so weit herabgesetzt wird, daß konzentrierte, wäßrige Zusammensetzungen hergestellt werden können, die auch bei Temperaturen unter 35 °C keine Kristallisationsneigung zeigen und über Monate lager- und farbstabil sind. Diese Mischungen sind somit auch bei üblichen Umgebungstemperaturen im Bereich von 10 bis 25 °C stabil und lagerfähig.It has now surprisingly been found that in the concentrated surfactant compositions according to the invention the tendency to crystallize of the longer-chain alkyl glucosides is reduced to such an extent that concentrated, aqueous compositions can be produced which show no tendency to crystallize even at temperatures below 35 ° C. and are stable in storage and color for months . These mixtures are therefore also common Ambient temperatures in the range of 10 to 25 ° C stable and storable.

Wie bereits anfangs ausgeführt, stellen Alkylglycoside bekannte Stoffe dar, die aus Fettalkoholen und reduzierenden Zuckern erhalten werden können (siehe z. B. EP-A1-0 301 298 und WO 90/3977).As already stated at the beginning, alkyl glycosides are known substances which can be obtained from fatty alcohols and reducing sugars (see, for example, EP-A1-0 301 298 and WO 90/3977).

Die Alkylglycoside können sich von Aldosen bzw. Ketosen mit 5 oder 6 Kohlenstoffatomen, vorzugsweise der Glucose, ableiten. Technische Bedeutung haben dabei nur die Alkylglucoside erlangt.The alkyl glycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. Only the alkyl glucosides have gained technical importance.

Die Indexzahl p in der allgemeinen Formel (I) gibt den Oligomerisierungsgrad, d. h. die Verteilung von Mono- und Oligoglucosiden, an und steht für eine Zahl zwischen 1 und 3. Während p in einer gegebenen Verbindung stets ganzzahlig sein muß, ist der Wert p für ein bestimmtes Alkylglucosid eine analytisch ermittelte rechnerische Größe, die meistens eine gebrochene Zahl darstellt. Vorzugsweise werden Alkylglucoside mit einem mittleren Oligomerisierungsgrad p von 1,1 bis 3,0 eingesetzt. Aus anwendungstechnischer Sicht sind solche Alkylglucoside bevorzugt, deren Oligomerisierungsgrad kleiner als 1,7 ist und insbesondere zwischen 1,2 und 1,6 liegt.The index number p in the general formula (I) indicates the degree of oligomerization, i.e. H. the distribution of mono- and oligoglucosides, and stands for a number between 1 and 3. While p must always be an integer in a given compound, the value p for a certain alkyl glucoside is an analytically determined arithmetic quantity, which usually represents a fractional number . Alkyl glucosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl glucosides are preferred whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.6.

Der Alkylrest R1 kann sich von primären Alkoholen mit 4 bis 22, vorzugsweise 12 bis 14 Kohlenstoffatomen ableiten. Typischerweise liegen sie als technische Gemische vor.The alkyl radical R 1 can be derived from primary alcohols having 4 to 22, preferably 12 to 14, carbon atoms. They are typically available as technical mixtures.

Geeignete Fettsäuren sind natürliche oder synthetische Fettsäuren mit 8 bis 18 Kohlenstoffatomen, wobei natürliche Fettsäurezusammensetzungen, wie zum Beispiel Kokosfettsäure oder Palmkernfettsäure, bevorzugt sind.Suitable fatty acids are natural or synthetic fatty acids with 8 to 18 carbon atoms, with natural fatty acid compositions such as coconut fatty acid or palm kernel fatty acid being preferred.

Bevorzugt ist dabei ein höherer Anteil mit der mittleren Kettenlänge von 12 bis 14 Kohlenstoffatomen. Bevorzugt werden die Fettsäuren in Mengen von 2,5 bis 10 Gew.-%, insbesondere 5 bis 7,5 Gew.-% eingesetzt.A higher proportion with an average chain length of 12 to 14 carbon atoms is preferred. The are preferred Fatty acids in amounts of 2.5 to 10 wt .-%, in particular 5 to 7.5 wt .-% used.

Gegebenfalls werden dem Gemisch als Elektrolyt Alkali- oder Erdalkalihalogenide zugegeben, wobei üblicherweise Natriumchlorid verwendet wird.If necessary, alkali metal or alkaline earth metal halides are added to the mixture as electrolyte, sodium chloride usually being used.

In der Regel wird der Elektrolyt in fester Form oder auch aus konzentrierter wäßriger Lösung zugegeben. Dies kann zu jedem Zeitpunkt der Herstellung der Mischung geschehen, gegebenenfalls bevorzugt vor einer abschließenden Einstellung des pH-Wertes der Zubereitung.As a rule, the electrolyte is added in solid form or from a concentrated aqueous solution. This can be done at any time during the preparation of the mixture, if appropriate preferably before finally adjusting the pH of the preparation.

Wenn notwendig, wird der pH-Wert der Zubereitung durch Zugabe einer Mineralsäure oder einer organischen Säure abschließend auf einen pH-Wert von ≦ 8, vorzugsweise ≦ 6 eingestellt.If necessary, the pH of the preparation is finally adjusted to a pH of ≦ 8, preferably ≦ 6, by adding a mineral acid or an organic acid.

Bevorzugte Säuren sind Phosphorsäure, Salzsäure, Schwefelsäure, Weinsäure, Citronensäure und Milchsäure.Preferred acids are phosphoric acid, hydrochloric acid, sulfuric acid, tartaric acid, citric acid and lactic acid.

Die erfindungsgemäßen Gemische können durch einfaches Mischen von handelsüblichen Alkylglucosidlösungen und Fettsäuren hergestellt werden. Das Mischen kann bei Raumtemperatur oder, um eine geringere Viskosität zu erzielen, bei schwach erhöhter Temperatur von 30 bis 80 °C stattfinden. Die Mischungen können natürlich auch aus festen Ausgangsstoffen durch Lösen in Wasser hergestellt werden.The mixtures according to the invention can be prepared by simply mixing commercially available alkyl glucoside solutions and fatty acids. Mixing can take place at room temperature or, in order to achieve a lower viscosity, at a slightly elevated temperature of 30 to 80 ° C. The mixtures can of course also be prepared from solid starting materials by dissolving them in water.

Die erfindungsgemäßen Zubereitungen sind im allgemeinen beständig gegenüber mikrobiellem Befall. Dies gilt insbesondere bei pH-Werten von < 6. Sie können in ihrer mikrobiologischen Stabilität durch Zugabe von Alkali- oder Erdalkalihalogeniden weiter verbessert werden.The preparations according to the invention are generally resistant to microbial attack. This applies in particular at pH values of <6. Their microbiological stability can be further improved by adding alkali or alkaline earth metal halides.

Die erfindungsgemäßen tensidischen Zusammensetzungen sind lagerstabil und zeigen keine Kristallisationstendenzen. Sie weisen eine ausgezeichnete tensidische Wirkung auf und besitzen hervorragende schmutzlösende und dabei hautfreundliche Eigenschaften. Sie eignen sich zur Herstellung von Wasch-, Spül- und Reinigungsmitteln sowie Produkten der Haar- und Körperpflege, in denen sie üblicherweise in Mengen von 3 bis 30 % (bezogen auf die wäßrige Zubereitung) eingesetzt werden.The surfactant compositions according to the invention are stable on storage and show no tendency towards crystallization. They have an excellent surfactant effect and have excellent dirt-removing and skin-friendly properties. They are suitable for the production of detergents, dishwashing detergents and cleaning products, as well as hair and body care products, in which they are usually used in amounts of 3 to 30% (based on the aqueous preparation).

Je nach Einsatzzweck können übliche Inhaltsstoffe, wie Cotenside, Builder, Farbstoffe, Viskositätsregler und Duftstoffe zu gesetzt werden.Depending on the intended use, conventional ingredients such as cosurfactants, builders, dyes, viscosity regulators and fragrances can be added.

BeispieleExamples Vergleichsbeispiel (nicht erfindungsgemäß)Comparative example (not according to the invention)

Ein trockenes Alkylglucosid, das etwa 4 Gew.-% Wasser enthält, wird in Wasser gelöst, so daß eine Lösung mit 50 Gew.-% Festkörper entsteht. Der pH-Wert der Lösung beträgt 7.A dry alkyl glucoside, which contains about 4% by weight of water, is dissolved in water, so that a solution with 50% by weight of solids is formed. The pH of the solution is 7.

Das Alkylglucosid ist wie folgt gekennzeichnet (Gew.-%): Zusammensetzung der Alkylreste: C8 10 % C10 10 % C12 58 % C14 14 % C16 6 % C18 2 % Oligomerisierungsgrad: n = 1,26 The alkyl glucoside is identified as follows (% by weight): Composition of the alkyl residues: C 8 10% C 10 10% C 12 58% C 14 14% C 16 6% C 18 2% Degree of oligomerization: n = 1.26

Die Lösung wird geteilt und in verschlossenen Gefäßen bei Temperaturen von 20 und 40 °C gelagert. Die bei 20 °C gelagerte Probe ist nach 14 Tagen weiß und fest, während die bei 40 °C gelagerte Probe auch nach 6monatiger Lagerung noch flüssig ist. Sie hat sich während der Lagerung allerdings deutlich dunkler gefärbt.The solution is divided and stored in closed vessels at temperatures of 20 and 40 ° C. The sample stored at 20 ° C is white and solid after 14 days, while the one at 40 ° C stored sample is still liquid even after 6 months of storage. However, it has turned much darker during storage.

Beispiel 1 (erfindungsgemäß) Example 1

Aus dem trockenen Alkylglucosid, das im oben dargestellten Vergleichsbeispiel beschrieben ist, Kokosfettsäure, Wasser und wenig wäßriger, konzentrierter Natronlauge wird eine Lösung bereitet, die sich wie folgt zusammensetzt (Gew.-%): Alkylglucosid: 60 % Wasser: 35 % gehärtete Kokosfettsäure: 5 % Natronlauge bis pH 7 A solution is prepared from the dry alkyl glucoside described in the comparative example presented above, coconut fatty acid, water and a little aqueous, concentrated sodium hydroxide solution, which is composed as follows (% by weight): Alkyl glucoside: 60% Water: 35% hardened coconut fatty acid: 5% Sodium hydroxide solution up to pH 7

Die Lösung wird geteilt und in verschlossenen Gefäßen bei Temperaturen von 20 und 40 °C für 6 Monate gelagert. Die Proben sind nach dieser Lagerzeit homogen und fließfähig; in keiner der Proben sind Kristallbildung oder Niederschlagsbildung zu erkennen.The solution is divided and stored in closed vessels at temperatures of 20 and 40 ° C for 6 months. After this storage period, the samples are homogeneous and flowable; no crystal formation or precipitation can be seen in any of the samples.

Beispiel 2 (erfindungsgemäß) Example 2

Ähnlich wie in Beispiel 1 wird aus einem trockenen Alkylglucosid, das etwa 3 Gew.-% Wasser enthält, Laurinsäure, Wasser, wäßriger, konzentrierter Salzsäure und Natriumchlorid eine Lösung hergestellt, die sich wie folgt zusammensetzt (Gew.-%): Alkylglucosid: 41,8 % Wasser: 49,0 % Laurinsäure: 7,2 % Natriumchlorid: 2,0 % Salzsäure bis pH 5 Similar to Example 1, a solution is prepared from a dry alkyl glucoside containing about 3% by weight of water, lauric acid, water, aqueous, concentrated hydrochloric acid and sodium chloride, which is composed as follows (% by weight): Alkyl glucoside: 41.8% Water: 49.0% Lauric acid: 7.2% Sodium chloride: 2.0% Hydrochloric acid up to pH 5

Das Alkylglucosid ist wie folgt gekennzeichnet (Gew.-%): Zusammensetzung der Alkylreste: C8 1 % C10 1 % C12 68 % C14 25 % C16 5 % Oligomerisierungsgrad: n = 1,52 The alkyl glucoside is identified as follows (% by weight): Composition of the alkyl residues: C 8 1 % C 10 1 % C 12 68% C 14 25% C 16 5% Degree of oligomerization: n = 1.52

Nach Lagerung dieser Lösung unter gleichen Bedingungen wie in Beispiel 1 sind auch diese Lösungen homogen und fließfähig. In keiner der Proben sind Kristallbildung oder Niederschlagsbildung zu erkennen.After storage of this solution under the same conditions as in Example 1, these solutions are also homogeneous and flowable. No crystal formation or precipitation can be seen in any of the samples.

Die Lösung wird darüber hinaus einem mikrobiologischen Belastungstest nach DAB 10 (Deutsches Arzneibuch) unterzogen. In diesem Test erweist sich die Zubereitung als mikrobiologisch stabil.The solution is also subjected to a microbiological load test according to DAB 10 (German Pharmacopoeia). In this test, the preparation proves to be microbiologically stable.

Claims (2)

Lagerstabile, konzentrierte, wäßrige Tensidzusammensetzung, enthaltend a) 40 bis 75 Gew.-% Alkylglucoside der Formel

        R1O-[G]p     (I)

wobei R1   einen Alkylrest mit 6 bis 22 C-Atomen, insbesondere 12 bis 18 C-Atomen, bedeutet, und G   der Glucosid-Rest und p   eine Zahl von 1 bis 3 ist,
b) 1 bis 15 Gew.-% Fettsäure, c) 0 bis 5 Gew.-% Elektrolyt aus Alkali- oder Erdalkalihalogeniden sowie d) 5 bis 59 Gew.-% Wasser.
Storage-stable, concentrated, aqueous surfactant composition containing a) 40 to 75 wt .-% alkyl glucosides of the formula

R 1 O- [G] p (I)

in which R 1 is an alkyl radical having 6 to 22 carbon atoms, in particular 12 to 18 carbon atoms, and G the glucoside residue and p is a number from 1 to 3,
b) 1 to 15% by weight of fatty acid, c) 0 to 5 wt .-% electrolyte from alkali or alkaline earth metal halides and d) 5 to 59 wt .-% water.
Tensidzusammensetzung gemäß Anspruch 1, dadurch gekennzeichnet, daß mindestens 50 % der Reste R1 12 oder mehr C-Atome aufweisen.Surfactant composition according to claim 1, characterized in that at least 50% of the radicals R 1 have 12 or more carbon atoms.
EP96109168A 1995-06-20 1996-06-07 Storage stable, concentrated surfactant composition based on alkylglycosides Expired - Lifetime EP0750034B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19522233 1995-06-20
DE19522233 1995-06-20

Publications (3)

Publication Number Publication Date
EP0750034A2 true EP0750034A2 (en) 1996-12-27
EP0750034A3 EP0750034A3 (en) 1997-03-05
EP0750034B1 EP0750034B1 (en) 2001-03-21

Family

ID=7764710

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96109168A Expired - Lifetime EP0750034B1 (en) 1995-06-20 1996-06-07 Storage stable, concentrated surfactant composition based on alkylglycosides

Country Status (5)

Country Link
US (1) US5941812A (en)
EP (1) EP0750034B1 (en)
JP (1) JPH093498A (en)
DE (1) DE59606611D1 (en)
ES (1) ES2157368T3 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0884048A1 (en) * 1997-06-06 1998-12-16 Beiersdorf Aktiengesellschaft Cosmetic and dermatological emulsions containing alkylglucosides and increased electrolyte concentrations
WO2000042141A1 (en) * 1999-01-14 2000-07-20 Cognis Deutschland Gmbh Method for inhibiting crystallisation in concentrates of surfactants
EP2048220A1 (en) * 2007-10-10 2009-04-15 Cognis IP Management GmbH Method for manufacturing liquid detergents

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1443887A2 (en) * 2001-11-07 2004-08-11 Beiersdorf AG Use of alkyl glucosides to obtain or enhance selectivity of cleaning formulations
JP5386113B2 (en) * 2008-06-05 2014-01-15 花王株式会社 Separation promoter composition for inorganic powder
WO2023285245A1 (en) * 2021-07-16 2023-01-19 Basf Se A premix comprising alkyl polyglycoside for use in preparing a liquid detergent formulation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986006404A1 (en) * 1985-04-26 1986-11-06 A.E. Staley Manufacturing Company Stability and compatibility of glycosides in acid systems
EP0444267A2 (en) * 1990-02-26 1991-09-04 Hüls Aktiengesellschaft Liquid foaming detergent
EP0510870A2 (en) * 1991-04-24 1992-10-28 Kao Corporation Milky detergent composition for hard surfaces
WO1993020179A1 (en) * 1992-03-30 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Detergents for hard surfaces
WO1994005751A1 (en) * 1992-08-31 1994-03-17 Henkel Corporation Hard surface cleaners based on apg, dicarboxylic acid and pine oil

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2754359C2 (en) * 1977-12-07 1986-11-20 Basf Ag, 6700 Ludwigshafen Process for the preparation of strongly alkaline, aqueous and solubilizer-containing solutions of non-ionic surfactants
US4240921A (en) * 1979-03-28 1980-12-23 Stauffer Chemical Company Liquid cleaning concentrate
US4565647B1 (en) * 1982-04-26 1994-04-05 Procter & Gamble Foaming surfactant compositions
DE3723826A1 (en) * 1987-07-18 1989-01-26 Henkel Kgaa METHOD FOR PRODUCING ALKYL GLYCOSIDES
DE3833780A1 (en) * 1988-10-05 1990-04-12 Henkel Kgaa METHOD FOR THE DIRECT PRODUCTION OF ALKYL GLYCOSIDES
DE4110506A1 (en) * 1991-03-30 1992-10-01 Huels Chemische Werke Ag EMULSIFIERS FOR THE PRODUCTION OF OIL-IN-WATER EMULSIONS OF ETHERIC OILS USED IN COSMETICS OR MEDICINE
DE4215390A1 (en) * 1992-05-11 1993-11-18 Basf Ag Use of a solubilizer mixture for the production of strongly alkaline, aqueous solutions of non-ionic surfactants
DE4225224A1 (en) * 1992-07-30 1994-02-03 Henkel Kgaa Process for the production of storage-stable nonionic surfactants
US6071429A (en) * 1992-09-21 2000-06-06 Henkel Corporation Viscosity-stabilized amide composition, methods of preparing and using same
US5352376A (en) * 1993-02-19 1994-10-04 Ecolab Inc. Thermoplastic compatible conveyor lubricant
US5534500A (en) * 1993-09-13 1996-07-09 Henkel Corporation Process for preparing surfactant mixtures having high solids content
US5567808A (en) * 1994-11-10 1996-10-22 Henkel Corporation Alkyl polyglycosides having improved aesthetic and tactile properties
US5783553A (en) * 1994-11-10 1998-07-21 Henkel Corporation Alkyl polyglycosides having improved aesthetic and tactile properties

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986006404A1 (en) * 1985-04-26 1986-11-06 A.E. Staley Manufacturing Company Stability and compatibility of glycosides in acid systems
EP0444267A2 (en) * 1990-02-26 1991-09-04 Hüls Aktiengesellschaft Liquid foaming detergent
EP0510870A2 (en) * 1991-04-24 1992-10-28 Kao Corporation Milky detergent composition for hard surfaces
WO1993020179A1 (en) * 1992-03-30 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Detergents for hard surfaces
WO1994005751A1 (en) * 1992-08-31 1994-03-17 Henkel Corporation Hard surface cleaners based on apg, dicarboxylic acid and pine oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0884048A1 (en) * 1997-06-06 1998-12-16 Beiersdorf Aktiengesellschaft Cosmetic and dermatological emulsions containing alkylglucosides and increased electrolyte concentrations
WO2000042141A1 (en) * 1999-01-14 2000-07-20 Cognis Deutschland Gmbh Method for inhibiting crystallisation in concentrates of surfactants
EP2048220A1 (en) * 2007-10-10 2009-04-15 Cognis IP Management GmbH Method for manufacturing liquid detergents

Also Published As

Publication number Publication date
DE59606611D1 (en) 2001-04-26
EP0750034B1 (en) 2001-03-21
US5941812A (en) 1999-08-24
JPH093498A (en) 1997-01-07
EP0750034A3 (en) 1997-03-05
ES2157368T3 (en) 2001-08-16

Similar Documents

Publication Publication Date Title
DE4207386C1 (en)
EP0376083B1 (en) Pourable pearlescent agent concentrate
EP0563079B1 (en) Process for making cleaning and maintenance agents
EP0541589B1 (en) Liquid washing agent with bleaching action
EP0743975B1 (en) Hard surface cleaning agent
DE3317909A1 (en) PEARL SHINE DISPERSION
EP0719324A1 (en) Toilet soap
EP0542801B1 (en) Liquid, free-flowing and pumpable tenside concentrate
EP0164058B1 (en) Free-flowing pearl lustre dispersions with a low share of surface-active agents
EP0300379A2 (en) Nacreous concentrate without alkanol amide
DE2821585C2 (en)
EP0817609B1 (en) Pearly lustre concentrate with newtonian viscosity
DE4435495C2 (en) Pumpable aqueous surfactant concentrates
DE4017922A1 (en) LIQUID ALKYL GLYCOSIDE-CONTAINING SURFACTANT
EP0652932B1 (en) Process for producing storable non-ionic tensides
EP0572776B1 (en) Electrolyte thickenable detergent composition
EP0750034B1 (en) Storage stable, concentrated surfactant composition based on alkylglycosides
DE4019790A1 (en) LIQUID ALKYL GLYCOSIDE-CONTAINING SURFACTANT
DE1669152A1 (en) Pearlescent agent for clouding liquid or pasty preparations
EP0553099B1 (en) Liquid washing agent with increased viscosity
DE4026809A1 (en) Liq. aq. washing compsn. - contains anionic surfactant, nonionic surfactant and alkyl poly:glycoside as thickener, improving washing
EP0728836A2 (en) Storage stable, concentrated surfactant composition based on alkyl glycosides
EP0486786A1 (en) Liquid, foaming detergent
EP0555258B1 (en) Enzymatic liquid detergent
EP0670877B1 (en) Viscous aqueous surfactant preparations

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19960613

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE ES FR GB IT NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE ES FR GB IT NL SE

17Q First examination report despatched

Effective date: 19990621

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: GOLDSCHMIDT AG

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE ES FR GB IT NL SE

REF Corresponds to:

Ref document number: 59606611

Country of ref document: DE

Date of ref document: 20010426

ITF It: translation for a ep patent filed

Owner name: JACOBACCI & PERANI S.P.A.

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 20010510

ET Fr: translation filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2157368

Country of ref document: ES

Kind code of ref document: T3

PLBQ Unpublished change to opponent data

Free format text: ORIGINAL CODE: EPIDOS OPPO

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

26 Opposition filed

Opponent name: COGNIS DEUTSCHLAND GMBH

Effective date: 20011221

PLBQ Unpublished change to opponent data

Free format text: ORIGINAL CODE: EPIDOS OPPO

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

R26 Opposition filed (corrected)

Opponent name: COGNIS DEUTSCHLAND GMBH

Effective date: 20011221

NLR1 Nl: opposition has been filed with the epo

Opponent name: COGNIS DEUTSCHLAND GMBH

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

NLR1 Nl: opposition has been filed with the epo

Opponent name: COGNIS DEUTSCHLAND GMBH

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

R26 Opposition filed (corrected)

Opponent name: COGNIS DEUTSCHLAND GMBH & CO. KG

Effective date: 20011221

NLR1 Nl: opposition has been filed with the epo

Opponent name: COGNIS DEUTSCHLAND GMBH & CO. KG

PLBO Opposition rejected

Free format text: ORIGINAL CODE: EPIDOS REJO

PLBN Opposition rejected

Free format text: ORIGINAL CODE: 0009273

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: OPPOSITION REJECTED

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20030530

Year of fee payment: 8

Ref country code: GB

Payment date: 20030530

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20030604

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20030611

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20030612

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20030617

Year of fee payment: 8

27O Opposition rejected

Effective date: 20030116

NLR2 Nl: decision of opposition

Effective date: 20030116

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040607

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040608

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040608

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040630

BERE Be: lapsed

Owner name: *GOLDSCHMIDT A.G.

Effective date: 20040630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050101

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20040607

EUG Se: european patent has lapsed
EUG Se: european patent has lapsed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050228

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20050101

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050607

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20050613

Year of fee payment: 10

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20040608

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070103