EP0485500B1 - Aqueous anionic tenside concentrates with oleic acid sulphonates as viscosity controls - Google Patents
Aqueous anionic tenside concentrates with oleic acid sulphonates as viscosity controls Download PDFInfo
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- EP0485500B1 EP0485500B1 EP90912661A EP90912661A EP0485500B1 EP 0485500 B1 EP0485500 B1 EP 0485500B1 EP 90912661 A EP90912661 A EP 90912661A EP 90912661 A EP90912661 A EP 90912661A EP 0485500 B1 EP0485500 B1 EP 0485500B1
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- alkyl
- oleic acid
- aqueous
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- anionic surfactant
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/37—Mixtures of compounds all of which are anionic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
Definitions
- a commercially available tallow fatty alcohol sulfate (chain distribution: 59 - 66 C18, 27 - 35 C16, rest: C12 - C22) was used, which was in the form of a water-containing paste with a content of 55% by weight of detergent substances.
- the commercial product was dried and was then present as an anhydrous, powdery mass with a content of 100% by weight of surface-active substance (OAS).
- OAS surface-active substance
Abstract
Description
Die Erfindung betrifft wäßrige Aniontensidkonzentrate, enthaltend
- a) mindestens 30 Gew.-%, bezogen auf wäßriges Konzentrat, Aniontenside aus der von wasserlöslichen Salzen von Alkylarylsulfonaten, Alkylpolyglykolethersulfaten, Alkylarylpolyglykolethersulfaten, Alkylpolyglykolethersulfosuccinaten, Alkylarylpolyglykolether-sulfosuccinaten, Alkylsulfaten und Alkylsulfosuccinaten gebildeten Gruppe und
- b) Ölsäuresulfonate.
- a) at least 30 wt .-%, based on aqueous concentrate, anionic surfactants from that of water-soluble salts of alkylarylsulfonates, alkylpolyglycol ether sulfates, alkylarylpolyglycol ether sulfates, alkylpolyglycol ether sulfosuccinates, alkylarylpolyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates
- b) oleic acid sulfonates.
Die Herstellung und Verarbeitung von wäßrigen Zubereitungen von Aniontensiden ist wegen der Abhängigkeit der Viskosität dieser Zubereitungen von der Aniontensidkonzentration mit verschiedenen Problemen verbunden.The production and processing of aqueous preparations of anionic surfactants is associated with various problems because of the dependence of the viscosity of these preparations on the anionic surfactant concentration.
Der Tensidgehalt technischer, wäßriger Aniontensidkonzentrate liegt z.B. im Fall der Alkylarylsulfonate und Alkylsulfate üblicherweise bei 30 Gew.-%, bezogen auf das Gesamtgewicht des Konzentrats. Pasten mit höherem Tensidgehalt lassen sich nur noch unter großen Schwierigkeiten oder überhaupt nicht mehr verarbeiten, da sie bei den üblichen Verarbeitungstemperaturen nicht mehr fließfähig bzw. pumpbar sind. Eine Besonderheit im rheologischen Verhalten dieser Aniontensidkonzentrate besteht darin, daß sie auf die Zugabe von Wasser nicht mit einer Viskositätsverminderung, sondern zunächst unter Verdickung zu einem gelartigen Zustand reagieren. Daraus ergeben sich für die Weiterverarbeitung verschiedene Probleme, und zwar beispielsweise dadurch, daß sich Ventile und Rohrleitungen verstopfen, oder daß sich gebildete Gelklumpen erst nach mechanischer Zerkleinerung wieder in Lösung bringen lassen.The surfactant content of technical, aqueous anionic surfactant concentrates, for example in the case of alkylarylsulfonates and alkyl sulfates, is usually 30% by weight, based on the total weight of the concentrate. Pastes with a higher surfactant content can only be processed with great difficulty or not at all Process because they are no longer flowable or pumpable at the usual processing temperatures. A peculiarity in the rheological behavior of these anionic surfactant concentrates is that they do not react to the addition of water with a reduction in viscosity, but initially with a thickening to a gel-like state. This results in various problems for further processing, for example in that valves and pipes become blocked, or in that gel clumps formed can only be brought back into solution after mechanical comminution.
Zur Lösung dieser Probleme sind verschiedene Zusätze zur Erniedrigung der Viskosität von hochkonzentrierten Aniontensidkonzentraten beschrieben worden. So betrifft z.B. die DE-A 2 251 405 Salze bestimmter Carbonsäuren, insbesondere von Hydroxycarbonsäuren, als Viskositätsregler für anionische Tensidkonzentrate. Andere bekannte Viskositätsregler sind sulfonierte aromatische Verbindungen (DE-A 2 305 554), Sulfate oder Sulfonate von aliphatischen, gegebenenfalls substituierten Kohlenwasserstoffen mit 1 bis 6 Kohlenstoffatomen (DE-A 2 326 006), Cumolsulfonat oder saure Phosphorsäureester (DE-B 16 17 160), mehrwertige Alkohole, Carbonsäuren oder Ester derselben (EP-A 00 08 060), Mono- und/oder Disulfate von Polyalkylenetherglykolen (EP-B 00 24 711), alkoxylierte Alkohole (DE-A 37 18 896) und Alkalimetallalkansulfonate mit endständigen Sulfonatgruppen (DE-A 34 47 859). Auch der Zusatz von niederen Alkoholen als Viskositätsregler ist aus einem Teil der vorgenannten Veröffentlichungen bekannt.To solve these problems, various additives for lowering the viscosity of highly concentrated anionic surfactant concentrates have been described. For example, DE-A 2 251 405 salts of certain carboxylic acids, in particular hydroxycarboxylic acids, as viscosity regulators for anionic surfactant concentrates. Other known viscosity regulators are sulfonated aromatic compounds (DE-A 2 305 554), sulfates or sulfonates of aliphatic, optionally substituted hydrocarbons having 1 to 6 carbon atoms (DE-A 2 326 006), cumene sulfonate or acidic phosphoric acid esters (DE-B 16 17 160 ), polyhydric alcohols, carboxylic acids or esters thereof (EP-A 00 08 060), mono- and / or disulfates of polyalkylene ether glycols (EP-B 00 24 711), alkoxylated alcohols (DE-A 37 18 896) and alkali metal alkane sulfonates with terminal sulfonate groups (DE-A 34 47 859). The addition of lower alcohols as viscosity regulators is also known from some of the publications mentioned above.
Von den vorgenannten Zusätzen wirken manche Jedoch nicht bei allen Tensidkonzentraten. Andere wiederum müssen in hohen Konzentrationen eingesetzt werden. Einige der Viskositätsregler, insbesondere niedere Alkanole, erniedrigen den Flammpunkt der Konzentrate.However, some of the aforementioned additives do not work for all surfactant concentrates. Others have to be used in high concentrations. Some of the viscosity regulators, especially lower alkanols, lower the flash point of the concentrates.
Somit ist die Erfindung auf wäßrige Aniontensidkonzentrate gerichtet, die trotz eines hohen Aniontensidgehaltes durch spezielle Viskositätsregler fließfähig bzw. verarbeitbar sind bzw. bei noch für die Verarbeitung geeigneten Viskositäten höhere Feststoffgehalte aufweisen; die wäßrigen Aniontensidkonzentrate der Erfindung sind weiterhin mit Wasser verdünnbar, ohne daß dabei ein wesentlicher Anstieg ihrer Viskosität zu beobachten ist.Thus, the invention is directed to aqueous anionic surfactant concentrates which, despite a high anionic surfactant content special viscosity regulators are flowable or processable or have higher solids contents if viscosities are still suitable for processing; the aqueous anionic surfactant concentrates of the invention can also be diluted with water without a significant increase in their viscosity being observed.
Diese Aufgabe wird erfindungsgemäß durch wäßrige Aniontensidkonzentrate gelöst, die
- a) mindestens 30 Gew.-%, bezogen auf wäßriges Konzentrat, Aniontenside aus der von wasserlöslichen Salzen von Alkylarylsulfonaten, Alkylpolyglykolethersulfaten, Alkylarylpolyglykolethersulfaten, Alkylpolyglykolethersulfosuccinaten, Alkylarylpolyglykolether-sulfosuccinaten, Alkylsulfaten und Alkylsulfosuccinaten gebildeten Gruppe und
- b) Ölsäuresulfonate
- a) at least 30 wt .-%, based on aqueous concentrate, anionic surfactants from that of water-soluble salts of alkylarylsulfonates, alkylpolyglycol ether sulfates, alkylarylpolyglycol ether sulfates, alkylpolyglycol ether sulfosuccinates, alkylarylpolyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates
- b) oleic acid sulfonates
Die in den wäßrigen Aniontensidkonzentraten der Erfindung enthaltenen Aniontenside sind bekannte Verbindungen, die z.B. in J. Falbe (Hrsg.), Surfactants in Consumer Products, S. 54 bis S. 132, Springer Verlag Berlin (1967), beschrieben sind. Im Rahmen der Erfindung besonders bevorzugte Aniontenside sind lineare Alkylbenzolsufonate, insbesondere solche mit einer C₁₂-Alkylgruppe, sowie Alkylsulfate mit 10 bis 22 Kohlenstoffatomen in den (linearen) Alkylketten, wie sie z.B. aus Laurylalkohol oder Stearylalkohol bzw. technischen Gemischen derselben wie Kokosfettalkohol oder Talgfettalkohol, zugänglich sind.The anionic surfactants contained in the aqueous anionic surfactant concentrates of the invention are known compounds which e.g. in J. Falbe (ed.), Surfactants in Consumer Products, p. 54 to p. 132, Springer Verlag Berlin (1967). Anionic surfactants which are particularly preferred in the context of the invention are linear alkylbenzenesulfonates, in particular those having a C₁₂-alkyl group, and also alkyl sulfates having 10 to 22 carbon atoms in the (linear) alkyl chains, such as those e.g. from lauryl alcohol or stearyl alcohol or technical mixtures thereof, such as coconut oil alcohol or tallow oil alcohol.
Die in den wäßrigen Aniontensidkonzentraten der Erfindung als Viskositätsregler enthaltenen Ölsäuresulfonate sind Verbindungen, die aus der GB-C 1 278 421 bekannt sind. Sie können erhalten werden, indem man Ölsäure bzw. technische Gemische derselben, wie sie aus natürlichen, nachwachsenden Rohstoffen, insbesondere Rindertalg, Sonnenblumenöl, Rapsöl, Olivenöl und dergleichen zugänglich sind, mit gasförmigem Schwefeltrioxid sulfoniert und die Sulfonierungsprodukte mit wäßrigen Basen neutralisiert und hydrolysiert. Die dabei erhaltenen Ölsäuresulfonate können in Abhängigkeit von ihrer Herkunft mehr oder weniger große Anteile an gesättigten Fettsäuren sowie Sulfonierungsprodukte anderer ungesättigter Fettsäuren derselben enthalten, die die Wirkung der Ölsäuresulfonate als Viskositätsregler nicht stören.The oleic acid sulfonates contained in the aqueous anionic surfactant concentrates of the invention as viscosity regulators are compounds which are known from GB-C 1 278 421. You can can be obtained by oleic acid or technical mixtures thereof, as are available from natural, renewable raw materials, in particular beef tallow, sunflower oil, rapeseed oil, olive oil and the like, sulfonated with gaseous sulfur trioxide and the sulfonation products neutralized and hydrolyzed with aqueous bases. Depending on their origin, the oleic acid sulfonates obtained can contain more or less large proportions of saturated fatty acids and sulfonation products of other unsaturated fatty acids which do not interfere with the action of the oleic acid sulfonates as viscosity regulators.
Gemäß einer vorteilhaften Ausführungsform der Erfindung enthalten die wäßrigen Aniontenside lineare Alkylbenzolsulfonate oder Alkylsulfate und Ölsäuresulfonate in Gewichtsverhältnissen zueinander von 90 : 10 bis 50 : 50.According to an advantageous embodiment of the invention, the aqueous anionic surfactants contain linear alkylbenzenesulfonates or alkylsulfates and oleic acid sulfonates in weight ratios to one another of from 90:10 to 50:50.
Die Erfindung betrifft weiterhin die Verwendung der obengenannten Ölsäuresulfonate als Viskositätsregler für wäßrige Aniontensidkonzentrate, die mindestens 30 Gew.-% Aniontenside aus der von wasserlöslichen Salzen von Alkylarylsulfonaten, Alkylpolyglykolethersulfaten, Alkylarylpolyglykolethersulfaten, Alkylpolyglykolether-sulfosuccinaten, Alkylarylpolyglykolether-sulfosuccinaten, Alkylsulfaten und Alkylsulfosuccinaten gebildeten Gruppe enthalten. Bevorzugt ist dabei die Verwendung der genannten Ölsäuresulfonate in Aniontensidkonzentraten, die lineare Alkylbenzolsulfonate oder Alkylsulfate und die Ölsäuresulfonate in Gewichtsverhältnissen von 90 : 10 bis 50 : 50 enthalten.The invention further relates to the use of the above oleic acid sulfonates as viscosity regulators for aqueous anionic surfactant concentrates, the sulfosuccinates alkyl polyglycol ether least 30 wt .-% of anionic surfactants from the water-soluble salts of alkylaryl sulfonates, alkyl polyglycol ether sulfates, Alkylarylpolyglykolethersulfaten, alkylaryl polyglycol ether-sulfosuccinates containing alkyl sulfates and alkyl sulfosuccinates group formed. It is preferred to use the oleic acid sulfonates mentioned in anionic surfactant concentrates which contain linear alkylbenzenesulfonates or alkyl sulfates and the oleic acid sulfonates in a weight ratio of from 90:10 to 50:50.
Die wäßrigen Aniontensidkonzentrate der Erfindung können gemäß einer ersten Verfahrensvariante hergestellt werden, indem man Aniontenside aus der von Alkylarylsulfonaten, Alkylpolyglykolethersulfaten, Alkylarylpolyglykolethersulfaten, Alkylpolyglykolether-sulfosuccinaten, Alkylarylpolyglykolethersulfosuccinaten, Alkylsulfaten und Alkylsulfosuccinaten gebildeten Gruppe mit der gewünschten Menge an Ölsäuresulfonaten, gegebenenfalls unter Zusatz von Wasser und/oder Erwärmen, mischt. Gemäß einer zweiten Verfahrensvariante können die wäßrigen Aniontensidkonzentrate der Erfindung hergestellt werden, indem man die Säureform der oben genannten Aniontenside mit der gewünschten Menge an Ölsäuresulfonaten mischt und das Gemisch mit konzentrierten wäßrigen Basen, insbesondere konzentrierter wäßriger Natronlauge, neutralisiert. Diese Verfahrensvariante ist besonders geeignet, wenn die Aniontenside Alkylarylsulfonate sind. Bei den übrigen Aniontensiden, z.B. Alkylsulfaten, ist zu beachten, daß diese in ihrer Säureform instabil sein können, so daß ihre Neutralisation in Gegenwart der Ölsäuresulfonate unmittelbar im Anschluß an ihre Herstellung erfolgen sollte.The aqueous anionic surfactant concentrates of the invention can be prepared according to a first process variant by preparing anionic surfactants from the amount of alkyl desired sulfate and alkyl sulfate succinates, the alkyl sulfate and alkyl sulfate succinates, the alkyl sulfate and alkyl sulfate succinate, the alkyl sulfate and alkyl sulfate succinate desired Oleic acid sulfonates, optionally with the addition of water and / or heating, mixes. According to a second process variant, the aqueous anionic surfactant concentrates of the invention can be prepared by mixing the acid form of the above-mentioned anionic surfactants with the desired amount of oleic acid sulfonates and neutralizing the mixture with concentrated aqueous bases, in particular concentrated aqueous sodium hydroxide solution. This process variant is particularly suitable if the anionic surfactants are alkylarylsulfonates. With the other anionic surfactants, for example alkyl sulfates, it should be noted that these can be unstable in their acid form, so that they should be neutralized in the presence of the oleic acid sulfonates immediately after their preparation.
Die wäßrigen Aniontensidkonzentrate der Erfindung weisen trotz ihres Gehaltes an Ölsäuresulfonaten, der, bezogen auf die Aniontenside, bis zu 50 Gew.-% betragen kann, im Vergleich zu Aniontensidkonzentraten ohne Zusatz an Ölsäuresulfonaten praktisch die gleiche oberflächenaktive Wirkung auf.The aqueous anionic surfactant concentrates of the invention, despite their content of oleic acid sulfonates, which, based on the anionic surfactants, can be up to 50% by weight, have practically the same surface-active effect as anionic surfactant concentrates without the addition of oleic acid sulfonates.
Die Erfindung wird im folgenden anhand von bevorzugten Ausführungsbeispielen näher erläutert.The invention is explained in more detail below on the basis of preferred exemplary embodiments.
Als lineare C₁₂-Alkylbenzolsulfonsäure wurde eine handelsübliche Qualität mit einer Säurezahl von 180 und einem Gehalt an sulfierten Anteilen von 97,5 Gew.-% verwendet.As a linear C₁₂-alkylbenzenesulfonic acid, a commercial grade with an acid number of 180 and a sulfated content of 97.5% by weight was used.
Das eingesetzte Ölsäuresulfonat-natriumsalz war durch Sulfonierung einer technischen Ölsäure aus Rindertalg (Zusammensetzung: 70,7 Gew.-% Ölsäure, 11,8 Gew.-% Linolsäure, Rest: andere C₁₂- bis C₂₀-Fettsäuren; Säurezahl 200,4, Jodzahl 93,8) mit Schwefeltrioxid und anschließender Neutralisation und Hydrolyse erhalten worden. Die Sulfonierung wurde in einem Fallfilmreaktor aus Glas vorgenommen, der im wesentlichen aus einem von einem Heiz- und Kühlmantel umgebenen Rohr mit einer Länge von 1100 mm und einem Innendurchmesser von 6 mm bestand. Der Reaktor war am Kopf mit einer Aufgabevorrichtung für die Ölsäure und mit einem Gaseinleitungsrohr versehen. Gasförmiges Schwefeltrioxid, erzeugt durch Erhitzen von Oleum, wurde mit Stickstoff auf eine Konzentration von 5 Vol.-% Schwefeltrioxid verdünnt und in der Sulfonierung eingesetzt. Die Ölsäure wurde mit einer konstanten Geschwindigkeit von 550 g/h aufgegeben. Die Zufuhr des Schwefeltrioxid/Stickstoff-Gemisches wurde so eingestellt, daß das Molverhältnis von in der technischen Ölsäure vorhandenen, olefinischen Doppelbindungen (errechnet aus der Jodzahl) zu Schwefeltrioxid 1 : 0,9 betrug. Mit Hilfe eines Wasserkreislaufs durch den Reaktormantel wurde die Reaktionstemperatur der Sulfonierung bei 50°C gehalten. Nach dem Verlassen des Reaktors wurde das Reaktionsgemisch in einem Becherglas, das 25 Gew.-%-ige Natronlauge enthielt, aufgefangen und anschließend bei einem pH-Wert von 8 bis 9 zwei Stunden auf 90°C erhitzt. Das gewünschte Produkt wurde in einer Konzentration von 59,5 Gew.-% in Wasser erhalten.The oleic acid sulfonate sodium salt used was sulfonation of a technical oleic acid from beef tallow (composition: 70.7% by weight oleic acid, 11.8% by weight linoleic acid, the rest: other C₁₂ to C₂ bis fatty acids; acid number 200.4, iodine number 93.8) with sulfur trioxide and subsequent neutralization and hydrolysis. The sulfonation was carried out in a falling film reactor made of glass, which essentially consisted of a tube surrounded by a heating and cooling jacket with a length of 1100 mm and an inner diameter of 6 mm. The head of the reactor was equipped with a feed device for oleic acid and with a gas inlet pipe. Gaseous sulfur trioxide, produced by heating oleum, was diluted with nitrogen to a concentration of 5% by volume of sulfur trioxide and used in the sulfonation. The oleic acid was applied at a constant rate of 550 g / h. The feed of the sulfur trioxide / nitrogen mixture was adjusted so that the molar ratio of olefinic double bonds present in technical oleic acid (calculated from the iodine number) to sulfur trioxide was 1: 0.9. The reaction temperature of the sulfonation was kept at 50 ° C. with the aid of a water circuit through the reactor jacket. After leaving the reactor, the reaction mixture was collected in a beaker containing 25% by weight sodium hydroxide solution and then two at a pH of 8 to 9 Heated to 90 ° C for hours. The desired product was obtained in a concentration of 59.5% by weight in water.
55 g der oben genannten C₁₂-Alkylbenzolsulfonsäure und 30,9 g des oben genannten Ölsäuresulfonat-natriumsalzes (in Form der oben beschriebenen wäßrigen Lösung) wurden mit 14,1 g Natronlauge (als 50 Gew.-%-ige wäßrige Lösung) neutralisiert. Es wurde ein Tensidgemisch erhalten, das 74,5 Gew.-% Tenside (Natriumsalze der C₁₂-Alkylbenzolsulfonsäure und des Ölsäuresulfonats) enthielt.55 g of the above C₁₂-alkylbenzenesulfonic acid and 30.9 g of the above-mentioned oleic acid sulfonate sodium salt (in the form of the aqueous solution described above) were neutralized with 14.1 g of sodium hydroxide solution (as a 50% by weight aqueous solution). There was obtained a surfactant mixture containing 74.5 wt .-% surfactants (sodium salts of C₁₂-alkylbenzenesulfonic acid and oleic acid sulfonate).
Unter Zusatz von Wasser zu dem vorgenannten Tensidgemisch wurden anschließend die in Tabelle 1 angegebenen Tensidkonzentrationen eingestellt; die Viskosität der dabei erhaltenen Gemische wurde mit einem Brookfield-Viskosimeter bestimmt (Brookfield-Heliphat RVF, 4U/min, 22°C, Spindel: T-E bzw. T-B).With the addition of water to the aforementioned surfactant mixture, the surfactant concentrations given in Table 1 were then set; the viscosity of the mixtures obtained was determined using a Brookfield viscometer (Brookfield heliphat RVF, 4 rpm, 22 ° C., spindle: T-E or T-B).
Die Tabelle 1 enthält weiterhin zu Vergleichszwecken die Viskosität von C₁₂-Alkylbenzolsulfonsäure-natriumsalz ohne Ölsäuresulfonat-Zusatz bei Tensidkonzentrationen von 75 bzw. 55 %.For comparison purposes, Table 1 also contains the viscosity of sodium C₁₂-alkylbenzenesulfonic acid without the addition of oleic acid sulfonate at surfactant concentrations of 75 or 55%.
Es zeigt sich, daß die wäßrigen Aniontensidkonzentrate der Erfindung bei vergleichbaren Tensidkonzentrationen eine deutlich verringerte Viskosität aufweisen.
Es wurde ein handelsübliches Talgfettalkoholsulfat (Kettenverteilung: 59 - 66 C₁₈, 27 - 35 C₁₆, Rest: C₁₂ - C₂₂) verwendet, das in Form einer wasserhaltigen Paste mit einem Gehalt von 55 Gew.-% an waschaktiven Substanzen vorlag. Das Handelsprodukt wurde getrocknet und lag dann als wasserfreie, pulverförmige Masse mit einem Gehalt von 100 Gew.-% an oberflächenaktiver Substanz (OAS) vor. Das getrocknete Talgfettalkoholsulfat, im folgenden mit TAS bezeichnet, wurde mit einer wäßrigen, 52,8 gew.-%-igen Lösung eines Ölsäuresulfonat-natriumsalzes, erhalten in der in Beispiel 1 beschriebenen Weise aus einer technischen Ölsäure der dort beschriebenen Zusammensetzung, im folgenden mit OS bezeichnet, vermischt; die gewünschte Tensidkonzentration (OAS) wurde durch Zugabe von Wasser eingestellt.A commercially available tallow fatty alcohol sulfate (chain distribution: 59 - 66 C₁₈, 27 - 35 C₁₆, rest: C₁₂ - C₂₂) was used, which was in the form of a water-containing paste with a content of 55% by weight of detergent substances. The commercial product was dried and was then present as an anhydrous, powdery mass with a content of 100% by weight of surface-active substance (OAS). The dried tallow fatty alcohol sulfate, hereinafter referred to as TAS, was obtained with an aqueous, 52.8% by weight solution of an oleic acid sulfonate sodium salt, obtained in the manner described in Example 1 from an industrial oleic acid of the composition described therein, hereinafter with OS referred to, mixed; the desired surfactant concentration (OAS) was set by adding water.
In der Tabelle 2 sind die zugesetzten Mengen an TAS, an der OS-Lösung und der entsprechenden, auf 100 Gew.-% umgerechneten OS-Menge und an Wasser zusammengefaßt, weiterhin das erhaltene Gewichtsverhältnis von TAS zu OS und der Gesamtgehalt der erhaltenen Lösung an Tensiden (OAS) sowie die nach Höppler am Kugelfallviskosimeter gemessenen Viskositäten in mPas bei 60°C und 80°C. Die Tabelle 2 enthält auch die Meßergebnisse, die zum Vergleich mit einer lediglich TAS enthaltenden Lösung erhalten wurden.Table 2 summarizes the added amounts of TAS, the OS solution and the corresponding amount of OS converted to 100% by weight and water, the weight ratio of TAS to OS obtained and the total content of the solution obtained Tensides (OAS) as well as the viscosities measured in mPas at 60 ° C and 80 ° C according to Höppler on the falling ball viscometer. Table 2 also contains the measurement results obtained for comparison with a solution containing only TAS.
Es zeigt sich, daß der erfindungsgemäße Zusatz von OS eine deutliche Verringerung der Viskosität der Tensidlösungen bewirkt.
Claims (6)
- Aqueous anionic surfactant concentrates containinga) at least 30% by weight, based on aqueous concentrate, of anionic surfactants from the group consisting of the water-soluble salts of alkylaryl sulfonates, alkyl polyglycol ether sulfates, alkylaryl polyglycol ether sulfates, alkyl polyglycol ether sulfosuccinates, alkylaryl polyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates andb) oleic acid sulfonates.
- Aqueous anionic surfactant concentrates as claimed in claim 1 containing a mixture of linear alkyl benzenesulfonates and oleic acid sulfonates in ratios by weight to one another of 90:10 to 50:50.
- Aqueous surfactant concentrates as claimed in claim 1 containing a mixture of alkyl sulfates and oleic acid sulfonates in a ratio by weight to one another of 90:10 to 50:50.
- The use of oleic acid sulfonates as viscosity regulators for aqueous anionic surfactant concentrates containing at least 30% by weight anionic surfactants from the group consisting of water-soluble salts of alkylaryl sulfonates, alkyl polyglycol ether sulfates, alkylaryl polyglycol ether sulfates, alkyl polyglycol ether sulfosuccinates, alkylaryl polyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates.
- The use claimed in claim 4, characterized in that the anionic surfactant concentrates contain linear alkyl benzenesulfonates and oleic acid sulfonates in ratios by weight to one another of 90:10 to 50:50.
- The use claimed in claim 4, characterized in that the anionic surfactant concentrates contain a mixture of alkyl sulfates and oleic acid sulfonates in a ratio by weight to one another of 90:10 to 50:50.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3926345 | 1989-08-09 | ||
| DE3926345A DE3926345A1 (en) | 1989-08-09 | 1989-08-09 | AQUEOUS ANCIENT SIDE CONCENTRATES WITH A CONTENT OF OIL ACID SULPHONATES AND THE USE OF OIL ACID SULPHONATES AS A VISCOSITY CONTROLLER FOR AQUEOUS ANION ANTENSIDE CONCENTRATES |
| PCT/EP1990/001249 WO1991002045A1 (en) | 1989-08-09 | 1990-07-31 | Aqueous anionic tenside concentrates with oleic acid sulphonates as viscosity controls |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0485500A1 EP0485500A1 (en) | 1992-05-20 |
| EP0485500B1 true EP0485500B1 (en) | 1994-09-21 |
Family
ID=6386812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90912661A Expired - Lifetime EP0485500B1 (en) | 1989-08-09 | 1990-07-31 | Aqueous anionic tenside concentrates with oleic acid sulphonates as viscosity controls |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0485500B1 (en) |
| JP (1) | JPH04506928A (en) |
| DE (2) | DE3926345A1 (en) |
| ES (1) | ES2062548T3 (en) |
| WO (1) | WO1991002045A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3926345A1 (en) * | 1989-08-09 | 1991-02-14 | Henkel Kgaa | AQUEOUS ANCIENT SIDE CONCENTRATES WITH A CONTENT OF OIL ACID SULPHONATES AND THE USE OF OIL ACID SULPHONATES AS A VISCOSITY CONTROLLER FOR AQUEOUS ANION ANTENSIDE CONCENTRATES |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4019172A1 (en) * | 1990-06-15 | 1991-12-19 | Henkel Kgaa | USE OF SALTS OF THE SULFONATION PRODUCTS OF UNSATURATED FATTY AS A VISCOSITATE REDUCER |
| DE4026639A1 (en) * | 1990-08-23 | 1992-02-27 | Henkel Kgaa | Detergent mixt. contg. alkylbenzene sulphonate salt, sodium sulphate - and oleic acid sulphonate di-salt, giving lower viscosity |
| DE4107414A1 (en) * | 1991-03-08 | 1992-09-10 | Henkel Kgaa | LIQUID CLEANING AGENT CONTAINING SULFOLOIC ACIDS |
| DE4109250A1 (en) * | 1991-03-21 | 1992-09-24 | Henkel Kgaa | METHOD FOR PRODUCING HIGHLY CONCENTRATED FATTY ALCOHOL SULFATE PASTE |
| US5538672A (en) * | 1991-08-03 | 1996-07-23 | Henkel Kommanditgesellschaft Auf Aktien | Free-flowing water-containing alkyl sulfate pastes |
| DE4125792A1 (en) * | 1991-08-03 | 1993-02-04 | Henkel Kgaa | FLOWABLE WAESSED ALKYLSULFATE PASTE |
| DE102007032670A1 (en) | 2007-07-13 | 2009-01-15 | Clariant International Ltd. | Aqueous compositions containing alkyl polyethylene glycol ether sulfates |
| US7998920B2 (en) | 2008-01-22 | 2011-08-16 | Stepan Company | Sulfonated estolide compositions containing magnesium sulfate and processes employing them |
| US7879790B2 (en) | 2008-01-22 | 2011-02-01 | Stepan Company | Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them |
| US7666828B2 (en) | 2008-01-22 | 2010-02-23 | Stepan Company | Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them |
| US8119588B2 (en) | 2009-01-21 | 2012-02-21 | Stepan Company | Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof |
| US7884064B2 (en) | 2009-01-21 | 2011-02-08 | Stepan Company | Light duty liquid detergent compositions of sulfonated estolides and other derivatives of fatty acids |
| US8058223B2 (en) | 2009-01-21 | 2011-11-15 | Stepan Company | Automatic or machine dishwashing compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof |
| US8124577B2 (en) | 2009-01-21 | 2012-02-28 | Stepan Company | Personal care compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3447859A1 (en) * | 1984-12-31 | 1986-07-10 | Henkel KGaA, 4000 Düsseldorf | USE OF ALKANESULPHONATES AS A VISCOSITY REGULATOR FOR HIGHLY VISCOSE ANIONTENSIDE CONCENTRATES |
| DE3902619A1 (en) * | 1989-01-30 | 1990-08-02 | Henkel Kgaa | LIQUID CLEANING AGENTS |
| DE3926345A1 (en) * | 1989-08-09 | 1991-02-14 | Henkel Kgaa | AQUEOUS ANCIENT SIDE CONCENTRATES WITH A CONTENT OF OIL ACID SULPHONATES AND THE USE OF OIL ACID SULPHONATES AS A VISCOSITY CONTROLLER FOR AQUEOUS ANION ANTENSIDE CONCENTRATES |
-
1989
- 1989-08-09 DE DE3926345A patent/DE3926345A1/en not_active Withdrawn
-
1990
- 1990-07-31 WO PCT/EP1990/001249 patent/WO1991002045A1/en active IP Right Grant
- 1990-07-31 EP EP90912661A patent/EP0485500B1/en not_active Expired - Lifetime
- 1990-07-31 JP JP2511715A patent/JPH04506928A/en active Pending
- 1990-07-31 ES ES90912661T patent/ES2062548T3/en not_active Expired - Lifetime
- 1990-07-31 DE DE59007286T patent/DE59007286D1/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3926345A1 (en) * | 1989-08-09 | 1991-02-14 | Henkel Kgaa | AQUEOUS ANCIENT SIDE CONCENTRATES WITH A CONTENT OF OIL ACID SULPHONATES AND THE USE OF OIL ACID SULPHONATES AS A VISCOSITY CONTROLLER FOR AQUEOUS ANION ANTENSIDE CONCENTRATES |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0485500A1 (en) | 1992-05-20 |
| DE3926345A1 (en) | 1991-02-14 |
| DE59007286D1 (en) | 1994-10-27 |
| WO1991002045A1 (en) | 1991-02-21 |
| ES2062548T3 (en) | 1994-12-16 |
| JPH04506928A (en) | 1992-12-03 |
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