EP0281028A2 - Shaped detergent - Google Patents
Shaped detergent Download PDFInfo
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- EP0281028A2 EP0281028A2 EP88102884A EP88102884A EP0281028A2 EP 0281028 A2 EP0281028 A2 EP 0281028A2 EP 88102884 A EP88102884 A EP 88102884A EP 88102884 A EP88102884 A EP 88102884A EP 0281028 A2 EP0281028 A2 EP 0281028A2
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- sodium
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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
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
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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
- C11D1/04—Carboxylic acids or salts thereof
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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
- C11D1/37—Mixtures of compounds all of which are anionic
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/0052—Cast detergent compositions
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
- C11D3/2013—Monohydric alcohols linear fatty or with at least 8 carbon atoms in the alkyl chain
-
- 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
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
Definitions
- the invention relates to shaped cleaning agents based on fatty alcohol sulfates with improved formability and surface smoothness.
- Syndet soap compositions based on fatty alcohol sulfates which contain fatty alcohols with 12 to 18 carbon atoms or fatty acids or partially saponified fatty acids as plasticizers and binders, have long been known and have been on the market.
- alpha-sulfofatty acid salts are also known to use as components of shaped cleaning agents based on synthetic detergent raw materials.
- DE-AS 12 31 376 was the addition of dialkali salts of alpha-sulfo fatty acids with 12 to 18 C atoms known for cleaning agent pieces based on alkali acylisäthionaten.
- DE-AS 16 17 220 describes the addition of alpha-sulfofatty acid alkali salts to synthetic detergent pieces based on alpha-olefin sulfonates.
- From DE-OS 24 03 895 the use of alpha-sulfofatty acid (C8-C16) alkali salts as a surfactant base for weakly acidic Syndet toilet soaps was known.
- the present invention is based on the observation that the formability and smoothness of shaped cleaning agents based on sodium alkyl sulfate, which contain fatty alcohols and fatty acids as plasticizers and binders, can be markedly improved in relatively small amounts by adding an alpha-sulfofatty acid salt. At the same time, such cleaning agents showed an improved skin feel when used. On the basis of this observation, it was possible to determine the proportions of the components which, in terms of manufacturability, strength and application properties, result in a particularly favorable, shaped detergent composition.
- the invention relates to shaped cleaning agents with a content of 30 to 70 wt .-% of a sodium alkyl sulfate with 12 to 18 carbon atoms, which is characterized in that to improve the formability and the application properties 5 to 25% by weight of a fatty alcohol with 12 to 18 carbon atoms, 5 to 25 wt .-% palmitic and / or stearic acid, optionally in partially saponified form and 1 to 30% by weight of an alpha-sulfofatty acid salt of the formula I.
- R1 is a linear alkyl group with 9 to 21 C atoms
- A is an alkali metal, ammonium or a mono-, di- or trialkanolammonium ion with 2 or 3 C atoms in the alkanol group and B is hydrogen or one of the meanings of A has, is contained.
- the sodium alkyl sulfate is in anhydrous or low-water form, e.g. B. as a spray-dried powder, as granules, in the form of needles or noodles or in recrystallized form.
- Uniform sodium alkyl sulfates e.g. B. Na lauryl sulfate or Na cetyl sulfate can be used as homolog mixtures.
- the fatty alcohols with 12 to 18 carbon atoms can also be used as uniform alcohols or as homolog mixtures, e.g. B. in the composition as obtained by hydrogenation of vegetable or animal fatty acid fractions, for. B. coconut oil alcohol C12-C18 or tallow alcohol. Saturated fatty alcohols with 16 to 18 carbon atoms, e.g. B. Cetyl-stearyl alcohol fractions.
- the palmitic acid and stearic acid can be used in pure form or as a mixture. Although saponification per se is not required, it may be useful to prevent the decomposition of the alkyl sulfate when mixing the components in the Kneaders use a small amount of an alkali metal hydroxide at elevated temperature. A small part of the palmitic and / or stearic acid can be saponified. However, care should be taken to ensure that no more than 50% of the fatty acid is saponified.
- Alpha sulfofatty acid salts of formula I are known from the literature. The production of alpha-sulfopalmitic acid disodium salt and its homologues from lauric, myristic and stearic acid and their properties are e.g. B. in J. Am. Oil Chem. Soc., May 1952, pages 198 to 201. In an analogous manner, other alpha-sulfofatty acid salts of the formula I, e.g. B. the ammonium and alkanolammonium salts, if you use the appropriate bases for neutralization. Suitable alkanolamines are e.g. B. mono-, di- and triethanolamine or mono-, di- or triisopropanolamine.
- mixed salts e.g. B.
- the sodium-triethanolammonium mixed salts can be carried out analogously by carrying out the neutralization with 1 mole of sodium hydroxide and 1 mole of triethanolamine per mole of alpha-sulfofatty acid.
- acid salts of alpha-sulfo fatty acids can also be prepared by neutralization with only 1 mol of the base.
- the shaped cleaning agents according to the invention can contain further suitable surfactants.
- a preferred position are the sulfosuccinic acid monoalkyl (C8-C18) ester disodium salts. These can be contained in amounts of up to 35% by weight, preferably in amounts of 5 to 25% by weight.
- the sulfosuccinic acid monoalkyl esters are prepared by known processes by reacting maleic anhydride with a fatty alcohol having 8 to 18 carbon atoms to form the maleic acid monoester of the fatty alcohol and sulfitating it with sodium sulfite to the sulfosuccinic acid ester.
- surfactants and auxiliaries can be contained in amounts of up to 20% by weight.
- Such surfactants and auxiliaries, if any, which are particularly suitable for use in the cleaning agents shaped according to the invention are, for.
- B. - anionic surfactants e.g. B. Alpha-olefin sulfonates with 15 to 18 carbon atoms, acyl sarcosines, acyl isethionates and acyl taurines each with 8 to 18 carbon atoms in the acyl group, alkyl (C8-C18) phosphates and acyl cyanamides with 8 to 18 carbon atoms in the acyl group
- - non-ionic surfactants e.g. B.
- fatty acid mono- and diglycerides sorbitan fatty acid esters, fatty acid alkanolamides and ethylene oxide addition products to these compounds, further addition products of ethylene oxide and / or propylene oxide to fatty alcohols with 8 to 22 carbon atoms, to C12-C18 fatty amines, to alkylphenols with 8 to 15 C- Atoms in the alkyl group.
- suitable nonionic surfactants are sugar fatty acid esters, alkyl glucosides and alkyl oligoglucosides with 8 to 18 carbon atoms in the alkyl group and methyl glucoside fatty acid partial esters and their ethylene oxide addition products, - ampholytic surfactants, e.g. B.
- 2-alkyl (C8-C18) aminopropionic acid, alkyl (C8-C18) aminoacetic acid, - zwitterionic surfactants such as B. N-alkyl (C8-C18) -dimethylammonio-glycinate, alkyl (C8-C1amin) -aminopropyl-dimethylammonio-glycinate, alkyl (C8-C18) -3-carboxymethyl-3-hydroxyethyl-imidazoline, - organic fillers and auxiliaries such.
- starch dextrin, carboxymethyl cellulose, sorbitol, mannitol, urea, proteins and protein hydrolyzates, polyethylene glycols, paraffin, - inorganic fillers and auxiliaries such.
- B sodium sulfate, sodium hydrogen phosphate, sodium hydrogen carbonate, layered silicates (e.g. bentonite, montmorillonite), zeolites (e.g. zeolite A), water glass, - complexing agents, - antimicrobials, preservatives, - dyes, - opacifiers and matting agents, e.g. B. pigments such as titanium dioxide, - fragrances.
- the cleaning agents shaped according to the invention contain 40 to 60 wt .-% alkyl (C10-C18) sulfate, sodium salt 10 to 20% by weight of cetyl and / or stearyl alcohol 10 to 20% by weight of an optionally partially saponified palmitic and / or stearic acid 5 to 20 wt .-% of an alpha-sulfofatty acid salt of the formula I and 0 to 20% by weight of other known surfactants and auxiliaries.
- the cleaning agents shaped in accordance with the invention can be produced in the manner customary for such products, the combination of additives according to the invention resulting in a particularly readily formable mass which is plastic in the heat and hard after cooling, and in which the shaped products have a smooth surface.
- Usual methods for mixing or homogenizing, kneading, optionally pelleting, extrusion, optionally pelleting, extruding, cutting and pressing, as described in the publication cited above in JAOCS, Vol. 59, No. 10 (October 1982) can be used for the production of the cleaning agents shaped according to the invention.
- the following procedure has proven particularly useful for the production of handy Syndet soap bars:
- the fusible components e.g. B. the fatty alcohol, the palmitic and / or stearic acid and optionally nonionic surfactants or meltable organic fillers and auxiliaries are melted at temperatures of 60 to 90 ° C in a heatable kneader or mixer and optionally mixed after adding a small amount of an alkali metal hydroxide solution. Then the addition of the sodium alkyl sulfate and optionally other components which cannot be melted at 60 to 90 ° C. and a quantity of water which adjusts the total water content of the batch to about 5 to 15% by weight of H 2 O, as well as mixing or kneading of the batch at a temperature of approx. 40 to 70 ° C.
- a further homogenization can be achieved in that the mass is pressed through sieves several times at 40 to 70 ° C and finally pressed at a head temperature of 40 to 70 ° C into a strand which is cut into uniform pieces. The pieces can finally be brought into a final shape in a molding press.
- extrusion can also take place through a perforated plate, the cleaning agents according to the invention being obtained after cooling in the form of needles or, if the perforated plate is followed by knives, in the form of granules.
- Cetyl stearyl alcohol, palmitin stearic acid and optionally hydrotalg alcohol oxyethylate were melted in a kneader at 70 ° C. Then the KOH solution heated to 60 ° C. was added and kneaded for 30 minutes. Then the fatty alcohol sulfate, the sulfosuccinic acid ester salt, the alpha-sulfo fatty acid salt and the water were added. After about 1 hour of further kneading, the water content of a sample was determined and a total water content of 11% by weight was set by adding more water and kneading for a further 30 minutes.
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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)
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- Detergent Compositions (AREA)
Abstract
Geformte Reinigungsmittel, z. B. Stückseifen, mit einem Gehalt von 30 bis 70 Gew.-% eines Natrium-C12-C18-Alkylsulfats enthalten zur Verbesserung der Formbarkeit und der Anwendungseigenschaften 5 bis 25 Gew.-% eines C12-C18-Fettalkohols, 5 bis 25 Gew.-% Palmitin- und/oder Stearinsäure, ggf. teilweise verseift, und 1 bis 30 Gew.-% eines Alpha-Sulfofettsäure-Salzes der Formel <IMAGE> in der R¹ eine C9-C21-Alkylgruppe, A ein Alkali-, Ammonium- oder Alkanolammonium-Kation und B Wasserstoff ist oder eine der Bedeutungen von A hat.Shaped cleaning agents, e.g. B. bar soaps, with a content of 30 to 70 wt .-% of a sodium C12-C18 alkyl sulfate contain 5 to 25 wt .-% of a C12-C18 fatty alcohol to improve the formability and the application properties, 5 to 25 wt. % Palmitic and / or stearic acid, optionally partially saponified, and 1 to 30% by weight of an alpha-sulfofatty acid salt of the formula <IMAGE> in which R¹ is a C9-C21-alkyl group, A is an alkali metal, ammonium or alkanolammonium cation and B is hydrogen or has one of the meanings of A.
Description
Gegenstand der Erfindung sind geformte Reinigungsmittel auf Basis von Fettalkoholsulfaten mit einer verbesserten Formbarkeit und Oberflächenglätte.The invention relates to shaped cleaning agents based on fatty alcohol sulfates with improved formability and surface smoothness.
Es ist bekannt, Fettalkoholsulfate ähnlich wie Seifen auf Fettsäurebasis durch Kneten, Pilieren, Strangpressen, Extrudieren, Schneiden und Stückpressen in eine geeignete Form für den Transport und für die Anwendung zu bringen. Auf diese Weise lassen sich Nadeln, Granulate, Nudeln, Riegel und handliche Stücke erzeugen. Die geringe Plastizität der Fettalkoholsulfate bedingt erhebliche Probleme bei der Verarbeitung zu geformten Produkten und es ist bekannt, daß man zur Verbesserung der Verarbeitungs- und Anwendungseigenschaften dem Fettalkoholsulfat weitere Tensidkomponenten, Plastifikatoren, Bindemittel, Füllstoffe und weitere Additive zusetzt. Eine Übersicht über bekannte Zusatzstoffe für synthetische Stückseifen ist in JAOCS, Vol. 59, No. 10 (Oktober 1982), Seiten 442 bis 448 veröffentlicht.It is known to convert fatty alcohol sulfates, like fatty acid-based soaps, into a suitable form for transport and use by kneading, piling, extruding, extruding, cutting and bar-pressing. In this way, needles, granules, pasta, bars and handy pieces can be produced. The low plasticity of the fatty alcohol sulfates causes considerable problems when processing them into shaped products, and it is known that to improve the processing and application properties, further surfactant components, plasticizers, binders, fillers and other additives are added to the fatty alcohol sulfate. An overview of known additives for synthetic bar soaps can be found in JAOCS, Vol. 59, No. 10 (October 1982), pages 442 to 448.
Syndet-Seifenmassen auf Basis von Fettalkoholsulfaten, die als Plastifikatoren und Bindemittel Fettalkohole mit 12 bis 18 C-Atomen oder Fettsäuren bzw. teilverseifte Fettsäuren enthalten, sind bereits seit langem bekannt und auf dem Markt.Syndet soap compositions based on fatty alcohol sulfates, which contain fatty alcohols with 12 to 18 carbon atoms or fatty acids or partially saponified fatty acids as plasticizers and binders, have long been known and have been on the market.
Es ist auch bekannt, Alpha-Sulfofettsäure-Salze als Komponenten von geformten Reinigungsmitteln auf Basis von synthetischen Waschrohstoffen zu verwenden. Aus DE-AS 12 31 376 war der Zusatz von Dialkalisalzen von Alpha-Sulfofettsäuren mit 12 bis 18 C-Atomen zu Reinigungsmittelstücken auf Basis von Alkali-acylisäthionaten bekannt. In DE-AS 16 17 220 wird der Zusatz von Alpha-Sulfofettsäure-Alkalisalzen zu synthetischen Detergensstücken auf Basis von Alpha-Olefinsulfonaten beschrieben. Aus DE-OS 24 03 895 war die Verwendung von Alpha-Sulfofettsäure(C₈-C₁₆)-Alkalisalzen als Tensidgrundlage für schwach saure Syndet-Toiletteseifen bekannt. In US 2,915,473 wird eine Kombination von 35 bis 45 Gew.-% Talgalkoholsulfat und 55 bis 65 Gew.-% Alpha-Sulfotalgfettsäure als Grundlage für Detergensstücke vorgeschlagen. In US-PS 3,503,888 schließlich wird Alpha-Sulfopalmitinsäure-Natriumsalz als Kalkseifendispergator in Detergensstücken auf Basis von Kokosfettsäure-phenolestersulfonaten und Kokosfettsäureseife vorgeschlagen.It is also known to use alpha-sulfofatty acid salts as components of shaped cleaning agents based on synthetic detergent raw materials. DE-AS 12 31 376 was the addition of dialkali salts of alpha-sulfo fatty acids with 12 to 18 C atoms known for cleaning agent pieces based on alkali acylisäthionaten. DE-AS 16 17 220 describes the addition of alpha-sulfofatty acid alkali salts to synthetic detergent pieces based on alpha-olefin sulfonates. From DE-OS 24 03 895 the use of alpha-sulfofatty acid (C₈-C₁₆) alkali salts as a surfactant base for weakly acidic Syndet toilet soaps was known. US Pat. No. 2,915,473 proposes a combination of 35 to 45% by weight tallow alcohol sulfate and 55 to 65% by weight alpha-sulfotallow fatty acid as the basis for detergent pieces. Finally, US Pat. No. 3,503,888 proposes the sodium sulfopalmitic acid sodium salt as a lime soap dispersant in detergent bars based on coconut fatty acid phenol ester sulfonates and coconut fatty acid soap.
Die vorliegende Erfindung beruht auf der Beobachtung, daß sich die Formbarkeit und Glätte von geformten Reinigungsmitteln auf Basis von Natriumalkylsulfat, die als Plastifikatoren und Bindemittel Fettalkohole und Fettsäuren enthalten, durch Zusatz eines Alpha-Sulfofettsäure-Salzes in relativ geringen Mengen merklich verbessern läßt. Gleichzeitig zeigten solche Reinigungsmittel bei der Anwendung ein verbessertes Hautgefühl. Auf der Grundlage dieser Beobachtung konnten die Mengenverhältnisse der Komponenten ermittelt werden, die bezüglich Herstellbarkeit, Festigkeit und Anwendungseigenschaften besonders günstige, geformte Reinigungsmittelzusammensetzung ergeben.The present invention is based on the observation that the formability and smoothness of shaped cleaning agents based on sodium alkyl sulfate, which contain fatty alcohols and fatty acids as plasticizers and binders, can be markedly improved in relatively small amounts by adding an alpha-sulfofatty acid salt. At the same time, such cleaning agents showed an improved skin feel when used. On the basis of this observation, it was possible to determine the proportions of the components which, in terms of manufacturability, strength and application properties, result in a particularly favorable, shaped detergent composition.
Gegenstand der Erfindung sind geformte Reinigungsmittel mit einem Gehalt von 30 bis 70 Gew.-% eines Natrium-alkylsulfats mit 12 bis 18 C-Atomen, das dadurch gekennzeichnet ist, daß zur Verbesserung der Formbarkeit und der Anwendungseigenschaften
5 bis 25 Gew.-% eines Fettalkohols mit 12 bis 18 C-Atomen,
5 bis 25 Gew.-% Palmitin- und/oder Stearinsäure, gegebenenfalls in teilweise verseifter Form und
1 bis 30 Gew.-% eines Alpha-Sulfofettsäure-Salzes der Formel I
5 to 25% by weight of a fatty alcohol with 12 to 18 carbon atoms,
5 to 25 wt .-% palmitic and / or stearic acid, optionally in partially saponified form and
1 to 30% by weight of an alpha-sulfofatty acid salt of the formula I.
Das Natrium-alkylsulfat wird in wasserfreier oder wasserarmer Form, z. B. als sprühgetrocknetes Pulver, als Granulat, in Form von Nadeln oder Nudeln oder in umkristallisierter Form eingesetzt. Es können einheitliche Natrium-alkylsulfate, z. B. Na-laurylsulfat oder Na-Cetylsulfat als Homologengemische eingesetzt werden. Bevorzugt werden Natriumalkylsulfate auf Basis von linearen Fettalkoholen und Fettalkoholfraktionen eingesetzt, die durch Hydrierung pflanzlicher oder tierischer Fettsäurefraktionen erhalten werden, z. B. Natrium-kokosfettalkohol(C₁₂-C₁₈)-sulfat oder Natrium-talgalkohol(C₁₆-C₁₈)-sulfat.The sodium alkyl sulfate is in anhydrous or low-water form, e.g. B. as a spray-dried powder, as granules, in the form of needles or noodles or in recrystallized form. Uniform sodium alkyl sulfates, e.g. B. Na lauryl sulfate or Na cetyl sulfate can be used as homolog mixtures. Sodium alkyl sulfates based on linear fatty alcohols and fatty alcohol fractions, which are obtained by hydrogenating vegetable or animal fatty acid fractions, e.g. B. sodium coconut fatty alcohol (C₁₂-C₁₈) sulfate or sodium tallow alcohol (C₁₆-C₁₈) sulfate.
Auch die Fettalkohole mit 12 bis 18 C-Atomen können als einheitliche Alkohole oder als Homologengemische eingesetzt werden, z. B. in der Zusammensetzung wie sie durch Hydrierung pflanzlicher oder tierische Fettsäurefraktionen gewonnen werden, z. B. Kokosfettalkohol C₁₂-C₁₈ oder Talgalkohol. Bevorzugt eignen sich gesättigte Fettalkohole mit 16 bis 18 C-Atomen, z. B. Cetyl-Stearylalkoholfraktionen.The fatty alcohols with 12 to 18 carbon atoms can also be used as uniform alcohols or as homolog mixtures, e.g. B. in the composition as obtained by hydrogenation of vegetable or animal fatty acid fractions, for. B. coconut oil alcohol C₁₂-C₁₈ or tallow alcohol. Saturated fatty alcohols with 16 to 18 carbon atoms, e.g. B. Cetyl-stearyl alcohol fractions.
Die Palmitinsäure und Stearinsäure können in reiner Form oder als Gemisch eingesetzt werden. Obwohl eine Verseifung an sich nicht erforderlich ist, kann es nützlich sein, zur Verhinderung der Zersetzung des Alkylsulfats beim Mischen der Komponenten im Kneter unter erhöhter Temperatur eine geringe Menge eines Alkalihydroxids einzusetzen. Dabei kann ein geringer Teil der Palmitin- und/oder Stearinsäure verseift werden. Es sollte aber dafür Sorge getragen werden, daß nicht mehr als 50 % der Fettsäure verseift wird.The palmitic acid and stearic acid can be used in pure form or as a mixture. Although saponification per se is not required, it may be useful to prevent the decomposition of the alkyl sulfate when mixing the components in the Kneaders use a small amount of an alkali metal hydroxide at elevated temperature. A small part of the palmitic and / or stearic acid can be saponified. However, care should be taken to ensure that no more than 50% of the fatty acid is saponified.
Alpha-Sulfofettsäuresalze der Formel I sind literaturbekannt. Die Herstellung von Alpha-Sulfopalmitinsäure-di-natriumsalz und dessen Homologen aus Laurin-, Myristin- und Stearinsäure sowie deren Eigenschaften sind z. B. in J. Am. Oil Chem. Soc., May 1952, Seiten 198 bis 201 beschrieben. Auf analoge Weise lassen sich auch andere Alpha-Sulfofettsäure-Salze der Formel I, z. B. die Ammonium- und Alkanolammonium-Salze, herstellen, wenn man zur Neutralisation die entsprechenden Basen verwendet. Geeignete Alkanolamine sind z. B. Mono-, Di- und Triethanolamin oder Mono-, Di- oder Triisopropanolamin. Auch die Herstellung gemischter Salze, z. B. der Natrium-Triethanolammonium-Mischsalze kann analog erfolgen, indem man die Neutralisation mit 1 Mol Natriumhydroxid und 1 Mol Triethanolamin pro Mol Alpha-Sulfofettsäure durchführt. Auch "saure" Salze der Alpha-Sulfofettsäuren sind durch Neutralisation mit nur 1 Mol der Base herstellbar.Alpha sulfofatty acid salts of formula I are known from the literature. The production of alpha-sulfopalmitic acid disodium salt and its homologues from lauric, myristic and stearic acid and their properties are e.g. B. in J. Am. Oil Chem. Soc., May 1952, pages 198 to 201. In an analogous manner, other alpha-sulfofatty acid salts of the formula I, e.g. B. the ammonium and alkanolammonium salts, if you use the appropriate bases for neutralization. Suitable alkanolamines are e.g. B. mono-, di- and triethanolamine or mono-, di- or triisopropanolamine. The production of mixed salts, e.g. B. the sodium-triethanolammonium mixed salts can be carried out analogously by carrying out the neutralization with 1 mole of sodium hydroxide and 1 mole of triethanolamine per mole of alpha-sulfofatty acid. "Acid" salts of alpha-sulfo fatty acids can also be prepared by neutralization with only 1 mol of the base.
Neben den genannten obligatorischen Komponenten können die erfindungsgemäßen geformten Reinigungsmittel weitere geeignete Tenside enthalten. Eine bevorzugte Stellung nehmen dabei die Sulfobernsteinsäure-monoalkyl(C₈-C₁₈)-ester-dinatriumsalze ein. Diese können in Mengen bis zu 35 Gew.-%, bevorzugt in Mengen von 5 bis 25 Gew.-% enthalten sein. Die Sulfobernsteinsäuremonoalkylester werden nach bekannten Verfahren dadurch hergestellt, daß man Maleinsäureanhydrid mit einem Fettalkohol mit 8 bis 18 C-Atomen zum Maleinsäure-monoester des Fettalkohols umsetzt und diesen mit Natriumsulfit zum Sulfobernsteinsäureester sulfitiert.In addition to the compulsory components mentioned, the shaped cleaning agents according to the invention can contain further suitable surfactants. A preferred position are the sulfosuccinic acid monoalkyl (C₈-C₁₈) ester disodium salts. These can be contained in amounts of up to 35% by weight, preferably in amounts of 5 to 25% by weight. The sulfosuccinic acid monoalkyl esters are prepared by known processes by reacting maleic anhydride with a fatty alcohol having 8 to 18 carbon atoms to form the maleic acid monoester of the fatty alcohol and sulfitating it with sodium sulfite to the sulfosuccinic acid ester.
Weitere bekannte Tenside und Hilfsmittel können in Mengen bis zu 20 Gew.-% enthalten sein. Solche gegebenenfalls enthaltenen Tenside und Hilfsmittel, die sich zum Einsatz in die erfindungsgemäß geformten Reinigungsmittel besonders eignen, sind z. B.
- anionische Tenside, z. B. Alpha-Olefinsulfonate mit 15 bis 18 C-Atomen, Acylsarkosine, Acylisethionate und Acyltaurine mit jeweils 8 bis 18 C-Atomen in der Acylgruppe, Alkyl(C₈-C₁₈)-phosphate und Acylcyanamide mit 8 bis 18 C-Atomen in der Acylgruppe,
- nichtionogene Tenside, z. B. Fettsäuremono- und diglyceride, Sorbitanfettsäureester, Fettsäurealkanolamide und Ethylenoxidanlagerungsprodukte an diese Verbindungen, weiterhin Anlagerungsprodukte von Ethylenoxid- und/oder Propylenoxid an Fettalkohole mit 8 bis 22 C-Atomen, an C₁₂-C₁₈-Fettamine, an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe. Weitere geeignete nichtionische Tenside sind Zucker-Fettsäureester, Alkylglucoside und Alkyloligoglucoside mit 8 bis 18 C-Atomen in der Alkylgruppe und Methylglucosid-Fettsäure-Partialester sowie deren Ethylenoxidanlagerungsprodukte,
- ampholytische Tenside, z. B. 2-Alkyl(C₈-C₁₈)-aminopropionsäure, Alkyl(C₈-C₁₈)-aminoessigsäure,
- zwitterionische Tenside wie z. B. N-Alkyl(C₈-C₁₈)-dimethylammonio-glycinat, Alkyl(C₈-C₁₈)-aminopropyl-dimethylammonio-glycinat, Alkyl(C₈-C₁₈)-3-carboxymethyl-3-hydroxyethyl-imidazolin,
- organische Füll- und Hilfsstoffe wie z. B. Stärke, Dextrin, Carboxymethylcellulose, Sorbit, Mannit, Harnstoff, Proteine und Proteinhydrolysate, Polyethylenglykole, Paraffin,
- anorganische Füll- und Hilfsstoffe wie z. B. Natriumsulfat, Natriumhydrogenphosphat, Natriumhydrogencarbonat, Schichtsilikate (z. B. Bentonit, Montmorillonit), Zeolithe (z. B. Zeolith A), Wasserglas,
- Komplexbildner,
- antimikrobielle Stoffe, Konservierungsmittel,
- Farbstoffe,
- Trübungs- und Mattierungsmittel, z. B. Pigmente wie Titandioxid,
- Duftstoffe.Other known surfactants and auxiliaries can be contained in amounts of up to 20% by weight. Such surfactants and auxiliaries, if any, which are particularly suitable for use in the cleaning agents shaped according to the invention are, for. B.
- anionic surfactants, e.g. B. Alpha-olefin sulfonates with 15 to 18 carbon atoms, acyl sarcosines, acyl isethionates and acyl taurines each with 8 to 18 carbon atoms in the acyl group, alkyl (C₈-C₁₈) phosphates and acyl cyanamides with 8 to 18 carbon atoms in the acyl group ,
- non-ionic surfactants, e.g. B. fatty acid mono- and diglycerides, sorbitan fatty acid esters, fatty acid alkanolamides and ethylene oxide addition products to these compounds, further addition products of ethylene oxide and / or propylene oxide to fatty alcohols with 8 to 22 carbon atoms, to C₁₂-C₁₈ fatty amines, to alkylphenols with 8 to 15 C- Atoms in the alkyl group. Other suitable nonionic surfactants are sugar fatty acid esters, alkyl glucosides and alkyl oligoglucosides with 8 to 18 carbon atoms in the alkyl group and methyl glucoside fatty acid partial esters and their ethylene oxide addition products,
- ampholytic surfactants, e.g. B. 2-alkyl (C₈-C₁₈) aminopropionic acid, alkyl (C₈-C₁₈) aminoacetic acid,
- zwitterionic surfactants such as B. N-alkyl (C₈-C₁₈) -dimethylammonio-glycinate, alkyl (C₈-C₁amin) -aminopropyl-dimethylammonio-glycinate, alkyl (C₈-C₁₈) -3-carboxymethyl-3-hydroxyethyl-imidazoline,
- organic fillers and auxiliaries such. B. starch, dextrin, carboxymethyl cellulose, sorbitol, mannitol, urea, proteins and protein hydrolyzates, polyethylene glycols, paraffin,
- inorganic fillers and auxiliaries such. B. sodium sulfate, sodium hydrogen phosphate, sodium hydrogen carbonate, layered silicates (e.g. bentonite, montmorillonite), zeolites (e.g. zeolite A), water glass,
- complexing agents,
- antimicrobials, preservatives,
- dyes,
- opacifiers and matting agents, e.g. B. pigments such as titanium dioxide,
- fragrances.
In einer besonders bevorzugten Ausführungsform enthalten die erfindungsgemäß geformten Reinigungsmittel
40 bis 60 Gew.-% Alkyl(C₁₀-C₁₈)-sulfat, Natriumsalz
10 bis 20 Gew.-% Cetyl und/oder Stearylalkohol
10 bis 20 Gew.-% einer gegebenenfalls teilweise verseiften Palmitin- und/oder Stearinsäure
5 bis 20 Gew.-% eines Alpha-Sulfofettsäure-Salzes der Formel I und
0 bis 20 Gew.-% weiterer bekannter Tenside und Hilfsmittel.In a particularly preferred embodiment, the cleaning agents shaped according to the invention contain
40 to 60 wt .-% alkyl (C₁₀-C₁₈) sulfate, sodium salt
10 to 20% by weight of cetyl and / or stearyl alcohol
10 to 20% by weight of an optionally partially saponified palmitic and / or stearic acid
5 to 20 wt .-% of an alpha-sulfofatty acid salt of the formula I and
0 to 20% by weight of other known surfactants and auxiliaries.
Die Herstellung der erfindungsgemäß geformten Reinigungsmittel kann in der für solche Produkte üblichen Weise erfolgen, wobei durch die erfindungsgemäße Kombination von Zusätzen eine besonders gut formbare, in der Wärme plastische und nach dem Erkalten harte Masse entsteht und wobei die geformten Produkte eine glatte Oberfläche aufweisen. Übliche Verfahren zum Mischen bzw. Homogenisieren, Kneten, gegebenenfalls Pilieren, Strangpressen, gegebenenfalls Pelletieren, Extrudieren, Schneiden und Stückpressen, wie sie in der bereits oben zitierten Publikation in JAOCS, Vol. 59, No. 10 (Oktober 1982) beschrieben sind, können für die Herstellung der erfindungsgemäß geformten Reinigungsmittel verwendet werden. Für die Herstellung von handlichen Syndet-Seifenstücken hat sich die folgende Verfahrensweise besonders bewährt:The cleaning agents shaped in accordance with the invention can be produced in the manner customary for such products, the combination of additives according to the invention resulting in a particularly readily formable mass which is plastic in the heat and hard after cooling, and in which the shaped products have a smooth surface. Usual methods for mixing or homogenizing, kneading, optionally pelleting, extrusion, optionally pelleting, extruding, cutting and pressing, as described in the publication cited above in JAOCS, Vol. 59, No. 10 (October 1982) can be used for the production of the cleaning agents shaped according to the invention. The following procedure has proven particularly useful for the production of handy Syndet soap bars:
Die schmelzbaren Komponenten, z. B. der Fettalkohol, die Palmitin- und/oder Stearinsäure und gegebenenfalls nichtionogene Tenside oder schmelzbare organische Füll- und Hilfsstoffe werden bei Temperaturen von 60 bis 90 °C in einem heizbaren Kneter oder Mischer aufgeschmolzen und gegebenenfalls nach Zusatz einer geringen Menge einer Alkalihydroxidlösung gemischt. Dann erfolgt die Zugabe des Natriumalkylsulfats und gegebenenfalls anderer bei 60 bis 90 °C nicht schmelzbarer Komponenten und einer Wassermenge, die den Gesamtwassergehalt des Ansatzes auf etwa 5 bis 15 Gew.-% H₂O einstellt, sowie eine Vermischung oder Verknetung des Ansatzes bei einer Temperatur von ca. 40 bis 70 °C. Eine weitere Homogensierung läßt sich dadurch erreichen, daß die Masse bei 40 bis 70 °C mehrfach durch Siebe gepreßt und schließlich bei einer Kopftemperatur von 40 bis 70 °C zu einem Strang verpreßt wird, der zu gleichmäßigen Stücken geschnitten wird. Die Stücke können schließlich in einer Formpresse in eine endgültige Form gebracht werden. Anstelle der Strangpresse kann auch eine Extrusion durch eine Lochplatte erfolgen, wobei die erfindungsgemäßen Reinigungsmittel nach dem Erkalten in Form von Nadeln oder, wenn der Lochplatte Messer nachgeschaltet sind, in Form von Granulaten erhalten werden.The fusible components, e.g. B. the fatty alcohol, the palmitic and / or stearic acid and optionally nonionic surfactants or meltable organic fillers and auxiliaries are melted at temperatures of 60 to 90 ° C in a heatable kneader or mixer and optionally mixed after adding a small amount of an alkali metal hydroxide solution. Then the addition of the sodium alkyl sulfate and optionally other components which cannot be melted at 60 to 90 ° C. and a quantity of water which adjusts the total water content of the batch to about 5 to 15% by weight of H 2 O, as well as mixing or kneading of the batch at a temperature of approx. 40 to 70 ° C. A further homogenization can be achieved in that the mass is pressed through sieves several times at 40 to 70 ° C and finally pressed at a head temperature of 40 to 70 ° C into a strand which is cut into uniform pieces. The pieces can finally be brought into a final shape in a molding press. Instead of the extrusion press, extrusion can also take place through a perforated plate, the cleaning agents according to the invention being obtained after cooling in the form of needles or, if the perforated plate is followed by knives, in the form of granules.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn hierauf zu beschränken.
Cetyl-Stearylalkohol, Palmitin-Stearinsäure und gegebenenfalls Hydrotalgalkoholoxethylat wurden in einem Kneter bei 70 °C geschmolzen. Dann wurde die auf 60 °C erwärmte KOH-Lösung zugegeben und 30 Minuten geknetet. Dann wurden das Fettalkoholsulfat, das Sulfobernsteinsäureestersalz, das Alpha-Sulfofettsäure-Salz und das Wasser zugesetzt. Nach ca. 1 Stunde weiteren Knetens wurde der Wassergehalt einer Probe bestimmt und durch weitere Wasserzugabe ein Gesamt-Wassergehalt von 11 Gew.-% eingestellt und noch weitere 30 Minuten geknetet. Nach Abkühlung der Masse auf 45 °C wurde diese in eine Doppelschnecken-Strangpresse überführt, pelletiert, zweimal durch ein 0,25-mm-Sieb gedrückt, extrudiert und bei einer Kopftemperatur von 50 °C zum Strang verpreßt, in Stücke geschnitten und in einer Formpresse zur fertigen Stückseife verarbeitet. Es wurden glatte, feste Syndet-Seifenstücke erhalten.Cetyl stearyl alcohol, palmitin stearic acid and optionally hydrotalg alcohol oxyethylate were melted in a kneader at 70 ° C. Then the KOH solution heated to 60 ° C. was added and kneaded for 30 minutes. Then the fatty alcohol sulfate, the sulfosuccinic acid ester salt, the alpha-sulfo fatty acid salt and the water were added. After about 1 hour of further kneading, the water content of a sample was determined and a total water content of 11% by weight was set by adding more water and kneading for a further 30 minutes. After the mass had cooled to 45 ° C., it was transferred to a twin-screw extruder, pelletized, pressed twice through a 0.25 mm sieve, extruded and at a head temperature of 50 ° C. to Pressed strand, cut into pieces and processed in a molding press to the finished bar soap. Smooth, solid Syndet bars of soap were obtained.
Claims (3)
5 bis 25 Gew.-% eines Fettalkohols mit 12 bis 18 C-Atomen,
5 bis 25 Gew.-% Palmitin- und/oder Stearinsäure, gegebenenfalls in teilweise verseifter Form und
1 bis 30 Gew.-% eines Alpha-Sulfofettsäure-Salzes der Formel (I)
5 to 25% by weight of a fatty alcohol with 12 to 18 carbon atoms,
5 to 25 wt .-% palmitic and / or stearic acid, optionally in partially saponified form and
1 to 30% by weight of an alpha-sulfofatty acid salt of the formula (I)
40 bis 60 Gew.-% Alkyl(C₁₀-C₁₈)-sulfat, Natriumsalz
10 bis 20 Gew.-% Cetyl- und/oder Stearylalkohol
10 bis 20 Gew.-% einer gegebenenfalls teilweise verseiften Palmitin- und/oder Stearinsäure
5 bis 20 Gew.-% eines Alpha-Sulfofettsäure-Salzes der Formel I gemäß Anspruch 1 und
0 bis 20 Gew.-% weiterer bekannter Tenside und Hilfsmittel
enthalten sind.3. Shaped cleaning agent according to claims 1 or 2, characterized in that
40 to 60 wt .-% alkyl (C₁₀-C₁₈) sulfate, sodium salt
10 to 20 wt .-% cetyl and / or stearyl alcohol
10 to 20% by weight of an optionally partially saponified palmitic and / or stearic acid
5 to 20 wt .-% of an alpha-sulfofatty acid salt of the formula I according to claim 1 and
0 to 20% by weight of other known surfactants and auxiliaries
are included.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3707035 | 1987-03-05 | ||
| DE19873707035 DE3707035A1 (en) | 1987-03-05 | 1987-03-05 | MOLDED DETERGENTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0281028A2 true EP0281028A2 (en) | 1988-09-07 |
| EP0281028A3 EP0281028A3 (en) | 1990-01-17 |
Family
ID=6322316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88102884A Withdrawn EP0281028A3 (en) | 1987-03-05 | 1988-02-26 | Shaped detergent |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4861508A (en) |
| EP (1) | EP0281028A3 (en) |
| JP (1) | JPS63230799A (en) |
| KR (1) | KR880011317A (en) |
| DE (1) | DE3707035A1 (en) |
| PH (1) | PH23568A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991019775A1 (en) * | 1990-06-15 | 1991-12-26 | Henkel Kommanditgesellschaft Auf Aktien | Use of salts of the sulphonation products of unsaturated fatty acids as viscosity reducers |
| WO1992007931A1 (en) * | 1990-10-30 | 1992-05-14 | The Procter & Gamble Company | Syndet bar with long chain alkyl sulfates for improved processability and bar characteristics |
| WO1992016610A1 (en) * | 1991-03-21 | 1992-10-01 | The Procter & Gamble Company | Mild personal cleansing bars with improved processability |
| WO1992013060A3 (en) * | 1991-01-28 | 1992-10-15 | Procter & Gamble | Binder systems for bar soaps |
| WO1993006205A1 (en) * | 1991-09-23 | 1993-04-01 | The Procter & Gamble Company | Mild personal cleansing bar composition with balanced surfactants, fatty acids, and paraffin wax |
| GB2278124A (en) * | 1993-05-17 | 1994-11-23 | Unilever Plc | Detergent composition |
| GB2278125A (en) * | 1993-05-17 | 1994-11-23 | Unilever Plc | Detergent composition |
| WO1995018214A1 (en) * | 1993-12-30 | 1995-07-06 | Ecolab Inc. | Method of making non-caustic solid cleaning compositions |
| WO1999020729A1 (en) * | 1997-10-21 | 1999-04-29 | Stepan Company | Soap bar compositions comprising alpha sulfonated fatty acid alkyl esters and long chain fatty acids |
| US6673765B1 (en) | 1995-05-15 | 2004-01-06 | Ecolab Inc. | Method of making non-caustic solid cleaning compositions |
| EP3272328A1 (en) * | 2016-07-19 | 2018-01-24 | Basf Se | Aqueous tenside compositions |
| WO2020094244A1 (en) | 2018-11-08 | 2020-05-14 | Symrise Ag | An antimicrobial surfactant based composition |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3827778A1 (en) * | 1988-08-16 | 1990-02-22 | Henkel Kgaa | PASTE-SHAPED DETERGENT AND CLEANING AGENT AND METHOD FOR PRODUCING THE SAME |
| US5391315A (en) * | 1991-09-27 | 1995-02-21 | Ashkin; Abraham | Solid cake detergent carrier composition |
| US5968892A (en) * | 1994-06-17 | 1999-10-19 | Hutchins; James Peyton | Non-brittle laundry bars comprising coconut alkyl sulfate and polyethylene glycol |
| KR980002224A (en) * | 1996-06-29 | 1998-03-30 | 이능희 | Synthetic Detergent Bar Composition Containing Alpha Sulfo Fatty Acid Diphosphate |
| US6458751B1 (en) * | 2001-07-23 | 2002-10-01 | Unilever Home & Personal Care Usa | Skin cleansing bar comprising a fatty alcohol with low mush |
| US20060003908A1 (en) * | 2004-07-01 | 2006-01-05 | Brennan Michael A | Mild synthetic detergent toilet bar composition |
| WO2012138685A1 (en) | 2011-04-04 | 2012-10-11 | The Procter & Gamble Company | Personal care article |
| WO2013025764A1 (en) | 2011-08-15 | 2013-02-21 | The Procter & Gamble Company | Personal care articles having multi-zone compliant personal care compositions |
| CN104202987B (en) | 2011-08-15 | 2017-09-01 | 宝洁公司 | Personal nursing method |
| US9554978B2 (en) | 2013-06-27 | 2017-01-31 | The Procter & Gamble Company | Personal care articles |
| EP3246010A1 (en) * | 2016-05-18 | 2017-11-22 | Basf Se | Aqueous tenside compositions |
| EP3252132A1 (en) | 2016-05-30 | 2017-12-06 | Basf Se | Aqueous tenside compositions |
| ES3023259T3 (en) * | 2019-05-07 | 2025-05-30 | Basf Se | Aqueous surfactant compositions and soap bars |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2915473A (en) * | 1956-04-17 | 1959-12-01 | Alexander J Stirton | Detergent compositions |
| GB954833A (en) * | 1960-02-23 | 1964-04-08 | Unilever Ltd | Detergent tablets |
| US3503888A (en) * | 1965-02-16 | 1970-03-31 | Dow Chemical Co | Synthetic detergent bar |
| GB1171617A (en) * | 1966-03-18 | 1969-11-26 | Unilever Ltd | Toilet Bar |
| BE756790A (en) * | 1969-10-01 | 1971-03-29 | Henkel & Cie Gmbh | DETERGENT FORMED WITH SYNTHETIC SURFACTANTS |
| DE2403895A1 (en) * | 1973-02-01 | 1974-08-15 | Unilever Nv | BAR OF SOAP |
| US3989647A (en) * | 1973-04-26 | 1976-11-02 | Lever Brothers Company | Quick lathering toilet bars and method of making same |
| IL61158A0 (en) * | 1980-02-19 | 1980-11-30 | Witco Chemical Corp | Synthetic detergent compositions and their preparation |
| US4543204A (en) * | 1983-08-17 | 1985-09-24 | Colgate-Palmolive Company | Sodium higher fatty alkyl sulfate detergent laundry bars and process for manufacture thereof |
-
1987
- 1987-03-05 DE DE19873707035 patent/DE3707035A1/en not_active Withdrawn
-
1988
- 1988-02-26 EP EP88102884A patent/EP0281028A3/en not_active Withdrawn
- 1988-03-03 PH PH36588A patent/PH23568A/en unknown
- 1988-03-04 US US07/164,157 patent/US4861508A/en not_active Expired - Fee Related
- 1988-03-05 KR KR1019880002354A patent/KR880011317A/en not_active Withdrawn
- 1988-03-05 JP JP63052476A patent/JPS63230799A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991019775A1 (en) * | 1990-06-15 | 1991-12-26 | Henkel Kommanditgesellschaft Auf Aktien | Use of salts of the sulphonation products of unsaturated fatty acids as viscosity reducers |
| TR27389A (en) * | 1990-10-30 | 1995-02-03 | Procter & Gamble | Synthetic detergent mold containing long chain alkyl sulphates for improved processability and texture properties. |
| WO1992007931A1 (en) * | 1990-10-30 | 1992-05-14 | The Procter & Gamble Company | Syndet bar with long chain alkyl sulfates for improved processability and bar characteristics |
| WO1992013060A3 (en) * | 1991-01-28 | 1992-10-15 | Procter & Gamble | Binder systems for bar soaps |
| WO1992016610A1 (en) * | 1991-03-21 | 1992-10-01 | The Procter & Gamble Company | Mild personal cleansing bars with improved processability |
| TR26617A (en) * | 1991-09-23 | 1995-03-15 | Procter & Gamble | SOFT PERSONAL CLEANER PATTERN REFLECTED WITH BALANCED SURFACE ACTIVE SUBSTANCES, FATTY ACIDS AND PARAFIN. |
| WO1993006205A1 (en) * | 1991-09-23 | 1993-04-01 | The Procter & Gamble Company | Mild personal cleansing bar composition with balanced surfactants, fatty acids, and paraffin wax |
| GB2278125A (en) * | 1993-05-17 | 1994-11-23 | Unilever Plc | Detergent composition |
| GB2278124A (en) * | 1993-05-17 | 1994-11-23 | Unilever Plc | Detergent composition |
| WO1995018214A1 (en) * | 1993-12-30 | 1995-07-06 | Ecolab Inc. | Method of making non-caustic solid cleaning compositions |
| US6060444A (en) * | 1993-12-30 | 2000-05-09 | Ecolab Inc. | Method of making non-caustic solid cleaning compositions |
| US6673765B1 (en) | 1995-05-15 | 2004-01-06 | Ecolab Inc. | Method of making non-caustic solid cleaning compositions |
| WO1999020729A1 (en) * | 1997-10-21 | 1999-04-29 | Stepan Company | Soap bar compositions comprising alpha sulfonated fatty acid alkyl esters and long chain fatty acids |
| US6172026B1 (en) | 1997-10-21 | 2001-01-09 | Stepan Company | Soap bar compositions comprising alpha sulfonated fatty acid alkyl esters and long chain fatty acids |
| EP3272328A1 (en) * | 2016-07-19 | 2018-01-24 | Basf Se | Aqueous tenside compositions |
| WO2018015035A1 (en) * | 2016-07-19 | 2018-01-25 | Basf Se | Aqueous surfactant compositions |
| WO2020094244A1 (en) | 2018-11-08 | 2020-05-14 | Symrise Ag | An antimicrobial surfactant based composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR880011317A (en) | 1988-10-27 |
| EP0281028A3 (en) | 1990-01-17 |
| PH23568A (en) | 1989-09-11 |
| DE3707035A1 (en) | 1988-09-15 |
| JPS63230799A (en) | 1988-09-27 |
| US4861508A (en) | 1989-08-29 |
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