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WO1995019416A1 - Aqueous solutions of quaternary fatty acid triethanolamine ester salts - Google Patents

Aqueous solutions of quaternary fatty acid triethanolamine ester salts Download PDF

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Publication number
WO1995019416A1
WO1995019416A1 PCT/EP1995/000047 EP9500047W WO9519416A1 WO 1995019416 A1 WO1995019416 A1 WO 1995019416A1 EP 9500047 W EP9500047 W EP 9500047W WO 9519416 A1 WO9519416 A1 WO 9519416A1
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WO
WIPO (PCT)
Prior art keywords
aqueous solutions
fatty acid
ester salts
weight
esters
Prior art date
Application number
PCT/EP1995/000047
Other languages
German (de)
French (fr)
Inventor
Nuria Bonastre
Joaquim Bigorra Llosas
Jörg KAHRE
Hermann Hensen
Holger Tesmann
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP7518816A priority Critical patent/JPH09508106A/en
Priority to EP95906310A priority patent/EP0739409A1/en
Publication of WO1995019416A1 publication Critical patent/WO1995019416A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/18—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters

Definitions

  • the invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts containing fatty acid oligoglycerol esters as thickeners, agents containing these components and the use of fatty acid oligoglycerol esters as thickeners for aqueous solutions of quaternized fatty acid triethanolamine ester salts.
  • Quaternized fatty acid triethanolamine ester salts so-called “esterquats” have become increasingly important in recent years as ecotoxicologically safe raw materials for fabric softeners.
  • the products are usually marketed as alcoholic concentrates and are diluted with water by the manufacturers of conditioning agents to a user concentration which, depending on requirements, can be in the range from 1 to 50% by weight of solids.
  • Viscosity problems arise both in the production of ester quat concentrates and in the formulation of the aqueous compositions which can contain these cationic surfactants in different amounts.
  • Esterquat concentrates with a solids content of approximately 80 to 90% by weight are viscous and require regulators to reduce the viscosity.
  • EP-A2 0 165 138 proposes the use of organic salts such as sodium gluconate or short-chain quaternary ammonium salts.
  • organic salts such as sodium gluconate or short-chain quaternary ammonium salts.
  • ester quats based on unsaturated fatty acids, quaternized fatty acid amidoamine salts, long-chain QAV and diquaternized fatty acid triethanola inester salts are also suitable for this purpose.
  • the object of the invention was therefore to provide aqueous solutions of quaternized fatty acid triethanolamine ester salts with improved viscosity behavior.
  • the invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts, which are characterized in that they are, if appropriate, 0.01 to 0.1, preferably 0.01 to 0.03% by weight, based on the solutions, as viscosity regulators contain alkoxylated esters of fatty acids with technical oligoglycerol mixtures.
  • fatty acid oligoglycerol esters and alkoxylated fatty acid oligoglycerol esters are particularly suitable as thickeners for aqueous solutions of esterquats.
  • the viscosity of the aqueous solutions can easily be raised to a value which enables easy metering.
  • the invention includes the knowledge that the products are stable in storage, i.e. the viscosity level which has been set remains practically unchanged even after prolonged storage.
  • the fact that the fatty acid oligoglycerol esters are only effective as a thickener in the range of very low concentrations is also particularly surprising.
  • Quaternized fatty acid triethanolamine ester salts are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • ester quats are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • esterquats as softening agents for textiles has been described, for example, in the review articles by O.Ponsati in CR CED-Kongress, Barcelona, 167 (1992) and R.Puchta in CR CED-Kongress, Sitges, 59 (1993).
  • R --- C0 for an acyl radical with 6 to 22 carbon atoms
  • R2 and R 3 independently of one another for hydrogen or R --- C0
  • R ⁇ for an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2 ⁇ ) gH- Group
  • m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
  • ester quats which can be used in the context of the invention are products based on capric acid, caprylic acid, capric acid, lauric acid, myristic acid, Palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid as well as their technical mixtures, such as are obtained, for example, in the pressure release of natural fats and oils.
  • industrial Ci2 be l8 ⁇ co ⁇ os f ⁇ ETT acids unc - in particular, partly hydrogenated Ci5 ⁇ g tallow or palm oil fatty acids and elaidic acid-rich CISS / ig fatty cuts used.
  • the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters.
  • an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical Cissig tallow or palm fatty acid (iodine number 0 to 40).
  • quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R --- CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R --- C0, R 3 for hydrogen, R 4 for a methyl group, m, n and p for 0 and X for methyl sulfate.
  • Esterquats are usually marketed as alcoholic concentrates with a solids content of approx. 80 to 90% by weight.
  • the aqueous solutions claimed to be thickened in the sense of the invention usually have Usually a solids content in the range of 1 to 50, preferably 3 to 15 wt .-%.
  • Possible viscosity regulators are alkoxylated esters of fatty acids with technical oligoglycerin chemicals and their addition products of an average of 1 to 10 and preferably 2 to 5 mol of alkylene oxide, which have long been known as such.
  • the viscosity regulators are preferably optionally alkoxylated esters which are derived from fatty acids of the formula (II)
  • R ⁇ CO stands for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1 to 3 double bonds.
  • Typical examples are esters of oligoglycerol mixtures with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, Isotridecan Text- acid, myristic acid, palmitic acid, palmoleic, re Stearinkla ⁇ , isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, gadoleic , Behenic acid and erucic acid and their technical mixtures, which are used, for example, in the pressure splitting of natural fats and oils, the reduction of aldehydes from Roelen's oxosynthesis or the dimerization of unsaturated fatty acids.
  • the viscosity regulators are preferably alkoxylated esters, which are also derived from industrial oligoglycerol mixtures of the formula (III),
  • Typical examples are fatty acid esters with technical oligoglycerol mixtures which have an average degree of self-condensation in the range from 1.5 to 10, preferably 2 to 5.
  • Fatty acid esters based on oligoglycerol mixtures with a high content of di- and triglycerol are particularly preferred.
  • the viscosity regulators are preferably optionally alkoxylated fatty acid oligoglycerol esters which finally have an average degree of esterification of 0.75 to 4. Although the products are generally mixtures of mono-, di-, tri- and optionally oligoesters due to the preparation, those viscosity regulators which have a statistical average of 1 to 3 ester groups are particularly preferred.
  • the alkoxylated esters are preferably addition products of ethylene oxide.
  • the degree of ethoxylation of the esters is usually in the range from 1 to 10 and in particular 2 to 5.
  • diesters of isostearic acid with technical triglycerol are used as viscosity regulators in quantities of 0.01 to 0.03% by weight, based on the solutions.
  • aqueous solutions according to the invention are characterized by an advantageous viscosity which is practically unchanged even after prolonged storage.
  • the invention further relates to aqueous laundry softening agents containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and, if appropriate, others Auxiliaries and additives.
  • the invention further relates to aqueous hair treatment compositions containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight. optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and optionally further auxiliaries and additives.
  • the invention relates to the use of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures as viscosity regulators for aqueous solutions of quaternized fatty acid triethanolamine ester salts, in which they are present in amounts of 0.01 to 0.1% by weight. -% - based on the solutions - may be included.

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Abstract

Aqueous solutions of quaternary fatty acid triethanolamine ester salts may be advantageously and permanently thickened by admixture of 0.01 to 0.1 % by weight (in relation to the solution) of possibly alkoxylated esters of fatty acids with technical oligoglycerine mixtures.

Description

Wäßrige Lösungen von quaternierten Fettsäuretriethanolam nester-Salzen Aqueous solutions of quaternized fatty acid triethanolam ester salts
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salzen mit einem Gehalt an Fett- säureoligoglycerinestern als Verdickungs itteln, Mittel, die diese Komponenten enthalten sowie die Verwendung von Fettsäu- reoligoglycerinestern als Verdickungsmittel für wäßrige Lö¬ sungen von quaternierten Fettsäuretriethanolaminester-Salzen.The invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts containing fatty acid oligoglycerol esters as thickeners, agents containing these components and the use of fatty acid oligoglycerol esters as thickeners for aqueous solutions of quaternized fatty acid triethanolamine ester salts.
Stand der TechnikState of the art
Quaternierte Fettsäuretriethanolaminester-Salze, sogenannte "Esterquats" , haben in den letzten Jahren als ökotoxikolo¬ gisch unbedenkliche Rohstoffe für Wäscheweichspuler zunehmend an Bedeutung gewonnen. Üblicherweise gelangen die Produkte als alkoholische Konzentrate in den Verkehr und werden von den Herstellern von Avivagemitteln mit Wasser auf eine Anwen¬ derkonzentration, die je nach Anforderung im Bereich von 1 bis 50 Gew.-% Feststoff liegen kann, verdünnt. Sowohl bei der Herstellung von Esterquat-Konzentraten, als auch bei der Formulierung der wäßrigen Mittel, die diese kat¬ ionischen Tenside in unterschiedlichen Mengen enthalten kön¬ nen, treten Viskositätsprobleme auf.Quaternized fatty acid triethanolamine ester salts, so-called "esterquats", have become increasingly important in recent years as ecotoxicologically safe raw materials for fabric softeners. The products are usually marketed as alcoholic concentrates and are diluted with water by the manufacturers of conditioning agents to a user concentration which, depending on requirements, can be in the range from 1 to 50% by weight of solids. Viscosity problems arise both in the production of ester quat concentrates and in the formulation of the aqueous compositions which can contain these cationic surfactants in different amounts.
Esterquat-Konzentrate mit einem Feststoffgehalt von etwa 80 bis 90 Gew.-% sind zähflüssig und benötigen als Regulatoren Stoffe, die die Viskosität herabsetzen. In der EP-A2 0 165 138 wird hierzu beispielsweise die Verwendung von organischen Salzen wie etwa Natriumgluconat oder kurzkettigen quartären Ammoniumsalzen vorgeschlagen. Gemäß der Lehre der WO 93/16157 (Henkel) kommen für diesen Zweck auch Esterquats auf Basis ungesättigter Fettsäuren, quatemierte Fettsäureamidoamin- Salze, langkettige QAV und diquaternierte Fettsäuretrietha- nola inester-Salze in Betracht.Esterquat concentrates with a solids content of approximately 80 to 90% by weight are viscous and require regulators to reduce the viscosity. EP-A2 0 165 138, for example, proposes the use of organic salts such as sodium gluconate or short-chain quaternary ammonium salts. According to the teaching of WO 93/16157 (Henkel), ester quats based on unsaturated fatty acids, quaternized fatty acid amidoamine salts, long-chain QAV and diquaternized fatty acid triethanola inester salts are also suitable for this purpose.
Bei wäßrigen Anwendungslösungen der quaternierten Fettsäure- triethanola inester-Salze, die einen geringen Feststoffgehalt aufweisen, liegt das Problem jedoch genau umgekehrt: die wä߬ rigen Lösungen sind äußerst dünnflüssig und lassen sich nur schwer dosieren. Übliche Verdickungsmittel, wie sie aus der Kosmetik bekannt sind (Elektrol te, Celluloseether, Fettsäu- realkanolamide etc.), erweisen sich entweder als wenig ge¬ eignet und/oder sind nicht in der Lage, die Produkte dauer¬ haft auf dem gewünschten Viskositätsniveau zu halten.In the case of aqueous application solutions of the quaternized fatty acid triethanola ester salts which have a low solids content, however, the problem is exactly the opposite: the aqueous solutions are extremely thin and difficult to dose. Usual thickening agents, as are known from cosmetics (electrolytes, cellulose ethers, fatty acid realanolamides, etc.), either prove to be unsuitable and / or are unable to permanently add the products to the desired viscosity level hold.
Die Aufgabe der Erfindung hat somit darin bestanden, wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester- Salzen mit verbessertem Viskositätsverhalten zur Verfügung zu stellen. Beschreibung der ErfindungThe object of the invention was therefore to provide aqueous solutions of quaternized fatty acid triethanolamine ester salts with improved viscosity behavior. Description of the invention
Gegenstand der Erfindung sind wäßrige Lösungen von quater¬ nierten Fettsäuretriethanolaminester-Salzen, die sich dadurch auszeichnen, daß sie als Viskositätsregulatoren 0,01 bis 0,1, vorzugsweise 0,01 bis 0,03 Gew.-% - bezogen auf die Lösungen - gegebenenfalls alkoxylierte Ester von Fettsäuren mit tech¬ nischen Oligoglyceringemischen enthalten.The invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts, which are characterized in that they are, if appropriate, 0.01 to 0.1, preferably 0.01 to 0.03% by weight, based on the solutions, as viscosity regulators contain alkoxylated esters of fatty acids with technical oligoglycerol mixtures.
Überraschenderweise wurde gefunden, daß sich Fettsäureoligo- glycerinester und alkoxylierte Fettsäureoligoglycerinester in besonderer Weise als Verdickungsmittel für wäßrige Lösungen von Esterquats eignen. Bei Zusatz dieser Stoffe kann die Vis¬ kosität der wäßrigen Lösungen problemlos auf einen Wert ange¬ hoben werden, der ein müheloses Dosieren ermöglicht. Die Er¬ findung schließt dabei die Erkenntnis ein, daß die Produkte lagerstabil sind, d.h. das einmal eingestellte Viskositätsni¬ veau bleibt auch bei längerer Lagerung praktisch unverändert erhalten. Als besonders überraschend ist ferner die Tatsache zu bewerten, daß die Fettsäureoligoglycerinester nur im Be¬ reich sehr niedriger Konzentrationen als Verdickungsmittel wirksam sind.It has surprisingly been found that fatty acid oligoglycerol esters and alkoxylated fatty acid oligoglycerol esters are particularly suitable as thickeners for aqueous solutions of esterquats. When these substances are added, the viscosity of the aqueous solutions can easily be raised to a value which enables easy metering. The invention includes the knowledge that the products are stable in storage, i.e. the viscosity level which has been set remains practically unchanged even after prolonged storage. The fact that the fatty acid oligoglycerol esters are only effective as a thickener in the range of very low concentrations is also particularly surprising.
Quaternierte Fettsäuretriethanolaminester-SalzeQuaternized fatty acid triethanolamine ester salts
Quaternierte Fettsäuretriethanolaminester-Salze ("Ester¬ quats") stellen bekannte Stoffe dar, die man nach den ein¬ schlägigen Methoden der präparativen organischen Chemie er¬ halten kann. In diesem Zusammenhang sei auf die Internatio¬ nale Patentanmeldung WO 91/01 295 (Henkel) verwiesen, nach der man Triethanolamin in Gegenwart von unterphosphoriger Säure mit Fettsäuren partiell verestert, Luft durchleitet und anschließend mit Dimethylsulfat 'oder Ethylenoxid quaterniert. Stellvertretend für den umfangreichen Stand der Technik sei an dieser Stelle auf die Druckschriften OS 3915867, US 4370272, EP-A2 0239910, EP-A2 0293955, EP-A2 0295739 und EP-A2 309052 verwiesen. Die Verwendung von Esterquats als Avivagemittel für Textilien ist beispielsweise in den Über¬ sichtsartikeln von O.Ponsati in C.R. CED-Kongress, Barcelona, 167 (1992) und R.Puchta in C.R. CED-Kongress, Sitges, 59 (1993) beschrieben worden.Quaternized fatty acid triethanolamine ester salts ("ester quats") are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the international patent application WO 91/01 295 (Henkel), after which triethanolamine in the presence of hypophosphorous acid partially esterified with fatty acids, air is passed through and then quaternized with dimethyl sulfate 'or ethylene oxide. As a representative of the extensive state of the art, reference is made to the documents OS 3915867, US 4370272, EP-A2 0239910, EP-A2 0293955, EP-A2 0295739 and EP-A2 309052. The use of esterquats as softening agents for textiles has been described, for example, in the review articles by O.Ponsati in CR CED-Kongress, Barcelona, 167 (1992) and R.Puchta in CR CED-Kongress, Sitges, 59 (1993).
Die quaternierten Fettsäuretriethanolaminester-Salze folgen der Formel (I)The quaternized fatty acid triethanolamine ester salts follow the formula (I)
R4R4
[R1CO-(OCH2CH2)mOCH2CH2- -CH2CH2θ-(CH2CH2θ)nR2] X" (I)[R 1 CO- (OCH2CH2) m OCH2CH2- -CH2CH2θ- (CH2CH2θ) n R 2 ] X "(I)
II.
CH2CH20(CH2CH20)pR3 CH2CH 2 0 (CH 2 CH 2 0) pR 3
in der R---C0 für einen Acylrest mit 6 bis 22 Kohlenstoffato- men, R2 und R3 unabhängig voneinander für Wasserstoff oder R---C0, R^ für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen oder eine (CH2CH2θ)gH-Gruppe, m, n und p in Summe für 0 oder Zahlen von 1 bis 12, q für Zahlen von 1 bis 12 und X für Ha- logenid, Alkylsulfat oder Alkylphosphat steht.in which R --- C0 for an acyl radical with 6 to 22 carbon atoms, R2 and R 3 independently of one another for hydrogen or R --- C0, R ^ for an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2θ) gH- Group, m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
Typische Beispiele für Esterquats, die im Sinne der Erfindung Verwendung finden können, sind Produkte auf Basis von Capron- säure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Isostearinsäure, Stearinsäure, Ölsäure, Elai- dinsäure, Arachinsäure, Behensäure und Erucasäure sowie deren technische Mischungen, wie sie beispielweise bei der Druck¬ spaltung natürlicher Fette und Öle anfallen. Vorzugsweise werden technische Ci2 l8~Ko^os-fetts^uren unc-- insbesondere teilgehärtete Ci5 ιg-Talg- bzw. Palmfettsäuren sowie elaidin- säurereiche Ciß/ig-Fettsäureschnitte eingesetzt.Typical examples of ester quats which can be used in the context of the invention are products based on capric acid, caprylic acid, capric acid, lauric acid, myristic acid, Palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid as well as their technical mixtures, such as are obtained, for example, in the pressure release of natural fats and oils. Preferably industrial Ci2 be l8 ~ co ^ os f ^ ETT acids unc - in particular, partly hydrogenated Ci5 ιg tallow or palm oil fatty acids and elaidic acid-rich CISS / ig fatty cuts used.
Zur Herstellung der quaternierten Ester können die Fettsäuren und das Triethanolamin im molaren Verhältnis von 1,1 : 1 bis 3 : 1 eingesetzt werden. Im Hinblick auf die anwendungstech¬ nischen Eigenschaften der Esterquats hat sich ein Einsatz¬ verhältnis von 1,2 : 1 bis 2,2 : 1, vorzugsweise 1,5 : 1 bis 1,9 : 1 als besonders vorteilhaft erwiesen. Die bevorzugten Esterquats stellen technische Mischungen von Mono-, Di- und Triestern mit einem durchschnittlichen Veresterungsgrad von 1,5 bis 1,9 dar und leiten sich von technischer Ciß ig-Talg- bzw. Palmfettsäure ( Iodzahl 0 bis 40) ab.The fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters. With regard to the application properties of the ester quats, an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1, has proven to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical Cissig tallow or palm fatty acid (iodine number 0 to 40).
Aus anwendungstechnischer Sicht haben sich quaternierte Fett- säuretriethanolaminestersalze der Formel (I) als besonders vorteilhaft erwiesen, in der R---CO für einen Acylrest mit 16 bis 18 Kohlenstoffatomen, R2 für R---C0, R3 für Wasserstoff, R4 für eine Methylgruppe, m, n und p für 0 und X für Methylsul¬ fat steht.From an application point of view, quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R --- CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R --- C0, R 3 for hydrogen, R 4 for a methyl group, m, n and p for 0 and X for methyl sulfate.
Esterquats kommen üblicherweise als alkoholische Konzentrate mit einem Feststoffgehalt von ca. 80 bis 90 Gew.-% in den Verkehr. Die im Sinne der Erfindung beanspruchten wäßrigen Lösungen, die es zu verdicken gilt, besitzen hingegen übli- cherweise einen Feststoffgehalt im Bereich von 1 bis 50, vorzugsweise 3 bis 15 Gew.-%.Esterquats are usually marketed as alcoholic concentrates with a solids content of approx. 80 to 90% by weight. The aqueous solutions claimed to be thickened in the sense of the invention, on the other hand, usually have Usually a solids content in the range of 1 to 50, preferably 3 to 15 wt .-%.
ViskositätsregulatorenViscosity regulators
Als Viskositätsregulatoren kommen gegebenenfalls alkoxylier¬ te Ester von Fettsäuren mit technischen Oligoglyceringemi¬ schen sowie deren Anlagerungsprodukte von durchschnittlich 1 bis 10 und vorzugsweise 2 bis 5 Mol Alkylenoxid in Betracht, die als solche seit langem bekannt sind.Possible viscosity regulators are alkoxylated esters of fatty acids with technical oligoglycerin chemicals and their addition products of an average of 1 to 10 and preferably 2 to 5 mol of alkylene oxide, which have long been known as such.
Vorzugsweise handelt es sich bei den Viskositätsregulatoren um gegebenenfalls alkoxylierte Ester, die sich von Fettsäuren der Formel (II) ableiten,The viscosity regulators are preferably optionally alkoxylated esters which are derived from fatty acids of the formula (II)
R5CO-OH (II)R 5 CO-OH (II)
in der R-^CO für einen aliphatischen, linearen oder verzweig¬ ten Acylrest mit 6 bis 22 Kohlenstoffatomen und 0 und/oder 1 bis 3 Doppelbindungen steht. Typische Beispiele sind Ester von Oligoglyceringemischen mit Capronsäure, Caprylsäure, 2- Ethylhexansäure, Caprinsäure, Laurinsäure, Isotridecansäu- re, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäu¬ re, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Elaeostearinsäure, Arachinsäure, Gadoleinsäure, Behensäure und Erucasäure sowie deren techni¬ sche Mischungen, die z.B. bei der Druckspaltung von natürli¬ chen Fetten und Ölen, der Reduktion von Aldehyden aus der Roelen'sehen Oxosynthese oder der Dimerisierung von ungesät- tigten Fettsäuren anfallen. Besonders bevorzugt sind Oligo- glycerinester auf Basis Isostearinsäure.in which R ^ CO stands for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1 to 3 double bonds. Typical examples are esters of oligoglycerol mixtures with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, Isotridecansäu- acid, myristic acid, palmitic acid, palmoleic, re Stearinsäu¬, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, gadoleic , Behenic acid and erucic acid and their technical mixtures, which are used, for example, in the pressure splitting of natural fats and oils, the reduction of aldehydes from Roelen's oxosynthesis or the dimerization of unsaturated fatty acids. Oligoglycerol esters based on isostearic acid are particularly preferred.
Vorzugsweise handelt es sich bei den Viskositätsregulatoren um gegebenenfalls alkoxylierte Ester, die sich weiterhin von technischen Oligoglyceringemischen der Formel (III) ableiten,The viscosity regulators are preferably alkoxylated esters, which are also derived from industrial oligoglycerol mixtures of the formula (III),
OH OHOH OH
I II I
HO-CH2-CH-CH20[CH2-CH-CH2θ]zH (III)HO-CH 2 -CH-CH 2 0 [CH2-CH-CH2θ] z H (III)
in der z für Zahlen von 0,5 bis 10 steht. Typische Beispiele stellen Fettsäureester mit technischen Oligoglyceringemischen dar, die einen mittleren Eigenkondensationsgrad im Bereich von 1,5 bis 10, vorzugsweise 2 bis 5 aufweisen. Besonders be¬ vorzugt sind Fettsäureester auf Basis von Oligoglyceringe¬ mischen mit einem hohen Gehalt an Di- und Triglycerin.in which z stands for numbers from 0.5 to 10. Typical examples are fatty acid esters with technical oligoglycerol mixtures which have an average degree of self-condensation in the range from 1.5 to 10, preferably 2 to 5. Fatty acid esters based on oligoglycerol mixtures with a high content of di- and triglycerol are particularly preferred.
Vorzugsweise handelt es sich bei den Viskositätsregulatoren um gegebenenfalls alkoxylierte Fettsäureoligoglycerinester, die schließlich einen durchschnittlichen Veresterungsgrad von 0,75 bis 4 aufweisen. Obschon die Produkte in der Regel her¬ stellungsbedingt Gemische von Mono-, Di-, Tri- und gegebenen¬ falls Oligoestern darstellen, sind doch solche Viskositätsre¬ gulatoren besonders bevorzugt, die im statistischen Mittel 1 bis 3 Estergruppen aufweisen.The viscosity regulators are preferably optionally alkoxylated fatty acid oligoglycerol esters which finally have an average degree of esterification of 0.75 to 4. Although the products are generally mixtures of mono-, di-, tri- and optionally oligoesters due to the preparation, those viscosity regulators which have a statistical average of 1 to 3 ester groups are particularly preferred.
Vorzugsweise handelt es sich bei den alkoxylierten Ester um Anlagerungsprodukte von Ethylenoxid. Der Ethoxylierungsgrad der Ester liegt üblicherweise im Bereich von 1 bis 10 und insbesondere 2 bis 5. In einer besonderen Ausführungsform der Erfindung werden als Viskositätsregulatoren Diester der Isostearinsäure mit tech¬ nischem Triglycerin in Mengen von 0,01 bis 0,03 Gew.-% - be¬ zogen auf die Lösungen - eingesetzt.The alkoxylated esters are preferably addition products of ethylene oxide. The degree of ethoxylation of the esters is usually in the range from 1 to 10 and in particular 2 to 5. In a particular embodiment of the invention, diesters of isostearic acid with technical triglycerol are used as viscosity regulators in quantities of 0.01 to 0.03% by weight, based on the solutions.
Zur Herstellung der Lösungen hat es sich als besonders vor¬ teilhaft erwiesen, zunächst etwa die Hälfte des Wasser vor¬ zulegen und auf etwa 30 bis 50°C zu erhitzen, dann die qua¬ ternierten Fettsäuretriethanolaminester-Salze und die Vis¬ kositätsregulatoren zuzugeben und anschließend die restliche Menge Wasser, die Umgebungstemperatur aufweisen kann, einzu¬ rühren. Hierbei handelt es sich um einen rein mechanischen Vorgang, eine chemische Reaktion findet nicht statt.For the preparation of the solutions, it has proven to be particularly advantageous first to initially add about half the water and to heat it to about 30 to 50 ° C., then to add the quaternized fatty acid triethanolamine ester salts and the viscosity regulators and then stir in the remaining amount of water, which may be at ambient temperature. This is a purely mechanical process, there is no chemical reaction.
Gewerbliche AnwendbarkeitIndustrial applicability
Die er indungsgemäßen wäßrigen Lösungen zeichnen sich durch eine vorteilhafte und auch bei längerer Lagerung praktisch unveränderte Viskosität aus .The aqueous solutions according to the invention are characterized by an advantageous viscosity which is practically unchanged even after prolonged storage.
Ein weiterer Gegenstand der Erfindung betrifft wäßrige Wä- scheweichspülmittel, enthaltend 1 bis 50 Gew.-% quaternier¬ te Fettsäuretriethanolaminester-Salze, 0,01 bis 0,1 Gew.-% gegebenenfalls alkoxylierte Ester von Fettsäuren mit techni¬ schen Oligoglyceringemischen sowie gegebenenfalls weitere Hilfs- und Zusatzstoffe.The invention further relates to aqueous laundry softening agents containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and, if appropriate, others Auxiliaries and additives.
Ein weiterer Gegenstand der Erfindung betrifft wäßrige Haar¬ behandlungsmittel, enthaltend 1 bis 50 Gew.-% quaternierte Fettsäuretriethanolaminester-Salze, 0,01 bis 0,1 Gew.-% gegebenenfalls alkoxylierte Ester von Fettsäuren mit techni¬ schen Oligoglyceringemischen sowie gegebenenfalls weitere Hilfs- und Zusatzstoffe.The invention further relates to aqueous hair treatment compositions containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight. optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and optionally further auxiliaries and additives.
Ein letzter Gegenstand der Erfindung betrifft schließlich die Verwendung von gegebenenfalls alkoxylierten Estern von Fett¬ säuren mit technischen Oligoglyceringemischen als Viskosi¬ tätsregulatoren für wäßrige Lösungen von quaternierten Fett- säuretriethanolaminester-Salzen, in denen sie in Mengen von 0,01 bis 0,1 Gew.-% - bezogen auf die Lösungen - enthalten sein können.Finally, the invention relates to the use of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures as viscosity regulators for aqueous solutions of quaternized fatty acid triethanolamine ester salts, in which they are present in amounts of 0.01 to 0.1% by weight. -% - based on the solutions - may be included.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken. The following examples are intended to explain the subject matter of the invention in more detail without restricting it.
BeispieleExamples
I. Eingesetzte StoffeI. Substances used
AI) Methylquaternierter Ciß i8-Talgfettsäuretriethanolamin- ester in Form des Methylsulfat-Salzes; Veresterungsgrad 1,64 Dehyquart(R) AU-46, Pulcra S.A., Barcelona/ESAI) methyl-quaternized Ciß i8 tallow fatty acid triethanolamine ester in the form of the methyl sulfate salt; Degree of esterification 1.64 Dehyquart ( R ) AU-46, Pulcra SA, Barcelona / ES
A2) Methylquaternierter Cis/ig-Talgfettsäuretriethanolamin- ester in Form des Methylsulfat-Salzes/Cetearylalkohol; Dehyquart(R) F 75, Henkel KGaA, Düsseldorf/FRGA2) Methyl-quaternized cis / ig tallow fatty acid triethanolamine ester in the form of the methyl sulfate salt / cetearyl alcohol; Dehyquart ( R ) F 75, Henkel KGaA, Düsseldorf / FRG
Bl ) TriglycerindiisostearatBl) triglycerol diisostearate
Lameform(R) TGi, Henkel KGaA, Düsseldorf/FRGLameform (R ) TGi, Henkel KGaA, Düsseldorf / FRG
B2) 01igoglycerin-2E0-tetrastearatB2) 01igoglycerin-2E0 tetrastearate
Lamecreme(R) DGE 18, Henkel KGaA, Düsseldorf/FRGLama cream ( R ) DGE 18, Henkel KGaA, Düsseldorf / FRG
II. ViskositätsmessungenII. Viscosity measurements
In einem 250-ml-Becherglas wurden 46 ml entionisierteε Wasser vorgelegt, auf 40°C erwärmt und mit 4,7 g des Esterquats (A) und 0,01 bis 1,1 g des Viskositätsregulators (B) versetzt. Anschließend wurde mit Wasser von 20°C auf 100 ml aufgefüllt und 5 min gerührt. Die Bestimmung der Viskosität erfolgte nach Brookfield (25°C, Spindel 5, 10 Up ) . Die Ergebnisse sind in Tabelle 1 zusammengefaßt (Prozentangaben als Gew.-%). Tabelle 1 Viskositätsmessungen46 ml of deionized water were placed in a 250 ml beaker, heated to 40 ° C. and treated with 4.7 g of the ester quat (A) and 0.01 to 1.1 g of the viscosity regulator (B). The mixture was then made up to 100 ml with water from 20 ° C. and stirred for 5 min. The viscosity was determined according to Brookfield (25 ° C., spindle 5, 10 up). The results are summarized in Table 1 (percentages as% by weight). Table 1 Viscosity measurements
Bsp. A c(A) B cfB. cfB) Viskosität g/i g/i % mPa.sEx. A c (A) B cfB. cfB) Viscosity g / i g / i% mPa.s
1 1 47,0 1 0,1 0,01 1161 1 47.0 1 0.1 0.01 116
2 1 47,0 1 0,3 0,03 1362 1 47.0 1 0.3 0.03 136
3 1 47,0 2 0,3 0,03 1513 1 47.0 2 0.3 0.03 151
4 2 47,0 2 0,3 0,03 2484 2 47.0 2 0.3 0.03 248
VI 1 47,0 1 _ _ 28VI 1 47.0 1 _ _ 28
V2 1 47,0 1 1,1 0,11 46V2 1 47.0 1 1.1 0.11 46
V3 1 47,0 1 10,0 1,00 36V3 1 47.0 1 10.0 1.00 36
Legende; c(A) = Konzentration Esterquat c(B) = Konzentration Viskositätεregulator Legend; c (A) = concentration of ester quat c (B) = concentration of viscosity regulator

Claims

Patentansprüche claims
1. Wäßrige Lösungen von quaternierten Fettsäuretriethanol- aminester-Salzen, dadurch gekennzeichnet, daß sie als Viskositätsregulatoren 0,01 bis 0,1 Gew.-% - bezogen auf die Lösungen - gegebenenfalls alkoxylierte Ester von Fettsäuren mit technischen Oligoglyceringemischen ent¬ halten.1. Aqueous solutions of quaternized fatty acid triethanolamine ester salts, characterized in that they contain 0.01 to 0.1% by weight, based on the solutions, of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures as viscosity regulators.
2. Wäßrige Lösungen nach Anspruch 1, dadurch gekennzeich¬ net, daß sie quaternierte Fettsäuretriethanolaminester- Salze der Formel (I) enthalten,2. Aqueous solutions according to claim 1, characterized gekennzeich¬ net that they contain quaternized fatty acid triethanolamine ester salts of the formula (I),
R4R4
ΓΓ
[ RlC0- ( 0CH2CH2 )ιn0CH2CH2-N-CH2CH20- ( CH2CH20 ) nR2 ] X~ ( I )[RlC0- (0CH 2 CH 2 ) ιn 0CH2CH2- N -CH2CH20- (CH2CH20) n R 2 ] X ~ (I)
II.
CH2CH20(CH2CH2θ)pR3 CH 2 CH 2 0 (CH 2 CH2θ) pR 3
in der R1C0 für einen Acylrest mit 6 bis 22 Kohlenstoff¬ atomen, R2 und R3 unabhängig voneinander für Wasserstoff oder R---C0, R4 für einen Alkylrest mit 1 bis 4 Kohlen¬ stoffatomen oder eine (CH2CH2θ)qH-Gruppe, m, n und p in Summe für 0 oder Zahlen von 1 bis 12, q für Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphos- phat steht.in which R 1 is C0 for an acyl radical with 6 to 22 carbon atoms, R 2 and R 3 independently of one another for hydrogen or R --- C0, R 4 for an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2θ) qH -Group, m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
3. Wäßrige Lösungen nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, daß sie einen Feεtstoffgehalt im Bereich von 1 bis 50 Gew.-% aufweisen. 3. Aqueous solutions according to Claims 1 and 2, characterized in that they have a solids content in the range from 1 to 50% by weight.
4. Wäßrige Lösungen nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß sie als Viskositätsregulatoren Ester enthalten, die sich von Fettsäuen der Formel (II) ablei¬ ten,4. Aqueous solutions according to claims 1 to 3, characterized in that they contain as viscosity regulators esters derived from fatty acids of the formula (II),
R5CO-OH (II)R 5 CO-OH (II)
in der R^CO für einen aliphatischen, linearen oder ver¬ zweigten Acylrest mit 6 bis 22 Kohlenstoffatomen und 0 und/oder 1 bis 3 Doppelbindungen steht.in which R ^ CO represents an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1 to 3 double bonds.
5. Wäßrige Lösungen nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß sie als Viskositätsregulatoren Ester enthalten, die einen Ethoxylierungsgrad im Bereich von 1 bis 10 aufweisen.5. Aqueous solutions according to claims 1 to 4, characterized in that they contain as viscosity regulators esters which have a degree of ethoxylation in the range from 1 to 10.
6. Wäßrige Lösungen nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß sie als Viskositätsregulatoren Ester enthalten, die sich von technischen Oligoglyceringe¬ mischen der Formel (III) ableiten,6. Aqueous solutions according to claims 1 to 5, characterized in that they contain as viscosity regulators esters derived from technical oligoglycerol mixtures of the formula (III),
OH OHOH OH
I II I
HO-CH2-CH-CH2θ[CH2-CH-CH20]zH (III)HO-CH 2 -CH-CH2θ [CH2-CH-CH 2 0] z H (III)
in der z für Zahlen von 0,5 bis 10 steht.in which z stands for numbers from 0.5 to 10.
7. Wäßrige Lösungen nach den Ansprüchen 1 bis 6, dadurch gekennzeichnet, daß die Viskositätsregulatoren einen Veresterungsgrad von 0,75 bis 4 aufweisen. 7. Aqueous solutions according to claims 1 to 6, characterized in that the viscosity regulators have a degree of esterification of 0.75 to 4.
8. Wäßrige Wäscheweichspülmittel, enthaltend 1 bis 50 Gew.-% quaternierte Fettsäuretriethanolaminester-Salze, 0,01 bis 0,1 Gew.-% gegebenenfalls alkoxylierte Ester von Fettsäuren mit technischen Oligoglyceringemischen sowie gegebenenfalls weitere Hilfs- und Zusatzstoffe.8. Aqueous fabric softener, containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and optionally other auxiliaries and additives.
9. Wäßrige Haarbehandlungsmittel, enthaltend 1 bis 50 Gew.-% quaternierte Fettsäuretriethanolaminester-Salze, 0,01 bis 0,1 Gew.-% gegebenenfalls alkoxylierte Ester von Fettsäuren mit technischen Oligoglyceringemischen sowie gegebenenfalls weitere Hilfs- und Zusatzstoffe.9. Aqueous hair treatment compositions containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and, if appropriate, further auxiliaries and additives.
10. Verwendung von gegebenenfalls alkoxylierten Estern von Fettsäuren mit technischen Oligoglyceringemischen als Viskositätsregulatoren für wäßrige Lösungen von qua- ernierten Fettsäuretriethanolaminester-Salzen. 10. Use of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures as viscosity regulators for aqueous solutions of quaternized fatty acid triethanolamine ester salts.
PCT/EP1995/000047 1994-01-14 1995-01-05 Aqueous solutions of quaternary fatty acid triethanolamine ester salts WO1995019416A1 (en)

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EP0762830B1 (en) * 1994-06-02 2001-12-19 Kao Corporation Method for enhancing the efficacy of agricultural chemicals
EP2576743B1 (en) 2010-05-28 2015-11-11 Colgate-Palmolive Company Fatty acid chain saturation in alkanol amine based esterquat
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