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EP0906269A1 - Acid addition compounds of fatty acid polyhydroxy alkyl amides - Google Patents

Acid addition compounds of fatty acid polyhydroxy alkyl amides

Info

Publication number
EP0906269A1
EP0906269A1 EP97925021A EP97925021A EP0906269A1 EP 0906269 A1 EP0906269 A1 EP 0906269A1 EP 97925021 A EP97925021 A EP 97925021A EP 97925021 A EP97925021 A EP 97925021A EP 0906269 A1 EP0906269 A1 EP 0906269A1
Authority
EP
European Patent Office
Prior art keywords
acid
weight
adduct
residue
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97925021A
Other languages
German (de)
French (fr)
Inventor
Bernd Papenfuhs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
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Filing date
Publication date
Application filed by Clariant GmbH filed Critical Clariant GmbH
Publication of EP0906269A1 publication Critical patent/EP0906269A1/en
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/22Amides or hydrazides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Definitions

  • the invention relates to strongly foaming acid adducts of fatty acid polyhydroxyalkylamides and a process for their preparation.
  • the invention further relates to compositions with these adducts and the use of the acid adducts and the compositions.
  • Adducts of tertiary fatty amines with acids or with alkylating agents such as alkyl halides, alkyl sulfates or alkylene oxides in the presence of an aqueous acid are effective and versatile cationic surfactants.
  • DE-A-42 38 207 and DE-A-42 38 211 describe adducts of fatty acid polyhydroxyalkylamides (as an amine compound) with alkylating agents. These quaternary ammonium salts are prepared by quaternization (alkylation) of a fatty acid polyhydroxyalkylamide with a
  • Alkylating agents such as methyl chloride, dimethyl sulfate, dimethyl phosphate or ethylene oxide and / or propylene oxide in the presence of an aqueous acid.
  • these adducts have high cold water dispersibility and excellent antistatic and wetting properties. It has now surprisingly been found that adducts of a fatty acid polyhydroxyalkylamide in the form of a tertiary amine and an acid (instead of an alkylating agent) have a high foaming power.
  • the acid adducts according to the invention correspond to the following formula (1)
  • Oligoglycoside residue with 2 to 6 glycose units, x is an integer from 2 to 4, R 1 is a C to C 4 alkyl or C 2 to C 4 hydroxyalkyl,
  • R 2 is a CL to C 4 alkyl or
  • CO-R is an aliphatic acyl radical having 6 to 22 carbon atoms and A- is an anionic radical of an inorganic or organic acid.
  • Preferred acid adducts are those in which Z is a reduced glycoside residue or oligoglycoside residue with 2 or 3 glycose units (that is a di- or triglycoside residue), x 3,
  • R 1 and R 2 are methyl or ethyl and CO-R is a fatty acyl radical with 8 to 18 carbon atoms.
  • the aliphatic acyl radical CO-R which is preferably the fatty acyl radical mentioned, can be saturated or unsaturated (preferably mono- to trisaturated). Examples include the acyl residues of caprylic, capric, lauric, palmitic, stearic and oleic acids as well as cocosacyl, tallow acyl, preferably hardened tallow acyl, and the like.
  • the fatty acid residue is often a mixture of two or more acyl groups, for example C 12 and C 14 acyl
  • the OB ne are the radical Z is derived, as already mentioned above, preferably sugar alcohols derived from mono- -, Di- or trisaccharides. Pentoses and hexoses are preferred as monosaccharides.
  • Examples of monosaccharides are glucose, galactose, mannose and talose as hexoses and arabinose, ribose and xylose as pentoses.
  • Examples of di- and trisaccharides (polysaccharides) are lactose, maltose, maltotriose and the like. Particularly preferred
  • Polyhydroxyalkyl residues originate from reduced hexoses, in particular from glucose (sorbityl residue).
  • the particularly preferred radical Z thus corresponds to the formula below
  • the anion A ⁇ of the adducts according to the invention generally comes from a mineral acid or from an (aliphatic or aromatic) carboxylic acid.
  • Preferred inorganic acids are Hydrogen halide acids such as HC1 or HBr, carbonic acid, phosphoric acid, nitric acid or sulfuric acid.
  • the anion is a carboxylate.
  • Preferred carboxylic acids are C 1 -C 3 -monocarboxylic acids such as formic acid, acetic acid or propionic acid; C 12 to C 18 monocarboxylic acid such as dodecanoic acid, palmitic acid, stearic acid or oleic acid; Dicarboxylic acids of the formula HOOC- (CH 2 ) n -COOH, where n is 0 or an integer from 1 to 8, such as oxalic, malonic, succinic, glutaric or adipic acid and the unsaturated dicarboxylic acids, fumaric and maleic acids; Monohydroxy monocarboxylic acids such as glycolic acid (hydroxyacetic acid) or lactic acid ( ⁇ -hydroxy-propionic acid); Monohydroxy dicarboxylic acids such as tartronic acid (monohydroxy malonic acid) or malic acid (monohydroxy succinic acid); Dihydroxy-dicarboxylic acids such as tartaric acid (dihydroxy-succinic acid); Monohydroxy-
  • the anion A ⁇ is therefore preferably a halide, carbonate, phosphate, nitrate, sulfate or carboxylate, carboxylate being particularly preferred.
  • a ⁇ is given for further explanation: halides such as Cl ⁇ , Br ⁇ ; Sulfates such as (S0 4 2 " ) 1 // 2 ; phosphates such as (P ⁇ 4 3 ⁇ ) ⁇ / 3?
  • carboxylates such as CH3C00 " , C 11 H 23 COO ⁇ , CH 3 -CH (OH) -COO- (anion der Lactic acid), ⁇ 0OC-CH (0H) -CH 2 -C00H (anion of malic acid), C 6 H 5 -C00 ⁇ (anion of benzoic acid).
  • the inventive method for producing the ammonium salts of formula (1) is characterized in that one
  • reaction components polyhydroxyalkylamide and acid within wide molar ratios.
  • Fatty acid polyhydroxyalkylamide used.
  • the temperature of the reaction taking place at atmospheric pressure is generally from 10 to 120 ° C. and preferably from 25 to 100 ° C.
  • the quaternization according to the invention is carried out by mixing the
  • Reaction components acid and polyhydroxyalkylamide. It can be carried out in bulk, that is to say in the absence of solvents, or in the presence of solvents, if appropriate in combination with other surfactants, the reaction in solution is preferred.
  • Suitable solvents are water; lower alcohols, preferably CI to C3 alkanols such as methanol, ethanol, propanol or isopropanol; lower glycols such as ethylene glycol or propylene glycol; Oxalkylene glycols with 2 to 6 ethylene oxide and / or propylene oxide units such as diethylene glycol, dipropylene glycol, triethylene glycol, pentaethylene glycol; Mono- or di-C to C 4 alkyl ethers of lower glycols or oxalkylene glycols; and fatty alcohol alkoxylates, preferably
  • solvents mentioned water, C 1 -C 6 -alkanols, lower glycols and mixtures thereof are preferred.
  • the amount of solvent can vary within wide limits. In general, 5 to 80% by weight of solvent are used, preferably 10 to 70% by weight, percentages by weight based on the mixture of fatty acid polyhydroxyalkylamide and solvent. It is preferred to present the mixture mentioned and to stir the salt-forming acid continuously or in portions into the mixture.
  • the inorganic or organic acid can be used as such; it is preferably used in the form of a solution in water and / or lower alcohols.
  • the reaction mixture can be stirred further for the after-reaction.
  • the course of the quaternization can be followed by titrimetric determination of the basic nitrogen content in the reaction mixture (decrease in fatty acid polyhydroxyalkylamide).
  • the quaternization is generally complete after 0.1 to 2 hours.
  • the desired salt formation is proceeding quantitative and leads to the formation of compounds of formula (1), which are obtained in the form of a solution when solvents are used.
  • the acid adducts can be obtained as such, for example by removing the solvent or isolating them from the reaction mixture.
  • compositions according to the invention are characterized by a content of at least 5% by weight, preferably 10 to 70% by weight, based on the composition, of at least one acid adduct of the formula (1).
  • Preferred compositions essentially consist of a) 10 to 70% by weight, preferably 15 to 50% by weight, of at least one acid adduct of the formula (1) as active ingredient and b) 30 to 90% by weight, preferably 50 to 85 wt .-%, of a solvent consisting essentially of water, lower alcohols, lower glycols or a mixture thereof, percentages by weight based on the composition.
  • compositions essentially consist of a ') 10 to 70% by weight, preferably 15 to 50% by weight, of at least one acid adduct of the formula (1) and b') 30 to 90% by weight, preferably 50 to 85% by weight of at least one other cationic and / or anionic and / or nonionic and / or amphoteric surfactant, percentages by weight based on the
  • compositions can be present as such, ie free of solvents, or in the form of a solution, the solvent being water, lower alcohols, lower glycols or a mixture thereof.
  • the solutions generally contain 10 to 70% by weight, preferably 15 to 50% by weight, of the sum of components a ') and b').
  • Suitable other cationic surfactants are, for example, the usual quaternary ammonium compounds with four alkyl radicals on the nitrogen atom and quaternary ones
  • Carboxylic acid ethanolamine ester salts (esterquats).
  • Suitable anionic surfactants are, for example, alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, alkyl sulfates, fatty alcohol ether sulfates,
  • Glycerin ether sulfates, fatty acid amide (ether) sulfates, sulfosuccinates, sarcosmates and taurides are, for example, fatty acid polyhydroxyalkylamides, fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, sorbitan esters and alkyl polyglycosides.
  • Suitable amphoteric or zwitterionic surfactants are, for example, alkyl betaines, alkyl amido betaines,
  • Aminopropionates aminoglycinates, imidazolinium betaines and sulfobetaines.
  • compositions according to the invention are obtained by mixing the specified components together at approximately
  • salt compounds of the formula (1) according to the invention and their compositions have an unexpectedly high foaming capacity and therefore represent an excellent foaming agent. Because of their further properties, such as good skin tolerance and high thickenability, they are also advantageous as detergents and cosmetics, preferably as hair and Personal care products used.
  • DMAP-G technical N- (3-dimethylamino) propylglucamine
  • a conventional stripping apparatus For this purpose, the solution is heated to about 100 ° C. and first dewatered at normal pressure to a residual water content of about 5% by weight. The solution is then heated to 130 ° C. for further dewatering and kept at this temperature, a vacuum of up to 25 mbar being gradually applied. It is dewatered up to a residual water content of 0.2% by weight. 104.1 g (0.473 mol) are stirred into the melt thus obtained at 130 ° C.
  • DMAP-G technical N- (3-dimethylamino) propylglucamine
  • the lactate according to the invention (adduct 2) is prepared by adding an aqueous solution of lactic acid instead of hydrochloric acid analogously to Example 1; if necessary, the dissolved product can of course also be obtained in substance by distilling off the water.
  • lactate (adduct 2) can be greatly thickened without the addition of electrolytes is absolutely exceptional and of great interest for various special applications.

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  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The description relates to acid addition compounds of formula (1) and compositions with such compounds. In said formula (1), Z is a reduced glycoside or oligoglycoside radical, x is a whole number from 2 to 4, R?1 and R2¿ are a C¿1? to C4 alkyl or a C2 to C4 hydroxy alkyl, CO-R is an aliphatic acyl radical with 6 to 22 carbon atoms and A?-¿ is an anion radical of an inorganic or organic acid. The addition compounds are produced by reacting a fatty acid polyhydroxy alkyl amide and an acid corresponding to formula (1). The addition compounds and the compositions are excellent blowing and thickening agents.

Description

Beschreibung description
Saure-Addukte von FettsaurepolyhydroxyalkylamidenAcid adducts of fatty acid polyhydroxyalkylamides
Die Erfindung betrifft stark schäumende Saure-Addukte von Fettsaurepolyhydroxyalkylamiden und ein Verfahren zu deren Herstellung. Die Erfindung betrifft ferner Kompositionen mit diesen Addukten und die Verwendung der Saure-Addukte und der Kompositionen.The invention relates to strongly foaming acid adducts of fatty acid polyhydroxyalkylamides and a process for their preparation. The invention further relates to compositions with these adducts and the use of the acid adducts and the compositions.
Addukte von tertiären Fettaminen mit Sauren oder mit Alkylierungsmitteln wie Alkylhalogeniden, Alkylsulfaten oder Alkylenoxiden in Gegenwart einer wäßrigen Saure stellen wirksame und vielseitig verwendbare kationische Tenside dar.Adducts of tertiary fatty amines with acids or with alkylating agents such as alkyl halides, alkyl sulfates or alkylene oxides in the presence of an aqueous acid are effective and versatile cationic surfactants.
In DE-A-42 38 207 und DE-A-42 38 211 werden Addukte von Fettsaurepolyhydroxyalkylamiden (als Aminverbindung) mit Alkylierungsmitteln beschrieben. Die Herstellung dieser quaternaren Ammoniumsalze erfolgt durch Quaternisierung (Alkylierung) von einem Fettsaurepolyhydroxyalkylamid mit einemDE-A-42 38 207 and DE-A-42 38 211 describe adducts of fatty acid polyhydroxyalkylamides (as an amine compound) with alkylating agents. These quaternary ammonium salts are prepared by quaternization (alkylation) of a fatty acid polyhydroxyalkylamide with a
Alkylierungsmittel wie Methylchlorid, Dimethylsulfat, Dimethylphosphat oder Ethylenoxid und/oder Propylenoxid in Gegenwart einer wäßrigen Saure. Wie in DE-A-42 38 207 ausgeführt wird, weisen diese Addukte eine hohe Kaltwasserdispergierbarkeit und ausgezeichnete antistatische und netzende Eigenschaften auf. Es wurde nun überraschenderweise gefunden, daß Addukte aus einem Fettsaurepolyhydroxyalkylamid in Form eines tertiären Amins und einer Saure (anstelle eines Alkylierungsmittels) ein hohes Schaumvermogen aufweisen. Die erfindungsgemaßen Saure-Addukte entsprechen der nachstehenden Formel (1)Alkylating agents such as methyl chloride, dimethyl sulfate, dimethyl phosphate or ethylene oxide and / or propylene oxide in the presence of an aqueous acid. As stated in DE-A-42 38 207, these adducts have high cold water dispersibility and excellent antistatic and wetting properties. It has now surprisingly been found that adducts of a fatty acid polyhydroxyalkylamide in the form of a tertiary amine and an acid (instead of an alkylating agent) have a high foaming power. The acid adducts according to the invention correspond to the following formula (1)
CO-R Rl Z-N-(CH2)χ-N+-R2 A" (1)CO-R Rl ZN- (CH 2 ) χ-N + -R2 A "(1)
II.
HH
worin Z ein reduzierter Glycosidrest oderwherein Z is a reduced glycoside residue or
Oligoglycosidrest mit 2 bis 6 Glycose- Einheiten, x eine ganze Zahl von 2 bis 4, R1 ein C- bis C4-Alkyl oder C2 bis C4-Hydroxyalkyl,Oligoglycoside residue with 2 to 6 glycose units, x is an integer from 2 to 4, R 1 is a C to C 4 alkyl or C 2 to C 4 hydroxyalkyl,
R2 ein C-L bis C4-Alkyl oderR 2 is a CL to C 4 alkyl or
C2 bis C4-Hydroxyalkyl, CO-R ein aliphatischer Acylrest mit 6 bis 22 Kohlenstoffatomen und A- ein Anionrest einer anorganischen oder organischen Saure ist.C 2 to C 4 hydroxyalkyl, CO-R is an aliphatic acyl radical having 6 to 22 carbon atoms and A- is an anionic radical of an inorganic or organic acid.
Bevorzugte Saure-Addukte sind solche wobei Z ein reduzierter Glycosidrest oder Oligoglycosidrest mit 2 oder 3 Glycose-Einheiten (das ist ein Di- oder Triglycoεidrest) , x 3,Preferred acid adducts are those in which Z is a reduced glycoside residue or oligoglycoside residue with 2 or 3 glycose units (that is a di- or triglycoside residue), x 3,
R1 und R2 (gleich oder verschieden) Methyl oder Ethyl und CO-R ein Fettacylrest mit 8 bis 18 Kohlenstoffatomen ist. Zu CO-R und Z sei im einzelnen noch folgendes gesagt: Der aliphatische Acylrest CO-R, der vorzugsweise der genannte Fettacylrest ist, kann gesattigt oder ungesättigt (vorzugsweise ein- bis dreifach ungesättigt) sein. Als Beispiele seien die Acylreste von Capryl-, Caprin-, Laurin-, Palmitin-, Stearin- und Olsaure genannt sowie Cocosacyl, Talgacyl, vorzugsweise gehärtetes Talgacyl, und dergleichen. Der Fettsaurerest stellt häufig eine Mischung von zwei oder mehreren Acylgruppen dar, zum Beispiel C12 und C14-AcylR 1 and R 2 (identical or different) are methyl or ethyl and CO-R is a fatty acyl radical with 8 to 18 carbon atoms. The following should be said in detail about CO-R and Z: The aliphatic acyl radical CO-R, which is preferably the fatty acyl radical mentioned, can be saturated or unsaturated (preferably mono- to trisaturated). Examples include the acyl residues of caprylic, capric, lauric, palmitic, stearic and oleic acids as well as cocosacyl, tallow acyl, preferably hardened tallow acyl, and the like. The fatty acid residue is often a mixture of two or more acyl groups, for example C 12 and C 14 acyl
(°12/14) ' C16 und C18-Acyl (Cl6/is) oder C12 kiΞ Ci8-Acyl- Der Üneare Rest Z stammt, wie oben bereits erwähnt, vorzugsweise von Zuckeralkoholen, abgeleitet aus Mono-, Di- oder Trisacchariden. Als Monosaccharide sind Pentosen und Hexosen bevorzugt. 12/14) 'C 16 and C 18 acyl (Cl6 / is), or C 12 ki Ξ C i8 yl -Ac The OB ne are the radical Z is derived, as already mentioned above, preferably sugar alcohols derived from mono- -, Di- or trisaccharides. Pentoses and hexoses are preferred as monosaccharides.
Beispiele für Monosaccharide sind Glucose, Galaktose, Mannose und Talose als Hexosen und Arabinose, Ribose und Xylose als Pentosen. Beispiele für Di- und Trisaccharide (Polysaccharide) sind Lactose, Maltose, Maltotriose und dergleichen. Besonders bevorzugteExamples of monosaccharides are glucose, galactose, mannose and talose as hexoses and arabinose, ribose and xylose as pentoses. Examples of di- and trisaccharides (polysaccharides) are lactose, maltose, maltotriose and the like. Particularly preferred
Polyhydroxyalkylreste stammen von reduzierten Hexosen, insbesondere von Glucose (Sorbitylrest) . Der besonders bevorzugte Rest Z entspricht also der nachstehenden FormelPolyhydroxyalkyl residues originate from reduced hexoses, in particular from glucose (sorbityl residue). The particularly preferred radical Z thus corresponds to the formula below
CH2- (CH-0H)4 CH 2 - (CH-0H) 4
CH2-OHCH 2 -OH
Das Anion A~ der erfindungsgemaßen Addukte stammt im allgemeinen von einer Mineralsaure oder von einer (aliphatischen oder aromatischen) Carbonsaure. Bevorzugte anorganische Sauren sind Halogenwasserstoffsauren wie HC1 oder HBr, Kohlensaure, Phosphorsaure, Salpetersaure oder Schwefelsaure. Im Falle einer Carbonsaure ist das Anion ein Carboxylat. Bevorzugte Carbonsauren sind C^ bis C3~Monocarbonsäuren wie Ameisensaure, Essigsäure oder Propionsaure; C12 bis C18-Monocarbonsaure wie Dodecansaure, Palmitinsaure, Stearinsäure oder olsaure; Dicarbonsauren der Formel HOOC- (CH2) n-COOH, worin n 0 oder eine ganze Zahl von 1 bis 8 ist, wie Oxal-, Malon-, Bernstein-, Glutar- oder Adipinsaure und die ungesättigten Dicarbonsauren, Fumar- und Maleinsäure; Monohydroxy-monocarbonsauren wie Glykolsaure (Hydroxy- essigsaure) oder Milchsaure (α-Hydroxy-propionsaure) ; Monohydroxy-dicarbonsauren wie Tartronsaure (Monohydroxy-malonsaure) oder Apfelsaure (Monohydroxy- bernsteinsaure) ; Dihydroxy-dicarbonsauren wie Weinsäure (Dihydroxy-bernsteinsaure) ; Monohydroxy-tricarbonsauren wie Citronensaure (Hydroxy-tricarballylsaure) ; Hydroxy- benzoesauren wie Salicylsaure oder Gallussäure; und aromatische Dicarbonsauren (Phthalsäuren) wie o-Phthalsaure oder p-Phthalsaure. Von den genannten organischen Sauren als Salzbildner sind die Cη^ bis C3~Monocarbonsauren, die Milchsaure und die Fruchtsauren besonders bevorzugt.The anion A ~ of the adducts according to the invention generally comes from a mineral acid or from an (aliphatic or aromatic) carboxylic acid. Preferred inorganic acids are Hydrogen halide acids such as HC1 or HBr, carbonic acid, phosphoric acid, nitric acid or sulfuric acid. In the case of a carboxylic acid, the anion is a carboxylate. Preferred carboxylic acids are C 1 -C 3 -monocarboxylic acids such as formic acid, acetic acid or propionic acid; C 12 to C 18 monocarboxylic acid such as dodecanoic acid, palmitic acid, stearic acid or oleic acid; Dicarboxylic acids of the formula HOOC- (CH 2 ) n -COOH, where n is 0 or an integer from 1 to 8, such as oxalic, malonic, succinic, glutaric or adipic acid and the unsaturated dicarboxylic acids, fumaric and maleic acids; Monohydroxy monocarboxylic acids such as glycolic acid (hydroxyacetic acid) or lactic acid (α-hydroxy-propionic acid); Monohydroxy dicarboxylic acids such as tartronic acid (monohydroxy malonic acid) or malic acid (monohydroxy succinic acid); Dihydroxy-dicarboxylic acids such as tartaric acid (dihydroxy-succinic acid); Monohydroxy-tricarboxylic acids such as citric acid (hydroxy-tricarballylic acid); Hydroxybenzoic acids such as salicylic acid or gallic acid; and aromatic dicarboxylic acids (phthalic acids) such as o-phthalic acid or p-phthalic acid. Of the organic acids mentioned as salt formers, the Cη ^ to C3 ~ monocarboxylic acids, lactic acid and fruit acids are particularly preferred.
Das Anion A~ ist also vorzugsweise ein Halogenid, Carbonat, Phosphat, Nitrat, Sulfat oder Carboxylat, wobei Carboxylat besonders bevorzugt ist. Ausgehend von den genannten Sauren seien zur weiteren Erläuterung einige Beispiele für A~ angeführt: Halogenide wie Cl~, Br~; Sulfate wie (S04 2")1//2; Phosphate wie (Pθ43~)ι/3? und Carboxylate wie CH3C00", C11H23COO~, CH3-CH(OH) -COO- (Anion der Milchsäure) , ~0OC-CH(0H)-CH2-C00H (Anion der Äpfelsaure), C6H5-C00~ (Anion der Benzoesaure) . Das erfindungsgemaße Verfahren zur Herstellung der Ammoniumsalze der Formel (1) ist dadurch gekennzeichnet, daß man einThe anion A ~ is therefore preferably a halide, carbonate, phosphate, nitrate, sulfate or carboxylate, carboxylate being particularly preferred. Starting from the acids mentioned, some examples of A ~ are given for further explanation: halides such as Cl ~, Br ~; Sulfates such as (S0 4 2 " ) 1 // 2 ; phosphates such as (Pθ4 3 ~ ) ι / 3? And carboxylates such as CH3C00 " , C 11 H 23 COO ~, CH 3 -CH (OH) -COO- (anion der Lactic acid), ~ 0OC-CH (0H) -CH 2 -C00H (anion of malic acid), C 6 H 5 -C00 ~ (anion of benzoic acid). The inventive method for producing the ammonium salts of formula (1) is characterized in that one
Fettsaurepolyhydroxyalkylamid der nachstehenden Formel (2)Fatty acid polyhydroxyalkylamide represented by formula (2) below
CO-R RlCO-R Rl
Z-N-(CH2)X~N-R2 (2)ZN- (CH 2 ) X ~ NR 2 (2)
worin Z, x, R1, R2 und CO-R die angegebenen Bedeutungen haben, mit einer Saure der nachstehenden Formel (3)wherein Z, x, R 1 , R 2 and CO-R have the meanings given, with an acid of the formula (3) below
HA (3)HA (3)
worin A die genannte Bedeutung hat, zum Saure-Addukt der Formel (1) umsetzt.where A has the meaning given, is converted to the acid adduct of the formula (1).
Bei der erfindungsgemaßen Umsetzung kann man dieIn the implementation according to the invention, the
Reaktionskomponenten Polyhydroxyalkylamid und Saure innerhalb weiter Molverhaltnisse einsetzen. So werden im allgemeinen 0,5 bis 1,5 mol Saure pro mol Fettsaurepolyhydroxyalkylamid, vorzugsweise 0,8 bis 1,2 mol und insbesondere 1 mol Saure pro molUse reaction components polyhydroxyalkylamide and acid within wide molar ratios. In general, 0.5 to 1.5 mol of acid per mol of fatty acid polyhydroxyalkylamide, preferably 0.8 to 1.2 mol and in particular 1 mol of acid per mol
Fettsaurepolyhydroxyalkylamid, eingesetzt. Die Temperatur der bei Atmospharendruck ablaufenden Umsetzung liegt im allgemeinen bei 10 bis 120 °C und vorzugsweise bei 25 bis 100 "C. Die erfindungsgemäße Quaternisierung erfolgt durch Zusammenmischen derFatty acid polyhydroxyalkylamide used. The temperature of the reaction taking place at atmospheric pressure is generally from 10 to 120 ° C. and preferably from 25 to 100 ° C. The quaternization according to the invention is carried out by mixing the
Reaktionskomponenten Saure und Polyhydroxyalkylamid. Sie kann in Substanz, das heißt in Abwesenheit von Losungsmitteln, oder in Gegenwart von Losungsmitteln, gegebenenfalls in Kombination mit anderen Tensiden, durchgeführt werden, wobei die Reaktion in Losung bevorzugt ist. Geeignete Losungsmittel sind Wasser; niedere Alkohole, vorzugsweise CI bis C3-Alkanole wie Methanol, Ethanol , Propanol oder Isopropanol; niedere Glykole wie Ethylenglykol oder Propylenglykol; Oxalkylenglykole mit 2 bis 6 Ethylenoxid- und/oder Propylenoxid-Einheiten wie Diethylenglykol, Dipropylenglykol, Triethylenglykol , Pentaethylenglykol; Mono- oder Di-C- bis C4-alkylether von niederen Glykolen oder Oxalkylenglykolen; und Fettalkoholalkoxylate, vorzugsweiseReaction components acid and polyhydroxyalkylamide. It can be carried out in bulk, that is to say in the absence of solvents, or in the presence of solvents, if appropriate in combination with other surfactants, the reaction in solution is preferred. Suitable solvents are water; lower alcohols, preferably CI to C3 alkanols such as methanol, ethanol, propanol or isopropanol; lower glycols such as ethylene glycol or propylene glycol; Oxalkylene glycols with 2 to 6 ethylene oxide and / or propylene oxide units such as diethylene glycol, dipropylene glycol, triethylene glycol, pentaethylene glycol; Mono- or di-C to C 4 alkyl ethers of lower glycols or oxalkylene glycols; and fatty alcohol alkoxylates, preferably
Fettalkoholethoxylate mit 8 bis 18 Kohlenstoffatomen im Fettalkylrest und mit 2 bis 12 Ethylenoxid-Einheiten; sowie Mischungen davon. Von den genannten Lösungsmitteln sind Wasser, C-ι_ bis Cß-Alkanole, niedere Glykole und Mischungen davon bevorzugt. Die Menge an Lösungsmittel kann in weiten Grenzen variieren. Im allgemeinen werden 5 bis 80 Gew.-% Losungsmittel eingesetzt, vorzugsweise 10 bis 70 Gew.-%, Gewichtsprozente bezogen auf die Mischung aus Fettsaurepolyhydroxyalkylamid und Losungsmittel. Es ist bevorzugt, die genannte Mischung vorzulegen und die salzbildende Saure kontinuierlich oder portionsweise in die Mischung einzurühren. Die anorganische oder organische Saure kann als solche eingesetzt werden, vorzugsweise wird sie in Form einer Losung in Wasser und/oder niederen Alkoholen eingesetzt. Nach Zugabe der Saureverbindung kann das Reaktionsgemisch zur Nachreaktion noch weitergeruhrt werden. Den Quaternisierungsverlauf kann man durch titrimetrische Bestimmung des basischen Stickstoffgehaltes im Reaktionsgemisch (Abnahme von Fettsaurepolyhydroxyalkylamid) verfolgen. Die Quaternisierung ist im allgemeinen nach 0,1 bis 2 Stunden beendet. Die angestrebte Salzbildung verläuft quantitativ und führt zur Bildung von Verbindungen der angegebenen Formel (1) , die im Falle des Einsatzes von Lösungsmitteln in Form einer Losung erhalten werden. Sofern erwünscht können die Saure-Addukte als solche gewonnen werden, zum Beispiel durch Entfernen des Lösungsmittels oder Isolierung aus dem Reaktionsgemisch.Fatty alcohol ethoxylates with 8 to 18 carbon atoms in the fatty alkyl radical and with 2 to 12 ethylene oxide units; as well as mixtures thereof. Of the solvents mentioned, water, C 1 -C 6 -alkanols, lower glycols and mixtures thereof are preferred. The amount of solvent can vary within wide limits. In general, 5 to 80% by weight of solvent are used, preferably 10 to 70% by weight, percentages by weight based on the mixture of fatty acid polyhydroxyalkylamide and solvent. It is preferred to present the mixture mentioned and to stir the salt-forming acid continuously or in portions into the mixture. The inorganic or organic acid can be used as such; it is preferably used in the form of a solution in water and / or lower alcohols. After the acid compound has been added, the reaction mixture can be stirred further for the after-reaction. The course of the quaternization can be followed by titrimetric determination of the basic nitrogen content in the reaction mixture (decrease in fatty acid polyhydroxyalkylamide). The quaternization is generally complete after 0.1 to 2 hours. The desired salt formation is proceeding quantitative and leads to the formation of compounds of formula (1), which are obtained in the form of a solution when solvents are used. If desired, the acid adducts can be obtained as such, for example by removing the solvent or isolating them from the reaction mixture.
Die erfindungsgemäßen Kompositionen sind gekennzeichnet durch einen Gehalt von mindestens 5 Gew.-%, vorzugsweise 10 bis 70 Gew.-%, bezogen auf die Komposition, von mindestens einem Saure-Addukt der Formel (1) . Bevorzugte Kompositionen bestehen im wesentlichen aus a) 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, von mindestens einem Saure-Addukt der Formel (1) als Wirkstoff und b) 30 bis 90 Gew.-%, vorzugsweise 50 bis 85 Gew.-%, von einem Lösungsmittel, bestehend im wesentlichen aus Wasser, niederen Alkoholen, niederen Glykolen oder einer Mischung davon, Gewichtsprozente bezogen auf die Komposition.The compositions according to the invention are characterized by a content of at least 5% by weight, preferably 10 to 70% by weight, based on the composition, of at least one acid adduct of the formula (1). Preferred compositions essentially consist of a) 10 to 70% by weight, preferably 15 to 50% by weight, of at least one acid adduct of the formula (1) as active ingredient and b) 30 to 90% by weight, preferably 50 to 85 wt .-%, of a solvent consisting essentially of water, lower alcohols, lower glycols or a mixture thereof, percentages by weight based on the composition.
Weitere bevorzugte Kompositionen bestehen im wesentlichen aus a') 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, von mindestens einem Saure-Addukt der Formel (1) und b') 30 bis 90 Gew.-%, vorzugsweise 50 bis 85 Gew.-%, von mindestens einem anderen kationischen und/oder anionischen und/oder nichtionischen und/oder amphoteren Tensid, Gewichtsprozente bezogen auf dieFurther preferred compositions essentially consist of a ') 10 to 70% by weight, preferably 15 to 50% by weight, of at least one acid adduct of the formula (1) and b') 30 to 90% by weight, preferably 50 to 85% by weight of at least one other cationic and / or anionic and / or nonionic and / or amphoteric surfactant, percentages by weight based on the
Komposition. Diese Kompositionen können als solche, das heißt frei von Losungsmitteln, oder in Form einer Losung vorliegen, wobei das Lösungsmittel Wasser, niedere Alkohole, niedere Glykole oder eine Mischung davon ist. Die Losungen enthalten im allgemeinen 10 bis 70 Gew.-%, vorzugsweise 15 bis 50 Gew.-%, der Summe der Komponenten a') und b'). Geeignete andere kationische Tenside sind zum Beispiel die üblichen quartaren Ammoniumverbindungen mit vier Alkylresten am Stickstoffatom und quartareComposition. These compositions can be present as such, ie free of solvents, or in the form of a solution, the solvent being water, lower alcohols, lower glycols or a mixture thereof. The solutions generally contain 10 to 70% by weight, preferably 15 to 50% by weight, of the sum of components a ') and b'). Suitable other cationic surfactants are, for example, the usual quaternary ammonium compounds with four alkyl radicals on the nitrogen atom and quaternary ones
Carbonsaureethanolaminester-Salze (Esterquats) . Geeignete anionische Tenside sind zum Beispiel Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, Alkylsulfate, Fettalkoholethersulfate,Carboxylic acid ethanolamine ester salts (esterquats). Suitable anionic surfactants are, for example, alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, alkyl sulfates, fatty alcohol ether sulfates,
Glycerinethersulfate, Fettsaureamid(ether) Sulfate, Sulfosuccinate, Sarcosmate und Tauride. Geeignete nichtionische Tenside sind zum Beispiel Fettsaurepolyhydroxyalkylamide, Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsaurepolyglycolester, Fettsaureamidpolyglycolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Sorbitanester und Alkylpolyglycoside. Geeignete amphotere oder zwitterionische Tenside sind zum Beispiel Alkylbetaine, Alkylamidobetaine,Glycerin ether sulfates, fatty acid amide (ether) sulfates, sulfosuccinates, sarcosmates and taurides. Suitable nonionic surfactants are, for example, fatty acid polyhydroxyalkylamides, fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, sorbitan esters and alkyl polyglycosides. Suitable amphoteric or zwitterionic surfactants are, for example, alkyl betaines, alkyl amido betaines,
Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine.Aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
Die erfindungsgemaßen Kompositionen werden durch Zusammenmischen der angegebenen Komponenten bei etwaThe compositions according to the invention are obtained by mixing the specified components together at approximately
15 bis 100 CC hergestellt oder werden bereits im Rahmen der Herstellung von Saure-Addukten der Formel (1) erhalten, worauf gegebenenfalls weitere Tenside hinzugefugt werden können. Die erfindungsgemaßen Salzverbindungen der Formel (1) und ihre Kompositionen weisen ein unerwartet hohes Schaumvermogen auf und stellen deshalb ein hervorragendes Schaummittel dar. Aufgrund ihrer weiteren Eigenschaften wie gute Hautvertraglichkeit und hohe Verdickbarkeit werden sie ferner vorteilhaft als Wasch- und Kosmetiktenside, vorzugsweise als Haar- und Korperpflegemittel, verwendet.15 to 100 C C are prepared or are already obtained in the course of the production of acid adducts of the formula (1), whereupon further surfactants can optionally be added. The salt compounds of the formula (1) according to the invention and their compositions have an unexpectedly high foaming capacity and therefore represent an excellent foaming agent. Because of their further properties, such as good skin tolerance and high thickenability, they are also advantageous as detergents and cosmetics, preferably as hair and Personal care products used.
Die Erfindung wird nun an Beispielen undThe invention will now be illustrated by examples and
Vergleichsbeispielen noch naher erläutert.Comparative examples explained in more detail.
Herstellung von Fettsaurepolyhydroxyalkylamid C12 /14-Dimethylaminopropyl-Glucamid (DMAP-GA) :Preparation of Fettsaurepolyhydroxyalkylamid C 12/14 dimethylaminopropyl glucamide (DMAP-GA):
304,5 g einer 41gew.%igen wäßrigen Losung eines technischen N-(3-Dimethylamino) -propylglucamins (im folgenden DMAP-G) mit einem DMAP-G-Gehalt von 96 Gew.-%, bezogen auf Festsubstanz (das sind 0,45 mol DMAP-G) , werden mit Hilfe einer üblichen Strippapparatur entwässert. Dazu wird die Losung auf etwa 100 'C erhitzt und zunächst bei Normaldruck bis zu einem Restwassergehalt von etwa 5 Gew.-I entwassert. Die Losung wird nun zur weiteren Entwässerung auf 130 °C erhitzt und bei dieser Temperatur gehalten, wobei schrittweise ein Vakuum von bis zu 25 mbar angelegt wird. Es wird bis zu einem Restwassergehalt von 0,2 Gew.-% entwassert. Zur so erhaltenen Schmelze werden bei 130 °C unter Rühren 104,1 g (0,473 mol)304.5 g of a 41% by weight aqueous solution of a technical N- (3-dimethylamino) propylglucamine (hereinafter DMAP-G) with a DMAP-G content of 96% by weight, based on the solid substance (that is 0 , 45 mol DMAP-G) are dewatered using a conventional stripping apparatus. For this purpose, the solution is heated to about 100 ° C. and first dewatered at normal pressure to a residual water content of about 5% by weight. The solution is then heated to 130 ° C. for further dewatering and kept at this temperature, a vacuum of up to 25 mbar being gradually applied. It is dewatered up to a residual water content of 0.2% by weight. 104.1 g (0.473 mol) are stirred into the melt thus obtained at 130 ° C.
C12 /14-Fettsauremethylester (Molmasse 220 g/mol, nach Verseifungszahl) gegeben. Die Mischung hat eine Temperatur von 120 °C. Nun werden noch 6,1 g Natriummethylat (30gew.%ig in Methanol, 7,5 Mol-%, bezogen auf DMAP-G) innerhalb von 3 Minuten zugetropft und die Reaktionsmischung bei etwa 100 'C gehalten. Das durch die Reaktion entstehende Methanol wird zunächst im System belassen. Nach etwa 20 Minuten liegt eine klare Reaktionslösung vor. Nun wird ein Vakuum von 60 mbar angelegt und eine Temperatur von circa 95 ° C eingestellt, wobei die Reaktionsmischung etwa 80 Minuten unter Abdestillation des Methanols weiterreagiert. Die so erhaltene Losung enthält circa 90 Gew.-% C12 /14-DMAP-GA, bezogen auf den Feststoffanteil.C 12/14 -Fettsauremethylester (molecular weight 220 g / mol, after saponification) was added. The mixture has a temperature of 120 ° C. Now 6.1 g of sodium methylate (30% by weight in methanol, 7.5 mol%, based on DMAP-G) was added dropwise within 3 minutes and the reaction mixture was kept at about 100 ° C. The methanol resulting from the reaction is initially left in the system. After about 20 minutes there is a clear reaction solution. A vacuum of 60 mbar is now applied and a temperature of approximately 95 ° C. is set, the reaction mixture continuing to react for about 80 minutes while the methanol is distilled off. The solution thus obtained contains about 90 wt .-% C 12/14 -DMAP-GA, based on the solids content.
Beispiel 1example 1
Herstellung von C12 /14-DMAP-GA-Hydrochlorid (Addukt 1) OH OHPreparation of C 12/14 -DMAP-GA-hydrochloride (adduct 1) OH OH
Zu einer 50gew.%igen wäßrigen Losung von C12 /14-DMAP-GA wird unter Rühren bei 70 °C innerhalb 20 Minuten eine aquimolare Menge konzentrierter Salzsäure zugetropft; anschließend laßt man die das erfindungsgemaße Produkt enthaltende Losung - bei Bedarf ist eine Isolierung des Saure-Addukts selbstverständlich möglich - unter fortgesetztem Ruhren erkalten.. To a 50% aqueous solution of C 12/14 -DMAP-GA is added dropwise with stirring at 70 ° C over 20 minutes an equimolar amount of concentrated hydrochloric acid; the solution containing the product according to the invention is then allowed to cool, with isolation of the acid adduct possible if necessary, with continued stirring.
Beispiel 2Example 2
Herstellung von C12/14-DMAP-GA-Milchsaure-Addukt (Addukt 2) : OH OH OHPreparation of C 12/14 -DMAP-GA-lactic acid adduct (adduct 2): OH OH OH
Das erfindungsgemäße Lactat (Addukt 2) wird hergestellt, indem man analog Beispiel 1 anstelle von Salzsaure eine wäßrige Milchsaurelosung zutropft; gegebenenfalls ist das geloste Produkt durch Abdestillation des Wassers naturlich auch in Substanz zu erhalten.The lactate according to the invention (adduct 2) is prepared by adding an aqueous solution of lactic acid instead of hydrochloric acid analogously to Example 1; if necessary, the dissolved product can of course also be obtained in substance by distilling off the water.
Die erfindungsgemaßen Losungen von Addukt 1 und Addukt 2 werden mit einer Losung des entsprechenden N-methylierten Quats (mit Chlorid als Gegenion) - dessen Herstellung erfolgt durch Umsetzung von C12 /14-DMAP-GA mit Methylchlorid analog DE-A-42 38 207 - verglichen, das ist C12/,14-DMAP-GA-Methylchlorid-Quat (Addukt 3) :The novel solutions of adduct 1 and adduct 2 were mixed with a solution of the corresponding N-methylated quats (with chloride as a counter ion) - whose preparation is carried out by reaction of C 12/14 -DMAP-GA with methylene chloride analogously to DE-A-42 38 207 - compared, this is C 12 / , 14- DMAP-GA-methyl chloride quat (adduct 3):
Vergleichsbeispiel 1Comparative Example 1
Schaumvermogen:Foam:
Die überraschenden Eigenschaften des Hydrochlorids (Addukt 1) und des Lactats (Addukt 2) gegenüber dem Methylchlorid-Quat (Addukt 3) zeigen sich beispielsweise beim Schaumvermogen der Einzeltenside. So weist die nach Ross-Miles (Temperatur 37 °C, Wasserharte 15° dH, Zeit: sofort/5 Minuten) bestimmte Schaumhohe in Millimetern bereits bei einer kritischen Konzentration von 0,03 % WAS (wirkungsaktive Substanz) über einen pH-Bereich von 4 bis 9 signifikante Unterschiede auf, wie die nachstehende Zusammenfassung zeigt (die Messung von Addukt 2 wird nur bei pH 7 durchgeführt) .The surprising properties of the hydrochloride (adduct 1) and the lactate (adduct 2) compared to the methyl chloride quat (adduct 3) are evident for example when the individual surfactants foam. According to Ross-Miles (temperature 37 ° C, water hardness 15 ° dH, time: immediately / 5 minutes), the foam height in millimeters already shows at a critical concentration of 0.03% WAS (active substance) over a pH range of 4 to 9 significant differences, as the summary below shows (the measurement of adduct 2 is only carried out at pH 7).
Vergleichsbeispiel 2Comparative Example 2
Viskositatsbeeinflussung: Bemerkenswert ist auch die unterschiedlicheInfluence on viscosity: The difference is also remarkable
Verdickbarkeit in Kombination mit Ethersulfat (als Einzeltensid lassen sich alle drei Produkte nicht verdicken!) unter neutralen Bedingungen (pH 7). Untersucht wurden Mischungen mit ®Genapol LRO (• = eingetragenes Warenzeichen von Hoechst) , einem durch Oxalkylierung eines C12/14-Fettalkohols mit 2 Moläquivalenten Ethylenoxid und anschließende Sulfierung hergestelltem Natriumethersulfat (Ethersulfat : Prufprodukt = 7 : 3) bei 15 % WAS (Meßgroße mPas) : NaCl-Zusatz Addukt 1 Addukt 2 Addukt 3Thickenability in combination with ether sulfate (all three products cannot be thickened as a single surfactant!) Under neutral conditions (pH 7). Analyzes were mixtures ® Genapol LRO (• = registered trade mark of Hoechst), a by oxyalkylation of a C 12/14 fatty alcohol with 2 molar equivalents of ethylene oxide, followed by sulfonation prepared Natriumethersulfat (ether sulfate: Prufprodukt = 7: 3) at 15% WAS (measured quantity mPas): Addition of NaCl adduct 1 adduct 2 adduct 3
ohne Zusatz < 100 26 000 < 100without addition <100 26 000 <100
+ 0,5 % 2 100 20 000 2 000+ 0.5% 2 100 20 000 2 000
+ 1,0 % 23 000 15 000 6 700+ 1.0% 23,000 15,000 6,700
+ 2,0 % Gel 21 000 20 000+ 2.0% gel 21,000 20,000
+ 3,0 % Gel nicht bestimmt 30 000+ 3.0% gel not determined 30,000
+ 4,0 % Gel nicht bestimmt 31 000+ 4.0% gel not determined 31,000
+ 5,0 % Gel nicht bestimmt 17 000+ 5.0% gel not determined 17 000
Daß sich das Lactat (Addukt 2) ohne Elektrolyt-Zusatz stark verdicken läßt, ist absolut außergewöhnlich und für verschiedene Spezialanwendungen von großem Interesse. The fact that the lactate (adduct 2) can be greatly thickened without the addition of electrolytes is absolutely exceptional and of great interest for various special applications.

Claims

AnsprücheExpectations
1. Saure-Addukte von Fettsaurepolyhydroxyalkylamiden der nachstehenden Formel (1)1. Acid adducts of fatty acid polyhydroxyalkylamides of the following formula (1)
CO-R RlCO-R Rl
Z-N-(CH2)X-N+-R2 A~ (1) |ZN- (CH 2 ) X -N + -R 2 A ~ (1) |
HH
worinwherein
Z ein reduzierter Glycosidrest oder Oligoglycosidrest mit 2 bis 6 Glycose-Z is a reduced glycoside residue or oligoglycoside residue with 2 to 6 glycose
Einheiten, x eine ganze Zahl von 2 bis 4, R1 ein C-^ bis C4-Alkyl oder C2 bis C4-Hydroxyalkyl, R2 ein Cχ bis C4-Alkyl oderUnits, x is an integer from 2 to 4, R 1 is a C 1 -C 4 -alkyl or C 2 to C 4 hydroxyalkyl, R 2 is a C χ to C 4 alkyl or
C2 bis C4-Hydrσxyalkyl, CO-R ein aliphatischer Acylrest mit 6 bisC 2 to C 4 -Hydrσxyalkyl, CO-R an aliphatic acyl radical with 6 to
22 Kohlenstoffatomen und A" ein Anionrest einer anorganischen oder organischen Saure ist.22 carbon atoms and A "is an anionic residue of an inorganic or organic acid.
2. Saure-Addukte nach Anspruch 1, dadurch gekennzeichnet, daß2. Acid adducts according to claim 1, characterized in that
Z ein reduzierter Glycosidrest oder ein Oligoglycosidrest mit 2 oder 3 Glycose-Z is a reduced glycoside residue or an oligoglycoside residue with 2 or 3 glycose
Einheiten, x 3,Units, x 3,
R1 und R2 Methyl oder Ethyl undR 1 and R 2 are methyl or ethyl and
CO-R ein Fettacylrest mit 8 bis 18 Kohlenstoffatomen ist. 3. Saure-Addukte nach Anspruch 1 oder 2 , dadurch gekennzeichnet, daß A~ ein Anionrest einer Mineralsaure oder Carbonsaure ist.CO-R is a fatty acyl radical having 8 to 18 carbon atoms. 3. Acid adducts according to claim 1 or 2, characterized in that A ~ is an anionic residue of a mineral acid or carboxylic acid.
4. Saure-Addukte nach Anspruch 1 oder 2 , dadurch gekennzeichnet, daß A~ ein Halogenid, Carbonat, Phosphat, Nitrat oder Sulfat oder ein Carboxylat ist.4. Acid adducts according to claim 1 or 2, characterized in that A ~ is a halide, carbonate, phosphate, nitrate or sulfate or a carboxylate.
5. Saure-Addukte nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß A~ ein Carboxylat ist.5. Acid adducts according to claim 1 or 2, characterized in that A ~ is a carboxylate.
6. Verfahren zur Herstellung von Saure-Addukten nach Anspruch 1, dadurch gekennzeichnet, daß man ein Fettsaurepolyhydroxyalkylamid der nachstehenden Formel (2)6. A process for the preparation of acid adducts according to claim 1, characterized in that a fatty acid polyhydroxyalkylamide of the following formula (2)
CO-R Rl Z-N 1-(CH2)χ-N l-R 22 (2)CO-R Rl ZN 1 - (CH 2 ) χ -N l -R 2 2 (2)
worin Z, x, R1, R2 und CO-R die angegebenen Bedeutungen haben, mit einer Saure der nachstehenden Formel (3)wherein Z, x, R 1 , R 2 and CO-R have the meanings given, with an acid of the formula (3) below
HA (3)HA (3)
worin A die genannte Bedeutung hat, zum Saure-Addukt der Formel (1) umsetzt.where A has the meaning given, is converted to the acid adduct of the formula (1).
Kompositionen, gekennzeichnet durch einen Gehalt von mindestens 5 Gew.-%, bezogen auf die Komposition, von mindestens einem Saure-Addukt nach Anspruch 1. 8. Kompositionen nach Anspruch 7, dadurch gekennzeichnet, daß der Gehalt an Säure-Addukt 10 bis 70 Gew.-% beträgt.Compositions characterized by a content of at least 5% by weight, based on the composition, of at least one acid adduct according to claim 1. 8. Compositions according to claim 7, characterized in that the content of acid adduct is 10 to 70 wt .-%.
9. Kompositionen nach Anspruch 7, dadurch gekennzeichnet, daß sie im wesentlichen bestehen aus a) 10 bis 70 Gew.-% von dem Saure-Addukt und b) 30 bis 90 Gew.-I von einem Losungsmittel, wobei das Losungsmittel im wesentlichen aus Wasser, niederen Alkoholen, niederen Glykolen oder einer Mischung davon gebildet ist, Gewichtsprozente bezogen auf die Komposition.9. Compositions according to claim 7, characterized in that they consist essentially of a) 10 to 70% by weight of the acid adduct and b) 30 to 90% by weight of a solvent, the solvent consisting essentially of Water, lower alcohols, lower glycols or a mixture thereof is formed, percentages by weight based on the composition.
10. Kompositionen nach Anspruch 7, dadurch gekennzeichnet, daß sie im wesentlichen bestehen aus a') 10 bis 70 Gew.-% von dem Saure-Addukt und b*) 30 bis 90 Gew.-% von mindestens einem anderen kationischen und/oder anionischen und/oder nichtionischen und/oder amphoteren Tensid, Gewichtsprozente bezogen auf die Komposition.10. Compositions according to claim 7, characterized in that they consist essentially of a ') 10 to 70 wt .-% of the acid adduct and b *) 30 to 90 wt .-% of at least one other cationic and / or anionic and / or nonionic and / or amphoteric surfactant, percentages by weight based on the composition.
11. Kompositionen nach Anspruch 10, dadurch gekennzeichnet, daß sie als 10 bis 70gew.%ige11. Compositions according to claim 10, characterized in that they are 10 to 70% by weight
Lösungen in Wasser, niederen Alkoholen, niederen Glykolen oder einer Mischung davon als Lösungsmittel vorliegen, Gewichtsprozente bezogen auf die Losung.Solutions in water, lower alcohols, lower glycols or a mixture thereof are present as solvents, percentages by weight based on the solution.
12. Verwendung der Saure-Addukte nach Anspruch 1 als Schaummittel und Verdickungsmittel.12. Use of the acid adducts according to claim 1 as a foaming agent and thickener.
13. Verwendung der Kompositionen nach Anspruch 7 als Schaummittel und Verdickungsmittel. 13. Use of the compositions according to claim 7 as foaming agents and thickeners.
EP97925021A 1996-06-08 1997-05-30 Acid addition compounds of fatty acid polyhydroxy alkyl amides Withdrawn EP0906269A1 (en)

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DE19622981A DE19622981A1 (en) 1996-06-08 1996-06-08 Acid adducts of fatty acid polyhydroxyalkylamides
DE19622981 1996-06-08
PCT/EP1997/002811 WO1997047591A1 (en) 1996-06-08 1997-05-30 Acid addition compounds of fatty acid polyhydroxy alkyl amides

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EP1314718A1 (en) * 2001-11-23 2003-05-28 Cognis Iberia, S.L. Quaternised fatty acid amidoamines
EP1894989A1 (en) * 2006-09-01 2008-03-05 The Procter and Gamble Company Pasty Composition for Sanitary Ware
US11116220B2 (en) 2017-12-22 2021-09-14 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy

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DE4238207A1 (en) * 1992-11-12 1994-05-19 Henkel Kgaa New quat. fatty acid poly:hydroxy:alkylamide(s) - useful in prodn. of antistatic agents for tissue and textile surfaces
DE4238211C2 (en) * 1992-11-12 1997-11-13 Henkel Kgaa Use of detergent mixtures containing cationic sugar surfactants and other surfactants for the production of softeners
US5534197A (en) * 1994-01-25 1996-07-09 The Procter & Gamble Company Gemini polyhydroxy fatty acid amides
US5512699A (en) * 1994-01-25 1996-04-30 The Procter & Gamble Company Poly polyhydroxy fatty acid amides
DE19512299A1 (en) * 1995-04-05 1996-10-10 Hoechst Ag New N-acyl-N-poly:hydroxy-hydrocarbyl di:amino-propane

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