EP0069948A1 - Quaternary N-alkyl-N,N'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use - Google Patents

Quaternary N-alkyl-N,N'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use Download PDF

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EP0069948A1
EP0069948A1 EP82105949A EP82105949A EP0069948A1 EP 0069948 A1 EP0069948 A1 EP 0069948A1 EP 82105949 A EP82105949 A EP 82105949A EP 82105949 A EP82105949 A EP 82105949A EP 0069948 A1 EP0069948 A1 EP 0069948A1
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alkyl
formula
compounds
methyl
quaternary
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EP0069948B1 (en
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Siegfried Dr. Billenstein
Herbert Dr. Hartung
Adolf Dr. May
Hans-Walter Dr. Bücking
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the compounds of formula (1) are obtained by using a compound of formula (2) in which R 1 , x, y, m, n and p have the meanings given in formula (1), with a fatty acid of the formula 3 wherein R 3 has the meaning given in formula (1), esterified and the reaction product obtained quaternized with an alkylating reagent with the addition of the radical R 2 .
  • the preparation of the compounds of formula (1) starts from the compounds of formula (2). They are obtained by known methods by oxalkylation of fatty alkyl alkylene diamines such as. B. tallow fat propylene diamine (Schönfeldt, Surface active Ethylene Oxide Adducts 1969 p. 97).
  • the esterification of these compounds is carried out by known methods with a fatty acid in higher-boiling inert solvents such as toluene or xylene or preferably without solvent in the melt and covered with a protective gas.
  • the reflux temperature of the reaction mixture is chosen as the reaction temperature and the water of reaction formed is removed azeotropically.
  • the water of reaction is distilled off directly from the reaction mixture. Aturen
  • the reaction Tempen are here at 140 to 220 ° C, preferably at 150 to 180 o C. using an acid catalyst to accelerate the reaction such as p-toluenesulfonic: onklarc. The completeness of the reaction is checked by determining the acid number.
  • the molar ratio of fatty acid to the compound of the formula (2) is 1 to 3, preferably 1 to 1.9 mol, of fatty acid to 1 mol of the compound of the formula 2.
  • the resulting mixture of the fatty acid ester is then dissolved in an alcohol, or dispersed in water and reacted with an alkylating agent at temperatures below 100 o C, preferably at 40 to 80 ° C to give the novel quaternary products.
  • This reaction can also be carried out without any solvent.
  • the water or the solvent has been distilled off, the compounds of the formula (1) are thus obtained.
  • the reaction mixture is adjusted to a pH of 6 to 7 by adding alkali and this solution is used directly as a fabric softener, optionally after appropriate dilution with water to the desired concentration and confection.
  • Preferred diamines on which the starting compounds of formula (2) are based are the industrially available products tallow fat propylene diamine or stearyl propylene diamine. However, it is equally possible according to the invention to use other diamines with a more or less broad alkyl chain distribution. Such diamines are produced in a known manner by adding acrylonitrile to primary fatty amines and then catalytically hydrogenating the propionitriles.
  • Fatty acids suitable for esterification are products on a natural or synthetic basis, such as, for example, palmitic acid, stearic acid, behenic acid, or branched-chain compounds from oxo synthesis, such as, for example, isostearic acid or mixtures of the above, such as those obtained from natural ones Cuts are made that are derived from coconut oil or tallow.
  • the alkylating agent used is preferably methyl chloride or dimethyl sulfate.
  • the compounds of the formula (1) according to the invention are suitable as fabric softeners and are in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4 to 10% by weight, of the compounds of the formula (1) after the laundry the textile material in the last rinsing bath. The textile material is then dried.
  • These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include, for example, cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers as well as colors and fragrances.
  • the products are used to additionally influence the handle of the goods or other properties of the textiles to be treated, or to adjust the viscosity, regulate the pH or increase the cold stability of the solutions.
  • the compounds according to the invention give any textile materials, especially those made of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel.
  • Use as a laundry treatment agent for terry towels and underwear is particularly advantageous.
  • coconut fatty acid, oleic acid or tallow fatty acid derivatives can be obtained in an analogous manner.
  • 177 g of distearic acid ester prepared according to 1. is mixed in a stirred flask with 180 g of isopropanol and heated to 40 to 50 ° C. At this temperature, 48 g of dimethyl sulfate are added dropwise within about 30 minutes. After 3 hours, 12 g of sodium methylate solution (35% in methanol) and 9 g of dimethyl sulfate are added and the mixture is stirred at about 50 ° C. for a further 2 hours. After adding a further 9 g of sodium methylate solution, which brought the pH to 6.6 and cooling to room temperature, the product can be used in fabric softener formulations.

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  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

Quartäre N-Alkyl,-N,N',N'-polyoxyalkyl-α,ω-diamino-alkylenfettsäur-ester der Formel (1) <IMAGE> worin R1 C8-C30 Alkyl oder C8-C30 Alkenyl, R2 C1-C4-Alkyl, R3 C7-C29 Alkyl der C7-C29-Alkenyl, x und y Wasserstoff oder Methyl, wobei x und y jedoch nicht gleichzeitig Methyl darstellen, a 0, 1 oder 2, n eine Zahl von 1 bis 11, vorzugsweise 1, m 1 oder 2, p eine Zahl von 1 bis 5, vorzugsweise 3 und A ein Anion, vorzugsweise ein Halogen-, Methosulfat- oder methophosphation bedeuten. Diese Verbindungen werden hergestellt durch Veresterung der zugrundeliegenden oxalkylierten Alkylendiamine mit Fettsäuren und anschließende Quaternisierung. Man verwendet diese Verbindungen als Wäscheweichspülmittel.Quaternary N-alkyl, -N, N ', N'-polyoxyalkyl-α, ω-diamino-alkylene fatty acid esters of the formula (1) <IMAGE> in which R1 is C8-C30 alkyl or C8-C30 alkenyl, R2 is C1-C4- Alkyl, R3 C7-C29 alkyl of C7-C29 alkenyl, x and y are hydrogen or methyl, where x and y are not methyl at the same time, a 0, 1 or 2, n is a number from 1 to 11, preferably 1, m 1 or 2, p is a number from 1 to 5, preferably 3 and A is an anion, preferably a halogen, methosulfate or methophosphate ion. These compounds are produced by esterification of the underlying alkoxylated alkylenediamines with fatty acids and subsequent quaternization. These compounds are used as fabric softeners.

Description

Gegenstand der Erfindung sind quartäre N-Alkyl-N,N',N'-poly- oxyalkyl-α,ω-diaminoalkylen-fettsäureester der Formel (1)

Figure imgb0001
worin

  • R, C8-C30-, vorzugsweise C16-C18-Alkyl oder C8-C30-, vorzugsweise C16-C18-Alkenyl ,
  • R2 C1-C4-Alkyl, vorzugsweise Methyl, R3 C7-C29-, vorzugs-weise C15-C17-Alkyl oder C7-C29-, vorzugsweise C15-C17-Alkenyl,
  • x und y Wasserstoff oder Methyl, wobei x und y jedoch nicht gleichzeitig Methyl darstellen,
  • a 0, 1 oder 2,
  • n eine Zahl von 1 bis 11, vorzugsweise 1,
  • m 1 oder 2,
  • p eine Zahl von 1 bis 5 , vorzugsweise 3 und
  • A ein Anion, vorzugsweise ein Halogen-, Methosulfat- oder Methophosphation bedeuten.
The invention relates to quaternary N-alkyl-N, N ', N'-polyoxyalkyl-α, ω-diaminoalkylene fatty acid esters of the formula (1)
Figure imgb0001
 wherein
  • R, C 8 -C 30 -, preferably C 16 -C 18 alkyl or C 8 -C 30 -, preferably C 16 -C 18 alkenyl,
  • R 2 C 1 -C 4 alkyl, preferably methyl, R 3 C 7 -C 29 -, preferably g s-wise C 15 -C 17 alkyl or C 7 -C 29 -, preferably C 15 -C 17 alkenyl ,
  • x and y are hydrogen or methyl, but x and y are not methyl at the same time,
  • a 0, 1 or 2,
  • n is a number from 1 to 11, preferably 1,
  • m 1 or 2,
  • p is a number from 1 to 5, preferably 3 and
  • A is an anion, preferably a halogen, methosulfate or methophosphate ion.

Die Verbindungen der Formel (1) werden erhalten, indem man eine Verbindung der Formel (2)

Figure imgb0002
in der R1, x, y, m, n und p die in Formel (1) angegebenen Bedeutungen haben, mit einer Fettsäure der Formel 3
Figure imgb0003
worin R3 die in Formel (1) angegebene Bedeutung hat, verestert und das erhaltene Reaktionsprodukt mit einem Alkylierungsreagenz unter Einfügung des Restes R2 quaterniert.The compounds of formula (1) are obtained by using a compound of formula (2)
Figure imgb0002
 in which R 1 , x, y, m, n and p have the meanings given in formula (1), with a fatty acid of the formula 3
Figure imgb0003
 wherein R 3 has the meaning given in formula (1), esterified and the reaction product obtained quaternized with an alkylating reagent with the addition of the radical R 2 .

Die Herstellung der Verbindungen der Formel (1) geht aus von den Verbindungen der Formel (2). Sie werden erhalten nach bekannten Verfahren durch Oxalkylierung von Fettalkyl-alkylendiaminen wie z. B. Talgfettpropylendiamin (Schönfeldt, Surface active Ethyleneoxide Adducts 1969 S. 97). Die Veresterung dieser Verbindungen erfolgt nach bekannten Methoden mit einer Fettsäure in höhersiedenden inerten Lösungsmitteln wie Toluol oder Xylol oder bevorzugt ohne Lösungsmittel in der Schmelze und unter Abdeckung mit einem Schutzgas. Bei Versterung in einem Lösungsmittel wählt man als Reaktionstemperatur die Ruckflußtemperatur des Reaktionsgemisches und entfernt das gebildete Reaktionswasser azeotnop. Bei Veresterung in Substanz wird das Reaktionswasser direkt aus der Reaktionsmischung abdestilliert. Die Reaktionstempen aturen liegen hier bei 140 bis 220°C, bevorzugt bei 150 bis 180oC. Zur Beschleunigung der Reaktion verwendet man einen sauren Katalysator wie z.B. p-Toluolsul:onsäurc. Die Vollständigkeit der Reaktion wird über die Bestimmung der Säurezahl kontrolliert.The preparation of the compounds of formula (1) starts from the compounds of formula (2). They are obtained by known methods by oxalkylation of fatty alkyl alkylene diamines such as. B. tallow fat propylene diamine (Schönfeldt, Surface active Ethylene Oxide Adducts 1969 p. 97). The esterification of these compounds is carried out by known methods with a fatty acid in higher-boiling inert solvents such as toluene or xylene or preferably without solvent in the melt and covered with a protective gas. In the case of esterification in a solvent, the reflux temperature of the reaction mixture is chosen as the reaction temperature and the water of reaction formed is removed azeotropically. In the case of esterification in bulk, the water of reaction is distilled off directly from the reaction mixture. Aturen The reaction Tempen are here at 140 to 220 ° C, preferably at 150 to 180 o C. using an acid catalyst to accelerate the reaction such as p-toluenesulfonic: onsäurc. The completeness of the reaction is checked by determining the acid number.

Das Molverhältnis von Fettsäure zur Verbindung der Formel (2) beträgt 1 bis 3, vorzugsweise 1 bis 1,9 Mol Fettsäure auf 1 Mol der Verbindung der Formel 2. Entsprechend dem gewählten Molverhältnis erhält man ein Gemisch der mono-, di- und tri-Fettsäureester, vorzugsweise ein Gemisch, das hauptsächlich die mono- und die di-Ester enthält.The molar ratio of fatty acid to the compound of the formula (2) is 1 to 3, preferably 1 to 1.9 mol, of fatty acid to 1 mol of the compound of the formula 2. A mixture of the mono-, di- and tri- Fatty acid esters, preferably a mixture mainly containing the mono- and di-esters.

Das so erhaltene Gemisch der Fettsäureester wird dann in einem Alkohol gelöst oder in Wasser dispergiert und mit einem Alkylierungsmittel bei Temperaturen unter 100oC, vorzugsweise bei 40 bis 80°C zu den erfindungsgemäßen quaternären Produkten umgesetzt. Man kann diese Reaktion auch ohne jedes Lösungsmittel durchführen. Nach Abdestillieren des Wassers oder des Lösungsmittels erhält man so die Verbindungen der Formel (1). Nach einer bevorzugten Ausführungsform stellt man nach der Alkylierung das Reaktionsgemisch durch Zugabe von Alkali auf einen pH-Wert von 6 bis 7 und verwendet diese Lösung direkt weiter als Wäscheweichspülmittel, gegebenenfalls nach entsprechender Verdünnung mit Wasser auf die gewünschte Konzentration und Konfektionierung.The resulting mixture of the fatty acid ester is then dissolved in an alcohol, or dispersed in water and reacted with an alkylating agent at temperatures below 100 o C, preferably at 40 to 80 ° C to give the novel quaternary products. This reaction can also be carried out without any solvent. After the water or the solvent has been distilled off, the compounds of the formula (1) are thus obtained. According to a preferred embodiment, after the alkylation, the reaction mixture is adjusted to a pH of 6 to 7 by adding alkali and this solution is used directly as a fabric softener, optionally after appropriate dilution with water to the desired concentration and confection.

Bevorzugte Diamine, die den Ausgangsverbindungen der Formel (2) zugrunde liegen, sind die technisch verfügbaren Produkte Talgfettpropylendiamin oder Stearylpropylendiamin. Es ist aber gemäß der Erfindung ebensogut möglich, andere Diamine mit mehr oder weniger breiter Alkylkettenverteilung zu verwenden. Solche Diamine werden in bekannter Weise durch Anlagerung von Acrylnitril an primäre Fettamine und anschließende katalytische Hydrierung der Propionitrile hergestellt.Preferred diamines on which the starting compounds of formula (2) are based are the industrially available products tallow fat propylene diamine or stearyl propylene diamine. However, it is equally possible according to the invention to use other diamines with a more or less broad alkyl chain distribution. Such diamines are produced in a known manner by adding acrylonitrile to primary fatty amines and then catalytically hydrogenating the propionitriles.

Zur Veresterung geeignete Fettsäuren sind Produkte auf natürlicher oder synthetischer Basis, wie z.B. Palmitinsäure, Stearinsäure, Behensäure oder verzweigtkettige Verbindungen aus der Oxo-Synthese, wie z.B. Isostearinsäure bzw. Gemische der genannten, wie sie z.B. aus natürlichen Schnitten anfallen, die sich vom Cocosöl oder Talg ableiten. Als Alkylierungsmittel verwendet man zweckmäßigerweise bevorzugt Methylchlorid oder Dimethylsulfat.Fatty acids suitable for esterification are products on a natural or synthetic basis, such as, for example, palmitic acid, stearic acid, behenic acid, or branched-chain compounds from oxo synthesis, such as, for example, isostearic acid or mixtures of the above, such as those obtained from natural ones Cuts are made that are derived from coconut oil or tallow. The alkylating agent used is preferably methyl chloride or dimethyl sulfate.

Die erfindungsgemäßen Verbindungen der Formel (1) eignen sich als Wäscheweichspülmittel und werden in Form wäßriger Dispersionen mit einem Wirksubstanzgehalt von 1 bis 15 Gew.-%, meist 4 bis 10 Gew.-% der Verbindungen der Formel (1) im Anschluß an die Wäsche des Textilmaterials in das letzte Spülbad gegeben. Danach wird das Textilmaterial getrocknet. Diese Wäscheweichspülmittel können außerdem noch weitere Substanzen und Hilfsmittel enthalten, wie sie üblicherweise in Wäscheweichspülmitteln mitverwendet werden. Hierzu gehören z.B, kationische oder nichtionische oberflächenaktive Substanzen, Elektrolyte, Absäuerungsmittel, organische Komplexbildner, optische Aufheller oder Lösungsvermittler sowie Farb- und Duftstoffe. Die Produkte dienen zur zusätzlichen Beeinflussung des Warengriffs oder sonstiger Eigenschaften der zu behandelnden Textilien oder zur' Viskositätseinstellung, der pH-Regulierung oder zur Erhöhung der Kältestabilität der Lösungen.The compounds of the formula (1) according to the invention are suitable as fabric softeners and are in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4 to 10% by weight, of the compounds of the formula (1) after the laundry the textile material in the last rinsing bath. The textile material is then dried. These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include, for example, cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers as well as colors and fragrances. The products are used to additionally influence the handle of the goods or other properties of the textiles to be treated, or to adjust the viscosity, regulate the pH or increase the cold stability of the solutions.

Die Verbindungen gemäß der Erfindung verleihen beliebigen Textilmaterialien, besonders solchen aus natürlicher oder regenerierter Cellulose, Wolle, Celluloseacetat, Triacetat, Polyamid, Polyacrylnitril, Polyester, Polypropylen-einen angenehmen und weichen Griff. Besonders vorteilhaft ist der Einsatz als Wäschenachbehandlungsmittel für Frottee- und Leibwäsche.The compounds according to the invention give any textile materials, especially those made of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel. Use as a laundry treatment agent for terry towels and underwear is particularly advantageous.

BEISPIELEXAMPLE 1. Herstellung von N-C16-C18-alkyl-H,N',N'-tris-(2-hydroxyethyl)-1,3-diaminopropan-di-stearinsäureester1. Preparation of NC 16 -C 18 alkyl-H, N ', N'-tris- (2-hydroxyethyl) -1,3-diaminopropane-di-stearic acid ester

In einen 2 1-Rührkolben mit Gaseinleitung und Heizung werden 467 g (1,0 Mol) N-C16-C18-alkyl-N,N',N'-tris-(2-hydroxyethyl)-1,3-diaminopropan, 534 g (2,0 Mol) Stearinsäure und 0,2 g Zn0 vorgelegt, zum Schmelzen gebracht und unter Stickstoffabdeckung und Rühren auf 170°C erhitzt. Nach 6-stündiger Reaktionszeit zeigte die Restsäurezahl.von 2,3 an, daß die Veresterung abgeschlossen war und das Produkt in die Quaternierstufe eingesetzt werden konnte.In a 2 1 stirring flask with gas inlet and heating 467 g (1.0 mol) of NC 16 -C 18 -alkyl-N, N ', N'-tris- (2-hydroxyethyl) -1,3-diaminopropane, 534 g (2.0 mol) of stearic acid and 0 , 2 g Zn0 submitted, melted and heated to 170 ° C under nitrogen blanket and stirring. After a reaction time of 6 hours, the residual acid number of 2.3 indicated that the esterification was complete and the product could be used in the quaternization stage.

Auf analoge Weise können die entsprechenden Cocosfettsäure-, Ölsäure- oder Talgfettsäure-Derivate gewonnen werden.The corresponding coconut fatty acid, oleic acid or tallow fatty acid derivatives can be obtained in an analogous manner.

Durch entsprechende Veränderung der stöchiometrischen Verhältnisse lassen sich auf gleiche Weise Mono- und Triester von N-C16-C18-alkyl-N,N',N'-tris-(2-hydroxyethyl)-1,3-diaminopropan herstellen.By appropriately changing the stoichiometric ratios, mono- and triesters of NC 16 -C 18 -alkyl-N, N ', N'-tris- (2-hydroxyethyl) -1,3-diaminopropane can be prepared in the same way.

. Quaternierung von N-C16-C18-alkyl,N,N',N'-tris-(2-hydroxyethyl)-1,3-diaminopropan-di-stearinsäureester mit Dimethylsulfat. Quaternization of NC 16 -C 18 alkyl, N, N ', N'-tris- (2-hydroxyethyl) -1,3-diaminopropane-di-stearic acid ester with dimethyl sulfate

177 g gemäß 1. hergestellter Distearinsäureester wird in einem Rührkolben mit 180 g Isopropanol vermischt und auf 40 bis 50°C aufgeheizt. Bei dieser Temperaatur werden innerhalb von ca. 30 Minuten 48 g Dimethylsulfat zugetropft. Nach 3 Stunden werden 12 g Natriummethylat-Lösung (35 %-ig in Methanol) und 9 g Dimethylsulfat zugegeben und weitere 2 Stunden bei ca. 50°C gerührt. Nach Zugabe von weiteren 9 g Natriummethylat-Lösung, wodurch der pH-Wert auf 6,6 eingestellt wurde und Abkühlen auf Raumtemperatur, kann das Produkt in Weichspulformulierungen eingesetzt werden.177 g of distearic acid ester prepared according to 1. is mixed in a stirred flask with 180 g of isopropanol and heated to 40 to 50 ° C. At this temperature, 48 g of dimethyl sulfate are added dropwise within about 30 minutes. After 3 hours, 12 g of sodium methylate solution (35% in methanol) and 9 g of dimethyl sulfate are added and the mixture is stirred at about 50 ° C. for a further 2 hours. After adding a further 9 g of sodium methylate solution, which brought the pH to 6.6 and cooling to room temperature, the product can be used in fabric softener formulations.

Die Quaternierung der Mono- und Tristearinsäureestcr mit Dimethylsulfat analog der angegebenen Vorschrift lieferten die entsprechenden Bis-Quats.The quaternization of the mono- and tristearic acid esters with dimethyl sulfate analogous to the specified procedure gave the corresponding bis-quats.

Claims (4)

1. Quartäre N-Alkyl-N,N',N'-polyoxyalkyl-α,ω-diamino- alkylen-fettsäureester der Formel (1)
Figure imgb0004
worin R1 C8-C30-Alkyl oder C8-C30-Alkenyl, R2 C1-C4-Alkyl, R3 C7-C29-Alkyl oder C7-C29-Alkenyl, x und y Wasserstoff oder Methyl, wobei x und y jedoch nicht gleichzeitig Methyl darstellen, a 0, 1 oder 2, n eine Zahl von 1 bis 11, m 1 oder 2, p eine Zahl von 1 bis 5 und - A ein Anion bedeutet.. 1st Quaternary N-alkyl-N, N ', N'-polyoxyalkyl-α, ω-diaminoalkylene fatty acid esters of the formula (1)
Figure imgb0004
 wherein R 1 is C 8 -C 30 alkyl or C 8 -C 30 alkenyl, R2 C 1 -C 4 alkyl, R 3 is C 7 -C 29 alkyl or C 7 -C 29 alkenyl, x and y are hydrogen or methyl, but x and y are not simultaneously methyl, a 0, 1 or 2, n is a number from 1 to 11, m 1 or 2, p is a number from 1 to 5 and - A means an anion .. 2. Verbindungen der Formel (1) nach Anspruch 1, wobei R1 C16-C18-Alkyl oder C16-C18-Alkenyl, R2 Methyl, x und y Wasserstoff, n 1, m 1, p 3 und A ein Halogenid-, Methosulfat- oder Methophosphat-Ion bedeutet. 2nd Compounds of formula (1) according to claim 1, wherein R 1 is C 16 -C 18 alkyl or C 16 -C 18 alkenyl, R 2 is methyl, x and y are hydrogen, n 1, m 1, p 3 and A is a halide -, methosulfate or methophosphate ion means. 3. Verfahren zur Herstellung von Verbindungen der Formel (1) nach Anspruch 1, dadurch gekennzeichnet, daß man eine Verbindung der Formel (2)
Figure imgb0005
in der R1, x, y, m, n und p die in Formel (1) angegebenen Bedeutungen haben, mit einer Fettsäure der Formel 3
Figure imgb0006
worin R3 die in Formel 1 angegebene Bedeutung hat, verestert und das erhaltene Reaktionsprodukt mit einem Alkylierungsreagenz unter Einfügung des Restes R2 quaterniert. 3rd A process for the preparation of compounds of formula (1) according to claim 1, characterized in that a compound of formula (2)
Figure imgb0005
 in which R 1 , x, y, m, n and p have the meanings given in formula (1), with a fatty acid of the formula 3
Figure imgb0006
 wherein R 3 has the meaning given in formula 1, esterified and the reaction product obtained quaternized with an alkylating reagent with the addition of the radical R 2 . 4. Verwendung der Verbindungen der Formel (1) nach Anspruch 1 als Wäscheweichspülmittel.4. Use of the compounds of formula (1) according to claim 1 as fabric softener.
EP82105949A 1981-07-10 1982-07-03 Quaternary n-alkyl-n,n'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use Expired EP0069948B1 (en)

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DE3127239 1981-07-10
DE19813127239 DE3127239A1 (en) 1981-07-10 1981-07-10 QUARTAERE N-ALKYL-N, N ', N'-POLYOXYALKYL- (ALPHA), (OMEGA) -DIAMINOALKYLENE FATTY ACID ESTER, METHOD FOR THE PRODUCTION AND USE THEREOF

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4476106A (en) * 1981-07-02 1984-10-09 Commissariat A L'energie Atomique Process for the extemporaneous preparation of an injectable fatty acid tagged in the omega position by means of radioactive iodine
EP0131865A1 (en) * 1983-07-13 1985-01-23 Hoechst Aktiengesellschaft Esterified oxyalkylated quaternary ammonium compounds, process for their preparation and their use as treating agents for fibres
WO1991001295A1 (en) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Process for preparing quaternary ammonium compounds
EP0648835A1 (en) * 1993-10-14 1995-04-19 The Procter & Gamble Company Use of alkaline polyammonium salts to increase cationic density in fabric softeners

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US5491240A (en) * 1994-09-29 1996-02-13 Witco Corporation Quaternary compound of a tertiary amine and methyl chloride
US6211139B1 (en) 1996-04-26 2001-04-03 Goldschmidt Chemical Corporation Polyester polyquaternary compounds, compositions containing them, and use thereof

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US4476106A (en) * 1981-07-02 1984-10-09 Commissariat A L'energie Atomique Process for the extemporaneous preparation of an injectable fatty acid tagged in the omega position by means of radioactive iodine
EP0131865A1 (en) * 1983-07-13 1985-01-23 Hoechst Aktiengesellschaft Esterified oxyalkylated quaternary ammonium compounds, process for their preparation and their use as treating agents for fibres
WO1991001295A1 (en) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Process for preparing quaternary ammonium compounds
EP0648835A1 (en) * 1993-10-14 1995-04-19 The Procter & Gamble Company Use of alkaline polyammonium salts to increase cationic density in fabric softeners

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ES513706A0 (en) 1983-03-16
DE3261758D1 (en) 1985-02-14
AU548545B2 (en) 1985-12-19
ES8304917A1 (en) 1983-03-16
US4515723A (en) 1985-05-07
BR8203996A (en) 1983-07-05
CA1195338A (en) 1985-10-15
DE3127239A1 (en) 1983-01-20
AU8577982A (en) 1983-01-13
EP0069948B1 (en) 1985-01-02
JPS5818341A (en) 1983-02-02

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