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EP0022562A2 - Quaternary ammonium compounds, their preparation and their use as fabric softener - Google Patents

Quaternary ammonium compounds, their preparation and their use as fabric softener Download PDF

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Publication number
EP0022562A2
EP0022562A2 EP80103954A EP80103954A EP0022562A2 EP 0022562 A2 EP0022562 A2 EP 0022562A2 EP 80103954 A EP80103954 A EP 80103954A EP 80103954 A EP80103954 A EP 80103954A EP 0022562 A2 EP0022562 A2 EP 0022562A2
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Prior art keywords
alkyl
formula
alkenyl
methyl
compounds
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German (de)
French (fr)
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EP0022562A3 (en
EP0022562B1 (en
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Erich Dr. Hoffmann
Wolfgang Dr. Wagemann
Günther Dr. Täuber
Adolf Dr. May
Hans-Walter Dr. Bücking
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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
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the invention relates to quaternary ammonium compounds of the formula 1 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 -C 4 alkyl, or benzyl, A is a group of the formulas
  • B has the same meaning as A and additionally a C 1 -C 4 alkylene group, RC 8 -C 30 alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A (-) is an anion.
  • Preferred compounds of formula 1 are those in which R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 14-24 C atoms, R 2 is methyl, RC 14 -C 24 alkyl or alkenyl, m is a number from 1 to 5, A. (-) means a halogen, methosulfate or methophosphate ion and A, B, X, Y and m have the meaning given above.
  • R 1 is C 16 -C 18 alkyl or alkenyl
  • R 2 is methyl
  • a and B are a group of the formula and
  • a (-) represents a chloride or methosulfate ion.
  • the reaction in the first stage is preferably carried out with the free fatty acid in the absence of solvents and at temperatures of approximately 130 to 180 ° C., preferably 150 to 170 ° C.
  • an acid catalyst such as p-toluenesulfonic acid.
  • the molar ratio of the fatty acid of formula 3 to the aminoxalkylate of formula 2 is 0.7 to 1.1, preferably 0.7 to 0.9 mol of fatty acid per 1 mol of aminoxalkylate.
  • the intermediate product of formula 4 thus obtained is then dissolved in an alcohol or dispersed in water and quaternized with a compound of the above formulas in a conventional manner at temperatures below 100 ° C., preferably at 40-80 ° C.
  • the compounds of formula 2 serving as starting products are known as such. They are obtained by oxyalkylating fatty alkyl amines or by reacting fatty amines with 2,3-epoxypropanol.
  • suitable fatty alkylamines are dodecyl-, myristyl-, cetyl-, oleyl-, behenyl- or preferably stearylamine or mixtures of such fatty alkylamines which are derived from naturally occurring fats such as coconut oil or tallow.
  • the compounds of formula 1 according to the invention are suitable as fabric softening agents and are in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4-10% by weight of the compounds of formula 1 following the washing of the textile material into the last Given 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 colorants 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 and underwear is particularly advantageous.
  • 171.5 g of the compound of the formula are placed in a 500 ml flask equipped with a stirrer, nitrogen inlet, contact thermometer and descending condenser 104 g of stearic acid, 2 g of hydrazine hydrate and 2 g of p-toluenesulfonic acid are introduced under nitrogen and slowly heated to 150.degree. After an hour, the temperature is raised to 175 ° C. and maintained until the acid number is less than 6. The water of reaction released is continuously distilled off. Then allowed to cool to 70 ° C, mixed with about 112 ml of warm water and transferred to the 70 ° C warm mixture in a 1 liter autoclave.
  • Example 2 120 g of the compound of the formula and 71.2 g of tallow fatty acid (molar ratio of aminoxethylate: tallow fatty acid 1: 0.8) as described in Example 1. After 7 h at 175 ° C., 179 g of ester with an acid number of 5.1 are obtained. 30 percent by weight of water are added and the 70-75 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, gaseous methyl chloride is pressed in from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. About 270 g of a waxy mass with a solids content of 73% are obtained.
  • Example 2 In an apparatus as in Example 1, 184 g. D i- (2,3-dihydroxypropyl) stearylamine and 100 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.89) are reacted as described in Example 1. After 7 h at 175 ° C., 270 g of monoesters with an acid number of 5 are obtained. About 30 percent by weight warm water is added and the 70 ° C warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 400 g of a mass which is waxy at room temperature and has a solids content of 75% are obtained.
  • Example 2 In an apparatus as in Example 1, 176 g of di-2-hydroxyethyl - (2-hydroxypentadecyl / octadecyl) amine and 117 g of stearic acid (molar ratio of aminoxethylate: stearic acid 1 / 0.91) are reacted as described. After 7 h at 175 ° C., 279 g of condensation product with an acid number of 6 are obtained. 30 percent by weight of warm water are added and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in from a bomb at 70-80 ° C. until a constant pressure of 5 bar is reached. Stirring is continued at 60 ° C. for two hours and the pressure is carefully released. 420 g of a mass which is waxy at room temperature and has a solids content of 72 are obtained
  • Example 2 In an apparatus as in Example 1, 156 g of methyl (2,3-dihydroxypropyl) stearylamine and 91 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.88) are the same described implemented. After 7 h at 175 ° C. 225 g of ester with an acid number of 6 are obtained. 30 percent by weight of warm water are stirred in and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 360 g of a mass which is waxy at room temperature and has a solids content of 71% are obtained.
  • Example 2 same end product as example 1
  • R 1 tallow fatty alkyl
  • R tallow fatty acyl
  • R 1 mixture of 2-hydroxipentadecyl and octadecyl

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • 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

Quaternäre Ammoniumverbindungen der Formel 1 <IMAGE> worin R1 Alkyl, 2-Hydroxyalkyl oder Alkenyl mit jeweils 8 bis 30 C-Atomen, R2 C1-C4-Alkyl oder Benzyl, A eine Gruppe der Formel <IMAGE> B die gleiche Bedeutung wie A hat und zusätzlich eine C1-C4-Alkenylgruppe, R C8-C30-Alkyl oder Alkenyl, X und Y Wasserstoff oder Methyl, wobei X und Y jedoch nicht gleichzeitig Methyl sind, m 1 oder 2, n eine Zahl von 1 bis 20 und A<(-)> ein Anion bedeutet, Verfahren zu deren Herstellung und deren Verwendung als Wäscheweichspülmittel.Quaternary ammonium compounds of the formula 1 <IMAGE> wherein R1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R2 C1-C4-alkyl or benzyl, A is a group of the formula <IMAGE> B has the same meaning as A. and additionally a C1-C4-alkenyl group, R C8-C30-alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not simultaneously methyl, m 1 or 2, n is a number from 1 to 20 and A < (-)> An anion means processes for their production and their use as fabric softeners.

Description

Gegenstand der Erfindung sind quaternäre Ammoniumverbindungen der Formel 1

Figure imgb0001
worin R1 Alkyl, 2-Hydroxialkyl oder Alkenyl mit jeweils 8 bis 30 C-Atomen, R2 C1-C4-Alkyl, oder Benzyl, A eine Gruppe der Formeln
Figure imgb0002
 The invention relates to quaternary ammonium compounds of the formula 1
Figure imgb0001
 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 -C 4 alkyl, or benzyl, A is a group of the formulas
Figure imgb0002

B die gleiche Bedeutung wie A hat und zusätzlich eine C1-C4-Alkylengruppe, R C8-C30-Alkyl oder Alkenyl, X und Y Wasserstoff oder Methyl, wobei X und Y jedoch nicht gleichzeitig Methyl sind, m 1 oder 2, n eine Zahl von 1 bis 20 und A(-) ein Anion bedeutet.B has the same meaning as A and additionally a C 1 -C 4 alkylene group, RC 8 -C 30 alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A (-) is an anion.

Bevorzugt sind solche Verbindungen der Formel 1, worin R1 Alkyl, 2-Hydroxialkyl oder Alkenyl mit jeweils 14 - 24 C-Atomen, R2 Methyl, R C14-C24-Alkyl oder Alkenyl, m eine Zahl von 1 bis 5, A(-) ein Halogen-, Methosulfat- oder Methophosphat-Ion bedeutet und A, B, X, Y und m die oben genannte Bedeutung haben.Preferred compounds of formula 1 are those in which R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 14-24 C atoms, R 2 is methyl, RC 14 -C 24 alkyl or alkenyl, m is a number from 1 to 5, A. (-) means a halogen, methosulfate or methophosphate ion and A, B, X, Y and m have the meaning given above.

Insbesondere bevorzugt sind Verbindungen der Formel 1, worin R1 C16-C18-Alkyl oder Alkenyl, R2 Methyl, R C16-C 18-Alkyl oder Alkenyl, A und B eine Gruppe der Formel

Figure imgb0003
und A(-) ein Chlorid- oder Methosulfat-Ion bedeutet.Particularly preferred are compounds of formula 1, wherein R 1 is C 16 -C 18 alkyl or alkenyl, R 2 is methyl, RC 16 - C 18 alkyl or alkenyl, A and B are a group of the formula
Figure imgb0003
 and A (-) represents a chloride or methosulfate ion.

Diese Verbindungen werden hergestellt, indem man eine Verbindung der Formel 2

Figure imgb0004
zunächst mit einer Säure der Formel 3
Figure imgb0005
oder dem entsprechenden Säurechlorid umsetzt. Dabei erhält man als Zwischenprodukt die Verbindung der Formel 4
Figure imgb0006
die dann mit einer Vebindung der Formeln
Figure imgb0007
quaterniert wird, wobei Z Halogen bedeutet.These compounds are prepared by using a compound of formula 2
Figure imgb0004
 first with an acid of formula 3
Figure imgb0005
 or the corresponding acid chloride. The compound of formula 4 is obtained as an intermediate
Figure imgb0006
 then with a connection of the formulas
Figure imgb0007
 is quaternized, where Z is halogen.

Die Umsetzung in der ersten Stufe erfolgt vorzugsweise mit der freien Fettsäure in Abwesenheit von Lösungsmitteln und bei Temperaturen von ca. 130 bis 180°C, vorzugsweise 150 bis 170°C. Zur Beschleunigung der Reaktion setzt man vorteilhaft geringe Mengen eines sauren Katalysators zu, wie etwa p-Toluolsulfonsäure. Das Molverhältnis der Fettsäure der Formel 3 zu dem Aminoxalkylat der Formel 2 beträgt 0,7 bis 1,1 vorzugsweise 0,7 bis 0,9 Mol Fettsäure auf 1 Mol Aminoxalkylat. Das so erhaltene Zwischenprodukt der Formel 4 wird dann in einem Alkohol gelöst oder in Wasser dispergiert und mit einer Verbindung der obigen Formeln in üblicher Weise quaterniert bei Temperaturen unterhalb 100°C, vorzugsweise bei 40 - 80°C. Man kann diese Reaktion auch in Abwesenheit eines Lösungsmittels durchführen. Beim Arbeiten in einem Lösungs- oder Verdünnungsmittel erhält man Konzentrate mit einem Gehalt von ca. 20 bis 35 Gew.-% der Verbindung der Formel 1. Durch Abdestillieren des Wassers bzw. Lösungsmittels lassen sich die Verbindungen der Formel 1 in reiner Form gewinnen. Die Konzentrate können aber auch zum weiteren Gebrauch direkt verdünnt werden auf einen Gehalt von ca. 1 bis 30, vorzugsweise 4 bis 10 Gew.-%.The reaction in the first stage is preferably carried out with the free fatty acid in the absence of solvents and at temperatures of approximately 130 to 180 ° C., preferably 150 to 170 ° C. To accelerate the reaction, it is advantageous to add small amounts of an acid catalyst, such as p-toluenesulfonic acid. The molar ratio of the fatty acid of formula 3 to the aminoxalkylate of formula 2 is 0.7 to 1.1, preferably 0.7 to 0.9 mol of fatty acid per 1 mol of aminoxalkylate. The intermediate product of formula 4 thus obtained is then dissolved in an alcohol or dispersed in water and quaternized with a compound of the above formulas in a conventional manner at temperatures below 100 ° C., preferably at 40-80 ° C. Man can carry out this reaction even in the absence of a solvent. When working in a solvent or diluent, concentrates containing about 20 to 35% by weight of the compound of the formula 1 are obtained. The compounds of the formula 1 can be obtained in pure form by distilling off the water or solvent. However, the concentrates can also be diluted directly for further use to a content of about 1 to 30, preferably 4 to 10% by weight.

Die als Ausgangsprodukte dienenden Verbindungen der Formel 2 sind als solche bekannt. Sie werden erhalten durch Oxalkylierung von Fettalkylaminen oder durch Reaktion von Fettaminen mit 2,3-Epoxypropanol. Als Fettalkylamine kommen beispielsweise Dodecyl-, Myristyl-, Cetyl-, Oleyl-, Behenyl- oder bevorzugt Stearylamin in Frage oder Gemische solcher Fettalkylamine, die sich von natürlich vorkommenden Fetten wie etwa Cocosöl oder Talg ableiten.The compounds of formula 2 serving as starting products are known as such. They are obtained by oxyalkylating fatty alkyl amines or by reacting fatty amines with 2,3-epoxypropanol. Examples of suitable fatty alkylamines are dodecyl-, myristyl-, cetyl-, oleyl-, behenyl- or preferably stearylamine or mixtures of such fatty alkylamines which are derived from naturally occurring fats such as coconut oil or tallow.

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 - 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 Aufhellungsmittel 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 formula 1 according to the invention are suitable as fabric softening agents and are in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4-10% by weight of the compounds of formula 1 following the washing of the textile material into the last Given 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 colorants 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, Celluloseaceat, 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 and underwear is particularly advantageous.

Die Herstellung der neuen quartären Ammoniumverbindung gemäß der vorliegenden Erfindung wird in folgenden Beispielen weiter erläutert. Sofern nicht anders angegeben beziehen sich alle Prozentangaben auf das Gewicht.The preparation of the new quaternary ammonium compound according to the present invention is further explained in the following examples. Unless otherwise stated, all percentages relate to the weight.

Beispiel 1example 1

In einem 500 ml Kolben, versehen mit Rührer, Stickstoffeinlaß, Kontaktthermometer und absteigendem Kühler, werden 171,5 g der Verbindung der Formel

Figure imgb0008
104 g Stearinsäure, 2 g Hydrazinhydrat und 2 g p-Toluolsulfonsäure unter Stickstoff vorgelegt und langsam auf 150°C erhitzt. Nach einer Stunde wird die Temperatur auf 175°C erhöht und solange beibehalten, bis die Säurezahl kleiner als 6 ist. Das freiwerdende Reaktionswasser wird dabei kontinuierlich abdestilliert. Danach läßt man auf 70°C abkühlen, versetzt mit ca. 112 ml warmen Wasser und überführt die 70°C warme Mischung in einen 1 Liter Autoklaven. Nach Verschließen des Autoklaven wird 2 x Stickstoff aufgedrückt und vorsichtig entspannt. Danach wird aus einer Bombe bei 70 - 80°C solange Methylchlorid gasförmig aufgedrückt, bis ein Druck von 5 bar erreicht ist. Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält ca. 400 g einer bei Raumtemperatur wachsartiger Masse mit einem Feststoffgehalt von ca. 75 %.171.5 g of the compound of the formula are placed in a 500 ml flask equipped with a stirrer, nitrogen inlet, contact thermometer and descending condenser
Figure imgb0008
 104 g of stearic acid, 2 g of hydrazine hydrate and 2 g of p-toluenesulfonic acid are introduced under nitrogen and slowly heated to 150.degree. After an hour, the temperature is raised to 175 ° C. and maintained until the acid number is less than 6. The water of reaction released is continuously distilled off. Then allowed to cool to 70 ° C, mixed with about 112 ml of warm water and transferred to the 70 ° C warm mixture in a 1 liter autoclave. After closing the autoclave, nitrogen is pressed in twice and the pressure is carefully released. Then a bomb is pressed in gaseous form from a bomb at 70 - 80 ° C until a pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. About 400 g of a mass which is waxy at room temperature are obtained a solids content of approx. 75%.

Beispiel 2Example 2

In einer Apparatur wie bei Beispiel 1 werden 231 g der Ausgangsverbindung aus Beispiel 1 und 109,5 g Stearinsäure (Molverhältnis Aminoxethylat: Stearinsäure 1 : 0,7 umgesetzt wie in Beispiel 1 beschrieben. Nach 7 h bei 175°C werden 323 g Monoester mit einer Säurezahl von 4,5 erhalten. Es werden 30 Gewichtsprozent warmes Wasser hinzugesetzt und die 70°C warme Mischung in einen 1 Liter Autoklaven überführt. Nach Spülung mit Stickstoff wird aus einer Bombe bei 70 - 80°C solange gasförmiges Methylchlorid aufgedrückt, bis ein konstanter Druck von 5 bar erreicht wird. Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält 440 g einer bei Raumtemperatur wachsartigen Masse mit einem Feststoffgehalt von 74 %.231 g of the starting compound from Example 1 and 109.5 g of stearic acid (molar ratio of aminoxethylate: stearic acid 1: 0.7 are reacted as described in Example 1 in an apparatus as in Example 1. After 7 hours at 175 ° C., 323 g of monoesters are reacted with having an acid number of 4.5, 30% by weight of warm water are added and the mixture, which is at 70 ° C., is transferred to a 1 liter autoclave, and after flushing with nitrogen, gaseous methyl chloride is injected from a bomb at 70-80 ° C. until a constant pressure of 5 bar is reached, stirring is continued for two hours at 60 ° C. and the mixture is cautiously released, giving 440 g of a mass which is waxy at room temperature and has a solids content of 74%.

Beispiel 3Example 3

In einer Apparatur wie in Beispiel 1 erwähnt werden 120 g der Verbindung der Formel

Figure imgb0009
und 71,2 g Talgfettsäure (Molverhältnis Aminoxethylat: Talgfettsäure 1:0,8) wie in Beispiel 1 beschrieben umgesetzt. Nach 7 h bei 175°C werden 179 g Ester mit einer Säurezahl von 5,1 erhalten. Es werden 30 Gewichtsprozente Wasser hinzugesetzt und die 70 - 75°C warme Mischung in einem 1 Liter Autoklaven überführt. Nach Spülung mit Stickstoff wird aus einer Bombe bei 70 - 80°C solange gasförmiges Methylchlorid aufgedrückt, bis ein konstanter Druck von 5 bar erreicht ist. Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält ca. 270 g einer wachsartigen Masse mit einem Feststoffgehalt von 73 %.In an apparatus as mentioned in Example 1, 120 g of the compound of the formula
Figure imgb0009
 and 71.2 g of tallow fatty acid (molar ratio of aminoxethylate: tallow fatty acid 1: 0.8) as described in Example 1. After 7 h at 175 ° C., 179 g of ester with an acid number of 5.1 are obtained. 30 percent by weight of water are added and the 70-75 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, gaseous methyl chloride is pressed in from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. About 270 g of a waxy mass with a solids content of 73% are obtained.

Beispiel 4Example 4

In einer Apparatur wie bei Beispiel 1 werden 184 g.Di-(2,3-dihydroxypropyl)stearylamin und 100 g Stearinsäure (Molverhältnis Aminoxalkylat : Stearinsäure 1:0,89) wie in Beispiel 1 beschrieben umgesetzt. Nach 7 h bei 175°C werden 270 g Monoester mit einer Säurezahl von 5 erhalten. Es werden ca. 30 Gewichtsprozente warmes Wasser hinzugesetzt und die 70°C warme Mischung in einen 1 Liter Autoklaven überführt. Nach Spülung mit Stickstoff wird aus einer Bombe bei 70 - 80°C solange Methylchlorid gasförmig aufgedrückt bis ein konstanter Druck von5 bar erreicht wird. Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält 400 g einer bei Raumtemperatur wachsartigen Masse mit einem Feststoffgehalt von 75 %.In an apparatus as in Example 1, 184 g. D i- (2,3-dihydroxypropyl) stearylamine and 100 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.89) are reacted as described in Example 1. After 7 h at 175 ° C., 270 g of monoesters with an acid number of 5 are obtained. About 30 percent by weight warm water is added and the 70 ° C warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 400 g of a mass which is waxy at room temperature and has a solids content of 75% are obtained.

Beispiel 5Example 5

In einer Apparatur wie bei Beispiel 1 werden 176 g Di-2-hydroxyethyl -(2-hydroxypentadecyl/octadecyl)amin und 117 g Stearinsäure (Molverhältnis Aminoxethylat : Stearinsäure 1/0,91) wie beschrieben umgesetzt. Nach 7 h bei 175°C werden 279 g Kondensationsprodukt mit einer Säurezahl von 6 erhalten. Es werden 30 Gewichtsprozent warmes Wasser hinzugesetzt und die 70°C warme Mischung in einen 1 Liter Autoklaven überführt. Nach Spülung mit Stickstoff wird aus einer Bombe bei 70 - 80°C solange Methylchlorid aufgedrückt, bis ein konstanter Druck von 5 bar erreicht ist, Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält 420 g einer bei Raumtemperatur wachsartigen Masse mit einem Feststoffgehalt von 72In an apparatus as in Example 1, 176 g of di-2-hydroxyethyl - (2-hydroxypentadecyl / octadecyl) amine and 117 g of stearic acid (molar ratio of aminoxethylate: stearic acid 1 / 0.91) are reacted as described. After 7 h at 175 ° C., 279 g of condensation product with an acid number of 6 are obtained. 30 percent by weight of warm water are added and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in from a bomb at 70-80 ° C. until a constant pressure of 5 bar is reached. Stirring is continued at 60 ° C. for two hours and the pressure is carefully released. 420 g of a mass which is waxy at room temperature and has a solids content of 72 are obtained

Beispiel 6Example 6

In einer Apparatur wie bei Beispiel 1 werden 156 g Methyl-(2,3-dihydroxypropyl)-stearylamin und 91 g Stearinsäure (Molverhältnis Aminoxalkylat : Stearinsäure 1:0,88) wie beschrieben umgesetzt. Nach 7 h bei 175°C werden 225 g Ester mit einer Säurezahl von 6 erhalten. Es werden 30 Gewichtsprozente warmes Wasser eingerührt und die 70°C warme Mischung in einen 1 Liter Autoklaven überführt. Nach Spülung mit Stickstoff wird aus einer Bombe bei 70 - 80°C solange Methylchlorid gasförmig aufgedrückt bis ein konstanter Druck von 5 bar erreicht wird. Man rührt zwei Stunden bei 60°C nach und entspannt vorsichtig. Man erhält 360 g einer bei Raumtemperatur wachsartigen Masse mit einem Feststoffgehalt von 71 %.In an apparatus as in Example 1, 156 g of methyl (2,3-dihydroxypropyl) stearylamine and 91 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.88) are the same described implemented. After 7 h at 175 ° C. 225 g of ester with an acid number of 6 are obtained. 30 percent by weight of warm water are stirred in and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 360 g of a mass which is waxy at room temperature and has a solids content of 71% are obtained.

Die Konstitution der nach den Beispielen 1 bis 6 erhaltenen Verbindungen der Formel 1 ist aus der folgenden Tabelle ersichtlichThe constitution of the compounds of formula 1 obtained according to Examples 1 to 6 can be seen from the following table

Beispiel 1:Example 1:

Figure imgb0010
Figure imgb0010

Beispiel 2: gleiches Endprodukt wie Beispiel 1Example 2: same end product as example 1 Beispiel 3:Example 3:

Figure imgb0011
Figure imgb0011

R1= Talgfettalkyl R= TalgfettacylR 1 = tallow fatty alkyl R = tallow fatty acyl

Beispiel 4:Example 4:

Figure imgb0012
A= Gemisch der Gruppen
Figure imgb0013
und
Figure imgb0012
 A = mixture of groups
Figure imgb0013
 and

Beispiel 5:Example 5:

Figure imgb0014
R1= Gemisch aus 2-Hydroxipentadecyl und Octadecyl
Figure imgb0014
 R 1 = mixture of 2-hydroxipentadecyl and octadecyl

Beispiel 6:Example 6:

Figure imgb0015
A= Gemisch der Gruppen
Figure imgb0016
Figure imgb0017
und
Figure imgb0015
 A = mixture of groups
Figure imgb0016
Figure imgb0017
 and

Claims (9)

1. Quaternäre Ammoniumverbindungen der Formel 1
Figure imgb0018
worin R1 Alkyl, 2-Hydroxialkyl oder Alkenyl mit jeweils 8 bis 30 C-Atomen, R2 C1-C4-Alkyl oder Benzyl, A eine Gruppe der Formeln
Figure imgb0019
B die gleiche Bedeutung wie A hat und zusätzlich eine C1-C4-Alkenylgruppe, R C8-C30-Alkyl oder Alkenyl, X und Y Wasserstoff oder Methyl, wobei X und Y jedoch nicht gleichzeitig Methyl sind, m 1 oder 2, n eine Zahl von 1 bis 20 und A(-) ein Anion bedeutet.1. Quaternary ammonium compounds of the formula 1
Figure imgb0018
 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 -C 4 alkyl or benzyl, A is a group of the formulas
Figure imgb0019
 B has the same meaning as A and additionally a C 1 -C 4 alkenyl group, RC 8 -C 30 alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A (-) is an anion. 2. Verbindungen der Formel 1 nach Anspruch 1, wobei R1 Alkyl, 2-Hydroxialkyl oder Alkenyl mit jeweils 14 bis 24 C-Atomen, R2 Methyl, R C14-C24-Alkyl oder Alkenyl, m eine Zahl von 1 bis 5, A ein Halogen-, Methosulfat- oder Methophosphat-Ion bedeutet und A, B, X, Y und m die in Anspruch 1 genannte Bedeutung haben.2. Compounds of formula 1 according to claim 1, wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 14 to 24 carbon atoms, R 2 methyl, RC 14 -C 24 alkyl or alkenyl, m is a number from 1 to 5 , A is a halogen, methosulfate or methophosphate ion and A, B, X, Y and m have the meaning given in claim 1. 3. Verbindungen der Formel 1 nach Anspruch 1, wobei R1 C16-C18-Alkyl oder Alkenyl, R2 Methyl, R C16-C18-Alkyl oder Alkenyl, A und B eine Gruppe der Formel
Figure imgb0020
und A(-) ein Chlorid- oder Methosulfat-Ion bedeutet.3. Compounds of formula 1 according to claim 1, wherein R 1 is C 16 -C 18 alkyl or alkenyl, R 2 is methyl, R C16-C18 alkyl or alkenyl, A and B are a group of the formula
Figure imgb0020
 and A (-) represents a chloride or methosulfate ion. 3. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß.man eine Verbindung der Formel
Figure imgb0021
zuerst mit einer Säure der Formel R-COOH oder dem entsprechenden Säurechlorid und dann mit einer Verbindung der Formeln
Figure imgb0022
umsetzt wobei Z Halogen bedeutet.3. A process for the preparation of the compounds according to claim 1, characterized in that.man a compound of the formula
Figure imgb0021
 first with an acid of the formula R-COOH or the corresponding acid chloride and then with a compound of the formulas
Figure imgb0022
 implemented where Z is halogen. 4. Verwendung der Verbindungen nach Anspruch 1 als Wäscheweichspülmittel.4. Use of the compounds according to claim 1 as fabric softener. Patentansprüche ÖsterreichClaims Austria 1. Verfahren zur Herstellung von Quaternären Ammoniumverbindungen der Formel 1
Figure imgb0023
worin R1 Alkyl, 2-Hydroxyalkyl oder Alkenyl mit jeweils 8 bis 30 C-Atomen, R2 C1-C4-Alkyl oder Benzyl, A eine Gruppe der Formeln
Figure imgb0024
B die gleiche Bedeutung wie A hat und zusätzlich eine C1-C4-Alkenylgruppe, R C8-C30-Alkyl oder Alkenyl, X und Y Wasserstoff oder Methyl, wobei X und Y jedoch nicht gleichzeitig Methyl sind, m 1 oder 2, n eine Zahl von 1 bis 20 und A(-) ein Anion bedeutet, dadurch gekennzeichnet, daß man eine Verbindung der Formel
Figure imgb0025
zuerst mit einer Säure der Formel
Figure imgb0026
oder dem entsprechenden Säurechlorid und dann mit einer Verbindung der Formeln
Figure imgb0027
umsetzt wobei Z Halogen bedeutet.1. Process for the preparation of quaternary ammonium compounds of the formula 1
Figure imgb0023
 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 -C 4 alkyl or benzyl, A is a group of the formulas
Figure imgb0024
 B has the same meaning as A and additionally a C 1 -C 4 alkenyl group, RC 8 -C 30 alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A (-) is an anion, characterized in that a compound of the formula
Figure imgb0025
 first with an acid of the formula
Figure imgb0026
 or the corresponding acid chloride and then with a compound of the formulas
Figure imgb0027
 implemented where Z is halogen. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man solche Verbindungen der Formel 1 herstellt, wobei R1 Alkyl, 2-Hydroxyalkyl oder Alkenyl mit jeweils 14 bis 24 C-Atomen, R2 Methyl, R C14-C24-Alkyl oder Alkenyl, m eine Zahl von 1 bis 5, A(-) ein Halogen-, Methosulfat- oder Methophosphat-Ion bedeutet und A, B, X, Y und m die in Anspruch 1 genannte Bedeutung haben.2. The method according to claim 1, characterized in that such compounds of formula 1 are prepared, wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl with each 14 to 24 carbon atoms, R 2 methyl, RC 14 -C 24 alkyl or alkenyl, m is a number from 1 to 5, A (-) is a halogen, methosulfate or methophosphate ion and A, B, X , Y and m have the meaning given in claim 1. 3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man solche Verbindungen der Formel 1 herstellt, wobei R1 C16-C18-Alkyl oder Alkenyl, R2 Methyl, R C16-C18-Alkyl oder Alkenyl, A und B eine Gruppe der Formel
Figure imgb0028
und A(-) ein Chlorid- oder Methosulfat-Ion bedeutet.3. The method according to claim 1, characterized in that such compounds of formula 1 are prepared, wherein R 1 C 16 -C 18 alkyl or alkenyl, R 2 methyl, R C16-C18 alkyl or alkenyl, A and B a group of the formula
Figure imgb0028
 and A (-) represents a chloride or methosulfate ion.
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JPS5618946A (en) 1981-02-23
CA1167054A (en) 1984-05-08
EP0022562B1 (en) 1985-06-19
US4339391A (en) 1982-07-13
DE3070775D1 (en) 1985-07-25
ATE13879T1 (en) 1985-07-15
DE2928603A1 (en) 1981-02-05
BR8004336A (en) 1981-02-03

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