EP0295385B1 - Process for preparing fatty acid diesters of a trialcanolamine and their use - Google Patents
Process for preparing fatty acid diesters of a trialcanolamine and their use Download PDFInfo
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- EP0295385B1 EP0295385B1 EP88106112A EP88106112A EP0295385B1 EP 0295385 B1 EP0295385 B1 EP 0295385B1 EP 88106112 A EP88106112 A EP 88106112A EP 88106112 A EP88106112 A EP 88106112A EP 0295385 B1 EP0295385 B1 EP 0295385B1
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- fatty acid
- trialkanolamine
- acid esters
- esters
- acid
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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
- esterification catalysts i.a. Alkali hydroxides, mineral acids, Lewis acids etc. are used.
- the quaternized trialkanolamine difatty acid esters are used as fabric softener components.
- the main component obtained due to the thermodynamic equilibrium is also portions of the corresponding mono- and triesters.
- This thermodynamic mixture is hereinafter to be understood as trialkanolamine difatty acid ester.
- esterification of the trialkanolamines is carried out with about two equivalents of fatty acid in the presence of the known esterification catalysts mentioned above, then after the usual quaternization, e.g. quaternary ammonium compounds obtained with dimethyl sulfate, e.g. N-methyl-triethanolammonium ditallow fatty acid ester methyl sulfate, properties which are undesirable for a raw material for fabric softeners.
- the products adjusted to a content of 85 to 90 percent by weight with water and lower alcohols, such as isopropyl alcohol, are not flowable, that is to say they are too solid, and they also tend to form strong crystals.
- the 85 percent by weight end product consists of a relatively thin melt containing crystallites. These settle out within a very short time when left standing. This affects the processability and even quality fluctuations can occur in the fabric softening agents made from it.
- the task thus arises to find a method of producing trialkanolamine difatty acid esters which can be operated at comparatively low cost and leads to products which are flowable in a highly concentrated setting (85 to 90 percent by weight) and do not tend to settle.
- the fatty acids of the fatty acid esters expediently contain 4 to 24, preferably 8 to 22, in particular 10 to 20, carbon atoms.
- the alcohols of the fatty acid esters advantageously contain 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms.
- the alcohols of the fatty acid esters should be 1 to 6 polyhydric alcohols, preferably 1 to 3 polyhydric alcohols.
- trialkanolamine fatty acid diesters produced according to the process of the invention are to be used as laundry softening agents after the usual quaternization with, for example, dimethyl sulfate.
- Suitable trialkanolamines which are to be implemented according to the invention are those which have the formula are sufficient, in which R, R1 and R2 can be different and are hydrogen or alkyl radicals having 1 to 6, preferably 1 to 4, in particular having one carbon atom (s). R, R1 and R2 are particularly preferably hydrogen.
- trialkanolamines are triethanolamine, triisopropanolamine, triisobutanolamine, triisopentanolamine, triisohexanolamine, diethanolmonoisopropanolamine, monoethanol-diisopropanolamine, monoethanol-diisobutanolamine and analogues.
- the fatty acids which are reacted with the trialkanolamines are expediently those having 8 to 24, preferably 12 to 22, in particular 16 to 20 carbon atoms in the linear or branched alkyl chain or the alkene chain.
- Examples include: carpylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid and their branched or unsaturated homologues, such as e.g. Oleic acid.
- the fatty acid esters present in the reaction of the fatty acids with the trialkanolamines are to be used in amounts of 0.05 to 5.0 percent by weight, preferably 0.1 to 2.0 percent by weight, in particular 0.2 to 1.0 percent by weight, based on the total mixture .
- fatty acid esters are derived, for example, from fatty acids with 4 to 24 carbon atoms, preferably 8 to 22, in particular 10 to 20 carbon atoms.
- branched isomers such as e.g. Isovaleric acid, or its unsaturated isomers, e.g. Oleic acid.
- Suitable alcohols from which the fatty acid esters can be derived, have 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms. They can be 1- to 6-valent, preferably 1- to 3-valent.
- Examples include: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, isohexanol, heptanol, octanol, 2-ethylhexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, butylene glycol 1,2, 1,4-butanediol, pentanediols, hexanediols, heptanediols, octanediols, glycerol, butanetriol, pentanetriols, hexanetriols, octanetriols, erythritol, pentaerythritol, pentites, hexites, such as sorbitol, mannitol, dulci
- the fatty acid esters that can be used are, for example: the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl esters of the above.
- Fatty acids with 4 to 24 carbon atoms preferably the esters of naturally occurring fatty acid mixtures such as tallow fatty acid methyl ester, ethyl ester, coconut fatty acid methyl ester, ethyl ester, palm oil fatty acid methyl ester, ethyl ester, with particular preference the naturally occurring glycerol esters of fatty acids or fatty acid mixtures, such as Tripalmitin, tristearin, tallow fat, coconut fat, palm oil fat.
- the use of partial esters of polyhydric alcohols is also possible, e.g. Glycerol monostearate, glycerol distearate, sorbitol monolaurate, sorbitol distearate, etc.
- fatty acid esters used in the esterification reaction have the same C number in the acyl part as the fatty acids intended for the esterification.
- the pressure and temperature conditions are the same as those used when using known esterification catalysts, namely, for example, 30 to 300 ° C, preferably 170 to 220 ° C and 3 to 3000, preferably 700 to 1100 mbar. Higher temperatures and pressures are also possible, but generally not necessary.
- the mixture is then cooled to 90 ° C. and quaternized with 124.7 g (0.99 mol) of dimethyl sulfate within 30 minutes.
- the product is then adjusted to a solids content of 85% with 140.6 g of isopropyl alcohol and bleached with 20 g (2.5%) of 30% hydrogen peroxide solution.
- the product is just as flowable as that produced according to Example 1.
- Example 1 The procedure is as described in Example 1. Instead of the tallow fatty acid methyl ester, 5 g of oleic acid ethyl ester are used. A product is obtained which is comparable in its properties to that prepared according to Example 1.
Abstract
Description
Die Herstellung von Fettsäurestern, wie auch Trialkanolaminfettsäureestern, ist wohlbekannt. Als Veresterungskatalysatoren werden i.a. Alkalihydroxide, Mineralsäuren, Lewissäuren etc. eingesetzt.The production of fatty acid esters, as well as trialkanolamine fatty acid esters, is well known. As esterification catalysts i.a. Alkali hydroxides, mineral acids, Lewis acids etc. are used.
Als Wäscheweichspülkomponenten werden die quaternierten Trialkanolamindifettsäureester eingesetzt. Bei der Reaktion von ca. zwei Äquivalenten Fettsäure mit Trialkanolamin erhält man neben diesem Trialkanolamindifettsäureester als Hauptkomponente aufgrund des thermodynamischen Gleichgewichtes auch Anteile der entsprechenden Mono- und Triester. Dieses thermodynamische Gemisch ist im weiteren unter der Bezeichnung Trialkanolamindifettsäureester zu verstehen.The quaternized trialkanolamine difatty acid esters are used as fabric softener components. In the reaction of approximately two equivalents of fatty acid with trialkanolamine, in addition to this trialkanolamine difatty acid ester, the main component obtained due to the thermodynamic equilibrium is also portions of the corresponding mono- and triesters. This thermodynamic mixture is hereinafter to be understood as trialkanolamine difatty acid ester.
Führt man die Veresterung der Trialkanolamine mit ca. zwei Äquivalenten Fettsäure in Gegenwart der oben genannten bekannten Veresterungskatalysatoren durch, so zeigen die nach der üblichen Quarternisierung, z.B. mit Dimethylsulfat, erhaltenen quarternären Ammoniumverbindungen, wie z.B. N-Methyl-triethanolammonium-ditalgfettsäureester-methylsulfat, Eigenschaften, die bei einem Rohstoff für Wäscheweichspülmittel unerwünscht sind. Die mit Wasser und niederen Alkoholen, wie Isopropylalkohol, auf einen Gehalt von 85 bis 90 Gewichtsprozent eingestellten Produkte sind nicht fließfähig, also zu fest, und außerdem neigen sie zu starker Kristallbildung.If the esterification of the trialkanolamines is carried out with about two equivalents of fatty acid in the presence of the known esterification catalysts mentioned above, then after the usual quaternization, e.g. quaternary ammonium compounds obtained with dimethyl sulfate, e.g. N-methyl-triethanolammonium ditallow fatty acid ester methyl sulfate, properties which are undesirable for a raw material for fabric softeners. The products adjusted to a content of 85 to 90 percent by weight with water and lower alcohols, such as isopropyl alcohol, are not flowable, that is to say they are too solid, and they also tend to form strong crystals.
In der US-A-3 915 867 wird die Herstellung von Triethanolaminfettsäurediestern durch Umsetzung von Triethanolamin mit Fettsäuremethylestern beschrieben. Die daraus durch Quarternisierung hergestellten quarternären Ammoniumverbindungen zeigen zwar nach der üblichen Einstellung mit Wasser und Isopropanol auf 85 bis 90 Gewichtsprozent die gewünschte fließfähige Beschaffenheit, jedoch ergeben sich in diesem Falle andere Probleme.US Pat. No. 3,915,867 describes the preparation of triethanolamine fatty acid diesters by reacting triethanolamine with fatty acid methyl esters. The quaternary ammonium compounds produced therefrom by quaternization show the desired flowability after the usual adjustment with water and isopropanol to 85 to 90 percent by weight, but in this case there are other problems.
Das 85 gewichtsprozentige Endprodukt besteht aus einer relativ dünnen Schmelze, in der sich Kristallite befinden. Diese setzen sich beim Stehenlassen innerhalb recht kurzer Zeit ab. Dadurch wird die Verarbeitbarkeit beeinträchtigt, und es können sogar Qualitätsschwankungen bei den daraus hergestellten Wäscheweichspülmitteln auftreten.The 85 percent by weight end product consists of a relatively thin melt containing crystallites. These settle out within a very short time when left standing. This affects the processability and even quality fluctuations can occur in the fabric softening agents made from it.
Außerdem ist zu bedenken, daß die als Reaktanten eingesetzten Methylester gegenüber den unveresterten Fettsäuren eine veredelte Verarbeitungsstufe darstellen und daß deren Einsatz somit erheblich kostenaufwendiger ist.It should also be borne in mind that the methyl esters used as reactants represent a refined processing stage compared to the unesterified fatty acids and that their use is therefore considerably more expensive.
Es ergibt sich somit die Aufgabenstellung, eine Methode der Herstellung von Trialkanolamindifettsäureestern zu finden, welche mit vergleichsweise geringem Kostenaufwand betrieben werden kann und zu Produkten führt, die in hochkonzentrierter Einstellung (85 bis 90 Gewichtsprozent) fließfähig sind und nicht zum Absetzen neigen.The task thus arises to find a method of producing trialkanolamine difatty acid esters which can be operated at comparatively low cost and leads to products which are flowable in a highly concentrated setting (85 to 90 percent by weight) and do not tend to settle.
Diese Aufgaben wurden gelöst durch ein Verfahren zur Herstellung von Trialkanolamindifettsäureestern durch Umsetzen von Trialkanolamin mit 1,5 bis 2,5, bevorzugt 1,8 bis 2,2, insbesondere 1,9 bis 2,1 Äquivalenten Fettsäure, das dadurch gekennzeichnet ist, daß man die Umsetzung in Gegenwart von 0,05 bis 5,0, vorzugsweise 0,1 bis 2,0, insbesondere von 0,2 bis 1,0 Gewichtsprozent, bezogen auf die Gesamtmischung, eines Fettsäureesters vornimmt.These objects were achieved by a process for the preparation of trialkanolamine difatty acid esters by reacting trialkanolamine with 1.5 to 2.5, preferably 1.8 to 2.2, in particular 1.9 to 2.1 equivalents of fatty acid, which is characterized in that the reaction is carried out in the presence of 0.05 to 5.0, preferably 0.1 to 2.0, in particular 0.2 to 1.0 percent by weight, based on the mixture as a whole, of a fatty acid ester.
Zweckmäßigerweise enthalten die Fettsäuren der Fettsäureester 4 bis 24, vorzugsweise 8 bis 22, insbesondere 10 bis 20 Kohlenstoffatome.The fatty acids of the fatty acid esters expediently contain 4 to 24, preferably 8 to 22, in particular 10 to 20, carbon atoms.
Die Alkohole der Fettsäureester enthalten zweckmäßigerweise 1 bis 8, vorzugsweise 1 bis 6, insbesondere 1 bis 3 Kohlenstoffatome.The alcohols of the fatty acid esters advantageously contain 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms.
Die Alkohole der Fettsäureester sollten 1- bis 6 wertige Alkohole, vorzugsweise 1- bis 3 wertige Alkohole, sein.The alcohols of the fatty acid esters should be 1 to 6 polyhydric alcohols, preferably 1 to 3 polyhydric alcohols.
Die gemäß dem Verfahren der Erfindung hergestellten Trialkanolaminfettsäurediester sind _ nach der üblichen Quarternisierung mit z.B. Dimethylsulfat _ als Wäscheweichspülmittel zu verwenden.The trialkanolamine fatty acid diesters produced according to the process of the invention are to be used as laundry softening agents after the usual quaternization with, for example, dimethyl sulfate.
Als Trialkanolamine, welche erfindungsgemäß umzusetzen sind, kommen zweckmäßigerweise solche infrage, die der Formel
Beispiele für Trialkanolamine sind Triethanolamin, Triisopropanolamin, Triisobutanolamin, Triisopentanolamin, Triisohexanolamin, Diethanolmonoisopropanolamin, Monoethanol-diisopropanolamin, Monoethanol-diisobutanolamin und Analoge.Examples of trialkanolamines are triethanolamine, triisopropanolamine, triisobutanolamine, triisopentanolamine, triisohexanolamine, diethanolmonoisopropanolamine, monoethanol-diisopropanolamine, monoethanol-diisobutanolamine and analogues.
Die Fettsäuren, welche mit den Trialkanolaminen zur Umsetzung kommen, sind zweckmäßigerweise solche mit 8 bis 24, vorzugsweise 12 bis 22, insbesondere mit 16 bis 20 Kohlenstoffatomen in der linearen oder verzweigten Alkylkette oder der Alkenkette.The fatty acids which are reacted with the trialkanolamines are expediently those having 8 to 24, preferably 12 to 22, in particular 16 to 20 carbon atoms in the linear or branched alkyl chain or the alkene chain.
Es kommen beispielsweise infrage: Carpylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Stearinsäure, Arachinsäure, Behensäure sowie deren verzweigte oder deren ungesättigte Homologe, wie z.B. Ölsäure.Examples include: carpylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid and their branched or unsaturated homologues, such as e.g. Oleic acid.
Die bei der Umsetzung der Fettsäuren mit den Trialkanolaminen anwesenden Fettsäureester sind in Mengen von 0,05 bis 5,0 Gewichtsprozent, vorzugsweise 0,1 bis 2,0 Gewichtsprozent, insbesondere 0,2 bis 1,0 Gewichtsprozent, bezogen auf die Gesamtmischung, einzusetzen.The fatty acid esters present in the reaction of the fatty acids with the trialkanolamines are to be used in amounts of 0.05 to 5.0 percent by weight, preferably 0.1 to 2.0 percent by weight, in particular 0.2 to 1.0 percent by weight, based on the total mixture .
Diese Fettsäureester leiten sich z.B. von Fettsäuren mit 4 bis 24 Kohlenstoffatomen, vorzugsweise 8 bis 22, insbesondere 10 bis 20 Kohlenstoffatomen ab.These fatty acid esters are derived, for example, from fatty acids with 4 to 24 carbon atoms, preferably 8 to 22, in particular 10 to 20 carbon atoms.
Es kommen z.B. infrage: Buttersäure, Valeriansäure, Capron-, Capryl-, Caprin-, Laurin-, Myristin-, Palmitin-, Stearin-, Arachin-, Behen- und Lignocerinsäure sowie deren verzweigte Isomere, wie z.B. Isovaleriansäure, oder deren ungesättigte Isomere, wie z.B. Ölsäure.For example, in question: butyric acid, valeric acid, capronic, caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic and lignoceric acid and their branched isomers, such as e.g. Isovaleric acid, or its unsaturated isomers, e.g. Oleic acid.
Geeignete Alkohole, von denen sich die Fettsäureester ableiten können, haben 1 bis 8, vorzugsweise 1 bis 6, insbesondere 1 bis 3 Kohlenstoffatome. Sie können 1- bis 6 wertig, vorzugsweise 1- bis 3 wertig, sein.Suitable alcohols, from which the fatty acid esters can be derived, have 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms. They can be 1- to 6-valent, preferably 1- to 3-valent.
Es lassen sich beispielsweise nennen: Methanol, Ethanol, Propanol, Isopropanol, Butanol, Isobutanol, Pentanol, Isopentanol, Hexanol, Isohexanol, Heptanol, Octanol, 2-Ethylhexanol, Ethylenglykol, Propandiol-1,2, Propandiol-1,3, Butylenglykol-1,2, Butandiol-1,4, Pentandiole, Hexandiole, Heptandiole, Octandiole, Glycerin, Butantriol, Pentantriole, Hexantriole, Octantriole, Erythrit, Pentaerythrit, Pentite, Hexite, wie Sorbit, Mannit, Dulcit, vorzugsweise Methanol, Ethanol und Glycerin.Examples include: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, isohexanol, heptanol, octanol, 2-ethylhexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, butylene glycol 1,2, 1,4-butanediol, pentanediols, hexanediols, heptanediols, octanediols, glycerol, butanetriol, pentanetriols, hexanetriols, octanetriols, erythritol, pentaerythritol, pentites, hexites, such as sorbitol, mannitol, dulcitol, preferably methanol, ethanol and glycerol.
Als Fettsäureester lassen sich somit beispielsweise einsetzen: die Methyl-, Ethyl-, Propyl-, Isopropyl-, Butyl-, Pentyl-, Hexylester der o.a. Fettsäuren mit 4 bis 24 C-Atomen, mit Vorzug die Ester der natürlich vorkommenden Fettsäuregemische, wie Talgfettsäuremethylester, -ethylester, Kokosfettsäuremethylester, -ethylester, Palmölfettsäuremethylester, -ethylester, mit besonderem Vorzug die natürlich vorkommenden Glycerinester der Fettsäuren bzw. Fettsäuregemische, wie z.B. Tripalmitin, Tristearin, Talgfett, Kokosfett, Palmölfett. Auch der Einsatz von Teilestern mehrwertiger Alkohole ist möglich, also z.B. Glycerinmonostearat, Glycerindistearat, Sorbitmonolaurat, Sorbitdistearat, etc.The fatty acid esters that can be used are, for example: the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl esters of the above. Fatty acids with 4 to 24 carbon atoms, preferably the esters of naturally occurring fatty acid mixtures such as tallow fatty acid methyl ester, ethyl ester, coconut fatty acid methyl ester, ethyl ester, palm oil fatty acid methyl ester, ethyl ester, with particular preference the naturally occurring glycerol esters of fatty acids or fatty acid mixtures, such as Tripalmitin, tristearin, tallow fat, coconut fat, palm oil fat. The use of partial esters of polyhydric alcohols is also possible, e.g. Glycerol monostearate, glycerol distearate, sorbitol monolaurate, sorbitol distearate, etc.
Es ist nicht notwendig, daß die bei der Veresterungsreaktion eingesetzten Fettsäureester im Acylteil dieselbe C-Zahl aufweisen wie die für die Veresterung bestimmten Fettsäuren.It is not necessary that the fatty acid esters used in the esterification reaction have the same C number in the acyl part as the fatty acids intended for the esterification.
Die Druck- und Temperaturbedingungen sind die gleichen, wie sie auch bei Einsatz bekannter Veresterungskatalysatoren angewendet werden, nämlich z.B. 30 bis 300°C, vorzugsweise 170 bis 220°C und 3 bis 3000, vorzugsweise 700 bis 1100 mbar. Es sind auch höhere Temperaturen und Drücke möglich, aber i.a. nicht notwendig.The pressure and temperature conditions are the same as those used when using known esterification catalysts, namely, for example, 30 to 300 ° C, preferably 170 to 220 ° C and 3 to 3000, preferably 700 to 1100 mbar. Higher temperatures and pressures are also possible, but generally not necessary.
Die nun folgenden Beispiele dienen der weiteren Erläuterung der Erfindung.The following examples serve to further explain the invention.
552 g (2 Mol) Talgfettsäure (z.B. EDENOR(R) Ti der Fa. Henkel) werden aufgeschmolzen vorgelegt, auf 90°C erwärmt und mit 4 g (=0,56% des gesamten Veresterungsgemisches) Talgfettsäuremethylester (z.B. EDENOR ME/Ti der Fa. Henkel) versetzt. Nachdem 15 Minuten gerührt wurde, werden 156 g (1,05 Mol) Triethanolamin hinzugegeben, das Reaktionsgemisch anschließend auf 195°C erwärmt und bei dieser Temperatur weitergerührt, bis eine Säurezahl von ≦1mg KOH/G erreicht ist. Dies ist nach ca. 3 Stunden der Fall, wobei 36 g Wasser abdestillieren.552 g (2 mol) of tallow fatty acid ( e.g. EDENOR (R) Ti from Henkel) are melted, heated to 90 ° C and with 4 g (= 0.56% of the total esterification mixture) tallow fatty acid methyl ester (e.g. EDENOR ME / Ti der Henkel). After stirring for 15 minutes, 156 g (1.05 mol) of triethanolamine are added, the reaction mixture is then heated to 195 ° C. and stirring is continued at this temperature until an acid number of ≦ 1 mg KOH / G is reached. This is the case after about 3 hours, with 36 g of water distilling off.
Anschließend wird auf 90°C abgekühlt und mit 124,7 g (0,99 Mol) Dimethylsulfat innerhalb 30 Minuten quarterniert. Danach wird das Produkt mit 140,6 g Isopropylalkohol auf einen Feststoffgehalt von 85% eingestellt und mit 20 g (2,5%) 30%iger Wasserstoffperoxidlösung gebleicht.The mixture is then cooled to 90 ° C. and quaternized with 124.7 g (0.99 mol) of dimethyl sulfate within 30 minutes. The product is then adjusted to a solids content of 85% with 140.6 g of isopropyl alcohol and bleached with 20 g (2.5%) of 30% hydrogen peroxide solution.
Man erhält ein fast farbloses fließfähiges Produkt, das sich durch eine gute Verarbeitbarkeit auszeichnet. Um diese helle Farbe zu erreichen, sollte während der gesamten Reaktionsdauer Sauerstoff aus dem Reaktionsgefäß ausgeschlossen sein. Es bietet sich ein Durchleiten von ca. 30 l/h Stickstoff an.
Nach sechsmonatigem Stehen bei Raumtemperatur konnten keine Separationserscheinungen beobachtet werden. Das Produkt war gleichbleibend fließfähig.An almost colorless, flowable product is obtained which is characterized by good processability. In order to achieve this bright color, oxygen should be excluded from the reaction vessel during the entire reaction period. It is advisable to pass about 30 l / h of nitrogen.
After standing for six months at room temperature, no signs of separation could be observed. The product was consistently flowable.
Man verfährt wie unter Beispiel 1 beschrieben, nur werden anstelle des Talgfettsäuremethylesters 6 g Kokosfett (=Glycerintrikokosfettsäureester) eingesetzt. Das Produkt ist ebenso fließfähig wie das nach Beispiel 1 hergestellte.The procedure is as described in Example 1, except that 6 g of coconut fat (= glycerol tricoconut fatty acid ester) are used instead of the tallow fatty acid methyl ester. The product is just as flowable as that produced according to Example 1.
Man verfährt wie unter Beispiel 1 beschrieben. Anstelle des Talgfettsäuremethylesters werden 5 g Ölsäureethylester eingesetzt. Man erhält ein Produkt, daß in seinen Eigenschaften dem nach Beispiel 1 hergestellten vergleichbar ist.The procedure is as described in Example 1. Instead of the tallow fatty acid methyl ester, 5 g of oleic acid ethyl ester are used. A product is obtained which is comparable in its properties to that prepared according to Example 1.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT88106112T ATE61565T1 (en) | 1987-06-19 | 1988-04-16 | PROCESS FOR THE PREPARATION OF TRIALKANOLAMINE DIFATTY ESTERS AND THEIR USE. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873720332 DE3720332A1 (en) | 1987-06-19 | 1987-06-19 | METHOD FOR PRODUCING TRIALKANOLAMINE DIFETIC ACID ESTERS AND THE USE THEREOF |
| DE3720332 | 1987-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0295385A1 EP0295385A1 (en) | 1988-12-21 |
| EP0295385B1 true EP0295385B1 (en) | 1991-03-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88106112A Expired - Lifetime EP0295385B1 (en) | 1987-06-19 | 1988-04-16 | Process for preparing fatty acid diesters of a trialcanolamine and their use |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4830771A (en) |
| EP (1) | EP0295385B1 (en) |
| AT (1) | ATE61565T1 (en) |
| AU (1) | AU1813188A (en) |
| DE (2) | DE3720332A1 (en) |
| ES (1) | ES2019855B3 (en) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3842571A1 (en) * | 1988-12-17 | 1990-06-21 | Pfersee Chem Fab | HYDROPHILIC SOFT HANDLE FOR FIBROUS MATERIALS AND THEIR USE |
| ES2021900A6 (en) * | 1989-07-17 | 1991-11-16 | Pulcra Sa | Process for preparing quaternary ammonium compounds. |
| US5516438A (en) * | 1989-09-19 | 1996-05-14 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
| GB8921168D0 (en) * | 1989-09-19 | 1989-11-08 | Unilever Plc | Fabric softening |
| DE4101251A1 (en) * | 1991-01-17 | 1992-07-23 | Huels Chemische Werke Ag | AQUEOUS EMULSIONS CONTAINING FATTY ACID ESTERS OF N-METHYL-N, N, N-TRIHYDROXYETHYL-AMMONIUM-METHYL SULFATE |
| ES2094893T3 (en) * | 1991-12-31 | 1997-02-01 | Stepan Europe | SURFACES BASED ON QUATERNARY AMMONIUM COMPOUNDS, PREPARATION PROCEDURES, BASES, AND DERIVED SOFTENING COMPOSITIONS. |
| DE4224714A1 (en) * | 1992-07-27 | 1994-02-03 | Henkel Kgaa | Foaming detergent mixtures |
| ZA936280B (en) * | 1992-09-16 | 1995-05-26 | Colgate Palmolive Co | Fabric softening composition based on higher fatty acid ester and dispersant for such ester |
| DE4232448A1 (en) * | 1992-09-28 | 1994-03-31 | Henkel Kgaa | Process for the preparation of powdered or granular detergent mixtures |
| DE4243862A1 (en) * | 1992-12-23 | 1994-06-30 | Huels Chemische Werke Ag | Process for the quaternization of triethanolamine fatty acid esters and imidazoline amides in alkoxylated fats or oils as the reaction medium and the use of the reaction mixtures as fabric softening agent components |
| DE4334365A1 (en) * | 1993-10-08 | 1995-04-13 | Henkel Kgaa | Quaternized fatty acid triethanolamine ester salts with improved water solubility |
| DE4405702A1 (en) * | 1994-02-23 | 1995-08-24 | Witco Surfactants Gmbh | Highly concentrated aqueous fabric softener with improved storage stability |
| US5463094A (en) * | 1994-05-23 | 1995-10-31 | Hoechst Celanese Corporation | Solvent free quaternization of tertiary amines with dimethylsulfate |
| DE4430721A1 (en) * | 1994-08-30 | 1996-03-07 | Hoechst Ag | Car gloss desiccant |
| US5503756A (en) * | 1994-09-20 | 1996-04-02 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
| DE4446137A1 (en) * | 1994-12-23 | 1996-06-27 | Huels Chemische Werke Ag | Quaternized triethanolamine difatty acid esters |
| US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
| DE59706886D1 (en) * | 1996-06-12 | 2002-05-08 | Akzo Nobel Nv | METHOD FOR PRODUCING ESTERQUATS |
| ATE262506T1 (en) | 1997-05-19 | 2004-04-15 | Procter & Gamble | QUARTERNARY FATTY ACID TRIETHANOLAMINE ESTER SALTS AND THEIR USE AS TISSUE PLASTICIZERS |
| US6759383B2 (en) | 1999-12-22 | 2004-07-06 | The Procter & Gamble Company | Fabric softening compound |
| WO1999035120A1 (en) * | 1998-01-09 | 1999-07-15 | Witco Corporation | Novel quaternary ammonium compounds, compositions containing them, and uses thereof |
| DE19821348B4 (en) * | 1998-05-13 | 2006-02-16 | Cognis Ip Management Gmbh | Ethoxylated esterquats |
| DE19855366A1 (en) | 1998-12-01 | 2000-06-08 | Witco Surfactants Gmbh | Low-concentration, highly viscous aqueous fabric softener |
| DE19855954A1 (en) * | 1998-12-04 | 2000-06-08 | Cognis Deutschland Gmbh | Process for the preparation of low-viscosity ester quat preparations |
| US6271185B1 (en) | 1999-10-29 | 2001-08-07 | Cargill, Incorporated | Water soluble vegetable oil esters for industrial applications |
| US8618316B1 (en) | 2004-03-05 | 2013-12-31 | Stepan Company | Low temperature ramp rate ester quat formation process |
| US7211556B2 (en) * | 2004-04-15 | 2007-05-01 | Colgate-Palmolive Company | Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient |
| DE602006014370D1 (en) | 2005-03-14 | 2010-07-01 | Akzo Nobel Nv | REMOVAL OF SULFUR DIOXIDE RESIDUES FROM DIMETHYL SULPHATE |
| EP1902083B1 (en) * | 2005-06-29 | 2010-10-20 | Colgate-Palmolive Company | Oligomeric amidoamines or amidoquats for fabric or hair treatment compositions |
| CN102336675A (en) * | 2010-07-21 | 2012-02-01 | 博兴华润油脂化学有限公司 | Production method of esterquats |
| GB2516862A (en) | 2013-08-01 | 2015-02-11 | M I Drilling Fluids Uk Ltd | Quaternary ammonium compounds and gas hydrate inhibitor compositions |
| EP3181667A1 (en) * | 2015-12-18 | 2017-06-21 | Kao Corporation, S.A. | Fabric softener active compositions |
| US10975339B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing articles |
| US10975338B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing three-dimensional articles |
| US10975340B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing fibrous structure articles |
| ES2802425T3 (en) * | 2017-06-20 | 2021-01-19 | Kao Corp Sa | Active fabric softener compositions |
| DK3418353T3 (en) * | 2017-06-20 | 2020-09-28 | Kao Corp Sa | RINSE RANGE ACTIVE COMPOSITIONS |
| PT3418355T (en) * | 2017-06-20 | 2020-07-27 | Kao Corp Sa | Fabric softener active compositions |
| CN112334443B (en) | 2018-06-26 | 2023-08-22 | 赢创运营有限公司 | Preparation method of oil-based esterquat |
| US20230092174A1 (en) | 2021-08-02 | 2023-03-23 | The Procter & Gamble Company | Active agent-containing articles |
| EP4282854A1 (en) | 2022-05-25 | 2023-11-29 | Unión Deriván, S.A. | Process for the production of esterquats |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2228985A (en) * | 1937-12-21 | 1941-01-14 | Petrolite Corp | Ricinoleic acid ester of triethanolamine |
| US2173058A (en) * | 1939-05-04 | 1939-09-12 | Kritchevsky Wolf | Acid substituted hydroxy alkylamines and process of making same |
| US3915867A (en) * | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
| DE2525610C2 (en) * | 1975-06-09 | 1985-04-11 | Henkel KGaA, 4000 Düsseldorf | Cationic softeners with improved cold water solubility |
| DD159263A3 (en) * | 1980-12-23 | 1983-03-02 | Peter Reinemann | WEICHSPUELMITTELKONZENTRATE |
| DE3137043A1 (en) * | 1981-09-17 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | AMMONIUM COMPOUNDS |
-
1987
- 1987-06-19 DE DE19873720332 patent/DE3720332A1/en not_active Withdrawn
-
1988
- 1988-04-16 AT AT88106112T patent/ATE61565T1/en not_active IP Right Cessation
- 1988-04-16 ES ES88106112T patent/ES2019855B3/en not_active Expired - Lifetime
- 1988-04-16 DE DE8888106112T patent/DE3861985D1/en not_active Expired - Lifetime
- 1988-04-16 EP EP88106112A patent/EP0295385B1/en not_active Expired - Lifetime
- 1988-06-17 US US07/208,054 patent/US4830771A/en not_active Expired - Fee Related
- 1988-06-17 AU AU18131/88A patent/AU1813188A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE3720332A1 (en) | 1988-12-29 |
| ATE61565T1 (en) | 1991-03-15 |
| ES2019855A4 (en) | 1991-07-16 |
| US4830771A (en) | 1989-05-16 |
| AU1813188A (en) | 1988-12-22 |
| DE3861985D1 (en) | 1991-04-18 |
| EP0295385A1 (en) | 1988-12-21 |
| ES2019855B3 (en) | 1991-12-01 |
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