WO1997012856A1 - Process for producing betaine surfactants with low salt content - Google Patents

Process for producing betaine surfactants with low salt content Download PDF

Info

Publication number
WO1997012856A1
WO1997012856A1 PCT/EP1996/004120 EP9604120W WO9712856A1 WO 1997012856 A1 WO1997012856 A1 WO 1997012856A1 EP 9604120 W EP9604120 W EP 9604120W WO 9712856 A1 WO9712856 A1 WO 9712856A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
carbon atoms
fatty acid
weight
salt content
Prior art date
Application number
PCT/EP1996/004120
Other languages
German (de)
French (fr)
Inventor
Nagao Totani
Kakushi Dohki
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1997012856A1 publication Critical patent/WO1997012856A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification

Definitions

  • the invention relates to a process for the production of betaine surfactants with a low salt content, in which nitrogen compounds are alkylated in aqueous-alcoholic dispersion and aftertreated in a manner known per se
  • Amphoteric surfactants of the betaine type are produced by reacting a fatty amine or fatty acid amidoamine with alkylating agents, preferably sodium chloroacetate, and are widely used as auxiliaries for detergents, dishwashing detergents, cleaning agents, cosmetics and textile products.
  • alkylating agents preferably sodium chloroacetate
  • larger amounts of inorganic are by-products Salts that have a corrosive effect on metals and can irritate the skin and mucous membranes. For this reason, there is a need in the market for betaine surfactants with a reduced salt content
  • Betaines are usually desalted by first producing a preliminary product with a low water content, dissolving the insoluble salt in an organic solvent, then filtering off the solvent and then removing the solvent in vacuo.
  • the evaporation of large amounts of water from the surfactant proves to be problematic in this process due to the high foam formation , with further disadvantages in the heat loss of the heat-induced discoloration and the time consuming process.
  • the production of a betaine surfactant with little use of water is associated with very great difficulties due to the extremely increasing viscosity.
  • Japanese patent JP-B Sho 51-113820 describes a desalination process in which a betaine solution with a low water content is treated with a strongly alkaline compound.
  • the solution is desalted by reducing the water content to below 20% by evaporation and then adjusting the pH of the solution to a value> 9.
  • the evaporation of the water from the surfactant solution is very good difficult and time consuming.
  • there is a very slow reaction rate the amine number of the fatty amine remaining unchanged if the alcohol content of the reaction system is too high and the water content is too low.
  • too high a water content ensures a smooth reaction process, but causes a large part of the salt to dissolve and the evaporation of the water is made more difficult.
  • the invention relates to a process for the production of betaine surfactants with a low salt content, in which fatty amines and / or fatty acid amidoamines in aqueous-alcoholic dispersion are filtered off with inorganic carbons or their alkali metal salts, the solvent is removed and the residue is adjusted to the desired active ingredient concentrate with water which is characterized in that the dispersant used is a mixture of 5 to 10% by weight of water and 35 to 50% by weight of ethanol and / or isopropyl alcohol, in each case based on the sum of the starting materials
  • R 1 represents a linear or branched, optionally hydroxyl-substituted alkyl radical having 6 to 22, preferably 12 to 18 carbon atoms and R 2 and R 3 independently of one another are R 1 or alkyl radicals having 1 to 4 carbon atoms.
  • Lauryldimethylamine is preferably used
  • fatty acid amidoamines of the formula (II) can also be used as further starting materials,
  • R 4 CO stands for a linear or branched acyl radical having 6 to 22, preferably 12 to 18 carbon atoms
  • R s , R ⁇ and R 7 independently of one another for hydrogen or an alkyl radical with 1 to 4 carbon atoms and n for numbers from 1 to 3
  • Typical examples are amidoamines derived from technical coconut fatty acid cuts and ethylenediamine, N, N-dimethylethylenediamine or N, N-dimethylpropylenediamine.
  • Suitable alkylating agents are both halocarboxylic acids and their salts. Typical examples are chloroacetic acid and preferably sodium chloroacetate, the amines or amidoamines and the alkylating agents generally being in a molar ratio of 1: 0.75 to 1: 1.05 and preferably 1: 0. 8 to 1: 0.95 method
  • the procedure is usually such that 1 mol of the alkali agent, preferably anhydrous sodium chloroacetate, is first dispersed in the aqueous alcohol. 0.8 to 0.95 mol of a molten fatty amine or fatty acid amidoamine are slowly added dropwise to this dispersion while stirring The reaction is carried out at temperatures in the range from 60 to 90 ° C. until the amine number has dropped below a value of at least 5, preferably below 2. After the reaction has ended, the salt formed as a by-product is filtered off, the alcohol portion of the mixture is evaporated in vacuo and the Betain concentration of the final product adjusted by adding water
  • the alkylating agent should advantageously be used as the finest, anhydrous powder possible. If the grain size is too coarse, the reaction rate slows down in the medium consisting of alcohol and water. Specifically, 10-20% by weight of the total powder should have a grain size of 50-100 mesh and over 95% by weight of the powder should have a particle size ⁇ 20 mesh.
  • the ratio of water to alcohol in the reaction system should preferably be chosen so that the alkylating agent is dispersed, the reaction with the fatty amine or fatty acid amidoamine proceeds smoothly and the salt formed as a by-product is salted out.
  • the rate of reaction of the alkylating agent with the fatty amine or fatty acid amidoamine can be slowed down, so that the solution has too high a residual amine number the reaction proceeds smoothly with water contents above 10% by weight or alcohol contents below 35% by weight, but the salt which is obtained as a by-product dissolves in the mixture instead of being salted out, so that the salt is difficult to separate off Industrial applicability
  • the betaine surfactants obtainable by the process according to the invention have a particularly low content of inorganic salts and therefore a particularly high skin-cosmetic compatibility. They are therefore particularly suitable for the production of surface-active agents that come into contact with human skin, such as hand dishwashing detergents or hair shampoos, in which they are used in amounts of 1 to 50, preferably 2 to 15,% by weight, based on the Means - may be included.
  • Example 2 Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 75 ml of ethanol and 10 ml of water and then reacted with 70 g (0.29 mol) of lauryidimethylamine. After the reaction had ended, the reactor was cooled to room temperature and the salted-out NaCl filtered off the ethanol evaporated and the active ingredient concentration of the solution adjusted to 30% by weight. The resulting solution had a salt content of 1.01% and an amine number of 1.35. Comparative Example V1
  • Example 2 32 g of sodium chloroacetate were dispersed in a mixture of 150 ml of isopropyl alcohol and 10 ml of water and reacted with 85 g of molten coconut fatty acid amidopropyldimethylamine 30 wt .-% adjusted The resulting solution contained 0.59 wt .-% NaCl with an amine number of 4.46.
  • Example 2 Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 75 ml of ethanol and 40 ml of water and 85 g of melted coconut fatty acid amidopropyldimethylamine were added dropwise. After the reaction had ended, the salt was filtered off, the ethanol was evaporated in vacuo and the active ingredient concentration was increased to 30% by adding water. -% adjusted The resulting solution contained 2.89% by weight NaCl; the amine number was 1.32
  • Example 2 Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 150 ml of ethanol and 40 ml of water. 85 g of melted coconut fatty acid amidopropyldimethylamine were added dropwise to this dispersion Water adjusted to 30 wt.% The resulting solution contained 2.11 wt.% NaCl with an amine number of 2.29.

Abstract

A process is disclosed for producing betaine surfactants with a reduced salt content. Fatty amines and/or fatty acid amidoamines are alkylated in an aqueous-alcoholic dispersion with halogenated carboxylic acids or their alkali salts, thus formed inorganic salts are filtered out, the solvent is removed and the residue is mixed with water to set the desired concentration of active substance.

Description

Verfahren zur Herstellung von Betaintensiden mit geπngem Salzgehalt Process for the preparation of betaine surfactants with a low salt content
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft ein Verfahren zur Herstellung von Betaintensiden mit geringem Salzgehalt bei dem man Stickstoffverbindungen in wäßrig-alkoholischer Dispersion alkyliert und in an sich bekannter Weise nachbehandeltThe invention relates to a process for the production of betaine surfactants with a low salt content, in which nitrogen compounds are alkylated in aqueous-alcoholic dispersion and aftertreated in a manner known per se
Stand der TechnikState of the art
Amphotere Tenside vom Betaintyp werden durch Reaktion eines Fettamins oder Fettsäureamidoamins mit Alkylierungsmitteln, vorzugsweise Natriumchloracetat hergestellt und weithin als Hilfsstoff für Wasch-, Spül- und Reinigungsmittel, Kosmetik- und Textilprodukte eingesetzt Bei der vorgenannten Reaktion zur Herstellung der Betainverbindungen fallen jedoch als Nebenprodukte größere Mengen anorganische Salze an, die korrodierend auf Metalle wirken und Haut und Schleimhäute reizen können. Aus diesem Grund besteht im Markt ein Bedürfnis nach Betaintensiden mit vermindertem SalzgehaltAmphoteric surfactants of the betaine type are produced by reacting a fatty amine or fatty acid amidoamine with alkylating agents, preferably sodium chloroacetate, and are widely used as auxiliaries for detergents, dishwashing detergents, cleaning agents, cosmetics and textile products. In the aforementioned reaction for the production of betaine compounds, however, larger amounts of inorganic are by-products Salts that have a corrosive effect on metals and can irritate the skin and mucous membranes. For this reason, there is a need in the market for betaine surfactants with a reduced salt content
Betaine werden in der Regel entsalzt indem man zunächst ein Vorprodukt mit niedrigem Wassergehalt hergestellt dieses in einem organischen Lösungsmittel löst das unlösliche Salz abfiltriert und anschließend das Lösungsmittel im Vakuum entfernt Die Verdampfung größerer Wassermengen aus dem Tensid erweist sich bei diesem Verfahren aufgrund der starken Schaumbildung als problematisch, wobei weitere Nachteile in dem Wärmeverlust der erhitzungsbedingten Verfärbung sowie der Zeitaufwendigkeit des Verfahrens bestehen. Die Herstellung eines Betaintensids unter geringem Wassereinsatz ist andererseits aufgrund der extrem zunehmenden Viskosität mit sehr großen Schwierigkeiten verbunden. Das japanische Patent JP-B Sho 51-113820 beschreibt ein Entsalzungsverfahren, bei dem eine Betainlösung von geringem Wassergehalt mit einer stark alkalischen Verbindung behandelt wird. Gemäß diesem Verfahren wird die Lösung entsalzt indem man den Wasseranteil durch Verdampfung auf unter 20% reduziert und der pH-Wert der Lösung dann auf einen Wert > 9 einstellt Die Verdamp¬ fung des Wassers aus der Tensidlösung gestaltet sich jedoch, wie vorstehend bereits erwähnt sehr schwierig und zeitraubend. Zudem ergibt sich eine sehr geringe Reaktionsgeschwindigkeit wobei die Aminzahl des Fettamins unverändert bleibt wenn der Alkoholgehalt des Reaktionssystems zu hoch und der Wassergehalt zu gering ist En zu hoher Wassergehalt gewährleistet andererseits einen rei¬ bungslosen Reaktionsverlauf, bewirkt jedoch, daß ein Großteil des Salzes in Lösung geht und die Ver¬ dampfung des Wassers erschwert wird.Betaines are usually desalted by first producing a preliminary product with a low water content, dissolving the insoluble salt in an organic solvent, then filtering off the solvent and then removing the solvent in vacuo.The evaporation of large amounts of water from the surfactant proves to be problematic in this process due to the high foam formation , with further disadvantages in the heat loss of the heat-induced discoloration and the time consuming process. On the other hand, the production of a betaine surfactant with little use of water is associated with very great difficulties due to the extremely increasing viscosity. Japanese patent JP-B Sho 51-113820 describes a desalination process in which a betaine solution with a low water content is treated with a strongly alkaline compound. According to this process, the solution is desalted by reducing the water content to below 20% by evaporation and then adjusting the pH of the solution to a value> 9. However, as already mentioned above, the evaporation of the water from the surfactant solution is very good difficult and time consuming. In addition, there is a very slow reaction rate, the amine number of the fatty amine remaining unchanged if the alcohol content of the reaction system is too high and the water content is too low. On the other hand, too high a water content ensures a smooth reaction process, but causes a large part of the salt to dissolve and the evaporation of the water is made more difficult.
Die Aufgabe der vorliegenden Erfindung hat daher darin bestanden, ein Verfahren zur Herstellung von Betaintensiden mit geringem Salzgehalt und niedriger Aminzahl zur Verfügung zu stellen, das frei von den geschilderten Nachteilen istThe object of the present invention was therefore to provide a process for the preparation of betaine surfactants with a low salt content and a low amine number which is free from the disadvantages described
Beschreibuno der ErfindungDescription of the invention
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Betaintensiden mit geringem Salzgehalt bei dem man Fettamine und/oder Fettsäureamidoamine in wäßrig-alkoholischer Dispersion mit Halogencarbonsäuren oder deren Alkalisalzen alkyliert gebildete anorganische Salze abfiitriert, das Lösungsmittel entfernt und den Rückstand mit Wasser auf die gewünschte Wirkstoffkonzentratjon einstellt das sich dadurch auszeichnet daß man als Dispergiermittel eine Mischung aus 5 bis 10 Gew.- % Wasser und 35 bis 50 Gew.-% Ethanol und/oder Isopropylalkohol -jeweils bezogen auf die Summe der Einsatzstoffe - einsetztThe invention relates to a process for the production of betaine surfactants with a low salt content, in which fatty amines and / or fatty acid amidoamines in aqueous-alcoholic dispersion are filtered off with inorganic carbons or their alkali metal salts, the solvent is removed and the residue is adjusted to the desired active ingredient concentrate with water which is characterized in that the dispersant used is a mixture of 5 to 10% by weight of water and 35 to 50% by weight of ethanol and / or isopropyl alcohol, in each case based on the sum of the starting materials
Überraschenderweise wurde gefunden, daß durch Dispergieren der Ausgangsstoffe in einer definierten wäßrig-alkoholischer Lösung ein Vorprodukt erhalten wird, das sich einerseits leicht entsalzen und von Lösungsmittel befreien läßt und andererseits eine niedrige Aminzahl aufweist FettamineSurprisingly, it was found that by dispersing the starting materials in a defined aqueous-alcoholic solution, a preliminary product is obtained which, on the one hand, can be easily desalted and freed from solvent and, on the other hand, has a low amine number Fatty amines
Fettamine, die als Einsatzstoffe in Betracht kommen, folgen üblicherweise der Formel (I),Fatty amines which are suitable as starting materials usually follow the formula (I),
R3 R 3
I R'-N-R' (I)I R'-N-R '(I)
in der R1 für einen linearen oder verzweigten, gegebenenfalls hydroxysubstituierten Alkylrest mit 6 bis 22, vorzugsweise 12 bis 18 Kohlenstoffatomen und R2 und R3 unabhängig voneinander für R1 oder Alkylreste mit 1 bis 4 Kohlenstoffatomen stehen. Vorzugsweise wird Lauryldimethylamin eingesetztin which R 1 represents a linear or branched, optionally hydroxyl-substituted alkyl radical having 6 to 22, preferably 12 to 18 carbon atoms and R 2 and R 3 independently of one another are R 1 or alkyl radicals having 1 to 4 carbon atoms. Lauryldimethylamine is preferably used
FettsäureamidoamineFatty acid amidoamines
Als weitere Ausgangsstoffe können anstelle der Fettamine auch Fettsäureamidoamine der Formel (II) eingesetzt werden,Instead of the fatty amines, fatty acid amidoamines of the formula (II) can also be used as further starting materials,
Rs RJR s RJ
I II I
R«CO-N-(CH2)„N.R« (II)R "CO-N- (CH 2 )" NR "(II)
in der R4CO für einen linearen oder verzweigten Acytrest mit 6 bis 22, vorzugsweise 12 bis 18 Kohlenstoffatomen, Rs, Rβ und R7 unabhängig voneinander für Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffatomen und n für Zahlen von 1 bis 3 steht Typische Beispiele sind Amidoamine die sich von technischen Kokosfettsäureschnitten und Ethylendiamin, N,N-Dimethylethylendiamin bzw. N,N-Dimethylpropylendiamin ableiten.in which R 4 CO stands for a linear or branched acyl radical having 6 to 22, preferably 12 to 18 carbon atoms, R s , R β and R 7 independently of one another for hydrogen or an alkyl radical with 1 to 4 carbon atoms and n for numbers from 1 to 3 Typical examples are amidoamines derived from technical coconut fatty acid cuts and ethylenediamine, N, N-dimethylethylenediamine or N, N-dimethylpropylenediamine.
AlkylierungsmittelAlkylating agent
Als Alkylierungsmittel kommen sowohl Halogencarbonsäuren als auch deren Salze in Betracht Typische Beispiele sind Chloressigsäure und vorzugsweise Natriumchloracetat wobei man die Amine bzw. Amidoamine und die Alkylierungsmittel in der Regel im Molverhältnis 1 : 0,75 bis 1 : 1,05 und vorzugsweise 1 : 0,8 bis 1 : 0.95 einsetzt VerfahrenSuitable alkylating agents are both halocarboxylic acids and their salts. Typical examples are chloroacetic acid and preferably sodium chloroacetate, the amines or amidoamines and the alkylating agents generally being in a molar ratio of 1: 0.75 to 1: 1.05 and preferably 1: 0. 8 to 1: 0.95 method
Zur Hersteilung der Betaintenside geht man üblicherweise so vor, daß zunächst 1 Mol des Alkviie- rungsmittels, vorzugsweise wasserfreies Natriumchloracetat in dem wäßrigen Alkohol dispergiert wird, in diese Dispersion werden unter Rühren langsam 0,8 bis 0,95 Mol eines geschmolzenen Fettamins oder Fettsäureamidoamins eingetropft Die Reaktion wird bei Temperaturen im Bereich von 60 bis 90aC solange durchgeführt bis die Aminzahl unter einen Wert von wenigstens 5, vorzugsweise unter 2 abgesunken ist Nach Abschluß der Reaktion wird das als Nebenprodukt gebildete Salz abfiltriert der Alkoholanteil des Gemisches im Vakuum verdampft und die Betainkonzentration des Endprodukts durch Hinzufügung von Wasser eingestelltTo prepare the betaine surfactants, the procedure is usually such that 1 mol of the alkali agent, preferably anhydrous sodium chloroacetate, is first dispersed in the aqueous alcohol. 0.8 to 0.95 mol of a molten fatty amine or fatty acid amidoamine are slowly added dropwise to this dispersion while stirring The reaction is carried out at temperatures in the range from 60 to 90 ° C. until the amine number has dropped below a value of at least 5, preferably below 2. After the reaction has ended, the salt formed as a by-product is filtered off, the alcohol portion of the mixture is evaporated in vacuo and the Betain concentration of the final product adjusted by adding water
Das Alkylierungsmittel sollte vorteilhafterweise als möglichst feines, wasserfreies Pulver eingesetzt werden. Bei zu grober Körnung verlangsamt sich die Reaktionsgeschwindigkeit in dem aus Alkohol und Wasser bestehenden Medium. Konkret sollten 10 - 20 Gew.-% des gesamten Pulvers eine Körnung von 50 - 100 mesh und über 95 Gew.-% des Pulvers eine Partikelgröße < 20 mesh aufweisen.The alkylating agent should advantageously be used as the finest, anhydrous powder possible. If the grain size is too coarse, the reaction rate slows down in the medium consisting of alcohol and water. Specifically, 10-20% by weight of the total powder should have a grain size of 50-100 mesh and over 95% by weight of the powder should have a particle size <20 mesh.
Das Verhältnis von Wasser zu Alkohol in dem Reaktionssystem ist vorzugsweise so zu wählen, daß das Alkylierungsmittel dispergiert wird, die Reaktion mit dem Fettamin bzw. Fettsäureamidoamin einwandfrei verläuft und das als Nebenprodukt anfallende Salz aussalzt Hierzu hat es sich als vorteil¬ haft erwiesen, beispielsweise 1 Mol Natriumchloracetat in einem Gemisch aus 5 bis 10 Gew.-% Wasser und 35 bis 50 Gew.-% Ethanol oder Isopropylalkohol zu. dispergieren. Enthält die Lösung weniger als 5 Gew.-% Wasser oder mehr als 50 Gew.-% Alkohol, so kann die Geschwindigkeit der Reaktion des Alkylierungsmrttels mit dem Fettamin oder Fettsäureamidoamin verlangsamt werden, so daß die Lö¬ sung eine zu hohe Restaminzahl aufweist Umgekehrt läuft die Reaktion bei Wasseranteilen über 10 Gew.-% oder Alkoholanteilen unter 35 Gew.-% zwar reibungslos ab, doch geht das als Nebenprodukt anfälende Salz in der Mischung in Lösung, anstatt auszusalzen, so daß sich das Salz schwer abtrennen läßt Gewerbliche AnwendbarkeitThe ratio of water to alcohol in the reaction system should preferably be chosen so that the alkylating agent is dispersed, the reaction with the fatty amine or fatty acid amidoamine proceeds smoothly and the salt formed as a by-product is salted out. For this purpose it has proven advantageous, for example 1 Moles of sodium chloroacetate in a mixture of 5 to 10% by weight of water and 35 to 50% by weight of ethanol or isopropyl alcohol. disperse. If the solution contains less than 5% by weight of water or more than 50% by weight of alcohol, the rate of reaction of the alkylating agent with the fatty amine or fatty acid amidoamine can be slowed down, so that the solution has too high a residual amine number the reaction proceeds smoothly with water contents above 10% by weight or alcohol contents below 35% by weight, but the salt which is obtained as a by-product dissolves in the mixture instead of being salted out, so that the salt is difficult to separate off Industrial applicability
Die nach dem erfindungsgemäßen Verfahren erhältlichen Betaintenside weisen einen besonders geringen Gehalt an anorganischen Salzen und daher eine besonders hohe hautkosmetische Verträglichkeit auf. Sie eignen sich daher in besonderer Weise zur Herstellung von oberflächenaktiven Mitteln, die mit der menschlichen Haut in Kontakt treten, wie beispielsweise Handgeschirrspülmitteln oder Haarshampoos, in denen sie in Mengen von 1 bis 50, vorzugsweise 2 bis 15 Gew.-% - bezogen auf die Mittel - enthalten sein können. The betaine surfactants obtainable by the process according to the invention have a particularly low content of inorganic salts and therefore a particularly high skin-cosmetic compatibility. They are therefore particularly suitable for the production of surface-active agents that come into contact with human skin, such as hand dishwashing detergents or hair shampoos, in which they are used in amounts of 1 to 50, preferably 2 to 15,% by weight, based on the Means - may be included.
BeispieleExamples
Beispiel 1example 1
In einen 2-l-Vierhalskolben mit Thermometer, Kondensator, Wasserabscheider, NrGaszuleitungsrohr und Rührer wurden 1083 g (5,3 mol) einer hydrierten Kokosfettsäure sowie 552 g (5,4 mol) N,N- Dimethylaminopropylamin gefüllt und unter Stickstoffstoffabdeckung auf 180*C erhitzt Das Kondens¬ wasser wurde kontinuierlich aus dem Reaktionsgefäß entfernt Die Reaktion wurde fortgesetzt bis die Säurezahl des Gemisches auf unter 5 abgesunken war. Danach wurde überschüssiges Dimethyl- propylamin im Vakuum entfernt Auf diese Weise wurden 1500 g Kokosfettsäureamidopropyldimethyr- amin mit einer Aminzahl von 187 gewonnen.1083 g (5.3 mol) of a hydrogenated coconut fatty acid and 552 g (5.4 mol) of N, N-dimethylaminopropylamine were introduced into a 2-liter four-necked flask equipped with a thermometer, condenser, water separator, No. gas feed pipe and stirrer, and the amount was increased to 180 * under nitrogen blanket. C heated The condensed water was continuously removed from the reaction vessel. The reaction was continued until the acid number of the mixture had dropped to below 5. Excess dimethylpropylamine was then removed in vacuo. In this way, 1500 g of coconut fatty acid amidopropyldimethyramine with an amine number of 187 were obtained.
Beispiel 2Example 2
In einen 500-ml-Vιerhalskolben mit Thermometer, Kondensator, Tropftrichter und Rührer wurden 32 g (0,29 mol) eines in feiner Pulverform vorliegenden Natriumchloracetats, 75 ml Ethanol und 10 ml Wasser gefüllt und gründlich gerührt Anschließend wurden dieser Dispersion innerhalb von 30 Minuten 85 g (0,29 mol) geschmolzenes Kokosfettsäureamidopropyldimethylamin aus Beispiel 1 zugetropft und das Gemisch auf 80*C erhitzt Sobald nach 5 h die Aminzahl auf unter 2,2 gesunken war, wurde das Gemisch auf Raumtemperatur abgekühlt und das ausgesalzene NaCl abfiltriert Das Ritrat wurde mit 75 ml Wasser aufgefüllt Durch allmähliches Erhitzen im Vakuum bei 0,1 bar wurde das Ethanol ver¬ dampft Die Wirkstoffkonzentration der Lösung wurde durch Verdünnen mit Wasser auf 30 Gew.-% eingestellt Die resultierende Lösung wies einen Salzgehalt von 0,98 Gew.-% und eine Aminzahl von 1,25 auf.In a 500 ml vial neck flask with thermometer, condenser, dropping funnel and stirrer, 32 g (0.29 mol) of a sodium chloroacetate in fine powder form, 75 ml of ethanol and 10 ml of water were introduced and stirred thoroughly. This dispersion was then stirred within 30 minutes 85 g (0.29 mol) of melted coconut fatty acid amidopropyldimethylamine from Example 1 were added dropwise and the mixture was heated to 80 ° C. As soon as the amine number had dropped to below 2.2 after 5 hours, the mixture was cooled to room temperature and the salted-out NaCl was filtered off made up with 75 ml of water The ethanol was evaporated by gradual heating in vacuo at 0.1 bar. The active substance concentration of the solution was adjusted to 30% by weight with water. The resulting solution had a salt content of 0.98% by weight. % and an amine number of 1.25.
Beispiel 3Example 3
Analog Beispiel 2 wurden 32 g Natriumchloracetat in einer Mischung aus 75 ml Ethanol und 10 ml Wasser dispergiert und anschließend mit 70 g (0,29 mol) Lauryidimethylamin umgesetzt Nach Ab¬ schluß der Reaktion wurde der Reaktor auf Raumtemperatur gekühlt das ausgesalzte NaCl abfiltriert das Ethanol verdampft und die Wirkstoffkonzentration der Lösung auf 30 Gew.-% eingestellt Die resul¬ tierende Lösung wies einen Salzgehalt von 1,01% und eine Aminzahl von 1,35 auf. Vergleichsbeispiel V1Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 75 ml of ethanol and 10 ml of water and then reacted with 70 g (0.29 mol) of lauryidimethylamine. After the reaction had ended, the reactor was cooled to room temperature and the salted-out NaCl filtered off the ethanol evaporated and the active ingredient concentration of the solution adjusted to 30% by weight. The resulting solution had a salt content of 1.01% and an amine number of 1.35. Comparative Example V1
Analog Beispiel 2 wurden 32 g Natriumchloracetat in einer Mischung aus 150 ml isopropylalkohol und 10 ml Wasser dispergiert und mit 85 g geschmolzenem Kokosfettsäureamidopropyldimethylamin umge¬ setzt Nach Abschluß der Reaktion wurde das ausgesalzene NaCl abfiltriert der Alkohol im Vakuum verdampft und die Wirkstoffkonzentration durch Hinzufügung von Wasser auf 30 Gew.-% eingestellt Die resultierende Lösung enthielt 0,59 Gew.-% NaCl bei einer Aminzahl von 4,46.Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 150 ml of isopropyl alcohol and 10 ml of water and reacted with 85 g of molten coconut fatty acid amidopropyldimethylamine 30 wt .-% adjusted The resulting solution contained 0.59 wt .-% NaCl with an amine number of 4.46.
Vergleichsbeispiel V2Comparative example V2
Analog Beispiel 2 wurden 32 g Natriumchloracetat in einer Mischung aus 75 ml Ethanol und 40 ml Wasser dispergiert und darin 85 g geschmolzenes Kokosfettsäureamidopropyldimethylamin eingetropft Nach Abschluß der Reaktion wurde das Salz abfiltriert das Ethanol im Vakuum verdampft und die Wirkstoffkonzentration durch Hinzufügung von Wasser auf 30 Gew.-% eingestellt Die resultierende Lösung enthielt 2,89 Gew.-% NaCl; die Aminzahl betrug 1,32-Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 75 ml of ethanol and 40 ml of water and 85 g of melted coconut fatty acid amidopropyldimethylamine were added dropwise. After the reaction had ended, the salt was filtered off, the ethanol was evaporated in vacuo and the active ingredient concentration was increased to 30% by adding water. -% adjusted The resulting solution contained 2.89% by weight NaCl; the amine number was 1.32
Vergleichsbeispiel V3Comparative Example V3
Analog Beispiel 2 wurden 32 g Natriumchloracetat in einer Mischung aus 150 ml Ethanol und 40 ml Wasser dispergiert In diese Dispersion wurden 85 g geschmolzenes Kokosfettsäureamidopropyldime- thylamin eingetropft Nach Abschluß der Reaktion wurde das ausgesalzene NaCl abfiltriert das Ethanol im Vakuum verdampft und die Wirkstoffkonzentration durch Hinzufügung von Wasser auf 30 Gew.-% eingestellt Die resultierende Lösung enthielt 2,11 Gew.-% NaCl bei einer Aminzahl von 2,29.Analogously to Example 2, 32 g of sodium chloroacetate were dispersed in a mixture of 150 ml of ethanol and 40 ml of water. 85 g of melted coconut fatty acid amidopropyldimethylamine were added dropwise to this dispersion Water adjusted to 30 wt.% The resulting solution contained 2.11 wt.% NaCl with an amine number of 2.29.
Vergleichsbeispiel V4Comparative Example V4
Analog Beispiel 2 wurden 32 g Natriumchloracetat in 198 ml Wasser dispergiert In diese Dispersion wurden 85 g geschmolzenes Kokosfettsäureamidopropyldimethylamin eingetropft Nach Abschluß der Reaktion wurde die Wirkstoffkonzentration durch Hinzufügung von Wasser auf 30 Gew.-% eingestellt Die resultierende Lösung enthielt 5,21 Gew.-% NaCl bei einer Aminzahl von 1,31. 32 g of sodium chloroacetate were dispersed in 198 ml of water analogously to Example 2. 85 g of melted coconut fatty acid amidopropyldimethylamine were added dropwise to this dispersion. After the reaction had ended, the active compound concentration was adjusted to 30% by weight by adding water. The resulting solution contained 5.21% by weight. NaCl with an amine number of 1.31.

Claims

Patentansprüche claims
1. Verfahren zur Herstellung von Betaintensiden mit geringem Salzgehalt bei dem man Fettamine und/oder Fettsäureamidoamine in wäßrig-alkoholischer Dispersion mit Halogencarboπsäuren oder deren Alkalisalzen alkyliert gebildete anorganische Salze abfiltnert das Lösungsmittel entfernt und den Rückstand mit Wasser auf die gewünschte Wirkstoffkonzentration einstellt dadurch ge¬ kennzeichnet, daß man als Dispergiermittel eine Mischung aus 5 bis 10 Gew.-% Wasser und 35 bis 50 Gew.-% Ethanol und/oder Isopropylalkohol - jeweils bezogen auf die Summe der Einsatz¬ stoffe - einsetzt1. A process for the preparation of betaine surfactants with a low salt content in which fatty amines and / or fatty acid amidoamines in aqueous-alcoholic dispersion with halogenated carboxylic acids or their alkali metal salts, alkylated inorganic salts are filtered off and the residue is adjusted with water to the desired active ingredient concentration that a mixture of 5 to 10% by weight of water and 35 to 50% by weight of ethanol and / or isopropyl alcohol is used as the dispersant, in each case based on the sum of the starting materials
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet daß man Fettamine der Formel (I) einsetzt2. The method according to claim 1, characterized in that fatty amines of the formula (I) are used
R3 R 3
I R'-N-R2 (I)I R'-NR 2 (I)
in der R1 für einen linearen oder verzweigten, gegebenenfalls hydroxysubstituierten Alkylrest mit 6 bis 22 Kohlenstoffatomen und R2 und R3 unabhängig voneinander für R1 oder Alkylreste mit 1 bis 4 Kohlenstoffatomen stehen.in which R 1 is a linear or branched, optionally hydroxy-substituted alkyl radical having 6 to 22 carbon atoms and R 2 and R 3 independently of one another are R 1 or alkyl radicals having 1 to 4 carbon atoms.
3. Verfahren nach Anspruch 1, dadurch gekennzeichnet daß man Fettsäureamidoamine der Formel (II) einsetzt3. The method according to claim 1, characterized in that fatty acid amidoamines of the formula (II) are used
R5 R7 l IR 5 R 7 l I
RCO-N-fCHa^N-R« (II)RCO-N-fCHa ^ N-R «(II)
in der R4CO für einen linearen oder verzweigten Acylrest mit 6 bis 22 Kohlenstoffatomen, R5, R6 und R7 unabhängig voneinander für Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffato¬ men und n für Zahlen von 1 bis 3 stehtin which R 4 CO represents a linear or branched acyl radical having 6 to 22 carbon atoms, R 5 , R 6 and R 7 independently of one another represent hydrogen or an alkyl radical having 1 to 4 carbon atoms and n represents numbers from 1 to 3
4. Verfahren nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet daß man als Alkylierungs¬ mittel Natriumchloracetat einsetzt4. Process according to claims 1 to 3, characterized in that sodium chloroacetate is used as the alkylating agent
5. Verfahren nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet daß man die Amine bzw. Amidoamine und die Alkylierungsmittel im Molverhältnis 1 : 0,75 bis 1 : 1,05 einsetzt 5. Process according to claims 1 to 4, characterized in that the amines or amidoamines and the alkylating agent are used in a molar ratio of 1: 0.75 to 1: 1.05
PCT/EP1996/004120 1995-09-29 1996-09-20 Process for producing betaine surfactants with low salt content WO1997012856A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP25220295A JPH0995473A (en) 1995-09-29 1995-09-29 Production of betaine type amphoteric surfactant having low salt content
JP7/252202 1995-09-29

Publications (1)

Publication Number Publication Date
WO1997012856A1 true WO1997012856A1 (en) 1997-04-10

Family

ID=17233928

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/004120 WO1997012856A1 (en) 1995-09-29 1996-09-20 Process for producing betaine surfactants with low salt content

Country Status (2)

Country Link
JP (1) JPH0995473A (en)
WO (1) WO1997012856A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0908510A1 (en) * 1997-10-08 1999-04-14 The Procter & Gamble Company Liquid bleaching compositions with improved safety to fabrics and colors
FR2786781A1 (en) * 1998-12-07 2000-06-09 Ceca Sa CONCENTRATED HYDROALCOHOLIC COMPOSITIONS ALKYLAMIDOPROPYLBETAN FLUIDS OF COPRAH OR HYDROGEN PALMISTS
US6316400B1 (en) 1997-10-08 2001-11-13 The Procter & Gamble Co. Liquid bleaching composition with improved safety to fabrics and colors
WO2002022552A1 (en) * 2000-09-16 2002-03-21 Huntsman International Llc Solid amphoteric surfactants
US6794041B2 (en) 2002-11-05 2004-09-21 Ppg Industries Ohio, Inc. Additives for low VOC aqueous coatings
WO2006063957A1 (en) * 2004-12-16 2006-06-22 Ciba Specialty Chemicals Holding Inc. Stabilized organic materials containing fillers

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6516056B1 (en) * 2018-08-29 2019-05-22 東洋インキＳｃホールディングス株式会社 Urethane pressure sensitive adhesive and adhesive sheet

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3639752A1 (en) * 1985-11-25 1987-05-27 Kao Corp METHOD FOR PRODUCING AMPHOTERIC SURFACE ACTIVE AGENTS
JPS6312333A (en) * 1986-07-03 1988-01-19 Matsumoto Yushi Seiyaku Kk Production of amphoteric surface active agent
JPH0551351A (en) * 1991-08-22 1993-03-02 Kao Corp Production of betaine compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3639752A1 (en) * 1985-11-25 1987-05-27 Kao Corp METHOD FOR PRODUCING AMPHOTERIC SURFACE ACTIVE AGENTS
JPS6312333A (en) * 1986-07-03 1988-01-19 Matsumoto Yushi Seiyaku Kk Production of amphoteric surface active agent
JPH0551351A (en) * 1991-08-22 1993-03-02 Kao Corp Production of betaine compound

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 8808, Derwent World Patents Index; Class D21, AN 88-054664, XP002022563 *
PATENT ABSTRACTS OF JAPAN vol. 017, no. 361 (C - 1080) 8 July 1993 (1993-07-08) *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0908510A1 (en) * 1997-10-08 1999-04-14 The Procter & Gamble Company Liquid bleaching compositions with improved safety to fabrics and colors
WO1999018179A1 (en) * 1997-10-08 1999-04-15 The Procter & Gamble Company Liquid bleaching compositions with improved safety to fabrics and colors
US6316400B1 (en) 1997-10-08 2001-11-13 The Procter & Gamble Co. Liquid bleaching composition with improved safety to fabrics and colors
FR2786781A1 (en) * 1998-12-07 2000-06-09 Ceca Sa CONCENTRATED HYDROALCOHOLIC COMPOSITIONS ALKYLAMIDOPROPYLBETAN FLUIDS OF COPRAH OR HYDROGEN PALMISTS
EP1008644A1 (en) * 1998-12-07 2000-06-14 Ceca S.A. Fluid concentrated hydroalcoholic compositions of copra or oil palm alkyl-amidopropylbetains
US6335375B1 (en) 1998-12-07 2002-01-01 Ceca S.A. Concentrated fluid aqueous-alcoholic compositions of hydrogenated coconut or palm kernel oil alkylamidopropylbetaines
WO2002022552A1 (en) * 2000-09-16 2002-03-21 Huntsman International Llc Solid amphoteric surfactants
US6794041B2 (en) 2002-11-05 2004-09-21 Ppg Industries Ohio, Inc. Additives for low VOC aqueous coatings
WO2006063957A1 (en) * 2004-12-16 2006-06-22 Ciba Specialty Chemicals Holding Inc. Stabilized organic materials containing fillers

Also Published As

Publication number Publication date
JPH0995473A (en) 1997-04-08

Similar Documents

Publication Publication Date Title
EP0623587B1 (en) Method for the preparation of amphoteric detergents
EP0243619B1 (en) Process for the preparation of a highly concentrated, flowable and pumpable betaine solution
EP0563747B1 (en) Process for the preparation of aqueous betaine solutions
EP0560114A2 (en) Betaine aqueous liquid solution with at least 40 weight-% of solid content
DE19622612C1 (en) Gemini surfactants having excellent surface-active properties
EP0656346B1 (en) Method for the preparation of highly concentrated flowable aqueous solutions of betaines
EP0671382B1 (en) Fluorinated carboxybetaines and alkylsulfobetaines as well as the mixtures thereof with saturated fluoroalkylamines
WO1997012856A1 (en) Process for producing betaine surfactants with low salt content
EP0557835B1 (en) Process for the preparation of betaines
EP0647613B1 (en) Process for the preparation of highly concentrated, freely flowable, aqueous solutions of betaines
EP0677509B1 (en) Process for the preparation of highly concentrated, freely flowable, aqueous solutions of betaines
EP0730572B1 (en) Low-viscosity aqueous concentrates of betaine surfactants
DE19607824A1 (en) Low melting ester quats
EP0452349B1 (en) Process for producing amphoteric surface-active imidazoline derivatives
DE2319429B2 (en) Process for the preparation of water-soluble sodium, potassium or ammonium salts of carboxyalkoxy succinic acid
EP0739878B1 (en) Process for the preparation of concentrated fluid aqueous betaine solutions
US4369123A (en) Stable emulsions of substantially pure alkenylsuccinic acid and their preparation
EP0749412B1 (en) Low-viscosity aqueous betaine surfactant concentrates
EP0688311B1 (en) Method of processing betaines and amphoteric surfactants
DE4307709C2 (en) Highly concentrated solutions of amphoteric glycine compounds and process for their preparation
DE3628916A1 (en) PHOSPHORIC ACID ESTER
DE19523477A1 (en) Process for the preparation of aqueous, low-viscosity betaine concentrates
EP0726890B1 (en) Process for producing detergent mixtures
DE19524265C2 (en) Process for the preparation of amphoteric surfactants
DE4430084B4 (en) Process for the production of betaines

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase