EP0295385B1 - Procédé de préparation de diesters d'une trialcanolamine avec des acides gras et leur application - Google Patents

Procédé de préparation de diesters d'une trialcanolamine avec des acides gras et leur application Download PDF

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Publication number
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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EP
European Patent Office
Prior art keywords
fatty acid
trialkanolamine
acid esters
esters
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP88106112A
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German (de)
English (en)
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EP0295385A1 (fr
Inventor
Wulf Dr. Ruback
Jan Dr. Schut
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huels AG
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Huels AG
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Publication date
Application filed by Huels AG filed Critical Huels AG
Priority to AT88106112T priority Critical patent/ATE61565T1/de
Publication of EP0295385A1 publication Critical patent/EP0295385A1/fr
Application granted granted Critical
Publication of EP0295385B1 publication Critical patent/EP0295385B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (4)

1. Procédé pour la préparation de diesters d'acides gras et de trialcanolamines par réaction d'une trialcanolamine sur 1,5 à 2,5 équivalents d'acide gras, caractérisé par le fait que l'on effectue la réaction en présence de 0,05 à 5,0% en poids, relativement au mélange total, d'un ester d'acide gras.
2. Procédé pour la préparation de diesters d'acides gras et de trialcanolamines selon la revendication 1, caractérisé par le fait que les acides gras des esters d'acide gras renferment de 4 à 24 atomes de carbone.
3. Procédé pour la préparation de diesters d'acides gras et de trialcanolamines selon la revendication 1 ou 2, caractérisé par le fait que les alcools des esters d'acide gras sont des mono- à hexa-alcools comportant de 1 à 8 atomes de carbone.
4. L'utilisation, en tant qu'agents de rinçage assouplissants pour le linge, des composés d'ammonium quaternaire obtenus en quaternisant de manière usuelle les diesters d'acide gras et de trialcanolamine des revendications 1 à 3.
EP88106112A 1987-06-19 1988-04-16 Procédé de préparation de diesters d'une trialcanolamine avec des acides gras et leur application Expired - Lifetime EP0295385B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88106112T ATE61565T1 (de) 1987-06-19 1988-04-16 Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3720332 1987-06-19
DE19873720332 DE3720332A1 (de) 1987-06-19 1987-06-19 Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung

Publications (2)

Publication Number Publication Date
EP0295385A1 EP0295385A1 (fr) 1988-12-21
EP0295385B1 true EP0295385B1 (fr) 1991-03-13

Family

ID=6329939

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88106112A Expired - Lifetime EP0295385B1 (fr) 1987-06-19 1988-04-16 Procédé de préparation de diesters d'une trialcanolamine avec des acides gras et leur application

Country Status (6)

Country Link
US (1) US4830771A (fr)
EP (1) EP0295385B1 (fr)
AT (1) ATE61565T1 (fr)
AU (1) AU1813188A (fr)
DE (2) DE3720332A1 (fr)
ES (1) ES2019855B3 (fr)

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DE3842571A1 (de) * 1988-12-17 1990-06-21 Pfersee Chem Fab Hydrophile weichgriffmittel fuer faserige materialien und deren verwendung
ES2021900A6 (es) * 1989-07-17 1991-11-16 Pulcra Sa Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester.
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 (de) * 1991-01-17 1992-07-23 Huels Chemische Werke Ag Fettsaeureester des n-methyl-n,n,n-trihydroxyethyl-ammonium-methyl- sulfat enthaltende waessrige emulsionen
DE69214618T2 (de) * 1991-12-31 1997-02-20 Stepan Europ Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher
DE4224714A1 (de) * 1992-07-27 1994-02-03 Henkel Kgaa Schäumende Detergensgemische
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 (de) * 1992-09-28 1994-03-31 Henkel Kgaa Verfahren zur Herstellung pulverförmiger oder granularer Detergensgemische
DE4243862A1 (de) * 1992-12-23 1994-06-30 Huels Chemische Werke Ag Verfahren zur Quaternierung von Triethanolaminfettsäureestern und Imidazolinamiden in alkoxylierten Fetten oder Ölen als Reaktionsmedium und die Verwendung der Reaktionsmischungen als Wäscheweichspülerwirkstoffkomponenten
DE4334365A1 (de) * 1993-10-08 1995-04-13 Henkel Kgaa Quaternierte Fettsäuretriethanolaminester-Salze mit verbesserter Wasserlöslichkeit
DE4405702A1 (de) * 1994-02-23 1995-08-24 Witco Surfactants Gmbh Hochkonzentrierte wäßrige Weichspülmittel mit verbesserter Lagerstabilität
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
DE4430721A1 (de) * 1994-08-30 1996-03-07 Hoechst Ag Autoglanztrocknungsmittel
US5503756A (en) * 1994-09-20 1996-04-02 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
DE4446137A1 (de) * 1994-12-23 1996-06-27 Huels Chemische Werke Ag Quaternierte Triethanolamindifettsäureester
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US6166232A (en) * 1996-06-12 2000-12-26 Akzo Nobel Nv Process for producing ester quats
CA2290734A1 (fr) 1997-05-19 1998-11-26 The Procter & Gamble Company Sels esters de triethanolamine d'acides gras quaternaires et leur utilisation comme adoucissants pour tissus
US6759383B2 (en) * 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
WO1999035120A1 (fr) * 1998-01-09 1999-07-15 Witco Corporation Composes d'ammonium quaternaire, compositions a base de ces composes, et utilisations correspondantes
DE19821348B4 (de) * 1998-05-13 2006-02-16 Cognis Ip Management Gmbh Ethoxylierte Esterquats
DE19855366A1 (de) 1998-12-01 2000-06-08 Witco Surfactants Gmbh Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel
DE19855954A1 (de) * 1998-12-04 2000-06-08 Cognis Deutschland Gmbh Verfahren zur Herstellung von niedrigviskosen Esterquatzubereitungen
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
US7777065B2 (en) * 2005-03-14 2010-08-17 Akzo Nobel N.V. Removal of residual sulfur dioxide from dimethyl sulfate
WO2007002913A1 (fr) 2005-06-29 2007-01-04 Colgate-Palmolive Company Amidoamines ou amidoquats oligomères pour des compositions de traitement de tissu ou des cheveux
CN102336675A (zh) * 2010-07-21 2012-02-01 博兴华润油脂化学有限公司 一种酯基季铵盐的生产方法
GB2516862A (en) * 2013-08-01 2015-02-11 M I Drilling Fluids Uk Ltd Quaternary ammonium compounds and gas hydrate inhibitor compositions
EP3181667A1 (fr) * 2015-12-18 2017-06-21 Kao Corporation, S.A. Compositions actives d'adoucissants pour tissus
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
PT3418354T (pt) * 2017-06-20 2020-07-07 Kao Corp Sa Composições de substâncias ativas amaciadoras de tecidos
DK3418353T3 (da) * 2017-06-20 2020-09-28 Kao Corp Sa Skyllemiddelaktivsammensætninger
PL3418355T3 (pl) 2017-06-20 2020-10-05 Kao Corporation, S.A. Kompozycje czynne do zmiękczania tkanin
CN112334443B (zh) 2018-06-26 2023-08-22 赢创运营有限公司 基于油的酯基季铵盐的制备方法
JP7776612B2 (ja) 2021-08-02 2025-11-26 ザ プロクター アンド ギャンブル カンパニー 活性剤を含む非水溶性繊維物品
EP4282854A1 (fr) 2022-05-25 2023-11-29 Unión Deriván, S.A. Procédé de production d'esterquats

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US2173058A (en) * 1939-05-04 1939-09-12 Kritchevsky Wolf Acid substituted hydroxy alkylamines and process of making same
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DD159263A3 (de) * 1980-12-23 1983-03-02 Peter Reinemann Weichspuelmittelkonzentrate
DE3137043A1 (de) * 1981-09-17 1983-03-24 Bayer Ag, 5090 Leverkusen Ammoniumverbindungen

Also Published As

Publication number Publication date
AU1813188A (en) 1988-12-22
US4830771A (en) 1989-05-16
EP0295385A1 (fr) 1988-12-21
ATE61565T1 (de) 1991-03-15
DE3861985D1 (de) 1991-04-18
DE3720332A1 (de) 1988-12-29
ES2019855B3 (es) 1991-12-01
ES2019855A4 (es) 1991-07-16

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