EP0295385A1 - 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
EP0295385A1
EP0295385A1 EP88106112A EP88106112A EP0295385A1 EP 0295385 A1 EP0295385 A1 EP 0295385A1 EP 88106112 A EP88106112 A EP 88106112A EP 88106112 A EP88106112 A EP 88106112A EP 0295385 A1 EP0295385 A1 EP 0295385A1
Authority
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.)
Granted
Application number
EP88106112A
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German (de)
English (en)
Other versions
EP0295385B1 (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
Original Assignee
Huels AG
Chemische Werke Huels AG
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 Huels AG, Chemische Werke 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 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 customary quaternization, e.g. B. with dimethyl sulfate, quaternary ammonium compounds obtained, such as. B. N-methyl-triethanolammonium ditallow fatty acid methyl sulfate, properties which are undesirable in 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, they are too solid, and they also tend to form strong crystals.
  • the 85% by weight end product consists of a relatively thin melt with crystallites in it. 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 alcohols, preferably 1 to 3 alcohols.
  • trialkanolamine fatty acid diesters produced according to the process of the invention are - after the usual quaternization with z.
  • Suitable trialkanolamines which are to be implemented according to the invention are those which have the formula suffice 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, diethanol-monoisopropanolamine, 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 having 16 to 20, carbon atoms in the linear or branched alkyl chain or the alkene chain.
  • carpyl acid For example, carpyl acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid and their branched or unsaturated homologs, such as. B. 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. B. from fatty acids with 4 to 24 carbon atoms, preferably 8 to 22, in particular 10 to 20 carbon atoms.
  • B. there are z. B. in question: butyric acid, valeric acid, capronic, caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic and lignoceric acid and their branched isomers, such as. B. isovaleric acid, or its unsaturated isomers, such as. B. 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
  • fatty acid esters 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 the 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.
  • partial esters of polyhydric alcohols is also possible.
  • 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 e.g. B. 30 to 300 ° C, preferably 170 to 220 ° C and 3 to 3,000, preferably 700 to 1 100 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.
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 true EP0295385A1 (fr) 1988-12-21
EP0295385B1 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)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001295A1 (fr) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de composes quaternaires de l'ammonium
EP0420465A2 (fr) * 1989-09-19 1991-04-03 Unilever Plc Agent assouplissant pour les tissus
EP0498050A2 (fr) * 1991-01-17 1992-08-12 Hüls Aktiengesellschaft Emulsions aqueuses contenantes des esters d'acides gras avec de N-methyl-N,N,N-trihydroxyethyl-ammonium
WO1994002575A1 (fr) * 1992-07-27 1994-02-03 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents moussants
WO1994007978A1 (fr) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules
EP0604726A1 (fr) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Procédé de quaternisation d'esters triéthanolaminiques d'acides gras et d'imidazolinamides avec des graisses et huiles alcoxylées comme milieu réactionnel et l'utilisation des melanges réactionnels comme composants d'un agent adoucissant
EP0718275A1 (fr) * 1994-12-23 1996-06-26 Hüls Aktiengesellschaft Esters de triéthanolamine d'acide gras quaternaires
WO1998052907A1 (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
WO1999035120A1 (fr) * 1998-01-09 1999-07-15 Witco Corporation Composes d'ammonium quaternaire, compositions a base de ces composes, et utilisations correspondantes
WO1999058492A1 (fr) * 1998-05-13 1999-11-18 Cognis Deutschland Gmbh Composes quaternaires d'ester ethoxyles
EP1006103A1 (fr) * 1998-12-04 2000-06-07 Cognis Deutschland GmbH Procédé de préparation de compositions de composés quaternaires d'ester de basse viscosité
US6759383B2 (en) 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
WO2015015211A1 (fr) * 2013-08-01 2015-02-05 M-I Drilling Fluids Uk Limited Composés d'ammonium quaternaire et compositions d'inhibiteur d'hydrate gazeux
EP4282854A1 (fr) 2022-05-25 2023-11-29 Unión Deriván, S.A. Procédé de production d'esterquats

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3842571A1 (de) * 1988-12-17 1990-06-21 Pfersee Chem Fab Hydrophile weichgriffmittel fuer faserige materialien und deren verwendung
US5516438A (en) * 1989-09-19 1996-05-14 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening
DE69214618T2 (de) * 1991-12-31 1997-02-20 Stepan Europe Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher
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
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
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
BR9709689A (pt) * 1996-06-12 1999-08-10 Akzo Nobel Nv Processo para a preparação de sais quaternários de éster de trialcanolamina
DE19855366A1 (de) 1998-12-01 2000-06-08 Witco Surfactants Gmbh Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel
US6271185B1 (en) 1999-10-29 2001-08-07 Cargill, Incorporated Water soluble vegetable oil esters for industrial applications
US7211556B2 (en) * 2004-04-15 2007-05-01 Colgate-Palmolive Company Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient
CN101142171B (zh) * 2005-03-14 2010-08-11 阿克佐诺贝尔股份有限公司 从硫酸二甲酯中去除残留二氧化硫
BRPI0612842A2 (pt) * 2005-06-29 2012-10-09 Colgate Palmolive Co amidoamina oligomérica, sal de amidoamina oligomérica, composto de amido-amÈnio quaternário oligomérico, composição amaciante de tecido, composição condicionadora capilar, métodos para amaciar tecidos e para condicionar cabelo, e, composição de tratamento capilar
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
EP3181667A1 (fr) * 2015-12-18 2017-06-21 Kao Corporation, S.A. Compositions actives d'adoucissants pour tissus
US10975340B2 (en) 2017-05-16 2021-04-13 The Procter & Gamble Company Active agent-containing fibrous structure articles
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
ES2802407T3 (es) 2017-06-20 2021-01-19 Kao Corp Sa Composiciones activas de suavizante textil
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
WO2020000172A1 (fr) 2018-06-26 2020-01-02 Evonik Operations Gmbh Procédé de préparation d'esterquats à base d'huile
US20230092174A1 (en) 2021-08-02 2023-03-23 The Procter & Gamble Company Active agent-containing articles

Citations (5)

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Publication number Priority date Publication date Assignee Title
US2173058A (en) * 1939-05-04 1939-09-12 Kritchevsky Wolf Acid substituted hydroxy alkylamines and process of making same
US2228985A (en) * 1937-12-21 1941-01-14 Petrolite Corp Ricinoleic acid ester of triethanolamine
US3915867A (en) * 1973-04-24 1975-10-28 Stepan Chemical Co Domestic laundry fabric softener
DE3137043A1 (de) * 1981-09-17 1983-03-24 Bayer Ag, 5090 Leverkusen Ammoniumverbindungen
DE2525610C2 (de) * 1975-06-09 1985-04-11 Henkel KGaA, 4000 Düsseldorf Kationische Avivagemittel mit verbesserter Kaltwasserlöslichkeit

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
DD159263A3 (de) * 1980-12-23 1983-03-02 Peter Reinemann Weichspuelmittelkonzentrate

Patent Citations (5)

* Cited by examiner, † Cited by third party
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 (de) * 1975-06-09 1985-04-11 Henkel KGaA, 4000 Düsseldorf Kationische Avivagemittel mit verbesserter Kaltwasserlöslichkeit
DE3137043A1 (de) * 1981-09-17 1983-03-24 Bayer Ag, 5090 Leverkusen Ammoniumverbindungen

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001295A1 (fr) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de composes quaternaires de l'ammonium
EP0420465A2 (fr) * 1989-09-19 1991-04-03 Unilever Plc Agent assouplissant pour les tissus
EP0420465A3 (en) * 1989-09-19 1993-02-24 Unilever Plc Softening agent for fabrics
EP0498050A2 (fr) * 1991-01-17 1992-08-12 Hüls Aktiengesellschaft Emulsions aqueuses contenantes des esters d'acides gras avec de N-methyl-N,N,N-trihydroxyethyl-ammonium
EP0498050A3 (en) * 1991-01-17 1992-08-26 Huels Aktiengesellschaft Aqueous emulsions comprising fatty acid esters of n-methyl-n,n,n-trihydroxyethyl-ammonium-methyl-sulfate
US5437801A (en) * 1991-01-17 1995-08-01 Huels Aktiengesellschaft Aqueous emulsions containing fatty acid esters of N-methyl-N,N,N-trihydroxyethyl ammonium methyl sulfate
US5580850A (en) * 1992-07-27 1996-12-03 Henkel Kommanditgesellschaft Auf Aktien Foaming detergent mixtures
WO1994002575A1 (fr) * 1992-07-27 1994-02-03 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents moussants
WO1994007978A1 (fr) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules
EP0604726A1 (fr) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Procédé de quaternisation d'esters triéthanolaminiques d'acides gras et d'imidazolinamides avec des graisses et huiles alcoxylées comme milieu réactionnel et l'utilisation des melanges réactionnels comme composants d'un agent adoucissant
US5443631A (en) * 1992-12-23 1995-08-22 Huels Aktiengesellschaft Process for the quaternization of triethanolamine fatty acid esters and imidazolinamides and the use of the reaction mixtures in laundry softener compositions
US5705663A (en) * 1994-12-23 1998-01-06 Servo Delden B.V. Quaternized triethanolamine difatty acid esters
EP0718275A1 (fr) * 1994-12-23 1996-06-26 Hüls Aktiengesellschaft Esters de triéthanolamine d'acide gras quaternaires
WO1998052907A1 (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
US7015187B2 (en) 1997-05-19 2006-03-21 The Procter & Gamble Company Fabric softening compound
US6521589B2 (en) 1997-05-19 2003-02-18 The Procter & Gamble Company Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners
EP1045891A4 (fr) * 1998-01-09 2003-01-22 Goldschmidt Chemical Corp Nouveaux composes d'ammonium quaternaire, compositions contenant ces composes et utilisation de ces compositions
EP1045891A1 (fr) * 1998-01-09 2000-10-25 Goldschmidt Chemical Corporation Nouveaux composes d'ammonium quaternaire, compositions contenant ces composes et utilisation de ces compositions
WO1999035120A1 (fr) * 1998-01-09 1999-07-15 Witco Corporation Composes d'ammonium quaternaire, compositions a base de ces composes, et utilisations correspondantes
WO1999058492A1 (fr) * 1998-05-13 1999-11-18 Cognis Deutschland Gmbh Composes quaternaires d'ester ethoxyles
EP1006103A1 (fr) * 1998-12-04 2000-06-07 Cognis Deutschland GmbH Procédé de préparation de compositions de composés quaternaires d'ester de basse viscosité
US6759383B2 (en) 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
WO2015015211A1 (fr) * 2013-08-01 2015-02-05 M-I Drilling Fluids Uk Limited Composés d'ammonium quaternaire et compositions d'inhibiteur d'hydrate gazeux
US10550304B2 (en) 2013-08-01 2020-02-04 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
EP4282854A1 (fr) 2022-05-25 2023-11-29 Unión Deriván, S.A. Procédé de production d'esterquats

Also Published As

Publication number Publication date
ES2019855B3 (es) 1991-12-01
EP0295385B1 (fr) 1991-03-13
DE3720332A1 (de) 1988-12-29
DE3861985D1 (de) 1991-04-18
ES2019855A4 (es) 1991-07-16
AU1813188A (en) 1988-12-22
ATE61565T1 (de) 1991-03-15
US4830771A (en) 1989-05-16

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