EP0295385B1 - Verfahren zur Herstellung von Trialkanolamindifettsäureestern und deren Verwendung - Google Patents
Verfahren zur Herstellung von Trialkanolamindifettsäureestern und deren Verwendung Download PDFInfo
- 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
- 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.)
- Expired - Lifetime
Links
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.
Landscapes
- 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)
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 |
---|---|---|---|
DE19873720332 DE3720332A1 (de) | 1987-06-19 | 1987-06-19 | Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung |
DE3720332 | 1987-06-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0295385A1 EP0295385A1 (de) | 1988-12-21 |
EP0295385B1 true EP0295385B1 (de) | 1991-03-13 |
Family
ID=6329939
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88106112A Expired - Lifetime EP0295385B1 (de) | 1987-06-19 | 1988-04-16 | Verfahren zur Herstellung von Trialkanolamindifettsäureestern und deren Verwendung |
Country Status (6)
Country | Link |
---|---|
US (1) | US4830771A (es) |
EP (1) | EP0295385B1 (es) |
AT (1) | ATE61565T1 (es) |
AU (1) | AU1813188A (es) |
DE (2) | DE3720332A1 (es) |
ES (1) | ES2019855B3 (es) |
Families Citing this family (41)
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 |
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 Europe | 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 |
JP2000512287A (ja) * | 1996-06-12 | 2000-09-19 | アクゾ ノーベル ナムローゼ フェンノートシャップ | エステルクォーツの製造方法 |
CA2290734A1 (en) | 1997-05-19 | 1998-11-26 | The Procter & Gamble Company | Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners |
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 (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 |
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 |
ATE485327T1 (de) | 2005-06-29 | 2010-11-15 | Colgate Palmolive Co | Oligomere amidoamine oder amidoquate für zusammensetzungen zur gewebe- oder haarbehandlung |
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 (en) | 2015-12-18 | 2017-06-21 | Kao Corporation, S.A. | Fabric softener active compositions |
US10975340B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing fibrous structure articles |
US10975338B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing three-dimensional articles |
US10975339B2 (en) | 2017-05-16 | 2021-04-13 | The Procter & Gamble Company | Active agent-containing articles |
PL3418355T3 (pl) | 2017-06-20 | 2020-10-05 | Kao Corporation, S.A. | Kompozycje czynne do zmiękczania tkanin |
PT3418353T (pt) * | 2017-06-20 | 2020-09-28 | Kao Corp Sa | Composições ativas de amaciadores de tecidos |
PL3418354T3 (pl) * | 2017-06-20 | 2020-10-19 | Kao Corporation, S.A. | Kompozycje czynne do zmiękczania tkanin |
US11434193B2 (en) | 2018-06-26 | 2022-09-06 | Evonik Operations Gmbh | Preparation method for esterquats based on oil |
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 (de) * | 1975-06-09 | 1985-04-11 | Henkel KGaA, 4000 Düsseldorf | Kationische Avivagemittel mit verbesserter Kaltwasserlöslichkeit |
DD159263A3 (de) * | 1980-12-23 | 1983-03-02 | Peter Reinemann | Weichspuelmittelkonzentrate |
DE3137043A1 (de) * | 1981-09-17 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Ammoniumverbindungen |
-
1987
- 1987-06-19 DE DE19873720332 patent/DE3720332A1/de not_active Withdrawn
-
1988
- 1988-04-16 DE DE8888106112T patent/DE3861985D1/de not_active Expired - Lifetime
- 1988-04-16 AT AT88106112T patent/ATE61565T1/de not_active IP Right Cessation
- 1988-04-16 EP EP88106112A patent/EP0295385B1/de not_active Expired - Lifetime
- 1988-04-16 ES ES88106112T patent/ES2019855B3/es 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 |
---|---|
EP0295385A1 (de) | 1988-12-21 |
ES2019855A4 (es) | 1991-07-16 |
DE3720332A1 (de) | 1988-12-29 |
AU1813188A (en) | 1988-12-22 |
ATE61565T1 (de) | 1991-03-15 |
ES2019855B3 (es) | 1991-12-01 |
DE3861985D1 (de) | 1991-04-18 |
US4830771A (en) | 1989-05-16 |
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