EP1006176B1 - Compositions adoucissantes très visqueuses et faiblement concentrées - Google Patents

Compositions adoucissantes très visqueuses et faiblement concentrées Download PDF

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Publication number
EP1006176B1
EP1006176B1 EP99113291A EP99113291A EP1006176B1 EP 1006176 B1 EP1006176 B1 EP 1006176B1 EP 99113291 A EP99113291 A EP 99113291A EP 99113291 A EP99113291 A EP 99113291A EP 1006176 B1 EP1006176 B1 EP 1006176B1
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EP
European Patent Office
Prior art keywords
approx
low
fatty acid
viscosity
compounds
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
EP99113291A
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German (de)
English (en)
Other versions
EP1006176A1 (fr
Inventor
Michael Fender
Hans-Jürgen Dr. Köhle
Simone Schüssler
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.)
Evonik Goldschmidt Rewo GmbH
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Goldschmidt Rewo GmbH
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Publication of EP1006176A1 publication Critical patent/EP1006176A1/fr
Application granted granted Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid

Definitions

  • the present invention relates to low-concentration, highly viscous aqueous Fabric softener in the form of aqueous emulsions or dispersions.
  • Cationic compounds are usually used as fabric softener, for example quaternary ammonium compounds, which are in addition to long-chain Alkyl radicals can also contain ester or amide groups, for example as in U.S. Patent 3,349,033, 3,644,203, 3,946,115, 3,997,453, 4,073,735, 4,119,545, etc. described. These components are used alone or in mixtures with others cationic or neutral substances in the form of aqueous Dispersions added to the rinsing bath.
  • Ammonium compounds containing ester bonds are frequently used as for example in EP-A-0 239 910, US-PS 3 915 867, US-PS 4 137 180, U.S. Patent 4,830,771.
  • plasticizers for textiles which act as active substance quaternary ester components with a balanced ratio degree of esterification (ratio of fatty acid to alkanolamine) and unsaturation (Iodine numbers) of the fatty acids in relation to their chain lengths and the "both good stability and good fluidity or pourability at relatively should have high concentrations ".
  • Ester compounds based on triethanolamine such as N-methyl, N, N-bis (beta-C 14-18 -acyloxyethyl), N-beta-hydroxyethyl ammonium methosulfate) are particularly widespread and are available under trade names such as TETRANYL® AT 75 (trademark of KAO Corp.), STEPANTEX® VRH 90 (trademark of Stepan Corp.) or REWOQUAT® WE 18 (trademark of Witco Surfactants GmbH).
  • esterquats have the previous raw materials distearyldimethylammonium chloride (DSDMAC) and imidazolinium quats within Europe replaced almost everywhere. Consumer demands on these funds fluctuate however, significant within this market.
  • DMDMAC distearyldimethylammonium chloride
  • imidazolinium quats within Europe replaced almost everywhere. Consumer demands on these funds fluctuate however, significant within this market.
  • the desired or required viscosities of these products to achieve the desired effect is in the range of about 500 mPa * s or preferably above.
  • This size was traditional with the laundry soft raw materials used (e.g. DSDMAC) easily accessible, without the need for additional viscosity regulators. With the esterquats it is due to the different viscosity behavior of these raw materials become difficult to achieve the desired high viscosities without additional to achieve high-priced thickeners.
  • the object of the invention was to overcome the above-mentioned disadvantages of conventional overcome low concentration fabric softener formulations and fabric softener to provide that in addition to good biodegradability much improved level of good soft grip while maintaining have good rewetting power and without the addition of thickeners Achieve viscosities of> 500 mPa * s.
  • Another object of the invention is a method for producing low-concentration, high-viscosity fabric softener formulations, which thereby is characterized in that the compounds of general formula (I) in Temperatures between 28 ° C and 45 ° C preheated water, if necessary with the use of solvents, dyes and perfume oils, be entered and dispersed.
  • the quaternary compounds of the general compounds used according to the invention Formula (I) are obtained by methods well known in the art by esterification of triethanolamine with fatty acid and subsequent Quaternization manufactured.
  • fat components for the esterification or transesterification are the known and usual monobasic fatty acids based on natural vegetable and animal oils with in particular 14-18 carbon atoms, used, such as tallow fatty acids and palm fatty acids or their methyl or Ethyl ester.
  • the iodine number as a measure of the average degree of saturation of a Fatty acid, is the amount of iodine, which is from 100 g of the compound for saturation of the double bonds.
  • Partially hydrogenated tallow fatty acids and palm fatty acids are preferred according to the invention with iodine numbers between 15-25. They are commercial products and are offered by various companies under their respective trade names.
  • the esterification or transesterification is carried out according to known methods.
  • the triethanolamine with the desired degree of esterification appropriate amount of fatty acid or fatty acid ester if appropriate in the presence of a catalyst, e.g. B. methanesulfonic acid, under nitrogen 160-240 ° C implemented and the water of reaction or alcohol formed distilled off continuously, optionally to complete the reaction the pressure can be reduced.
  • a catalyst e.g. B. methanesulfonic acid
  • the subsequent quaternization is also carried out using known processes.
  • the procedure according to the invention is preferably such that the ester, if appropriate using a solvent, preferably with in particular Isopropanol, ethanol, 1,2-propylene glycol and / or dipropylene glycol, at 60-90 ° C with equimolar amounts of the quaternizing agent with stirring, optionally under pressure, and the completion of the reaction is monitored by checking the total number of amines.
  • Examples of the quaternizing agents used are short-chain dialkyl phosphates and sulfates such as diethyl sulfate, dimethyl phosphate, diethyl phosphate, short chain halogenated hydrocarbons; in particular according to the invention Dimethyl sulfate used.
  • Triethanolamine was used to produce the quaternary ammonium compounds (TEA) and fatty acids implemented according to the usual procedures and quaternized.
  • the fatty acids were also used
  • the fabric softener is produced by emulsifying or dispersing of the individual components in water. This can be done on this Conventional procedures are applied.
  • the fabric softener according to the invention can the specified components within the in this area Desired limits, such as 3 to 10 wt .-%, preferably 4 to 5% by weight of the compounds of the general formula (I); 0.2-2 % By weight of a solvent such as in particular isopropanol, ethanol, propylene glycol, dipropylene; 0.1-1.0% by weight of perfume oil and the rest of 100 % By weight (ad 100) water.
  • a solvent such as in particular isopropanol, ethanol, propylene glycol, dipropylene
  • perfume oil 0.1-1.0% by weight of perfume oil and the rest of 100 % By weight (ad 100) water.
  • the application concentration after dilution with water lies in the range depending on the application 0.1-1.0 g of at least one of the compounds of the general formula (I) per rinse cycle.
  • Example 1 (Comparative example ):
  • Example 2 (Comparative example ):
  • Example 3 (Comparative example ):

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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)

Claims (2)

  1. Utilisation d'au moins une des compositions répondant à la formule générale (I)
    Figure 00150001
    dans laquelle R représente le reste d'un acide gras ayant 14 à 18 atomes de carbone, avec un indice d'iode dans la plage de 15-25, et a = 1, 2 ou 3, à condition que le rapport entre les groupes OH et le reste R soit de 1:1,6 à 1:2,
    en tant que seul composant actif plastifiant pour la fabrication d'agents de rinçage adoucissants aqueux très visqueux, faiblement concentrés, contenant 3 à 10 % en poids, de préférence 4 à 5 % en poids des compositions répondant à la formule générale (I).
  2. Utilisation d'au moins une des compositions répondant à la formule générale (I) selon la revendication 1,
    dans laquelle
    R représente le reste d'un acide gras de suif ou acide gras de palme, avec un indice d'iode de 15 à 25.
EP99113291A 1998-12-01 1999-07-09 Compositions adoucissantes très visqueuses et faiblement concentrées Expired - Lifetime EP1006176B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19855366A DE19855366A1 (de) 1998-12-01 1998-12-01 Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel
DE19855366 1998-12-01

Publications (2)

Publication Number Publication Date
EP1006176A1 EP1006176A1 (fr) 2000-06-07
EP1006176B1 true EP1006176B1 (fr) 2004-12-22

Family

ID=7889605

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99113291A Expired - Lifetime EP1006176B1 (fr) 1998-12-01 1999-07-09 Compositions adoucissantes très visqueuses et faiblement concentrées

Country Status (6)

Country Link
US (1) US6180594B1 (fr)
EP (1) EP1006176B1 (fr)
CA (1) CA2288255C (fr)
DE (2) DE19855366A1 (fr)
ES (1) ES2235404T3 (fr)
PL (1) PL336869A1 (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
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DE10028453B4 (de) * 2000-06-08 2013-06-27 Cognis Ip Management Gmbh Esterquatmischungen
CA2439512A1 (fr) * 2001-03-07 2002-09-19 The Procter & Gamble Company Composition de conditionnement pour tissus a ajouter au rincage en cas de detergent residuel
ATE321834T1 (de) * 2001-12-24 2006-04-15 Cognis Ip Man Gmbh Kationische zubereitungen für die reinigung harter oberflächen
US7125835B2 (en) * 2002-10-10 2006-10-24 International Flavors & Fragrances Inc Encapsulated fragrance chemicals
US7585824B2 (en) 2002-10-10 2009-09-08 International Flavors & Fragrances Inc. Encapsulated fragrance chemicals
BR0303954A (pt) * 2002-10-10 2004-09-08 Int Flavors & Fragrances Inc Composição, fragrância, método para divisão de uma quantidade efetiva olfativa de fragrância em um produto sem enxague e produto sem enxague
US20040097395A1 (en) 2002-11-14 2004-05-20 Andre Crutzen Fabric softening composition containing esterquat with specific ester distribution and sequestrant
US20040097396A1 (en) * 2002-11-14 2004-05-20 Myriam Peeters Concentrated fabric softening composition containing esterquat with specific ester distribution and an electrolyte
DE10320433A1 (de) * 2003-05-08 2005-02-17 Henkel Kgaa Frostresistente Konditioniermittel
US20050112152A1 (en) * 2003-11-20 2005-05-26 Popplewell Lewis M. Encapsulated materials
US20050113282A1 (en) * 2003-11-20 2005-05-26 Parekh Prabodh P. Melamine-formaldehyde microcapsule slurries for fabric article freshening
US20050226900A1 (en) * 2004-04-13 2005-10-13 Winton Brooks Clint D Skin and hair treatment composition and process for using same resulting in controllably-releasable fragrance and/or malodour counteractant evolution
US20050227907A1 (en) * 2004-04-13 2005-10-13 Kaiping Lee Stable fragrance microcapsule suspension and process for using same
US7594594B2 (en) * 2004-11-17 2009-09-29 International Flavors & Fragrances Inc. Multi-compartment storage and delivery containers and delivery system for microencapsulated fragrances
US20070207174A1 (en) * 2005-05-06 2007-09-06 Pluyter Johan G L Encapsulated fragrance materials and methods for making same
CA2606449A1 (fr) * 2005-05-12 2006-11-23 The Procter & Gamble Company Compositions adoucissantes pour tissus restant stables en conditions de congelation-decongelation
CA2609058A1 (fr) * 2005-05-18 2006-11-23 Stepan Company Compositions contenant des agents adoucissants, a faible teneur en solides et a haute viscosite destinees aux textiles et leur procede de production
US8865640B2 (en) 2010-05-28 2014-10-21 Colgate-Palmolive Company Fatty acid chain saturation in alkanol amine based esterquat
CA2850511A1 (fr) * 2011-10-20 2013-04-25 The Procter & Gamble Company Procede continu de fabrication d'une composition de produit assouplissant
EP2817401A4 (fr) * 2012-02-21 2015-04-22 Stepan Co Compositions de produits assouplissants
CN104471044B (zh) * 2012-05-07 2017-07-25 赢创德固赛有限公司 织物软化剂活性组合物及其制备方法
US20150250166A1 (en) 2012-08-23 2015-09-10 Allylix, Inc. Nootkatone as an insecticide and insect repellent
WO2014099821A2 (fr) 2012-12-18 2014-06-26 Allylix, Inc. Solavétivone et 5-épi-bêta-vétivone en tant qu'agents répulsifs de nuisibles et pesticides
EP2970827B1 (fr) 2013-03-15 2018-03-28 Stepan Company Compositions d'assouplissant pour textile
BR102014025172B1 (pt) * 2013-11-05 2020-03-03 Evonik Degussa Gmbh Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa
EP2997959B1 (fr) 2014-09-22 2019-12-25 Evonik Operations GmbH Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine
EP2997958B1 (fr) 2014-09-22 2021-03-10 Evonik Operations GmbH Émulsion contenant des esterquats liquides et polymères épaississants
UA119182C2 (uk) 2014-10-08 2019-05-10 Евонік Дегусса Гмбх Активна композиція для пом'якшувача тканини
CA3014810A1 (fr) 2016-02-26 2017-08-31 Evonik Degussa Gmbh Amides de polyamines aliphatiques et d'acide 12-hydroxyoctadecanoique et compositions d'epaississants stables aux lipases

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US3946115A (en) 1974-07-10 1976-03-23 Ralston Purina Company High performance horse feed and method of making
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GB1567947A (en) 1976-07-02 1980-05-21 Unilever Ltd Esters of quaternised amino-alcohols for treating fabrics
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DE3720332A1 (de) 1987-06-19 1988-12-29 Huels Chemische Werke Ag Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung
ES2094893T3 (es) * 1991-12-31 1997-02-01 Stepan Europe Tensioactivos a base de compuestos de amonio cuaternario, procedimientos de preparacion, bases, y composiciones suavizantes derivadas.
JPH08507766A (ja) * 1993-03-01 1996-08-20 ザ、プロクター、エンド、ギャンブル、カンパニー 濃縮生分解性四級アンモニウム布帛柔軟剤組成物、および中間ヨウ素価不飽和脂肪酸鎖を含む化合物
DE4402852C1 (de) * 1994-01-31 1995-02-16 Henkel Kgaa Detergensgemische und deren Verwendung
US5869716A (en) * 1994-03-18 1999-02-09 Henkel Kommanditgesellschaft Auf Aktien Process for the production of esterquats
US5503756A (en) * 1994-09-20 1996-04-02 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
EP0707059B1 (fr) * 1994-10-14 2004-09-08 Kao Corporation Composition adoucissante liquide
DE4446137A1 (de) * 1994-12-23 1996-06-27 Huels Chemische Werke Ag Quaternierte Triethanolamindifettsäureester
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DE19756434A1 (de) * 1997-12-18 1999-06-24 Witco Surfactants Gmbh Wäßrige Weichspülmittel mit verbessertem Weichgriff

Also Published As

Publication number Publication date
DE59911323D1 (de) 2005-01-27
DE19855366A1 (de) 2000-06-08
ES2235404T3 (es) 2005-07-01
CA2288255A1 (fr) 2000-06-01
PL336869A1 (en) 2000-06-05
EP1006176A1 (fr) 2000-06-07
CA2288255C (fr) 2007-02-06
US6180594B1 (en) 2001-01-30

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