EP1006176B1 - Niedrigkonzentrierte, hochviskose wässrige Weichspülmittel - Google Patents
Niedrigkonzentrierte, hochviskose wässrige Weichspülmittel Download PDFInfo
- 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
- Authority
- 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
Links
- 0 CN(C*)CC[O-] Chemical compound CN(C*)CC[O-] 0.000 description 2
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
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening 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)
Description
Co-Komponenten Fettsäureester mono- oder polyfunktioneller Alkohole, worin zur Reduzierung der Viskosität der Mischung zusätzliche Elektrolyte mitverwendet werden müssen.
Talgfettsäure mit einer Säurezahl von 202-208, einer Jodzahl von 36-44 und einer C-Kettenverteilung von | ||
<C 16 | ca. 2 % | |
C 16 | ca. 25 % | |
C 16' | ca. 2 % | (' einfach ungesättigt) |
C 17 | ca. 2 % | |
C 18 | ca. 28 % | |
C 18' | ca. 37 % | |
C 18" | ca. 3 % | ("zweifach ungesättigt) |
>C 18 | ca. 2 % |
Palmfettsäure mit einer Säurezahl von 205-212, einer Jodzahl von 30-40 und einer C-Kettenverteilung von | |
<C 16 | ca. 2 % |
C 16 | ca. 46 % |
C 16' | ca. 1 % |
C17 | - |
C18 | ca. 13 % |
C 18' | ca. 36 % |
C 18" | ca. 2 % |
>C 18 | ca. 1 % |
Talgfettsäure mit einer Säurezahl von 202-208, einer Jodzahl von 15-25 und einer C-Kettenverteilung von | |
<C 16 | ca. 2 % |
C 16 | ca. 30 % |
C 16' | - |
C 17 | ca. 2 % |
C 18 | ca. 47 % |
C 18' | ca. 17 % |
C 18" | ca. 1 % |
>C 18 | ca. 2% |
5,5 g | Komponente A |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 40 °C |
5,5 g | Komponente B |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 30 °C |
5,5 g | Komponente C |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 45 °C |
5,5 g | Komponente D |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 30 °C |
5,5 g | Komponente E |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 45°C |
5,5 g | Komponente E |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 35 °C |
5,5 g | Komponente F |
0,20 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0,20 g | Parfümöl Fragrance® (D 60515 W der Fa. Haarmann und Reimer GmbH) |
ad 100 | Wasser, 9°dH, 35°C |
Claims (2)
- Verwendung von mindestens einer der Verbindungen der allgemeinen Formel (I) worin R der Rest einer Fettsäure mit 14 bis 18 Kohlenstoffatomen und Jodzahlen im Bereich von 15-25 ist und a = 1, 2, 3 sein kann mit der Maßgabe, dass das Verhältnis von OH-Gruppen zu dem Rest R = 1:1,6 bis 1:2 beträgt, als alleinige weichmachende Wirkkomponente zur Herstellung niedrigkonzentrierter, enthaltend 3 bis 10 Gew.-%, vorzugsweise 4 bis 5 Gew.-% der Verbindungen der allgemeinen Formel (I), hochviskoser wässriger Weichspülmittel.
- Verwendung von mindestens einer der Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1,
worin R der Rest einer Talgfettsäure oder Palmfettsäure mit Jodzahlen von 15 bis 25 ist.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19855366 | 1998-12-01 | ||
DE19855366A DE19855366A1 (de) | 1998-12-01 | 1998-12-01 | Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1006176A1 EP1006176A1 (de) | 2000-06-07 |
EP1006176B1 true EP1006176B1 (de) | 2004-12-22 |
Family
ID=7889605
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99113291A Expired - Lifetime EP1006176B1 (de) | 1998-12-01 | 1999-07-09 | Niedrigkonzentrierte, hochviskose wässrige Weichspülmittel |
Country Status (6)
Country | Link |
---|---|
US (1) | US6180594B1 (de) |
EP (1) | EP1006176B1 (de) |
CA (1) | CA2288255C (de) |
DE (2) | DE19855366A1 (de) |
ES (1) | ES2235404T3 (de) |
PL (1) | PL336869A1 (de) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10028453B4 (de) * | 2000-06-08 | 2013-06-27 | Cognis Ip Management Gmbh | Esterquatmischungen |
CA2439512A1 (en) * | 2001-03-07 | 2002-09-19 | The Procter & Gamble Company | Rinse-added fabric conditioning composition for use where residual detergent is present |
DE50109370D1 (de) * | 2001-12-24 | 2006-05-18 | Cognis Ip Man Gmbh | Kationische Zubereitungen für die Reinigung harter Oberflächen |
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 |
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 |
US20040097396A1 (en) * | 2002-11-14 | 2004-05-20 | Myriam Peeters | Concentrated fabric softening composition containing esterquat with specific ester distribution and an electrolyte |
US20040097395A1 (en) † | 2002-11-14 | 2004-05-20 | Andre Crutzen | Fabric softening composition containing esterquat with specific ester distribution and sequestrant |
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 |
US20050227907A1 (en) * | 2004-04-13 | 2005-10-13 | Kaiping Lee | Stable fragrance microcapsule suspension and process for using same |
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 |
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 |
RU2379335C2 (ru) * | 2005-05-12 | 2010-01-20 | Дзе Проктер Энд Гэмбл Компани | Составы с мягчителем ткани, стабильные в условиях замораживания-размораживания |
CA2609058A1 (en) * | 2005-05-18 | 2006-11-23 | Stepan Company | Low solids, high viscosity fabric softener compositions and process for making the same |
US8865640B2 (en) | 2010-05-28 | 2014-10-21 | Colgate-Palmolive Company | Fatty acid chain saturation in alkanol amine based esterquat |
US8778866B2 (en) * | 2011-10-20 | 2014-07-15 | The Procter & Gamble Company | Continuous process of making a fabric softener composition |
CN104169410B (zh) * | 2012-02-21 | 2018-02-09 | 斯蒂潘公司 | 织物软化剂组合物 |
JP5992605B2 (ja) * | 2012-05-07 | 2016-09-14 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | 織物柔軟剤活性組成物およびその製造方法 |
US20150250166A1 (en) | 2012-08-23 | 2015-09-10 | Allylix, Inc. | Nootkatone as an insecticide and insect repellent |
US9839214B2 (en) | 2012-12-18 | 2017-12-12 | Evolva, Inc. | Solavetivone and 5-epi-beta-vertivone as pest repellants and pesticides |
JP6397883B2 (ja) | 2013-03-15 | 2018-09-26 | ステパン カンパニー | 柔軟剤組成物 |
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 (de) | 2014-09-22 | 2019-12-25 | Evonik Operations GmbH | Formulierung enthaltend esterquats basierend auf isopropanolamin und tetrahydroxypropylethylenediamin |
EP2997958B1 (de) | 2014-09-22 | 2021-03-10 | Evonik Operations GmbH | Emulsion enthaltend flüssige esterquats und polymerverdicker |
UA119182C2 (uk) | 2014-10-08 | 2019-05-10 | Евонік Дегусса Гмбх | Активна композиція для пом'якшувача тканини |
WO2017144340A1 (en) | 2016-02-26 | 2017-08-31 | Evonik Degussa Gmbh | Amides of aliphatic polyamines and 12-hydroxyoctadecanoic acid and lipase stable thickener compositions |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
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US3349033A (en) | 1964-08-26 | 1967-10-24 | Millmaster Onyx Corp | Stable microbiologically active laundry softener |
DK131432A (de) | 1968-12-09 | |||
US3915867A (en) | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
US3997453A (en) | 1974-02-11 | 1976-12-14 | Colgate-Palmolive Company | Softener dispersion |
US3946115A (en) | 1974-07-10 | 1976-03-23 | Ralston Purina Company | High performance horse feed and method of making |
US4073735A (en) | 1976-02-19 | 1978-02-14 | Colgate Palmolive Company | Rinse cycle fabric softener |
GB1567947A (en) | 1976-07-02 | 1980-05-21 | Unilever Ltd | Esters of quaternised amino-alcohols for treating fabrics |
US4119545A (en) | 1977-03-28 | 1978-10-10 | Colgate Palmolive Company | Concentrated fabric softening composition |
GB2188653A (en) | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
DE3720332A1 (de) | 1987-06-19 | 1988-12-29 | Huels Chemische Werke Ag | Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung |
EP0550361B1 (de) * | 1991-12-31 | 1996-10-16 | Stepan Europe | Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher |
ATE191743T1 (de) * | 1993-03-01 | 2000-04-15 | Procter & Gamble | Konzentrierte biologisch abbaubare weichspülerzusammensetzungen auf der basis von quartären ammoniumverbindungen |
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 (de) * | 1994-10-14 | 2004-09-08 | Kao Corporation | Flüssige Weichspülerzusammensetzung |
DE4446137A1 (de) * | 1994-12-23 | 1996-06-27 | Huels Chemische Werke Ag | Quaternierte Triethanolamindifettsäureester |
ES2171708T3 (es) * | 1995-08-31 | 2002-09-16 | Colgate Palmolive Co | Composiciones suavizantes estables para telas. |
US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
DE19756434A1 (de) * | 1997-12-18 | 1999-06-24 | Witco Surfactants Gmbh | Wäßrige Weichspülmittel mit verbessertem Weichgriff |
-
1998
- 1998-12-01 DE DE19855366A patent/DE19855366A1/de not_active Withdrawn
-
1999
- 1999-07-09 EP EP99113291A patent/EP1006176B1/de not_active Expired - Lifetime
- 1999-07-09 ES ES99113291T patent/ES2235404T3/es not_active Expired - Lifetime
- 1999-07-09 DE DE59911323T patent/DE59911323D1/de not_active Expired - Lifetime
- 1999-11-02 CA CA002288255A patent/CA2288255C/en not_active Expired - Lifetime
- 1999-11-11 US US09/438,695 patent/US6180594B1/en not_active Expired - Lifetime
- 1999-11-30 PL PL99336869A patent/PL336869A1/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CA2288255C (en) | 2007-02-06 |
ES2235404T3 (es) | 2005-07-01 |
CA2288255A1 (en) | 2000-06-01 |
EP1006176A1 (de) | 2000-06-07 |
DE59911323D1 (de) | 2005-01-27 |
DE19855366A1 (de) | 2000-06-08 |
US6180594B1 (en) | 2001-01-30 |
PL336869A1 (en) | 2000-06-05 |
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