EP1006176A1 - Compositions adoucissantes très visqueuses et faiblement concentrées - Google Patents
Compositions adoucissantes très visqueuses et faiblement concentrées Download PDFInfo
- Publication number
- EP1006176A1 EP1006176A1 EP99113291A EP99113291A EP1006176A1 EP 1006176 A1 EP1006176 A1 EP 1006176A1 EP 99113291 A EP99113291 A EP 99113291A EP 99113291 A EP99113291 A EP 99113291A EP 1006176 A1 EP1006176 A1 EP 1006176A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- low
- fatty acid
- concentration
- highly viscous
- approx
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 29
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- 229930195729 fatty acid Natural products 0.000 claims abstract description 29
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 25
- 239000002979 fabric softener Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003921 oil Substances 0.000 claims description 11
- 239000002304 perfume Substances 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract description 6
- -1 triethanolamine fatty acid esters Chemical class 0.000 abstract description 6
- 239000006185 dispersion Substances 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- 101000916289 Ctenocephalides felis Salivary antigen 1 Proteins 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 3
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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 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. These components are used alone or in Mixtures with other cationic or neutral substances in 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.
- 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. The consumer requirements for these funds fluctuate however, significant within this market.
- DMDMAC distearyldimethylammonium chloride
- imidazolinium quats within Europe replaced almost everywhere. The consumer requirements for 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.
- the object is achieved by using quaternary fatty acid amino alcohol esters from triethanolamine with partially hydrogenated fatty acids in the ratio of 1: 1.6 to 1: 2 in alcohols or glycols.
- 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 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 glycol; 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 glycol
- 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.
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)
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 true EP1006176A1 (fr) | 2000-06-07 |
| EP1006176B1 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001093653A3 (fr) * | 2000-06-08 | 2002-04-04 | Cognis Deutschland Gmbh | Melanges de composes quaternaires d'ester |
| EP2576743B1 (fr) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Saturation d'une chaîne d'acides gras dans un esterquat à base d'alcanolamine |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1370634B1 (fr) * | 2001-03-07 | 2005-06-08 | The Procter & Gamble Company | Composition de conditionnement pour tissus a ajouter au rin age en cas de detergent residuel |
| EP1323817B1 (fr) * | 2001-12-24 | 2006-03-29 | Cognis IP Management GmbH | Compositions cationiques de nettoyage de surfaces dures |
| 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 |
| US20050113282A1 (en) * | 2003-11-20 | 2005-05-26 | Parekh Prabodh P. | Melamine-formaldehyde microcapsule slurries for fabric article freshening |
| US20050112152A1 (en) * | 2003-11-20 | 2005-05-26 | Popplewell Lewis M. | Encapsulated materials |
| US7105064B2 (en) | 2003-11-20 | 2006-09-12 | International Flavors & Fragrances Inc. | Particulate fragrance deposition on surfaces and malodour elimination from surfaces |
| 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 |
| EP1879991A1 (fr) * | 2005-05-12 | 2008-01-23 | The Procter and Gamble Company | Compositions adoucissantes pour tissus restant stables en conditions de congelation-decongelation |
| MX2007014173A (es) * | 2005-05-18 | 2008-02-07 | Stepan Co | Composiciones suavizantes de tejidos de alta viscosidad con bajo contenido de solidos y procedimiento para elaborar las mismas. |
| US8778866B2 (en) * | 2011-10-20 | 2014-07-15 | The Procter & Gamble Company | Continuous process of making a fabric softener composition |
| WO2013126335A1 (fr) * | 2012-02-21 | 2013-08-29 | Stepan Company | Compositions de produits assouplissants |
| EP2847307B1 (fr) | 2012-05-07 | 2016-04-06 | Evonik Degussa GmbH | Composition d'agent actif assouplissant pour tissus et son procédé de fabrication |
| 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 |
| WO2014143182A1 (fr) | 2013-03-15 | 2014-09-18 | 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 |
| EP2997958B1 (fr) | 2014-09-22 | 2021-03-10 | Evonik Operations GmbH | Émulsion contenant des esterquats liquides et polymères épaississants |
| EP2997959B1 (fr) | 2014-09-22 | 2019-12-25 | Evonik Operations GmbH | Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine |
| UA119182C2 (uk) | 2014-10-08 | 2019-05-10 | Евонік Дегусса Гмбх | Активна композиція для пом'якшувача тканини |
| EP3420062B1 (fr) | 2016-02-26 | 2020-05-27 | Evonik Operations GmbH | Amides de polyamines aliphatiques et d'acide 12-hydroxyoctadécanoïque et compositions d'épaississants stables aux lipases |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994020597A1 (fr) * | 1993-03-01 | 1994-09-15 | The Procter & Gamble Company | Compositions adoucissantes pour tissus concentrees et biodegradables a base d'ammonium quaternaire et composes contenant des chaines d'acide gras insature a indice d'iode intermediaire |
| EP0704522A2 (fr) * | 1994-09-20 | 1996-04-03 | The Procter & Gamble Company | Compositions adoucissants du linge, activées dans un séchoir, contenant un acide gras insaturé |
| EP0707059A2 (fr) * | 1994-10-14 | 1996-04-17 | Kao Corporation | Composition adoucissante liquide, son utilisation et procédé de préparation d'un sel d'ammonium quaternaire |
| WO1997008285A1 (fr) * | 1995-08-31 | 1997-03-06 | Colgate-Palmolive Company | Compositions d'assouplisseur stables pour textiles |
| US5637743A (en) * | 1991-12-31 | 1997-06-10 | Stepan Europe | Quaternary ammonium surfactants derived from tertiary amines and fabric softeners containing quaternary ammonium surfactants |
| WO1997042279A1 (fr) * | 1996-05-03 | 1997-11-13 | Akzo Nobel N.V. | Compose d'ammonium quaternaire a base de triethanolamine a haute teneur en di(alkylesters d'acides gras) produit a partir de triethanolamine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349033A (en) | 1964-08-26 | 1967-10-24 | Millmaster Onyx Corp | Stable microbiologically active laundry softener |
| CH1824769D (fr) | 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 |
| 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 |
| DE4446137A1 (de) * | 1994-12-23 | 1996-06-27 | Huels Chemische Werke Ag | Quaternierte Triethanolamindifettsäureester |
| 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 DE DE59911323T patent/DE59911323D1/de not_active Expired - Lifetime
- 1999-07-09 ES ES99113291T patent/ES2235404T3/es not_active Expired - Lifetime
- 1999-07-09 EP EP99113291A patent/EP1006176B1/fr not_active Expired - Lifetime
- 1999-11-02 CA CA002288255A patent/CA2288255C/fr 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
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637743A (en) * | 1991-12-31 | 1997-06-10 | Stepan Europe | Quaternary ammonium surfactants derived from tertiary amines and fabric softeners containing quaternary ammonium surfactants |
| WO1994020597A1 (fr) * | 1993-03-01 | 1994-09-15 | The Procter & Gamble Company | Compositions adoucissantes pour tissus concentrees et biodegradables a base d'ammonium quaternaire et composes contenant des chaines d'acide gras insature a indice d'iode intermediaire |
| EP0704522A2 (fr) * | 1994-09-20 | 1996-04-03 | The Procter & Gamble Company | Compositions adoucissants du linge, activées dans un séchoir, contenant un acide gras insaturé |
| EP0707059A2 (fr) * | 1994-10-14 | 1996-04-17 | Kao Corporation | Composition adoucissante liquide, son utilisation et procédé de préparation d'un sel d'ammonium quaternaire |
| WO1997008285A1 (fr) * | 1995-08-31 | 1997-03-06 | Colgate-Palmolive Company | Compositions d'assouplisseur stables pour textiles |
| WO1997042279A1 (fr) * | 1996-05-03 | 1997-11-13 | Akzo Nobel N.V. | Compose d'ammonium quaternaire a base de triethanolamine a haute teneur en di(alkylesters d'acides gras) produit a partir de triethanolamine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001093653A3 (fr) * | 2000-06-08 | 2002-04-04 | Cognis Deutschland Gmbh | Melanges de composes quaternaires d'ester |
| EP2576743B1 (fr) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Saturation d'une chaîne d'acides gras dans un esterquat à base d'alcanolamine |
Also Published As
| Publication number | Publication date |
|---|---|
| US6180594B1 (en) | 2001-01-30 |
| DE19855366A1 (de) | 2000-06-08 |
| ES2235404T3 (es) | 2005-07-01 |
| CA2288255A1 (fr) | 2000-06-01 |
| CA2288255C (fr) | 2007-02-06 |
| PL336869A1 (en) | 2000-06-05 |
| DE59911323D1 (de) | 2005-01-27 |
| EP1006176B1 (fr) | 2004-12-22 |
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