US20050022312A1 - Pearlescent preparations containing quaternized triethanolamine fatty acid esters, processes for preparing the same, and methods of use therefor - Google Patents
Pearlescent preparations containing quaternized triethanolamine fatty acid esters, processes for preparing the same, and methods of use therefor Download PDFInfo
- Publication number
- US20050022312A1 US20050022312A1 US10/876,037 US87603704A US2005022312A1 US 20050022312 A1 US20050022312 A1 US 20050022312A1 US 87603704 A US87603704 A US 87603704A US 2005022312 A1 US2005022312 A1 US 2005022312A1
- Authority
- US
- United States
- Prior art keywords
- fatty acid
- pearlescent
- esterification product
- molar ratio
- triethanolamine
- 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.)
- Abandoned
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
-
- 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
- C11D3/0089—Pearlescent compositions; Opacifying agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/436—Interference pigments, e.g. Iridescent, Pearlescent
Definitions
- Quaternized fatty acid triethanolamine ester salts which belong to the group of esterquats, are cationic surfactants which are readily taken up by synthetic and natural fibers and which provide them with substantivity and a pleasant soft feel. Accordingly, aqueous dispersions of these compounds are used as fabric softeners and as hair conditioners. They are generally produced from fatty acids which are partly esterified with triethanolamine in the presence of hypophosphorous acid and then quaternized with alkyl halides or dialkyl sulfates, preferably methyl chloride or dimethyl sulfate, in a solution of lower alcohols or polyols. A molar ratio of triethanolamine to fatty acid of 1:1.2 to 1:2.2 is generally described in the literature, a ratio of 1:1.5 to 1:1.9 being preferred for performance reasons.
- the problem addressed by the present invention was to provide new water-containing preparations based on quaternized fatty acid triethanolamine ester salts which would have pearlescent properties without the addition of waxes and which would match known products in their performance properties.
- the present invention relates to pearlescent water-containing preparations which can be obtained by: (a) reacting triethanolamine and C 12-22 fatty acids in a molar ratio of 1:1.3 to 1:1.4, (b) subsequently quaternizing the esterification products in known manner and (c) dispersing the quaternization products in water.
- esterquats which have pearlescent properties in the form of aqueous dispersions can be produced by controlling the degree of esterification and the fatty acid, so that there is no need to use typical pearlizing waxes, for example of the glycol fatty acid ester type.
- the invention includes the observation that the molar ratio between triethanolamine and the fatty acids selected is the critical parameter: too low a ratio would lead to low pearlescence and, in particular, to unsatisfactory performance properties whereas, if the ratio is too high, no pearlescent effect at all is observed.
- the present invention also relates to a process for the production of pearlescent water-containing preparations, in which (a) triethanolamine and C 12-22 fatty acids are reacted in a molar ratio of 1:1.3 to 1:1.4, (b) the esterification products are then quaternized in known manner and (c) the quaternization products are dispersed in water.
- the preparations preferably contain 1 to 20% by weight, preferably 3 to 15% by weight and more particularly 5 to 10% by weight of free C 12-22 fatty acids.
- the esterquats may be produced both from fatty acids and from the corresponding triglycerides.
- the condensation of the alkanolamines with the fatty acids may also be carried out in the presence of defined quantities of dicarboxylic acids such as, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and/or dodecanedioic acid. This results in a partly oligomeric structure of the esterquats.
- the quaternized fatty acid triethanolamine ester salts according to the invention are produced in the presence of lower aliphatic alcohols or polyols which are added to the intermediate products before the quaternization.
- C 1-4 alcohols and C 2-10 alkylene glycols, especially isopropyl alcohol or propylene glycol, are suitable for this purpose. Their production is described, for example, in DE 19738645 C1 (Cognis).
- the quaternization generally gives 60 to 95% by weight and preferably 75 to 85% by weight preparations of the quaternized fatty acid triethanolamine ester salts in the lower alcohols or polyols which are then diluted with water to a solids concentration of 5 to 40% by weight and preferably 10 to 30% by weight and show pearlescence even in this concentration range.
- the present invention also relates to the use of the new pearlescent water-containing preparations for the production of softeners for synthetic and/or natural fibers in which they may be present in quantities of 10 to 100% by weight, based on the final preparation.
- the preparations themselves may be used as softeners, although they may also be further diluted with water and/or other typical auxiliaries and additives may be incorporated. This is particularly the case when the preparations are to be used as hair conditioners. So far as the additives in question are concerned, reference is again made to the above-cited DE 19738645 C1.
- 1 kg terry towelling was washed at 60° C. in a standard domestic washing machine of the Miele type and a measuring capful of the softener dispersions was added to the liquor.
- the results are set out in Table 1. Examples 1 to 3 correspond to the invention, Examples C1 to C3 are intended for comparison.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (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 |
---|---|---|---|
EP03014144.4 | 2003-06-24 | ||
EP03014144A EP1491617B1 (fr) | 2003-06-24 | 2003-06-24 | Compositions aqueuses nacrées |
Publications (1)
Publication Number | Publication Date |
---|---|
US20050022312A1 true US20050022312A1 (en) | 2005-02-03 |
Family
ID=33395853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/876,037 Abandoned US20050022312A1 (en) | 2003-06-24 | 2004-06-24 | Pearlescent preparations containing quaternized triethanolamine fatty acid esters, processes for preparing the same, and methods of use therefor |
Country Status (5)
Country | Link |
---|---|
US (1) | US20050022312A1 (fr) |
EP (1) | EP1491617B1 (fr) |
JP (1) | JP2005015997A (fr) |
DE (1) | DE50305183D1 (fr) |
ES (1) | ES2274142T3 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090069207A1 (en) * | 2006-03-22 | 2009-03-12 | The Procter & Gamble Company | Liquid treatment composition |
US20090156455A1 (en) * | 2007-06-15 | 2009-06-18 | Francesc Corominas | Compositions With Durable Pearlescent Aesthetics |
US9458412B2 (en) | 2012-10-19 | 2016-10-04 | Henkel Ag & Co. Kgaa | Fabric softener composition with trialkanolamine-based ester quat |
US11434193B2 (en) * | 2018-06-26 | 2022-09-06 | Evonik Operations Gmbh | Preparation method for esterquats based on oil |
Citations (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3915867A (en) * | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
US4212749A (en) * | 1974-07-05 | 1980-07-15 | Bayer Aktiengesellschaft | Liquid preparation of fatty acid/alkanolamine condensates |
US4268402A (en) * | 1978-09-21 | 1981-05-19 | Basf Aktiengesellschaft | Liquefaction of aqueous textile softeners |
US5372749A (en) * | 1992-02-19 | 1994-12-13 | Beijing Technology Of Printing Research Institute Chinese | Method for surface treating conductive copper powder with a treating agent and coupler |
US5422021A (en) * | 1989-09-19 | 1995-06-06 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
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 |
US5660759A (en) * | 1994-05-06 | 1997-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Cationic formulations for oiling leathers and skins |
US5670677A (en) * | 1993-03-18 | 1997-09-23 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts |
US5716498A (en) * | 1996-04-12 | 1998-02-10 | Witco Corporation | Process for softening paper in manufacture |
US5718841A (en) * | 1996-03-26 | 1998-02-17 | Rheox, Inc. | Organoclay compositions manufactured with organic acid derived ester quaternary ammonium compounds |
US5718891A (en) * | 1993-03-18 | 1998-02-17 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of solid esterquats with improved dispersibility in water |
US5750490A (en) * | 1994-01-31 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Detergent mixtures |
US5877145A (en) * | 1996-03-22 | 1999-03-02 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
US5886201A (en) * | 1993-10-08 | 1999-03-23 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized fatty acid triethanolamine ester salts with improved solubility in water |
US6159383A (en) * | 1998-04-17 | 2000-12-12 | Caterpillar Inc. | Filter head assembly |
US6190427B1 (en) * | 1998-11-23 | 2001-02-20 | Pure Energy Corporation | Diesel fuel composition |
US6362142B1 (en) * | 1997-07-17 | 2002-03-26 | Cognis Deutschland Gmbh | Detergent mixtures containing ester quats, chitosan and/or chitosan derivatives and protein hydrolyzates |
US6402976B1 (en) * | 1996-08-16 | 2002-06-11 | Henkel Kommanditgesellschaft Auf Aktien | Textile finishing agent |
US6410502B1 (en) * | 1998-06-10 | 2002-06-25 | Kao Corporation | Softener compositions |
US6429324B1 (en) * | 1997-12-13 | 2002-08-06 | Cognis Deutschland And Gmbh | Method for producing alkoxylated dimer fatty acids |
US6486121B2 (en) * | 1998-04-15 | 2002-11-26 | The Procter & Gamble Company | Softener active derived from acylated triethanolamine |
US6494920B1 (en) * | 1999-02-04 | 2002-12-17 | Cognis Deutschland Gmbh & Co. Kg | Detergent mixtures |
US6521589B2 (en) * | 1997-05-19 | 2003-02-18 | The Procter & Gamble Company | Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners |
US6616706B1 (en) * | 1997-05-12 | 2003-09-09 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing hair dye products |
US6623746B1 (en) * | 1998-07-16 | 2003-09-23 | Cognis Deutschland Gmbh & Co. Kg | PIT emulsions, methods of softening paper using the same, and paper substrates treated therewith |
US6755201B1 (en) * | 1999-06-15 | 2004-06-29 | Cognis Deutschland Gmbh & Co. Kg | Method for the durable shaping of keratin fibers |
US6794356B2 (en) * | 2000-05-24 | 2004-09-21 | The Procter & Gamble Company | Fabric softening composition comprising a malodor controlling agent |
US6855682B2 (en) * | 2001-03-08 | 2005-02-15 | Kao Corporation | Softener composition |
US6875735B1 (en) * | 1997-11-24 | 2005-04-05 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte content and optional phase stabilizer |
US6881359B2 (en) * | 2000-01-26 | 2005-04-19 | Cognis Deutschland Gmbh & Co. Kg | Processes for the preparation of low dust, limited particle size distribution, surfactant granules |
US6958313B2 (en) * | 2000-05-11 | 2005-10-25 | The Procter & Gamble Company | Highly concentrated fabric softener compositions and articles containing such compositions |
US6995131B1 (en) * | 1999-05-10 | 2006-02-07 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte and optional phase stabilizer |
US7012053B1 (en) * | 1999-10-22 | 2006-03-14 | The Procter & Gamble Company | Fabric care composition and method comprising a fabric care polysaccharide and wrinkle control agent |
US7015187B2 (en) * | 1997-05-19 | 2006-03-21 | The Procter & Gamble Company | Fabric softening compound |
US7087570B2 (en) * | 1999-12-24 | 2006-08-08 | Cognis Deutschland Gmbh & Co. Kg | Detergent tablets |
US7091168B2 (en) * | 2000-06-29 | 2006-08-15 | Cognis Deutschland Gmbh & Co. Kg | Liquid detergents |
US7309685B2 (en) * | 2003-02-10 | 2007-12-18 | Cognis Ip Management Gmbh | Textile finishing agents for imparting a sensory effect during use |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19732708C1 (de) * | 1997-07-30 | 1999-03-18 | Henkel Kgaa | Verwendung von Fettethern |
-
2003
- 2003-06-24 ES ES03014144T patent/ES2274142T3/es not_active Expired - Lifetime
- 2003-06-24 DE DE50305183T patent/DE50305183D1/de not_active Expired - Fee Related
- 2003-06-24 EP EP03014144A patent/EP1491617B1/fr not_active Expired - Lifetime
-
2004
- 2004-06-23 JP JP2004185140A patent/JP2005015997A/ja active Pending
- 2004-06-24 US US10/876,037 patent/US20050022312A1/en not_active Abandoned
Patent Citations (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3915867A (en) * | 1973-04-24 | 1975-10-28 | Stepan Chemical Co | Domestic laundry fabric softener |
US4212749A (en) * | 1974-07-05 | 1980-07-15 | Bayer Aktiengesellschaft | Liquid preparation of fatty acid/alkanolamine condensates |
US4268402A (en) * | 1978-09-21 | 1981-05-19 | Basf Aktiengesellschaft | Liquefaction of aqueous textile softeners |
US5422021A (en) * | 1989-09-19 | 1995-06-06 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening |
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 |
US5372749A (en) * | 1992-02-19 | 1994-12-13 | Beijing Technology Of Printing Research Institute Chinese | Method for surface treating conductive copper powder with a treating agent and coupler |
US5718891A (en) * | 1993-03-18 | 1998-02-17 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of solid esterquats with improved dispersibility in water |
US5670677A (en) * | 1993-03-18 | 1997-09-23 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts |
US5886201A (en) * | 1993-10-08 | 1999-03-23 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized fatty acid triethanolamine ester salts with improved solubility in water |
US5750490A (en) * | 1994-01-31 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Detergent mixtures |
US5660759A (en) * | 1994-05-06 | 1997-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Cationic formulations for oiling leathers and skins |
US5877145A (en) * | 1996-03-22 | 1999-03-02 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
US5718841A (en) * | 1996-03-26 | 1998-02-17 | Rheox, Inc. | Organoclay compositions manufactured with organic acid derived ester quaternary ammonium compounds |
US5716498A (en) * | 1996-04-12 | 1998-02-10 | Witco Corporation | Process for softening paper in manufacture |
US6402976B1 (en) * | 1996-08-16 | 2002-06-11 | Henkel Kommanditgesellschaft Auf Aktien | Textile finishing agent |
US6616706B1 (en) * | 1997-05-12 | 2003-09-09 | Henkel Kommanditgesellschaft Auf Aktien | Method for producing hair dye products |
US6521589B2 (en) * | 1997-05-19 | 2003-02-18 | The Procter & Gamble Company | Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners |
US7015187B2 (en) * | 1997-05-19 | 2006-03-21 | The Procter & Gamble Company | Fabric softening compound |
US6362142B1 (en) * | 1997-07-17 | 2002-03-26 | Cognis Deutschland Gmbh | Detergent mixtures containing ester quats, chitosan and/or chitosan derivatives and protein hydrolyzates |
US6875735B1 (en) * | 1997-11-24 | 2005-04-05 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte content and optional phase stabilizer |
US7037887B2 (en) * | 1997-11-24 | 2006-05-02 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte content and optional phase stabilizer |
US6429324B1 (en) * | 1997-12-13 | 2002-08-06 | Cognis Deutschland And Gmbh | Method for producing alkoxylated dimer fatty acids |
US6486121B2 (en) * | 1998-04-15 | 2002-11-26 | The Procter & Gamble Company | Softener active derived from acylated triethanolamine |
US6159383A (en) * | 1998-04-17 | 2000-12-12 | Caterpillar Inc. | Filter head assembly |
US6410502B1 (en) * | 1998-06-10 | 2002-06-25 | Kao Corporation | Softener compositions |
US6623746B1 (en) * | 1998-07-16 | 2003-09-23 | Cognis Deutschland Gmbh & Co. Kg | PIT emulsions, methods of softening paper using the same, and paper substrates treated therewith |
US6190427B1 (en) * | 1998-11-23 | 2001-02-20 | Pure Energy Corporation | Diesel fuel composition |
US6494920B1 (en) * | 1999-02-04 | 2002-12-17 | Cognis Deutschland Gmbh & Co. Kg | Detergent mixtures |
US6995131B1 (en) * | 1999-05-10 | 2006-02-07 | The Procter & Gamble Company | Clear or translucent aqueous fabric softener compositions containing high electrolyte and optional phase stabilizer |
US6755201B1 (en) * | 1999-06-15 | 2004-06-29 | Cognis Deutschland Gmbh & Co. Kg | Method for the durable shaping of keratin fibers |
US7012053B1 (en) * | 1999-10-22 | 2006-03-14 | The Procter & Gamble Company | Fabric care composition and method comprising a fabric care polysaccharide and wrinkle control agent |
US7087570B2 (en) * | 1999-12-24 | 2006-08-08 | Cognis Deutschland Gmbh & Co. Kg | Detergent tablets |
US6881359B2 (en) * | 2000-01-26 | 2005-04-19 | Cognis Deutschland Gmbh & Co. Kg | Processes for the preparation of low dust, limited particle size distribution, surfactant granules |
US6958313B2 (en) * | 2000-05-11 | 2005-10-25 | The Procter & Gamble Company | Highly concentrated fabric softener compositions and articles containing such compositions |
US7108725B2 (en) * | 2000-05-11 | 2006-09-19 | The Procter & Gamble Company | Highly concentrated fabric softener compositions and articles containing such compositions |
US7115173B2 (en) * | 2000-05-11 | 2006-10-03 | The Procter & Gamble Company | Highly concentrated fabric softener compositions and articles containing such compositions |
US6794356B2 (en) * | 2000-05-24 | 2004-09-21 | The Procter & Gamble Company | Fabric softening composition comprising a malodor controlling agent |
US7091168B2 (en) * | 2000-06-29 | 2006-08-15 | Cognis Deutschland Gmbh & Co. Kg | Liquid detergents |
US6855682B2 (en) * | 2001-03-08 | 2005-02-15 | Kao Corporation | Softener composition |
US7115779B2 (en) * | 2001-03-08 | 2006-10-03 | Kao Corporation | Softener composition |
US7309685B2 (en) * | 2003-02-10 | 2007-12-18 | Cognis Ip Management Gmbh | Textile finishing agents for imparting a sensory effect during use |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8003589B2 (en) | 2006-03-22 | 2011-08-23 | The Procter & Gamble Company | Laundry composition |
US20090069207A1 (en) * | 2006-03-22 | 2009-03-12 | The Procter & Gamble Company | Liquid treatment composition |
US8969281B2 (en) | 2006-03-22 | 2015-03-03 | The Procter & Gamble Company | Liquid treatment composition |
US20090186797A1 (en) * | 2006-03-22 | 2009-07-23 | The Procter & Gamble Company | Laundry composition |
US20090209445A1 (en) * | 2006-03-22 | 2009-08-20 | The Procter & Gamble Company | Liquid treatment unitized dose composition |
US7910535B2 (en) | 2006-03-22 | 2011-03-22 | The Procter & Gamble Company | Liquid treatment composition comprising a pearlescent agent |
US20090069206A1 (en) * | 2006-03-22 | 2009-03-12 | The Procter & Gamble Company | Liquid treatment composition |
US8188026B2 (en) | 2006-03-22 | 2012-05-29 | The Procter & Gamble Company | Liquid treatment composition |
US8236745B2 (en) | 2006-03-22 | 2012-08-07 | The Procter & Gamble Company | Liquid treatment composition |
US8357648B2 (en) | 2006-03-22 | 2013-01-22 | The Procter & Gamble Company | Liquid treatment unitized dose composition |
US20090156455A1 (en) * | 2007-06-15 | 2009-06-18 | Francesc Corominas | Compositions With Durable Pearlescent Aesthetics |
US8648029B2 (en) | 2007-10-29 | 2014-02-11 | The Procter & Gamble Company | Composition comprising a diester quaternary ammonium fabric softener with durable pearlescent aesthetics |
US9458412B2 (en) | 2012-10-19 | 2016-10-04 | Henkel Ag & Co. Kgaa | Fabric softener composition with trialkanolamine-based ester quat |
US11434193B2 (en) * | 2018-06-26 | 2022-09-06 | Evonik Operations Gmbh | Preparation method for esterquats based on oil |
Also Published As
Publication number | Publication date |
---|---|
EP1491617A1 (fr) | 2004-12-29 |
EP1491617B1 (fr) | 2006-09-27 |
ES2274142T3 (es) | 2007-05-16 |
JP2005015997A (ja) | 2005-01-20 |
DE50305183D1 (de) | 2006-11-09 |
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