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 PDF

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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
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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
Application number
US10/876,037
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English (en)
Inventor
Joaquim Bigorra Llosas
Nuria Bonastre Gilabert
Agustin Sanchez
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.)
Cognis Iberia SL
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Cognis Iberia SL
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis Iberia SL filed Critical Cognis Iberia SL
Assigned to COGNIS IBERIA S.L. reassignment COGNIS IBERIA S.L. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BIGORRA LLOSAS, JOAQUIM, BONASTRE GILABERT, NURIA, SANCHEZ, AGUSTIN
Publication of US20050022312A1 publication Critical patent/US20050022312A1/en
Abandoned legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • C11D3/0089Pearlescent compositions; Opacifying agents
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/325Amines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes
    • A61K2800/436Interference 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)
US10/876,037 2003-06-24 2004-06-24 Pearlescent preparations containing quaternized triethanolamine fatty acid esters, processes for preparing the same, and methods of use therefor Abandoned US20050022312A1 (en)

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

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Family Applications (1)

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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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
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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
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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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19732708C1 (de) * 1997-07-30 1999-03-18 Henkel Kgaa Verwendung von Fettethern

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* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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