EP0625184A1 - Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises. - Google Patents

Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises.

Info

Publication number
EP0625184A1
EP0625184A1 EP93917366A EP93917366A EP0625184A1 EP 0625184 A1 EP0625184 A1 EP 0625184A1 EP 93917366 A EP93917366 A EP 93917366A EP 93917366 A EP93917366 A EP 93917366A EP 0625184 A1 EP0625184 A1 EP 0625184A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
quaternized
carbon atoms
formula
viscosity
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
Application number
EP93917366A
Other languages
German (de)
English (en)
Other versions
EP0625184B1 (fr
Inventor
Oriol Ponsati
Joaquim Bigorra
Nuria Bonastre
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6451139&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0625184(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0625184A1 publication Critical patent/EP0625184A1/fr
Application granted granted Critical
Publication of EP0625184B1 publication Critical patent/EP0625184B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • D06M13/322—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
    • D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • 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
    • D06M13/144—Alcohols; Metal alcoholates
    • 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
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • 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
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material

Definitions

  • the invention relates to a process for the preparation of low-viscosity aqueous ester quat concentrates, in which aqueous solutions of quaternized di-fatty acid trialkanolamine ester salts are mixed with selected viscosity regulators.
  • the American patent US 23 40 881 describes aqueous dispersions of condensation products, Made from a hydroxyalkyl poly in and a fatty acid glyceride, which improve the lubricity and the softness of the textiles treated with it.
  • Esterquats are not only characterized by excellent anti-static and anti-static properties, but also have a surprisingly good biodegradability for cationic surfactants. It is disadvantageous, however, that aqueous esterquat concentrates behave dilutantly at low shear forces and are structurally viscous only when shear is strong. In practice, this means that the viscosity of aqueous ester quat concentrates increases by leaps and bounds when pumping, and conveying these products through pipelines is therefore extremely problematic.
  • the object of the invention was therefore to develop a new process for producing low-viscosity textile treatment agents which is free from the disadvantages described.
  • the invention relates to a process for the preparation of low-viscosity aqueous ester quat concentrates, which is characterized in that aqueous solutions of quaternized di-fatty acid trialkanolamine ester salts of the formula (I)
  • R 1 CO is an aliphatic, linear or branched saturated acyl radical having 6 to 22 carbon atoms
  • At least one viscosity regulator which is selected from the group consisting of
  • Quaternized di-fatty acid tialkanolamine ester salts are known substances which are accessible by the relevant methods of preparative organic chemistry. They are usually prepared from fatty acids which are esterified in the first step with trialkanolamines, such as, for example, triethanolamine, tripropanolamine or triisopropanolamine. The difatty acid ester formed can then, for example, in a manner known per se Methyl chloride or dimethyl sulfate can be quaternized.
  • concentration includes 12 to 40, preferably 15 to 25% by weight solutions of the ester quat base in water and the term "ester quat base” 70 to 95, preferably 80 to 90% by weight. To understand% solutions of the ester quats in isopropyl alcohol.
  • Typical examples of the fatty acid components of these compounds are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid and behenic acid, as well as their technical mixtures, which are obtained, for example, from the splitting of vegetable oils or animal fats.
  • Textile treatment agents with a particularly low viscosity under shear can be produced by using quaternized di-fatty acid trialkanolamine ester salts of the formula (I) in which R ⁇ -CO is an acyl radical having 12 to 18 carbon atoms, Z is an ethylene group and / or X represents chloride or methosulfate.
  • Suitable viscosity regulators a) are quaternized unsaturated di-fatty acid trialkanolamine ester salts which follow the formula (II)
  • R 2 CO is an aliphatic, linear or branched acyl radical having 16 to 22 carbon atoms and 1, 2 or 3 double bonds,
  • unsaturated fatty acids for example palmoleic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, gadoleic acid and / or erucic acid and their technical mixtures, which in the first stage are mixed with trialkanolamines, such as ethanol be implemented in, propanolamine or isopropanolamine.
  • the resulting difatty acid esters can then be quaternized in a manner known per se, for example with methyl chloride or dimethyl sulfate.
  • Preferred viscosity regulators are quaternized unsaturated di-fatty acid trialkanolamine ester salts of the formula (II), the fatty acid components of which are derived from oleic acid and / or elaidic acid.
  • Quaternized or pseudoquaternized fatty acid amidoamines of the formula (purple), (Illb) and / or (IIIc) can be used as viscosity-regulating component b), CH 3
  • R 3 CO is an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds,
  • Diamines for example ethylene or propylene diamine, dimethylamine methylamine (DAMA), diethylamine ethyl in (DAEA) or dimethylamine propylamine (DAPA) and subsequent methylation can be obtained.
  • DAMA dimethylamine methylamine
  • DAEA diethylamine ethyl in
  • DAPA dimethylamine propylamine
  • the components (purple), (Illb) and (IIIc) can be present side by side in a mixture, the weight ratio within the mixture triangle being 1: 1: 8; 1: 8: 1 and 8: 1: 1 may vary.
  • Quaternized fatty acid amidoamines of the formulas (purple), (Illb) and / or (IIIc), the fatty acid components of which have 12 to 18 and in particular 12 to 14 or 16 to 18 carbon atoms.
  • Quaternized fatty acid amido acids are also particularly preferred, the fatty acid components of which are derived from oleic acid and / or elaidic acid.
  • long-chain quaternized ammonium compounds of the formula (IV) are suitable as viscosity-regulating component c),
  • R 4 for alkyl and / or alkenyl radicals with 12 to 22 carbon atoms and for chloride, bromide, sulfate, methosulfate or phosphate
  • R 4 in the formula (IV) represents alkyl radicals having 16 to 18 carbon atoms and X represents chloride.
  • Possible viscosity-regulating component d) are diquaterized fatty acid trialkanolamine ester salts of the formula (V),
  • R 5 CO is an aliphatic, linear or branched acyl radical having 12 to 18 carbon atoms
  • the viscosity regulators can be added to the aqueous esterquat concentrates in amounts of 0.1 to 10, preferably 1 to 8 and in particular 3 to 7% by weight, based on the 100% by weight di-fatty acid trialkanoamine salt.
  • the mixing can take place mechanically, for example by stirring or dispersing; a chemical reaction does not take place.
  • aqueous ester quat concentrates obtainable by the process according to the invention are low-viscosity, easily pumpable even with short, low shear and have excellent anti-static and anti-static properties. They are therefore suitable for the production of textile treatment agents in which they can be present in amounts of 5 to 95, preferably 10 to 90% by weight, based on the agent.
  • AI product based on cig / ig tallow fatty acid, 90% by weight solution in water; Sales product of Pulcra s.a., Barcelona
  • test mixtures were optionally tempered to 20 ° C. after addition of the viscosity regulators and pumped in a circle over a period of 30 min using a peristaltic pump (Heidolph RZR2, 800 rpm).
  • the viscosity of the mixtures was determined using a Brookfield RVT viscometer (spindle 2 to 7, 10 rpm) before carrying out the test and after the pumping tests had ended. The results are summarized in Table 1.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des concentrés aqueux, de faible viscosité, d'esters quaternisés sont obtenus en mélangeant des solutions aqueuses de sels de trialcanolamine-esters de diacides gras quaternisés, de formule (I) dans laquelle R1CO désigne un reste acyle saturé aliphatique, linéaire ou ramifié, de 6 à 22 atomes de carbone, [Z] désigne un groupe éthylène, propylène ou isopropylène, et X désigne un chorure, un bromure, un sulfate, méthosulfate ou phosphate, avec au moins un régulateur de viscosité choisi dans le groupe comprenant a) des sels de trialcanolamine-esters de diacides gras insaturés quaternisés, b) des sels d'amido-amines d'acides gras quaternisés, c) des composés d'ammonium quaternaire à chaînes longues, et, d) des sels de triéthanolamine-esters d'acides gras di-quaternisés.
EP93917366A 1992-02-07 1993-01-29 Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises Expired - Lifetime EP0625184B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4203489 1992-02-07
DE19924203489 DE4203489A1 (de) 1992-02-07 1992-02-07 Verfahren zur herstellung niedrigviskoser waessriger esterquat-konzentrate
PCT/EP1993/000203 WO1993016157A1 (fr) 1992-02-07 1993-01-29 Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Publications (2)

Publication Number Publication Date
EP0625184A1 true EP0625184A1 (fr) 1994-11-23
EP0625184B1 EP0625184B1 (fr) 1995-12-20

Family

ID=6451139

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93917366A Expired - Lifetime EP0625184B1 (fr) 1992-02-07 1993-01-29 Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Country Status (5)

Country Link
EP (1) EP0625184B1 (fr)
JP (1) JPH07503503A (fr)
DE (2) DE4203489A1 (fr)
ES (1) ES2081719T3 (fr)
WO (1) WO1993016157A1 (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0640121B2 (fr) * 1992-05-12 2003-08-27 The Procter & Gamble Company Compositions concentrees assouplissantes liquides contenant des produits assouplissants biodegradables
DE4243550C1 (de) * 1992-12-22 1994-06-01 Henkel Kgaa Faserhilfsmittel und deren Verwendung
DE4324395A1 (de) * 1993-07-21 1995-01-26 Henkel Kgaa Verfahren zur Herstellung von Weichspüler-Dispersionen
EP0648835A1 (fr) * 1993-10-14 1995-04-19 The Procter & Gamble Company Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles
JP3746294B2 (ja) * 1993-12-13 2006-02-15 ザ、プロクター、エンド、ギャンブル、カンパニー 粘度安定な濃縮液体布帛柔軟組成物
DE4402527A1 (de) * 1994-01-28 1995-08-03 Henkel Kgaa Wäßrige Lösungen von Esterquats
DE4405702A1 (de) * 1994-02-23 1995-08-24 Witco Surfactants Gmbh Hochkonzentrierte wäßrige Weichspülmittel mit verbesserter Lagerstabilität
DE4435386A1 (de) * 1994-10-04 1996-04-11 Henkel Kgaa Wäßrige Weichspülerdispersionen
DE19649285A1 (de) 1996-11-28 1998-06-04 Henkel Kgaa Verfahren zum Schutz von Metalloberflächen gegenüber Korrosion in flüssigen oder gasförmigen Medien
DE69927034T2 (de) * 1998-06-11 2006-07-13 Kao Corporation Weichmacherzusammensetzung
US6211140B1 (en) * 1999-07-26 2001-04-03 The Procter & Gamble Company Cationic charge boosting systems
DE19962874A1 (de) * 1999-12-24 2001-06-28 Cognis Deutschland Gmbh Transparente Avivagemittel
CA2609058A1 (fr) * 2005-05-18 2006-11-23 Stepan Company Compositions contenant des agents adoucissants, a faible teneur en solides et a haute viscosite destinees aux textiles et leur procede de production
EP2082805A1 (fr) * 2008-01-28 2009-07-29 Basf Se Procédé pour la préparation d'une suspension colloïdale aqueuse de métaux précieux
WO2019048556A1 (fr) * 2017-09-06 2019-03-14 Evonik Degussa Gmbh Microémulsion comprenant un composé d'ammonium quaternaire, en particulier pour la production de formulations d'assouplissant
WO2019057754A1 (fr) 2017-09-25 2019-03-28 Evonik Degussa Gmbh Concentrés stables au stockage contenant des polysiloxanes et leur utilisation de préférence dans des compositions de soin des textiles
EP3818137B1 (fr) 2018-07-05 2022-11-09 Evonik Operations GmbH Substances actives pour formulations de lavage et de nettoyage fortement visqueuses

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013780B2 (fr) * 1979-01-11 1988-08-31 THE PROCTER & GAMBLE COMPANY Composition concentrée d'adoucissement pour tissus
AU544660B2 (en) * 1980-11-18 1985-06-06 Procter & Gamble Company, The Quaternary ammonium softener compositions
DE3588115T3 (de) * 1984-05-16 2003-03-27 Stepan Europe, Voreppe Konzentrierte Weichmacherzusammensetzungen auf der Basis von quaternären ammoniumhaltigen kationischen oberflächenaktiven Verbindungen
GB2188653A (en) * 1986-04-02 1987-10-07 Procter & Gamble Biodegradable fabric softeners
WO1988002985A1 (fr) * 1986-10-24 1988-05-05 Gaf Corporation Composes quaternises contenant de l'azote
JPH01501492A (ja) * 1987-06-16 1989-05-25 コートル・ソシエテ・アノニム 濃厚な柔軟剤組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9316157A1 *

Also Published As

Publication number Publication date
ES2081719T3 (es) 1996-03-16
DE4203489A1 (de) 1993-08-12
WO1993016157A1 (fr) 1993-08-19
DE59301215D1 (de) 1996-02-01
EP0625184B1 (fr) 1995-12-20
JPH07503503A (ja) 1995-04-13

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