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WO1993021291A1 - Agents de traitement aqueux a faible viscosite, pour textiles - Google Patents

Agents de traitement aqueux a faible viscosite, pour textiles Download PDF

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Publication number
WO1993021291A1
WO1993021291A1 PCT/EP1993/000794 EP9300794W WO9321291A1 WO 1993021291 A1 WO1993021291 A1 WO 1993021291A1 EP 9300794 W EP9300794 W EP 9300794W WO 9321291 A1 WO9321291 A1 WO 9321291A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty
quaternary ammonium
ammonium compounds
treatment agent
agent according
Prior art date
Application number
PCT/EP1993/000794
Other languages
German (de)
English (en)
Inventor
Martina Kihn-Botulinski
Theodor Völkel
Rolf Puchta
Peter Sandkühler
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1993021291A1 publication Critical patent/WO1993021291A1/fr

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
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • 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
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • Quaternary ammonium compounds which due to their cationic character easily and completely absorb onto the negatively charged fiber surface, are particularly popular active ingredients. Because of their easy biodegradability, quaternary ammonium compounds which contain fatty acyloxyalkyl radicals bound to nitrogen have recently attracted interest. Such compounds have also been known for a long time, for example from DE-A-16 19 058, DE-A-19 35 499 or US Pat. No. 3,915,867. These compounds can easily be obtained, for example, by esterification of alkanolamines with fatty acid or by transesterification of fatty acid esters with alkanolamine and subsequent quaternization. Corresponding processes for manufacturing on an industrial scale have also been known for a long time.
  • the object of the present invention is therefore to provide an aqueous textile softener concentrate with low viscosity which contains the quaternary ammonium compounds which are interesting because of their easy biodegradability and which contain 1, * 2 or 3 fatty acyloxyalkyl radicals bound to the nitrogen atom, and also their viscosity does not increase or increases only slightly after long storage.
  • the proportion of fatty acyl groups which are wholly or partly derived from unsaturated fatty acids present in cis form have an influence on the viscosity and the storage behavior.
  • the invention therefore relates to aqueous fabric softener concentrates with low viscosity, containing quaternary ammonium compounds which contain 1, 2 or 3 fatty acyloxyalkyl radicals bound to the nitrogen atom and which are characterized in that the fatty acyl groups are derived in whole or in part from unsaturated fatty acids which lead to at least 30% are in cis form.
  • low viscosity means a viscosity of at most 1000 mPas.
  • a high proportion of fatty acyl groups in cis form has an extremely favorable effect on the viscosity during the production and storage of textile softener concentrates according to the invention.
  • Textile plasticizer concentrates for the purposes of the present patent application are to be understood as meaning aqueous preparations which contain quaternary ammonium compounds with 1, 2 or 3 fatty acyloxyethyl radicals in a concentration of 4 to 55% by weight, based on the total amount of the concentrate; such fabric softener concentrates are therefore preferred.
  • the textile softeners described above can in principle contain quaternary ammonium compounds as the active ingredient which contain either 1 or 2 or 3 fatty acyloxyalkyl radicals. Since such compounds can only be prepared on an industrial scale in a complex manner, textile-plasticizer concentrates are preferred which contain quaternary ammonium compounds in the form of a mixture of compounds having 1, 2 or 3 fatty acyloxyalkyl radicals, in particular having 1, 2 and 3 fatty acyloxyethyl radicals.
  • Preferred textile softener concentrates are those which contain such compounds in the mixture of the quaternary ammonium compounds, in which the proportion with 2 fatty acyloxyalkyl radicals is greater than the proportion of quaternary ammonium compounds with 1 or 3 fatty acyloxyethyl radicals.
  • the fabric softener concentrates according to the invention additionally contain auxiliaries customary in aqueous fabric softener concentrates, such as, for example, dispersants, preservatives, inorganic or organic acids, buffer substances, electrolytes, viscosity regulators, dyes, fragrances or solvents.
  • auxiliaries customary in aqueous fabric softener concentrates, such as, for example, dispersants, preservatives, inorganic or organic acids, buffer substances, electrolytes, viscosity regulators, dyes, fragrances or solvents.
  • the auxiliaries mentioned can optionally additionally be present in aqueous textile softener concentrates according to the invention.
  • the fabric softener concentrates according to the invention contain, in addition to quaternary ammonium compounds with 1, 2 or 3 fatty acyloxyethyl radicals, additionally one or more other softening active ingredients of other classes of compounds.
  • Examples include sorbitan esters, swellable layered silicates, fatty acid combination products with polyamines, quaternary ammonium compounds with fatty alkyl or alkenyl radicals, alkyl polyglycosides or fatty acids.
  • the textile softener concentrates according to the invention are expediently brought to a pH in the range from 2.5 to 7, preferably in the range from 2.5 to 5, measured at 20 ° C. after dilution with distilled water to a concentration between 0. 5 and 5 wt .-% quaternary ammonium compounds with 1, 2 or 3 fatty acyloxyethyl radicals.
  • fabric softener concentrates which have a pH in the range from 2.5 to 4.5, measured at a concentration between 0.5 and 2.0% by weight of quaternary ammonium compounds with 1 Have 2 or 3 fatty acyloxyethyl residues. Such fabric softener concentrates are therefore particularly preferred.
  • a cis / trans ratio of 30:70 at all storage temperatures with and without shear stress leads to an undesirable increase in viscosity after only a few days, whereas with a cis / trans ratio of 70:30 no irrelevant regardless of the shear stress Viscosity increases even after 12 weeks of storage.
  • This effect caused by a cis / trans ratio of over 50:50 could not be achieved by adding organic solvents (glycerol, dipropylene glycol), magnesium chloride or ammonium chloride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Agents de traitement aqueux à faible viscosité pour textiles, contenant comme assouplisseur, des composés d'ammonium quaternaires avec 1, 2 ou 3 restes acyloxyalkyle gras liés à l'azote. Lesdits agents ont une faible viscosité, lorsque les groupes acyle gras sont dérivés totalement ou partiellement d'acides gras insaturés qui sont présents au moins à 30 % sous forme cis.
PCT/EP1993/000794 1992-04-10 1993-04-01 Agents de traitement aqueux a faible viscosite, pour textiles WO1993021291A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4212156.6 1992-04-10
DE19924212156 DE4212156A1 (de) 1992-04-10 1992-04-10 Wäßrige Textil-Behandlungsmittel mit geringer Viskosität

Publications (1)

Publication Number Publication Date
WO1993021291A1 true WO1993021291A1 (fr) 1993-10-28

Family

ID=6456599

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/000794 WO1993021291A1 (fr) 1992-04-10 1993-04-01 Agents de traitement aqueux a faible viscosite, pour textiles

Country Status (2)

Country Link
DE (1) DE4212156A1 (fr)
WO (1) WO1993021291A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994014935A1 (fr) * 1992-12-23 1994-07-07 Henkel Kommanditgesellschaft Auf Aktien Dispersions aqueuses d'adoucissants textiles
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
US5407589A (en) * 1991-07-05 1995-04-18 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
WO1998047991A1 (fr) * 1997-05-19 1998-10-29 The Procter & Gamble Company Agent adoucissant derive de triethanolamine acyle
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US5919750A (en) * 1997-07-24 1999-07-06 Akzo Nobel Nv Fabric softener composition
US6486121B2 (en) 1998-04-15 2002-11-26 The Procter & Gamble Company Softener active derived from acylated triethanolamine
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1935499A1 (de) * 1969-07-12 1971-01-14 Basf Ag Avivagemittel
EP0370675A2 (fr) * 1988-11-21 1990-05-30 Kao Corporation Composition adoucissante
WO1991017974A1 (fr) * 1990-05-17 1991-11-28 Henkel Kommanditgesellschaft Auf Aktien Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1935499A1 (de) * 1969-07-12 1971-01-14 Basf Ag Avivagemittel
EP0370675A2 (fr) * 1988-11-21 1990-05-30 Kao Corporation Composition adoucissante
WO1991017974A1 (fr) * 1990-05-17 1991-11-28 Henkel Kommanditgesellschaft Auf Aktien Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8921, Derwent Publications Ltd., London, GB; AN 89-153907 *
DATABASE WPI Week 9032, Derwent Publications Ltd., London, GB; AN 90-243078 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5407589A (en) * 1991-07-05 1995-04-18 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
WO1994014935A1 (fr) * 1992-12-23 1994-07-07 Henkel Kommanditgesellschaft Auf Aktien Dispersions aqueuses d'adoucissants textiles
US5574179A (en) * 1993-03-01 1996-11-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains
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
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5562849A (en) * 1993-03-01 1996-10-08 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US6004913A (en) * 1996-05-03 1999-12-21 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compound in esteramine from triethanolamine
US6037315A (en) * 1996-05-03 2000-03-14 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions
US6323167B1 (en) 1996-05-03 2001-11-27 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions
WO1998047991A1 (fr) * 1997-05-19 1998-10-29 The Procter & Gamble Company Agent adoucissant derive de triethanolamine acyle
US5919750A (en) * 1997-07-24 1999-07-06 Akzo Nobel Nv Fabric softener composition
US6486121B2 (en) 1998-04-15 2002-11-26 The Procter & Gamble Company Softener active derived from acylated triethanolamine
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process

Also Published As

Publication number Publication date
DE4212156A1 (de) 1993-10-14

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