EP0675941A1 - Dispersions aqueuses d'adoucissants textiles. - Google Patents

Dispersions aqueuses d'adoucissants textiles.

Info

Publication number
EP0675941A1
EP0675941A1 EP94903767A EP94903767A EP0675941A1 EP 0675941 A1 EP0675941 A1 EP 0675941A1 EP 94903767 A EP94903767 A EP 94903767A EP 94903767 A EP94903767 A EP 94903767A EP 0675941 A1 EP0675941 A1 EP 0675941A1
Authority
EP
European Patent Office
Prior art keywords
compounds
dispersions
quaternary ammonium
ammonium compounds
fatty
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
EP94903767A
Other languages
German (de)
English (en)
Other versions
EP0675941B1 (fr
Inventor
Rolf Puchta
Thomas Engels
Theodor Voelkel
Fred Schambil
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6476278&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0675941(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 EP0675941A1 publication Critical patent/EP0675941A1/fr
Application granted granted Critical
Publication of EP0675941B1 publication Critical patent/EP0675941B1/fr
Anticipated expiration legal-status Critical
Revoked legal-status Critical Current

Links

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
    • D06M13/322Treating 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
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • 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
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions

Definitions

  • the present invention relates to aqueous fabric softener dispersions which, despite their particularly high content of fabric softening active ingredients, have a low viscosity which does not increase or increases only insignificantly even after a long period of use.
  • Aqueous textile softener dispersions tend to thicken during storage, especially at temperatures below or above room temperature. This behavior is particularly pronounced in textile softener dispersions with a high active ingredient content.
  • the commercially available textile softener concentrates contain approximately 15 to 25% by weight of active ingredient.
  • a low initial viscosity is generally set with the aid of different electrolytes to ensure storage-stable dispersions.
  • B an even higher active substance content, but also in the presence of electrolyte during storage, a significant increase in viscosity is observed, d either immediately after production, especially after a shear stress caused by stirring or pumping, or in the course of storage.
  • the object of the present invention is therefore to provide aqueous textile plasticizer dispersions with a high active ingredient content, the viscosity of which is low and which does not increase, or does not increase significantly, even after storage.
  • the active ingredient of the dispersions according to the invention should be biologically easy and completely degradable; the products should also be easy to dilute with cold water, and the parts treated with them should have good softness and good rewetting properties after drying.
  • Another object of the present invention is to provide textile softener dispersions whose proportion of non-textile softening constituents is as small as possible.
  • the present invention relates to concentrated fabric softener dispersions containing quaternary ammonium compounds which are derived from triethanolamine and contain one, two or three fatty acyloxyethyl groups which are characterized in that the proportion of compounds having two fatty acyloxyethyl groups is greater than 50 mol -%, based on the total amount of quaternary ammonium compounds.
  • the quaternary ammonium compounds mentioned are readily biodegradable because of the ester groups contained therein in the long residues and have therefore recently gained interest.
  • the compounds mentioned include, for example, the compounds known from DE-A-16 19058, DE-A-1935499 or US Pat. No. 3,915,867 with one, two or three fatty acyloxyethyl radicals on the nitrogen atom. These compounds can be easily produced, for example, by esterification of triethanolamines with fatty acid or by transesterification of fatty acid esters with triethanolamine and subsequent quaternization. Corresponding processes for the manufacture in large-scale industrial rod have also been known for a long time. Compounds produced by these processes are commercially available compounds. Depending on the stoichiometric ratio of fatty acids or fatty acid esters and triethanolamine, the reaction products contain different amounts of compounds having one, two or three fatty acyloxy alkyl groups.
  • Quaternary ammonium compounds suitable according to the invention contain a proportion of compounds with two acyloxyethyl groups of more than 50 mol%, based on the total amount of quaternary ammonium compounds. This is all the more surprising since according to the teaching of EP-A-498050 emulsions, ie more than 15% by weight of fatty acid esters of N-methyl-N, N, N-trihydroxyethyl-ammo nium methyl sulfate, have a viscosity of less than 100 mPas at 25 ° C if the quaternary ammonium compounds contain an average of 1.1 to 1.7 fatty acid residues.
  • the content of quaternary ammonium compounds with one and with three acyloxyethyl groups in the molecule is of a certain application-technical importance: it has been found in corresponding studies that it is advantageous for the stability of the dispersions if the content of quaternary ammonium compounds with only one acyloxyethyl group not higher than 40 mol% and the content of quaternary ammonium compounds with three acyloxyethyl groups not higher than 1 mol%, based on the total amount of quaternary ammonium compounds
  • R * C0 is a fatty acyl group with 12 - 22 C atoms
  • R 4 is an alkyl group with 1 - 4 C atoms or a hydroxyalkyl group with 2 - 4 C atoms
  • a ( ⁇ ) is a halide or methoxysulfate anion , and which contain no more than 4 mol% of compounds in which R 2 and R 3 are hydrogen, and which contain no more than 10 mol% of compounds in which R 2 and R is an R ⁇ O group and which contain more than 50 mol% of compounds in which R 2 is hydrogen and R 3 is a RicO group.
  • Preferred fatty acyl groups R * C0 are unsaturated fatty acyl groups such as, for example, the oleoyl group, or else mixtures which are derived from unsaturated technical fatty acid mixtures with a high proportion of oleoyl groups, for example v soybean oil fatty acid, tallow fatty acid or palm oil fatty acid.
  • Another object of the present invention is therefore concentrated textile plasticizer dispersions, which are characterized in that the dispersions contain more than% by weight of quaternary ammonium compounds, which in turn are mixtures of quaternary ammonium compounds with one, two or three fatty acyloxyalkyl groups , the proportion of compounds having two fatty acyloxyethyl groups being greater than 50 mol%, based on the total amount of quaternary ammonium compounds.
  • Concentrated textile plasticizer dispersions of the type described above with a viscosity of less than 1,000 mP at 20 ° C. are particularly preferred. It is particularly advantageous that Te plasticizer dispersions according to the invention even have a viscosity of less than 500 mP at 20 ° C. These are therefore a further subject of the present invention.
  • the textile softener dispersions according to the invention can additionally comprise other constituents customary in textile softening dispersions. However, they are not necessary to achieve the effect according to the invention, but instead serve to complete, if possible, a rounded property of the dispersions, so that they are easily accepted by the consumer the.
  • Suitable auxiliaries and additives which are usually present in textile plasticizer dispersions are, for example, electrolytes, nonionic dispersants, in particular fatty alcohols or polyols, to which ethylene oxide and / or propylene oxide are attached.
  • Fatty amine ethoxylates like sorbitan esters and sorbitan ester derivatives, can also be used as dispersants.
  • Electrolytes suitable for influencing the viscosity are inorganic or organic salts, such as magnesium chloride or sodium acetate.
  • auxiliaries or additives are organic solvents; These include in particular lower alcohols, such as ethanol or isopropyl alcohol, but also glycol and polyglycols or else glycol ethers or glycol ether acetates. Furthermore, fragrances or dyes or even additive imparting gloss can be used; To improve the durability of the textile plasticizer dispersions according to the invention, these can also contain suitable preservatives.
  • the dispersions mentioned are distinguished by the fact that their initial viscosity does not increase or only increases insignificantly after production and after prolonged storage, especially after a previous shear stress, that they have a high active ingredient content, and that they can also be easily diluted in cold water
  • What is particularly noticeable when washing in i automatic washing machines is that they are easily and completely biodegradable and that the textiles treated with them not only have a soft feel after drying but also good rewettability, which is particularly true for textiles, ie of the skin is of particular importance.
  • the textile plasticizer dispersions according to the invention do not necessarily have to contain additional auxiliaries and additives, the requirement for the highest possible proportion of textile-softening compounds or for the smallest possible proportion of non-textile-softening components is also met.
  • the viscosity is given in mPas at 20 ° C, measured with a Brookfield viscosi at 20 revolutions per minute. The viscosity was measured after a shear stress caused by pumping the dispersion immediately after production and days later.
  • the dispersions of experiments 1 and 2 according to the invention have a low viscosity, which increases only slightly after storage.
  • the dispersions of experiments 3 to 8 not according to the invention have a higher viscosity even in the fresh state, that is to say they also increase to values of 1000 to 10000 mPas within 3 days.

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)
EP94903767A 1992-12-23 1993-12-14 Dispersions aqueuses d'adoucissants textiles Revoked EP0675941B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4243701A DE4243701A1 (de) 1992-12-23 1992-12-23 Wäßrige Textilweichmacher-Dispersionen
DE4243701 1992-12-23
PCT/EP1993/003525 WO1994014935A1 (fr) 1992-12-23 1993-12-14 Dispersions aqueuses d'adoucissants textiles

Publications (2)

Publication Number Publication Date
EP0675941A1 true EP0675941A1 (fr) 1995-10-11
EP0675941B1 EP0675941B1 (fr) 1996-08-28

Family

ID=6476278

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94903767A Revoked EP0675941B1 (fr) 1992-12-23 1993-12-14 Dispersions aqueuses d'adoucissants textiles

Country Status (5)

Country Link
EP (1) EP0675941B1 (fr)
AT (1) ATE141943T1 (fr)
DE (2) DE4243701A1 (fr)
ES (1) ES2091130T3 (fr)
WO (1) WO1994014935A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6855682B2 (en) 2001-03-08 2005-02-15 Kao Corporation Softener composition
US7214718B1 (en) 1999-11-01 2007-05-08 Kao Corporation Quaternary ammonium salt composition
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4446137A1 (de) * 1994-12-23 1996-06-27 Huels Chemische Werke Ag Quaternierte Triethanolamindifettsäureester
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
DE10134224B4 (de) * 2001-07-13 2012-12-20 Clariant Produkte (Deutschland) Gmbh Additive zur Inhibierung der Gashydratbildung
EP1876223B1 (fr) * 2006-07-06 2009-02-18 Clariant (Brazil) S.A. Composition concentré de composé quaternaire d'ester
US8361953B2 (en) 2008-02-08 2013-01-29 Evonik Goldschmidt Corporation Rinse aid compositions with improved characteristics
AP3143A (en) 2010-04-01 2015-02-28 Evonik Degussa Gmbh Fabric softener active composition
MA34103B1 (fr) 2010-04-01 2013-03-05 Evonik Degussa Gmbh Composition active d'assouplissant pour textile
ES2627705T3 (es) 2010-04-28 2017-07-31 Evonik Degussa Gmbh Composición suavizante textil
US8507425B2 (en) 2010-06-29 2013-08-13 Evonik Degussa Gmbh Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making
WO2013113453A1 (fr) 2012-01-30 2013-08-08 Evonik Industries Ag Composition active d'assouplissant pour textile
SG11201405008SA (en) 2012-02-21 2014-09-26 Stepan Co Fabric softener compositions
DK2847307T3 (en) 2012-05-07 2016-07-25 Evonik Degussa Gmbh ACTIVE SOFT COMPOSITION FOR TEXTILES AND PROCEDURES FOR MANUFACTURING THEREOF
JP6453244B2 (ja) 2013-02-15 2019-01-16 ローディア オペレーションズ 布帛柔軟剤
WO2014154234A1 (fr) 2013-03-25 2014-10-02 Rhodia Operations Produit assouplissant
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
WO2015074692A1 (fr) 2013-11-20 2015-05-28 Rhodia Operations Composition d'assouplissant pour textile
UA119182C2 (uk) 2014-10-08 2019-05-10 Евонік Дегусса Гмбх Активна композиція для пом'якшувача тканини

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1619058A1 (de) * 1967-12-01 1971-01-28 Hoechst Ag Mittel zur Behandlung von Textilien
DE1935499A1 (de) * 1969-07-12 1971-01-14 Basf Ag Avivagemittel
DE3612479A1 (de) * 1986-04-14 1987-10-15 Henkel Kgaa Waessriges konzentriertes textilweichmachungsmittel
JPH02139480A (ja) * 1988-11-21 1990-05-29 Kao Corp 柔軟仕上剤
DE4101251A1 (de) * 1991-01-17 1992-07-23 Huels Chemische Werke Ag Fettsaeureester des n-methyl-n,n,n-trihydroxyethyl-ammonium-methyl- sulfat enthaltende waessrige emulsionen
DE4212156A1 (de) * 1992-04-10 1993-10-14 Henkel Kgaa Wäßrige Textil-Behandlungsmittel mit geringer Viskosität
DE4224067A1 (de) * 1992-07-21 1994-01-27 Henkel Kgaa Tumblerhilfsmittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9414935A1 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7214718B1 (en) 1999-11-01 2007-05-08 Kao Corporation Quaternary ammonium salt composition
US6855682B2 (en) 2001-03-08 2005-02-15 Kao Corporation Softener composition
US7115779B2 (en) 2001-03-08 2006-10-03 Kao Corporation Softener composition
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
WO1994014935A1 (fr) 1994-07-07
DE4243701A1 (de) 1994-06-30
ES2091130T3 (es) 1996-10-16
EP0675941B1 (fr) 1996-08-28
ATE141943T1 (de) 1996-09-15
DE59303601D1 (de) 1996-10-02

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