EP0675941B1 - Dispersions aqueuses d'adoucissants textiles - Google Patents

Dispersions aqueuses d'adoucissants textiles Download PDF

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Publication number
EP0675941B1
EP0675941B1 EP94903767A EP94903767A EP0675941B1 EP 0675941 B1 EP0675941 B1 EP 0675941B1 EP 94903767 A EP94903767 A EP 94903767A EP 94903767 A EP94903767 A EP 94903767A EP 0675941 B1 EP0675941 B1 EP 0675941B1
Authority
EP
European Patent Office
Prior art keywords
dispersions
compounds
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.)
Revoked
Application number
EP94903767A
Other languages
German (de)
English (en)
Other versions
EP0675941A1 (fr
Inventor
Rolf Puchta
Thomas Engels
Theodor Völkel
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
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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

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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

  • 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 prolonged storage.
  • Aqueous textile softener dispersions tend to thicken when stored, especially at temperatures below or above room temperature. This behavior is particularly pronounced in textile softener dispersions with a high active ingredient content.
  • the commercial fabric softener concentrates contain approximately 15 to 25% by weight of active ingredient.
  • a low initial viscosity is generally set using different electrolytes. If the active substance content is even higher, an appreciable increase in viscosity is observed even in the presence of electrolyte during storage, which either takes place immediately after production, in particular after a shear stress caused by stirring or pumping, or during 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 easily and completely biodegradable; the products should also be easy to dilute with cold water, and the textiles 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, the proportion of non-textile softening components is as low as possible.
  • the present invention relates to concentrated textile plasticizer dispersions containing quaternary ammonium compounds derived from triethanolamine and containing 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 19 058, DE-A-19 35 499 or US 3,915,867 with one, two or three fatty acyloxyethyl radicals on the nitrogen atom. These compounds can easily be prepared, 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 production on an industrial scale have also been known for a long time; Compounds made by these methods 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 with one, two or three fatty acyloxyalkyl 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-498 050 emulsions, the more than 15% by weight of fatty acid esters of N-methyl-N, N, N-trihydroxyethyl-ammonium-methyl sulfate contain, 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 importance in terms of application technology: it has been found in corresponding studies that it is advantageous for the stability of the dispersions if the content of quaternaries Ammonium compounds with only one acyloxyethyl group is not higher than 40 mol% and the content of quaternary ammonium compounds with three acyloxyethyl groups is not higher than 10 mol%, based on the total amount of quaternary ammonium compounds.
  • a particularly preferred embodiment of the invention therefore results in a concentrated textile plasticizer dispersion containing quaternary ammonium compounds of the formula I.
  • R 1 CO 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 40 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 3 is an R 1 CO group and which contain more than 50 mol% of compounds, in which R 2 is hydrogen and R 3 is an R 1 CO group.
  • Preferred fatty acyl groups R 1 CO are unsaturated fatty acyl groups such as the oleoyl group or also mixtures which are derived from unsaturated technical fatty acid mixtures with a high proportion of oleoyl groups, for example soybean oil fatty acid, tallow fatty acid or palm oil fatty acid.
  • the effect described on which the present invention is based can be used particularly in the case of textile plasticizer dispersions with a high content of quaternary ammonium compounds.
  • Another object of the present invention are therefore concentrated fabric softener dispersions, which are characterized in that the dispersions contain more than 15% by weight of quaternary ammonium compounds, which in turn are mixtures of quaternary ammonium compounds with one, two or three fatty acyloxyalkyl groups, the The proportion of compounds with two fatty acyloxyethyl groups is 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 mPas at 20 ° C. are particularly preferred. It is particularly advantageous that textile softener dispersions according to the invention even have a viscosity of less than 500 mPas at 20 ° C. These are therefore a further subject of the present invention.
  • the textile softener dispersions according to the invention may additionally contain other constituents customary in textile softener dispersions. However, they are not necessary to achieve the effect according to the invention, but at best serve to complete the most complete possible property profile of the dispersions, so that they are easily accepted by the consumer.
  • 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, for example, magnesium chloride or sodium acetate.
  • auxiliaries or additives are organic solvents; These include, in particular, lower alcohols, such as, for example, ethanol or isopropyl alcohol, but also glycols and polyglycols or else glycol ethers or glycol ether acetates. It is also possible to use fragrances or dyes or additives which impart gloss. To improve the durability of the textile plasticizer dispersions according to the invention, they 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, above all after a previous shear stress, that they have a high active ingredient content, that they can easily be diluted in cold water, which is particularly noticeable when washing in automatic washing machines that they are easily biodegradable and completely biodegradable and that the textiles treated with them not only have a soft feel after drying, but also good rewettability, especially for textiles worn on the skin be of particular importance. Because 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 constituents is also met.
  • the viscosity is given in mPas at 20 ° C., measured with a Brookfield viscometer at 20 revolutions per minute. The viscosity was measured after a shear stress caused by pumping the dispersion immediately after production and 3 days later.
  • Table 1 attempt Mol% content Viscosity mPas fresh 3 days 1 56 105 190 2nd 62 175 180 3rd 45 1000 2000 4th 38 8000 10,000 5 48 4500 8000 6 49 400 5400 7 47 225 1000 8th 46 275 4600
  • 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, which in addition rises to values of 1000 to 10,000 mPas within 3 days.

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  • 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)

Claims (6)

  1. Dispersions concentrées d'adoucissants textiles possédant une certaine concentration en composés quaternaires de l'ammonium, qui dérivent de la triéthanolamine et comportent un, deux ou trois groupes acyloxyéthyle gras, caractérisées en ce que la proportion de composés comportant deux groupes acyloxyéthyle gras est supérieure à 50 moles %, par rapport à la quantité totale de composés quaternaires de l'ammonium.
  2. Dispersions concentrées d'adoucissants textiles selon la revendication 1, caractérisées en ce que la proportion de composés ne possédant qu'un seul groupe acyloxyéthyle n'est pas supérieure à 40 moles % et le pourcentage de composés comportant trois groupes acyloxyéthyle n'est pas supérieur à 10 moles %, par rapport à la quantité totale de composés quaternaires de l'ammonium.
  3. Dispersions concentrées d'adoucissants textiles selon la revendication 1 ou 2, caractérisées en ce que les dispersions renferment plus de 15 % en poids de composés quaternaires de l'ammonium.
  4. Dispersions concentrées d'adoucissants textiles selon une des revendications 1 à 3, caractérisées en ce que les dispersions renferment plus de 30 % en poids de composés quaternaires de l'ammonium.
  5. Dispersions concentrées d'adoucissants textiles selon une des revendications 1 à 4, caractérisées en ce que leur viscosité à 20 °C est inférieure à 1000 mPas.
  6. Dispersions concentrées d'adoucissants textiles selon une des revendications 1 à 5, caractérisées en ce que leur viscosité est inférieure à 500 mPas.
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 EP0675941A1 (fr) 1995-10-11
EP0675941B1 true 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)

Families Citing this family (21)

* 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
JP4024438B2 (ja) 1999-11-01 2007-12-19 花王株式会社 第４級アンモニウム塩組成物
EP1239024B1 (fr) 2001-03-08 2007-11-21 Kao Corporation Composition adoucissante
DE10134224B4 (de) 2001-07-13 2012-12-20 Clariant Produkte (Deutschland) Gmbh Additive zur Inhibierung der Gashydratbildung
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
ES2318622T3 (es) * 2006-07-06 2009-05-01 Clariant (Brazil) S.A. Composicion esterquat concentrada.
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
PL2553067T3 (pl) 2010-04-01 2015-07-31 Evonik Degussa Gmbh Kompozycje czynne środków do zmiękczania tkanin
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
CN104169410B (zh) * 2012-02-21 2018-02-09 斯蒂潘公司 织物软化剂组合物
JP5992605B2 (ja) 2012-05-07 2016-09-14 エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ 織物柔軟剤活性組成物およびその製造方法
US10017715B2 (en) 2013-02-15 2018-07-10 Rhodia Operations Fabric softener
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

Also Published As

Publication number Publication date
ATE141943T1 (de) 1996-09-15
EP0675941A1 (fr) 1995-10-11
DE4243701A1 (de) 1994-06-30
WO1994014935A1 (fr) 1994-07-07
ES2091130T3 (es) 1996-10-16
DE59303601D1 (de) 1996-10-02

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