EP0413249A1 - Adoucissant pour textile - Google Patents

Adoucissant pour textile Download PDF

Info

Publication number
EP0413249A1
EP0413249A1 EP90115229A EP90115229A EP0413249A1 EP 0413249 A1 EP0413249 A1 EP 0413249A1 EP 90115229 A EP90115229 A EP 90115229A EP 90115229 A EP90115229 A EP 90115229A EP 0413249 A1 EP0413249 A1 EP 0413249A1
Authority
EP
European Patent Office
Prior art keywords
acid
component
fabric softeners
compound
preparation
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
EP90115229A
Other languages
German (de)
English (en)
Other versions
EP0413249B1 (fr
Inventor
Horst Birkhan
Hans Jürgen Dr. Dipl.-Chem. Köhle
Joachim Dr. Dipl.-Chem. Weigand
Winfried Dr. Dipl.-Chem. Wehner
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.)
Evonik Goldschmidt Rewo GmbH
Original Assignee
Rewo Chemische Werke GmbH
Witco Surfactants GmbH
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 Rewo Chemische Werke GmbH, Witco Surfactants GmbH filed Critical Rewo Chemische Werke GmbH
Publication of EP0413249A1 publication Critical patent/EP0413249A1/fr
Application granted granted Critical
Publication of EP0413249B1 publication Critical patent/EP0413249B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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

Definitions

  • the present invention relates to fabric softeners in the form of aqueous emulsions or dispersions.
  • Cationic compounds are usually used as fabric softeners, for example quaternary ammonium compounds which, in addition to long-chain alkyl radicals, can also contain ester or amide groups. Mixtures of various softening components which are added to the rinsing bath in the form of aqueous dispersions are also advantageously used.
  • Backwetting capacity is generally understood to mean the absorption of moisture by the fiber. Inadequate rewetting capacity has an adverse effect where larger amounts of moisture are to be absorbed by the skin surface. e.g. B. with hand or bath towels as well as with body or bed linen.
  • the object of the present invention was to overcome the above-mentioned disadvantages of conventional fabric softener formulations and to provide fabric softening detergents which, in addition to good biodegradability and soft feel, have significantly improved dispersibility and improved rewetting capacity.
  • the fabric softener consisting of mixtures of water-insoluble ammonium compounds containing quaternary ester groups with salts of mono- or polyamine compounds, which can be prepared by protonation with inorganic or organic acids, meets these requirements.
  • the compounds according to A a) used according to the invention are prepared by processes known per se, wherein generally an alkanolamine with a long-chain fatty acid methyl ester in the presence of basic catalysts such as sodium methylate, sodium carbonate, transesterified at temperatures of 140-180 ° C. and the resulting methanol is continuously distilled off.
  • basic catalysts such as sodium methylate, sodium carbonate, transesterified at temperatures of 140-180 ° C. and the resulting methanol is continuously distilled off.
  • fatty acid methyl esters fatty acid glycerides can also be used.
  • the compounds according to A b) used according to the invention are commercially available products which are protonated in a manner known per se with organic or inorganic acids.
  • the procedure is preferably such that the amine is melted and the protic acid is added to this melt with vigorous stirring.
  • organic acids used are formic acid, acetic acid, methylsulfuric acid, ethylsulfuric acid, in particular lactic acid, malic acid, tartaric acid, citric acid, oxalic acid, glycolic acid; inorganic acids such as hydrohalic acids, especially hydrochloric acid, sulfuric acid, phosphoric acid. Lactic acid and hydrochloric acid are preferred according to the invention.
  • Examples of the quaternizing agents used are short-chain dialkyl phosphates and sulfates such as, in particular, dimethyl sulfate, diethyl sulfate, dimethyl phosphate, diethyl phosphate, short-chain halogenated hydrocarbons, in particular methyl chloride.
  • fabric softeners can be produced which have good dispersibility and textile materials, especially those made from natural and regenerated cellulose loose, as well as wool and terrycloth, in addition to a pleasantly soft handle, give an improved reed-wetting ability.
  • the fabric softeners according to the invention are therefore used in particular where larger amounts of moisture and moisture are to be removed from the body surface within a short time, such as in hand towels or bath towels.
  • the fabric softeners according to the invention can also be used successfully where moisture has to be absorbed directly by the skin within a relatively long period of time, such as for bedclothes or bed linen.
  • the fabric softener is produced by emulsifying or dispersing the individual components in water. The usual procedures in this field can be applied.
  • the fabric softeners according to the invention can each contain one or more components a) and b) within the specified limits.
  • auxiliaries and additives can also be used to produce the fabric softener according to the invention.
  • auxiliaries and additives can also be used to produce the fabric softener according to the invention. These are, in particular, complexing agents, optical brighteners, dyes and fragrances, electrolytes and higher molecular weight ether compounds for viscosity regulation, small amounts of organic solvents and - provided they do not adversely affect the raking wettability - conventional surfactants.
  • the fabric softeners according to the invention are added in the last rinse cycle after the actual washing process.
  • the application concentration after dilution with water is in the range of 0.1 - 10 g of fabric softener per liter of treatment liquor.
  • the textile material made of wool, cotton, polyester / cotton 50: 3 and polyester is treated for about 3 minutes with a liquor of tap water (about 13 ° dH) and 1 g of the dispersion according to the invention.
  • the dried textiles were checked by five people with appropriate experience in evaluating the softness of textiles for their soft feel and compared to untreated textiles. After drying, the textile goods treated in this way have an excellent, soft, fluffy feel and a greatly improved smoke-wetting ability compared to commercially available agents.
  • the x-ray power is measured in accordance with DIN 53 924 with the modification that the strips of the fabric (test pieces) are 1.5 cm wide.
  • the fabric softener dispersions according to the invention are prepared from the components given in the examples below in accordance with the following instructions or in analogy thereto:
  • the dye solution and then the plasticizer components Aa) and Ab) preheated to 45 ° C are first successively dispersed in the water preheated to 35 ° C. with good stirring (propeller stirrer). A portion of the 25% calcium chloride solution is then added, in an amount such that the entire batch remains readily stirrable. After a 10 minute dispersion phase, the perfume oil is added at approx. 35 ° C, then the viscosity is adjusted to the desired value at approx. 30 ° C with the remaining amount of the calcium chloride solution. Allow to cool to room temperature while continuing to stir well and if possible avoid air pockets.
  • the washed textiles are treated in a washing-up liquor which treats the agent according to the invention in a conventional manner in concentrations of 0.1 to 10 g / l, preferably 0.5-3 g / l.
  • the treated textiles had an excellent soft feel and an x-ray power of 70% (average of 10 measurements).
  • Example 2 was carried out analogously to Example 1 with the modification that 12 g of component Aa) as in Example 1 3 g of component Ab) as in Example 1 0.11 g CaCl2 were used.
  • Example 3 was carried out analogously to Example 1 with the modification that 18 g of component Aa) as in Example 1 2 g of component Ab) as in Example 1 0.34 g CaCl2 were used.
  • Example 4 was carried out analogously to Example 1 with the modification that 9 g of component Aa) as in Example 1 9 g of component Ab) as in Example 1 0.19 g CaCl2 were used.
  • Example 5 was dispersed as stated above, with the modification to Example 1 12 g of component Aa) as in Example 1 3 g of component Ab) as in Example 1 0.3 g CaCl2 were used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (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)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Detergent Compositions (AREA)
EP90115229A 1989-08-12 1990-08-08 Adoucissant pour textile Expired - Lifetime EP0413249B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3926740A DE3926740C2 (de) 1989-08-12 1989-08-12 Wässrige Weichspülmittel und deren Verwendung
DE3926740 1989-08-12

Publications (2)

Publication Number Publication Date
EP0413249A1 true EP0413249A1 (fr) 1991-02-20
EP0413249B1 EP0413249B1 (fr) 1997-12-10

Family

ID=6387039

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90115229A Expired - Lifetime EP0413249B1 (fr) 1989-08-12 1990-08-08 Adoucissant pour textile

Country Status (5)

Country Link
US (2) US5180508A (fr)
EP (1) EP0413249B1 (fr)
AT (1) ATE161035T1 (fr)
DE (2) DE3926740C2 (fr)
ES (1) ES2111525T3 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0503155A1 (fr) * 1991-03-13 1992-09-16 Witco Surfactants GmbH Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires
EP0634475A2 (fr) * 1993-07-15 1995-01-18 Colgate-Palmolive Company Composition concentrée liquide pour adoucir le linge
EP0669391A2 (fr) * 1994-02-23 1995-08-30 Witco Surfactants GmbH Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée
US5468398A (en) * 1993-05-20 1995-11-21 Colgate-Palmolive Company Liquid fabric softening composition
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
EP0675943B1 (fr) * 1992-12-22 2000-03-01 Colgate-Palmolive Company Composition de traitement de tissus

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3926740C2 (de) * 1989-08-12 1997-05-15 Witco Surfactants Gmbh Wässrige Weichspülmittel und deren Verwendung
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
MY108928A (en) * 1992-12-22 1996-11-30 Colgate Palmolive Co Liquid fabric softening composition containing amidoamine softening compound
US5403499A (en) * 1993-04-19 1995-04-04 Lever Brothers Company, Division Of Conopco, Inc. Concentrated fabric conditioning compositions
US5501806A (en) * 1993-07-15 1996-03-26 Colgate-Palmolive Co. Concentrated liquid fabric softening composition
US5523433A (en) * 1994-09-29 1996-06-04 Witco Corporation Process for the preparation of diethyl ester dimethyl ammonium chloride
DE19633104C1 (de) * 1996-08-16 1997-10-16 Henkel Kgaa Verwendung von Tensidmischungen
US5961966A (en) * 1996-12-09 1999-10-05 Croda, Inc. Quaternary fatty diesters of hydroxypropyl diethanol amine
US5747108A (en) * 1997-03-19 1998-05-05 Colgate-Palmolive Co. Super-concentrated liquid rinse cycle fabric softening composition
US5747109A (en) * 1997-03-19 1998-05-05 Colgate-Palmolive Co. Method of preparing super-concentrated liquid rinse cycle fabric softening composition
DE19754283B4 (de) * 1997-12-08 2004-09-30 Cognis Deutschland Gmbh & Co. Kg Verwendung von Detergensgemischen
GB9820554D0 (en) * 1998-09-21 1998-11-11 Unilever Plc Use of cationic materials and compositions
US6759246B1 (en) * 2001-11-30 2004-07-06 Research & Diagnostic Systems, Inc. Hematology control composition including lymphocyte analogs and method for preparation and use
GB2404923B (en) * 2003-07-10 2007-05-09 Fabric Care Res Ass Ltd A method of laundering articles
US20140050687A1 (en) 2011-04-28 2014-02-20 Estman Chemical Company Betaine esters and process for making and using
EP2997959B1 (fr) 2014-09-22 2019-12-25 Evonik Operations GmbH Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine
EP2997958B1 (fr) 2014-09-22 2021-03-10 Evonik Operations GmbH Émulsion contenant des esterquats liquides et polymères épaississants
CN111684072A (zh) 2018-02-13 2020-09-18 伊士曼化工公司 制备可用作酯季铵化合物前体的中间体的酶促方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0079643A2 (fr) * 1981-11-17 1983-05-25 THE PROCTER & GAMBLE COMPANY Compositions adoucissantes concentrées pour matières textiles
EP0165138A2 (fr) * 1984-05-16 1985-12-18 STEPAN EUROPE, Société anonyme dite: Compositions adoucissantes concentrées à base d'agents tensio-actifs cationiques d'ammonium quaternaire
EP0293955A2 (fr) * 1987-05-01 1988-12-07 The Procter & Gamble Company Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles
EP0295386A2 (fr) * 1987-06-19 1988-12-21 Hüls Aktiengesellschaft Compositions adoucissantes concentrées
EP0296995A1 (fr) * 1987-06-16 1988-12-28 Cotelle S.A. Compositions adoucissantes concentrées
EP0302567A2 (fr) * 1987-08-07 1989-02-08 The Procter & Gamble Company Procédé pour préparer des compositions adoucissantes biodégradables pour le linge

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US4073735A (en) * 1976-02-19 1978-02-14 Colgate Palmolive Company Rinse cycle fabric softener
US4187289A (en) * 1976-12-03 1980-02-05 Ciba-Geigy Corporation Softening agents containing diester/amine adducts and quaternary ammonium salts, valuable for use as after-rinse softeners and after-shampoo hair conditioners
ZA79485B (en) * 1978-02-24 1980-03-26 Ici Ltd Quaternary ammonium compounds
LU82836A1 (fr) * 1980-10-10 1982-05-10 Lilachim Sa Melanges de sels d'ammonium quaternaire
US4844823A (en) * 1985-01-30 1989-07-04 Colgate-Palmolive Company Fabric softener composition containing di-esterified long chain fatty acid quaternary ammonium salt
JPS62141176A (ja) * 1985-12-16 1987-06-24 花王株式会社 柔軟仕上剤
US5066414A (en) * 1989-03-06 1991-11-19 The Procter & Gamble Co. Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
DE3926740C2 (de) * 1989-08-12 1997-05-15 Witco Surfactants Gmbh Wässrige Weichspülmittel und deren Verwendung
ZA907746B (en) * 1989-10-16 1992-05-27 Colgate Palmolive Co New softening compositions and methods for making and using same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0079643A2 (fr) * 1981-11-17 1983-05-25 THE PROCTER & GAMBLE COMPANY Compositions adoucissantes concentrées pour matières textiles
EP0165138A2 (fr) * 1984-05-16 1985-12-18 STEPAN EUROPE, Société anonyme dite: Compositions adoucissantes concentrées à base d'agents tensio-actifs cationiques d'ammonium quaternaire
EP0293955A2 (fr) * 1987-05-01 1988-12-07 The Procter & Gamble Company Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles
EP0296995A1 (fr) * 1987-06-16 1988-12-28 Cotelle S.A. Compositions adoucissantes concentrées
EP0295386A2 (fr) * 1987-06-19 1988-12-21 Hüls Aktiengesellschaft Compositions adoucissantes concentrées
EP0302567A2 (fr) * 1987-08-07 1989-02-08 The Procter & Gamble Company Procédé pour préparer des compositions adoucissantes biodégradables pour le linge

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0503155A1 (fr) * 1991-03-13 1992-09-16 Witco Surfactants GmbH Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires
EP0675943B1 (fr) * 1992-12-22 2000-03-01 Colgate-Palmolive Company Composition de traitement de tissus
US5468398A (en) * 1993-05-20 1995-11-21 Colgate-Palmolive Company Liquid fabric softening composition
EP0634475A3 (fr) * 1993-07-15 1996-12-11 Colgate Palmolive Co Composition concentrée liquide pour adoucir le linge.
TR28733A (tr) * 1993-07-15 1997-02-20 Colgate Palmolive Co Konsantre, sivi camasir yumusatici bilesim.
EP0634475A2 (fr) * 1993-07-15 1995-01-18 Colgate-Palmolive Company Composition concentrée liquide pour adoucir le linge
EP0669391A2 (fr) * 1994-02-23 1995-08-30 Witco Surfactants GmbH Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée
EP0669391A3 (fr) * 1994-02-23 1998-08-19 Witco Surfactants GmbH Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée
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
US6770608B2 (en) 1996-05-03 2004-08-03 Akzo Nobel N.V. High di(alkyl fatty ester) amines and quaternary ammonium compounds derived therefrom

Also Published As

Publication number Publication date
ES2111525T3 (es) 1998-03-16
DE3926740C2 (de) 1997-05-15
DE59010779D1 (de) 1998-01-22
DE3926740A1 (de) 1991-02-28
ATE161035T1 (de) 1997-12-15
US5180508A (en) 1993-01-19
US5364542A (en) 1994-11-15
EP0413249B1 (fr) 1997-12-10

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