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EP0503155B1 - Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires - Google Patents

Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires Download PDF

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Publication number
EP0503155B1
EP0503155B1 EP91121957A EP91121957A EP0503155B1 EP 0503155 B1 EP0503155 B1 EP 0503155B1 EP 91121957 A EP91121957 A EP 91121957A EP 91121957 A EP91121957 A EP 91121957A EP 0503155 B1 EP0503155 B1 EP 0503155B1
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Prior art keywords
compounds
radical
general formula
radicals
weight
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EP91121957A
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German (de)
English (en)
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EP0503155A1 (fr
Inventor
Horst Birkhan
Michael Dipl.-Ing. Fender
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Witco Surfactants GmbH
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Witco Surfactants GmbH
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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
    • 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

Definitions

  • the present invention relates to fabric softeners in the form of aqueous solutions, 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 plasticizing 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. Poor network assets have a negative impact where larger amounts of moisture are to be absorbed from the skin surface by textile fabrics, e.g. B. with hand or bath towels as well as underwear or bed linen.
  • fabric softening agents consisting of ammonium compounds containing ester groups and a liquid carrier material meet these requirements.
  • the polyoxyalkylene alcohols are prepared by adding an alkylene oxide, essentially propylene oxide, ethylene oxide or a mixture of both, using a conventional method to a compound containing one or more active hydrogen atoms or by polymerizing alkylene oxides.
  • Monoalcohols such as ethanol, isopropanol, butanol, lauryl alcohol, stearyl alcohol, but especially methanol or glycols such as ethylene glycol, propylene glycol, diethylene glycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, polyglycerol, polyvinyl alcohols can be used as compounds which contain one or more active hydrogen atoms.
  • the polyoxyalkylene alcohols have molecular weights in the range from approximately 100 to 10,000, preferably approximately 130 to 5000 and particularly preferably approximately 150 to 2000.
  • the further conversion to the amines is carried out according to methods known per se by aminolysis of the free hydroxyl groups or their esters, in particular the sulfuric acid esters.
  • the OH group is replaced by the amino group by means of homogeneous, but in particular heterogeneous, catalysis on fixed contacts.
  • two methods are available here. The one works with dehydrating, the other with hydrodehydrogenating catalysts.
  • the compounds of formula (2) are then alkoxylated by methods known per se, i.e. H. preferably ethoxylated or propoxylated.
  • the procedure is such that the amines in a pressure reactor at 120-160.degree. C., optionally in the presence of basic, in particular alkaline, catalysts at 1-4 bar with an amount of alkylene oxide corresponding to the desired degree of alkoxylation; ethylene oxide and propylene oxide are preferred according to the invention or their mixtures, reacted.
  • the fatty acids for the esterification or the transesterification are the monobasic synthetic fatty acids known and customary in this field, but in particular the fatty acids based on natural vegetable and animal oils with 6-22 C atoms, in particular with 8-18 C atoms, such as coconut fatty acids, palm, tallow, castor fatty acids. These can be used both as glycerides, as esters with short-chain alcohols or as free acids.
  • the alkanolamines of the formula (4) are reacted with an amount of fatty acid or fatty acid ester corresponding to the desired degree of esterification, optionally in the presence of a catalyst, at 160-240 ° C. and the water of reaction or the alcohol formed is distilled off continuously, to complete the If necessary, a negative pressure is applied.
  • the salts are generally prepared by adding the acids, if appropriate as aqueous or alcoholic solutions in an amount corresponding to the desired degree of salt formation, to the poly (oxyalkylene) alkanolamine esters at 20 ° -80 ° C. and, if necessary with stirring, in portions with cooling.
  • the quaternization is carried out in accordance with the generally known processes, the poly (oxyalkylene) alkanolamine esters, optionally with the use of a solvent, being heated to 40-80 ° C. and the quaternizing agent being added in portions in an amount corresponding to the desired degree of quaternization.
  • the anions Cl ⁇ , SO42 ⁇ , and or where several anions can also be present side by side and are added in an amount such that the resulting pH of the total mixture of a 30% mixture is between 2-6, preferably 3-5.
  • the compounds of the general formula (1) which are also used according to the invention can be used alone or as mixtures, the triester of the general formula (1) being predominantly in dispersions, the diesters of the - depending on the structure of the compounds of the general formula (3) general formula (1) can be converted into solutions.
  • these solutions are quaternized even without the use of conventional ammonium salts
  • Ammonium compounds and other auxiliaries and additives customary in this field give the textiles treated with them, in addition to a soft feel, an excellent rewetting capacity.
  • the diester compounds are prepared by simply dissolving in cold or accelerated in heated water, as described, the triester compounds are emulsified or dispersed by the known processes, with the customary equipment and the known auxiliaries and additives also being used.
  • the compounds according to the invention can also be used at room temperature (20-25 ° C.) be incorporated. With thorough stirring, the dye solution, then the antifoam emulsion that may be required and finally the individual plasticizers are dispersed in succession or in a mixture. After adding a portion of an electrolyte solution (if necessary), perfume oil is added, followed by the remaining amount of the electrolyte solution. According to the invention, work is preferably carried out without the addition of electrolyte solutions.
  • the customary auxiliaries and additives can also be used to produce the fabric softener according to the invention.
  • fabric softeners By combining the components according to general formula (1) and optionally the commercially available quaternary ammonium compounds and optionally auxiliaries, fabric softeners can be produced which are clearly soluble in water or have good emulsifying or dispersing properties and give textile materials, in particular those made from natural and regenerated cellulose, as well as wool and terry cloth, an improved softness and an improved rewetting capacity.
  • 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 the case of 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 softeners according to the invention are added after the actual washing process in the last rinse cycle.
  • the application concentration is in the range of 0.1 - 10 g of fabric softener per liter of treatment liquor, depending on the area of application.
  • GAZ Total amine number
  • TEZ tertiary amine number
  • the total amine number indicates the number of milligrams of potassium hydroxide equivalent to the total amine basicity of 1 g of the amine compound (mg KOH / g).
  • the tertiary amine number indicates the number of milligrams of potassium hydroxide equivalent to the tertiary amine basicity of 1 g of the amine compound.
  • the saponification number is a measure of the free and bound acids contained in fats and technical fatty acids. It indicates the number of milligrams of potassium hydroxide required to saponify 1 gram of fat or technical fatty acids (mg KOH / g).
  • DGF German Society for Fat Chemistry
  • the hydroxyl number is used to determine the hydroxyl group content and indicates the number of milligrams of potassium hydroxide required to neutralize the acetic acid consumed by 1 gram of fat in acetylation (mg KOH / g).
  • the values are determined according to the DGF standard method C-V17a.
  • the acid number is a measure of the fat or technical fatty acid content of free acids and indicates the milligrams of potassium hydroxide that are necessary to neutralize 1 gram of substance.
  • the values are determined according to the DGF standard method C-V4.
  • cation-active substances are long-chain compounds which contain quaternary ammonium groups.
  • the content is given in% quaternary compound, calculated as an SO3 equivalent with a molecular weight of 80 g / mol.
  • the content is determined by a two-phase titration according to ISO standards 2871-1 and 2871-2 (1988 E).
  • This compound had a total amine number (GAZ) of 179 mg KOH / g, a tertiary amine number (TAZ) of 175 mg KOH / g and a hydroxyl number (OHZ) of 348 mg KOH / g.
  • the mixture results in a homogeneous emulsion or solution.
  • the mixture results in a homogeneous emulsion or solution.
  • the textile material made of wool, cotton, polyester / cotton 50: 3 and polyester is soaked for about 10 minutes with a liquor of tap water (about 9 ° dH and a temperature of 15-20 ° C) and an emulsion according to the invention, Dispersion or solution treated.
  • the concentration of the compounds according to the invention in the liquor is 0.025% by weight, based on the total active substance.
  • the dried textiles were checked for their soft feel by nine people with appropriate experience in evaluating the softness of textiles and compared to textiles not treated with fabric softeners. The assessment is based on a graded point system, with the final assessment being represented by the arithmetic mean. After drying, the textile goods treated in this way have an excellent soft, fluffy feel and a greatly improved rewetting capacity compared to commercially available agents.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Claims (4)

  1. Agents adoucissants aqueux, contenant :
    A) de 5 à 35 % en poids d'un au moins des composés de formule générale (I) :
    Figure imgb0046
     dans laquelle
    les radicaux R, identiques ou différents, représentent H ou -CH₃,
    R¹, R, R³, R⁴, identiques ou différents, représentent des radicaux R⁵-(O-CH (R) -CH₂)m- avec
    R⁵ pouvant être un radical acyle avec 6 à 22 atomes de carbone éventuellement substitué, éventuellement contenant des liaisons multiples, ou pouvant être H au moins une fois, et où
    R⁵ représente au moins une fois, un radical acyle et doit être au moins une fois H, et
    R⁶, R⁷, identiques ou différents, représentent H, -CH₃, -C₂H₅, -C₂H₄OH,
    A représente au moins un anion organique et/ou minéral,
    n va de 1 à 30,
    m va de 1 à 5 et la somme de tous les m est d'au moins 4 et éventuellement
    B) de 10 à 90 % en poids, par rapport à A, de composés d'ammonium usuels et éventuellement
    C) de 1 à 5 % en poids de colorants, de parfums usuels et d'autres adjuvants et additifs usuels dans les agents adoucissants et
    D) complété d'eau jusqu'à 100 % en poids.
  2. Agents adoucissants aqueux selon la revendication 1, caractérisé en ce qu'il contiennent comme constituant A :
       de 15 à 30 % en poids d'un au moins composé de formule générale (1) dans laquelle R représente -CH₃, deux ou trois des radicaux R¹, R, R³, R⁴ représentent R⁵-O-CH₂-CH₂- avec R⁵ étant un radical acyle avec 8 à 18 atomes de carbone et une ou deux fois HO-CH₂-CH₂-, n va de 1 à 15, R⁶, R⁷, identiques ou différents, représentent H ou -CH₃ et A⁻ le radical d'un acide carboxylique éventuellement substitué avec 1 à 8 atomes de carbone dans la chaîne principale, ou le radical méthosulfate ou bien éthosulfate.
  3. Agents adoucissants aqueux selon la revendication 1, caractérisé en ce qu'il contiennent comme constituant A :
       de 15 à 30 % en poids d'un au moins composé de formule générale (1), dans laquelle R représente -CH₃, trois des radicaux R¹, R, R³, R⁴ représentent R⁵-O-CH₂-CH₂- avec R⁵ étant un radical acyle avec 8 à 18 atomes de carbone, sont une fois le radical avec R⁵ étant égal à H, n va de 2 à 8, R⁶, R⁷ représentent H et A⁻ est le radical lactate.
  4. Agents adoucissants aqueux selon la revendication 1, caractérisé en ce qu'il contiennent comme constituant B:
       de 10 à 50 % en poids, par rapport à A), au moins un des composés pris dans le groupe de formule générale (5) :

            R¹¹-CO-NH-R¹³-N(-R¹OH)-COR¹¹     (5)

    dans laquelle les radicaux R¹¹ représentent un radical alkyle ou alcényle avec 15 à 21 atomes de carbone éventuellement substitué, R¹ et R¹³ sont des radicaux alkylène en C₁-C₃ bivalents, et/ou
    des imidazolines substituées de formule générale (6) :
    Figure imgb0047
    dans laquelle R¹¹, R¹ ont les significations données ci-dessus, R¹⁴ représente H ou un radical hydroxyalkyle ou alkyle en C₁-C₄ et/ou
    des composés de formule (7) :
    Figure imgb0048
    dans laquelle R¹¹, R¹, R¹⁴ ont la signification donnée ci-dessus, et/ou
    les produits de réaction des acides gras en C₁₆-C₂₂ avec des dialkylènetriamines dans un rapport molaire de 2:1

            R¹¹-CO-NH-R¹-N(R¹⁴)₂-R¹³-NHCOR¹¹     (8)


    dans laquelle R¹¹, R¹, R¹³, R¹⁴ ont les significations données ci-dessus, et/ou
    des imidazolines substituées de formule générale (9) :
    Figure imgb0049
    dans laquelle R¹¹, R¹ et R¹⁴ ont la signification donnée ci-dessus et dans laquelle les composés de formules (5) à (9),
    indépendamment les uns des autres, peuvent être présents entièrement ou partiellement sous forme de leurs sels avec des acides organiques et/ou minéraux ou encore leurs composés quaternaires, et/ou les composés d'ammonium quaternaire de formule générale :

            [NR¹⁵R¹⁶R¹⁷R¹⁸]⁺ A⁻     (10)

    dans laquelle R¹⁵ représente un radical alkyle ou alcényle avec 16 à 22 atomes de carbone éventuellement substitué, R¹⁶ et R¹⁷, indépendamment l'un de l'autre, représentent des radicaux hydroxyalkyle ou alkyle en C₁-C₄ et R¹⁸ est égal à R¹⁵ ou R¹⁶ et A⁻ représente un anion.
EP91121957A 1991-03-13 1991-12-20 Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires Expired - Lifetime EP0503155B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4108025A DE4108025A1 (de) 1991-03-13 1991-03-13 Waescheweichspuelmittel auf basis von quaternaeren poly(oxyalkylen)alkanolaminestern
DE4108025 1991-03-13

Publications (2)

Publication Number Publication Date
EP0503155A1 EP0503155A1 (fr) 1992-09-16
EP0503155B1 true EP0503155B1 (fr) 1996-05-01

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EP91121957A Expired - Lifetime EP0503155B1 (fr) 1991-03-13 1991-12-20 Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires

Country Status (5)

Country Link
US (1) US5254270A (fr)
EP (1) EP0503155B1 (fr)
CA (1) CA2062848A1 (fr)
DE (2) DE4108025A1 (fr)
ES (1) ES2089104T3 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0637625A1 (fr) * 1993-08-02 1995-02-08 The Procter & Gamble Company Emulsions superconcentrés avec adoucissants pour textiles
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
DE4405702A1 (de) * 1994-02-23 1995-08-24 Witco Surfactants Gmbh Hochkonzentrierte wäßrige Weichspülmittel mit verbesserter Lagerstabilität
CA2378163A1 (fr) * 1999-07-06 2001-01-11 The Procter & Gamble Company Compositions aqueuses adoucissantes limpides ou translucides pour textiles, a l'ammonium polyquaternaire, contenant une faible quantite de solvant
US6884767B1 (en) 1999-07-06 2005-04-26 The Procter & Gamble Company Clear or translucent aqueous polyquaternary ammonium fabric softener compositions containing low solvent
US7371718B2 (en) * 2005-04-22 2008-05-13 The Dial Corporation Liquid fabric softener
WO2009027925A2 (fr) * 2007-08-31 2009-03-05 The Procter & Gamble Company Procédés visant à modifier une perception visuelle et compositions associées

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB384714A (en) * 1930-08-27 1932-12-15 Du Pont Improvements in or relating to the catalytic production of amines from alcohols and a
US2017051A (en) * 1931-02-06 1935-10-15 Du Pont Synthesis of amines
US2078922A (en) * 1934-06-28 1937-05-04 Du Pont Synthesis of higher amines
EP0296995B1 (fr) * 1987-06-16 1994-05-04 Cotelle S.A. Compositions adoucissantes concentrées
DE3720331A1 (de) * 1987-06-19 1988-12-29 Huels Chemische Werke Ag Konzentrierte waescheweichspuelmittel
MY103439A (en) * 1987-10-29 1993-06-30 Kao Corp Detergent composition
DE68919236T2 (de) * 1988-01-28 1995-04-06 Unilever Nv Textilbehandlungszubereitung und deren Herstellung.
EP0345842A3 (fr) * 1988-05-27 1990-04-11 The Procter & Gamble Company Compositions adoucissantes pour le linge contenant des mélanges des esters d'imidazoline substitués et des sels quaternaires d'ammonium ester
US4946627A (en) * 1989-07-19 1990-08-07 National Starch And Chemical Investment Holding Corporation Hydrophobically modified polycarboxylate polymers utilized as detergent builders
DE3926740C2 (de) * 1989-08-12 1997-05-15 Witco Surfactants Gmbh Wässrige Weichspülmittel und deren Verwendung
DE4018750A1 (de) * 1990-06-12 1991-12-19 Rewo Chemische Werke Gmbh Poly(oxyalkylen)aminoalkanolester, deren ammoniumverbindungen, verfahren zu ihrer herstellung und ihre verwendung in emulgatoren, reinigungsmitteln, desinfektionsmitteln und konservierungsmitteln

Also Published As

Publication number Publication date
DE59107766D1 (de) 1996-06-05
CA2062848A1 (fr) 1992-09-14
DE4108025A1 (de) 1992-09-17
US5254270A (en) 1993-10-19
ES2089104T3 (es) 1996-10-01
EP0503155A1 (fr) 1992-09-16

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