EP0417987B1 - Weichmachen von Gewebe - Google Patents

Weichmachen von Gewebe Download PDF

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Publication number
EP0417987B1
EP0417987B1 EP90309792A EP90309792A EP0417987B1 EP 0417987 B1 EP0417987 B1 EP 0417987B1 EP 90309792 A EP90309792 A EP 90309792A EP 90309792 A EP90309792 A EP 90309792A EP 0417987 B1 EP0417987 B1 EP 0417987B1
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EP
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Prior art keywords
amine
materials
softening
acid
fabric softening
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Revoked
Application number
EP90309792A
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English (en)
French (fr)
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EP0417987A3 (en
EP0417987A2 (de
Inventor
Huw Unilever Research Port Sunlight Lab. Evans
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
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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
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2082—Polycarboxylic acids-salts thereof
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof

Definitions

  • the present invention relates to fabric softening compositions, in particular to fabric softening compositions containing one or more amines as active materials, which are intended for use in the rinse cycle of a fabric washing process.
  • US 3 954 630 (Ramachandran) describes the use of a complexing acid to prevent staining of fabrics.
  • the comprising acid may be used in conjunction with a cationic fabric softening agent.
  • EP-A-0 331 230 (Procter & Gamble) describes imidazole-type fabric conditioners having improved stability over other cyclic amines.
  • Compositions of the reference include a Bronstedt acid as dispersing aid.
  • EP-A-0 276 501 (Akzo N.V.) describes thickened compositions for surface cleaning.
  • the compositions include an amine and a weak acid among other ingredients.
  • One of the problems with amine-containing fabric softener compositions is that they often do not soften as well as conventional softeners containing quaternary ammonium softener materials.
  • the concentration of amine materials in the rinse water will generally be from 30 to 1000 ppm, preferably around 200. It has been found that improved softening can be obtained when the pH of an aqueous rinse liquor comprising the amine softener materials at a concentration of 200 ppm is equal to or below the pK a of the amine.
  • the present invention relates to a fabric softening composition
  • a fabric softening composition comprising one or more amine softening materials and one or more pH adjusting agents, wherein the pH of an aqueous liquor obtained by diluting said fabric softening composition to a concentration of 200 ppm of the amine materials has a pH which is equal to or below the pK a of the amine materials.
  • amine softening material can refer to any amine material which can be used for the softening of fabrics, for example one or more amines of the following formula can be used:
  • ARMEEN M2HT ARMEEN M2HT
  • the pH of a 200 ppm rinse liquor is preferably 4.5 or less, more preferred less than 3.5.
  • hydrocarbyl group refers to alkyl or alkenyl groups optionally substituted or interrupted by functional groups such as -OH, -O-, -CONH, -COO-, etc.
  • the pK a value is a well-known parameter related to the protonation of materials.
  • the pK a can be determined by considering the protonation reaction of the amine material: amine + H+ -------- amineH+
  • the pK a of the amine is the pH value, at which the amount of unprotonated amine is equal to the amount of protonated amine.
  • a possible method of determining the pK a of a substance is to determine the titration curve of a 1% dispersion of the material with increasing amounts of acid; the pK a of the material is the pH value at the midpoint of the steep part of the titration curve.
  • amine materials having a pK a of less than 6.5, more preferred less than 5.5, especially preferred between 5.2 and 4.0.
  • the pK a value of the amine material should be taken as the weight average pK a value of the amine mixture.
  • compositions of the present invention may take a variety of forms such as liquids, pastes, gels, powders, tablets, flakes etc.
  • compositions of the present invention are liquids, comprising an aqueous phase.
  • the water level in such aqueous liquids is from 97 to 20% by weight of the composition, more preferred from 95 to 70%.
  • the level of amine softener materials in products of the invention, especially liquid products of the invention is preferably more than 1% by weight of the composition, more preferred more than 2%, most preferred more than 3%.
  • the level of amine softener materials will not exceed 70% by weight of the composition, more preferred the level is less than 30%, especially preferred are compositions comprising from 3 to 20% by weight of amine softener materials.
  • a problem in the formulation of liquid products according to the invention is that the low pH requirement for the rinse liquor, generally requires high levels of pH adjusting agents in the undiluted product. These high levels of pH adjusting agents, however, often cause the undiluted product to be unstable due to the flocculation of the dispersed amine phase resulting in phase separation.
  • a second object of the present invention is to prevent instability of the undiluted product, while still ensuring that an adequate amount of pH adjusting materials are present.
  • pH adjusting agent which satisfies the following condition: 1.5 ⁇ pK a (pH adjuster) ⁇ pK a (amine) More preferably: 2.0 ⁇ pK a (pH adjuster) ⁇ pK a (amine) -0.5 Most preferably: 2.5 ⁇ pK a (pH adjuster) ⁇ pK a (amine) -1.0
  • the pK a (pH adjuster) for use in the above given equations is the lowest pK a value of the pH adjusting material.
  • citric acid has pK a values of 3.1, 4.8 and 6.4.
  • the value 3.1 is used as the pK a (citric acid).
  • the pK a value for the mixture of pH adjusters is the weight average pK a of the mixture of pH adjusting materials.
  • compositions according to the invention also comprise one or more pH adjusting agents.
  • the pH adjusting agents should provide a certain pH for the rinse water. As soon as the required pH for the rinse water has been determined in line with the teaching as given above, it is believed to be well within the ambit of the skilled person, to select the types and amounts of pH adjusting materials necessary to obtain the required pH. Generally the pH adjusting agents will be acid materials.
  • the product of the invention is a liquid product, comprising an aqueous base
  • the pH adjusting materials have a pK a which is above 1.5, but below the pK a of the amine.
  • Typical concentrations for the pH adjusting materials in the liquid undiluted products are from 0.1 to 2.0 mole per litre, more preferably from 0.2 to 1.5 mole per litre, especially preferred from 0.25 to 1.0 mole per litre.
  • Preferred pH adjusting materials have a pK a of between 2.5 and 3.5.
  • these materials are p-Aminobenzosulphonic acid, bromoacetic acid, chloroacetic acid, o-chloroacetic acid, alpha chlorobutyric acid, citric acid, dihydroxybenzoic acid, dimethylmalic acid, dimethylmalonic acid, dinicotinic acid, fumaric acid, furancarboxylic acid, iodoacetic acid, lactic acid, malic acid, malonic acid, methyl malonic acid, quinolinic acid, sulfanilic acid and tartaric acid.
  • tartaric acid, lactic acid, citric acid, malonic acid or mixtures thereof is preferred.
  • the pH adjusting materials having a pK a of between 2.5 and 3.5 are used in combination with amines of formula (i), which comprise two long hydrocarbyl groups (C6-C24) and one short hydrocarbyl group (C1-C3).
  • amines of formula (i) which comprise two long hydrocarbyl groups (C6-C24) and one short hydrocarbyl group (C1-C3).
  • ARMEEN M2HT Akzo
  • compositions of the present invention may comprise in addition to the above mentioned amine and pH adjusting materials one or more other softener materials selected from cationic, amphoteric and nonionic softening materials. Suitable materials are for example described in EP 239 910 (P&G), US 3 915 865 (STEPAN) and US 4 137 180 (LEVER BROTHERS). Preferably the weight ratio of these additional softening materials to the total of the amine softening materials is less than 3:1, more preferred less than 1:1, especially preferred less than 0.5:1.
  • the composition can also contain one or more optional ingredients selected from non-aqueous solvents such as C1-C4 alkanols and polyhydric alcohols, rewetting agents, viscosity modifiers such as electrolytes or long (e.g. 25-40 EO) alkoxylated fatty alcohols, for example calcium chloride, antigelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, emulsifiers, anti-shrinking agents, anti-wrinkle agents, fabric crisping agents, anti-spotting agents, soil-release agents, germicides, linear or branched silicones, fungicides, anti-oxidants, anti-corrosion agents, preservatives such as Proxel, ascorbic acid, Bronopol (Trade Mark), a commercially available form of 2-bromo-2-nitro
  • These optional ingredients if added, preferably are present at levels up to 5% by weight of the composition.
  • compositions according to the invention may be prepared by a variety of methods.
  • One suitable method to prepare liquid products according to the invention is to form a molten mixture of the amine materials eventually in combination with other softening materials, and adding this premix to water under stirring to form a dispersion and thereafter adding the pH adjusting materials and any optional ingredients.
  • a di hardened tallow methyl amine (Armeen M2HT) was dispersed in water of ambient temperature to a concentration of 200 ppm of the amine.
  • the pK a of the amine is 4.5.
  • 1 litre of the 200 ppm amine dispersion was adjusted to the pH as indicated with HCl.
  • Pieces of terry towelling of a total weight of 40g were rinsed for 5 minutes in the amine dispersion. The pieces were line dried.
  • the amount of deposited amine was determined by measuring the change in turbidity of the rinse liquor. A higher deposition percentage corresponds to a better softening.
  • a wash load of 1.25 kg of terry towelling and 1.25 kg of cotton sheeting fabrics was washed at 40°C in a Miele 756 automatic with 100g of Persil Automatic (UK).
  • 90 mls (corresponding to about 200 ppm for the amine concentration) of a rinse conditioner containing 5wt% Armeen M2HT, 1wt% tallow 35EO and a variable amount of pH adjusting material was added to the last rinse cycle.
  • table 3 the stability of the undiluted product, the pH of the undiluted product and the pH of the rinse water are given. A lower value for the pH of the rinse corresponds to a better softening performance.
  • succinic acid is used, also stable products are obtained, but high levels of the acid material are necessary to obtain the preferred pH in the rinse liquor, these high levels of acid materials are sometimes less preferred for cost reasons.

Claims (8)

  1. Gewebeerweichungszusammensetzung mit einem oder mehreren Aminerweichungsmaterialien und einem oder mehreren den pH-Wert einstellenden Mitteln, wobei der pH-Wert einer durch Verdünnen der Gewebeerweichungszusammensetzung auf eine Konzentration von 200 ppm an den Aminmaterialien erhaltenen wäßrigen Flüssigkeit einen Wert besitzt, der dem pKa-Wert der Aminmaterialien entspricht oder diesen unterschreitet, wobei ein oder mehrere Aminerweichungsmaterialien aus Gewebeerweichungsaminen der Formel (I) ausgewählt sind:
    Figure imgb0007
     worin entweder (a) R₁₅ und R₁₆ für C₆-C₂₄-Kohlenwasserstoffgruppen stehen und R₁₇ eine C₁-C₃-Kohlenwasserstoffgruppe bedeutet oder (b) R₁₅ für eine Kohlenwasserstoffgruppe mit mindestens 22 Kohlenstoffatomen steht und R₁₆ und R₁₇ C₁-C₃-Kohlenwasserstoffgruppen bedeuten.
  2. Gewebeerweichungszusammensetzung nach Anspruch 1, wobei der pH-Wert der verdünnten Aminflüssigkeit mindestens 0,5 Einheiten unter dem pKa-Wert des Amins liegt.
  3. Gewebeerweichungszusammensetzung nach Anspruch 1 oder 2, bei der es sich um eine Flüssigkeit mit einer wäßrigen Base handelt, wobei das den pH-Wert einstellende Mittel der folgenden Gleichung genügt:
    1,5 < pKa-Wert (den pH-Wert einstellendes Mittel) < pKa-Wert (Amin).
  4. Gewebeerweichungszusammensetzung nach Anspruch 3, wobei der pKa-Wert des den pH-Wert einstellenden Mittels 2,5 bis 3,5 beträgt.
  5. Gewebeerweichungszusammensetzung nach Anspruch 3 oder 4, wobei die den pH-Wert einstellenden Mittel unter Weinsäure, Milchsäure, Citronensäure und Malonsäure oder Gemischen hiervon ausgewählt sind.
  6. Gewebeerweichungszusammensetzung nach einem der Ansprüche 3 bis 5, wobei die Konzentration des den pH-Wert einstellenden Materials 0,25 bis 1,0 mol/l beträgt.
  7. Gewebeerweichungszusammensetzung nach einem der vorhergehenden Ansprüche, die als Gewebeerweichungsamin der Formel (I)(b) digehärtetes 1,2-Talgoxydimethylpropanamin umfaßt.
  8. Verwendung eines oder mehrerer Aminerweichungsmaterialien und eines oder mehrerer den pH-Wert einstellender Mittel bei der Herstellung einer Gewebeerweichungszusammensetzung zur Erweichung von Geweben, die nach Verdünnen auf eine Konzentration von 200 ppm an dem Aminmaterial einen pH-Wert aufweist, der dem pKa-Wert des Aminmaterials entspricht oder diesen unterschreitet, wobei ein oder mehrere Aminerweichungsmaterialien unter den Gewebeerweichungsaminen der Formel (I) ausgewählt sind:
    Figure imgb0008
     worin entweder (a) R₁₅ und R₁₆ für C₆-C₂₄-Kohlenwasserstoffgruppen stehen und R₁₇ eine C₁-C₃-Kohlenwasserstoffgruppe bedeutet oder (b) R₁₅ für eine Kohlenwasserstoffgruppe mit mindestens 22 Kohlenstoffatomen steht und R₁₆ und R₁₇ C₁-C₃-Kohlenwasserstoffgruppen bedeuten.
EP90309792A 1989-09-11 1990-09-07 Weichmachen von Gewebe Revoked EP0417987B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8920468 1989-09-11
GB898920468A GB8920468D0 (en) 1989-09-11 1989-09-11 Fabric softening

Publications (3)

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EP0417987A2 EP0417987A2 (de) 1991-03-20
EP0417987A3 EP0417987A3 (en) 1991-08-14
EP0417987B1 true EP0417987B1 (de) 1996-02-07

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EP90309792A Revoked EP0417987B1 (de) 1989-09-11 1990-09-07 Weichmachen von Gewebe

Country Status (9)

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EP (1) EP0417987B1 (de)
JP (1) JP2566177B2 (de)
AU (1) AU635767B2 (de)
BR (1) BR9004440A (de)
CA (1) CA2024699C (de)
DE (1) DE69025246T2 (de)
ES (1) ES2084004T3 (de)
GB (1) GB8920468D0 (de)
ZA (1) ZA907142B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ239522A (en) * 1990-09-04 1993-10-26 Chapman Chem Co Pesticidal compositions containing an amine salt of a phosphonic or orthophosphoric acid
US5312558A (en) * 1991-04-04 1994-05-17 Ibc Manufacturing Company Pesticide composition
US5612372A (en) * 1990-09-04 1997-03-18 Ibc Manufacturing Company Liquid dispersants for pesticides
EP0658185A1 (de) * 1992-08-21 1995-06-21 Colgate-Palmolive Company Gewebekonditionierungszusammensetzung
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
EP0637625A1 (de) * 1993-08-02 1995-02-08 The Procter & Gamble Company Emulsionssuperkonzentrate mit Textilweichmachern
EP0799887B1 (de) * 1996-04-01 2003-06-11 The Procter & Gamble Company Textilweichmacherzusammensetzungen
US10570567B2 (en) * 2016-02-29 2020-02-25 Kemira Oyj Softener composition

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3904359A (en) * 1972-09-07 1975-09-09 Colgate Palmolive Co Post-wash fabric treating method
GB1514276A (en) * 1975-10-22 1978-06-14 Unilever Ltd Fabric-softening compositions
US4157307A (en) * 1978-08-07 1979-06-05 The Procter & Gamble Company Liquid fabric softener
DE2841076C2 (de) * 1978-09-21 1980-02-14 Basf Ag, 6700 Ludwigshafen Verfahren zur Verflüssigung wäßriger Textilweichmacher
US4320013A (en) * 1980-06-10 1982-03-16 The Procter & Gamble Company Fabric conditioning compositions
EP0056695B2 (de) * 1981-01-16 1987-09-09 THE PROCTER &amp; GAMBLE COMPANY Textilbehandlungsmittel
GB8508129D0 (en) * 1985-03-28 1985-05-01 Procter & Gamble Ltd Textile treatment composition
GB2172910B (en) * 1985-03-28 1989-06-21 Procter & Gamble Detergent containing a fabric conditioner
DE3661481D1 (en) * 1985-05-28 1989-01-26 Unilever Nv Liquid cleaning and softening compositions
US4828722A (en) * 1986-07-10 1989-05-09 Colgate-Palmolive Co. Through the wash fabric conditioning compositions
MX169902B (es) * 1986-07-10 1993-07-30 Colgate Palmolive Co Mejoras a composiciones acondicionadoras de tela a traves del lavado
NO170944C (no) * 1987-01-24 1992-12-30 Akzo Nv Fortykkede, vandige preparater, samt anvendelse av slike
GB8804555D0 (en) * 1988-02-26 1988-03-30 Procter & Gamble Imidazole compounds & textile treatment compositions containing them
US4869836A (en) * 1988-05-03 1989-09-26 Colgate-Palmolive Co. Wash cycle fabric conditioning compositions: tertiaryamine-multi-functional carboxylic acid complex
US4863620A (en) * 1988-10-18 1989-09-05 The Procter & Gamble Company Acidic liquid fabric softener with yellow color that changes to blue upon dilution
GB8916308D0 (en) * 1989-07-17 1989-08-31 Unilever Plc Fabric softening

Also Published As

Publication number Publication date
AU635767B2 (en) 1993-04-01
AU6223490A (en) 1991-03-14
ZA907142B (en) 1992-05-27
DE69025246D1 (de) 1996-03-21
DE69025246T2 (de) 1996-06-27
EP0417987A3 (en) 1991-08-14
BR9004440A (pt) 1991-09-10
CA2024699A1 (en) 1991-03-12
CA2024699C (en) 2002-01-08
EP0417987A2 (de) 1991-03-20
GB8920468D0 (en) 1989-10-25
JPH03137280A (ja) 1991-06-11
ES2084004T3 (es) 1996-05-01
JP2566177B2 (ja) 1996-12-25

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