EP0409504A2 - Fabric softening composition - Google Patents

Fabric softening composition Download PDF

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Publication number
EP0409504A2
EP0409504A2 EP19900307693 EP90307693A EP0409504A2 EP 0409504 A2 EP0409504 A2 EP 0409504A2 EP 19900307693 EP19900307693 EP 19900307693 EP 90307693 A EP90307693 A EP 90307693A EP 0409504 A2 EP0409504 A2 EP 0409504A2
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Prior art keywords
quaternary ammonium
fabric softening
materials
softening composition
ester
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Application number
EP19900307693
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German (de)
French (fr)
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EP0409504A3 (en )
EP0409504B1 (en )
Inventor
Amrat Paul Singh
Graham Andrew Turner
Edwin Willis
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • C11D1/66Non-ionic compounds
    • C11D1/835Mixtures of non-ionic with cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • C11D1/645Mixtures of compounds all of which are cationic
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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 AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • C11D1/66Non-ionic compounds
    • C11D1/667Neutral esters, e.g. sorbitan esters; see also C11D1/74 and C11D1/78
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND 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
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols

Abstract

A fabric softening composition which comprises:
  • (i) an ester-linked quaternary ammonium material of the formula:
    Figure imga0001
    wherein each R1 group is independently selected from C1 -4 alkyl, alkenyl or hydroxyalkyl groups; each R2 group is independently selected from C8-28 alkyl or alkenyl groups; T is
    Figure imga0002
    and
    n is an integer from 0-5; and
  • (ii) an extender material selected from:
    • (a) quaternary ammonium compounds, comprising one long alkyl or alkenyl group;
    • (b) predominantly linear nonionic materials; or
    • (c) mixtures thereof; said composition being obtainable by heating a mixture comprising the materials (i) and (ii) to a temperature of above 40°C, followed by dispersing the mix into water.

Description

  • The present invention relates to a fabric softening composition and to a method for its preparation. Specifically the present invention relates to a fabric softening composition for use in the rinse step of a fabric washing process.
  • In US 4 137 180 (Lever Brothers Company) cationic diesters of the formula:
    Figure imgb0001
    wherein R1, R2 and R3 are each an alkyl or hydroxyalkyl group containing from 1 to 4 carbon atoms, or a benzyl group, R4 and R5 are each alkyl chains containing from 11 to 23 carbon atoms and X- is a water soluble anion are disclosed.
  • It has been proposed in EP 239,910 (P&G) to formulate fabric conditioning compositions comprising ester-linked quaternary ammonium materials of the following formula:
    Figure imgb0002
  • Wherein each R1 group is independently selected from C1-4 alkyl, alkenyl or hydroxyalkyl groups; each R2 group is independently selected from C12-24 alkyl or alkenyl groups; T is
    Figure imgb0003
    and
    n is an integer from 0-5.
  • These ester-linked quaternary ammonium materials are particularly preferred for use in fabric conditioners because they are more biodegradable than conventional quaternary ammonium materials.
  • In the past difficulty was experienced in preparing fabric softening compositions containing solely the above mentioned softening material at levels above 0.1% by weight by the known method of pre-melting the material followed by dispersing the melt into hot water while stirring because upon melting a highly viscous phase was formed which was very difficult to disperse. The products obtained from such a method were not of satisfactory stability and tended to thicken on storage to an unacceptably high viscosity. Attempts to prepare fabric softening compositions by cold dispersion resulted in inhomogeneous products of unacceptably high viscosity.
  • It is an object of the present invention to provide fabric softening compositions which comprise the above mentioned biodegradable quaternary ammonium compounds. It is a second object of the invention to provide biodegradable fabric softening compositions which are of acceptable stability. Further objects of the invention are to provide fabric softening compositions which can easily be prepared and which provide adequate softening to fabrics treated therewith.
  • Surprisingly, it has been found that one or more of the above mentioned problems can be overcome and/or one or more of the above mentioned objects can be met, if the specific ester-linked quaternary ammonium materials as mentioned above are used in combination with one or more specific extender materials.
  • Accordingly the present invention relates to a fabric softening composition which comprises:
    • (i) at least 1 % by weight of an ester-linked quaternary ammonium material of the formula:
      Figure imgb0004
      Wherein each R1 group is independently selected from C1 -4 alkyl, alkenyl or hdyroxyalkyl groups; each Rε group is independently selected from C8-28 alkyl or alkenyl groups; T is
      Figure imgb0005
      and
      n is an integer from 0-5; and
    • (ii) at least 0.1% by weight of an extender material selected from:
      • (a) tertiary or quaternary ammonium compounds, comprising one long alkyl or alkenyl group;
      • (b) predominantly linear nonionic materials; or
      • (c) mixtures thereof; said composition being obtainable by heating a mixture comprising the materials (i) and (ii) to a temperature of above 40 C followed by dispersing the mix into water.
  • The compositions of the invention may take a variety of forms such as pastes, liquids etc and also they may be impregnated onto substrates for example for use in tumble dryers. Preferably compositions of the invention are liquids, comprising an aqueous base, wherein the active ingredients are dispersed.
  • Suitable ester-linked quaternary ammonium materials (i) and their method of preparation are for example described in US 4 137 180 (LEVER BROTHERS). A preferred material is 1,2-ditallow oxy-3-trimethyl ammoniumpropane chloride.
  • Preferably the level of ester-linked quaternary ammonium material (i) is at least 3% by weight of the composition, especially interesting are compositions of high active level, e.g. which comprise more than 8% of the ester linked quaternary ammonium compound. The level of ester-linked quaternary ammonium materials (i) preferably is less than 70% by weight of the composition, more preferred less than 50%, typically from 3 to 30% by weight of the composition.
  • The extender material (ii) can be selected from mono-long alkyl or alkenyl tertiary or quaternary ammonium compounds and predominantly linear nonionic materials or mixtures thereof. In this specification the expression predominantly linear nonionic material refers to materials having a molecular backbone whereto no- or only a small number of side groups are attached. Preferably the molecular backbone constitutes more than 75% by weight of the molecule, more preferred more than 90%. In selecting the extender materials for use in a composition of the invention it is preferred only the use materials which are of acceptable biodegradability.
  • Especially useful extender materials are:
    • (A) Tertiary amines containing one C 8-28 alkyl or alkenyl group and two C1-4 alkyl, alkenyl or hydroxyalkyl groups. These materials preferably are used in protonated form.
    • (B) Ester-linked mono-long alkyl or alkenyl quaternary ammonium compounds, containing one C8-28 alkyl or alkenyl group, connected to the quaternary ammonium molecule via an ester link. Preferred materials within this class are materials of the formula:
      Figure imgb0006
      or
      Figure imgb0007
      wherein R1 R2, T and n are as defined for formula (I) and R3 is a hydrogen or hydroxy group. Of these materials, those are preferred, wherein R3 is an hydroxy-group. These materials show a surprisingly good softening performance.
    • (C) Predominantly linear nonionic ester materials, for example esters of C8-28 fatty acids and C1-30 monohydric alcohols. Especially preferred is the use of ethylstearate, lanolin and Jojoba oil.
    • (D) Predominantly linear C8-28 fatty alcohol materials, C8-28 fatty acid materials or their salts. Of these materials especially the use of free monocarboxylic fatty acid materials is preferred.
    • (E) Esters of predominantly linear C8-28 fatty acids with polyhydric alcohols. Preferred esters are glycerol monostearate, sorbitan monostearate and the monoesters of polyethyleneglycol of molecular weight between 200 and 2000.
  • Preferably the level of extender material is more than 0.2%, especially preferred are systems comprising more than 0.5% of extender material. The level of extender material will usually not exceed 50% by weight of the composition, more preferred the level is less than 30%, typically from 0.5 to 10% by weight of the composition.
  • The weight ratio of ester-linked quaternary ammonium materials (i) to extender materials (ii) is preferably from 20:1 to 1:10, more preferred from 10:1 to 1:2, especially preferred from 9:1 to 1:1.
  • Compositions of the invention are obtainable by heating a mixture of the materials (i) and (ii) to a temperature of above 40 C followed by dispersing the mix into water. Preferably the materials are heated to a temperature of above 50 * C and dispersed in water of elevated temperature. Compositions made by this method show a surprising good stability and no or only a small viscosity increase upon storage. It is believed that this increased stability may be caused by the particularly good homogeneity of the products obtained by using this method. Therefore particular preferred products in accordance with the present invention comprise the above mentioned two materials (i) and (ii) dispersed in water, wherein the mean particle diameter of the dispersed softener phase is less than 10µm, preferably less than 7µm, especially preferred less than 3u.m. Such small particle dispersion are often referred to as microdispersions.
  • The compositions of the invention preferably have a pH of more than 2.0. Preferably the pH of the composition is less than 8.0, more preferably less than 5.0. Especially preferred are pH values in the range of from 2.5 to 4.0.
  • Compositions of the invention may in addition to the above described two ingredients also comprise other active ingredients such as further fabric conditioning materials.
  • In selecting the optional ingredients it is preferred to use materials which do not substantially affect the biodegradability of the composition. Therefore it is preferred to minimize the level of non-biodegradable or less bio-degradable materials.
  • Preferably compositions of the invention do not comprise large amounts of conventional non-ester linked quaternary ammonium compounds, preferably the compositions of the invention are substantially free of these quaternary ammonium compounds.
  • Softening materials which may be incorporated in a composition of the invention are amines, such as for instance described in EP 89200113.2, or biodegradable amphoteric softener materials such as for instance described in EP 89200113.2.
  • Preferably the amount of active materials other than the above mentioned ester-linked materials and extender materials is relatively low, i.e. the weight ratio of other softener materials to the total of the two essential softener components is preferably less than 2:1, more preferred less than 1:1, most 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, pH buffering agents such as strong or weak acid e.g. HCI, H2SO4. phosphoric, benzoic or citric acids, rewetting agents, viscosity modifiers such as electrolutes, 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 Bronopol (Trade Mark), a commercially available form of 2-bromo-2-nitropropane-1,3-diol, dyes, bleaches and bleach precursors, drape imparting agents, antistatic agents and ironing aids.
  • These optional ingredients, if added, preferably are present at levels up to 5% by weight of the composition.
  • A preferred method to prepare compositions according to the invention is to form a molten mixture of the ester-linked quaternary ammonium materials (i) and the extender materials (ii) eventually in combination with other softening materials and/or other optional ingredients, and adding this premix to water under stirring to form a dispersion and thereafter adding any other optional ingredients.
  • In use, the fabric conditioning composition of the invention may be added to a large volume of water to form a liquor with which the fabrics to be treated are contacted. Generally, the total concentration of the ester linked quaternary ammonium compounds (i) and the extender compound in this liquor will be between about 30ppm and 1000ppm. The weight ratio of the fabrics to liquor will generally be between 1:1 and 1:20.
  • The invention will be further illustrated by means of the following examples.
  • EXAMPLE I
  • The following compositions were prepared by heating the active ingredients to a temperature of 60 C and dispersing the premelt into water of 60° C under stirring. The resulting compositions according to the invention were homogeneous dispersions, wherein the mean diameter of the dispersed active particles was less than turn.
    Figure imgb0008
  • 2g of the formulations A-D was added to 1 liter of tap water of ambient temperature containing 0.001% by weight of sodium alkyl benzene sulphonate to simulate the carry over of anionic detergent active from the wash. 800ml of the obtained solution was put in a tergotometer pot and four pieces of terry towel (40g total weight) were added. The cloths were treated for 5 minutes at 60rpm, spin dried and line dried. The dried fabrics were assessed for softness by an expert panel using a Round Robin test protocol.
  • The order of preference for the above mentioned compositions was:
  • B>C>A>D
  • These results show a surprisingly good softening effect for compositions of the present invention (A-C) compared to currently available biodegradable softener actives (D).
  • EXAMPLE 2
  • The following compositions were prepared as in example 1.
    Figure imgb0009
  • EXAMPLE 3
  • The following compositions were prepared as in example 1.
    Figure imgb0010
  • EXAMPLE 4
  • The following compositions were prepared as in example 1.
    Figure imgb0011
  • EXAMPLE 5
  • The following compositions were prepared as in Example 1.
    Figure imgb0012

Claims (10)

1. A fabric softening composition comprising
(i) at least 1 % by weight of an ester-linked quaternary ammonium material of the formula:
Figure imgb0013
wherein each R1 group is independently selected from C1-4 alkyl, alkenyl or hydroxyalkyl groups; each R2 group is independently selected from C8-28 alkyl or alkenyl groups; T is
Figure imgb0014
and
n is an integer from 0-5; and
(ii) at least 0.1% by weight of an extender material selected from:
(a) quaternary ammonium compounds, comprising one long alkyl or alkenyl group;
(b) predominantly linear nonionic mateials; or
(c) mixtures thereof said composition being obtainable by heating a mixture comprising the materials (i) and (ii) to a temperature of above 40 C, followed by dispersing the mix into water.
2. A fabric softening composition which comprises a dispersion in water of:
(i) at least 1 % by weight of an ester-linked quaternary ammonium material of the formula:
Figure imgb0015
wherein each R1 group is independently selected from C1 -4 alkyl, alkenyl or hydroxyalkyl groups; each R2 group is independently selected from C8-28 alkyl or alkenyl groups; T is
Figure imgb0016
and
n is an integer from 0-5; and
(ii) at least 0.1% by weight of an extender material selected from:
(a) quaternary ammonium compounds, comprising one long alkyl or alkenyl group;
(b) predominantly linear nonionic materials; or
(c) mixtures thereof;

said dispersion having mean partice diameter of less than 10µm.
3. A fabric softening composition as claimed in claim 1 or 2 comprising at least 3% by weight of the ester-linked quaternary ammonium material of formula (1).
4. A fabric softening composition as claimed in any preceding claim comprising at least 8% by weight of the ester-linked quaternary ammonium material of formula (1).
5. A fabric softening composition as claimed in any preceding claim comprising from 3 to 30% by weight of an ester-linked quaternary ammonium material of formula (1).
6. A fabric softening composition as claimed in any preceding claim comprising as an extender material a quaternary ammonium compound comprising one long alkyl or alkenyl group connected via an ester link.
7. A fabric softening composition as claimed in any preceding claim comprising as an extender material an ester-linked quaternary ammonium material selected from materials of formula (II) and (III) as hereinbefore defined.
8. A fabric softening composition as claimed in any preceding claim comprising at least 0.5% of the extender material.
9. A fabric softening composition as claimed in any preceding claim comprising from 0.5% to 10% of the extender material.
10. A fabric softening composition as claimed in any preceding claim having a pH in the range from 2 to 8.
EP19900307693 1989-07-17 1990-07-13 Fabric softening composition Expired - Lifetime EP0409504B1 (en)

Priority Applications (2)

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GB8916307 1989-07-17
GB8916307A GB8916307D0 (en) 1989-07-17 1989-07-17 Fabric softening composition

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EP0409504A2 true true EP0409504A2 (en) 1991-01-23
EP0409504A3 true EP0409504A3 (en) 1991-10-02
EP0409504B1 EP0409504B1 (en) 1996-09-25

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EP (1) EP0409504B1 (en)
JP (1) JP2611035B2 (en)
CA (1) CA2021010C (en)
DE (2) DE69028667T2 (en)
ES (1) ES2093016T3 (en)
GB (1) GB8916307D0 (en)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0409502A2 (en) * 1989-07-17 1991-01-23 Unilever Plc Fabric softening composition
WO1993001265A1 (en) 1991-07-05 1993-01-21 Unilever Plc Fabric softening composition
WO1993019147A1 (en) * 1992-03-16 1993-09-30 The Procter & Gamble Company Fabric softening compositions containing mixtures of softener material and highly ethoxylated curd dispersant
EP0571086A1 (en) * 1992-04-22 1993-11-24 Unilever Plc Hair care composition
WO1993023510A1 (en) * 1992-05-12 1993-11-25 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
EP0585040A1 (en) * 1992-08-28 1994-03-02 Unilever Plc Use of fabric softening composition
WO1994013772A1 (en) * 1992-12-16 1994-06-23 Henkel Kommanditgesellschaft Auf Aktien Aqueous textile softener dispersions
WO1994019439A1 (en) * 1993-02-25 1994-09-01 Unilever Plc Use of fabric softening composition
US5376287A (en) * 1993-08-06 1994-12-27 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing ethoxylated/propoxylated sugar derivatives
WO1995004802A1 (en) * 1993-08-06 1995-02-16 The Procter & Gamble Company Dryer-activated fabric conditioning and antistatic compositions containing biodegradable compounds having unsaturation
US5403500A (en) * 1992-04-28 1995-04-04 Lever Brothers Company Rinse conditioner
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
US5503756A (en) * 1994-09-20 1996-04-02 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
EP0728737A1 (en) * 1995-02-24 1996-08-28 Kao Corporation Quaternary ammonium salt, method for production thereof, and softener composition using salt
US5552137A (en) * 1994-08-05 1996-09-03 Witco Corporation Biodegradable quaternary hair conditioners
GB2301843A (en) * 1996-05-10 1996-12-18 Unilever Plc Stable fabric conditioning composition
WO1997009403A1 (en) * 1995-09-04 1997-03-13 Unilever Plc Fabric softening composition
WO1997015651A1 (en) * 1995-10-23 1997-05-01 Unilever Plc Fabric softening composition
US5721205A (en) * 1994-04-29 1998-02-24 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5773409A (en) * 1994-04-07 1998-06-30 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US5856287A (en) * 1995-03-01 1999-01-05 Colgate-Palmolive Co. Laundry concentrates
WO1999050378A1 (en) * 1998-03-27 1999-10-07 Unilever Plc Fabric softening composition
EP1096055A1 (en) * 1998-06-11 2001-05-02 Kao Corporation Softener composition
US6797689B2 (en) 2001-09-10 2004-09-28 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of reducing the viscosity of fabric conditioning compositions
US6849592B2 (en) 2001-09-10 2005-02-01 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Fabric conditioning compositions
EP0789070B2 (en) 1996-02-09 2009-01-21 Unilever Plc Fabric softening composition

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Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0409502A3 (en) * 1989-07-17 1991-11-13 Unilever Plc Fabric softening composition
EP0409502A2 (en) * 1989-07-17 1991-01-23 Unilever Plc Fabric softening composition
US5407589A (en) * 1991-07-05 1995-04-18 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
WO1993001265A1 (en) 1991-07-05 1993-01-21 Unilever Plc Fabric softening composition
WO1993019147A1 (en) * 1992-03-16 1993-09-30 The Procter & Gamble Company Fabric softening compositions containing mixtures of softener material and highly ethoxylated curd dispersant
US5368756A (en) * 1992-03-16 1994-11-29 The Procter & Gamble Company Fabric softening compositions containing mixtures of softener material and highly ethoxylated curd dispersant
EP0571086A1 (en) * 1992-04-22 1993-11-24 Unilever Plc Hair care composition
US5403500A (en) * 1992-04-28 1995-04-04 Lever Brothers Company Rinse conditioner
EP0894848A1 (en) * 1992-05-12 1999-02-03 THE PROCTER & GAMBLE COMPANY Concentrated fabric softener compositions containing biodegradable fabric softeners
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
WO1993023510A1 (en) * 1992-05-12 1993-11-25 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
EP0585040A1 (en) * 1992-08-28 1994-03-02 Unilever Plc Use of fabric softening composition
WO1994013772A1 (en) * 1992-12-16 1994-06-23 Henkel Kommanditgesellschaft Auf Aktien Aqueous textile softener dispersions
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JP2611035B2 (en) 1997-05-21 grant
CA2021010C (en) 2000-10-31 grant
EP0409504A3 (en) 1991-10-02 application
DE69028667D1 (en) 1996-10-31 grant
EP0409504B1 (en) 1996-09-25 grant
CA2021010A1 (en) 1991-01-18 application
JPH0390677A (en) 1991-04-16 application
DE69028667T2 (en) 1997-03-06 grant
ES2093016T3 (en) 1996-12-16 grant
GB8916307D0 (en) 1989-08-31 grant

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