EP0507478A1 - Fabric softening composition - Google Patents

Fabric softening composition Download PDF

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Publication number
EP0507478A1
EP0507478A1 EP19920302452 EP92302452A EP0507478A1 EP 0507478 A1 EP0507478 A1 EP 0507478A1 EP 19920302452 EP19920302452 EP 19920302452 EP 92302452 A EP92302452 A EP 92302452A EP 0507478 A1 EP0507478 A1 EP 0507478A1
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Prior art keywords
composition
fabric softening
agent
weight
nonionic stabilising
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EP19920302452
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German (de)
French (fr)
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EP0507478B1 (en
Inventor
Simon Richard Unilever Research Ellis
Graham Andrew Unilever Research Turner
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR 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 OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR 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 OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR 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 OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR 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

Definitions

  • the present invention relates to fabric softening compositions, in particular the invention relates to aqueous dispersions of biodegradable fabric softening compositions comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent suitable as rinse-added fabric softener compositions.
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates.
  • fabric softening compositions desirably have other benefits. One is the ability to confer soil release properties to fabrics, particularly those woven from polyester fibres.
  • viscosity control agents In the past physical stability of rinse added fabric softener compositions has been improved by the addition of viscosity control agents or anti-gelling agents.
  • viscosity control agents For example in EP 13780 (Procter and Gamble) viscosity control agents are added to certain concentrated compositions. The agents may include C10-C18 fatty alcohols.
  • EP 280550 Unilever it has been proposed to improve the physical stability of dilute compositions comprising biodegradable, ester-linked quaternary ammonium compounds and fatty acid by the addition of nonionic surfactants.
  • compositions comprising biodegradable ester-linked quaternary ammonium compounds the problem of physical instability is more acute than with traditional quaternary ammonium compounds.
  • a nonionic emulsifier/stabiliser is added to a concentrate comprising an ester-linked quaternary ammonium compound to form a viscous gel.
  • the stabiliser is a C12 to C14 alcohol ethoxylated with 9 molecules of ethylene oxide. The degree of branching of the alcohol is not, however, mentioned.
  • Certain nonionic stabilising agents not only stabilise concentrated compositions comprising biodegradable quaternary ammonium compounds but are also environmentally friendly, in that they show acceptable biodegradability and are not substantially toxic in aquatic systems.
  • Soil release properties are generally imparted to fabrics by the use of separate soil-release agents, usually a high molecular weight polymer, in a detergent composition or separate treatment.
  • separate soil-release agents usually a high molecular weight polymer
  • a cationic polymeric soil release agent for use in a fabric conditioning composition.
  • a disadvantage of such compositions is that the soil release agent increases the number of components in the formulation, increasing cost and making the product less environmentally acceptable.
  • fabric softening compositions comprising biodegradable ester-linked quaternary ammonium compounds may confer improved soil release properties to fabrics.
  • a fabric softening composition comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent characterised in that the water insoluble cationic fabric softening agent is a biodegradable quaternary ammonium material with at least one ester link and the nonionic stabilising agent is
  • nonionic stabilising agent is a linear C 8 to C22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide
  • compositions of the invention are liquids comprising an aqueous base.
  • the fabric softening composition comprises a water insoluble cationic which is a compound having two C12 ⁇ 28 alkyl or alkenyl groups connected to the N atom via one or more ester links.
  • a preferred type of ester-linked quaternary ammonium material for use in the compositions according to the invention can be represented by the formula: wherein each R 1 group is independently selected from C1 ⁇ 4 alkyl, alkenyl or hydroxyalkyl groups; and wherein each R 2 group is independently selected from C8 ⁇ 28 alkyl or alkenyl groups; T is or and n is an integer from 0-5.
  • a second preferred type of quaternary ammonium material can be represented by the formula: wherein R 1 , n and R 2 are as defined above.
  • Preferred materials of this class and their method of preparation are, for example, described in US 4 137 180 (Lever Brothers).
  • these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-tallowoxy, 2-hydroxytrimethyl ammonium propane chloride.
  • the level of ester linked quaternary ammonium compounds is at least 1% by weight of the composition, more preferably more than 3% by weight of the composition; especially interesting are concentrated compositions which comprise more than 7% of ester-linked quaternary ammonium compound.
  • the level of ester-linked quaternary ammonium compounds preferably is between 1% and 80% by weight, more preferably 3% to 50%, most preferably 8% to 50%.
  • Suitable nonionic stabilisers which can be used include the condensation products of C 8 - C22 primary linear alcohols with 10 to 20 moles of ethylene oxide.
  • linear alcohol means a primary alcohol attached directly to a hydrocarbon backbone structure.
  • An HLB of greater than about 12 gives rise to an acceptable acute aquatic toxicity value of >1mg/1;EC50 48 hours for daphnia and algae and EC50 96 hours for fish.
  • nonionic stabiliser has an HLB of between 10 and 20, more preferably 12 and 20.
  • the level of nonionic stabiliser is within the range from 0.1 to 10% by weight, more preferably from 0.5 to 5% by weight, most preferably from 1 to 4% by weight.
  • the mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to about 1:1, preferably within the range from 18:1 to about 3:1.
  • the composition can also contain fatty acids for example C 8 - C24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • fatty acids for example C 8 - C24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • saturated fatty acids are used, in particular, hardened tallow C16-C18 fatty acids.
  • the fatty acid is non-saponified, more preferably the fatty acid is free for example oleic acid, lauric acid or tallow fatty acid.
  • the level of fatty acid material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight.
  • the weight ratio of quaternary ammonium material to fatty acid material is preferably from 10:1 to 1:10.
  • compositions of the invention preferably have a pH of more than 2.0, more preferably less than 5.
  • the composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • optional ingredients selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • composition may also contain nonionic fabric softening agents such as lanolin and derivatives thereof.
  • Liquid fabric softening compositions were made as follows.
  • the cationic fabric softening agent, fatty acid and nonionic stabilising agent where appropriate were premixed and heated together to form a clear melt.
  • the molten mixture thus formed was added over a period of at least one minute, to water at 70°C to 80°C with constant stirring to form a dispersion.
  • the viscosity of the compositions was measured by Haake rotoviscometer following 21 days storage at ambient temperature or at 5°C.
  • composition A fabric softening compositions comprising conventional quaternary ammonium compounds do not show physical instability on short term storage at 5°C
  • compositions comprising ester-linked quaternaries and fatty acid composition E
  • composition E composition E
  • Liquid fabric softening compositions as given below were made as described in Example 1.
  • the soil release properties imparted to polyester test pieces by treatment with the compositions was assessed by measuring the change in reflectance following staining and a subsequent wash in a proprietary detergent composition.
  • the pieces were first rinsed for 5 minutes in 1 litre of 14°FH water containing 0.67 ml of either composition.
  • the pieces were then line dried and stained with 100 micro litres of olive oil containing 0.06% sudan red dye.
  • the stain was allowed to spread for a minimum of two days following which the reflectance of the stained piece (R 1 ) was measured using an ICS micromatch.
  • compositions according to the invention are as follows:

Abstract

A fabric softening composition comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent wherein the water insoluble cationic fabric softening agent is a biodegradable quaternary ammonium material with at least one ester link and the nonionic stabilising agent is selected from:
  • i. a linear C8 to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide, or
  • ii. a C₁₀ to C₂₀ alcohol or mixtures thereof.
The invention also provides a process for making the liquid fabric softening composition comprising the steps of
  • i. mixing and heating the cationic fabric softening agent and nonionic stabilising agent to form a melt and
  • ii. dispersing the melt in water.

Description

  • The present invention relates to fabric softening compositions, in particular the invention relates to aqueous dispersions of biodegradable fabric softening compositions comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent suitable as rinse-added fabric softener compositions.
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates. In addition to softening, fabric softening compositions desirably have other benefits. One is the ability to confer soil release properties to fabrics, particularly those woven from polyester fibres.
  • One of the problems associated with fabric softening compositions is the physical instability of such compositions when stored. This problem is accentuated by having a concentrated composition and by storage at low temperatures.
  • Concentrates and storage stability at low temperatures are however desired by the consumer. Physical instability manifests as a thickening on storage of the composition to a level where the composition is no longer pourable and can even lead to the formation of an irreversible gel. The thickening is very undesirable since the composition can no longer be conveniently used.
  • In the past physical stability of rinse added fabric softener compositions has been improved by the addition of viscosity control agents or anti-gelling agents. For example in EP 13780 (Procter and Gamble) viscosity control agents are added to certain concentrated compositions. The agents may include C₁₀-C₁₈ fatty alcohols. More recently in. EP 280550 (Unilever) it has been proposed to improve the physical stability of dilute compositions comprising biodegradable, ester-linked quaternary ammonium compounds and fatty acid by the addition of nonionic surfactants.
  • With concentrated compositions comprising biodegradable ester-linked quaternary ammonium compounds the problem of physical instability is more acute than with traditional quaternary ammonium compounds.
  • In EP 0 040 562 (Lesieur Cotelle) a nonionic emulsifier/stabiliser is added to a concentrate comprising an ester-linked quaternary ammonium compound to form a viscous gel. The stabiliser is a C₁₂ to C₁₄ alcohol ethoxylated with 9 molecules of ethylene oxide. The degree of branching of the alcohol is not, however, mentioned.
  • Certain nonionic stabilising agents not only stabilise concentrated compositions comprising biodegradable quaternary ammonium compounds but are also environmentally friendly, in that they show acceptable biodegradability and are not substantially toxic in aquatic systems.
  • Soil release properties are generally imparted to fabrics by the use of separate soil-release agents, usually a high molecular weight polymer, in a detergent composition or separate treatment. For example in EP 0 398 133A (Procter & Gamble) there is disclosed a cationic polymeric soil release agent for use in a fabric conditioning composition.
  • A disadvantage of such compositions is that the soil release agent increases the number of components in the formulation, increasing cost and making the product less environmentally acceptable.
  • We have now found that fabric softening compositions comprising biodegradable ester-linked quaternary ammonium compounds may confer improved soil release properties to fabrics.
  • Thus, according to one aspect of the invention there is provided a fabric softening composition comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent characterised in that the water insoluble cationic fabric softening agent is a biodegradable quaternary ammonium material with at least one ester link and the nonionic stabilising agent is
    • i. a linear C8 to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide
      or
    • ii. a C₁₀ to C₂₀ alcohol or mixtures thereof.
  • Advantageously the nonionic stabilising agent is a linear C8 to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide
  • Preferably the compositions of the invention are liquids comprising an aqueous base.
  • Advantageously the fabric softening composition comprises a water insoluble cationic which is a compound having two C₁₂₋₂₈ alkyl or alkenyl groups connected to the N atom via one or more ester links.
  • A preferred type of ester-linked quaternary ammonium material for use in the compositions according to the invention can be represented by the formula:
    Figure imgb0001

    wherein each R1 group is independently selected from C₁₋₄ alkyl, alkenyl or hydroxyalkyl groups; and wherein each R2 group is independently selected from C₈₋₂₈ alkyl or alkenyl groups;
    T is
    Figure imgb0002

    or
    Figure imgb0003

    and
    n is an integer from 0-5.
  • A second preferred type of quaternary ammonium material can be represented by the formula:
    Figure imgb0004

    wherein R1, n and R2 are as defined above.
  • Preferred materials of this class and their method of preparation are, for example, described in US 4 137 180 (Lever Brothers). Preferably these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-tallowoxy, 2-hydroxytrimethyl ammonium propane chloride.
  • Preferably the level of ester linked quaternary ammonium compounds is at least 1% by weight of the composition, more preferably more than 3% by weight of the composition; especially interesting are concentrated compositions which comprise more than 7% of ester-linked quaternary ammonium compound. The level of ester-linked quaternary ammonium compounds preferably is between 1% and 80% by weight, more preferably 3% to 50%, most preferably 8% to 50%.
  • Suitable nonionic stabilisers which can be used include the condensation products of C8 - C₂₂ primary linear alcohols with 10 to 20 moles of ethylene oxide. The term linear alcohol means a primary alcohol attached directly to a hydrocarbon backbone structure. Use of less than 10 moles of ethylene oxide, especially when the alkyl chain is in the tallow range, leads to unacceptably high aquatic toxicity. Since the aquatic toxicity is related to both the number of moles of ethylene oxide and the length of the alkyl chain we have found that the HLB value can be used as an indication of likely aquatic toxicity. An HLB of greater than about 12 gives rise to an acceptable acute aquatic toxicity value of >1mg/1;EC₅₀ 48 hours for daphnia and algae and EC₅₀ 96 hours for fish. The selection of linear alcohols and the use of 20 moles or less of ethylene oxide gives acceptable biodegradability to the nonionic stabiliser. However the use of nonionic stabilisers with more than 20 ethylene oxide units will also provide the stability benefit .The alcohols may be saturated or unsaturated. In particular Genapol T-110, Genapol T-150, Genapol T-200, Genapol C-200 all ex Hoeschst AG, Lutensol AT18 ex BASF, Genapol 0-100 and Genapol 0-150 ex Hoechst, or fatty alcohols for example Laurex CS, ex Albright and Wilson or Adol 340 ex Sherex. Preferably the nonionic stabiliser has an HLB of between 10 and 20, more preferably 12 and 20.
  • Preferably, the level of nonionic stabiliser is within the range from 0.1 to 10% by weight, more preferably from 0.5 to 5% by weight, most preferably from 1 to 4% by weight. The mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to about 1:1, preferably within the range from 18:1 to about 3:1.
  • The composition can also contain fatty acids for example C8 - C₂₄ alkyl or alkenyl monocarboxylic acids or polymers thereof. Preferably saturated fatty acids are used, in particular, hardened tallow C₁₆-C₁₈ fatty acids. Preferably the fatty acid is non-saponified, more preferably the fatty acid is free for example oleic acid, lauric acid or tallow fatty acid.
  • The level of fatty acid material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight. The weight ratio of quaternary ammonium material to fatty acid material is preferably from 10:1 to 1:10.
  • The compositions of the invention preferably have a pH of more than 2.0, more preferably less than 5.
  • The composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • The composition may also contain nonionic fabric softening agents such as lanolin and derivatives thereof.
  • The invention will now be illustrated by the following non-limiting examples. In the examples all percentages are expressed by weight.
  • Example 1
  • Liquid fabric softening compositions were made as follows.
  • The cationic fabric softening agent, fatty acid and nonionic stabilising agent where appropriate were premixed and heated together to form a clear melt. The molten mixture thus formed was added over a period of at least one minute, to water at 70°C to 80°C with constant stirring to form a dispersion.
  • The viscosity of the compositions was measured by Haake rotoviscometer following 21 days storage at ambient temperature or at 5°C.
    Figure imgb0005
    Figure imgb0006
  • The results show that while known fabric softening compositions comprising conventional quaternary ammonium compounds do not show physical instability on short term storage at 5°C (composition A) a problem is experienced with compositions comprising ester-linked quaternaries and fatty acid (composition E). The results also show that addition of selected nonionic stabilising agents counteract destabilisation to give stable concentrated compositions.
  • Example 2
  • Liquid fabric softening compositions as given below were made as described in Example 1. The soil release properties imparted to polyester test pieces by treatment with the compositions was assessed by measuring the change in reflectance following staining and a subsequent wash in a proprietary detergent composition. The pieces were first rinsed for 5 minutes in 1 litre of 14°FH water containing 0.67 ml of either composition. The pieces were then line dried and stained with 100 micro litres of olive oil containing 0.06% sudan red dye. The stain was allowed to spread for a minimum of two days following which the reflectance of the stained piece (R1) was measured using an ICS micromatch. The pieces were then washed, rinsed and line dried using 5g/1 New System Persil Automatic ex Lever in 14°FH water for a 15 minute wash cycle. The reflectance of the pretreated, washed piece (R2) was measured and the percentage detergency calculated according to the following equation: % Detergency = Ks 1 - Ks 2 Ks 1 x 100
    Figure imgb0007
    where Ks 1 = (1 - R 1 ) 2 2R 1 and Ks 2 = (1 - R 2 ) 2 2R 2
    Figure imgb0008
  • The higher the percentage detergency, the greater the soil release benefit.
    Figure imgb0009
    Figure imgb0010
  • Example 3
  • Preferred compositions according to the invention are as follows:
    Figure imgb0011

Claims (10)

  1. A fabric softening composition comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent characterised in that the water insoluble cationic fabric softening agent is a biodegradable quaternary ammonium material with at least one ester link and the nonionic stabilising agent is
    i. a linear C8 to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide, or
    ii. a C₁₀ to C₂₀ alcohol or mixtures thereof.
  2. A composition as claimed in claim 1 wherein the nonionic stabilising agent is a linear C8 to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide.
  3. A composition as claimed in claim 1 or claim 2 characterised in that the composition comprises at least 1% by weight of the quaternary ammonium material.
  4. A composition as claimed in any preceding claim characterised in that the composition comprises from 0.1 to 10% by weight of the nonionic stabilising agent.
  5. A composition as claimed in any preceding claim characterised in that the composition also comprises more than 0.1% by weight of a fatty acid material.
  6. A composition as claimed in any preceding claim characterised in that the composition comprises from 3% to 50% by weight of the quaternary ammonium material, from 0.5% to 5% by weight of the nonionic stabilising agent and from 0.5 to 20% by weight of fatty acid material.
  7. A composition as claimed in any preceding claim characterised in that the nonionic stabilising agent has an HLB of between 10 and 20.
  8. A composition as claimed in claim 7 wherein the nonionic stabilising agent has an HLB of between 12 and 20.
  9. A fabric softening composition as claimed in any preceding claim wherein the water insoluble cationic comprises a compound having two C₁₂₋₂₈ alkyl or alkenyl groups connected to the N atom via one or more ester links.
  10. Process for making a liquid fabric softening composition as claimed in any of claims 1 to 9 comprising the steps of
    i. mixing and heating the cationic fabric softening agent and nonionic stabilising agent to form a melt and
    ii. dispersing the melt in water.
EP92302452A 1991-03-25 1992-03-20 Fabric softening composition Revoked EP0507478B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919106308A GB9106308D0 (en) 1991-03-25 1991-03-25 Fabric softening composition
GB9106308 1991-03-25

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EP0507478A1 true EP0507478A1 (en) 1992-10-07
EP0507478B1 EP0507478B1 (en) 1996-06-05

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EP92302453A Expired - Lifetime EP0506312B1 (en) 1991-03-25 1992-03-20 Use of fabric softening composition
EP92302452A Revoked EP0507478B1 (en) 1991-03-25 1992-03-20 Fabric softening composition

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JP (1) JP2937306B2 (en)
AU (1) AU652429B2 (en)
BR (1) BR9201017A (en)
CA (1) CA2063463C (en)
DE (2) DE69207624T2 (en)
ES (2) ES2083084T3 (en)
GB (1) GB9106308D0 (en)
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Cited By (20)

* Cited by examiner, † Cited by third party
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EP0523922A2 (en) * 1991-07-15 1993-01-20 Unilever Plc Fabric softening composition
WO1993023510A1 (en) * 1992-05-12 1993-11-25 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
WO1993025648A1 (en) * 1992-06-10 1993-12-23 The Procter & Gamble Company Stable biodegradable fabric softening compounds and compositions
WO1994017168A1 (en) * 1993-01-28 1994-08-04 Unilever Plc Fabric softening composition
EP0658618A2 (en) * 1993-12-17 1995-06-21 INTERNATIONAL FLAVORS & FRAGRANCES INC. Use of special surfactants to control viscosity in fabric softeners
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5460736A (en) * 1994-10-07 1995-10-24 The Procter & Gamble Company Fabric softening composition containing chlorine scavengers
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
EP0704522A2 (en) * 1994-09-20 1996-04-03 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
WO1997008286A1 (en) * 1995-08-25 1997-03-06 Unilever Plc Soil release agent and its use in fabric conditioning compositions
US5643865A (en) * 1994-05-18 1997-07-01 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing quaternary ammonium compounds with short fatty acid alkyl chains
WO1997023590A1 (en) * 1995-12-21 1997-07-03 Unilever Plc Fabric softening composition
GB2313379A (en) * 1996-05-23 1997-11-26 Unilever Plc A detergent composition comprising perfume
US5700387A (en) * 1994-04-07 1997-12-23 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US5721205A (en) * 1994-04-29 1998-02-24 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
US5773409A (en) * 1994-04-07 1998-06-30 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US6559117B1 (en) 1993-12-13 2003-05-06 The Procter & Gamble Company Viscosity stable concentrated liquid fabric softener compositions
US6992059B2 (en) 2001-09-10 2006-01-31 Unilever Home & Personal Care Usa Divisionof Conopco, Inc. Fabric conditioning compositions

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* Cited by examiner, † Cited by third party
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GB9503596D0 (en) * 1995-02-23 1995-04-12 Unilever Plc Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
BR9701287A (en) * 1997-03-14 1998-11-10 Unilever Nv Fabric treatment composition in washing and process to treat fabrics to provide them with dirt repellent properties
EP1354872A1 (en) 2002-04-17 2003-10-22 Kao Corporation Sulfuric acid ester amine salts, sulfonic acid amine salts, production thereof and softener composition
DE602004015129D1 (en) * 2003-10-16 2008-08-28 Procter & Gamble AQUEOUS COMPOSITIONS WITH VESICLES WITH CERTAIN VASCULAR PERMEABILITY
US7655609B2 (en) 2005-12-12 2010-02-02 Milliken & Company Soil release agent
US9926516B2 (en) 2014-06-05 2018-03-27 The Procter & Gamble Company Mono alcohols for low temperature stability of isotropic liquid detergent compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2257728A1 (en) * 1974-01-11 1975-08-08 Procter & Gamble
US4789491A (en) * 1987-08-07 1988-12-06 The Procter & Gamble Company Method for preparing biodegradable fabric softening compositions
EP0293953A2 (en) * 1987-05-01 1988-12-07 The Procter & Gamble Company Quaternary mono-ester ammonium compounds as fibre and fabric treatment compositions
EP0309052A2 (en) * 1987-09-23 1989-03-29 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
EP0331237A2 (en) * 1988-03-01 1989-09-06 Unilever N.V. Fabric softening composition
EP0346634A1 (en) * 1988-05-27 1989-12-20 Henkel Kommanditgesellschaft auf Aktien Liquid aqueous composition for the aftertreatment of laundry

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1567947A (en) * 1976-07-02 1980-05-21 Unilever Ltd Esters of quaternised amino-alcohols for treating fabrics
ATE8660T1 (en) * 1980-06-17 1984-08-15 The Procter & Gamble Company DETERGENT COMPOSITION WITH A LOW CONTENT OF SUBSTITUTED POLYAMINE.
DE3605716A1 (en) * 1986-02-22 1987-09-03 Henkel Kgaa USE OF INSOLUBLE DIRT COLLECTORS FOR REGENERATING WASHING AND CLEANING SOLUTIONS
GB8704711D0 (en) * 1987-02-27 1987-04-01 Unilever Plc Fabric softening composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2257728A1 (en) * 1974-01-11 1975-08-08 Procter & Gamble
EP0293953A2 (en) * 1987-05-01 1988-12-07 The Procter & Gamble Company Quaternary mono-ester ammonium compounds as fibre and fabric treatment compositions
US4789491A (en) * 1987-08-07 1988-12-06 The Procter & Gamble Company Method for preparing biodegradable fabric softening compositions
EP0309052A2 (en) * 1987-09-23 1989-03-29 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
EP0331237A2 (en) * 1988-03-01 1989-09-06 Unilever N.V. Fabric softening composition
EP0346634A1 (en) * 1988-05-27 1989-12-20 Henkel Kommanditgesellschaft auf Aktien Liquid aqueous composition for the aftertreatment of laundry

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0523922A3 (en) * 1991-07-15 1993-06-09 Unilever Plc Fabric softening composition
AU662536B2 (en) * 1991-07-15 1995-09-07 Unilever Plc Fabric softening composition
EP0523922A2 (en) * 1991-07-15 1993-01-20 Unilever Plc Fabric softening composition
US5417868A (en) * 1992-01-28 1995-05-23 Unilever Patent Holdings B.V. Fabric softening composition
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
EP0894848A1 (en) * 1992-05-12 1999-02-03 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
WO1993025648A1 (en) * 1992-06-10 1993-12-23 The Procter & Gamble Company Stable biodegradable fabric softening compounds and compositions
WO1994017168A1 (en) * 1993-01-28 1994-08-04 Unilever Plc Fabric softening composition
AU680232B2 (en) * 1993-01-28 1997-07-24 Unilever Plc Fabric softening composition
US5574179A (en) * 1993-03-01 1996-11-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains
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
US5562849A (en) * 1993-03-01 1996-10-08 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
US6559117B1 (en) 1993-12-13 2003-05-06 The Procter & Gamble Company Viscosity stable concentrated liquid fabric softener compositions
EP0658618A2 (en) * 1993-12-17 1995-06-21 INTERNATIONAL FLAVORS & FRAGRANCES INC. Use of special surfactants to control viscosity in fabric softeners
EP0658618A3 (en) * 1993-12-17 1996-12-11 Int Flavors & Fragrances Inc Use of special surfactants to control viscosity in fabric softeners.
US5700387A (en) * 1994-04-07 1997-12-23 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US5773409A (en) * 1994-04-07 1998-06-30 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening composition
US5721205A (en) * 1994-04-29 1998-02-24 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5643865A (en) * 1994-05-18 1997-07-01 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing quaternary ammonium compounds with short fatty acid alkyl chains
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
EP0704522A2 (en) * 1994-09-20 1996-04-03 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
EP0704522A3 (en) * 1994-09-20 1996-05-01 Procter & Gamble
US5460736A (en) * 1994-10-07 1995-10-24 The Procter & Gamble Company Fabric softening composition containing chlorine scavengers
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
WO1997008286A1 (en) * 1995-08-25 1997-03-06 Unilever Plc Soil release agent and its use in fabric conditioning compositions
WO1997023590A1 (en) * 1995-12-21 1997-07-03 Unilever Plc Fabric softening composition
US5985820A (en) * 1995-12-21 1999-11-16 Lever Brothers Company Fabric softening composition
AU721656B2 (en) * 1995-12-21 2000-07-13 Unilever Plc Fabric softening composition
GB2313379A (en) * 1996-05-23 1997-11-26 Unilever Plc A detergent composition comprising perfume
US6992059B2 (en) 2001-09-10 2006-01-31 Unilever Home & Personal Care Usa Divisionof Conopco, Inc. Fabric conditioning compositions

Also Published As

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AU652429B2 (en) 1994-08-25
JP2937306B2 (en) 1999-08-23
ES2083084T3 (en) 1996-04-01
AU1312592A (en) 1992-10-01
EP0507478B1 (en) 1996-06-05
DE69207624T2 (en) 1996-05-30
ES2088542T3 (en) 1996-08-16
ZA922173B (en) 1993-09-27
DE69211203T2 (en) 1996-10-10
DE69207624D1 (en) 1996-02-29
GB9106308D0 (en) 1991-05-08
DE69211203D1 (en) 1996-07-11
JPH05106166A (en) 1993-04-27
EP0506312A1 (en) 1992-09-30
CA2063463C (en) 1999-04-27
EP0506312B1 (en) 1996-01-17
BR9201017A (en) 1992-11-24
CA2063463A1 (en) 1992-09-26

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