EP0506312A1 - Use of fabric softening composition - Google Patents
Use of fabric softening composition Download PDFInfo
- Publication number
- EP0506312A1 EP0506312A1 EP19920302453 EP92302453A EP0506312A1 EP 0506312 A1 EP0506312 A1 EP 0506312A1 EP 19920302453 EP19920302453 EP 19920302453 EP 92302453 A EP92302453 A EP 92302453A EP 0506312 A1 EP0506312 A1 EP 0506312A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- quaternary ammonium
- weight
- ammonium material
- fabric softening
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic 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
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Definitions
- the present invention relates to the use as a soil release agent in a fabric softening composition of a biodegradable quaternary ammonium material.
- 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 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.
- 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 soil release properties to fabrics without the use of a separate soil release agent.
- a soil release agent in a fabric softening composition of a quaternary ammonium material comprising a compound having two C12 ⁇ 28 alkyl or alkenyl groups connected via an ester link to the quaternary nitrogen atom.
- composition is a liquid comprising an aqueous base.
- 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 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).
- 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%.
- the softening composition may be stabilised at low temperatures by the addition of nonionic stabilisers.
- 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 alcohols may be saturated or unsaturated.
- 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.
- the nonionic stabiliser has an HLB of between 10 and 20, more preferably 12 and 20.
- the nonionic stabiliser is biodegradable and has low aquatic toxicity.
- Use of less than 10 moles of ethylene oxide results in an acceptable acute aquatic toxicity value of > 1 mg/l EC50 48 hours for daphnia and algae and EC50 96 hours for fish, especially if the HLB of the nonionic is less than 12.
- 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.
- fatty acids for example C8 - 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 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.
- composition B shows a smaller soil release benefit than compositions according to the invention (Composition A).
- Liquid fabric softening compositions as given below were made as described in Example 1.
- the soil release properties of the compositions were measured as described in Example 1 excepting that the pieces were first rinsed in 1 litre of 14°FH water containing 2ml of either composition.
- compositions comprising ester-linked quaternaries show a soil release benefit greater than that obtained from compositions comprising conventional quaternary and that the benefit is seen in the absence of a nonionic stabilising agent.
- Example 2 was repeated with a composition which did not contain any nonionic to show that the improved soil release benefit is due entirely to the use of the biodegradable ester linked quaternary ammonium compound.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- The present invention relates to the use as a soil release agent in a fabric softening composition of a biodegradable quaternary ammonium material.
- 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 itself 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 soil release properties to fabrics without the use of a separate soil release agent.
- According to the invention there is provided the use as a soil release agent in a fabric softening composition of a quaternary ammonium material comprising a compound having two C₁₂₋₂₈ alkyl or alkenyl groups connected via an ester link to the quaternary nitrogen atom.
- Preferably the composition is a liquid comprising an aqueous base.
-
- 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%.
- The softening composition may be stabilised at low temperatures by the addition of nonionic stabilisers. 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 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.
- Advantageously the nonionic stabiliser is biodegradable and has low aquatic toxicity. Use of less than 10 moles of ethylene oxide results in an acceptable acute aquatic toxicity value of > 1 mg/l EC₅₀ 48 hours for daphnia and algae and EC₅₀ 96 hours for fish, especially if the HLB of the nonionic is less than 12.
- 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.
- 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 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 5q/1 New System Persil Automatic 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:
-
- These results show that known compositions comprising conventional quaternary ammonium compositions (Composition B) show a smaller soil release benefit than compositions according to the invention (Composition A).
-
- These results show that compositions comprising ester-linked quaternaries show a soil release benefit greater than that obtained from compositions comprising conventional quaternary and that the benefit is seen in the absence of a nonionic stabilising agent.
-
- This example clearly demonstrates the superior soil release behaviour of use of the softening composition according to the invention. The difference is statistically significant; P<0.05.
Claims (9)
- Use as a soil release agent in a fabric softening composition of at least 1% by weight of a quaternary ammonium material comprising a compound having two C₁₂₋₂₈ alkyl or alkenyl groups connected via an ester link to a hydrocarbon chain which is connected to the quaternary nitrogen atom.
- Use of a quaternary ammonium material as claimed in claim 1 wherein the fabric softening composition comprises a nonionic stabilising agent which isi. a linear C₈ to C₂₂ alcohol alkoxylated with 10 to 20 moles of alkylene oxide orii. a C₁₀ to C₂₀ alcohol or mixtures thereof.
- Use of a quaternary ammonium material as claimed in claim 1 or claim 2 wherein the fabric softening composition comprises a fatty acid material.
- Use of a quaternary ammonium material as claimed in claim 2 wherein the composition comprises from 0.1 to 10% by weight of the nonionic stabilising agent.
- Use of a quaternary ammonium material as claimed in claim 3 wherein the composition also comprises more than 0.1% by weight of a fatty acid material.
- Use of a quaternary ammonium material as claimed in any preceding claim wherein 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.
- Use of a quaternary ammonium material as claimed in any one of claims 2 to 6 wherein the nonionic stabilising agent has an HLB of between 10 and 20.
- Use of a quaternary ammonium material as claimed in claim 7 wherein the nonionic stabilising agent has an HLB of between 12 and 20.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9106308 | 1991-03-25 | ||
GB919106308A GB9106308D0 (en) | 1991-03-25 | 1991-03-25 | Fabric softening composition |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0506312A1 true EP0506312A1 (en) | 1992-09-30 |
EP0506312B1 EP0506312B1 (en) | 1996-01-17 |
Family
ID=10692165
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92302452A Revoked EP0507478B1 (en) | 1991-03-25 | 1992-03-20 | Fabric softening composition |
Country Status (9)
Country | Link |
---|---|
EP (2) | EP0506312B1 (en) |
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) |
ZA (1) | ZA922173B (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0523922A2 (en) * | 1991-07-15 | 1993-01-20 | Unilever Plc | Fabric softening composition |
WO1997008286A1 (en) * | 1995-08-25 | 1997-03-06 | Unilever Plc | Soil release agent and its use in fabric conditioning compositions |
US5741765A (en) * | 1995-02-23 | 1998-04-21 | Lever Brothers Company, Division Of Conopco, Inc. | Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant |
US6075003A (en) * | 1997-03-14 | 2000-06-13 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric laundry treatment composition |
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 |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9301728D0 (en) * | 1993-01-28 | 1993-03-17 | Unilever Plc | Fabric softening composition |
JP3442387B2 (en) * | 1992-05-12 | 2003-09-02 | ザ、プロクター、エンド、ギャンブル、カンパニー | Concentrated fabric softener composition containing biodegradable fabric softener |
ATE150481T1 (en) * | 1992-06-10 | 1997-04-15 | Procter & Gamble | STABLE, BIODEGRADABLE TISSUE PLASTICIZER COMPOSITIONS |
AU6271294A (en) * | 1993-03-01 | 1994-09-26 | Procter & Gamble Company, The | 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 |
US5413723A (en) * | 1993-12-17 | 1995-05-09 | Munteanu; Marina A. | Use of special surfactants to control viscosity in fabric softeners |
CZ290568B6 (en) * | 1994-04-07 | 2002-08-14 | Unilever N. V. | Fabric softening composition |
GB9406824D0 (en) * | 1994-04-07 | 1994-06-01 | Unilever Plc | Fabric softening composition |
AU2399295A (en) * | 1994-04-29 | 1995-11-29 | Procter & Gamble Company, The | Cellulase fabric-conditioning compositions |
MA23554A1 (en) * | 1994-05-18 | 1995-12-31 | Procter & Gamble | SOFTENING COMPOSITIONS FOR BIODEGRADABLE AND CONCENTRATED QUATERNARY AMMONIUM BASED LAUNDRY 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 |
US5503756A (en) * | 1994-09-20 | 1996-04-02 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
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 |
GB9526182D0 (en) * | 1995-12-21 | 1996-02-21 | Unilever Plc | Fabric softening composition |
GB2313379A (en) * | 1996-05-23 | 1997-11-26 | Unilever Plc | A detergent composition comprising perfume |
GB0121802D0 (en) | 2001-09-10 | 2001-10-31 | Unilever Plc | Fabric conditioning compositions |
EP1354872A1 (en) | 2002-04-17 | 2003-10-22 | Kao Corporation | Sulfuric acid ester amine salts, sulfonic acid amine salts, production thereof and softener composition |
JP4633722B2 (en) * | 2003-10-16 | 2011-02-16 | ザ プロクター アンド ギャンブル カンパニー | Aqueous composition comprising vesicles having specific vesicle permeability |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0042187A1 (en) * | 1980-06-17 | 1981-12-23 | THE PROCTER & GAMBLE COMPANY | Detergent composition containing low level of substituted polyamines |
EP0234311A1 (en) * | 1986-02-22 | 1987-09-02 | Henkel Kommanditgesellschaft auf Aktien | Use of insoluble dirt-collectors for the at least partial regeneration of washing and cleaning solutions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3974076A (en) * | 1974-01-11 | 1976-08-10 | The Procter & Gamble Company | Fabric softener |
GB1567947A (en) * | 1976-07-02 | 1980-05-21 | Unilever Ltd | Esters of quaternised amino-alcohols for treating fabrics |
GB8704711D0 (en) * | 1987-02-27 | 1987-04-01 | Unilever Plc | Fabric softening composition |
US4808321A (en) * | 1987-05-01 | 1989-02-28 | The Procter & Gamble Company | Mono-esters as fiber and fabric treatment compositions |
US4789491A (en) * | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
EP0309052B1 (en) * | 1987-09-23 | 1992-11-25 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols |
GB8804818D0 (en) * | 1988-03-01 | 1988-03-30 | Unilever Plc | Fabric softening composition |
DE3818061A1 (en) * | 1988-05-27 | 1989-12-07 | Henkel Kgaa | LIQUID, AQUEOUS LAUNDRY TREATMENT AGENT |
-
1991
- 1991-03-25 GB GB919106308A patent/GB9106308D0/en active Pending
-
1992
- 1992-03-19 CA CA002063463A patent/CA2063463C/en not_active Expired - Lifetime
- 1992-03-20 ES ES92302453T patent/ES2083084T3/en not_active Expired - Lifetime
- 1992-03-20 DE DE69207624T patent/DE69207624T2/en not_active Expired - Lifetime
- 1992-03-20 ES ES92302452T patent/ES2088542T3/en not_active Expired - Lifetime
- 1992-03-20 EP EP92302453A patent/EP0506312B1/en not_active Expired - Lifetime
- 1992-03-20 DE DE69211203T patent/DE69211203T2/en not_active Revoked
- 1992-03-20 EP EP92302452A patent/EP0507478B1/en not_active Revoked
- 1992-03-23 AU AU13125/92A patent/AU652429B2/en not_active Ceased
- 1992-03-24 BR BR929201017A patent/BR9201017A/en not_active IP Right Cessation
- 1992-03-25 JP JP4067575A patent/JP2937306B2/en not_active Expired - Fee Related
- 1992-03-25 ZA ZA922173A patent/ZA922173B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0042187A1 (en) * | 1980-06-17 | 1981-12-23 | THE PROCTER & GAMBLE COMPANY | Detergent composition containing low level of substituted polyamines |
EP0234311A1 (en) * | 1986-02-22 | 1987-09-02 | Henkel Kommanditgesellschaft auf Aktien | Use of insoluble dirt-collectors for the at least partial regeneration of washing and cleaning solutions |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0523922A2 (en) * | 1991-07-15 | 1993-01-20 | Unilever Plc | Fabric softening composition |
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 |
US5741765A (en) * | 1995-02-23 | 1998-04-21 | Lever Brothers Company, Division Of Conopco, Inc. | Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant |
WO1997008286A1 (en) * | 1995-08-25 | 1997-03-06 | Unilever Plc | Soil release agent and its use in fabric conditioning compositions |
US6075003A (en) * | 1997-03-14 | 2000-06-13 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric laundry treatment composition |
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 |
Also Published As
Publication number | Publication date |
---|---|
DE69207624T2 (en) | 1996-05-30 |
GB9106308D0 (en) | 1991-05-08 |
BR9201017A (en) | 1992-11-24 |
ZA922173B (en) | 1993-09-27 |
DE69207624D1 (en) | 1996-02-29 |
AU1312592A (en) | 1992-10-01 |
EP0506312B1 (en) | 1996-01-17 |
EP0507478A1 (en) | 1992-10-07 |
DE69211203D1 (en) | 1996-07-11 |
DE69211203T2 (en) | 1996-10-10 |
EP0507478B1 (en) | 1996-06-05 |
JPH05106166A (en) | 1993-04-27 |
CA2063463A1 (en) | 1992-09-26 |
ES2088542T3 (en) | 1996-08-16 |
CA2063463C (en) | 1999-04-27 |
JP2937306B2 (en) | 1999-08-23 |
ES2083084T3 (en) | 1996-04-01 |
AU652429B2 (en) | 1994-08-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0506312B1 (en) | Use of fabric softening composition | |
CA2021010C (en) | Fabric softening composition | |
US5368756A (en) | Fabric softening compositions containing mixtures of softener material and highly ethoxylated curd dispersant | |
CA2021322C (en) | Fabric softening composition | |
EP0060003B1 (en) | Textile treatment compositions and preparation thereof | |
US5409621A (en) | Fabric softening composition | |
CA2378114C (en) | Fabric conditioning composition containing fatty acid-derived quaternary ammonium compounds and oils | |
US5858960A (en) | Fabric softening composition | |
WO1994019439A1 (en) | Use of fabric softening composition | |
EP0746603B1 (en) | Fabric softening composition | |
EP0280550A2 (en) | Fabric-softening composition | |
US6878684B2 (en) | Fabric conditioning composition | |
US5417868A (en) | Fabric softening composition | |
CA2073517C (en) | Fabric softening composition | |
CA2024699C (en) | Fabric softening | |
CA2619353A1 (en) | Concentrated fabric conditioner compositions | |
AU3410299A (en) | Fabric softening composition | |
JPH03113074A (en) | Composition for softening liquid textile product | |
US5516437A (en) | Fabric softening composition | |
CA2399441C (en) | Fabric conditioning compositions | |
EP0848748A1 (en) | Soil release agent and its use in fabric conditioning compositions |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: UNILEVER PLC Owner name: UNILEVER N.V. |
|
17P | Request for examination filed |
Effective date: 19930223 |
|
17Q | First examination report despatched |
Effective date: 19940909 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
REF | Corresponds to: |
Ref document number: 69207624 Country of ref document: DE Date of ref document: 19960229 |
|
ITF | It: translation for a ep patent filed |
Owner name: JACOBACCI & PERANI S.P.A. |
|
ET | Fr: translation filed | ||
REG | Reference to a national code |
Ref country code: CH Ref legal event code: NV Representative=s name: R. A. EGLI & CO. PATENTANWAELTE |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2083084 Country of ref document: ES Kind code of ref document: T3 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19970228 Year of fee payment: 6 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19980217 Year of fee payment: 7 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19980320 Year of fee payment: 7 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19980331 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19980331 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990321 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19991001 |
|
EUG | Se: european patent has lapsed |
Ref document number: 92302453.3 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 19991001 |
|
EUG | Se: european patent has lapsed |
Ref document number: 92302453.3 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20100326 Year of fee payment: 19 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20100406 Year of fee payment: 19 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20100326 Year of fee payment: 19 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20100329 Year of fee payment: 19 Ref country code: DE Payment date: 20100329 Year of fee payment: 19 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20110320 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST Effective date: 20111130 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20110331 Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20111001 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R119 Ref document number: 69207624 Country of ref document: DE Effective date: 20111001 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20110320 Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20110320 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20120424 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20110321 |