EP0409504A2 - Fabric softening composition - Google Patents
Fabric softening composition Download PDFInfo
- 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
- Authority
- EP
- European Patent Office
- Prior art keywords
- quaternary ammonium
- fabric softening
- materials
- ester
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/645—Mixtures of compounds all of which are cationic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- C11D1/662—Carbohydrates or derivatives
-
- 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
- C11D1/667—Neutral esters, e.g. sorbitan esters
-
- 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 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.
- each R 1 group is independently selected from C 1-4 alkyl, alkenyl or hydroxyalkyl groups; each R 2 group is independently selected from C12-24 alkyl or alkenyl groups; T is and n is an integer from 0-5.
- ester-linked quaternary ammonium materials are particularly preferred for use in fabric conditioners because they are more biodegradable than conventional quaternary ammonium materials.
- the present invention relates to a fabric softening composition which comprises:
- 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.
- 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.
- 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.
- predominantly linear nonionic material refers to materials having a molecular backbone whereto no- or only a small number of side groups are attached.
- the molecular backbone constitutes more than 75% by weight of the molecule, more preferred more than 90%.
- 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:
- 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.
- 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.
- 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 10 ⁇ m, preferably less than 7 ⁇ m, especially preferred less than 3u.m.
- Such small particle dispersion are often referred to as microdispersions.
- compositions of the invention preferably have a pH of more than 2.0.
- pH of the composition is less than 8.0, more preferably less than 5.0.
- 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.
- 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.
- 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 C 1 -C 4 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-brom
- 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.
- 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.
- 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.
- 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.
- compositions of the present invention A-C
- biodegradable softener actives D
- compositions were prepared as in example 1.
- compositions were prepared as in example 1.
- compositions were prepared as in example 1.
Abstract
- (i) an ester-linked quaternary ammonium material of the formula:
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:
-
-
- 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:
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:
- (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.
- 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.
- 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:
- These results show a surprisingly good softening effect for compositions of the present invention (A-C) compared to currently available biodegradable softener actives (D).
-
-
-
-
Claims (10)
n is an integer from 0-5; and
n is an integer from 0-5; and
said dispersion having mean partice diameter of less than 10µm.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898916307A GB8916307D0 (en) | 1989-07-17 | 1989-07-17 | Fabric softening composition |
GB8916307 | 1989-07-17 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0409504A2 true EP0409504A2 (en) | 1991-01-23 |
EP0409504A3 EP0409504A3 (en) | 1991-10-02 |
EP0409504B1 EP0409504B1 (en) | 1996-09-25 |
Family
ID=10660146
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90307693A Expired - Lifetime EP0409504B1 (en) | 1989-07-17 | 1990-07-13 | Fabric softening composition |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0409504B1 (en) |
JP (1) | JP2611035B2 (en) |
AU (1) | AU637803B2 (en) |
BR (1) | BR9003454A (en) |
CA (1) | CA2021010C (en) |
DE (1) | DE69028667T2 (en) |
ES (1) | ES2093016T3 (en) |
GB (1) | GB8916307D0 (en) |
ZA (1) | ZA905608B (en) |
Cited By (29)
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 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5851982A (en) * | 1994-07-27 | 1998-12-22 | Kao Corporation | Liquid softener compositions and quaternary ammonium salt |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2356627A1 (en) * | 1976-07-02 | 1978-01-27 | Unilever Nv | CLOTH TREATMENT AGENTS |
US4260529A (en) * | 1978-06-26 | 1981-04-07 | The Procter & Gamble Company | Detergent composition consisting essentially of biodegradable nonionic surfactant and cationic surfactant containing ester or amide |
EP0239910A2 (en) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biodegradable fabric softeners |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3138181A1 (en) * | 1981-09-25 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | TEXTILE TREATMENT AGENTS AND THEIR USE FOR FINISHING TEXTILE MATERIALS |
US4789491A (en) * | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
DE3876196T2 (en) * | 1987-09-23 | 1993-04-15 | Procter & Gamble | LINEAR ALCOXYLATED ALCOHOLS CONTAINING STABLE, BIODEGRADABLE SOFTEN SOFTENER COMPOSITIONS. |
-
1989
- 1989-07-17 GB GB898916307A patent/GB8916307D0/en active Pending
-
1990
- 1990-07-12 CA CA002021010A patent/CA2021010C/en not_active Expired - Fee Related
- 1990-07-13 DE DE69028667T patent/DE69028667T2/en not_active Expired - Fee Related
- 1990-07-13 ES ES90307693T patent/ES2093016T3/en not_active Expired - Lifetime
- 1990-07-13 EP EP90307693A patent/EP0409504B1/en not_active Expired - Lifetime
- 1990-07-13 AU AU58947/90A patent/AU637803B2/en not_active Ceased
- 1990-07-17 JP JP2189297A patent/JP2611035B2/en not_active Expired - Lifetime
- 1990-07-17 ZA ZA905608A patent/ZA905608B/en unknown
- 1990-07-17 BR BR909003454A patent/BR9003454A/en not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2356627A1 (en) * | 1976-07-02 | 1978-01-27 | Unilever Nv | CLOTH TREATMENT AGENTS |
US4260529A (en) * | 1978-06-26 | 1981-04-07 | The Procter & Gamble Company | Detergent composition consisting essentially of biodegradable nonionic surfactant and cationic surfactant containing ester or amide |
EP0239910A2 (en) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biodegradable fabric softeners |
Cited By (46)
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 |
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 |
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 |
US5403500A (en) * | 1992-04-28 | 1995-04-04 | Lever Brothers Company | Rinse conditioner |
WO1993023510A1 (en) * | 1992-05-12 | 1993-11-25 | 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 |
CN1045109C (en) * | 1992-05-12 | 1999-09-15 | 普罗格特-甘布尔公司 | 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 |
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 |
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 |
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 |
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 |
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 |
US5463094A (en) * | 1994-05-23 | 1995-10-31 | Hoechst Celanese Corporation | Solvent free quaternization of tertiary amines with dimethylsulfate |
US5552137A (en) * | 1994-08-05 | 1996-09-03 | Witco Corporation | Biodegradable quaternary hair conditioners |
US5610187A (en) * | 1994-08-05 | 1997-03-11 | Witco Corporation | Biodegradable quaternary hair and skin conditioners |
US5445747A (en) * | 1994-08-05 | 1995-08-29 | The Procter & Gamble Company | Cellulase fabric-conditioning compositions |
US5578234A (en) * | 1994-09-20 | 1996-11-26 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
US5503756A (en) * | 1994-09-20 | 1996-04-02 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
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 |
EP0728737A1 (en) * | 1995-02-24 | 1996-08-28 | Kao Corporation | Quaternary ammonium salt, method for production thereof, and softener composition using salt |
US5696070A (en) * | 1995-02-24 | 1997-12-09 | Kao Corporation | Quarternary ammonium salt, method for production thereof, and softener composition using salt |
US6040071A (en) * | 1995-03-01 | 2000-03-21 | Colgate-Palmolive Co | Laundry concentrates |
US5856287A (en) * | 1995-03-01 | 1999-01-05 | Colgate-Palmolive Co. | Laundry concentrates |
US6040287A (en) * | 1995-03-01 | 2000-03-21 | Colgate-Palmolive Co | Laundry concentrates |
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 |
EP1179582A2 (en) * | 1995-10-23 | 2002-02-13 | Unilever Plc | Fabric softening composition |
EP1179582A3 (en) * | 1995-10-23 | 2003-07-16 | Unilever Plc | Fabric softening composition |
EP0789070B2 (en) † | 1996-02-09 | 2009-01-21 | Unilever Plc | Fabric softening composition |
GB2301843A (en) * | 1996-05-10 | 1996-12-18 | Unilever Plc | Stable fabric conditioning composition |
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 |
EP1096055A4 (en) * | 1998-06-11 | 2002-06-26 | Kao Corp | Softener composition |
US6521588B1 (en) | 1998-06-11 | 2003-02-18 | 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 |
Also Published As
Publication number | Publication date |
---|---|
EP0409504A3 (en) | 1991-10-02 |
CA2021010C (en) | 2000-10-31 |
BR9003454A (en) | 1991-08-27 |
ES2093016T3 (en) | 1996-12-16 |
EP0409504B1 (en) | 1996-09-25 |
DE69028667D1 (en) | 1996-10-31 |
GB8916307D0 (en) | 1989-08-31 |
AU637803B2 (en) | 1993-06-10 |
ZA905608B (en) | 1992-03-25 |
DE69028667T2 (en) | 1997-03-06 |
AU5894790A (en) | 1991-01-17 |
JP2611035B2 (en) | 1997-05-21 |
JPH0390677A (en) | 1991-04-16 |
CA2021010A1 (en) | 1991-01-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2021010C (en) | Fabric softening composition | |
EP0409502B1 (en) | Fabric softening composition | |
EP0507478B1 (en) | Fabric softening composition | |
EP0326213B1 (en) | A fabric treatment composition and the preparation thereof | |
EP0060003B1 (en) | Textile treatment compositions and preparation thereof | |
US5858960A (en) | Fabric softening composition | |
EP0746603B1 (en) | Fabric softening composition | |
IL168583A (en) | Fabric softening composition containing esterquat with specific ester distribution and sequestrant | |
EP0754221B1 (en) | Process for softening fabrics | |
EP0125031A1 (en) | Liquid fabric-softening composition | |
CA2153487A1 (en) | Fabric softening composition | |
AU2003297264B2 (en) | Concentrated fabric softening composition containing esterquat with specific ester distribution and an electrolyte | |
CA2021128C (en) | Fabric softening composition | |
EP0754217B1 (en) | Fabric softening composition | |
US20030114335A1 (en) | Blend of imidazolinium quat and dialkyl dimethyl quat for use in high-solids fabric softeners with premium softening and viscosity properties |
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: A2 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
17P | Request for examination filed |
Effective date: 19911005 |
|
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: UNILEVER N.V. Owner name: UNILEVER PLC |
|
17Q | First examination report despatched |
Effective date: 19940824 |
|
GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
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 |
|
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 FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 19960925 Ref country code: LI Effective date: 19960925 Ref country code: CH Effective date: 19960925 |
|
REF | Corresponds to: |
Ref document number: 69028667 Country of ref document: DE Date of ref document: 19961031 |
|
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: ES Ref legal event code: FG2A Ref document number: 2093016 Country of ref document: ES Kind code of ref document: T3 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Effective date: 19961225 |
|
NLV1 | Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act | ||
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
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 | ||
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: FR Payment date: 20020619 Year of fee payment: 13 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20020710 Year of fee payment: 13 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20020730 Year of fee payment: 13 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20020807 Year of fee payment: 13 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20030713 |
|
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: 20030714 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040203 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20030713 |
|
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: 20040331 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20030714 |
|
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: 20050713 |