WO2009150017A1 - Improvements relating to fabric conditioners - Google Patents
Improvements relating to fabric conditioners Download PDFInfo
- Publication number
- WO2009150017A1 WO2009150017A1 PCT/EP2009/056126 EP2009056126W WO2009150017A1 WO 2009150017 A1 WO2009150017 A1 WO 2009150017A1 EP 2009056126 W EP2009056126 W EP 2009056126W WO 2009150017 A1 WO2009150017 A1 WO 2009150017A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- perfume
- composition
- fabric softening
- water
- softening active
- Prior art date
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Classifications
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- 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
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- 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
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
Definitions
- the present invention concerns a process for the preparation of encapsulated perfume in fabric softener compositions.
- encapsulated perfume components in fabric conditioners is advantageous in that it enables the improved storage and delivery of perfumes and perfume components.
- Such technologies provide enhanced fragrance delivery over conventional free perfume oil by overcoming the issue of perfume loss during the drying process by protecting the perfume in the capsule.
- the encaps themselves are relatively fragile and contain volatile perfume components which are depleted if rupture of the encap casing occurs. Accordingly, in a typical method of manufacture, the encaps are introduced into the active mixture at a late stage of the process in order to preserve them. Typically, water and minor ingredients such as antifoam and preservative are heated whilst the softening active is melted separately. The molten active is then added to the hot water with agitation before being allowed to cool. Only then is the encapsulated perfume added to the mixture, along with any free perfume oil. Such a sequence of steps, with the addition of the encaps taking place after the addition of the molten active to the water phase, helps to preserve the fragile encaps and minimises damage to these relatively delicate components.
- a process for preparing a composition comprising an ester- linked quaternary ammonium fabric softening active, an encapsulated perfume and a non-confined perfume, wherein the process comprises the step of dispersing the encapsulated perfume in water before the addition of the fabric softening active to the water, and wherein the composition is free from calcium chloride and benzalkonium chloride.
- composition obtainable from the process of the first aspect of the invention.
- the encapsulated perfume is added to the water phase, before the addition of the molten active.
- the water phase may also contain minor components such as preservatives and antifoam.
- Non-confined perfume oil is added in the conventional way, after the active and water phases have been combined and cooled.
- a preferred process of the invention comprises the steps of:- 1) mixing perfume encaps, and optional minors such as preservatives and anti-foam, with heated water to form a water phase;
- the molten active is added to the water phase, wherein the water phase contains perfume encapsulates. It is preferable that 100 % of the molten active is added at this stage, although the addition of a minor amount of molten active to the water phase before the encaps are added is also covered by the present invention.
- minor amount is meant, for example, from 0.0001 to 25 %, for example 20, or 10 %.
- Suitable fabric softening actives which may be used in the process and compositions of the present invention include cationic or non-ionic conditioning agents, but preferably they will be cationic.
- the softening active for use in the process and compositions of the invention is a quaternary ammonium compound, more specifically an ester-linked quaternary ammonium compound.
- Preferred quaternary ammonium compounds for use in the process of the invention have unsaturated chains, i.e. are the so-called "soft" quats.
- Such compounds are typically derived from fatty acyl or fatty acid feed stock having an Iodine Value of from 20 to 140, preferably from 20 to 60, more preferably from 20 to 50, most preferably from 25 to 45.
- the unsaturated chains come from the unsaturated fatty feed stock.
- the iodine value represents the mean iodine value of the parent fatty acyl compounds or fatty acids of all of the quaternary ammonium materials present.
- the iodine value represents the mean iodine value of the parent fatty acyl compounds or fatty acids of all of the quaternary ammonium materials present.
- Iodine value is defined as the number of grams of iodine absorbed per 100 g of test material.
- NMR spectroscopy is a suitable technique for determining the iodine value of the softening agents of the present invention, using the method described in Anal. Chem. , 34, 1136 (1962) by Johnson and Shoolery and in EP 593,542 (Unilever, 1993) .
- the quaternary ammonium compound is preferably present in the compositions of the invention at a level of from 8 % to 20 %, preferably from 10 % to 15 %, for example from 8 to 16 % by weight of the total composition.
- the compositions of the invention are preferably concentrated fabric conditioners .
- such TEA-based fabric softening compounds comprise a mixture of mono, di- and tri-ester forms of the compound.
- the di-ester linked component comprises no more than 70 % by weight of the fabric softening compound, preferably no more than 60 %, e.g. no more than 55 %, or even no more than 45 % of the fabric softening compound and at least 10 % of the monoester linked component .
- TEA ester quats preparations which are rich in the di-esters of triethanolammonium methylsulphate, otherwise referred to as "TEA ester quats".
- Commercial examples include TetranylTM ex Kao, AT-I (di- [tallow ester] of triethanolammonium methylsulphate) , and L5/90 (di- [palm ester] of triethanolammonium methylsulphate) , both ex Kao, and RewoquatTM WE15 (a di-ester of triethanolammonium methylsulphate having fatty acyl residues deriving from C10-C20 and C16-C18 unsaturated fatty acids) , ex Witco Corporation and the Stepantex (ex Stepan) soft range, Stepantex VT90, VA90 and SP90.
- each R 1 group is independently selected from C1-4 alkyl, hydroxyalkyl or C 2 - 4 alkenyl groups; and wherein each R 2 group is independently selected from Cs-28 alkyl or alkenyl groups; and wherein n, T, and X ⁇ are as defined above.
- Preferred materials of this second group include 1,2 bis [ tallowoyloxy] -3-trimethylammonium propane chloride, 1,2 and 1, 2-bis [oleoyloxy] -3-trimethylammonium propane chloride. Such materials are described in US 4,137,180 (Lever Brothers) . Preferably, these materials also comprise an amount of the corresponding mono-ester.
- compositions derived from the process of the present invention comprise one or more perfumes.
- the perfume is present in encapsulated and non-confined forms.
- the total amount of encapsulated and non-confined perfume present is preferably an amount of from 0.01 to 10 % by weight, more preferably from 0.05 to 5 % by weight, even more preferably from 0.1 to 4.0 %, most preferably from 0.5 to 3.0 % by weight, based on the total weight of the composition.
- the amount of encaps present is from 0.01 to 0.9 %, preferably from 0.05 to 0.7 %, more preferably from 0.15 to 0.5 % and most preferably from 0.2 to 0.5 % by weight of the total composition .
- the encapsulated perfume is preferably in the form of a slurry having a viscosity of from greater than water to 1000 cps at 21 s "1 and 25 0 C.
- the perfume loading of the encaps that is to say the amount of the total encap weight that is perfume, is preferably from 20 to 40 wt %, more preferably from 28 to 32 wt %, by total weight of the encaps.
- the encaps (or "capsules") for use in the process of the present invention comprise a shell.
- the shell is preferably comprised of materials including aminoplasts, proteins, polyurethanes, polysaccharides, gums, celluloses, and any other encapsulating material which may be used effectively in the present invention, such as polymethylmethacrylate.
- Preferred encapsulating polymers include those formed from melamine formaldehyde or urea formaldehyde condensates, as well as similar types of aminoplasts.
- Most preferably the shell comprises melamine formaldehyde.
- microcapsules made via the simple or complex coacervation of gelatin are also preferred for use with the coating.
- Microcapsules having shell walls comprised of polyurethane, polyamide, polyolefin, polysaccaharide, protein, silicone, lipid, modified cellulose, gums, polyacrylate, polystyrene, and polyesters or combinations of these materials are also possible.
- a representative process used for aminoplast encapsulation is disclosed in U.S. Patent No. 3,516,941 though it is recognized that many variations with regard to materials and process steps are possible.
- a representative process used for gelatin encapsulation is disclosed in U.S. Patent No, 2,800,457 though it is recognized that many variations with regard to materials and process steps are possible. Both of these processes are discussed in the context of fragrance encapsulation for use in consumer products in U.S. Patent Nos. 4,145,184 and USA 5,112,688 respectively.
- Encapsulation can provide pore vacancies or interstitial openings depending on the encapsulation techniques employed.
- Fragrance capsules known in the art and suitable for use in the present invention comprise a wall or shell comprising a three-dimensional cross-linked network of an aminoplast resin, more specifically a substituted or un-substituted acrylic acid polymer or co-polymer cross-linked with a urea- formaldehyde pre-condensate or a melamine-formaldehyde pre- condensate .
- Microcapsule formation using mechanisms similar to the foregoing mechanism, using (i) melamine-formaldehyde or urea-formaldehyde pre-condensates and (ii) polymers containing substituted vinyl monomeric units having proton- donating functional group moieties (e.g. sulfonic acid groups or carboxylic acid anhydride groups) bonded thereto is disclosed in U.S. Patent 4,406,816 (2-acrylamido-2- methyl-propane sulfonic acid groups) , UK published Patent Application GB 2,062,570 A (styrene sulfonic acid groups) and UK published Patent Application GB 2,006,709 A (carboxylic acid anhydride groups) .
- Particle size and average diameter of the capsules can vary from about 10 nanometers to about 1000 microns, preferably from about 50 nanometers to about 100 microns, more preferably from about preferably from about 2 to about 40 microns, even more preferably from about 3 to 30 microns. A particularly preferred range is from about 5 to 10 microns, for example 6 to 7 microns.
- the capsule distribution can be narrow, broad or multimodal. Multimodal distributions may be composed of different types of capsule chemistries.
- Useful components of the perfume include materials of both natural and synthetic origin. They include single compounds and mixtures. Specific examples of such components may be found in the current literature, e.g., in Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press; Synthetic
- perfume in this context is not only meant a fully formulated product fragrance, but also selected components of that fragrance, particularly those which are prone to loss, such as the so-called ⁇ top notes' .
- Top notes are defined by Poucher (Journal of the Society of Cosmetic Chemists 6(2) : 80 [1955]) .
- Examples of well known top-notes include citrus oils, linalool, linalyl acetate, lavender, dihydromyrcenol, rose oxide and cis-3-hexanol .
- Top notes typically comprise 15-25%wt of a perfume composition and in those embodiments of the invention which contain an increased level of top-notes it is envisaged at that least 20%wt would be present within the encapsulate.
- perfume components which have a low Clog P (i.e. those which will be partitioned into water), preferably with a Clog P of less than 3.0.
- Clog P i.e. those which will be partitioned into water
- materials, of relatively low boiling point and relatively low Clog P have been called the "delayed blooming" perfume ingredients and include the following materials:
- ClogP values can be readily calculated from a program called "CLOGP" which is available from Daylight Chemical Information Systems Inc., Irvine Calif., USA. Octanol/water partition coefficients are described in more detail in U.S. Pat. No. 5,578,563.
- Perfume components with a ClogP above 3 comprise: Iso E super, citronellol, Ethyl cinnamate, Bangalol, 2,4,6- Trimethylbenzaldehyde, Hexyl cinnamic aldehyde, 2,6- Dimethyl-2-heptanol, Diisobutylcarbinol, Ethyl salicylate, Phenethyl isobutyrate, Ethyl hexyl ketone, Propyl amyl ketone, Dibutyl ketone, Heptyl methyl ketone, 4,5- Dihydrotoluene, Caprylic aldehyde, Citral, Geranial,
- Isopropyl benzoate Cyclohexanepropionic acid, Campholene aldehyde, Caprylic acid, Caprylic alcohol, Cuminaldehyde, l-Ethyl-4-nitrobenzene, Heptyl formate, 4-Isopropylphenol, 2-Isopropylphenol, 3-Isopropylphenol, Allyl disulfide, 4- Methyl-l-phenyl-2-pentanone, 2-Propylfuran, Allyl caproate, Styrene, Isoeugenyl methyl ether, Indonaphthene, Diethyl suberate, L-Menthone, Menthone racemic, p-Cresyl isobutyrate, Butyl butyrate, Ethyl hexanoate, Propyl valerate, n-Pentyl propanoate, Hexyl acetate, Methyl heptanoate, trans
- perfumes with which the present invention can be applied are the so-called ⁇ aromatherapy' materials. These include many components also used in perfumery, including components of essential oils such as Clary Sage, Eucalyptus, Geranium, Lavender, Mace Extract, Neroli, Nutmeg, Spearmint, Sweet Violet Leaf and Valerian.
- Co-softeners may be used. When employed, they are typically present at from 0.1 to 20% and particularly at from 0.5 to 10%, based on the total weight of the composition.
- Preferred co-softeners include fatty esters, and fatty N- oxides.
- Fatty esters that may be employed include fatty monoesters, such as glycerol monostearate, fatty sugar esters, such as those disclosed WO 01/46361 (Unilever) .
- compositions of the present invention will preferably comprise a fatty alcohol.
- the fatty complexing material improves the viscosity profile of the composition by complexing with mono-ester component of the fabric conditioner material thereby providing a composition which has relatively higher levels of di-ester and tri-ester linked components.
- the di-ester and tri-ester linked components are more stable and do not affect initial viscosity as detrimentally as the mono-ester component.
- the higher levels of mono-ester linked component present in compositions comprising quaternary ammonium materials based on TEA may destabilise the composition through depletion flocculation .
- depletion flocculation is significantly reduced.
- the fatty complexing agent at the increased levels as required by the present invention, "neutralises" the mono-ester linked component of the quaternary ammonium material. This in situ di-ester generation from mono-ester and fatty alcohol also improves the softening of the composition .
- Preferred fatty acids include hardened tallow fatty acid (available under the trade name PristereneTM, ex Uniqema) .
- Preferred fatty alcohols include hardened tallow alcohol (available under the trade names StenolTM and HydrenolTM, ex Cognis and LaurexTM CS, ex Albright and Wilson) .
- the fatty complexing agent is preferably present in an amount greater than 0.3 to 5% by weight based on the total weight of the composition. More preferably, the fatty component is present in an amount of from 0.4 to 4%.
- agent is preferably from 5:1 to 1:5, more preferably 4:1 to 1:4, most preferably 3:1 to 1:3, e.g. 2:1 to 1:2.
- compositions may further comprise a nonionic surfactant, especially where the level of quaternary ammonium compound is above about 8 % by weight of the total composition. Typically these can be included for the purpose of stabilising the compositions.
- Suitable nonionic surfactants include addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids and fatty amines. Any of the alkoxylated materials of the particular type described hereinafter can be used as the nonionic surfactant.
- Suitable surfactants are substantially water soluble surfactants of the general formula:
- R is selected from the group consisting of primary, secondary and branched chain alkyl and/or acyl hydrocarbyl groups; primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and branched chain alkenyl-substituted phenolic hydrocarbyl groups; the hydrocarbyl groups having a chain length of from 8 to about 25, preferably 10 to 20, e.g. 14 to 18 carbon atoms.
- Y is typically:
- R has the meaning given above or can be hydrogen; and Z is at least about 8, preferably at least about 10 or 11.
- the nonionic surfactant has an HLB of from about 7 to about 20, more preferably from 10 to 18, e.g. 12 to 16.
- GenapolTM C200 (Clariant) based on coco chain and 20 EO groups is an example of a suitable nonionic surfactant.
- the nonionic surfactant is present in an amount from 0.01 to 10%, more preferably 0.1 to 5 by weight, based on the total weight of the composition.
- Alternative stabilising agents may be used.
- Alternative stabilisers include single long chain ethoxylated cationic surfactant with a counter ion which is preferably an alkyl sulphate, such as methyl sulphate and ethyl sulphate, and most preferably is a methylsulphate counter-ion.
- the single long chain cationic surfactants alternatives are alkoxylated cationic quaternary ammonium surfactants.
- Those suitable for use in this invention are generally derived from fatty alcohols, fatty acids, fatty methyl esters, alkyl substituted phenols, alkyl substituted benzoic acids, and/or alkyl substituted benzoate esters, and/or fatty acids that are converted to amines which can optionally be further reacted with another long chain alkyl or alkyl-aryl group; this amine compound is then alkoxylated with one or two alkylene oxide chains each having less than or equal to about 50 moles alkylene oxide moieties (e.g. ethylene oxide and/or propylene oxide) per mole of amine.
- alkylene oxide moieties e.g. ethylene oxide and/or propylene oxide
- Typical of this class are products obtained from the quaternization of aliphatic saturated or unsaturated, primary, secondary, or branched amines having one hydrocarbon chain from about 12 to about 22 carbon atoms alkoxylated with one or two alkylene oxide chains on the amine atom each having less than or equal to about 50 alkylene oxide moieties.
- the amine hydrocarbons for use herein have from about 12 to about 22 carbon atoms, and are preferably in a straight chain configuration.
- Suitable quaternary ammonium surfactants are made with one or two alkylene oxide chains attached to the amine moiety, in average amounts of less than or equal to about 50 moles of alkylene oxide per alkyl chain, more preferably from about 3 to about 20 moles of alkylene oxide, and most preferably from about 5 to about 12 moles of alkylene oxide per hydrophobic, e.g., alkyl group.
- Suitable stabilizers of this type include Ethoquad® 18/25, C/25, and 0/25 from Akzo and Variquat®-66 (soft tallow alkyl bis (polyoxyethyl) ammonium ethyl sulfate with a total of about 16 ethoxy units) from Goldschmidt.
- non-ionic stabilisers are the long chain cationic surfactants based on quaternized amido-amine surfactants of the general structure;
- Rl C12-30-alkyl, -alkenyl, -arylalkyl, and - (cycloalkyl) alkyl;
- R2 and R3 H or Cl-4-alkyl;
- R4 and R5 Cl-4-alkyl, -alkoxyalkyl, and -hydroxyalkyl;
- Preferred commercial surfactants include Rewoquat V3351, a tallow alkyl amido-amine methyl sulphate quat (ex Goldschmidt) , Surfac ARF, a tallow amine ethoxy ammonium methyl sulphate (ex Surfachem) .
- amido-amine single long chain cationic surfactants for use in the present invention may be alkoxylated.
- These alkoxylated amido-amine single chain cationic surfactants comprise one or more alkylene oxide chains each having less than or equal to about 50 moles alkylene oxide moieties (e.g. ethylene oxide and/or propylene oxide) per mole of amine.
- the preferred alkoxylated surfactants for use in the present invention comprise at least one ethoxylate group.
- WO 95/27771 and include amphoteric surfactants including betaines and tegobetaines .
- amphoteric surfactants including betaines and tegobetaines .
- compositions of the invention may contain one or more other ingredients.
- ingredients include photobleaches, fluorescent agents, dyes, preservatives (e.g. bactericides), pH buffering agents, preferably inorganic or organic based such as hydrochloric acid, lactic acid and sodium lactate, etc, perfume carriers, hydrotropes, anti-redeposition agents, soil-release agents, polyelectrolytes, anti- shrinking agents, anti-wrinkle agents, anti-oxidants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents and ironing aids.
- cationic polymeric deposition aids include cationic guar polymers such as JaguarTM (ex Rhone Poulenc) , cationic cellulose derivatives such as CelquatsTM (ex National Starch), FlocaidTM (ex
- a composition for use in the invention may be in solid or liquid form.
- the composition may be a concentrate to be diluted, rehydrated and/or dissolved in a solvent, including water, before use.
- the composition may also be a ready-to- use (in-use) composition.
- the composition is provided as a ready to use liquid comprising an aqueous phase.
- the aqueous phase may comprise water-soluble species, such as mineral salts or short chain (Ci_ 4 ) alcohols .
- the mineral salts may aid the attainment of the required phase volume for the composition, as may water soluble organic salts and cationic deflocculating polymers, as described in EP 41,698 A2 (Unilever) .
- Such salts may be present at from 0.001 to 1% and preferably at from 0.005 to 0.1% by weight of the total composition.
- suitable mineral salts for this purpose include calcium chloride and magnesium chloride.
- the compositions of the invention may also contain pH modifiers such as hydrochloric acid.
- the short chain alcohols include primary alcohols, such as ethanol, propanol, and butanol, and secondary alcohols such as isopropanol. The short chain alcohol may be added with the cationic softening agent during the preparation of the composition.
- the composition being a fabric softener or fabric conditioner composition, is preferably for use in the rinse cycle of a home textile laundering operation, where, it may be added directly in an undiluted state to a washing machine, e.g. through a dispenser drawer or, for a top- loading washing machine, directly into the drum. Alternatively, it can be diluted prior to use.
- the compositions may also be used in a domestic hand-washing laundry operation.
- Example 1 Preparation of Composition 1 and Comparative Example A
- Composition 1 and Comparative Example A both have the same composition but Composition 1 was prepared using the process of the invention, whilst Comparative Example A was prepared using the process of the prior art.
- Stepantex UL90 (Stepan) 2Free perfume oil is Azure (IFF) Encapsulated perfume slurry is Blue Touch (IFF)
- compositions were studied using light microscopy to assess dispersion of the encaps in the compositions.
- the comparative example had poor visual properties with significant aggregation of the encaps.
- the composition according to the invention showed minimal aggregation and had excellent visual appearance.
Abstract
Description
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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CN2009801217681A CN102057028B (en) | 2008-06-11 | 2009-05-20 | Improvements relating to fabric conditioners |
EP09761580.1A EP2294167B1 (en) | 2008-06-11 | 2009-05-20 | Improvements relating to fabric conditioners |
BRPI0915359A BRPI0915359B1 (en) | 2008-06-11 | 2009-05-20 | a process for preparing a fabric softener composition, and a composition made from the same |
ES09761580.1T ES2592692T3 (en) | 2008-06-11 | 2009-05-20 | Improvements related to tissue conditioners |
ZA2010/08203A ZA201008203B (en) | 2008-06-11 | 2010-11-16 | Improvement relating of fabric conditioners |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP08158038.3 | 2008-06-11 | ||
EP08158038 | 2008-06-11 |
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WO2009150017A1 true WO2009150017A1 (en) | 2009-12-17 |
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PCT/EP2009/056126 WO2009150017A1 (en) | 2008-06-11 | 2009-05-20 | Improvements relating to fabric conditioners |
Country Status (7)
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EP (1) | EP2294167B1 (en) |
CN (1) | CN102057028B (en) |
AR (1) | AR072079A1 (en) |
BR (1) | BRPI0915359B1 (en) |
ES (1) | ES2592692T3 (en) |
WO (1) | WO2009150017A1 (en) |
ZA (1) | ZA201008203B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011020652A1 (en) * | 2009-08-20 | 2011-02-24 | Unilever Plc | Improvements relating to fabric conditioners |
WO2013040115A1 (en) * | 2011-09-13 | 2013-03-21 | The Procter & Gamble Company | Fluid fabric enhancer compositions |
WO2013087364A1 (en) * | 2011-12-16 | 2013-06-20 | Unilever Plc | Improvements relating to fabric treatment compositions |
WO2013189661A1 (en) * | 2012-06-21 | 2013-12-27 | Unilever Plc | Improvements relating to fabric conditioners |
WO2017102306A1 (en) * | 2015-12-15 | 2017-06-22 | Unilever Plc | Fabric conditioning composition |
WO2018169531A1 (en) * | 2017-03-16 | 2018-09-20 | The Procter & Gamble Company | Benefit agent containing delivery particle slurries |
US11708546B2 (en) | 2017-03-16 | 2023-07-25 | The Procter & Gamble Company | Benefit agent containing delivery particle |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2587553T3 (en) * | 2011-12-16 | 2016-10-25 | Unilever N.V. | Tissue treatment |
Citations (1)
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WO2007028495A1 (en) | 2005-09-09 | 2007-03-15 | Unilever Plc | Fabric conditioning composition |
Family Cites Families (1)
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EP0955994B1 (en) * | 1996-08-19 | 2010-11-03 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
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2009
- 2009-05-20 BR BRPI0915359A patent/BRPI0915359B1/en active IP Right Grant
- 2009-05-20 EP EP09761580.1A patent/EP2294167B1/en active Active
- 2009-05-20 WO PCT/EP2009/056126 patent/WO2009150017A1/en active Application Filing
- 2009-05-20 ES ES09761580.1T patent/ES2592692T3/en active Active
- 2009-05-20 CN CN2009801217681A patent/CN102057028B/en active Active
- 2009-06-09 AR ARP090102064 patent/AR072079A1/en active IP Right Grant
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2007028495A1 (en) | 2005-09-09 | 2007-03-15 | Unilever Plc | Fabric conditioning composition |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011020652A1 (en) * | 2009-08-20 | 2011-02-24 | Unilever Plc | Improvements relating to fabric conditioners |
WO2013040115A1 (en) * | 2011-09-13 | 2013-03-21 | The Procter & Gamble Company | Fluid fabric enhancer compositions |
US8835373B2 (en) | 2011-09-13 | 2014-09-16 | The Procter & Gamble Company | Fluid fabric enhancer compositions |
WO2013087364A1 (en) * | 2011-12-16 | 2013-06-20 | Unilever Plc | Improvements relating to fabric treatment compositions |
WO2013189661A1 (en) * | 2012-06-21 | 2013-12-27 | Unilever Plc | Improvements relating to fabric conditioners |
WO2017102306A1 (en) * | 2015-12-15 | 2017-06-22 | Unilever Plc | Fabric conditioning composition |
EP3390601B1 (en) | 2015-12-15 | 2019-04-10 | Unilever Plc. | Fabric conditioning composition |
WO2018169531A1 (en) * | 2017-03-16 | 2018-09-20 | The Procter & Gamble Company | Benefit agent containing delivery particle slurries |
CN110431220A (en) * | 2017-03-16 | 2019-11-08 | 宝洁公司 | Delivery of particles slurries containing beneficial agent |
US11708546B2 (en) | 2017-03-16 | 2023-07-25 | The Procter & Gamble Company | Benefit agent containing delivery particle |
US11713437B2 (en) | 2017-03-16 | 2023-08-01 | The Procter & Gamble Company | Benefit agent containing delivery particle slurries |
Also Published As
Publication number | Publication date |
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EP2294167B1 (en) | 2016-06-22 |
BRPI0915359A2 (en) | 2015-11-03 |
EP2294167A1 (en) | 2011-03-16 |
ES2592692T3 (en) | 2016-12-01 |
AR072079A1 (en) | 2010-08-04 |
BRPI0915359B1 (en) | 2019-01-29 |
CN102057028B (en) | 2012-10-10 |
ZA201008203B (en) | 2012-02-29 |
CN102057028A (en) | 2011-05-11 |
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