WO2010069733A1 - Improvements relating to fabric treatment compositions - Google Patents
Improvements relating to fabric treatment compositions Download PDFInfo
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- WO2010069733A1 WO2010069733A1 PCT/EP2009/065893 EP2009065893W WO2010069733A1 WO 2010069733 A1 WO2010069733 A1 WO 2010069733A1 EP 2009065893 W EP2009065893 W EP 2009065893W WO 2010069733 A1 WO2010069733 A1 WO 2010069733A1
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- powder
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- cationic
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- fabric
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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
- C11D3/16—Organic compounds
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/382—Vegetable products, e.g. soya meal, wood flour, sawdust
Definitions
- the present invention relates to fabric conditioning compositions comprising micro powders of botanical origin.
- US2003/0087788 discloses water dispersible granules comprising a hydrophobic fragrance in the form of droplets, which is finely divided in and encapsulated by a water-soluble/dispersible solid organic matrix, which may be polypeptides of plant or synthetic origin, such as soya or wheat.
- EP0908171 (Gem Energy Industry Ltd) discloses a dry powder herbal cleaning composition containing (a) a herb which acts as a soap or detergent; (b) a herb which acts as a foaming accelerating agent; (c) a herb which acts as a foaming agent; (d) a herb which acts as a pigmentation or colour restoring or maintenance agent; and (e) a herb which acts as a conditioner.
- WO00/77153 discloses a detergent tablet containing (a) particles which contain organic surfactant and detergency builder; and (b) water insoluble but water swellable particles of plant material which contain both cellulose and lignin, such as coconut husk, obtainable by fragmentation of plant material without separation of its fibres into a liquid dispersion.
- a detergent tablet containing (a) particles which contain organic surfactant and detergency builder; and (b) water insoluble but water swellable particles of plant material which contain both cellulose and lignin, such as coconut husk, obtainable by fragmentation of plant material without separation of its fibres into a liquid dispersion.
- Such powders include ginger for fragrance; lime, lemon or orange rind for freshness; flower petals for perfume; exfoliating agents such as oat kernel flour, rice or rice bran flour; various pigments of natural origin, such as turmeric powder for anti-inflammatory benefit; seed derivatives such as cardamom and coriander for perfuming; various dried herbs such as mint, oregano, green tea, bay leaf and tea-tree for perfuming and anti-microbial benefits.
- the present invention provides a fabric conditioning composition, which comprises:
- the powder of botanical origin has a particle size of from 0.1 to
- a method of preparing a composition comprising the step of pulverizing the powder of botanical origin to a particle size of from 0.1 to 100 microns preferably from 0.2 to 90 microns, more preferably from 0.5 to 60, even more preferably from 1 to 45 microns and most preferably from 2 to 30 microns.
- the present invention requires the use of ultra-fine powders.
- the powders suitable for use in the compositions of the invention are sparingly soluble, preferably insoluble particulate structures of botanical origin. They are preferably aromatic and as such preferably comprise one or more aromatic essential oils.
- the powders of the present invention can be of any shape and are not necessarily spherical and can have aspect ratio (ratio of length to diameter) greater than 1.
- aspect ratio ratio of length to diameter
- micronised, ultra-fine, or finely divided particle sizes having a maximum axis of from 0.1 to 100 microns preferably from 0.2 to 90 microns, more preferably from 0.5 to 60, even more preferably from 1 to 45 microns and most preferably from 2 to 30 microns.
- Particles of suitable size may be obtained by any suitable process, for example pulverizing, milling, etc. Fractionation, for example by sieving, may be used to separate the required particle size range.
- the powder is a material of botanical origin, and may be derived from any part of the plant, such as tubers, fruits, flowers, flower parts (calyx, stamen, etc), seeds, beans, pods, pith, woods, barks, stalks, stems, leaves, roots, rhizomes, husks, skins, rinds and mixtures thereof.
- aromatic powders examples include vanilla bean powder, ginger powder, cinnamon powder, cocoa powder, clove powder, cardamom powder, coriander - A -
- herb powders for example, rosemary, thyme, sweet bay, sage, tarragon, mint, basil, balm, lemon verbena, red bergamot, marjoram, lavender and oregano
- chamomile powder for example, rosemary, thyme, sweet bay, sage, tarragon, mint, basil, balm, lemon verbena, red bergamot, marjoram, lavender and oregano
- chamomile powder for example, rosemary, thyme, sweet bay, sage, mint, basil, balm, lemon verbena, red bergamot, marjoram, lavender and oregano
- chamomile powder for example, rosemary, thyme, sweet bay, sage, mint, basil, balm, lemon verbena, red bergamot, marjoram, lavender and oregano
- chamomile powder for example, rosemary, thyme, sweet bay, sage, mint, basil, balm, lemon verbena, red berga
- Preferred non-aromatic powders include ginseng powder, rice husk flour, wheat husk flour, buckwheat husk flour and mixtures thereof.
- the powdered material can be in native form or may result from processes such as ageing, fermenting and roasting that would increase or alter the constituent aroma chemicals.
- the plant powders of the invention can be incorporated into laundry compositions in a similar fashion as other powdered ingredients.
- the powder of botanical origin is present in an amount of from 0.1 to 10 wt %, preferably from 0.3 to 6 wt %, more preferably from 0.4 to 4 wt % and most preferably from 0.5 to 3 wt % by weight of the total composition.
- the powders of botanical origin suitable for use in the invention are not extracted or isolated materials, such as polymers, for example lignin, starches or proteins, but are plant parts that are powdered in their bulk state.
- the powders are not intended to include cellulose or cellulose derivatives such as polymeric derivatives such as cellulose ethers.
- the plant parts (i.e. pre-powdered) and the powders are not subject to chemical purification, for example, to remove components such as lignin or pigments (but may, of course, be washed or cleaned).
- Deposition of micro-powder from the laundry formulations of the invention onto a substrate may be achieved by any suitable route.
- the particle size of the powder is such that the particles are trapped between the fibres of the fabric.
- the filtration mechanism requires particles or clusters of primary particles of a size comparable with the interyarn pore size.
- the particle size suitable for filtration is typically in the range of from 1 to 30 microns. Larger particles begin to be visible to the unaided eye, whereas smaller particles tend to be removed in the wash. Particles of around from 5 to 15 microns are preferred as they tend to be invisible to the eye and exhibit good deposition by filtration onto fabrics.
- Deposition of micro-powders from laundry formulations of the invention may also be achieved and enhanced over and above the delivery by filtration method, by polymer aided deposition.
- the polymeric deposition aid is suitably present at a level of from 0.01 to 5% by total weight of the composition preferably from 0.02 to 3%, more preferably from 0.2 to 2 % and most preferably from 0.5 to 1 .6 %.
- Polymeric deposition agent suitable for use in the present invention include modified natural polymers and synthetic polymers.
- Polymers suitable for the deposition of micro-powders are disclosed in WO9709406, particularly high MW polyethylene oxides (PEO) which are used to deposit clay particles in the main wash;
- EP0299575B1 and WO9527037 disclose high MW PEO, polyacrylates, polyacryl amides, poly vinyl alcohol and poly ethylene imines, which are used to deposit clay particles in the main wash;
- EP0387426B1 which utilizes a similar list of polymers as well as guar gums.
- WO 01/07546 A1 discloses suitable rinse stage polymeric deposition aids for emulsion droplets including cationic guar polymers, cationic polyacrylamides, cationic potato starch, and cationic cellulose derivates.
- Preferred modified natural polymers suitable for use in the present invention may be selected from the group consisting of cationic starches, cationic guars, cationic cellulose, and nonionic locust bean gums (LBGs).
- a preferred cationic starch is a cation ical Iy modified potato starch.
- cationic polymers include cationic guar polymers such as Jaguar (ex Rhone Poulenc), cationic cellulose derivatives such as Celquats (ex National Starch), Flocaid (ex National Starch), cationic potato starch such as Softgel (ex Aralose) and cationic polyacrylamides such as PCG (ex Allied Colloids).
- cationic guar polymers such as Jaguar (ex Rhone Poulenc), cationic cellulose derivatives such as Celquats (ex National Starch), Flocaid (ex National Starch), cationic potato starch such as Softgel (ex Aralose) and cationic polyacrylamides such as PCG (ex Allied Colloids).
- Suitable non-ionic deposition aids include high molecular weight polyethylene glycols, for example PEO WSRN 750 (ex Union Carbide).
- Preferred synthetic polymers for use as a deposition aid, may be selected from the group consisting of polyethylene oxide (PEO), polyethylene imine (PEI), poly (acrylate), poly (acrylamide), polyethylene terephthalate-polyoxyethylene terephthalate (PET/POET) polymers and mixtures thereof.
- PEO polyethylene oxide
- PEI polyethylene imine
- PET polyoxyethylene terephthalate
- the fabric conditioning composition of the invention is suitable for use in a laundry process.
- a rinse treatment e.g. conditioner or finisher
- a post-treatment 'wet tissue' type product e.g. conditioner or finisher
- the compositions of the present invention are preferably rinse-added softening compositions.
- compositions of the invention may be in any physical form e.g. a tablet, a bar, a paste, gel or liquid, spray, stick, impregnated substrate, foam or mousse.
- compositions may be liquid or unit dose such as a pouch.
- the liquid products of the invention may have pH ranging from 2.5 to 7. This pH range preferably remains stable over the shelf life of the product.
- the active ingredient in the compositions is a fabric conditioning agent. More than one active ingredient may be included.
- the conditioning agents may be cationic or non-ionic. They may for example be used in amounts from 0.5% to 35%, preferably from 1 % to 30% more preferably from 3% to 25% by weight of the composition.
- the preferred softening active for use in rinse conditioner compositions of the invention is a quaternary ammonium compound.
- the quaternary ammonium fabric softening material for use in compositions of the present invention can be an ester-linked triethanolamine (TEA) quaternary ammonium compound comprising a mixture of mono-, di- and tri-ester linked components.
- TAA ester-linked triethanolamine
- TEA-based fabric softening compounds comprise a mixture of mono, di- and tri-ester forms of the compound where 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 by weight of the fabric softening compound.
- a first group of quaternary ammonium compounds (QACs) suitable for use in the present invention is represented by formula (I):
- each R is independently selected from a C 5-35 alkyl or alkenyl group;
- R 1 represents a Ci -4 alkyl, C 2-4 alkenyl or a Ci -4 hydroxyalkyl group;
- T is generally O- CO. (i.e. an ester group bound to R via its carbon atom), but may alternatively be CO-O (i.e. an ester group bound to R via its oxygen atom);
- n is a number selected from 1 to 4;
- m is a number selected from 1 , 2, or 3;
- X ⁇ is an anionic counter- ion, such as a halide or alkyl sulphate, e.g. chloride or methylsulphate.
- Di-esters variants of formula I i.e.
- each R 1 group is independently selected from Ci -4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from Cs- 2 s alkyl or alkenyl groups; and wherein n, T, and X " are as defined above.
- Preferred materials of this second group include 1 ,2 ⁇ b/s[tallowoyloxy]-3- trimethylamine propane chloride, 1 ,2 ⁇ b/s[hardened tallowoyloxy]-3-thmethylamine propane chloride, 1 ,2- ⁇ b/s[oleoyloxy]-3-thmethylanr ⁇ ine propane chloride, and 1 ,2 ib/s[stearoyloxy]-3-thmethylamine propane chloride.
- Such materials are described in US 4,137,180 (Lever Brothers).
- these materials also comprise an amount of the corresponding mono-ester.
- a third group of QACs suitable for use in the invention is represented by formula
- each R 1 group is independently selected from Ci -4 alkyl, or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8- 28 alkyl or alkenyl groups; and n, T, and X " are as defined above.
- Preferred materials of this third group include bis(2-tallowoyloxyethyl)dimethyl ammonium chloride and hardened versions thereof.
- the iodine value of the quaternary ammonium fabric softening material is from 0 to 60, preferably from 0 to 45, more preferably from 0 to 30, and most preferably from 0 to 20.
- 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 non-ester softening compound preferably has the alkyl or alkenyl chain lengths referred to above for the non-ester softening compound.
- non-ester softening compound is a quaternary ammonium material represented by formula (IV):-
- each R 1 group is independently selected from Ci -4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; R 2 group is independently selected from C 8- 28 alkyl or alkenyl groups, and X " is as defined above.
- compositions may comprise a total amount of from 0.5 wt % to 40 wt % by weight of the fabric softening compounds, preferably from 1.5 wt % to 30 wt %, more preferably from 4 to 25 wt %, most preferably from 10 to 30 wt %, based on the total weight of the composition.
- compositions may alternatively or additionally contain nonionic fabric softening agents such as lanolin and derivatives thereof.
- nonionic fabric softening agent suitable for use in the compositions of the invention is Castor oil, for example, from Now Chemicals.
- Lecithins and other phospholipids are also suitable softening compounds.
- a further preferred type of softening agent is a sugar polyester.
- the sugar polyester is preferably selected from the group consisting of sucrose polyesters, glucose polyesters and cellobiose polyesters, and is most preferably a sucrose polyester.
- the sugar polyester may be liquid, soft solid or solid.
- the preferred sucrose polyesters for use in the present invention have 2 to 4 hydrocarbon chains per sugar ring, where the hydrocarbon chain has a length of from 12 to 22 carbon atoms.
- a particularly preferred sucrose polyester is sucrose tetraerucate.
- sucrose polyester is Ryoto Sugar Ester ER290 supplied by Mitsubishi Kagaku Foods Corporation, which is a sucrose tetraerucate and according to the manufacturer's specification is mainly Tetraerucate, Pentaerucate and Hexaerucate and has a HLB value of 2.
- the sugar polyester may be pure, or may contain impurities.
- the impurities are preferably selected from the group consisting of free fatty acid, fatty acid methyl ester, soap, inorganic salts and mixtures thereof.
- the most preferred SPEs are commercially available, such as Emanon SCR-PK (ex KAO), which is a palm kernel derived SPE containing mainly C12-C14 with about 20% C18 mono unsaturatation and SPE-THSBO (ex Clahant), which is derived from touch hardened soy bean oil, having mainly C16-C18 chains with about 80% mono and di unsaturation.
- Emanon SCR-PK ex KAO
- SPE-THSBO (ex Clahant)
- the average degree of esterification of the above preferred SPEs is from 4.2 to 4.7.
- SCR-PK contains up to 20% impurities but SPE-THSBO is pure.
- SCR-PK contains from 4 to 6 wt% of K soap, 2.5 wt% of free fatty acid, from 10 to 15 wt% of fatty acid methyl ester and less than 1 % of KCI.
- the sugar polyester being non-ionic oil, requires an emulsifier, that is to say, the sugar polyester must be in an emulsified form.
- the emulsifier is preferably selected from cationic surfactant, anionic surfactant, non-ionic surfactant, and mixtures thereof.
- the ultra-fine particles of the invention themselves can act as stabilizer and emulsifier for the nonionic softeners such as sugar polyesters (SPEs).
- SPEs sugar polyesters
- a nonionic stabilising agent may be present in fabric softening compositions.
- Suitable nonionic stabilising agents may be present such as linear Cs to C22 alcohols alkoxylated with 10 to 20 moles of alkylene oxide, C10 to C20 alcohols, or mixtures thereof.
- Other stabilising agents include the deflocculating polymers as described in EP 0415698A2 and EP 0458599B1.
- the nonionic stabilising agent is a linear Cs to C22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide.
- 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 and/or other cationic softening agent to the nonionic stabilising agent is suitably 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 Cs to C2 4 alkyl or alkenyl monocarboxylic acids or polymers thereof.
- 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.
- Concentrated compositions may comprise from 0.5 to 20% by weight of fatty acid, more preferably 1 % to 10% by weight.
- the weight ratio of quaternary ammonium material or other cation ic softening agent to fatty acid material is preferably from 10:1 to 1 :10.
- Cationic surfactants which can be used in main-wash compositions for fabrics.
- Cationic surfactants that may be used include quaternary ammonium salts of the general formula R1 R2R3R4NT X " wherein the R groups are long or short hydrocarbon chains, typically alkyl, hydroxyalkyl or ethoxylated alkyl groups, and X is a counter-ion (for example, compounds in which R1 is a C8-C22 alkyl group, preferably a Cs-Cio or C12-C14 alkyl group, R2 is a methyl group, and R3 and R4, which may be the same or different, are methyl or hydroxyethyl groups); and cationic esters (for example, choline esters).
- aqueous rinse added conditioners the level of cationic or nonionic softener varies from 3 to 30% more preferably from 5 to 25%.
- botanical powders can be incorporated in predominately non-aqueous systems containing up to 60% fabric softening actives.
- the fabric conditioning compositions of the invention can also contain adjuvants that are normal in the cosmetic, pharmaceutical and/or dermatological field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preserving agents, antioxidants, solvents, fragrances, fillers, screening agents, bactericides, odour absorbers, photobleaches (singlet oxygen or radical type) and dyestuffs.
- adjuvants that are normal in the cosmetic, pharmaceutical and/or dermatological field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preserving agents, antioxidants, solvents, fragrances, fillers, screening agents, bactericides, odour absorbers, photobleaches (singlet oxygen or radical type) and dyestuffs.
- the amounts of these various adjuvants are those conventionally used in the field under consideration and are, for example, from 0.01 to 20% of the total weight of the composition. Depending on their nature, these adjuvants can be introduced into the
- the substrate When used in laundering, the substrate may be any substrate onto which it is desirable to deposit the botanical particles and which is subjected to treatment such as a washing or rinsing process.
- the substrate may be a textile fabric.
- the treatment of the substrate with the composition of the invention can be made by any suitable method such as washing, soaking or rinsing of the substrate but also by direct application such as spraying, rubbing, spotting, smearing, etc.
- the treatment may involve contacting the substrate with an aqueous medium comprising the material of the invention.
- the treatment may be provided as a spray composition e.g., for domestic (or industrial) application to fabric in a treatment separate from a conventional domestic laundering process.
- Suitable spray dispensing devices are disclosed in WO 96/15310 (Procter & Gamble) and are incorporated herein by reference.
- the compositions of the invention may be used to provide a perfume and/or odour benefit, for example a reduction in malodour, to fabric.
- Example 1 Preparation of powders for use in the invention
- Plant powders having a particle size within the claimed range were prepared using a Retsch ZM1000 Ultra Centrifugal Mill operating at a speed of 10,000 rpm. The mill was fitted with a 24 tooth rotor and a 0.12 mm screen.
- Table 1 gives two examples of the size fractions that remained on each sieve from 10g of the starting powder.
- Table 1 Weight fractions remaining on the sieve from 10g of starting powder after 30 minutes of shaking (for ginger) and by brushing (for cardamom).
- Example 2 Softener compositions 1 to 4 comprising herbs and spices, according to the invention Fabric conditioner compositions 1 to 4 in Table 2 containing herbs and spices according to the invention.
- ** TEA quat is a cationic softener based on thethanolamine with tallow or hard tallow chains and 15% IPA as solvent.
- Emanon SCR-PK is Sucrose Poly Ester softening oil derived from palm kernel oil.
- Example 3 Evaluation of deposition of powders onto fabrics
- the level of deposition of the particles from a rinse solution can be quantified by measuring the turbidity, or light transmission, of the rinse solution before and after the solution is contacted with the fabrics.
- Light transmission or turbidity measurements for this purpose cannot be conducted in the presence of cationic softeners because of their inherent milkiness.
- CAC cationic surfactant
- CAC Cetylthmethylammonium chloride
- the Linitester temperature was set to 40 0 C.
- Table 3 summarizes the deposition from the rinse solution for mint particles ⁇ 45 ⁇ m in the presence of 3 different deposition polymers. Deposition is expressed as a percentage of the total amount of added particles in the solution.
- Table 3 Deposition of mint particles onto cotton, polycotton and polyester in the presence of Softgel BDA, Locust Bean Gum and Polymer JR from rinse solutions containing 0.002 % polymeric deposition aids.
- Softgel BDA (Avebe) is a cationic potato starch with low, 0.05%, degree of substitution (charge).
- Ucare polymer JR-30M (Amerchol) is a cationic hydroxyethyl cellulose with a 1.5-
- LBG (Sigma) is a non-ionic locust bean gum polysaccharide.
- the level of delivery from the rinse solution simulating the washing machine condition is surprisingly good from the cationic solution alone compared to water.
- the polymers have improved the deposition except for polyester where the high charged density JR polymer has improved deposition over and above that of control CTAC.
- LBG has improved the deposition on cotton and polycotton (positively charged substrates in CTAC) most likely through its affinity and recognition of cellulose units.
- the wet monitors had a strong smell of the deposited particles which on drying had a faint remnant. On synthetics like polyester this was sufficient to mask the dusty vinegar smell of polyester fabric to a pleasant smell.
Abstract
Description
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES09756758T ES2406058T3 (en) | 2008-12-16 | 2009-11-26 | Improvements related to compositions for the treatment of fabrics |
EP09756758A EP2366011B1 (en) | 2008-12-16 | 2009-11-26 | Improvements relating to fabric treatment compositions |
BRPI0922529A BRPI0922529A2 (en) | 2008-12-16 | 2009-11-26 | tissue conditioning composition, process for tissue treatment, method of preparing the composition, and use of the composition |
CN200980156838.7A CN102317427B (en) | 2008-12-16 | 2009-11-26 | Improvements relating to fabric treatment compositions |
PL09756758T PL2366011T3 (en) | 2008-12-16 | 2009-11-26 | Improvements relating to fabric treatment compositions |
ZA2011/03931A ZA201103931B (en) | 2008-12-16 | 2011-05-27 | Improvements relating to fabric treatment compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP08171732.4 | 2008-12-16 | ||
EP08171732 | 2008-12-16 |
Publications (1)
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WO2010069733A1 true WO2010069733A1 (en) | 2010-06-24 |
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PCT/EP2009/065893 WO2010069733A1 (en) | 2008-12-16 | 2009-11-26 | Improvements relating to fabric treatment compositions |
Country Status (8)
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EP (1) | EP2366011B1 (en) |
CN (1) | CN102317427B (en) |
AR (1) | AR074747A1 (en) |
BR (1) | BRPI0922529A2 (en) |
ES (1) | ES2406058T3 (en) |
PL (1) | PL2366011T3 (en) |
WO (1) | WO2010069733A1 (en) |
ZA (1) | ZA201103931B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US20130344225A1 (en) * | 2011-03-11 | 2013-12-26 | Takasago International Corporation | Coffee extract |
Families Citing this family (4)
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CN104804890A (en) * | 2014-01-25 | 2015-07-29 | 无锡市拓普科技开发中心 | Decontaminating and deoiling agent for fabric dyeing |
KR101637473B1 (en) * | 2014-02-25 | 2016-07-08 | 주식회사 엘지생활건강 | Fabric softener composition |
CN104762811B (en) * | 2015-03-26 | 2017-01-25 | 海门市金麒麟红木投资发展有限公司 | Special natural softener for textiles and preparation method for special natural softener |
WO2017107819A1 (en) * | 2015-12-22 | 2017-06-29 | Rhodia Operations | Compositions comprising quat and polysaccharides |
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CA2015736A1 (en) * | 1989-05-11 | 1990-11-11 | Diane G. Schmidt | Perfume particles for use in cleaning and conditioning compositions |
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2009
- 2009-11-26 WO PCT/EP2009/065893 patent/WO2010069733A1/en active Application Filing
- 2009-11-26 CN CN200980156838.7A patent/CN102317427B/en not_active Expired - Fee Related
- 2009-11-26 ES ES09756758T patent/ES2406058T3/en active Active
- 2009-11-26 BR BRPI0922529A patent/BRPI0922529A2/en active Search and Examination
- 2009-11-26 PL PL09756758T patent/PL2366011T3/en unknown
- 2009-11-26 EP EP09756758A patent/EP2366011B1/en active Active
- 2009-12-15 AR ARP090104865A patent/AR074747A1/en not_active Application Discontinuation
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2011
- 2011-05-27 ZA ZA2011/03931A patent/ZA201103931B/en unknown
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EP2366011A1 (en) | 2011-09-21 |
BRPI0922529A2 (en) | 2016-08-09 |
PL2366011T3 (en) | 2013-08-30 |
AR074747A1 (en) | 2011-02-09 |
ES2406058T3 (en) | 2013-06-05 |
ZA201103931B (en) | 2012-08-29 |
CN102317427A (en) | 2012-01-11 |
CN102317427B (en) | 2014-08-27 |
EP2366011B1 (en) | 2013-02-20 |
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