EP1062312B1 - Concentre de conditionnement pour tissus - Google Patents

Concentre de conditionnement pour tissus Download PDF

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Publication number
EP1062312B1
EP1062312B1 EP99936088A EP99936088A EP1062312B1 EP 1062312 B1 EP1062312 B1 EP 1062312B1 EP 99936088 A EP99936088 A EP 99936088A EP 99936088 A EP99936088 A EP 99936088A EP 1062312 B1 EP1062312 B1 EP 1062312B1
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EP
European Patent Office
Prior art keywords
oil
water
fabric
conditioning composition
composition according
Prior art date
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Expired - Lifetime
Application number
EP99936088A
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German (de)
English (en)
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EP1062312A1 (fr
Inventor
Mansur S. Unilever Res. Port Sunlight MOHAMMADI
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers

Definitions

  • the present invention relates to fabric conditioning concentrates with less than 10% by weight of water that easily disperse and self-emulsify on dilution with cold or warm water (10-70°C) and when emulsified in water give stable emulsions with controlled viscosity and creaming and which have excellent perfume delivery and softening for laundry.
  • Conventional rise conditioners are obtained by dispersing a cationic softening material and perfume into hot water.
  • the problem with such conventional aqueous rinse conditioners is that although the rinse conditioners soften laundry they do not deliver perfume onto the fabric well because as much as one third of the perfume in the formulation remains in the rinse water.
  • the dilute versions of such conventional aqueous fabric rinse conditioner may typically have a relatively low viscosity making them less attractive for use by consumers.
  • thickener such as cationic starch as disclosed in EP-A-0596580 in the name of Avebe.
  • cationic fabric softeners are typically added to aqueous compositions as concentrated aqueous solutions and viscosity control is difficult.
  • European patent application EP-A-0 813 862 relates to concentrates containing cationic fabric softeners, perfume oil, alkyl glucoside emulsifier, and water, which concentrates are in the form of microemulsions.
  • European patent application EP-A-0 829 531 discloses a conditioning concentrate comprising a cationic fabric softening compound and oil in which the cationic fabric softening compound is suspended in the oil. When the concentrate is mixed with water, an oil-in-water emulsion is produced.
  • GB 2 007 734 (Cargo Fleet) discloses a liquid fabric softener concentrate which consists of a quaternary ammonium salt in a dissolved state having at least one C 8 -C 30 long chain alkyl group and an oil.
  • the concentrate can be dispersed or emulsified with water. No mention of improved perfume delivery is made.
  • the concentrate compositions of the prior art are typically used by dosing the concentrate directly into the washing machine so that it is diluted with cold water during the rinse cycle. It has been found that if emulsions are produced using the concentrate compositions of the prior art, the emulsions are sometimes not stable on storage under ambient conditions (temperatures of 0-45°C). The emulsions are found to be particularly unstable at relatively high ambient temperatures or at relatively low.concentrations of fabric conditioner (approximately 5% by weight). Further, emulsions produced using prior art concentrates tend to have relatively low viscosities or viscosities which vary from batch to batch, making them unattractive for the consumer to use.
  • EP-A-0730023 discloses laundry concentrate compositions comprising a mixture of at least one non-ionic surfactant, and at least one water-insoluble fatty oil containing a hydrophilic polar group and having a melting point below 30°C, wherein the concentrate has viscosity in excess of about 10 mPas.
  • the concentrate Upon dilution with at least about one volume of water per volume of concentrate, the concentrate is converted at least partially into a liquid crystal phase dispersion, providing a diluted concentrate having a viscosity of at least about 50 mPas.
  • US 5429754 discloses fabric conditioning compositions comprising a water soluble polymer having a hydrophilic backbone associated with an acidic group, a hydrocarbon based fabric conditioning component and an electrolyte. No mention of improved perfume delivery is made.
  • the water-soluble polymeric structurant can be included in a fabric conditioning concentrate composition comprising fabric softener and oil.
  • This fabric conditioner concentrate can be diluted with water to produce an emulsion.
  • the water-soluble polymeric structurant can be dissolved in water to the final desired concentration and the solution of water-soluble structurant then used to dilute a fabric conditioning concentrate composition comprising a fabric softening compound and oil.
  • water-soluble polymeric structurant overcomes the problems associated with the prior art.
  • it can provide a fabric conditioning concentrate which can be diluted to give a stable, dilute emulsion (have concentrations of cationic fabric softener in the region 1-15%, preferably around 5% by weight).
  • emulsions can have viscosity which is relatively consistent from batch to batch and in the desired range (being in the range 10-100 mPa.s at shear rate of 106 s -1 ).
  • the emulsions produced using the rinse conditioner concentrates of the present invention have excellent perfume delivery and further improved fabric softening properties.
  • the present invention has overcome the undesirable greasy softness feeling that oil-based conditioners impart to fabrics, achieving instead a silky softened feeling.
  • present invention can provide fabric conditioning concentrates which are not detrimental to the absorbency of fabric and which also reduce the creasing of fabric.
  • Fabric softened with the compositions of the present invention show better ease of ironing than conventional fabric softeners.
  • the present invention provides a fabric conditioning concentrate composition
  • a fabric softening compound mixed with oil wherein the composition contains a water-soluble polymeric structurant.
  • the present invention further provides a method of manufacturing a fabric conditioning concentrate composition as described above comprising mixing together a fabric softening compound, oil and a water-soluble polymeric structurant.
  • the present invention also provides a method of preparing an aqueous emulsion containing a fabric conditioning compound, comprising diluting the fabric conditioning concentrate of the invention with water.
  • the method can for example be carried out in a batch process at a factory or in a bottle at home.
  • the present invention further provides a method of preparing an aqueous emulsion containing a fabric conditioning compound, comprising dissolving a water-soluble polymeric structurant in water to provide a solution of polymeric structurant of a concentration substantially equal to the desired final concentration of water-soluble polymeric structurant in the emulsion, using the solution of polymeric structurant to dilute a fabric conditioning concentrate composition comprising a fabric softening compound mixed with oil.
  • this method is carried out as a batch process.
  • the present invention further provides a fabric conditioning composition
  • a fabric conditioning composition comprising an aqueous emulsion, the aqueous emulsion comprising a fabric softening compound, oil and a water-soluble polymeric structurant.
  • the conditioning concentrate and methods of the present invention are distinguished from the prior art in that the water-soluble structurant is dissolved to its final desired concentration before or simultaneously with the production of an emulsion of fabric softening component in water.
  • the water soluble polymeric structurant component By mixing the water soluble polymeric structurant component with oil, it becomes possible to disperse in water the fabric softening compound and oil with little loss of the structure provided in the emulsion by the polymeric structurant.
  • concentrate in the context of the present invention means that little or no water is present in the formulation.
  • the maximum level of water that can be present in the formulation is 10% or less by weight of the total formulation, more preferably 5% or less by weight, most preferably 2% or less by weight. In some situations less than 0.5% by weight of water may be present.
  • a structurant is here defined as a material which increases the viscosity of an aqueous emulsion of the present invention or an aqueous emulsion formed by diluting the concentrate of the invention in water, both at gravitational or zero shear rate and at normal pouring shear rates.
  • Normal pouring shear rates are in the range 10 to about 110 s -1 .
  • the viscosity of an emulsion according to the present invention is in the range 40-80 mPa.s at 106 s -1 , preferably around 60 mPas at 106 s -1 . It is found that little or no phase separation occurs under these conditions.
  • the increase in the zero shear rate viscosity of the composition provides kinetic stabilisation against gravitational creaming or settling of dispersed droplets in an aqueous emulsion of the present invention.
  • the increase in the viscosity at normal pouring shear rates allows emulsions prepared using the concentrates of the present invention to have properties which are attractive to consumers.
  • aqueous emulsions of the present invention can have viscosities which are relatively consistent between batches. That is, particularly with emulsions produced by home dilution, the emulsions are not excessively affected by conditions such as local temperature, concentration variations of concentrate in water, salinity and hardness of dilution water etc. This allows a consistently attractive product to be provided.
  • the presence of the polymeric structurant in oil emulsions of the present invention also gives improved softening and perfume deposition.
  • the softening feel given to fabric is found to be improved, being silky rather than greasy.
  • aqueous emulsions of the present invention contain droplets of generally spherical shape comprising an outer layer of fabric softening component in lamellar liquid crystalline phase and a liquid core of oil and perfume. It is believed that this structure contributes to the good deposition of perfume onto the fabric.
  • the cationic fabric softening compound in the concentrates of the present invention may be suspended, dispersed or dissolved in the oil.
  • the concentrate compositions of the invention can be described as having a physical state wherein a network of solid crystallites of controlled strength is formed to contain the liquid phase and the structurant.
  • the strength of the solid network is controlled such that concentrate composition does not undergo gravitational sedimentation under quiescent conditions but flows under agitation and stirring.
  • the emulsified product when added to water, has an oil droplet size (D 43 volume average droplet size) of under 5 ⁇ m and more preferably under 3 ⁇ m.
  • Droplet size (D 10 ) is typically in the range 0.2 ⁇ m-50 ⁇ m.
  • Stability of the emulsions according to the present invention can be measured by studying the creaming level, for example as discussed below.
  • the water-soluble polymeric structurant is a material which will increase viscosity of an aqueous emulsion of the present invention in water at zero shear rate and at normal pouring shear rates.
  • the structurant will be present in the form of small solid particles in the concentrate composition of the invention.
  • the particles may typically be of size in the range 2-100 micrometres depending on their source. Particle size may be measured by light microscopy.
  • the structurant is present as microcrystals.
  • the polymeric structurant of the invention Upon dilution with water, the polymeric structurant of the invention becomes fully or partially gelatinised.
  • compositions containing structurants in which the structurant is usually already present in hydrated form, being in the form of a gel or solution, which is post- or pre-dosed into the emulsion.
  • the preferred prior art order of addition of polymers for examples as set out in EP-A-0596580 in the name of Avebe is to add a concentrated solution of water-soluble polymer after an aqueous emulsion has been prepared.
  • water-soluble indicates that the polymeric structurant, gelatinises in water at a characteristic temperature range at concentrations of interest, i.e. around 0.1-2% by weight.
  • the polymeric structurant when mixed with water does not form a separate phase.
  • the structurant preferably does not have substantial surfactant properties.
  • the structurant is preferably selected from nonionically or cationically modified natural polymers such as protein or plant derived polymers, particularly polysaccharide compositions such as starch.
  • any type of starch can be used such as potato starch, corn starch, wheat starch, tapioca starch or pea starch.
  • the degree of substitution of the cationic starch to be used in accordance with the present invention is preferably in the range 0.005-1 preferably between 0.01 and 0.05.
  • Particularly preferred are forms of starch that have an amylopectin content of more than 95% by weight based on solids.
  • Suitable methods of manufacturing structurant polymers suitable for use in the present invention are set forth in EP-A-0596580 in the name of Avebe.
  • Naturally obtained polymers include cellulose compounds, which may be modified by substituting them with alkyl groups, such as hydrophillically modified hydroxy ethyl cellulose, carboxy methyl cellulose etc.
  • Naturally derived gums such as galactomannan gum or guar gum can be used.
  • Protein derived polymers may include gelatin.
  • the polymeric structurant used may depend upon the eventual use for which the concentrate is intended. As explained below, the concentrates of the present invention may be used in an industrial or domestic context. Further, the behaviour of some of the concentrates may depend upon the local temperature, hardness of water etc.
  • Cationically modified potato starch such as Solvitose BPN and cationically modified Galactomannan, 2-hydroxypropyl trimethyl ammonium chloride ether (Jaguar C-13-S, C-14-S, C-15, C-17 or C-162 - Trade Mark), guar gum or 2 hydroxy-3-(trimethylammonium) propyl ether chloride (HICARE 1000, Registered Trade Mark) and Polygel (Trade Mark) K100 and K200 are preferred for home dilution purposes.
  • Concentrates suitable for dilution under factory suitably comprise cationic potato starches such as SOFTGEL BDA (Trade Mark), SOFTGEL BD (Trade Mark), AMYLOFAX HS (Trade Mark), RAISAMYL 125 (Trade Mark), RAISAMYL 135 (Trade Mark), RAISAMYL 145 (Trade Mark) and synthetic cationic polyacrylic POLYGEL (Trade Mark) K Series, K100 and K200 (3V Sigma).
  • cationic potato starches such as SOFTGEL BDA (Trade Mark), SOFTGEL BD (Trade Mark), AMYLOFAX HS (Trade Mark), RAISAMYL 125 (Trade Mark), RAISAMYL 135 (Trade Mark), RAISAMYL 145 (Trade Mark) and synthetic cationic polyacrylic POLYGEL (Trade Mark) K Series, K100 and K200 (3V Sigma).
  • the amount of polymeric structurant included in the concentrate of the present invention depends upon the desired concentration of polymeric structurant in emulsions of the present invention.
  • polymeric structurant are required in the emulsions according to the present invention to give the desired viscosities.
  • the quantity in the aqueous emulsion is preferably in the range 0.05-2% by weight, more preferably 0.1-1 wt%, most preferably 0.1-0.5% by weight.
  • the concentration of polymeric structurant in the concentrate is suitably in the range 1-10% by weight, more preferably 2-5%, most preferably 3-4% by weight.
  • water-soluble polymeric structurant is present in the oil as a suspended phase.
  • compositions of the present invention comprise at least one oil.
  • the oil may act as a lubricating oil.
  • the oil may be a mineral oil, an ester oil or a sugar ester oil. Some natural oils, such as vegetable oils may be included if appropriate.
  • Fatty alcohols for example as defined as coactives in EP-A-0394133 are not suitable for use as oils in the present invention. It is preferred that the oils used in the present invention are liquid, whereas the preferred fatty alcohols of EP-A-0394133 are soft solids.
  • ester oils are esters of straight chain or branch chain, saturated or unsaturated carboxylic acids.
  • oils used in the present invention are hydrophobic. Further, it is preferred that they either comprise sugar ester oils or an oil with substantially no surface activity. Fatty alcohols as defined in EP-A-0349133 are not substantially hydrophobic and are surface active.
  • oil is an ester oil, sugar ester oil or mineral oil.
  • suitable oils include those in the Sirius range of mineral oils (ex Silkolene).
  • Suitable ester oils include the saturated ester oils (ex Unichema) and the unsaturated sugar ester oils (ex Mitsubishi Kagaku).
  • ester oils of the invention are hydrophobic in nature. It is further preferred if the ester oil is saturated (hardened) in nature, unless it is a sugar ester oil or a plant derivative, for which unsaturation is preferred.
  • Suitable ester oils are the fatty ester of a mono or polyhydric alcohol having from 1 to about 24 carbon atoms in the hydrocarbon chain and mono or polycarboxylic acids having from 1 to about 24 carbon atoms in the hydrocarbon chain with the proviso that the total number of carbon atoms in the ester oil is equal to or greater than 16 and that at least one of the hydrocarbon radicals in the ester oil has 12 or more carbon atoms.
  • Ester oils most suitable for use in the present invention are the PRIOLUBES from Unichema.
  • PRIOLUBE 1407, PRIOLUBE 1447, PRIOLUBE 1415, PRIOLUBE 1446, PRIOLUBE 1427, PRIOLUBE 1445, PRIOLUBE 2045, PRIOLUBE 3988, PRIOLUBE 3987, PRIOLUBE 2091, ESTOL 1545, and ESTOL 1527 are advantageously employed.
  • ESTOL 1545 which is a 2-ethyl hexyl stearate are particularly useful.
  • Suitable mineral oils include Esso Marcol technical grade range of oils and particularly preferred is the Silkolene medicinal Sirius range (e.g. M40, M70 and M180).
  • the molecular weight of the mineral oil is typically within the range 150 to 400.
  • the density of the mineral oil is from 0.80 to 0.90 g/cm 2 , more preferably from 0.83 to 0.88 g/cm 2 .
  • the viscosity of the ester oil or mineral oil is from 2 mPa.s to 400 mPa.s at a temperature of 25°C, more preferably a viscosity from 2 to 150 mPa.s, most preferably a viscosity from 10 to 100 mPa.s.
  • the viscosity of the sugar ester oil is above 50,000 mPas, preferably 5,000 to 20,000 mPas, most preferably 6,000 to 20,000 mPas. All viscosities are measured at 25°C.
  • the refractive index of the oil is from 1.445 to 1.490, more preferred from 1.460 to 1.485.
  • the level of oil in the emulsion is preferably in the range 1-15 %wt.
  • the level of oil in the fabric conditioner concentrate is preferably from 20 to 78 wt% of the composition, most preferably from 50 to 70 wt%.
  • the oil used in the present invention will, when combined with a suitable deposition aid such as conventional cationic fabric softening compounds, have fabric softening properties.
  • the fabric softening compound is a quaternary ammonium material comprising a polar head group and two alkyl or alkenyl chains.
  • the fabric softening compound of the invention has two long chain alkyl or alkenyl chains with an average chain length greater than C 14 , more preferably each chain has an average chain length greater than C 14 , more preferably at least 50% of each long chain alkyl or alkenyl group has a chain length of C 18 .
  • the long chain alkyl or alkenyl groups of the fabric softening compound are predominantly linear.
  • the fabric softening compounds of the invention are substantially water-insoluble.
  • Substantially insoluble fabric softening compounds in the context of this invention are defined as fabric softening compounds having a solubility less than 1 x 10 -3 wt% in demineralised water at 20°C, preferably the fabric softening compounds have a solubility less than 1 x 10 -4 , most preferably the fabric softening compounds have a solubility at 20°C in demineralised water from 1 x 10 -3 to 1 x 10 -6 .
  • R 1 and R 2 represent hydrocarbyl groups having from 12 to 24 carbon atoms
  • R 3 and R 4 represent hydrocarbyl groups containing 1 to 4 carbon atoms
  • X is an anion, preferably selected from halide, methyl sulphate and ethyl sulphate radicals are preferred.
  • quaternary softeners include di(tallow alkyl) dimethyl ammonium methyl sulphate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow alkyl) dimethyl ammonium chloride; dioctadecyl dimethyl ammonium chloride; di(hydrogenated tallow alkyl) dimethyl ammonium methyl sulphate; dihexadecyl diethyl ammonium chloride; di(coconut alkyl) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium chloride and di(hydrogenated tallow alkyl) dimethyl ammonium chloride (Arquad 2HT Trade Mark).
  • esters or amide links for example those available under the trade names Accosoft 580, Varisoft 222, and Stepantex.
  • Particularly preferred fabric softening compounds are water-insoluble quaternary ammonium materials which comprise a compound having two C 12-18 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present.
  • the preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula: wherein each R 1 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups; T is X - is any suitable anion and n is an integer from 0-5. Particularly preferred is di(ethyl ester) dimethyl ammonium chloride (DEEDMAC).
  • a second preferred type of quaternary ammonium material can be separated by the formula: wherein R 1 , n, X - and R 2 are as defined above.
  • the quaternary ammonium material is biologically degradable.
  • Preferred materials of this class such as 1,2 bis[hardened] tallow oyloxy]-3-trimethylammonium propane chloride and their methods of preparation are, for example, described in US 4 137 180 (Lever Brothers).
  • these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-hardened tallowoyloxy-2-hydroxy trimethylammonium propane chloride.
  • the fabric softening agent may also be a polyol ester quat (PEQ) as described in EP 0 638 639 (Akzo).
  • PEQ polyol ester quat
  • the weight ratio of softening compound to oil is less than 5:1, suitably less than 3:1, preferably less than 1:1.
  • the weight ratio of softening compound to oil is greater than 1:10, preferably greater than 1:3.
  • the level of softening compound in the concentrate is preferably from 3 wt% to 60 wt% of the total composition, more preferably from 10 wt% to 40 wt%.
  • dilute emulsions produced according to the present invention contain in the range 0.5-5% by weight cationic active fabric softening compound, more preferably 1-3% by weight, most preferably 1.0-2% by weight.
  • the composition contains less than 25 wt% of the total composition of organic solvent, more preferably less than 20 wt%, most preferably less than 10 wt%.
  • the solvents are nonaqueous. In any case level of water must be kept below 10% of the total composition.
  • the cationic fabric softening compound in the concentrate of the present invention may be dissolved, suspended or dispersed in the oil.
  • a cationic fabric softening compound may be soluble in oil if, for example, it comprises carbon chains derived from soft tallow, i.e. tallow having a high iodine.
  • the cationic fabric softening compound may be made soluble in the oil by inclusion of a suitable solvent.
  • Solvents which may be used include ethanol, proponol, isoproponol, ethylene glycol, 1,2 propylene glycol, 1,3-propylene glycol and glycerol.
  • Suitable solvents preferably have low flash point, for example IPA (isopropyl alcohol).
  • organic solvents are included in the compositions. It is preferred that less than half of the amount of any solvent present is flammable solvent (i.e. has a flash point of less than 25°C). The major proportion of the solvent should most preferably be a non-flammable solvent (i.e. have a flashpoint of higher than 25°C). Suitable examples include propylene glycol and especially hexylene glycol and butyl digol for reasons of viscosity and appearance of the melt. A mixture of solvents may provide advantageous results, especially with respect to viscosity. In some compositions solvent may be present as a result of being a component of an ingredient of the composition.
  • compositions of the present invention help to control the size of the crystals of the fabric softening compound, or to make the fabric softening compound soluble in the oil.
  • compositions of the present invention and the method of the present invention are particularly suitable for giving enhanced perfume deposition onto fabric during rinse conditioning.
  • the concentrate according to the present invention contains perfume suitably at a level in the range 1-10% by weight, preferably 3-6% by weight.
  • Suitable perfume compounds may be selected by the person skilled in the art.
  • the perfume is substantially hydrophobic.
  • the perfume is soluble in oil.
  • the concentrate or emulsions of the present invention may include a crystal growth inhibitor. It is preferred that the crystal growth inhibitor forms part of the concentrate, particularly for non-batch dilution by the consumer at home.
  • the crystal growth inhibitors are compounds that have highly polarisable hydrophilic groups.
  • Particularly preferred crystal growth modifiers are organic acids of alkyl chain length C 13 or less and nonionic surfactants having an average alkyl chain length between C 13 and C 22 and from 10 to 30 ethoxylate groups.
  • Particularly preferred crystal growth inhibitors are tallow and coco nonionic surfactants having from 15 to 22 ethoxylate groups, organic acids such as lactic acid (which contains about 20% linear polymeric self-esterified esters), stearic acid, and hardened or unhardened tallow or coco fatty acids. Mixtures of crystal growth inhibitors may also be used.
  • the crystal growth inhibitor or mixtures thereof should preferably be present at a level of from 1 wt% to 20 wt% of the composition, more preferably the crystal growth inhibitor should be present at a level from 2 wt% to 11 wt%.
  • compositions comprise a co-emulsifier for rapid dispersion of the composition when it is added to water.
  • the co-emulsifier may comprise nonionic surfactant.
  • a nonionic ethoxylated surfactant is used as the crystal growth inhibitor then this will function as both the inhibitor and as a co-emulsifier to provide good dispersion.
  • the preferred co-emulsifiers are C 8 -C 22 alcohol alkoxylates with an average of 3 to 10 alkoxylate groups, preferably 5 to 7 alkoxylate groups.
  • Ethoxylates are the preferred alkoxylates although mixed ethoxylates/propoxylates or propoxylates may also be used.
  • the emulsions of the invention when dispersed in water at use concentration preferably have a pH of more than 1.5, more preferably less than 5.
  • Concentrates of the present invention are preferably in the form of a paste or high viscosity liquid.
  • the concentrate may be added to water by the consumer or at a factory, to form an emulsion which can then be stored for later use by addition to the rinse liquor.
  • the consistency of concentrate compositions produced by the cold grinding method depends upon the melting point of the cationic fabric softener and varies between a liquid dispersion and a paste, whereas products of the hot melt method, discussed below, can have the consistency of a gel if cooled naturally or a pourable paste if cooled while agitating.
  • the concentrates or emulsions of the invention can also contain one or more optional ingredients, selected from pH buffering agents, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • optional ingredients selected from pH buffering agents, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • the concentrate compositions according to the present invention may be produced according to any suitable method. Two methods are particularly preferred, namely the melt process and the cold grinding (milling) process.
  • the polymeric structurant will generally remain solid in both methods of production.
  • a melt as referred to herein is a liquid mixture of two or more substances, at least one of which would solidify on cooling to ambient temperature.
  • the melt may contain dispersed non-liquid material, such as polymeric structurant.
  • dispersed non-liquid material such as polymeric structurant.
  • typically one or two of the components solidify on cooling (usually fabric softening compound, nonionic surfactant and fatty acids, if present).
  • the fabric softening compound is heated until it is mobile, preferably liquid, followed by addition to an oil phase (which may contain a perfume) to produce a melt.
  • the polymeric structurant is added to this melt while the melt is still warm and liquid, the structurant being present as dispersed solid.
  • the additional components of the composition may be incorporated into the composition via a mobile fabric conditioning compound or via the oil, or they may be added after the fabric conditioning compound and the oil have been mixed together.
  • the melt is formed at a temperature of at least 35°C, preferably of at least 40°C, e.g. at a temperature of 45°C to 70°C.
  • the fabric softening compound and nonionic surfactant(s) are mixed with the oil and then heated to form a liquid to which structurant may be added. Perfume may be added upon cooling to a lower temperature.
  • the melt can cool to a room temperature naturally or while being stirred mechanically. In this manner, the final viscosity of the melt can be further controlled.
  • the concentrate compositions of the present invention may be produced by a cold grinding (milling) method wherein the fabric softening compound, polymeric structurant and the oil are mixed together, at ambient temperature typically at high shear rates, without the fabric softening composition being heated prior to mixing.
  • the concentrate compositions of the present invention can be used to prepare an aqueous emulsion by diluting the concentrate composition with water.
  • a concentrate composition comprising a fabric softening component mixed with oil may be diluted to form an emulsion using a solution of water-soluble polymeric structurant, which solution comprises water-soluble polymeric structurant at the desired final concentration of the aqueous emulsion.
  • the concentrate is diluted with ambient or hot water.
  • the temperature of the dilution water is in the range ambient-100°C, preferably 40-70°C, more preferably 50-60°C for batch dilution.
  • the concentrate may be heated to become a liquid before mixing with water. Mixing of the concentrate with water may take place over a time period of 2-30 minutes, depending on the scale of the mixing process, the equipment used etc.
  • the concentrate and water may be agitated in any suitable way, for example stirring or shaking.
  • an emulsion is produced by diluting a fabric conditioning concentrate according to the present invention with water
  • the polymer is present in the concentrate in substantially solid form.
  • it has not been gelatinised by mixing with water before being introduced into the concentrate. Accordingly, in this aspect of the invention, gelatinisation and emulsification can occur simultaneously. This has been found to give surprising advantages including the ability to control the viscosity and droplet size of the emulsion.
  • the viscosity of emulsions produced according to the present invention may depend upon the conditions under which the emulsion is produced by dilution of fabric conditioning concentrate. Further, when producing an emulsion according to the present invention, there is a danger that an undesirable flocculation of the droplets will occur leading to a creaming and unattractive composition.
  • the following procedure may be used to determine the optimum conditions for production of emulsion according to the present invention.
  • the optimum batch mixing temperature range is suitably around 40-70°C, more preferably 50-60°C.
  • water may be added to the concentrate while mixing (phase inversion route) or concentrate may be added to water.
  • phase inversion route phase inversion route
  • concentrate may be added to water.
  • Dilution may be carried out by the household user or in an industrial plant.
  • inclusion of the polymeric structurant in the concentrate helps the emulsification process and the break-up of droplets such that no extensive processing equipment is required to produce stable emulsions from the concentrates.
  • compositions prepared according to the invention and comparative compositions were subjected to the following tests.
  • cationic active refers to pure cationic fabric softening compound.
  • fabric softener refers to the commercial product, which is typically 80% pure cationic active and approximately 20% solvent, eg IPA.
  • active softener is defined below.
  • Softening performance is evaluated by adding to 1 ltr of demineralised water at ambient temperature in a Tergotometer enough product to give 0.1 g of active softener material.
  • the active softener is defined as cationic active or (if oil is present), cationic active plus oil. In this way, the level of active softener was equal in the rinse liquor for all examples according to the invention.
  • Three pieces of terry towelling (19 cm x 19.5 cm weighing 40 g in total) were added to the Tergotometer pot. The terry towelling was already rinsed in a 0.00045% by weight sodium alkyl benzene sulphonate solution to simulate the anionic of detergent from a main wash.
  • the towels were treated for 5 minutes at 65 rpm, spin-dried to remove excess liquor and line-dried overnight.
  • a panel of 20 trained people evaluated the towels by comparing against set standards. A low number indicates a greater degree of softness (2 is very soft and 8 is harsh).
  • Perfume delivery was evaluated by rinsing in a Tergotometer three pieces of terry towelling (19 x 19.5 cm weighing 40 g in total) per product in a similar manner to that previously described for softening evaluation above. Instead of being line-dried the cloths were immediately assessed for perfume intensity by a trained group of twenty panellists who ranked each cloth on a scale of zero to five corresponding to descriptors ranging from no perfume to very strong perfume. Further assessments were made after five hours when the cloths were dry and again after twenty-four hours or longer. The level of product was 0.1 g/l active matter with a perfume level in the rinse liquor of 4.76 mg/l.
  • phase separation was also observed. In particular, it was noted whether or not the separated layer appeared clear (indicating the loss of all droplets into the separated layer) or milky or cloudy (indicating the presence of fine submicron droplets remaining in the aqueous layer).
  • Viscosities were measured using a standard Haake viscometer with a NV cup and bob, at a shear rate of 106 s -1 .
  • compositions having the following general compositions were prepared by a cold grinding route.
  • the specific components will be set out further below.
  • fabric softener, oil, perfume and (if included) polymeric structurant were mixed together and then homogenised by a Silverson mixer or overhead Heidolph mixer.
  • the polymeric structurant may be included in the final emulsion by a different route (route (B)) and be absent from the concentrate.
  • oil and structurant used are varied, as will be explained further below.
  • the fabric softener used in these examples is Arquad 2HT which typically contains 80% wt pure cationic active and contains ⁇ 20% wt isopropyl alcohol (IPA) solvent.
  • Fabric softener (80% cationic active 20% IPA) 41.07 36.26 35.36 27.25 Oil (100% pure) 44.97 50.17 57.19 65.11 Hardened tallow fatty acid 5.19 4.64 - - Perfume (100%) 3.90 3.97 4.06 4.17 Structurant Polymer (100% pure) 4.87 4.97 3.38 3.47
  • the oil:cationic weight ratio is based on the content of pure cationic active.
  • Active:perfume ratio is in most cases fixed at ⁇ 20.
  • Aqueous emulsions were prepared by one of the following procedures:
  • the concentrates were melted first.
  • the water in both routes (A) and (B) was at a temperature in the range 40-70°C. Water and concentrate were mixed for a period of 5-10 minutes. Mixing was carried out in a baffled batch-based apparatus comprising a jacketed vessel linked to a water bath. Stirring was provided by an impeller connected to a overhead Heidolph mixer. A pitch-blade three stage impeller was used, rotating at a rate in the range 300-1,000 rpm.
  • the fabric softener in each case is Arquad 2HT, as above, unless indicated otherwise.
  • the oil and structurant used are varied, as explained further below. Oil:Cationic active wt.
  • a fabric conditioning concentrate was prepared by mixing a fabric softener material, perfume and oil by the cold grinding route and mixed with water by the method described above.
  • Examples 1-24 and Comparative Examples A-E were prepared by preparing the compositions described above using the oils and structurants described below.
  • the compositions, mixing conditions and viscosity of the products are shown in Tables 3 to 5.
  • Ratio of oil to cationic active 2:1. Emulsion manufactured by route "B”.
  • SOFTGEL BDA, Amylofax HS and SOFTGEL BD are supplied by AVEBE BA, Holland.
  • HI-CARE 1000 is supplied by Rhone-Poulenc.
  • JAGUAR C-13-S is supplied by Meyhall.
  • Guar gum is supplied by ROHM & HAAS
  • Ratio of oil to cationic active 2:1
  • Ratio of oil to cationic active 3:1
  • Example 20 Comparison of Example 20 with the Comparative Example A (having no structurant polymer) clearly shows that excessive creaming occurs with the comparative example but is absent over a substantial period and normal temperature range for an emulsion produced by the present invention.
  • Example 4 shows substantially less creaming for compositions of the present invention having structurant polymer. In Example 4, some creaming did occur, but the product is clear rather than turbid, indicating that flocculation has not occurred.
  • compositions of the present invention provide much higher perfume intensity than the current premium conventional fabric conditioner.
  • compositions having polymeric structurant have similar perfuming properties to emulsions based on oil based concentrate not having polymeric structurant.
  • Softness Score (CONTROL in brackets) A 6.63 (5.75) 20 5.13 (5.75) 4.75 (4.00) B 4.25 (3.75) 4.88 (3.38) 1 3.63 (3.75) 4.75 (3.63) 18 - 4 - 10 - 21 - 22 - 23 - 27 - C 5.00 (4.63) 5.75 (3.38) D 4.75 (3.75) 2 - 3 4.75 (5.88) 7.0 (5.75) 5 4.25 (3.88) 6 4.25 (3.88) 7 - 8 - 9 - 19 - 25 - 26 - 28 - 11 4.63 (6.19) 1B 4.30 (4.40 2B 2 4.00 (3.50) 4B 2 4.38 (4.00) 1C 2 3.60 (3.50) 2C 2 4.40 (4.00)
  • compositions of the present invention give similar or better softening compared to the premium conventional fabric softening compositions.
  • Compositions made according to the present invention have similar softening to compositions not having any polymeric structurant.
  • Fabric conditioning concentrates were manufactured by route (B) described above.
  • compositions were then tested as follows. 6.0 g of concentrate was weighed into a bottle and 94 g of tap water added to the bottle. The mixture is shaken for about two minutes. Emulsions are found to form spontaneously. The viscosity and softening results are set out below. The tap water was supplied at 15°C. The compositions had the following general composition. Oil:cationic active 2:1 fabric softener (80% cationic active) (Arquad 2HT) 35.43 oil (100%) (M180 - ex-SILKOLENE) 53.81 nonionic coco (EO)20 (100%) 5.38 perfume (100%) 5.38 structurant polymer variable
  • Solvitose BPN is a cationic potato starch polymer supplied by AVEBE.
  • the absorbency results are a measure of the hydrophobicity given to fabrics treated with the fabric softening composition.
  • the results show that emulsions produced by the present invention have very good re-wetting non-hydrophobising properties so that towels treated with these can be used to dry effectively.

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  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Claims (22)

  1. Composition de conditionnement comprenant (i) un composé ammonium quaternaire assouplissant d'étoffe mélangé à une huile et (ii) de l'eau en une quantité de 10 % ou moins en poids total de la formulation, dans laquelle la composition contient un structurant polymérique soluble dans l'eau.
  2. Composition de conditionnement selon la revendication 1, dans laquelle le structurant polymérique soluble dans l'eau est présent sous la forme de particules solides.
  3. Composition de conditionnement selon la revendication 1 ou 2, dans laquelle le structurant polymérique soluble dans l'eau n'a sensiblement aucune propriété tensioactive.
  4. Composition de conditionnement selon la revendication 1, 2 ou 3, dans laquelle le structurant polymérique soluble dans l'eau comprend un polymère naturel modifié non ioniquement ou cationiquement.
  5. Composition de conditionnement selon l'une quelconque des revendications 1 à 4, comprenant 1 à 10 % en poids de structurant polymérique soluble dans l'eau.
  6. Composition de conditionnement selon l'une quelconque des revendications 1 à 5, dans laquelle l'huile est sensiblement hydrophobe.
  7. Composition de conditionnement selon l'une quelconque des revendications 1 à 6, dans laquelle l'huile est choisie dans le groupe constitué par les huiles minérales, les huiles d'ester, les huiles d'ester de sucre ou les mélanges de celles-ci.
  8. Composition de conditionnement selon l'une quelconque des revendications précédentes, comprenant 20 à 78 % en poids d'huile.
  9. Composition de conditionnement selon l'une quelconque des revendications précédentes, comprenant de 3 à 60 % en poids de composé assouplissant d'étoffe.
  10. Composition de conditionnement selon l'une quelconque des revendications précédentes, comprenant en outre un parfum.
  11. Méthode de fabrication d'une composition de conditionnement selon l'une quelconque des revendications 1 à 9, comprenant le mélange d'un composé assouplissant d'étoffe, d'une huile et d'un structurant polymérique soluble dans l'eau.
  12. Méthode de préparation d'une émulsion aqueuse contenant un composant de conditionnement d'étoffe, comprenant la dilution de la composition de conditionnement selon l'une quelconque des revendications 1 à 9 avec de l'eau.
  13. Méthode de préparation d'une émulsion aqueuse contenant un composant de conditionnement d'étoffe, comprenant la dissolution d'un structurant polymérique soluble dans l'eau dans de l'eau pour former une solution du structurant polymérique d'une concentration sensiblement égale à la concentration finale souhaitée du structurant polymérique soluble dans l'eau dans l'émulsion, l'utilisation de la solution du structurant polymérique pour diluer une composition de conditionnement comprenant (i) un composé ammonium quaternaire assouplissant d'étoffe mélangé avec une huile et (ii) de l'eau en une quantité de 10 % ou moins en poids de la formulation totale.
  14. Méthode selon la revendication 12 ou 13, dans laquelle le structurant polymérique soluble dans l'eau est choisi dans le groupe constitué par les polymères naturels modifiés non ioniquement ou cationiquement ou les mélanges de ceux-ci.
  15. Méthode selon la revendication 12, 13 ou 14, dans laquelle l'huile est choisie dans le groupe constitué par les huiles minérales, les huiles d'ester ou les huiles d'ester de sucre.
  16. Composition de conditionnement d'étoffe comprenant une émulsion aqueuse, l'émulsion aqueuse comprenant un structurant polymérique soluble dans l'eau, une huile et un composé ammonium quaternaire assouplissant d'étoffe.
  17. Composition de conditionnement d'étoffe selon la revendication 16, dans laquelle le structurant polymérique est choisi dans le groupe constitué par les polymères naturels modifiés non ioniquement ou cationiquement ou les mélanges de ceux-ci.
  18. Composition de conditionnement d'étoffe selon la revendication 16 ou 17, comprenant 0,05 à 2 % en poids de structurant polymérique soluble dans l'eau.
  19. Composition de conditionnement d'étoffe selon la revendication 16, 17 ou 18, dans laquelle l'huile est choisie dans le groupe constitué par les huiles minérales, les huiles d'ester, les huiles d'ester de sucre et les mélanges de celles-ci.
  20. Composition de conditionnement d'étoffe selon l'une quelconque des revendications 16 à 19, comprenant 1 à 15 % en poids d'huile.
  21. Composition de conditionnement d'étoffe selon l'une quelconque des revendications 16 à 20, dans laquelle le composé assouplissant d'étoffe est présent en une quantité de 0,5 à 5 % en poids.
  22. Composition de conditionnement d'étoffe selon l'une quelconque des revendications 16 à 21, ayant une viscosité dans la gamme de 10 à 100 mPa.s à 106 s-1.
EP99936088A 1998-02-27 1999-01-26 Concentre de conditionnement pour tissus Expired - Lifetime EP1062312B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9804283.1A GB9804283D0 (en) 1998-02-27 1998-02-27 Fabric conditioning concentrate
GB9804283 1998-02-27
PCT/EP1999/000497 WO1999043777A1 (fr) 1998-02-27 1999-01-26 Concentre de conditionnement pour tissus

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EP1062312A1 EP1062312A1 (fr) 2000-12-27
EP1062312B1 true EP1062312B1 (fr) 2005-04-20

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CN (1) CN1174086C (fr)
AR (1) AR018292A1 (fr)
AU (1) AU3251099A (fr)
BR (1) BR9908293A (fr)
CA (1) CA2316788A1 (fr)
DE (1) DE69924835T2 (fr)
ES (1) ES2239452T3 (fr)
GB (1) GB9804283D0 (fr)
ID (1) ID25815A (fr)
IN (1) IN192724B (fr)
WO (1) WO1999043777A1 (fr)

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WO2013070655A1 (fr) * 2011-11-11 2013-05-16 The Dial Corporation Procédé d'augmentation de la performance d'assouplissants de tissus cationiques
KR20170020860A (ko) * 2014-06-18 2017-02-24 로디아 오퍼레이션스 향료와의 안정적인 조성물의 제조 방법
US20180010070A1 (en) * 2015-01-28 2018-01-11 Rhodia Operations Composition containing ester quat, cationic polysaccharide and nonionic polysaccharide
US10155918B2 (en) * 2014-12-22 2018-12-18 Rhodia Operations Solid composition comprising a polysaccharide and a hydrophobic compound, the process and use thereof

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GB9930436D0 (en) * 1999-12-22 2000-02-16 Unilever Plc A method of stabilising fabric softening compositions
GB9930433D0 (en) * 1999-12-22 2000-02-16 Unilever Plc Use of fabric conditioning compositions for ironing benefits
US20020055452A1 (en) * 2000-07-07 2002-05-09 Givaudan Sa Process for imparting a fragrance to a product and fragrance and conditioning to a dry fabric
EP1299514A1 (fr) * 2000-07-07 2003-04-09 Givaudan SA Procede con u pour conferer une perception de conditionnement et de parfum agreable aux tissus humides et secs
EP1279726A1 (fr) * 2001-07-27 2003-01-29 Givaudan SA Compositions adoucissantes
GB0130556D0 (en) * 2001-12-20 2002-02-06 Unilever Plc Fabric conditioning compositions
ATE284942T1 (de) * 2002-09-05 2005-01-15 Procter & Gamble Strukturierte flüssige weichmacherzusammensetzungen
US7135451B2 (en) * 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch
ATE476954T1 (de) 2003-05-07 2010-08-15 Kemira Pigments Oy Zusammensetzungen zur gezielten freisetzung von duftstoffen und aromen
AT412286B (de) * 2003-05-27 2004-12-27 Koenig Manja Kathrin Zusammensetzung zur ausrüstung von textilien
MX269457B (es) * 2003-10-10 2009-08-25 Firmenich & Cie Composicion para limpieza de telas.
EP1711231A1 (fr) 2003-10-31 2006-10-18 Firmenich Sa Systeme de liberation de parfums pour produits de nettoyage et d'entretien de surfaces
FR2887450B1 (fr) * 2005-06-23 2007-08-24 Rhodia Chimie Sa Ingredient concentre pour le traitement et/ou la modification de surfaces, et son utilisation dans des compositions cosmetiques
GB0623005D0 (en) * 2006-11-17 2006-12-27 Unilever Plc Fabric treatment method and composition
CN102758353B (zh) * 2011-04-27 2016-08-17 赢创德固赛特种化学(上海)有限公司 柔软剂产品原料及制备柔软剂产品的方法
EP2791307B1 (fr) * 2011-12-16 2016-03-16 Unilever PLC Améliorations associées aux compositions de traitement de tissu
WO2013189661A1 (fr) * 2012-06-21 2013-12-27 Unilever Plc Améliorations relatives à des conditionneurs de tissus
CN104837977A (zh) 2012-12-11 2015-08-12 高露洁-棕榄公司 织物调理组合物
DE102013226421A1 (de) * 2013-12-18 2015-06-18 Henkel Ag & Co. Kgaa Waschmittel enthaltend Alkylcarbonsäureester
WO2015107155A1 (fr) * 2014-01-17 2015-07-23 Rhodia Operations Méthode de stabilisation d'une composition d'adoucissement
CN107250456B (zh) * 2014-12-22 2020-12-25 罗地亚经营管理公司 包含季铵化合物和多糖的固体组合物、其工艺和用途
US20210395646A1 (en) * 2016-12-14 2021-12-23 Rhodia Operations Method of use of composition comprising a quaternary ammonium compound, a cationic polysaccharide and a nonionic polysaccharide
BR112019011431A2 (pt) * 2016-12-15 2019-10-22 Rhodia Operations composição para tratamento de tecido
CN107998925B (zh) * 2017-12-15 2018-12-25 安徽儒商生物科技有限公司 一种水溶性颗粒混合搅拌设备

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WO2013070655A1 (fr) * 2011-11-11 2013-05-16 The Dial Corporation Procédé d'augmentation de la performance d'assouplissants de tissus cationiques
KR20170020860A (ko) * 2014-06-18 2017-02-24 로디아 오퍼레이션스 향료와의 안정적인 조성물의 제조 방법
US20170121639A1 (en) * 2014-06-18 2017-05-04 Rhodia Operations Composition comprising a quaternary ammonium compound, a cationic polysaccharide and a nonionic polysaccharide
US10155918B2 (en) * 2014-12-22 2018-12-18 Rhodia Operations Solid composition comprising a polysaccharide and a hydrophobic compound, the process and use thereof
US20180010070A1 (en) * 2015-01-28 2018-01-11 Rhodia Operations Composition containing ester quat, cationic polysaccharide and nonionic polysaccharide

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ES2239452T3 (es) 2005-09-16
BR9908293A (pt) 2000-10-31
CN1174086C (zh) 2004-11-03
DE69924835D1 (de) 2005-05-25
ID25815A (id) 2000-11-09
DE69924835T2 (de) 2005-11-17
AR018292A1 (es) 2001-11-14
WO1999043777A1 (fr) 1999-09-02
CA2316788A1 (fr) 1999-09-02
EP1062312A1 (fr) 2000-12-27
IN192724B (fr) 2004-05-15
GB9804283D0 (en) 1998-04-22
AU3251099A (en) 1999-09-15
CN1292024A (zh) 2001-04-18

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