WO2008127766A2 - Compositions contenant des composites d'agent bénéfique pré-émulsifiées à l'aide de particules cationiques colloïdales - Google Patents

Compositions contenant des composites d'agent bénéfique pré-émulsifiées à l'aide de particules cationiques colloïdales Download PDF

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Publication number
WO2008127766A2
WO2008127766A2 PCT/US2008/053490 US2008053490W WO2008127766A2 WO 2008127766 A2 WO2008127766 A2 WO 2008127766A2 US 2008053490 W US2008053490 W US 2008053490W WO 2008127766 A2 WO2008127766 A2 WO 2008127766A2
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Prior art keywords
composition
water
benefit agent
cationic
range
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PCT/US2008/053490
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English (en)
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WO2008127766A3 (fr
Inventor
Ashoke K. Sengupta
Ilona Lin
Jason St. Onge
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Amcol International Corporation
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Application filed by Amcol International Corporation filed Critical Amcol International Corporation
Priority to EP08729454A priority Critical patent/EP2180874A2/fr
Priority to CA002677825A priority patent/CA2677825A1/fr
Publication of WO2008127766A2 publication Critical patent/WO2008127766A2/fr
Publication of WO2008127766A3 publication Critical patent/WO2008127766A3/fr

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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
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246—Silicates, e.g. diatomaceous earth
    • C11D3/1253—Layer silicates, e.g. talcum, kaolin, clay, bentonite, smectite, montmorillonite, hectorite or attapulgite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/65—Characterized by the composition of the particulate/core
    • A61K2800/654—The particulate/core comprising macromolecular material
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations

Definitions

  • the present invention relates to compositions that allow increased deposition and retention of benefit agents contained therein, onto a substrate, namely, the for example, a fabric; hair; skin; teeth, and other hard surfaces, while the substrate is being treated with these compositions.
  • Cleansing products such as the conditioning shampoos, bodywashes, soaps, detergents, toothpaste, and counter or floor cleaning products, as well as surface-conditioning products such as fabric softeners are some of the exemplary product forms that these compositions represent. Silicone, fragrance, emollient, ultraviolet (UV) ray absorbers, and antimicrobial agents are typical examples of the benefit agents.
  • compositions disclosed herein show an extraordinarily high level of performance properties, namely, hair-conditioning, fabric softening, and skin-moisturizing, which is attributed to the specific additive-form in which the benefit agents are incorporated into these compositions, and in particular to the composition of this additive-form, hitherto not disclosed in the prior art.
  • the benefit agent is added to the claimed compositions, only after it is decidedly bonded to a deposition-aid, utilizing physical interaction-mediated bonding (i.e., not a chemical bond) between the two materials.
  • the benefit agent prior to being bonded to a deposition- aaid, the benefit agent preferably undergoes a physical change, to serve multiple purposes critical to the object of the present invention.
  • it is a composite material comprising a hydrophobic liquid and an exfoliated, organophilic smectite clay, with the composite material further containing a benefit agent dispersed homogeneously throughout the entire mass of the composite material.
  • the resulting benefit agent composite is necessarily a highly viscous material, having a sufficiently high viscosity for strongly opposing the "roll-up" mechanism, known in the art as being the mechanism by which surfactants remove "oily-soils" from a surface undergoing cleansing by surfactants.
  • the Hamaker constant, a direct proportionality factor for a measure of the van der Waals attractionn between material bodies, of the composite material is significantly higher than that of the benefit agent taken individually.
  • the specific gravity of the benefit agent composite can be varied starting at a minimum value of about 1, which might be critical to achieving good stability against settling/creaming (by virtue of density-matching between dispersed and continuous phases) of the benefit agent composite when dispersed in the claimed compositions whose solution phase could have a specific gravity of 1 or higher.
  • a water-immiscible, composite material composition comprising a hydrophobic liquid (which itself can be a benefit agent), an exfoliated smectite clay, and a benefit agent, is dispersed in water using a dispersing agent (an emulsifier system) comprising colloidal, water-insoluble, cationic particles having a relatively high cationic surface charge.
  • a dispersing agent an emulsifier system
  • colloidal, water-insoluble, cationic particles having a relatively high cationic surface charge The surface properties, including hydrophobicity and surface charge (as defined and characterized by methods known in the art), of these cationic particles and the benefit agent composite are such that the cationic particles can remain adsorbed on the surface of the benefit agent composite.
  • a cationic polymer may be an integral part of a capsule wall enclosing a benefit agent, with the capsule wall comprising a complex coascervate of a polycation and a polyanion, as revealed in WO 98/11870.
  • the cleansing composition may further contain a cationic polymer-based thickening agent which remains dissolved in the aqueous solution phase of the composition.
  • the encapsulated droplets have a particle size distribution such that at least 10% by weight of the droplets comprises relatively large particles having a diameter of at least 100 microns.
  • the efficacy of the claimed compositions relies heavily on parameters such as the relative hardness/softness and the thickness of the complex coascervate capsule wall, as well as the size of the encapsulated droplets of hydrophobic benefit agents, which would be hard to control in a cost-effective manner, especially during bulk manufacturing.
  • a thickening agent in certain cleansing products such as shampoo and bodywash, for minimizing gravity-separation of relatively large suspended droplets (particle size » 1 micron) from a product formulation, avoiding product instability in the way of gravity-separation of a key ingredient, might be impossible for liquid detergents which are generally required to have a relatively low viscosity and hence have a relatively low particulate-suspending ability.
  • liquid detergents which are generally required to have a relatively low viscosity and hence have a relatively low particulate-suspending ability.
  • one skilled in the art would be particularly wary about a major limitation that applies, in general, to any encapsulation approach, as discussed below.
  • the silicone is encapsulated within a polymeric capsule, and should the encapsulated silicone droplet deposit on a substrate, it is the outer surface of the capsule wall and not the strongly hydrophobic surface of the silicone droplet, which would ultimately impart any effect in the way of modification of the substrate-surface.
  • the capsule wall is derived from hydrophilic, water- soluble polymers, as disclosed in US 7,118,057 B2, US 7,294,612, and WO 98/11870B2
  • the outer surface of the capsule wall may not be able to provide for hydrophobic-modification of the hair or the fabric surface, essential to delivering benefits such as hair-conditioning and fabric-softening.
  • Such subdued or partial availability of the benefit agent may provide for a level of end-use benefit (e.g., fragrance emission) that may be sufficient, for example, for post-wash fragrance-extension, but too little for any appreciable hair-conditioning and fabric-softening.
  • a level of end-use benefit e.g., fragrance emission
  • compositions and methods described herein do not involve encapsulation of benefit agents within any capsule wall, are relatively inexpensive, involve manufacturing steps that are easy to implement or control, and do not adversely affect the stability, detergency, and foaming properties of the cleansing product compositions.
  • a related object is to provide stable, low-cost, compositions that allow significantly high deposition and retention of hydrophobic benefit agents onto substrates being treated with the compositions, including the fabric, hair, and skin.
  • compositions for use as cleansing and surface-conditioning products like shampoos, body-washes, liquid soaps, laundry detergents, fabric softeners, and toothpaste, which allow substantive retention on the hair, skin, fabric, and tooth/gum, of one or more hydrophobic benefit agents contained therein.
  • the hydrophobic actives are incorporated into the compositions, as cationic oil-in- water (O/W) emulsions.
  • the compositions may further contain surfactants present either in aqueous solutions or in powder/granular forms, polymers, and hydrophilic solvents selected from water, lower alcohols, glycols, and glycerine.
  • Emulsions stabilized by particulate- and/or polymer-based emulsifiers generally tend to exhibit a relatively high stability against flocculation and coalescence.
  • the present invention embodies the use of these emulsif ⁇ ers in producing cationic oil-in-water (O/W) emulsions of the hydrophobic benefit agents.
  • O/W oil-in-water
  • a key component of the emulsifier system used in making the claimed cationic emulsions of hydrophobic benefit agents is preferably a cationic particulate material, comprising an inorganic moiety, or an organic moiety, or a hybrid of inorganic and organic moieties.
  • This particulate component of the emulsifier system has a relatively high cationic surface charge (as determined by methods known in the art), as characterized by a zeta potential value of at least +25 millivolts, and a particle size of less than 2 microns, preferably much less than 1 micron.
  • one way to produce the cationic emulsifier particles that would serve the object of the present invention is by combining certain water-soluble cationic polymers with at least one water-insoluble anionic polymer, so long as certain material property, composition, and processing requirements are met during the manufacturing of the particles.
  • These water-insoluble, polymeric particles bear a relatively high cationic surface charge which stabilizes them against particle-to- particle aggregation.
  • these particles do not form any particulate network structures, being stable against aggregation, and are typically much smaller than 1 micron in size.
  • One way to achieve good interfacial adsorption of cationic polymers is to use cationic, amphiphilic copolymers that have both hydrophilic and hydrophobic segments in the polymer chain. Such copolymers could adsorb at the oil-water interface with their hydrophobic segments anchored onto the oil phase. Albeit, such copolymers might be functionally suitable for the present invention, they tend to be costly.
  • the other type of cationic polymer that might be effective, are the hydrophobically-modif ⁇ ed cationic polymers which also tend to be expensive.
  • Hydrophilic cationic polymers are relatively low-cost materials, and hence are preferred for the compositions and methods described herein. These polymers, however, may not be sufficiently surface-active for adsorption at the oil-water interface. Therefore, according to an important embodiment of the present invention, anionic polymers and surfactants that are capable of adsorbing at the oil-surface are used to facilitate the interfacial adsorption of the hydrophilic cationic polymers. These anionic polymers or surfactants electrostatically attract, onto themselves, the cationic polymers, serving as a coupling agent for the cationic polymers to co-adsorb at the interface.
  • the most preferred option for the cationic component of the emulsifier system is to use certain combinations of high molecular weight (molecular weight in the range of 50,000 - 1,000,000 Dalton) and ultra high molecular weight (molecular weight > 1,000,000 Dalton) cationic polymers. Since a very high molecular weight polymer can flocculate emulsion droplets by what is known as bridging flocculation, for the object of the present invention, it is important that the cationic charge of the emulsion droplets is relatively high, for example, wherein the droplets show a cationic zeta potential of more than 25 millivolts, as measured using the methods known in the art.
  • Bridging flocculation of suspended particles occurs when a single polymer chain simultaneously adsorbs on more than one particle. Accordingly, before undergoing bridging flocculation by a polymer chain, two or more suspended particles must approach one another as closely as where the particle-to- particle separation distance is equal to or less than the length of the polymer chain. Such close approach of the suspended particles may not be possible if there is sufficient electrostatic repulsion between the particles due to their surface charge, inhibiting the prospects of bridging flocculation even by a very high molecular weight polymer.
  • the Hamaker constant a direct proportionality factor for a measure of van der Waals attraction between material bodies, of the particulate-based thickener is such that the Hamaker constant (as may be derived using methods described in the colloid chemistry literature) of the composite oil phase is significantly higher, at least 4% higher, than that of a hydrophobic benefit agent by itself.
  • the specific type of particulate-based thickeners that are suitable include the hydrophobically-modified smectite clays for which only the face-surfaces of the clay platelets are rendered hydrophobic by the adsorption of long-chain (C 8 - C22) onium ions, e.g., from quaternary ammonium compounds, while the edge-surfaces remain hydrophilic and bears an anionic charge when wetted by an aqueous solution having a pH of greater than 3.
  • long-chain (C 8 - C22) onium ions e.g., from quaternary ammonium compounds
  • the materials that lend themselves easily to selective surface- modification are the smectite clays, because of the differences in the surface properties of between the face surfaces and the edge surfaces of the clay platelets.
  • the face-surfaces of smectite clays bear an anionic charge due to the isomorphic substitution of aluminum by magnesium in the clay-crystal structure.
  • the electrical charge of the edge- surfaces depends on the type (anionic or cationic) of potential determining ions that adsorb on the edge surfaces when the clay platelets are dispersed in water or in an electrolyte solution.
  • long-chain (C8 - C22) quaternary surfactants can be made to adsorb only on the face-surfaces of clay platelets via ion- exchange, acting as counterions for the anionic platelet surface charge.
  • the typical loading level for the quarternary ammonium compound can be in the range of about 10-80% by weight based on the of dry weight of the smectite clay.
  • a important feature of one embodiment of the compositions and methods described herein relates to the final viscosity of the composite material (oil phase) containing the benefit agent, prior to the emulsification of the oil phase.
  • the final (low shear-rate,e.g., 0.5 - 2 rpm of spindle speed in a Brookfield viscometer) viscosity of the composite is preferably greater than 5,000,000 cps, more preferably greater than 1,000,000 cps, and most preferably greater than 5,000,000 cps, with the viscosity measured using a Brookfield viscometer.
  • the viscosity of the composite is preferably so high that the oil phase takes on a "stiff" consistency.
  • the hydrophobically-modif ⁇ ed smectite clay thickener is adequately exfoliated or delaminated (separation of clay platelets across their face surfaces, as described in the art) in the oil phase, using high-shear dispersion methods known in the art.
  • the oil phase may further contain other particulate materials in the form of inorganic and organic solids or liquids.
  • the oil phase itself can be a dispersion of an inorganic or an organic solid, or an emulsion of an inorganic or an organic liquid, comprising two or more immiscible liquids.
  • compositions and methods described herein pertains to the hydrophobic or oil-based benefit agents that are appreciably soluble in concentrated solutions of detersive surfactants, typically used in various cleansing products.
  • benefit agents are either dissolved, dispersed, or diluted in one or more hydrophobic solvent or liquid that has a relatively low solubility in concentrated surfactant solutions, in order to minimize the dissolution of the benefit agent in the detersive surfactant solutions.
  • hydrophobic solvents have a solubility of less than 2% by weight in an aqueous surfactant solution containing at least 3% (preferably 3%) by weight of one or more surfactant.
  • the oil-phase comprising one or more benefit agent and the hydrophobic solvent
  • the increased viscosity of the composite oil phase due to the formation of a particulate network structure of the exfoliated organophilic clay, is expected to provide an addition barrier to the diffusion of the benefit agent from the oil phase to the surrounding aqueous phase of the emulsion or of the final cleansing product composition.
  • the concentrated emulsions thus produced are eventually mixed or diluted with reagents selected from surfactants, polymers, and/or hydrophilic solvents to produce the compositions described herein.
  • the claimed compositions are produced upon mixing or diluting the foregoing cationic O/W emulsions of the benefit agent with reagents selected from surfactants and hydrophilic solvents including water, glycols, alcohols, and glycerol.
  • the resulting cationic emulsions of the benefit agents are highly stable against coalescence, the phenomenon that leads to the separation of the oil phase from the water phase in O/W emulsions.
  • the stability (tested using methods known in the art) is retained even when the emulsions are diluted with water, for example, in the amount of 1 part by weight of emulsion to 50 parts by weight of water.
  • the surface properties, including hydrophobicity and surface charge (as defined and characterized by methods known in the art), of these cationic particles and the benefit agent composite are such that the cationic particles can remain adsorbed on the surface of the benefit agent composite.
  • the enhanced substrate-deposition of the benefit agents from the claimed compositions, to a large extent, is attributed to having the cationic emulsifier particles pre- adsorbed on the emulsion droplets containing the benefit agent.
  • the benefit agent is not subjected to encapsulation within any capsule-like enclosure.
  • This allows full manifestation of the intended benefits (for example, fragrance emission and hair conditioning), once the benefit agents deposit onto the substrates being treated by the compositions described herein.
  • the foregoing cationic emulsions of the hydrophobic benefit agents do not adversely affect the foaming properties of surfactant-laden claimed compositions to any profound extent.
  • the emulsifier system used in producing the aforementioned additive-form for the benefit agent is not a surfactant type of an emulsifier, but rather comprises at least two components: i) a cationic particle having a relatively high surface charge (at least +25 millivolts of, zeta- potential) and a particle size of less than 21 micron; and ii) a surface-modified smectite clay that is dispersible in a water-immiscible organic liquid but not in water, with the clay modified by the adsorption of onium ions, e.g., obtained by dissolution of C8 - 22 alkyl ammonium compounds onto specific sections of the clay surface.
  • component (i) can be added only to the water phase and component (ii) only to the oil phase of the claimed OAV emulsions of benefit agents.
  • the emulsified oil phase with a benefit agent contained therein, prior to emulsification is a composite material providing for several beneficial features important to achieve certain objects of the present invention, such as: i) the composite material containing the benefit agent is considerably more viscous than the benefit agent itself, with the viscous consistency retained even upon heating; ii) the Hamaker constant of the composite material is considerably higher (at least 4% higher) than that of the benefit agent; and iii) the specific gravity of the composite material can be in the range of > 1.
  • a further distinguishing feature is that the benefit agent is not encapsulated in its entirety within a capsule wall, and accordingly there is no solid shell-wall separating an inner core comprising the benefit agent, from the surrounding solution phase of any cleansing or wash-off product composition that were to contain the benefit agent. Rather, the benefit agent composite is bonded to a particulate -based, cationic deposition-aid material that also serves as an emulsif ⁇ er for the OAV emulsion of the composite material in water, without forming any capsule-like enclosure around the composite.
  • compositions and methods described herein are an integral part of the multi-component emulsifier system used to emulsify the benefit agent-laden composite oil phase in a water phase, unlike in the prior art compositions wherein such a deposition polymer is not pre-adsorbed or bound to any non- encapsulated hydrophobic benefit agent emulsified in the water phase of these compositions.
  • Reagents selected from the group consisting of surfactants and hydrophilic solvents and mixtures thereof, with the surfactants selected from the group consisting of anionic, nonionic, zwitterionic, and cationic surfactants, and the hydrophilic solvents selected from water, alcohols, glycols, and glycerine;
  • Benefit agent selected from the group consisting of hydrophobic compounds, oils, oil-soluble or dispersible compounds, and water-immiscible compounds, offering hair-care, skin-care, fabric-care, and/or aesthetic or sensory property-boosting benefits.
  • these compositions may further contain ingredients selected from fatty alcohols having 8 to 22 carbon atoms, opacif ⁇ ers or pearlescers such as ethylene glycol esters of fatty acids (e.g., ethylene glycol distearate), viscosity modifiers, buffering or pH adjusting chemicals, water- soluble polymers including cross-linked and non cross-linked polymers, foam boosters, perfumes, dyes, coloring agents or pigments, herb extracts, preservatives, hydrotopes, enzymes, bleaches, fabric conditioners, optical brighteners, antioxidants, stabilizers, dispersants, soil release agents, anti-wrinkle agents, chelants, anti corrosion agents, and teeth cleansing and whitening agents, and mixtures thereof.
  • fatty alcohols having 8 to 22 carbon atoms such as ethylene glycol esters of fatty acids (e.g., ethylene glycol distearate), viscosity modifiers, buffering or pH adjusting chemicals, water- soluble polymers including cross-linked and non cross-linked polymers
  • the benefit agents are incorporated into the compositions as cationic oil-in-water (OAV) emulsions of a viscous composite material containing the benefit agent(s).
  • OAV oil-in-water
  • the cationic emulsion of the benefit agent(s) is produced using a multicomponent, particulate-based emulsifier system comprising mixtures of certain hydrophilic cationic polymers and water-insoluble or surface-active anionic polymers.
  • the benefit agents that have appreciable solubility in concentrated (amount > 3% by weight) surfactant solutions are first dissolved or dispersed or diluted in a suitable hydrophobic cosmetically acceptable liquid or solvent that has a relatively low ( ⁇ 1% by wt.) solubility in concentrated surfactant solutions.
  • a particularly useful cosmetic-solvent is a triglyceride, while equally useful is a silicone fluid, preferably a dimethicone fluid.
  • the oil-phase comprising a hydrophobic, water- immiscible liquid or solvent with the benefit agent(s) contained therein, is thickened using one or more organophilic smectite clay for which only the face-surface of the clay platelets is rendered hydrophobic, while the edge-surface remains hydrophilic, while capable of bearing an anionic surface charge when exposed to aqueous solutions at a pH of > 3.
  • the oil phase preferably has a viscosity of greater than 5,000,000 cps, as measured using a Brookfield RVT viscometer operated at 1 rpm (revolution per minute) of spindle speed with spindle number 7.
  • Non-limiting examples of suitable anionic surfactants are the sodium, ammonium, and mono-, di-, and tri-ethanolamine salts of alkyl sulfates, alkyl ether sulfates, alkaryl sulfonates, alkyl succinates, alkyl sulfosuccinate, N-alkoyl sarcosinates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, and ⁇ -olefm sulfonates.
  • the alkyl groups generally contain from 8 to 18 carbon atoms and may be unsaturated.
  • alkyl ether sulfates, alkyl ether phosphates, and alkyl ether carboxylates may contain from 1 to 10 ethylene oxide or propylene oxide units per molecule, and preferably contain 2 to 3 ethylene oxide units per molecule.
  • anionic surfactants include sodium or ammonium lauryl sulfate and sodium or ammoinium lauryl ether sulfate.
  • Suitable nonionic surfactants include, but not limited to, aliphatic, primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, generally ethylene oxide and generally 6-30 ethylene oxide groups.
  • Other suitable nonionic surfactants include mono- or di-alkyl alkanolamides, alkyl polyglucosides, and polyhydroxy fatty acid amides.
  • amphoteric surfactants suitable for use in the present invention include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulfobetaines, alkyl glycinates, alkyl carboxyglycinates, alkyl amphopropionates, alkyl amidopropyl hydroxysultaines, acyl taurates, and acyl glutamates wherein the alkyl and acyl groups have from 8 to 18 carbon atoms.
  • the level of surfactants may range from 0.5 to 95%, preferably from 2 to 90%, and most preferably from 3 to 90% by weight of the claimed compositions.
  • hydrophilic solvents suitable for use include water and hydrophilic organic liquids and mixtures thereof.
  • preferred hydrophilic organic liquids include glycerol, ethanol, isopropanol, propylene glycol, butylene glycol, hexylene glycol, polyethylene glycol and mixtures thereof.
  • the level of hydrophilic solvents may range from 0.1 to 95%, preferably from 1 to 90%, and most preferably from 3 to 90% by weight of the claimed compositions.
  • Preferred benefit agents include, but not limited to, the following: a) silicone oils, resins, and modifications thereof such as linear and cyclic polydimethylsiloxanes, amino-modified, alkyl, aryl, and alkylaryl silicone oils, which preferably have a viscosity » 50,000 cst; b) fragrance, perfumery, and essential oils and resins; c) organic sunscreen actives, for example, octylmethoxy cinnamate; d) antimicrobial agents, for example, 2-hydroxy-4,2,4-trichlorodiphenylether; e) ester solvents; for example, isopropyl myristate; f) lipids and lipid like substance, for example, cholesterol; g) hydrocarbons such as paraffins, petrolatum, and mineral oil h) fish and vegetable oils i) hydrophobic plant extracts; j) therapeutic and skin-care reagents; k) hydroquinone 1) waxes; and m)
  • One or more of the foregoing benefit agents is included in the compositions described herein in an amount varying from 0.05 to 99%, preferably from 0.1 to 40%, and most preferably from 0.5 to 20% by weight of the detersive composition.
  • the benefit agents are incorporated into the detersive compositions by mixing or diluting concentrated emulsions of the benefit agents with detersive surfactants, wherein in the preferred embodiment, the emulsions are produced in accordance with the following sequential steps (i) through (iii).
  • the benefit agent is dissolved or dispersed or diluted in a hydrophobic liquid or solvent with poor surfactant- phase solubility (herein defined as having a solubility ⁇ 2% by weight in an aqueous detersive surfactant solution with a surfactant content in the range of 3 - 25%).
  • a preferred diluent is a triglyceride, castor oil, or a silicone fluid, dimethicone fluid, having a viscosity of > 50 centistokes.
  • the triglyceride- or dimethicone-content of the resulting oil-phase is preferably at least 50% by weight, e.g., 50 - 95% by weight, while the amount of the benefit agent is the range of 0.1 - 60%.
  • the oil-phase containing the benefit agent, or the silicone-based benefit agent is thickened using an organophilic smectite clay. Not all commercially available organophilic smectite clays are ideal for obtaining the full advantage of the compositions and methods described herein.
  • the preferred organophilic smectite clays are those for which only the face surface is rendered hydrophobic by the adsorption of fatty quaternary ammonium compounds with 8 to 22 carbon atoms in the alkyl chain, while the edge-surface remains hydrophilic.
  • suitable organoclays include, but not limited to, the organophilic bentonite clays available from Nanocor, a subsidiary of AMCOL International Corporation.
  • the amount of organoclay added to the oil- or silicone-phase can be 3 - 60% by weight, preferably 20 - 50%, and ideally 25 - 45%, based on the weight of the oil- or silicone phase.
  • one or more polar materials such as propylene carbonate, ethanol, alkylene glycol, and water and mixtures thereof may be added at the level of 10 - 60% by weight, based on the weight of the organoclay.
  • the organoclay is dispersed in the hydrophobic liquid using high-shear equipment such as rotor-stator homogenizer and extruder.
  • high-shear equipment such as rotor-stator homogenizer and extruder.
  • the thickened oil- or silicone-phase is emulsified in water using an emulsif ⁇ er system comprising in part a cationic particle having a relatively high cationic surface charge and a size of ⁇ 2 microns.
  • the cationic particle component of the emulsifier comprises three polymeric components, an anionic polymer and two hydrophilic cationic polymers, as described in more detail to follow. However, not all three of these polymeric components of the emulsifier system are added to the emulsion batch at the same time. Two of the three components, the anionic polymer, and one of the cationic polymers are added to the batch prior to adding the third component. These two components are collectively referred to herein as part A of the emulsifier system. The third polymeric component, added at a later stage of the emulsification process, is referred to herein as part B of the emulsifier system.
  • the water-phase of the emulsion is prepared by combining in a given sequential fashion de-ionized water, the anionic polymer of part A of the emulsifier system, and a preservative, and subsequently homogenizing the mixture in a rotor-stator homogenizer, for example.
  • the next step is to add the cationic polymer of part A of the emulsifier system, and subsequently homogenizing the mixture under high shear.
  • the subsequent step is to add the thickened oil- or silicone-phase to the water-phase, while the batch remains under agitation. Subsequently, the batch is homogenized using high- shear agitation provided by an agitator.
  • the emulsion may further contain ingredients such as one or more pH adjustment chemicals, buffering chemicals, one or more water-phase thickener selected from non-ionic and cationic polymer-based thickeners, and one or more optical brightener pigments.
  • ingredients such as one or more pH adjustment chemicals, buffering chemicals, one or more water-phase thickener selected from non-ionic and cationic polymer-based thickeners, and one or more optical brightener pigments.
  • the amount of thickened oil- or silicone-phase in the emulsion may range from 10 to 60% by weight of the final composition, but most preferably from 25 to 45%.
  • the emulsifier system used in producing the concentrated, cationic emulsions of the benefit agents is comprised of three essential components: (1) an anionic polymer that is sufficiently surface-active for adsorption at the oil-water interface, and is preferably water- insoluble; (2) a medium-to-high molecular weight, hydrophilic, cationic polymer that is virtually insoluble (soluble less than 1.0% by weight) in 3 weight% or higher anionic surfactant solutions; and (3) a high-to-very high molecular weight, hydrophilic, cationic polymer.
  • the anionic polymer is dissolved or dispersed in water, prior to adding the cationic polymer (component 2).
  • component 2 For the anionic polymers having weak-acid groups, for example, the phosphate and carboxylate groups, a base is added prior to adding component (2), in order to ensure that these anionic groups are fully or partially dissociated, producing anionic charge sites on the polymer chain.
  • component (3) is preferably added at a later stage of emulsification.
  • components (2) and (3) are both hydrophilic, cationic polymers, they are preferably not interchangeable in terms of their order of addition, in order to achieve the full advantage of the compositions and methods described herein.
  • colloidal- stability stability against particle aggregation or flocculation, which may be determined using methods (e.g., determining particle size as a function of time, stability under large centrifugal forces, measuring dispersion viscosity as a function of shear-rate) known in the art.
  • This is selected from water-soluble anionic polymers, such as polyphosphate, polysulfonates (e.g., polyvinyl sulfonate, lignosulfonates), polycarboxylates (e.g. sodium polyacrylate), polysulfates (e.g., polyvinyl sulfate), and silicone polymers with a pendant anionic group selected from carboxylate, sulfate, and phosphate groups.
  • the polymer is sufficiently surface-active for adsorption at the oil-water interface, if it is capable of reducing the surface tension of water, when added at a level of 1% by weight, preferably reducing the surface tension by at least 15%.
  • the most suitable polymer is poly(diallyl dimethyl ammonium chloride) which will be referred to herein as PoIy(DADMAC). It has a cationic nitrogen content of about 8.67% by weight. Due to their relatively high solubility in concentrated surfactant solutions, examples of hydrophilic cationic polymers which may not be best suited to serve as component (2) of the aforementioned emulsif ⁇ er system include copolymers of DADMAC and acrylamide monomers, also known as polyquaternium-7, quaternized copolymers of vinylpyrrolidone and dimethylaminomethylmethacryalte, also known as polyquaternium-11, copolymer of vinylpyrrolidone and methacrylamidopropyltrimethylammonium chloride, also known as polyquaternium 28, and cationic derivatives of natural polymers such as cellulose, starch, and guar gum. Some of these polymers, however, may be suitable as component (3) of the emulsifier system.
  • This is selected from high-to-very high molecular cationic polymers having molecular weight preferably in the range of greater than 600,000 Dalton, more preferably in the range of 2,000,000 - 6,000,000 Dalton, and most preferably in the range of 1,000,000 - 4,000,000 Dalton.
  • the cationic charge content of these polymers is preferably in the range of 0.1 - 4.5% by weight of cationic nitrogen group.
  • examples of such polymers include cationic copolymers of acrylamide, and cationic derivatives of natural polymers such as cellulose ether polymers, guar gum, and starch.
  • the most preferred component (3)-polymer are the cationic derivatives of cellulose, guar, and starch.
  • the silicone- and castorlatum-based benefit agents were thickened following a procedure similar to the one above, except that these benefit agents were not diluted in a triglyceride prior to undergoing thickening. Also, once the composition appeared to be lump-free, a polar activator, propylene carbonate, was added, and the batch was subsequently homogenized further until it looked uniform and viscous.
  • the organophilic smectite clay used in Mix Nos. 1, 3, and 5 is an organophilic sodium bentonite clay from AMCOL International Corporation, while a mixture of two different organophilic sodium bentonite clays was used in Mix No. 4.
  • the particle size as measured based on video-microscopy or on a Malvern Zetasizer particle size analyzer would indicate that the particle size is in the colloidal range, i.e., less than 2 micron; and iii) the particles are sufficiently small for to be able to resist centrifugal separation (i.e., virtually no separation of the dispersed material) when the dispersion (having a Brookfield viscosity of ⁇ 200 cps for the spindle-speed range of 1-10 rpm) is centrifuged at 4,500 rpm for a period of 30 minutes.
  • the thickened benefit agent composite -phase was added to the batch in small portions, while keeping the batch under high-speed agitation using a dispersion blade agitator.
  • the mixture was homogenized adequately under high-shear agitation to form a homogeneous emulsion.
  • Polymer JR 30M was added next in the form of an aqueous solution containing 2% by weight of the polymer.
  • the emulsion was homogenized further, following the addition of the polymer solution.
  • the composition for the resulting final emulsion is presented in Table II, wherein the Brookfield viscosity of the final emulsion is at least 10,000 cps at 1 rpm of spindle speed. TABLE II
  • Conditioning (i.e., 2-in-l type) shampoos, Shampoo Nos. 1 and 2 were manufactured using a dimethicone (silicone) emulsion prepared as per the specifications in EXAMPLE II, wherein the thickened silicone composition corresponds to Mix No. 5 in Table I of EXAMPLE I.
  • Bodywash No. 2 contained a castorlatum emulsion produced as per the specifications in EXAMPLE II, using the thickened castorlatum composition of Mix No. 2 in Table I.
  • a primary function or benefit of a hair-conditioning agent is to reduce the hair- combining strength, especially when the hair is wet.
  • the silicone deposition efficiency of the shampoo compositions of the present invention was evaluated by conducting panel testing.
  • Shampoo No. 1 of Table III was tested against a reference product comprising a leading commercial conditioner product that is rated by the manufacturer to yield a good hair- conditioning level of 5 on a scale of 1 to 10 (the higher the number, the greater the level of conditioning).
  • the panel testing was carried out at Cantor Research Laboratories, New York, wherein a panel often panelists was convened at two different times, i.e., a total of twenty panelists were involved in evaluating Shampoo No. 1.
  • the test protocol followed is as follows.
  • a technical staff from Cantor Laboratories washed the panelist's hair first with a clarifying shampoo free of silicone and any other hair-conditioning agent, in order to wash off any residual hair-conditioning agent from prior use. This washing process was repeated (typically 2-3 times) until the panelist and the technician individually rated the ease of combing for the wet hair at the score of 2-3 on a scale of 1-10 (the higher the number, the greater the ease of combing).
  • the washed hair was dried and the dried hair was tested again for ease of combing individually by the panelist and the technician, following the same scoring protocol as noted above. Subsequently, the panelist's hair was split into two halves. Shampoo No. 1 was applied on one half, and the leading conditioner on the other half of the hair.
  • the panelist and the technician evaluated the ease of combing of the wet hair using the above scoring protocol. This evaluation was repeated after the hair was dried. The panelist and the technician also rated the smoothness and the shine for the two halves of the dried hair.
  • the composite average (averaged over all panelist scores and technician scores for all panelists) rating provided by the twenty panelists and the technician is presented in Table IV, wherein the term "enhancement" denotes the difference in score for a conditioning property between post-clarifying shampoo and post-shampoo 1 or post-conditioner (i.e., Score after shampoo No.
  • the leading conditioner was tested (involving the same twenty panelists) also against a leading commercial conditioning (2-in-l type) shampoo that is rated by the manufacturer to yield deep conditioning. Based on certain findings, this 2-in-l shampoo appears to resemble shampoo No. 1 considerably, in terms of levels of detersive surfactants and the conditioning agents.
  • the leading 2-in-l shampoo contains a cationic deposition polymer, cationic hydroxyethyl cellulose. The average ratings for the two products are also presented in Table IV (Test 2).
  • the conditioning shampoo, Shampoo No. 1, an example of one embodiment of the present invention came considerably close to matching the hair conditioning performance of a leading conditioner.
  • the leading commercial conditioning shampoo fell much short of the leading conditioner in providing for hair- conditioning.
  • Shampoo No. 2 in Table III provided slightly better hair-conditioning, as compared to the leading commercial 2-in-l shampoo (containing 1.2 wt.% dimethicone plus two additional conditioning oils), even though Shampoo No. 2 had a significantly lower level (0.75 wt.% dimethicone) of conditioning agent(s).
  • the conditioning shampoo compositions described herein showed good foaming properties, no worse than the leading commercial conditioning shampoo.
  • the test method used for evaluating the foaming property involves 2OX dilution of the shampoo with water in a 100-mL graduated centrifuge tube, under mixing in a rotary mixer for 5 minutes, followed by noting the volume of the resulting foam in the centrifuge tube.
  • Bodywash 2OX dilution of the shampoo with water in a 100-mL graduated centrifuge tube, under mixing in a rotary mixer for 5 minutes, followed by noting the volume of the resulting foam in the centrifuge tube.
  • the leading commercial bodywash product likely has a much higher (potentially as much as about 3X) level of a skin- moisturizing emollient, petrolatum, as compared to Bodywash No. 1, containing silicone as the skin-moisturizing agent.
  • the reduction in the TEWL rate was about 2.7 unit with the leading commercial bodywash, closely followed by the 2.1 unit reduction in the TEWL rate with Bodywash No. 1.
  • detersive compositions described herein have been evaluated for applications such as fabric softening (due to silicone deposition) and fragrance extension from laundry detergent wash, yielding results that further confirm the prospects of achieving good deposition of hydrophobic benefit agents from a wide variety of detersive compositions.

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Abstract

L'invention concerne une composition nettoyante ou de conditionnement de surface comprenant un mélange de (i) et (ii) dans de l'eau : i) un agent tensioactif choisi dans le groupe constitué par les agents tensioactifs anioniques, non ioniques, zwitterioniques, cationiques et leurs mélanges ; et ii) un agent bénéfique hydrophobe sous forme particulaire ayant une taille moyenne de particule allant de 1 à 1 000 microns et une gravité spécifique ' 1, nonencapsulé dans un film ou une enceinte de type capsule, l'agent bénéfique hydrophobe particulaire comprenant : a) une forme physiquement modifiée de l'agent bénéfique hydrophobe ; et b) un matériau facilitant le dépôt lié à la surface du matériau d'agent bénéfique physiquement modifié, la liaison entre lesdits deux matériaux étant réalisée avant l'ajout à i), ledit matériau facilitant le dépôt n'étant pas un agent tensioactif ayant un poids moléculaire moyen en poids inférieur à 5 000 Daltons.
PCT/US2008/053490 2007-02-08 2008-02-08 Compositions contenant des composites d'agent bénéfique pré-émulsifiées à l'aide de particules cationiques colloïdales WO2008127766A2 (fr)

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Cited By (5)

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WO2009126960A3 (fr) * 2008-04-11 2010-01-14 Amcol International Corporation Encapsulation d'une fragrance dans un multicouche
EP2155846A2 (fr) * 2007-12-03 2010-02-24 Amcol International Corporation Compositions contenant des composites d'agents utiles pré-émulsifiés en utilisant des particules cationiques colloïdales
WO2010105922A1 (fr) 2009-03-19 2010-09-23 Unilever Plc Améliorations liées à l'administration d'une substance apportant un bénéfice
US8188022B2 (en) 2008-04-11 2012-05-29 Amcol International Corporation Multilayer fragrance encapsulation comprising kappa carrageenan
WO2013107778A1 (fr) * 2012-01-18 2013-07-25 Unilever Plc Compositions pour traitement capillaire

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JP4046193B2 (ja) * 2002-06-04 2008-02-13 ザ プロクター アンド ギャンブル カンパニー アミノシリコーン含有コンディショニングシャンプー
EP1838393A1 (fr) * 2005-01-12 2007-10-03 Amcol International Corporation Compositions detersives contenant des agents benefiques pre-emulsifies au moyen de particules cationiques colloidales
CA2691036A1 (fr) * 2007-05-14 2008-11-27 Amcol International Corporation Compositions contenant des composites d'agents utiles preemulsifies a l'aide de particules cationiques colloidales

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2155846A2 (fr) * 2007-12-03 2010-02-24 Amcol International Corporation Compositions contenant des composites d'agents utiles pré-émulsifiés en utilisant des particules cationiques colloïdales
EP2155846A4 (fr) * 2007-12-03 2012-07-04 Amcol International Corp Compositions contenant des composites d'agents utiles pré-émulsifiés en utilisant des particules cationiques colloïdales
WO2009126960A3 (fr) * 2008-04-11 2010-01-14 Amcol International Corporation Encapsulation d'une fragrance dans un multicouche
US8188022B2 (en) 2008-04-11 2012-05-29 Amcol International Corporation Multilayer fragrance encapsulation comprising kappa carrageenan
WO2010105922A1 (fr) 2009-03-19 2010-09-23 Unilever Plc Améliorations liées à l'administration d'une substance apportant un bénéfice
WO2013107778A1 (fr) * 2012-01-18 2013-07-25 Unilever Plc Compositions pour traitement capillaire
CN104053477A (zh) * 2012-01-18 2014-09-17 荷兰联合利华有限公司 毛发处理组合物
JP2015507639A (ja) * 2012-01-18 2015-03-12 ユニリーバー・ナームローゼ・ベンノートシヤープ 毛髪処理組成物
EA030101B1 (ru) * 2012-01-18 2018-06-29 Унилевер Н.В. Композиция шампуня и способ обработки волос

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