+

WO2008005693A2 - composition de microcapsules stabilisées à base de polymère cationique - Google Patents

composition de microcapsules stabilisées à base de polymère cationique Download PDF

Info

Publication number
WO2008005693A2
WO2008005693A2 PCT/US2007/071782 US2007071782W WO2008005693A2 WO 2008005693 A2 WO2008005693 A2 WO 2008005693A2 US 2007071782 W US2007071782 W US 2007071782W WO 2008005693 A2 WO2008005693 A2 WO 2008005693A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
shell
cross
polymer
microcapsule
Prior art date
Application number
PCT/US2007/071782
Other languages
English (en)
Other versions
WO2008005693A3 (fr
Inventor
Amjad Farooq
Marija Heibel
Myriam Peeters
Alain Jacques
Mary Holmgren
Original Assignee
Colgate-Palmolive Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colgate-Palmolive Company filed Critical Colgate-Palmolive Company
Priority to AU2007269428A priority Critical patent/AU2007269428A1/en
Priority to EP07798887A priority patent/EP2046935A2/fr
Priority to CA002656326A priority patent/CA2656326A1/fr
Priority to BRPI0713074-0A priority patent/BRPI0713074A2/pt
Priority to MX2008016479A priority patent/MX2008016479A/es
Publication of WO2008005693A2 publication Critical patent/WO2008005693A2/fr
Publication of WO2008005693A3 publication Critical patent/WO2008005693A3/fr
Priority to IL196157A priority patent/IL196157A0/en
Priority to NO20090477A priority patent/NO20090477L/no

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • 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
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Definitions

  • Consumer products such as fabric care products, personal care products and home care products are well known in the art and usually comprise one or more perfumes to impart the consumer product and/or a substrate treated or applied with the consumer product with a fragrance; however, these perfumes dissipate over time from the consumer product or substrate.
  • Another problem with perfumes in consumer products is that they are released prior to an optimal delivery time, and the user of the consumer product is deprived of experiencing the perfume's fragrance.
  • a perfume it is desirable for a perfume to be present on clothes treated with a detergent and/or fabric softener long after such treatment, and there is a tendency for perfumes to evaporate or diffuse from the clothes over time.
  • Clog P The calculated log P (Clog P) of many perfumes is known in the art, and has been reported, for example, in the Ponoma92 database, available from Daylight Chemical Information Systems, Inc. (Daylight CIS) Irvine. CA. Methods of calculating Clog P are also known in the art. Perfumes with lower Clog P values may be more volatile and exhibit higher aqueous solubility than perfumes having higher Clog P values, and are therefore preferred to be used in consumer products. However when lower Clog P materials are encapsulated, they may have a greater tendency to leach out of, or diffuse out of the shell into the consumer product (preventing optimal delivery of fragrances), and the perfumes may eventually diffuse out of the consumer product prior to use by the consumer.
  • fragrance microcapsules are incorporated in consumer products containing solvents and/or surfactants, e.g., shampoos
  • stability problems may arise.
  • the encapsulated perfume may leach out of the shell.
  • the shell may also absorb a solvent, surfactant, or any other material in the consumer product, causing the shell's integrity to be compromised.
  • the shell may swell because additional materials diffuse into the shell or the core, or the shell may shrink as materials of the core diffuse out of the shell. Indeed, components of the shell may even diffuse into the consumer product.
  • compositions suitable for use in compositions that provide for stability of microcapsules encapsulating fragrance or antimicrobial materials are provided.
  • the invention provides a composition
  • a microcapsule comprising a shell encapsulating a material having an average Clog P of at least about 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3
  • a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 mole percent acrylamide. and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross-linking agent.
  • the invention provides a method of improving the stability of a product that comprises at least one microcapsule comprising admixing with the product (before, after, or simultaneously with the addition of the at least one microcapsule) a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 percent acrylamide, and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross-linking agent, wherein the microcapsule comprises a shell encapsulating a material having an average ClogP of at least 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3.
  • ranges are used as a shorthand for describing each and every value that is within the range. Any value within the range can be selected as the terminus of the range. Percentages given below are percent of total weight unless otherwise indicated.
  • the present invention is related to the benefit that is provided by use of a cationic polymer in a composition containing microcapsules, in particular to microcapsules having an average Clog P of at least about 2.5 with more than 60% by weight of the material having a Clog P of at least 3.3.
  • the addition of the cationic polymer to the composition increases the stability of the microcapsule in the composition compared to compositions lacking such cationic polymer.
  • Perfumes are known in the art and may include odoriferous materials which are able to provide a fragrance to consumer products and/or impart a fragrance to a substrate, e.g.. shampoos and conditioners treat hair, laundry detergents and rinse cycle fabric softeners treat fabrics and clothes, glass cleaners treat glass and hard surfaces, colognes, soaps, deodorants, antiperspirants and shower gels treat skin and hair. Perfumes may also counteract malodors and/or provide a fragrance.
  • the perfumes may be in liquid state at ambient temperature, although solid perfumes may also be useful.
  • Perfumes may include aldehydes, ketones, esters and other chemicals and compounds known in the art, including natural, synthetic perfumes, and mixtures thereof.
  • Perfumes useful for the present invention may have relatively simple compositions or may comprise complex mixtures of natural and synthetic chemical components, all of which are intended to provide an odor or fragrance in consumer products, and/or to the substrate. It is understood in the present application that a perfume may be substituted with flavors known in the art, and that the term perfume, as used herein, also includes flavors. Generally, perfumes may be present in consumer products between 0.00001 - 10%.
  • Formulations of the invention may comprise unencapsulated fragrance materials in addition to any fragrance material present in the microcapsules.
  • Fragrance microcapsules are generally known in the art, see ,e.g., WO/2004016234. US 2005/0153135. US 2005/0256027, US2004/0072719A1, US2004/0072720A1 , US20040071742A1 , US2004/0071746A1 , US 6,194,375, WO 02/074430A1; US 6.620.777, the contents of each patent publication are incorporated herein by reference.
  • a fragrance microcapsule generally has a shell which encapsulates a perfume, and optionally other materials, such as solvents, surfactants, hydrophobic polymers, and other materials known in the art.
  • the shell may be considered to be made up of a tight collection of strands of polymer(s) and may have a diameter less than 1000 ⁇ m, and the shells may have a mean diameter in the range 1 to 500 ⁇ m, preferably 1 to 300 ⁇ m, more preferably 1 to 50 ⁇ m and most preferably 1 to 10 ⁇ m.
  • the size of the shell may be modified by methods known in the art. Preferred sizes for the shell will depend upon their intended use.
  • the shell generally prevents leaching of the perfumes from the consumer product.
  • the shell may also bind to substrates, and release the perfume under predetermined conditions, i.e., while fabric is being ironed, a fragrance microcapsule on the fabric bursts due to change in temperature, or while fabric is being worn, a fragrance microcapsule bursts due to friction, shearing, or other physical/mechanical stress caused by the movement of the wearer.
  • a microcapsule's shell may be made by any of the methods known in the art.
  • the shell may be a polymer or resin known in the art. Shells comprised of polyurethane, polyamide, polyolefin, polysaccaharide, protein, silicone, lipid, modified cellulose, gums, polyacrylate, polyphosphate, polystyrene, and polyesters or combinations thereof may be suitable for use in the present invention.
  • Preferred shells may be an aminoplast which is formed by the reaction of one of more amines known in the art with one or more aldehydes known in the art, such as formaldehyde.
  • aminoplasts may be prepared by polycondensation.
  • a preferred aminoplast may be a melamine-formaldehyde or urea-formaldehyde condensate, such as melamine resin or urea-formaldehyde resin.
  • Aminoplasts preferably a melamine resin, may be used singularly or in combination with other suitable amides known in the art. crosslinking agents known in the art (e.g.. toluene diisocyanate, divinyl benzene, butane diol diacrylate), and secondary polymers known in the art. such as polymers and co-polymers of maleic anhydride.
  • Aminoplasts may also be mixed resins of urea-formalehyde, maleic anhydride copolymers, and melamine-formalehyde.
  • the microcapsules of the present invention have a shell, the shell having an inner surface, and an outer surface.
  • the inner surface and/or outer surface of the shell may be coated, e.g., with a polymer.
  • the coaling on the inner surface and/or outer surface may improve the barrier properties of the shell and thus may enhance retention of the encapsulated materials in surfactant- containing and/or solvent containing consumer products.
  • a cationically charged water-soluble polymer known in the art can be coated on shell.
  • the water-soluble polymer can also be an amphoteric polymer with a ratio of cationic and anionic functionalities resulting in a net total charge of zero and positive.
  • Methods for coating the cationically charged polymer onto the microcapsule are also known in the art.
  • the application of a coating to the inner surface of the shell capsules may be carried out by a number of methods known in the art.
  • One approach known in the art involves the use of a suitable material for the coating which is insoluble in the material to be encapsulated, but can be dissolved in a water soluble solvent e.g., ethanol, carbitol, which is miscible with the material to be encapsulated.
  • the coating material typically a polymer, is dissolved in the solvent and then the solution is dissolved in the material to be encapsulated.
  • the material to be encapsulated is then emulsified into a standard aminoplast capsule forming aqueous solution.
  • the solvent is lost to the water and the polymer precipitates out from solution at the surface of the emulsion droplets, forming a film at the interface of water/material to be encapsulated.
  • An encapsulation process known in the art may then be carried out and the coating may be deposited on the inner surface of the shell.
  • a coating material e.g., silicone
  • a coating material used may be immiscible with materials to be encapsulated and immiscible with water, and is capable of forming a thin film at the water interface.
  • a shell encapsulate comprising a coating of silicone on the inner surface of the shell can be prepared by dispersing the material to be encapsulated within the silicone and then emulsifying this mixture so that an emulsion is formed where droplets of encapsulated material are surrounded by a thin film of silicone. The encapsulation process is then carried out as known in the art.
  • a thin film may be formed at the surface by dispersing the material to be encapsulated in water, adding the second material e.g., silicone and allowing it to coat the encapsulating material droplets subsequently.
  • An inner surface coating may also be made from a film-forming polymer known in the art, for example: poly(ethylene-maleic anhydride), povidones, waxes e.g. carbowax.
  • polyvinylpyrrolidone (PVP) and its co-polymers such as polyvinylpyrrolidone-ethyl acrylate (PVP-EA). polyvinylpyrrolidone-vinyl acrylate.
  • polyvinylpyrrolidone methylacrylate PVP-MA
  • polyvinylpyrrolidone/vinyl acetate polyvinyl acetal
  • polyvinyl butyral polysiloxane
  • poly(propylene maleic anhydride) maleic anhydride derivatives and co-polymers of the above, e.g. polyvinyl methyl ether/maleic anhydride.
  • the inner wall coating comprises polysiloxane, PVP or PVP co-polymers, more preferably PVP or PVP co- polymers, and even more preferably PVP co-polymers, particularly PVP-MA or PVP-EA.
  • a coating may be applied to the outer surface of a shell techniques known in the art, such as by including spraying, fluid bed coating, or precipitating.
  • a coating e.g., of a polymer
  • a coating may be precipitated from aqueous solution to condense onto the outer surface of the shell or microcapsule, e.g., in the form of a capsules slurry, with precipitation being caused by change of temperature, pH. addition of salt, and other variables and conditions known in the art.
  • the shell capsule to be coated is thus formed in a separate first step, prior to the application of the coating to the outer surface of the shell wall.
  • a coated shell capsule may be prepared for example, by coacervation or polycondensation.
  • the outer surface coating may comprise high molecular weight, film- forming polymers known in the art. which may optionally be cross-linked. "High molecular weight” is meant a molecular weight average of greater than 2000 Da. preferably greater than 4000 Da, more preferably greater than 5000 Da.
  • the polymer maybe water-soluble or water- insoluble, preferably water-soluble.
  • Suitable polymers for use may include, polyvinyl alcohol (PVOH), styrene-butadiene latex, gelatin, gum arabic, carboxymethyl cellulose, carboxymethyl hydroxyethyl cellulose, hydroxyethyl cellulose, other modified celluloses, sodium alginate, chitosan, casein, pectin, modified starch, polyvinyl acetal. polyvinyl butyral, polyvinyl methyl ether/maleic anhydride. PVP and its co-polymers (e.g. polyvinylpyrro Ii done/vinyl acetate (PVP/VA).
  • polyvinyl pyrrolidone/dimethylaminoethyl methacrylate) PVP/DMAEMA
  • poly(vinyl pyrrolidone/methacrylamidopropyl trimethyl ammonium chloride) melamine- formaldehyde and urea-formaldehyde.
  • the outer surface of the shell is coated with PVOH, PVP or a PVP co-polymer.
  • a preferred coated shell may be an aminoplast capsule having a coating of PVOH, PVP or a co-polymer PVP (preferably PVP/DMAEMA) on the outer surface of the shell and/or a coating of a film- forming polymer (preferably PVP-EP) on the inner surface.
  • the coating may be cross-linked in any known manner, e.g., by interfacial cross-linking.
  • a shell capsule useful herein may have more than one coating on the outer surface of the shell.
  • Coated shell capsules typically have a wall thickness in the range of about 0.01 to about 30 ⁇ m, preferably about 0.01 to about 5 ⁇ m. more preferably about 0.03 to about 1 ⁇ m, most preferably about 0.03 to about 0.5 ⁇ m.
  • the wall thickness may be regulated and controlled according to the encapsulate size and by varying the relative proportions of coating and shell polymer.
  • the weight ratio of coating to shell wall is typically in the range of about 0.01 to about 10: 1 , preferably about 0.1 : 1 to about 10: 1 , more preferably about 0.1 : 1 to about 3:1.
  • the weight ratio of polymer shell wall material to encapsulated material is in the range of about 1: 10 to about 3:2 and preferably in the range of about 1:10 to about 1:2.
  • the coating on the inner surface and/or outer surface will increase these weight ratios.
  • materials having an average Clog P value equal to or greater than 2.5 may be encapsulated, preferably within the range of about 3 to about 5.
  • Materials used in uncoated microcapsules may include materials wherein at least about 60% have a Clog P equal to or greater than about 3.3, preferably greater than about 4.
  • average Clog P is meant the average Clog P for all of the encapsulated materials.
  • the average Clog P of the encapsulated materials may be raised, for example, by adding a solvent having a high ClogP, e.g., about 6 or greater, wherein the solvent is miscible with the other encapsulated materials.
  • One or more perfumes may be used in the present invention as a mixture of perfumes.
  • a mixture of perfumes greater than about 60 weight percent of the fragrance materials have a Clog P of greater than about 3.3.
  • more than about 80 weight percent of the fragrances have a Clog P value of greater than about 4.0, and more preferably, more than about 90 weight percent of the fragrances have a Clog P value of greater than about 4.5 may be used.
  • the microcapsule contains a core within the shell, and the core comprises a perfume or other benefit agent, such as a flavorant or antibacterial material, and may optionally contain other materials known in the art, for example, hydrophobic solvents such as triglyceride oil, mono and diglycerides, mineral oil, silicone oil. diethyl phthalate, polyalphaolefins, fatty alcohols, castor oil and isopropyl myristate.
  • suitable solvents include those having reasonable affinity for the perfume, and the solvent may have a Clog P greater than 3.3, preferably greater than 6 and most preferably greater that 10.
  • a preferred solvent may be isopropyl myristate.
  • a preferred solvent may also be silicone, such polydimethylsiloxane and polydimethylcyclosiloxane.
  • a preferred solvent may be diethyl phthalate.
  • the solvent may be greater than about 30 weight percent, preferably greater than about 50 weight percent and more preferably greater than about 70 weight percent of the core.
  • hydrophobic polymers in a microcapsule may also improve stability of the microcapsule by slowing diffusion of the perfume from the shell.
  • the amount of the hydrophobic polymer may be less than 80% of the microcapsule by weight, preferably less than 50%, and most preferably less than 20%.
  • a hydrophobic polymer may be ethyl cellulose, hydroxypropyl cellulose, cellulose acetate butyrate. ethylene vinyl acetate, polystyrene, and PVP and ester terminated polyamides or amide terminated polyamides.
  • a cationic polymer is added to the consumer product to increase the stability of the microcapsule.
  • the cationic polymer in the present invention is a cross-linked polymer which is cross-linked using a cross-linking agent of a difunctional vinyl addition monomer at a level of about 5-500 ppm. preferably about 70 to about 300 ppm, preferably about 75 to about 200ppm, and most preferably of from about 80 to about 150 ppm.
  • the cationic polymer may be a cationic vinyl polymer.
  • a cationic vinyl polymer may be derived from the polymerization of from about 5 to 100 mole percent of a cationic vinyl addition monomer and 0 to about 95 mole percent of acrylamide.
  • the difunctional vinyl addition monomer may be a polyethylene glycol diacrylic ester having a weight average molecular weight of from 300 to 3,000.
  • the cationic polymer may be derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 mole percent of acrylamide, and about 70 to about 300 ppm of a difunctional vinyl addition monomer crosslinking agent.
  • the difunctional vinyl addition monomer may be a polyethylene glycol diacrylic ester having a weight average molecular weight of about 300 to about 3,000.
  • the cationic polymer may also be a cross-linked cationic vinyl addition polymer derived from the polymerization of about 15 to about 70 mole percent of a quaternary ammonium salt of dimethyl/aminoethylmethacrylate and about 30 to about 85 mole percent of acrylamide, and about 0.005 to about 0.025 weight percent of the polyethylene glycol diacrylic ester.
  • the polyethylene glycol diacrylic ester may be polyethylene glycol dimethacrylate.
  • the cationic polymer may be prepared as water in oil emulsions, wherein the cross-linked polymers are dispersed in the oil, preferably a mineral oil.
  • a cationic polymer may be a cross-linked copolymer of a quaternary ammonium acrylate or methacrylate in combination with an acrylamide comonomer. Additional description of cationic polymers useful in the present invention may be found in U.S. Patent Nos. 4,806,345 and 6,864,223, which are incorporated herein by reference.
  • a composition may comprise about 0.001 % to about 40% total weight of the cationic polymer, preferably about 0.01% to about 10%, more preferably, about 0.01% to about 5%.
  • the amount of cationic polymer present will depend upon the composition and the microcapsule used therein.
  • the cationic polymer may be admixed to the consumer product before, during or after the addition of a microcapsule to the consumer product.
  • the cationic polymer is well suited for use in a variety of well-known consumer products comprising a microcapsule, such as oral care products, toothpastes, mouthwashes, personal care products, lotions, creams, shampoos, conditioners, hair gel, antiperspirants, deodorants, shaving creams, hair spray, colognes, body wash, home care products, laundry detergent, fabric softeners, liquid dish detergents, tumble dryer sheets, automatic dish washing detergents, and hard surface cleaners.
  • These consumer products may employ surfactant, solvents and emulsifying systems that are well known in the art.
  • a fragrance is used to provide the consumer with a pleasurable fragrance during and after using the product or to mask unpleasant odors from some of the functional ingredients used in the product.
  • a problem with the use of encapsulated fragrance in product bases is the loss of the fragrance before the optimal time for fragrance delivery.
  • the microcapsule may be in an aqueous solution of a consumer product.
  • the microcapsule may be in the continuous phase of an oil-in- water emulsion of a consumer product.
  • the microcapsule may be in the discontinuous phase of an oil-in-water emulsion of a consumer product.
  • the microcapsule may be in the discontinuous phase of a water-in-oil emulsion of a consumer product.
  • the microcapsule may be in the continuous phase of a water-in-oil emulsion of a consumer product.
  • Consumer products may be made using an aqueous base containing a surfactant, although some products use glycols, polyhydric alcohols, alcohols, or silicone oils as the dominant solvent or carrier.
  • Suitable surfactant agents for use in the present invention include those surfactants that are commonly used in consumer products such as laundry detergents, fabric softeners and the like.
  • the products commonly include cationic surfactants which also are used as fabric softeners; as well as nonioinic and anionic surfactants which are known in the art.
  • Surfactants are normally present at levels of about 1 to 30 weight %. In some instances the surfactant loading may be more than 85, typically more than 95 and greater than about 99 weight % of the formulated product.
  • the present invention is further illustrated for use in a consumer product, such as a fabric softener composition.
  • Fabric softener compositions are known in the art, and contain a fabric softening component, and other optional materials such as perfumes, chelators, preservatives, dyes, soil release polymers, and thickeners.
  • Other optional ingredients may also include solvents, alcohols, amphoteric and non-ionic surfactants, fatty alcohols, fatty acids, organic or inorganic salts, pH buffers, antifoams, germicides, fungicides, antioxidants, corrosion inhibitors, enzymes, optical brighteners, antifoams, and other materials known in the art.
  • a fabric softener composition may be substantially free of anionic surfactants known in the art, such as. lithium dodecyl sulfate, or sodium dodecyl sulfate.
  • substantially free is meant that the fabric softener composition contains less than 5% weight of anionic surfactant, preferably less than 1% by weight, more preferably less than .5% by weight and still more preferably less than 0.1 % by weight of an anionic surfactant.
  • a fabric softener composition may be substantially free of water soluble builder salts known in the art, such as alkali metal phosphates, such as sodium phosphate and potassium phosphate.
  • substantially free is meant that the fabric softener composition contains less than 5% weight of a builder salt, preferably less than 1% by weight, more preferably less than 0.5% by weight and still more preferably less than 0.1% by weight an water soluble builder salt.
  • Fabric softening components in fabric softener compositions are well known in the art. and may include cationic surfactants, quaternary ammonium salts (acyclic quaternary ammonium salts, ester quaternary ammonium salts, cyclic quaternary ammonium salts, diamido quaternary ammonium salts, biodegradable quaternary ammonium salt, polymeric ammonium salts), polyquats, tertiary fatty amines, carboxylic acids, esters of polyhydric alcohols, fatty alcohols, ethoxylated fatty alcohols, alkyphenols. ethoxylated alkyphenols, ethoxylated fatty amines, difatty. ethoxylated monolycerides, ethoxylated diglycerides, mineral oils, clays, and polyols.
  • quaternary ammonium salts acyclic quaternary ammonium salts, ester quaternary
  • a fabric softener composition may comprise about 0.01% to about 35% by weight of one or more fabric softening components.
  • the present invention may comprise about 0.5% to about 25% weight of a fabric softening component.
  • the present invention may comprise about 1.5% to about 12% of a fabric softening component.
  • the present invention may comprise about 15% to about 24% of a fabric softening component.
  • the amount of the components in a fabric softener composition will depend on the purpose of the formulation, i.e., whether the formulation concentrated or dilute.
  • the fabric softening component may, for example, be about 0.1% to about 50% of the total weight of the composition, e.g.. about 10% to about 25% for a concentrated composition and about 1 to about 10% for a dilute composition.
  • the fabric softener composition may also have one or more chelators, dyes, fatty alcohols, preservatives and/or perfumes, and/or other ingredients as known in the art.
  • a fabric softening component may be an esterquat (or mixture of esterquats) having the formula of structure 1
  • R ⁇ represents -(CH 2 )
  • R 2 and R 3 represent -(CH 2 ) s -R 5 where R 5 represents an acyloxy group containing from 8 to 22 carbon atoms, benzyl, phenyl. (Cl -C4)-alkyl substituted phenyl, OH or H;
  • R 4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms; q, s, and t, each independently, represent an integer from 1 to 3; and
  • X " is a softener compatible anion.
  • a particular softener for use in the present invention is produced by reacting two moles of fatty acid methyl ester with one mole of triethanolamine followed by quaternization with dimethyl sulfate (further details on this preparation method are disclosed in US 3,915.867, which is incorporated herein by reference). The reaction products are distributed as follows: (a) 50% diesterquat material; (b) 20% monoesterquat; and (c) 30% triesterquat.
  • esterquat compounds described herein are prepared by quaternizing the product of the condensation reaction between a fatty acid fraction containing at least one saturated or unsaturated linear or branched fatty acid, or derivative, and at least one functional ized tertiary amine, wherein the molar ratio of the fatty acid fraction to tertiary amine is about 1.7 : 1.
  • the method of manufacture for such a esterquat surfactant is described in US Patent 5,637,743 (Stepan), the disclosure of which is incorporated herein by reference.
  • the aforementioned molar ratio will determine the equilibrium between the mono, di and tri-esterquat compounds in the products. For example, using a molar ratio of about 1.7 results in a normalized distribution of about 34% mono-esterquat, about 56% of di-esterquat and about 10% of tri-esterquat which is a fatty ester quat compound in accordance with the invention. On the other hand, for example, using a molar ratio of about 1.96 results in a normalized distribution of about 21% mono-esterquat, 61% of di-esterquat and 18% of tri- esterquat.
  • a preferred fabric softening component may thus include a quaternized fatty acid triethanolamine ester salt, e.g., a triethanolamine-esterquat tallow.
  • a preferred fabric softening component of the present invention may include a di-alkyl ester of triethanol ammonium methyl sulfate, or a dihydrogenated tallowoylethyl hydroxyethylmonium methosulfate.
  • Fabric softening components may be purchased from Kao Corporation under the product name Tetranyl L 1/90 or Tetranyl ATl-75.
  • Fabric softener compositions may also comprise soil release polymers (SRP's).
  • SRP's are well known in the art, and may include polymers which are absorbed onto fabric fibers where they counteract resoiling of the fibers.
  • the polymers may include polyesters and copolymers of terephthalic acid, polyesters of and co-polymers of ethylene glycol, copolymers of ethylene glycol and benzene, and polyethylene terephthalate.
  • the polymers may include nonionic polyesters.
  • the polymers may be modified whereby a portion of the ethylene glycol is removed and replaced with a high molecular weight hydroxy-terminated polyethylene glycol.
  • Chelating agents are well known in the art. and may be present at a level of at least about 0.001%, by weight, of the fabric softening composition, preferably about 0.001% to about 1%, more preferably about 0.01% to about 0.5%, more preferably about 0.06% - 0.1% by weight.
  • the chelating agents may be selected from among amino carboxylic acid compounds and organo aminophosphonic acid compounds, and mixtures of the same.
  • Suitable amino carboxylic acid compounds may include: ethylenediamine tetraacetic acid, N- hydroxyethylenediamine triacetic acid, nitrilotriacetic acid, and diethylenelriamine pentaacetic acid.
  • Suitable organo aminophosphonic acid compounds may include methylenephosphonic acid, 1-hydroxyethane 1.1-diphosphonic acid, and aminotrimethylene phosphonic acid.
  • a preferred chelating agent may be an aminotrimethylene phosphonic acid, which may be obtained from Solutia, Inc. (St. Louis, Missouri, USA) as Dequest 2000.
  • Preservatives are well known in the art, and may include lactic acid, formaldehyde, or other preservatives known in the art.
  • a fabric softener composition may comprise 0% to about 10% weight of a preservative, preferably, about 0.01 % to about 2%, more preferably about 0.05% to about 0.5%.
  • a preferred preservative in the present invention may be lactic acid.
  • Fatty alcohols and aliphatic alcohols are known in the art.
  • Fatty alcohols may have carbon chain which are fully saturated or unsaturated.
  • Preferred fatty alcohols include Cm- C 28 alcohols, preferably Ci 6 - is- Ci 3 -Ci 5 alcohols, and mixtures thereof.
  • a fabric softener composition may comprise 0% to about 10% weight of a fatty alcohol, preferably about 0.1% to about 5%. and more preferably about 0.1% to about 0.5% of a fatty alcohol.
  • Dyes are well known in the art and may comprise 0% to about 5% of a product.
  • the invention provides a method of delivering a fragTance or antimcrobial material in a product comprising admixing any of compositions into a consumer product.
  • the consumer product may be a oral care product, toothpaste, mouthwash, personal care product, lotion, cream, shampoo, conditioner, hair gel. antiperspirant, deodorant, antiperspirant and deodorant, shaving cream, hair spray, cologne, body wash, home care product, laundry detergent, fabric softener, liquid dish detergent, tumble dryer sheet, automatic dish detergent, or hard surface cleaner.
  • compositions are prepared by mixing in deionized water to create an emulsion (percentages are percentage of total weight):
  • compositions are prepared by mixing in deionized water to create an emulsion (percentages are percentage of total weight):
  • Cotton terry towels are washed in laundry washing machines with equal amounts of compositions FC#3 and FC#4. Following washing, the towels are stored for 1 week at temperature for 1 week. 3 months at 35°C. and one month at 43°C. Following storage. a panel of 20 judges is asked to rate the intensity of the perfume on the towel, and the intensity of the perfume on the towel after rubbing the towel several times. The results are shown in the chart below. The towels washed in FC#4 with the encapsulated fragrance with the cationic polymer outperformed the towels washed in FC#3 without the encapsulated fragrance.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne l'utilisation d'un polymère cationique permettant une stabilité des microcapsules dans une composition, dans laquelle la microcapsule comprend un matériau d'encapsulation d'enveloppe ayant un ClogP moyen d'au moins 2,5 et plus de 60 % en poids des substances encapsulées ont un ClogP d'au moins 3,3. Le polymère cationique est dérivé de la polymérisation d'environ 5 à 100 moles pour cent d'un monomère d'addition vinylique cationique, de 0 à environ 95 pour cent d'acrylamide, et d'environ 5 à environ 500 ppm d'un agent de réticulation monomère d'addition vinylique bifonctionnel. Le polymère cationique et la substance encapsulée peuvent être utilisés, par exemple, dans une composition d'assouplissant.
PCT/US2007/071782 2006-06-30 2007-06-21 composition de microcapsules stabilisées à base de polymère cationique WO2008005693A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2007269428A AU2007269428A1 (en) 2006-06-30 2007-06-21 Cationic polymer stabilized microcapsule composition
EP07798887A EP2046935A2 (fr) 2006-06-30 2007-06-21 Composition de microcapsules stabilisees a base de polymere cationique
CA002656326A CA2656326A1 (fr) 2006-06-30 2007-06-21 Composition de microcapsules stabilisees a base de polymere cationique
BRPI0713074-0A BRPI0713074A2 (pt) 2006-06-30 2007-06-21 composição, e, método para melhorar a estabilidade de um produto.
MX2008016479A MX2008016479A (es) 2006-06-30 2007-06-21 Composicion de microcapsula estabilizada con polimero cationico.
IL196157A IL196157A0 (en) 2006-06-30 2008-12-24 Cationic polymer stabilized microcapsule composition
NO20090477A NO20090477L (no) 2006-06-30 2009-01-29 Mikrokapselsammensetning stabilisert med kationisk polymer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47967906A 2006-06-30 2006-06-30
US11/479,679 2006-06-30

Publications (2)

Publication Number Publication Date
WO2008005693A2 true WO2008005693A2 (fr) 2008-01-10
WO2008005693A3 WO2008005693A3 (fr) 2008-02-21

Family

ID=38658485

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/071782 WO2008005693A2 (fr) 2006-06-30 2007-06-21 composition de microcapsules stabilisées à base de polymère cationique

Country Status (11)

Country Link
EP (1) EP2046935A2 (fr)
CN (1) CN101506344A (fr)
AU (1) AU2007269428A1 (fr)
BR (1) BRPI0713074A2 (fr)
CA (1) CA2656326A1 (fr)
IL (1) IL196157A0 (fr)
MX (1) MX2008016479A (fr)
NO (1) NO20090477L (fr)
RU (1) RU2009102970A (fr)
WO (1) WO2008005693A2 (fr)
ZA (1) ZA200900074B (fr)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009153695A1 (fr) * 2008-06-16 2009-12-23 Firmenich Sa Procédé de préparation de microcapsules de polyurée
US7745386B2 (en) * 2006-05-24 2010-06-29 The Procter & Gamble Company Process of incorporating microcapsules into dryer-added fabric care articles
WO2011079209A1 (fr) 2009-12-22 2011-06-30 Isp Investments Inc. Copolymères lactamiques polymérisables appropriés pour la formation d'enrobages sur des particules micro-encapsulées
WO2011123730A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Procédé pour former un revêtement de polymères cationiques sur des microcapsules
WO2011127011A1 (fr) * 2010-04-06 2011-10-13 The Procter & Gamble Company Eléments encapsulés
WO2012022034A1 (fr) * 2010-08-18 2012-02-23 Unilever Plc Améliorations apportées à des compositions de traitement des tissus comprenant des agents améliorants cibles
US8563498B2 (en) 2010-04-01 2013-10-22 The Procter & Gamble Company Fabric care compositions comprising copolymers
EP2689835A1 (fr) 2012-07-26 2014-01-29 Papierfabrik August Koehler AG Aromatic oil encapsulation
WO2014092693A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
WO2014092692A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
US20140227328A1 (en) * 2010-04-28 2014-08-14 The Procter & Gamble Company Delivery Particles
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
EP2576743B1 (fr) 2010-05-28 2015-11-11 Colgate-Palmolive Company Saturation d'une chaîne d'acides gras dans un esterquat à base d'alcanolamine
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US20160024434A1 (en) * 2014-07-23 2016-01-28 The Procter & Gamble Company Treatment compositions
US20160024433A1 (en) * 2014-07-23 2016-01-28 The Procter & Gamble Company Treatment compositions
US20160032220A1 (en) * 2014-07-23 2016-02-04 The Procter & Gamble Company Treatment compositions
US9351910B2 (en) 2011-08-24 2016-05-31 Conopco, Inc. Benefit agent delivery particles comprising dextran
WO2017087718A1 (fr) * 2015-11-17 2017-05-26 Elc Management Llc Composition de mascara et procédé associé
WO2017091227A1 (fr) * 2015-11-25 2017-06-01 Kimberly-Clark Worldwide, Inc. Monomère fonctionnel pour libération de parfum déclenchée par de l'eau ou de l'acide et système polymère
WO2017102306A1 (fr) * 2015-12-15 2017-06-22 Unilever Plc Composition de conditionnement de tissu
WO2018093759A1 (fr) * 2016-11-18 2018-05-24 The Procter & Gamble Company Compositions de traitement de textile ayant des polymères à faible densité de charge cationique calculée et des agents actifs assouplissants pour textile, et procédés apportant un bénéfice
US10058501B2 (en) 2015-11-17 2018-08-28 Elc Management Llc Mascara composition and method
US10064806B2 (en) 2015-11-17 2018-09-04 Elc Management Llc Mascara composition and method
US10064808B2 (en) 2015-11-17 2018-09-04 Elc Management Llc Mascara composition and method
US20180264425A1 (en) * 2017-03-16 2018-09-20 The Procter & Gamble Company Consumer Product Compositions Comprising Microcapsules
US10357410B2 (en) 2014-11-06 2019-07-23 The Procter & Gamble Company Pre-strained laminates and methods for making the same
US10626351B2 (en) 2014-07-23 2020-04-21 The Procter & Gamble Company Treatment compositions
US10676701B2 (en) 2017-03-16 2020-06-09 The Procter & Gamble Company Consumer product compositions comprising microcapsules
US10676693B2 (en) 2014-07-23 2020-06-09 The Procter & Gamble Company Treatment compositions
US10689600B2 (en) 2016-01-25 2020-06-23 The Procter & Gamble Company Treatment compositions
US10723975B2 (en) 2014-07-23 2020-07-28 The Procter & Gamble Company Treatment compositions
US10806233B2 (en) 2015-11-17 2020-10-20 Elc Management Llc Mascara composition and method
US10844321B2 (en) 2014-07-23 2020-11-24 The Procter & Gamble Company Treatment compositions
US11098270B2 (en) 2016-11-18 2021-08-24 The Procter & Gamble Company Fabric treatment compositions and methods for providing a benefit
EP3880779A1 (fr) * 2018-11-14 2021-09-22 Unilever Global Ip Limited Compositions de conditionneur de tissu
US20210315794A1 (en) * 2018-09-20 2021-10-14 Givaudan Sa Improvements in or relating to organic compounds
US11213436B2 (en) 2017-02-16 2022-01-04 The Procter & Gamble Company Substrates having repeating patterns of apertures for absorbent articles
US11261402B2 (en) 2016-01-25 2022-03-01 The Procter & Gamble Company Treatment compositions
US20230107594A1 (en) * 2019-12-27 2023-04-06 Kao Corporation Aqueous microcapsule dispersion
US12127925B2 (en) 2018-04-17 2024-10-29 The Procter & Gamble Company Webs for absorbent articles and methods of making the same
US12227720B2 (en) 2020-10-16 2025-02-18 The Procter & Gamble Company Consumer product compositions with at least two encapsulate populations

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2436720T3 (es) * 2009-12-18 2014-01-03 The Procter & Gamble Company Composición que comprende microcápsulas
CN101935949B (zh) * 2010-08-27 2012-01-18 上海制皂有限公司 衣物柔顺剂
CN104039944B (zh) * 2011-08-25 2017-04-26 荷兰联合利华有限公司 包囊的有益剂
WO2013113453A1 (fr) * 2012-01-30 2013-08-08 Evonik Industries Ag Composition active d'assouplissant pour textile
GB201706762D0 (en) * 2017-04-28 2017-06-14 Givaudan Sa Improvements in or relating to organic compounds
JP7107970B2 (ja) * 2017-05-31 2022-07-27 ローム アンド ハース カンパニー 自立型分散剤フィルム
CN111065673B (zh) * 2017-09-15 2021-10-01 株式会社Lg化学 可聚合组合物、包含其的聚合物胶囊和织物柔软剂组合物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19932144A1 (de) * 1999-07-09 2001-01-11 Basf Ag Mikrokapselzubereitungen und Mikrokapseln enthaltende Wasch- und Reinigungsmittel
DE10000223A1 (de) * 2000-01-05 2001-07-12 Basf Ag Mikrokapselzubereitungen und Mikrokapseln enthaltende Wasch- und Reinigungsmittel
DE50104385D1 (de) * 2000-02-23 2004-12-09 Henkel Kgaa Wasch- oder reinigungsmittel mit komponenten in form von mikro- und/oder nanokapseln
GB0114921D0 (en) * 2001-06-19 2001-08-08 Ciba Spec Chem Water Treat Ltd Particles containing fabric conditioner
US6620777B2 (en) * 2001-06-27 2003-09-16 Colgate-Palmolive Co. Fabric care composition comprising fabric or skin beneficiating ingredient
AU2003251377A1 (en) * 2002-08-14 2004-03-03 Quest International Services B.V. Compositions comprising encapsulated material
US20050112152A1 (en) * 2003-11-20 2005-05-26 Popplewell Lewis M. Encapsulated materials
US7304026B2 (en) * 2004-04-15 2007-12-04 Colgate-Palmolive Company Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient
US20060252669A1 (en) * 2005-05-06 2006-11-09 Marija Heibel Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient

Cited By (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7745386B2 (en) * 2006-05-24 2010-06-29 The Procter & Gamble Company Process of incorporating microcapsules into dryer-added fabric care articles
US8426353B2 (en) 2008-06-16 2013-04-23 Firmenich Sa Process for preparing polyurea microcapsules
WO2009153695A1 (fr) * 2008-06-16 2009-12-23 Firmenich Sa Procédé de préparation de microcapsules de polyurée
WO2011079209A1 (fr) 2009-12-22 2011-06-30 Isp Investments Inc. Copolymères lactamiques polymérisables appropriés pour la formation d'enrobages sur des particules micro-encapsulées
EP2515875A4 (fr) * 2009-12-22 2015-03-04 Isp Investments Inc Copolymères lactamiques polymérisables appropriés pour la formation d'enrobages sur des particules micro-encapsulées
JP2013514885A (ja) * 2009-12-22 2013-05-02 アイエスピー インヴェストメンツ インコーポレイテッド マイクロカプセル化粒子のコーティングの形成に適した重合性ラクタム共重合体
US8765659B2 (en) 2010-04-01 2014-07-01 The Procter & Gamble Company Cationic polymer stabilized microcapsule composition
WO2011123730A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Procédé pour former un revêtement de polymères cationiques sur des microcapsules
US8563498B2 (en) 2010-04-01 2013-10-22 The Procter & Gamble Company Fabric care compositions comprising copolymers
EP2674477A1 (fr) 2010-04-01 2013-12-18 The Procter and Gamble Company Composition comprenant des microcapsules stabilisées par un polymère cationique
US8633148B2 (en) 2010-04-06 2014-01-21 The Procter & Gamble Company Encapsulates
US8822402B2 (en) 2010-04-06 2014-09-02 The Procter & Gamble Company Encapsulates
US9023783B2 (en) 2010-04-06 2015-05-05 The Procter & Gamble Company Encapsulates
WO2011127011A1 (fr) * 2010-04-06 2011-10-13 The Procter & Gamble Company Eléments encapsulés
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US12133906B2 (en) 2010-04-28 2024-11-05 The Procter & Gamble Company Delivery particle
US11096875B2 (en) 2010-04-28 2021-08-24 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
US9221028B2 (en) 2010-04-28 2015-12-29 The Procter & Gamble Company Delivery particles
US20140227328A1 (en) * 2010-04-28 2014-08-14 The Procter & Gamble Company Delivery Particles
EP2576743B1 (fr) 2010-05-28 2015-11-11 Colgate-Palmolive Company Saturation d'une chaîne d'acides gras dans un esterquat à base d'alcanolamine
US8637445B2 (en) 2010-08-18 2014-01-28 Conopco Inc. Fabric treatment compositions comprising targeted benefit agents
WO2012022034A1 (fr) * 2010-08-18 2012-02-23 Unilever Plc Améliorations apportées à des compositions de traitement des tissus comprenant des agents améliorants cibles
US9334469B2 (en) 2010-08-18 2016-05-10 Conopco, Inc. Fabric treatment compositions comprising targeted benefit agents
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US9561169B2 (en) 2011-04-07 2017-02-07 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US10143632B2 (en) 2011-04-07 2018-12-04 The Procter And Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9351910B2 (en) 2011-08-24 2016-05-31 Conopco, Inc. Benefit agent delivery particles comprising dextran
WO2014016395A1 (fr) 2012-07-26 2014-01-30 Papierfabrik August Koehler Ag Encapsulation d'huile parfumée
EP2689835A1 (fr) 2012-07-26 2014-01-29 Papierfabrik August Koehler AG Aromatic oil encapsulation
WO2014092693A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
US9732307B2 (en) 2012-12-11 2017-08-15 Colgate-Palmolive Company Esterquat composition having high triesterquat content
US9388367B2 (en) 2012-12-11 2016-07-12 Colgate-Palmolive Company Esterquat composition having high triesterquat content
WO2014092692A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
US9476012B2 (en) 2012-12-11 2016-10-25 Colgate-Palmolive Company Esterquat composition having high triesterquat content
US20160032220A1 (en) * 2014-07-23 2016-02-04 The Procter & Gamble Company Treatment compositions
US10676693B2 (en) 2014-07-23 2020-06-09 The Procter & Gamble Company Treatment compositions
US10844321B2 (en) 2014-07-23 2020-11-24 The Procter & Gamble Company Treatment compositions
US12215299B2 (en) 2014-07-23 2025-02-04 The Procter & Gamble Company Treatment compositions
US20160024433A1 (en) * 2014-07-23 2016-01-28 The Procter & Gamble Company Treatment compositions
US20160024434A1 (en) * 2014-07-23 2016-01-28 The Procter & Gamble Company Treatment compositions
US10723975B2 (en) 2014-07-23 2020-07-28 The Procter & Gamble Company Treatment compositions
US10407646B2 (en) 2014-07-23 2019-09-10 The Procter & Gamble Company Treatment compositions
US11306275B2 (en) 2014-07-23 2022-04-19 The Procter & Gamble Company Treatment compositions
US11643618B2 (en) 2014-07-23 2023-05-09 The Procter & Gamble Company Treatment compositions
US10626351B2 (en) 2014-07-23 2020-04-21 The Procter & Gamble Company Treatment compositions
US10538719B2 (en) 2014-07-23 2020-01-21 The Procter & Gamble Company Treatment compositions
US10266792B2 (en) 2014-07-23 2019-04-23 The Procter & Gamble Company Treatment compositions
US10519402B2 (en) 2014-07-23 2019-12-31 The Procter & Gamble Company Treatment compositions
US11998431B2 (en) 2014-11-06 2024-06-04 The Procter & Gamble Company Patterned apertured webs
US11324645B2 (en) 2014-11-06 2022-05-10 The Procter & Gamble Company Garment-facing laminates and methods for making the same
US10357410B2 (en) 2014-11-06 2019-07-23 The Procter & Gamble Company Pre-strained laminates and methods for making the same
US11633311B2 (en) 2014-11-06 2023-04-25 The Procter & Gamble Company Patterned apertured webs
US12226295B2 (en) 2014-11-06 2025-02-18 The Procter & Gamble Company Patterned apertured webs
US11766367B2 (en) 2014-11-06 2023-09-26 The Procter & Gamble Company Patterned apertured webs
US11813150B2 (en) 2014-11-06 2023-11-14 The Procter & Gamble Company Patterned apertured webs
US11135103B2 (en) 2014-11-06 2021-10-05 The Procter & Gamble Company Apertured webs and methods for making the same
US12144711B2 (en) 2014-11-06 2024-11-19 The Procter & Gamble Company Patterned apertured webs
US12138144B2 (en) 2014-11-06 2024-11-12 The Procter & Gamble Company Patterned apertured webs
US10058501B2 (en) 2015-11-17 2018-08-28 Elc Management Llc Mascara composition and method
US10806233B2 (en) 2015-11-17 2020-10-20 Elc Management Llc Mascara composition and method
WO2017087718A1 (fr) * 2015-11-17 2017-05-26 Elc Management Llc Composition de mascara et procédé associé
US10064807B2 (en) 2015-11-17 2018-09-04 Elc Management Llc Mascara composition and method
US10064806B2 (en) 2015-11-17 2018-09-04 Elc Management Llc Mascara composition and method
US10064808B2 (en) 2015-11-17 2018-09-04 Elc Management Llc Mascara composition and method
GB2556848A (en) * 2015-11-25 2018-06-06 Kimberly Clark Co Water-or acid-triggered fragrance release functional monomer and polymer system
WO2017091227A1 (fr) * 2015-11-25 2017-06-01 Kimberly-Clark Worldwide, Inc. Monomère fonctionnel pour libération de parfum déclenchée par de l'eau ou de l'acide et système polymère
EP3390601B1 (fr) 2015-12-15 2019-04-10 Unilever Plc. Composition de conditionnement de tissu
WO2017102306A1 (fr) * 2015-12-15 2017-06-22 Unilever Plc Composition de conditionnement de tissu
US10689600B2 (en) 2016-01-25 2020-06-23 The Procter & Gamble Company Treatment compositions
US11261402B2 (en) 2016-01-25 2022-03-01 The Procter & Gamble Company Treatment compositions
WO2018093759A1 (fr) * 2016-11-18 2018-05-24 The Procter & Gamble Company Compositions de traitement de textile ayant des polymères à faible densité de charge cationique calculée et des agents actifs assouplissants pour textile, et procédés apportant un bénéfice
JP2019532195A (ja) * 2016-11-18 2019-11-07 ザ プロクター アンド ギャンブルカンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 低計算カチオン電荷密度ポリマー及び布地柔軟化活性物質を有する布地処理組成物並びに利益をもたらすための方法
US10870816B2 (en) 2016-11-18 2020-12-22 The Procter & Gamble Company Fabric treatment compositions having low calculated cationic charge density polymers and fabric softening actives and methods for providing a benefit
US11098270B2 (en) 2016-11-18 2021-08-24 The Procter & Gamble Company Fabric treatment compositions and methods for providing a benefit
US11834631B2 (en) 2016-11-18 2023-12-05 The Procter & Gamble Company Fabric treatment compositions having low calculated cationic charge density polymers and fabric softening actives and methods for providing a benefit
US11213436B2 (en) 2017-02-16 2022-01-04 The Procter & Gamble Company Substrates having repeating patterns of apertures for absorbent articles
US20180264425A1 (en) * 2017-03-16 2018-09-20 The Procter & Gamble Company Consumer Product Compositions Comprising Microcapsules
US10676701B2 (en) 2017-03-16 2020-06-09 The Procter & Gamble Company Consumer product compositions comprising microcapsules
US12127925B2 (en) 2018-04-17 2024-10-29 The Procter & Gamble Company Webs for absorbent articles and methods of making the same
US20210315794A1 (en) * 2018-09-20 2021-10-14 Givaudan Sa Improvements in or relating to organic compounds
EP3880779A1 (fr) * 2018-11-14 2021-09-22 Unilever Global Ip Limited Compositions de conditionneur de tissu
EP4082653A4 (fr) * 2019-12-27 2023-11-29 Kao Corporation Solution de dispersion aqueuse de microcapsules
US20230107594A1 (en) * 2019-12-27 2023-04-06 Kao Corporation Aqueous microcapsule dispersion
US12227720B2 (en) 2020-10-16 2025-02-18 The Procter & Gamble Company Consumer product compositions with at least two encapsulate populations

Also Published As

Publication number Publication date
CN101506344A (zh) 2009-08-12
WO2008005693A3 (fr) 2008-02-21
CA2656326A1 (fr) 2008-01-10
RU2009102970A (ru) 2010-08-10
AU2007269428A1 (en) 2008-01-10
EP2046935A2 (fr) 2009-04-15
ZA200900074B (en) 2010-03-31
IL196157A0 (en) 2009-09-22
MX2008016479A (es) 2009-01-22
BRPI0713074A2 (pt) 2012-07-17
NO20090477L (no) 2009-01-29

Similar Documents

Publication Publication Date Title
EP2046935A2 (fr) Composition de microcapsules stabilisees a base de polymere cationique
AU2005236011B2 (en) Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient
CA2562011C (fr) Composition de produit d'entretien textile contenant un ingredient polymere encapsule benefique au tissu ou a la peau
EP2674477B1 (fr) Composition comprenant des microcapsules stabilisées par un polymère cationique
CA2606626A1 (fr) Composition pour l'entretien des textiles, comprenant un ingredient pour l'entretien des tissus ou du cuir encapsule dans un polymere
US9540489B2 (en) Blocky cationic organopolysiloxane
WO2003002699A1 (fr) Composition de traitement de tissu comportant un ingredient benefique au tissu ou a la peau
IL178380A (en) Fabric treatment product containing a latent polymer component that benefits fabrics or leather

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780031750.3

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07798887

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 2007269428

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: MX/A/2008/016479

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 2656326

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 196157

Country of ref document: IL

WWE Wipo information: entry into national phase

Ref document number: PI 20085366

Country of ref document: MY

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2007269428

Country of ref document: AU

Date of ref document: 20070621

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2007798887

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2009102970

Country of ref document: RU

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: PI0713074

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20081229

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载