EP2265702A1 - Compositions containing cationically surface-modified microparticulate carrier for benefit agents - Google Patents
Compositions containing cationically surface-modified microparticulate carrier for benefit agentsInfo
- Publication number
- EP2265702A1 EP2265702A1 EP09709193A EP09709193A EP2265702A1 EP 2265702 A1 EP2265702 A1 EP 2265702A1 EP 09709193 A EP09709193 A EP 09709193A EP 09709193 A EP09709193 A EP 09709193A EP 2265702 A1 EP2265702 A1 EP 2265702A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polymer
- type
- microparticulate
- composition
- cationic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
-
- 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)
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/22—Coating
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
Definitions
- the present invention is directed to carrier materials containing one or more benefit agents, e.g., a liquid fragrance, that have increased deposition onto substrates as a result of a plurality of cationic coating materials.
- benefit agents e.g., a liquid fragrance
- fragrance is an important ingredient in successful commercial fabric care products because, in addition to imparting an esthetically pleasing odor, a fragrance conveys a positive image of product performance to the consumer, e.g., the fabric is clean and fresh.
- Fragrances typically are added to fabric care products to provide a fresh, clean impression for the product itself, as well as to the fabric treated with the product. Although the fragrance does not enhance the performance of a fabric care product, the fragrance makes these products more esthetically pleasing, and consumers expect and demand a pleasing odor for such products.
- a fragrance plays an important, and often a determining, role when the consumer selects and purchases a fabric care product. Many consumers desire the fragrance to be deposited on the fabric and remain on the fabric for an extended time in order to convey a continuing impression of freshness. Consumers also desire fabric care products that impart a sufficient fragrance level to the fabric, and, in some embodiments, release the fragrance when the fabric is ironed.
- Typical fabric care products such as laundry detergent compositions and fabric softener compositions, contain about 0.1% to about 1%, by weight, of a fragrance.
- U.S. Pat. No. 6,051,540 discloses that in the course of the washing clothes with a standard powdered laundry detergent, or a fabric softener rinse, only a small fraction of the fragrance present in these fabric care products is actually transferred to the fabric, i.e., as low as 1% of the original amount of fragrance present in these products.
- One approach uses a carrier to introduce the fragrance to the fabric.
- the carrier is formulated to contain a fragrance and to adhere to the fabric during a washing cycle through particle entrainment or chemical change.
- Fragrances have been adsorbed onto various materials, such as silica and clay, for delivery of the fragrance from detergents and fabric softeners to fabrics.
- U.S. Pat. No. 4,954,285 discloses fragrance particles especially for use with dryer-released fabric softening/antistatic agents.
- the fragrance particles are formed by adsorbing the fragrance onto silica particles having a diameter of greater than about one micron.
- the fragrance particles are included in dryer-activated solid fabric softener compositions including coated particles of fabric softener. The compositions release softener to fabrics in the dryer, and the fragrance particles improve the esthetic character of the fabric softener deposited on the fabric.
- the fragrance particles also can be admixed with detergent granules and can be coated or uncoated. This system has a drawback in that the fragrance is not sufficiently protected, and frequently is lost or destabilized during processing,
- U.S. Patent No. 6,790,814 discloses that a fragrance loaded into a porous carrier, such as zeolite particles, can be effectively protected from premature release of the fragrance by coating the loaded carrier particles with a hydrophobic oil, then encapsulating the resulting carrier particles with a water-soluble or water-dispersible, but oil-insoluble, material, such as a starch or modified starch.
- U.S. Pat. Nos. 4,946,624; 5,112,688; and 5,126,061 disclose microcapsules prepared by a coacervation process.
- the microcapsules have a complex structure, with a large central core of encapsulated material, preferably a fragrance, and walls that contain small wall inclusion particles of either the core material or another material that can be activated to disrupt the wall.
- the microcapsules are incorporated into a fabric softener composition having a pH of about 7 or less and which further contains a cationic fabric softener.
- the encapsulated fragrance preferably is free of large amounts of water-soluble ingredients.
- the microcapsules are added separately to the fabric softener compositions.
- fragrance ingredients that have high and low volatilities, compared to desired fragrance, either can be added to or removed from the fragrance to achieve the desired volatility.
- This type of controlled release system cannot be used with all types of fragrance ingredients, in particular, with fragrance ingredients that are relatively water soluble and/or are incapable of depositing onto a fabric.
- U.S. Pat. No. 4,402,856 discloses a coacervation technique to provide fragrance particles for fabric care products containing gelatin or a mixture of gelatin with gum arabic, carboxymethylcellulose, and/or anionic polymers.
- the gelatin is hardened with a natural and/or synthetic tanning agent and a carbonyl compound.
- the particles adhere to the fabric during rinse cycles, and are carried over to the dryer. Diffusion of the fragrance from the capsules occurs only in the heat-elevated conditions of a dryer.
- U.S. Pat. No. 4,152,272 discloses incorporating a fragrance into wax particles to protect the fragrance during storage and through the laundry process.
- the fragrance/wax particles are incorporated into an aqueous fabric conditioner composition.
- the fragrance diffuses from the particles onto the fabric in the heat-elevated conditions of the dryer.
- U.S. Pat. Nos. 4,446,032 and 4,464,271 disclose liquid or solid fabric softener compositions comprising microencapsulated fragrance suspensions.
- the compositions contain sustained release fragrances prepared by combining nonconfined fragrance oils with encapsulated or physically entrapped fragrance oils. These combinations are designed such that the nonconfined fragrance oil is bound in a network of physically entrapped fragrance oil and suspending agent.
- the controlled release system comprises a mixture of (i) a nonconfined fragrance composition, (ii) one or more fragrance oils which are physically entrapped in one or more types of solid particles, and (iii) a suspending agent such as hydroxypropyl cellulose, silica, xanthan gum, ethyl cellulose, or combinations thereof.
- the nonconfined fragrance, the entrapped fragrance, and the suspending agent are premixed prior to preparation of the liquid or solid fabric softener compositions.
- U.S. Pat. Nos. 4,973,422 and 5,137,646 disclose fragrance particles for use in cleaning and conditioning compositions.
- the particles comprise a fragrance dispersed within a wax material.
- the particles further can be coated with a material that renders the particles more substantive to the surface being treated, for example, a fabric in a laundry process. Such materials help deliver the particles to the fabric and maximize fragrance release directly on the fabric.
- the coating materials are water-insoluble cationic materials.
- U.S. Pat. No. 6,024,943 discloses particles containing absorbed liquids and methods of making the particles.
- a fragrance is absorbed within organic polymer particles, which further have a polymer at their exterior.
- the external polymer has free hydroxyl groups, which promote deposition of the particles from a wash or rinse liquor.
- the external polymer can be a component of an encapsulating shell, but typically is used as a stabilizer during polymerization of the particles.
- a highly hydrolyzed polyvinyl alcohol is a preferred external polymer.
- U.S. Pat. No. 6,740,631 discloses a free-flowing powder formed from solid hydrophobic, positively-charged nanospheres containing an active ingredient, such as a fragrance, encapsulated in a moisture sensitive microsphere.
- an active ingredient such as a fragrance
- particle size is optimized to ensure entrainment of the particles within the fabric fibers, and a sufficiently high cationic charge density on the particle surface is provided to maximize an ionic interaction between the particles and the fabric.
- U.S. Pat. No. 7,1 19,057 discloses a polymeric encapsulated fragrance where the fragrance encapsulating polymer is coated with one cationic polymer.
- the cationic polymer aids in the deposition and stability of the polymeric encapsulated fragrance.
- the load of the cationic polymer is preferably from about 10% to about 500% of the fragrance containing composition, based on a ratio with the fragrance on a dry basis.
- U.S. Pat. No. 7,119,060 discloses solid spheres comprising a crystallized waxy material.
- the waxy material may have a fragrance or other active agent incorporated therein, together with a cationic, hydrophobic charge-enhancing agent and a cationic softening agent.
- the spheres adhere to a fabric because of the cationic charge, and when ironing a dried fabric, a burst of fragrance occurs.
- the load of fragrance or other active agent is limited to about 30%, by weight, of the waxy material.
- U.S. Pat. App. No. 11/231,082 discloses the delivery of a benefit agent that is introduced into a formulation after admixture with a carrier.
- the agent and carrier composition requires a viscosity of at least 400 cps.
- the prior art does not sufficiently teach or suggest a composition having a rnicroparticulate material coated with one or more layers of two different cationic polymers for increased deposition of the microparticulate onto a substrate, such as a fabric.
- the prior art does not teach or suggest a methodology for making a microparticulate material containing a benefit agent, such as a fragrance, coated with layers of two different cationic polymers.
- compositions comprising a cationically surface- modified microparticulate material, containing at least one benefit agent.
- Benefit agents include flavors, fragrances, insect repellents, silicone oils, fabric softening agents, anti-static agents, anti-wrinkle agents, stain-resistant agents, emollients, moisturizing agents, waxes, ultraviolet (UV) ray absorbers, antimicrobial agents, antioxidants, pigments, film-forming agents, skin-care agents, hair-care agents, scalp-care agents, anti-dandruff agents, hair- coloring agents, hair-conditioning agents, and the like.
- UV ultraviolet
- the cationic surface modification comprises two different cationic coating materials which increase the deposition and retention of the benefit agent-containing microparticulate material on a substrate, for example fabric, hair, skin, teeth, and hard surfaces.
- the disclosed compositions can further include additives, for example water, organic solvents, and surfactants, to formulate commercial products.
- Examples of compositions employing the disclosed benefit agent-containing microparticulate materials having a plurality of deposition-enhancing cationic coating materials include cleansing products, such as shampoos, conditioners, body washes, moisturizing agents, creams, shower gels, soaps, detergents, toothpastes, surface cleansing agents, and surface-conditioning agents, such as fabric softeners.
- the microparticulate material can be a mixture of the benefit agent and a carrier agent or can be entirely composed of one or more benefit agents.
- a microparticulate that is a porous solid carrier loaded with a benefit agent.
- the carrier can be a polymer (including film-forming polymers, phase-separated or coacervated polymers, and water-insoluble polymers, copolymers, and cross-polymers), wax, water-insoluble organic solid or liquid, and/or water-insoluble inorganic solid.
- the microparticulates can be emulsion droplets formed, for example, from one or more benefit agents dispersed in two immiscible liquids.
- the microparticulate can further be a mixture of a benefit agent and a clay, such as a smectite clay, an organoclay, a water-insoluble inorganic microparticulate solid, hydrophilic liquid, hydrophobic liquid, gel, gum, solid including hydrocarbon solid, ester and/or ether solvent, silicone fluid, elastomer, wax, polymer, and/or mixtures, or the like.
- a clay such as a smectite clay, an organoclay, a water-insoluble inorganic microparticulate solid, hydrophilic liquid, hydrophobic liquid, gel, gum, solid including hydrocarbon solid, ester and/or ether solvent, silicone fluid, elastomer, wax, polymer, and/or mixtures, or the like.
- the present disclosure additionally relates to the eationic surface modification of the microparticulate with two different polymers, a Type-1 Polymer and a Type-2 Polymer.
- the Type-1 Polymer is a polymer having a cationic atom content in the range of about 3 to about 20 wt. % and a weight average molecular weight in the range of about 300,000 to 800,000 Dalton.
- the Type-2 Polymer is a polymer having a cationic atom content of about 0.1 to about 3 wt. % and a weight average molecular weight greater than about 1,000,000 Dalton.
- the present improved characteristics of the disclosed composition are not obtained if the microparticulate is coated with only the Type-1 Polymer or coated with only the Type-2 Polymer, if the microparticulate is only coated with less than about 10%, more often less than about 60% of the Type-2 Polymer, or if the microparticulate is coated with two polymers where one or both do not meet weight average molecular weight and/or cationic atom content requirements.
- compositions and methods provide compositions with improved characteristics and use much lower amounts of cationic polymer(s) than previously employed in the prior art, making the disclosed compositions more commercially and industrially applicable.
- One important aspect of compositions that employ significantly lower amounts of cationic polymer(s) is that the resulting compositions can have a much higher concentration of benefit agent(s). Raising the concentration of the benefit agent in benefit agent containing compositions, with the herein defined improved characteristics, decreases the costs and formulation problems associated with the inclusion of benefit agent containing compositions in commercial products.
- the improved characteristics of the disclosed composition include stability against strong coagulation, enhanced deposition, and enhanced retention on a substrate.
- strong coagulation means the average particle size in a dispersion of agglomerated particles is at least three times greater than the average particle size in a dispersion of unagglomerated particle. Additional scope and description can be found below.
- microparticulates are a plurality of different types of individual particulates having an average particle diameter that varies from about one to about 500 ⁇ m, preferably from about three to about 100 ⁇ m, more preferably from about six to about 50 ⁇ m, and still more preferably from about eight to about ten microns.
- microparticulates have at least one benefit agent.
- Microparticulates can be entirely made of one or more benefit agents or can be combinations of benefit agent(s) and particulate ca ⁇ er(s).
- Benefit agents are those compositions, chemicals, and formulations that impart a desired effect on a substrate whether the benefit agent or substrate is solid, liquid, gas, or combination.
- substrates include teeth, hair, skin, fabric, plastic, polymer, glass, metal, insects, plants, fungus, yeast, foods, drinks, and the like.
- a benefit agent can itself be a solid, liquid, gas, or mixture.
- Benefit agents include volatile and non- volatile compounds and/or compositions. Examples of volatile compounds include fragrances, insect repellants, therapeutic agents, and the like.
- Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry, musk, and flower scents such as lavender-like, rose-like, iris-like, and carnation-like.
- Other fragrances include herbal scents such as rosemary, thyme, and sage; and woodland scents derived from pine, spruce and other forest smells.
- Fragrances may also be derived from various oils, such as essential oils, or from plant materials such as peppermint, spearmint and the like. Fragrances can be familiar and popular smells such as baby powder, popcorn, pizza, cotton candy and the like. Applicable fragrances can be found in U.S. Pat. Nos.
- fragrances included in these references include acacia, cassie, chypre, cylamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchids, reseda, sweet pea, trefle, tuberose, vanilla, violet, wallflower, and the like.
- Applicable insect repellant benefit agents include dichlorvos, pyrethrin, allethrin, naled and/or fenthion pesticides disclosed in the U.S. Pat. No. 4,664,064, incorporated herein by reference.
- Preferable insect repellants are citronellal (3,7-dimethyl-6-octanal), N,N- diethyl-3-methylbenzamide (DEET), vanillin, and the volatile oils extracted from turmeric (Curcuma longa), kaffir lime (Citrus hystrix), citronella grass (Cyrnbopogon winterianus) and hairy basil (Ocimum americanum).
- applicable insect repellants can be mixtures of insect repellants.
- therapeutic benefit agents include creams or lotions, pharmaceuticals, neutraceuticals, homeopathic agents, and/or other materials.
- non-volatile benefit agents include silicone oils, resins, and modifications thereof such as linear and/or cyclic polydimethylsiloxanes, amino-modified, alkyl, aryl, and alkylaryl silicone oils, which preferably have a viscosity greater than about 50,000 centistokes; organic and inorganic sunscreen actives, for example, octylmethoxy cinnamate; antimicrobial agents, for example, 2-hydroxy-2,4,4-trichlorodiphenylether; ester solvents, for example, isopropyl myristate; lipids and lipid like substance, for example, cholesterol; hydrocarbons such as paraffins, petrolatum, and mineral oil; fish and vegetable oils; hydrophobic plant extracts; therapeutic and skin-care reagents, for example, salicylic acid, benzoyl peroxide, and retinol; various waxes and soft solids; organic and inorganic fabric softening agents; and pigments including inorgan
- Particulate carriers include those materials for encapsulating a benefit agent.
- Particulate carriers can be porous polymeric or solid state materials, encapsulating shells, and the like.
- encapsulated benefit agents include those described in U.S. Pat. App. No. 10/823,033, incorporated herein by reference, where the fragrances were encapsulated in substituted or un-substituted acrylic acid polymer or copolymer cross-linked with a melamine-fonnaldehyde pre-condensate or a urea-formaldehyde pre-condensate.
- porous particulate carriers for holding benefit agents include various adsorbent polymeric microparticles available from AMCOL Int'l Corp., as noted below.
- One class of adsorbent polymeric microparticles is prepared by suspension polymerization techniques, as set forth in U.S. Pat. Nos. 5,677,407; 5,712,358; 5,777,054; 5,830,967; 5,834,577; 5,955,552; and 6,107,429, each incorporated herein by reference (available commercially under the tradename of POLY-PORE® E200, INCI name, ally methacrylates crosspolymer, from AMCOL Int'l, Arlington Heights, JL).
- Another class of adsorbent polymeric microparticle is prepared by a precipitation polymerization technique, as set forth in U.S. Patent Nos. 5,830,960; 5,837,790; 6,248,849; and 6,387,995, each incorporated herein by reference (available commercially under the trade name of POLY-PORE® L200 from AMCOL Int'l).
- adsorbent polymeric microparticle is prepared by a precipitation polymerization technique as disclosed in U.S. Pat. Nos. 4,962,170; 4,948,818; and 4,962,133, each incorporated herein by reference.
- Examples of this class of absorbent polymeric microparticle are available commercially under the trade name of POLYTRAP by AMCOL Int'l (INCI name of lauryl methacrylate / glycol dimethacrylate cross polymer).
- adsorbent polymeric microparticles have been developed, for example those disclosed in U.S. Pat. Re. 33,429, incorporated herein by reference, and sold under the trade name of MACROBEAD by AMCOL Int'l (INCI name of lauryl methacrylate / glycol dimethacrylate cross polymer).
- MACROBEAD by AMCOL Int'l
- Other adsorbent polymeric microparticles that are commercially available include, for example, MICROSPONGE® (INCI name of methyl methacrylate / glycol dimethylacrylate crosspolymer), as disclosed in U.S. Pat. No.
- particulate carriers include combinations of porous polymeric or solid state materials, encapsulating shells, absorbent polymeric microparticles, adsorbent polymers, and the like.
- a microparticulate having a plurality of particulate carriers is an absorbent polymeric microparticle including a benefit agent and within an encapsulating shell.
- the amount of the particulate carrier may range from about 10% to about 99% by weight of the microparticulate.
- One or more of the foregoing benefit agents is included in the compositions described herein in an amount varying from about 0.01 to about 80%, preferably from about 0.1 to about 40%, and most preferably from about 0.5 to about 20% of the total weight of the composition.
- encapsulating polymers include those formed from melamine-formaldehyde or urea-formaldehyde condensates, as well as similar types of aminoplasts. Additionally, capsules made by the simple or complex coacervation of gelatin are also preferred for use with the coating.
- Capsules having shell walls comprised of polyurethane, polyamide, polyolefm, polysaccaharide, protein, silicone, lipid, modified cellulose, gums, polyacrylate, polyphosphazines, polystyrene, and polyesters or combinations of these materials are also applicable.
- the microparticulate has a neutral or anionic surface charge.
- the surface charge on the microparticulate can often be determined by a measurement of the zeta ( ⁇ )- potential and/or electrophoretic mobility.
- the microparticulate is often treated with an anionic polymer.
- the microparticulate material may be surface-treated with an anionic polymer or an anionic surfactant or mixtures thereof (herein termed anionic treatment agents), prior to the claimed surface-modification.
- the resulting anionic microparticulate material has approximately one monolayer of the anionic polymer and/or surfactant on the surface and is subsequently further surface-treated as described below for achieving the claimed cationic surface-modification.
- the anionic polymer and cationic polymer are not pre-mixed in the solution phase prior to adding to the microparticulate.
- the anionic polymer and/or surfactant on the surface of the microparticulate is coated with the cationic polymer(s) disclosed herein and is neither entangled nor quatemized with the cationic polymer coating.
- the required amount of an anionic polymer or surfactant that may be used for the aforementioned anionic pre-treatment of the microparticulate material is such that the anionic surface charge resulting from the pre- treatment is relatively low, wherein the ⁇ -potential of the microparticulate material in a dilute, approximately 0.1 wt. %, aqueous dispersion is preferably less than about -50 mV, while the conductivity of the dispersion is in the range of about 0.01 to about 0.5 mS/cm.
- Applicable anionic polymers include water-soluble anionic polymers and water- insoluble anionic polymers.
- applicable water-soluble anionic polymers include 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.
- a water-insoluble anionic polymer is the copolymer of castor oil phosphate and 3-isocyanato-methyl-3,5,5-trimethyl cyclohexyl isocyanate, referred to herein as castor oil phosphate/IPDI copolymer.
- coating means the polymer deposits onto the surface of the microparticulate and is not incorporated into the core of the microparticulate. Effectively, coating means the creation of an encapsulating layer of cationic polymer. This is distinct and significantly different from the entanglement or quaterization of a cationic polymer and an anionic polymer forming a particulate, known in the art, therein the particulate is not coated with the cationic polymer but encompasses the cationic polymer.
- these polymers are termed Type-1 Polymer and Type-2 Polymer.
- the Type-1 Polymer can be a homopolymer or a copolymer including an amphiphilic polymer or copolymer, a hydrophobically-modified polymer or copolymer, and the like.
- the preferred Type-1 cationic polymer is poly(diallyldimethyl ammonium halide), poly(DADMAC).
- the Type-2 Polymer can be a cationic guar gum, a cationic cellulose, a cationic starch, a hydrophobically-modified thereof, or the like.
- Type-1 Polymers are selected from the cationic polymers that have a high cationic charge content. As used herein a high cationic charge content is measured by the cationic atom content.
- the cationic atom content is a measure of the total atomic weight of the atoms bearing cationic charge in/on the polymer chain divided by the molecular weight of the polymer, times 100, expressed as a weight percentage.
- all of the cationic nitrogen atoms in the polymer poly(D ADMAC) are quaternary ammonium ions, thereby the cationic atom content (here, the cationic nitrogen content) can be determined either by elemental analysis of a sample of the poly(D ADMAC) or by the weight average molecular weight of the polymer. The elemental analysis would provide the weight percentage of nitrogen atoms in a sample of polymer, that is the cationic atom content.
- a Type-1 Polymer has a cationic atom content in the range of about 3 wt. % to about 20 wt. %. More preferably, a Type-1 Polymer has a cationic atom content in the range of about 5 to about 15 wt. %, and still more preferably this polymer has a cationic atom content in the range of about 8 wt. % to about 10 wt. %. Even more preferably, a Type-1 Polymer has a cationic nitrogen content of at least 3 wt. %.
- Type-1 Polymers preferably, have a weight average molecular weight in the range of about 300,000 to about 800,000 Dalton, more preferably in the range of about 350,000 to about 600,000 Dalton, and still more preferably in the range of about 400,000 to about 550,000 Dalton.
- the preferred Type-1 Polymer should have a solubility of less than 2 wt. % in a solution of anionic surfactant(s) containing 3 wt. % of an anionic surfactant. More preferably, the solubility of the Type-1 Polymer is less than about 1 wt. %, and even more preferably the solubility is less than about 0.5 wt. % in a 3 wt. % solution of an anionic surfactant, e.g., sodium laurylsulfate.
- an anionic surfactant e.g., sodium laurylsulfate.
- the preferred Type-1 Polymer is poly(diallyl dimethyl ammonium chloride), referred to herein as PoIy(DADMAC), that has a cationic nitrogen content of about 8.7 wt. %.
- Other useful Type-1 Polymers include polyacrylates and polyolefms with pendant quaternary ammonium groups.
- polymers that meet the above referenced weight average molecular weight, solubility, and cationic nitrogen content and also having the following compositions: polyquaternium 1 (CAS#: 68518-54-7); polyquaternium-2 (CAS#: 63451-27- 1); polyquaternium-4 (copolymer of hydroxyethylcellulose and diallyldimethyl ammonium chloride); polyquaternium-5 (CAS#: 26006-22-4); polyquaternium-6 (polyallyldimethylammonium chloride (CAS#: 26062-79-3); polyquaternium-7 (CAS#: 26590-05-6); polyquaternium-8 (poly((methyl, stearyl) dimethylaminoethyl methacrylate), polyq ⁇ taternium-9 (polydimethylaminoethylmethacrylate bromide); polyquaternium-10 (CAS#s: 53568-66-4, 55353-19-0, 54351-50-7, 81859-24-7; 68
- Type-2 Polymers are the cationic polymers that have a moderate to low cationic charge content. As used herein a moderate to low cationic charge content is measured by the cationic atom content, as defined above.
- a Type-2 Polymer has a cationic atom content less than about 3 wt. %. More preferably, the Type-2 Polymer has a cationic atom content in the range of about 0.01 wt. % to about 3 wt. %, still more preferably in the range of about 0.1 wt. % to about 2 wt. %, and even more preferably in the range of about 0.5 wt. % to about 1 wt. %.
- Type-2 Polymers preferably, have a weight average molecular weight in the range of about 1,000,000 to about 15,000,000 Dalton, more preferably in the range of about 1,000,000 to about 10,000,000 Dalton, and still more preferably in the range of about 1,000,000 to about 5,000,000 Dalton.
- Type-2 Polymers are those cationic polymers disclosed in U.S. Pat. No. 7,119,057, incorporated herein by reference, though herein used in significantly lower weight percentages.
- Preferable Type-2 Polymers include cationic copolymers of acrylamide, and cationic derivatives of natural polymers such as cellulose ether polymers, guar gum, and starch.
- Preferred Type-2 Polymers are those cationic derivatives of guar, cellulose, and/or starch that satisfy the above defined weight average molecular weight, and cationic weight percentage.
- the relative amounts of the Type-1 Polymer and Type-2 Polymer, in specific weight ratios, that are coated onto the benefit agent-containing microparticulate is the relative amounts of the Type-1 Polymer and Type-2 Polymer, in specific weight ratios, that are coated onto the benefit agent-containing microparticulate.
- the ratio of the weight of the Type-1 Polymer to the weight of the Type-2 Polymer should be in the range of about 0.1 to about 100.
- the weight ratio of the Type-1 Polymer to the Type-2 Polymer should be in the range of about 1 to 20, more preferably in the range of about 2 to about 20, and even more preferably in the range of about 2 to about 10, and most preferably about 3 to about 7.
- the weight percentage of the Type-1 Polymer to the combined weight of the Type-1 and Type-2 polymer is in the range of about 50 to less than 100 wt. %, preferably in the range of about 60 to about 95 wt. %, and more preferably in the range of about 70 to about 90 wt. %.
- the weight percentage of the Type-2 Polymer to the combined weight of the Type-1 and Type-2 polymer is in the range of about one to about 50 wt. %, preferably in the range of about 5 to about 40 wt. %, and more preferably in the range of about 10 to about 30 wt. %.
- the cationically-modified benefit agent-containing microparticulate materials, compositions and methods described herein is the addition of the Type-1 Polymer and Type-2 Polymer (the cationic polymers) to the microparticulate in a specific weight ratio, irrespective of other materials, water, solvents, or items in the composition.
- the ratio of the weight of the cationic polymers to the weight of the microparticulate is in the range of about 0.01 to about 10.
- the ratio is in the range of about 0.05 to about 5, more preferably in the range of about 0.1 to about 1, and most preferably about 0.1 to about 0.3.
- the Type-1 Polymer and Type-2 Polymer are combined with the microparticulate to form a composition where the weight percentage of the microparticulate in the coated microparticulate composition is in the range of about 1 to about 99.9 wt. %, preferably in the range of about 35 to about 99.5 wt. %, and more preferably in the range of about 50 to about 99.0 wt. %, irrespective of other materials, water, solvents, or items in the composition.
- the weight percentage of the Type-1 Polymer in the total composition is in the range of about 5 to about 20 wt. % and the weight percentage of the Type-2 Polymer is in the range of about 0.1 to about 5 wt. %, irrespective of other materials, water, solvents, or items in the composition.
- the cationically-modified benefit agent-containing microparticulate materials, compositions and methods described herein can be made by any of a plurality of methods.
- the first involves the admixing of the Type-1 Polymer with the benefit agent-containing microparticulate followed by the admixing of the product from the addition of the Type-1 Polymer to the microparticulate with the Type-2 Polymer.
- One embodiment of this method is the surface-modification, surface- treatment, or coating of the microparticulate with the Type-
- a second method involves the admixing of the Type-1 Polymer with the Type-2 Polymer followed by the admixing of this cationic polymer mixture with the benefit agent-containing microparticulate to coat the benefit agent-containing microparticulate with both cationic polymers simultaneously. It is believed that this method yields a composition having the Type-1 Polymer preferentially bound to the microparticulate surface and the Type-
- Type-1 Polymer bound to the Type-1 Polymer in a layered structure similar to the structure produced from the sequential addition of Type-1 then Type-2 Polymers.
- the higher concentration, higher cationic atom content, and lower molecular weight of the Type-1 Polymer theoretically allow the Type-1 Polymer to more rapidly (based on relative reaction rates) add to the anionic microparticulate; such that the Type-1 Polymer coats greater than 50% of the microparticulate's surface area, preferably greater than 70%, more preferably greater than 90, and even more preferably greater than 95% of the microparticulate's surface area.
- a third method involves the admixing of the Type-1 Polymer with the Type-2 Polymer, followed by the admixing of this cationic polymer mixture with the benefit agent-containing microparticulate to coat the benefit agent-containing microparticulate with both cationic polymers simultaneously, followed by the admixing of this coated microparticulate with additional Type-2 Polymer. It is believed that this method yields a composition having an outer coating layer that is greater than 95% Type-2 Polymer, theoretically this method assures that the outer coating layer is 100% Type-2 Polymer.
- the surface-modification, surface-treatment, or coating of the micropartieulate material may be carried out by repeatedly adding the micropartieulate material, either in a powder- form (generally, with a moisture content of less than 30% by weight) or as an aqueous dispersion, to an aqueous solution or dispersion containing a cationic polymer, and subsequently shearing the resulting dispersion.
- the micropartieulate material in a powder- form may be blended with a mixture of a Type-1 Polymer and a Type-2 Polymer, wherein the two cationic polymers are used, respectively, in a form selected from a powder, a solution, a dispersion, and/or mixtures thereof.
- the surface-modification, surface-treatment, or coating of the benefit agent-containing micropartieulate material with the Type-1 Polymer is preferably carried out by adding the benefit agent-containing micropartieulate material to an aqueous solution/dispersion of the polymer under high-shear agitation.
- the required amount of the Type-1 Polymer is such that the anionic surface-charge of the micropartieulate material is partially or fully neutralized by the cationic charge of the Type-1 Polymer, inasmuch as the net surface-charge of the modified micropartieulate-surface is cationic, and is sufficiently high for preventing strong coagulation amongst or between the dispersed particles of the micropartieulate material, due to what is known in the art as the electrical double layer repulsion between electrically charged particles in a dispersion.
- an optimum dosage (amount added to the micropartieulate material) of the Type-1 cationic polymer may be determined by a two step process.
- cationically-modified micropartieulate materials, compositions and methods described herein is the incorporation of the cationically-modified benefit agent-containing micropartieulate materials in commercial products.
- the cationically- modified benefit agent-containing micropartieulate materials can be used in products such as shampoo, liquid soap, bodywash, laundry detergent, fabric softener, toothpaste, and antiseptic ointments.
- These commercial products that contain cationically-modi fied benefit agent- containing microparticulate materials can further include solvents and/or other ingredients for the coated eationically-modified microparticulates.
- solvents and/or added ingredients include fatty alcohols, opacifiers, pearlescers, viscosity modifiers, rheology modifiers, inorganic oxides, buffering or pH adjusting chemicals, foam-boosters, perfumes, dyes, coloring agents or pigments, herb extracts, preservatives, hydrotopes, enzymes, bleaches, fabric conditioners, optical brighteners, antioxidants, stabilizers, thickeners, dispersants, soil release agents, anti-wrinkle agents, polymers, chelants, anti-corrosion agents, teeth cleansing and whitening agents, polymers, coplymers, cross-polymers, smectite clays, silica, silicate minerals, and the like.
- these products employ surfactant and emulsifying systems that are well known.
- fabric softener systems are described in U.S. Pat. Nos. 6,335,315, 5,674,832, 5,759,990, 5,877,145, 5,574,179; 5,562,849, 5,545,350, 5,545,340, 5,411,671, 5,403,499, 5,288,417, 4,767,547, 4,424,134, each hereby incorporated by reference.
- Liquid dish detergents are described in U.S. Pat. Nos. 6,069,122 and 5,990,065; automatic dish detergent products are described in U.S. Pat. Nos.
- Liquid laundry detergents which can use the present invention include those systems described in U.S. Pat. Nos.
- Non-limiting examples of suitable anionic surfactants that can be combined with the herein described microparticulate composition 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 ⁇ -olefin sulfonates.
- the alkyl groups generally contain from 8 to 18 carbon atoms and may be unsaturated.
- the 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.
- Non-limiting examples of nonionic surfactants that can be combined with the herein described mieroparticulate composition include, but are 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.
- Non-limiting examples of amphoteric surfactants that can be combined with the herein described mieroparticulate composition include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulfobetaines, alkyl glycinates, alkyl carboxyglyci nates, alkyl amphopropionates, alkyl amidopropyl hydroxysultaines, acyl taurates, and acyl glutamates wherein the alkyl and acyl groups have from 8 to 18 carbon atoms.
- Nonlimiting examples of suitable cationic surfactants that can be combined with the herein described mieroparticulate composition include water-soluble or water-dispersible or water-insoluble compounds containing at least one amine group which is preferably a quaternary amine group, and at least one hydrocarbon group which is preferably a long-chain hydrocarbon group.
- the hydrocarbon group may be hydroxylated and/or alkoxylated and may comprise ester- and/or amido- and/or aromatic-groups.
- the hydrocarbon group may be fully saturated or unsaturated.
- the surfactant is combined with the mieroparticulate composition in a range from about 1 to about 95%, preferably from about 2 to about 90%, and most preferably from 3 to 90% by weight of the total compositions.
- the mieroparticulate composition can be formed into a commercial product by admixing the mieroparticulate composition with a hydrophilic solvent.
- Suitable hydrophilic solvents include water, glycerol, ethanol, isopropanol, propylene glycol, butylene glycol, hexylene glycol, polyethylene glycol and mixtures thereof.
- the solvent is combined with the mieroparticulate composition in a range from about 0.1 to about 95%, preferably from 1 to 90%, and most preferably from 3 to 90% by weight of the total compositions.
- the cationic surface-treatment of the microparticulate material may be carried out by adding the microparticulate material, either in a powder-form (with a moisture content of less than 30% by weight) or as an aqueous dispersion, to an aqueous solution or dispersion containing the Type-1 Polymer and then adding the Type-1 coated microparticulate material to a solution or dispersion containing the Type-2 Polymer, and respectively shearing the resulting dispersions.
- the microparticulate material in a powder-form may be blended with a mixture of a Type-1 Polymer and a Type-2 Polymer, wherein the two polymers are used, respectively, in a form selected from a powder, a solution or a dispersion, and mixtures thereof.
- the adsorption of the Type-1 Polymer onto the surface of the microparticulate material is preferably carried out by adding the microparticulate material to an aqueous solution/dispersion of the polymer under high-shear agitation.
- Example 3 was prepared as follows: 60 g of a poly(DADMAC) solution (Zetag 7122, also called Magnafloc LT-7992, available from Ciba Specialty Chemicals, with 20% active) and 60 g of deionized water were added to a suitable flask.
- DADMAC poly(DADMAC) solution
- the batch was mixed for 6 minutes at a mixing speed of 200 rpm using a caframo mixer fitted with a dispersion blade agitator. After increasing the speed to 1,000 rpm, 300 g of an aqueous dispersion of an encapsulated fragrance (BL-AWAY-478A from International Flavors & Fragrances, Inc. (IFF, Inc.) New York, NY, with 40% encapsulated solids, including a fragrance) was added to the batch. The mixing speed was increased to at least 1,500 rpm, once about half of the dispersion-amount was added to the batch.
- an aqueous dispersion of an encapsulated fragrance BL-AWAY-478A from International Flavors & Fragrances, Inc. (IFF, Inc.) New York, NY, with 40% encapsulated solids, including a fragrance
- a 1 g aliquot of a 50% (w/w) solution of sodium hydroxide was added to the batch within one minute after the completion of addition of the above dispersion, while the batch remained under agitation at a mixing speed of 1,500 rpm.
- the batch was mixed for 30 minutes at 1,500 rpm, counted from the time of completion of addition of the foregoing dispersion.
- the above dosage of the poly(D ADMAC) solution corresponds to 10% poly(DADMAC), based on the weight of encapsulated solids, including a fragrance.
- Table 1 shows examples of compositions of microparticulates coated with Type-1 Polymer, specifically poly(D ADMAC) as prepared in the above described example 3. These samples became the starting materials for those samples shown in Table 2.
- Example 7 was prepared as follows: to 124 g of the resulting dispersion from Example 3 was added 26 g of a 2.5% (w/w) solution of a cationic guar (Jaguar C-14S from Rhodia), Type-2 Polymer, in a suitable vessel. The resulting mixture was mixed at a mixing speed of 1,000 rpm for 2.5 minutes, using a caframo mixer fitted with a dispersion blade agitator. The mixing speed was then increased to 1 ,500 rpm, and the batch was mixed for an additional 27.5 minutes. The amount of Type-1 Polymer and Type-2 Polymer correspond to 10 wt. % and 1.8 wt. %, respectively, based on the weight of encapsulated solids, including a fragrance.
- a cationic guar Jaguar C-14S from Rhodia
- Type-2 Polymer Type-2 Polymer
- Table 2 shows examples of microparticulate compositions corresponding to the present disclosure.
- the samples were prepared from the samples shown in Table 1 as described in the procedure for Example 7, above.
- three Type-2 Polymers were employed. These are Jaguar C-17 (INCI Name: Guar hydroxypropyltrimonium chloride; CAS: 65497-29-2) available from Rhodia Inc. Cranberry NJ; Jaguar C-14S (INCI Name: Guar hydroxypropyltrimonium chloride; CAS: 65497-29-2) available from Rhodia Inc.; and Soft-Cat SL-30 (INCI Name: Polyquaternium-67) available from Dow Chemical Co., Midland, MI. (00691 TABLE 2.
- Example 21 was prepared by the method described for example 3 but no NaOH solution was added to the dispersion.
- Examples 22, 23, and 24 were prepared as described for example 7 but example 21 was used as the precursor sample.
- Example 25 was prepared by the sequential treatment of the microparticulate material with the Type-1 Polymer and the Type-2 Polymer.
- Example 26 was prepared by the method described for example 3 but no NaOH solution was added to the dispersion and SN-SBOO-1001 AE from IFF, Inc., with 40% encapsulated solids, including a fragrance was used.
- Examples 27 and 28 were prepared as described for example 7 but example 26 was used at the precursor sample.
- Example 29 was prepared by the sequential treatment of the microparticulate material with the Type- 1 Polymer and the Type-2 Polymer.
- Example 30 was prepared by the method described for example 3 but no NaOH solution was added to the dispersion and a galaxolide containing melamine capsule ("encapsulated galaxolide") dispersion from IFF, Inc., with 40% encapsulated solids, including the fragrance was used.
- Examples 31, 32, and 33 were prepared as described for example 7 but example 30 was used at the precursor sample.
- Example 34 was prepared by the method described for example 3 but an encapsulated galaxolide dispersion from IFF, Inc., with 40% encapsulated solids, including the fragrance was used.
- Examples 35, 36, and 37 were prepared as described for example 7 but example 34 was used at the precursor sample.
- Examples 38 and 39 were prepared by the sequential treatment of the microparticulate material with the Type-1 Polymer and the Type-2 Polymer without the addition of NaOH.
- Example 40 was prepared by the sequential treatment of the microparticulate material with the Type-1, then a NaOH solution, then the Type-2 polymer.
- Example 41 was prepared by the addition of the microparticulate material to a premixed sample of the Type-1 Polymer and the Type-2 Polymer .
- Example 42 was prepared by the subsequent addition of additional Type-2 polymer to the product of example 41.
- the sample with the Type-1 Polymer that is the polymer that has a weight average molecular weight between about 300,000 and about 800,000 Dalton, shows significantly higher ⁇ -potential and electrophoretic mobility indicating higher charge on the microparticulate and very limited to no coagulation in a dispersion.
- Tables 7 shows examples of shower gel compositions employing the herein described microparticulate compositions.
- Tables 8 shows examples of shampoo compositions employing the herein described microparticulate compositions.
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Abstract
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US12/028,685 US7915214B2 (en) | 2006-01-12 | 2008-02-08 | Compositions containing benefit agent composites pre-emulsified using colloidal cationic particles |
US4438108P | 2008-04-11 | 2008-04-11 | |
US12/152,364 US7888306B2 (en) | 2007-05-14 | 2008-05-14 | Compositions containing benefit agent composites pre-emulsified using colloidal cationic particles |
US10133608P | 2008-09-30 | 2008-09-30 | |
US12/327,570 US7871972B2 (en) | 2005-01-12 | 2008-12-03 | Compositions containing benefit agents pre-emulsified using colloidal cationic particles |
PCT/US2009/035871 WO2009100464A1 (en) | 2008-02-08 | 2009-03-03 | Compositions containing cationically surface-modified microparticulate carrier for benefit agents |
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US10806233B2 (en) * | 2015-11-17 | 2020-10-20 | Elc Management Llc | Mascara composition and method |
CN108472237B (en) * | 2015-11-17 | 2021-12-28 | Elc 管理有限责任公司 | Mascara compositions and methods |
US10064807B2 (en) * | 2015-11-17 | 2018-09-04 | Elc Management Llc | Mascara composition and method |
WO2017167552A1 (en) | 2016-04-01 | 2017-10-05 | Unilever Plc | Personal cleansing composition |
Family Cites Families (89)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2800457A (en) | 1953-06-30 | 1957-07-23 | Ncr Co | Oil-containing microscopic capsules and method of making them |
NL104256C (en) | 1958-12-22 | |||
US3415758A (en) | 1960-03-09 | 1968-12-10 | Ncr Co | Process of forming minute capsules en masse |
US3516941A (en) | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
GB1316464A (en) | 1969-08-22 | 1973-05-09 | Kanebo Ltd | Process of treating fibrous articles with microcapsules containing hydrophobic treating agent |
US4145184A (en) | 1975-11-28 | 1979-03-20 | The Procter & Gamble Company | Detergent composition containing encapsulated perfume |
US4318818A (en) | 1979-11-09 | 1982-03-09 | The Procter & Gamble Company | Stabilized aqueous enzyme composition |
US4387090A (en) | 1980-12-22 | 1983-06-07 | The Procter & Gamble Company | Hair conditioning compositions |
USRE33429E (en) | 1981-03-23 | 1990-11-06 | Dow Corning Corporation | Lattice-entrapped emollient-moisturizer composition |
US4446032A (en) | 1981-08-20 | 1984-05-01 | International Flavors & Fragrances Inc. | Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same |
US4464271A (en) | 1981-08-20 | 1984-08-07 | International Flavors & Fragrances Inc. | Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same |
US4561998A (en) | 1982-05-24 | 1985-12-31 | The Procter & Gamble Company | Near-neutral pH detergents containing anionic surfactant, cosurfactant and fatty acid |
US4446042A (en) | 1982-10-18 | 1984-05-01 | The Procter & Gamble Company | Brightener for detergents containing nonionic and cationic surfactants |
US4534891A (en) | 1982-11-12 | 1985-08-13 | International Flavors & Fragrances Inc. | Branched C13 -alk-1-en-5-ones and use thereof in perfumery |
US4550862A (en) | 1982-11-17 | 1985-11-05 | The Procter & Gamble Company | Liquid product pouring and measuring package with self draining feature |
US4597898A (en) | 1982-12-23 | 1986-07-01 | The Proctor & Gamble Company | Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties |
US4424134A (en) | 1983-06-15 | 1984-01-03 | The Procter & Gamble Company | Aqueous fabric softening compositions |
US4515705A (en) | 1983-11-14 | 1985-05-07 | The Procter & Gamble Company | Compositions containing odor purified proteolytic enzymes and perfumes |
ATE45085T1 (en) | 1984-03-21 | 1989-08-15 | Richardson Vicks Ltd | HAIR TREATMENTS. |
LU85303A1 (en) | 1984-04-13 | 1985-11-27 | Oreal | HAIR COMPOSITION AND METHOD FOR TREATING HAIR |
US4537706A (en) | 1984-05-14 | 1985-08-27 | The Procter & Gamble Company | Liquid detergents containing boric acid to stabilize enzymes |
US4537707A (en) | 1984-05-14 | 1985-08-27 | The Procter & Gamble Company | Liquid detergents containing boric acid and formate to stabilize enzymes |
US4664064A (en) | 1985-03-21 | 1987-05-12 | Lowe H Edward | Cat box filler with incorporated pesticide |
US4690825A (en) | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
GB2188653A (en) | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
US5145842A (en) | 1986-06-11 | 1992-09-08 | Alder Research Center Limited Partnership | Protein kinase c. modulators. d. |
US4714562A (en) | 1987-03-06 | 1987-12-22 | The Procter & Gamble Company | Automatic dishwasher detergent composition |
US4968451A (en) | 1988-08-26 | 1990-11-06 | The Procter & Gamble Company | Soil release agents having allyl-derived sulfonated end caps |
US4973422A (en) | 1989-01-17 | 1990-11-27 | The Procter & Gamble Company | Perfume particles for use in cleaning and conditioning compositions |
CA2009047C (en) | 1989-02-27 | 1999-06-08 | Daniel Wayne Michael | Microcapsules containing hydrophobic liquid core |
US5137646A (en) | 1989-05-11 | 1992-08-11 | The Procter & Gamble Company | Coated perfume particles in fabric softener or antistatic agents |
US4948818A (en) | 1989-05-15 | 1990-08-14 | Dow Corning Corporation | Method of making porous hydrophilic-lipophilic copolymeric powders |
US4962170A (en) | 1989-08-31 | 1990-10-09 | Dow Corning Corporation | Method of making highly absorptive polymers |
US4962133A (en) | 1989-09-05 | 1990-10-09 | Dow Corning Corporation | Method of making highly adsorptive copolymers |
US5169552A (en) | 1989-10-04 | 1992-12-08 | The Procter & Gamble Company | Stable thickened liquid cleaning composition containing bleach |
EP0432951B2 (en) | 1989-12-04 | 2004-06-30 | Unilever Plc | Hair treatment composition |
FR2662175B1 (en) | 1990-05-18 | 1994-05-13 | Oreal | WASHING COMPOSITIONS BASED ON SILICONE AND FATTY ALCOHOLS WITH ETHER AND / OR THIOETHER OR SULFOXIDE GROUPS. |
US5194639A (en) | 1990-09-28 | 1993-03-16 | The Procter & Gamble Company | Preparation of polyhydroxy fatty acid amides in the presence of solvents |
FR2673179B1 (en) | 1991-02-21 | 1993-06-11 | Oreal | CERAMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS IN COSMETICS AND DERMOPHARMACY. |
DE69325578T3 (en) | 1992-05-12 | 2004-06-03 | The Procter & Gamble Company, Cincinnati | CONCENTRATED LIQUID TISSUE SOFTENER COMPOSITIONS WITH BIODEGRADABLE TISSUE SOFTENERS |
AU4398793A (en) | 1992-06-15 | 1994-01-04 | Procter & Gamble Company, The | Liquid laundry detergent compositions with silicone antifoam agent |
US5288417A (en) | 1992-07-06 | 1994-02-22 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric conditioning compositions and process for making them |
EP0581753B1 (en) | 1992-07-15 | 1998-12-09 | The Procter & Gamble Company | Dye transfer inhibiting compositions comprising polymeric dispersing agents |
EP0581752B1 (en) | 1992-07-15 | 1998-12-09 | The Procter & Gamble Company | Built dye transfer inhibiting compositions |
US5458809A (en) | 1992-07-15 | 1995-10-17 | The Procter & Gamble Co. | Surfactant-containing dye transfer inhibiting compositions |
US5458810A (en) | 1992-07-15 | 1995-10-17 | The Procter & Gamble Co. | Enzymatic detergent compositions inhibiting dye transfer |
CA2157178C (en) | 1993-03-01 | 2002-08-20 | Errol Hoffman Wahl | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5403499A (en) | 1993-04-19 | 1995-04-04 | Lever Brothers Company, Division Of Conopco, Inc. | Concentrated fabric conditioning compositions |
AU8079794A (en) | 1993-10-14 | 1995-05-04 | Procter & Gamble Company, The | Protease-containing cleaning compositions |
US5466802A (en) | 1993-11-10 | 1995-11-14 | The Procter & Gamble Company | Detergent compositions which provide dye transfer inhibition benefits |
FR2718961B1 (en) | 1994-04-22 | 1996-06-21 | Oreal | Compositions for washing and treating hair and skin based on ceramide and polymers with cationic groups. |
PE6995A1 (en) | 1994-05-25 | 1995-03-20 | Procter & Gamble | COMPOSITION INCLUDING A PROPOXYLATED POLYKYLENE OAMINE POLYKYLENE OAMINE POLYMER AS DIRT SEPARATION AGENT |
US6107429A (en) | 1994-10-24 | 2000-08-22 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
US5830967A (en) | 1994-10-24 | 1998-11-03 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
US5677407A (en) | 1995-06-07 | 1997-10-14 | Amcol International Corporation | Process for producing an oil sorbent polymer and the product thereof |
US5837790A (en) | 1994-10-24 | 1998-11-17 | Amcol International Corporation | Precipitation polymerization process for producing an oil adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
DE69608541T2 (en) | 1995-02-02 | 2001-01-18 | The Procter & Gamble Company, Cincinnati | MACHINE DISHWASHER COMPOSITIONS WITH COBALT CHELATE CATALYSTS |
US5968881A (en) | 1995-02-02 | 1999-10-19 | The Procter & Gamble Company | Phosphate built automatic dishwashing compositions comprising catalysts |
US5674832A (en) | 1995-04-27 | 1997-10-07 | Witco Corporation | Cationic compositions containing diol and/or diol alkoxylate |
US5712358A (en) | 1995-06-07 | 1998-01-27 | Amcol International Corporation | Process for producing an oil sorbent copolymer and the product thereof |
US5581005A (en) | 1995-06-16 | 1996-12-03 | The Procter & Gamble Company | Method for manufacturing cobalt catalysts |
CN1192774A (en) | 1995-06-16 | 1998-09-09 | 普罗格特-甘布尔公司 | Automatic dishwashing compositions comprising cobalt catalysts |
ES2158312T3 (en) | 1995-06-16 | 2001-09-01 | Procter & Gamble | WHITENING COMPOSITIONS THAT INCLUDE COBALT CATALYSTS. |
US5597936A (en) | 1995-06-16 | 1997-01-28 | The Procter & Gamble Company | Method for manufacturing cobalt catalysts |
US5916862A (en) | 1995-06-20 | 1999-06-29 | The Procter & Gamble Company | Detergent compositions containing amines and anionic surfactants |
US5559261A (en) | 1995-07-27 | 1996-09-24 | The Procter & Gamble Company | Method for manufacturing cobalt catalysts |
WO1997014405A1 (en) | 1995-10-16 | 1997-04-24 | The Procter & Gamble Company | Conditioning shampoos containing polyalkylene glycol |
US5703034A (en) | 1995-10-30 | 1997-12-30 | The Procter & Gamble Company | Bleach catalyst particles |
WO1997016517A1 (en) | 1995-10-30 | 1997-05-09 | The Procter & Gamble Company | Thickened, highly aqueous, cost effective liquid detergent compositions |
TR199801137T2 (en) | 1995-12-20 | 1998-10-21 | The Procter&Gamble Company | Enzyme par�a��klar� art� a�artma kataliz�r�. |
US5776443A (en) | 1996-03-18 | 1998-07-07 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Hair care compositions |
US5759990A (en) | 1996-10-21 | 1998-06-02 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
AR006355A1 (en) | 1996-03-22 | 1999-08-25 | Procter & Gamble | BIODEGRADABLE SOFTENING ASSET AND CONTAINING COMPOSITION |
US5932203A (en) | 1996-03-27 | 1999-08-03 | Proctor & Gamble Company | Conditioning shampoo compositions containing select hair conditioning esters |
US5935561A (en) | 1996-03-27 | 1999-08-10 | Procter & Gamble Company | Conditioning shampoo compositions containing select hair conditioning agents |
US5756436A (en) | 1996-03-27 | 1998-05-26 | The Procter & Gamble Company | Conditioning shampoo compositions containing select cationic conditioning polymers |
FR2751532B1 (en) | 1996-07-23 | 1998-08-28 | Oreal | WASHING AND CONDITIONING COMPOSITIONS BASED ON SILICONE AND DIALKYLETHER |
US5929022A (en) | 1996-08-01 | 1999-07-27 | The Procter & Gamble Company | Detergent compositions containing amine and specially selected perfumes |
US5914307A (en) | 1996-10-15 | 1999-06-22 | The Procter & Gamble Company | Process for making a high density detergent composition via post drying mixing/densification |
JP3222145B2 (en) | 1996-10-21 | 2001-10-22 | ザ、プロクター、エンド、ギャンブル、カンパニー | Concentrated fabric softening composition |
US5990065A (en) | 1996-12-20 | 1999-11-23 | The Procter & Gamble Company | Dishwashing detergent compositions containing organic diamines for improved grease cleaning, sudsing, low temperature stability and dissolution |
US6069122A (en) | 1997-06-16 | 2000-05-30 | The Procter & Gamble Company | Dishwashing detergent compositions containing organic diamines for improved grease cleaning, sudsing, low temperature stability and dissolution |
BR9713619A (en) | 1996-12-23 | 2000-04-11 | Quest Int | Particles containing organic polymer, process for producing them, and product and sunscreen product containing them |
US5968286A (en) | 1997-10-03 | 1999-10-19 | Helene Curtis, Inc. | Heat-mediated conditioning from shampoo and conditioner hair care compositions containing silicone |
DE19835114A1 (en) | 1998-08-04 | 2000-02-10 | Basf Ag | Microcapsules made from low-formaldehyde melamine-formaldehyde resins |
US6844302B1 (en) | 2000-10-27 | 2005-01-18 | International Flavors & Fragrances Inc. | Encapsulated flavor and fragrance |
US6740631B2 (en) | 2002-04-26 | 2004-05-25 | Adi Shefer | Multi component controlled delivery system for fabric care products |
US7585824B2 (en) | 2002-10-10 | 2009-09-08 | International Flavors & Fragrances Inc. | Encapsulated fragrance chemicals |
MX2007008451A (en) * | 2005-01-12 | 2008-03-13 | Amcol International Corp | Detersive compositions containing hydrophobic benefit agents pre-emulsified using colloidal cationic particles. |
-
2009
- 2009-03-03 EP EP09709193A patent/EP2265702A1/en not_active Withdrawn
- 2009-03-03 WO PCT/US2009/035871 patent/WO2009100464A1/en active Application Filing
- 2009-03-03 CA CA2725814A patent/CA2725814A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
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See references of WO2009100464A1 * |
Also Published As
Publication number | Publication date |
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CA2725814A1 (en) | 2009-08-13 |
WO2009100464A1 (en) | 2009-08-13 |
WO2009100464A4 (en) | 2009-10-01 |
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