WO2016000912A1 - Particule de libération d'agent bénéfique et composition comprenant ladite particule - Google Patents

Particule de libération d'agent bénéfique et composition comprenant ladite particule Download PDF

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Publication number
WO2016000912A1
WO2016000912A1 PCT/EP2015/062753 EP2015062753W WO2016000912A1 WO 2016000912 A1 WO2016000912 A1 WO 2016000912A1 EP 2015062753 W EP2015062753 W EP 2015062753W WO 2016000912 A1 WO2016000912 A1 WO 2016000912A1
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WO
WIPO (PCT)
Prior art keywords
particle
composition
hair
benefit agent
aromatic
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Application number
PCT/EP2015/062753
Other languages
English (en)
Inventor
Christopher Clarkson Jones
Xiaoyun Pan
Haitao QIAN
Yuanyuan Zhang
Original Assignee
Unilever N.V.
Unilever Plc
Conopco, Inc., D/B/A Unilever
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
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Application filed by Unilever N.V., Unilever Plc, Conopco, Inc., D/B/A Unilever filed Critical Unilever N.V.
Publication of WO2016000912A1 publication Critical patent/WO2016000912A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/622—Coated by organic compounds

Definitions

  • the present invention relates to a benefit agent delivery particle and composition comprising the particle.
  • the benefit agent delivery particle comprises a core comprising benefit agent, an inner shell, and an outer shell comprising at the outside surface of the particle aromatic compound having dihydroxylphenyl group.
  • the deposition efficiency of the encapsulating particles may be affected by the various ingredients in the composition, such as surfactants.
  • the performance for deposition may be a problem, especially on hair, scalp, and/or skin.
  • a benefit agent delivery particle comprising, a core comprising benefit agent, an inner shell, and an outer shell comprising at the outside surface of the particle aromatic compound having dihydroxylphenyl group. It was surprisingly found that when included into a shampoo and/or conditioner, the particles have better deposition onto virgin hair, damaged hair and/or skin.
  • the present invention provides a benefit agent delivery particle comprising a core comprising benefit agent, an inner shell, and an outer shell comprising at the outside surface of the particle, aromatic compound having dihydroxylphenyl group.
  • the present invention provides a home care or personal case composition comprising at least one particle of the present invention.
  • the present invention provides a method of treating a substrate, the method comprising a step of treating the substrate with a composition comprising particle of the present invention.
  • the present invention provides use of particle of the present invention for improved deposition.
  • Particle size refers to particle diameter unless otherwise stated.
  • diameter means the z- average particle size measured, for example, using dynamic light scattering (see international standard ISO 13321 ) with an instrument such as a Zetasizer NanoTM (Malvern Instruments Ltd, UK).
  • diameter means the apparent volume median diameter (D50, also known as x50 or sometimes d(0.5)) of the particles measurable for example, by laser diffraction using a system (such as a MastersizerTM 2000 available from Malvern Instruments Ltd) meeting the requirements set out in ISO 13320.
  • the particle has an average particle size of 50 nm to 800 ⁇ , more preferably from 300 nm to 200 ⁇ , and even more preferably from 0.5 to 100 ⁇ and most preferably from 1 to 50 ⁇ .
  • the zeta potential of the particles as measured using a Malvern Nano ZS90 apparatus, in Dl water at a solid content of 50 ppm and pH of 7 at 25°C is preferably at least -39 mV, more preferably at least -35 mV, even more preferably from -30 to 80mV, and still even more preferably from -24 to 60 mV.
  • Benefit agents according to the present invention refers to agents which may provide a range of benefits to hair, skin and/or fabrics, more preferably to hair and/or skin, even more preferably to hair and/or scalp, and most preferably to hair and/or scalp of human.
  • the benefit agent is typically present in an amount of from 10-90% by total weight of the particle, more preferably from 15 to 60% by total weight of the particle.
  • benefit agents can be incorporated into the particles.
  • any compatible benefit agent which can provide a benefit to a substrate which is treated with a preferably surfactant-containing composition can be used.
  • Advantages of the particles of the invention are a good deposition onto skin and/or hair, even in the presence of surfactant.
  • the benefit agents may include fragrance, pro-fragrance, hair conditioning agent, anti- dandruff agent, moisturizers, emollients, sunscreens, skin lightening agents, anti-aging active, dyes and/or pigments, colour care additives (including dye fixing agents), or a mixture thereof.
  • the benefit agent comprises fragrance, pro-fragrance, hair conditioning agent or a mixture thereof. More preferably, the benefit agent comprises fragrance and/or pro-fragrance, and most preferably the benefit agent is fragrance.
  • the core comprises at least 5% of fragrance by weight of the core, more preferably from 10% to 100% by weight of the core, even more preferably from 35% to 100% by weight of the core.
  • Useful components of the fragrance include materials of both natural and synthetic origin. They include single compounds and mixtures. Specific examples of such components may be found in the current literature, e.g., in Fenaroli's Handbook of Flavour Ingredients, 1975, CRC Press; Synthetic Food Adjuncts, 1947 by M. B.
  • fragrance in this context is not only meant a fully formulated product fragrance, but also selected components of that fragrance, particularly those which are prone to loss, such as the so-called 'top notes'.
  • Top notes are defined by Poucher (Journal of the Society of Cosmetic Chemists 6(2):80 [1955]). Examples of well known top-notes include citrus oils, linalool, linalyl acetate, lavender, dihydromyrcenol, rose oxide and cis-3-hexanol. Top notes typically comprise 15-25%wt of a fragrance composition and in those embodiments of the invention which contain an increased level of top-notes it is envisaged at that least 20%wt would be present within the particle.
  • fragrances with which the present invention can be applied are the so-called 'aromatherapy' materials. These include many components also used in fragrancery, including components of essential oils such as Clary Sage, Eucalyptus, Geranium, Lavender, Mace Extract, Neroli, Nutmeg, Spearmint, Sweet Violet Leaf and Valerian.
  • Typical fragrance components which it is advantageous to employ in the embodiments of the present invention include those with a relatively low boiling point, preferably those with a boiling point of less than 300, preferably 100-250 Celsius, measured at one atmosphere.
  • fragrance components which have a low LogP (i.e. those which will be partitioned into water), preferably with a LogP of less than 3.0.
  • the pro-fragrance can, for example, be a food lipid.
  • Food lipids typically contain structural units with pronounced hydrophobicity.
  • the majority of lipids are derived from fatty acids. In these 'acyl' lipids the fatty acids are predominantly present as esters and include mono-, di-, triacyl glycerols, phospholipids, glycolipids, diol lipids, waxes, sterol esters and tocopherols.
  • the fragrance is typically present in an amount of from 10-85% by total weight of the particle, preferably from 15 to 75% by total weight of the particle.
  • the fragrance suitably has a molecular weight of from 50 to 500 Dalton.
  • Pro-fragrances can be of higher molecular weight, being typically 1 -10 kD.
  • Hair conditioning agent may be selected from silicone conditioning agent, cationic surfactant, cationic deposition polymer, non-silicone oily material or a combination thereof. More preferably the hair condition agent comprises silicone conditioning agent, cationic deposition polymer or mixture thereof and most preferably the hair conditioning agent is silicone conditioning agent.
  • Suitable silicone conditioning agents include polydiorganosiloxanes, in particular polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Also suitable are silicone gums as described for example in WO
  • 96/31 188 These materials can impart body, volume and stylability to hair, as well as good wet and dry conditioning. Also suitable are functionalised silicones, particularly amino-functionalised silicones. Suitable non-silicone oily conditioning agents are selected from hydrocarbon oils, fatty esters and mixtures thereof.
  • Antidandruff agents are compounds that are active against dandruff and are typically antimicrobial agents and preferably antifungal agents. Antifungal agents typically display a minimum inhibitory concentration of about 50 mg/ml or less against
  • Suitable antidandruff agents include compounds selected from azole based antifungal agents, octopirox, selenium sulfide, metal pyrithione salts, and mixtures thereof.
  • the preferred azole based antifungal agents are ketoconazole and climbazole.
  • Preferred metal pyrithione salts are zinc, copper, silver and
  • zirconium pyrithione The most preferred is zinc pyrithione.
  • the inner shell is preferably substantially free of protein.
  • the inner shell may comprise inorganic material, polymer, or a mixture thereof.
  • Inorganic material may be selected from clay, zeolite, silica, amorphous silicate, crystalline nonlayer silicate, layer silicate, calcium carbonate, sodium carbonate, sodalite, and alkali metal phosphates.
  • the inner shell comprises polymer and more preferably is polymer.
  • the polymer may be bio-polymer and/or synthetic polymer.
  • Suitable polymer may comprise derivative of alginate, chitosan, collegen, dextran, gelatin, cellulose, gum, starch, polyvinyl pyrrolidone, polyvinyl alcohol, cellulose ether, polystyrene, polyacrylate, polymethacrylate, polyolefin, aminoplast polymer, polyacrylamide, acrylate-acrylamide copolymer, melamine-formaldehyde condensate, urea- formaldehyde condensate, polyurethane, polysiloxane, polyurea, polyamide, polyimide, polyanhydride, polyolefin, polysulfone, polysaccaharide, polylactide, polyglycolide, polyorthoester, polyphosphazene, silicone, lipid, polyester, ethylene maleic anyhydride copolymer, styrene maleic anyhydride copoly
  • the inner shell comprises polystyrene, polyvinyl alcohol, polyacrylate, polymethacrylates, polyolefins, aminoplast polymer, polyacrylamide, acrylate-acrylamide copolymer, melamine-formaldehyde condensate, urea-formaldehyde condensate, polyurethane, polysaccaharide or a mixture thereof. More preferably, the inner shell comprises polystyrene, modified polyvinyl alcohol, polyacrylate, polymethacrylate, polyolefin, aminoplast polymers, melamine-formaldehyde condensate, urea-formaldehyde condensate, polyurethane or a mixture thereof.
  • the inner shell comprises polystyrene, modified polyvinyl alcohol, polyolefin, polyurethane or a mixture thereof. Still even more preferably, the inner shell comprises polystyrene, modified polyvinyl alcohol or a combination thereof and most preferably, the inner shell is polystyrene, modified polyvinyl alcohol, or a combination thereof.
  • the outer shell is different from the inner shell.
  • the outer shell comprises aromatic compound having
  • the outer shell is aromatic compound which comprises catechol group, resorcinol group or a combination thereof.
  • the outer shell is preferably substantially free from protocatechuic acid.
  • the aromatic compound may be selected from aromatic polymer, aromatic small molecule, or a combination thereof.
  • the aromatic compound is aromatic small molecule.
  • the aromatic polymer is formed by polymerization of the aromatic small molecule.
  • Aromatic polymer as used herein refers to polymer having more than 2 repeating units which comprises aromatic ring, preferably benzene ring, more preferably catechol group, resorcinol group or a combination thereof.
  • the aromatic polymer usually has a weight-average molecular weight of greater than 2,000, more preferably greater than 20,000 Daltons and even more preferably from 50,000 to 1 ,000,000 Daltons.
  • the weight-average molecular weight may be measured by following the standard of ASTM D4001 -2013.
  • the molecule weight of aromatic small molecule is typically no greater than 2000 Daltons, preferably from 100 to 800 Daltons, more preferably from 1 10 to 300 Daltons.
  • lecule preferably has a molecular structure of
  • R 1 is a hydroxyl group
  • R 2 is a hydrogen or hydroxyl group
  • R 3 is a hydroxyl group when R 2 is a hydrogen
  • R 3 is a hydrogen or hydroxyl group when R 2 is a hydroxyl group.
  • R may be any group but preferably is group containing hydrogen, carbon, oxygen, nitrogen, sulfur, halogen or a combination thereof. More preferably R is selected from hydrogen, hydroxyl, alkyl, alkenyl, aryl, amide, ester, oxy, carbonyl, carboxyl, halogen or any combination thereof.
  • the aromatic small molecule comprises dopamine, 3,4-dihydroxybenzylamine, catechol, protocatechuic acid, gallic acid, 3,4-dihydroxybenzaldehyde, resorcinol, resveratrol, piceatannol, propyl gallate, their salts, or a mixture thereof.
  • the aromatic small molecule comprises catechol, piceatannol, dopamine, 3,4-dihydroxybenzylamine, 3,4-dihydroxybenzaldehyde, resveratrol, gallic acid, their salts, or a mixture thereof and most preferably the aromatic small molecule comprises catechol, piceatannol, 3,4- dihydroxybenzylamine, 3,4-dihydroxybenzylquaternium salts, 3,4- dihydroxybenzaldehyde, or a combination thereof.
  • the aromatic compounds are preferably aggregated together with non-covalent forces at the outside surface of the particle.
  • the strong non-covalent forces may include charge transfer, ⁇ -stacking, hydrogen bonding or combination thereof. More preferably, the strong non-covalent force comprises ⁇ -stacking.
  • the dihydroxylphenyl group has strong interaction with hair and skin and therefore helps the deposition of the particles.
  • the outer shell may further comprise accelerant which may help and/or accelerate the formation of outer shell.
  • the accelerant may be selected from inorganic salt, organic amine or a mixture thereof but preferably is organic amine. More preferably, the organic amine comprises alkyl amine and most preferably the organic amine is hexamethylenediamine.
  • the particle of the present invention may be manufactured by any process, however, it is preferred that the process for producing the benefit agent delivery particle comprises the step of:
  • the benefit agent may be encapsulated when the capsule having the inner shell is formed.
  • the capsules having the inner shell can be formed which does not contain the benefit agent (hollow capsule) and subsequently exposed them to a benefit agent which can be adsorbed into the inner region.
  • the outer shell is formed by aromatic small molecule.
  • the weight ratio of the inner shell to the aromatic small molecule is preferably in the range of 0.001 to 30, more preferably from 0.005 to 10, even more preferably from 0.01 to 5 and most preferably from 0.02 to 2.
  • the accelerant is preferably present.
  • the molar ratio of the accelerant to the aromatic small molecule is preferably in the range of 1 :100 to 50:1 , more preferably from 1 :20 to 10:1 and most preferably from 1 :10 to 5:1.
  • the ratio of the thickness of the inner shell to the outer shell is from 1 :100 to 1000: 1 , more preferably from 1 :40 to 200: 1 to and even more preferably from 1 : 10 to 50:1 .
  • the outer shell has a thickness of 30 nm to 10 ⁇ , more preferably from 50 nm to 2 ⁇ " ⁇ . The thickness of the inner shell may be measured, for example, by scanning electron microscopy.
  • the thickness of the outer layer may be measured by halving the absolute difference of particle sizes before and after the formation of the outer shell.
  • the weight ratio of outer shell to inner shell is in the range of is in the range of 0.001 to 50, more preferably from 0.005 to 20, even more preferably from 0.01 to 10 and most preferably from 0.04 to 4.
  • the present invention also provides a home care or personal case composition comprising at least one particle of the present invention.
  • the composition may be a laundry detergent, laundry conditioner, deodorant, antiperspirant, shampoo, hair conditioner or skin care or skin cleansing product.
  • the composition is a personal care composition. More preferably, the composition is a skin or hair treatment composition and most preferably the composition is a hair treatment composition.
  • the end-product composition of the invention may be in any physical form e.g., a solid bar, a paste, gel or liquid but preferably a gel or liquid.
  • the composition is more preferably an aqueous-based liquid.
  • the composition is a hair treatment composition and is a liquid or gel.
  • the particle is typically included in the composition at levels of from 0.001 % to 10%, preferably from 0.005% to 7.55%, most preferably from 0.01 % to 5% by weight of the total composition.
  • surfactants which may be anionic, cationic, non-ionic, zwitterionic and amphoteric
  • silicone conditioning agents and non-silicone oily conditioning agents suspending agents, anti-dandruff agents, thickeners, cationic deposition polymers and shading agents.
  • Preferred anionic surfactants are the alkyl sulfates and alkyl ether sulfates. These materials have the respective formulae R2OSO3M and R1O (C2H4O) xSC M, wherein R2 is alkyl or alkenyl of from 8 to 18 carbon atoms, x is an integer having a value of from about 1 to about 10, and M is a cation such as ammonium, alkanolamines, such as triethanolamine, monovalent metals, such as sodium and potassium, and polyvalent metal cations, such as magnesium, and calcium. Most preferably R2 has 12 to 14 carbon atoms, in a linear rather than branched chain.
  • the total amount of anionic cleansing surfactant in hair treatment compositions of the invention generally ranges from 0.5 to 45 wt%, more preferably from 1 .5 to 20 wt%.
  • the surfactant comprises at least 3 wt% on total composition of an alkyl ether sulphate, in for example, a shampoo.
  • a cationic surfactant is preferably included such as an alkyl ammonium material.
  • Hair treatment compositions according to the invention such as shampoos and conditioners suitably contain conditioning agents such as silicone conditioning agents and non-silicone oily conditioning agents.
  • Suitable silicone conditioning agents include polydiorganosiloxanes, in particular polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable for use in compositions of the invention (particularly shampoos and conditioners) are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Also suitable for use in compositions of the invention are silicone gums having a slight degree of cross-linking, as are described for example in WO 96/31 188. These materials can impart body, volume and stylability to hair, as well as good wet and dry conditioning. Also suitable are functionalised silicones, particularly amino- functionalised silicones.
  • the silicone conditioning agent is suitably present in hair treatment compositions at a level of from 0.05 to 10, preferably from 0.2 to 5, more preferably from 0.5 to 3 percent based on total weight of the composition.
  • Suitable non-silicone oily conditioning agents are preferably selected from hydrocarbon oils, fatty esters and mixtures thereof.
  • the hair treatment composition comprises a cationic deposition polymer, which may assist in deposition of ingredients in the composition.
  • the cationic deposition polymer is (or comprises) cationic polygalactomannan, especially guar or cassia derived polygalactomannan modified with hydroxypropyl trimonium chloride.
  • compositions according to the invention should contain from 0.01 % to 2% wt. of the composition cationic deposition polymer, more preferably from 0.05 to 0.5% wt. and most preferably from 0.08 to 0.25% by weight of the composition.
  • Antidandruff agents are compounds that are active against dandruff and are typically antimicrobial agents and preferably antifungal agents.
  • Antifungal agents typically display a minimum inhibitory concentration of about 50 mg/ml or less against Malassezia spp.
  • Suitable antidandruff agents include compounds selected from azole based antifungal agents, octopirox, selenium sulfide, metal pyrithione salts, and mixtures thereof.
  • the preferred azole based antifungal agents are ketoconazole and climbazole.
  • Preferred metal pyrithione salts are zinc, copper, silver and zirconium pyrithione. The most preferred is zinc pyrithione.
  • the antidandruff agent is present at from 0.01 to 5% wt. of the composition, more preferably from 0.1 to 2.5% wt. of the composition.
  • Suspending agent if included, will preferably be present in a composition of the invention at levels of from 0.1 to 10%, more preferably from 0.5 to 6%, even more preferably from 0.9 to 4% by total weight of suspending agent based on the total weight of the composition.
  • composition of the invention may contain other ingredients for enhancing performance and/or consumer acceptability.
  • ingredients include dyes and pigments, pH adjusting agents, pearlescers or opacifiers, viscosity modifiers, and preservatives or antimicrobials.
  • Each of these ingredients will be present in an amount effective to accomplish its purpose.
  • these optional ingredients are included individually at a level of up to 5% by weight of the total composition.
  • the composition preferably comprises at least 30% of water by weight of the composition, more preferably from 35 to 95%, even more preferably from 45 to 88%, still even more preferably from 55 to 82%, most preferably from 65 to 80% by weight of the total composition.
  • the particles of the invention may be incorporated into home care composition, preferably laundry composition.
  • the active ingredient in the compositions for these laundry compositions is preferably a surface active agent or a fabric conditioning agent. More than one active ingredient may be included. For some applications a mixture of active ingredients may be used.
  • the compositions may be liquid, powder or tablet laundry composition. Liquids are particularly preferred.
  • the laundry compositions are preferably main wash (fabric washing) compositions or rinse-added softening compositions.
  • the main wash compositions may include a fabric softening agent and the rinse-added fabric softening compositions may include surface-active compounds, particularly non-ionic surface- active compounds.
  • laundry compositions according to the invention comprise one or more enzymes.
  • the enzymes may be present at levels from about 0.00001 wt.% to about 2 wt.%, from about 0.0001 wt.% to about 1 wt.% or even from about 0.001 wt.% to about 0.5 wt.% enzyme protein by weight of the composition.
  • the present invention also provides a method of treating a substrate, the method comprising a step of treating the substrate with a composition comprising the particle of the present invention.
  • the substrate is selected from skin, hair, scalp and/or textile material, even more preferably the substrate is selected from skin, hair and/or scalp, and most preferably the substrate is hair and/or scalp.
  • the particle is preferably included in a composition as described above.
  • This example demonstrates the preparation of PS latex particles coated by aromatic compound.
  • the capability of forming aggregate of a series of catechol and resorcinol derivatives was tested.
  • the catechol and resorcinol derivatives (together with accelerant if present) were dissolved in THAM-HCI buffer (10 mM, pH 8.5) in vial.
  • the vial was kept open to air for one to five days. Then, it was checked that whether there was precipitate in the vial. If there was precipitate, that aromatic small molecule was used for the preparation of benefit delivery particles.
  • the Polystyrene (PS) latex was purified through centrifugation and washed by Dl water for three times.
  • the latex particles were coated by the aromatic compound.
  • dopamine hydrochloride As an example, the dopamine hydrochloride was dissolved in THAM-HCI buffer to prepare a solution with concentration of 3.0 mg/ml. 500 ⁇ _ of the dopamine hydrochloride solution was added to the tube containing the centrifuge pellet (as described above). The feeding weight ratio of the dopamine hydrochloride to microspheres was 60%. The mixture was stirred for 1 day while shielded from light with aluminum foil. The mixture was then purified through centrifugation and washed by Dl water for three times. The obtained pellet was dispersed in Dl water to form dispersion with solid content of 0.5% (w/w).
  • the coating process using other aromatic small molecule was similar with that of dopamine hydrochloride.
  • the feeding weight ratio of the aromatic small molecule to microspheres was 0.6.
  • the coating time for each molecule was listed in Table 2.
  • a sample without addition of aromatic compound was prepared by diluting the original latex with Dl water to obtain an aqueous latex solution with solid content 0.5% (w/w). Table 2
  • the zeta potentials of the particles were measured by zeta potential analyzer (Zetasizer Nano ZS90, Malvern, USA) at 25°C.
  • the particles were dispersed in water with solid content of 50 ppm and the pH of the dispersion was adjusted to about 7 for measurement of zeta potential. Each test was repeated three times.
  • the average results of zeta potentials were listed in Table 2.
  • the change of Zeta potential of particles coated by the aromatic compound indicates that second shells were formed by the coating process.
  • the shampoo base was formulated by following standard process for shampoo.
  • the shampoo base contained 12 wt% of sodium laurethsulfate, 1 .60 wt% of
  • the conditioner base was also formulated by following standard process for conditioner.
  • the conditioner base contained 3.18 wt% of behenyltrimethylammonium chloride, 4.44 wt% of cetearyl alcohol, 0.22 wt% of hydroxyethyl cellulose, 0.15 wt% of preservative, and was balanced by water.
  • Hair switches (length of 5.5 cm, weight of 750 mg) were soaked into aqueous solution of 14 wt% of SLES at 40°C with continuous shaking for 30 minutes. Then these hair switches were rinsed by tap water thoroughly and dried at ambient environment overnight.
  • Three hair switches were wetted with tap water and swung to remove excess water.
  • the three hair switches were rubbed respectively with a mixture of 70 mg of shampoo base (or condition base) and 20 ⁇ of 0.5 wt% of particles water dispersion of Table 2, and rinsed by 500ml of tap water.
  • the switch was swung dry and then immersed in a vial containing 20 milliliters of ethyl acetate for 30 minutes. 200 microliters of the extraction liquid was withdrawn from the vial and added to a 96-well microplate for fluorescence measurement (excitation 441 nm, emission 500 nm) to afford a reading of EL.
  • the second switch was wetted with tap water and swung dry, to which 20 ⁇ of the 0.5% of uncoated polystyrene latex was added. The switch was also extracted with 20 milliliters of ethyl acetate for 30 minutes.
  • Table 3 shows the deposition results on virgin and damage hair via incorporating the particles into shampoo base or conditioner base. The averages and standard derivations are calculated from 5 tests.
  • This example demonstrates the deposition performance on skin of PS latex particles coated by aromatic compound.
  • Skin from towards the back of female pig was bought from the pork market, and was used as simulation of human skin/scalp.
  • the pig skin was first defatted using a normal scalpel to remove subcutaneous fat and get a flat underside surface. The final thickness of the defatted pig skin was around 4 mm.
  • the pig skin was then pre-washed by lightly finger rub using commercial washing liquid and rinsed with tap water thoroughly to remove excess oil on the surface. After that, the pig skin was cut into small pieces of 2 cmx2 cm in size and wrapped with cling film and tin foil in sequence, then frozen at -20°C for storage.
  • a typical skin wash procedure is shown as follows. Skin pieces were thaw out under about 25°C before use. One skin piece was placed in a Petri dish, to which 25 mg of the shampoo base (or hair conditioner base, as prepared in 2.1 of Example 2) was added together with 20 ⁇ of 0.5 wt% of particles water dispersion of Table 2. The skin with the mixture onto it was then gently rubbed with another piece of pig skin for 30 seconds and the two pieces rinsed with totally 250 ml of tap water. The two pieces of skin were then immersed in a vial containing 10 milliliters of ethyl acetate for 20 minutes. 200 microliters of the extraction liquid was withdrawn from the vial and added to a 96-well microplate for fluorescence measurement (excitation 441 nm, emission
  • one skin piece was placed in a Petri dish, to which 20 ⁇ of the 0.5% of uncoated polystyrene was added.
  • the skin with the latex was then immersed in a vial containing 10 milliliters of ethyl acetate for 20 minutes. 200 microliters of the extraction liquid was withdrawn from the vial and added to a 96-well microplate for fluorescence measurement (excitation 441 nm, emission 500 nm) to afford a reading of Eo.
  • the benefit delivery particles of the present invention had better deposition performance on at least one substrate selected from virgin hair, damage hair in at least one composition with at least one base.
  • This example demonstrates the deposition performance on skin of crosslinked modified polyvinyl alcohol (mPVOH) particles coated by aromatic compound.
  • the concentration of aldehyde group (-CHO concentration) of dextran-CHO product was measured to be 0.2 mol/L.
  • the flask was transferred into a water bath and heated from room temperature to 50°C at rate of about 1°C/min under mild magnetic stir. After being kept at 50°C for 1 .5 hour, 500 ⁇ of 1 M HCI was added to adjust pH of the mixture to 2-3 and the resultant mixture stirred for another 4.5 h at 50°C. The flask was then taken out from the water bath and the perfume capsules could be found enriched in upside of the mixture.
  • the sizes of the particles were measured based upon 10 capsules from the
  • zeta potentials of the particles were measured by zeta potential analyzer (Zetasizer Nano ZS90, Malvern, USA). The particles were dispersed in water with solid content of 50 ppm and the pH of the dispersion was adjusted to about 7 for measurement of zeta potential. The results of zeta potentials and particle sizes were listed in Table 6.
  • the deposition performance of the particles in Table 6 was tested by following similar procedure as described in 3.1 of Example 3 except that acetone was used as extraction solvent instead of ethyl acetate; the pig skin was immersed into 10ml of acetone for 30 minutes followed by ultrasonication for 2 minutes; and the excitation and emission wavelength are 470 and 618 nm, respectively.
  • the particles of the present invention have better deposition on pig skin than the capsules without coating of aromatic compound.

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Abstract

L'invention concerne une particule de libération d'agent bénéfique, qui comprend un noyau contenant un agent bénéfique, une coque intérieure; et une coque extérieure comprenant au niveau de la surface extérieure de la particule un composé aromatique présentant un groupe dihydroxyphényle.
PCT/EP2015/062753 2014-06-30 2015-06-09 Particule de libération d'agent bénéfique et composition comprenant ladite particule WO2016000912A1 (fr)

Applications Claiming Priority (4)

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CNPCT/CN2014/081291 2014-06-30
CN2014081291 2014-06-30
EP14182854.1 2014-08-29
EP14182854 2014-08-29

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10722436B2 (en) 2015-08-10 2020-07-28 Mary Kay Inc. Topical compositions
US11253458B2 (en) 2016-10-28 2022-02-22 Conopco, Inc. Personal care composition comprising particles
US11471396B2 (en) 2016-10-28 2022-10-18 Conopco, Inc. Personal care compositions comprising surface-modified particles and non-volatile funcationalised silicone

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2133374A (en) * 1983-01-14 1984-07-25 Kureha Chemical Ind Co Ltd Adhesive-containing microcapsules
WO2009103615A1 (fr) * 2008-02-21 2009-08-27 Unilever Plc Améliorations de particules utiles
US20100009893A1 (en) * 2007-02-13 2010-01-14 Givaudan Sa Microcapsules
WO2014064121A2 (fr) * 2012-10-25 2014-05-01 Unilever Plc Améliorations se rapportant à des compositions de traitement de surface

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2133374A (en) * 1983-01-14 1984-07-25 Kureha Chemical Ind Co Ltd Adhesive-containing microcapsules
US20100009893A1 (en) * 2007-02-13 2010-01-14 Givaudan Sa Microcapsules
WO2009103615A1 (fr) * 2008-02-21 2009-08-27 Unilever Plc Améliorations de particules utiles
WO2014064121A2 (fr) * 2012-10-25 2014-05-01 Unilever Plc Améliorations se rapportant à des compositions de traitement de surface

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10722436B2 (en) 2015-08-10 2020-07-28 Mary Kay Inc. Topical compositions
US11179305B2 (en) 2015-08-10 2021-11-23 Mary Kay Inc. Topical compositions
US11253458B2 (en) 2016-10-28 2022-02-22 Conopco, Inc. Personal care composition comprising particles
US11471396B2 (en) 2016-10-28 2022-10-18 Conopco, Inc. Personal care compositions comprising surface-modified particles and non-volatile funcationalised silicone

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