WO2024083677A1 - Wax-based microcapsules - Google Patents

Wax-based microcapsules Download PDF

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Publication number
WO2024083677A1
WO2024083677A1 PCT/EP2023/078498 EP2023078498W WO2024083677A1 WO 2024083677 A1 WO2024083677 A1 WO 2024083677A1 EP 2023078498 W EP2023078498 W EP 2023078498W WO 2024083677 A1 WO2024083677 A1 WO 2024083677A1
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WO
WIPO (PCT)
Prior art keywords
wax
phase
microcapsules
methyl
perfume
Prior art date
Application number
PCT/EP2023/078498
Other languages
French (fr)
Inventor
Philipp ERNI
Romane ANDRE
Original Assignee
Firmenich Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich Sa filed Critical Firmenich Sa
Publication of WO2024083677A1 publication Critical patent/WO2024083677A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • 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
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5063—Compounds of unknown constitution, e.g. material from plants or animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5089—Processes
    • 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
    • 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
    • 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
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • B01J13/043—Drying and spraying
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
    • 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
    • C11D3/2093—Esters; Carbonates
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • the present invention relates to a new process for the preparation of microcapsules.
  • Microcapsules are also an object of the invention.
  • Consumer products comprising said microcapsules, in particular perfumed consumer products or flavoured consumer products are also part of the invention.
  • Polyurea and polyurethane-based microcapsule slurry are widely used for example in perfumery industry for instance as they provide a long lasting pleasant olfactory effect after their applications on different substrates. Those microcapsules have been widely disclosed in the prior art.
  • Wax-based microcapsules are also known.
  • the wax is a material hard to handle especially as the wax needs to be heated above its melting point and the crystallization needs to be avoided during the preparation of the microcapsules. This issue becomes more critical and difficult to handle at an industrialisation scale.
  • the present invention is proposing a solution to the above-mentioned problem by providing microcapsules comprising hydrophobic material entrapped in a wax matrix. Furthermore, the present invention provides a simple and cost-effective process for preparing wax-based microcapsules.
  • the present invention solves the above-mentioned problems by providing new microcapsules encapsulated hydrophobic material, for example perfume or flavour, in a wax matrix and a new process for preparing said microcapsules.
  • the presence of the wax retains the hydrophobic material (for example perfume or flavor) until the final application on different substrates (e.g. on textiles, skin or hair).
  • the process disclosed in the present invention there is no need to handle the melted phase of the wax and crystallization of the wax is therefore prevented.
  • a first object of the invention is therefore a process for preparing a microcapsule slurry, wherein it comprises the steps of:
  • step iii) Adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii), wherein the melted wax and the hydrophobic active ingredient form a second phase,
  • Another object of the invention is a microcapsule obtainable according to the process disclosed above.
  • the present invention relates to a consumer product in the form of a perfumed consumer product or a flavored consumer product.
  • Figure 1 represents a SEM image of the microcapsules of the present invention.
  • hydrophobic material it is meant any hydrophobic material - single material or a mixture of materials - which forms a two-phase dispersion when mixed with water.
  • ingredient it is meant a single compound or a combination of ingredients.
  • perfume or flavour oil it is meant a single perfuming or flavouring compound or a mixture of several perfuming or flavouring compounds.
  • consumer product or “end-product” it is meant a manufactured product ready to be distributed, sold and used by a consumer.
  • microcapsule in the present invention it is meant microcapsules that are in a matrix form and have preferably a particle size distribution in the micron range (e.g. a mean diameter (Dv(50) comprised between about 0.1 and 500 microns, preferably between 1 and 100 microns.
  • Dv(50) mean diameter
  • the matrix material comprises a wax and the microcapsule has to entrap preferably at least 5%, more preferably at least 10%, even more preferably at least 20 wt.%, even more preferably at least 30 wt.%, even more preferably at least 35 wt.% of the hydrophobic material, based on the total weight of the microcapsule.
  • microcapsule slurry it is meant microcapsule(s) that is (are) dispersed in a liquid.
  • the slurry is an aqueous slurry, i.e the microcapsule(s) is (are) dispersed in an aqueous phase.
  • dispersion in the present invention it is meant a system in which particles, aggregates, precipitates, complexes and/or emulsion droplets are dispersed in a continuous phase of a different composition and it specifically includes a suspension or an emulsion.
  • Dispersion according to the invention can encompass two-phases dispersion.
  • emulsion denotes a mixture of two or more liquids that are normally immiscible (i.e. not mixable).
  • one liquid the dispersed phase
  • the continuous phase the continuous phase
  • oilin water emulsions comprising a continuous hydrophilic phase, preferably comprising water, in which the hydrophobic phase is dispersed.
  • fat used in the present invention refers to lipid components that are solid or in the form of a paste at room temperature (typically between 20 and 25°C) whereas the term “oil” used in the present invention refers to lipid components that are liquid at room temperature. Fat has typically a melting temperature equals or less than 35°C.
  • wax used in the present invention refers to lipid components that are solid or in the form of a paste at room temperature (typically between 20 and 25°C) and that have a melting temperature greater than 35°C.
  • a first object of the invention is therefore a process for preparing a microcapsule slurry, wherein it comprises the steps of: (i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
  • step iii) Adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii), wherein the melted wax and the hydrophobic active ingredient form a second phase,
  • no hydrophobic material is added in step ii).
  • the process comprises the steps of:
  • the process of the invention is preferably “one pot” process meaning that a single reactor is needed during the process for preparing microcapsules leading to an efficient process for preparing microcapsules (crystallization of the wax is avoided). It is understood therefore that the person skilled in the art is also able to perform the process in ways that do not fall under the description of “one pot”, for example but not limited to pre-mixing some of the phases or materials in additional containers, or by using continuous or semi-continuous processing equipment.
  • a dispersing phase comprising optionally an emulsifier to form a first phase is prepared.
  • the dispersing phase comprises water. According to an embodiment, the dispersing phase consists of water.
  • At least one part of water (between 1 and 99%) is substituted with alcohol preferably chosen in the group consisting of glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
  • the dispersing phase consists of alcohol preferably chosen in the group consisting of glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
  • the emulsifier comprises plant-based non digestible fibers and plant-based or polysaccharides.
  • the emulsifier comprises a plant-based protein.
  • the emulsifier may also comprise certain proteins of animal origins, including casein or caseinates, whey proteins, or other milk proteins.
  • the emulsifier is a modified starch.
  • the emulsifier is a hydrophobically modified starch including but not limited to octenyl succinic anhydride starch.
  • the emulsifier is gum arabic.
  • the emulsifier comprises a protein, most preferably a plant-based protein.
  • the emulsifier can be chosen in the group consisting of SDS (sodium dodecyl sulfate), phospholipids including lecithin, mono and diglycerides of fatty acids, fatty alcohols, saponins, proteins, polysaccharides and other hydrocolloids, sugar esters, sorbitan esters, polysorbates, polyglycol ethers, modified starch, fibers and mixtures thereof.
  • the proteins used in the present invention can be plant-based protein (including for example lupin, potato, faba, red lentil, soy, pea protein), protein from animal proteins (including for example casein or caseinates, whey proteins, or other milk proteins).
  • Polysaccharides used in the present invention can be pectins, carrageenans, alginates, cellulose gums, modified cellulose, starches.
  • the emulsifier is preferably used in an amount comprised between 0.01% and 10%, preferably 0.5 and 2% by weight based on the total weight of the slurry.
  • a second step of the process consists in adding a wax, preferably a solid wax, and optionally a hydrophobic material on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax (step (ii)).
  • step ii) at least one solid wax is added.
  • a mixture of waxes can be used, a mixture of wax(s) and oil(s) can be used, a mixture of wax(s) and fat(s) can be used or a mixture of wax(s), oil(s), and fat(s) can be used.
  • the wax is a plant-based wax and/or a wax of animal origins.
  • the wax can be chosen in the group consisting of rice bran wax, candelilla wax, carnauba wax and sunflower seed wax, beeswax, olive wax, paraffin wax, synthetic wax, berry wax, myrica wax, rapeseed wax, hydrolyzed sunflower wax, orange wax, jasmin wax, tea wax, rose wax, and mixtures thereof.
  • the wax is typically used in an amount that comprises between 1% w/w and 20% w/w, preferably 1% w/w and 10% w/w, based on the total weight of the slurry.
  • the wax is typically used in an amount comprises between 30% w/w and 99.9999% w/w, preferably 40% w/w and 99% w/w, more preferably 40% w/w and 95% w/w, based on the total weight of the microcapsules.
  • the oil can be chosen in the group consisting of sunflower oil, canola oil, olive oil, palm oil, almond oil, MTC (medium chain triglycerides) oil.
  • the fat can be chosen in the group consisting of cocoa butter, coco fat, animal fat such as beef fat, duck fat, pork fat.
  • step ii) no mixing step is carried out (to avoid any emulsification). Indeed, at the end of step (ii), a biphasic system is obtained.
  • step ii) the system containing the wax, preferably solid wax, and the dispersing phase is heated greater than the melting point of the wax.
  • Tm melting point
  • the melting point can be measured by differential scanning calorimeter, for example Q2000 (TA Instruments, New Castle, DE, USA.
  • the system is heated at a temperature comprised between 70 and 90°C.
  • a thirst step of the process consists of adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii) wherein the melted wax and the hydrophobic active ingredient form a second phase (step (iii)).
  • step iii) the first phase and the second phase are two separate phases (biphasic system).
  • Hydrophobic material that can be added in step ii) and/or step iii) can be the same or different.
  • Hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
  • a single hydrophobic material or mixture of hydrophobic materials can be used.
  • the hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
  • hydrophobic material is an active ingredient, it is preferably chosen from the group consisting of flavors, flavor ingredients, perfumes, perfume ingredients, nutraceuticals, cosmetics, pest control agents, biocide actives and mixtures thereof.
  • the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents and biocide actives.
  • the hydrophobic material comprises a phase change material (PCM).
  • PCM phase change material
  • the hydrophobic material comprises a mixture of biocide actives with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, pest control agents.
  • the hydrophobic material comprises a mixture of pest control agents with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, biocide actives.
  • the hydrophobic material comprises a perfume.
  • the hydrophobic material consists of a perfume.
  • the hydrophobic material consists of biocide actives.
  • the hydrophobic material consists of pest control agents.
  • perfume or also “perfume oil”
  • perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition.
  • perfuming ingredient it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor.
  • perfume oil also includes a combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
  • perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils (for example Thyme oil), and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.
  • perfuming ingredients which are commonly used in perfume formulations, such as:
  • Aromatic-herbal ingredients eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1 ,0 2 ’ 7 ]undecan-4-one, 1 -methoxy-3-hexanethiol, 2-ethyl-4,4- dimethyl-1 ,3-oxathiane, 2, 2, 7/8, 9/10-tetramethylspiro[5.5]undec-8-en-1 -one, menthol and/or alpha-pinene;
  • Floral ingredients methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4- tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, methyl 2- (methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1 -yl)-3-buten-
  • Fruity ingredients gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2- methyl-4-propyl-1 ,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-1 ,3-dioxolane-2-acetate, diethyl 1 ,4- cyclohexanedicarboxylate, 3-methyl-2-hexen-1 -yl acetate, 1 -[3,3- dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and/or diethyl 1 ,4-cyclohexane dicarboxylate;
  • ingredients e.g. amber, powdery spicy or watery: dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1 -b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(1 ,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H-1 ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- 1 ,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1 -phenylvinyl acetate, 6-methyl-7-oxa-1- thia-4-azaspiro[4.4]nonane and/or 3-(3-isopropyl-1 -phenyl)butanal.
  • ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance.
  • suitable properfumes may include 4-(dodecylthio)-4- (2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1 - cyclohexen-1 -yl)-2-butanone, 3-(dodecylthio)-1 -(2,6,6-trimethyl-3-cyclohexen-1 -y I)- 1 - butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-1 -yl oxo(phenyl)acetate, (Z)-hex-3-en-1
  • the perfuming ingredients may be dissolved in a solvent of current use in the perfume industry.
  • the solvent is preferably not an alcohol.
  • solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins.
  • the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate.
  • the perfume comprises less than 30% of solvent. More preferably the perfume comprises less than 20% and even more preferably less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.
  • Preferred perfuming ingredients are those having a high steric hindrance (bulky materials) and in particular those from one of the following groups:
  • Group 1 perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched Ci to C4 alkyl or alkenyl substituent;
  • Group 2 perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4 to Cs alkyl or alkenyl substituent;
  • Group 3 perfuming ingredients comprising a phenyl ring or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C 5 to Cs alkyl or alkenyl substituent or with at least one phenyl substituent and optionally one or more linear or branched Ci to C3 alkyl or alkenyl substituents;
  • Group 4 perfuming ingredients comprising at least two fused or linked C 5 and/or Cs rings
  • Group 5 perfuming ingredients comprising a camphor-like ring structure
  • Group 6 perfuming ingredients comprising at least one C 7 to C20 ring structure
  • Group 7 perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substitutent;
  • Group 1 2,4-dimethyl-3-cyclohexene-1 -carbaldehyde (origin: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2, 2-dimethyl-6-methylene-1 - cyclohexanecarboxylate (origin: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1 ,8-p-menthadiene-7-ol (origin: Firmenich SA, Geneva, Switzerland), 1 -p-menthene-4-ol, (1 RS,3RS,4SR)-3-p-mentanyl acetate, (1 R,2S,4R)- 4,6,6-trimethyl-bicyclo[3,1 ,1]heptan-2-o
  • Group 3 damascones, 1-(5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one (origin: Firmenich SA, Geneva, Switzerland), (1 'R)-2-[2-(4'-methyl-3'-cyclohexen-1 '- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of 1 -(5,5- dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one and 1 -(3,3-dimethyl-1 -cyclohexen-1 -yl)-4- penten-1 -one (origin: Firmenich SA, Geneva, Switzerland), 1 -(2,6,6-trimethyl-1- cyclohexen-1 -yl)-2-buten-1 -one (origin: Firmenich SA, Geneva, Switzerland), (1 S,1 'R)-[1 - (3',3'-D
  • Group 4 Methyl cedryl ketone (origin: International Flavors and Fragrances, USA), a mixture of (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,0 2 ’ 6 ]dec-3-en-8-yl 2-methylpropanoate and (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,0 2 ’ 6 ]dec-4-en-8-yl 2-methylpropanoate, vetyverol, vetyverone, 1 -(octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone (origin: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10- tetramethyl-1 -oxaspiro[4.5]deca-3,6-diene and the (5RS,9SR,10RS) isomer, 6-ethyl- 2,
  • Group 5 camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5- ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8- tetramethyl-tricyclo[5.3.1.0(1 ,5)]undecane (origin: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1 ,0(2,7)]undecan-4- one and 10-ethylidene-3-oxatricyclo[6.2.1 ,0 2 ’ 7 ]undecan-4-one (origin: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (origin: Firmenich SA, Geneva,
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75.
  • the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols.
  • the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
  • the oil phase comprises:
  • a density balancing material having a density greater than 1 .07 g/cm 3 .
  • “High impact perfume raw materials” should be understood as perfume raw materials having a LogT ⁇ -4.
  • the odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass.
  • the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
  • a “density balancing material’ should be understood as a material having a density greater than 1 .07 g/cm 3 and having preferably low or no odor.
  • the odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GC”). Specifically, the gas chromatograph is calibrated to determine the exact volume of the perfume oil ingredient injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chainlength distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of the perfuming compound. To determine the threshold concentration, solutions are delivered to the sniff port at the back-calculated concentration.
  • GC gas chromatograph
  • a panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average across all panelists determines the odor threshold concentration of the perfuming compound. The determination of odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September, 2008, pages 54-61 .
  • the high impact perfume raw materials having a Log T ⁇ - 4 are selected from the group consisting of (+-)-1 -methoxy-3-hexanethiol, 4-(4-hydroxy-1 - phenyl)-2-butanone, 2-methoxy-4-(1 -propenyl)-1 -phenyl acetate, pyrazobutyle, 3- propylphenol, 1-(3-methyl-1 -benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1 - (3,3/5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one , 1 -(5,5-dimethyl-1 -cyclohexen-1 -y l)-4- penten-1 -one, a mixture comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl- benzo[b]furan-2-one and (3SR,3a
  • perfume raw materials having a Log T ⁇ -4 are chosen in the group consisting of aldehydes, ketones, alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof.
  • perfume raw materials having a Log T ⁇ -4 comprise at least one compound chosen in the group consisting of alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof, preferably in amount comprised between 20 and 70% by weight based on the total weight of the perfume raw materials having a Log T ⁇ - 4.
  • perfume raw materials having a Log T ⁇ -4 comprise between 20 and 70% by weight of aldehydes, ketones, and mixtures thereof based on the total weight of the perfume raw materials having a Log T ⁇ -4.
  • the remaining perfume raw materials contained in the oil phase may have therefore a Log T>-4.
  • the perfume raw materials having a Log T>-4 are chosen in the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+- )-6/8- sec-butylquinoline, (+-)-3-(1 ,3-benzodioxol-5-yl)-2-methylpropanal, verdyl propionate, 1 - (octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-1 -ethanone, methyl 2-((1 RS,2RS)-3-oxo-2- pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1 - carbaldehyde, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, tetrahydro-4-methyl
  • the perfume formulation comprises 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation),
  • a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all of the following characteristics: o at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a log P above 3, preferably above 3.5, o at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of Bulky materials of groups 1 to 6, preferably 3 to 6 as defined previously and o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high impact perfume materials having a Log T ⁇ -4 as defined previously, optionally, further hydrophobic active ingredients.
  • the perfume comprises 0 to 60 wt.% of a hydrophobic solvent.
  • the hydrophobic solvent is a density balancing material preferably chosen in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.
  • the hydrophobic solvent has Hansen Solubility Parameters compatible with entrapped perfume oil.
  • Hansen solubility parameter refers to a solubility parameter approach proposed by Charles Hansen used to predict polymer solubility and was developed around the basis that the total energy of vaporization of a liquid consists of several individual parts. To calculate the "weighted Hansen solubility parameter” one must combine the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces, and (molecular) hydrogen bonding (electron exchange).
  • the weighted Hansen solubility parameter is calculated as (5D 2 + 5P 2 + 5H 2 ) 05 , wherein 5D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore), 5P is the Hansen polarizability value (also referred to in the following as the dipole moment), and 5H is the Hansen Hydrogenbonding ("h-bonding") value (also referred to in the following as hydrogen bonding).
  • 5D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore)
  • 5P is the Hansen polarizability value (also referred to in the following as the dipole moment)
  • 5H is the Hansen Hydrogenbonding (“h-bonding”) value (also referred to in the following as hydrogen bonding).
  • Euclidean difference in solubility parameter between a fragrance and a solvent is Calculated as (4 (5Dsolvenf6Dfragrance) ⁇ + (5P solvenf6Pfragrance) ⁇ + (dHsolvent-SHfragrance) ⁇ ) ⁇ , in which 6D SO ivent, SPsender, and 5H SO ivent, are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and 5D fr agrance, QPfragrance, and SHfragrance are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the fragrance, respectively.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (5D) from 12 to 20, a dipole moment (5P) from 1 to 8, and a hydrogen bonding (5H) from 2.5 to 11 .
  • Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (5D) from 12 to 20, a dipole moment (5P) from 1 to 8, and a hydrogen bonding (5H) from 2.5 to 11 .
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (5D) from 12 to 20, preferably from 14 to 20, a dipole moment (5P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (5H) from 2.5 to 11 , preferably from 4 to 11 .
  • 5D atomic dispersion force
  • P dipole moment
  • H hydrogen bonding
  • At least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least of 98% of the perfume oil has at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (5D) from 12 to 20, a dipole moment (5P) from 1 to 8, and a hydrogen bonding (5H) from 2.5 to 11 .
  • 5D atomic dispersion force
  • P dipole moment
  • H hydrogen bonding
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (5D) from 12 to 20, preferably from 14 to 20, a dipole moment (5P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (5H) from 2.5 to 11 , preferably from 4 to 11 .
  • the perfuming formulation comprises a fragrance modulator (that can be used in addition to the hydrophobic solvent when present or as substitution of the hydrophobic solvent when there is no hydrophobic solvent).
  • the fragrance modulator is defined as a fragrance material with i. a vapor pressure of less than 0.0008 Torr at 22°C;
  • a clogP of 3.5 and higher, preferably 4.0 and higher and more preferably 4.5 ill. at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force from 12 to 20, a dipole moment from 1 to 7, and a hydrogen bonding from 2.5 to 11 , iv. at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force from 14 to 20, a dipole moment from 1 to 8, and a hydrogen bonding from 4 to 11 , when in solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C.
  • the following ingredients can be listed as modulators but the list in not limited to the following materials: alcohol C12, oxacyclohexadec-12/13-en-2-one, 3- [(2',2',3'-trimethyl-3'-cyclopenten-T-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4- cyclopentadecen-1 -one, cyclopentadecanone, (8Z)-oxacycloheptadec-8-en-2-one, 2-[5- (tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, muguet aldehyde, 1 ,5,8-trimethyl-13-oxabicyclo[10.1 .0]trideca-4,8-diene, (+-)-4,6,6,7,8,8- hexamethyl-1 ,3,4,6,7
  • biocide refers to a chemical substance capable of killing living organisms (e.g. microorganisms) or reducing or preventing their growth and/or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and in industry where they prevent the fouling of, for example, water, agricultural products including seed, and oil pipelines.
  • a biocide can be a pesticide, including a fungicide, herbicide, insecticide, algicide, molluscicide, miticide and rodenticide; and/or an antimicrobial such as a germicide, antibiotic, antibacterial, antiviral, antifungal, antiprotozoal and/or antiparasite.
  • a "pest control agent” indicates a substance that serves to repel or attract pests, to decrease, inhibit or promote their growth, development or their activity.
  • Pests refer to any living organism, whether animal, plant or fungus, which is invasive or troublesome to plants or animals, pests include insects notably arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.
  • the hydrophobic material is free of any active ingredient (such as perfume).
  • it comprises, preferably consists of hydrophobic solvents, preferably chosen in the group consisting of isopropyl myristate, tryglycerides (e.g.
  • hydrophilic solvents preferably chosen in the group consisting of 1 ,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1 ,2-propanediol), 1 ,3-propanediol, dipropylene glycol, glycerol,
  • the hydrophobic material is used in an amount comprises between 0.0001% w/w and 70% w/w, preferably between 1% w/w and 50%w/w and, more preferably between 5% w/w and 50% w/w, based on the microcapsule.
  • the hydrophobic material is used in an amount comprises between 0.0001% w/w and 70% w/w, preferably between 1% w/w and 50%w/w and, more preferably between 5% w/w and 50% w/w, based on the slurry.
  • flavoring ingredient or “flavor” or the like is understood to define a variety of flavor and fragrance materials of both natural and synthetic origins, including single compounds or mixtures. Specific examples of such components may be found in the literature, e.g. in Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press; synthetic Food Adjuncts, 1947 by M.B. Jacobs, edited by van Nostrand; or Perfume and Flavor Chemicals by S. Arctander 1969, Montclair, N.J. (USA). These substances are well known to the person skilled in the art of flavoring and/or aromatizing foods and consumer products.
  • the flavoring ingredient may be a taste modifier.
  • a "taste modifier” is understood as an active ingredient that operates on a consumer's taste receptors, or provides a sensory characteristic related to mouthfeel (such as body, roundness, or mouth-coating) to a product being consumed.
  • Non-limiting examples of taste modifiers include active ingredients that enhance, modify or impart saltiness, fattiness, umami, kokumi, heat sensation or cooling sensation, sweetness, acidity, tingling, bitterness or sourness.
  • the flavoring ingredients can be a complex flavor emulating certain organoleptic characteristics, such as sweet and savory tonalities as for example in chicken, beef, pork or shrimp flavor.
  • step (iv)) the second phase containing the melted wax and the hydrophobic material is mixed to obtain a homogeneous solution.
  • this mixing step is carried out by using a stirring device type IKA (mechanical mixing) with a stirring mobile type sawtooth stirrer or 4 pitched blades. It should be understood that the stirring device in step iv) is set in height to not reach the first phase (dispersing phase).
  • step (v) the second phase in emulsified into the first phase to obtain a two phases dispersion, preferably an oil-in-water emulsion.
  • this mixing step is carried out by any well-known techniques such as high-speed mechanical disperser or ultrasonic dispersers.
  • the emulsion is cooled at a temperature below the melting point of the wax to obtain a microcapsule slurry.
  • the cooling step is carried out by any well-known techniques. A rapid cooling is preferred.
  • active cooling is performed in the reactor, for example by circulating a cooling fluid in the jacket of the reactor or with another dedicated heat exchanger device.
  • the cooling occurs passively.
  • the process comprises a further step of removing water for the slurry (i.e a drying step).
  • any drying method known to a skilled person in the art can be used; in particular the slurry may be spray-dried preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans or cellulose derivatives to provide microcapsules in a powder form.
  • a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans or cellulose derivatives to provide microcapsules in a powder form.
  • Alternative drying methods can be used including lyophilization, fluidized bed drying, and powder blending with a desiccant.
  • Microcapsule powder may also comprise free perfume.
  • Another object of the invention is a microcapsule slurry or a microcapsule powder obtainable by the process disclosed above.
  • the microcapsule has a hardness of the microcapsule above 2000g, preferably above 6500g.
  • the hardness of the microcapsules can be determined by mechanical testing using an instrument allowing to move a probe along a vertical axis while measuring the force exerted on a probe.
  • a standard method is ASTM method D937-92 (published by ASTM International, Pennsylvania, USA).
  • the microcapsules provide stability against forces or thermodynamic conditions experienced during industrial processing and storage conditions, including mechanical processing and high moisture environment.
  • the microcapsules provide stability against mechanical processing of food products preparation and high moisture environment of the food products.
  • the microcapsules provide release under heat. According to an embodiment, the microcapsules provide long lasting release by diffusion. According to an embodiment, the microcapsules provide physical barrier against leaking in high moisture environment.
  • the microcapsules provide stability against high concentration of surfactant.
  • the microcapsules provide stability in body care and home products made of a high concentration of surfactant such as detergent, softener, shampoo and conditioner.
  • the microcapsule has a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301 F.
  • the oil preferably perfume oil
  • OECD301 F is a standard test method on the biodegradability from the Organization of Economic Co-operation and Development.
  • microcapsules according to the invention comprise an outer coating material selected from the group consisting of a polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724) and mixtures thereof to form an outer coating to the microcapsule.
  • Polysaccharide polymers are well known to a person skilled in the art.
  • Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose, pectin and mixtures thereof.
  • the coating consists of a cationic coating.
  • Cationic polymers are also well known to a person skilled in the art.
  • Preferred cationic polymers have cationic charge densities of at least 0.5 meq/g, more preferably at least about 1 .5 meq/g, but also preferably less than about 7 meq/g, more preferably less than about 6.2 meq/g.
  • the cationic charge density of the cationic polymers may be determined by the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for Nitrogen determination.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto.
  • the weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 2M Dalton.
  • copolymers shall be selected from the group consisting of polyquaternium-5, polyquaternium- 6, polyquaternium-7, polyquaterniumI O, polyquaternium-11 , polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
  • Salcare®SC60 cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF
  • Luviquat® such as the PQ 11 N, FC 550 or Style (polyquaternium-11 to 68 or quaternized copolymers of vinylpyrrolidone origin: BASF), or also the Jaguar® (C13S or C17, origin Rhodia).
  • an amount of polymer described above comprised between about 0% and 5% w/w, or even between about 0.1% and 2% w/w, percentage being expressed on a w/w basis relative to the total weight of the slurry. It is clearly understood by a person skilled in the art that only part of said added polymers will be incorporated into/deposited on the microcapsule shell.
  • the outer coating is applied using a fluidized bed coating process, or a liquid/powder blending process.
  • Another object of the invention is a consumer product comprising the microcapsules or microcapsule slurry of the invention.
  • a consumer product comprising the microcapsules or microcapsule slurry of the invention.
  • a product is a flavored or fragranced product.
  • the present disclosure provides a flavored article comprising the microcapsules or microcapsule slurry according to an aspect presented herein.
  • the flavored article is selected from the group consisting of: protein powders, protein drinks, protein bars, meat analogues, seefood analogues and savory goods.
  • Meat analogues can include pork analogues, venison analogues, beef analogues, veal analogues, rabbit analogues, sausage analogues, deli meat analogues, ham analogues, salami analogues, pepperoni analogues, chicken analogues, turkey analogues, goose analogues, pheasant analogues, pigeon analogues, whale analogues, lamb analogues, goat analogues, donkey analogues, and squirrel analogues.
  • Seafood analogues can include fish analogues, scallop analogues, shrimp analogues, crabmeat analogues, shellfish analogues, clam analogues, squid analogues, conch analogues, and sea pineapple analogues.
  • the dry particles may easily be added thereto by dry-mixing.
  • Typical flavored articles are selected from the group consisting of an instant soup or sauce, a breakfast cereal, a powdered milk, a baby food, a powdered drink, a powdered chocolate drink, a spread, a powdered cereal drink, a chewing gum, an effervescent tablet, a cereal bar, and a chocolate bar.
  • the powdered foods or drinks may be intended to be consumed after reconstitution of the product with water, milk and/or a juice, or another aqueous liquid.
  • the dry particles provided herein may be suitable for conveying flavors to beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candy, chewing gum and other food products.
  • Beverages include, without limitation, carbonated soft drinks, including cola, lemonlime, root beer, heavy citrus (“dew type”), fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and cordials; coffee and coffee-based drinks, coffee substitutes and cereal-based beverages; teas, including dry mix products as well as ready-to-drink teas (herbal and tealeaf based); fruit and vegetable juices and juice flavored beverages as well as juice drinks, nectars, concentrates, punches and “ades”; sweetened and flavored waters, both carbonated and still; sport/energy/health drinks; alcoholic beverages plus alcohol-free and other low-alcohol products including beer and malt beverages, cider, and wines (still, sparkling, fortified wines and wine coolers); other beverages processed with heating (infusions, pasteurization, ultra-high temperature, ohmic heating or commercial aseptic sterilization) and hot-filled packaging; and cold-filled products made through filtration or other preservation techniques.
  • Fluid dairy products include, without limitation, non-frozen, partially frozen and frozen fluid dairy products such as, for example, milks, ice creams, sorbets and yogurts.
  • Condiments include, without limitation, ketchup, mayonnaise, salad dressing, Worcestershire sauce, fruit-flavored sauce, chocolate sauce, tomato sauce, chili sauce, and mustard.
  • Baked goods include, without limitation, cakes, cookies, pastries, breads, donuts and the like.
  • Bakery fillings include, without limitation, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold make-up fillings and nonfat to full-fat fillings.
  • composition of the invention can be of particular interest in the following examples of products:
  • Baked goods e.g. bread, dry biscuits, cakes, other baked goods
  • Cereal products e.g. breakfast cereals, pre-cooked ready-made rice products, rice flour products, millet and sorghum products, raw or pre-cooked noodles and pasta products
  • Milk products e.g. fresh cheese, soft cheese, hard cheese, milk drinks, whey, butter, partially or wholly hydrolysed milk protein-containing products, fermented milk products, condensed milk and analogues
  • Dairy based products e.g. fruit or flavoured yoghurt, ice cream, fruit ices, frozen desserts
  • Dairy analogues (imitation dairy products) containing non-dairy ingredients (plantbased proteins, vegetable fats),
  • Confectionary products e.g. chewing gum, hard and soft candy
  • Products based on fat and oil or emulsions thereof e.g. mayonnaise, spreads, margarines, shortenings, remoulade, dressings, spice preparations
  • mayonnaise e.g. mayonnaise, spreads, margarines, shortenings, remoulade, dressings, spice preparations
  • Products made of soya protein or other soya bean fractions e.g. soya milk and products made therefrom, soya lecithin-containing preparations, fermented products such as tofu or tempeh or products manufactured therefrom, soya sauces
  • soya protein or other soya bean fractions e.g. soya milk and products made therefrom, soya lecithin-containing preparations, fermented products such as tofu or tempeh or products manufactured therefrom, soya sauces
  • Vegetable preparations e.g. ketchup, sauces, processed and reconstituted vegetables, dried vegetables, deep frozen vegetables, pre-cooked vegetables, vegetables pickled in vinegar, vegetable concentrates or pastes, cooked vegetables, potato preparations
  • Spices or spice preparations e.g. mustard preparations, horseradish preparations
  • spice mixtures e.g., pepper mixtures, horseradish preparations
  • seasonings which are used, for example, in the field of snacks.
  • Snack articles e.g. baked or fried potato crisps or potato dough products, bread dough products, extrudates based on maize, rice or ground nuts
  • Ready dishes e.g. instant noodles, rice, pasta, pizza, tortillas, wraps
  • soups and broths e.g. stock, savory cube, dried soups, instant soups, pre-cooked soups, retorted soups
  • sauces instant sauces, dried sauces, ready-made sauces, gravies, sweet sauces
  • Extended meat products e.g. meat patties, sausages, chili, Salisbury steaks, pizza toppings, meatballs, ground meat, bolognas, chicken nuggets, pork frankfurters, beef).
  • the flavored consumer product is preferably chosen in the group consisting of meat- and/or fish-based food or analogue including those of the burger, nugget or filet type, dairy analogue and dairy product including fermented products, baked good, cereal, spices and seasonings, sauces, dressings, marinades, confectionery products, spreads, or nutritional product.
  • microcapsules of the invention can be used in combination with active ingredients.
  • An object of the invention is therefore a composition comprising:
  • an active ingredient preferably chosen in the group consisting of a cosmetic ingredient, skin caring ingredient, perfume ingredient, flavor ingredient, malodour counteracting ingredient, bactericide ingredient, fungicide ingredient, pharmaceutical or agrochemical ingredient, a sanitizing ingredient, an insect repellent or attractant, and mixtures thereof.
  • the capsules of the invention show a good performance in terms of stability in challenging medium.
  • Another object of the present invention is a perfuming composition
  • a perfuming composition comprising:
  • an emulsifying system i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
  • a solvent and a surfactant system or a solvent commonly used in perfumery.
  • a detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
  • solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-1 -ethanol or ethyl citrate, which are the most commonly used.
  • compositions which comprise both a perfumery carrier and a perfumery co-ingredient can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • perfumery co- ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as defined above.
  • perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
  • Co-ingredients may be chosen in the group consisting of 4- (dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6- trimethyl- 1 -cyclohexen-1 -yl)-2-butanone, trans-3-(dodecylthio)-1 -(2,6,6-trimethyl-3- cyclohexen-1 -yl)-1 -butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1 -yl oxo(phenyl)acetate, (Z)-hex-3-en-1 -yl oxo(phenyl)acetate, 3,7- dimethyl-2,6-octadien-1-y
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
  • the perfuming composition according to the invention comprises between 0.01 and 30 % by weight of microcapsules as defined above.
  • microcapsules can advantageously be used in many application fields and used in consumer products.
  • Microcapsules can be used in liquid form applicable to liquid consumer products as well as in powder form, applicable to powder consumer products.
  • the consumer product as defined above is liquid and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a microcapsule slurry or microcapsules as defined above, d) optionally non-encapsulated perfume.
  • the consumer product as defined above is in a powder form and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) a microcapsule powder as defined above. c) optionally perfume powder that is different from the microcapsules defined above.
  • microcapsules including a perfume oil the products of the invention, can in particular be of used in perfumed consumer products such as product belonging to fine fragrance or “functional” perfumery.
  • Functional perfumery includes in particular personal-care products including hair-care, body cleansing, skin care, hygiene-care as well as home-care products including laundry care, surface care and air care.
  • Another object of the present invention consists of a perfumed consumer product comprising as a perfuming ingredient, the microcapsules defined above or a perfuming composition as defined above.
  • the perfume element of said consumer product can be a combination of perfume microcapsules as defined above and free or non-encapsulated perfume, as well as other types of perfume microcapsules than those here-disclosed.
  • liquid consumer product comprising: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a perfuming composition as defined above is another object of the invention.
  • inventions microcapsules can therefore be added as such or as part of an invention’s perfuming composition in a perfumed consumer product.
  • perfumed consumer product it is meant a consumer product which is expected to deliver among different benefits a perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, paper, or home surface) or in the air (air-freshener, deodorizer etc.).
  • a perfumed consumer product according to the invention is a manufactured product which comprises a functional formulation also referred to as “base”, together with benefit agents, among which an effective amount of microcapsules according to the invention.
  • the perfumed consumer product is preferably chosen in the group consisting of a home care product or a personal care product, including laundry dryer sheets, laundry detergents (powdered) cosmetic cream, skin lotions, sunscreen, toothpaste and other oral care products, soap bars, lipstick, solid or roll-on deodorant sticks, and textile products including face masks.
  • a home care product or a personal care product including laundry dryer sheets, laundry detergents (powdered) cosmetic cream, skin lotions, sunscreen, toothpaste and other oral care products, soap bars, lipstick, solid or roll-on deodorant sticks, and textile products including face masks.
  • Non-limiting examples of suitable perfumed consumer products can be a perfume, such as a fine perfume, a cologne, an after-shave lotion, a body-splash; a fabric care product, such as a liquid or solid detergent, tablets and unit dose (single or multi-chambers), a fabric softener, a dryer sheet, a fabric refresher, an ironing water, or a bleach; a personal-care product, such as a hair-care product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skin-care product (e.g.
  • a hair-care product e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray
  • a cosmetic preparation e.g. a vanishing cream, body lotion or a deodorant or antiperspirant
  • a skin-care product e.g.
  • a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product
  • an air care product such as an air freshener or a “ready to use” powdered air freshener
  • a home care product such all-purpose cleaners, liquid or power or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces, for example sprays & wipes intended for the treatment I refreshment of textiles or hard surfaces (floors, tiles, stone-floors etc.); a hygiene product such as sanitary napkins, diapers, toilet paper.
  • Another object of the invention is a consumer product comprising: - a personal care active base, and microcapsules or microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a personal care composition.
  • the personal care active bases in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
  • the personal care composition is preferably chosen in the group consisting of a hair-care product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skincare product (e.g.
  • Another object of the invention is a consumer product comprising: a home care or a fabric care active base, and microcapsules or microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a home care or a fabric care composition.
  • the consumer product comprises from 0.1 to 15 wt%, more preferably between 0.2 and 5 wt% of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product.
  • concentrations may be adapted according to the benefit effect desired in each product.
  • An object of the invention is a consumer product, preferably a home care or a fabric care consumer product comprising the microcapsules or the microcapsule slurry as defined above, wherein the consumer product has a pH less than 7.
  • An object of the invention is a consumer product, preferably a home care or a fabric care consumer product comprising the microcapsules or the microcapsule slurry as defined above, wherein the consumer product has a pH equals or greater than 7.
  • active base For liquid consumer product mentioned below, by “active base”, it should be understood that the active base includes active materials (typically including surfactants) and water.
  • active base includes active materials (typically including surfactants) and auxiliary agents (such as bleaching agents, buffering agent; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, antifoaming, sud suppressing agents; dyes, fillers, and mixtures thereof).
  • active materials typically including surfactants
  • auxiliary agents such as bleaching agents, buffering agent; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, antifoaming, sud suppressing agents; dyes, fillers, and mixtures thereof.
  • An object of the invention is a consumer product in the form of a fabric softener composition comprising:
  • a fabric softener active base preferably comprising at least one active material chosen in the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquat (HEQ), TEAQ (triethanolamine quat), silicones and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
  • An object of the invention is a consumer product in the form of a liquid detergent composition comprising:
  • liquid detergent active base preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
  • anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol s
  • microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
  • An object of the invention is a consumer product in the form of a solid detergent composition comprising:
  • a solid detergent active base preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
  • anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol
  • microcapsule powder or microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
  • An object of the invention is a consumer product in the form of a shampoo or a shower gel composition comprising:
  • a shampoo or a shower gel active base preferably comprising at least one active material chosen in the group consisting of sodium alkylether sulfate, ammonium alkylether sulfates, alkylamphoacetate, cocamidopropyl betaine, cocamide MEA, alkylglucosides and aminoacid based surfactants and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
  • microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
  • An object of the invention is a consumer product in the form of a rinse-off conditioner composition
  • a rinse-off conditioner active base preferably comprising at least one active material chosen in the group consisting of cetyltrimonium chloride, stearyl trimonium chloride, benzalkonium chloride, behentrimonium chloride and mixture thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
  • An object of the invention is a consumer product in the form of a solid scent booster composition comprising:
  • a solid carrier preferably chosen in the group consisting of urea, sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, saccharides such as sucrose, mono-, di-, and polysaccharides and derivatives such as starch, cellulose, methyl cellulose, ethyl cellulose, propyl cellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PEG, PVP, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof,
  • microcapsule slurry or microcapsules as defined above in a powdered form, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
  • An object of the invention is a consumer product in the form of a liquid scent booster composition comprising:
  • a surfactant system essentially consisting of one or more than one non-ionic surfactant, wherein the surfactant system has a mean HLB between 10 and 14, preferably chosen in the group consisting of ethoxylated aliphatic alcohols, POE/PPG (polyoxyethylene and polyoxypropylene) ethers, mono and polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxylesters, alkyl polyglucosides, amine oxides and combinations thereof; a linker chosen in the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxyl carboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactant having an HLB less than 10 and mixtures thereof, and a microcapsule slurry or microcapsules as defined above, in the form of a slurry, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 w
  • An object of the invention is a consumer product in the form of an oxidative hair coloring composition
  • an oxidizing phase comprising an oxidizing agent and an alkaline phase comprising an alkakine agent, a dye precursor and a coupling compound; wherein said dye precursor and said coupling compound form an oxidative hair dye in the presence of the oxidizing agent, preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
  • the consumer product is in the form of a perfuming composition
  • a perfuming composition comprising:
  • microcapsule slurry or microcapsules as defined previously,
  • a flavor composition B (chicken or beef flavor) were added in the reactor, and a dissolver stirrer (R 1303 Dissolver stirrer from IKA) was now placed in the reactor inside the upper oily phase consisting of the melted wax/flavor mixture (second phase), and set in rotation at a low speed of 150rpm to first homogenize the flavor/melted (liquid) wax mixture by itself during 2 minutes.
  • the stirrer was lowered to now be located in a location ensuring intensive mixing in the whole reactor, and the speed was increased to 1500 rpm to emulsify the first and second phases.
  • This procedure allows therefore a one-pot process providing first a homogeneous mixture of wax and flavor, followed by formation of droplets of said mixture by shearing, all in one process.
  • Microcapsules B1 The same protocol as described in Example 1 was used except that Candelilla wax was used instead of rice bran wax.
  • Microcapsules B were observed by scanning electron microscopy revealing spherical to ellipsoid particles with longest diameters between 1 and 100 micrometers (see Figure 1 ).
  • Microcapsules B2 The same protocol as described in Example 1 was used except that Candelilla wax was used instead of rice bran wax and wherein flavor has been replaced by a perfume oil.
  • Microcapsules C The same protocol as described in Example 1 was used except that beeswax was used instead of rice bran wax.
  • Microcapsules B2 were blended into a cosmetic skin cream (see composition below) at a concentration of 5%w/w.
  • Microcapsules B2 were blended into a shampoo composition (see composition below) at a concentration of 5%w/w.
  • Soap bar A soap bar composition including microcapsules B2 was prepared at a concentration of 7.5% w/w.
  • Fabric softener Microcapsules B2 were blended into a fabric softener composition (see composition below) at a concentration of 20%w/w.
  • Microcapsules B2 were blended into a liquid detergent composition (see composition below) at a concentration of 10%w/w.
  • Microcapsules B2 were added to the powdered detergent (see composition below) by powder blending a dry mixture of 90%w/w detergent powder with 10%w/w fragranced wax particles.
  • Microcapsules according to the invention resist typical washing water temperatures below 90°C and therefore provide a way to deliver fragrance to laundry with a longer lasting persistence and higher effective fragrance concentration after the washing process.
  • Microcapsules B2 are dispersed in a rinse-off conditioner base described below to obtain a concentration of encapsulated perfume oil at 0.5%.
  • Antiperspirant roll-on emulsion composition
  • Microcapsules B2 are weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A and B are heated separately to 75°C; Part A is added to Part B under stirring and the mixture is homogenized for 10 min. Then, the mixture is cooled under stirring; and Part C is slowly added when the mixture reached 45°C and Part D when the mixture reached at 35 °C while stirring. Then the mixture is cooled to room temperature.
  • Example 12
  • Microcapsules B2 are weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Microcapsules B2 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • CARBOPOL AQUA SF-1 POLYMER trademark and origin: NOVEON 3) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ
  • KATHON CG trademark and origin: ROHM & HASS
  • the unit dose formulation can be contained in a PVOH (polyvinyl alcohol) film.
  • Meat analogue products 0.25%w/w of microcapsules as prepared in example 1 containing 21 %w/w chicken flavor were added to a mixture to form vegan chicken fillet analogues.
  • the nuggets were treated by standard steamer treatment, stored, and prepared in a frying pan for degustation. In parallel, the same nuggets were prepared but with free flavor instead.
  • a trained panel observed far stronger flavor release compared to iso-load free flavor.

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Abstract

The present invention relates to a new process for the preparation of microcapsules. Microcapsules are also an object of the invention. Consumer products comprising said microcapsules, in particular perfumed consumer products or flavoured consumer products are also part of the invention.

Description

WAX-BASED MICROCAPSULES
Technical Field
The present invention relates to a new process for the preparation of microcapsules. Microcapsules are also an object of the invention. Consumer products comprising said microcapsules, in particular perfumed consumer products or flavoured consumer products are also part of the invention.
Background of the Invention
One of the problems faced by the perfume and flavour industry lies in the relatively rapid loss of olfactive benefit provided by active compounds due to their volatility. The encapsulation of those active substances provides at the same time a protection of the ingredients there-encapsulated against “aggressions” such as oxidation or moisture and allows, on the other hand, a certain control of the kinetics of flavour or fragrance release to induce sensory effects through sequential release.
Polyurea and polyurethane-based microcapsule slurry are widely used for example in perfumery industry for instance as they provide a long lasting pleasant olfactory effect after their applications on different substrates. Those microcapsules have been widely disclosed in the prior art.
Wax-based microcapsules are also known. However, the wax is a material hard to handle especially as the wax needs to be heated above its melting point and the crystallization needs to be avoided during the preparation of the microcapsules. This issue becomes more critical and difficult to handle at an industrialisation scale.
Despite those prior disclosures, there is still a need to provide new microcapsules while not compromising on their performance, in particular in terms of stability in a consumer product, as well as in delivering a good performance in terms of hydrophobic material delivery.
The present invention is proposing a solution to the above-mentioned problem by providing microcapsules comprising hydrophobic material entrapped in a wax matrix. Furthermore, the present invention provides a simple and cost-effective process for preparing wax-based microcapsules.
Summary of the Invention
The present invention solves the above-mentioned problems by providing new microcapsules encapsulated hydrophobic material, for example perfume or flavour, in a wax matrix and a new process for preparing said microcapsules. In particular, the presence of the wax retains the hydrophobic material (for example perfume or flavor) until the final application on different substrates (e.g. on textiles, skin or hair). Furthermore, with the process disclosed in the present invention, there is no need to handle the melted phase of the wax and crystallization of the wax is therefore prevented.
A first object of the invention is therefore a process for preparing a microcapsule slurry, wherein it comprises the steps of:
(i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
(ii) Adding a wax and optionally a hydrophobic material on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax,
(iii) Adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii), wherein the melted wax and the hydrophobic active ingredient form a second phase,
(iv) Mixing the second phase to obtain a homogeneous solution,
(v) Emulsifying the second phase into the first phase to obtain an emulsion,
(vi) Cooling the emulsion at a temperature below the melting point of the wax to obtain a microcapsule slurry, wherein at least steps (ii), (iii), (iv) and (v) are carried out at a temperature greater than the melting point of the wax.
Another object of the invention is a microcapsule obtainable according to the process disclosed above.
In other aspects, the present invention relates to a consumer product in the form of a perfumed consumer product or a flavored consumer product.
Description of the figures
Figure 1 represents a SEM image of the microcapsules of the present invention.
Detailed description of the invention
Unless stated otherwise, percentages (%) are meant to designate a percentage by weight of a composition.
By “hydrophobic material”, it is meant any hydrophobic material - single material or a mixture of materials - which forms a two-phase dispersion when mixed with water.
By “ingredient”, it is meant a single compound or a combination of ingredients. By “perfume or flavour oil”, it is meant a single perfuming or flavouring compound or a mixture of several perfuming or flavouring compounds.
By “consumer product” or “end-product” it is meant a manufactured product ready to be distributed, sold and used by a consumer.
A “microcapsule”, or the similar, in the present invention it is meant microcapsules that are in a matrix form and have preferably a particle size distribution in the micron range (e.g. a mean diameter (Dv(50) comprised between about 0.1 and 500 microns, preferably between 1 and 100 microns.
According to the invention, the matrix material comprises a wax and the microcapsule has to entrap preferably at least 5%, more preferably at least 10%, even more preferably at least 20 wt.%, even more preferably at least 30 wt.%, even more preferably at least 35 wt.% of the hydrophobic material, based on the total weight of the microcapsule.
By “microcapsule slurry”, it is meant microcapsule(s) that is (are) dispersed in a liquid. According to an embodiment, the slurry is an aqueous slurry, i.e the microcapsule(s) is (are) dispersed in an aqueous phase.
For the sake of clarity, by the expression “dispersion” in the present invention it is meant a system in which particles, aggregates, precipitates, complexes and/or emulsion droplets are dispersed in a continuous phase of a different composition and it specifically includes a suspension or an emulsion. “Dispersion” according to the invention can encompass two-phases dispersion.
The term "emulsion", as used herein, denotes a mixture of two or more liquids that are normally immiscible (i.e. not mixable). In an emulsion, one liquid (the dispersed phase) is dispersed in the other (the continuous phase). In the present invention, it is described an oilin water emulsions comprising a continuous hydrophilic phase, preferably comprising water, in which the hydrophobic phase is dispersed.
The term “fat” used in the present invention refers to lipid components that are solid or in the form of a paste at room temperature (typically between 20 and 25°C) whereas the term “oil” used in the present invention refers to lipid components that are liquid at room temperature. Fat has typically a melting temperature equals or less than 35°C.
The term “wax” used in the present invention refers to lipid components that are solid or in the form of a paste at room temperature (typically between 20 and 25°C) and that have a melting temperature greater than 35°C.
PROCESS FOR PREPARING A MICROCAPSULE SLURRY
A first object of the invention is therefore a process for preparing a microcapsule slurry, wherein it comprises the steps of: (i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
(ii) Adding a wax and optionally a hydrophobic material on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax,
(iii) Adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii), wherein the melted wax and the hydrophobic active ingredient form a second phase,
(iv) Mixing the second phase to obtain a homogeneous solution,
(v) Emulsifying the second phase into the first phase to obtain an emulsion,
(vi) Cooling the emulsion at a temperature below the melting point of the wax to obtain a microcapsule slurry, wherein at least steps (ii), (iii), (iv) and (v) are carried out at a temperature greater than the melting point of the wax.
According to a particular embodiment, no hydrophobic material is added in step ii).
According to an embodiment, the process comprises the steps of:
(i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
(ii) Adding a wax on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax,
(iii) Adding a hydrophobic active material on the melted wax, wherein the melted wax and the hydrophobic active ingredient form a second phase,
(iv) Mixing the second phase to obtain a homogeneous solution,
(v) Emulsifying the second phase into the first phase to obtain an emulsion,
(vi) Cooling the emulsion at a temperature below the melting point of the wax to obtain a microcapsule slurry, wherein at least steps (ii), (iii), (iv) and (v) are carried out at a temperature greater than the melting point of the wax.
The process of the invention is preferably “one pot” process meaning that a single reactor is needed during the process for preparing microcapsules leading to an efficient process for preparing microcapsules (crystallization of the wax is avoided). It is understood therefore that the person skilled in the art is also able to perform the process in ways that do not fall under the description of “one pot”, for example but not limited to pre-mixing some of the phases or materials in additional containers, or by using continuous or semi-continuous processing equipment.
It should be understood that the whole process is preferably carried out in a closed reactor to avoid any evaporation.
In a first step of the process (step (i)), a dispersing phase comprising optionally an emulsifier to form a first phase is prepared.
There is no limitation regarding the nature of the dispersing as long as wax can dissolve.
According to an embodiment, the dispersing phase comprises water. According to an embodiment, the dispersing phase consists of water.
According to an embodiment, at least one part of water (between 1 and 99%) is substituted with alcohol preferably chosen in the group consisting of glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
According to an embodiment, the dispersing phase consists of alcohol preferably chosen in the group consisting of glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
According to an embodiment, the emulsifier comprises plant-based non digestible fibers and plant-based or polysaccharides.
According to an embodiment, the emulsifier comprises a plant-based protein.
According to an embodiment, the emulsifier may also comprise certain proteins of animal origins, including casein or caseinates, whey proteins, or other milk proteins.
According to an embodiment, the emulsifier is a modified starch.
According to an embodiment, the emulsifier is a hydrophobically modified starch including but not limited to octenyl succinic anhydride starch.
According to an embodiment, the emulsifier is gum arabic.
According to an embodiment, the emulsifier comprises a protein, most preferably a plant-based protein.
According to an embodiment, the emulsifier can be chosen in the group consisting of SDS (sodium dodecyl sulfate), phospholipids including lecithin, mono and diglycerides of fatty acids, fatty alcohols, saponins, proteins, polysaccharides and other hydrocolloids, sugar esters, sorbitan esters, polysorbates, polyglycol ethers, modified starch, fibers and mixtures thereof. The proteins used in the present invention can be plant-based protein (including for example lupin, potato, faba, red lentil, soy, pea protein), protein from animal proteins (including for example casein or caseinates, whey proteins, or other milk proteins).
Polysaccharides used in the present invention can be pectins, carrageenans, alginates, cellulose gums, modified cellulose, starches.
The emulsifier is preferably used in an amount comprised between 0.01% and 10%, preferably 0.5 and 2% by weight based on the total weight of the slurry.
A second step of the process consists in adding a wax, preferably a solid wax, and optionally a hydrophobic material on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax (step (ii)).
It should be understood that in step ii), at least one solid wax is added. However, a mixture of waxes can be used, a mixture of wax(s) and oil(s) can be used, a mixture of wax(s) and fat(s) can be used or a mixture of wax(s), oil(s), and fat(s) can be used.
According to an embodiment, the wax is a plant-based wax and/or a wax of animal origins.
The wax can be chosen in the group consisting of rice bran wax, candelilla wax, carnauba wax and sunflower seed wax, beeswax, olive wax, paraffin wax, synthetic wax, berry wax, myrica wax, rapeseed wax, hydrolyzed sunflower wax, orange wax, jasmin wax, tea wax, rose wax, and mixtures thereof.
The wax is typically used in an amount that comprises between 1% w/w and 20% w/w, preferably 1% w/w and 10% w/w, based on the total weight of the slurry.
The wax is typically used in an amount comprises between 30% w/w and 99.9999% w/w, preferably 40% w/w and 99% w/w, more preferably 40% w/w and 95% w/w, based on the total weight of the microcapsules.
The oil can be chosen in the group consisting of sunflower oil, canola oil, olive oil, palm oil, almond oil, MTC (medium chain triglycerides) oil.
The fat can be chosen in the group consisting of cocoa butter, coco fat, animal fat such as beef fat, duck fat, pork fat.
It should be understood that in step ii) no mixing step is carried out (to avoid any emulsification). Indeed, at the end of step (ii), a biphasic system is obtained.
In step ii), the system containing the wax, preferably solid wax, and the dispersing phase is heated greater than the melting point of the wax.
The melting point (Tm) of a material can be easily determined by the person skilled in the art or found in the literature.
The melting point can be measured by differential scanning calorimeter, for example Q2000 (TA Instruments, New Castle, DE, USA. Typically, in step ii), the system is heated at a temperature comprised between 70 and 90°C.
A thirst step of the process consists of adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii) wherein the melted wax and the hydrophobic active ingredient form a second phase (step (iii)).
It should be understood that in step iii), the first phase and the second phase are two separate phases (biphasic system).
Hydrophobic material that can be added in step ii) and/or step iii) can be the same or different.
Hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
A single hydrophobic material or mixture of hydrophobic materials can be used.
The hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
When the hydrophobic material is an active ingredient, it is preferably chosen from the group consisting of flavors, flavor ingredients, perfumes, perfume ingredients, nutraceuticals, cosmetics, pest control agents, biocide actives and mixtures thereof.
According to a particular embodiment, the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents and biocide actives.
According to an embodiment, the hydrophobic material comprises a phase change material (PCM).
According to a particular embodiment, the hydrophobic material comprises a mixture of biocide actives with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, pest control agents.
According to a particular embodiment, the hydrophobic material comprises a mixture of pest control agents with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, biocide actives.
According to a particular embodiment, the hydrophobic material comprises a perfume. According to a particular embodiment, the hydrophobic material consists of a perfume. According to a particular embodiment, the hydrophobic material consists of biocide actives.
According to a particular embodiment, the hydrophobic material consists of pest control agents. By “perfume” (or also “perfume oil”) what is meant here is an ingredient or a composition that is a liquid at about 20°C. According to any one of the above embodiments said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition. As a “perfuming ingredient” it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor. In other words such an ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. For the purpose of the present invention, perfume oil also includes a combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
The nature and type of the perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils (for example Thyme oil), and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.
In particular one may cite perfuming ingredients which are commonly used in perfume formulations, such as:
- Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and/or nonenal;
- Aromatic-herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1 ,02’7]undecan-4-one, 1 -methoxy-3-hexanethiol, 2-ethyl-4,4- dimethyl-1 ,3-oxathiane, 2, 2, 7/8, 9/10-tetramethylspiro[5.5]undec-8-en-1 -one, menthol and/or alpha-pinene;
- Balsamic ingredients: coumarin, ethylvanillin and/or vanillin;
- Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1 -p-menthen-8-yl acetate and/or 1 ,4(8)-p-menthadiene;
Floral ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4- tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, methyl 2- (methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1 -yl)-3-buten-
2-one, (1 E)-1 -(2,6,6-trimethyl-2-cyclohexen-1 -yl)-1 -penten-3-one, 1 -(2,6,6-trimethyl- 1 ,3-cyclohexadien-1 -yl)-2-buten-1 -one, (2E)-1 -(2,6,6-trimethyl-2-cyclohexen-1 -yl)-2- buten-1 -one, (2E)-1 -[2,6,6-trimethyl-3-cyclohexen-1 -yl]-2-buten-1 -one, (2E)-1 -(2,6,6- trimethyl-1 -cyclohexen-1-yl)-2-buten-1 -one, 3-(3,3/1 ,1 -dimethyl-5-indanyl)propanal, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexene-1 -carboxylate, 3-(4,4- dimethyl-1 -cyclohexen-1 -yl)propanal, hexyl salicylate, 3,7-dimethyl-1 ,6-nonadien-3-ol,
3-(4-isopropylphenyl)-2-methylpropanal, verdyl acetate, geraniol, p-menth-1-en-8-ol,
4-(1 ,1 -dimethylethyl)-1 -cyclohexyle acetate, 1 ,1-dimethyl-2-phenylethyl acetate, 4- cyclohexyl-2-methyl-2-butanol, amyl salicylate , high cis methyl dihydrojasmonate, 3- methyl-5-phenyl-1 -pentanol, verdyl proprionate, geranyl acetate, tetrahydro linalool, cis-7-p-menthanol, propyl (S)-2-(1 ,1 -dimethylpropoxy)propanoate, 2- methoxynaphthalene, 2, 2, 2-trichloro-1 -phenylethyl acetate, 4/3-(4-hydroxy-4- methylpentyl)-3-cyclohexene-1 -carbaldehyde, amylcinnamic aldehyde, 8-decen-5- olide, 4-phenyl-2-butanone, isononyle acetate, 4-(1 , 1 -dimethylethyl)-1 -cyclohexyl acetate, verdyl isobutyrate and/or mixture of methylionones isomers;
Fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2- methyl-4-propyl-1 ,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-1 ,3-dioxolane-2-acetate, diethyl 1 ,4- cyclohexanedicarboxylate, 3-methyl-2-hexen-1 -yl acetate, 1 -[3,3- dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and/or diethyl 1 ,4-cyclohexane dicarboxylate;
Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1 - carbaldehyde, 2-tert-butyl-1 -cyclohexyl acetate, styrallyl acetate, allyl (2- methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1 -ol and/or 1 -(5, 5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one;
Musk ingredients: 1 ,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1 - one, 3-methylcyclopentadecanone, 1 -oxa-12-cyclohexadecen-2-one, 1 -oxa-13- cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1 -one, 2-{(1 S)-1 -[(1 R)-3,3- dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclopentadecen-1 - one, 4,6,6,7,8,8-hexamethyl-1 ,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1 S,1 'R)-2-[1-(3',3'-dimethyl-1 '-cyclohexyl)ethoxy]-2-methylpropyl propanoate, oxacyclohexadecan-2-one and/or (1 S,1 'R)-[1 -(3',3'-dimethyl-1 '- cyclohexyl)ethoxycarbonyl]methyl propanoate; Woody ingredients: 1 -[(1 RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl- 5-[(1 R)-2,2,3-trimethyl-3-cyclopenten-1 -yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane- 2,9'-tricyclo[6.2.1 ,027]undec[4]ene, (l-ethoxyethoxy)cyclododecane, 2,2,9,11- tetramethylspiro[5.5]undec-8-en-1 -yl acetate, 1 -(octahydro-2, 3,8, 8-tetramethyl-2- naphtalenyl)-1 -ethanone, patchouli oil, terpenes fractions of patchouli oil, Clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3- trimethyl-3-cyclopenten-1 -yl)-2-buten-1 -ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3- cyclopentenyl)-3-methylpentan-2-ol, 1 -(2,3,8,8-tetramethyl-1 ,2,3,4,6,7,8,8a- octahydronaphthalen-2-yl)ethan-1-one and/or isobornyl acetate;
Other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1 -b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(1 ,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H-1 ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- 1 ,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1 -phenylvinyl acetate, 6-methyl-7-oxa-1- thia-4-azaspiro[4.4]nonane and/or 3-(3-isopropyl-1 -phenyl)butanal.
It is also understood that said ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance. Non-limiting examples of suitable properfumes may include 4-(dodecylthio)-4- (2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1 - cyclohexen-1 -yl)-2-butanone, 3-(dodecylthio)-1 -(2,6,6-trimethyl-3-cyclohexen-1 -y I)- 1 - butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-1 -yl oxo(phenyl)acetate, (Z)-hex-3-en-1 -yl oxo(phenyl)acetate, 3,7-dimethyl-2,6- octadien-1 -yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1 -yl) succinate, (2-((2- methylundec-1 -en-1 -yl)oxy)ethyl)benzene, 1 -methoxy-4-(3-methyl-4-phenethoxybut-3-en-1 - yl)benzene, (3-methyl-4-phenethoxybut-3-en-1 -yl)benzene, 1 -(((Z)-hex-3-en-1 -yl)oxy)-2- methylundec-1 -ene, (2-((2-methylundec-1 -en-1 -yl)oxy)ethoxy)benzene, 2-methyl-1 -(octan-3- yloxy)undec-1 -ene, 1 -methoxy-4-(1 -phenethoxyprop-1 -en-2-yl)benzene, 1 -methyl-4-(1 - phenethoxyprop-1 -en-2-yl)benzene, 2-(1 -phenethoxyprop-1 -en-2-yl)naphthalene, (2- phenethoxyvinyl)benzene, 2-(1 -((3,7-dimethyloct-6-en-1 -yl)oxy)prop-1 -en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1 -((2-methoxy-2- phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1 -isopropyl- 4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1 -((2- pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2- phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or a mixture thereof.
The perfuming ingredients may be dissolved in a solvent of current use in the perfume industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate. Preferably the perfume comprises less than 30% of solvent. More preferably the perfume comprises less than 20% and even more preferably less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.
Preferred perfuming ingredients are those having a high steric hindrance (bulky materials) and in particular those from one of the following groups:
Group 1 : perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched Ci to C4 alkyl or alkenyl substituent;
Group 2: perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4 to Cs alkyl or alkenyl substituent;
Group 3: perfuming ingredients comprising a phenyl ring or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5 to Cs alkyl or alkenyl substituent or with at least one phenyl substituent and optionally one or more linear or branched Ci to C3 alkyl or alkenyl substituents;
Group 4: perfuming ingredients comprising at least two fused or linked C5 and/or Cs rings; Group 5: perfuming ingredients comprising a camphor-like ring structure;
Group 6: perfuming ingredients comprising at least one C7 to C20 ring structure;
Group 7: perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substitutent;
Examples of ingredients from each of these groups are:
Group 1 : 2,4-dimethyl-3-cyclohexene-1 -carbaldehyde (origin: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2, 2-dimethyl-6-methylene-1 - cyclohexanecarboxylate (origin: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1 ,8-p-menthadiene-7-ol (origin: Firmenich SA, Geneva, Switzerland), 1 -p-menthene-4-ol, (1 RS,3RS,4SR)-3-p-mentanyl acetate, (1 R,2S,4R)- 4,6,6-trimethyl-bicyclo[3,1 ,1]heptan-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (origin: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1 ,4- cyclohexane diethyldicarboxylate (origin: Firmenich SA, Geneva, Switzerland), (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (origin: Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (origin: Firmenich SA, Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1 ,3-dioxane, 2,4,6- trimethyl-3-cyclohexene-1 -carbaldehyde;
Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (origin: Givaudan SA, Vernier, Switzerland), (1 'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-r- yl)-2-buten-1 -ol (origin: Firmenich SA, Geneva, Switzerland), (1 'R,E)-3,3-dimethyl-5- (2',2',3'-trimethyl-3'-cyclopenten-1 '-yl)-4-penten-2-ol (origin: Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone, methyl-cis-3-oxo-2-pentyl-1 -cyclopentane acetate (origin: Firmenich SA, Geneva, Switzerland), 2, 2, 5-trimethyl-5-pentyl-1 -cyclopentanone (origin: Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3- cyclopenten-1 -yl)-4-penten-2-ol (origin: Firmenich SA, Geneva, Switzerland), 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1 -yl)-2-pentanol (origin, Givaudan SA, Vernier, Switzerland);
Group 3: damascones, 1-(5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one (origin: Firmenich SA, Geneva, Switzerland), (1 'R)-2-[2-(4'-methyl-3'-cyclohexen-1 '- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of 1 -(5,5- dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one and 1 -(3,3-dimethyl-1 -cyclohexen-1 -yl)-4- penten-1 -one (origin: Firmenich SA, Geneva, Switzerland), 1 -(2,6,6-trimethyl-1- cyclohexen-1 -yl)-2-buten-1 -one (origin: Firmenich SA, Geneva, Switzerland), (1 S,1 'R)-[1 - (3',3'-Dimethyl-1 '-cyclohexyl)ethoxycarbonyl]methyl propanoate (origin: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1 -cyclohexyl acetate (origin: International Flavors and Fragrances, USA), 1 -(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (origin: Firmenich SA, Geneva, Switzerland), trans-1 -(2,2,6-trimethyl-1 -cyclohexyl)-3-hexanol (origin: Firmenich SA, Geneva, Switzerland), (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1 -yl)-3-buten-2- one, terpenyl isobutyrate, 4-(1 , 1 -dimethylethyl)-1 -cyclohexyl acetate (origin: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, (1 S, 1 'R)-2-[1 -(3',3'-dimethyl-1 '- cyclohexyl) ethoxy]-2-methylpropyl propanoate (origin: Firmenich SA, Geneva, Switzerland), para tert-butylcyclohexanone, menthenethiol, 1 -methyl-4-(4-methyl-3- pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate;
Group 4: Methyl cedryl ketone (origin: International Flavors and Fragrances, USA), a mixture of (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,02’6]dec-3-en-8-yl 2-methylpropanoate and (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,02’6]dec-4-en-8-yl 2-methylpropanoate, vetyverol, vetyverone, 1 -(octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone (origin: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10- tetramethyl-1 -oxaspiro[4.5]deca-3,6-diene and the (5RS,9SR,10RS) isomer, 6-ethyl- 2,10,10-trimethyl- 1 -oxaspiro[4.5]deca-3,6-diene, 1 ,2,3,5,6,7-hexahydro-1 ,1 ,2,3,3- pentamethyl-4-indenone (origin: International Flavors and Fragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1 ,1 -dimethyl-5-indanyl)propanal (origin: Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1 ,0(2,7)]undec-4-ene-9- spiro-2'-oxirane (origin: Firmenich SA, Geneva, Switzerland), 9/10-ethyldiene-3- oxatricyclo[6.2.1 ,0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate (origin: Firmenich SA, Geneva, Switzerland), octalynol, (dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1 -b]furan, origin: Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1 ,0(2,6)]dec-4-en-8-yl acetate as well as tricyclo[5.2.1 ,0(2,6)]dec-3-en-8-yl propanoate and tricyclo[5.2.1 ,0(2,6)]dec-4- en-8-yl propanoate, (+)-(1 S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1 .1]heptane-3-spiro-2'- cyclohexen-4'-one;
Group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5- ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8- tetramethyl-tricyclo[5.3.1.0(1 ,5)]undecane (origin: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1 ,0(2,7)]undecan-4- one and 10-ethylidene-3-oxatricyclo[6.2.1 ,02’7]undecan-4-one (origin: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (origin: Firmenich SA, Geneva, Switzerland);
Group 6: (trimethyl-13-oxabicyclo-[10.1 .0]-trideca-4,8-diene (origin: Firmenich SA, Geneva, Switzerland), 9-hexadecen-16-olide (origin: Firmenich SA, Geneva, Switzerland), pentadecenolide (origin: Firmenich SA, Geneva, Switzerland), 3-methyl-(4/5)- cyclopentadecenone .(origin: Firmenich SA, Geneva, Switzerland), 3- methylcyclopentadecanone (origin: Firmenich SA, Geneva, Switzerland), pentadecanolide (origin: Firmenich SA, Geneva, Switzerland), cyclopentadecanone (origin: Firmenich SA, Geneva, Switzerland), 1-ethoxyethoxy)cyclododecane (origin: Firmenich SA, Geneva, Switzerland), 1 ,4-dioxacycloheptadecane-5, 17-dione, 4,8-cyclododecadien-1 -one;
Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal (origin: Givaudan SA, Vernier, Switzerland), 2, 2, 2-trichloro-1 -phenylethyl acetate.
Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
According to another preferred embodiment, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75. According to a particular embodiment, the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols. Advantageously, the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
According to an embodiment, the oil phase comprises:
25-100wt%, preferably 25-98% of a perfume oil comprising at least 15wt% of high impact perfume raw materials having a Log T<-4, and
0-75wt%, preferably 2-75% of a density balancing material having a density greater than 1 .07 g/cm3.
“High impact perfume raw materials" should be understood as perfume raw materials having a LogT<-4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass. For convenience, the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
A “density balancing material’ should be understood as a material having a density greater than 1 .07 g/cm3 and having preferably low or no odor.
The odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GC”). Specifically, the gas chromatograph is calibrated to determine the exact volume of the perfume oil ingredient injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chainlength distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of the perfuming compound. To determine the threshold concentration, solutions are delivered to the sniff port at the back-calculated concentration. A panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average across all panelists determines the odor threshold concentration of the perfuming compound. The determination of odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September, 2008, pages 54-61 .
The nature of high impact perfume raw materials having a Log T<-4 and density balancing material having a density greater than 1.07 g/cm3 are described in WO2018115250, the content of which are included by reference.
According to an embodiment, the high impact perfume raw materials having a Log T<- 4 are selected from the group consisting of (+-)-1 -methoxy-3-hexanethiol, 4-(4-hydroxy-1 - phenyl)-2-butanone, 2-methoxy-4-(1 -propenyl)-1 -phenyl acetate, pyrazobutyle, 3- propylphenol, 1-(3-methyl-1 -benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1 - (3,3/5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one , 1 -(5,5-dimethyl-1 -cyclohexen-1 -y l)-4- penten-1 -one, a mixture comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl- benzo[b]furan-2-one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[b]furan-2- one, (+-)-1 -(5-ethyl-5-methyl-1 -cyclohexen-1 -yl)-4-penten-1 -one, (1 'S,3'R)-1 -methyl-2- [(r,2',2'-trimethylbicyclo[3.1 .0]hex-3'-yl)methyl]cyclopropyl}methanol, (+-)-3-mercaptohexyl acetate, (2E)-1 -(2 , 6, 6-trimethy I- 1 ,3-cyclohexadien-1 -yl)-2-buten-1 -one, H-methyl-2h-1 ,5- benzodioxepin-3(4H)-one, (2E,6Z)-2,6-nonadien-1 -ol, (4Z)-4-dodecenal, (+-)-4-hydroxy-2,5- dimethyl-3(2H)-furanone, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 3-methylindole, (+-)- perhydro-4alpha,8abeta-dimethyl-4a-naphthalenol, patchoulol, 2-methoxy-4-(1 - propenyl)phenol, mixture comprising (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylene-2-phenyl-2H-pyran, mixture comprising 4-methylene-2- phenyltetrahydro-2H-pyran and (+-)-4-methyl-2-phenyl-3,6-dihydro-2H-pyran, 4-hydroxy-3- methoxybenzaldehyde, nonylenic aldehyde, 2-methoxy-4-propylphenol, 3-methyl-5-phenyl-2- pentenenitrile, 1 -(spiro[4.5]dec-6/7-en-7-yl)-4-penten-1-one(, 2-methoxynaphthalene, (-)- (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1 -b]furan, 5-nonanolide, (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1 -b]furan, 7-isopropyl- 2H,4H-1 ,5-benzodioxepin-3-one, coumarin, 4-methylphenyl isobutyrate, (2E)-1 -(2,6,6- trimethyl- 1 ,3-cyclohexadien-1 -yl)-2-buten-1 -one, beta, 2,2, 3-tetramethyl-delta-methylene-3- cyclopentene-1 -butanol, delta damascene ((2E)-1 -[(1 RS,2SR)-2,6,6-trimethyl-3-cyclohexen- 1 -yl]-2-buten-1 -one), (+-)-3,6-dihydro-4,6-dimethyl-2-phenyl-2h-pyran, anisaldehyde, paracresol, 3-ethoxy-4-hydroxybenzaldehyde, methyl 2-aminobenzoate, ethyl methylphenylglycidate, octalactone gamma, ethyl 3-phenyl-2-propenoate, (-)-(2E)-2-ethyl-4- [(1 R)-2,2,3-trimethyl-3-cyclopenten-1 -yl]-2-buten-1 -ol, paracresyl acetate, dodecalactone, tricyclone, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1 -one, undecalactone, (1 R,4R)-8- mercapto-3-p-menthanone, (3S,3AS,6R,7AR)-3,6-dimethylhexahydro-1 -benzofuran-2(3H)- one, beta ionone, (+-)-6-pentyltetrahydro-2H-pyran-2-one, (3E,5Z)-1 ,3,5-undecatriene, 10- undecenal, (9E)-9-undecenal (9Z)-9-undecenal, (Z)-4-decenal, (+-)-ethyl 2- methylpentanoate, 1 ,2-diallyldisulfane, 2-tridecenenitrile, 3-tridecenenitrile, , (+-)-2-ethyl-4,4- dimethyl-1 ,3-oxathiane, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1 -one, 3-(4-tert- butylphenyl)propanal, allyl (cyclohexyloxy)acetate, methylnaphthylketone, (+-)-(4E)-3-methyl- 4-cyclopentadecen-1 -one, (+-)-5E3-methyl-5-cyclopentadecen-1 -one, cyclopropylmethyl 3- hexenoate, (4E)-4-methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1 -(5-propyl-1 ,3-benzodioxol-2- yl)ethanone, 4-methyl-2-pentylpyridine, (+-)-(E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1 - yl)-3-buten-2-one, (3aRS,5aSR,9aSR,9bRS)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1- b]furan, (2S,5R)-5-methyl-2-(2-propanyl)cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran- 2-one, (+-)-3-(3-isopropyl-1 -phenyl)butanal, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-
(2 , 6, 6-t ri methy I- 1 -cyclohex-2-enyl)pent-1 -en-3-one, indol, 7-propyl-2H,4H-1 ,5- benzodioxepin-3-one, ethyl praline, (4-methylphenoxy)acetaldehyde, ethyl tricyclo[5.2.1 ,0.2’6]decane-2-carboxylate, (+)-(TS,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'- cyclopenten-1 '-yl)-4-penten-2-ol, (4E)-3,3-dimethyl-5-[(1 R)-2,2,3-trimethyl-3-cyclopenten-1 - yl]-4-penten-2-ol, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, methylnonylacetaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropanoate, (E)-4-decenal, (+- )-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1 -yl)-2-buten-1 -ol, (1 R,5R)-4,7,7-trimethyl-6- thiabicyclo[3.2.1]oct-3-ene, (1 R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane, (-)-(3R)- 3,7-dimethyl-1 ,6-octadien-3-ol, (E)-3-phenyl-2-propenenitrile, 4-methoxybenzyl acetate, (E)-
3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1 -yl)-4-penten-2-ol, allyl (2/3- methylbutoxy)acetate, (+-)-(2E)-1 -(2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-buten-1 -one, (1 E)-1 - (2,6,6-trimethyl-1-cyclohexen-1 -yl)-1 -penten-3-one, and mixtures thereof.
According to an embodiment, perfume raw materials having a Log T<-4 are chosen in the group consisting of aldehydes, ketones, alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof.
According to an embodiment, perfume raw materials having a Log T<-4 comprise at least one compound chosen in the group consisting of alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof, preferably in amount comprised between 20 and 70% by weight based on the total weight of the perfume raw materials having a Log T<- 4.
According to an embodiment, perfume raw materials having a Log T<-4 comprise between 20 and 70% by weight of aldehydes, ketones, and mixtures thereof based on the total weight of the perfume raw materials having a Log T<-4.
The remaining perfume raw materials contained in the oil phase may have therefore a Log T>-4.
According to an embodiment, the perfume raw materials having a Log T>-4 are chosen in the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+- )-6/8- sec-butylquinoline, (+-)-3-(1 ,3-benzodioxol-5-yl)-2-methylpropanal, verdyl propionate, 1 - (octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-1 -ethanone, methyl 2-((1 RS,2RS)-3-oxo-2- pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1 - carbaldehyde, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, tetrahydro-4-methyl-2-(2-methyl-1 - propenyl)-2H-pyran, dodecanal, 1 -oxa-12/13-cyclohexadecen-2-one, (+-)-3-(4- isopropylphenyl)-2-methylpropanal, aldehyde C11 , (+-)-2,6-dimethyl-7-octen-2-ol, allyl 3- cyclohexylpropanoate, (Z)-3-hexenyl acetate, 5-methyl-2-(2-propanyl)cyclohexanone, allyl heptanoate, 2-(2-methyl-2-propanyl)cyclohexyl acetate, 1 ,1 -dimethyl-2-phenylethyl butyrate, geranyl acetate, neryl acetate, (+-)-1 -phenylethyl acetate, 1 ,1 -dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutanoate, (2Z)-ethyl 3-hydroxy-2-butenoate, 8-p- menthanol, 8-p-menthanyl acetate, 1-p-menthanyl acetate, (+-)-2-(4-methyl-3-cyclohexen-1 - yl)-2-propanyl acetate, (+-)-2-methylbutyl butanoate, 2-{(1 S)-1 -[(1 R)-3,3- dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3,5,6-trimethyl-3-cyclohexene-1 - carbaldehyde, 2,4,6-trimethyl-3-cyclohexene-1 -carbaldehyde, 2-cyclohexylethyl acetate, octanal, ethyl butanoate, (+-)-(3E)-4-(2,6,6-trimethyl-1/2-cyclohexen-1 -yl)-3-buten-2-one, 1 - [(1 RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, ethyl hexanoate, undecanal, decanal, 2-phenylethyl acetate, (1 S,2S,4S)-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, (1 S,2R,4S)-1 ,7,7- trimethylbicyclo[2.2.1]heptan-2-ol ), (+-)-3,7-dimethyl-3-octanol, 1 -methyl-4-(2- propanylidene)cyclohexene, (+)-(R)-4-(2-methoxypropan-2-yl)-1 -methylcyclohex-1 -ene, verdyl acetate, (3R)-1 -[(1 R,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (3S)-1 -[(1 R,6S)-2,2,6- trimethylcyclohexyl]-3-hexanol, (3R)-1 -[(1 S,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (+)- (1 S,1 'R)-2-[1-(3',3'-dimethyl-1 '-cyclohexyl)ethoxy]-2-methylpropyl propanoate, and mixtures thereof.
According to an embodiment, the perfume formulation comprises 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation),
- 40 to 100 wt.% of a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all of the following characteristics: o at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a log P above 3, preferably above 3.5, o at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of Bulky materials of groups 1 to 6, preferably 3 to 6 as defined previously and o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high impact perfume materials having a Log T < -4 as defined previously, optionally, further hydrophobic active ingredients.
According to a particular embodiment, the perfume comprises 0 to 60 wt.% of a hydrophobic solvent.
According to a particular embodiment, the hydrophobic solvent is a density balancing material preferably chosen in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof. In a particular embodiment, the hydrophobic solvent has Hansen Solubility Parameters compatible with entrapped perfume oil.
The term "Hansen solubility parameter" is understood refers to a solubility parameter approach proposed by Charles Hansen used to predict polymer solubility and was developed around the basis that the total energy of vaporization of a liquid consists of several individual parts. To calculate the "weighted Hansen solubility parameter" one must combine the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces, and (molecular) hydrogen bonding (electron exchange). The weighted Hansen solubility parameter" is calculated as (5D2+ 5P2+ 5H2)05, wherein 5D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore), 5P is the Hansen polarizability value (also referred to in the following as the dipole moment), and 5H is the Hansen Hydrogenbonding ("h-bonding") value (also referred to in the following as hydrogen bonding). For a more detailed description of the parameters and values, see Charles Hansen, The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, Danish Technical Press (Copenhagen, 1967).
Euclidean difference in solubility parameter between a fragrance and a solvent is Calculated as (4 (5Dsolvenf6Dfragrance)^ + (5P solvenf6Pfragrance)^ + (dHsolvent-SHfragrance)^)^, in Which 6DSOivent, SPsoivent, and 5HSOivent, are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and 5Dfragrance, QPfragrance, and SHfragrance are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the fragrance, respectively.
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (5D) from 12 to 20, a dipole moment (5P) from 1 to 8, and a hydrogen bonding (5H) from 2.5 to 11 .
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (5D) from 12 to 20, preferably from 14 to 20, a dipole moment (5P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (5H) from 2.5 to 11 , preferably from 4 to 11 .
In a particular embodiment, at least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least of 98% of the perfume oil has at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (5D) from 12 to 20, a dipole moment (5P) from 1 to 8, and a hydrogen bonding (5H) from 2.5 to 11 .
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (5D) from 12 to 20, preferably from 14 to 20, a dipole moment (5P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (5H) from 2.5 to 11 , preferably from 4 to 11 . According to an embodiment, the perfuming formulation comprises a fragrance modulator (that can be used in addition to the hydrophobic solvent when present or as substitution of the hydrophobic solvent when there is no hydrophobic solvent).
Preferably, the fragrance modulator is defined as a fragrance material with i. a vapor pressure of less than 0.0008 Torr at 22°C;
II. a clogP of 3.5 and higher, preferably 4.0 and higher and more preferably 4.5 ill. at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force from 12 to 20, a dipole moment from 1 to 7, and a hydrogen bonding from 2.5 to 11 , iv. at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force from 14 to 20, a dipole moment from 1 to 8, and a hydrogen bonding from 4 to 11 , when in solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C.
Preferably, as examples the following ingredients can be listed as modulators but the list in not limited to the following materials: alcohol C12, oxacyclohexadec-12/13-en-2-one, 3- [(2',2',3'-trimethyl-3'-cyclopenten-T-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4- cyclopentadecen-1 -one, cyclopentadecanone, (8Z)-oxacycloheptadec-8-en-2-one, 2-[5- (tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, muguet aldehyde, 1 ,5,8-trimethyl-13-oxabicyclo[10.1 .0]trideca-4,8-diene, (+-)-4,6,6,7,8,8- hexamethyl-1 ,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (+)-(1 S,2S,3S,5R)-2,6,6- trimethylspiro[bicyclo[3.1 .1]heptane-3,1 '-cyclohexane]-2'-en-4'-one, oxacyclohexadecan-2- one, 2-{(1 S)-1 -[(1 R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, (+)-(4R,4aS,6R)- 4,4a-dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone, amylcinnamic aldehyde, hexylcinnamic aldehyde, hexyl salicylate, (1 E)-1 -(2,6,6-trimethyl-1 -cyclohexen-1 - yl)-1 ,6-heptadien-3-one, (9Z)-9-cycloheptadecen-1 -one.
The term "biocide" refers to a chemical substance capable of killing living organisms (e.g. microorganisms) or reducing or preventing their growth and/or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and in industry where they prevent the fouling of, for example, water, agricultural products including seed, and oil pipelines. A biocide can be a pesticide, including a fungicide, herbicide, insecticide, algicide, molluscicide, miticide and rodenticide; and/or an antimicrobial such as a germicide, antibiotic, antibacterial, antiviral, antifungal, antiprotozoal and/or antiparasite.
As used herein, a "pest control agent" indicates a substance that serves to repel or attract pests, to decrease, inhibit or promote their growth, development or their activity. Pests refer to any living organism, whether animal, plant or fungus, which is invasive or troublesome to plants or animals, pests include insects notably arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms. According to a particular embodiment, the hydrophobic material is free of any active ingredient (such as perfume). According to this particular embodiment, it comprises, preferably consists of hydrophobic solvents, preferably chosen in the group consisting of isopropyl myristate, tryglycerides (e.g. Neobee® MCT oil, vegetable oils), D-limonene, silicone oil, mineral oil, and mixtures thereof with optionally hydrophilic solvents preferably chosen in the group consisting of 1 ,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1 ,2-propanediol), 1 ,3-propanediol, dipropylene glycol, glycerol, glycol ethers and mixtures thereof.
According to any one of the invention’s embodiments, the hydrophobic material is used in an amount comprises between 0.0001% w/w and 70% w/w, preferably between 1% w/w and 50%w/w and, more preferably between 5% w/w and 50% w/w, based on the microcapsule.
According to any one of the invention’s embodiments, the hydrophobic material is used in an amount comprises between 0.0001% w/w and 70% w/w, preferably between 1% w/w and 50%w/w and, more preferably between 5% w/w and 50% w/w, based on the slurry.
The term "flavoring ingredient" or “flavor” or the like is understood to define a variety of flavor and fragrance materials of both natural and synthetic origins, including single compounds or mixtures. Specific examples of such components may be found in the literature, e.g. in Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press; synthetic Food Adjuncts, 1947 by M.B. Jacobs, edited by van Nostrand; or Perfume and Flavor Chemicals by S. Arctander 1969, Montclair, N.J. (USA). These substances are well known to the person skilled in the art of flavoring and/or aromatizing foods and consumer products.
The flavoring ingredient may be a taste modifier. A "taste modifier" is understood as an active ingredient that operates on a consumer's taste receptors, or provides a sensory characteristic related to mouthfeel (such as body, roundness, or mouth-coating) to a product being consumed. Non-limiting examples of taste modifiers include active ingredients that enhance, modify or impart saltiness, fattiness, umami, kokumi, heat sensation or cooling sensation, sweetness, acidity, tingling, bitterness or sourness.
The flavoring ingredients can be a complex flavor emulating certain organoleptic characteristics, such as sweet and savory tonalities as for example in chicken, beef, pork or shrimp flavor.
In a further step (step (iv)), the second phase containing the melted wax and the hydrophobic material is mixed to obtain a homogeneous solution. Typically, this mixing step is carried out by using a stirring device type IKA (mechanical mixing) with a stirring mobile type sawtooth stirrer or 4 pitched blades. It should be understood that the stirring device in step iv) is set in height to not reach the first phase (dispersing phase).
Then, in step (v), the second phase in emulsified into the first phase to obtain a two phases dispersion, preferably an oil-in-water emulsion. Typically, this mixing step is carried out by any well-known techniques such as high-speed mechanical disperser or ultrasonic dispersers.
Finally, the emulsion is cooled at a temperature below the melting point of the wax to obtain a microcapsule slurry. Typically, the cooling step is carried out by any well-known techniques. A rapid cooling is preferred. According to an embodiment, active cooling is performed in the reactor, for example by circulating a cooling fluid in the jacket of the reactor or with another dedicated heat exchanger device. According to another embodiment, the cooling occurs passively.
According to an embodiment, the process comprises a further step of removing water for the slurry (i.e a drying step).
Any drying method known to a skilled person in the art can be used; in particular the slurry may be spray-dried preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans or cellulose derivatives to provide microcapsules in a powder form.
Alternative drying methods can be used including lyophilization, fluidized bed drying, and powder blending with a desiccant.
Microcapsule powder may also comprise free perfume.
MICROCAPSULES
Another object of the invention is a microcapsule slurry or a microcapsule powder obtainable by the process disclosed above.
All of the embodiments disclosed for the process also applies for the description of the microcapsules.
According to an embodiment, the microcapsule has a hardness of the microcapsule above 2000g, preferably above 6500g.
The hardness of the microcapsules can be determined by mechanical testing using an instrument allowing to move a probe along a vertical axis while measuring the force exerted on a probe. A standard method is ASTM method D937-92 (published by ASTM International, Pennsylvania, USA).
According to an embodiment, the microcapsules provide stability against forces or thermodynamic conditions experienced during industrial processing and storage conditions, including mechanical processing and high moisture environment.
According to an embodiment, the microcapsules provide stability against mechanical processing of food products preparation and high moisture environment of the food products.
According to an embodiment, the microcapsules provide release under heat. According to an embodiment, the microcapsules provide long lasting release by diffusion. According to an embodiment, the microcapsules provide physical barrier against leaking in high moisture environment.
According to an embodiment, the microcapsules provide stability against high concentration of surfactant.
According to an embodiment, the microcapsules provide stability in body care and home products made of a high concentration of surfactant such as detergent, softener, shampoo and conditioner.
In a particular embodiment, the microcapsule has a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301 F.
In a particular embodiment, the oil, preferably perfume oil, has a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301 F.
OECD301 F is a standard test method on the biodegradability from the Organization of Economic Co-operation and Development.
Outer coating
According to a particular embodiment of the invention, microcapsules according to the invention comprise an outer coating material selected from the group consisting of a polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724) and mixtures thereof to form an outer coating to the microcapsule.
Polysaccharide polymers are well known to a person skilled in the art. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose, pectin and mixtures thereof.
According to a particular embodiment, the coating consists of a cationic coating.
Cationic polymers are also well known to a person skilled in the art. Preferred cationic polymers have cationic charge densities of at least 0.5 meq/g, more preferably at least about 1 .5 meq/g, but also preferably less than about 7 meq/g, more preferably less than about 6.2 meq/g. The cationic charge density of the cationic polymers may be determined by the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for Nitrogen determination. The preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto. The weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 2M Dalton.
According to a particular embodiment, one will use cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N- dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1 -vinyl-1 H-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride. Preferably copolymers shall be selected from the group consisting of polyquaternium-5, polyquaternium- 6, polyquaternium-7, polyquaterniumI O, polyquaternium-11 , polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
As specific examples of commercially available products, one may cite Salcare®SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF) or Luviquat®, such as the PQ 11 N, FC 550 or Style (polyquaternium-11 to 68 or quaternized copolymers of vinylpyrrolidone origin: BASF), or also the Jaguar® (C13S or C17, origin Rhodia).
According to any one of the above embodiments of the invention, there is added an amount of polymer described above comprised between about 0% and 5% w/w, or even between about 0.1% and 2% w/w, percentage being expressed on a w/w basis relative to the total weight of the slurry. It is clearly understood by a person skilled in the art that only part of said added polymers will be incorporated into/deposited on the microcapsule shell.
According to an embodiment, the outer coating is applied using a fluidized bed coating process, or a liquid/powder blending process. CONSUMER PRODUCTS
Another object of the invention is a consumer product comprising the microcapsules or microcapsule slurry of the invention. Preferably such product is a flavored or fragranced product.
FLAVORED CONSUMER PRODUCTS
In one aspect, the present disclosure provides a flavored article comprising the microcapsules or microcapsule slurry according to an aspect presented herein.
In one aspect, the flavored article is selected from the group consisting of: protein powders, protein drinks, protein bars, meat analogues, seefood analogues and savory goods.
Meat analogues can include pork analogues, venison analogues, beef analogues, veal analogues, rabbit analogues, sausage analogues, deli meat analogues, ham analogues, salami analogues, pepperoni analogues, chicken analogues, turkey analogues, goose analogues, pheasant analogues, pigeon analogues, whale analogues, lamb analogues, goat analogues, donkey analogues, and squirrel analogues.
Seafood analogues can include fish analogues, scallop analogues, shrimp analogues, crabmeat analogues, shellfish analogues, clam analogues, squid analogues, conch analogues, and sea pineapple analogues.
When the flavored article is a particulate or powdery food, the dry particles may easily be added thereto by dry-mixing. Typical flavored articles are selected from the group consisting of an instant soup or sauce, a breakfast cereal, a powdered milk, a baby food, a powdered drink, a powdered chocolate drink, a spread, a powdered cereal drink, a chewing gum, an effervescent tablet, a cereal bar, and a chocolate bar. The powdered foods or drinks may be intended to be consumed after reconstitution of the product with water, milk and/or a juice, or another aqueous liquid.
The dry particles provided herein may be suitable for conveying flavors to beverages, fluid dairy products, condiments, baked goods, frostings, bakery fillings, candy, chewing gum and other food products.
Beverages include, without limitation, carbonated soft drinks, including cola, lemonlime, root beer, heavy citrus (“dew type”), fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and cordials; coffee and coffee-based drinks, coffee substitutes and cereal-based beverages; teas, including dry mix products as well as ready-to-drink teas (herbal and tealeaf based); fruit and vegetable juices and juice flavored beverages as well as juice drinks, nectars, concentrates, punches and “ades”; sweetened and flavored waters, both carbonated and still; sport/energy/health drinks; alcoholic beverages plus alcohol-free and other low-alcohol products including beer and malt beverages, cider, and wines (still, sparkling, fortified wines and wine coolers); other beverages processed with heating (infusions, pasteurization, ultra-high temperature, ohmic heating or commercial aseptic sterilization) and hot-filled packaging; and cold-filled products made through filtration or other preservation techniques.
Fluid dairy products include, without limitation, non-frozen, partially frozen and frozen fluid dairy products such as, for example, milks, ice creams, sorbets and yogurts.
Condiments include, without limitation, ketchup, mayonnaise, salad dressing, Worcestershire sauce, fruit-flavored sauce, chocolate sauce, tomato sauce, chili sauce, and mustard.
Baked goods include, without limitation, cakes, cookies, pastries, breads, donuts and the like. Bakery fillings include, without limitation, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold make-up fillings and nonfat to full-fat fillings.
The composition of the invention can be of particular interest in the following examples of products:
• Baked goods (e.g. bread, dry biscuits, cakes, other baked goods),
• Cereal products (e.g. breakfast cereals, pre-cooked ready-made rice products, rice flour products, millet and sorghum products, raw or pre-cooked noodles and pasta products),
• Milk products (e.g. fresh cheese, soft cheese, hard cheese, milk drinks, whey, butter, partially or wholly hydrolysed milk protein-containing products, fermented milk products, condensed milk and analogues),
• Dairy based products (e.g. fruit or flavoured yoghurt, ice cream, fruit ices, frozen desserts)
• Dairy analogues (imitation dairy products) containing non-dairy ingredients (plantbased proteins, vegetable fats),
• Confectionary products (e.g. chewing gum, hard and soft candy),
• Chocolate and compound coatings,
• Products based on fat and oil or emulsions thereof (e.g. mayonnaise, spreads, margarines, shortenings, remoulade, dressings, spice preparations),
• Spiced, marinated or processed fish products (e.g. fish sausage, surimi),
• Eggs or egg products (dried egg, egg white, egg yolk, custard),
• Desserts (e.g. gelatins and puddings),
• Products made of soya protein or other soya bean fractions (e.g. soya milk and products made therefrom, soya lecithin-containing preparations, fermented products such as tofu or tempeh or products manufactured therefrom, soya sauces),
• Vegetable preparations (e.g. ketchup, sauces, processed and reconstituted vegetables, dried vegetables, deep frozen vegetables, pre-cooked vegetables, vegetables pickled in vinegar, vegetable concentrates or pastes, cooked vegetables, potato preparations),
• Spices or spice preparations (e.g. mustard preparations, horseradish preparations), spice mixtures and, in particular seasonings which are used, for example, in the field of snacks.
• Snack articles (e.g. baked or fried potato crisps or potato dough products, bread dough products, extrudates based on maize, rice or ground nuts),
• Ready dishes (e.g. instant noodles, rice, pasta, pizza, tortillas, wraps) and soups and broths (e.g. stock, savory cube, dried soups, instant soups, pre-cooked soups, retorted soups), sauces (instant sauces, dried sauces, ready-made sauces, gravies, sweet sauces).
• Extended meat products (e.g. meat patties, sausages, chili, Salisbury steaks, pizza toppings, meatballs, ground meat, bolognas, chicken nuggets, pork frankfurters, beef).
The flavored consumer product is preferably chosen in the group consisting of meat- and/or fish-based food or analogue including those of the burger, nugget or filet type, dairy analogue and dairy product including fermented products, baked good, cereal, spices and seasonings, sauces, dressings, marinades, confectionery products, spreads, or nutritional product.
PERFUMED CONSUMER PRODUCTS
The microcapsules of the invention can be used in combination with active ingredients. An object of the invention is therefore a composition comprising:
(i) microcapsules or microcapsule slurry as defined above;
(ii) an active ingredient, preferably chosen in the group consisting of a cosmetic ingredient, skin caring ingredient, perfume ingredient, flavor ingredient, malodour counteracting ingredient, bactericide ingredient, fungicide ingredient, pharmaceutical or agrochemical ingredient, a sanitizing ingredient, an insect repellent or attractant, and mixtures thereof.
The capsules of the invention show a good performance in terms of stability in challenging medium.
Another object of the present invention is a perfuming composition comprising:
(i) microcapsules or microcapsule slurry as defined above, wherein the oil comprises a perfume; (ii) at least one ingredient selected from the group consisting of a perfumery carrier, a perfumery co-ingredient and mixtures thereof;
(iii) optionally at least one perfumery adjuvant.
As liquid perfumery carriers one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-1 -ethanol or ethyl citrate, which are the most commonly used. For the compositions which comprise both a perfumery carrier and a perfumery co-ingredient, other suitable perfumery carriers than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company). By “perfumery co- ingredient” it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as defined above. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
The nature and type of the perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds. Co-ingredients may be chosen in the group consisting of 4- (dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1 -yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6- trimethyl- 1 -cyclohexen-1 -yl)-2-butanone, trans-3-(dodecylthio)-1 -(2,6,6-trimethyl-3- cyclohexen-1 -yl)-1 -butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1 -yl oxo(phenyl)acetate, (Z)-hex-3-en-1 -yl oxo(phenyl)acetate, 3,7- dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1 -yl) succinate, (2- ((2-methylundec-1 -en-1 -yl)oxy)ethyl)benzene, 1 -methoxy-4-(3-methyl-4-phenethoxybut-3-en- 1 -yl)benzene, (3-methyl-4-phenethoxybut-3-en-1 -yl)benzene, 1 -(((Z)-hex-3-en-1 -yl)oxy)-2- methylundec-1 -ene, (2-((2-methylundec-1 -en-1 -yl)oxy)ethoxy)benzene, 2-methyl-1 -(octan-3- yloxy)undec-1 -ene, 1 -methoxy-4-(1 -phenethoxyprop-1 -en-2-yl)benzene, 1 -methyl-4-(1 - phenethoxyprop-1 -en-2-yl)benzene, 2-(1 -phenethoxyprop-1 -en-2-yl)naphthalene, (2- phenethoxyvinyl)benzene, 2-(1 -((3,7-dimethyloct-6-en-1 -yl)oxy)prop-1 -en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1 -((2-methoxy-2- phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1 -isopropyl- 4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1 -((2- pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2- phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or a mixture thereof or a mixture thereof.
By “perfumery adjuvant” we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
Preferably, the perfuming composition according to the invention comprises between 0.01 and 30 % by weight of microcapsules as defined above.
The invention’s microcapsules can advantageously be used in many application fields and used in consumer products. Microcapsules can be used in liquid form applicable to liquid consumer products as well as in powder form, applicable to powder consumer products.
According to a particular embodiment, the consumer product as defined above is liquid and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a microcapsule slurry or microcapsules as defined above, d) optionally non-encapsulated perfume.
According to a particular embodiment, the consumer product as defined above is in a powder form and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) a microcapsule powder as defined above. c) optionally perfume powder that is different from the microcapsules defined above. In the case of microcapsules including a perfume oil, the products of the invention, can in particular be of used in perfumed consumer products such as product belonging to fine fragrance or “functional” perfumery. Functional perfumery includes in particular personal-care products including hair-care, body cleansing, skin care, hygiene-care as well as home-care products including laundry care, surface care and air care. Consequently, another object of the present invention consists of a perfumed consumer product comprising as a perfuming ingredient, the microcapsules defined above or a perfuming composition as defined above. The perfume element of said consumer product can be a combination of perfume microcapsules as defined above and free or non-encapsulated perfume, as well as other types of perfume microcapsules than those here-disclosed.
In particular a liquid consumer product comprising: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a perfuming composition as defined above is another object of the invention.
Also a powder consumer product comprising
(a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; and
(b) a perfuming composition as defined above is part of the invention.
The invention’s microcapsules can therefore be added as such or as part of an invention’s perfuming composition in a perfumed consumer product.
For the sake of clarity, it has to be mentioned that, by “perfumed consumer product” it is meant a consumer product which is expected to deliver among different benefits a perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, paper, or home surface) or in the air (air-freshener, deodorizer etc.). In other words, a perfumed consumer product according to the invention is a manufactured product which comprises a functional formulation also referred to as “base”, together with benefit agents, among which an effective amount of microcapsules according to the invention.
The perfumed consumer product is preferably chosen in the group consisting of a home care product or a personal care product, including laundry dryer sheets, laundry detergents (powdered) cosmetic cream, skin lotions, sunscreen, toothpaste and other oral care products, soap bars, lipstick, solid or roll-on deodorant sticks, and textile products including face masks.
The nature and type of the other constituents of the perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product. Base formulations of consumer products in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
Non-limiting examples of suitable perfumed consumer products can be a perfume, such as a fine perfume, a cologne, an after-shave lotion, a body-splash; a fabric care product, such as a liquid or solid detergent, tablets and unit dose (single or multi-chambers), a fabric softener, a dryer sheet, a fabric refresher, an ironing water, or a bleach; a personal-care product, such as a hair-care product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skin-care product (e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product); an air care product, such as an air freshener or a “ready to use” powdered air freshener; or a home care product, such all-purpose cleaners, liquid or power or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces, for example sprays & wipes intended for the treatment I refreshment of textiles or hard surfaces (floors, tiles, stone-floors etc.); a hygiene product such as sanitary napkins, diapers, toilet paper.
Another object of the invention is a consumer product comprising: - a personal care active base, and microcapsules or microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a personal care composition.
Personal care active bases in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature. The personal care composition is preferably chosen in the group consisting of a hair-care product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skincare product (e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product); Another object of the invention is a consumer product comprising: a home care or a fabric care active base, and microcapsules or microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a home care or a fabric care composition.
Home care or fabric care active bases in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
Preferably, the consumer product comprises from 0.1 to 15 wt%, more preferably between 0.2 and 5 wt% of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, the above concentrations may be adapted according to the benefit effect desired in each product.
An object of the invention is a consumer product, preferably a home care or a fabric care consumer product comprising the microcapsules or the microcapsule slurry as defined above, wherein the consumer product has a pH less than 7.
An object of the invention is a consumer product, preferably a home care or a fabric care consumer product comprising the microcapsules or the microcapsule slurry as defined above, wherein the consumer product has a pH equals or greater than 7.
For liquid consumer product mentioned below, by “active base”, it should be understood that the active base includes active materials (typically including surfactants) and water.
For solid consumer product mention below, by “active base”, it should be understood that the active base includes active materials (typically including surfactants) and auxiliary agents (such as bleaching agents, buffering agent; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, antifoaming, sud suppressing agents; dyes, fillers, and mixtures thereof).
Fabric softener
An object of the invention is a consumer product in the form of a fabric softener composition comprising:
- a fabric softener active base; preferably comprising at least one active material chosen in the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquat (HEQ), TEAQ (triethanolamine quat), silicones and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
- optionally free perfume oil.
Liquid detergent
An object of the invention is a consumer product in the form of a liquid detergent composition comprising:
- a liquid detergent active base; preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
- a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
- optionally free perfume oil.
Solid detergent
An object of the invention is a consumer product in the form of a solid detergent composition comprising:
- a solid detergent active base; preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
- a microcapsule powder or microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
Shampoo/shower gel
An object of the invention is a consumer product in the form of a shampoo or a shower gel composition comprising:
- a shampoo or a shower gel active base; preferably comprising at least one active material chosen in the group consisting of sodium alkylether sulfate, ammonium alkylether sulfates, alkylamphoacetate, cocamidopropyl betaine, cocamide MEA, alkylglucosides and aminoacid based surfactants and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
- a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
- optionally free perfume oil.
Rinse-Off Conditioner
An object of the invention is a consumer product in the form of a rinse-off conditioner composition comprising: a rinse-off conditioner active base; preferably comprising at least one active material chosen in the group consisting of cetyltrimonium chloride, stearyl trimonium chloride, benzalkonium chloride, behentrimonium chloride and mixture thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
Solid scent booster
An object of the invention is a consumer product in the form of a solid scent booster composition comprising:
- a solid carrier, preferably chosen in the group consisting of urea, sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, saccharides such as sucrose, mono-, di-, and polysaccharides and derivatives such as starch, cellulose, methyl cellulose, ethyl cellulose, propyl cellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PEG, PVP, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof,
- a microcapsule slurry or microcapsules as defined above, in a powdered form, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
- optionally free perfume oil.
Liquid scent booster
An object of the invention is a consumer product in the form of a liquid scent booster composition comprising:
- an aqueous phase,
- a surfactant system essentially consisting of one or more than one non-ionic surfactant, wherein the surfactant system has a mean HLB between 10 and 14, preferably chosen in the group consisting of ethoxylated aliphatic alcohols, POE/PPG (polyoxyethylene and polyoxypropylene) ethers, mono and polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxylesters, alkyl polyglucosides, amine oxides and combinations thereof; a linker chosen in the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxyl carboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactant having an HLB less than 10 and mixtures thereof, and a microcapsule slurry or microcapsules as defined above, in the form of a slurry, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
Hair coloration
An object of the invention is a consumer product in the form of an oxidative hair coloring composition comprising: an oxidizing phase comprising an oxidizing agent and an alkaline phase comprising an alkakine agent, a dye precursor and a coupling compound; wherein said dye precursor and said coupling compound form an oxidative hair dye in the presence of the oxidizing agent, preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition,
- optionally free perfume oil
Perfuming composition
According to a particular embodiment, the consumer product is in the form of a perfuming composition comprising:
0.1 to 30%, preferably 0.1 to 20% of or microcapsule slurry or microcapsules as defined previously,
- 0 to 40%, preferably 3-40% of perfume, and
- 20-90%, preferably 40-90% of ethanol, by weight based on the total weight of the perfuming composition.
The invention will now be further described by way of examples. It will be appreciated that the invention as claimed is not intended to be limited in any way by these examples.
Example 1
Preparation of microcapsules according to the invention
Microcapsules A: In a closed reactor, 50 grams of a solution A of an emulsifier (3.6%w/w HICAP 100 - modified starch, Ingredion in deionized water) were prepared (first phase), and 9 grams of rice bran wax (Origin: Kahlwax, Germany) were added by layering on top of 50 grams of solution A. The system was heated at a temperature of Tm = 85°C until complete melting of the wax has occurred, as confirmed by visual observation. It is understood that Tm is a temperature selected to be above the melting temperature of the wax, which can be obtained, for example, using the method of DSC (differential scanning calorimetry).
Then, 3 grams of a flavor composition B (chicken or beef flavor) were added in the reactor, and a dissolver stirrer (R 1303 Dissolver stirrer from IKA) was now placed in the reactor inside the upper oily phase consisting of the melted wax/flavor mixture (second phase), and set in rotation at a low speed of 150rpm to first homogenize the flavor/melted (liquid) wax mixture by itself during 2 minutes. Following this step, the stirrer was lowered to now be located in a location ensuring intensive mixing in the whole reactor, and the speed was increased to 1500 rpm to emulsify the first and second phases.
After 2 minutes of shear emulsification, heating was turned off and 150 grams of cold water at a temperature of 4°C were added in the reactor with the stirrer set to a reduced speed of 250 rpm, resulting in a suspension of solid wax beads comprising the encapsulated flavor composition. These microcapsules (also called beads) were further filtered (Buchner filter) and dried in a fume hood.
This procedure allows therefore a one-pot process providing first a homogeneous mixture of wax and flavor, followed by formation of droplets of said mixture by shearing, all in one process.
Separate complementary tests were performed using alternative drying methods in this step, including lyophilization, fluidized bed drying, and powder blending with a desiccant.
Example 2
Preparation of microcapsules according to the invention
Microcapsules B1 : The same protocol as described in Example 1 was used except that Candelilla wax was used instead of rice bran wax.
Microcapsules B were observed by scanning electron microscopy revealing spherical to ellipsoid particles with longest diameters between 1 and 100 micrometers (see Figure 1 ).
Microcapsules B2: The same protocol as described in Example 1 was used except that Candelilla wax was used instead of rice bran wax and wherein flavor has been replaced by a perfume oil.
Example 3
Preparation of microcapsules according to the invention
Microcapsules C: The same protocol as described in Example 1 was used except that beeswax was used instead of rice bran wax.
Example 4
Cosmetic day cream
Microcapsules B2 were blended into a cosmetic skin cream (see composition below) at a concentration of 5%w/w.
Table 1 : Cream composition
Figure imgf000037_0001
Figure imgf000038_0001
1) ARLATONE 985
2) TEFOSE 2561
3) COSBIOL 4) GLYDANT PLUS
Example 5
Shampoo composition
Microcapsules B2 were blended into a shampoo composition (see composition below) at a concentration of 5%w/w.
Table 2: Shampoo composition
Figure imgf000038_0002
Figure imgf000039_0001
2) Schweizerhall
3) Glydant, Lonza
4) Texapon NSO IS, Cognis
5) Tego Betain F 50, Evonik
6) Amphotensid GB 2009, Zschimmer & Schwarz
7) Monomuls 90 L-12, Gruenau
8) Nipagin Monosodium, NIPA
Example 6
Soap bar A soap bar composition including microcapsules B2 was prepared at a concentration of 7.5% w/w.
Table 3: composition of soap formulation
Figure imgf000040_0001
Example 7
Fabric softener Microcapsules B2 were blended into a fabric softener composition (see composition below) at a concentration of 20%w/w.
Table 4: Fabric Conditioner composition
Figure imgf000041_0001
Example 8
Liquid detergent
Microcapsules B2 were blended into a liquid detergent composition (see composition below) at a concentration of 10%w/w.
Table 5: Liquid detergent composition
Figure imgf000041_0002
Figure imgf000042_0001
1) Hostapur® SAS 60; Origin: Clariant
2) Edenor® K 12-18; Origin: Cognis
3) Genapol® LA 070; Origin: Clariant
4) Aculyn® 88; Origin: Dow Chemical
Example 9
Solid detergent composition Microcapsules B2 were added to the powdered detergent (see composition below) by powder blending a dry mixture of 90%w/w detergent powder with 10%w/w fragranced wax particles.
Table 6: Liquid detergent composition
Figure imgf000042_0002
Figure imgf000043_0001
1) Hostapur® SAS 60; Origin: Clariant
2) Edenor® K 12-18; Origin: Cognis
3) Genapol® LA 070; Origin: Clariant
4) Aculyn® 88; Origin: Dow Chemical
Microcapsules according to the invention resist typical washing water temperatures below 90°C and therefore provide a way to deliver fragrance to laundry with a longer lasting persistence and higher effective fragrance concentration after the washing process.
Example 10
Rinse-off conditioner
Microcapsules B2 are dispersed in a rinse-off conditioner base described below to obtain a concentration of encapsulated perfume oil at 0.5%.
Table 7: Rinse-off conditioner composition
Figure imgf000043_0002
Figure imgf000044_0001
1) Genamin KDM P, Clariant
2) Tylose H10 Y G4, Shin Etsu
3) Lanette O, BASF
4) Arlacel 165-FP-MBAL-PA-(RB), Croda
5) Incroquat Behenyl TMS-50-MBAL-PA-(MH) HA4112, Croda
6) SP Brij S20 MBAL-PA(RB), Croda
7) Xiameter DC MEM-0949 Emulsion, Dow Corning
8) Alfa Aesar
Example 11
Antiperspirant roll-on emulsion composition
Microcapsules B2 are weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
Table 8: Antiperspirant roll-on emulsion composition
Figure imgf000044_0002
1) BRIJ 72; origin : ICI
2) BRIJ 721 ; origin : ICI
3) ARLAMOL E; origin : UNIQEMA-CRODA
4) LOCRON L; origin : CLARIAN
Part A and B are heated separately to 75°C; Part A is added to Part B under stirring and the mixture is homogenized for 10 min. Then, the mixture is cooled under stirring; and Part C is slowly added when the mixture reached 45°C and Part D when the mixture reached at 35 °C while stirring. Then the mixture is cooled to room temperature. Example 12
Deodorant spray composition
Microcapsules B2 are weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
Table 9: Deodorant spray composition
Figure imgf000045_0001
1 ) Irgasan® DP 300; trademark and origin : BASF
All the ingredients according to the sequence of Table 9 are mixed and dissolved. Then the aerosol cans are filled, crimp and the propellant is added (Aerosol filling: 40% active solution 60% Propane I Butane 2.5 bar).
Example 13
Shower-gel composition
Microcapsules B2 are weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
Table 10: Shower gel composition
Figure imgf000045_0002
1) EDETA B POWDER; trademark and origin: BASF
2) CARBOPOL AQUA SF-1 POLYMER; trademark and origin: NOVEON 3) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ
4) TEGO-BETAIN F 50; trademark and origin: GOLDSCHMIDT
5) KATHON CG; trademark and origin: ROHM & HASS
Example 14
Unit dose formulation
Microcapsules B2 weighed and mixed in a unit dose formulation to add the equivalent of 0.2% perfume. The unit dose formulation can be contained in a PVOH (polyvinyl alcohol) film.
Table 11 : Unit dose composition
Figure imgf000046_0001
Example 15
Meat analogue products 0.25%w/w of microcapsules as prepared in example 1 containing 21 %w/w chicken flavor were added to a mixture to form vegan chicken fillet analogues. The nuggets were treated by standard steamer treatment, stored, and prepared in a frying pan for degustation. In parallel, the same nuggets were prepared but with free flavor instead. A trained panel observed far stronger flavor release compared to iso-load free flavor.

Claims

CLAIMS - Process for preparing a microcapsule slurry, wherein it comprises the steps of:
(i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
(ii) Adding a wax and optionally a hydrophobic material on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax,
(iii) Adding a hydrophobic active material if not added in step ii) on the melted wax, or optionally adding an additional hydrophobic material if a hydrophobic material is already added in step ii), wherein the melted wax and the hydrophobic active ingredient form a second phase,
(iv) Mixing the second phase to obtain a homogeneous solution,
(v) Emulsifying the second phase into the first phase to obtain an emulsion,
(vi) Cooling the emulsion at a temperature below the melting point of the wax to obtain a microcapsule slurry, wherein at least steps (ii), (iii), (iv) and (v) are carried out at a temperature greater than the melting point of the wax.
2. The process according to claim 1 , wherein it comprises the steps of:
(i) Preparing a dispersing phase comprising optionally an emulsifier to form a first phase,
(ii) Adding a wax on the dispersing phase and heating at a temperature greater than the melting point of the wax to obtain a melted wax,
(iii) Adding a hydrophobic active material on the melted wax, wherein the melted wax and the hydrophobic active ingredient form a second phase,
(iv) Mixing the second phase to obtain a homogeneous solution,
(v) Emulsifying the second phase into the first phase to obtain an emulsion,
(vi) Cooling the emulsion at a temperature below the melting point of the wax to obtain a microcapsule slurry, wherein at least steps (ii), (iii), (iv) and (v) are carried out at a temperature greater than the melting point of the wax.
3. The process according to claim 1 or 2, wherein the emulsifier is chosen in the group consisting of phospholipids including lecithin, mono and diglycerides of fatty acids, fatty alcohols, saponins, proteins, modified starch, polysaccharides and other hydrocolloids, fibers and mixtures thereof.
4. The process according to anyone of the preceding claims, wherein the wax is chosen in the group consisting of rice bran wax, candelilla wax, carnauba wax and sunflower seed wax, beeswax, olive wax, paraffin wax, synthetic wax, berry wax, myrica wax, rapeseed wax, hydrolyzed sunflower wax, orange wax, jasmin wax, tea wax, rose wax, and mixtures thereof.
5. The process according to anyone of the preceding claims, wherein the hydrophobic material comprises a perfume oil or a flavor oil.
6. The process according to anyone of the preceding claims, wherein the wax is used in an amount comprises between 1% w/w and 20% w/w based on the total weight of the microcapsule slurry.
7. The process according to anyone of the preceding claims, wherein the emulsifier is used in an amount of 0.01% and 10%, preferably 0.5 and 2% by weight based on the total weight of the microcapsule slurry.
8. Microcapsule slurry obtainable by the process according to anyone of claims 1 to 7.
9. The slurry according to claim 8, wherein the hardness of the microcapsule is above 2000g, preferably above 6500g
10. A consumer product comprising the microcapsule slurry as defined in claims 8 or 9 or prepared according to anyone of claims 1 to 7.
11. A consumer product according to claim 10, wherein it is a flavored consumer product preferably chosen in the group consisting of meat- and/or fish-based food or analogue including those of the burger, nugget or filet type, dairy analogue and dairy product including fermented products, baked good, cereal, spices and seasonings, sauces, dressings, marinades, confectionery products, spreads, or nutritional product. A consumer product according to claim 10, wherein it is a perfumed consumer product preferably chosen in the group consisting of a home care product or a personal care product, including laundry dryer sheets, laundry detergents (powdered) cosmetic cream, skin lotions, sunscreen, toothpaste and other oral care products, soap bars, lipstick, solid or roll-on deodorant sticks, and textile products including face masks.
PCT/EP2023/078498 2022-10-18 2023-10-13 Wax-based microcapsules WO2024083677A1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002045575A2 (en) * 2000-10-25 2002-06-13 Salvona L.L.C. Multicomponent biodegradable bioadhesive controlled release system for oral care products
EP2047838A1 (en) * 2007-10-10 2009-04-15 Cognis IP Management GmbH Microcapsules based on waxes
WO2018115250A1 (en) 2016-12-22 2018-06-28 Firmenich Sa Density balanced high impact perfume microcapsules
US20180338501A1 (en) * 2015-10-13 2018-11-29 Botanocap Ltd. Spoilage retardant compositions for treatment of crops
WO2021185724A1 (en) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules coated with a polysuccinimide derivative

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002045575A2 (en) * 2000-10-25 2002-06-13 Salvona L.L.C. Multicomponent biodegradable bioadhesive controlled release system for oral care products
EP2047838A1 (en) * 2007-10-10 2009-04-15 Cognis IP Management GmbH Microcapsules based on waxes
US20180338501A1 (en) * 2015-10-13 2018-11-29 Botanocap Ltd. Spoilage retardant compositions for treatment of crops
WO2018115250A1 (en) 2016-12-22 2018-06-28 Firmenich Sa Density balanced high impact perfume microcapsules
WO2021185724A1 (en) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules coated with a polysuccinimide derivative

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Title
C. VUILLEUMIER ET AL.: "Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach", FRAGRANCE DEVELOPMENT, PERFUME & FLAVORIST, vol. 33, September 2008 (2008-09-01), pages 54 - 61
JELENA MILANOVIC ET AL: "Microencapsulation of Flavors in Carnauba Wax", SENSORS, vol. 10, no. 1, 1 January 2010 (2010-01-01), CH, pages 901 - 912, XP055375526, ISSN: 1424-8220, DOI: 10.3390/s100100901 *

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