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WO2025190840A1 - Microcapsules coeur-écorce à base de phosphore - Google Patents

Microcapsules coeur-écorce à base de phosphore

Info

Publication number
WO2025190840A1
WO2025190840A1 PCT/EP2025/056407 EP2025056407W WO2025190840A1 WO 2025190840 A1 WO2025190840 A1 WO 2025190840A1 EP 2025056407 W EP2025056407 W EP 2025056407W WO 2025190840 A1 WO2025190840 A1 WO 2025190840A1
Authority
WO
WIPO (PCT)
Prior art keywords
phosphate
tris
groups
microcapsules
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/056407
Other languages
English (en)
Inventor
Damien Berthier
Lahoussine Ouali
Geraldine Leon
Nicolas Paret
Yongtao WU
Jia-jun SHEN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
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 WO2025190840A1 publication Critical patent/WO2025190840A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles

Definitions

  • the present invention relates to phosphorous based microcapsules.
  • a process for the preparation of said microcapsules is also an object of the invention.
  • Perfuming compositions and consumer products comprising said microcapsules, in particular perfumed consumer products in the form of home care or personal care 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.
  • the present invention is proposing a solution to the above-mentioned problem by providing new phosphorous based microcapsules and a process for preparing said microcapsules.
  • active 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.
  • dispersion in the present invention it is meant a system in which particles are dispersed in a continuous phase of a different composition and it specifically includes a suspension or an emulsion.
  • a “microcapsule”, or the similar, in the present invention it is meant that core-shell microcapsules have a particle size distribution in the micron range (e.g. a mean diameter (d(v, 0.5)) comprised preferably between about 1 and 3000 microns, more preferably between 1 and 500 microns) and comprise an external solid polymeric shell and an internal continuous oil phase enclosed by the external shell.
  • a mean diameter d(v, 0.5)
  • the shell comprises a phosphorous compound, in particular a phosphate compound.
  • the shell is an inorganic/organic hybrid-based shell.
  • 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.
  • Disposing phase and “continuous phase” can be used indifferently in the present invention.
  • polyfunctional monomer it is meant a molecule that, as unit, reacts or binds chemically to form a polymer or a supramolecular polymer.
  • the polyfunctional monomer of the invention has at least two functional groups that are capable to react with or bind to functional groups of another component and/or are capable to polymerize to form a polymeric shell.
  • the present invention relates to a core-shell microcapsule comprising:
  • a core comprising a hydrophobic material, preferably comprising a perfume oil, and - a shell obtainable from a polymerization reaction of at least one phosphorous compound of formula (I) and/or one compound of formula (II), and/or one compound of formula (III), wherein the compound of formula (I) to (III) are as following:
  • X each independently, represents O, S, and/or N-R 2 ,
  • R 1 each independently, represents R 4 -Y n with n representing an integer from 1 to 6,
  • R 2 each independently, represent H or a Ci to C10 hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms,
  • R 3 each independently, represent a H, Na + , K + , or a Ci to C hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms,
  • R 4 each independently, represents a Ci to C20 hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms, and
  • the core-shell microcapsule comprises a core comprising a hydrophobic material.
  • the core is an oil-based core.
  • the hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
  • hydrophobic material any hydrophobic material which forms a two-phase dispersion when mixed with water.
  • the hydrophobic material is typically liquid at about 20°C.
  • the hydrophobic material is a hydrophobic active ingredient.
  • hydrophobic materials When the hydrophobic materials is an active ingredient, it is preferably chosen from the group consisting of flavor(s), flavor ingredient(s), perfume(s), perfume ingredient(s), nutraceutical (s), cosmetic(s), agrochemical ingredient(s), pest control agent(s), biocide active(s) and mixtures thereof.
  • the hydrophobic material comprises a phase change material (PCM).
  • PCM phase change material
  • the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents, agrochemical ingredients and biocide actives.
  • 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.
  • the hydrophobic material comprises, preferably consists, of phytosanitary compounds. According to a particular embodiment, the hydrophobic material comprises preferably consists of crop fertilizers.
  • phytosanitary compound refers to substances, formulations, or compositions designed to protect plants from pests, diseases, or other harmful organisms. These compounds include, but are not limited to, fungicides, insecticides, herbicides, nematicides, bactericides, acaricides, molluscicides, growth regulators, biopesticides, and other plant- protecting agents. Phytosanitary compounds may be of synthetic or natural origin and can function by inhibiting the growth or activity of target organisms, repelling pests, or enhancing plant resistance to biotic and abiotic stress factors.
  • Crop fertilizer refers to any substance or composition that is applied to soil, plants, or other growing media to supply essential nutrients, enhance soil fertility, or promote plant growth and development.
  • Crop fertilizers include, but are not limited to, macronutrient and micronutrient formulations, organic and inorganic fertilizers, controlled-release fertilizers, biofertilizers, composts, manure-based fertilizers, and soil amendments. These fertilizers may be in solid, or liquid form and can be applied through various methods, including foliar application, soil incorporation, fertigation, and hydroponic solutions.
  • perfume an ingredient or a composition that is a liquid at about 20°C.
  • said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition.
  • a perfuming ingredient it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor.
  • 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.
  • 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 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;
  • 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-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(
  • 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 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 Cs 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;
  • 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, t
  • Group 3 damascenes, 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-T- 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), (1S,1'R)-[1- (3',3'-Dimethyl-T-cyclohexy
  • 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- 2,10,10-trimethyl-1
  • 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 oil phase (or the oil-based core) 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. 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/cm 3 and having preferably low or no odor.
  • the odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GO”). 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.
  • GO 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-yl)-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
  • 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-based core 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-2-(2-methyl-1- propen
  • the core comprises a perfume formulation comprising:
  • 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 herein defined 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, 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 + 6H 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 bH 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)
  • bH 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 (bDsolvent-bDfragrance) ⁇ + (bP solvent-bPfragrance) ⁇ + (bHsolvent-bHfragrance) ⁇ ) ⁇ in Which SDsassemble, SPsassemble, and 5H S rete, are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and bDf ra grance, bPf ra grance, 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 (bD) from 12 to 20, a dipole moment (bP) from 1 to 8, and a hydrogen bonding (bH) 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 (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) from 2.5 to 11 , preferably from 4 to 11.
  • a second group consisting of: an atomic dispersion force (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) from 2.5 to 11 , preferably from 4 to 11.
  • 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 (bD) from 12 to 20, a dipole moment (bP) from 1 to 8, and a hydrogen bonding (bH) 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 (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) from 2.5 to 11 , preferably from 4 to 11 .
  • a second group consisting of: an atomic dispersion force (bD) from 12 to 20, preferably from 14 to 20, a dipole moment (bP) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (bH) 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; ii. a clogP of 3.5 and higher, preferable 4.0 and higher and more preferable 4.5 iii. 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.
  • 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.
  • 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-1'-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-diene, (+-)
  • 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, glycol
  • 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 anti parasite.
  • 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.
  • flavor oil it is meant here a flavoring ingredient or a mixture of flavoring ingredients, solvents or adjuvants of current use for the preparation of a flavoring formulation, i.e. a particular mixture of ingredients which is intended to be added to an edible composition or chewable product to impart, improve or modify its organoleptic properties, in particular its flavor and/or taste.
  • flavoring ingredients are well known to a person skilled in the art and their nature does not warrant a detailed description here, which in any case would not be exhaustive, the skilled flavorist being able to select them on the basis of his general knowledge and according to the intended use or application and the organoleptic effect it is desired to achieve. Many of these flavoring ingredients are listed in reference texts such as in the book by S.
  • the flavor is a mint flavor.
  • the mint is selected from the group consisting of peppermint and spearmint.
  • the flavor is a cooling agent or mixtures thereof.
  • the flavor is a menthol flavor.
  • Flavors that are derived from or based on fruits where citric acid is the predominant, naturally-occurring acid include but are not limited to, for example, citrus fruits (e.g. lemon, lime), limonene, strawberry, orange, and pineapple.
  • the flavors food is lemon, lime or orange juice extracted directly from the fruit.
  • Further embodiments of the flavor comprise the juice or liquid extracted from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, and any other citrus fruit, or variation or hybrid thereof.
  • the flavor comprises a flavor selected from the group comprising strawberry, orange, lime, tropical, berry mix, and pineapple.
  • flavor includes not only flavors that impart or modify the smell of foods but include taste imparting or modifying ingredients.
  • the latter do not necessarily have a taste or smell themselves but are capable of modifying the taste that other ingredients provides, for instance, salt enhancing ingredients, sweetness enhancing ingredients, umami enhancing ingredients, bitterness blocking ingredients and so on.
  • suitable sweetening components may be included in the particles described herein.
  • a sweetening component is selected from the group consisting of sugar (e.g., but not limited to sucrose), a stevia component (such as but not limited to stevioside or rebaudioside A), sodium cyclamate, aspartame, sucralose, sodium saccharine, and Acesulfam K or mixtures thereof.
  • the core-shell microcapsule comprises a shell obtainable from a polymerization reaction of at least one phosphorous compound of formula (I) and/or one compound of formula (II), and/or one compound of formula (III), wherein the phosphorous compound of formula (I) to (III) are as following:
  • X each independently, represents O, S, and/or N-R 2 ,
  • R 1 each independently, represents R 4 -Y n with n representing an integer from 1 to 6,
  • R 2 each independently, represents H or a Ci to Cw hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms,
  • R 3 each independently, represents a Ci to C hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms,
  • R 4 each independently, represents a H, Na + , K + or a Ci to C20 hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms, and
  • a 5- or 6- membered ring comprising and/or wherein Z is H or -CHO;
  • alkyl and alkenyl are understood as comprising branched, alicyclic and linear alkyl and alkenyl groups.
  • alkenyl cycloalkenyl and “heterocycloalkenyl” are understood as comprising 1, 2 or 3 olefinic double bonds, preferably 1 or 2 olefinic double bonds, provided that the cycloalkenyl group is not an aryl group.
  • cycloalkyl cycloalkenyl
  • heterocycloalkyl and “heterocycloalkenyl” are understood as comprising a monocyclic or fused, spiro and/or bridged bicyclic or tricyclic cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl groups, preferably monocyclic cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl groups.
  • alkoxy is understood as an -OR’ group wherein R’ is a linear branched or cyclic alkyl group.
  • aryl is understood as comprising any group comprising at least one aromatic group such as phenyl, indenyl, indanyl, benzodioxolyl, dihydrobenzodioxinyl, tetrahydronaphthalenyl or naphthalenyl group.
  • ... hydrocarbon group consists of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), a linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g. cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e. aryl group, or can also be in the form of a mixture of said type of groups, e.g.
  • a specific group may comprise a linear alkyl, a branched alkenyl (e.g. having one or more carbon-carbon double bonds), a (poly)cycloalkyl and an aryl moiety, unless a specific limitation to only one type is mentioned.
  • a group when a group is mentioned as being in the form of more than one type of topology (e.g. linear, cyclic or branched) and/or being saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is also meant a group which may comprise moieties having any one of said topologies or being saturated or unsaturated, as explained above.
  • a group when a group is mentioned as being in the form of one type of saturation or unsaturation, (e.g. alkyl), it is meant that said group can be in any type of topology (e.g. linear, cyclic or branched) or having several moieties with various topologies.
  • hydrocarbon group optionally comprising one or more oxygen atoms
  • hydrocarbon group optionally comprises one, two, three or more oxygen atoms in a form of alcohol, ketone, aldehyde, ether, ester, carboxylic acid, carbonate groups.
  • These groups can either substitute a hydrogen atom of the hydrocarbon group and thus be laterally attached to said hydrocarbon, or substitute a carbon atom (if chemically possible) of the hydrocarbon group and thus be inserted into the hydrocarbon chain.
  • a -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group comprising an alcohol group (substitution of a hydrogen atom), i.e.
  • a C4 hydrocarbon comprising an oxygen atom a -CH2-CH2-COO-CH2-CH2CH2-CH2- group represents a C7 hydrocarbon group comprising one ester group (substitution of carbon atoms/insertion into the hydrocarbon chain), i.e. a C7 hydrocarbon comprising two oxygen atoms and, similarly, a -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a C6 hydrocarbon group comprising two ether groups, i.e. a C6 hydrocarbon comprising two oxygen atoms.
  • any one of its stereoisomers or a mixture thereof can be a pure enantiomer or diastereomer.
  • the compound of formula (I) may possess several stereocenters and each of said stereocenter can have two different stereochemistries (e.g. R or S).
  • the compound of formula (I) may even be in the form of a pure enantiomer or in the form of a mixture of enantiomers or diastereoisomers.
  • the compound of formula (I) can be in a racemic form or scalemic form. Therefore, the compound of formula (I) can be one stereoisomer or in the form of a composition of matter comprising, or consisting of, various stereoisomers.
  • each independently it is herein understood, that each functional group to which the expression is referring to can independently be from each other one of the defined functionalities.
  • each “each independently” can be understood as comprising different or the same functionalities, preferably as comprising the same functionalities.
  • the bond marked with “*” is understood as the direct connection of the Y moiety to the R 4 moiety.
  • the * is understood to represent the R 4 moiety when being used in the context with Y.
  • the term “polymerization reaction” refers to a chemical process in which monomers undergo a reaction to form polymer chains or networks. This includes homopolymerization, wherein identical monomer units react to form a polymer consisting of repeating units of a single type, and copolymerization, wherein two or more different types of monomers react to form a polymer with varying structural units.
  • the polymerization reaction may proceed through various mechanisms, including but not limited to free-radical, ionic, coordination, or step-growth polymerization, depending on the monomers and reaction conditions employed.
  • the phosphorous compound of formula (I) and/or phosphorous compound of formula (II) and/or phosphorous compound of formula (III) may be preferably a phosphorous compound of formula (I) and/or phosphorous compound of formula (II), most preferably a phosphorous compound of formula (I).
  • the phosphorous compound of formula (I) and/or phosphorous compound of formula (II) and/or phosphorous compound of formula (III) may be one of the following:
  • X each independently, represents O and/or N-R 2 , preferably O.
  • R 1 each independently, represents R 4 -Y n with n representing an integer from 1 to 4, preferably n is 1 to 3, more preferably n is 1 to 2.
  • R 2 each independently, represent H or a Ci to Cw hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 2 each independently, represent H or a Ci to C hydrocarbon moiety, more preferably H.
  • R 3 each independently, represent H, Na + , K + , or a Ci to Cw hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 3 each independently, represent a Ci to Cw hydrocarbon moiety, more preferably Ci to Cs hydrocarbon moiety, more preferably Ci to C3 hydrocarbon moiety.
  • R 3 each independently, represent a Ci to Cw alkyl or alkenyl group, more preferably Ci to C3 alkyl or alkenyl group, more preferably methyl, ethyl, propyl or isopropyl group, most preferably ethyl group.
  • R 4 each independently, represents a Ci to C hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 4 each independently, represents a Ci to Cw hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms. In an embodiment, R 4 , each independently, represents a Ci to C12 hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 4 each independently, represents a Ci to C10 hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 4 each independently, represents a Ci to Cs hydrocarbon moiety, optionally comprising one or more O, S and/or N atoms.
  • R 4 each independently, represents a Ci to C18 hydrocarbon moiety, optionally comprising one or more O and/or N atoms, preferably optionally one or more O atoms.
  • R 4 each independently, represents a Ci to C15 hydrocarbon moiety, optionally comprising one or more O and/or N atoms, preferably optionally one or more O atoms.
  • R 4 each independently, represents a Ci to C12 hydrocarbon moiety, optionally comprising one or more O and/or N atoms, preferably optionally one or more O atoms.
  • R 4 each independently, represents a Ci to C10 hydrocarbon moiety, optionally comprising one or more O and/or N atoms, preferably optionally one or more O atoms.
  • R 4 each independently, represents a Ci to Cs hydrocarbon moiety, optionally comprising one or more O and/or N atoms, preferably optionally one or more O atoms.
  • R 4 each independently, represents Ce to C10 aryl group, optionally substituted with one or more Ci to C4 alkoxy groups, preferably one or more methoxy or ethoxy groups, and/or carboxy group, or a Ci to C10 linear or branched alkyl group, optionally substituted with one or more Ci to C4 alkoxy groups.
  • R 4 each independently, represents Cs aryl group, optionally substituted with one or more Ci to C4 alkoxy groups, and/or carboxy group, preferably one or more methoxy or ethoxy groups, or a Ci to Cs linear or branched alkyl group, optionally substituted with one or more Ci to C4 alkoxy groups.
  • R 4 each independently, represents phenyl group, optionally substituted with one or more Ci to C4 alkoxy groups, and/or carboxy group, preferably one or more methoxy or ethoxy groups, or a Ci to C4 linear or branched alkyl group, optionally substituted with one or more Ci to C4 alkoxy groups.
  • Y each independently, represents - -OH, -NHR 2 , -CHO, -NCO, and/or -COCI;
  • Y each independently, represents
  • the compound of formula (I) to (III) is selected from the group consisting of tris(4-formylphenyl) phosphate, tris(4-formyl-2-methoxyphenyl) phosphate, triallyl 3,3',3"-((oxo-X 5 -phosphanetriyl)tris(oxy))tribenzoate, tris(3-chlorocarbonyl phenyl) phosphate, tris(3-formyl phenyl) phosphate, tris(3-hydroxypropyl) phosphate, 3-[bis(3- acetoxypropoxy)phosphoryloxy]propyl acetate, tris(2-ethoxy-4-formyl-phenyl) phosphate, tris(2,2-dimethyl-3-oxo-propyl) phosphate, tris(3-oxopropyl) phosphate, tris(2-vinyloxyethyl) phosphate, tris[(2-vinyl
  • the pKa of the corresponding monomer H-X-R 1 and/or H-X-R 2 is between 6 and 11 , more preferably between 7 and 10, even more preferably between 7.5 and 9.
  • the compounds of formula (I) to (III) are polymerized to a structure as for example following formula (IV) or more specifically (IVa): wherein the definitions for X, R 1 and R 4 are as defined herein-above for phosphorous compounds of formula (I) to (III) and Z is an integer of at least 1 , preferably 1 to 50.
  • Y each independently, represents
  • a strained heterocycle of the following structures a 5- or 6- membered ring comprising wherein Z is H or -CHO;
  • Y with regard to formula (III) does not represent OH, -SH, -NHR 2 , -CHO, - NCO and/or -COCI.
  • the core-shell microcapsule comprises a shell obtainable from a polymerization reaction of at least one of the phosphorous compounds of formula (l)-(lll) and at least one polyfunctional monomer, preferably a polymerisation compatible polyfunctional monomer.
  • polyfunctional monomer preferably a polymerisation compatible polyfunctional monomer
  • polyfunctional monomer A preferably a polymerisation compatible polyfunctional monomer
  • polymerisation compatible polyfunctional monomer it is herein understood that the polyfunctional monomer has functional groups that are polymerizable with the functional groups Y of the phosphorous compound.
  • the polyfunctional monomer is polymerisation compatible in the sense that it comprises nucleophilic functional groups such as nucleophilic enol or phenol carbon groups.
  • the polyfunctional monomer is polymerisation compatible in the sense that it comprises nucleophilic functional groups such as -OH, amino groups or the like.
  • the polyfunctional monomer is a nucleophilic polyfunctional monomer.
  • the nucleophilic polyfunctional monomer comprises nucleophilic nitrogen groups, nucleophilic sulfur groups, nucleophilic enol or phenol carbon groups, nucleophilic oxygen groups, nucleophilic phosphor groups or mixtures thereof.
  • the nucleophilic polyfunctional monomer comprises alcohol groups, amine groups, thiol groups, or nucleophilic enol or phenol carbon groups or mixtures thereof.
  • the polyfunctional monomer is selected from the group consisiting of phloroglucinol, resorcinol, gallic acid, cardanol, propyl gallate and mixture thereof, preferably the polyfunctional monomer is phloroglucinol.
  • the polyfunctional monomer is an electrophilic polyfunctional monomer.
  • the polyfunctional monomer comprises electrophilic acyl groups, preferably acyl chloride groups, isocyanate groups, anhydride groups, aldehyde groups, epoxy groups or mixtures thereof.
  • the polyfunctional monomer is an acyl chloride.
  • the acyl chloride has the following formula (II) wherein n is an integer varying between 1 and 8, preferably between 1 and 6, more preferably between 1 and 4, and wherein X is an (n+1)-valent C2 to C45 hydrocarbon group optionally comprising at least one group selected from (i) to (xi), wherein R is a hydrogen atom or an alkyl group, preferably a hydrogen atom.
  • the acyl chloride is chosen from the group consisting of benzene- 1 , 3, 5-tricarbonyl trichloride (trimesoyl chloride), benzene-1 ,2,4-tricarbonyl trichloride, benzene-1 ,2,4,5-tetracarbonyl tetrachloride, cyclohexane- 1 , 3, 5-tricarbonyl trichloride, isophthalyol dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaryl dichloride, adipoyl dichloride, succinic dichloride, propane-1 , 2, 3-tricarbonyl trichloride, cyclohexane- 1 , 2,4,5- tetracarbonyl tetrachloride, 2,2'-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo- ethyl)s
  • the acyl chloride is chosen from the group consisting of fumaryl dichloride, adipoyl dichloride, succinic dichloride, propane-1 , 2, 3-triyl tris(4-chloro-4- oxobutanoate), propane-1 , 2-diyl bis(4-chloro-4-oxobutanoate), and mixtures thereof.
  • the acyl chloride is a mixture of acyl chlorides.
  • the weight ratio between acyl chloride and the hydrophobic material is preferably comprised between 0.005 and 0.5, more preferably between 0.01 and 0.07.
  • the acyl chloride is used in a concentration between 0.05 % to 50 %, preferably between 0.1 to 15%, by weight based on the oil phase (or hydrophobic material).
  • the polyfunctional monomer is a polyisocyanate having at least two isocyanate functional groups.
  • Suitable polyisocyanates used according to the invention can include aromatic polyisocyanate, aliphatic polyisocyanate and mixtures thereof. Said polyisocyanate comprises at least 2, preferably at least 3 but may comprise up to 6, or even only 4, isocyanate functional groups. According to a particular embodiment, a triisocyanate (3 isocyanate functional group) is used.
  • said polyisocyanate is an aromatic polyisocyanate.
  • aromatic polyisocyanate is meant here as encompassing any polyisocyanate comprising an aromatic moiety. Preferably, it comprises a phenyl, a toluyl, a xylyl, a naphthyl or a diphenyl moiety, more preferably a toluyl or a xylyl moiety.
  • Preferred aromatic polyisocyanates are biurets, polyisocyanurates and trimethylol propane adducts of diisocyanates, more preferably comprising one of the above-cited specific aromatic moieties.
  • the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® RC), a trimethylol propane-adduct of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® L75), a trimethylol propane-adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the tradename Takenate® D-110N).
  • the aromatic polyisocyanate is a trimethylol propane-adduct of xylylene diisocyanate.
  • said polyisocyanate is an aliphatic polyisocyanate.
  • aliphatic polyisocyanate is defined as a polyisocyanate which does not comprise any aromatic moiety.
  • Preferred aliphatic polyisocyanates are a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a trimethylol propane-adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or a biuret of hexamethylene diisocyanate (commercially available from Bayer under the tradename Desmodur® N 100), among which a biuret of hexamethylene di isocyanate is even more preferred.
  • the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and of at least one aromatic polyisocyanate, both comprising at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate with a polyisocyanurate of toluene diisocyanate and a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of toluene diisocyanate.
  • it is a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of xylylene diisocyanate.
  • the molar ratio between the aliphatic polyisocyanate and the aromatic polyisocyanate is ranging from 80:20 to 10:90.
  • Other preferred aliphatic polyisocyanates are L-lysine diisocyanate ethyl ester.
  • the polyfunctional monomer comprises epoxy groups.
  • the polyfunctional monomer comprises a radical polymerisable group.
  • the polyfunctional monomer comprises a reactive olefinic group.
  • the polyfunctional monomer comprises vinyl groups, allyl groups, butadienyl groups, acrylate groups or mixtures thereof.
  • the polyfunctional monomer comprises a silane group.
  • the polyfunctional monomer comprises alkoxysilane groups.
  • the polyfunctional monomer comprises furfuryl groups.
  • the polyfunctional monomer comprises maleimide groups.
  • the core-shell microcapsule comprises a shell obtainable from a polymerization reaction of at least one of the phosphorous compounds of formula (I) to (III) and at least one polyfunctional monomer, preferably a polymerisation compatible polyfunctional monomer, and an additional polyfunctional monomer, preferably polyfunctional monomer having the same polymerizable groups as the phosphorous compounds of formula (I) to (III).
  • polyfunctional monomer preferably polyfunctional monomer having the same polymerizable groups as the phosphorous compounds of formula (I) to (III)” and “polyfunctional monomer B” are herein used interchangeably.
  • polyfunctional monomer having the same polymerizable groups as the phosphorous compounds of formula (I) to (III) it is herein understood that the additional polyfunctional monomer has the same polymerizable functional groups as the phosphorous compounds of formula (I) to (III).
  • the additional polyfunctional monomer B comprises an electrophilic functional group Y such as -CHO so that the polyfunctional monomer A comprising for example nucleophilic carbon phenol groups can react with the -CHO functional groups of the phosphorous compound and the additional polyfunctional monomer B.
  • the additional polyfunctional monomer B is selected from the group of 4-formylphenyl-4-formyl benzoate, bis(4-formylphenyl) succinate, succindialdehyde, adipaldehyde, glutaraldehyde, glyoxal, malondialdehyde, oleocanthal, oxidized saccharide, isophthaldehyde, and terephthaldehyde.
  • the additional polyfunctional monomer B is selected from the group of 4-formylphenyl-4-formyl benzoate, bis(4-formylphenyl) succinate, succindialdehyde, adipaldehyde, malondialdehyde, isophthaldehyde, and terephthaldehyde.
  • the additional polyfunctional monomer B is selected from the group of 4-formylphenyl-4-formylbenzoate, bis(4-formylphenyl) succinate, and terephthaldehyde.
  • the shell material is a biodegradable material.
  • the shell has a biodegradability of at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%, within 60 days according to OECD301 F.
  • the core-shell 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 core-shell microcapsule including all components, such as the core, shell and optionally coating may have 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 core preferably perfume oil
  • OECD301 F is a standard test method on the biodegradability from the Organization of Economic Co-operation and Development.
  • a typical method for extracting the shell for measuring the biodegradability is disclosed in Gasparini and all in Molecules 2020, 25,718.
  • the microcapsule comprises an outer coating, wherein the outer coating comprises a coating material selected from the group consisting of a non-ionic polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724), an anionic polymer and mixtures thereof to form an outer coating to the microcapsule.
  • the outer coating comprises a coating material selected from the group consisting of a non-ionic polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724), an anionic polymer and mixtures thereof to form an outer coating to the microcapsule.
  • Non-ionic polysaccharide polymers are well known to a person skilled in the art and are described for instance in WO 2012/007438 page 29, lines 1 to 25 and in WO 2013/026657 page 2, lines 12 to 19 and page 4, lines 3 to 12.
  • Preferred non-ionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose.
  • Cationic polymers are 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 1.5M Dalton.
  • Mw weight average molecular weight
  • 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.
  • copolymers shall be selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaterniumIO, 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).
  • anionic polymers are well known to a person skilled in the art.
  • Preferred anionic polymers have anionic 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 anionic charge density of the anionic polymers may be determined by standard titration methods, such as polyelectrolyte titration using a cationic titrant.
  • the preferred anionic polymers are chosen from those that contain units comprising carboxylate, sulfonate, sulfate, or phosphate groups, which 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 anionic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 1.5M Dalton.
  • the anionic polymer is selected from the group consisting of carboxymethylcellulose and salts thereof, anionic modified starch and salts thereof, gum Arabic and salts thereof, pectin and salts thereof, alginate and salts thereof, carrageenan and salts thereof, polyvinyl alcohol and salts thereof, polyaspartate and salts thereof and mixtures thereof.
  • 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 microcapsule of the present invention comprises a mineral layer.
  • the mineral layer preferably comprises a material chosen in the group consisting of iron oxides, iron oxyhydroxide, titanium oxides, zinc oxides, calcium carbonates, calcium phosphates, barium salt, strontium salt, magnesium salt, and mixtures thereof and mixtures thereof.
  • the shell comprises a coacervate or coacervate-like structure comprising as first polyelectrolyte and a second polyelectrolyte.
  • a coacervate structure is formed by a phase-separation process of polymers and is formed by the spontaneous aggregation of macromolecules/polymers (mainly due to electrostatic interactions, hydrogen bonding, or hydrophobic effects among polymer chains).
  • a coacervate-like structure exhibits polymer aggregation by forming a crosslinked network among polymer chains (such as crosslinked polymer layer) via physical interactions (electrostatic interactions, hydrogen bonding), but also via additional chemical cross-linkage (with chemical crosslinker or enzyme).
  • the coacervate or coacervate-like structure comprises a first polyelectrolyte, preferably is selected from the group consisting of gum arabic, modified starch, pectin, carboxymethyl cellulose, sodium carboxymethyl guar gum, carrageenan, lignin, plant gums, glycogen, polyaspartate, proteins and mixtures thereof and a second polyelectrolyte, preferably is selected from the group consisting of poly(L-lysine), animal proteins, gelatin, casein, plant proteins, chitin, chitosan, silk protein and mixtures thereof.
  • a first polyelectrolyte preferably is selected from the group consisting of gum arabic, modified starch, pectin, carboxymethyl cellulose, sodium carboxymethyl guar gum, carrageenan, lignin, plant gums, glycogen, polyaspartate, proteins and mixtures thereof
  • a second polyelectrolyte preferably is selected from the group consisting of poly
  • the pectin is selected from the group consisting of high methoxy pectin, low methoxy pectin, sugar beet pectin and mixtures thereof.
  • the coacervate material can be either hardened by the inventive process during the curing step and/or by adding a suitable cross-linker such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin or can be hardened enzymatically using an enzyme.
  • a suitable cross-linker such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin or can be hardened enzymatically using an enzyme.
  • the present invention also relates to a process for preparing a core-shell microcapsule comprising the steps of: a) Dispersing an oil phase comprising a hydrophobic material into a continuous phase C1 to form a two-phases dispersion; b) Optionally, dispersing the two-phases dispersion into a continuous phase C2 to form a multiple dispersion, c) curing the dispersion obtained in step a) or in step b) to form microcapsules in the form of a slurry, wherein a phosphorous compound of formula (I) and/or formula (II), and/or formula (III) is added in the continuous phase(s) and/or in the oil phase and optionally, wherein a polyfunctional monomer is added in the continuous phase(s) and/or in the oil phase.
  • the embodiments disclosed for the core-shell microcapsules also apply for the process for preparing core-shell microcapsules. It applies notably to the phosphorous compound of formula (I) to (III), the polyfunctional monomer and the hydrophobic material.
  • the continuous phase C1 and/or C2 each independently, comprises, preferably consists of water.
  • the continuous phase C1 and/or C2, each independently, is a water phase.
  • the two-phases dispersion is an oil-in-water emulsion.
  • the continuous phase C1 and/or C2 each independently, comprises water and an alcohol such as glycerol, 1 ,4-butanediol, propane diols, such as 1 ,3-propane diol or 1,2-propane diol, ethylene glycol and mixtures thereof.
  • an alcohol such as glycerol, 1 ,4-butanediol, propane diols, such as 1 ,3-propane diol or 1,2-propane diol, ethylene glycol and mixtures thereof.
  • the continuous phase C1 and/or C2, each independently, consists of alcohol.
  • the multiple dispersion is a two-phases dispersion, preferably an oil- in-water emulsion.
  • a stabilizer is added in the oil phase and/or in the continuous phase C1 and/or C2.
  • the stabilizer is added in the continuous phase C1 and/or C2.
  • stabilizer it is meant a compound capable to stabilize oil/dispersing phase interface (typically oil/water interface) as an emulsion.
  • the stabilizer is preferably used in an amount comprised between 0.05% to 20 %, preferably between 0.1 to 10%, even more preferably between 0.5 and 5% by weight based on the two-phases dispersion, preferably oil-in-water emulsion.
  • Stabilizer or “emulsifier” can be used indifferently in the present invention.
  • the stabilizer is a colloidal stabilizer.
  • the colloidal stabilizer can be a polymeric emulsifier (standard emulsion), a surfactant, or solid particles (Pickering emulsion).
  • polymeric emulsifier By “polymeric emulsifier”, it meant an emulsifier having both a polar group with an affinity for water (hydrophilic) and a nonpolar group with an affinity for oil (hydrophobic). The hydrophilic part will dissolve in the water phase and the hydrophobic part will dissolve in the oil phase providing a film around droplets.
  • surfactant it meant a substance with a polar and a non-polar group that is added to the liquid to reduce the liquid surface tension.
  • the stabilizer is chosen in the group consisting of inorganic particles, polymeric particles, polymeric emulsifier such as polysaccharides, proteins, glycoproteins, and mixtures thereof.
  • the stabilizer when it is solid particles, it can be chosen in the group consisting of calcium phosphate, silica, silicates, titanium dioxide, aluminium oxide, zinc oxide, iron oxide, mica, kaolin, montmorillonite, laponite, bentonite, perlite, dolomite, diatomite, vermiculite, hectorite, gibbsite, illite, kaolinite, aluminosilicates, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomaceous earth and mixtures thereof.
  • the stabilizer is polymer particles
  • it can be chosen in the group consisting of starch particles, lignin particles, silk fibroin particles, zein particles, gliadin particles, coacervate particles comprising a first polymer and a second polymer, and mixtures thereof.
  • the stabilizer is a biopolymer.
  • biopolymers it is meant biomacromolecules produced by living organisms. Biopolymers are characterized by molecular weight distributions ranging from 1 ,000 (1 thousand) to 1,000,000,000 (1 billion) Daltons. These macromolecules may be carbohydrates (sugar based) or proteins (amino-acid based) or a combination of both (gums) and can be linear or branched.
  • the polymeric emulsifier is chosen in the group consisting of gum Arabic, modified starch, polyvinyl alcohol, polyvinylpyrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, sodium polyaspartate, acrylamide copolymer, protein such as soy protein, rice protein, whey protein, white egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
  • Potato proteins are typically extracted from potato tuber (Solanum tuberosum).
  • the potato protein is a native potato protein and preferably patatin.
  • the stabilizer is selected from the group consisting of inorganic particles, surfactant, polymeric emulsifier such as polysaccharides, proteins, glycoproteins and mixtures thereof.
  • the polyfunctional monomer is added in the oil phase or in the continuous phase C1 and/or C2.
  • the polyfunctional monomer is added to the continuous phase C1 and/or C2.
  • the polyfunctional monomer is preferably used in an amount comprised between 0.01% and 30%, preferably between 0.1 % and 10%, preferably between 0.5 and 5% based on the total weight of the two-phases dispersion, preferably oil-in-water emulsion.
  • the polyfunctional monomer is added in an amount comprised between 0.1 and 10%, preferably between 0.2 and 4.0 % by weight, based on the total weight of the two-phases dispersion, preferably oil-in-water emulsion.
  • the phosphorous compound of formula (I) to (III) is added in the oil phase or in the continuous phase C1 and/or C2.
  • the phosphorous compound of formula (I) to (III) is added in the oil phase.
  • Any compound of formula (I) and/or formula (II) and/or formula (III) can be used in an amount comprised between 0.01% and 30%, preferably between 0.05% and 8%, more preferably between 0.5 and 5% based on the total weight of the two phases dispersion, preferably oil-in-water emulsion.
  • any compound of formula (I) and/or formula (II) and/or formula (III) is added in an amount comprised between 0.01% and 10%, preferably between 0.5% and 5%, more preferably between 1% and 3% by weight, based on the total weight of the two-phases dispersion, preferably oil-in-water emulsion.
  • At least one salt is added in the dispersing phase and/or in the oil phase and/or in the two-phases dispersion.
  • the salt is preferably used in an amount comprised between 0.01% and 10% by weight based on the two-phases dispersion.
  • the salt added in the aqueous phase can be chosen in the group consisting of calcium, zinc, sodium, potassium, lithium, magnesium, aluminum, iron, manganese, copper, titanium, barium, sulphates, phosphates, nitrates, bromides, chlorides, iodides, acetates, and ammonium salts.
  • the salt is chosen in the group consisting of CaCl2, NaCI, KCI, ZnCI 2 , ZnSO 4 , Zn(NO 3 ) 2 , LiCI, Ca(NO 3 ) 2 , MgCI 2 , CaBr 2 , Cal 2 , NaBr, Nal, NaNO 3 , KBr, KI, KNO 3 , LiBr, Lil, MgBr 2 ,CuCI 2 , FeCI 2 , FeCI 3 , TiCI 4 , MnCI 2 , and mixtures thereof.
  • the pH of the dispersing phase is preferably comprised between 2 and 12, preferably between 3 and 8, more preferably between 3 and 5.
  • a base is added in step a) and/or b).
  • the base is selected from the group consisting of guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydroxide or mixtures thereof.
  • an acid is added in step a) and/or b).
  • the acid is selected from the group consisting of formic acid, acetic acid, HCI or nitric acid or mixtures thereof.
  • the pH is adjusted in step a) and/or b) to a pH value from 2 to 9, preferably to a pH value from 2.5 to 7, more preferably to a pH value from 3.0 to 6.5.
  • the curing in step c) is performed in a temperature range of 20 to 90°C, preferably 50 to 88°C, more preferably 70 to 85°C.
  • the curing in step c) is performed over a time period from 1 h to 24 h, preferably over a time period from 2 h to 18 h, more preferably over a time period from 3 h and 16 h, more preferably over a time period from 4 to 12 h.
  • the process comprises an optional step after the curing step c) (i.e. step d) of adding a solution of a stabilizer, preferably an anionic colloidal stabilizer or a first polyelectrolyte.
  • a stabilizer preferably an anionic colloidal stabilizer or a first polyelectrolyte.
  • a solution of a stabilizer preferably an anionic colloidal stabilizer or a first polyelectrolyte, is an aqueous solution.
  • the solution of a stabilizer is added at about the curing temperature of step c), such as in a temperature range of 20 to 90°C, preferably 50 to 88°C, more preferably 70 to 85°C.
  • the process comprises an optional step after the curing step c) and/or step d) (i.e. step e) of adjusting, preferably cooling down, the dispersion to a temperature comprised between 0 and 70°C, preferably 5 to 60°C, more preferably 10 to 40°C.
  • the adjustment, preferably cooling down is achieved by air cooling or cooling with cooling means, such as ice cooling.
  • the process comprises an optional step after the curing step c) and/or step d) and/or step e) (i.e. step f) of adding a second polyelectrolyte, preferably a cationic polymer, preferably to form a coacervate.
  • the process steps d) and f) are mandatory in order to form the coacervate.
  • the process comprises an optional step after the curing step c) and/or step d) and/or step e) and/or step f) (step g) of additional curing the mixture.
  • the curing in step g) is performed in a temperature range of 20 to 90°C, preferably 40 to 88°C, more preferably 50 to 70°C.
  • the curing in step g) is performed over a time period from 10 min to 12 h, preferably over a time period from 30 min to 4 h, more preferably over a time period from 45 min and 2 h.
  • the process comprises a further optional step after the curing step g) (i.e. step h) of adding a solution of a stabilizer, preferably an anionic colloidal stabilizer or a first polyelectrolyte as described herein-above.
  • a stabilizer preferably an anionic colloidal stabilizer or a first polyelectrolyte as described herein-above.
  • a solution of a stabilizer preferably an anionic colloidal stabilizer or a first polyelectrolyte, is an aqueous solution.
  • the solution of a stabilizer is added at about the curing temperature of step c), such as in a temperature range of 20 to 90°C, preferably 40 to 88°C, more preferably 50 to 70°C.
  • the process comprises an optional step after the curing step g) and/or step h) (i.e. step i) of adjusting, preferably cooling down, the dispersion to a temperature comprised between 0 and 70°C, preferably 5 to 60°C, more preferably 10 to 40°C, more preferably room temperature (i.e. 21°C).
  • the adjustment preferably cooling down, is achieved by air cooling or cooling with cooling means, such as ice cooling.
  • the microcapsules of the invention can be used in combination with a second type of microcapsules.
  • Another object of the invention is a microcapsule delivery system comprising:
  • microcapsules of the present invention as a first type of microcapsule
  • the microcapsule delivery system is in the form of a slurry.
  • the wall of the second type of microcapsules can vary.
  • the polymer shell of the second type of microcapsules comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyhydroxyalkanoates, polyacrylate, polyesters, polyaminoesters, polyepoxides, organosilicon, polycarbonate, polysulfonamide, urea formaldehyde, melamine formaldehyde resin, melamine formaldehyde resin cross-linked with polyisocyanate or aromatic polyols, melamine urea resin, melamine glyoxal resin, gelatin/ gum arabic shell wall, and mixtures thereof.
  • the second type of microcapsule can comprise an oil-based core comprising a hydrophobic active, preferably perfume, and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, the first material is a coacervate, the second material is a polymeric material.
  • the weight ratio between the first material and the second material is comprised between 50:50 and 99.9:0.1.
  • the coacervate comprises a first polyelectrolyte, preferably selected among proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), most preferably Gelatin and a second polyelectrolyte, preferably alginate salts, cellulose derivatives guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or yet plant gums such as acacia gum (Gum Arabic), most preferably Gum Arabic.
  • proteins such as gelatin
  • polypeptides or polysaccharides such as chitosan
  • a second polyelectrolyte preferably alginate salts, cellulose derivatives guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or yet plant gums such as acacia gum (Gum Arabic), most preferably Gum Arabic.
  • the coacervate first material can be hardened chemically using a suitable cross-linker such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin or can be hardenedenzymatically using an enzyme such as transglutaminase.
  • the second polymeric material can be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, organosilicon, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof, preferably polyurea and/or polyurethane.
  • the second material is preferably present in an amount less than 3 wt.%, preferably less than 1 wt.% based on the total weight of the second type of microcapsule slurry.
  • the shell of the second type of microcapsules can be aminoplast-based, polyurea-based or polyurethane-based.
  • the shell of the second type of microcapsules can also be hybrid, namely organic-inorganic such as a hybrid shell composed of at least two types of inorganic particles that are cross-linked, or yet a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macro-monomeric composition.
  • the shell of the second type of microcapsules comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
  • aminoplast copolymer such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
  • the shell of the second type of microcapsules is polyurea- based made from, for example but not limited to isocyanate-based monomers and amine- containing crosslinkers such as guanidine carbonate and/or guanazole.
  • Certain polyurea microcapsules comprise a polyurea wall which is the reaction product of the polymerisation between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of an amine (for example a water- soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated perfume.
  • an amine for example a water- soluble guanidine salt and guanidine
  • a colloidal stabilizer or emulsifier for example a colloidal stabilizer or emulsifier
  • an encapsulated perfume for example a water- soluble guanidine salt and guanidine
  • an amine for example a water-
  • the colloidal stabilizer includes an aqueous solution of between 0.1% and 0.4% of polyvinyl alcohol, between 0.6% and 1 % of a cationic copolymer of vinylpyrrolidone and of a quaternized vinylimidazol (all percentages being defined by weight relative to the total weight of the colloidal stabilizer).
  • the emulsifier is an anionic or amphiphilic biopolymer, which may be, in one aspect, chosen from the group consisting of gum Arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.
  • the microcapsule wall material of the second type of microcapsules may comprise any suitable resin and especially including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc.
  • suitable resins include the reaction product of an aldehyde and an amine
  • suitable aldehydes include, formaldehyde and glyoxal.
  • suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof.
  • Suitable melamines include, methylol melamine, methylated methylol melamine, imino melamine and mixtures thereof.
  • Suitable ureas include, dimethylol urea, methylated dimethylol urea, urearesorcinol, and mixtures thereof.
  • Suitable materials for making may be obtained from one or more of the following companies Solutia Inc. (St Louis, Missouri U.S.A.), Cytec Industries (West Paterson, New Jersey U.S.A.), Sigma-Aldrich (St. Louis, Missouri U.S.A.).
  • the second type of microcapsules is a one-shell aminoplast core-shell microcapsule obtainable by a process comprising the steps of:
  • the second type of microcapsules is a formaldehyde-free capsule.
  • a typical process for the preparation of aminoplast formaldehyde-free microcapsules slurry comprises the steps of
  • oligomeric composition comprising the reaction product of, or obtainable by reacting together: a. a polyamine component in the form of melamine or of a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups; b. an aldehyde component in the form of a mixture of glyoxal, a C4-62,2-dialkoxy- ethanal and optionally a glyoxalate, said mixture having a molar ratio glyoxal/C4- 6 2,2-dialkoxy-ethanal comprised between 1/1 and10/1 ; and c. a protic acid catalyst;
  • an oil-in-water dispersion wherein the droplet size is comprised between 1 and 600 microns, and comprising: a. an oil; b. a water medium: c. at least an oligomeric composition as obtained in step 1 ; d. at least a cross-linker selected amongst: i. C4-C12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimmers, trimethylol propane-adduct and mixtures thereof; and/or ii. a di- or tri-oxiran compounds of formula:
  • n stands for 2 or 3 and 1 represents a C2-C6 group optionally comprising from 2 to 6 nitrogen and/or oxygen atoms; e. optionally a C1-C4 compounds comprising two NH2 functional groups;
  • the second type of microcapsule comprises
  • an oil-based core comprising a hydrophobic active, preferably perfume
  • biopolymer shell comprising a protein, wherein at least one protein is cross-linked.
  • the protein is chosen in the group consisting of milk proteins, caseinate salts such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed proteins, gelatins, gluten, pea protein, soy protein, silk protein and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate
  • the protein comprises sodium caseinate and a globular protein, preferably chosen in the group consisting of whey protein, beta-lactoglobulin, ovalbumine, bovine serum albumin, vegetable proteins, and mixtures thereof.
  • the protein is preferably a mixture of sodium caseinate and whey protein.
  • the biopolymer shell comprises a crosslinked protein chosen in the group consisting of sodium caseinate and/or whey protein.
  • the second type of microcapsules slurry comprises at least one microcapsule made of:
  • an oil-based core comprising the hydrophobic active, preferably perfume
  • an inner shell made of a polymerized polyfunctional monomer; preferably a polyisocyanate having at least two isocyanate functional groups
  • biopolymer shell comprising a protein, wherein at least one protein is cross-linked; wherein the protein contains preferably a mixture comprising sodium caseinate and a globular protein, preferably whey protein,
  • sodium caseinate and/or whey protein is (are) crosslinked protein (s).
  • the weight ratio between sodium caseinate and whey protein is preferably comprised between 0.01 and 100, preferably between 0.1 and 10, more preferably between 0.2 and 5.
  • the second type of microcapsules is a polyamide coreshell polyamide microcapsule comprising:
  • an oil-based core comprising comprising a hydrophobic active, preferably perfume, and
  • polyamide shell comprising or being obtainable from:
  • the second type of microcapsules comprises:
  • an oil-based core comprising a hydrophobic active, preferably perfume, and
  • polyamide shell comprising or being obtainable from:
  • an acyl chloride preferably in an amount comprised between 5 and 98%, preferably between 20 and 98%, more preferably between 30 and 85% w/w
  • a first amino compound preferably in an amount comprised between 1 % and 50% w/w, preferably between 7 and 40% w/w; • a second amino compound, preferably in an amount comprised between
  • a stabilizer preferably a biopolymer, preferably in an amount comprised between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%,
  • the second type of microcapsules comprises:
  • an oil-based core comprising a hydrophobic active, preferably perfume, and
  • polyamide shell comprising or being obtainable from:
  • a first amino-compound being an amino-acid, preferably chosen in the group consisting of L-Lysine, L-Arginine, L-Histidine, L-Tryptophane and/or mixtures thereof.
  • a second amino-compound preferably chosen in the group consisting of ethylene diamine, diethylene triamine, cystamine and/or mixtures thereof, and
  • a biopolymer preferably chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, soy protein, rice protein, whey protein, white egg albumin, casein, sodium caseinate, gelatin (preferably fish gelatin), bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, gelatin and mixtures thereof,
  • a carbohydrate preferably selected from the group consisting of anionic salt of alginic acid, preferably alginic acid sodium salt, pectin, lignin, anionic modified starch, carboxymethylcellulose, carrageenan and mixtures thereof.
  • the shell of the second type of microcapsules is polyurea- or polyurethane-based.
  • processes for the preparation of polyurea and polyurethane-based microcapsule slurry are for instance described in International Patent Application Publication No. W02007/004166, European Patent Application Publication No. EP 2300146, and European Patent Application Publication No. EP25799.
  • a process for the preparation of polyurea or polyurethane-based microcapsule slurry include the following steps: a) Dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase; b) Preparing an aqueous solution of an emulsifier or colloidal stabilizer to form a dispersing phase; c) Adding the oil phase to the dispersing phase to form an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 500 pm, preferably between 5 and 50 pm; and d) Applying conditions sufficient to induce interfacial polymerisation and form microcapsules in form of a slurry.
  • the present invention also relates to a perfuming composition
  • a perfuming composition comprising a core-shell microcapsule or core-shell microcapsule slurry as described hereinabove or obtained by the process according to the present invention, at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base, and optionally, at least one perfumery adjuvant.
  • composition comprises:
  • 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.
  • a core-shell microcapsule or core-shell microcapsule slurry as described herein-above or as obtained by the process according to the present invention can also be added in different perfumed consumer products.
  • present invention relates to a perfuming composition
  • a perfuming composition comprising
  • the perfuming composition according to the invention comprises between 0.1 and 40 %, preferably between 0.1 and 30% by weight of a core-shell microcapsule or coreshell microcapsule slurry as described herein-above or obtained by the process according to the present invention.
  • free perfume it is herein understood a perfume or perfume oil which is comprised in the perfuming composition and not entrapped in the core-shell microcapsule or core-shell microcapsule slurry as described herein-above or as obtained by the process according to the present invention.
  • the total amount of the core-shell microcapsule or core-shell microcapsule slurry as described herein-above or as obtained by the process according to the present invention is 0.05 to 5 wt.% (based on the total weight of the perfuming composition) and the total amount of the free perfume oil is 0.05 to 5 wt.% (based on the total weight of the perfuming composition).
  • the total perfume oil of the perfume formulation entrapped in the core-shell microcapsule or core-shell microcapsule slurry as described herein-above or as obtained by the process according to the present invention and total free perfume oil are present in the perfuming composition in a weight ratio of 1 :20 to 20:1 , preferably 10:1 to 1 :10.
  • the perfuming composition can further comprise at least one perfuming co-ingredient and, optionally a perfumery adjuvant.
  • perfuming co-ingredient it is herein understood a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as 20 defined above.
  • 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 impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • 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 sulfur heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • Many of these co-30 ingredients are in any case listed in reference texts such as the book by S.
  • 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
  • perfumery adjuvant an ingredient capable of imparting additional 5 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 core-shell microcapsule or core-shell microcapsule slurry as described hereinabove or as obtained by the process according to the present invention can advantageously be used in many application fields and used in consumer products.
  • the present invention also relates to a perfumed consumer product comprising a core-shell microcapsule or core-shell microcapsule slurry as described hereinabove or as obtained by the process according to the present invention, and a personal care, home care, or fabric care active base.
  • the consumer 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 and air care.
  • liquid consumer product comprising:
  • a 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.
  • Non-limiting examples of suitable perfumed consumer products can be a fine perfume, a splash or eau de perfume, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a mono or multi chamber unidose detergent , a fabric softener, a fabric refresher, liquid or solid scent-boosters (PEG I urea or salts), a dryer sheet, an ironing water, a paper, a bleach, a carpet cleaners, curtain-care products, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a hair conditioning product, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdere
  • the perfumed consumer product is preferably selected from the group consisting of personal care composition, home care composition or fabric care composition, most preferably in form of antiperspirants, hair care products, such as shampoo or hair-conditioner, body care products such as a shower gel, oral care products, laundry care products, preferably a detergent or a fabric softener.
  • the present invention also relates to a consumer product comprising:
  • microcapsules or a 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 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).
  • 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 skincare product e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product.
  • the present invention also relates to a consumer product comprising:
  • 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.
  • 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).
  • 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.
  • the home or fabric care composition is preferably chosen in the group consisting of fabric softener, liquid detergent, powder detergent, liquid scent booster and solid scent booster.
  • 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,
  • microcapsules or a microcapsule slurry 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 poly( ethylene 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
  • microcapsules or a microcapsule slurry 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 poly(ethylene 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
  • microcapsule powder or microcapsule slurry 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 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, cocam idopropyl 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, - microcapsules or a microcapsule slurry 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 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,
  • microcapsules or a microcapsule slurry 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 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,
  • microcapsules or a microcapsule slurry 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,
  • Liquid scent booster An object of the invention is a consumer product in the form of a liquid scent booster composition comprising:
  • 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;
  • POE/PPG polyoxyethylene and polyoxypropylene
  • 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
  • microcapsules or a microcapsule slurry 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,
  • An object of the invention is a consumer product in the form of an oxidative hair coloring composition
  • 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,
  • microcapsules or a microcapsule slurry 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:
  • microcapsules preferably 0.1 to 20% of microcapsules or a microcapsule slurry as defined previously,
  • the core-shell microcapsules disclosed herein may be part of a mulch film.
  • the term 'mulch film' refers to a thin polymeric or composite sheet applied to the soil surface to protect crops by regulating soil temperature, retaining moisture, suppressing weed growth, and reducing erosion.
  • Mulch films may be composed of synthetic or biodegradable materials and are typically designed for temporary use during a crop cycle, often requiring collection and disposal after use.
  • a further advantage of the present invention is that the biodegradable core-shell microcapsules incorporated within the mulch film provide an environmentally friendly solution, as they can naturally degrade in the soil, reducing long-term environmental impact and minimizing residue accumulation.
  • the core-shell microcapsules disclosed herein may also be used as a component in a mulch film, preferably in a biodegradable mulch film.
  • the core-shell microcapsules disclosed herein may be used as a mulch film.
  • the shell of the core-shell microcapsules disclosed herein may be used as a fertilizer.
  • Phosphorus is an essential macronutrient for plant growth, playing a crucial role in energy transfer, root development, and overall crop yield.
  • phosphorus can gradually release into the soil as the shell degrades, ensuring sustained nutrient availability to plants. This controlled release mechanism enhances phosphorus uptake efficiency, minimizing leaching losses and environmental runoff, which are common concerns with conventional phosphorus fertilizers.
  • the core-shell microcapsule disclosed herein may also be used as a delivery system for additional fertilizing product.
  • the tris(3,3-diethoxypropyl) phosphate (11) was purified by liquid chromatography with a mixture of ethyl acetate: n-heptane 5:5.
  • Phosphate triester 26 (0.3 g) was dissolved in a mixture of dichloromethane and trifluoroacetic acid (4:1 , v:v) (12 mL) at room temperature for 24 h. The solvents were distilled off. The resulting solid was dissolved in ethyl acetate (25 mL) and washed with water (25 mL) and brine (25 mL). The organic phase was dried over sodium sulfate and the solvent was distilled off to afford the product.
  • the dispersion was cured at 80°C during 4h.
  • the mixture was cooled down from 80°C to 20°C.
  • a solution of chitosan (source: Kitozyme, Belgium, 1.29 g) in 0.3 M HCI (17.86 g) was added over 30 minutes.
  • the dispersion was cured at 60°C over the period of 1 h.
  • Capsules were prepared according to the protocol of Example 2 and using tris(3-formylphenyl) phosphate.
  • %m 250 100 dm % _ %m 250 - %m 5Q dt 200
  • microcapsules of Examples 2 and 3 have the capacity to retain fragrance oil at 50°C compared to free oil.
  • Microcapsule shells were purified from slurries according to the protocol published by Gasparini et al. Resulting polymers were submitted to OECD 301 F testing conditions and results are listed in the Table below.
  • Capsules were prepared according to the protocol of Example 2 at pH 3.2 and using different parameters listed in Table 4.
  • microcapsules of Example 5 have the capacity to retain fragrance oil at 50°C compared to free oil.
  • the biodegradation of microcapsules A-5, B-5, C-5 and E-5 was tested, and a yield greater than 60% after 60 days was obtained for these microcapsules.
  • Capsules were prepared according to the protocol of Example 2 at pH 3.2 and different anionic polymers in Table 5.
  • microcapsules of Example 6 have the capacity to retain fragrance oil at 50°C compared to free oil.
  • the biodegradation of microcapsules B-6, E-6 and N-6 was tested, and a yield greater than 60% after 60 days was obtained for these microcapsules.
  • Capsules were prepared according to the protocol of Example 2 at pH 3.2 and different cationic polymers in Table 6.
  • Example 7 has the capacity to retain fragrance oil at 50°C compared to free oil.
  • Capsules were prepared according to the protocol of Example 2 at pH 3.2 with different multifunctional aldehydes in Table 7.
  • Example 8 has the capacity to retain fragrance oil at 50°C compared to free oil.
  • the dispersion was cured at 80°C during 4h. The mixture was cooled down from 80°C to 20°C over 30 minutes. A solution of chitosan (source: Kitozyme, Belgium, 1.29 g) in 0.3 M HCI (17.86 g) was added. After 30 minutes, a solution of gum Arabic (5.00 g) in water (14.29 g) was added to the composition. The dispersion was cured at 60°C over the period of 1 h. To avoid agglomeration, a solution of gum Arabic (0.71 g) in water (2.14 g) was added to the composition. After two hours at 60°C, the composition was cooled to room temperature to afford the final dispersion. Table 9: Multifunctional aldehydes of the invention in formulations and results of retention
  • the dispersion was cured at 80°C during 4h. The mixture was cooled down from 80°C to 20°C over 30 minutes. A solution of chitosan (source: Kitozyme, Belgium, 1.29 g) in 0.3 M HCI (17.86 g) was added over 30 minutes. The dispersion was warmed up to 60°C over 30 minutes and cured for two hours. The composition was cooled to room temperature to afford the final dispersion.
  • Microcapsules A-12 Potato protein (0.56 g) was dissolved in DI water (27.44 g) with stirring to give a solution as aqueous phase. Tris(4-isocyanatophenyl) thiophosphate (Desmodur RFE) (0.936 g) was vacuumed for 1 min and dissolved in mixture of neobee (1.2 g) and the perfume composition (Perfume Oil A herein-above; 10.6137 g) with stirring to give a solution as oil phase. The prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion.
  • Desmodur RFE Tris(4-isocyanatophenyl) thiophosphate
  • Table 11 Composition of microcapsules A-12.
  • Neobee M5 Microcapsules B-12 Potato protein (0.56 g) was dissolved in DI water (27.44 g) with stirring to give a solution as aqueous phase. Desmodur RFE (0.936 g) was vacuumed for 1 min and dissolved in mixture of neobee (1.2 g) and Perfume Oil A (10.6137 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion.
  • 5% sugar beet pectin (10 g) was added drop wise with stirring.
  • the pH value was adjusted to 4 by diluted NaOH. It was stirred at 90°C for 1 h, then cooled to 40°C, followed by adding laccase (0.36 g of 1 ll/g aqueous solution) and stirred for 4 h, next, it was stirred at 90°C for 0.5 h. Stable microcapsules were obtained.
  • Table 12 Composition of microcapsules B-12.
  • Microcapsules C-12 Potato protein (0.56 g) was dissolved in DI water (27.44 g) with stirring to give a solution as aqueous phase. Desmodur RFE (0.936 g) was vacuumed for 1 min and dissolved in mixture of neobee (1.2 g) and Perfume Oil A (10.6137 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion.
  • 5% Gum Arabic 4.5 g was added drop wise with stirring.
  • the pH value was adjusted to 4 by diluted NaOH. It was stirred at 90°C for 1 h, then cooled to 40°C, and stirred for 4 h, next, it was stirred at 90°C for 0.5 h. Stable microcapsules were obtained.
  • Table 13 Composition of microcapsules C-12. 1) Solanic 200, origin: Avebe
  • Neobee M5 Microcapsules D-12 Potato protein (0.75 g) was dissolved in DI water (23.25 g) with stirring to give a solution as aqueous phase. Desmodur RFE (1.248 g) and neobee (1.6 g) and Perfume Oil A (13.152 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion.
  • 5% Gum Arabic (10 g) was added drop wise with stirring.
  • the pH value was adjusted to 4 by diluted NaOH. It was stirred at 90°C for 1 h, then cooled to 40°C, followed by adding 50% glutaraldehyde (0.75 g) and stirred for 4 h, next, it was stirred at 90°C for 0.5 h. Stable microcapsules were obtained.
  • Table 14 Composition of microcapsules D-12.
  • Microcapsules E-12 In a four stream multi-inlet vortex, 4.0% potato protein aqueous solution (adjusted to pH 4) were injected into two steams and 2% Gum Arabic aqueous solution (adjusted to pH 4) were injected into another two streams. The injection was made using the pump (PHD ULTRA, Harvard) under the speed at 40 mL/min. The obtained suspension was used as aqueous phase.
  • Desmodur RFE (1.17 g) was vacuumed for 1 min and dissolved in mixture of neobee (1.5 g) and L-Lysine diisocyanate ethyl ester (0.3 g) and Perfume Oil A (12.9424 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion. It was stirred at 90°C for 2 h. Stable microcapsules were obtained.
  • Table 15 Composition of microcapsules E-12.
  • Microcapsules F-12 In a four stream multi-inlet vortex, 4.0% potato protein aqueous solution (adjusted to pH 4) were injected into two steams and 2% Gum Arabic aqueous solution (adjusted to pH 4) were injected into another two streams. The injection was made using the pump (PHD ULTRA, Harvard) under the speed at 40 mL/min. The obtained suspension was used as aqueous phase.
  • Desmodur RFE (2.34 g) was vacuumed for 1 min and dissolved in mixture of benzyl benzoate (4.5 g) and Perfume Oil A (9.8804 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 13.5k rpm for 2 min to obtain a emulsion. It was stirred at 90°C for 2 h. Stable microcapsules were obtained.
  • Table 16 Composition of microcapsules F-12.
  • Microcapsules G-12 Potato protein (0.7 g) was dissolved in DI water (31 g) with stirring to give a solution, lysine ethyl ester dihydrochloride (0.7875 g) was added to it, followed by adjusting the pH value to 10 by 30% NaOH, and stirred to give a solution, then a solution with calcium chloride (0.14 g) dissolved in DI water (2.3725 g) was added with stirring to give a suspension as the water phase. Desmodur RFE (2.34 g) was vacuumed for 2 min and dissolved in mixture of benzyl benzoate (4.5 g) and Perfume Oil A (10 g) with stirring to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 18k rpm for 1 min to obtain an emulsion.
  • the pH value of the obtained emulsion was adjusted to 5 by acetic acid. It was stirred at 90°C for 2 h. Stable microcapsules were obtained.
  • Table 17 Composition of microcapsules G-12.
  • Microcapsules H-12 Potato protein (0.7 g) was dissolved in DI water (31 g) with stirring to give a solution, lysine ethyl ester dihydrochloride (0.7875 g) was added to it, followed by adjusting the pH value to 10 by 30% NaOH, and stirred to give a solution, then a solution with calcium chloride (0.14 g) dissolved in DI water (2.3725 g) was added with stirring to give a suspension as the water phase.
  • Desmodur RFE (2.34 g) was vacuumed for 2 min and dissolved in mixture of benzyl benzoate (1.5 g) and Perfume Oil A (6.26 g) with stirring to give a solution; PCL-diol (0.75 g) was dissolved in mixture of benzyl benzoate (3 g) and Perfume Oil A (3 g) with stirring at 50°C to give a solution, and it was mixed with the solution containing Desmodur RFE at RT to give a solution as oil phase.
  • the prepared two phases were mixed using ULTRA-TURRAX at 18k rpm for 1 min to obtain an emulsion.
  • the pH value of the obtained emulsion was adjusted to 5 by acetic acid. It was stirred at 90°C for 2 h. Stable microcapsules were obtained.
  • Table 18 Composition of microcapsules H-12.
  • the storage stability of the capsules in liquid fabric conditioner composition was evaluated.
  • Microcapsule dispersions (i.e slurry) of the present invention were diluted in the fabric conditioner composition described below to obtain a concentration of encapsulated perfume of 0.116%.
  • the fabric conditioner was stored at 38°C. The amount of perfume having leaked out of the capsules was then measured by solvent extraction and GC-MS analysis.
  • Microcapsules of Example 3 show a leakage of 12%.
  • Microcapsule dispersions (i.e slurry) of the present invention were diluted in the liquid detergent composition (P&G US Tide Free & Gentle HE, ingredients listed below) to obtain a concentration of encapsulated perfume of 0.116%.
  • the detergent was stored at 38°C.
  • the amount of perfume having leaked out of the capsules was then measured by solvent extraction and GC-MS analysis. Leakage results after three days at 38°C are listed below.
  • Table 20 Liquid detergent composition
  • Microcapsules of Example 3 show a leakage of 17%.
  • Capsules were prepared according to the protocol of Example 2 and using other phenols (see table below) instead of phloroglucinol.
  • Emulsions A-E having the following ingredients are prepared. Table 22: Composition of Emulsions A-E and composition of granulated powder A-E after spray-drying 1) CapsulTM, Ingredion
  • Methyl dihydrojasmonate Firmenich SA, Switzerland 6
  • Components for the polymeric matrix (Maltodextrin and capsulTM, or capsulTM , citric acid and tripotassium citrate) are added in water at 45-50°C until complete dissolution.
  • emulsion D free perfume C is added to the aqueous phase.
  • Microcapsules slurry is added to the obtained mixture. Then, the resulting mixture is then mixed gently at 25°C (room temperature).
  • Granulated powder A-E are prepared by spray-drying Emulsion A-E using a Sodeva Spray Dryer (Origin France), with an air inlet temperature set to 215°C and a throughput set to 500 ml per hour. The air outlet temperature is of 105°C. The emulsion before atomization is at ambient temperature.
  • Liquid scent booster composition Liquid scent booster composition
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a liquid scent booster to add the equivalent of 0.2% perfume.
  • compositions 1-6 Plantacare 2000UP; trademark and origin : BASF Different ringing gel compositions are prepared (compositions 1-6) according to the following protocol.
  • aqueous phase water
  • solvent propylene glycol
  • surfactants are mixed together at room temperature under agitation with magnetic stirrer at 300 rpm for 5 min.
  • the linker is dissolved in the hydrophobic active ingredient (fragrance) at room temperature under agitation with magnetic stirrer at 300 rpm. The resulting mixture is mixed for 5 min.
  • the aqueous phase and the oil phase are mixed together at room temperature for 5 min leading to the formation of a transparent or opalescent ringing gel.
  • Liquid detergent composition A sufficient amount of exemplified microcapsules is weighed and mixed in a liquid detergent to add the equivalent of 0.2% perfume.
  • Unit dose formulation A sufficient amount of exemplified microcapsules is 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.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a powder detergent composition to add the equivalent of 0.2% perfume.
  • Concentrated All Purpose Cleaner composition A sufficient amount of exemplified microcapsules is weighed and mixed in a concentrated allpurpose cleaner composition to add the equivalent of 0.2% perfume.
  • Neodol 91-8 ® trademark and origin : Shell Chemical
  • compositions are prepared.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • Polyquaternium-10 is dispersed in water.
  • the remaining ingredients of phase A are mixed separately by addition of one after the other while mixing well after each adjunction.
  • this pre-mix is added to the Polyquaternium-10 dispersion and was mixed for 5 min.
  • Phase B and the premixed Phase C are added.
  • Shampoo composition A sufficient amount of exemplified microcapsules is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • D-Panthenol, Roche A premix comprising Guar Hydroxypropyltrimonium Chloride and Polyquaternium-10 are added to water and Tetrasodium EDTA while mixing.
  • NaOH is added.
  • Phase C ingredients are added and the mixture was heat to 75 °C.
  • Phase D ingredients are added and mixed till homogeneous. The heating is stopped and temperature of the mixture is decreased to RT.
  • ingredients of Phase E while mixing final viscosity is adjusted with 25% NaCI solution and pH of 5.5-6 is adjusted with 10% NaOH solution.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a rinse-off composition to add the equivalent of 0.2% perfume.
  • Phase A Ingredients of Phase A are mixed until an uniform mixture was obtained. Tylose is allowed to completely dissolve. Then the mixture is heated up to 70-75°C. Ingredients of Phase B are combined and melted at 70-75°C. Then ingredients of Phase B are added to Phase A with good agitation and the mixing is continued until cooled down to 60°C. Then, ingredients of Phase C are added while agitating and keeping mixing until the mixture cooled down to 40°C. The pH is adjusted with citric acid solution till pH: 3.5 - 4.0.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in an antiperspirant spray anhydrous composition to add the equivalent of 0.2% perfume.
  • Aerosil® 200 trademark and origin : Evonik
  • Antiperspirant spray emulsion composition A sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant spray emulsion composition to add the equivalent of 0.2% perfume.
  • Sensiva sc 50 trademark and origin : KRAFT
  • Aerosil R 812 trademark and origin : Evonik
  • Nipagin mna trademark and origin : CLARIANT
  • Part A and Part B are weighted separately. Ingredients of Part A are heated up to 60°C and ingredients of Part B are heated to 55 °C. Ingredients of Part B are poured small parts while continuous stirring into A. Mixture were stirred well until the room temperature was reached. Then, ingredients of part C are added. The emulsion is mixed and is introduced into the aerosol cans. The propellant is crimped and added. Aerosol filling: 30% Emulsion: 70% Propane / Butane 2,5 bar
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant deodorant spray composition to add the equivalent of 0.2% perfume.
  • Irgasan® DP 300 trademark and origin : BASF
  • Antiperspirant roll-on emulsion composition
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant rollon emulsion composition to add the equivalent of 0.2% perfume.
  • Table 37 antiperspirant roll-on emulsion composition 1) BRU 72; origin : ICI
  • 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 minutes. Then, the mixture is cooled down 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 down to RT.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant rollon composition to add the equivalent of 0.2% perfume.
  • part B The ingredients of part B are mixed in the vessel then ingredient of part A is added. Then dissolved part C in part A and B. With perfume, 1 part of Cremophor RH40 for 1 part of perfume is added while mixing well
  • Antiperspirant roll-on composition A sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant rollon emulsion composition to add the equivalent of 0.2% perfume.
  • Part A is prepared by sprinkling little by little the Hydroxyethylcellulose in the water whilst rapidly stirring with the turbine. Stirring is continued until the Hydroxyethylcellulose is entirely swollen and giving a limpid gel. Then, Part B is poured little by little in Part A whilst continuing stirring until the whole is homogeneous. Part C is added.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Cremophor® RH 40 trademark and origin : BASF
  • Ingredients from Part B are mixed together. Ingredients of Part A are dissolved according to the sequence of the Table and are poured into part B.
  • a sufficient amount of granules A-E is weighed and mixed in introduced in a standard talc base: 100% talc, very slight characteristic odor, white powder, origin: LUZENAC to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • CARBOPOLAQUA SF-1 POLYMER trademark and origin: NOVEON
  • KATHON CG trademark and origin: ROHM & HASS
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • EUPERLAN PK 3000 AM trademark and origin: COGNIS
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Tixosil 73 trademark and origin :
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Aerosil®200 trademark and origin:
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Example 41 Mouthwash formulation A sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor. Table 49: Mouthwash formulation

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Abstract

La présente invention concerne des microcapsules à base de phosphore. Un procédé de préparation desdites microcapsules est également un objet de l'invention. L'invention concerne également des compositions parfumantes et des produits de consommation comprenant lesdites microcapsules, en particulier des produits de consommation parfumés sous la forme de produits ménagers ou de soins personnels.
PCT/EP2025/056407 2024-03-11 2025-03-10 Microcapsules coeur-écorce à base de phosphore Pending WO2025190840A1 (fr)

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EP24162581.3 2024-03-11

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025799A1 (fr) 1979-03-28 1981-04-01 Grace W R & Co Procede cyclique de preparation d'un catalyseur de haute purete du type zsm-5.
WO2007004166A1 (fr) 2005-06-30 2007-01-11 Firmenich Sa Microcapsules de polyurethane et de polyuree
EP2300146A1 (fr) 2008-06-16 2011-03-30 Firmenich S.A. Procédé de préparation de microcapsules de polyurée
WO2012007438A1 (fr) 2010-07-15 2012-01-19 Unilever Plc Particule pour libération avantageuse, procédés d'élaboration de ladite particule, compositions comprenant ladite particule et procédé de traitement de substrats
WO2013026657A1 (fr) 2011-08-24 2013-02-28 Unilever Plc Particules d'administration d'agent traitant contenant des polysaccharides non-ioniques
US20170189280A1 (en) * 2016-01-06 2017-07-06 The Procter & Gamble Company Methods Of Forming A Slurry With Microcapsules Formed From Phosphate Esters
WO2018115250A1 (fr) 2016-12-22 2018-06-28 Firmenich Sa Microcapsules de parfum à impact élevé et à densité équilibrée
WO2021185724A1 (fr) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules revêtues d'un dérivé de polysuccinimide
US20220119738A1 (en) * 2019-01-22 2022-04-21 Calyxia Detergent compositions having improved olfactory properties
WO2023006533A1 (fr) * 2021-07-29 2023-02-02 Firmenich Sa Microcapsules présentant une couche minérale
WO2024018014A1 (fr) * 2022-07-21 2024-01-25 Firmenich Sa Microcapsules composites

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025799A1 (fr) 1979-03-28 1981-04-01 Grace W R & Co Procede cyclique de preparation d'un catalyseur de haute purete du type zsm-5.
WO2007004166A1 (fr) 2005-06-30 2007-01-11 Firmenich Sa Microcapsules de polyurethane et de polyuree
EP2300146A1 (fr) 2008-06-16 2011-03-30 Firmenich S.A. Procédé de préparation de microcapsules de polyurée
WO2012007438A1 (fr) 2010-07-15 2012-01-19 Unilever Plc Particule pour libération avantageuse, procédés d'élaboration de ladite particule, compositions comprenant ladite particule et procédé de traitement de substrats
WO2013026657A1 (fr) 2011-08-24 2013-02-28 Unilever Plc Particules d'administration d'agent traitant contenant des polysaccharides non-ioniques
US20170189280A1 (en) * 2016-01-06 2017-07-06 The Procter & Gamble Company Methods Of Forming A Slurry With Microcapsules Formed From Phosphate Esters
WO2018115250A1 (fr) 2016-12-22 2018-06-28 Firmenich Sa Microcapsules de parfum à impact élevé et à densité équilibrée
US20220119738A1 (en) * 2019-01-22 2022-04-21 Calyxia Detergent compositions having improved olfactory properties
WO2021185724A1 (fr) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules revêtues d'un dérivé de polysuccinimide
WO2023006533A1 (fr) * 2021-07-29 2023-02-02 Firmenich Sa Microcapsules présentant une couche minérale
WO2024018014A1 (fr) * 2022-07-21 2024-01-25 Firmenich Sa Microcapsules composites

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Biodegradability of microcapsules: Microcapsule shells were purified from slurries", GASPARINI
C. VUILLEUMIER ET AL.: "Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development", PERFUME & FLAVORIST, vol. 33, 2008, pages 54 - 61
M. B. JACOBS: "Fenaroli's Handbook of Flavor Ingredients", 1975, CRC PRESS OR SYNTHETIC FOOD ADJUNCTS
OUALI ET AL., POLYMERS FOR ADVANCED TECHNOLOGIES, vol. 17, no. 1, 2006, pages 45 - 52
S. ARCTANDER, PERFUME AND FLAVOR CHEMICALS, 1969
S. ARCTANDER: "Perfume and Flavor Chemicals", 1969

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