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WO2025068225A1 - Microcapsules et procédé de préparation de microcapsules - Google Patents

Microcapsules et procédé de préparation de microcapsules Download PDF

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Publication number
WO2025068225A1
WO2025068225A1 PCT/EP2024/076849 EP2024076849W WO2025068225A1 WO 2025068225 A1 WO2025068225 A1 WO 2025068225A1 EP 2024076849 W EP2024076849 W EP 2024076849W WO 2025068225 A1 WO2025068225 A1 WO 2025068225A1
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WO
WIPO (PCT)
Prior art keywords
microcapsules
compound
group
dispersion
nucleophile
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/EP2024/076849
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English (en)
Inventor
Damien Berthier
Lahoussine Ouali
Laura ETCHENAUSIA
Marlène JACQUEMOND
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
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Firmenich SA
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Publication of WO2025068225A1 publication Critical patent/WO2025068225A1/fr
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Anticipated expiration legal-status Critical

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Classifications

    • 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
    • B01J13/16—Interfacial polymerisation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/22—Coating
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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

Definitions

  • the present invention relates to core-shell 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 microcapsules and a process for preparing said microcapsules. Summary of the invention
  • microcapsules of the invention therefore provide a solution to the above-mentioned problems as it allows preparing eco-friendly microcapsules with the desired stability in challenging bases.
  • the present invention relates to a core-shell microcapsule comprising:
  • Another object of the invention is a core-shell microcapsule slurry comprising at least one microcapsule, the microcapsule comprising:
  • Another object of the invention is a process for preparing a core-shell microcapsule slurry comprising the steps of: a) Optionally, providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the optional compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) Optionally, dispersing the two-phases dispersion into a continuous phase C2 comprising optionally at least one compound having at least two P-CI functions to form a multiple dispersion; e) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e).
  • the present invention also relates to perfumed consumer products and flavoured edible products comprising the microcapsules or microcapsule slurry as defined above. Detailed description of the invention
  • 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 coreshell 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)
  • 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.
  • the present invention relates to a core-shell microcapsule comprising:
  • 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 flavors, flavor ingredients, perfumes, perfume ingredients, nutraceuticals, cosmetics, pest control agents, biocide actives, agrochemical ingredients 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 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.
  • 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;
  • Balsamic ingredients coumarin, ethylvanillin and/or vanillin;
  • Citrus ingredients dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and/or 1 ,4(8)-p- menthadiene;
  • ingredients e.g. amber, powdery spicy or watery: dodecahydroSa, 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.
  • dodecahydroSa 6,6, 9a
  • 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-
  • 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.
  • 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 C5 and/or Cs rings;
  • Group 5 perfuming ingredients comprising a camphor-like ring structure
  • Group 6 perfuming ingredients comprising at least one C7 to C20 ring structure
  • Group 7 perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substitutent;
  • 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,
  • 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-1 '- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of 1- (5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1- cyclohexen-1-yl)-4-penten-1-one (origin: Firmenich SA, Geneva, Switzerland), 1- (2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (origin: Firmenich SA, Geneva, Switzerland), (1S,1'R)-[1-(3',3'-Dimethyl-1 '-cyclohexyl)ethoxycarbon
  • 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-ethy I-2 , 10, 10-tricycl
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75.
  • the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols.
  • the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
  • the oil phase (or the oil-based core) comprises:
  • “High impact perfume raw materials” should be understood as perfume raw materials having a LogT ⁇ -4.
  • the odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass.
  • the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
  • a “density balancing material’ should be understood as a material having a density greater than 1.07 g/cm 3 and having preferably low or no odor.
  • the odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“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 chain-length 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 GO 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
  • 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
  • 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 (6D 2 + 6P 2 + 6H 2 ) 0 5 , wherein 6D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore), 6P is the Hansen polarizability value (also referred to in the following as the dipole moment), and 6H is the Hansen Hydrogenbonding ("h-bonding") value (also referred to in the following as hydrogen bonding).
  • 6D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore)
  • 6P is the Hansen polarizability value (also referred to in the following as the dipole moment)
  • 6H is the Hansen Hydrogenbonding ("h-bonding") value (also referred to in the following as hydrogen bonding).
  • 6D SO ivent, QPshield, and 6H SO ivent are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and 6Df ra grance, 6Pf ra grance, and 6Hf ra grance 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 (6D) from 12 to 20, a dipole moment (6P) from 1 to 8, and a hydrogen bonding (6H) from 2.5 to 1 1 .
  • 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 (6D) from 12 to 20, preferably from 14 to 20, a dipole moment (6P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (6H) from 2.5 to 11 , preferably from 4 to 11 .
  • 6D atomic dispersion force
  • 6P dipole moment
  • 6H hydrogen bonding
  • At least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least of 98% of the perfume oil has at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (6D) from 12 to 20, a dipole moment (6P) from 1 to 8, and a hydrogen bonding (6H) from 2.5 to 11 .
  • 6D atomic dispersion force
  • 6P dipole moment
  • 6H hydrogen bonding
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (6D) from 12 to 20, preferably from 14 to 20, a dipole moment (6P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (6H) from 2.5 to 11 , preferably from 4 to 11.
  • 6D atomic dispersion force
  • 6P dipole moment
  • 6H hydrogen bonding
  • 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-T-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4-cyclopentadecen-1-one, cyclopentadecanone, (8Z)- oxacycloheptadec-8-en-2-one, 2-[5-(tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5- methyl-2-furyl]-2-propanol, muguet aldehyde, 1 ,5, 8-trimethyl-13- oxabicyclo[10.1.0]trideca-4,8-diene, (+-)-4,6,6,7,8,8-hexamethyl-1 , 3, 4, 6,7,
  • 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 antiparasite.
  • 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 liquid extracted or distilled from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, any other citrus fruit or variation or hybrid thereof, pomegranates, kiwifruits, watermelons, apples, bananas, blueberries, melons, ginger, bell peppers, cucumbers, passion fruits, mangos, pears, tomatoes, and strawberries.
  • the flavor comprises a composition that comprises limonene, in a particular embodiment, the composition is a citrus that further comprises limonene.
  • 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 shell of the microcapsule comprises the reaction product between at least one compound having at least two P-CI functions and a nucleophile.
  • P-CI function refers to a covalent bond between a P atom and a Cl atom.
  • the at least two Cl functions are on the same P atom.
  • the compound having at least two P-CI functions comprises a P atom that is connected to at least two Cl atoms via covalent bonds.
  • the compound having at least two P-CI functions can be selected from the group consisting of compound with formula PXC , where X is O, S, or NH or NR 1 where R 1 is any hydrocarbon group, optionally comprising heteroatoms.
  • the compound having at least two P-CI functions can be selected from the group consisting of compound phosphorus oxy trichloride (POCI3), thiophosphorus trichloride (PSCI3), phosphorimidic trichloride (PNHCI3), N-substituted-phosphorimidic trichloride (PNR 1 Cl3), phosphorus trichloride, phosphorus pentachloride, hexachlorocyclophosphazene (HCCP) and its derivatives, R1OPXCI2 (with X is O, NH, NR 1 or S), such as alkyl phosphorodichloridate (R 1 OPOCl2) and/or alkyl dichlorothiophosphate (R 1 OPSCh)
  • the compound having at least two P-CI functions can be selected from the group consisting of compounds with formula PXCI3, PNHCI3 and PNR 1 C , where X is O, S, where R 1 is any hydrocarbon group, optionally comprising heteroatoms.
  • the compound having at least two P-CI functions can be selected from the group consisting of compound phosphorus oxy trichloride (POCI3), thiophosphorus trichloride (PSCI3), phosphorimidic trichloride (PNHCI3), N-substituted-phosphorimidic trichloride (PNR 1 Cls), phosphorus trichloride, phosphorus pentachloride, hexachlorocyclophosphazene (HCCP), 2,2,4,4-tetraamino-6,6- dichlorocyclotriphosphazene (TCPA), a copolymer of hexa-(4-aldehyde-phenoxy)- cyclo-triphosphazene and
  • the hydrocarbon group is a functional or not C1- C50 hydrocarbon 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 ...” it is meant that said hydrocarbon group optionally comprises one, two, three or more heteroatoms.
  • 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 Ce hydrocarbon group comprising two ether groups, i.e. a Ce hydrocarbon comprising two oxygen atoms.
  • the compound having at least two P-CI functions is hexachlorocyclophosphazene (HCCP) or its derivatives or its polymer.
  • the compound having at least two P-CI functions is selected from the group consisting of hexachlorocyclophosphazene (HCCP), 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (TCPA), a copolymer of hexa-(4-aldehyde-phenoxy)-cyclo-triphosphazene (HACP) and 2,2,4,4-tetraamino- 6,6-dichlorocyclotriphosphazene (HACP-co-TCPA) or mixtures thereof.
  • HCCP hexachlorocyclophosphazene
  • TCPA 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene
  • HACP-co-TCPA 2,2,4,4-tetraamino- 6,6-dichlorocyclotriphosphazene
  • the compound having at least two P-CI functions is not p-(chlorocarbonyl)-phenyl-dichlorophosphate, [2,2-bis-(4-hydroxyphenyl)- propane]-bisdichlorophosphate, phenylphosphonic dichloride or reaction products thereof or mixtures thereof.
  • a nucleophile compound is defined as a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction.
  • the nucleophile compound may be chosen in the group consisting of nitrogen nucleophile, sulfur nucleophile, oxygen nucleophile, carbon nucleophile, phosphor nucleophile, and mixtures thereof.
  • Nitrogen nucleophile compound may have at least one functional group chosen in the group consisting of ammonia, azide, amines, nitrites, hydroxylamine, hydrazin, carbazide, phenylhydrazine, semicarbazide, and amide, and mixtures thereof.
  • Sulfur nucleophile compound may have at least one functional group chosen in the group consisting of hydrogen sulfide and its salts, thiols (RSH), thiolate anions (RS-), anions of thiolcarboxylic acids (RC(O)-S-), and anions of dithiocarbonates (RO-C(S)-S-) and dithiocarbamates (R2N-C(S)-S-) and mixtures thereof.
  • RSH thiols
  • RS- thiolate anions
  • R(O)-S- anions of thiolcarboxylic acids
  • R2N-C(S)-S- dithiocarbamates
  • Oxygen nucleophile compound may have at least one functional group chosen in the group consisting of water, hydroxide anion, alcohols, alkoxide anions, carboxylate anions, carbonates, sulfonate, sulfate, sodium phosphates, sodium silicates, borax, sodium tetraborate, and mixtures thereof.
  • Carbone nucleophile compound may have at least one functional group chosen in the group consisting of enols carbon nucleophiles, malonate and acetoacetate.
  • Phosphor nucleophile compound may have at least one functional group chosen in the group consisting of phosphine, phosphite anion and mixture thereof.
  • the nucleophile is chosen in the group consisting of alcohol, amine, thiol and mixtures thereof.
  • Alcohol and “polyol” can be used indifferently in the present invention.
  • the amine is chosen in the group consisting of cystamine, EDA, DETA, Pentamethylenediamine, hexamethylenediamine, poly(L-lysine) (that can be modified), L-lysine, L-lysine ethyl ester, cystine dimethyl ester, and mixtures thereof.
  • the amine is chosen in the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride, a xylylene diamine, 1 ,2- diaminocyclohexane, 1 ,4-diaminocyclohexane, polyetheramines, ethylene diamine, diethylene triamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 1 ,4 Diaminobutane, 2,2Dimethyl-1 ,3- propanediamine, 1 ,3-diaminopentane (Dytek EP diamine), 1 ,2 Diaminopropane, triethylenetetramine , 1 ,3-diaminopropane; urea; ethylene urea; aminoguan
  • the alcohol (or polyol) is chosen in the group consisting of phloroglucinol, Hydroquinone, Hydroquinone bis(2- hydroxyethyl)ether, 1 ,4-cyclohexanedimethanol, Resorcinol, Isosorbide, Pentaerythritol, Erythritol, Trimethylolpropane, Di-trimethylolpropane, sorbitol, mannitol, xylitol, triethanolamine, diglycerol, triglycerol and corresponding partial esters, polyglycerol and corresponding partial esters, and mixtures thereof.
  • the thiol (or polythiol) is chosen Ethylene glycol bis-mercaptoacetate, dithiothreitol, trimethylolpropane tris(3- mercaptopropionate), 2,2'-Thiodiethanethiol, Pentaerythritol tetrakis(3- mercaptopropionate), 2-mercaptoethanol, 3-Aminopropane-1 -thiol, 3-Aminopropane- 1-thiol hydrochloride, 3-mercapto-1 ,2-propanediol, 3-Mercapto-1 -propanol, 1- Mercapto-2-propanol, 6-Mercapto-1 -hexanol, Mercapto-acetic acid 4- mercaptoacetoxy-butyl ester, 1 -Thioglycerol, 2- ⁇ 2-[2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-
  • the nucleophile is not an amine or an alcohol.
  • the nucleophile is not hexamethylenediamine, polyvinyl alcohol, ethyylenediamine, diethylenetriamine, a melamine-based crosslinker or any reaction product thereof or mixtures thereof.
  • the nucleophile and the compound having at least two P-CI functions are the same molecule.
  • the nucleophile and the compound having at least two P-CI functions are the same molecule, wherein the molecule is 2,2,4,4-tetraamino- 6,6-dichlorocyclotriphosphazene.
  • the nucleophile and the compound having at least two P-CI functions are not the same molecule.
  • the core-shell microcapsule does not comprise a silicon containing monomer or a reaction product thereof. According to an embodiment, the core-shell microcapsule does not comprise silicon.
  • 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 polymer (such as non-ionic polysaccharide), anionic polymer (such as polysaccharide), a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724) and mixtures thereof to form an outer coating to the microcapsule.
  • a non-ionic polymer such as non-ionic polysaccharide
  • anionic polymer such as polysaccharide
  • a cationic polymer such as sodium quaternary ammonide
  • a polysuccinimide derivative as described for instance in WO2021185724
  • the microcapsule does not comprise an outer coating.
  • Non-ionic polysaccharide polymers are well known to a person skilled in the art and are described for instance in W02012/007438 page 29, lines 1 to 25 and in WO2013/026657 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).
  • 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.
  • Another object of the invention is a solid particle comprising:
  • a carrier material preferably a polymeric carrier material chosen in the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carragenans, cellulose derivatives and mixtures thereof, and
  • Solid particle as defined above and microcapsule powder can be used indifferently in the present invention.
  • Another object of the invention is a process for preparing a core-shell microcapsule slurry comprising the steps of: a) Optionally, providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the optional compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) Optionally, dispersing the two-phases dispersion into a continuous phase C2 comprising optionally at least one compound having at least two P-CI functions to form a multiple dispersion; e) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e).
  • step a) at least one compound having at least two P-CI functions is added in step a) and/or in step d).
  • the at least one compound having at least two P-CI functions used in step a) and/or in step d) can be used as a pure compound (meaning without any reaction with a reactant) or can be used as a modified compound if a reactant is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e).
  • the reactant is a nucleophile which can be the same or a different nucleophile defined in the present invention.
  • the process comprises the steps of: a) Providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) curing the dispersion obtained in step c) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d).
  • the process comprises the steps of: a) Providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) dispersing the two-phases dispersion into a continuous phase C2 comprising optionally at least one compound having at least two P-CI functions to form a multiple dispersion; e) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e).
  • the process comprises the steps of: a) Providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) dispersing the two-phases dispersion into a continuous phase C2 comprising at least one compound having at least two P-CI functions to form a multiple dispersion; e) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e).
  • the compound having at least two P-CI functions of step d) and be the same or can be different from the compound having at least two P-CI functions of step a).
  • the process comprises the steps of: a) providing at least one hydrophobic material to form an oil phase; b) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; c) dispersing the two-phases dispersion into a continuous phase C2 comprising at least one compound having at least two P-CI functions to form a multiple dispersion; d) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d).
  • the process comprises the steps of a) Optionally, providing at least one compound having at least two P-CI functions b) admixing at least one hydrophobic material with the optional compound obtained in step a) to form an oil phase; c) Dispersing the oil phase into a continuous phase C1 or dispersing a continuous phase C1 into the oil phase to form a two-phases dispersion; d) Optionally, dispersing the two-phases dispersion into a continuous phase C2 comprising optionally at least one compound having at least two P-CI functions to form a multiple dispersion; e) curing the dispersion obtained in step c) or d) to form microcapsules in the form of a slurry, wherein a nucleophile is added in step a) and/or step b) and/or step c) and/or step d) and/or in step e), and wherein a compound having at least two P-CI functions is added in step a) and/
  • the embodiments disclosed for the core-shell microcapsules also apply for the process for preparing core-shell microcapsules. It applies notably to the compound having at least two P-CI functions, the hydrophobic material, or the nucleophile.
  • step a) of the process a solution comprising at least one compound having at least two P-CI functions is prepared.
  • the compound having at least two P-CI functions is defined as previously.
  • the compound having at least two P-CI functions is added in an amount comprised between 0.5 and 10%, preferably between 2 and 6% by weight based on the total weight of the two-phases dispersion.
  • the continuous phase C1 comprises, preferably consists of water.
  • the continuous phase C1 is a water phase.
  • the two-phases dispersion is an oil-in-water emulsion.
  • the two-phases dispersion is a water-in-oil emulsion.
  • the continuous phase C1 comprises water and an alcohol such as glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
  • an alcohol such as glycerol, 1 ,4-butanediol, ethylene glycol and mixtures thereof.
  • the continuous phase C1 consists of alcohol.
  • step d) the two-phases dispersion is dispersed into a continuous phase C2 to form a multiple dispersion.
  • the continuous phase C2 can be any hydrophobic solvent or free oil.
  • the multiple dispersion can be an O/W/O (oil in water in oil) or W/O/W (water in oil in water) emulsions.
  • a stabilizer can be added in the oil phase and/or in the continuous phase C1 .
  • 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 0.1 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 can act as a nucleophile. Therefore, according to an embodiment, the stabilizer is the nucleophile of 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 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 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.
  • 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, 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.
  • 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
  • Potato proteins are typically extracted from potato tuber (Solanum tuberosum). According to an embodiment, the potato protein is a native potato protein and preferably patatin.
  • the protein used in this invention may be native, partially or completely denaturated by any suitable method.
  • Denaturation is a process which modify the conformational structure of a protein by unfolding, i.e., it involves the disruption and possible destruction of both the secondary and tertiary structures of the protein. Indeed, denaturation implicates the breaking of many of the weak linkages, or bonds (e.g., hydrogen bonds), within a protein molecule that are responsible for the highly ordered structure of the protein in its native state. Denaturation is reversible (the proteins can regain their native state when the denaturating influence is removed) or irreversible.
  • Denaturation can be brought about in various ways. Proteins can be denatured by exposure to temperature, radiation or mechanical stress including shear, changes in pH (treatment with a base or an acid), treatment with oxidizing or reducing agents, inorganic salt, certain organic solvents, chaotropic agents (i.e, compounds having a positive chaotropic value - kJ Kg -1 mole on the Hallsworth Scale - such as guanidine salts - e.g., guanidine carbonate, guanidine hydrochloride -, urea, calcium chloride, n- butanol, ethanol, lithium perchlorate, lithium acetate, magnesium chloride, phenol, 2- propanol, sodium dodecyl sulfate, thiourea).
  • chaotropic agents i.e, compounds having a positive chaotropic value - kJ Kg -1 mole on the Hallsworth Scale - such as guanidine salts - e.
  • the protein used in this invention can also be derivatized or modified (e.g., derivatized or chemically modified).
  • the protein can be modified by covalently attaching sugars, lipids, peptides or chemical groups such as phosphates or methyl.
  • a base is added in the continuous phase C1.
  • the base is chosen in the group consisting of guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, and mixtures thereof.
  • the base When used, the base is typically used in an amount comprised between 0.1 and 10%, preferably between 3 and 7% by weight based on the total weight of the continuous phase C1.
  • the nucleophile is defined as previously.
  • the nucleophile is added in the oil phase and/or in the continuous phase C1 .
  • the nucleophile can be added in an amount comprised between 0.5 and 10%, preferably between 1 and 4% by weight based on the total weight of the two-phases dispersion.
  • step d) the dispersion obtained in step c) or d) is cured to form microcapsules in the form of a slurry.
  • a non-ionic polymer such as non-ionic polysaccharide
  • anionic polymer such as polysaccharide
  • a cationic polymer such as polysaccharide
  • a polysuccinimide derivative as described for instance in WO2021185724
  • said step is performed at a temperature comprised between 5 and 90°C, possibly under pressure, for 1 to 24 hours. More preferably it is performed at between 10 and 80°C for between 30 minutes and 5 hours.
  • the process does not comprise the addition of a silicon containing monomer.
  • 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 hardened enzymatically 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 ureaformaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
  • aminoplast copolymer such as melamine-formaldehyde or ureaformaldehyde 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
  • 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-soluble guanidine salt and
  • 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 C4-6 2,2- 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.
  • 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 crosslinked.
  • 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, betalactoglobulin, 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 crosslinked; wherein the protein contains preferably a mixture comprising sodium caseinate and a globular protein, preferably whey protein, - optionally at least an outer mineral layer.
  • sodium caseinate and/or whey protein is (are) cross-linked 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 core-shell 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 1% and 50% w/w, preferably between 2 and 25% w/w
  • 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 the form of a slurry.
  • the present invention also relates to a perfuming composition
  • a perfuming composition comprising
  • the 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 obtained by the process according to the present invention or as described herein-above 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 core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above.
  • 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 obtained by the process according to the present invention or as described herein-above.
  • the total amount of the core-shell microcapsule or core-shell microcapsule slurry obtained by the process according to the present invention or as described herein-above 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 obtained by the process according to the present invention or as described herein-above 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 coingredient 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 coingredients 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-
  • 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 obtained by the process according to the present invention or as described herein-above 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 obtained by the process according to the present invention or as described herein-above, and
  • 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 homecare 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.
  • Another object of the invention is a consumer product comprising: a personal care active base, and 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 skin-care 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 skin-care product e.g. a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product
  • Another object of the invention is a consumer product comprising: - a home care or a fabric care active base, and
  • Home care or fabric care active bases in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
  • 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).
  • 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 polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, - microcapsules or a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more
  • An object of the invention is a consumer product in the form of a solid detergent composition comprising:
  • a solid detergent active base preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxydes, alkyl polyglucosides, alkyl polyglucosamides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition,
  • anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol
  • microcapsule powder or microcapsule slurry 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, cocamidopropyl betaine, cocamide MEA, alkylglucosides and aminoacid based surfactants and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, - 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
  • 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 nonionic 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,
  • Example 4-1 (Capsules D1 - NICP2712): e-Poly(L-lysine) (1 g), 2,2-dimethoxyethanal (60%, 0.22 g), glyoxylic acid (40%, 0.23 g), and n-octanal (0.04 g) were dissolved in water (10 g). The pH value was adjusted above 10 with a solution of sodium hydroxide in water at 30%. The reaction mixture was added to a solution of potato protein 15 (Solanic 200, origin: Avebe, NL, 0.8 g) in water (79.2 g) and the pH value was measured at 10.1. HCCP (0.21 g) was dissolved in perfume oil (20 g).
  • the pH value was reduced to 6.1 with acetic acid.
  • the emulsion was transferred to a 250 mL reactor and stirred with an anchor. The temperature increased to 80°C over the period of 1 h and was maintained at 80°C for 3 h.
  • the dispersion was cooled down to room temperature to afford a slurry.
  • Example 4-2 Capsules D2 - NICP2776: The capsules were prepared according to the protocol of example 4-1 with an aqueous phase comprising e-Poly(L-lysine) (2 g), 2,2-dimethoxyethanal (60%, 0.45 g), glyoxylic acid (40%, 0.48 g), n-octanal (0.09 g) in water (10 g) and a solution of potato protein (1.6 g) in water (78.4 g) and an oil phase comprising HCCP (0.42 g) and perfume oil (20 g).
  • aqueous phase comprising e-Poly(L-lysine) (2 g), 2,2-dimethoxyethanal (60%, 0.45 g), glyoxylic acid (40%, 0.48 g), n-octanal (0.09 g) in water (10 g) and a solution of potato protein (1.6 g) in water (78.4 g) and an oil phase comprising
  • Capsules of example 5-2 (Capsules E1): e-Poly(L-lysine) (2 g), 2,2-dimethoxyethanal (60%, 0.45 g), glyoxylic acid (40%, 0.47 g), and n-octanal (0.09 g) were dissolved in water (10 g). The pH value was adjusted to 12.2 with a solution of sodium hydroxide in water at 30%. The reaction mixture was added to a solution of Solanic 200 (1 .6 g) in water (78.4 g) and the pH value was measured at 9.9. Tri(4-formylphenoxy)- trichlorocyclophosphazenes (1 .07 g) were dissolved in perfume oil (20 g).
  • the emulsion was stirred at room temperature for 30 minutes.
  • the pH value was reduced to 5.5 with acetic acid.
  • the emulsion was transferred to a 250 mL Schmizo reactor and stirred with an anchor.
  • the dispersion was cooled down to room temperature to afford a slurry.
  • HACP 4-hydroxybenzaldehyde (3.75 g, 30.7 mmol), anhydrous K2CO3 (4.20 g, deacidification reagent) were dissolved in anhydrous THF (15 mL) in a 25 mL three-necked round-bottom flask equipped with a condenser and a stirring bar under N2. Then a solution of HCCP (1 .5 g, 4.27 mmol) in anhydrous THF (3 mL) was added dropwise at 0°C and the mixture was heated at 60°C for 7 h. Then the solution was poured in water, a white solid precipitated. The product was washed with excess of water and then isopropanol.
  • HACP-TCPA copolymer Preparation of HACP-TCPA copolymer: HACP (0.086 g, 0.1 mmol) and TCPA (0.162 g, 0.6 mmol) were mixed and dissolved in DMSO (5 ml_) in a 10 mL screw-cap vial equipped with a stirring bar. Formic acid (0.3 mL, 80 mmol) was added, and the vial was placed in water bath at 80°C for 5 h. Then the vial was left stirring at rt overnight. Precipitate was filtered and washed with acetone, ethanol, and water, and dried on air overnightto afford a red solid (0.1 g).
  • Polymer shell of microcapsules from example 5 was purified according to the protocol published by Gasparini et al. in Molecules (2020), 25(3), 718. The polymer was characterized by solid-state NMR and then tested under the OECD301 F conditions to afford a biodegradation greater than 60% after 28 days.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a fabric softener composition to add the equivalent of 0.116% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a powder detergent composition to add the equivalent of 0.2% perfume.
  • Emulsions A-E having the following ingredients are prepared.
  • Table 8 Composition of Emulsions A-E and composition of granulated powder A-E after spray-drying
  • Components for the polymeric matrix are added in water at45-50°C until complete dissolution.
  • free perfume B 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 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.
  • 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.
  • Table 11 Unit dose composition
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a concentrated all-purpose cleaner composition to add the equivalent of 0.2% perfume.
  • Neodol 91-8 ® trademark and origin : Shell Chemical
  • Solid scent booster composition The following 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 (heat to melt Monomuls 90L-12 in Texapon NSO IS) are added.
  • the mixture is mixed well.
  • Phase D and Phase E are added while agitating.
  • the pH was adjusted with citric acid solution till pH: 5.5 - 6.0.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • a premix comprising Guar Hydroxypropyltrimonium Chloride and Polyquaternium-10 are added to water and Tetrasodium EDTA while mixing. When the mixture is homogeneous, NaOH is added. Then, 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. At 45 °C, 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.
  • Rinse-off hair composition 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 Alfa Aesar 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
  • 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 I 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 roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A and B are heated separately to 75°C; Part A is added to part B under stirring and the mixture is homogenized for 10 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.
  • antiperspirant roll-on composition A sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant roll-on composition to add the equivalent of 0.2% perfume. Table 22: antiperspirant roll-on composition
  • 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
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant roll-on 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.
  • Asufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Asufficient 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.
  • Asufficient 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.
  • CARBOPOL AQUA SF-1 POLYMER trademark and origin: NOVEON
  • KATHON CG trademark and origin: ROHM & HASS
  • Asufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Asufficient 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 a soap bar formulation a concentration of 7.5% w/w.
  • a sufficient amount of exemplified microcapsules is weighed and mixed into a cosmetic skin cream (see composition below) at a concentration of 5%w/w.
  • Hand Dishwash Asufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • 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.
  • 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.
  • 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.
  • 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 35 Mouthwash formulation

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Abstract

La présente invention concerne des microcapsules de type cœur-écorce. L'invention concerne également un procédé de préparation desdites microcapsules. L'invention concerne en outre des compositions parfumantes et des produits de consommation comprenant lesdites microcapsules, en particulier des produits de consommation parfumés qui se présentent sous la forme de produits de soins à domicile ou de soins personnels.
PCT/EP2024/076849 2023-09-28 2024-09-25 Microcapsules et procédé de préparation de microcapsules Pending WO2025068225A1 (fr)

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3624248A (en) * 1967-03-07 1971-11-30 Pennwalt Corp New phosphorus-containing polymers and the process of making said polymers
US4025455A (en) * 1974-06-19 1977-05-24 The Mead Corporation Cross-linked hydroxypropylcellulose microcapsules and process for making
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
WO2018115250A1 (fr) 2016-12-22 2018-06-28 Firmenich Sa Microcapsules de parfum à impact élevé et à densité équilibrée
US20190255502A1 (en) * 2016-09-20 2019-08-22 Firmenich Sa Hybrid microcapsules
WO2021185724A1 (fr) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules revêtues d'un dérivé de polysuccinimide
US20230001373A1 (en) * 2019-12-13 2023-01-05 Firmenich Sa Hybrid Microcapsules

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3624248A (en) * 1967-03-07 1971-11-30 Pennwalt Corp New phosphorus-containing polymers and the process of making said polymers
US4025455A (en) * 1974-06-19 1977-05-24 The Mead Corporation Cross-linked hydroxypropylcellulose microcapsules and process for making
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
US20190255502A1 (en) * 2016-09-20 2019-08-22 Firmenich Sa Hybrid microcapsules
WO2018115250A1 (fr) 2016-12-22 2018-06-28 Firmenich Sa Microcapsules de parfum à impact élevé et à densité équilibrée
US20230001373A1 (en) * 2019-12-13 2023-01-05 Firmenich Sa Hybrid Microcapsules
WO2021185724A1 (fr) 2020-03-16 2021-09-23 Firmenich Sa Microcapsules revêtues d'un dérivé de polysuccinimide

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Title
"Fenaroli's Handbook of Flavor Ingredients", 1975, CRC PRESS
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 (2008-09-01), pages 54 - 61
GASPARINI ET AL., MOLECULES, vol. 25, no. 3, 2020, pages 718
M. B. JACOBS: "Synthetic Food Adjuncts", 1947, VAN NOSTRAND CO., INC.
S. ARCTANDER: "Perfume and Flavor Chemicals", 1969

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