Polyamide-based microcapsules

Abstract

The present invention relates to a new method for preparing polyamide-based microcapsules. The polyamide-based microcapsules are also the subject of the present invention. Perfumed compositions and consumer products, especially perfumed consumer products in the form of home care or personal care products, comprising said microcapsules are also part of the present invention.

Description

[Technical field]

[0001] The present invention relates to a new method for preparing polyamide-based microcapsules. The polyamide-based microcapsules are also the subject of the present invention. Perfumed compositions and consumer products, especially perfumed consumer products in the form of home care or personal care products, comprising said microcapsules are also part of the present invention.

[0002] 2. Background of the Invention One of the problems faced by the fragrance industry is that the olfactory benefits provided by odoriferous compounds are lost relatively quickly due to their volatility, especially the volatility of "top notes". In order to control the release rate of volatile substances, delivery systems such as perfume-containing microcapsules need to protect the core payload and release it later when triggered. A key requirement by the industry for these systems is to withstand suspension in a challenging base without physical dissociation or decomposition. This is referred to as the stability of the delivery system. For example, perfumed personal and household cleaners that contain high levels of aggressive surfactant detergents are very challenging for the stability of microcapsules.

[0003] Polyurea and polyurethane based microcapsule slurries are widely used, for example, in the perfume industry, since they provide a long-lasting and pleasant olfactory effect after application on various substrates. These microcapsules have been widely disclosed in the prior art (see, for example, the applicant's WO 2007 / 004166 or EP 2300146).

[0004] In addition to performance in terms of stability and olfactory performance, consumer demand for environmentally friendly delivery systems is becoming increasingly important and is driving the development of new delivery systems.

[0005] There is therefore still a need to provide new microcapsules using more environmentally friendly materials, without compromising the performance of the microcapsules in terms of stability, especially in hostile media such as consumer product bases, and also in providing good performance in terms of delivery of active ingredients, e.g. olfactory performance in the case of perfumery ingredients.

[0006] The present invention proposes a solution to the above mentioned problems by providing new polyamide-based microcapsules and a method for preparing said microcapsules.

[0007] Summary of the Invention It has now surprisingly been found that by reacting acyl chloride with at least one amino compound and protein in the presence of a crosslinking agent, preferably an enzymatic crosslinking agent, it is possible to obtain high performance core-shell microcapsules encapsulating hydrophobic materials.The method of the present invention therefore provides a solution to the above-mentioned problems, since it allows the preparation of microcapsules with the desired stability in a troublesome base.

[0008] In a first aspect, the present invention provides a method for preparing a polyamide-based core-shell microcapsule slurry, comprising the steps of: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to form an oil-in-water emulsion; c) carrying out a curing step to form polyamide-based microcapsules in the form of a slurry. Including, adding at least one amino compound A to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), Adding the protein to the oil and / or water phase; A cross-linking agent is added in step b) and / or in step c) and / or after step c). It concerns the method.

[0009] In a second aspect, the present invention relates to a polyamide-based core-shell microcapsule slurry obtainable by a method according to any of the preceding claims.

[0010] A third subject of the invention is a polyamide-based core-shell microcapsule, the microcapsule having an oily core containing a hydrophobic material, preferably a fragrance; a polyamide-based shell, Acyl chlorides, Amino compounds A, Proteins, and Optionally, an amino compound B The shell and Including, The shell is a polyamide-based core-shell microcapsule having a breaking stress of less than 10 MPa.

[0011] Another subject of the present invention is a polyamide-based core-shell microcapsule slurry comprising at least one microcapsule, the microcapsule being a core comprising a hydrophobic material, preferably a fragrance, preferably an oily core; a polyamide-based shell, Acyl chlorides, Amino compounds A, optionally an amino compound B, ·protein The shell and Including, The shell is a polyamide-based core-shell microcapsule slurry having a breaking stress of less than 10 MPa.

[0012] In a fifth and sixth aspect, the present invention relates to perfumed consumer products and flavoured edible products comprising microcapsules as defined above.

[0013] Detailed Description of the Invention Unless otherwise stated, percentages (%) are intended to refer to percentages by weight of the composition.

[0014] "Active ingredient" means a single compound or a combination of ingredients.

[0015] By "fragrance or flavor oil" is meant a single fragrance or flavoring compound or a mixture of several fragrance or flavoring compounds.

[0016] "Consumer product" or "final product" means a manufactured item that is ready for distribution, sale and use by a consumer.

[0017] For the sake of clarity, the expression "dispersion" in the present invention means a system in which particles are dispersed in a continuous phase of different composition, and specifically includes a suspension or an emulsion.

[0018] By "microcapsule" or the like in the present invention is meant a core-shell microcapsule having a particle size distribution in the micron range (e.g. mean diameter (d(v,0.5)) comprised between about 1 and 3000 microns, preferably between 1 and 500 microns) and comprising an outer solid polyamide-based shell and an inner continuous oil phase surrounded by the outer shell.

[0019] "Microcapsule slurry" means microcapsules dispersed in a liquid. According to one embodiment, the slurry is an aqueous slurry, i.e., the microcapsules are dispersed in an aqueous phase.

[0020] By "amino compound" is to be understood a compound which has at least two reactive amine groups.

[0021] In the present invention, the terms "acyl chloride" and "acid chloride" are used interchangeably.

[0022] By "polyamide-based microcapsule" is meant that the shell of the microcapsule comprises a polyamide material. The expression "polyamide-based microcapsule" may also encompass a shell made of a composite material that includes a polyamide material and another material, such as a protein.

[0023] "Polyamide-based microcapsules" and "polyamide microcapsules" are used interchangeably in the present invention.

[0024] It has been found that reacting an acyl chloride with at least one amino compound and a protein in the presence of a cross-linking agent (e.g. transglutaminase) during the process can result in core-shell polyamide-based microcapsules with good overall performance in a challenging base.

[0025] Method for preparing a polyamide-based microcapsule slurry In a first aspect, the present invention provides a method for preparing a polyamide-based core-shell microcapsule slurry, comprising the steps of: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to form an oil-in-water emulsion; c) carrying out a curing step to form polyamide-based microcapsules in the form of a slurry. Including, adding at least one amino compound A to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), Adding the protein to the oil and / or water phase; A cross-linking agent is added in step b) and / or in step c) and / or after step c). It concerns the method.

[0026] In one step of the process, an oil phase is formed by combining at least one hydrophobic material with at least one acyl chloride.

[0027] Hydrophobic Materials The hydrophobic material according to the present invention may be an "inert" material such as a solvent or an active ingredient. The core is preferably an oily core.

[0028] When the hydrophobic material is an active ingredient, the active ingredient is preferably selected from the group consisting of flavors, flavor ingredients, fragrances, fragrance ingredients, dietary supplements, cosmetics, pest control agents, biocidal active agents and mixtures thereof.

[0029] According to certain embodiments, the hydrophobic material comprises a mixture of a fragrance and another ingredient selected from the group consisting of dietary supplements, cosmetics, pest control agents and biocidal actives.

[0030] In one embodiment, the hydrophobic material comprises a phase change material (PCM).

[0031] According to certain embodiments, the hydrophobic material comprises a mixture of a biocidal active and another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, and pest control agents.

[0032] According to certain embodiments, the hydrophobic material comprises a mixture of a pesticide and another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, and biocide actives.

[0033] According to certain embodiments, the hydrophobic material comprises a fragrance.

[0034] According to a particular embodiment, the hydrophobic material consists of a fragrance.

[0035] According to a particular embodiment, the hydrophobic material consists of a biocidal active agent.

[0036] According to certain embodiments, the hydrophobic material comprises a pesticide.

[0037] By "perfume" (or also "perfume oil") herein is meant an ingredient or composition that is liquid at about 20°C. According to any one of the above embodiments, said perfume oil may be a perfuming ingredient alone or a mixture of ingredients in the form of a perfume composition. By "perfuming ingredient" herein is meant a compound that is used for the primary purpose of imparting or modulating an odor. In other words, such an ingredient, in order to be considered a perfuming ingredient, must not only have an odor, but must be recognized by the skilled artisan as being at least capable of imparting or modifying the odor of the composition in a positive or pleasant way. For the purposes of the present invention, perfume oil also includes combinations of perfuming ingredients with any substance that both improves, enhances or modifies the delivery of the perfuming ingredient, such as perfume precursors, modifiers, emulsions or dispersions, and combinations that provide additional benefits beyond modifying or imparting an odor, such as persistence, blooming, deodorization, antibacterial action, microbial stability, pest control.

[0038] The nature and type of perfume ingredients present in the oil phase do not require a more detailed description here, and are in any case not comprehensive, and those skilled in the art can select them based on their general knowledge according to the intended use or application and the desired organoleptic effect.Generally, these perfume ingredients belong to various chemical classes, such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds, and essential oils (e.g. thyme oil), and said perfume co-ingredients can be of natural or synthetic origin.Many of these co-ingredients are described in any case in reference literature, for example in the book Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or its more recent editions, or other treatises of the same kind, and in the abundant patent literature in the field of perfumery.

[0039] Mention may in particular be made of perfuming ingredients commonly used in perfume formulations such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and / or nonenal; - Aromatic Herbal Ingredients: Eucalyptus Oil, Camphor, Eucalyptol, 5-Methyltricyclo[6.2.1.0 2,7 ]undecane-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 α-pinene; - Balsam components: coumarin, ethyl vanillin and / or vanillin; - Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; - Floral components: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta-ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2 ,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, 2,5-dimethyl-2-indanethanol, 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylphenyl)propanal, 1,2-dimethylphenylacetate, 1,3-dimethylphenylacetate, 1,4-dimethylphenylacetate, 1,5-dimethylphenylacetate, 1,6-dimethylphenylacetate ...6-dimethylphenylacetate, 1,7-dimethylphenylacetate, 1,6-dimethylphenylacetate, 1,7-dimethylphenylacetate, 1,8-dimethylphenylacetate, 1,8-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9-dimethylphenylacetate, 1,9 ethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, cis-high methyl dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, vergyl proprionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-Trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or methyl ionone isomeric mixture;, - Fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate, and / or diethyl 1,4-cyclohexanedicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styralyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, 3-methyl-5-cyclo pentadecen-1-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody Ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.02,7]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, Patchouli Oil, terpene fraction of patchouli oil, Clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; - other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any stereoisomers thereof, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, 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.

[0040] It is also understood that the above ingredients may be compounds known to provide a controlled release of various types of perfuming compounds, also known as properfumes or profragrances. Non-limiting examples of suitable properfumes include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 3-(dodecylthio)-4-(2,6,6-trimethyl-2 ... O)Octan-4-one, 2-phenylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-ylhexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2 -((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl) )oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof.

[0041] The perfuming ingredients can be dissolved in solvents currently used in the perfume industry. The solvent is preferably not alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (a rosin-based resin available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, such as Abalyn® or benzyl benzoate. Preferably, the perfume contains less than 30% solvent. More preferably, the perfume contains less than 20% and even more preferably less than 10% solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially solvent-free.

[0042] Preferred perfuming ingredients are those with high steric hindrance (bulky substances), in particular from one of the following groups: - Group 1: Perfuming ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C1-C4 alkyl or alkenyl substituent; - Group 2: Perfuming ingredients containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4-C8 alkyl or alkenyl substituent; - Group 3: Perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5-C8 alkyl or alkenyl substituent, or substituted with at least one phenyl substituent and optionally one or more linear or branched C1-C3 alkyl or alkenyl substituents; - Group 4: Perfuming ingredients containing at least two fused or linked C5 and / or C6 rings; - Group 5: Odour components containing camphor-like ring structures; - Group 6: at least one C7-C 20 Fragrance components containing ring structures; - Group 7: Perfuming ingredients having a logP value of more than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent; Examples of members of each of these groups are as follows: - group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (supplier: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (supplier: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylates, rose oxide, (S)-1,8-p-menthadien-7-ol (supplier: Firmenich SA, Geneva, Switzerland), 1-p-menthen-4-ol, (1RS,3RS,4SR)-3-p-menthanyl acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (Supplied by: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1,4-cyclohexanediethyl dicarboxylate (Supplied by: Firmenich SA, Geneva, Switzerland), (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Supplied by: Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (supplied by Firmenich SA, Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde; - group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (supplied by Givaudan SA, Vernier, Switzerland), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol (supplied by Firmenich SA, Geneva, Switzerland), (1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol (supplied by Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone, methyl-cis-3-oxo-2-pentyl-1-cyclopentane acetate (supplied by Firmenich SA, Geneva, Switzerland), 2,2,5-trimethyl-5-pentyl-1-cyclopentanone (supplied by Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (supplied by Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (supplied by Givaudan SA, Vernier, Switzerland); - group 3: damascone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (supplied by Firmenich SA, Geneva, Switzerland), (1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'-yl)propyl]cyclopentanone, α-ionone, β-ionone, damascenone, a 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 (supplied by Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (supplied by Firmenich SA, Geneva, Switzerland); SA, Geneva, Switzerland), (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate (Supplied by: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1-cyclohexyl acetate (Supplied by: International Flavors and Fragrances, USA), 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (Supplied by: Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (Supplied by: Firmenich SA, Geneva, Switzerland), (E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, terpenyl isobutyrate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate (Supplied by Firmenich SA, Geneva, Switzerland), 8-Methoxy-1-p-menthene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate (Supplied by Firmenich SA, Geneva, Switzerland).Switzerland), para-tert-butylcyclohexanone, menthenethiol, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate;, - Group 4: Methyl cedryl ketone (Supplier: International Flavors and Fragrances, USA), (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2,6 ]dec-3-en-8-yl 2-methylpropanoate and (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2,6]dec-4-en-8-yl 2-methylpropanoate, vetiverol, vetiveron, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone (supplied by International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10-tetramethyl-1-oxaspiro[4.5]deca-3,6-diene and (5RS,9SR,10RS) isomer, 6-ethyl-2,10,10-trimethyl-1-oxaspiro[4.5]deca-3,6-diene, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4-indenone (supplied by International Flavors and Fragrances, USA). Fragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal (Supplied by Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9-spiro-2'-oxirane (Supplied by Firmenich SA, Geneva, Switzerland), 9 / 10-ethyldiene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate (Supplied by Firmenich SA, Geneva, Switzerland), octalinol, (dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan (Supplied by Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl acetate, and tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl propanoate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl propanoate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'-cyclohexen-4'-one; - Group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane (supplier: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecane-4-one and 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecane-4-one. 2,7 ]undecane-4-one (supplied by Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (supplied by Firmenich SA, Geneva, Switzerland); - group 6: (trimethyl-13-oxabicyclo-[10.1.0]-trideca-4,8-diene (supplier: Firmenich SA, Geneva, Switzerland), 9-hexadecen-16-olide (supplier: Firmenich SA, Geneva, Switzerland), pentadecenolide (supplier: Firmenich SA, Geneva, Switzerland), 3-methyl-(4 / 5)-cyclopentadecenone, (supplier: Firmenich SA, Geneva, Switzerland), 3-methylcyclopentadecanone (supplier: Firmenich SA, Geneva, Switzerland), pentadecanolide (supplier: Firmenich SA, Geneva, Switzerland), cyclopentadecanone (supplier: Firmenich SA, Geneva, Switzerland), (1-ethoxyethoxy)cyclododecane (Supplier: Firmenich SA, Geneva, Switzerland), 1,4-dioxacycloheptadecane-5,17-dione, 4,8-cyclododecadien-1-one; - Group 7: (+-)-2-Methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal (Supplier: Givaudan SA, Vernier, Switzerland), 2,2,2-trichloro-1-phenylethyl acetate.

[0043] Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from groups 1 to 7 as defined above. More preferably, said perfume comprises at least 30%, preferably at least 50% of ingredients from groups 3 to 7 as defined above. Most preferably, said perfume comprises at least 30%, preferably at least 50% of ingredients from groups 3, 4, 6 or 7 as defined above.

[0044] According to another preferred embodiment, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP greater than 3, preferably greater than 3.5, even more preferably greater than 3.75.

[0045] According to a particular embodiment, the perfume used in the present invention contains less than 10% by weight of primary alcohols, less than 15% by weight of secondary alcohols, and less than 20% by weight of tertiary alcohols. Advantageously, the perfume used in the present invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.

[0046] According to one embodiment, the oil phase (or oily core) comprises: - 25-100% by weight, preferably 25-98% by weight, of perfume oil containing at least 15% by weight of high impact perfume raw materials having a LogT of less than -4, and - 1.07g / cm 3 0 to 75% by weight, preferably 2 to 75% by weight, of a density adjusting material having a density of more than Includes.

[0047] A "high impact perfume raw material" is to be understood as a perfume raw material having a LogT of less than -4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charge and molecular mass. For convenience, the odor threshold concentration is expressed as the base 10 logarithm of the threshold concentration, i.e., Log[Threshold] ("LogT").

[0048] The density adjustment material is 1.07 g / cm 3 and preferably low or no odor. According to one embodiment, the density adjusting material is selected in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenoxyacetate, triacetin, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof.

[0049] The density of a component is the ratio of its mass to its volume (g / cm 3 )

[0050] Several methods are available for determining the density of a component.

[0051] For example, reference may be made to the ISO 298:1998 method for determining the d20 density of essential oils.

[0052] The odor threshold concentration of the fragrance compound is determined using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact amount of fragrance oil component injected by syringe, the exact split ratio, and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate is precisely measured and the sampling volume is calculated, assuming a human inhalation time lasts 12 seconds. Since the exact concentration at the detector at any time is known, the mass per inhalation volume and therefore the concentration of the fragrance compound is known. To determine the threshold concentration, a solution of the back-calculated concentration is sent to a sniff port. Panelists sniff the GC eluate and identify the retention time when they notice an odor. The average of all panelists determines the odor threshold concentration of the fragrance compound. Determination of odor thresholds 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.

[0053] High impact fragrance ingredients with LogT less than -4 and 1.07 g / cm 3 The properties of density adjusting materials having a density of greater than 1000 nm are described in WO2018115250, the contents of which are incorporated by reference.

[0054] According to one embodiment, the high impact perfume raw materials having a LogT of less than -4 are (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1-phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1-phenylacetate, 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, (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[b]furan-2-one and a mixture containing (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[b]furan-2-one, (+-)-1-(5-ethyl-5-methyl-1-cyclohexen-1-yl)-4-penten-1-one, (1'S,3'R)-1-methyl-2-[ (1',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl}methanol, (+-)-3-mercaptohexyl acetate, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, H-methyl-2h-1,5-benzodioxepin-3(4H)-one, (2E,6Z)-2,6-nonadien-1-ol, (4Z)-4-dodecenal, (+-)-4-hydroxy-2,5-dimethyl-3(2H)-furanium Mixture containing non, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 3-methylindole, (+-)-perhydro-4α,8aβ-dimethyl-4a-naphthalenol, patchoulol, 2-methoxy-4-(1-propenyl)phenol, (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylene-2-phenyl-2H-pyran, 4-methylene-2-phenyltetrahydro-2H-pyran and (+-)-4-methyl-2-phenyl-3,Mixture containing 6-dihydro-2H-pyran, 4-hydroxy-3-methoxybenzaldehyde, nonylene aldehyde, 2-methoxy-4-propylphenol, 3-methyl-5-phenyl-2-pentenenitrile, 1-(spiro[4.5]dec-6 / 7-en-7-yl)-4-penten-1-one, 2-methoxynaphthalene, (-)-(3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 5-nonanolide, (3aR,5AS,9AS,9BR)-3a,6,6, 9a-Tetramethyldodecahydronaphtho[2,1-b]furan, 7-isopropyl-2H,4H-1,5-benzodioxepin-3-one, coumarin, 4-methylphenyl isobutyrate, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, β,2,2,3-tetramethyl-δ-methylene-3-cyclopentene-1-butanol, δ-damascone ((2E)-1-[(1RS,2SR)-2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one), (+-)-3,6-dihydro-4,6-dimethyl-2-phenyl-2h-pyran, anisaldehyde, paracresol, 3-ethoxy-4-hydroxybenzaldehyde, methyl 2-aminobenzoate, ethyl methylphenylglycidate, octalactone gamma, ethyl 3-phenyl-2-propenoate, (-)-(2E)-2-ethyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol, paracresyl acetate, dodecalactone, tricyclone, (+)-(3R,5Z)-3-methyl 1-5-cyclopentadecen-1-one, undecalactone, (1R,4R)-8-mercapto-3-p-menthanone, (3S,3AS,6R,7AR)-3,6-dimethylhexahydro-1-benzofuran-2(3H)-one, β-ionone, (+-)-6-pentyltetrahydro-2H-pyran-2-one, (3E,5Z)-1,3,5-undecatriene, 10-undecenal, (9E)-9-undecenal, (9Z)-9-undecenal, (Z)-4-decenal, (+-)-ethyl 2-methylpentanoate, 1,2-Diallyldisulfane, 2-Tridecenenitrile, 3-Tridecenenitrile, (+-)-2-Ethyl-4,4-dimethyl-1,3-oxathiane, (+)-(3R,5Z)-3-Methyl-5-cyclopentadecen-1-one, 3-(4-tert-butylphenyl)propanal, allyl(cyclohexyloxy)acetate, methyl naphthyl ketone, (+-)-(4E)-3-Methyl-4-cyclopentadecen-1-one, (+-)-5E3-Methyl-5-cyclopentadecen-1-one, cyclopropylmethyl 3-hexenoate, (4E )-4-Methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1-(5-propyl-1,3-benzodioxol-2-yl)ethanone, 4-Methyl-2-pentylpyridine, (+-)-(E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (3aRS,5aSR,9aSR,9bRS)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, (2S,5R)-5-Methyl-2-(2-propanyl)cyclohexanone oxime, 6-hexyl Tetrahydro-2H-pyran-2-one, (+-)-3-(3-isopropyl-1-phenyl)butanal, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, indole, 7-propyl-2H,4H-1,5-benzodioxepin-3-one, ethyl praline, (4-methylphenoxy)acetaldehyde, ethyl tricyclo[5.2.1.0.2,6]decane-2-carboxylate, (+)-(1'S, 2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol, (4E)-3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, methylnonylacetaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropanoate, (E)-4-decenal, (+-)-2-ethyl-4-(2,2,3-Trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, (1R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene, (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane, (-)-(3R)-3,7-dimethyl-1,6-octadien-3-ol, (E)-3-phenyl-2-propenenitrile, 4-methoxybenzyl acetate, (E) -3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, allyl (2 / 3-methylbutoxy)acetate, (+-)-(2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-penten-3-one, and mixtures thereof.

[0055] According to one embodiment, the perfume raw materials having a LogT of less than -4 are selected in the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.

[0056] According to one embodiment, the perfume raw material having a LogT less than -4 comprises at least one compound selected from the group consisting of alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof, preferably in an amount comprised between 20 and 70% by weight, based on the total weight of the perfume raw material having a LogT less than -4.

[0057] According to one embodiment, the perfume raw materials having a LogT less than -4 comprise 20-70% by weight of aldehydes, ketones and mixtures thereof based on the total weight of the perfume raw materials having a LogT less than -4.

[0058] Therefore, the remaining perfume raw materials contained in the oily core may have a LogT greater than -4.

[0059] According to one embodiment, the perfume raw materials having a LogT greater than -4 are ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6 / 8-sec-butylquinoline, (+-)-3-(1,3-benzodioxol-5-yl)-2-methylpropanal, vergyl propionate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, methyl 2-((1RS,2RS)-3-oxo-2-pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]Octane, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, dodecanal, 1-oxa-12 / 13-cyclohexadecen-2-one, (+-)-3-(4-isopropylphenyl)-2-methylpropanal, aldehyde C11, (+-)-2,6-dimethyl-7-octen-2-ol, 3-cyclohexylpropanoic acid allyl, (Z)-3-hexenyl acetate, 5-methyl-2-(2-propanyl)cyclohexanone, heptanoic acid allyl, 2-(2-methyl-2-propanyl)cyclohexanone lopanyl)cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl butyrate, geranyl acetate, neryl acetate, (+-)-1-phenylethyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutanoate, (2Z)-ethyl 3-hydroxy-2-butenoate, 8-p-menthanol, 8-p-menthanyl acetate, 1-p-menthanyl acetate, (+-)-2-(4-methyl-3-cyclohexen-1-yl)-2- Propanyl acetate, (+-)-2-methylbutyl butanoate, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3,5,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2-cyclohexylethyl acetate, octanal, ethyl butanoate, (+-)-(3E)-4-(2,6,6-trimethyl-1 / 2-cyclohexen-1-yl)-3-butanoate Ten-2-one, 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, ethyl hexanoate, undecanal, decanal, 2-phenylethyl acetate, (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol), (+-)-3,7-dimethyl-3-octanol, 1-methyl-4-(2-propanylidene)cyclohexene, (+)-(R)-4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene, vergyl acetate, (3R)-1-[(1R,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (3S)-1 -[(1R,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (3R)-1-[(1S,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (+)-(1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, and mixtures thereof.

[0060] According to one embodiment, the fragrance formulation comprises: - 0 to 60% by weight of a hydrophobic solvent (based on the total weight of the fragrance formulation), - 40-100% by weight of perfume oil (based on the total weight of the perfume formulation) and the perfume oil has at least two, and preferably all, of the following properties: at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a logP greater than 3, preferably greater than 3.5, at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of bulky materials of groups 1 to 6, preferably 3 to 6, as defined above, and 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 LogT of less than -4 as defined above, Optionally, a further hydrophobic active ingredient.

[0061] According to a particular embodiment, the perfume comprises 0-60% by weight of hydrophobic solvent.

[0062] According to a particular embodiment, the hydrophobic solvent is a density adjusting material, preferably selected in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof.

[0063] In certain embodiments, the hydrophobic solvent has a Hansen solubility parameter that matches the encapsulated perfume oil.

[0064] The term "Hansen Solubility Parameter" is understood to refer to the solubility parameter approach proposed by Charles Hansen, used to predict the solubility of polymers, developed on the basis that the total energy of vaporization of a liquid consists of several individual parts. To calculate the "weighted Hansen Solubility Parameter", it is necessary to combine the effects of (atomic) dispersion forces, (molecular) permanent dipole-dipole forces and (molecular) hydrogen bonding (electron exchange). The "weighted Hansen Solubility Parameter" is calculated by the weighting factor (δD 2 +δP 2 +δH 2 ) 0.5 where δD is the Hansen dispersion value (hereinafter also referred to as atomic dispersion force), δP is the Hansen polarizability value (hereinafter also referred to as dipole moment), and δH is the Hansen hydrogen bond ("h-bond") value (hereinafter also referred to as hydrogen bond). For a more detailed description of the parameters and values, see Charles Hansen, The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, Danish Technical Press (Copenhagen, 1967).

[0065] The Euclidean difference in solubility parameters between the fragrance and the solvent is (4 × (δDsolvent – ​​δDfragrance) 2 + (δP solvent - δP fragrance) 2 + (δH solvent - δH fragrance) 2) 0.5 where δDsolvent, δPsolvent and δHsolvent are the Hansen dispersion, Hansen polarizability and Hansen h-bonding values ​​of the solvent, respectively, and δDfragrance, δPfragrance and δHfragrance are the Hansen dispersion, Hansen polarizability and Hansen h-bonding values ​​of the fragrance, respectively.

[0066] In certain embodiments, 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 (δD) of 12-20, a dipole moment (δP) of 1-8, and a hydrogen bond (δH) of 2.5-11.

[0067] In certain embodiments, 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 (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δH) of 2.5 to 11, preferably 4 to 11.

[0068] In certain embodiments, at least 90% of the perfume oils, preferably at least 95% of the perfume oils, and most preferably at least 98% of the perfume oils have at least two Hansen Solubility Parameters selected from a first group consisting of an atomic dispersion force (δD) of 12-20, a dipole moment (δP) of 1-8, and a hydrogen bond (δH) of 2.5-11.

[0069] In certain embodiments, 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 (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δH) of 2.5 to 11, preferably 4 to 11.

[0070] According to one embodiment, the fragrance formulation comprises an odor modifier (which can be used in addition to the hydrophobic solvent, if one is present, or instead of the hydrophobic solvent, if one is not present).

[0071] Preferably, odor control agents are defined as odoriferous materials having: i. A vapor pressure of less than 0.0008 Torr at 22°C; ii. a clogP of 3.5 or greater, preferably 4.0 or greater, more preferably 4.5; iii. at least two Hansen solubility parameters selected from a first group consisting of atomic dispersion forces of 12-20, dipole moments of 1-7, and hydrogen bonds of 2.5-11; iv. at least two Hansen solubility parameters selected from a second group consisting of atomic dispersion forces of 14-20, dipole moments of 1-8, and hydrogen bonds of 4-11 in a solution with a compound having a vapor pressure range of 0.0008-0.08 Torr at 22 °C.

[0072] Preferably, the following ingredients can be mentioned as regulators by way of example, but the list is not limited to the following materials: alcohol C12, oxacyclohexadec-12 / 13-en-2-one, 3-[(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4-cyclopentadecen-1-one, cyclopentadecanone, (8Z)-oxacycloheptadeca-8-en-2-one, 2-[5-(tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, muguetaldehyde (muguet aldehyde), 1,5,8-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene, (+-)-4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (+)-(1S,2S,3S,5R)-2,6,6-trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one, oxacyclohexadecan-2-one, 2-{(1S)-1-[(1R)-3, 3-Dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, (+)-(4R,4aS,6R)-4,4a-dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone, amylcinnamaldehyde, hexylcinnamaldehyde, hexyl salicylate, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,6-heptadiene-3-one, (9Z)-9-cycloheptadecen-1-one.

[0073] According to a particular embodiment, the hydrophobic material does not include any active ingredients (such as fragrances). According to this particular embodiment, the hydrophobic material comprises, preferably consists of, a hydrophobic solvent, preferably isopropyl myristate, triglycerides (e.g. Neobee® MCT oil, vegetable oils), D-limonene, silicone oils, mineral oils and mixtures thereof, and optionally a hydrophilic solvent, preferably selected in the group consisting of 1,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1,2-propanediol), 1,3-propanediol, dipropylene glycol, glycerol, glycol ethers and mixtures thereof.

[0074] According to certain embodiments, the hydrophobic material comprises an active ingredient (preferably a fragrance) and a hydrophobic solvent such as isopropyl myristate, triglycerides (e.g., vegetable oils such as Neobee® MCT oil, sunflower oil, etc.), D-limonene, silicone oil, mineral oil, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof.

[0075] The term "biocide" refers to a chemical that can kill or reduce or prevent the growth and / or accumulation of living organisms (e.g., microorganisms). Biocides are commonly used in the medical, agricultural, forestry, and forestry industries to prevent fouling of, for example, water, agricultural products including seeds, and oil pipelines. Biocides can be pesticides, including fungicides, herbicides, insecticides, algaecides, molluscicides, acaricides, and rodenticides, and / or antimicrobials, such as bactericides, antibiotics, antibacterial agents, antivirals, antifungals, antiprotozoals, and / or antiparasitics.

[0076] As used herein, "pesticide" refers to a substance that acts to repel or attract pests, reduce, inhibit or promote their growth, development or activity. A pest refers to any organism, whether animal, plant or fungus, that invades or is a nuisance to plants or animals, and includes insects, particularly arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.

[0077] By "flavor oil" is meant herein a flavoring ingredient or a mixture of flavoring ingredients, solvents or auxiliaries currently used for the preparation of flavoring formulations, i.e. a specific mixture of ingredients 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 those skilled in the art, their nature does not require a detailed description here, which is in any case not comprehensive, and the skilled flavorist can select them on the basis of general knowledge, depending on the intended use or application, and the organoleptic effect that it is desired to achieve. Many of these flavoring ingredients are described in references, for example in the book Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA, by S. Arctander, or its more recent editions, or other treatises of the same kind, for example Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press, or Synthetic Food Adjuncts, 1947, by MB Jacobs, van Nostrand Co., Inc. Solvents and adjuvants currently used for the preparation of flavoring formulations are also well known in the art.

[0078] In a particular embodiment, the flavor is a mint flavor, hi a more particular embodiment, the mint is selected from the group consisting of peppermint and spearmint.

[0079] In a further embodiment, the flavoring is a cooling agent or mixtures thereof.

[0080] In another embodiment, the flavor is a menthol flavor.

[0081] Flavors derived from or based on fruits in which citric acid is the predominant natural acid include, but are not limited to, citrus fruits (e.g., lemon, lime), limonene, strawberry, orange, and pineapple. In one embodiment, the flavored food product is lemon, lime, or orange juice extracted directly from the fruit. Further embodiments of the flavor include juices or liquids extracted from orange, lemon, grapefruit, key lime, citron, clementine, mandarin, tangerine, and any other citrus fruit, or any variety or hybrid thereof. In a particular embodiment, the flavor includes liquids extracted or distilled from orange, lemon, grapefruit, key lime, citron, clementine, mandarin, tangerine, any other citrus fruit, or any variety or hybrid thereof, pomegranate, kiwi fruit, watermelon, apple, banana, blueberry, melon, ginger, bell pepper, cucumber, passion fruit, mango, pear, tomato, and strawberry.

[0082] In certain embodiments, the flavor comprises a composition comprising limonene, and in certain embodiments, the composition is a citrus that further comprises limonene.

[0083] In another particular embodiment, the flavor comprises a flavor selected from the group including strawberry, orange, lime, tropical, berry mix, and pineapple.

[0084] The expression flavour not only includes flavours that impart or modify the smell of a food product, but also ingredients that impart or modify tastes, which do not necessarily have a taste or smell of their own, but can modify the tastes imparted by other ingredients, for example ingredients that enhance saltiness, enhance sweetness, enhance umami, reduce bitterness, etc.

[0085] In further embodiments, a suitable sweetening component can be included in the particles described herein. In certain embodiments, the sweetening component is selected from the group consisting of sugar (such as, but not limited to, sucrose), stevia components (such as, but not limited to, stevioside or rebaudioside A), sodium cyclamate, aspartame, sucralose, sodium saccharin, and acesulfame K, or mixtures thereof.

[0086] According to one embodiment, the hydrophobic material comprises about 10% to 95% by weight based on the total weight of the oil phase. According to another embodiment, the hydrophobic material comprises about 10% to 80% by weight based on the total weight of the oil phase. According to another embodiment, the hydrophobic material comprises about 10% to 60% by weight based on the total weight of the oil phase. According to another embodiment, the hydrophobic material comprises about 15% to 45% by weight based on the total weight of the oil phase.

[0087] Acyl chloride According to a particular embodiment, the acyl chloride has the following formula (I): [ka] [In the formula, n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is (i)-(xi), especially (i)-(vi). [ka] (n+1)-valent C2 to C optionally containing at least one group selected from 45 is a hydrocarbon group, R is a hydrogen atom or an alkyl group such as a methyl or ethyl group, preferably a hydrogen atom. has.

[0088] "...hydrocarbon group..." is understood to mean that said group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), saturated cyclic hydrocarbon (e.g. cycloalkyl) or unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or aromatic hydrocarbon, i.e. aryl group, or may be in the form of a mixture of the above types of groups, for example, a particular group may contain linear alkyl, branched alkenyl (e.g. having one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties, unless a specific limitation to only one type is mentioned. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of more than one type of topology (e.g. linear, cyclic or branched) and / or saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is also meant that the group may have any one of the above topologies or contain moieties that are saturated or unsaturated, as explained above. Similarly, in all embodiments of the present invention, when a group is referred to as being in one type of saturated or unsaturated (e.g., alkyl) form, it is meant that said group may be of any type of topology (e.g., linear, cyclic or branched) or may have some moieties with different topologies.

[0089] The term "hydrocarbon radical optionally containing ..." is understood to mean that said hydrocarbon radical optionally contains heteroatoms, forming ether, aryl ether, amine, nitrile or carboxylic acid groups and derivatives including, for example, esters, acids, amides. These groups may be attached laterally to said hydrocarbon radical by replacing a hydrogen atom of the hydrocarbon radical, or may be inserted into a hydrocarbon chain or ring by replacing a carbon atom of the hydrocarbon radical (if chemically possible).

[0090] According to a particular embodiment, the acyl chloride is selected from the group consisting of benzene-1,3,5-tricarbonyl trichloride (trimesoyl trichloride), benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthaloyl dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaryl dichloride, adipoyl chloride, succinic acid dichloride, propane-1, 2,3-Tricarbonyl trichloride, cyclohexane-1,2,4,5-tetracarbonyl tetrachloride, 2,2'-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo 2-[2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl]4-chloro-4-oxo-butanoate, 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate, [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl

[0036] The aryl ester is selected from the group consisting of 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, propane-1,2,3-triyltris(4-chloro-4-oxobutanoate), propane-1,2-diylbis(4-chloro-4-oxobutanoate) and mixtures thereof.

[0091] According to a particular embodiment, the acyl chloride is selected from the group consisting of benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthaloyl dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaryl dichloride, adipoyl dichloride, succinic acid dichloride, propane-1,2,3-tricarbonyl trichloride, cyclohexane-1, 2,4,5-Tetracarbonyltetrachloride, 2,2'-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-Chloro-4-oxo-butanoate, [2-[2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl] 4-chloro-4-oxo-butanoate, 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate, [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl] butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, propane-1,2,3-triyltris(4-chloro-4-oxobutanoate), propane-1,2-diylbis(4-chloro-4-oxobutanoate) and mixtures thereof.

[0092] According to another particular embodiment, the acyl chloride is selected from the group consisting of fumaryl dichloride, adipoyl dichloride, succinic acid dichloride, propane-1,2,3-triyltris(4-chloro-4-oxobutanoate), propane-1,2-diylbis(4-chloro-4-oxobutanoate) and mixtures thereof.

[0093] The weight ratio between the acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.09, more preferably between 0.02 and 0.07.

[0094] According to a particular embodiment, the acyl chloride is used in an amount comprised between 1.7 and 7% by weight, preferably between 2.5 and 5% by weight, based on the total weight of the hydrophobic material.

[0095] The acyl chlorides can be dissolved (or dispersed) directly in the perfume oil or can be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfume solvent / ingredient, such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oils (such as sunflower oil), hexyl salicylate, Neobee (caprylic / capric triglyceride), isopropyl myristate, triglycerides, D-limonene, silicone oils, mineral oils, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof, prior to mixing with the perfume oil.

[0096] According to one embodiment, the multifunctional monomer is added to the oil phase.

[0097] By "multifunctional monomer" is meant molecules that chemically react or bond as units to form a polymer or supramolecular polymer. The multifunctional polymer of the present invention has at least two functional groups capable of forming a microcapsule shell.

[0098] It should be understood that when added, the multifunctional monomer is added in addition to the acyl chloride.

[0099] The multifunctional monomer is preferably selected in the group consisting of at least one isocyanate, maleic anhydride, acyl chloride, epoxide, acrylate monomer, alkoxysilane, and mixtures thereof.

[0100] According to one embodiment, the polyfunctional monomer used in the process of the present invention is present in an amount representing 0.1 to 15% by weight, preferably 0.5 to 10% by weight, more preferably 0.8 to 6% by weight, even more preferably 1 to 3% by weight, based on the total amount of the oil phase.

[0101] According to a particular embodiment, in addition to the acyl chloride, a polyisocyanate having at least two isocyanate functional groups is further added to the oil phase.

[0102] Suitable polyisocyanates for use according to the present invention include aromatic polyisocyanates, aliphatic polyisocyanates and mixtures thereof. The polyisocyanates contain at least two, preferably at least three, isocyanate functional groups, but may contain up to six, or even only four, isocyanate functional groups. According to a particular embodiment, triisocyanates (three isocyanate functional groups) are used.

[0103] According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.

[0104] The term "aromatic polyisocyanate" is intended to encompass any polyisocyanate containing an aromatic moiety. Preferably, the aromatic polyisocyanate contains a phenyl, toluyl, xylyl, naphthyl or diphenyl moiety, more preferably a toluyl or xylyl moiety. Preferred aromatic polyisocyanates include biurets, polyisocyanurates and trimethylolpropane adducts of diisocyanates, more preferably one of the specific aromatic moieties listed above. More preferably, the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (available under the trade name Desmodur® RC from Bayer), a trimethylolpropane adduct of toluene diisocyanate (available under the trade name Desmodur® L75 from Bayer), a trimethylolpropane adduct of xylylene diisocyanate (available under the trade name Takenate® D-110N from Mitsui Chemicals, Inc.). In a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0105] According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain any aromatic moiety. The preferred aliphatic polyisocyanate is the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, the trimethylolpropane adduct of hexamethylene diisocyanate (available from Mitsui Chemicals, Inc.), or the biuret of hexamethylene diisocyanate (available from Bayer under the trade name Desmodur® N 100), of which the biuret of hexamethylene diisocyanate is more preferred.

[0106] According to another embodiment, the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and at least one aromatic polyisocyanate, both containing at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate and a polyisocyanurate of toluene diisocyanate, and a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of toluene diisocyanate. Most preferably, the polyisocyanate is a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylene diisocyanate. Preferably, when used as a mixture, the molar ratio of aliphatic polyisocyanate to aromatic polyisocyanate is in the range of 80:20 to 10:90.

[0107] According to one embodiment, the at least one polyisocyanate used in the process of the invention is present in an amount representing from 0.1 to 15% by weight, preferably from 0.5 to 10% by weight, more preferably from 0.8 to 6% by weight, even more preferably from 1 to 3% by weight, based on the total amount of the oil phase.

[0108] In another step of the process according to the invention, the oil phase of step a) is dispersed in an aqueous solution to form an oil-in-water emulsion.

[0109] The average droplet size of the emulsion is preferably comprised between 1 and 1000 microns, more preferably between 1 and 500 microns, and even more preferably between 5 and 50 microns.

[0110] Oil-in-water emulsions can be prepared using high speed mechanical or ultrasonic dispersers well known to those skilled in the art.

[0111] Amino Compound A According to the invention, at least one amino compound A is added to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0112] According to a particular embodiment, at least one amino compound A is added to the aqueous phase prior to the formation of the oil-in-water emulsion.

[0113] According to a particular embodiment, at least one amino compound A is added to the oil-in-water emulsion obtained after step b).

[0114] According to a particular embodiment, at least one amino compound A is added to the aqueous phase prior to the formation of the oil-in-water emulsion and to the oil-in-water emulsion obtained after step b).

[0115] The amino compound A is preferably xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine (Jeffamine®), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, 1,4-diaminobutane, 2,2-dimethyl-1,3-propanediamine, 1,3-diaminopentane (Dytek EP diamine), 1,2-diaminopropane, amines having a disulfide bond, such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides; 1,3-diaminopropane; urea; ethyleneurea; aminoguanidine bicarbonate; 1-(2-aminoethyl)imidazolidin-2-one; N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine; N1-(2-aminoethyl)-N1-dodecyl-1,2-ethanediamine; aminoethylethanolamine; N1-(3-aminopropyl)propane-1,3-diamine and mixtures thereof.

[0116] According to a particular embodiment, the amino compound A is ethylenediamine and is added to the aqueous phase and / or to the oil-in-water emulsion obtained after step b).

[0117] According to one embodiment, the molar ratio between the functional group NH2 of the amino compound A and the functional group COCl of the acyl chloride is comprised between 0.2 and 3, preferably between 0.5 and 2, and more preferably between 0.2 and 1.

[0118] base According to one embodiment, the aqueous phase comprises a base, preferably selected in the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, guanidine carbonate, triethanolamine and mixtures thereof.

[0119] According to a particular embodiment, the base is not an amino compound.

[0120] According to one embodiment, the aqueous phase comprises a base, preferably selected in the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide and mixtures thereof.

[0121] The base can be added in an amount comprised between 0.01 and 1.5% by weight, preferably between 0.01 and 0.7% by weight, based on the total weight of the aqueous phase.

[0122] protein According to certain embodiments, the protein is added to the oil phase and / or the water phase. According to certain embodiments, the protein is added to the oil phase.

[0123] The protein is preferably used in an amount comprised between 0.1 and 10% by weight, preferably between 0.5 and 7% by weight, based on the total weight of the oil or aqueous phase.

[0124] According to one embodiment, the protein is a biopolymer.

[0125] According to one embodiment, the protein is selected from the group consisting of whey protein, sodium caseinate, bovine serum albumin, casein, gelatin (preferably fish gelatin), vegetable protein and mixtures thereof.

[0126] According to one embodiment, the protein is selected from the group consisting of soy protein, rice protein, whey protein, white egg albumin, casein, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, gelatin and mixtures thereof. According to a particular embodiment, the protein is sodium caseinate.

[0127] According to another embodiment, the protein is selected 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 and mixtures thereof.

[0128] According to another embodiment, the protein is selected in the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, soy protein, rice protein, whey protein, egg albumin, casein, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, gelatin and mixtures thereof.

[0129] The potato protein is typically extracted from potato tubers (Solanum tuberosum). According to one embodiment, the potato protein is a native potato protein and preferably comprises or consists of patatin.

[0130] The protein used in the present invention may be native or may be partially or completely denatured by any suitable method. Denaturation is the process of changing the conformational structure of a protein by unfolding, i.e., involving the destruction, and possibly degradation, of both the secondary and tertiary structure of the protein. In fact, denaturation implies that many of the weak links or bonds (e.g. hydrogen bonds) within the protein molecule that are responsible for the highly ordered structure of the protein in the native state are broken. Denaturation can be reversible (protein can return to native state when the effect of denaturation is removed) or irreversible.

[0131] Denaturation can be achieved in a variety of ways. Proteins can be denatured by temperature, radiation, or mechanical stress, including shear, by changes in pH (treatment with base or acid), by treatment with oxidizing or reducing agents, by inorganic salts, by certain organic solvents, by chaotropic agents (i.e., those with a positive chaotropic value (kJ Kg on the Holdsworth scale)). -1 The molecule can be denatured by exposure to a compound having a molecular weight of 1000 to 15000, such as a guanidine salt, 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.

[0132] Proteins used in the present invention can also be derivatized or modified (e.g., derivatized or chemically modified). For example, proteins can be modified by the covalent attachment of sugars, lipids, peptides, or chemical groups such as phosphate or methyl.

[0133] According to one embodiment, the protein acts as a stabilizer.

[0134] A stabilizer may further be added to the aqueous phase and / or the oil phase to form the emulsion. According to one embodiment, the stabilizer is a colloidal stabilizer.

[0135] By "stabilizer" is meant a compound capable of stabilizing the oil / water interface of an emulsion, typically by lowering the interfacial tension between the oil and water phases.

[0136] The terms "stabilizer" and "emulsifier" may be used interchangeably in the present invention.

[0137] According to one embodiment, the stabilizer is a colloidal stabilizer.

[0138] The colloidal stabilizer can be a polymeric emulsifier (standard emulsion), a surfactant or a solid particle (Pickering emulsion).

[0139] "Molecular emulsifier" and "polymeric emulsifier" are used interchangeably in the present invention.

[0140] "Polymer emulsifier" means an emulsifier that has both a polar group (hydrophilic) that has an affinity for water and a non-polar group (hydrophobic) that has an affinity for oil. The hydrophilic portion dissolves in the water phase, and the hydrophobic portion dissolves in the oil phase, forming a membrane around the droplets.

[0141] "Surfactant" means a non-polymeric substance containing polar and non-polar groups.

[0142] According to one embodiment, the stabilizer is selected in the group consisting of inorganic particles, polymeric emulsifiers such as polysaccharides, proteins, glycoproteins and mixtures thereof.

[0143] When the stabilizer is a solid particle, it can be selected in the group consisting of calcium phosphate, silica, silicates, titanium dioxide, aluminum oxide, zinc oxide, iron oxide, mica, kaolin, montmorillonite, laponite, bentonite, perlite, dolomite, diatomaceous earth, vermiculite, hectorite, gibbsite, illite, kaolinite, aluminosilicates, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomaceous earth and mixtures thereof.

[0144] According to certain embodiments, the stabilizer is a biopolymer.

[0145] According to a particular embodiment, the stabilizer is a polymer as defined above.

[0146] "Biopolymer" means a biological macromolecule produced by an organism. Biopolymers are characterized by a molecular weight distribution ranging from 1000 (one thousand) to 1000 million (billion) daltons. These macromolecules may be carbohydrates (sugar based) or proteins (amino acid based), or a combination of both (rubbers), and may be linear or branched.

[0147] According to one embodiment, the colloidal stabilizer is selected in the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder and mixtures thereof.

[0148] According to a particular embodiment, the stabilizer is a protein, such as a biopolymer selected in the group consisting of whey protein, casein, sodium caseinate, bovine serum albumin and mixtures thereof.

[0149] According to another embodiment, the stabilizer is selected in the group consisting of potato proteins, chickpea proteins, pea proteins, algae proteins, faba bean proteins, barley proteins, oat proteins, wheat gluten proteins, lupin proteins and mixtures thereof.

[0150] According to another embodiment, the stabilizer is selected 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, egg albumin, casein, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, gelatin and mixtures thereof.

[0151] When added to the oil phase, the stabilizer can be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfume solvent / ingredient such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oils (such as sunflower oil), hexyl salicylate, Neobee (caprylic / capric triglyceride), isopropyl myristate, triglycerides, D-limonene, silicone oil, mineral oil, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof, or can be mixed into the active ingredients, preferably including perfume oils.

[0152] The stabilizer and acyl chloride may be premixed, preferably prior to mixing with the hydrophobic material including the perfume oil, and may be heated, for example at a temperature of 10 to 80°C.

[0153] If a colloidal stabilizer is added to the aqueous phase, it is preferably selected in the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder and mixtures thereof.

[0154] According to any one of the above embodiments of the invention, the dispersion comprises about 0.01% to 3.0% of at least one stabilizer, preferably a colloidal stabilizer, the percentage being expressed on a w / w basis relative to the total weight of the oil-in-water emulsion as obtained after step b). In yet another aspect of the invention, the dispersion comprises about 0.05% to 2.0%, preferably 0.05 to 1%, of at least one stabilizer, preferably a colloidal stabilizer. In yet another aspect of the invention, the dispersion comprises about 0.1% to 1.6%, preferably 0.1% to 0.8% by weight of at least one stabilizer, preferably a colloidal stabilizer.

[0155] Crosslinking Agent According to the present invention, a cross-linking agent is added during the process to cross-link the proteins.

[0156] Although the presence of a cross-linking agent is an essential feature of the present invention, said cross-linking agent can be added at different stages of the process.

[0157] According to the invention, the crosslinking agent can be added in step b) and / or in step c) and / or after step c).

[0158] If added in step b), the crosslinker may be added to the aqueous phase before the formation of the oil-in-water emulsion and / or after the oil-in-water emulsion has been formed.

[0159] The crosslinking agent can be added during and / or after the curing step c).

[0160] The cross-linking agents used in the present invention may be enzymatic cross-linking agents, such as enzymes, or non-enzymatic cross-linking agents, such as glutaraldehyde or genipin.

[0161] According to a particular embodiment, the cross-linking agent is an enzyme.

[0162] According to a particular embodiment, the enzyme is transglutaminase.

[0163] The enzyme can be used in an amount comprised between 0.001 and 5%, preferably between 0.001 and 1%, preferably between 0.001 and 0.1%, preferably between 0.005 and 0.02%, based on the total weight of the slurry of step c).

[0164] In some commercial products, the enzyme is dispersed in a carrier. For example, Activa® TI (supplier: Ajinomoto Co., Inc.) can be mentioned. In other words, the commercial product is added to the process to have an amount of enzyme activity of preferably 0.001-5%, preferably 0.001-1%, even more preferably 0.001-0.1%, even more preferably 0.005-0.02%, based on the total weight of the slurry in step c).

[0165] According to one embodiment, if the crosslinking agent is added before the hardening step c) (typically when the crosslinking agent is added in step b) before the formation of the oil-in-water emulsion and / or in the aqueous phase after the formation of the oil-in-water emulsion), the process typically comprises a hardening step c) which makes it possible to end up with microcapsules in the form of a slurry and at the same time crosslink the proteins in the shell. According to a preferred embodiment, said hardening step is carried out at a temperature comprised between 5 and 90°C, possibly under pressure, for a period of 1 to 8 hours, in order to improve the kinetics. More preferably, said hardening step is carried out at a temperature comprised between 10 and 80°C, for a period of 30 minutes to 5 hours.

[0166] If the cross-linking agent is an enzyme, once the shell has formed and the proteins have been cross-linked, the slurry can be subjected to a heat treatment to inactivate the enzyme. Typically, the heat treatment can be carried out at a temperature comprised between 70°C and 90°C.

[0167] According to one embodiment, if a crosslinking agent is added during the hardening step c), the process typically comprises a hardening step c), which makes it possible to end up with microcapsules in the form of a slurry and at the same time crosslink the proteins in the shell. According to a preferred embodiment, said hardening step is carried out at a temperature comprised between 5 and 90°C, possibly under pressure, for a time period between 1 and 8 hours, in order to improve the kinetics. More preferably, said hardening step is carried out at a temperature comprised between 10 and 80°C, for a time period between 30 minutes and 5 hours.

[0168] If the cross-linking agent is an enzyme, once the shell has formed and the proteins have been cross-linked, the slurry can be subjected to a heat treatment to inactivate the enzyme. Typically, the heat treatment can be carried out at a temperature comprised between 70°C and 90°C.

[0169] According to one embodiment, if a cross-linking agent is added after the hardening step c), in addition to the hardening step c) making it possible to end up with microcapsules in the form of a slurry, the process further comprises an additional hardening step d) after the addition of the cross-linking agent, in order to cross-link the proteins in the shell.

[0170] The curing step c) and / or the curing step d) can be carried out at a temperature comprised between 5 and 90° C., optionally under pressure, for a period of 1 to 8 hours. More preferably, said curing step is carried out at a temperature comprised between 10 and 80° C., for a period of 30 minutes to 5 hours.

[0171] If the cross-linking agent is an enzyme, once the shell has formed and the protein has been cross-linked, the slurry can be subjected to an additional heat treatment to inactivate the enzyme. Typically, the heat treatment can be carried out at a temperature comprised between 70°C and 90°C.

[0172] According to the invention, the curing step c) and / or the curing step d) can be carried out at room temperature under stirring or can include a heating step to improve the kinetics.

[0173] Amino Compound B According to one embodiment, at least one amino compound B is added to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0174] According to a particular embodiment, at least one amino compound B is added to the aqueous phase prior to the formation of the oil-in-water emulsion.

[0175] According to a particular embodiment, at least one amino compound B is added to the oil-in-water emulsion obtained after step b).

[0176] According to a particular embodiment, at least one amino compound B is added to the aqueous phase prior to the formation of the oil-in-water emulsion and to the oil-in-water emulsion obtained after step b).

[0177] According to one embodiment, amino compound A and amino compound B are the same.

[0178] According to another embodiment, amino compound A and amino compound B are different.

[0179] According to a particular embodiment, the amino compound B is preferably an amino acid selected in the group consisting of L-lysine, L-leucine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine and / or their derived oligomers and polymers, and mixtures thereof, preferably L-lysine, L-arginine, L-histidine, L-tryptophan and mixtures thereof, more preferably L-lysine, L-arginine, L-histidine and mixtures thereof.

[0180] The amino acid preferably has two nucleophilic groups.

[0181] According to a particular embodiment, the amino compound B may be selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane and mixtures thereof. According to a particular embodiment, the amino compound B is L-lysine.

[0182] According to one embodiment, the amino compound B is L-lysine and is added to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0183] According to one embodiment, the weight percentage of amino compound B in the aqueous phase is comprised between 0 and 5%, preferably between 0.1 and 5%, and more preferably between 0.1 and 2%.

[0184] According to a particular embodiment, a multivalent salt (calcium chloride, magnesium chloride, zinc chloride, iron trichloride, etc.) is added after step b) and before or during step c).

[0185] carbohydrates According to one embodiment, carbohydrates are added to the aqueous and / or oil phase.

[0186] According to one embodiment, "carbohydrate" is to be understood as a polymer or oligomer having more than two units.

[0187] According to another embodiment, the carbohydrate, the amino compound A and the amino compound B are different moieties.

[0188] According to one embodiment, at least one carbohydrate is added to the oil phase and / or the water phase.

[0189] According to one embodiment, the carbohydrate is not a polyphenol.

[0190] According to one embodiment, the carbohydrate is not a functionalized carbohydrate.

[0191] According to one embodiment, the carbohydrate is a polysaccharide.

[0192] According to one embodiment, the polysaccharide is an anionic polysaccharide.

[0193] According to a particular embodiment, the polysaccharide is added to the aqueous phase.

[0194] The polysaccharide is preferably selected in the group consisting of anionic salts of alginic acid, preferably sodium alginate, pectin, lignin, anionically modified starch, carboxymethylcellulose and mixtures thereof.

[0195] According to a particular embodiment, the carbohydrate is an anionic salt of alginic acid, preferably sodium alginate.

[0196] "Sodium alginate" and "sodium alginate" may be used interchangeably.

[0197] According to a particular embodiment, the carbohydrate is used in an amount comprised between 0.1 and 5% by weight, preferably between 0.5 and 1.1% by weight, based on the total weight of the aqueous phase.

[0198] Optional outer coating According to a particular embodiment of the present invention, at the end of step c) or during step c), a polymer selected from the group consisting of non-ionic polysaccharides, cationic polymers, polysuccinimide derivatives (for example as described in WO2021185724) and mixtures thereof can also be added to the slurry of the present invention to form an outer coating on the microcapsules.

[0199] Nonionic polysaccharide polymers are well known to those skilled in the art and are described, for example, in WO 2012 / 007438, page 29, lines 1-25, and in WO 2013 / 026657, page 2, lines 12-19, and page 4, lines 3-12. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methylcellulose.

[0200] Cationic polymers are well known to those skilled in the art. Preferred cationic polymers have a cationic charge density of at least 0.5 meq / g, more preferably at least about 1.5 meq / g, even more preferably less than about 7 meq / g, more preferably less than about 6.2 meq / g. The cationic charge density of the cationic polymer can be determined by the Kjeldahl method described in the United States Pharmacopoeia Chemical Test for Nitrogen Determination. Preferred cationic polymers are selected from those having units containing primary, secondary, tertiary and / or quaternary amine groups which may form part of the main polymer chain or may be carried on side chain substituents directly attached thereto. The weight average (Mw) molecular weight of the cationic polymer is preferably 10,000 to 3.5 M Daltons, more preferably 50,000 to 1.5 M Daltons. According to particular embodiments, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylamino methacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1-vinyl-1H-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 are used. Preferably, the copolymer is selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, 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.Specific examples of commercially available products include Salcare® SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, supplier: BASF) or Luviquat®, such as PQ 11N, FC 550 or Style (polyquaternium-11-68 or quaternized copolymer of vinylpyrrolidone, supplier: BASF), or Jaguar® (C13S or C17, supplier: Rhodia).

[0201] According to any one of the above embodiments of the present invention, said polymer is added in an amount comprised between about 0% and 5% (w / w), or even between about 0.1% and 2% (w / w), the percentage being expressed on a w / w basis with respect to the total weight of the slurry as obtained after step c) or d).It is clearly understood by those skilled in the art that only a part of said polymer added is incorporated / attached to the microcapsule shell.

[0202] Another subject of the invention is a method for preparing a microcapsule powder, comprising the steps defined above and an additional step d) or e), consisting in subjecting the slurry obtained in step c) or d) to drying, such as spray drying, to obtain the microcapsules as such, i.e. in powder form. It is understood that any standard method known to the skilled artisan for carrying out such drying is applicable. In particular, the slurry can be spray-dried, preferably in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginate, carrageenan or a cellulose derivative, to obtain the microcapsules in powder form.

[0203] According to a particular embodiment, the carrier material contains a non-encapsulated perfume oil, which may be the same as or different from the perfume from the core of the microcapsule.

[0204] However, other drying methods may also be mentioned, such as extrusion, coating, spray granulation, fluidized bed or even drying at room temperature using materials (carriers, desiccants) that meet certain criteria, as disclosed in WO 2017 / 134179.

[0205] Core-shell microcapsules Another subject of the invention are the microcapsules or the microcapsule slurries obtainable by the process described above.

[0206] Another subject of the present invention is a composition comprising at least one microcapsule, the microcapsule comprising: a core comprising a hydrophobic material, preferably a fragrance, preferably an oily core; a polyamide-based shell, Acyl chlorides, Amino compounds A, optionally an amino compound B, ·protein The shell and Including, The shell is a polyamide-based core-shell microcapsule or a polyamide-based core-shell microcapsule slurry having a breaking stress of less than 10 MPa.

[0207] According to one embodiment, the shell comprises a carbohydrate as defined above.

[0208] According to one embodiment, the shell has a break stress of less than 9 MPa. According to one embodiment, the shell has a break stress of less than 8 MPa. According to one embodiment, the shell has a break stress of less than 7 MPa. According to one embodiment, the shell has a break stress of less than 6 MPa. According to one embodiment, the shell has a break stress of less than 5 MPa. According to one embodiment, the shell has a break stress of less than 4 MPa. According to one embodiment, the shell has a break stress of less than 3 MPa.

[0209] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 10 MPa. According to one embodiment, the shell has a breaking stress comprised between 0.1 and 9 MPa.

[0210] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 8 MPa.

[0211] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 7 MPa.

[0212] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 6 MPa.

[0213] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 5 MPa.

[0214] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 4 MPa.

[0215] According to one embodiment, the shell has a breaking stress comprised between 0.1 and 3 MPa.

[0216] Methods for determining the breaking stress are well known to those skilled in the art. A typical method is as follows: 2 drops of the microcapsule suspension are diluted in 10 ml of demineralized water. The diluted solution is applied to a 20x20 mm glass microscope slide and then removed. This is repeated once more, leaving a small single drop of about 1 mm on the slide, which is dried at room temperature with controlled relative humidity. The sample is allowed to dry overnight. Once the sample is dry, the slide is placed under a microscope and analyzed with a Femto Tools microforce probe.

[0217] A setup using a microforce probe / xyz robot / microscope assembly was used for the measurements. The "zero distance" point of the probe is set at 100 μm from the glass slide. The probe is then positioned on the microcapsule, approximately 20 μm from the glass. The program is started and the microforce probe moves downwards, exerting pressure on the capsule. The force is recorded versus distance. The force curves are processed with the R statistical programming package (https: / / www.r-project.org / ) applying R scripts developed to extract the mechanical properties from the curves.

[0218] The breaking stress is a well-known parameter obtained by dividing the breaking force by the average size of the microcapsules (both parameters are provided by the program defined above).

[0219] According to one embodiment, the polyamide shell comprises: Acyl chlorides, Amino compounds A, optionally an amino compound B, ·protein in the presence of a crosslinking agent as defined above.

[0220] According to one embodiment, the shell comprises cross-linked proteins.

[0221] Another subject of the present invention is a composition comprising at least one microcapsule, the microcapsule comprising: a core comprising a hydrophobic material, preferably a fragrance, preferably an oily core; a polyamide-based shell, Acyl chloride in an amount of 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% w / w, an amino compound A in an amount between 1% and 50% w / w, preferably between 7% and 40% w / w; optionally an amino compound B in an amount comprised between 1% and 50% w / w, preferably between 2 and 25% w / w, Optionally, a protein content of 0.1 to 90%, preferably 0.1 to 75%, more preferably 1 to 70%. The shell and The polyamide-based core-shell microcapsule or polyamide-based core-shell microcapsule slurry comprises:

[0222] The embodiments described above for the method according to the invention also apply to the microcapsules or microcapsule slurries according to the invention, in particular to the hydrophobic materials, cross-linking agents, proteins, acyl chlorides, amino compounds and stabilizers.

[0223] According to one embodiment, amino compound A and amino compound B are different.

[0224] According to certain embodiments, the polyamide microcapsules comprise an inner shell of polyurea.

[0225] The composition of the shell can be quantified, for example, by elemental analysis and identified by solid-state NMR, two techniques well known to those skilled in the art.

[0226] In certain embodiments, the shell material is a biodegradable material.

[0227] In certain embodiments, the shell is at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% biodegradable within 60 days according to OECD 301F.

[0228] In certain embodiments, the core-shell microcapsules are at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% biodegradable within 60 days according to OECD 301F.

[0229] Thereby it is understood that the core-shell microcapsules, 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 OECD 301F.

[0230] In certain embodiments, the oil core, preferably the perfume oil, has a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD 301F.

[0231] OECD301F is a standard test method for biodegradability established by the Organization for Economic Cooperation and Development.

[0232] Exemplary methods for extraction of shells for the determination of biodegradability are disclosed in Gasparini and all in Molecules 2020, 25,718.

[0233] In certain embodiments, the microcapsules have a stability or chemical stability of 50% or less, preferably 40% or less, preferably 35% or less, preferably 30% or less. Typically, the stability or chemical stability of the microcapsules is determined as 50% or less, preferably 40% or less, preferably 35% or less, preferably 30% or less of the perfume leaking out of the microcapsules when incorporated into a consumer product at a particular storage time and temperature, and the microcapsules are preferably stable in a fabric softener, liquid detergent, body wash, deodorant or antiperspirant after storage at 37°C for 15 days, more preferably 30 days at 37°C, and are stable in a body lotion, shampoo or hair conditioner after storage at 40°C for at least 2 weeks.

[0234] Furthermore, the microcapsules preferably exhibit a detectable frictional effect in fresh samples, and preferably exhibit a detectable frictional effect after application and storage at 37°C for 15 days, and even more preferably for 30 days at 37°C.

[0235] Another subject of the present invention is a carrier material, preferably a polymeric carrier material selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginates, carrageenans, cellulose derivatives and mixtures thereof, - microcapsules as defined above encapsulated in said carrier material; - optionally with non-encapsulated flavorings encapsulated in said carrier material; are solid particles comprising:

[0236] The solid particles and microcapsule powders defined above can be used interchangeably in the present invention.

[0237] Optional Ingredients When the microcapsules are in the form of a slurry, the microcapsule slurry may contain auxiliary ingredients selected from the group of thickeners / rheology modifiers, antimicrobial agents, opacity enhancers, mica particles, salts, pH stabilizers / buffering ingredients, preferably in an amount comprised between 0 and 15% by weight based on the total weight of the slurry.

[0238] According to another embodiment, the microcapsule slurry of the present invention comprises additional non-encapsulated (ie, non-encapsulated) flavoring, preferably in an amount comprised between 5 and 50% by weight based on the total weight of the slurry.

[0239] Multiple microcapsule system According to one embodiment, the microcapsules of the present invention (first type of microcapsules) may be used in combination with a second type of microcapsules.

[0240] Another subject of the present invention is - microcapsules of the invention as a first type of microcapsule, - a second type of microcapsule; wherein the first type of microcapsules and the second type of microcapsules differ in their hydrophobic material and / or their wall material and / or their coating material.

[0241] According to certain embodiments, the microcapsule delivery system is in the form of a slurry.

[0242] The wall of the second type of microcapsules may be different. As a non-limiting example, the polymer shell of the second type of microcapsule comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyhydroxyalkanoate, polyacrylate, polyester, polyaminoester, polyepoxide, polysiloxane, polycarbonate, polysulfonamide, urea formaldehyde, melamine formaldehyde resin, melamine formaldehyde resin crosslinked with polyisocyanate or aromatic polyol, melamine urea resin, melamine glioxal resin, gelatin / gum arabic shell wall and mixtures thereof.

[0243] The second type of microcapsule may comprise an oily core comprising a hydrophobic active agent, preferably a fragrance, and a composite shell comprising a first material and a second material, the first material being a coacervate and the second material being a polymeric material, the first and second materials being different from each other. In a particular embodiment, the weight ratio of the first material to the second material is comprised between 50:50 and 99.9:0.1. In a particular embodiment, the coacervate comprises a first polyelectrolyte, preferably selected from proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), most preferably gelatin, and a second polyelectrolyte, preferably an alginate, a cellulose derivative, a guar gum, a pectinate, a carrageenan, a polyacrylic acid and a methacrylic acid, or a xanthan gum, or even a vegetable gum, such as gum acacia (gum arabic), most preferably gum arabic. The coacervate of the first material can be chemically hardened using a suitable crosslinking agent such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin, or enzymatically hardened using an enzyme such as transglutaminase. The second polymeric material can be selected from the group consisting of polyureas, polyurethanes, polyamides, polyesters, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea or melamine and glyoxal, and mixtures thereof, preferably polyureas and / or polyurethanes. The second material is preferably present in an amount of less than 3% by weight, preferably less than 1% by weight, based on the total weight of the slurry of second type of microcapsules.

[0244] As non-limiting examples, 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, i.e. organic-inorganic, such as a hybrid shell composed of at least two types of inorganic particles crosslinked, or even a shell obtained by hydrolysis and condensation reactions of polyalkoxysilane macromonomer compositions.

[0245] According to one embodiment, the shell of the second type of microcapsule comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glioxal.

[0246] According to another embodiment, the shell of the second type of microcapsule is polyurea-based, for example, but not limited to, made of isocyanate-based monomers and amine-containing crosslinkers such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall that is the reaction product of polymerization between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from the group consisting of amines (e.g., water-soluble guanidine salts and guanidine); colloidal stabilizers or emulsifiers; and encapsulated fragrances. However, the use of amines can be omitted. According to a particular embodiment, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages defined by weight relative to the total weight of the colloidal stabilizer). According to another embodiment, the emulsifier is an anionic or amphiphilic biopolymer, which in one embodiment may be selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0247] According to another embodiment, the microcapsule wall material of the second type of microcapsule may comprise any suitable resin, including in particular melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include reaction products of aldehydes and amines, 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, urea-resorcinol, and mixtures thereof. Materials suitable for fabrication can be obtained from one or more of the following companies: Solutia Inc. (St Louis, Missouri USA), Cytec Industries (West Paterson, New Jersey USA), Sigma-Aldrich (St. Louis, Missouri USA).

[0248] According to another embodiment, the second type of microcapsules comprises: 1) combining a perfume oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) dispersing or dissolving an aminoplast resin and, optionally, a stabilizer in water to form an aqueous phase; 3) preparing an oil-in-water dispersion having an average droplet size comprised between 1 and 100 microns by mixing an oil phase and an aqueous phase; 4) performing a curing step to form the walls of the microcapsules; 5) Optionally, drying the final dispersion to obtain dry core-shell microcapsules. and (b) preparing one-shell aminoplast core-shell microcapsules comprising:

[0249] According to one embodiment, the second type of microcapsules are formaldehyde-free capsules. A typical process for preparing a slurry of aminoplast formaldehyde-free microcapsules is as follows: 1) a. a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound containing two NH2 functional groups; b. Glyoxal, C 4~6 An aldehyde component in the form of a mixture of 2,2-dialkoxy-ethanal and optionally glyoxalate, said mixture having a glyoxal / C ratio of 1 / 1 to 10 / 1. 4~6 an aldehyde component having a molar ratio of 2,2-dialkoxy-ethanal; and c. Protonic acid catalyst preparing an oligomeric composition comprising or obtained by reacting the reaction product of 2) The droplet size is between 1 and 600 microns; a. Oil, b.Aqueous medium, c. at least one oligomeric composition obtained in step 1; d. i.C4~C 12 Aromatic or aliphatic di- or tri-isocyanates, and their biuret, triuret, trimer, trimethylolpropane adducts, and mixtures thereof, and / or ii.Formula: A-(Oxirane-2-ylmethyl) n [In the formula, n represents 2 or 3, and A represents a C2-C6 group optionally containing 2-6 nitrogen and / or oxygen atoms. Di- or tri-oxirane compounds of at least one crosslinking agent selected from e. Optionally, a C1-C4 compound containing two NH2 functional groups preparing an oil-in-water dispersion comprising: 3) heating the dispersion; 4) cooling the dispersion; Includes.

[0250] In another particular embodiment, the second type of microcapsules comprises: an oily core containing a hydrophobic active agent, preferably a fragrance; - optionally an inner shell made of polymerized multifunctional monomers, - a protein-containing biopolymer shell, cross-linked by at least one protein; Includes.

[0251] According to a particular embodiment, the protein is selected in the group consisting of milk proteins, caseinates such as sodium or calcium caseinate, casein, whey proteins, hydrolyzed proteins, gelatin, gluten, pea proteins, soy proteins, silk proteins and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate.

[0252] According to a particular embodiment, the proteins include sodium caseinate and preferably globular proteins selected in the group consisting of whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins, and mixtures thereof.

[0253] The protein is preferably a mixture of sodium caseinate and whey protein.

[0254] According to a particular embodiment, the biopolymer shell comprises cross-linked proteins selected in the group consisting of sodium caseinate and / or whey protein.

[0255] According to a particular embodiment, the slurry of the second type of microcapsules is an oily core containing a hydrophobic active agent, preferably a fragrance; - an inner shell made of polymerized multifunctional monomers, preferably polyisocyanates having at least two isocyanate functional groups; - a biopolymer shell comprising at least one protein cross-linked, the protein preferably comprising a mixture comprising sodium caseinate and a globular protein, preferably whey protein; - optionally at least one outer mineral layer The composition comprises at least one microcapsule made of

[0256] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0257] The weight ratio of sodium caseinate to whey protein is preferably comprised between 0.01 and 100, preferably between 0.1 and 10, more preferably between 0.2 and 5.

[0258] In another particular embodiment, the second type of microcapsules comprises: an oily core containing a hydrophobic active agent, preferably a fragrance; - a polyamide shell, Acyl chlorides, a first amino compound, and ·Second Amino Compound and a polyamide shell comprising or derived therefrom. The polyamide core-shell polyamide microcapsule comprises:

[0259] According to a particular embodiment, the second type of microcapsules comprises: an oily core containing a hydrophobic active agent, preferably a fragrance; A polyamide shell, Acyl chloride in an amount of preferably 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% (w / w), the first amino compound in an amount preferably between 1% and 50% (w / w), preferably between 7 and 40% (w / w); a second amino compound in an amount preferably between 1% and 50% (w / w), preferably between 2 and 25% (w / w), A stabilizer, preferably a biopolymer, in an amount preferably between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%. and a polyamide shell comprising or derived therefrom. Includes.

[0260] According to a particular embodiment, the second type of microcapsules comprises: an oily core containing a hydrophobic active agent, preferably a fragrance; - a polyamide shell, Acyl chlorides, a first amino compound selected from the group consisting of amino acids, preferably L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof, a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, and A biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and / or mixtures thereof. and a polyamide shell comprising or derived therefrom. Includes.

[0261] According to another embodiment, the shell of the second type of microcapsule is polyurea or polyurethane based. Examples of methods for preparing polyurea and polyurethane based microcapsule slurries are described, for example, in WO 2007 / 004166, EP 2300146 and EP 25799. Typically, the method for preparing polyurea or polyurethane based microcapsule slurries comprises the following steps: a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding an oil phase to an aqueous phase to form an oil-in-water dispersion with an average droplet size comprised between 1 and 500 μm, preferably between 5 and 50 μm; and d) applying conditions sufficient to induce interfacial polymerization to form microcapsules in the form of a slurry.

[0262] Perfuming compositions and consumer products The microcapsules of the invention can be used in combination with active ingredients. The subject of the invention is therefore (i) a microcapsule as defined above, (ii) an active ingredient, preferably selected from the group consisting of cosmetic ingredients, skin care ingredients, fragrance ingredients, flavor ingredients, deodorant ingredients, bactericidal ingredients, fungicidal ingredients, pharmaceutical or pesticide ingredients, disinfecting ingredients, insect repellents or attractants, and mixtures thereof; A composition comprising:

[0263] The capsules of the present invention exhibit good performance in terms of stability in hostile media.

[0264] Another subject of the present invention is (i) a microcapsule as defined above, wherein the oil comprises a fragrance; (ii) at least one ingredient selected from the group consisting of perfume carriers, perfume co-ingredients, and mixtures thereof; (iii) optionally, at least one flavoring adjuvant; A fragrance composition comprising:

[0265] Liquid perfume carriers can include, as non-limiting examples, emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be comprehensive. However, as non-limiting examples, the most commonly used solvents can be dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate. For compositions that include both perfume carriers and perfume co-ingredients, suitable perfume carriers other than those specified above can also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (supplied by Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (supplied by Dow Chemical Company). By "perfume co-ingredient" is meant herein a compound that is used in perfume preparations or compositions to impart a hedonic effect and is not a microcapsule as defined above. In other words, to be considered a perfuming co-ingredient, such a co-ingredient must not only have an odor, but must also be recognized by those skilled in the art as being at least capable of imparting or modifying the odor of the composition in a positive or pleasant way.

[0266] The nature and type of perfuming co-ingredients present in the perfuming composition do not require a more detailed description here, and are in any case not comprehensive, and a person skilled in the art can select them based on his general knowledge, depending on the intended use or application, and the desired organoleptic effect.Generally, these perfuming co-ingredients belong to various chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds, and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.Many of these co-ingredients are described in any case in reference literature, for example in the book Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or its more recent editions, or other treatises of the same kind, and in the abundant patent literature in the field of perfumery.It is also understood that said co-ingredients may be compounds known to release various kinds of perfuming compounds in a controlled manner. The co-ingredients are 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-ylhexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methyl undec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof.

[0267] By "perfuming adjuvant" is meant herein an ingredient capable of imparting additional added benefits such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfuming bases cannot be comprehensive, but it is necessary to mention that said ingredients are well known to those skilled in the art.

[0268] Preferably, the perfuming composition according to the invention comprises 0.01 to 30% by weight of microcapsules as defined above.

[0269] The microcapsules of the present invention can be advantageously used in many fields of application and can be used in consumer products: they can be used in liquid form, which is applicable in liquid consumer products, and also in powder form, which is applicable in powder consumer products.

[0270] According to a particular embodiment, the consumer product defined above is a liquid, a) 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; c) microcapsules or a microcapsule slurry as defined above, d) optionally, a non-encapsulated flavoring; Includes.

[0271] According to a particular embodiment, the consumer product defined above is in powder form, a) 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) a microcapsule powder as defined above, c) Optionally, a flavor powder different from the microcapsules defined above. Includes.

[0272] In the case of microcapsules containing a perfume oil-based core, the products of the invention can be used in particular in perfumed consumer products, such as those belonging to fine fragrances or "functional" perfumery. Functional perfumery includes in particular personal care products, including hair care, body cleansing, skin care, hygiene care, and home care products, including laundry care, surface care and air care. As a result, another subject of the invention consists of perfumed consumer products, which contain, as perfuming ingredient, a microcapsule as defined above or a perfuming composition as defined above. The perfume element of said consumer products may be a combination of perfume microcapsules as defined above and non-encapsulated or non-encapsulated perfumes, as well as perfume microcapsules of other types than those disclosed herein.

[0273] especially, a) 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; c) a flavoring composition as defined above; A liquid consumer product comprising the compound is another subject of the present invention.

[0274] Also, (a) 2 to 65 weight percent of at least one surfactant, based on the total weight of the consumer product; (b) a flavouring composition as defined above; A powdered consumer product comprising the compound is part of the present invention.

[0275] Thus, the microcapsules of the present invention can be added to perfumed consumer products either as such or as part of the perfume composition of the present invention.

[0276] For the sake of clarity, it is necessary to mention that by "perfumed consumer product" it is meant a consumer product which is expected to provide, among other benefits, a perfuming effect on the surface to which it is applied (for example skin, hair, fabric, paper or residential surfaces) or in the air (air freshener sprays, deodorants, etc.) In other words, the perfumed consumer product according to the invention is a manufactured article comprising a functional formulation, also called a "base", together with a benefit agent, among other things an effective amount of the microcapsules according to the invention.

[0277] The nature and type of other components of the perfumed consumer product do not require a more detailed description herein, and are in any case not comprehensive, and a person skilled in the art can select them based on general knowledge, depending on the nature and desired effect of said product.The basic formulations of consumer products that can incorporate the microcapsules of the present invention can be found in the abundant literature on such products.These formulations do not require a more detailed description herein, and are in any case not comprehensive.A person skilled in the formulation of such consumer products is entirely capable of selecting suitable ingredients based on general knowledge and available literature.

[0278] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, colognes, aftershaves, body splashes; fabric care products, such as liquid or solid detergents, tablets and unit doses (single or multi-chamber), fabric softeners, dryer sheets, fabric deodorants, ironing waters or bleaches; personal care products, such as hair care products (e.g. shampoos, hair conditioners, colorants or hairsprays), cosmetics (e.g. vanishing creams, body lotions, or deodorants or antiperspirants), or It may be a skin care product (e.g. a perfumed soap, a shower or bath smooth, a body wash, an oil or gel, a bath salt, or a hygiene product); an air care product, e.g. a deodorising spray, or a "ready to use" powder deodorising spray; or a home care product, e.g. an all-purpose cleaner, a liquid or powder or tablet dishwashing product, a toilet cleaner, or a product for cleaning various surfaces, e.g. sprays & wipes for treating / refreshing fabrics or hard surfaces (floors, tiles, stone paving, etc.); a hygiene product, e.g. sanitary napkins, diapers, toilet paper.

[0279] Another subject of the present invention is - a personal care active base; - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above; A consumer product comprising: The consumer product is in the form of a personal care composition.

[0280] The personal care active bases in which the microcapsules of the present invention can be incorporated can be found in the abundant literature on such products.These formulations do not require detailed description here, and are in any case not comprehensive.Those skilled in the formulation of such consumer products are entirely capable of selecting suitable ingredients based on general knowledge and available literature.

[0281] The personal care composition is preferably selected in the group consisting of a hair care product (e.g. shampoo, hair conditioner, colorant or hairspray), a cosmetic product (e.g. vanishing cream, body lotion, or deodorant or antiperspirant), or a skin care product (e.g. perfumed soap, shower or bath smooth, body wash, oil or gel, bath salts, or hygiene product).

[0282] Another subject of the present invention is - a home or fabric care active base; - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above; A consumer product comprising: The consumer product is in the form of a home care or fabric care composition.

[0283] Home care or fabric care active bases in which the microcapsules of the present invention can be incorporated can be found in the abundant literature on such products. Their formulations do not require a detailed description here, and are in any case not comprehensive. Those skilled in the formulation of such consumer products are entirely capable of selecting suitable ingredients based on general knowledge and available literature.

[0284] Preferably, the consumer product comprises 0.1-15% by weight, more preferably 0.2-5% by weight, of the microcapsules of the invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, the above concentrations can be adapted depending on the beneficial effect desired for each product.

[0285] A subject of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising a microcapsule or a microcapsule slurry as defined above, wherein the consumer product has a pH of less than 7.

[0286] A subject of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising microcapsules or a microcapsule slurry as defined above, wherein the consumer product has a pH of 7 or higher.

[0287] Another object of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising microcapsules, the consumer product having a pH of 7 or more, the microcapsules being a core comprising a hydrophobic material, preferably a fragrance, preferably an oily core; a polyamide-based shell, Acyl chlorides, Amino compounds A, optionally an amino compound B, ·protein and a shell comprising the reaction product of, preferably in the presence of a crosslinker as defined above. Including, The shell is a consumer product that is at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% biodegradable within 60 days according to OECD 301F.

[0288] Another subject of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising microcapsules, the consumer product having a pH of less than 7, the microcapsules being a core comprising a hydrophobic material, preferably a fragrance, preferably an oily core; a polyamide-based shell, Acyl chlorides, Amino compounds A, optionally an amino compound B, ·protein and a shell comprising the reaction product of, preferably in the presence of a crosslinker as defined above. Including, The shell is a consumer product that is at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% biodegradable within 60 days according to OECD 301F.

[0289] For the liquid consumer products described below, by "active base" it should be understood that the active base comprises active ingredients (typically including surfactants) and water.

[0290] With respect to the solid consumer products described below, by "active base" it should be understood that the active base includes active materials (which typically include surfactants) and adjuvants (such as bleaches, buffers; builders; stain removing or stain suspending polymers; granular enzyme particles, rust inhibitors, antifoam agents, suds suppressors; dyes, fillers and mixtures thereof).

[0291] Fabric softener The subject of the present invention is a fabric softener active base, preferably comprising at least one active material selected from the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (ester quats), Hamburg esterquats (HEQ), TEAQ (triethanolamine quats), silicones and mixtures thereof, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil and a fabric softener composition comprising:

[0292] Liquid detergent The subject of the present invention is a liquid detergent active base, preferably comprising at least one active material chosen from the group consisting of anionic surfactants such as alkylbenzenesulfonates (ABS), secondary alkylsulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil A consumer product in the form of a liquid detergent composition comprising:

[0293] Solid detergent The subject of the present invention is a solid detergent active base, preferably comprising at least one active material chosen from the group consisting of anionic surfactants such as alkylbenzenesulfonates (ABS), secondary alkylsulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides, and preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule powder or a microcapsule slurry or a microcapsule as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil and a solid detergent composition comprising:

[0294] Shampoo / Shower gel The subject of the present invention is a shampoo or shower gel active base, preferably comprising at least one active material chosen from the group consisting of sodium alkyl ether sulfates, ammonium alkyl ether sulfates, alkyl amphoacetates, cocamidopropyl betaine, cocamide MEA, alkyl glucosides and amino acid surfactants, and mixtures thereof, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil A consumer product in the form of a shampoo or shower gel composition comprising:

[0295] Rinse-off conditioner The subject of the present invention is a rinse-off conditioner active base, preferably comprising at least one active material selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride and mixtures thereof, preferably used in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil and a rinse-off conditioner composition comprising:

[0296] Solid fragrance enhancer The subject of the present invention is - solid carriers, preferably selected from the group consisting of urea, sodium chloride, sodium sulfate, sodium acetate, zeolites, sodium carbonate, sodium bicarbonate, clays, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars, such as sucrose, mono-, di- and polysaccharides, and derivatives, such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols, such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid, or any water-soluble solid acid, fatty alcohol or fatty acid, and mixtures thereof, - a microcapsule slurry or microcapsules as defined above, preferably in the form of a powder in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil A consumer product in the form of a solid fragrance enhancer composition comprising:

[0297] Liquid fragrance enhancer The subject of the present invention is an aqueous phase; - a surfactant system consisting essentially of one or more non-ionic surfactants having an average HLB between 10 and 14, preferably selected in the group consisting of ethoxylated fatty alcohols, POE / PPG (polyoxyethylene and polyoxypropylene) ethers, mono- and polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxyesters, alkyl polyglucosides, amine oxides, and combinations thereof; - a linker selected from 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, surfactants with an HLB of less than 10, and mixtures thereof; - a microcapsule slurry or microcapsules as defined above, preferably in the form of a slurry, in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; - optionally with non-encapsulated perfume oil and a liquid fragrance enhancer composition comprising:

[0298] Hair Coloring The subject of the present invention is - an oxidizing phase comprising an oxidizing agent and an alkaline phase comprising an alkalizing agent, a dye precursor and a coupling compound, said dye precursor and said coupling compound forming an oxidizing hair dye in the presence of an 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 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, - optionally, unencapsulated perfume oil and a consumer product in the form of an oxidative hair coloring composition comprising:

[0299] Perfuming composition According to a particular embodiment, the consumer product comprises: - 0.1 to 30%, preferably 0.1 to 20%, of microcapsules or a microcapsule slurry as defined above, - 0-40%, preferably 3-40% fragrance, and 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol, based on the total weight of the perfuming composition The fragrance composition is in the form of a fragrance composition comprising:

[0300] The invention will now be further illustrated by examples, it being understood that the invention as claimed is not intended to be limited in any way by these examples.

[0301] Working Example General protocol: Process A: Adding a crosslinker (TG) to the aqueous phase before the emulsification process Sodium caseinate is dispersed in Neobee (an inert organic solvent) in a water bath under magnetic stirring at 60°C for 30 minutes. This premix and the acyl chloride compound are added to the perfume (see Table 2) to form the oil phase. The water phase is formed with L-lysine at a concentration of 2.5% by weight and kept at 45°C. Just before the emulsification step, an enzyme (e.g. transglutaminase) is added to the water phase at a concentration of 1.5%. The oil phase is mixed with the water solution and stirred with an Ultra Turrax at 25,000 rpm for 30 seconds to obtain an emulsion. A solution of ethylenediamine and a base such as sodium hydroxide is added dropwise to the suspension. The reaction mixture is stirred at 45°C for 3 hours to obtain a white dispersion, and then the enzyme is inactivated at 70°C for 1 hour.

[0302] Process B: Adding a cross-linking agent (TG) to the slurry after the curing process Sodium caseinate is dispersed in Neobee in a water bath under magnetic stirring at 60°C for 30 minutes. This premix and the acyl chloride compound are added to the perfume to form the oil phase. The water phase is formed with L-lysine at a concentration of 2.5% by weight and kept at 45°C. The oil phase is mixed with the water solution and stirred with an Ultra Turrax at 25,000 rpm for 30 seconds to obtain an emulsion. A solution of ethylenediamine and a base such as sodium hydroxide is added dropwise to the suspension. The reaction mixture is stirred at 60°C for 4 hours to obtain a white dispersion. The suspension is adjusted to pH 7. A solution of CaCl2 (0.5 g in 2 g water) and a solution of transglutaminase (1 g in 5 g water) are added successively to the dispersion. The mixture is then left under stirring at 45°C for 3 hours and then at 70°C for 1 hour to inactivate the enzyme.

[0303] [Table 1]

[0304] Fragrance: [Table 2]

[0305] Example 1 Preparation of microcapsules according to the invention (Process A) Preparation of capsule A using 1,3,5-benzenetricarbonyl chloride (BTC - acyl chloride), sodium caseinate (NaCas - stabilizer), ethylenediamine (EDA - amino compound A), L-lysine (amino compound B), sodium hydroxide (NaOH - base), transglutaminase (Tg - cross-linker), calcium chloride (salt) and perfume oil (see Table 2).

[0306] [Table 3]

[0307] Example 2 Preparation of microcapsules according to the invention (Process B) Preparation of capsule B using 1,3,5-benzenetricarbonyl chloride (BTC - acyl chloride), sodium caseinate (NaCas - stabilizer), ethylenediamine (EDA - amino compound A), L-lysine (amino compound B), sodium hydroxide (NaOH - base), transglutaminase (Tg - cross-linker), calcium chloride (salt) and perfume oil (see Table 2).

[0308] [Table 4]

[0309] Example 3 Stable performance The microcapsules of the present invention are dispersed in a fabric softener composition as set forth in Table 18 or a liquid detergent composition as set forth in Table 6 to obtain a concentration of 0.116% encapsulated perfume oil.

[0310] [Table 5]

[0311] [Table 6]

[0312] Weigh 2g of sample (base including capsules) into a 20mL vial. Add 10mL of extraction solvent isooctane to the vial containing the internal standard 1,4-dibromobenzene with a precisely known concentration of approximately 90ng / uL. Shake at 40RPM for 45 minutes to extract the unencapsulated flavorings. Remove the solvent phase.

[0313] To measure leakage to the base, an Agilent GCFID7890A is used with the injector set to 250 °C, helium used as the carrier gas at a flow rate of 1 mL / min, and the oven temperature programmed from 120 °C, held for 5 min, ramped to 170 °C at 10 °C / min, ramped to 220 °C at 25 °C / min, then ramped to 260 °C at 25 °C / min. A final post run is performed at 260 °C to finish the measurement.

[0314] Calibration solutions are prepared at 100, 300 and 600ng / uL of fragrance oil in isooctane. It is important that the fragrance oil used to generate the calibration curve is from the same batch as that used to make the microcapsules.

[0315] [Table 7]

[0316] [Table 8]

[0317] It can be concluded that the microcapsules prepared by the method of the present invention show satisfactory stability in consumer products.

[0318] Example 4 Mechanical property measurements A. Sample Description Microcapsules were prepared according to process A.

[0319] [Table 9]

[0320] B. Protocol Two drops of the microcapsule suspension are diluted in 10 ml of demineralized water. The diluted solution is applied to a 20 x 20 mm glass microscope slide and then removed. This is repeated once more, leaving a small single drop of about 1 mm on the slide, which is dried at room temperature with controlled relative humidity. The sample is allowed to dry overnight. Once the sample is dry, the slide is placed under a microscope and analyzed with a Femto Tools microforce probe.

[0321] A setup using a microforce probe / xyz robot / microscope assembly was used for the measurements. The "zero distance" point of the probe was set at 100 μm from the glass slide. The probe was then positioned on the microcapsule, approximately 20 μm from the glass. The program was started and the microforce probe moved downwards, exerting pressure on the capsule. The force was recorded versus distance. The force curves were processed with the R statistical programming package (version 3.1.2; http: / / www.R-project.org) applying R scripts developed to extract the mechanical properties from the curves.

[0322] These parameters are also described in Hybrid microcapsules with tunable properties via Pickering emulsions templates for the encapsulation of bioactives volatiles (RCS Adv., 2016, 6, 102595).

[0323] C. Overview [Table 10]

[0324] Microcapsule C (with enzyme reaction) showed a high percentage of broken microcapsules, which is favorable for sensory performance.

[0325] Sample B showed high adhesion, which may also favor sensory performance due to improved build-up during customer application.

[0326] D. Conclusion It can be emphasized that the enzymatic reaction confers good mechanical properties to the microcapsule shell.

[0327] Example 5 Preparation of spray-dried microcapsules Emulsions A through E are prepared having the following components:

[0328] [Table 11-1] [Table 11-2]

[0329] [Table 12-1] [Table 12-2]

[0330] The ingredients of the polymer matrix (maltodextrin and capsul™, or capsul™, citric acid and tripotassium citrate) are added to 45-50°C water until completely dissolved.

[0331] For Emulsion D, non-encapsulated fragrance C is added to the water phase.

[0332] The microcapsule slurry is added to the resulting mixture, which is then gently mixed at 25° C. (room temperature).

[0333] Granular powders A-E are prepared by spray drying emulsions A-E using a Sodeva Spray Dryer (supplied from France) with the air inlet temperature set at 215° C. and the throughput set at 500 ml per hour. The air outlet temperature is 105° C. The emulsions before atomization are at room temperature.

[0334] Example 6 Liquid fragrance enhancer composition A sufficient amount of the exemplary microcapsules is weighed out and mixed into a liquid fragrance enhancer to add the equivalent of 0.2% perfume.

[0335] [Table 13]

[0336] Prepare various ringing gel compositions according to the following protocol (Compositions 1-6).

[0337] In the first step, the aqueous phase (water), the solvent (propylene glycol), if present, and the surfactant are mixed under magnetic stirring at 300 rpm at room temperature for 5 minutes.

[0338] In the second step, the linker is dissolved in the hydrophobic active ingredient (fragrance) at room temperature under magnetic stirring at 300 rpm. The resulting mixture is mixed for 5 minutes.

[0339] The aqueous and oil phases are then mixed at room temperature for 5 minutes to form a clear or milky ringing gel.

[0340] Example 7 Liquid detergent composition A sufficient amount of the exemplary microcapsules is weighed out and mixed into a liquid detergent to add the equivalent of 0.2% perfume.

[0341] [Table 14]

[0342] Example 8 Unit Dose Formulations A sufficient amount of the exemplary microcapsules is weighed out and mixed into a unit dose formulation to add the equivalent of 0.2% flavor.

[0343] The unit dose formulation can be contained in a PVOH (polyvinyl alcohol) film.

[0344] [Table 15]

[0345] Example 9 Powder detergent composition A sufficient amount of the exemplary microcapsules is weighed out and mixed into a powder detergent composition to add the equivalent of 0.2% perfume.

[0346] [Table 16]

[0347] Example 10 Concentrated all-purpose cleaner composition A sufficient amount of the exemplary microcapsules is weighed and mixed into a concentrated all-purpose cleaner composition to add the equivalent of 0.2% fragrance.

[0348] [Table 17]

[0349] Example 11 Solid fragrance enhancer composition The following compositions are prepared:

[0350] [Table 18]

[0351] [Table 19]

[0352] Example 12 Shampoo Composition A sufficient amount of the exemplary microcapsules is weighed and mixed into a shampoo composition to add the equivalent of 0.2% fragrance.

[0353] [Table 20]

[0354] Polyquaternium-10 is dispersed in water. The remaining ingredients of Phase A are mixed separately by adding them in order with thorough mixing after each addition. This premix is ​​then added to the Polyquaternium-10 dispersion and mixed for 5 minutes. Phase B and premixed Phase C (Monomuls 90L-12 heat melted in Texapon NSO IS) are then added. The mixture is mixed well. Phase D and Phase E are then added with stirring. The pH is adjusted to pH 5.5-6.0 with citric acid solution.

[0355] Example 13 Shampoo Composition A sufficient amount of the exemplary microcapsules is weighed and mixed into a shampoo composition to add the equivalent of 0.2% fragrance.

[0356] [Table 21-1] [Table 21-2]

[0357] The premix containing guar hydroxypropyltrimonium chloride and polyquaternium-10 is added to the water and tetrasodium EDTA while mixing. When the mixture is uniform, NaOH is added. Phase C ingredients are then added and the mixture is heated to 75°C. Phase D ingredients are added and mixed until uniform. Heat is removed and the mixture is allowed to cool to room temperature. At 45°C, the final viscosity is adjusted with 25% NaCl solution while mixing Phase E ingredients, and the pH is adjusted to 5.5-6 with 10% NaOH solution.

[0358] Example 14 Rinse-off hair composition A sufficient amount of the exemplary microcapsules is weighed out and mixed into a rinse-off composition to add the equivalent of 0.2% perfume.

[0359] [Table 22]

[0360] The ingredients of Phase A are mixed until a homogenous mixture is obtained. The Tylose is completely dissolved. The mixture is then heated to 70-75°C. The ingredients of Phase B are combined and melted at 70-75°C. The ingredients of Phase B are then added to Phase A with good mixing and mixing is continued until the mixture has cooled to 60°C. The ingredients of Phase C are then added with mixing and mixing is continued until the mixture has cooled to 40°C. The pH is adjusted to pH 3.5-4.0 with citric acid solution.

[0361] Example 15 Antiperspirant spray anhydrous composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant spray anhydrous composition to add the equivalent of 0.2% perfume.

[0362] [Table 23]

[0363] Using a high speed stirrer, add the silica and quaternium-18-hectorite to the mixture of isopropyl myristate and cyclomethicone. After complete swelling, add the aluminum chlorohydrate in small portions under stirring until the mixture is homogenous and free of lumps. Fill an aerosol can with 25% of the suspension and 75% of propane / butane (2.5 bar).

[0364] Example 16 Antiperspirant spray emulsion composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant spray emulsion composition to add the equivalent of 0.2% perfume.

[0365] [Table 24]

[0366] The ingredients of Part A and Part B are weighed separately. The ingredients of Part A are heated to 60°C and the ingredients of Part B are heated to 55°C. The ingredients of Part B are poured into A in small portions with continuous stirring. The mixture is stirred well until it reaches room temperature. The ingredients of Part C are then added. The emulsion is mixed and introduced into an aerosol can. The propellant is crimped and added. Aerosol filling: 30% Emulsion: 70% Propane / Butane 2.5bar

[0367] Example 17 Deodorant spray composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant deodorant spray composition to add the equivalent of 0.2% fragrance.

[0368] [Table 25]

[0369] All ingredients are mixed and dissolved according to the order in Table 24. Aerosol cans are then filled, crimped and propellant added (aerosol fill: 40% active solution: 60% propane / butane 2.5 bar).

[0370] Example 18 Antiperspirant roll-on emulsion composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.

[0371] [Table 26]

[0372] Parts 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. The mixture is then cooled under stirring, and Part C is added slowly with stirring when the mixture reaches 45°C, and Part D is added slowly with stirring when the mixture reaches 35°C. The mixture is then cooled to room temperature.

[0373] Example 19 Antiperspirant roll-on composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant roll-on composition to add the equivalent of 0.2% perfume.

[0374] [Table 27]

[0375] The ingredients of Part B are mixed in a container and then the ingredients of Part A are added. Part C is then dissolved in Parts A and B. Along with the fragrance, 1 part Cremophor RH40 for every 1 part fragrance is added with good mixing.

[0376] Example 20 Antiperspirant roll-on composition A sufficient amount of the exemplary microcapsules is weighed and mixed into an antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.

[0377] [Table 28]

[0378] Prepare Part A by sprinkling hydroxyethyl cellulose into water in small portions while stirring rapidly with a turbine. Continue stirring until the hydroxyethyl cellulose is completely swollen and a clear gel is obtained. Then pour Part B into Part A in small portions while continuing to stir until the mixture is homogenous. Add Part C.

[0379] Example 21 Alcohol-free deodorant pump A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0380] [Table 29]

[0381] All ingredients are mixed in the order listed and the mixture is heated slightly to dissolve the cetyl lactate.

[0382] Example 22 Deodorant pump containing alcohol A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0383] [Table 30]

[0384] Mix the ingredients of Part B. Dissolve the ingredients of Part A in the order shown and pour into Part B.

[0385] Example 23 Talc Compound A sufficient amount of granules A to E is weighed out and mixed and introduced into a standard talc base: 100% talc, very slight characteristic odor, white powder, supplier: LUZENAC, and an equivalent amount of 0.2% flavor is added.

[0386] Example 24 Shower gel reference A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0387] [Table 31]

[0388] Mix the ingredients and adjust the pH to 6-6.3 (viscosity: 4500 cPo ± 1500 cPo (Brookfield RV / spindle #4 / 20 RPM)).

[0389] Example 25 Shower gel composition A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0390] [Table 32]

[0391] The ingredients are mixed and the pH adjusted to 4.5 (viscosity: 3000 cPo ± 1500 cPo (Brookfield RV / spindle #4 / 20 RPM)).

[0392] Example 26 Shower gel composition A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0393] [Table 33]

[0394] The ingredients are mixed and the pH is adjusted to 4.5 (viscosity: 4000 cPo ± 1500 cPo (Brookfield RV / spindle #4 / 20 RPM)).

[0395] Example 27 Hand Dishwash A sufficient amount of the exemplified microcapsules is weighed out and mixed into the following composition to add the equivalent of 0.2% fragrance.

[0396] [Table 34]

[0397] Mix water with sodium hydroxide and diethanolamide. Add LAS. After LAS is neutralized, add remaining ingredients. Check pH (=7-8) and adjust if necessary.

[0398] Example 28 Toothpaste formulations A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in Example 1 except that menthol flavor is encapsulated) is weighed and mixed into the following composition to add the equivalent of 0.2% flavor.

[0399] [Table 35]

[0400] Example 29 Dicalcium phosphate-based toothpaste formulations A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in Example 1 except that menthol flavor is encapsulated) is weighed and mixed into the following composition to add the equivalent of 0.2% flavor.

[0401] [Table 36]

[0402] Example 30 Alcohol-free mouthwash formulation A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in Example 1 except that menthol flavor is encapsulated) is weighed and mixed into the following composition to add the equivalent of 0.2% flavor.

[0403] [Table 37]

[0404] Example 31 Mouthwash formulations A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in Example 1 except that menthol flavor is encapsulated) is weighed and mixed into the following composition to add the equivalent of 0.2% flavor.

[0405] [Table 38]

Claims

1. A method for preparing a polyamide-based core-shell microcapsule slurry, comprising: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to form a water-in-oil emulsion; c) performing a curing step to form polyamide-based microcapsules in the form of a slurry including adding at least one amino compound A to the aqueous phase before the formation of the water-in-oil emulsion and / or to the water-in-oil emulsion obtained after step b); adding a protein to the oil phase and / or the aqueous phase; adding a crosslinking agent in step b) and / or in step c) and / or after step c). A method.

2. The method according to claim 1, wherein the crosslinking agent is preferably an enzyme crosslinking agent selected from the group consisting of transglutaminase, or the crosslinking agent is preferably a non-enzyme crosslinking agent selected from the group consisting of glutaraldehyde, genipin and mixtures thereof.

3. The method according to claim 2, wherein the crosslinking agent is transglutaminase.

4. The method according to claim 1, wherein the protein is a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algal protein, broad bean protein, barley protein, rye protein, wheat gluten protein, lupinus protein, soybean protein, rice protein, whey protein, ovalbumin, casein, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soybean protein, hydrolyzed sericin, pseudo-collagen, silk protein, sericin powder, gelatin and mixtures thereof.

5. The method according to claim 1, wherein the amino compound A is selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, 1,4-diaminobutane, 2,2-dimethyl-1,3-propanediamine, 1,3-diaminopentane, 1,2-diaminopropane, cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride, 1,3-diaminopropane; urea; ethyleneurea; aminoguanidine bicarbonate; 1-(2-aminoethyl)imidazolidin-2-one; N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine; N1-(2-aminoethyl)-N1-dodecyl-1,2-ethanediamine; aminoethylethanolamine; N1-(3-aminopropyl)propane-1,3-diamine and mixtures thereof.

6. The method according to claim 1, wherein at least one amino compound B is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

7. The method according to claim 6, wherein the amino compound B is preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-leucine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine and mixtures thereof.

8. The method according to claim 1, wherein the aqueous phase preferably contains a base selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, guanidine carbonate, triethanolamine and mixtures thereof.

9. The acyl chloride is of formula (I) 【Chemical 1】 [wherein, n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4, X is (i) to (xi) 【Chemical 2】 optionally containing at least one group selected from, a (n + 1)-valent C ２ ~C ４５ hydrocarbon group, R is a hydrogen atom, or an alkyl group such as a methyl or ethyl group, preferably a hydrogen atom] and the method according to claim 1.

10. A polyamide-based core-shell microcapsule slurry obtained by the method according to any one of claims 1 to 9.

11. A polyamide-based core-shell microcapsule, comprising: - a core containing a hydrophobic material, preferably a fragrance, preferably an oily core; - a polyamide-based shell, · an acyl chloride, · an amino compound A, · optionally an amino compound B, · a protein and a shell containing a reaction product of and wherein the shell has a breaking stress of less than 10 MPa, a polyamide-based core-shell microcapsule.

12. The polyamide-based shell of claim 11, wherein · an acyl chloride, · an amino compound A, · optionally an amino compound B, · a protein and the reaction product of is included in the presence of a crosslinking agent, the polyamide-based core-shell microcapsule according to claim 11.

13. A flavoring composition, comprising: (i) the fragrance microcapsule according to claim 11, wherein the hydrophobic material contains a fragrance; (ii) at least one component selected from the group consisting of a fragrance carrier and a fragrance base; (iii) optionally at least one fragrance adjuvant and a flavoring composition.

14. A consumer product, comprising: - a personal care active base; - the microcapsule according to claim 11, or the flavoring composition according to claim 13 and wherein the consumer product is in the form of a personal care composition. A consumer product.

15. A consumer product, comprising: - a home care or fabric care active base; - the microcapsule according to claim 11, or the flavoring composition according to claim 13 and wherein the consumer product is in the form of a home care or fabric care composition. A consumer product.

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