Microcapsules and methods of making microcapsules

Abstract

The invention relates to core-shell microcapsules. The method for preparing the microcapsules is also an object of the invention. Perfuming compositions and consumer products comprising said microcapsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the invention.

Description

Technical Field

[0001] This invention relates to core-shell microcapsules. Methods for preparing said microcapsules are also an object of this invention. Fragrance compositions and consumer products containing said microcapsules, particularly fragranced consumer products in the form of home care or personal care products, are also part of this invention. Background Technology

[0002] One of the challenges facing the fragrance industry is that the olfactory benefits offered by scented compounds, particularly the "top notes," are lost relatively quickly due to their volatility. To mitigate the release rate of these volatiles, delivery systems, such as fragrance-containing microcapsules, are needed to protect and release the core payload upon triggering. A key requirement for these systems is their ability to remain suspended in challenging base materials without physical decomposition or degradation. This is known as the stability of the delivery system. For example, the stability of microcapsules is particularly challenging for aromatic personal and household cleaners containing detergents with high levels of aggressive surfactants.

[0003] Polyurea and polyurethane-based microcapsule slurries are widely used in industries such as fragrance because they provide a lasting and pleasant olfactory effect when coated on various substrates. These microcapsules are extensively disclosed in the prior art.

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

[0005] Therefore, there remains a need to provide novel microcapsules using more eco-friendly materials without compromising their performance, particularly in terms of stability in challenging media such as consumer product bases, and in terms of delivering good olfactory performance in the case of active ingredient delivery, such as in the case of flavored ingredients.

[0006] The present invention provides a solution to the above-mentioned problems by providing novel microcapsules and a method for preparing said microcapsules. Summary of the Invention

[0007] It has been discovered that core-shell microcapsules encapsulating hydrophobic materials can be obtained by reacting at least one compound having at least two P-Cl functional groups with at least one compound containing an inorganic moiety. Therefore, the microcapsules of the present invention provide a solution to the aforementioned problems because they allow for the preparation of eco-friendly microcapsules with the desired stability in challenging substrates.

[0008] In a first embodiment, the present invention relates to a core-shell microcapsule comprising:

[0009] - The core, which contains hydrophobic materials, and

[0010] - A shell comprising the reaction product of at least one compound containing an inorganic portion and at least one compound having at least two P-Cl functional groups.

[0011] Another object of the present invention is a core-shell microcapsule slurry comprising at least one microcapsule, the microcapsule comprising:

[0012] - The core, which contains hydrophobic materials, and

[0013] - A shell comprising the reaction product of at least one compound containing an inorganic portion and at least one compound having at least two P-Cl functional groups.

[0014] Another object of the present invention is a method for preparing core-shell microcapsule slurry, comprising the following steps:

[0015] a) Optionally, at least one compound having at least two P-Cl functional groups is provided;

[0016] b) Mix at least one hydrophobic material with an optional compound obtained in step a) to form an oil;

[0017] c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0018] d) Optionally, the two-phase dispersion is dispersed into a continuous phase C2, which optionally contains at least one compound having at least two P-Cl functional groups to form a multiple dispersion;

[0019] e) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form.

[0020] A compound having an inorganic moiety is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

[0021] The present invention also relates to flavored consumer products and flavored (seasoned) edible products containing microcapsules or microcapsule slurries as described above. Detailed Implementation

[0022] Unless otherwise stated, percentages (%) refer to the weight percentage of the composition.

[0023] "Active ingredient" refers to a single compound or a combination of multiple components.

[0024] "Flavor oil or flavor (seasoning) oil" refers to a single flavoring or flavoring compound, or a mixture of several flavoring or flavoring compounds.

[0025] "Consumer goods" or "final products" refer to manufactured goods that are ready for distribution, sale, and use by consumers.

[0026] For clarity, the term "dispersion" in this invention refers to a system in which particles are dispersed in a continuous phase of different compositions, and specifically includes suspensions or emulsions.

[0027] In this invention, "microcapsule" or similar term means a core-shell microcapsule having a particle size distribution in the micrometer range (e.g., an average diameter (d(v, 0.5)) of about 1 to 3000 micrometers, preferably 1 to 500 micrometers) and comprising an outer solid polymer shell and an inner continuous oil phase surrounded by the shell.

[0028] "Microencapsulated slurry" refers to microcapsules dispersed in a liquid. According to one embodiment, the slurry is an aqueous slurry, meaning the microcapsules are dispersed in an aqueous phase.

[0029] In this invention, the terms "dispersed phase" and "continuous phase" can be used interchangeably.

[0030] Core-shell microcapsules

[0031] In a first embodiment, the present invention relates to a core-shell microcapsule comprising:

[0032] - The core, which contains hydrophobic materials, and

[0033] - A shell comprising the reaction product of at least one compound containing an inorganic portion and at least one compound having at least two P-Cl functional groups.

[0034] Hydrophobic materials

[0035] According to one implementation scheme, the core is an oil-based core.

[0036] The hydrophobic material according to the present invention can be an "inert" material, such as a solvent or active ingredient.

[0037] The term "hydrophobic material" refers to any hydrophobic material that can form a two-phase dispersion when mixed with water. Hydrophobic materials are typically liquid at around 20°C.

[0038] According to one implementation scheme, the hydrophobic material is the hydrophobic active ingredient.

[0039] When hydrophobic materials are active ingredients, they are preferably selected from the group consisting of flavors, flavoring ingredients, fragrances, flavoring ingredients, nutritional supplements, cosmetics, pest control agents, biocidal active ingredients, and mixtures thereof.

[0040] According to one particular implementation, the hydrophobic material includes a phase change material (PCM).

[0041] According to one particular embodiment, the hydrophobic material comprises a mixture of fragrance and another ingredient selected from the group consisting of active ingredients of nutritional supplements, cosmetics, pest control agents, and biocides.

[0042] According to one particular embodiment, the hydrophobic material comprises a mixture of a biocidal active ingredient and another ingredient selected from the group consisting of fragrances, nutritional supplements, cosmetics, and pest control agents.

[0043] According to one particular embodiment, the hydrophobic material comprises a mixture of a pest control agent and another ingredient selected from the group consisting of fragrances, nutritional supplements, cosmetics, and biocidal active ingredients.

[0044] According to one particular implementation, the hydrophobic material contains fragrance.

[0045] According to one particular implementation scheme, the hydrophobic material is composed of fragrance.

[0046] According to one specific implementation scheme, the hydrophobic material is composed of a biocide active ingredient.

[0047] According to a specific implementation scheme, the hydrophobic material is composed of a pest control agent.

[0048] The term "fragrance" (or "fragrant oil") refers herein to an ingredient or composition that is liquid at about 20°C. According to any of the above embodiments, the fragrant oil may be a single fragrance ingredient or a mixture of multiple ingredients in the form of a fragrant composition. As a "fragrant ingredient," it refers herein to a compound whose primary purpose is to impart or modify an odor. In other words, for an ingredient to be considered a fragrance ingredient, it must be recognized by those skilled in the art as capable of imparting or modifying an odor to the composition, at least in an active or pleasant manner, and not merely having an odor. For the purposes of this invention, the fragrant oil also includes combinations of the fragrance ingredient with substances that jointly improve, enhance, or modify the delivery of the fragrance ingredient, such as fragrance precursors, modifiers, emulsions, or dispersions, and combinations that impart benefits other than altering or imparting an odor, such as persistence, bursting, odor neutralization, antimicrobial effects, microbial stability, and pest control.

[0049] The nature and type of flavoring components present in the oil phase are not guaranteed to be described in greater detail here, and it is impossible to be exhaustive in any way. Those skilled in the art can select them based on their general knowledge and according to the intended use or application and the desired sensory effect. Generally, these flavoring components belong to different chemical categories, such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen- or sulfur-containing heterocyclic compounds, and essential oils (e.g., thyme oil), and the flavoring auxiliaries may be of natural or synthetic origin. In any case, many of these auxiliaries are listed in references such as S. Arctander's *Perfume and Flavor Chemicals*, 1969, Montclair, New Jersey, USA, or later editions thereof, or other works of a similar nature, as well as in the extensive patent literature in the field of fragrances.

[0050] In particular, one can list flavoring ingredients commonly used in flavor formulations, such as:

[0051] - Aldehyde components: decanal, dodecanal, 2-methylundecaldehyde, 10-undecenal, octanal, nonanal and / or nonenal;

[0052] - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0] 2,7 Undec-4-one, 1-methoxy-3-hexethiol, 2-ethyl-4,4-dimethyl-1,3-oxothionecyclohexane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene;

[0053] - Balsam ingredients: coumarin, ethyl vanillin and / or vanillin;

[0054] - Citrus flavoring components: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellol, orange terpene, limonene, 1-p-menthene-8-yl acetate and / or 1,4(8)-p-menthadiene;

[0055] - Floral fragrance components: Methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone (β-violaceone), 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- Ketones, 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-indanylmethanol, 2, 6,6-Trimethyl-3-cyclohexen-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-ylpropanal), Hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, Tricyclodecenyl acetate, Geraniol, p-menth-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, Amyl salicylate, Methyl jasmonate, 3-methyl-5-benzene Mixtures of 1-pentanol, tricyclodecenyl propionate, geraniol acetate, tetrahydrolinalool, cis-7-p-menthol, (S)-2-(1,1-dimethylpropoxy)propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, pentylcinnamaldehyde, 8-decen-5-lactone, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or methyl ionone isomers;

[0056] - Fruity flavor components: γ-undecyl lactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxothiacyclohexane, 4-decyl lactone, ethyl 2-methyl-valerate, hexyl acetate, ethyl 2-methylbutyrate, γ-nonyl lactone, allyl heptaate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-ethyl acetate, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl [3-ethyl-2-epoxyethylene]acetate and / or diethyl 1,4-cyclohexanedicarboxylate;

[0057] - Green fragrance components: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrax acetate, (2-methylbutoxy) allyl 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;

[0058] - Musk components: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecane-1-one, 3-methylcyclopentadecaneone, 1-oxa-12-cyclohexadecene-2-one, 1-oxa-13-cyclohexadecene-2-one, (9Z)-9-cycloheptadecene-1-one, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl ester of propionic acid, 3-methyl-5- Cyclopentadecan-1-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isobenzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl ester, oxetane-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl ester;

[0059] - Costus root components: 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[ethylene oxide-2,9'-tricyclo[6.2.1.0] 2,7 Undecene[4], (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl ester, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethyl ketone, 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 cypressone, 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-octahydronaphthyl-2-yl) ethyl-1-one and / or isobornyl acetate;

[0060] - Other components (e.g., amber, powdery, spicy, or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any stereoisomers thereof, piperaldehyde, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxacyclopenten-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxacycloheptan-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4,4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0061] It should also be understood that the ingredient may also be a compound known to release various types of fragrance compounds in a controlled manner, also known as a property or profragrance. Non-limiting examples of suitable property precursors may include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octane-4-one, 2-phenylethyl oxo(phenyl)acetic acid, 3,7-dimethyloctane-2,6-diene-1-oxo(phenyl)acetic acid. 3,7-dimethyl-2,6-octadien-1-yl ester of hexadecanoate, bis(3,7-dimethyloct-2,6-dien-1-yl) ester of succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenylethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenylethoxybut-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-(oct-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-pentylcyclopentyl)methoxy) (2-(2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentyl)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentyl)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentyl)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof.

[0062] Fragrance ingredients can be dissolved in solvents currently used in the fragrance industry. The solvent is preferably not an alcohol. Examples of such solvents include diethyl phthalate, isopropyl myristate, and Abalyn. ®(Rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes or isoparaffins. Preferably, the solvent is highly hydrophobic and sterically hindered, such as Abalyn. ® Or benzyl benzoate. Preferably, the fragrance contains less than 30% solvent. More preferably, the fragrance contains less than 20%, and even more preferably less than 10% solvent, all of which are by weight relative to the total weight of the fragrance. Most preferably, the fragrance is substantially solvent-free.

[0063] Preferred flavoring ingredients are those with high steric hindrance (bulky materials), particularly those from one of the following groups:

[0064] - Group 1: Fragrance ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one straight-chain or branched C1-C4 alkyl or alkenyl substituent;

[0065] - Group 2: Fragrance ingredients containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one straight-chain or branched C4-C8 alkyl or alkenyl substituent;

[0066] - Group 3: Fragrance ingredients containing a benzene ring, or fragrance ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one straight-chain or branched C5-C8 alkyl or alkenyl substituent, or substituted with at least one phenyl substituent and optionally substituted with one or more straight-chain or branched C1-C3 alkyl or alkenyl substituents.

[0067] - Group 4: Fragrance ingredients containing at least two fused or linked C5 and / or C6 rings;

[0068] - Group 5: Fragrance ingredients containing camphor-like ring structures;

[0069] Group 6: Contains at least one C7-C 20 Fragrant ingredients with cyclic structures;

[0070] - Group 7: Flavoring ingredients with a logP value greater than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent;

[0071] Examples of components from each of these groups are:

[0072] Group 1: 2,4-Dimethyl-3-cyclohexene-1-carboxaldehyde (Source: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (Source: Firmenich SA, Geneva, Switzerland), nerol, terpineol, dihydroterpineol, terpene acetate, dihydroterpene acetate, dipentene, eucalyptol, hexylate, rose ether, (S)-1,8-p-menthadien-7-ol (Source: Firmenich SA, Geneva, Switzerland) SA, Geneva, Switzerland), l-menthene-4-ol, (1RS,3RS,4SR)-3-p-menthene acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]hept-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (Source: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, trimethylcyclohexyl acetate (cyclanol), 1,4-cyclohexanediethyl dicarboxylate (Source: Firmenich SA, Geneva, Switzerland), (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Source: Firmenich SA, Geneva, Switzerland), (6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Source: Firmenich SA, Geneva, Switzerland) SA (Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde;

[0073] Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (Source: Givaudan SA, Vergne, Switzerland), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol (Source: Firmenich SA, Geneva, Switzerland), (1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol (Source: Firmenich SA, Geneva, Switzerland), 2-heptacyclopentanone, methyl-cis-3-oxo-2-pentyl-1-cyclopentane acetate (Source: Firmenich SA, Geneva, Switzerland), 2,2,5-trimethyl-5-pentyl-1-cyclopentanone (Source: Firmenich SA, Geneva, Switzerland) SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (Source: Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (Source: Givaudan SA, Vergne, Switzerland);

[0074] Group 3: Damasne, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (Source: Firmenich SA, Geneva, Switzerland), (1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'-yl)propyl]cyclopentanone, α-ionone, β-ionone, damasne, 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 (Source: Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (Source: Firmenich SA, Geneva, Switzerland) SA, Geneva, Switzerland), (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl ester (Source: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1-cyclohexyl acetate (Source: International Flavors and Fragrances, USA), 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (Source: Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (Source: Firmenich SA, Geneva, Switzerland), (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, isobutyric acid terpene ester, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate (Source: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate (Source: Firmenich SA, Geneva, Switzerland), p-tert-butylcyclohexanone, menthylenethiol, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, methyl 2-methoxy-4-methylphenyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, methyl 4-ethyl-2-methoxyphenyl carbonate;

[0075] - Group 4: Methyl cypressone (Source: International Flavors and Fragrances, USA), 2-Methylpropionic acid (1RS, 2SR, 6RS, 7RS, 8SR)-tricyclic [5.2.1.0] 2,6 ] Dec-3-en-8-yl ester and 2-methylpropionic acid (1RS,2SR,6RS,7RS,8SR)-tricyclic [5.2.1.0] 2,6Mixtures of dec-4-en-8-yl esters, vetyverol, vetyverone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethyl ketone (Source: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10-tetramethyl-1-oxaspiro[4.5]dec-3,6-diene and (5RS,9SR,10RS) isomers, 6-ethyl-2,10,10-trimethyl-1-oxaspiro[4.5]dec-3,6-diene, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4-indanone (Source: International Flavors) andFragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal (Source: Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-en-9-spiro-2'-ethylene oxide (Source: Firmenich SA, Geneva, Switzerland), 9 / 10-ethyldiene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthyl acetate (Source: Firmenich SA, Geneva, Switzerland), 1-naphthol (octalynol), (dodecylhydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (Source: Firmenich SA, Geneva, Switzerland) 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 propionate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl propionate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'-cyclohexen-4'-one;

[0076] - Group 5: Camphor, Borneol, Isoborneol Acetate, 8-Isopropyl-6-methyl-bicyclo[2.2.2]oct-5-en-2-carboxaldehyde, Pinene, Camphene, 8-Methoxycedrine, (8-Methoxy-2,6,6,8-Tetramethyl-Tricyclo[5.3.1.0(1,5)]Undecane (Source: Firmenich SA, Geneva, Switzerland), Cedrusene, Cedrusenol, Cedrusol, 9-Ethylene-3-oxatricyclo[6.2.1.0(2,7)]Undec-4-one and 10-Ethylene-3-oxatricyclo[6.2.1.0] 2,7A mixture of undecane-4-ones (source: Firmenich SA, Geneva, Switzerland) and 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (source: Firmenich SA, Geneva, Switzerland).

[0077] - Group 6: (trimethyl-13-oxabicyclo-[10.1.0]-tridec-4,8-diene (source: Firmenich SA, Geneva, Switzerland), 9-hexadecene-16-lactone (source: Firmenich SA, Geneva, Switzerland), cyclopentadenin lactone (source: Firmenich SA, Geneva, Switzerland), 3-methyl(4 / 5)-cyclopentadeninone (source: Firmenich SA, Geneva, Switzerland), 3-methylcyclopentadeninone (source: Firmenich SA, Geneva, Switzerland), pentadecyl lactone (source: Firmenich SA, Geneva, Switzerland), cyclopentadeninone (source: Firmenich SA, Geneva, Switzerland), (1-ethoxyethoxy)cyclododecane (source: Firmenich SA, Geneva, Switzerland), 1,4-dioxacycloheptadecane-5,17-dione, 4,8-cyclododecene-1-one;

[0078] - Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propyl)phenyl]propanal (Source: Givaudan SA, Vergne, Switzerland), 2,2,2-trichloro-1-phenylethyl acetate.

[0079] Preferably, the flavoring contains at least 30%, more preferably at least 50%, and more preferably at least 60% of the ingredients selected from groups 1 to 7 as defined above. More preferably, the flavoring contains at least 30%, more preferably at least 50% of the ingredients selected from groups 3 to 7 as defined above. Most preferably, the flavoring contains at least 30%, more preferably at least 50% of the ingredients selected from groups 3, 4, 6, or 7 as defined above.

[0080] According to another preferred embodiment, the flavoring contains at least 30%, preferably at least 50%, more preferably at least 60% of the component with a logP greater than 3, preferably greater than 3.5, and even more preferably greater than 3.75.

[0081] According to one particular embodiment, the fragrance used in this invention contains less than 10% by its own weight of primary alcohol, less than 15% by its own weight of secondary alcohol, and less than 20% by its own weight of tertiary alcohol. Advantageously, the fragrance used in this invention contains no primary alcohol, but contains less than 15% of secondary and tertiary alcohols.

[0082] According to one embodiment, the oil phase (or oil-based core) comprises:

[0083] - 25~100% by weight of fragrance oil, containing at least 15% by weight of high-impact fragrance ingredients with Log T <-4, and

[0084] - 0~75% by weight of density equilibrium material with a density greater than 1.07 g / cm³ 3 .

[0085] "High-impact flavoring raw materials" should be understood as flavoring raw materials with Log T < -4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charge, and molecular weight. For convenience, the odor threshold concentration is expressed as the commonly used logarithm of the threshold concentration, i.e., Log[threshold] ("LogT").

[0086] "Density equilibrium material" should be understood as having a density greater than 1.07 g / cm³. 3 Furthermore, materials with low or no odor are preferred.

[0087] The odor threshold concentration of the flavoring compound was determined using gas chromatography (“GC”). Specifically, the GC was calibrated to determine the precise volume, precise split ratio, and hydrocarbon response of the flavoring oil component injected by the syringe using hydrocarbon standards with known concentrations and chain length distributions. The airflow rate was accurately measured, and the sampling volume was calculated assuming a duration of 12 seconds for human inhalation. Since the precise concentration at the detector at any given time point was known, the mass per volume inhaled was known, and therefore the concentration of the flavoring compound was known. To determine the threshold concentration, the solution was delivered to the olfactory port at a back-calculated concentration. Panel members sniffed the GC effluent and determined the retention time at which the odor was detected. The average of all panel members determined the odor threshold concentration of the flavoring compound. The determination of the odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September, 2008, pages 54-61.

[0088] WO2018115250 describes high-impact flavoring raw materials with Log T < -4 and those with greater than 1.07 g / cm³. 3 The density of the material is a property of the density equilibrium, the contents of which are included by reference.

[0089] According to one embodiment, the high-impact fragrance ingredient with Log T < -4 is selected from the group consisting of: (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1-phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1-acetic acid phenyl ester, pyrazolyl butyl ether, 3-propylphenol, 1-(3-methyl-1-benzofuran-2-yl)ethyl ketone, 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-pentene. -1-one, mixtures comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one, (+-)-1-(5-ethyl-5-methyl-1-cyclohexen-1-yl)-4-penten-1-one, (1'S,3'R)-1-methyl-2-[(1',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl}methanol , Acetate (+-)-3-mercaptohexyl acetate, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, H-methyl-2h-1,5-benzodioxane-3(4H)-one, (2E,6Z)-2,6-nonadien-1-ol, (4Z)-4-dodecenal, (+-)-4-hydroxy-2,5-dimethyl-3(2H)-furanone, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 3-methylindole, (+-)-perhydro-4α,8Aβ-dimethyl -4a-naphthol, patchouli alcohol, 2-methoxy-4-(1-propenyl)phenol, a mixture containing (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methyl-2-phenyl-2H-pyran, a mixture containing 4-methyl-2-phenyltetrahydro-2H-pyran and (+-)-4-methyl-2-phenyl-3,6-dihydro-2H-pyran, 4-hydroxy-3-methoxybenzaldehyde, nonenal, 2-methoxy-4-propylphenol, 3-methyl-5-phenyl-2-pentenonitrile, 1-(spiro[4.5] Dec-6 / 7-en-7-yl)-4-penten-1-one, 2-methoxynaphthalene, (-)-(3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecanonaphtho[2,1-b]furan, 5-nonanolactone, (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecanonaphtho[2,1-b]furan, 7-isopropyl-2H,4H-1,5-benzodioxane-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-methyl-3 -Cyclopenten-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, p-cresol, 3-ethoxy-4-hydroxybenzaldehyde, methyl 2-aminobenzoate, ethyl methylphenyl glycidyl ester, γ-octanolide, ethyl 3-phenyl-2-acrylate, (-)-(2E)-2-ethyl-4-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol, p-cresol acetate, dodecyl lactone, dimethyltricyclo[7.1.1.0]. 2,7Undecyl-2-en-4-one (tricyclone), (+)-(3R,5Z)-3-cyclopentadecane-1-one, undecyl lactone, (1R,4R)-8-mercapto-3-p-menthone, (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-undecyltriene, 10-undecenal, (9E)-9-undecyl Enal, (9Z)-9-undecenal, (Z)-4-decenal, 2-methylpentanoic acid (+-)-ethyl ester, 1,2-diallyl dithiocarbamate, 2-tetracene acrylonitrile, 3-tetracene acrylonitrile, (+-)-2-ethyl-4,4-dimethyl-1,3-oxothiacyclohexane, (+)-(3R,5Z)-3-methyl-5-cyclopentadecane-1-one, 3-(4-tert-butylphenyl)propanal, (cyclohexyloxy)acetic acid allyl ester, methylnaphthyl ketone, (+-)-(4E)-3-methyl-4-cyclopentadecane-1- Ketones, (+-)-5E3-methyl-5-cyclopentadecen-1-one, cyclopropyl methyl 3-hexenoic acid, (4E)-4-methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1-(5-propyl-1,3-benzodioxane-2-yl)ethyl ketone, 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-Tetramethyldodecano[2,1-b]furan, (2S,5R)-5-methyl-2-(2-propyl)cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran-2-one, (+-)-3-(3-isopropyl-1-phenyl)butanal, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(2,6,6-trimethyl-1-cyclohexyl-2-enyl)pent-1-en-3-one, indole, 7-propyl-2H,4H-1,5-benzodioxane-heptane-3-one, ethyl praline, (4-methylphenoxy)acetaldehyde, tricyclic [5.2.1.0]. 2,6Ethyl decanoate, (+)-(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-en-2-carboxaldehyde, methylnonylacetaldehyde, 4-formyl-2-methoxyphenyl ester of 2-methylpropionic acid, (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-thiazoline Bicyclo[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-acrylonitrile, 4-methoxybenzyl acetate, (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (2 / 3-methylbutoxy)allylic 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.

[0090] According to one embodiment, the fragrance raw materials with Log T<-4 are selected from the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.

[0091] According to one embodiment, the flavoring ingredient with Log T < -4 comprises at least one compound selected from the group consisting of alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof, preferably in a content of 20 to 70% by weight based on the total weight of the flavoring ingredient with Log T < -4.

[0092] According to one embodiment, based on the total weight of flavoring raw materials with Log T < -4, the flavoring raw materials with Log T < -4 contain 20 to 70% by weight of aldehydes, ketones, and mixtures thereof.

[0093] Therefore, the remaining flavoring raw materials contained in the oil-based core may have Log T>-4.

[0094] According to one embodiment, the fragrance raw material with Log T>-4 is selected from the group consisting of: ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6 / 8-sec-butylquinoline, (+-)-3-(1,3-benzodioxacyclopentan-5-yl)-2-methylpropanal, tricyclodecenyl propionate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethyl ketone, methyl 2-((1RS,2RS)-3-oxo-2-pentylcyclopentanyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, 1,3,3-trimethyl-2-oxabis(ethyl)-2-ethyl ... Cyclo[2.2.2]octane, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, dodecaldehyde, 1-oxa-12-cyclohexadecen-2-one, (+-)-3-(4-isopropylphenyl)-2-methylpropanal, C11 aldehyde, (+-)-2,6-dimethyl-7-octen-2-ol, allyl 3-cyclohexylpropionate, (Z)-3-hexenyl acetate, 5-methyl-2-(2-n-propyl)cyclohexanone, allyl heptaate, 2-(2-methyl-2-n-propyl)cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl butyrate, geraniol acetate, nerol acetate, (+-)-1-phenylethyl acetate Esters, 1,1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutyrate, ethyl 3-hydroxy-2-butenoic acid (2Z)-ester, 8-p-menthol, 8-p-menthyl acetate, 1-p-menthyl acetate, (+-)-2-(4-methyl-3-cyclohexen-1-yl)-2-propyl acetate, (+-)-2-methylbutyl butyrate, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl acetate, 3,5,6-trimethyl-3-cyclohexen-1-carboxaldehyde, 2,4,6-trimethyl-3-cyclohexen-1-carboxaldehyde, 2-cyclohexylethyl acetate Ester, octanal, ethyl butyrate, (+-)-(3E)-4-(2,6,6-trimethyl-1 / 2-cyclohexen-1-yl)-3-buten-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, undecaldehyde, decanal, 2-phenylethyl acetate, (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ol, (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ol, (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.2].[1] Heptan-2-ol), (+-)-3,7-dimethyl-3-octanol, 1-methyl-4-(2-propanediyl)cyclohexene, (+)-(R)-4-(2-methoxypropyl-2-yl)-1-methylcyclohex-1-ene, tricyclodecenyl 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-methylpropyl propionate, and mixtures thereof.

[0095] According to one embodiment, the core comprises a flavoring compound, the flavoring compound comprising:

[0096] - 0 to 60% by weight of hydrophobic solvents (based on the total weight of the flavoring compound).

[0097] - 40 to 100% by weight of spice oil (based on the total weight of the spice blend), wherein the spice oil has at least two of the following properties, preferably all of the following properties:

[0098] ○ The flavoring ingredient has a log P greater than 3, preferably greater than 3.5, at least 35%, preferably 40%, preferably at least 50%, and more preferably at least 60%.

[0099] ○ At least 20%, preferably 25%, preferably at least 30%, more preferably at least 40% of the large steric hindrance material as defined above in groups 1 to 6, preferably groups 3 to 6, and

[0100] ○ At least 15%, preferably at least 20%, more preferably at least 25%, and even more preferably at least 30% of the previously defined high-impact fragrance material, Log T < -4.

[0101] - Optionally, additional hydrophobic active ingredients.

[0102] According to one particular implementation, the fragrance contains 0 to 60% by weight of a hydrophobic solvent.

[0103] According to a particular embodiment, the hydrophobic solvent is a density-balanced material, preferably selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, methyl phenylacetate, ethyl phenylacetate, triacetyl glycerol, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.

[0104] In one particular embodiment, the hydrophobic solvent has a Hansen solubility parameter that is compatible with the embedded fragrance oil.

[0105] The term "Hansen solubility parameter" is understood to refer to the solubility parameter method proposed by Charles Hansen for predicting polymer solubility, and is developed based on the premise that the total vaporization energy of a liquid is composed of several separate components. To calculate the "weighted Hansen solubility parameter," the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces, and (molecular) hydrogen bonding (electron exchange) must be considered. The "weighted Hansen solubility parameter" is calculated as (δD... 2 +δP 2 +δH 2 ) 0.5 δD is the Hansen dispersion value (hereinafter also called atomic dispersion force), δP is the Hansen polarizability value (hereinafter also called dipole moment), and δH is the Hansen hydrogen bond (“h-bond”) value (hereinafter also called hydrogen bond). For a more detailed explanation of this parameter and its value, please refer to Charles Hansen’s The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, Danish Technical Press (Copenhagen, 1967).

[0106] The Euclidean difference in the solubility parameters of the fragrance and the solvent is calculated as (4*(δD)). solvent -δD fragrance ) 2 +(δP solvent -δP fragrance ) 2 + (δH solvent -δH fragrance ) 2 ) 0.5 , where δD solvent δP solvent and δH solvent These represent the Hansen dispersion value, Hansen polarizability value, and Hansen hydrogen bond value of the solvent, respectively; while δD fragrance δ fragrance and δH fragrance These are the Hansen dispersion value, Hansen polarizability value, and Hansen hydrogen bond value of the fragrance, respectively.

[0107] In one particular embodiment, the fragrance 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 to 20, a dipole moment (δP) of 1 to 8, and a hydrogen bond (δH) of 2.5 to 11.

[0108] In one particular embodiment, the fragrance 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.

[0109] In one particular embodiment, at least 90% of the fragrance oil, preferably at least 95% of the fragrance oil, and most preferably at least 98% of the fragrance oil, have at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (δD) of 12 to 20, a dipole moment (δP) of 1 to 8, and a hydrogen bond (δH) of 2.5 to 11.

[0110] In one particular embodiment, the fragrance 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.

[0111] According to one embodiment, the fragrance formulation includes a fragrance modifier (which can be used with a hydrophobic solvent when it is present, or as a substitute for a hydrophobic solvent when it is absent).

[0112] Preferably, the fragrance modifier is defined as a fragrance material having:

[0113] i. Vapor pressure less than 0.0008 Torr at 22°C;

[0114] ii. clogP of 3.5 or higher, preferably 4.0 or higher, and more preferably 4.5;

[0115] iii. At least two Hansen solubility parameters selected from the first group consisting of: atomic dispersion force of 12 to 20, dipole moment of 1 to 7, and hydrogen bond of 2.5 to 11.

[0116] iv. At least two Hansen solubility parameters selected from the second group consisting of: atomic dispersion force of 14 to 20, dipole moment of 1 to 8, and hydrogen bond of 4 to 11, when in solution with a compound having a vapor pressure in the range of 0.0008 to 0.08 Torr at 22 °C.

[0117] Preferably, as an example, the following components may be listed as modifiers, but this list is not limited to the following substances: alcohol C12, oxetane-12 / 13-en-2-one, 3-[(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)methoxy]-2-butanol, cyclohexadecane, (Z)-4-cyclopentadecane-1-one, cyclopentadecane, (8Z)-oxetane-8-en-2-one, 2-[5-(tetrahydro-5-methyl-5-vinyl-2-furanyl)-tetrahydro-5-methyl-2-furanyl]-2-propanol, lily aldehyde, 1,5,8-trimethyl-13-oxabicyclo[10.1.0]tetane-4,8-diene, (+-)-4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexamethyl-1,3,4,6,7,8-hexadecane Hydrocyclopentano[g]isobenzopyran, (+)-(1S,2S,3S,5R)-2,6,6-trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one, oxacyclohexadecane-2-one, propionic acid 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl ester, (+)-(4 R,4aS,6R)-4,4a-dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthol, pentylcinnamaldehyde, hexylcinnamaldehyde, hexyl salicylate, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,6-heptadien-3-one, (9Z)-9-cycloheptadecene-1-one.

[0118] According to one particular embodiment, the hydrophobic material is free of any active ingredients (e.g., fragrance). According to this particular embodiment, it comprises a hydrophobic solvent, preferably composed of, and preferably selected from isopropyl myristate, triglycerides (e.g., Neobee® MCT oil, vegetable oils), D-limonene, silicone oil, mineral oil, and mixtures thereof, and optionally preferably from the following hydrophilic solvents: 1,4-butanediol, benzyl alcohol, triethyl citrate, triglyceride, benzyl acetate, ethyl acetate, propylene glycol (1,2-propanediol), 1,3-propanediol, dipropylene glycol, glycerol, glycol ethers, and mixtures thereof.

[0119] The term "biocide" refers to a chemical substance that can kill living organisms (such as microorganisms) or reduce or prevent their growth and / or accumulation. Biocides are commonly used in pharmaceuticals, agriculture, forestry, and industries that prevent scaling, such as in water, agricultural products (including seeds), and oil pipelines. Biocides can be pesticides, including fungicides, herbicides, insecticides, algaecides, molluscicides, acaricides, and rodenticides; and / or antimicrobial agents, such as fungicides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoa and / or antiparasitic drugs.

[0120] As used herein, “pest control agent” refers to a substance used to repel or attract pests in order to reduce, inhibit, or promote their growth, development, or activity. Pests are any organism that is invasive or troublesome to plants or animals, whether animal, plant, or fungus. Pests include insects, especially arthropods, mites, spiders, fungi, weeds, bacteria, and other microorganisms.

[0121] By "flavor oil," the term refers to a flavoring ingredient, or a mixture of flavoring ingredients, solvents, or adjuvants currently used in the preparation of flavoring formulations, that is, a specific mixture of components intended to be added to an edible composition or chewable product to impart, improve, or modify its sensory properties, particularly its flavor and / or taste. Flavoring ingredients are well known to those skilled in the art, and their properties are not guaranteed to be described in greater detail herein; in any case, they cannot be exhaustive, and a skilled flavorist is able to select them based on their general knowledge and according to the intended use or application and the desired sensory effect. Many of these flavoring ingredients are listed in references such as S. Arctander's *Perfume and Flavor Chemicals*, 1969, Montclair, NJ, USA, or its latest edition, or other works of a similar nature, such as Fenaroli's *Handbook of Flavor Ingredients*, 1975, CRC Press, or MB Jacobs' *Synthetic Food Adjuncts*, 1947, van Nostrand Co., Inc. Solvents and adjuvants currently used in the preparation of flavoring formulations are also well known in the art.

[0122] In one particular embodiment, the flavoring agent is a peppermint flavoring agent. In a more specific embodiment, the peppermint is selected from the group consisting of peppermint and spearmint.

[0123] In a further embodiment, the flavoring agent is a cooling agent or a mixture thereof.

[0124] In another embodiment, the flavoring agent is menthol.

[0125] Flavoring agents derived from or based on fruits in which citric acid is the predominant naturally occurring acid include, but are not limited to, citrus fruits (e.g., lemons, limes), limonene, strawberries, oranges, and pineapples. In one embodiment, the flavored food is lemon juice, lime juice, or orange juice extracted directly from the fruit. Other embodiments of the flavoring agent include juices or liquids extracted from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, and any other citrus fruits or their varieties or hybrids. In a particular embodiment, the flavoring agent includes liquids extracted or distilled from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, any other citrus fruits or their varieties or hybrids, pomegranates, kiwifruits, watermelons, apples, bananas, blueberries, cantaloupes, ginger, bell peppers, cucumbers, passion fruit, mangoes, pears, tomatoes, and strawberries.

[0126] In one particular embodiment, the flavoring agent comprises a composition containing limonene. In another particular embodiment, the composition is a citrus fruit that further contains limonene.

[0127] In another specific implementation, the flavoring agent comprises a flavoring agent selected from the group consisting of strawberry, orange, lime, tropical fruit, berry mixture and pineapple.

[0128] Phrase flavorings include not only flavoring agents that impart or modify the aroma of food, but also components that impart or modify the taste. The latter may not necessarily have a taste or aroma themselves, but can improve the taste provided by other components such as salt-enhancing components, sweet-enhancing components, umami-enhancing components, bitterness-blocking components, etc.

[0129] In a further embodiment, a suitable sweetening component may be included in the particles described herein. In one particular embodiment, the sweetening component is selected from the group consisting of sugars (e.g., but not limited to sucrose), stevia components (e.g., but not limited to steviol glycosides or rebaudioside A), sodium cyclohexylsulfamate (cyclamate), aspartame, sucralose, sodium saccharin, and acesulfame potassium, or mixtures thereof.

[0130] Compounds having at least two P-Cl functional groups

[0131] According to the present invention, the shell of the microcapsule comprises a reaction product of at least one compound having at least two P-Cl functional groups and a compound having an inorganic moiety.

[0132] The phrase "a compound having at least two P-Cl functional groups" should be understood to mean that the P-Cl functional group can be located on the same P atom or on two different P atoms in the same molecule.

[0133] According to one implementation, the term "P-Cl functional group" refers to the covalent bond between a P atom and a Cl atom.

[0134] According to one implementation, the at least two Cl functional groups are located on the same P atom.

[0135] According to one embodiment, the compound having at least two P-Cl functional groups contains a P atom that is covalently bonded to at least two Cl atoms.

[0136] The compound having at least two P-Cl functional groups can be selected from the group consisting of compounds of the formula PXCl3, where X is O, S, NH, or NR. 1 , where R 1 The optional hydrocarbon group may contain any heteroatom. Preferably, the compound having at least two P-Cl functional groups may be selected from the group consisting of: phosphorus oxychloride (POCl3), phosphorus trichloride (PSCl3), phosphorus trichloride imide (PNHCl3), N-substituted phosphorus trichloride imide (PNR). 1 Cl3), phosphorus trichloride, phosphorus pentachloride, hexachlorocyclotriphosphazene (HCCP) and its derivatives, R 1 OPXCl2 (where X is O, NH, or NR) 1 Or S), for example, alkyl phosphorus dichloride (R 1 OPOCl2) and / or alkyl dichlorothiophosphate (R 1 OPSCl2) (where R 1 It can be any hydrocarbon moiety having heteroatoms; poly(dichlorophosphazene), 3,9-dichloro-2,4,8,10-tetraoxa-3λ5,9λ5-diphosphaspiro[5.5]undecane 3,9-dioxide, and mixtures thereof.

[0137] According to one embodiment, the hydrocarbon group is a functional or functional C1-C group. 50 Hydrocarbon group.

[0138] The compound having at least two P-Cl functional groups can be selected from the group consisting of: PXCl3, PNHCl3, and PNR. 1 Compounds of Cl3, where X is O, S, and R. 1 The optional hydrocarbon group may contain any heteroatom. Preferably, the compound having at least two P-Cl functional groups may be selected from the group consisting of: phosphorus oxychloride (POCl3), phosphorus trichloride (PSCl3), phosphorus trichloride imide (PNHCl3), N-substituted phosphorus trichloride imide (PNR). 1Cl3), phosphorus trichloride, phosphorus pentachloride, hexachlorocyclotriphosphazene (HCCP), 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (TCPA), a copolymer of hexa(4-aldehyde phenoxy)-cyclotriphosphazene and 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (HACP-co-TCPA), R 1 OPXCl2 (where X is O, NH, or NR) 1 Or S), for example, alkyl phosphorus dichloride (R 1 OPOCl2) and / or alkyl dichlorothiophosphate (R 1 OPSCl2) (where R 1 It can be any hydrocarbon moiety having heteroatoms; poly(dichlorophosphazene), 3,9-dichloro-2,4,8,10-tetraoxa-3λ5,9λ5-diphosphaspiro[5.5]undecane 3,9-dioxide, and mixtures thereof.

[0139] It should be understood that by “...alkyl group…”, the term refers to a group consisting of hydrogen and carbon atoms, and may be in the form of an aliphatic hydrocarbon, i.e., a straight-chain or branched saturated hydrocarbon (e.g., alkyl), a straight-chain or branched unsaturated hydrocarbon (e.g., alkenyl or ynyl), a saturated cyclic hydrocarbon (e.g., cycloalkyl), or an unsaturated cyclic hydrocarbon (e.g., cycloalkenyl or cycloynyl), or may be in the form of an aromatic hydrocarbon, i.e., an aryl, or may be in the form of a mixture of groups of the aforementioned types. For example, unless specifically limited to only one type mentioned, a particular group may comprise a straight-chain alkyl, a branched alkenyl (e.g., having one or more carbon-carbon double bonds), a (poly)cycloalkyl, and an aryl moiety. Similarly, in all embodiments of the invention, when a group is mentioned as being in more than one type of topological (e.g., straight-chain, cyclic, or branched) and / or saturated or unsaturated (e.g., alkyl, aromatic, or alkenyl) form, it also means that it may comprise a group having any of the aforementioned topological or saturated or unsaturated moieties as explained above. Similarly, in all embodiments of the invention, when a group is referred to as being in a saturated or unsaturated form (e.g., alkyl), it means that the group can be any type of topology (e.g., straight-chain, cyclic, or branched) or have several parts with various topological structures.

[0140] It should be understood that the term "...hydrocarbon group, optionally containing..." means that the hydrocarbon group optionally contains one, two, three or more heteroatoms. These groups may replace the hydrogen atom of the hydrocarbon group and thus side-attach to the hydrocarbon, or replace the carbon atom of the hydrocarbon group (if chemically possible) and thus insert into the hydrocarbon chain. For example, the -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group containing an alcohol group (substitution of hydrogen atoms), i.e., a C4 hydrocarbon group containing an oxygen atom; the -CH2-CH2-COO-CH2-CH2CH2-CH2- group represents a C7 hydrocarbon group containing an ester group (substitution / insertion of carbon atoms into the hydrocarbon chain), i.e., a C7 hydrocarbon group containing two oxygen atoms; and similarly, the -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a C6 hydrocarbon group containing two ether groups, i.e., a C6 hydrocarbon group containing two oxygen atoms.

[0141] According to one particular embodiment, the compound having at least two P-Cl functional groups is hexachlorocyclotriphosphazene (HCCP) or a derivative thereof or a polymer thereof.

[0142] According to a particular embodiment, the compound having at least two P-Cl functional groups is a hexachlorocyclotriphosphazene (HCCP), 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (TCPA), a copolymer of hexa(4-aldehyde-phenoxy)cyclotriphosphazene (HACP) and 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (HACP-co-TCPA), or a mixture thereof.

[0143] According to one embodiment, the compound having at least two P-Cl functional groups is only PCl5 when the inorganic part is not silicone or Ca(OH)2, or when the compound having the inorganic part does not contain a hydrocarbon part.

[0144] According to one embodiment, the compound having at least two P-Cl functional groups is not PCl5.

[0145] Compounds with inorganic components

[0146] According to one implementation, the term "inorganic part" refers to non-carbon-based structural units, particularly structural units whose bonding does not depend on a carbon framework.

[0147] According to one embodiment, a compound having an inorganic moiety is a compound in which carbon-carbon bonds and / or carbon-hydrogen bonds constitute a minority (based on the total number of covalent bonds, preferably no more than 50%, more preferably no more than 30%, more preferably no more than 20%, no more than 10%, more preferably no more than 4%) or even no carbon-carbon bonds and / or carbon-hydrogen bonds.

[0148] According to one embodiment, a compound having an inorganic moiety is a compound in which carbon-carbon bonds and / or carbon-hydrogen bonds constitute a minority (based on the total number of covalent bonds, preferably no more than 30%, preferably no more than 20%, no more than 10%, more preferably no more than 4%) or even no carbon-carbon bonds and / or carbon-hydrogen bonds.

[0149] According to one embodiment, the compound having an inorganic portion is a monomer, polymer, oligomer, particulate, or mixture thereof.

[0150] When the compound containing the inorganic portion is particulate, it can be selected from the group consisting of calcium phosphate, silicon dioxide, silicates, titanium dioxide, aluminum oxide, zinc oxide, iron oxide, mica, kaolin, montmorillonite, laponite, bentonite, perlite, dolomite, diatomite, vermiculite, lithium montmorillonite, gibbsite, illite, kaolinite, aluminosilicates, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomaceous earth, and mixtures thereof.

[0151] According to one embodiment, the compound having an inorganic moiety is 1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexane-1,3,5-triene-2,2,4,4,6,6-hexamine.

[0152] According to one embodiment, the compound having an inorganic portion is a silicon-containing monomer, polymer, oligomer, particulate, or mixture thereof, preferably selected from the group consisting of amino-functional silanes, sulfur-functional silanes, non-functional silanes, or mixtures thereof.

[0153] The amino-functionalized silane may be selected from bis[3-(triethoxysilyl)propyl]amine, 3-aminopropyltriethoxysilane, 3-(2-aminoethylamino)propyltriethoxysilane, 1,1,1-triethoxysilaneamine and its polymers and mixtures.

[0154] The sulfur-functionalized silane can be selected from 3-mercaptopropyltriethoxysilane.

[0155] The nonfunctional silane may be selected from 1,2-bis(triethoxysilyl)ethane, silicone, 1-(triethoxysilyl)-2-(diethoxymethylsilyl)ethane and triethoxysilane, and mixtures thereof.

[0156] According to one implementation, the compound having an inorganic portion is not a mineral.

[0157] According to one implementation, the compound having an inorganic portion is not an inert mineral.

[0158] According to one embodiment, the compound having an inorganic moiety is not the same molecule as the compound having at least two P-Cl functional groups.

[0159] According to one embodiment, the shell contains inorganic and organic portions, preferably composed of both.

[0160] According to one implementation, the shell contains at least 10% inorganic components.

[0161] According to one implementation, the shell contains at least 20% inorganic components.

[0162] According to one implementation, the shell contains at least 30% inorganic components.

[0163] According to one implementation, the shell contains at least 40% inorganic components.

[0164] According to one implementation, the shell is essentially inorganic.

[0165] The phrase "substantially inorganic" should be understood to mean that the shell contains at least 50% inorganic content, preferably at least 70% inorganic content, more preferably at least 90% inorganic content, and most preferably 100% inorganic content.

[0166] nucleophilic reagents

[0167] According to one particular embodiment, the shell comprises at least one compound containing an inorganic moiety, at least one compound having at least two P-Cl functional groups, and a reaction product of at least one nucleophile.

[0168] According to the present invention, nucleophilic compounds are defined as chemical substances that donate electron pairs to electrophilic reagents in a reaction to form chemical bonds.

[0169] Nucleophiles can be selected from the group consisting of nitrogen nucleophiles, sulfur nucleophiles, oxygen nucleophiles, carbon nucleophiles, phosphorus nucleophiles, and mixtures thereof.

[0170] Nitrogen nucleophiles may have at least one functional group selected from the group consisting of ammonia, azides, amines, nitrites, hydroxylamine, hydrazine, carbazide, phenylhydrazine, aminourea, and amides, and mixtures thereof.

[0171] A sulfur nucleophile may have at least one functional group selected from the group consisting of hydrogen sulfide and its salts, thiols (RSH), thiols anions (RS-), thiocarboxylic acid anions (RC(O)-S-), dithiocarbonate anions (RO-C(S)-S-), and dithiocarbamate anions (R2NC(S)-S-), and mixtures thereof.

[0172] Oxynucleophiles may have at least one functional group selected from the group consisting of water, hydroxide anions, alcohols, alkoxide anions, carboxylate anions, carbonates, sulfonates, sulfates, sodium phosphates, sodium silicates, borax, sodium tetraborate, and mixtures thereof.

[0173] A carbon nucleophile may have at least one functional group selected from the group consisting of an enol carnucleophile, malonate, and acetoacetate.

[0174] Phosphorus nucleophiles may have at least one functional group selected from the group consisting of phosphine, phosphite anions, and mixtures thereof.

[0175] According to one embodiment, the nucleophile is selected from the group consisting of alcohols, amines, thiols, and mixtures thereof.

[0176] In this invention, "alcohol" and "polyol" can be used interchangeably.

[0177] According to a particular embodiment, the amine is selected from the group consisting of: cystamine, EDA, DETA, pentamethylenediamine, hexamethylenediamine, poly(L-lysine) (modifiable), L-lysine, L-lysine ethyl ester, dimethyl cystine ester, and mixtures thereof.

[0178] According to a particular embodiment, the amine is selected from the group consisting of: cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride, xylene diamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamide amine (PAMAM), guanidine carbonate, chitosan, tris(2-aminoethyl)amine, 1,4-diaminobutane, 2,2-dimethyl-1,3-propanediamine, 1,3-diaminopentane (Dytek) EP diamine), 1,2-diaminopropane, triethylenetetramine, 1,3-diaminopropane; urea; ethylidene urea; aminoguanidine bicarbonate; 1-(2-aminoethyl)imidazolidine-2-one; N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine; N1-(2-aminoethyl)-N1-dodecyl-1,2-ethylenediamine; aminoethylethanolamine; N1-(3-aminopropyl)propane-1,3-diamine, polyethyleneimine, C36-alkyldiamine (e.g., Priamine) TM—(1E,19E)-10,11-dioctyleicosico-1,19-diene-1,20-diamine (low viscosity, bio-based, dimer diamine)), amino acids (e.g., lysine, arginine, leucine, histidine, tryptophan, serine, glutamine, threonine, alanine, asparagine, aspartic acid, cysteine, glutamic acid, glycine, isoleucine, methionine, phenylalanine, proline, tyrosine, valine), 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene (TCPA), and mixtures thereof.

[0179] According to a particular embodiment, the alcohol (or polyol) is selected from the group consisting of: phloroglucinol, hydroquinone, hydroquinone bis(2-hydroxyethyl) ether, 1,4-cyclohexanediol, resorcinol, isosorbide, pentaerythritol, erythritol, trimethylolpropane, bis-trimethylolpropane, sorbitol, mannitol, xylitol, triethanolamine, diglycerides, triglycerides and their respective fractional esters, polyglycerol and their respective fractional esters, and mixtures thereof.

[0180] According to a particular embodiment, the thiol (or polythiol) is selected from: ethylene glycol dimercaptoacetate, dithiothreitol, trimethylolpropane tris(3-mercaptopropionate), 2,2'-thiodiethylthiol, pentaerythritol tetra(3-mercaptopropionate), 2-mercaptoethanol, 3-aminopropane-1-thiol, 3-aminopropane-1-thiol hydrochloride, 3-mercapto-1,2-propanediol, 3-mercapto-1-propanol, 1-mercapto-2-propanol, 6-mercapto-1-hexanol, 4-mercaptoacetoxybutyl thioacetate, 1-thioglycerol, 2-{2-[2-(2-mercaptoethoxy)ethoxy]ethoxy}ethanol, cysteine, cysteine ​​hydrochloride, 4-mercaptophenol, 4,6-diamino-2-pyrimidinethiol, 4,6-dihydroxy-2-mercaptopyrimidine, propane-1,3-dithiol, and mixtures thereof.

[0181] According to one embodiment, the nucleophile is the same molecule as the compound having at least two P-Cl functional groups.

[0182] According to one embodiment, the nucleophile is the same molecule as the compound having at least two P-Cl functional groups, wherein the molecule is 2,2,4,4-tetraamino-6,6-dichlorocyclotriphosphazene.

[0183] According to one embodiment, the nucleophile is not the same molecule as the compound having at least two P-Cl functional groups.

[0184] Biodegradable

[0185] In one particular implementation, the shell material is a biodegradable material.

[0186] In one particular implementation, the organic portion of the shell is biodegradable.

[0187] In one particular embodiment, the shell has a biodegradability of at least 40% within 60 days according to OECD301F, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 98%.

[0188] In one particular embodiment, the core-shell microcapsule has a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 98% within 60 days according to OECD301F.

[0189] Therefore, it should be understood that the biodegradability of core-shell microcapsules, including all components such as the core, shell and optional coating, within 60 days according to OECD 301F can be at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%.

[0190] In one particular embodiment, the oil core, preferably a flavoring 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.

[0191] OECD 301F is the standard test method of the Organization for Economic Cooperation and Development for biodegradability.

[0192] Gasparini et al. in Molecules 2020, 25, 718 disclose a typical method for extracting shells to measure biodegradability.

[0193] outer coating layer

[0194] According to a particular embodiment of the invention, the microcapsule comprises an outer coating layer (coating), wherein the outer coating layer comprises a coating material selected from the group consisting of nonionic polymers (e.g., nonionic polysaccharides), anionic polymers (e.g., polysaccharides), cationic polymers, polysuccinimide derivatives (e.g., described in WO2021185724), and mixtures thereof, for forming the outer coating of the microcapsule.

[0195] According to one particular implementation, the microcapsule does not contain an outer coating layer.

[0196] Nonionic polysaccharide polymers are well known to those skilled in the art and are described, for example, on page 29, lines 1 to 25 of WO2012 / 007438 and on page 2, lines 12 to 19 of WO2013 / 026657 and on page 4, lines 3 to 12. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar gum, hydroxypropyl cellulose, and hydroxypropyl methylcellulose.

[0197] 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, but also preferably less than about 7 meq / g, more preferably less than about 6.2 meq / g. The cationic charge density of the cationic polymer can be determined by the Kjeldahl method, as described in the United States Pharmacopeia under Chemical Tests for Nitrogen Determination. Preferred cationic polymers are selected from units containing primary, secondary, tertiary, and / or quaternary amine groups, which may form part of the main polymer chain or may be supported by side substituents directly connected thereto. The weight-average molecular weight (Mw) of the cationic polymer is preferably from 10,000 to 3.5 M Daltons, more preferably from 50,000 to 1.5 M Daltons. According to a specific implementation scheme, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylaminomethacrylate, diallyl dimethylammonium chloride, quaternized vinylimidazolium (3-methyl-1-vinyl-1H-imidazolium-3-onium chloride), vinylpyrrolidone, acrylamide propyltrimethylammonium chloride, cassia gum hydroxypropyltrimethylammonium chloride, guar gum hydroxypropyltrimethylammonium chloride, or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimethylammonium chloride, and cellulose hydroxypropyltrimethylammonium chloride will be used. Preferably, the copolymer should be 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 gum hydroxypropyltrimethylammonium chloride, guar gum hydroxypropyltrimethylammonium chloride, or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimethylammonium chloride, and cellulose hydroxypropyltrimethylammonium chloride. Salcare can be cited as a specific example of a commercially available product. ® SC60 (a cationic copolymer of acrylamide propyltrimethylammonium chloride and acrylamide, source: BASF) or Luviquat®, such as PQ 11N, FC 550 or Style (a quaternized copolymer of polyquaternium salts-11~68 or vinylpyrrolidone, source: BASF), or Jaguar® (C13S or C17, source: Rhodia).

[0198] According to any of the above embodiments of the present invention, the amount of the added polymer is about 0% to 5% w / w, or even about 0.1% to 2% w / w, the percentage being expressed on a w / w basis relative to the total weight of the slurry. Those skilled in the art will clearly understand that only a portion of the added polymer will be incorporated into / deposited onto the microcapsule shell.

[0199] According to one particular embodiment, the microcapsules of the present invention comprise a mineral layer. The mineral layer preferably comprises a material selected from the group consisting of iron oxide, iron hydroxyl oxide, titanium oxide, zinc oxide, calcium carbonate, calcium phosphate, barium salts, strontium salts, magnesium salts, and mixtures thereof.

[0200] solid particles

[0201] Another object of the present invention is a solid particle comprising:

[0202] - The carrier material, preferably a polymeric carrier material selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, plant gums, pectin, xanthan gum, alginate, carrageenan, cellulose derivatives, and mixtures thereof, and

[0203] - Microcapsules as defined above embedded in the carrier material, and

[0204] - Optionally, free fragrance embedded in the carrier material.

[0205] Solid particles and microcapsule powders as defined above are used interchangeably in this invention.

[0206] Methods for preparing microcapsules

[0207] Another object of the present invention is to provide a method for preparing core-shell microcapsule slurry, comprising the following steps:

[0208] a) Optionally, at least one compound having at least two P-Cl functional groups is provided;

[0209] b) Mix at least one hydrophobic material with an optional compound obtained in step a) to form an oil phase;

[0210] c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0211] d) Optionally, the two-phase dispersion is dispersed into a continuous phase C2, which optionally contains at least one compound having at least two P-Cl functional groups to form a multiple dispersion;

[0212] e) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form.

[0213] A compound having an inorganic moiety is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

[0214] It should be understood that, according to the present invention, at least one compound having at least two P-Cl functional groups is added in step a) and / or step d).

[0215] It should also be understood that at least one compound having at least two P-Cl functional groups used in step a) and / or step d) can be used as a pure compound (i.e., not reacting with any reactants), or as a modified compound if reactants are added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

[0216] According to a particular implementation scheme, the method includes the following steps:

[0217] a) Provide at least one compound having at least two P-Cl functional groups,

[0218] b) Mix at least one hydrophobic material with the compound obtained in step a) to form an oil phase;

[0219] c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0220] d) Solidify the dispersion obtained in step c) to form microcapsules in slurry form.

[0221] In step a) and / or step b) and / or step c) and / or step d), a compound having an inorganic moiety is added.

[0222] According to one embodiment, a method for preparing core-shell microcapsule slurry includes the following steps:

[0223] a) Prepare a solution containing at least one compound having at least two P-Cl functional groups.

[0224] b) Mix at least one active ingredient with the solution obtained in step a) to form an oil phase;

[0225] c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0226] d) Optionally, the two-phase dispersion is dispersed into the continuous phase C2 to form a multi-phase dispersion;

[0227] e) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form.

[0228] A compound having an inorganic moiety is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

[0229] According to a particular implementation scheme, the method includes the following steps:

[0230] a) Provide at least one compound having at least two P-Cl functional groups,

[0231] b) Mix at least one hydrophobic material with the compound obtained in step a) to form an oil phase;

[0232] c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0233] d) Disperse the two-phase dispersion into a continuous phase C2, which optionally contains at least one compound having at least two P-Cl functional groups to form a multiple dispersion;

[0234] e) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form.

[0235] A compound having an inorganic moiety is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

[0236] The compound having at least two P-Cl functional groups in step d) can be the same as or different from the compound having at least two P-Cl functional groups in step a).

[0237] According to a particular implementation scheme, the method includes the following steps:

[0238] a) Provide at least one hydrophobic material to form the oil phase;

[0239] b) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion;

[0240] c) Disperse the two-phase dispersion into a continuous phase C2, which contains at least one compound having at least two P-Cl functional groups to form a multiple dispersion;

[0241] d) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form.

[0242] In step a) and / or step b) and / or step c) and / or step d), a compound having an inorganic moiety is added.

[0243] The disclosed embodiments for core-shell microcapsules are also applicable to methods for preparing core-shell microcapsules. They are particularly applicable to compounds having at least two P-Cl functional groups, hydrophobic materials, compounds having an inorganic moiety, or nucleophiles.

[0244] According to one embodiment, the continuous phase C1 contains water, preferably water.

[0245] According to one implementation scheme, the continuous phase C1 is the aqueous phase.

[0246] According to one implementation, the two-phase dispersion is an oil-in-water emulsion.

[0247] According to one implementation, the two-phase dispersion is a water-in-oil emulsion.

[0248] According to one embodiment, the continuous phase C1 comprises water and alcohols, such as glycerol, 1,4-butanediol, ethylene glycol, and mixtures thereof.

[0249] According to one embodiment, the continuous phase C1 is composed of alcohols.

[0250] Stabilizers can be added to the oil phase and / or the continuous phase C1.

[0251] "Stabilizer" refers to a compound that can stabilize the oil / dispersed phase interface (usually the oil / water interface) to form an emulsion.

[0252] Based on a two-phase dispersion, preferably based on an oil-in-water emulsion, the stabilizer is preferably used in an amount of 0.05 to 20% by weight, more preferably 0.1 to 10% by weight, and even more preferably 0.1 to 5% by weight.

[0253] In this invention, "stabilizer" or "emulsifier" can be used indiscriminately.

[0254] According to one embodiment, the stabilizer can function as a nucleophile. Therefore, according to one embodiment, the stabilizer is the nucleophile of the present invention.

[0255] According to one embodiment, the stabilizer is a colloidal stabilizer.

[0256] Colloidal stabilizers can be polymer emulsifiers (standard emulsions), surfactants, or solid particles (Pickerling emulsions).

[0257] "Polymer / polyemulsifier" refers to an emulsifier that simultaneously possesses polar groups that are affinity for water (hydrophilic) and nonpolar groups that are affinity for oil (lipophilic). The hydrophilic portion dissolves in the aqueous phase, while the hydrophobic portion dissolves in the oil phase, thereby forming a thin film around the droplet.

[0258] "Surfactant" refers to a substance with both polar and nonpolar groups that, when added to a liquid, can reduce the liquid's surface tension.

[0259] According to one embodiment, the stabilizer is selected from the group consisting of inorganic particles, polymeric emulsifiers such as polysaccharides, proteins, glycoproteins, and mixtures thereof.

[0260] When the stabilizer is a solid particulate, it can be selected from the group consisting of calcium phosphate, silicon dioxide, silicates, titanium dioxide, aluminum oxide, zinc oxide, iron oxide, mica, kaolin, montmorillonite, lithium saponite, bentonite, perlite, dolomite, diatomite, vermiculite, lithium montmorillonite, gibbsite, illite, kaolinite, aluminosilicate, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomite, and mixtures thereof.

[0261] In one particular implementation, the stabilizer is a biopolymer.

[0262] "Biopolymers" refers to biological macromolecules produced by living organisms. Biopolymers are characterized by a molecular weight distribution ranging from 1,000 (1,000) to 1,000,000,000 (1 billion) Daltons. These macromolecules can be carbohydrates (glycosyl groups), proteins (amino acid groups), or a combination of both (gums), and can be linear or branched.

[0263] According to one embodiment, the polymeric emulsifier is selected from the group consisting of: gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethyl cellulose (CMC), anionic polysaccharides, acrylamide copolymers, proteins such as soy protein, rice protein, whey protein, egg white protein, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.

[0264] Potato protein is typically extracted from potato tubers (Solanum tuberosum). According to one embodiment, the potato protein is a natural potato protein, preferably a patatin (a potato tuber-specific protein).

[0265] The proteins used in this invention can be native or partially or completely denatured by any suitable method. Denaturation is a process of altering the conformational structure of a protein through unfolding; that is, it involves the breaking and possible disruption of the protein's secondary and tertiary structures. In fact, denaturation means the breaking of many weak connections or bonds (e.g., hydrogen bonds) within the protein molecule that are responsible for the highly ordered structure of the protein in its native state. Denaturation can be reversible (the protein can return to its native state when the denaturing effects are removed) or irreversible.

[0266] Denaturation can occur in a variety of ways. Proteins may denature due to exposure to temperature, radiation, or mechanical stress (including shearing), pH changes (treatment with alkalis or acids), treatment with oxidizing or reducing agents, inorganic salts, certain organic solvents, or dissociation agents (i.e., those with a positive dissociation value – measured in kJ / kg on the Hallsworth scale). -1 The compounds in the molar form of guanidine salts, such as guanidine carbonate, guanidine hydrochloride, urea, calcium chloride, n-butanol, ethanol, lithium perchlorate, lithium acetate, magnesium chloride, phenol, 2-propanol, sodium dodecyl sulfate, and thiourea, are denatured.

[0267] The proteins used in this invention can also be derivatized or modified (e.g., derivatized or chemically modified). For example, proteins can be modified by covalently linking sugars, lipids, peptides, or chemical groups such as phosphate groups or methyl groups.

[0268] According to one embodiment, the compound having at least two P-Cl functional groups is added in an amount of 0.5 to 10% by weight, preferably 1 to 5% by weight, based on the total weight of the multiple dispersion.

[0269] According to one embodiment, the compound having the inorganic portion is added in an amount of 1 to 15% by weight, preferably 1 to 8% by weight, based on the total weight of the multi-dispersion.

[0270] According to one embodiment, an alkali is added to the continuous phase C1. Preferably, the alkali is selected from the group consisting of guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, and mixtures thereof.

[0271] When used, the alkali is typically used in amounts of 0.1 to 10% by weight, preferably 3 to 7% by weight, based on the total weight of the continuous phase C1.

[0272] According to one embodiment, in step a) and / or step b) and / or step c) and / or step d) and / or step e), a nucleophile selected from the group consisting of nitrogen nucleophiles, sulfur nucleophiles, enol carbon nucleophiles, oxygen nucleophiles, phosphorus nucleophiles, and mixtures thereof is added.

[0273] Nucleophiles are defined as described above.

[0274] According to one embodiment, a nucleophile is added to the oil phase and / or the continuous phase C1.

[0275] Based on the total weight of the two-phase dispersion, the nucleophile can be added in an amount of 0.5 to 10% by weight, preferably 1 to 4% by weight.

[0276] In step e), the dispersion obtained in step d) or e) is solidified to form microcapsules in the form of a slurry.

[0277] Optionally, nonionic polymers (e.g., nonionic polysaccharides), anionic polymers (e.g., polysaccharides), cationic polymers, polysuccinimide derivatives (e.g., as described in WO2021185724), and mixtures thereof, as defined above, may be added in or after step e) to form an outer coating layer.

[0278] According to a preferred embodiment, in order to improve kinetic performance, the step is performed at a temperature of 5 to 90°C and may be carried out under pressure for 1 to 24 hours. More preferably, the step is performed at a temperature of 10 to 80°C for 30 minutes to 5 hours.

[0279] Multiple microcapsule systems

[0280] According to one embodiment, the microcapsules of the present invention (first type microcapsules) can be used in combination with second type microcapsules.

[0281] Another object of the present invention is a microcapsule delivery system comprising:

[0282] • The microcapsules of the present invention, as a first type of microcapsule, and

[0283] • Type II microcapsules, wherein Type I microcapsules differ from Type II microcapsules in their hydrophobic materials and / or their wall materials and / or their coating materials.

[0284] According to one particular implementation, the microcapsule delivery system is in the form of a slurry.

[0285] The walls of the second type of microcapsules can vary. As a non-limiting example, the polymer shell of the second type of microcapsules comprises materials selected from the group consisting of polyurea, polyurethane, polyamide, polyhydroxyalkanoates, polyacrylates, polyesters, polyurethanes, polyepoxides, silicones, polycarbonates, polysulfonamides, urea-formaldehyde resins, melamine-formaldehyde resins, melamine-formaldehyde resins crosslinked with polyisocyanates or aromatic polyols, melamine urea resins, melamine glyoxal resins, gelatin / gum arabic shell walls, and mixtures thereof.

[0286] The second type of microcapsule may comprise an oil-based core and a composite shell. The oil-based core contains a hydrophobic active substance, preferably a fragrance. The composite shell comprises a first material and a second material, wherein the first material and the second material are different; the first material is a coagulation layer, and the second material is a polymeric material. In a particular embodiment, the weight ratio between the first material and the second material is from 50:50 to 99.9:0.1. In a particular embodiment, the coagulation layer comprises a first polyelectrolyte and a second polyelectrolyte. The first polyelectrolyte is preferably selected from proteins (e.g., gelatin), polypeptides, or polysaccharides (e.g., chitosan), most preferably gelatin. The second polyelectrolyte is preferably alginate, cellulose derivative, guar gum, pectinate, carrageenan, polyacrylic acid, and methacrylic acid or xanthan gum, or plant gum such as acacia gum (gum arabic), most preferably gum arabic. The first material of the coagulation layer may 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 may be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof, with polyurea and / or polyurethane being preferred. Based on the total weight of the second type of microcapsule slurry, the second material is preferably present in an amount of less than 3% by weight, preferably less than 1% by weight.

[0287] As a non-limiting example, the shell of the second type of microcapsule may be based on amino-plastic, polyurea, or polyurethane. The shell of the second type of microcapsule may also be composite, i.e., organic-inorganic, such as a composite shell composed of at least two types of cross-linked inorganic particles, or a shell produced by the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0288] According to one morphology, the shell of the second type of microcapsule contains an amino plastic copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine-formaldehyde or melamine-glyoxal.

[0289] According to another form, the shell of the second type of microcapsule is polyurea-based, made of, for example but not limited to, isocyanate-based monomers and amine-containing crosslinking agents such as guanidine carbonate and / or guanidineazole. Some polyurea microcapsules comprise a polyurea wall, which is the product of a polymerization reaction between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from amines (e.g., water-soluble guanidine salts and guanidine); a colloidal stabilizer or emulsifier; and an encapsulating fragrance. However, the use of amines may be omitted. According to one particular form, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% vinylpyrrolidone, and a cationic copolymer of quaternized vinylimidazolium (all percentages are defined relative to the total weight of the colloidal stabilizer). According to another form, the emulsifier is an anionic or amphiphilic biopolymer, in one form of which may be selected, for example, from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0290] According to another embodiment, the microcapsule wall material of the second type of microcapsule may comprise any suitable resin, particularly including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include reaction products of aldehydes and amines, with suitable aldehydes including formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanidine, glycyrrhizin, and mixtures thereof. Suitable melamines include hydroxymethyl melamine, methylated hydroxymethyl melamine, iminomelamine, and mixtures thereof. Suitable ureas include dihydroxymethyl urea, methylated dihydroxymethyl urea, urea-resorcinol, and mixtures thereof. Suitable materials for manufacture may be obtained from one or more of the following companies: Solutia Inc. (St. Louis, Missouri USA), Cytec Industries (West Paterson, New Jersey USA), and Sigma-Aldrich (St. Louis, Missouri USA).

[0291] According to another embodiment, the second type of microcapsule is a single-shell amino-plastic core-shell microcapsule, which can be obtained by a method including the following steps:

[0292] 1) The fragrance oil is mixed with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase;

[0293] 2) Disperse or dissolve the amino plastic resin and optional stabilizer in water to form an aqueous phase;

[0294] 3) Prepare oil-in-water dispersions by mixing oil and aqueous phases, wherein the average droplet size is 1 to 100 micrometers;

[0295] 4) Perform a curing step to form the wall of the microcapsules; and

[0296] 5) Optionally, the final dispersion is dried to obtain dried core-shell microcapsules.

[0297] According to one embodiment, the second type of microcapsule is a formaldehyde-free capsule. A typical method for preparing formaldehyde-free microcapsule slurry of amino plastics includes the following steps:

[0298] 1) Prepare an oligomer composition comprising the reaction product of the following components, or obtain an oligomer composition by reacting the following components together:

[0299] 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;

[0300] b. Glyoxal, C 4-6 An aldehyde component in the form of a mixture of 2,2-dialkoxyacetaldehyde and optionally glyoxylate, wherein the glyoxal / C ratio of the mixture is... 4-6 The molar ratio of 2,2-dialkoxyethanol is from 1 / 1 to 10 / 1; and

[0301] c. Protic acid catalyst;

[0302] 2) Prepare an oil-in-water dispersion, wherein the droplet size is 1 to 600 micrometers, and comprises:

[0303] a. oil;

[0304] b. Water medium

[0305] c. At least one oligomer composition as obtained in step 1;

[0306] d. At least one crosslinking agent selected from the following:

[0307] i.C4-C 12 Aromatic or aliphatic di or triisocyanates and their biuret, triuret, trimers, trimethylolpropane adducts and mixtures thereof; and / or

[0308] ii. Di- or tri-epoxyethylene compounds of the following formula

[0309] A-(ethylene oxide-2-ylmethyl) n

[0310] Where n represents 2 or 3, and A represents a C2-C6 group that optionally contains 2 to 6 nitrogen and / or oxygen atoms;

[0311] e. Optionally, a C1-C4 compound containing two NH2 functional groups;

[0312] 3) Heat the dispersion;

[0313] 4) Cool the dispersion.

[0314] In another specific implementation, the second type of microcapsule comprises:

[0315] - An oil-based core containing hydrophobic active substances, preferably fragrances.

[0316] - Optionally, the inner shell is made of polymerized multifunctional monomers;

[0317] - A biopolymer shell containing proteins, wherein at least one protein is cross-linked.

[0318] According to a particular embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed protein, gelatin, gluten, pea protein, soy protein, silk protein, and mixtures thereof, with sodium caseinate being preferred and most preferred.

[0319] According to a particular embodiment, the protein comprises sodium caseinate and globular protein, preferably selected from the group consisting of whey protein, β-lactoglobulin, ovalbumin, bovine serum albumin, plant protein, and mixtures thereof.

[0320] The preferred protein is a mixture of sodium caseinate and whey protein.

[0321] According to one particular embodiment, the biopolymer shell comprises a cross-linked protein selected from the group consisting of sodium caseinate and / or whey protein.

[0322] According to one specific embodiment, the second type of microcapsule slurry comprises at least one microcapsule made of the following material:

[0323] -Oil-based core, which contains hydrophobic active substances, preferably fragrances;

[0324] - An inner shell made of polymerized multifunctional monomers; preferably a multiisocyanate having at least two isocyanate functional groups;

[0325] - A biopolymer shell comprising a protein, wherein at least one protein is cross-linked; wherein the protein preferably comprises a mixture comprising sodium caseinate and globular protein, preferably whey protein;

[0326] - Optionally, at least one outer mineral layer.

[0327] According to one embodiment, sodium caseinate and / or whey protein are cross-linked proteins.

[0328] The weight ratio of sodium caseinate to whey protein is preferably 0.01 to 100, more preferably 0.1 to 10, and even more preferably 0.2 to 5.

[0329] In another specific embodiment, the second type of microcapsule is a polyamide core-shell polyamide microcapsule, which comprises:

[0330] - An oil-based core containing hydrophobic active substances, preferably fragrances, and

[0331] - A polyamide shell, which comprises or may be derived from:

[0332] • Acyl chloride,

[0333] • First amino compound,

[0334] • Second amino compound,

[0335] •Optional, carbohydrates.

[0336] According to one specific implementation scheme, the second type of microcapsule comprises:

[0337] - An oil-based core containing hydrophobic active substances, preferably fragrances, and

[0338] - A polyamide shell, which comprises or may be derived from:

[0339] • Acyl chloride, preferably 5 to 98%, more preferably 20 to 98%, and more preferably 30 to 85% w / w;

[0340] • The first amino compound, preferably in a content of 1% to 50% w / w, more preferably 7% to 40% w / w;

[0341] • The second amino compound, preferably in a content of 1% to 50% w / w, more preferably 2% to 25% w / w;

[0342] • Stabilizer, preferably a biopolymer, preferably in a content of 0 to 90%, more preferably 0.1 to 75%, and even more preferably 1 to 70%.

[0343] •Optional, carbohydrates.

[0344] According to one specific implementation scheme, the second type of microcapsule comprises:

[0345] - An oil-based core containing hydrophobic active substances, preferably fragrances, and

[0346] - A polyamide shell, which comprises or may be derived from:

[0347] • Acyl chloride,

[0348] • The first amino compound, which is an amino acid, is preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof.

[0349] • Second amino compounds, selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine, and / or mixtures thereof, and

[0350] • Biopolymers, preferably selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, soybean protein, rice protein, whey protein, egg white protein, casein, sodium caseinate, gelatin (preferably fish gelatin), bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, gelatin, and mixtures thereof.

[0351] • Optionally, the carbohydrate is preferably selected from the group consisting of anionic alginate, preferably sodium alginate, pectin, lignin, anionic modified starch, carboxymethyl cellulose, carrageenan, and mixtures thereof.

[0352] According to another formulation, the shell of the second type of microcapsule is polyurea-based or polyurethane-based. Examples of methods for preparing polyurea-based and polyurethane-based microcapsule slurries are described, for example, in International Patent Application Publication No. WO2007 / 004166, European Patent Application Publication No. EP 2300146, and European Patent Application Publication No. EP25799. Typically, a method for preparing polyurea-based or polyurethane-based microcapsule slurries includes the following steps:

[0353] a) Dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase;

[0354] b) Prepare an aqueous solution of the emulsifier or colloidal stabilizer to form a dispersed phase;

[0355] c) Adding the oil phase to the aqueous phase to form an oil-in-water dispersion, wherein the average droplet size is 1 to 500 μm, preferably 5 to 50 μm; and

[0356] d) Apply conditions sufficient to initiate interfacial polymerization and form microcapsules in slurry form.

[0357] Fragrance compositions and consumer products

[0358] The present invention also relates to a flavoring composition comprising:

[0359] - Core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above.

[0360] - At least one ingredient selected from the group consisting of a spice carrier and a spice base, and

[0361] -Optionally, at least one spice adjuvant.

[0362] In one particular embodiment, the composition comprises:

[0363] - Core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above.

[0364] - The active ingredient is preferably selected from the group consisting of: cosmetic ingredients, skin care ingredients, fragrance ingredients, flavoring ingredients, odor-dispelling ingredients, bactericides, fungicides, pharmaceutical or agricultural chemicals, disinfectants, insect repellents or attractants, and mixtures thereof.

[0365] In one particular embodiment, core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above can also be added to various flavored consumer products.

[0366] In one particular embodiment, the present invention relates to a flavoring composition comprising:

[0367] • Core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above

[0368] •Optional, free spice oil.

[0369] Preferably, the fragrance composition according to the invention comprises 0.1 to 40% by weight, preferably 0.1 to 30% by weight, of core-shell microcapsules or core-shell microcapsule slurry obtained by the method of the invention or by the method described above.

[0370] "Free fragrance" is understood herein to mean a fragrance or fragrance oil that is contained in a flavoring composition and is not embedded in a core-shell microcapsule or core-shell microcapsule slurry obtained by the method of the present invention or by the method described above.

[0371] In one particular embodiment, the total amount of core-shell microcapsules or core-shell microcapsule slurry obtained by the method of the present invention or by the method described above is 0.05 to 5% by weight (based on the total weight of the flavoring composition), and the total amount of free fragrance oil is 0.05 to 5% by weight (based on the total weight of the flavoring composition).

[0372] In one particular embodiment, the total fragrance oil of the fragrance blend embedded in the core-shell microcapsules or core-shell microcapsule slurry obtained by the method of the present invention or as described above is in a weight ratio of 1:20 to 20:1, preferably 10:1 to 1:10, to all free fragrance oils in the flavoring composition.

[0373] The flavoring composition may also contain at least one flavoring auxiliary ingredient, and optionally, a flavoring adjuvant.

[0374] By "fragrance aid," this refers to a compound used in fragrance preparations or compositions to impart a pleasurable effect, and is not a microcapsule as defined above. In other words, to be considered a fragrance aid, it must be recognized by those skilled in the art as capable of actively or pleasantly imparting or modifying the odor of a composition, and not merely possessing an odor. The nature and type of fragrance aid present in fragrance compositions are not guaranteed to be described in greater detail here, and are by no means exhaustive; those skilled in the art can select them based on their common sense and according to the intended use or application and the desired sensory effect. Generally, these fragrance aids belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen- or sulfur-containing heterocyclic compounds, and essential oils, and said fragrance aids may be of natural or synthetic origin. In any case, many of these auxiliary ingredients are listed in references such as S. Arctander's *Perfume and Flavor Chemicals*, 1969, Montclair, New Jersey, USA, or later editions thereof, or other works of a similar nature, as well as in the extensive patent literature within the fragrance industry. It is also understood that the auxiliary ingredients can be compounds known to release various types of flavoring compounds in a controlled manner.The auxiliary ingredients can be selected from the group consisting of: 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)oct-4-one, 2-phenylethyl oxo(phenyl)acetic acid, 3,7-dimethyloct-2,6-diene-1-oxo(phenyl)acetic acid. - esters, oxo(phenyl)acetic acid (Z)-hex-3-en-1-yl ester, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethyloct-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-(oct-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-pentylcyclopentyl)methoxy) (2-(2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentyl)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentyl)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentyl)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof.

[0375] The term "fragrance adjuvant" refers to ingredients that can impart additional benefits, such as color, specific lightfastness, chemical stability, etc. A detailed description of the properties and types of adjuvants typically used in fragrance bases is impossible to exhaustively cover, but it must be mentioned that these ingredients are well known to those skilled in the art.

[0376] Core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above can be advantageously used in many application areas and in consumer products.

[0377] This invention also relates to a scented consumer product, comprising:

[0378] - Core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above, and

[0379] - Active base material for personal care, home care, or fabric care.

[0380] The consumer products of this invention are particularly applicable to scented consumer products, such as products that belong to the category of fine fragrances or "functional" fragrances. Functional fragrances include, in particular, personal care products (including hair care, body cleansing, skin care, and hygiene care) and home care products (including laundry care and air care).

[0381] Specifically, a liquid consumer product comprises:

[0382] - At least one surfactant comprising 2 to 65% by weight of the total weight of the consumer product;

[0383] - Water or a water-miscible hydrophilic organic solvent; and

[0384] - Fragrance compositions or core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above.

[0385] There is also a type of powdered consumer product that includes:

[0386] - At least one surfactant comprising 2 to 65% by weight of the total weight of the consumer product; and

[0387] - Fragrance compositions or core-shell microcapsules or core-shell microcapsule slurries obtained by the method of the present invention or by the method described above.

[0388] For clarity, it must be mentioned that "fragrant consumer product" refers to a consumer product intended to deliver the fragrance effect, among various benefits, to surfaces to which it is applied (e.g., skin, hair, fabric, paper, or household surfaces) or into the air (air fresheners, deodorants, etc.). In other words, the fragrant consumer product according to the invention is a processed product comprising a functional formulation (also referred to as a "base") and beneficial agents, including an effective amount of microcapsules according to the invention.

[0389] The nature and type of other ingredients in flavored consumer products are not guaranteed to be described in greater detail here, as it is impossible to exhaustively describe them in any way. Those skilled in the art can select them based on their general knowledge and the properties and desired effects of the product. Formulations of base materials for consumer products in which the microcapsules of this invention can be incorporated can be found in a large body of literature relating to such products. These formulations are not guaranteed to be described in detail here, as it is impossible to exhaustively describe them in any way. Those skilled in the art of formulating such consumer products are fully capable of selecting suitable components based on their general knowledge and available literature.

[0390] Suitable, non-restrictive examples of scented consumer products may include fine perfumes, spray perfumes, or eau de parfums. Perfume, cologne, shaving lotion or aftershave, liquid or solid detergents, single-compartment or multi-compartment single-dose detergents, fabric softeners, fabric fresheners, liquid or solid fragrance enhancers (PEG / urea or salt), dryersheets, ironing solutions, paper, bleach, carpet cleaners, curtain care products, shampoos, colorants, color care products, hair styling products, dental care products, disinfectants, feminine hygiene products, hair sprays, hair conditioning products, cold cream, deodorants or antiperspirants, hair removal products, tanning or sun protection products, nail products, skin cleansers, cosmetics, soaps, shower or bath mousse, bath oils or shower gels, or foot / hand care products, hygiene products, air fresheners, "ready-to-use" powder air fresheners, mildew removers, furniture care products, wipes, dishwashing liquids or hard surface cleaners, leather care products, car care products.

[0391] In one particular embodiment, the scented consumer product is preferably selected from the group consisting of personal care compositions, home care compositions or fabric care compositions, with the most preferred forms being antiperspirants, hair care products (e.g., shampoos or conditioners), body care products (e.g., shower gels), oral care products, and laundry care products (preferably detergents or fabric softeners).

[0392] Another object of the present invention is a consumer product comprising:

[0393] - Personal care active base, and

[0394] - Microcapsules or microcapsule slurries as defined above, or flavored compositions as defined above,

[0395] Consumer products are in the form of personal care compositions.

[0396] Personal care active ingredients that can be incorporated into the microcapsules of this invention can be found in a large body of literature relating to this product. These formulations are not guaranteed to be described in detail here, and are by no means exhaustive. Those skilled in the art of formulating such consumer products are fully capable of selecting appropriate components based on their general knowledge and available literature.

[0397] Personal care compositions are preferably selected from the group consisting of: hair care products (e.g., shampoos, hair conditioners, coloring agents or hair sprays), cosmetic preparations (e.g., cold creams, body lotions, or deodorants or antiperspirants), or skin care products (e.g., soaps, bath or shower mousse, bath gels, bath oils or shower gels, bath salts, or hygiene products).

[0398] Another object of the present invention is a consumer product comprising:

[0399] - Active base materials for home care or fabric care, and

[0400] - Microcapsules or microcapsule slurries as defined above, or flavored compositions as defined above,

[0401] The consumer products are in the form of home care or fabric care compositions.

[0402] Numerous documents relating to this product can be found on home care or fabric care bases in which the microcapsules of this invention can be incorporated. These formulations are not guaranteed to be described in detail here, and are by no means exhaustive. Those skilled in the art of formulating such consumer products are fully capable of selecting appropriate components based on their general knowledge and available literature.

[0403] Preferably, the consumer product contains 0.1 to 15% by weight, more preferably 0.2 to 5% by weight, of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, the above concentrations can be adjusted according to the desired beneficial effects for each product.

[0404] For liquid consumer products mentioned below, "active base material" should be understood as including active materials (usually including surfactants).

[0405] For solid consumer products mentioned below, "active base material" should be understood to include active materials (usually including surfactants) and additives (such as bleaching agents, buffers; detergent builders; detergents or soilsuspension polymers; granular enzyme particles, corrosion inhibitors, defoamers, foam suppressants; dyes, fillers and mixtures thereof).

[0406] Home or fabric care compositions are preferably selected from the group consisting of fabric softeners, liquid detergents, powdered detergents, liquid fragrance enhancers and solid fragrance enhancers.

[0407] fabric softener

[0408] One object of the present invention is a consumer product in the form of a fabric softener composition, comprising:

[0409] - Fabric softener active base material; preferably comprising at least one active material selected from the group consisting of: dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquat), Hamburg ester quaternary ammonium salts (HEQ), TEAQ (triethanolamine quaternary ammonium salt), organosilicon, and mixtures thereof, wherein the active base material is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition.

[0410] - As defined above, the microcapsules or microcapsule slurries preferably contain 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0411] -Optional, free spice oil.

[0412] liquid detergent

[0413] One object of the present invention is a consumer product in the form of a liquid detergent composition comprising:

[0414] - Liquid detergent active base material; preferably comprising at least one active material selected from the group consisting of: anionic surfactants, such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES); and nonionic 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 polyglucamides. The active base material is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition.

[0415] - As defined above, the microcapsules or microcapsule slurries preferably contain 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0416] -Optional, free spice oil.

[0417] solid detergent

[0418] One object of the present invention is a consumer product in the form of a solid detergent composition, comprising:

[0419] - Solid detergent active base material; preferably comprising at least one active material selected from the group consisting of: anionic surfactants, such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES); and nonionic 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 polyglucamides. The active base material is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition.

[0420] - As defined above, the microcapsule powder or microcapsule slurry preferably contains 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0421] -Optional, free spice oil.

[0422] Shampoo / Shower Gel

[0423] One object of the present invention is a consumer product in the form of a shampoo or shower gel composition, comprising:

[0424] - Shampoo or shower gel active base; preferably comprising at least one active material selected from the group consisting of: sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoteric acetate, cocamidopropyl betaine, cocamidopropyl betaine, cocamidopropylamine, alkyl glucoside, and amino acid-based surfactants and mixtures thereof, wherein the active base is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition.

[0425] - As defined above, the microcapsules or microcapsule slurries preferably contain 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0426] -Optional, free spice oil.

[0427] Rinse-off conditioners

[0428] One object of the present invention is a consumer product in the form of a rinse-off conditioner composition, comprising:

[0429] - A rinsing conditioner active base material; preferably comprising at least one active material selected from the group consisting of: hexadecyltrimethylammonium chloride, stearyltrimethylammonium chloride, benzalkonium chloride, behenyltrimethylammonium chloride, and mixtures thereof, wherein the active base material is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition.

[0430] - As defined above, the microcapsules or microcapsule slurries preferably contain 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0431] -Optional, free spice oil.

[0432] Solid aroma enhancer

[0433] One object of the present invention is a consumer product in the form of a solid scent booster, comprising:

[0434] - Solid carriers, preferably selected from the group consisting of: urea, sodium chloride, sodium sulfate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars such as sucrose, monosaccharides, disaccharides and polysaccharides and their derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomaltitol, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohols or fatty acids and mixtures thereof.

[0435] - Microcapsules or microcapsule slurries as defined above, which are in powder form, preferably in a content of 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0436] -Optional, free spice oil.

[0437] Liquid fragrance enhancer

[0438] One object of the present invention is a consumer product in the form of a liquid fragrance enhancer, comprising:

[0439] -Aqueous phase,

[0440] - A surfactant system consisting essentially of one or more nonionic surfactants, wherein the average HLB of the surfactant system is 10 to 14, preferably selected from the group consisting of: ethoxylated aliphatic alcohols, POE / PPG (polyoxyethylene and polyoxypropylene) ethers, monoglycerides and polyglycerides, sucrose ester compounds, polyoxyethylene hydroxy esters, alkyl polyglucosides, amine oxides and combinations thereof.

[0441] - Linking groups selected from the group consisting of: alcohols, salts and esters of carboxylic acids, salts and esters of hydroxycarboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactants with an HLB of less than 10, and mixtures thereof, and

[0442] - Microcapsules or microcapsule slurries as defined above, which are in slurry form, preferably in a content of 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0443] -Optional, free spice oil.

[0444] hair dye

[0445] One object of the present invention is a consumer product in the form of an oxidative hair dye composition, comprising:

[0446] - An oxidizing phase comprising an oxidizing agent and an alkaline phase comprising an alkaline reagent, a dye precursor, and a coupling compound; wherein the dye precursor and the coupling compound form an oxidizing hair dye in the presence of the oxidizing agent, preferably in a content of 85 to 99.95% by weight based on the total weight of the composition.

[0447] - As defined above, the microcapsules or microcapsule slurries preferably contain 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.

[0448] -Optional, free spice oil.

[0449] Fragrance composition

[0450] According to one particular embodiment, the consumer product is in the form of a flavored composition, which, based on the total weight of the flavored composition, comprises:

[0451] - 0.1 to 30% by weight, preferably 0.1 to 20% by weight, of the microcapsules or microcapsule slurry as defined above.

[0452] - 0 to 40% by weight, preferably 3 to 40% by weight of spices, and

[0453] - 20 to 90% by weight, preferably 40 to 90% by weight of ethanol.

[0454] The invention will now be further described by way of examples. It should be understood that the claimed invention is not intended to be limited in any way by these examples.

[0455] Example

[0456] Example 1

[0457] HCCP modified with silane-containing monomers

[0458] In a 500 mL round-bottom flask, hexachlorocyclotriphosphazene (HCCP; source: Sigma Aldrich, Switzerland) (15 g, 43 mmol) was dissolved in anhydrous ethyl acetate (150 mL). The solution was cooled to 0 °C in an ice-water bath under a nitrogen atmosphere. Simultaneously, a solution of bis[3-(triethoxysilyl)propyl]amine (source: Gelest, Switzerland) (19 mL, 43 mmol) and triethylamine (6 mL, 43 mmol) in anhydrous ethyl acetate (150 mL) was prepared. This solution was added dropwise to the HCCP solution over approximately 1 hour and 30 minutes. The reaction mixture was then heated to 60 °C and maintained at 60 °C for 3 hours. The reaction mixture was then cooled to room temperature and filtered. The filtrate was recovered and concentrated under reduced pressure to give an orange / brown viscous oil (approximately 30 g).

[0459] Example 2

[0460] HCCP is present in the oil phase, along with bis[3-(triethoxysilyl)propyl]amine, sodium hydroxide, and optionally L-lysine. Preparation of capsules containing acid and gum arabic in a continuous phase of 80 glycerol / 20 water.

[0461] The oil phase was prepared by mixing 30 g of fragrance oil A (see Table 1), hexachlorocyclotriphosphazene (HCCP), and optionally Solanic 200 (potato protein, source: Avebe, Netherlands). In a separate container, the continuous phase was prepared by first dissolving L-lysine (source: Sigma Aldrich, Switzerland), sodium hydroxide, and gum arabic (Superstab AA; source: Nexira, France) in 14 g of water, and then mixing this solution with 56 g of glycerol (source: Sigma Aldrich, Switzerland) (80% glycerol / 20% water). Bis[3-(triethoxysilyl)propyl]amine was added to the continuous phase prior to the emulsification process.

[0462] The continuous phase was introduced into a double-jacketed reactor preheated to 80°C, and the oil phase was poured into the continuous phase. The mixture was emulsified by stirring at 900 rpm for 2 minutes and 30 seconds using a stirrer to form a glycerol / oil-in-water emulsion. The reaction mixture was then stirred at 80°C for 6 hours. The final product was a milky white dispersion.

[0463] Table 1: Formulas for Spice Oils

[0464]

[0465] Table 2: Composition of the capsules:

[0466]

[0467] Example 3:

[0468] HCCP and potato protein in the oil phase, and bis[3-(triethoxysilyl)propyl]amine, sodium hydroxide, L-lysine Preparation of capsules containing amino acids and gum arabic in a continuous phase of 80 glycerol / 20 water.

[0469] The oil phase was prepared by mixing 30 g of fragrance oil, 4 g of hexachlorocyclotriphosphazene (HCCP), and 0.5 g of Solanic 200 (potato protein). In a separate container, the continuous phase was prepared by first dissolving 1 g of L-lysine, 0.7 g of gum arabic, and 0.44 g of sodium hydroxide in 14 g of water, and then mixing this solution with 56 g of glycerol (80% glycerol / 20% water). Different amounts of bis[3-(triethoxysilyl)propyl]amine were added to the continuous phase prior to the emulsification process.

[0470] The continuous phase was introduced into a double-jacketed reactor, and the oil phase was poured into the continuous phase. The mixture was emulsified by stirring at 500 rpm for 2 minutes and 30 seconds using a stirrer to form a glycerol / oil-in-water emulsion. The reaction mixture was then heated to 80°C and stirred at 80°C for 6 hours. The final product was a milky white dispersion.

[0471] Table 3: Composition of the capsules:

[0472]

[0473] Example 4

[0474] HCCP is present in the oil phase, along with bis[3-(triethoxysilyl)propyl]amine, sodium hydroxide, L-lysine, and arabinocyanin. Preparation of capsules glued in a continuous phase of 80 glycerol / 20 water.

[0475] Capsules were prepared according to the same procedure disclosed in Example 3, except that the emulsification process was carried out at a speed of 700 rpm. Furthermore, the oil phase consisted of fragrance oil and / or a hydrophobic solvent (benzyl benzoate), the amount of L-lysine was variable, while the amount of bis[3-(triethoxysilyl)propyl]amine was fixed at 7.3 g.

[0476] Table 4: Composition of the capsules:

[0477]

[0478] Example 5:

[0479] HCCP and bis[3-(triethoxysilyl)propyl]amine in the oil phase, and sodium hydroxide, L-lysine and aramid... Preparation of capsules with primary gum in 80% glycerol / 20% water or in water as the continuous phase.

[0480] Capsules were prepared according to the same procedure as disclosed in Example 4, except that bis[3-(triethoxysilyl)propyl]amine was introduced into the oil phase consisting of 22.5 g of fragrance oil and 7.5 g of hydrophobic solvent, instead of into the continuous phase.

[0481] Table 5: Composition of the capsules:

[0482]

[0483] Example 6

[0484] Elemental analysis method for determining the composition of the shell

[0485] The polymer shells of the microcapsules in Examples 1 to 5 were purified according to the protocol published by Gasparini et al. in Molecules (2020), 25(3), 718.

[0486] The composition of the shell was analyzed by elemental analysis, and the results showed that the shell of the microcapsule contained more than 50% inorganic components.

[0487] Example 7

[0488] HCCP and bis[3-(triethoxysilyl)propyl]amine in the oil phase, and sodium hydroxide, L-lysine and aramid... Preparation of capsules with primary gum as the continuous phase in water.

[0489] The oil phase was prepared by mixing 22.5 g of fragrance oil, 7.5 g of benzyl benzoate, 4 g of hexachlorocyclotriphosphazene (HCCP), and 7.30 g of bis[3-(triethoxysilyl)propyl]amine. The continuous phase was prepared in another container by dissolving L-lysine (amount variable), 0.7 g of gum arabic, and 0.44 g of sodium hydroxide in 70 g of water.

[0490] The oil phase was emulsified into the aqueous phase using Ultraturax (10000 RPM, 2 min), and the emulsion was introduced into a double-jacketed reactor. The reaction mixture was then stirred for 6 hours at a given temperature. The final product was a milky white dispersion.

[0491] Table 6: Composition of the capsules:

[0492]

[0493] Example 8

[0494] HCCP and bis[3-(triethoxysilyl)propyl]amine in the oil phase, and sodium hydroxide, L-lysine and aramid... Preparation of capsules with primary gum as the continuous phase in water.

[0495] The oil phase was prepared by mixing 22.5 g of fragrance oil, 7.5 g of benzyl benzoate, 2 g of hexachlorocyclotriphosphazene (HCCP), and 1.83 g of bis[3-(triethoxysilyl)propyl]amine. The continuous phase was prepared in another container by dissolving L-lysine (amount variable), 0.7 g of gum arabic, and sodium hydroxide (amount variable) in 70 g of water.

[0496] The oil phase was emulsified into the aqueous phase using Ultraturax (10000 RPM, 2 min), and the emulsion was introduced into a double-jacketed reactor. The reaction mixture was then stirred at room temperature for 6 hours. The final product was a milky white dispersion.

[0497] Table 7: Composition of the capsules:

[0498]

[0499] Example 9

[0500] HCCP and bis[3-(triethoxysilyl)propyl]amine in the oil phase, and sodium hydroxide, L-lysine and aramid... Preparation of capsules with primary gum as the continuous phase in water.

[0501] The procedure was the same as before, except that a variable amount of bis[3-(triethoxysilyl)propyl]amine was introduced into the oil phase. The amounts of L-lysine and sodium hydroxide in the aqueous phase were kept constant at 1.5 g and 0.22 g, respectively.

[0502] Table 8: Composition of the capsules:

[0503]

[0504] Example 10

[0505] HCCP and bis[3-(triethoxysilyl)propyl]amine in the oil phase, and sodium hydroxide, different amino acids and Preparation of capsules with gum arabic as the continuous phase in water.

[0506] An oil phase was prepared by mixing 22.5 g of fragrance oil, 7.5 g of benzyl benzoate, 2 g of hexachlorocyclotriphosphazene (HCCP), and 1.83 g of bis[3-(triethoxysilyl)propyl]amine. A continuous phase was prepared in another container by dissolving varying amounts of amino acids, 0.7 g of gum arabic, and 0.22 g of sodium hydroxide in 70 g of water.

[0507] The oil phase was emulsified into the aqueous phase using Ultraturax (10000 RPM, 2 min), and the emulsion was introduced into a double-jacketed reactor. The reaction mixture was then stirred at room temperature for 6 hours. The final product was a milky white dispersion.

[0508] Table 9: Composition of the capsules:

[0509]

[0510] Example 11

[0511] A mixture of HCCP and silane in the oil phase, and sodium hydroxide, L-lysine, and gum arabic in water as a continuous phase. Preparation of phase capsules.

[0512] An oil phase was prepared by mixing 22.5 g of fragrance oil, 7.5 g of benzyl benzoate, 2 g of hexachlorocyclotriphosphazene (HCCP), and a mixture of varying amounts of silane-containing monomers. A continuous phase was prepared in another container by dissolving L-lysine (amount variable), 0.7 g of gum arabic, and sodium hydroxide (amount variable) in 70 g of water.

[0513] The oil phase was emulsified into the aqueous phase using Ultraturax (10000 RPM, 2 min), and the emulsion was introduced into a double-jacketed reactor. The reaction mixture was then stirred at room temperature for 6 hours. The final product was a milky white dispersion.

[0514] Table 10: Composition of the capsules:

[0515]

[0516] Example 12

[0517] HCCP, bis[3-(triethoxysilyl)propyl]amine and polyfunctional polyols in the oil phase, and sodium hydroxide, L- Preparation of capsules containing lysine and gum arabic in water as a continuous phase.

[0518] The oil phase was prepared by mixing 22.5 g of fragrance oil, 7.5 g of benzyl benzoate, 2 g of hexachlorocyclotriphosphazene (HCCP), 3.65 g of bis[3-(triethoxysilyl)propyl]amine, and a polyfunctional polyol (volume variable). The continuous phase was prepared in another container by dissolving 1.5 g of L-lysine, 0.7 g of gum arabic, and 0.3 g of sodium hydroxide in 70 g of water.

[0519] The oil phase was emulsified into the aqueous phase using Ultraturax (10000 RPM, 2 min), and the emulsion was introduced into a double-jacketed reactor. The reaction mixture was then stirred at room temperature for 6 hours. The final product was a milky white dispersion.

[0520] Table 11: Composition of the capsules:

[0521]

[0522] Example 13

[0523] Based on 6,6-dichloro-1,3,5,2l 5 4l 5 ,6l 5 - Triazatriphosphazenecyclohexane-2,2,4,4-tetramine (TCPA) and Preparation of HCCP microcapsules

[0524] 6,6-Dichloro-1,3,5,2l 5 4l 5 ,6l 5 Preparation of triazatriphosphazenecyclohexane-2,2,4,4-tetraamine (TCPA): A 0.5 M ammonia solution in 77 mL (38.5 mmol) of 1,4-dioxane was placed in a 250 mL three-necked round-bottom flask equipped with a condenser and stir bar, and purged with N2. HCCP (1.04 g, 3 mmol) was dissolved in acetone (30 mL) and added dropwise to the flask over 30 minutes using a dropping funnel. The reaction mixture was stirred for 2 hours, resulting in a white precipitate. The precipitate was then filtered and washed with excess hot acetonitrile. The filtrate was concentrated, and the solid obtained from the filtrate was precipitated with diethyl ether. The product was air-dried overnight to give a white powder (m = 0.59 g). Yield: 73%. 1H NMR, δ ppm (500 MHz, DMSO-d6): 3.87 (s, NH2); 31 P NMR (202.5 MHz, DMSO-d6), δ (ppm): 19.50 (t, J = 52 Hz, 1P, P-Cl), 12.45 (d, J = 52 Hz, 2P, P-NH2). HRMS, m / z: for [M+H] + Calculated value: 269.94; Measured value: 269.95. IR: P = N(1347, 1216, 1159 cm⁻¹) -1 ), PN (1405, 944 cm -1 ), HNH (1563 cm -1 ), NH (797 cm -1 And P-Cl (608 cm) -1 ).

[0525] Preparation of TCPA / HCCP microcapsules: TCPA (0.55 g) was dissolved in 25 mL of 1 wt% HDK® H30 silica DMSO dispersion. HCCP (1.1 g) and TBA (2 mL) were dissolved in 8 mL of cyclohexane. 4.5 mL of the TCPA / SiO2 / DMSO fraction and 0.5 mL of the HCCP / TBA fraction were placed in a 10 mL vial and stirred with Ultra Turrax for 1 min. The vial was then placed in a water bath and stirred at 80 °C for 8 hours. The mixture was then stirred overnight at room temperature.

[0526] Example 14

[0527] Fabric softener composition

[0528] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the fabric softener composition to add fragrance equivalent to 0.116%.

[0529] Table 12: Fabric Softener Compositions

[0530]

[0531] Example 15

[0532] Powder detergent composition

[0533] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the powder detergent composition to add the equivalent of 0.2% fragrance.

[0534] Table 13: Powder Detergent Compositions

[0535]

[0536] Example 16

[0537] Preparation of spray-dried microcapsules

[0538] Prepare emulsions A through E with the following components.

[0539] Table 14: Composition of emulsions A-E and composition of spray-dried granular powders A-E

[0540]

[0541] 1) Capsul™, Ingredion

[0542] 2) Maltodextrin 10DE source: Roquette

[0543] 3) Maltose, Lehmann & Voss

[0544] 4) Silica, Evonik

[0545] 5) See Table 8

[0546] Table 15: Composition of Flavor B

[0547]

[0548] 1) Firmenich SA, Switzerland

[0549] 2) 3-(4-tert-butylphenyl)-2-methylpropanal, Givaudan SA, Switzerland

[0550] 3) 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethyl ketone, International Flavors & Fragrances, USA

[0551] 4) Firmenich SA, Switzerland

[0552] 5) Methyl dihydrojasmonic acid, Firmenich SA, Switzerland

[0553] 6) Firmenich SA, Switzerland

[0554] The components of the polymer matrix (maltodextrin and capsulant) were added at 45-50°C. TM Add (or capsul™, citric acid, and tripotassium citrate) to water until completely dissolved.

[0555] For emulsion D, add free fragrance B to the aqueous phase.

[0556] The microcapsule slurry was added to the resulting mixture. The resulting mixture was then gently mixed at 25°C (room temperature).

[0557] Granular powders A through E were prepared by spray drying emulsions A through E using a Sodeva spray dryer (source: France), with the inlet air temperature set at 215°C and the flow rate set at 500 mL per hour. The outlet air temperature was 105°C. The emulsions before atomization were at ambient temperature.

[0558] Example 17

[0559] Liquid Fragrance Enhancer Composition

[0560] Weigh out a sufficient amount of the example microcapsules and mix them into the liquid flavor enhancer to add the equivalent of 0.2% fragrance.

[0561] Table 16: Liquid Fragrance Enhancer Compositions

[0562]

[0563] 1) Decanol polyether-8; Trademark and source: KLK Oleo

[0564] 2) Laureth-9; Trademark and source:

[0565] 3) Plantacare 2000UP; Trademark and source: BASF

[0566] Different ringing gel compositions (compositions 1-6) were prepared according to the following schemes.

[0567] In the first step, the aqueous phase (water), solvent (propylene glycol) (if present) and surfactant are mixed together at room temperature by stirring with a magnetic stirrer at 300 rpm for 5 minutes.

[0568] In the second step, the binder is dissolved in the hydrophobic active ingredient (fragrance) at room temperature with a magnetic stirrer at 300 rpm. The resulting mixture is then mixed for 5 minutes.

[0569] Then, the aqueous and oil phases are mixed together at room temperature for 5 minutes to form a transparent or milky-white ringing gel.

[0570] Example 18

[0571] Liquid detergent composition

[0572] Weigh out a sufficient amount of the example microcapsules and mix them into a liquid detergent to add the equivalent of 0.2% fragrance.

[0573] Table 17: Liquid Detergent Compositions

[0574]

[0575] 1) Hostapur SAS 60; Source: Clariant

[0576] 2) Edenor K 12-18; Source: Cognis

[0577] 3) Genapor LA 070; Source: Clariant

[0578] 4) Source: Genencor International

[0579] 5) Aculyn 88; Source: Dow Chemical

[0580] Example 19

[0581] Unit dose preparation

[0582] Weigh out an adequate amount of the exemplary microcapsules and mix them into a unit dose formulation to add the equivalent of 0.2% flavoring.

[0583] The unit dose can be contained in a PVOH (polyvinyl alcohol) film.

[0584] Table 18: Composition of Unit Dosage

[0585]

[0586] Example 20

[0587] Concentrated general-purpose cleaning agent composition

[0588] Weigh out an adequate amount of the exemplary microcapsules and mix them into a concentrated general-purpose cleaning composition to add the equivalent of 0.2% fragrance.

[0589] Table 19: Concentrated General Purpose Cleaning Compositions

[0590]

[0591] 1) Neodol 91-8®; Trademark and source: Shell Chemical

[0592] 2) Biosoft D-40®; Trademark and source: Stepan Company

[0593] 3) Stepanate SCS®; Trademark and source: Stepan Company

[0594] 4) Kathon CG®; Trademark and source: Dow Chemical Company

[0595] Mix all ingredients together, then dilute the mixture to 100% with water.

[0596] Example 21

[0597] Solid aroma enhancer composition

[0598] Prepare the following composition.

[0599] Table 20: Compositions of Basic Solid Flavor Enhancers

[0600]

[0601] Table 21: Urea-based solid flavor enhancer compositions

[0602]

[0603] Example 22

[0604] Shampoo composition

[0605] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the shampoo composition to add the equivalent of 0.2% fragrance.

[0606] Table 22: Shampoo Compositions

[0607]

[0608] 1)Ucare Polymer JR-400, Noveon

[0609] 2) Schweizerhall

[0610] 3) Glydant, Lonza

[0611] 4) Texapon NSO IS, Cognis

[0612] 5) Tego Betain F 50, Evonik

[0613] 6)Amphotensid GB 2009, Zschimmer & Schwarz

[0614] 7) Monomuls 90 L-12, Gruenau

[0615] 8) Sodium Niparaben, NIPA

[0616] Polyquaternium-10 was dispersed in water. The remaining components of phase A were added individually and mixed thoroughly after each addition. This premix was added to the polyquaternium-10 dispersion and mixed for another 5 minutes. Then, while stirring, premixed phases B and C (Monomuls 90L-12 was heated to melt in Texapon NSO IS) were added. Phases D and E were added while stirring. The pH was adjusted to 5.5–6.0 with citric acid solution.

[0617] Example 23

[0618] Shampoo composition

[0619] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the shampoo composition to add fragrance equivalent to 0.2%.

[0620] Table 23: Shampoo Compositions

[0621]

[0622] 1) EDETA B powder, BASF

[0623] 2) Jaguar C14 S, Rhodia

[0624] 3) Ucare Polymer JR-400, Noveon

[0625] 4) Sulfetal LA BE, Zschimmer & Schwarz

[0626] 5) Zetesol LA, Zschimmer & Schwarz

[0627] 6) Tego Betain F 50, Evonik

[0628] 7) Xiameter MEM-1691, Dow Corning

[0629] 8) Lanette 16, BASF

[0630] 9) Comperlan 100, Cognis

[0631] 10) Cutina AGS, Cognis

[0632] 11) Kathon CG, Rohm & Haas

[0633] 12) D-Panthenol, Roche

[0634] A premixture containing guar hydroxypropyltrimethylammonium chloride and polyquaternium-10 was added to water and tetrasodium EDTA and mixed simultaneously. When the mixture was homogeneous, NaOH was added. Then, phase C was added. The mixture was heated to 75°C. Phase D was added and mixed until homogeneous. Heating was stopped, and the mixture was allowed to cool to room temperature. At 45°C, phase E was added and mixed simultaneously. The final viscosity was adjusted with a 25% NaCl solution, and the pH was adjusted to 5.5–6 with a 10% NaOH solution.

[0635] Example 24

[0636] Hair rinse composition

[0637] Weigh a sufficient amount of the exemplary microcapsules and mix them into the rinsing composition to add the equivalent of 0.2% fragrance.

[0638] Table 24: Eluting Compositions

[0639]

[0640] 1) Genamin KDMP, Clariant

[0641] 2) Tylose H10 Y G4, Shin Etsu

[0642] 3) Lanette O, BASF

[0643] 4) Arlacel 165, Croda

[0644] 5)Incroquat Behenyl TMS-50-PA- (MH), Croda

[0645] 6) Brij S20, Croda

[0646] 7)Xiameter MEM-949, Dow Corning

[0647] 8) Alfa Aesar

[0648] Mix the components of phase A until a homogeneous mixture is obtained. Allow the tylose to dissolve completely. Then heat the mixture to 70–75°C. Combine the components of phase B and melt them at 70–75°C. Then add the components of phase B to phase A with good stirring and continue mixing until the temperature of the mixture reaches 60°C. Then, add the components of phase C while stirring and keep mixing until the mixture cools to 40°C. Adjust the pH to 3.5–4.0 with citric acid solution.

[0649] Example 25

[0650] Anhydrous composition of antiperspirant spray

[0651] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the anhydrous composition of the antiperspirant spray to add fragrance equivalent to 0.2%.

[0652] Table 25: Anhydrous Compositions for Antiperspirant Sprays

[0653]

[0654] 1) Dow Corning ® 345 Fluid; Trademark and source: Dow Corning

[0655] 2) Aerosil ® 200; Trademark and source: Evonik

[0656] 3) Bentone ® 38; Trademark and source: Elementis Specialities

[0657] 4) Micro Dry Ultrafine; Source: Reheis

[0658] Using a high-speed stirrer, add silica and quaternary ammonium salt-18-hydropyrite to the mixture of isopropyl myristate and cyclodimethylsiloxane. Once fully swollen, add aluminum hydroxyl chloride in batches with stirring until the mixture is homogeneous and free of lumps. Fill the aerosol can with 25% suspension and 75% propane / butane (2.5 bar).

[0659] Example 26

[0660] Antiperspirant spray emulsion composition

[0661] Weigh out an adequate amount of the exemplary microcapsules and mix them into the antiperspirant spray emulsion composition to add the equivalent of 0.2% fragrance.

[0662] Table 26: Antiperspirant Spray Emulsion Compositions

[0663]

[0664] 1) Tween 65; Trademark and source: CRODA

[0665] 2) Dehymuls PGPH; Trademark and source: BASF

[0666] 3) Abil EM-90; Trademark and source: BASF

[0667] 4) Dow Corning 345 fluid; Trademark and source: Dow Corning

[0668] 5) Crodamol ipis; Trademark and source: CRODA

[0669] 6) Phenoxyethanol; Trademark and source: LANXESS

[0670] 7) Sensiva SC 50; Trademark and source: KRAFT

[0671] 8) Tegosoft TN; Trademark and source: Evonik

[0672] 9) Aerosil R 812; Trademark and source: Evonik

[0673] 10) Nipagin mna; Trademark and source: CLARIANT

[0674] 11) Locron L; Trademark and source: CLARIANT

[0675] Weigh the components of Part A and Part B separately. Heat the component of Part A to 60°C and the component of Part B to 55°C. Pour a small portion of the component of Part B into Part A while continuously stirring. Stir the mixture thoroughly until it reaches room temperature. Then, add the component of Part C. Mix the emulsion and introduce it into an aerosol can. Compact the propellant and add it.

[0676] Aerosol filling: 30% emulsion: 70% propane / butane 2.5 bar.

[0677] Example 27

[0678] Deodorant spray composition

[0679] Weigh out an adequate amount of the exemplary microcapsules and mix them into the antiperspirant deodorant spray composition to add the equivalent of 0.2% fragrance.

[0680] Table 27: Deodorant Spray Compositions

[0681]

[0682] 1) Irgasan ® DP 300; Trademark and source: BASF

[0683] Mix and dissolve all ingredients in the order listed in Table 24. Then fill and compact the aerosol can and add propellant (aerosol filling: 40% active solution, 60% propane / butane 2.5 bar).

[0684] Example 28

[0685] Antiperspirant roll-on lotion composition

[0686] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the antiperspirant roll-on lotion composition to add the equivalent of 0.2% fragrance.

[0687] Table 28: Antiperspirant Roll-on Lotion Compositions

[0688]

[0689] 1) BRIJ 72; Source: ICI

[0690] 2) BRIJ 721; Source: ICI

[0691] 3) ARLAMOL E; Source: UNIQEMA-CRODA

[0692] 4) LOCRON L; Source: CLARIAN

[0693] Heat parts A and B separately to 75°C; add part A to part B while stirring, and homogenize the mixture for 10 minutes. Then, cool the mixture while stirring. When the mixture reaches 45°C, slowly add part C, and when the mixture reaches 35°C, slowly add part D while stirring. Then cool the mixture to room temperature.

[0694] Example 29

[0695] Antiperspirant roll-on composition

[0696] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the antiperspirant roll-on composition to add the equivalent of 0.2% fragrance.

[0697] Table 29: Antiperspirant Roll-On Compositions

[0698]

[0699] 1) LOCRON L; Source: CLARIANT

[0700] 2) EUMULGIN B-1; Source: BASF

[0701] 3) EUMULGIN B-3; Source: BASF

[0702] Mix the ingredients of part B in a container, then add the ingredients of part A. Then dissolve part C into parts A and B. For the spices, add 1 part Cremophor RH40 to 1 part spice and mix well.

[0703] Example 30

[0704] Antiperspirant roll-on composition

[0705] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the antiperspirant lotion composition to add fragrance equivalent to 0.2%.

[0706] Table 30: Antiperspirant Roll-on Lotion Compositions

[0707]

[0708] 1) Natrosol ® 250 H; Trademark and source: Ashland

[0709] 2) Irgasan ® DP 300; Trademark and source: BASF

[0710] 3) Cremophor ® RH 40; Trademark and source: BASF

[0711] Part A was prepared by gradually sprinkling hydroxyethyl cellulose into water while rapidly stirring with a turbine. Stirring continued until the hydroxyethyl cellulose was fully swollen and formed a clear gel. Then, Part B was gradually poured into Part A while continuing to stir until the mixture was homogeneous. Part C was then added.

[0712] Example 31

[0713] Alcohol-free deodorant pump

[0714] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0715] Table 31: Deodorant Compositions

[0716]

[0717] 1) Ceraphyl 41; Trademark and source: ASHLAND

[0718] 2) DOW CORNING 200 FLUID 0.65cs; Trademark and source: DOW CORNING CORPORATION

[0719] 3) Ceraphyl 28; Trademark and source: ASHLAND

[0720] 4) Eutanol G; Trademark and source: BASF

[0721] 5) Irgasan ® DP 300; Trademark and source: BASF

[0722] Mix all ingredients in the order listed in the table, and heat the mixture slightly to dissolve hexadecyl lactate.

[0723] Example 32

[0724] Deodorant pumps containing alcohol

[0725] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0726] Table 32: Deodorant Compositions

[0727]

[0728] 1) Softigen 767; Trademark and source: CRODA

[0729] 2) Cremophor ® RH 40; Trademark and source: BASF

[0730] Mix the ingredients in Part B together. Dissolve the ingredients in Part A in the order shown in the table, and then pour them into Part B.

[0731] Example 32

[0732] Talc formulation

[0733] Weigh out sufficient amounts of particles A to E and mix them into a standard talc matrix: 100% talc, very slight characteristic odor, white powder, source: LUZENAC, to add the equivalent of 0.2% fragrance.

[0734] Example 33

[0735] Shower Gel Reference

[0736] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0737] Table 33: Shower Gel Compositions

[0738] 1)

[0739] 2) ETETA B powder; Trademark and source: BASF

[0740] 3) CARBOPOL AQUA SF-1 polymer; trademark and source: NOVEON

[0741] 4) ZETESOL AO 328 U; Trademark and source: ZSCHIMMER & SCHWARZ

[0742] 5) TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0743] 6) KATHON CG; Trademark and source: ROHM & HASS

[0744] Mix the components and adjust the pH to 6-6.3 (viscosity: 4500cPo + / - 1500cPo (Brookfield RV / Spindle #4 / 20RPM)).

[0745] Example 34

[0746] Shower Gel Composition

[0747] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0748] Table 34: Shower Gel Compositions

[0749]

[0750] 1) ETETA B powder; Trademark and source: BASF

[0751] 2) ZETESOL AO 328 U; Trademark and source: ZSCHIMMER & SCHWARZ

[0752] 3) TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0753] 4) MERQUAT 550; Trademark and source: LUBRIZOL

[0754] Mix the ingredients and adjust the pH to 4.5 (viscosity: 3000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0755] Example 35

[0756] Shower Gel Composition

[0757] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0758] Table 35: Shower Gel Compositions

[0759]

[0760] 1) ETETA B powder; Trademark and source: BASF

[0761] 2) Texapon NSO IS; Trademark and source: COGNIS

[0762] 3) MERQUAT 550; Trademark and source: LUBRIZOL

[0763] 4) DEHYTON AB-30; Trademark and source: COGNIS

[0764] 5) GLUCAMATE LT; Trademark and source: LUBRIZOL

[0765] 6) EUPERLAN PK 3000 AM; Trademark and source: COGNIS

[0766] 7) CREMOPHOR RH 40; Trademark and source: BASF

[0767] Mix the ingredients and adjust the pH to 4.5 (viscosity: 4000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0768] Example 36

[0769] soap bars

[0770] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the soap bar formulation at a concentration of 7.5% w / w.

[0771] Table 36: Composition of Soap Blends

[0772]

[0773] Example 37

[0774] Beauty Day Cream

[0775] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the beauty skin cream (see composition below) at a concentration of 5% w / w.

[0776] Table 37: Composition of Creams

[0777]

[0778] 1) ARLATONE 985

[0779] 2) TEFOSE 2561

[0780] 3) COSBIOL

[0781] 4) GLYDANT PLUS

[0782] Example 38

[0783] Hand dishwashing detergent

[0784] Weigh out a sufficient amount of the exemplary microcapsules and mix them into the following composition to add the equivalent of 0.2% flavoring.

[0785] Table 38: Handwashing Dishwashing Detergent Compositions

[0786]

[0787] 1) Biosoft S-118®; Trademark and source: Stepan Company

[0788] 2) Ninol 40-CO®; Trademark and source: Stepan Company

[0789] 3) Stepanate SXS®; Trademark and source: Stepan Company

[0790] 4) Tergitol 15-S-9®; Trademark and source: Dow Chemical Company

[0791] Mix water with sodium hydroxide and diethanolamide. Add LAS. Neutralize the LAS, then add the remaining ingredients. Check the pH (= 7~8) and adjust as necessary.

[0792] Example 39

[0793] Toothpaste ingredients

[0794] Weigh out a sufficient amount of microcapsule slurry M (prepared according to the scheme disclosed in Example 1, except that it is encapsulated with menthol flavoring agent) and mix it into the following composition to add the equivalent of 0.2% flavoring agent.

[0795] Table 39: Toothpaste Ingredients

[0796]

[0797] 1) Tixosil 73

[0798] 2) Tixosil 43

[0799] Example 40

[0800] Calcium hydrogen phosphate toothpaste formulation

[0801] Weigh out a sufficient amount of microcapsule slurry M (prepared according to the scheme disclosed in Example 1, except that it is encapsulated with menthol flavoring agent) and mix it into the following composition to add 0.2% of the flavoring agent.

[0802] Table 40: Toothpaste Ingredients

[0803]

[0804] 1) Aerosil® 200

[0805] Example 41

[0806] Mouthwash without alcohol ingredients

[0807] Weigh out a sufficient amount of microcapsule slurry M (prepared according to the scheme disclosed in Example 1, except that it is encapsulated with menthol flavoring agent) and mix it into the following composition to add 0.2% of the flavoring agent.

[0808] Table 41: Mouthwash Ingredients

[0809]

[0810] Example 42

[0811] Mouthwash ingredients

[0812] Weigh out a sufficient amount of microcapsule slurry M (prepared according to the scheme disclosed in Example 1, except that it is encapsulated with menthol flavoring agent) and mix it into the following composition to add the equivalent of 0.2% flavoring agent.

[0813] Table 42: Mouthwash Ingredients

[0814] .

Claims

1. A core-shell microcapsule comprising: - The core, which contains hydrophobic materials, and - A shell comprising the reaction product of at least one compound containing an inorganic portion and at least one compound having at least two P-Cl functional groups.

2. The core-shell microcapsule according to claim 1, wherein the shell contains at least 50%, preferably at least 70%, more preferably at least 90%, and even most preferably 100% inorganic components.

3. The core-shell microcapsule according to claim 1 or 2, wherein the compound having at least two P-Cl functional groups is selected from the group consisting of compounds of the formula PXCl3, wherein X is O, S, NH, or NR. 1 , where R 1 The optional hydrocarbon group may contain any heteroatom. Preferably, the compound having at least two P-Cl functional groups may be selected from the group consisting of: phosphorus oxychloride (POCl3), phosphorus trichloride (PSCl3), phosphorus trichloride imide (PNHCl3), N-substituted phosphorus trichloride imide (PNR). 1 Cl3), phosphorus trichloride, phosphorus pentachloride, hexachlorocyclotriphosphazene (HCCP) and its derivatives, R 1 OPXCl2 (where X is O, NH, or NR) 1 Or S), for example, alkyl phosphorus dichloride (R 1 OPOCl2) and / or alkyl dichlorothiophosphate (R 1 OPSCl2) (where R 1 It can be any hydrocarbon moiety having heteroatoms; poly(dichlorophosphazene), 3,9-dichloro-2,4,8,10-tetraoxa-3λ5,9λ5-diphosphaspiro[5.5]undecane 3,9-dioxide, and mixtures thereof.

4. The core-shell microcapsule according to claim 3, wherein the compound having at least two P-Cl functional groups is hexachlorocyclotriphosphazene (HCCP) or a derivative thereof or a polymer thereof.

5. The core-shell microcapsule according to any one of the preceding claims, wherein the compound having the inorganic portion is a silicon-containing monomer, polymer, oligomer or particulate and mixture thereof, preferably selected from the group consisting of amino-functional silanes, sulfur-functional silanes, non-functional silanes and mixtures thereof.

6. The core-shell microcapsule according to claim 5, wherein the amino-functionalized silane is selected from bis[3-(triethoxysilyl)propyl]amine, 3-aminopropyltriethoxysilane, 3-(2-aminoethylamino)propyltriethoxysilane, N-phenylaminomethyltriethoxysilane, 1,1,1-triethoxysilaneamine and its polymers and mixtures thereof; wherein the sulfur-functionalized silane is selected from 3-mercaptopropyltriethoxysilane; wherein the non-functionalized silane is selected from 1,2-bis(triethoxysilyl)ethane, 1-(triethoxysilyl)-2-(diethoxymethylsilyl)ethane and triethoxysilane and mixtures thereof.

7. The core-shell microcapsule according to any one of the preceding claims, wherein the hydrophobic material comprises a fragrance.

8. A method for preparing core-shell microcapsule slurry, comprising the following steps: a) Optionally, at least one compound having at least two P-Cl functional groups is provided; b) Mix at least one hydrophobic material with an optional compound obtained in step a) to form an oil; c) Disperse the oil phase into the continuous phase C1, or disperse the continuous phase C1 into the oil phase to form a two-phase dispersion; d) Optionally, the two-phase dispersion is dispersed into a continuous phase C2, which optionally contains at least one compound having at least two P-Cl functional groups to form a multiple dispersion; e) Solidify the dispersion obtained in step c) or d) to form microcapsules in slurry form. A compound having an inorganic moiety is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

9. The method according to claim 8, wherein a stabilizer is added to the oil phase and / or the continuous phase C1.

10. The method of claim 8, wherein the stabilizer is selected from the group consisting of inorganic particles, surfactants, polymeric emulsifiers such as polysaccharides, proteins, glycoproteins, and mixtures thereof.

11. The method according to any one of claims 8 to 10, wherein a nucleophile selected from the group consisting of nitrogen nucleophiles, sulfur nucleophiles, enol carbon nucleophiles, oxygen nucleophiles, phosphorus nucleophiles, and mixtures thereof is added in step a) and / or step b) and / or step c) and / or step d) and / or step e).

12. The method according to any one of claims 8 to 11, wherein, Based on the total weight of the multidisperse, the compound having at least two P-Cl functional groups is added in an amount of 0.5 to 10% by weight, preferably 1 to 5% by weight.

13. The method according to any one of claims 8 to 12, wherein, Based on the total weight of the multidisperse, the compound having the inorganic portion is added in an amount of 1 to 15% by weight, preferably 1 to 8% by weight.

14. The method according to any one of claims 8 to 13, wherein the multiple dispersion is a two-phase dispersion.

15. A consumer product, preferably in the form of a home care product, personal care product or fabric care product, comprising microcapsules as defined in any one of claims 1 to 7.

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