Coacervate core-shell microcapsules

Abstract

The present invention relates to plant-based coacervate core-shell microcapsules wherein the shell comprises Moringa oleifera extract, as well as to methods and uses thereof.

Description

Technical Field

[0001] The present invention relates to plant-based coacervate core-shell microcapsules, wherein the shell comprises Moringa oleifera extract, and methods and uses thereof. Background Art

[0002] The typical steps of the coacervation process generally involve (a) emulsification of a material, typically hydrophobic, in a solution containing hydrocolloids, (b) coacervation (phase separation), which means the formation of a coacervate phase, (c) wall formation by aggregation of hydrocolloids around droplets of the emulsified hydrophobic material, and (d) hardening of the wall, which is generally achieved by crosslinking the hydrocolloids that form the wall, thereby making the process irreversible and the resulting microcapsules insoluble in water and resistant to mechanical stress, thermal exposure and surfactant-based media.

[0003] The wall formation step is typically driven by the surface tension difference between the coacervate phase, water, and the hydrophobic material. In most coacervation processes, one of the hydrocolloids used in the coacervation process is gelatin due to its various advantages.

[0004] However, the use of gelatin-containing capsules is not possible for food consumers and food products where the use of animal-derived ingredients is not permitted due to regulatory requirements, potential health hazards (mad cow disease or bovine spongiform encephalopathy), cultural or religious restrictions. In addition, the use of plant-based ingredients is often desirable to achieve better sustainability in the final consumer product compared to animal-based ingredients, primarily because the water requirements for producing comparable quantities of protein directly from plants are much more limited than for proteins from animal production.

[0005] Furthermore, consumer demand for environmentally friendly delivery systems is becoming increasingly important and driving the development of new delivery systems.

[0006] Last but not least, there is a growing consumer demand for products containing natural extracts with antimicrobial properties. These natural products not only enhance product quality but also instill consumer confidence as they are found in nature and therefore are not perceived as artificial additives.

[0007] It would therefore be desirable to provide new plant-based coacervate microcapsules. BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 An optical microscope image of microcapsule A according to the present invention is shown.

[0009] Figure 2 An optical microscope image of microcapsule B according to the present invention is shown.

[0010] Figure 3a and 3bAn optical microscope image of microcapsule C according to the present invention is shown.

[0011] Figure 4 Microscope images showing microcapsules according to the present invention.

[0012] Figure 5 Microscope images showing microcapsules according to the present invention.

[0013] Figure 6 Shows a scanning electron micrograph of microcapsule D according to the present invention.

[0014] Figures 7 to 10 Microscope images showing microcapsules according to the present invention. Summary of the Invention

[0015] Unless otherwise indicated, percentages (%) are by weight of the composition.

[0016] A first object of the present invention is a coacervate core-shell microcapsule comprising a hydrophobic material, preferably a flavor (edible flavor) or a perfume (daily chemical flavor), wherein:

[0017] a) the hydrophobic material is encapsulated in the core of a coacervate core-shell microcapsule, and

[0018] b) the shell of the coacervate core-shell microcapsules comprises at least one Moringa extract,

[0019] and wherein the shell is cross-linked.

[0020] Another object of the present invention is a coacervate core-shell microcapsule slurry comprising at least one coacervate core-shell microcapsule comprising a hydrophobic material, preferably a flavor or fragrance, wherein:

[0021] a) the hydrophobic material is encapsulated in the core of a coacervate core-shell microcapsule, and

[0022] b) the shell of the coacervate core-shell microcapsules comprises at least one Moringa extract,

[0023] and wherein the shell is cross-linked. DETAILED DESCRIPTION

[0024] By "coacervate core-shell microcapsule" is meant a microcapsule comprising an oily or solid core material ("hydrophobic material") surrounded by a hydrogel shell (also referred to as a "membrane" or "layer") comprising the coacervate material. The core material may be partially or completely surrounded by the hydrogel shell.

[0025] Preferably, the coacervate core-shell microcapsules of the present invention comprise a core that is completely surrounded by a coacervate shell. According to this embodiment, it is understood that the core is completely encapsulated by the coacervate shell.

[0026] According to one embodiment, the degree of cross-linking of the coacervate core-shell capsules is 10% to 70% according to the method described in Soft Matter, 2011, 7, 3315-3322 (Determination of covalent cross-linker efficacy of gelatin strands using calorimetric analyses of the gel state).

[0027] According to a specific embodiment, the rupture force of the coacervate core-shell microcapsules is 0.01 to 10 N, preferably 0.1 to 2 N. The rupture force can be measured by compressing the capsules between parallel plates in a mechanical testing instrument such as a texture analyzer (Food Technology Corporation, USA), an Instron mechanical testing machine (Instron, USA), or a rheometer device equipped with a normal force transducer (e.g., a DHR-2 rheometer manufactured by TA Instruments, USA or an MCR rheometer manufactured by Anton Paar GmbH, Germany).

[0028] The median capsule size of the coacervate core-shell microcapsules may be 5 to 1000 μm, preferably 5 to 500 μm, more preferably 5 to 400 μm, and even more preferably 5 to 300 μm. The median microcapsule size of the coacervate core-shell microcapsules can be determined by standard laser diffraction particle size analysis or by optical microscopy combined with image analysis. Here, for the present invention, microcapsule size refers to a value based on a number-based size distribution measured by optical microscopy (e.g., using a Nikon TE2000 microscope) and image analysis (performed using Nikon NIS Elements software). Methods for obtaining median and mean size distributions are described in the scientific literature, for example, in RJ Hunter, "Introduction to Modern Colloid Science", Oxford University Press, 1994).

[0029] Coacervate core-shell microcapsules can be prepared by both "simple" coacervation and "complex" coacervation. Simple coacervation is understood as a process where the Moringa extract is phase separated and then used to form the capsule wall. Complex coacervation is understood as a process where a non-protein polymer and the Moringa extract are combined to form the microcapsule shell.

[0030] According to the present invention, the shell of the core-shell microcapsule comprises a Moringa oleifera extract. The shell may comprise a mixture of various plant protein extracts.

[0031] Moringa is a tree in the Moringaceae family, native to the Indian subcontinent. The tree has been cultivated since ancient times for its beneficial food and health properties. In particular, the Moringa tree offers multifunctional benefits. Its leaves are extremely nutritious (iron, calcium, vitamin C, and other micronutrients), its seeds can be pressed to produce cosmetic oils or biofuels, and it contains water-soluble cationic proteins, which have been used for centuries as antimicrobial flocculants for water purification. As a shade-providing, nutrient-rich tree, Moringa is crucial for communities that need greater access to clean water and nutrients.

[0032] The Moringa plant contains a series of coagulation peptides (Moringa coagulation proteins (MOCPs)) that bind to anionic surfaces, rendering certain bacteria and microorganisms unable to survive. Coagulation proteins can be cationic, and due to the way they electrostatically interact with anionic biological surfaces, membranes, and microorganisms, such proteins can have antimicrobial effects. Cationic materials may also promote deposition and interaction with biological surfaces and fibers (such as skin, hair, and natural fabrics, which are generally considered to be negatively charged), and can be used to improve the deposition properties, substantivity, and tenacity of different active substances.

[0033] The Moringa extract may be a Moringa seed extract or a Moringa leaf extract, preferably a Moringa seed extract.

[0034] According to one embodiment, the Moringa seed extract is an extract from Moringa seed flour, preferably de-oiled Moringa seed flour.

[0035] According to one embodiment, the Moringa seed extract includes Moringa protein extract.

[0036] According to the present invention, "plant protein extract" or "plant protein concentrate" is used indifferently. Typically, the protein content in the Moringa extract (preferably Moringa seed extract, or concentrate) is 30% to 90%, preferably 40% to 80%.

[0037] According to one embodiment, the Moringa extract is present in an amount of 0.1% to 30%, preferably 1% to 15%, based on the total weight of the microcapsules.

[0038] According to one embodiment, the shell of the core-shell microcapsules comprises a non-protein polymer or polyelectrolyte in addition to the Moringa extract.

[0039] According to one embodiment, the shell of the core-shell microcapsule further comprises a protein polymer, such as soy protein, pea protein, wheat protein, rice protein, potato protein, quinoa protein, amaranth protein, lentil protein, oat protein, buckwheat protein, chickpea protein, canola protein, lupin seed protein and mixtures thereof, preferably, the protein polymer is canola protein.

[0040] The non-protein polymer can be selected from the group consisting of gum arabic, carboxymethyl cellulose, chitosan, xanthan gum, agar, alginate, pectin, pectate or carrageenan, polyallylamine hydrochloride, polystyrene sulfonate, polyethyleneimine, polylysine, polyvinyl pyrrolidone, polyvinyl alcohol, preferably, wherein the non-protein polymer is gum arabic or pectin, more preferably, the non-protein polymer is gum arabic.

[0041] According to one embodiment, when a non-protein polymer is used, the weight ratio between the Moringa extract and the non-protein polymer is 0.1 to 10, particularly 0.1 to 5, more particularly 0.5 to 5, more particularly 0.5 to 2, more particularly 0.5 to 1.5.

[0042] According to one embodiment, when a protein polymer is used, the weight ratio between the Moringa extract and the protein polymer is from 0.1 to 10, particularly from 0.1 to 5, more particularly from 0.25 to 5, more particularly from 0.5 to 5, more particularly from 0.5 to 2, more particularly from 0.5 to 1.5.

[0043] According to one embodiment, the coacervate shell is free of animal protein.

[0044] According to one embodiment, the coacervate shell is free of gelatin.

[0045] According to the present invention, the coacervate core-shell microcapsules comprise a hydrophobic material.

[0046] According to one embodiment, the hydrophobic material is a hydrophobic active ingredient.

[0047] By "hydrophobic active ingredient" is meant any hydrophobic active ingredient - a single ingredient or a mixture of ingredients - which forms a two-phase dispersion when mixed with water. The hydrophobic active ingredient is preferably liquid at about 20°C.

[0048] By "active ingredient" is meant a single compound or a combination of ingredients.

[0049] By "spice or flavoring oil" is meant a single flavoring or flavoring compound or a mixture of several flavoring or flavoring compounds.

[0050] The hydrophobic material according to the present invention may be an "inert" material, such as a solvent or an active ingredient.

[0051] When the hydrophobic materials are active ingredients, they are preferably selected from the group consisting of flavors, flavor ingredients, fragrances, fragrance ingredients, nutraceuticals, cosmetics, pest control agents, biocide active ingredients, and mixtures thereof.

[0052] According to a particular embodiment, the hydrophobic material comprises a mixture of a fragrance and another ingredient selected from the group consisting of a nutraceutical, a cosmetic, a pest control agent, and a biocide active ingredient.

[0053] According to one embodiment, the hydrophobic material comprises a phase change material (PCM).

[0054] According to a specific embodiment, the hydrophobic material comprises a mixture of a biocide active ingredient and another ingredient selected from the group consisting of a fragrance, a nutraceutical, a cosmetic, a pest control agent.

[0055] According to a specific embodiment, the hydrophobic material comprises a mixture of a pest control agent and another ingredient selected from the group consisting of a fragrance, a nutraceutical, a cosmetic, a biocide active ingredient.

[0056] According to one particular embodiment, the hydrophobic material comprises a fragrance.

[0057] According to a particular embodiment, the hydrophobic material consists of a fragrance.

[0058] According to a particular embodiment, the hydrophobic material consists of a biocide active ingredient.

[0059] According to a particular embodiment, the hydrophobic material consists of a pest control agent.

[0060] By "fragrance" (or also referred to as "fragrance oil") it is meant here an ingredient or composition that is liquid at about 20°C. According to any of the above embodiments, the fragrance oil may be a single fragrance ingredient or a mixture of ingredients in the form of a fragrance composition. As a "fragrance ingredient" it is meant here a compound whose primary purpose is to impart or modify an odor. In other words, to be considered a fragrance ingredient such an ingredient must be recognized by a person skilled in the art as being capable of imparting or modifying the odor of a composition in at least an active or pleasant manner, rather than merely having an odor. For the purposes of the present invention, fragrance oils also include combinations of fragrance ingredients with substances that together improve, enhance or modify the delivery of the fragrance ingredient, such as fragrance precursors, emulsions or dispersions, as well as combinations that impart other benefits in addition to changing or imparting odor, such as long-lastingness, burst, malodor counteracting, antimicrobial effects, microbial stability, pest control.

[0061] The character and type of the perfuming ingredients present in the oil phase do not guarantee to be described in more detail here, and it is all that cannot be exhaustive in any case, and the technical staff can select them based on its general knowledge and according to expected use or application and required organoleptic effect. Generally speaking, these perfuming ingredients belong to different chemical classes, as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfur-containing heterocyclic compounds and essential oils, and the perfuming auxiliary component can be natural origin or synthetic origin. In any case, many in these auxiliary components are listed in references such as the work Perfume and Flavor Chemicals of S.Arctander, 1969, Montclair, New Jersey, USA or its updated version or other works of similar nature, and in the patent documentation enriched in the spices field.

[0062] In particular, one may cite the perfuming ingredients commonly used in perfume formulations, for example:

[0063] -Aldehyde aroma components: decanal, dodecanal, 2-methylundecanal, 10-undecanal, octanal, nonanal and / or nonenal;

[0064] - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0 2,7 ]Undec-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiinane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene;

[0065] - Balsamic ingredients: coumarin, ethyl vanillin and / or vanillin;

[0066] - Citrus aroma ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthenadiene;

[0067] - Floral fragrance ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone (β-violet ketone), methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Ketone, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butene-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butene-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-butene-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-one, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, 2,5-dimethyl-2-indanmethanol, 2, 6,6-Trimethyl-3-cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-ylpropanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, tricyclodecenyl acetate, geraniol, p-menthen-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 homocis-dihydrojasmonate, 3-methyl-5-phenylbenzene 1-Hydroxy-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, (S)-2-(1,1-dimethylpropoxy)propyl propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decene-5-lactone, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or a mixture of methylionone isomers;

[0068] - Fruity aroma ingredients: γ-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanoic acid ethyl ester, hexyl acetate, 2-methylbutyric acid ethyl ester, γ-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate;

[0069] - Green fragrance ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;

[0070] Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 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 propionate, 3-methyl-5- Cyclopentadecen-1-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, oxacyclohexadecane-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate;

[0071] - Wood fragrance ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ] Undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate;

[0072] - Other ingredients (e.g., ambery, powdery, spicy, or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, and / or 3-(3-isopropyl-1-phenyl)butanal.

[0073] It will also be understood that the ingredients may also be compounds known to release various types of perfuming compounds in a controlled manner, also known as pro-fragrances or pro-fragrances. Non-limiting examples of suitable pro-fragrances may include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxy(phenyl)acetate, 3,7-dimethylocta-2,6-diene-1-oxo(phenyl)acetate. 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-phenylethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenylethoxyprop-1-en-2-yl)benzene, 2-(1-phenylethoxyprop-1-en-2-yl)naphthalene, (2-phenylethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)benzene benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde, or a mixture thereof.

[0074] The perfuming ingredients can be dissolved in solvents currently used in the perfume industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, (rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, e.g. 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 these percentages being by weight relative to the total weight of the fragrance. Most preferably, the fragrance is substantially free of solvent.

[0075] Preferred perfuming ingredients are those with high steric hindrance (bulky materials), in particular ingredients from one of the following groups:

[0076] - Group 1: perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted by at least one linear or branched C1-C4 alkyl or alkenyl substituent;

[0077] - Group 2: perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted by at least one linear or branched C4-C8 alkyl or alkenyl substituent;

[0078] - Group 3: perfuming ingredients comprising a benzene ring, or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted by at least one linear or branched C5-C8 alkyl or alkenyl substituent, or substituted by at least one phenyl substituent and optionally substituted by one or more linear or branched C1-C3 alkyl or alkenyl substituents;

[0079] - Group 4: perfuming ingredients comprising at least two fused or linked C5 and / or C6 rings;

[0080] - Group 5: Perfuming ingredients containing a camphor-like ring structure;

[0081] - Group 6: Contains at least one C7-C 20 Ring-structured flavoring ingredients;

[0082] - Group 7: perfuming ingredients having a logP value higher than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent;

[0083] Examples of components from each of these groups include:

[0084] - Group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (source: Firmenich SA, Geneva, Switzerland), isocitral, 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 oxide, (S)-1,8-menthadien-7-ol (source: Firmenich SA, Geneva, Switzerland) SA, Geneva, Switzerland), l-p-menthen-4-ol, (1RS,3RS,4SR)-3-p-menthyl acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-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), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde;

[0085] - 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-heptylcyclopentanone, 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);

[0086] - Group 3: damascenone, 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, damascenone, a mixture of 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (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 propionate (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, terpene isobutyrate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate (Source: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-menthene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate (Source: Firmenich SA, Geneva, Switzerland), p-tert-butylcyclohexanone, menthyl mercaptan, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, 2-methoxy-4-methylphenyl ethyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate;

[0087] - Group 4: Methyl cedryl ketone (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)-tricyclo[5.2.1.0 2,6] mixture of dec-4-en-8-yl esters, vetyverol, vetyverone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone (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 and Fragrances, USA) and Fragrances, 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-ene-9-spiro-2'-oxirane (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), (dodecahydro-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;

[0088] - Group 5: Camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, pinene, camphene, 8-methoxycedane, (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane (source: Firmenich SA, Geneva, Switzerland), cedrene, cedrene alcohol, cedrol, 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one and 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one 2,7] a mixture of undec-4-one (source: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (source: Firmenich SA, Geneva, Switzerland);

[0089] - 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), cyclopentadecenolactone (source: Firmenich SA, Geneva, Switzerland), 3-methyl(4 / 5)-cyclopentadecenone (source: Firmenich SA, Geneva, Switzerland), 3-methylcyclopentadecanone (source: Firmenich SA, Geneva, Switzerland), pentadecanolide (source: Firmenich SA, Geneva, Switzerland), cyclopentadecanone (source: Firmenich SA, Geneva, Switzerland), (1-ethoxyethoxy)cyclododecane (source: Firmenich SA, Geneva, Switzerland), 1,4-dioxaheptadecan-5,17-dione, 4,8-cyclododecadien-1-one;

[0090] - Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propyl)phenyl]propanal (source: Givaudan SA, Vergne, Switzerland), 2,2,2-trichloro-1-phenylethyl acetate.

[0091] Preferably, the fragrance comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7 as defined above. More preferably, the fragrance comprises at least 30%, preferably at least 50% of ingredients selected from Groups 3 to 7 as defined above. Most preferably, the fragrance comprises at least 30%, preferably at least 50% of ingredients selected from Group 3, Group 4, Group 6 or Group 7 as defined above.

[0092] According to another preferred embodiment, the fragrance comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP higher than 3, preferably higher than 3.5, even more preferably higher than 3.75.

[0093] According to a specific embodiment, the fragrance used in the present invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols. Advantageously, the fragrance used in the present invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.

[0094] According to one embodiment, the oil phase (or oil-based core) comprises:

[0095] - 25 to 100 wt%, preferably 25 to 98 wt% of a fragrance oil comprising at least 15 wt% of a high impact fragrance raw material having a Log T < -4, and

[0096] - 0 to 75% by weight, preferably 2 to 75% by weight, with a density greater than 1.07 g / cm 3 Density balanced material.

[0097] "High impact fragrance raw materials" are understood to be fragrance raw materials with a 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 common logarithm of the threshold concentration, i.e., Log[threshold] ("LogT").

[0098] "Density balanced material" should be understood as having a density greater than 1.07 g / cm 3 And preferably materials with low odor or no odor.

[0099] The odour threshold concentration of the flavouring compounds is determined by using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact volume of the flavouring oil component injected by the syringe, the exact split ratio and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate is accurately measured and the sample volume is calculated assuming that the duration of a human inhalation lasts 12 seconds. Since the exact concentration at the detector at any point in time is known, the mass per volume inhaled is known and so is the concentration of the flavouring compound. To determine the threshold concentration, a solution is delivered to a sniffing port with a back-calculated concentration. The panellist sniffs the GC effluent and determines the retention time at which the odour is perceived. The average of all panellists determines the odour threshold concentration of the flavouring compound. The determination of odor thresholds is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.

[0100] In WO2018115250, high impact fragrance raw materials with Log T < -4 and with a density greater than 1.07 g / cm 3 The density of the density balance material properties, the contents of which are incorporated by reference.

[0101] According to one embodiment, the high impact fragrance raw materials with Log T<-4 are selected from the group consisting of: (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1-phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1-phenyl acetate, pyrazole butyl ether, 3-propylphenol, 1-(3-methyl-1-benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1-(3,3 / 5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, -1-one, a mixture comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one, (+-)-1-(5-ethyl-5-methyl-1-cyclohexen-1-yl)-4-penten-1-one, (1'S,3'R)-1-methyl-2-[(1',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl}methanol , (+-)-3-mercaptohexyl acetate, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, H-methyl-2h-1,5-benzodioxepin-3(4H)-one, (2E,6Z)-2,6-nonadien-1-ol, (4Z)-4-dodecenal, (+-)-4-hydroxy-2,5-dimethyl-3(2H)-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 comprising (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylidene-2-phenyl-2H-pyran, a mixture comprising 4-methylidene-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-pentenenitrile, 1-(spiro[4.5]dec-6 / 7-en-7-yl)-4-penten-1-one, 2-methoxynaphthalene, (-)-(3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 5-nonalactone, (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 7-isopropyl-2H,4H-1,5-benzodioxepin-3-one, coumarin, 4-methylphenyl isobutyrate, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, β,2,2,3-tetramethyl-δ-formylidene-3-one -cyclopentene-1-butanol, δ-damascenone ((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 glycidate, γ-octalactone, 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, lauroyl lactone, dimethyl tricyclo[7.1.1.0. 2,7] Undec-2-en-4-one (tricyclone), (+)-(3R,5Z)-3-cyclopentadecen-1-one, undecyl lactone, (1R,4R)-8-mercapto-3-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-undecatriene, 10-undecenal, (9E)-9-undecene Aldehyde, (9Z)-9-undecenal, (Z)-4-decenal, (+-)-ethyl 2-methylpentanoate, 1,2-diallyldisulfane, 2-tridecenenitrile, 3-tridecenenitrile, (+-)-2-ethyl-4,4-dimethyl-1,3-oxathiinane, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1-one, 3-(4-tert-butylphenyl)propanal, allyl (cyclohexyloxy)acetate, methyl naphthyl ketone, (+-)-(4E)-3-methyl-4-cyclopentadecen-1-one ketone, (+-)-5E3-methyl-5-cyclopentadecen-1-one, cyclopropyl methyl 3-hexenoate, (4E)-4-methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1-(5-propyl-1,3-benzodioxol-2-yl)ethanone, 4-methyl-2-pentylpyridine, (+-)-(E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (3aRS,5aSR,9aSR,9bRS)-3a,6, 6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, (2S,5R)-5-methyl-2-(2-propyl)cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran-2-one, (+-)-3-(3-isopropyl-1-phenyl)butanal, 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, indole, 7-propyl-2H,4H-1,5-benzodioxepin-3-one, ethyl maltol (ethyl praline), (4-methylphenoxy)acetaldehyde, tricyclo[5.2.1.0.(2,6)]decane-2-carboxylic acid ethyl ester, (+)-(1'S,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol, (4E)-3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 8-isopropyl-6-methyl-bicyclo[2.2.2] oct-5-ene-2-carbaldehyde, methylnonyl acetaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropionate, (E)-4-decenal, (+-)-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, (1R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene, (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane, (-)-(3R)-3,7-dimethyl-1 ,6-octadien-3-ol, (E)-3-phenyl-2-propenenitrile, 4-methoxybenzyl acetate, (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (2 / 3-methylbutoxy) allyl 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.

[0102] According to one embodiment, the fragrance raw material with Log T < -4 is selected from the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.

[0103] According to one embodiment, the fragrance raw material 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 an amount of 20 to 70 wt % based on the total weight of the fragrance raw materials with Log T < -4.

[0104] According to one embodiment, the fragrance raw materials with Log T <-4 comprise 20 to 70 wt. % of aldehydes, ketones and mixtures thereof, based on the total weight of the fragrance raw materials with Log T <-4.

[0105] Therefore, the remaining fragrance raw materials contained in the oil-based core may have a Log T > -4.

[0106] According to one embodiment, the fragrance raw materials with Log T>-4 are selected from the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6 / 8-sec-butylquinoline, (+-)-3-(1,3-benzodioxol-5-yl)-2-methylpropanal, tricyclodecenyl propionate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, methyl 2-((1RS,2RS)-3-oxo-2-pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 1,3,3-trimethyl-2-oxadiazol-1-ol, Cyclo[2.2.2]octane, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, dodecanal, 1-oxa-12-cyclohexadecene-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 heptanoate, 2-(2-methyl-2-n-propyl)cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl butyrate, geranyl acetate, neryl acetate, (+-)-1-phenylethyl acetate Ester, 1,1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutanoate, (2Z)-ethyl 3-hydroxy-2-butenoate, 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 propionate, 3,5,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde, 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, undecanal, decanal, 2-phenylethyl acetate, (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1] heptane-2-ol), (+-)-3,7-dimethyl-3-octanol, 1-methyl-4-(2-propylidene)cyclohexene, (+)-(R)-4-(2-methoxyprop-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.

[0107] According to one embodiment, the fragrance formulation comprises:

[0108] - 0 to 60% by weight of a hydrophobic solvent (based on the total weight of the fragrance formulation),

[0109] - 40 to 100 wt. % of a fragrance oil (based on the total weight of the fragrance formulation), wherein the fragrance oil has at least two, preferably all, of the following properties:

[0110] o at least 35%, preferably 40%, preferably at least 50%, more preferably at least 60% of the perfuming ingredients have a log P greater than 3, preferably greater than 3.5,

[0111] o at least 20%, preferably 25%, preferably at least 30%, more preferably at least 40% of bulky materials of Groups 1 to 6, preferably Groups 3 to 6, as defined above, and

[0112] o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of the high impact fragrance material as defined above having a Log T < -4,

[0113] - Optionally, additional hydrophobic active ingredients.

[0114] According to a particular embodiment, the fragrance comprises from 0 to 60% by weight of a hydrophobic solvent.

[0115] According to a particular embodiment, the hydrophobic solvent is a density balancing material, preferably selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate and mixtures thereof.

[0116] In a particular embodiment, the hydrophobic solvent has a Hansen Solubility Parameter that is compatible with the entrapped fragrance oil.

[0117] The term "Hansen solubility parameter" is understood to refer to the solubility parameter method proposed by Charles Hansen for predicting the solubility of polymers and is based on the fact that the total vaporization energy of a liquid consists of several individual 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 combined. The "weighted Hansen solubility parameter" is calculated as (δD 2 +δP 2 +δH 2 ) 0.5 , where δD is the Hansen dispersion value (hereinafter also referred to as atomic dispersion force), δP is the Hansen polarizability value (hereinafter also referred to as dipole moment), and δH is the Hansen hydrogen bond ("h-bond") value (hereinafter also referred to as hydrogen bond). For a more detailed explanation of this parameter and this value, please refer to Charles Hansen's "The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient", Danish Technical Press (Copenhagen, 1967).

[0118] The Euclidean difference of the solubility parameters of the fragrance and the solvent was 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 are the Hansen dispersion value, Hansen polarizability value and Hansen hydrogen bond value of the solvent respectively; and δD fragrance , δ fragrance and δH fragrance They are the Hansen dispersion value, Hansen polarizability value and Hansen hydrogen bond value of the fragrance respectively.

[0119] In a particular embodiment, the fragrance oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from the first group consisting of: atomic dispersion force (δD) of 12 to 20, dipole moment (δP) of 1 to 8, and hydrogen bonding (δH) of 2.5 to 11.

[0120] In a particular embodiment, the fragrance oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from the second group consisting of: atomic dispersion forces (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and hydrogen bonds (δH) of 2.5 to 11, preferably 4 to 11.

[0121] In a particular embodiment, at least 90% of the fragrance oils, preferably at least 95% of the fragrance oils, and most preferably at least 98% of the fragrance oils have at least two Hansen solubility parameters selected from the first group consisting of: atomic dispersion forces (δD) of 12 to 20, dipole moments (δP) of 1 to 8, and hydrogen bonding (δH) of 2.5 to 11.

[0122] In a particular embodiment, the fragrance oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from the second group consisting of: atomic dispersion forces (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and hydrogen bonds (δH) of 2.5 to 11, preferably 4 to 11.

[0123] According to one embodiment, the perfuming formulation comprises a fragrance modulator (which may be used together with the hydrophobic solvent when present, or as a substitute for the hydrophobic solvent when not present).

[0124] Preferably, a fragrance modulator is defined as a fragrance material having:

[0125] i. Vapor pressure less than 0.0008 Torr at 22°C;

[0126] ii. clogP of 3.5 or more, preferably 4.0 or more, more preferably 4.5;

[0127] iii. at least two Hansen solubility parameters selected from the first group consisting of: atomic dispersion forces of 12 to 20, dipole moments of 1 to 7, and hydrogen bonding of 2.5 to 11,

[0128] iv. at least two Hansen solubility parameters selected from the second group consisting of: atomic dispersion forces of 14 to 20, dipole moments of 1 to 8, hydrogen bonds 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.

[0129] Preferably, as examples, the following ingredients can be listed as regulators, but the list is not limited to the following substances: alcohol C12, oxahedral, 3-[(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4-cyclopentadecen-1-one, cyclopentadecanone, (8Z)-oxahedral, 2-[5-(tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, lilyral, 1,5,8-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene, (+-)-4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexa Hydrocyclopenta[g]isochromene, (+)-(1S,2S,3S,5R)-2,6,6-trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one, oxahedralidone, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, (+)-(4 R,4aS,6R)-4,4a-dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone, amylcinnamaldehyde, hexylcinnamaldehyde, hexyl salicylate, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,6-heptadien-3-one, (9Z)-9-cycloheptadecene-1-one.

[0130] According to a particular embodiment, the hydrophobic material does not contain any active ingredient (e.g. fragrance). According to this particular embodiment, it comprises, preferably consists of, a hydrophobic solvent, preferably selected from isopropyl myristate, triglycerides (e.g. MCT oil, vegetable oil), D-limonene, silicone oil, mineral oil and mixtures thereof, and optionally a hydrophilic solvent preferably selected from the group consisting of 1,4-butylene glycol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1,2-propylene glycol), 1,3-propylene glycol, dipropylene glycol, glycerol, glycol ethers and mixtures thereof.

[0131] The term "biocide" refers to a chemical substance that kills living organisms (e.g., microorganisms) or reduces or prevents their growth and / or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and industry to prevent scaling of, for example, water, agricultural products (including seeds), and oil pipelines. Biocides can be pesticides, including fungicides, herbicides, insecticides, algaecides, molluscicides, acaricides, and rodenticides; and / or antimicrobials, such as bactericides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, and / or antiparasitics.

[0132] As used herein, "pest control agent" refers to a substance used to repel or attract pests to reduce, inhibit or promote their growth, development or activity. Pests are any organisms, whether animals, plants or fungi, that are invasive or troublesome to plants or animals, including insects, especially arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.

[0133] By "flavor oil" is meant a flavoring ingredient, or a mixture of flavoring ingredients, solvents, or adjuvants currently used to prepare flavoring formulations, i.e., a specific mixture of ingredients intended to be added to an edible composition or chewable product to impart, improve, or modify its sensory properties, particularly its flavor and / or taste. Flavoring ingredients are well known to those skilled in the art, and their properties do not warrant a more detailed description here, which is in no way exhaustive, and a skilled flavorist can select them based on their general knowledge and the intended use or application and the desired sensory effect. Many of these flavoring ingredients are listed in the literature, such as S. Arctander's book Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA, or its latest edition, or other works of similar nature, such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press, or M.B. Jacobs' Synthetic Food Adjuncts, 1947, van Nostrand Co., Inc. The solvents and adjuvants currently used to prepare flavoring formulations are also well known in the art.

[0134] In a specific embodiment, the flavoring agent is a mint flavoring agent. In a more specific embodiment, the mint is selected from the group consisting of peppermint and spearmint.

[0135] In a further embodiment, the flavoring agent is a cooling agent or a mixture thereof.

[0136] In another embodiment, the flavor is a menthol flavor.

[0137] Flavorings derived from or based on fruits in which citric acid is the primary 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 flavorings include juices or liquids extracted from oranges, lemons, grapefruits, limes, citrons, clementines, mandarins, tangerines, and any other citrus fruits or their variants or hybrids. In a specific embodiment, flavorings include liquids extracted or distilled from oranges, lemons, grapefruits, limes, citrons, clementines, tangerines, any other citrus fruits or their variants or hybrids, pomegranates, kiwis, watermelons, apples, bananas, blueberries, melons, ginger, bell peppers, cucumbers, passion fruit, mangoes, pears, tomatoes, and strawberries.

[0138] In a specific embodiment, the flavor comprises a limonene-containing composition. In a specific embodiment, the composition is citrus further comprising limonene.

[0139] In another specific embodiment, the flavor comprises a flavor selected from the group consisting of strawberry, orange, lime, tropical fruit, berry mix, and pineapple.

[0140] The flavoring ingredient may be a flavor modifier. "Taste modifier" is understood to be an active ingredient that acts on the taste receptors of the consumer or provides sensory characteristics associated with mouthfeel (e.g., body, roundness, or mouth-coating) to the consumed product. Non-limiting examples of flavor modifiers include active ingredients that enhance, modify, or impart saltiness, fat, umami, kokumi, heat or cooling, sweetness, sourness, tingling, bitterness, or acidity.

[0141] In further embodiments, suitable sweetening components may be included in the particles described herein. In a specific embodiment, the sweetening component is selected from the group consisting of sugars (such as, but not limited to, sucrose), stevia components (such as, but not limited to, stevioside or rebaudioside A), sodium cyclamate (cyclamate), aspartame, sucralose, saccharin sodium, and acesulfame potassium, or mixtures thereof.

[0142] The flavoring ingredients can be complex flavorants that mimic certain sensory characteristics, such as the sweet and savory notes found in chicken, beef, pork, or shrimp flavors.

[0143] The core material may be in liquid or solid state at a temperature of 20°C to 30°C.

[0144] According to one embodiment, the core material is liquid at a temperature of 20°C to 30°C.

[0145] According to another embodiment, the core material is solid at a temperature of 20°C to 30°C.

[0146] The core material may be hydrophobic, meaning that it is immiscible with water at temperatures between 20°C and 30°C and exists as a separate hydrophobic phase.

[0147] The core may comprise at least 5 wt.%, more preferably at least 10 wt.%, even more preferably at least 20 wt.%, most preferably at least 30 wt.%, e.g. at least 40 wt.% of compounds having a vapour pressure above 0.007 Pa (vapour pressure based on a reference temperature of 25°C).

[0148] Preferably, at least 10 wt.% of the core material has a vapor pressure above 0.1 Pa, more preferably at least 10 wt.% has a vapor pressure >1 Pa at 25°C, most preferably at least 10 wt.% has a vapor pressure >10 Pa at 25°C.

[0149] The given value of 0.007 Pa for vapor pressure at 25° C. is generally considered to be the limit for identifying compounds with volatility. For the purposes of the present invention, vapor pressure is determined by calculation using the method disclosed in the “EPIsuite” software of the U.S. Environmental Protection Agency in 2000.

[0150] Preferably, the core of the coacervate core-shell microcapsule comprises the flavor ingredient. In other words, the flavor ingredient is encapsulated in the core of the coacervate core-shell microcapsule.

[0151] The core of the coacervate core-shell microcapsule may comprise a fat matrix, preferably wherein the fat matrix comprises a food grade oil.

[0152] According to one embodiment, the core comprises fat and / or wax.

[0153] The fat matrix may comprise (i) hydrogenated oil or (ii) hydrogenated fat or (iii) cocoa butter or (iv) a mixture of i-iii.

[0154] Preferably, the hydrogenated oils include hydrogenated palm oil, hydrogenated soybean oil and hydrogenated cottonseed oil.

[0155] Preferably, the hydrogenated fat comprises cocoa fat.

[0156] More preferably, the fat base comprises a mixture of fat and hydrogenated oil.Even more preferably, the fat base comprises a mixture of hydrogenated palm oil and cocoa fat and / or cocoa butter.

[0157] According to a particular embodiment, the shell of the microcapsule further comprises an additional polymeric material, wherein the polymeric material is preferably selected from the group consisting of polyureas, polyurethanes, polyamides, polyesters, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof.

[0158] According to one particular embodiment, the shell of the microcapsules comprises polyurea.

[0159] According to a particular embodiment, the shell of the microcapsules is free of additional polymeric material.

[0160] According to one embodiment, the shell is a composite shell made of coacervate material and polymeric material.

[0161] According to a particular embodiment, the additional polymeric material forms an inner layer.

[0162] According to one embodiment, the shell of the microcapsule comprises an inner layer made of a polymeric material and an outer coacervate comprising the Moringa extract.

[0163] According to the invention, the shell is cross-linked.

[0164] The shell of the microcapsule can be cross-linked using different types of cross-linking agents. Typically, a cross-linking agent can be used to harden the shell of the microcapsule.

[0165] Cross-linking agents may include formaldehyde, genipin, tannins (eg, polyphenols), acetaldehyde, glutaraldehyde, glyoxal, chrome alum, or transglutaminase.

[0166] Typically, the crosslinking agent is used in an amount of 0.001 to 5%, preferably 0.005 to 2%, based on the total weight of the emulsion and / or suspension (slurry).

[0167] According to one embodiment, the cross-linking agent is glutaraldehyde and is typically used in an amount of 0.005 to 5 wt. %, based on the total weight of the emulsion and / or suspension (slurry).

[0168] Glutaraldehyde is well described in the public domain and is commercially available.

[0169] According to another embodiment, the cross-linking agent is an enzyme, typically transglutaminase.

[0170] In some commercial products, the enzyme is dispersed in a carrier. For example, TI (Source: Ajinomoto). In other words, the commercially available product is added in the process so that the content of enzyme active matter is preferably from 0.001% to 5%, preferably from 0.001% to 1%, more preferably from 0.001% to 0.1%, even more preferably from 0.005% to 0.02%, based on the protein content and the total weight of the emulsion and / or suspension (slurry).

[0171] The actions required to induce cross-linking of Moringa extract by a cross-linking agent are well known to those skilled in the art.

[0172] Preferably, crosslinking is performed at a temperature in the range of 5 to 60°C, preferably 15 to 50°C, more preferably 20 to 45°C.

[0173] Preferably, the pH value during the cross-linking process is adjusted to a level that enables effective cross-linking. Preferably, if transglutaminase is used for cross-linking, the pH value can be adjusted to 43 to 8, more preferably 4 to 7.

[0174] Preferably, cross-linking is performed for a period of 1 to 20 hours, preferably 2 to 12 hours, more preferably 7 to 10 hours.

[0175] Alternatively, cross-linking is performed for a period of 1 to 15 hours, preferably 1 to 4 hours.

[0176] When the cross-linking agent is an enzyme, the slurry may be subjected to a heat treatment to inactivate the enzyme. Typically, the heat treatment may be performed at a temperature of 70°C to 90°C.

[0177] Alternatively, the shell may be hardened by other methods other than cross-linking using the aforementioned cross-linking agents. Such methods include (i) hardening the shell by thermal annealing, which is achieved by heating the capsule; preferably, the heating is performed at a temperature close to the protein denaturation temperature, most preferably at or above the protein denaturation temperature; (ii) hardening the shell by changing the pH value (which may be referred to as "pH quenching") to a range where the shell density increases; (iii) hardening the shell by changing the ionic strength to a range where the shell density of the protein increases, which may be achieved by adding a solute, preferably by adding a salt; (iv) hardening the shell by modifying the continuous aqueous phase by adding a water-miscible additive so that the shell density increases, preferably by adding glycerol, propylene glycol, ethanol or isopropanol; (v) hardening the shell by any combination of methods i to iv, performed sequentially or simultaneously, or by combining any combination of methods i to iv sequentially and simultaneously.

[0178] According to a particular embodiment, the shell is crosslinked only by heat treatment.

[0179] When the shell comprises an additional polymeric material, the polymeric material may act as a cross-linking agent.

[0180] In a particular embodiment, the shell material is a biodegradable material.

[0181] In a particular embodiment, the shell has a biodegradability according to OECD 30 IF within 60 days of at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%.

[0182] In a particular embodiment, the core-shell microcapsules have a biodegradability within 60 days according to OECD 30 IF of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%.

[0183] It will thus be appreciated that the core-shell microcapsules including all components, e.g. core, shell and optional coating, may have a biodegradability within 60 days according to OECD 301F of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%.

[0184] In a particular embodiment, the oil core, preferably a fragrance oil, has a biodegradability within 60 days of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% according to OECD 301F.

[0185] OECD301F is the Organization for Economic Co-operation and Development's standard test method for biodegradability.

[0186] A typical method for extracting shells to measure biodegradability is disclosed in Gasparini et al. in Molecules 2020, 25, 718.

[0187] Outer coating layer

[0188] According to a specific embodiment of the present invention, the microcapsules comprise an outer coating layer (coating), wherein the outer coating layer is selected from the group consisting of polysaccharides, cationic polymers, polysuccinimide derivatives (such as those described in WO2021185724), Moringa extracts, and mixtures thereof to form the outer coating layer of the microcapsules.

[0189] Polysaccharide polymers are well known to those skilled in the art. Preferred polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar gum, hydroxypropyl cellulose, hydroxypropyl methylcellulose, pectin and mixtures thereof.

[0190] According to a particular embodiment, the coating layer consists of a cationic coating.

[0191] Cationic polymers are also 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 US Pharmacopoeia in the chemical test for nitrogen determination. Preferred cationic polymers are selected from units containing primary, secondary, tertiary and / or quaternary amine groups, which units may form part of the main polymer chain or may be carried by side substituents directly attached thereto. The weight average molecular weight (Mw) of the cationic polymer is preferably 10,000 to 3.5 M Daltons, more preferably 50,000 to 2 M Daltons.

[0192] According to a particular embodiment, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1-vinyl-1H-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride are 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 hydroxypropyltrimonium chloride, guar gum hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.

[0193] Specific examples of commercially available products include SC60 (cationic copolymer of acrylamidopropyltrimethylammonium chloride and acrylamide, source: BASF) or For example PQ 11N, FC 550 or Style (polyquaternium-11 to 68 or vinylpyrrolidone quaternized copolymers, source: BASF), or (C13S or C17, source: Rhodia).

[0194] According to any of the above embodiments of the present invention, the amount of the above polymer added is about 0% to 5% w / w, or even about 0.1% to 2% w / w, with the percentages being expressed on a w / w basis relative to the total weight of the slurry. It will be understood by those skilled in the art that only a portion of the added polymer will be incorporated into / deposited on the shell of the microcapsules.

[0195] Another object of the present invention is a process for preparing coacervate core-shell microcapsules as defined above, wherein the process comprises the following steps:

[0196] a) preparing a solution by dissolving at least one Moringa extract in an aqueous solution, preferably water;

[0197] b) optionally, preparing a solution by dissolving at least one non-protein polymer and / or at least one protein polymer in an aqueous solution, preferably water;

[0198] c) optionally, mixing the prepared solution comprising at least one plant protein extract and at least one non-protein polymer and / or at least one protein polymer;

[0199] d) preparing an emulsion and / or suspension by emulsifying and / or suspending a hydrophobic material and optionally a multifunctional monomer in a solution;

[0200] e) forming a coacervate shell comprising the Moringa extract and optionally a non-proteinaceous polymer and / or a proteinaceous polymer, surrounding droplets and / or particles of a hydrophobic material present in the emulsion and / or suspension; and

[0201] f) crosslinking the shell.

[0202] According to one embodiment, the aqueous phase also comprises an alcohol, such as glycerol, 1,4-butanediol, ethylene glycol, propylene glycol and mixtures thereof.

[0203] According to one embodiment, the aqueous phase consists of water.

[0204] It can be understood that any one of steps c to e can be performed sequentially or simultaneously.

[0205] In another embodiment, any one or several of the process steps a) to e) described above may additionally comprise a dilution step, wherein additional solvent (preferably water) is added to any solution or mixture thereof.

[0206] In a particular alternative embodiment, process step e) as described above additionally comprises changing the pH of the mixture.

[0207] While the order of the process steps described above is a preferred order, the order of certain steps may be adjusted. In a specific alternative embodiment, step c) may be performed after step d), meaning that the hydrophobic material is first emulsified in the solution prepared in step a), and then the solution prepared in step b) is added only after emulsification.

[0208] In another specific alternative embodiment, step e) is performed before step d), meaning that the coacervate is formed first and then the hydrophobic material and optionally the multifunctional monomer are added.

[0209] According to a particular embodiment, the Moringa seed extract is obtained by extracting Moringa seed powder, the extraction typically being carried out at a pH ranging from 3 to 10, preferably from 4 to 7.

[0210] Typically, the extraction is performed as follows: Moringa seed powder is dispersed in water, the pH is adjusted to a range of 3 to 10, the solution is heated to a temperature of 40 to 70 degrees, the dispersion is centrifuged, and the extract is collected as a protein-rich supernatant. The collected supernatant is then freeze-dried or spray-dried to obtain soluble Moringa protein powder.

[0211] In the method of the present invention, the first solution may comprise dissolving at least one Moringa extract in an aqueous solution, preferably water.

[0212] In the first solution, the Moringa extract protein may be present in the aqueous solution in an amount of 0.5 to 30 wt%, more preferably 1 to 15 wt%, even more preferably 5 to 15 wt%.

[0213] The second solution may comprise at least one non-protein polymer or polyelectrolyte, preferably gum arabic, dissolved in an aqueous solution, preferably water.

[0214] Alternatively, in the second solution, the non-protein polymer or polyelectrolyte may be present in an amount of 0.5 to 20 wt%, more preferably 1 to 15 wt%, even more preferably 5 to 15 wt% in the aqueous solution.

[0215] The first solution is then diluted, preferably to less than 90% of its initial concentration, to form a coacervate. Indeed, it has been found that dilution of the solution can induce the formation of coacervates. Typically, after the dilution step, the concentration of the Moringa extract in the aqueous phase is between 0.5% and 15%, preferably between 1% and 10%.

[0216] Alternatively, the first and second solutions may be mixed with stirring to form a third solution.

[0217] Optionally, the pH of the third aqueous solution may be adjusted to below 4.7, preferably below 4.3, most preferably below 3.5.

[0218] The pH value of the third aqueous solution can be adjusted by adding a food-grade acid solution, preferably by adding an aqueous lactic acid solution.

[0219] The hydrophobic material may be introduced into the first or third solution under shear to form an emulsion or suspension.

[0220] Emulsions or suspensions can be prepared in conventional manner.

[0221] The emulsion or suspension may be prepared by adding the hydrophobic material to the third solution over a period of time of about 3 to 10 minutes, preferably 4 to 6 minutes.

[0222] The emulsion or suspension can be prepared using an impeller stirrer adjusted to a speed of 300 to 400 rpm. The stirrer speed can be adjusted as needed.

[0223] In this step, also known as the "coacervation" step, two separate phases are produced, namely the coacervate phase (polymer-rich) and the coexisting solvent (polymer-poor). The coacervate phase typically consists of the Moringa extract and optionally a non-protein polymer.

[0224] Coagulation can be promoted by changing the pH value.

[0225] The pH is adjusted by adding food grade acid or base solutions, preferably by adding aqueous lactic acid and sodium hydroxide solutions.

[0226] Phase separation can also be induced by various other means, such as by changing the physicochemical environment of the solution, such as salting out or adding a second high molecular weight component to induce phase separation.

[0227] According to a particular embodiment, when the core-shell microcapsules comprise additional polymeric materials, the polyfunctional monomers are added in the oil phase (in addition to the hydrophobic material) and / or in the aqueous phase.

[0228] According to a particular embodiment, the reactants are added during the process, preferably in aqueous phase. Suitable reactants include alcohols, amines, phenols, thiols.

[0229] By "multifunctional monomer" is meant a molecule that, as a unit, chemically reacts or combines to form a polymer or supramolecular polymer. The multifunctional monomer of the present invention has at least two functional groups capable of forming a microcapsule shell.

[0230] The polyfunctional monomer may be selected from the group consisting of at least one polyisocyanate, polymaleic anhydride, polyacyl chloride, polyepoxide, acrylate monomer, polyalkoxysilane, melamine-based resin, and mixtures thereof.

[0231] According to a particular embodiment, the polyfunctional monomer used in the process of the invention is present in an amount ranging from 0.1 to 15%, preferably from 0.5 to 10%, more preferably from 0.8 to 6%, even more preferably from 1 to 3% by weight of the oil phase or the aqueous phase.

[0232] According to one particular embodiment, the monomer added in step a) is at least one polyisocyanate having at least two isocyanate functional groups.

[0233] Suitable polyisocyanates for use according to the present invention include aromatic polyisocyanates, aliphatic polyisocyanates and mixtures thereof. The polyisocyanates contain at least 2, preferably at least 3, but may contain up to 6, or even only 4 isocyanate functional groups. According to a specific embodiment, triisocyanates (3 isocyanate functional groups) are used.

[0234] According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.

[0235] The term "aromatic polyisocyanate" is intended herein to encompass any polyisocyanate containing an aromatic moiety. Preferably, it contains a phenyl, toluoyl, xylyl, naphthyl or diphenyl moiety. More preferably, a toluoyl or xylyl moiety. Preferred aromatic polyisocyanates are biuret, polyisocyanurate and trimethylolpropane adducts of diisocyanates, more preferably containing one of the above-mentioned specific aromatic moieties. More preferably, the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (available from Bayer under the trade name RC), trimethylolpropane adduct of toluene diisocyanate (available from Bayer under the trade name L75), trimethylolpropane adduct of xylylenediisocyanate (available from Mitsui Chemicals under the trade name In a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylenediisocyanate.

[0236] According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain any aromatic moieties. Preferred aliphatic polyisocyanates are trimers of hexamethylene diisocyanate, trimers of isophorone diisocyanate, trimethylolpropane adducts of hexamethylene diisocyanate (available from Mitsui Chemicals) or biuret of hexamethylene diisocyanate (available from Bayer under the trade name N 100 is commercially available), among which the biuret of hexamethylene diisocyanate is more preferred.

[0237] According to another embodiment, the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and at least one aromatic polyisocyanate, both of which contain at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylenediisocyanate, a mixture of a biuret of hexamethylene diisocyanate and a polyisocyanurate of toluene diisocyanate, and a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of toluene diisocyanate. Most preferably, it is a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylenediisocyanate. Preferably, when used as a mixture, the molar ratio between the aliphatic polyisocyanate and the aromatic polyisocyanate is 80:20 to 10:90.

[0238] According to one embodiment, the multifunctional monomer is an acid chloride.

[0239] According to a particular embodiment, the acid chloride conforms to the following formula (I),

[0240]

[0241] wherein n is an integer from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4, and

[0242] Where X is a C2 to C 45 a hydrocarbon group, optionally comprising at least one group selected from (i) to (xi), in particular a group selected from (i) to (vi):

[0243]

[0244] wherein R is a hydrogen atom or an alkyl group, such as a methyl group or an ethyl group, preferably a hydrogen atom.

[0245] It is understood that by "hydrocarbyl..." it is meant that the group is composed of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e. a straight-chain or branched saturated hydrocarbon (e.g. an alkyl), a straight-chain or branched unsaturated hydrocarbon (e.g. an alkenyl or alkynyl), a saturated cyclic hydrocarbon (e.g. a cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. a cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e. an aryl, or can also be in the form of a mixture of the types of groups mentioned, for example, unless specifically limited to only one type mentioned, a particular group may contain straight-chain alkyl, branched alkenyl (e.g. having one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties. Similarly, in all embodiments of the present invention, when a group is mentioned in the form of more than one type of topology (e.g. straight-chain, cyclic or branched) and / or saturation or unsaturation (e.g. alkyl, aromatic or alkenyl), it is also meant that the group may contain moieties having any of the said topologies or saturation or unsaturation as explained above. Similarly, in all embodiments of the present invention, when a group is referred to as being in one form (e.g., alkyl) that is saturated or unsaturated, it is meant that the group can be of any type of topology (e.g., linear, cyclic, or branched) or have several moieties with various topologies.

[0246] It is understood that the term "...hydrocarbyl, optionally containing..." means that the hydrocarbyl group optionally contains heteroatoms to form ether, thioether, amine, nitrile or carboxylic acid groups and derivatives (including, for example, esters, acids, amides). These groups can replace hydrogen atoms of the hydrocarbyl group and thus be pendant to the hydrocarbon, or replace carbon atoms of the hydrocarbyl group (if chemically possible) and thus be inserted into the hydrocarbon chain or ring.

[0247] According to a specific embodiment, the acyl chloride is selected from the group consisting of benzene-1,3,5-triacyl trichloride (trimesoyl chloride), benzene-1,2,4-triacyl trichloride, benzene-1,2,4,5-tetraacyl tetrachloride, cyclohexane-1,3,5-triacyl trichloride, isophthaloyl dichloride, diglycolyl chloride (diglycolyl chloride) dichloride), phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, fumaroyl dichloride, adipoyl chloride, succinyl dichloride, propane-1,2,3-trichloride, cyclohexane-1,2,4,5-tetrachloride, 2,2'-disulfanediyl disuccinyl dichloride, 2-(2-chloro-2-oxoethyl)thiobutanedichloride, (4-chloro-4-oxobutanoyl)-L-glutamyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 4-chloro-4-oxo-butyric acid 2,2-bis[(4-chloro-4-oxo-butyryl)oxymethyl]butyl ester, 4-chloro-4-oxo-butyric acid [2-[2,2-bis[(4 2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] ester, 2-chlorocarbonylbenzoic acid 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl ester, 2-chlorocarbonylbenzoic acid [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] ester, 2,4,5-trichlorocarbonyl-benzoic acid 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl ester, tris(4-chloro-4-oxobutyric acid)propane-1,2,3-triyl ester, di(4-chloro-4-oxobutyric acid)propane-1,2-diyl ester and mixtures thereof.

[0248] Another object of the present invention is the coacervate core-shell microcapsules obtained by the above process.

[0249] Another object of the present invention is a method for preparing a microcapsule powder, which comprises the steps as defined above and an additional step of drying the slurry obtained in step e) or f), for example spray drying, to provide the microcapsules as is, i.e., in powder form. It will be appreciated that any standard method for such drying known to those skilled in the art is also suitable. In particular, the slurry may be spray dried, preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan gum, alginate, carrageenan, or a cellulose derivative, to provide the microcapsules in powder form.

[0250] However, other drying methods may also be cited, such as extrusion, coating, spray granulation, fluidized bed, or even drying at room temperature using materials (carrier, desiccant) that meet specific criteria as disclosed in WO 2017 / 134179.

[0251] According to one particular embodiment, the carrier material contains free fragrance oil, which may be the same as or different from the fragrance from the microcapsule core.

[0252] Optional Ingredients

[0253] When the microcapsules are in the form of a slurry, the microcapsule slurry may contain auxiliary ingredients selected from the group consisting of thickeners / rheology modifiers, antimicrobial agents, opacity enhancers, mica particles, salts, pH stabilizers / buffering components, preferably in an amount of 0 to 15 wt % based on the total weight of the slurry.

[0254] According to another embodiment, the microcapsule slurry of the present invention comprises additional free (ie unencapsulated) fragrance, preferably in an amount of 5 to 50 wt. %, based on the total weight of the slurry.

[0255] Multiple microcapsule systems

[0256] According to one embodiment, the microcapsules of the present invention (microcapsules of the first type) can be used in combination with microcapsules of the second type.

[0257] Another object of the present invention is a microcapsule delivery system comprising:

[0258] - microcapsules of the present invention as first type of microcapsules, and

[0259] - microcapsules of a second type, wherein the microcapsules of the first type differ from the microcapsules of the second type in their hydrophobic material and / or their wall material and / or their coacervate particles and / or their coating material.

[0260] According to a particular embodiment, the microcapsule delivery system is in the form of a slurry.

[0261] consumer goods

[0262] By "consumer product" or "final product" we mean a finished product that is ready for distribution, sale and use by consumers.

[0263] The microcapsules according to the invention can be used for the preparation of perfuming or flavoring compositions, which are likewise an object of the present invention.

[0264] Flavored consumer goods

[0265] The microcapsules of the present invention can be used in a variety of edible end products.

[0266] The final product is more particularly a food product, pet food or feed product. Since the microcapsules of the present invention are plant-based microcapsules, they are particularly suitable for vegetarian meat analogs or meat substitutes, vegetarian burgers, sausages, meat patties, imitation chicken nuggets, etc., meat products (such as processed meat, poultry, beef, pork, ham, fresh sausages or raw meat products, spiced or acid-marinated fresh meat or dry-cured meat products, reformed meat) or extended meat products using combinations of animal and plant proteins in different proportions, usually co-extruded or mixed with textured plant proteins and animal proteins.

[0267] For the purposes of the present invention, meat includes red meat such as beef, pork, mutton, lamb, game and poultry such as chicken, turkey, goose and duck. Preferably, the food of the present invention is meat selected from beef, poultry and pork.

[0268] In one form, the flavored consumable is selected from the group consisting of protein powders, protein drinks, protein bars, meat analogs, seafood analogs, and savory items.

[0269] Meat analogs can include pork analogs, venison analogs, beef analogs, veal analogs, rabbit analogs, sausage analogs, deli meat analogs, ham analogs, salami analogs, pepperoni analogs, chicken analogs, turkey analogs, goose analogs, pheasant analogs, pigeon analogs, whale analogs, lamb analogs, goat analogs, donkey analogs, and squirrel analogs.

[0270] Seafood analogs may include fish analogs, scallop analogs, shrimp analogs, crab analogs, shellfish analogs, clam analogs, squid analogs, conch analogs, and sea pineapple analogs.

[0271] When the flavored consumable product is a granular or powdered food product, dry granules can be easily added thereto by dry mixing. Typical flavored products are selected from the group consisting of instant soups or sauces, breakfast cereals, milk powder, baby food, powdered beverages, powdered chocolate beverages, spreads, powdered cereal beverages, chewing gum, effervescent tablets, cereal bars, and chocolate bars. The powdered food product or beverage may be intended for consumption after reconstitution with water, milk, and / or juice or another aqueous liquid.

[0272] The dry particles provided herein can be suitable for imparting flavor to beverages, fluid dairy products, condiments, baked goods, frostings, bread fillings, candies, chewing gum, and other food products.

[0273] Beverages include, but are not limited to, carbonated soft drinks, including colas, lemon-lime, root beer, hard citrus ("coolers"), fruit-flavored and cream sodas; powdered beverages, and liquid concentrates such as fountain syrups and cordials; hot beverages, including malt beverages, cocoa, coffee and coffee-based beverages, coffee substitutes, and cereal-based beverages; teas, including dry mixes and ready-to-drink teas (herbal and tea-based); fruit and vegetable juices and juice-flavored beverages, as well as juice drinks, nectars, concentrates, punches, and various fruit drinks ("ades"); sweetened and flavored waters, both carbonated and still; sports / energy / health drinks; alcoholic beverages and non-alcoholic and other low-alcohol products, including beer and malt beverages, cider, and wine (still, sparkling, fortified, and wine-based juice drinks). other beverages that are thermally processed (infusion, pasteurization, ultra-high temperature, electric heating or commercial aseptic sterilization) and hot-filled; and cold-filled products made by filtration or other preservation technologies.

[0274] Fluid dairy products include, but are not limited to, non-frozen, partially frozen, and frozen fluid dairy products, such as milk, ice cream, sorbet, and yogurt.

[0275] Condiments include, but are not limited to, ketchup, mayonnaise, salad dressing, Worcestershire sauce, relish, chocolate sauce, tomato sauce, hot sauce, and mustard.

[0276] Baked goods include but are not limited to cakes, cookies, pastries, bread, donuts, etc.

[0277] Bakery fillings include, but are not limited to, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk based (pudding type or mousse type) fillings, hot or cold supplemental fillings, and fat-free to full fat fillings.

[0278] Nevertheless, the microcapsules of the invention may also be of particular interest in the following examples of products:

[0279] baked goods (e.g. bread, dry biscuits, cakes, other baked goods),

[0280] Non-alcoholic beverages (e.g., carbonated soft drinks, bottled water, sports / energy drinks, fruit drinks, vegetable juices, vegetable juice preparations),

[0281] Alcoholic beverages (such as beer and malt drinks, spirituous drinks),

[0282] Instant beverages (e.g. instant vegetable drinks, powdered soft drinks, instant coffee and tea),

[0283] Cereal (wheat) products (e.g. breakfast cereals, pre-cooked rice products, rice flour products, millet and sorghum products, raw or pre-cooked noodles and pasta products),

[0284] milk products (e.g. fresh cheese, soft cheese, hard cheese, milk beverages, whey, butter, partially or fully hydrolysed milk protein-containing products, fermented milk products, condensed milk and the like),

[0285] Dairy products (e.g. fruit or flavoured yoghurt, ice cream, fruit smoothies),

[0286] Confectionery products (such as chewing gum, hard candy, and soft candy),

[0287] Chocolate and compound icings,

[0288] products based on fats and oils or their emulsions (e.g. mayonnaise, spreads, margarine, shortening, remoulade, dressings, spiced preparations),

[0289] Spiced, preserved or processed fish products (e.g. fish intestines, surimi),

[0290] Eggs or egg products (dried eggs, egg whites, egg yolks, custards),

[0291] Desserts (such as gelatin and pudding),

[0292] Products made from soy protein or other parts of soy beans (e.g. soy milk and products made from it, preparations containing soy lecithin, fermented products such as tofu or tempeh or products made from them, soy sauce),

[0293] Vegetable products (e.g. ketchup, sauces, processed and reconstituted vegetables, dried vegetables, deep-frozen vegetables, pre-cooked vegetables, vegetables pickled in vinegar, vegetable concentrates or pastes, cooked vegetables, potato products),

[0294] Vegetarian meat substitutes, vegetarian burgers,

[0295] spices or spice preparations (e.g. mustard preparations, horseradish preparations), spice mixtures, in particular seasonings for use, for example, in the snacks sector,

[0296] Snacks (e.g. baked or fried potato chips or potato dough products, bread dough products, extrudates based on corn, rice or chopped nuts),

[0297] Meat products (e.g. processed meat, poultry, beef, pork, ham, fresh sausage or raw meat products, spiced or acid-cured fresh meat or dry-cured meat products, reconstituted meat),

[0298] Ready-to-eat dishes (e.g., instant noodles, rice, pasta, pizza, tacos, wraps) and soups and broths (e.g., stock, savory cubes, dry soup, instant soup, pre-cooked soup, distilled soup), sauces (instant sauce, dry sauce, prepared sauce, gravy, sweet sauce).

[0299] Preferably, the microcapsules according to the present invention are applied in a product selected from the group consisting of baked goods, instant beverages, cereal products, milk products, dairy products, products based on fats and oils or their emulsions, desserts, vegetable products, vegetarian meat substitutes, spices and seasonings, snacks, meat products, ready meals, broths, stocks and sauces.

[0300] According to a specific embodiment, the flavored product is selected from the group consisting of: meat and / or fish products or analogs, puree bases, soup blocks, powder mixes, beef or pork products, seafood, surimi, instant noodles, rice, broth, sauces, ready meals, frozen or refrigerated pizza, pasta, potato chips or fried potatoes, noodles, potato chips / corn chips, microwave popcorn, nuts, pretzels, rice cakes, rice crackers, fermented dairy analog beverages, acidified dairy analog beverages, non-fermented dairy analog beverages, cheese or cheese analogs, yogurt or yogurt analogs, nutritional supplements, nutritional bars, cereal products, ice cream, dairy-free ice cream, confectionery products, chewing gum, hard candy, and powdered beverages.

[0301] According to one embodiment, the food product, pet food or feed product comprises 0.01 to 10% by weight, preferably 0.1 to 5% by weight, of the microcapsules according to the invention.

[0302] Typically, food products, pet food or feed products also contain proteins, in particular plant proteins or animal proteins, and mixtures thereof.

[0303] Advantageously, the vegetable protein is preferably selected from the group consisting of soy protein, corn, pea, canola, sunflower, sorghum, rice, amaranth, potato, cassava, arrowroot, chickpea, lupin, rapeseed, wheat, oats, rye, barley, and mixtures thereof.

[0304] The microcapsules of the present invention are particularly suitable for extruded and / or baked food, pet food or feed products, more particularly comprising animal and / or plant proteins. Typically, the extruded and / or baked food, pet food or feed product can be selected from meat and / or fish food or analogs and mixtures thereof (in other words, meat food and / or fish food or meat analogs or fish analogs and mixtures thereof); extruded and / or baked meat analogs or extruded and / or baked fish analogs are preferred. Non-limiting examples of extruded and / or baked food, pet food or feed products are snack products or extruded plant proteins, the purpose of which is to give texture to the proteins used in preparing meat analogs (e.g. hamburgers). The powdered composition can be added to non-extruded plant protein isolates / concentrates or to textured plant proteins that can be formed into hamburgers or nuggets (etc.) before or after extrusion.

[0305] Perfuming composition and consumer product

[0306] The microcapsules of the present invention can be used in combination with active ingredients. Therefore, one object of the present invention is a composition comprising:

[0307] (i) microcapsules or microcapsule slurries as defined above;

[0308] (ii) an active ingredient, preferably selected from the group consisting of a cosmetic ingredient, a skin care ingredient, a perfume ingredient, a flavoring ingredient, a malodor counteracting ingredient, a bactericide ingredient, a fungicide ingredient, a pharmaceutical or agrochemical ingredient, a disinfectant ingredient, an insect repellent or attractant, and mixtures thereof.

[0309] The capsules of the present invention show good performance in terms of stability in challenging media.

[0310] Another object of the present invention is a perfuming composition comprising:

[0311] (i) microcapsules or microcapsule slurries as defined above, wherein the oil comprises fragrance;

[0312] (ii) at least one ingredient selected from the group consisting of a fragrance carrier, a fragrance co-ingredient, and mixtures thereof;

[0313] (iii) optionally, at least one flavor adjuvant.

[0314] As liquid fragrance carriers there may be mentioned, as non-limiting examples, emulsifying systems, i.e. solvent and surfactant systems, or solvents commonly used in the perfumery industry. A detailed description of the properties and types of solvents commonly used in the perfumery industry is not exhaustive. However, there may be mentioned, as non-limiting examples, solvents such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used. For compositions comprising both fragrance carriers and fragrance co-ingredients, in addition to those previously specified, other suitable fragrance carriers may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, for example those sold under the trademark Benzol. (Source: Exxon Chemical) Those known as glycol ethers and glycol ether esters, such as those sold under the trademark (Source: Dow Chemical Company) are known to those skilled in the art. By "fragrance co-ingredient" is meant a compound used in a perfuming preparation or composition to impart a hedonic effect and which is not a microcapsule as defined above. In other words, to be considered a perfuming co-ingredient, it must be recognized by those skilled in the art as being capable of imparting or modifying the odor of a composition in an active or pleasant manner, rather than merely possessing an odor.

[0315] The nature and type of the flavoring co-ingredients present in the perfuming compositions do not guarantee a more detailed description here, and they are all impossible to be exhaustive in any case, and the skilled person can select them according to their common sense and according to the intended use or application and the required organoleptic effect. Generally speaking, these flavoring co-ingredients belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds and essential oils, and the flavoring co-ingredients can be of natural or synthetic origin. In any case, many of these co-ingredients are listed in references such as the work Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated version or other works of similar nature, as well as in the patent literature rich in the field of spices. It is also understood that the co-ingredients can also be compounds known to release various types of flavoring compounds in a controlled manner.The auxiliary component 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)octan-4-one, 2-phenylethyl oxy(phenyl)acetate, 3,7-dimethylocta-2,6-diene-1-ol oxy(phenyl)acetate. -yl ester, (Z)-hex-3-en-1-yl oxy(phenyl)acetate, 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-en-1-yl , (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(oct-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenylethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenylethoxyprop-1-en-2-yl)benzene, 2-(1-phenylethoxyprop-1-en-2-yl)naphthalene, (2-phenylethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)benzene benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde, or a mixture thereof.

[0316] By "perfuming adjuvants" it is meant here ingredients capable of imparting additional added benefits such as colour, specific lightfastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming bases is not exhaustive, but it must be mentioned that said ingredients are well known to those skilled in the art.

[0317] Preferably, the perfuming composition according to the invention comprises from 0.01 to 30% by weight of microcapsules as defined above.

[0318] The microcapsules of the present invention can be advantageously used in many fields of application and in consumer products. The microcapsules can be used in liquid form for liquid consumer products or in powder form for powder consumer products.

[0319] According to a particular embodiment, the consumer product as defined above is a liquid and comprises:

[0320] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0321] b) water or a water-miscible hydrophilic organic solvent; and

[0322] c) a microcapsule slurry or microcapsules as defined above,

[0323] d) Optionally, non-encapsulated flavors.

[0324] According to a particular embodiment, the consumer product as defined above is in powder form and comprises:

[0325] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0326] b) Microcapsule powder as defined above.

[0327] c) Optionally, a spice powder, which is different from the microcapsules as defined above.

[0328] In the case where the microcapsules contain a perfume oil-based core, the products of the present invention are particularly useful for perfumed consumer products, such as products belonging to the category of fine fragrances or "functional" fragrances. Functional fragrances include in particular personal care products, including hair care, body cleansing, skin care, hygiene care, and home care products, including clothing care, surface care and air care. Therefore, another object of the present invention is a perfumed consumer product comprising as a perfume ingredient the microcapsules as defined above or the perfume composition as defined above. The perfume ingredient of the consumer product may be a combination of perfume microcapsules as defined above and free or non-encapsulated perfumes, as well as other types of perfume microcapsules than those disclosed herein.

[0329] In particular, the following liquid consumer product is another object of the present invention, comprising:

[0330] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0331] b) water or a water-miscible hydrophilic organic solvent; and

[0332] c) A perfuming composition as defined above.

[0333] Likewise, the following powdered consumer product is also part of the present invention, comprising:

[0334] (a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product; and

[0335] (b) A perfuming composition as defined above.

[0336] Thus, the microcapsules of the invention can be added as such or as part of a perfuming composition of the invention to already perfumed consumer products.

[0337] For the sake of clarity, it must be mentioned that a "perfumed consumer product" is a consumer product intended to deliver, among other benefits, a perfumed effect to the surface to which it is applied (e.g. skin, hair, fabrics, paper or household surfaces) or to the air (air fresheners, deodorants (deodorants), etc.). In other words, a perfumed consumer product according to the present invention is a processed product comprising a functional formulation (also called a "base") and a benefit agent, comprising an effective amount of microcapsules according to the present invention.

[0338] The nature and types of the other ingredients of the perfumed consumer product do not warrant a detailed description here, which is in no way exhaustive; the skilled person will be able to select them based on his general knowledge and the properties and desired effects of the product in question. The extensive literature on such products contains formulations of base materials for consumer products into which the microcapsules according to the invention can be incorporated. These formulations do not warrant a detailed description here, which is in no way exhaustive. A skilled person in the art of formulating such consumer products will be fully capable of selecting suitable components based on his general knowledge and the available literature.

[0339] Non-limiting examples of suitable perfumed consumer products may be perfumes, such as fine perfumes, colognes, aftershaves, body-splashes; fabric care products, such as liquid or solid detergents, tablets and sachets (single or multi-chamber), fabric softeners, dryer sheets, fabric refreshers, ironing water, or bleaching agents; personal care products, such as hair care products (e.g. shampoo, hair conditioner, coloring preparations or hair sprays), cosmetic preparations (e.g. vanishing creams, body lotions, or deodorants or antiperspirants), or skin care products (e.g. soaps, bath or shower mousses, body washes, etc.). wash), bath oil or shower gel, bath salts, or hygiene products); air care products, such as air fresheners or "ready-to-use" powdered air fresheners; or home care products, such as all-purpose cleaners, liquid or powdered or tablet dishwashing products, toilet bowl cleaners or products for cleaning various surfaces, such as sprays and wipes for treating / refreshing textiles or hard surfaces (floors, tiles, stone floors, etc.); hygiene products, such as sanitary napkins, diapers, toilet paper.

[0340] Another object of the present invention is a consumer product comprising:

[0341] - personal care active bases, and

[0342] - microcapsules or microcapsule slurries as defined above or perfuming compositions as defined above,

[0343] Wherein the consumer product is in the form of a personal care composition.

[0344] The personal care active bases into which the microcapsules of the present invention can be incorporated can be found in a large amount of literature related to such products. These formulations do not warrant a detailed description here, which is by no means exhaustive. A person skilled in the art of formulating such consumer products is fully capable of selecting suitable components based on his general knowledge and the available literature.

[0345] The personal care composition is preferably selected from the group consisting of a hair care product (e.g. a shampoo, a hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, a body lotion, or a deodorant or an antiperspirant), or a skin care product (e.g. a soap, a bath or shower mousse, a body wash, a bath oil or shower gel, bath salts or a hygiene product).

[0346] Another object of the present invention is a consumer product comprising:

[0347] - home care or fabric care active bases, and

[0348] - microcapsules or microcapsule slurries as defined above or perfuming compositions as defined above,

[0349] Wherein the consumer product is in the form of a home care or fabric care composition.

[0350] Home care or fabric care bases, into which the microcapsules of the present invention can be incorporated, can be found in the extensive literature relating to such products. These formulations do not warrant a detailed description here, which is by no means exhaustive. A person skilled in the art of formulating such consumer products will be well able to select suitable components based on his general knowledge and the available literature.

[0351] Preferably, the consumer product comprises 0.1 to 15 wt %, more preferably 0.2 to 5 wt % of the microcapsules or microcapsule slurry 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 of each product.

[0352] An object of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising the microcapsules or microcapsule slurry as defined above, wherein the pH of the consumer product is less than 7.

[0353] An object of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising the microcapsules or microcapsule slurry as defined above, wherein the pH of the consumer product is equal to or greater than 7.

[0354] For liquid consumer products referred to hereinafter, "active base" is to be understood as an active base comprising active materials (typically including surfactants) and water.

[0355] For solid consumer products referred to hereinafter, "active base" is to be understood as meaning the active base comprising active materials (typically including surfactants) and adjuvants (e.g. bleaches, buffers; builders; soil removers or soil suspension polymers; granular enzyme particles, corrosion inhibitors, defoamers, suds suppressors; dyes, fillers and mixtures thereof).

[0356] fabric softener

[0357] An object of the present invention is a consumer product in the form of a fabric softener composition comprising:

[0358] - a fabric softener active base; preferably comprising at least one active material selected from the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg ester quaternary ammonium salts (HEQ), TEAQ (triethanolamine quaternary ammonium salts), silicones and mixtures thereof, the active base preferably being used in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0359] - microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0360] -Optionally, free fragrance oil.

[0361] liquid detergent

[0362] An object of the present invention is a consumer product in the form of a liquid detergent composition comprising:

[0363] - a liquid detergent active base; 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 preferably being used in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0364] - microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0365] -Optionally, free fragrance oil.

[0366] Solid detergent

[0367] An object of the present invention is a consumer product in the form of a solid detergent composition comprising:

[0368] a solid detergent active base; preferably comprising at least one active material selected from the group consisting of anionic surfactants such as alkylbenzenesulfonates (ABS), secondary alkylsulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and nonionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), copolymers of ethylene oxide (EO) and propylene oxide (PO), amine oxides, alkyl polyglucosides, alkyl polyglucamides, the active base preferably being used in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0369] - microcapsule powder or microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0370] -Optionally, free fragrance oil.

[0371] Shampoo / shower gel

[0372] An object of the present invention is a consumer product in the form of a shampoo or shower gel composition comprising:

[0373] - a 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 amphoacetate, cocamidopropyl betaine, cocamide MEA, alkyl glucoside and amino acid-based surfactants and mixtures thereof, the active base preferably being used in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0374] - microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0375] -Optionally, free fragrance oil.

[0376] Rinse-off conditioner

[0377] An object of the present invention is a consumer product in the form of a rinse-off conditioner composition comprising:

[0378] - a rinse-off conditioner active base; preferably comprising at least one active material selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behenyltrimonium chloride and mixtures thereof, the active base preferably being used in an amount of 85 to 99.95% by weight based on the total weight of the composition,

[0379] - microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0380] -Optionally, free fragrance oil.

[0381] Solid flavor enhancer

[0382] An object of the present invention is a consumer product in the form of a solid scent booster comprising:

[0383] a solid carrier, 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, mono-, disaccharides and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohols or fatty acids and mixtures thereof,

[0384] - microcapsule slurry or microcapsules as defined above, in powder form, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0385] -Optionally, free fragrance oil.

[0386] Liquid Fragrance Enhancer

[0387] An object of the present invention is a consumer product in the form of a liquid flavor enhancer comprising:

[0388] - aqueous phase,

[0389] - a surfactant system consisting essentially of one or more than one nonionic surfactant, wherein the surfactant system has an average HLB of 10 to 14, preferably selected from the group consisting of ethoxylated aliphatic alcohols, POE / PPG (polyoxyethylene and polyoxypropylene) ethers, mono- and polyglycerol esters, sucrose ester compounds, polyoxyethylene hydroxy esters, alkyl polyglucosides, amine oxides and combinations thereof;

[0390] - a linker 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

[0391] - Microcapsule slurry or microcapsules as defined above, in the form of a slurry, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0392] -Optionally, free fragrance oil.

[0393] hair dye

[0394] An object of the present invention is a consumer product in the form of an oxidative hair dyeing composition comprising:

[0395] - an oxidizing phase comprising an oxidizing agent and a basic phase comprising an alkaline agent, a dye precursor and a coupling compound; wherein the dye precursor and the coupling compound form an oxidative hair dye in the presence of the oxidizing agent, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0396] - microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition,

[0397] -Optionally, free fragrance oil.

[0398] Perfuming composition

[0399] According to a particular embodiment, the consumer product is in the form of a perfuming composition comprising, based on the total weight of the perfuming composition:

[0400] - 0.1 to 30% by weight, preferably 0.1 to 20% by weight, of microcapsules or microcapsule slurry as defined above,

[0401] - 0 to 40% by weight, preferably 3 to 40% by weight, of fragrance, and

[0402] - 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol.

[0403] The present invention will now be further described by way of examples. It should be understood that the invention as claimed is not intended to be limited in any way by these examples.

[0404] Example 1

[0405] Preparation of soluble Moringa seed protein extract

[0406] De-oiled Moringa seed powder was purchased from Lifetime Tea (Chandler, AZ, USA). The protein content was 52% by weight, as determined by nitrogen determination using a factor of 6.25 (assuming a 16% nitrogen content for protein). A soluble Moringa seed extract was prepared according to the following protocol.

[0407] 1. Add at least 50 grams of de-oiled Moringa seed powder to a 1 kg batch of deionized water.

[0408] 2. Mix the solution using a Silverson L4RT homogenizer at 7000 rpm for 20 minutes

[0409] 3. Keep the protein aqueous solution batch at 60°C for 20 minutes

[0410] 4. Remix the solution at 7000 rpm for 5 minutes

[0411] 5. Centrifuge the sample at 8000 rpm for 10 minutes

[0412] 6. Collect the supernatant

[0413] 7. The collected supernatant was freeze-dried to obtain soluble Moringa protein powder.

[0414] Example 2

[0415] Preparation of microcapsules A according to the present invention

[0416] Freeze-dried Moringa oleifera seed extract with an extract solid content of 10% was prepared according to the protocol described in Example 1. Limonene capsules were prepared according to the following steps.

[0417] 1. Reconstitute the freeze-dried Moringa protein extract to 10%.

[0418] 2. Dilute the reconstituted solution to 4% to obtain a clear solution.

[0419] 3. Combine 13.5 g of the 4% dilution obtained in step 2 with 3.2 g of limonene in a glass jar and stir with a stir bar for 20 minutes to form an emulsion.

[0420] 4. Dilute the emulsion with 8.1 g of deionized water.

[0421] 5. Stir the diluted emulsion for 20 minutes

[0422] 6. Transglutaminase (Activa Source: Ajinomoto) (enzyme to protein ratio 1:100) was added to the diluted emulsion and stirred overnight.

[0423] 7. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature. Figure 1 As shown, the coacervate was found to be deposited on the limonene droplets.

[0424] Example 3

[0425] Preparation of microcapsules B according to the present invention

[0426] Freeze-dried Moringa protein extract with a solid content of 10% was prepared. Limonene capsules were prepared according to the following steps.

[0427] 1. Reconstitute the freeze-dried Moringa protein extract to 5%.

[0428] 2. Dilute 10 g of the 5% solution obtained in step 1 to 2.5% with deionized water.

[0429] 3. Combine the 2.5% dilution obtained in step 2 with 3 g of limonene in a glass jar and stir with a stirring rod for 20 minutes to form an emulsion.

[0430] 4. Mix the emulsion for 20 minutes

[0431] 5. Add transglutaminase (enzyme to protein ratio of 1:100) to the diluted emulsion and stir overnight.

[0432] 6. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature. Figure 2 As shown in (microcapsule B), coacervates were found to be deposited on the limonene droplets.

[0433] Example 4

[0434] Preparation of microcapsules C according to the present invention

[0435] Freeze-dried Moringa protein extract with an extract solid content of 25% was prepared. Limonene capsules were prepared according to the following steps.

[0436] 1. Reconstitute the freeze-dried Moringa protein extract to 20%.

[0437] 2. Dilute the 20% solution with deionized water to different concentrations (10%, 8%, 5%, 3%, 2%).

[0438] 3. Mix 90 g of the diluted solution obtained in step 2 with 10 g of limonene in a glass jar and stir at 5000-7000 rpm for 5 minutes using a benchtop biohomogenizer.

[0439] 4. Add transglutaminase (enzyme to protein ratio of 1:3) to the diluted emulsion and stir overnight.

[0440] 5. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature. Figure 3a (3% Moringa Protein Extract - Microcapsule C1) and Figure 3b As shown in (10% Moringa protein extract - microcapsules C2), the coacervate was found to be deposited at the limonene interface.

[0441] Example 5

[0442] Preparation of Moringa Protein-Gum Arabic Coacervate

[0443] Mixtures of Moringa protein extract and gum arabic were evaluated. To prepare mixed solutions, stock solutions of 10% gum arabic and 20% Moringa protein extract were prepared (freeze-dried Moringa protein extract with a solid content of 20% was reconstituted into a 20% solution). The total solid content of the mixed solution was 5%, and the mass ratios of gum arabic to Moringa protein extract were 0.5, 0.75, 1.0, 1.25, and 1.5, respectively. A mixture with a total solid content of 7% was also prepared, with a mass ratio of gum arabic to Moringa protein extract of 1.0. It was found that coacervates formed in all of these mixed solutions.

[0444] Limonene microcapsules stabilized by Moringa protein extract-gum arabic coacervate were prepared according to the following steps.

[0445] 1. Add 10 g of limonene to 90 g of Moringa protein-gum Arabic coagulant solution with a total solid content of 5% and a ratio of gum Arabic to Moringa protein extract of 0.75.

[0446] 2. Use a benchtop bio-homogenizer to mix at 3000-5000 rpm for 5 minutes.

[0447] 3. Transglutaminase (Activa Source: Ajinomoto) (enzyme to protein ratio 1:100) was added to the batch and mixed at 45°C for 3 hours.

[0448] 4. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature.

[0449] Microscopic images showed that the moringa protein-gum arabic coacervate was deposited on the limonene oil droplets, and the rough surface of the prepared microcapsules could be observed.

[0450] Example 6

[0451] Preparation of Moringa Protein-Rapeseed Protein Coacervate

[0452] Moringa protein extract and rapeseed protein ( To prepare the mixed solution, a 5% canola protein solution (adjusted to pH 7.9 with sodium hydroxide solution) and a 20% Moringa protein extract solution (freeze-dried Moringa protein extract with a 20% solids content was reconstituted to a 20% solution) were prepared. The total solids content of the mixed solution was 3%, and the mass ratio of canola protein to Moringa protein extract was 1.0.

[0453] Limonene microcapsules stabilized by Moringa protein extract-canola protein coacervate were prepared according to the following steps.

[0454] 1. Add 10 grams of limonene to 90 grams of Moringa protein-canola protein coagulant solution with a total solid content of 3% and a ratio of canola protein to Moringa protein extract of 1.0.

[0455] 2. Use a benchtop bio-homogenizer to mix at 3000-5000 rpm for 5 minutes.

[0456] 3. Transglutaminase (Activa Source: Ajinomoto) (enzyme to protein ratio 1:100) was added to the batch and mixed at 45°C for 3 hours.

[0457] 4. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature.

[0458] like Figure 4 As shown, protein coacervates were clearly deposited on the limonene oil droplets. The coacervates appeared to aggregate at the surface and form a thick interfacial layer, which could contribute to the stability of the microcapsules.

[0459] Example 7

[0460] Preparation of Moringa Protein-Pectin Coacervates

[0461] Moringa protein extract and pectin ( A mixture of β-pectin (CP Kelco) was evaluated. To prepare the mixed solution, a stock solution of 2% pectin and 20% Moringa protein extract was prepared (freeze-dried Moringa protein extract with a solid content of 20% was reconstituted into a 20% solution). The total solid content of the mixed solution was 3%, and the mass ratio of pectin to Moringa protein extract was 0.25.

[0462] Limonene microcapsules stabilized by Moringa protein extract-pectin coacervates were prepared according to the following steps.

[0463] 1. Add 10 g of limonene to 90 g of Moringa protein-pectin coagulant solution with a total solid content of 3% and a ratio of pectin to Moringa protein extract of 0.25.

[0464] 2. Use a benchtop bio-homogenizer to mix at 3000-5000 rpm for 5 minutes.

[0465] 3. Transglutaminase (Activa Source: Ajinomoto) (enzyme to protein ratio 1:100) was added to the batch and mixed at 45°C for 3 hours.

[0466] 4. Heat the mixture to 85°C for 15 minutes to inactivate the enzyme. Cool the sample to room temperature. Figure 5 As shown, a coacervate layer was observed at the droplet interface.

[0467] Example 8

[0468] Preparation of polyurea-based microcapsules according to the present invention

[0469] Polyurea microcapsules (D to I) were prepared according to the following general procedure:

[0470] A 10 wt% or 20 wt% solution of Moringa seed extract was prepared, and undissolved solids were optionally removed by centrifugation (8,000 rpm, 20 minutes). The supernatant was then diluted to the desired final Moringa concentration to form a coacervate (diluted to 5%). An oil phase (spice oil A - see Table 1) containing Takenate D-110N (75% ethyl acetate solution, trimethylolpropane adduct of xylylenediisocyanate, source: Mitsui Chemicals, Inc., Japan) at 2.0% or 2.5% based on the oil phase was added to the Moringa coacervate solution and homogenized using an IKA Ultra Turrax T25 (18G) at 7,000 rpm for 2 minutes. The emulsion was transferred to a reactor and stirred with an overhead anchor stirrer. The emulsion was heated to 45°C, and transglutaminase (Activa TI) was added. The mixture was stirred at 45°C for 3 hours (pH maintained at 5.0-5.3 using 10% NaOH). The slurry was then heated to 85°C and stirred for 30 minutes, and then cooled to room temperature. Figure 6 ——Microcapsules D).

[0471] The preparation of polyurea microcapsules (J) is as follows:

[0472] A 10 wt% Moringa seed extract solution was prepared and undissolved solids were removed by centrifugation (8000 rpm, 20 minutes). The supernatant was then diluted to the desired final Moringa concentration to form a coacervate (diluted to 5%). The oil phase (spice oil A - see Table 1) containing Takenate D-110N (2.0% based on the oil phase) was added to the Moringa coacervate solution and homogenized using an IKA Ultra Turrax T25 (18G) at 7,000 rpm for 2 minutes. The emulsion was transferred to a reactor and stirred with an overhead anchor stirrer. The emulsion was heated to 45°C and stirred for 3 hours (the pH was maintained at 5.0-5.3 using 10% NaOH). The slurry was then heated to 85°C and stirred for 30 minutes and then cooled to room temperature. The pH was then adjusted to 4.45, glutaraldehyde solution (1 wt%) was added, and stirred at room temperature for 10 hours.

[0473] Table 1: Fragrance ingredients

[0474] Element % in oil 2-Methylvalerate Ethyl ester 3.2％ Eucalyptol 7.8％ 2,4-Dimethyl-3-cyclohexene-1-carbaldehyde 0.75％ <![CDATA[Aldehyde C 10 > 0.75％ Citronellyl nitrile 4.3％ Isobornyl acetate 3％ 2-tert-Butyl-1-cyclohexyl acetate 9.8％ Citronellyl acetate 1.3％ 2-Methylundecanal 3％ diphenyl ether 0.8％ <![CDATA[Aldehyde C 12 > 1.3％ Dicyclopentadienyl acetate 9.85％ β-ionone 3.3％ γ-Undecalactone 18.75％ Hexyl salicylate 15.9％ Benzyl salicylate 16.2％

[0475] Table 2: Composition of microcapsules

[0476]

[0477] Example 9

[0478] Performance of the microcapsules according to the present invention

[0479] Sufficient exemplary microcapsules were weighed and mixed into liquid detergent and fabric softener compositions to add the equivalent of 0.2% perfume.

[0480] Concentrated liquid detergent base is commercially available Free&Gentle (trademark of Procter and Gamble, USA).

[0481] The composition of fabric softener is as follows:

[0482] Table 3: Composition of fabric softener

[0483] product weight% Stepantex VL 90A 8.88 Calcium chloride solution 10% 0.36 Proxel GXL 0.04 spices 1.00 water 89.72 total 100

[0484] plan: Weigh 2 g of sample (matrix including capsules) into a 20 mL vial. Add 10 mL of the extraction solvent (isooctane) containing the internal standard 1,4-dibromobenzene at a precisely known concentration of approximately 90 ng / μL. Shake at 40 RPM for 45 minutes to extract the free fragrance. Remove the solvent phase.

[0485] To measure the leakage in the base material, an Agilent GCFID7890A was used with the injector set at 250°C, helium as the carrier gas at a flow rate of 1 mL / min, and the oven temperature was programmed to start at 120°C, hold for 5 minutes, increase to 170°C at 10°C / min, increase to 220°C at 25°C / min, and then increase to 260°C at 25°C / min. For subsequent runs, measurements were completed at 260°C.

[0486] Calibration solutions of 100, 300, and 600 ng / μL of the aromatic oil were prepared in isooctane. It is important that the aromatic oil used to prepare the calibration curves comes from the same batch used to produce the microcapsules.

[0487] Table 4: Stability results

[0488]

[0489] NM: Not Measured

[0490] These results emphasize that the microcapsules of the present invention are stable in surfactant-based consumer products.

[0491] Example 10

[0492] Preparation of polyurea-based microcapsules according to the present invention

[0493] Polyurea microcapsules (K to N) were prepared according to the following general procedure:

[0494] A 15 wt% or 20 wt% solution of Moringa seed extract was prepared, and undissolved solids were optionally removed by centrifugation (8,000 rpm, 15 minutes). The supernatant was then mixed with another biopolymer solution pre-dissolved with either gum arabic (2.9 wt%) or canola protein (3 wt%) to form a coacervate (5 wt%, a 1:1 ratio of Moringa seed extract to the other biopolymer). An oil phase (spice oil A - see Table 1 above) containing Takenate D-110N (75% ethyl acetate solution, trimethylolpropane adduct of xylylenediisocyanate, source: Mitsui Chemicals, Inc., Japan) at 1.0 or 2.0 wt% based on the oil phase was added to the Moringa coacervate solution and homogenized using an IKA Ultra Turrax T25 (18G) at 7,000 rpm for 2 minutes. The emulsion was transferred to a reactor and stirred with an overhead anchor stirrer. The emulsion was heated to 45°C and transglutaminase (Activa TI) was added. The emulsion was stirred at 45°C for 3 hours. The slurry was then heated to 85°C and stirred for 30 minutes and then cooled to room temperature. Microcapsules were obtained (see Figures 7 to 10 , representing microcapsules K to N, respectively).

[0495] Table 5: Composition of microcapsules

[0496]

[0497] The stability of the prepared microcapsules was evaluated after storage in a softener at 37° C. for 3 days. The results are shown in Table 6. The test protocol was the same as in Example 9 above.

[0498] Table 6: Stability results

[0499] microcapsules 3-day stability in softener K 8.9％ L 0.9％ M 1.6％ N 5.9％

[0500] Example 11

[0501] Powder detergent compositions

[0502] Sufficient exemplary microcapsules were weighed and mixed into a powder detergent composition to add the equivalent of 0.2% perfume.

[0503] Table 7: Powder detergent composition

[0504] Element Number of copies Anion (linear alkylbenzene sulfonate) 20％ Nonionic (alcohol ethoxylate (5-9 ethylene oxide)) 6％ Detergents (zeolite, sodium carbonate) 25％ silicates 6％ sodium sulfate 35％ Others (enzymes, polymers, bleaching agents) 7.5％ Spray-dried microparticle powders A to E 0.5％

[0505] Example 12

[0506] Liquid detergent compositions

[0507] The microcapsules of the present invention were dispersed in the liquid detergent base described below to obtain a concentration of 0.22% encapsulated fragrance oil.

[0508] Table 8: Composition of liquid detergent

[0509] Element Concentration [wt%] <![CDATA[Sodium C14-17 secondary alkyl sulfonate 1) > 7 <![CDATA[C12-18 fatty acids and C18-unsaturated fatty acids 2) > 7.5 <![CDATA[C12 / 14 fatty alcohol polyethylene glycol ether with 7 mol EO 3) > 17 triethanolamine 7.5 Propylene glycol 11 citric acid 6.5 potassium hydroxide 9.5 Protease 0.2 amylase 0.2 Mannanase 0.2 <![CDATA[Acrylate / Steareth-20 Methacrylate Structured Crosslinked Polymer 4) > 6 Deionized water 27.4

[0510] 1) SAS 60; Source: Clariant

[0511] 2) K 12-18; Source: Cognis

[0512] 3) LA 070; Source: Clariant

[0513] 4) 88; Source: Dow Chemical

[0514] Example 13

[0515] Rinse-off conditioner

[0516] The microcapsules of the present invention were dispersed in the following rinse-off conditioner base to provide a 0.5% concentration of encapsulated fragrance oil.

[0517] Table 9: Composition of rinse-off conditioners

[0518]

[0519] 1)Genamin KDM P,Clariant

[0520] 2)Tylose H10 Y G4,Shin Etsu

[0521] 3) Lanette O, BASF

[0522] 4)Arlacel 165-FP-MBAL-PA-(RB),Croda

[0523] 5)Incroquat Behenyl TMS-50-MBAL-PA-(MH)HA4112,Croda

[0524] 6)SP Brij S20 MBAL-PA(RB),Croda

[0525] 7) Xiameter DC MEM-0949 Emulsion, Dow Corning

[0526] 8) Alfa Aesar

[0527] Example 14

[0528] Shampoo composition

[0529] The microcapsules of the present invention were weighed and mixed into the shampoo composition to add the equivalent of 0.2% of fragrance.

[0530] Table 10: Composition of shampoo

[0531]

[0532] 1)Ucare Polymer JR-400, Noveon

[0533] 2) Schweizerhall

[0534] 3) Glydant, Lonza

[0535] 4)Texapon NSO IS, Cognis

[0536] 5) Tego Betain F 50, Evonik

[0537] 6)Amphotensid GB 2009,Zschimmer&Schwarz

[0538] 7) Monomuls 90L-12, Gruenau

[0539] 8) Monosodium paraben, NIPA

[0540] Example 15

[0541] Antiperspirant roll-on lotion composition

[0542] The microcapsules of the present invention were weighed and mixed into an antiperspirant roll-on composition to add fragrance equivalent to 0.2%.

[0543] Table 11: Composition of antiperspirant roll-on lotion

[0544] Element Amount (weight %) <![CDATA[Polyethylene glycol (2) stearyl ether 1) (Part A)]]> 3.25 <![CDATA[Polyoxyl 21 Stearyl Ether 2) (Part A)]]> 0.75 <![CDATA[PPG-15 Stearyl Ether 3) (Part A)]]> 4 Deionized water (Part B) 51 <![CDATA[50% aqueous solution of aluminum chlorohydrate 4) (Part C)]]> 40 Fragrances (Section D) 1

[0545] 1) BRIJ 72; Source: ICI

[0546] 2) BRIJ 721; Source: ICI

[0547] 3) ARLAMOL E; Source: UNIQEMA-CRODA

[0548] 4) LOCRON L; Source: CLARIAN

[0549] 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. When the mixture reaches 35°C, slowly add Part D while stirring. Then, cool the mixture to room temperature.

[0550] Example 16

[0551] Deodorant spray composition

[0552] The microcapsules of the present invention were weighed and mixed into an antiperspirant roll-on composition to add fragrance equivalent to 0.2%.

[0553] Table 12: Composition of Deodorant Spray

[0554] Element Amount (weight %) Ethanol 95% 90.65 <![CDATA[Triclosan 1) > 0.26 Isopropyl myristate 9.09

[0555] 1) DP 300; Trademark and source: BASF

[0556] All ingredients were mixed and dissolved according to the order of Table 12. The aerosol can was then filled, compacted and the propellant added (aerosol fill: 40% active solution, 60% propane / butane 2.5 bar).

[0557] Example 17

[0558] Shower gel composition

[0559] The microcapsules of the present invention were weighed and mixed in the following composition to add fragrance equivalent to 0.2%.

[0560] Table 13: Composition of shower gel

[0561] Element Amount (weight %) Function Deionized water 49.350 solvent <![CDATA[Sodium EDTA 1) > 0.050 chelating agents <![CDATA[Acrylic copolymer 2) > 6.000 thickener <![CDATA[Sodium C12 - C15 alcohol polyether sulfate 3) > 35.000 surfactants 20% sodium hydroxide aqueous solution 1.000 pH adjusters <![CDATA[Cocamidopropyl betaine 4) > 8.000 surfactants <![CDATA[Methylchloroisothiazolinone and methylisothiazolinone 5) > 0.100 preservative Citric acid (40%) 0.500 pH adjusters

[0562] 1) EDETA B powder; Trademark and source: BASF

[0563] 2) CARBOPOL AQUA SF-1 polymer; Trademark and source: NOVEON

[0564] 3) ZETESOL AO 328U; Trademark and source: ZSCHIMMER & SCHWARZ

[0565] 4) TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0566] 5) KATHON CG; Trademark and source: ROHM & HASS

[0567] Example 18

[0568] Unit dose formulations

[0569] Sufficient exemplary microcapsules were weighed and mixed into the unit dose formulation to add the equivalent of 0.2% flavor.

[0570] The unit dose formulation may be contained in a PVOH (polyvinyl alcohol) film.

[0571] Table 14: Composition of unit dose

[0572] Element Concentration [wt%] C12-C14 alkyl polyethoxylate 15 C12-C14 Alkyl Polyethoxylate Sulfate Monoethanolamine Salt 9.5 Linear alkylbenzene sulfonic acid 17 citric acid 0.5 C12-C18 fatty acids 17 enzymes 1.2 fluorescent brightener 0.3 1,2-Propanediol 12 glycerin 9 Sodium hydroxide 1 Monoethanolamine 6 PDMS 2.5 Potassium sulfite 0.2 water 8.8 total 100

[0573] Example 19

[0574] Soap bars

[0575] Sufficient amount of exemplary microcapsules were weighed and mixed into the soap bar formulation at a concentration of 7.5% w / w.

[0576] Table 15: Composition of soap formulations

[0577] Element Soap formulation (%) surfactants Sodium linear alkylbenzene sulfonate soap 10 to 25 α-Olefin Sulfonate (AOS) Sodium lauryl sulfate detergent sodium carbonate 5 to 15 Sodium tripolyphosphate zeolite filler sodium sulfate 5 to 30 talc 5 to 30 dolomite 5 to 50 porcelain clay 5 to 50 Calcite - calcium carbonate Sodium chloride 5 to 20 Structural ingredients aluminum sulfate 0.5 to 5 Alkaline silicates 1 to 5 other pigment 0.1 to 1 spices 0.1 to 1 Moisture 5 to 15

[0578] Example 20

[0579] Beauty Day Cream

[0580] Sufficient amount of exemplary microcapsules were weighed and blended into a cosmetic skin cream (see composition below) at a concentration of 5% w / w.

[0581] Table 16: Composition of cream

[0582]

[0583] 1) ARLATONE 985

[0584] 2)TEFOSE 2561

[0585] 3) COSBIOL

[0586] 4) GLYDANT PLUS

[0587] Example 21

[0588] Toothpaste formulations

[0589] A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in Example 1, except that menthol flavor was encapsulated) was weighed and mixed into the following composition to add the equivalent of 0.2% flavor.

[0590] Table 17: Toothpaste formulation

[0591]

[0592]

[0593] 1) Tixosil 73; Trademark and Source:

[0594] 2) Tixosil 43; Trademark and source:.

Claims

1. A coacervate core-shell microcapsule comprising a hydrophobic material, preferably a flavoring agent or fragrance, wherein: a) the hydrophobic material is encapsulated in the core of a coacervate core-shell microcapsule, and b) the shell of the coacervate core-shell microcapsules comprises at least one Moringa extract, and wherein the shell is cross-linked.

2. The microcapsule according to claim 1, wherein the Moringa extract is a Moringa seed extract.

3. Microcapsules according to claim 1 or 2, wherein the Moringa extract is in an extract from Moringa seed powder, preferably de-oiled Moringa seed powder.

4. Microcapsules according to any one of the preceding claims, wherein the protein content in the Moringa extract is 30% to 90%, preferably 40% to 80% by weight, based on the total weight of the extract.

5. Microcapsules according to any one of the preceding claims, wherein the Moringa extract is present in an amount of 0.1% to 30%, preferably 1% to 15%, based on the total weight of the microcapsules.

6. Microcapsules according to any one of the preceding claims, wherein the shell comprises a non-protein polymer and / or a protein polymer.

7. The microcapsule according to any one of the preceding claims, wherein the shell of the microcapsule is cross-linked using formaldehyde, genipin, tannin, acetaldehyde, glutaraldehyde, glyoxal, chrome alum, transglutaminase and mixtures thereof.

8. Microcapsules according to any one of the preceding claims, wherein the shell comprises additional polymeric material.

9. The microcapsule of claim 8, wherein the polymeric material is 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.

10. The microcapsule according to claim 8 or 9, wherein the polymeric material is used in an amount of 0.5 to 20% based on the total weight of the microcapsule.

11. A method for preparing the coacervate core-shell microcapsules according to any one of the preceding claims, wherein the method comprises the following steps: a) preparing a solution by dissolving at least one Moringa extract in an aqueous solution, preferably water; b) optionally, preparing a solution by dissolving at least one non-protein polymer and / or at least one protein polymer in an aqueous solution, preferably water; c) optionally, mixing the prepared solution comprising at least one plant protein extract and at least one non-protein polymer and / or at least one protein polymer; d) preparing an emulsion and / or suspension by emulsifying and / or suspending a hydrophobic material and optionally a multifunctional monomer in a solution; e) forming a coacervate shell comprising the Moringa extract and optionally a non-proteinaceous polymer and / or a proteinaceous polymer, surrounding droplets and / or particles of a hydrophobic material present in the emulsion and / or suspension; and f) crosslinking the shell.

12. The process according to claim 11, wherein step f) is carried out using a crosslinking agent in an amount of 0.005 to 5%, preferably 0.5 to 2%, based on the total weight of the emulsion and / or suspension.

13. A consumer product comprising the coacervate core-shell microcapsules according to claims 1 to 10, wherein the product is a flavored or aromatized product.

14. The consumer product of claim 13, wherein the aromatized product is selected from the group consisting of a liquid or solid detergent, a fabric softener, a liquid or solid fragrance enhancer, a shampoo, a body wash, a hair conditioning product, a deodorant, or an antiperspirant.

15. The consumer product of claim 13, wherein the flavored product is selected from the group consisting of: meat and / or fish foods or analogs, broth bases, soup blocks, powder mixes, beef or pork products, seafood, surimi, instant noodles, rice, broths, sauces, ready meals, frozen or refrigerated pizzas, pasta, potato chips or fried potatoes, noodles, potato chips / corn chips, microwave popcorn, nuts, pretzels, rice cakes, rice crackers, fermented dairy analog beverages, acidified dairy analog beverages, non-fermented dairy analog beverages, cheese or cheese analogs, yogurt or yogurt analogs, nutritional supplements, nutritional bars, cereals, ice cream, dairy-free ice cream, confectionery products, chewing gum, hard candy, and powdered beverages.

Images