Hybrid microcapsules

Abstract

The present invention relates to a new method for preparing hybrid microcapsules. The hybrid microcapsules are also an object of the present invention. Fragranced consumer products in the form of fragrance compositions and consumer products containing said microcapsules, in particular home care products or personal care products, are also part of the present invention.

Description

Technical Field

[0001] The present invention relates to a new method for preparing hybrid microcapsules. The hybrid microcapsules are also an object of the present invention. Perfumed consumer products in the form of perfume compositions and consumer products containing said microcapsules, in particular home care products or personal care products, are also part of the present invention.

[0002] Background of the Invention One of the problems faced by the perfume industry is that due to their volatility, especially the volatility of "top notes", the olfactory benefits provided by perfume compounds are lost relatively rapidly. In order to adjust the release rate of volatile substances, delivery systems such as microcapsules containing perfume are necessary to protect the core payload and release it when triggered later. A major requirement from the industry for these systems is to withstand suspension in harsh bases without physically dissociating or decomposing. This is called the stability of the delivery system. For example, aromatic personal cleansers and household cleansers containing high levels of aggressive surfactants are very harsh on the stability of microcapsules.

[0003] In addition to performance regarding stability and olfactory performance, consumer demands for environmentally friendly delivery systems are becoming increasingly important and are driving the development of new delivery systems.

[0004] Therefore, there is still a need to provide new microcapsules using more environmentally friendly materials without compromising on the performance of microcapsules, especially with regard to stability in difficult media such as consumer product bases, and providing good performance in active ingredient delivery (e.g., olfactory performance in the case of perfume ingredients).

[0005] The present invention proposes a solution to the above problems by providing new hybrid microcapsules and a method for preparing said microcapsules.

[0006] Summary of the Invention A first object of the present invention is a method for preparing a microcapsule slurry, comprising: 1) suspending coacervate particles in a solvent to form a dispersed phase; 2) mixing at least one polyfunctional monomer with a hydrophobic material to form an oil phase; 3) adding the oil phase to the dispersed phase and mixing them to form a two-phase Pickering emulsion under conditions that enable the formation of a microcapsule slurry by interfacial polymerization. The method includes the above steps.

[0007] A second object of the present invention is a microcapsule slurry obtained by the method according to any one of the preceding claims.

[0008] The present invention also relates to a scented consumer product and a scented food product comprising the microcapsule slurry or microcapsules as defined above. BRIEF DESCRIPTION OF THE DRAWINGS

[0009]

Figure 1

Figure 2

Figure 3

[0010] DETAILED DESCRIPTION OF THE INVENTION Unless otherwise specified, percentages (%) mean weight percentages of the composition.

[0011] "Active ingredient" means a single compound or a combination of components.

[0012] "Spice or flavor oil" means a single spice or flavor compound, or a mixture of several spices or flavor compounds.

[0013] "Consumer product" or "end product" means a manufactured product that is ready for distribution, sale, and use by consumers.

[0014] For the sake of clarity, the expression "dispersion" in the present invention means a system in which particles are dispersed in a continuous phase of a different composition, specifically including suspensions or emulsions.

[0015] "Microcapsules" or the like in the present invention means that the core-shell microcapsules have a particle size distribution in the micron range (for example, between about 1 and 3000 microns, preferably between 1 and 500 microns, more preferably between 5 and 50 microns in average diameter), and include an external solid polymer shell and an internal continuous oil phase surrounded by the external shell.

[0016] "Microcapsule size" or "particle size" means the volume average diameter (D[4,3]) of the relevant capsules / particles, capsule / particle suspension obtained by laser light scattering of a diluted sample in a Malvern Mastersizer 3000.

[0017] Therefore, microcapsules are defined as "hybrid" or "composite" with respect to the nature of the shell composed of a polymer shell formed by interfacial polymerization, and the coacervate particles are embedded within the polymer shell. The coacervate particles are used to stabilize the pickering emulsion during the process.

[0018] "Microcapsule slurry" means microcapsules dispersed in a liquid. According to one embodiment, the slurry is an aqueous slurry, that is, the microcapsules are dispersed in the aqueous phase.

[0019] "Multifunctional monomer" means a molecule that chemically reacts or binds as a unit to form a polymer or supramolecular polymer. The multifunctional monomer of the present invention has at least two functional groups that can react or bind with the functional groups of other components and / or can polymerize to form a polymer shell.

[0020] It has been found that hybrid microcapsules having overall good performance in a harsh base can be obtained.

[0021] Method for preparing microcapsules A first object of the present invention is a method for preparing a microcapsule slurry, comprising: 1) suspending coacervate particles in a solvent to form a dispersed phase; 2) mixing at least one multifunctional monomer with a hydrophobic material to form an oil phase; 3) adding the oil phase to the dispersed phase and mixing them to form a two-phase Pickering emulsion under conditions that allow the formation of a microcapsule slurry by interfacial polymerization. The method includes the above steps.

[0022] According to one embodiment, a method for preparing a microcapsule slurry includes: 1) suspending coacervate particles in water to form an aqueous phase; 2) mixing at least one multifunctional monomer with a hydrophobic material to form an oil phase; 3) adding the oil phase to the aqueous phase and mixing them to form a water-in-oil Pickering emulsion under conditions that allow the formation of a microcapsule slurry by interfacial polymerization. The method includes the above steps.

[0023] According to one embodiment, the solvent contains water and preferably consists of water.

[0024] According to one embodiment, the dispersed phase is an aqueous phase.

[0025] According to one embodiment, the biphasic dispersion is an oil-in-water emulsion.

[0026] According to one embodiment, the solvent includes water and an alcohol such as glycerol, 1,4-butanediol, ethylene glycol, and mixtures thereof.

[0027] According to one embodiment, the second polyfunctional monomer is added to the aqueous phase in step 1) and / or to the Pickering emulsion in step 3).

[0028] The second polyfunctional monomer can be selected from the group consisting of melamine resins or urea resins.

[0029] According to one embodiment, in the present invention, two processes are combined, that is, microcapsules having good properties are obtained by the formation of coacervate particles prepared by the flash nanoprecipitation (FNP) process and the interfacial polymerization (or interfacial reaction) process.

[0030] The method of the present invention includes forming a Pickering emulsion that is further subjected to interfacial polymerization (or interfacial reaction).

[0031] Although not wishing to be bound by theory, it is believed that the Pickering emulsion determines the morphology and surface properties (size, density, zeta potential, rigidity) of the membrane, and the interfacial reaction determines the permeability and rigidity of the capsule.

[0032] FIG. 1 shows the formation of a Pickering emulsion when coacervate particles are used as a colloidal stabilizer to stabilize oil droplets.

[0033] According to a specific embodiment, the polymeric emulsifier is added to the aqueous phase in step 1).

[0034] The term "polymer emulsifier" means an emulsifier having both a polar group (hydrophilic) with an affinity for water and a non-polar group (lipophilic) with an affinity for oil. The hydrophilic portion can dissolve in the aqueous phase, and the hydrophobic portion can dissolve in the oil phase, providing a film around the droplets. The coacervate particles used in the present invention are not polymer emulsifiers. Coacervate particles belong to the category of colloid stabilizers.

[0035] This optional polymer emulsifier can help stabilize the oil droplets in the presence of coacervate particles. The polymer emulsifier can be an ionic or non-ionic surfactant. As non-limiting examples, non-ionic polymers include polyvinyl alcohol, gum arabic, cellulose derivatives such as hydroxyethyl cellulose, polyethylene oxide, copolymers of polyethylene oxide with polyethylene or polypropylene oxide, copolymers of alkyl acrylate with N-vinylpyrrolidone, and non-ionic polysaccharides. Ionic polymers include copolymers of acrylamide and acrylic acid, acidic anionic surfactants (such as sodium dodecyl sulfate), acrylic copolymers having sulfonic acid groups, and copolymers of vinyl ether and maleic anhydride, and ionic polysaccharides.

[0036] According to one embodiment, no polymer emulsifier is added at any stage of the method.

[0037] In the first step of the method, the core cell wall particles are dispersed in a solvent having a pH preferably between 2 and 8, preferably in the aqueous phase. Typically, this is done under ultrasonic or high mechanical agitation conditions. In the second step, at least one polyfunctional monomer is dissolved in a hydrophobic material (e.g., a fragrance or flavor oil) to form an oil phase, which is then added to the dispersed phase (typically the aqueous phase) to form a Pickering emulsion, the average droplet size of which is preferably between 1 and 3000 microns, more preferably between 1 and 500 microns, even more preferably between 5 and 50 microns. The two-phase Pickering dispersion (typically an oil-in-water Pickering emulsion) is prepared, for example, at room temperature by using a high-speed mechanical disperser or an ultrasonic disperser.

[0038] Once the Pickering emulsion is formed, the pH value is adjusted to a value preferably above 8.5, preferably 11 or less. However, this step can be omitted.

[0039] Interfacial polymerization is typically carried out at a temperature between 50 °C and 80 °C with stirring for 2 to 40 hours to complete the reaction and form microcapsules in the form of a slurry.

[0040] The form of the microcapsules of the present invention can vary from core-shell type to matrix type. According to one embodiment, this is of the core-shell type. In this case, the microcapsules comprise a core based on a hydrophobic active ingredient, typically a fragrance or flavor oil, and a polymer shell containing core cell wall particles embedded within the polymer shell.

[0041] oil phase According to the present invention, at least one polyfunctional monomer is admixed with the hydrophobic material to form an oil phase.

[0042] According to one embodiment, the polyfunctional monomer used in the method of the present invention is present in an amount corresponding to 0.1 to 40% by weight, preferably 0.1 to 30% by weight, more preferably 0.2 to 20% by weight, based on the total amount of the oil phase.

[0043] According to one embodiment, the polyfunctional monomer is selected from the group consisting of at least one isocyanate, anhydride or maleic anhydride, acyl chloride, epoxide, (meth)acrylate monomer, alkoxysilane, and mixtures thereof.

[0044] Suitable polyfunctional isocyanates used in accordance with the present invention have at least two or three isocyanate functional groups and include aromatic isocyanates, aliphatic isocyanates, and mixtures thereof.

[0045] According to a particular embodiment, the polyfunctional isocyanate contains at least three isocyanate functional groups, but may contain up to six, or even only four, isocyanate functional groups, and the oil phase is essentially free of diisocyanate.

[0046] According to a particular embodiment, a triisocyanate (three isocyanate functional groups) is used.

[0047] According to one embodiment, the polyfunctional isocyanate is an aromatic polyfunctional isocyanate.

[0048] As used herein, the term "aromatic polyfunctional isocyanate" means any polyfunctional isocyanate containing an aromatic moiety. Preferably, the aromatic moiety contains a phenyl, toluyl, xylyl, naphthyl or diphenyl moiety, more preferably a toluyl or xylyl moiety. Preferred aromatic polyfunctional isocyanates are biuret and polyisocyanurate, more preferably containing one of the specific aromatic moieties described above. More preferably, the aromatic polyfunctional isocyanate is a polyisocyanurate of toluene diisocyanate (commercially available from Bayer under the trade name Desmodur® RC), a trimethylolpropane adduct of toluene diisocyanate (commercially available from Bayer under the trade name Desmodur® L75), or a trimethylolpropane adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the trade name Takenate® D-110N). In the most preferred embodiment, the aromatic polyfunctional isocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0049] According to another embodiment, the polyfunctional isocyanate is an aliphatic polyfunctional isocyanate. The term "aliphatic polyfunctional isocyanate" is defined as a polyfunctional isocyanate that does not contain an aromatic moiety. Preferred aliphatic polyfunctional isocyanates are the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, the trimethylolpropane adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or the biuret of hexamethylene diisocyanate (commercially available from Bayer under the trade name Desmodur® N 100), among which the biuret of hexamethylene diisocyanate is even more preferred.

[0050] According to another embodiment, the at least one polyfunctional isocyanate is in the form of a mixture of at least one aliphatic polyfunctional isocyanate and at least one aromatic polyfunctional isocyanate, both containing at least two or three isocyanate functional groups, for example, a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate, a mixture of biuret of hexamethylene diisocyanate and polyisocyanurate of toluene diisocyanate, and a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of toluene diisocyanate. Most preferably, it is a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate.

[0051] According to one embodiment, the polyfunctional monomer is an acyl chloride.

[0052] According to a particular embodiment, the acyl chloride has the following formula (I).

Chemical formula

Chemical formula

[0053] " ... hydrocarbon group ... " means that the group consists of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e., a straight-chain or branched-chain saturated hydrocarbon (e.g., an alkyl group), a straight-chain or branched-chain unsaturated hydrocarbon (e.g., an alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g., cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g., cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e., an aryl group, or can also be in the form of a mixture of the above types of groups. For example, a particular group, unless a specific limitation to only one type is mentioned, is understood to be able to include a straight-chain alkyl, a branched-chain alkenyl (e.g., having one or more carbon-carbon double bonds), a (poly)cycloalkyl, and an aryl moiety. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of two or more topologies (e.g., straight-chain, cyclic or branched-chain) and / or saturated or unsaturated (e.g., alkyl, aromatic or alkenyl), it also means a group that can include a moiety having any one of the topologies described above or a moiety that is saturated or unsaturated. Similarly, in all embodiments of the present invention, when a group is referred to as being in one type of saturated or unsaturated form (e.g., alkyl), it means that the group can be of any type of topology (e.g., straight-chain, cyclic or branched-chain) or can have several moieties having different topologies.

[0054] The term " ... hydrocarbon group optionally containing ... " is understood to mean that the hydrocarbon group optionally contains heteroatoms and forms an ether, thioether, amine, nitrile or carboxylic acid group and derivatives (e.g., including esters, acids, amides). These groups can replace the hydrogen atoms of the hydrocarbon group and thus can be bonded laterally to the hydrocarbon, or can replace the carbon atoms of the hydrocarbon group (where chemically possible) and thus can be inserted into the hydrocarbon chain or ring.

[0055] According to certain embodiments, the acyl chloride is selected from the group consisting of benzene-1,3,5-tricarbonyl trichloride (trimesityl trichloride), benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthaloyl dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaroyl dichloride, adipoyl chloride, succinyl dichloride, propane-1,2,3-tricarbonyl trichloride, cyclohexane-1,2,4,5-tetracarbonyl tetrachloride, 2,2'-disulfanediyl disuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate, [2-[2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl] 4-chloro-4-oxo-butanoate, 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate, [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, propane-1,2,3-triyltris(4-chloro-4-oxobutanoate), propane-1,2-diylbis(4-chloro-4-oxobutanoate) and mixtures thereof.

[0056] According to certain embodiments, the oil phase concentration is between 5% and 60%, preferably between 20% and 40%, of the pickering emulsion.

[0057] Hydrophobic material According to one embodiment, the core is an oil-based core.

[0058] The hydrophobic material according to the present invention can be a "non-active" material such as a solvent or an active ingredient.

[0059] When the hydrophobic material is an active ingredient, the hydrophobic material is preferably selected from the group consisting of flavors, flavor components, fragrances, fragrance components, dietary supplements, cosmetics, pesticides, biocidal active substances, and mixtures thereof.

[0060] According to a particular embodiment, the hydrophobic material comprises a mixture of a fragrance and another component selected from the group consisting of dietary supplements, cosmetics, pesticides, and biocidal active substances.

[0061] According to one embodiment, the hydrophobic material comprises a phase change material (PCM).

[0062] According to a particular embodiment, the hydrophobic material comprises a mixture of a biocidal active substance and another component selected from the group consisting of fragrances, dietary supplements, cosmetics, and pesticides.

[0063] According to a particular embodiment, the hydrophobic material comprises a mixture of a pesticide and another component selected from the group consisting of fragrances, dietary supplements, cosmetics, and biocidal active substances.

[0064] According to a particular embodiment, the hydrophobic material comprises a fragrance.

[0065] According to a particular embodiment, the hydrophobic material consists of a fragrance.

[0066] According to a particular embodiment, the hydrophobic material consists of a biocidal active substance.

[0067] According to a particular embodiment, the hydrophobic material consists of a pesticide.

[0068] "Fragrance" (or also "perfume oil") means, in this specification, a component or composition that is liquid at about 20 °C. According to any one of the above embodiments, the perfume oil can be a perfume component alone or a mixture of components in the form of a perfume composition. As "perfume component", this specification means a compound used for the main purpose of imparting or regulating odor. In other words, such a component must be recognized by those skilled in the art as not only having an odor, but also being able to positively or at least pleasantly impart or modify the odor of the composition. For the purposes of the present invention, the perfume oil also includes a combination of a perfume precursor, a modifier, an emulsion or a dispersion, etc. with a perfume component to improve, enhance or modify the delivery of the perfume component together, and a combination that imparts additional benefits beyond those that modify or impart odor such as long-lasting, blooming, malodor prevention, antimicrobial effect, microbial stability, pest control, etc.

[0069] The nature and type of perfume components present in the oil phase are not guaranteed by the more detailed description herein, are not exhaustive in any case, and those skilled in the art can select them based on their general knowledge according to the intended use or application and the desired sensory stimulation effect. Generally speaking, these perfume components belong to various chemical classifications such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds and essential oils (e.g., thyme oil), and the perfume adjuvant components can be of natural or synthetic origin. Many of these co-components are listed in references such as the book, S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent version, or other works of a similar nature, as well as the abundant patent literature in the field of cosmetics.

[0070] In particular, perfume components commonly used in perfume formulations, such as - Aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and / or nonenal; - Aromatic herb components: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0 2,7 undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or alpha-pinene; - Balsamic components: coumarin, ethyl vanillin and / or vanillin; - Citrus components: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpene, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; - Floral components: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta-ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, 2,5-dimethyl-2-indanemethanol, 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, verdyl acetate, geraniol, p-menth-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl high cis-dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, verdyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,A mixture of 2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amyl cinnamic aldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, verdyl isobutyrate and / or methyl ionone isomers; - Fruity components: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - Green components: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk components: 1,4-dioxaspiro[4.5]decane-2,6-dione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-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 propanoate, oxacyclohexadecan-2-one and / or (1S,1’R)-[1-(3’,3’-dimethyl-1’-cyclohexyl)ethoxycarbonyl]methyl propanoate; - Woody components: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4’-dimethylspiro[oxirane-2,9’-tricyclo[6.2.1.0 2,7 undeca[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, Clearwood (registered trademark), (1’R,E)-2-ethyl-4-(2’,2’,3’-trimethyl-3’-cyclopenten-1’-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; - Other ingredients (e.g., amber, powdery spicy or watery): either dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal may be mentioned.

[0071] It is also understood that the foregoing component may also be a compound known to release various types of fragrance compounds, also known as pro-fragrances or pro-fragrances, in a controlled manner. Non-limiting examples of suitable pro-fragrances include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yl oxo(phenyl)acetate, (Z)-hex-3-en-1-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl) succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-en, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-en, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-(dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or mixtures thereof may be mentioned.,

[0072] The fragrance component may be dissolved in a solvent currently used in the fragrance industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffin. Preferably, the solvent is very hydrophobic and highly sterically hindered, such as, for example, Abalyn® or benzyl benzoate. Preferably, the fragrance contains less than 30% solvent. More preferably, the fragrance contains less than 20%, even more preferably less than 10% solvent, all of these percentages being defined by weight relative to the total weight of the fragrance. Most preferably, the fragrance is essentially solvent-free.,

[0073] Preferred fragrance components are those having high steric hindrance (bulky materials), in particular those from one of the following groups: Group 1: fragrance components containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C1-C4 alkyl or alkenyl substituent; Group 2: A fragrance ingredient containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4-C8 alkyl or alkenyl substituent; Group 3: A fragrance ingredient containing a phenyl ring, or a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5-C8 alkyl or alkenyl substituent or at least one phenyl substituent and optionally one or more linear or branched C1-C3 alkyl or alkenyl substituents; Group 4: A fragrance ingredient containing at least two fused or linked C5 and / or C6 rings; Group 5: A fragrance ingredient containing a camphor-like ring structure; Group 6: A fragrance ingredient containing at least one C7-C 20 ring structure; Group 7: A fragrance ingredient having a logP value greater than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent.

[0074] Examples of the components from each of these groups are as follows. Group 1: 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde (manufactured by Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (manufactured by Firmenich SA, Geneva, Switzerland), nerol, terpineol, dihydroterpineol, terphenyl acetate, dihydroterphenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1,8-p-menthadien-7-ol (manufactured by Firmenich SA, Geneva, Switzerland), 1-p-menthen-4-ol, (1RS,3RS,4SR)-3-p-menthanyl acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (manufactured by Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1,4-cyclohexanedicarboxylic acid diethyl ester (manufactured by Firmenich SA, Geneva, Switzerland), (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benz[B]furan-2-one (manufactured by Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benz[B]furan-2-one (manufactured by Firmenich SA, Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde; Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (manufactured by Givaudan SA, Vernier, Switzerland), (1’R,E)-2-ethyl-4-(2’,2’,3’-trimethyl-3’-cyclopenten-1’-yl)-2-buten-1-ol (manufactured by Firmenich SA, Geneva, Switzerland), (1’R,E)-3,3-dimethyl-5-(2’,2’,3’-trimethyl-3’-cyclopenten-1’-yl)-4-penten-2-ol (manufactured by Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone, methyl-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (manufactured by Firmenich SA, Geneva, Switzerland), 2,2,5-trimethyl-5-pentyl-1-cyclopentanone (manufactured by Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (manufactured by Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (manufactured by Givaudan SA, Vernier, Switzerland); Group 3: Damascone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (manufacturer: Firmenich SA, Geneva, Switzerland), (1’R)-2-[2-(4’-methyl-3’-cyclohexen-1’-yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damasconone, 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 (manufacturer: Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (manufacturer: Firmenich SA, Geneva, Switzerland), (1S,1’R)-[1-(3’,3’-dimethyl-1’-cyclohexyl)ethoxycarbonyl]methyl propanoate (manufacturer: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1-cyclohexyl acetate (manufacturer: International Flavors and Fragrances, USA), 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (manufacturer: Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (manufacturer: Firmenich SA, Geneva, Switzerland), (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, terpenyl isobutyrate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate (manufacturer: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, (1S,1’R)-2-[1-(3’,3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propanoate (manufacturer: Firmenich SA, Geneva, Switzerland), para-tert-butylcyclohexanone, menthol thiol, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexyl propionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate; Group 4: methyl cedryl ketone (manufacturer: International Flavors and Fragrances, USA), (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2,6 dec-3-en-8-yl 2-methylpropanoate and (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2,6Mixture with deca-4-en-8-yl 2-methylpropanoate, vetiverol, vetivenone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone (manufacturer: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10-tetramethyl-1-oxaspiro[4.5]deca-3,6-diene and (5RS,9SR,10RS) isomer, 6-ethyl-2,10,10-trimethyl-1-oxaspiro[4.5]deca-3,6-diene, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4-indenone (manufacturer: International Flavors and Fragrances, USA), mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal (manufacturer: Firmenich SA, Geneva, Switzerland), 3’,4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-en-9-spiro-2’-oxirane (manufacturer: Firmenich SA, Geneva, Switzerland), 9 / 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate (manufacturer: Firmenich SA, Geneva, Switzerland), octalinol, (dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan, manufacturer: Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]deca-3-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]deca-4-en-8-yl acetate, and tricyclo[5.2.1.0(2,6)]deca-3-en-8-yl propanoate and tricyclo[5.2.1.0(2,6)]deca-4-en-8-yl propanoate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2’-cyclohexen-4’-one; Group 5: Camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane (manufacturer: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one and 10-ethylidene-3-oxatricyclo 2,7 undecan-4-one and its mixture (manufacturer: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (manufacturer: Firmenich SA, Geneva, Switzerland); Group 6: (Trimethyl-13-oxabicyclo-[10.1.0]-trideca-4,8-diene (manufacturer: Firmenich SA, Geneva, Switzerland), 9-hexadecen-16-olide (manufacturer: Firmenich SA, Geneva, Switzerland), pentadecenolide (manufacturer: Firmenich SA, Geneva, Switzerland), 3-methyl-(4 / 5)-cyclopentadecenone (manufacturer: Firmenich SA, Geneva, Switzerland), 3-methylcyclopentadecanone (manufacturer: Firmenich SA, Geneva, Switzerland), pentadecanolide (manufacturer: Firmenich SA, Geneva, Switzerland), cyclopentadecanone (manufacturer: Firmenich SA, Geneva, Switzerland), 1-ethoxyethoxy)cyclododecane (manufacturer: Firmenich SA, Geneva, Switzerland), 1,4-dioxacycloheptadecane-5,17-dione, 4,8-cyclododecadien-1-one; Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal (manufacturer: Givaudan SA, Vernier, Switzerland), 2,2,2-trichloro-1-phenylethyl acetate.

[0075] Preferably, the fragrance contains components selected from Groups 1 to 7, which are defined as at least 30%, preferably at least 50%, more preferably at least 60%. More preferably, the fragrance contains components of Groups 3 to 7, which are defined as at least 30%, preferably at least 50%. Most preferably, the fragrance contains components of Groups 3, 4, 6 or 7, which are defined as at least 30%, preferably at least 50%.

[0076] According to another preferred embodiment, the fragrance contains components having a logP of more than 3, preferably more than 3.5, even more preferably more than 3.75, which are at least 30%, preferably at least 50%, more preferably at least 60%.

[0077] According to a specific embodiment, the fragrance used in the present invention contains a primary alcohol of less than 10% of its own weight, a secondary alcohol of less than 15% of its own weight, and a tertiary alcohol of less than 20% of its own weight. Advantageously, the fragrance used in the present invention does not contain any primary alcohol and contains less than 15% of secondary and tertiary alcohols.

[0078] According to one embodiment, the oil phase (or oil-based core) contains 25 to 100% by weight, preferably 25 to 98% by weight of a fragrance oil containing at least 15% by weight of a high-impact fragrance raw material with LogT < -4, 0 to 75% by weight, preferably 2 to 75% by weight of a density equalizing material having a density exceeding 1.07 g / cm 3 and contains.

[0079] The "high-impact fragrance raw material" should be understood as a fragrance raw material with LogT < -4. The odor threshold concentration of a chemical compound is partially determined by its shape, polarity, partial charge, and molecular mass. For convenience, the odor threshold concentration is expressed as the common logarithm of the threshold concentration, i.e., Log[threshold] ("LogT").

[0080] The "density equalizing material" should be understood as a material having a density exceeding 1.07 g / cm 3 and preferably having a low odor or being odorless.

[0081] The odor threshold concentration of a fragrance compound is determined using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact volume of the fragrance oil component injected by syringe, the exact split ratio, and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate is accurately measured, and the sampled volume is calculated assuming a 12-second duration of human inhalation. Since the exact concentration at the detector at any given time is known, the mass per volume inhaled, and thus the concentration of the fragrance compound, is known. To determine the threshold concentration, the solution is delivered to the sniff port at the back-calculated concentration. The panelist sniffs the GC effluent and identifies the retention time when the odor is perceived. The odor threshold concentration of the fragrance compound is determined by averaging across all panelists. The determination of the odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September, 2008, pages 54 - 61.

[0082] The properties of high-impact fragrance raw materials with LogT < -4 and density equalizing materials having a density exceeding 1.07 g / cm 3 are described in International Publication No. WO 2018 / 115250, the content of which is incorporated by reference.

[0083] According to one embodiment, high-impact fragrance raw materials with LogT < -4 are (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1-phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1-phenyl acetate, pyrazobutyl, 3-propylphenol, 1-(3-methyl-1-benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1-(3,3 / 5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, a mixture containing (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benz[b]furan-2-one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benz[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-4alpha,8abeta-dimethyl-4a-naphthalenol, patchoulol, 2-methoxy-4-(1-propenyl)phenol, a mixture containing (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylene-2-phenyl-2H-pyran, 4-methylene-2-phenyltetrahydro-2H-pyran and (+-)-4-methyl-2-phenyl-3,A mixture containing 6-dihydro-2H-pyran, 4-hydroxy-3-methoxybenzaldehyde, nonenal, 2-methoxy-4-propylphenol, 3-methyl-5-phenyl-2-pentenenitrile, 1-(spiro[4.5]deca-6 / 7-ene-7-yl)-4-penten-1-one, 2-methoxynaphthalene, (-)-(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 5-nonanolid, (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, beta,2,2,3-tetramethyl-delta-methylene-3-cyclopentene-1-butanol, deltadamascone ((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, octalactone gamma, ethyl 3-phenyl-2-propenoate, (-)-(2E)-2-ethyl-4-[(1R)-2,2,3-trimethyl-3-cyclopentene-1-yl]-2-buten-1-ol, p-cresyl acetate, dodecalactone, tricyclon, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1-one, undecalactone, (1R,4R)-8-mercapto-3-p-menthanone, (3S,3aS,6R,7aR)-3,6-dimethylhexahydro-1-benzofuran-2(3H)-one, beta-ionone, (+-)-6-pentyltetrahydro-2H-pyran-2-one, (3E,5Z)-1,3,5-undecatriene, 10-undecenal, (9E)-9-undecenal (9Z)-9-undecenal, (Z)-4-decenal, (+-)-ethyl 2-methylpentanoate, 1,2-Diallyl disulfide, 2-tridecenenitrile, 3-tridecenenitrile, (+-)-2-ethyl-4,4-dimethyl-1,3-oxathiane, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1-one, 3-(4-tert-butylphenyl)propanal, allyl(cyclohexyloxy)acetate, methyl naphthyl ketone, (+-)-(4E)-3-methyl-4-cyclopentadecen-1-one, (+-)-5E3-methyl-5-cyclopentadecen-1-one, cyclopropylmethyl 3-hexenoate, (4E)-4-methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1-(5-propyl-1,3-benzodioxol-2-yl)ethanone, 4-methyl-2-pentylpyridine, (+-)-(E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (3aRS,5aSR,9aSR,9bRS)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, (2S,5R)-5-methyl-2-(2-propanyl)cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran-2-one, (+-)-3-(3-isopropyl-1-phenyl)butanal, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)penta-1-en-3-one, indole, 7-propyl-2H,4H-1,5-benzodioxepin-3-one, ethyl praline, (4-methylphenoxy)acetaldehyde, ethyl tricyclo[5.2.1.0., 2,6Selected from the group consisting of decane-2-carboxylate, (+)-(1’S,2S,E)-3,3-dimethyl-5-(2’,2’,3’-trimethyl-3’-cyclopentene-1’-yl)-4-penten-2-ol, (4E)-3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopentene-1-yl]-4-penten-2-ol, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, methylnonylacetaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropanoate, (E)-4-decenal, (+-)-2-ethyl-4-(2,2,3-trimethyl-3-cyclopentene-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-cyclopentene-1-yl)-4-penten-2-ol, allyl (2 / 3-methylbutoxy) acetate, (+-)-(2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl]-2-buten-1-one, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl]-1-penten-3-one, and mixtures thereof.

[0084] According to one embodiment, the flavor raw material with LogT < -4 is selected from the group consisting of aldehydes, ketones, alcohols, phenols, ester lactones, ethers, epoxides, nitriles, and mixtures thereof.

[0085] According to one embodiment, the flavor raw material with LogT < -4 contains at least one compound selected from the group consisting of alcohols, phenols, ester lactones, ethers, epoxides, nitriles, and mixtures thereof, preferably in an amount between 20% and 70% by weight based on the total weight of the flavor raw material with LogT < -4.

[0086] According to one embodiment, the fragrance raw material with LogT < -4 contains aldehydes, ketones, and mixtures thereof in an amount between 20% and 70% by weight based on the total weight of the fragrance raw materials with LogT < -4.

[0087] Therefore, the remaining fragrance raw materials contained in the oil-based core may have LogT > -4.

[0088] According to one embodiment, fragrance raw materials with LogT > -4 are ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6 / 8-sec-butylquinoline, (+-)-3-(1,3-benzodioxol-5-yl)-2-methylpropanal, benzyl propionate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, methyl 2-((1RS,2RS)-3-oxo-2-pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 1,3,3-trimethyl-2-oxabicyclo[2.2.2] Octane, Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, Dodecanal, 1-oxa-12 / 13-cyclohexadecene-2-one, (+-)-3-(4-isopropylphenyl)-2-methylpropanal, Aldehyde C11, (+-)-2,6-dimethyl-7-octen-2-ol, Allyl 3-cyclohexylpropanoate, (Z)-3-hexenyl acetate, 5-methyl-2-(2-propanyl)cyclohexanone, Allyl heptanoate, 2-(2-methyl-2-propanyl)cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl butyrate, Geranyl acetate, Neryl acetate, (+-)-1-phenylethyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, Ethyl 3-oxobutanoate, (2Z)-Ethyl 3-hydroxy-2-butenoate, 8-p-menthanol, 8-p-menthanyl acetate, 1-p-menthanyl acetate, (+-)-2-(4-methyl-3-cyclohexen-1-yl)-2-propanyl acetate, (+-)-2-methylbutyl butanoate, 2-{ (1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3,5,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2-cyclohexylethyl acetate, Octanal, Ethyl butanoate, (+-)-(3E)-4-(2,6,6-trimethyl-1 / 2-cyclohexen-1-yl)-3-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) Selected from the group consisting of heptan-2-ol, (+-)-3,7-dimethyl-3-octanol, 1-methyl-4-(2-propanilidene) cyclohexene, (+)-(R)-4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene, benzyl 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 propanoate, and mixtures thereof.

[0089] According to one embodiment, the fragrance formulation is 0 to 60% by weight of a hydrophobic solvent (relative to the total weight of the fragrance formulation), and 40 to 100% by weight of a fragrance oil (relative to the total weight of the fragrance formulation), having the following characteristics: At least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of fragrance components having a logP greater than 3, preferably greater than 3.5, At least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of the bulky materials of groups 1 to 6, preferably 3 to 6, defined above, and At least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high-impact fragrance materials having a defined LogT < -4 having at least two, preferably all, of the above, a fragrance oil, and Optionally, further hydrophobic active ingredients, and comprises.

[0090] According to a particular embodiment, the fragrance contains 0 to 60% by weight of a hydrophobic solvent.

[0091] According to certain embodiments, the hydrophobic solvent is preferably a density equilibration material selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl salicylate and ethyl salicylate, benzyl cinnamate, and mixtures thereof.

[0092] In certain embodiments, the hydrophobic solvent has Hansen solubility parameters that are compatible with the encapsulated fragrance oil.

[0093] The term "Hansen solubility parameter" refers to the solubility parameter approach proposed by Charles Hansen, which is used to predict polymer solubility and is understood to be developed based on the basis that the total energy of vaporization of a liquid consists of several individual parts. 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 +δΡ 2 +δΗ 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 bonding ("h-bonding") value (hereinafter also referred to as hydrogen bonding). For a more detailed explanation of the parameters and values, see Charles Hansen, The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, Danish Technical Press (Copenhagen, 1967).

[0094] The Euclidean difference in solubility parameters between the fragrance and the solvent is (4*(δD solvent -δD fragrance ) 2 +(δPsolvent -δP fragrance ) 2 +(δH solvent -δH fragrance ) 2 ) 0.5 calculated as δD solvent δP solvent and δH solvent are the Hansen dispersion value, the Hansen polarizability value, and the Hansen h-bonding value of the solvent, respectively, and δD fragrance δP fragrance and δH fragrance are the Hansen dispersion value, the Hansen polarizability value, and the Hansen h-bonding value of the fragrance, respectively.

[0095] In certain embodiments, the fragrance oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from the first group consisting of an atomic dispersion force (δD) of 12 to 20, a dipole moment (δP) of 1 to 8, and a hydrogen bond (δH) of 2.5 to 11.

[0096] In certain embodiments, the fragrance oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from the second group consisting of an atomic dispersion force (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δH) of 2.5 to 11, preferably 4 to 11.

[0097] In certain embodiments, at least 90%, preferably at least 95%, most preferably at least 98% of the fragrance oil has at least two Hansen solubility parameters selected from the first group consisting of an atomic dispersion force (δD) of 12 to 20, a dipole moment (δP) of 1 to 8, and a hydrogen bond (δH) of 2.5 to 11.

[0098] In certain embodiments, the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of an atomic dispersive force (δD) of 12 to 20, preferably 14 to 20, a dipole moment (δP) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δH) of 2.5 to 11, preferably 4 to 11.

[0099] According to one embodiment, the perfume formulation includes a fragrance modifier (which can be used in addition to the hydrophobic solvent if present, or as a replacement for the hydrophobic solvent if the hydrophobic solvent is absent).

[0100] Preferably, the fragrance modifier has i. a vapor pressure of less than 0.0008 Torr at 22 °C, and ii. a clogP of 3.5 or greater, preferably 4.0 or greater, more preferably 4.5, and iii. at least two Hansen solubility parameters selected from a first group consisting of an atomic dispersive force of 12 to 20, a dipole moment of 1 to 7, and a hydrogen bond of 2.5 to 11, and iv. when in a solution containing a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22 °C, at least two Hansen solubility parameters selected from a second group consisting of an atomic dispersive force of 14 to 20, a dipole moment of 1 to 8, and a hydrogen bond of 4 to 11, and is defined as a fragrance material having the above properties.

[0101] Preferably, by way of example, the following components can be listed as modifiers, but the list is not limited to the following materials: Alcohol C12, Oxacyclohexadec-12 / 13-en-2-one, 3-[(2’,2’,3’-trimethyl-3’-cyclopenten-1’-yl)methoxy]-2-butanol, Cyclohexadecanone, (Z)-4-Cyclopentadecen-1-one, Cyclopentadecanone, (8Z)-Oxacycloheptadec-8-en-2-one, 2-[5-(Tetrahydro-5-methyl-5-vinyl-2-furyl)-tetrahydro-5-methyl-2-furyl]-2-propanol, Muguet aldehyde, 1,5,8-Trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene, (+-)-4,6,6,7,8,8-Hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (+)-(1S,2S,3S,5R)-2,6,6-Trimethylspiro[bicyclo[3.1.1]heptane-3,1’-cyclohexane]-2’-en-4’-one, Oxacyclohexadecan-2-one, 2-{ (1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, (+)-(4R,4aS,6R)-4,4a-Dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone, Amyl cinnamic aldehyde, Hexyl cinnamic aldehyde, Hexyl salicylate, (1E)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1,6-heptadien-3-one, (9Z)-9-Cycloheptadecen-1-one.

[0102] According to certain embodiments, the hydrophobic material does not contain any active ingredients (such as fragrances). According to this particular embodiment, the hydrophobic material preferably comprises a hydrophobic solvent selected from the group consisting of isopropyl myristate, triglycerides (such as Neobee® MCT oil, vegetable oils), D-limonene, silicone oils, mineral oils, and mixtures thereof, preferably consisting of them, and optionally preferably contains a hydrophilic solvent selected from the group consisting of 1,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1,2-propanediol), 1,3-propanediol, dipropylene glycol, glycerol, glycol ethers, and mixtures thereof.

[0103] The term "biocide" refers to a chemical substance that can kill organisms (such as microorganisms) or reduce or prevent their growth and / or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and industries such as preventing the contamination of, for example, water, agricultural products including seeds, and oil pipelines. Biocides can be pesticides including fungicides, herbicides, insecticides, algicides, molluscicides, acaricides, and rodenticides; and / or antimicrobial agents such as bactericides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal agents, and / or antiparasitic agents.

[0104] As used herein, "pest control agent" refers to a substance that repels or attracts pests and helps to reduce, inhibit, or promote their growth, development, or their activities. Pests refer to any organism that is invasive or troublesome to plants or animals, regardless of whether they are animals, plants, or fungi, and pests include insects, especially arthropods, mites, spiders, fungi, weeds, bacteria, and other microorganisms.

[0105] As used herein, "flavor oil" means a flavor component currently used in the preparation of flavor formulations, or a mixture of flavor components, solvents or adjuvants, i.e., a specific mixture of components intended to be added to an edible composition or chewable product to impart, improve or modify its sensory properties, particularly its flavor and / or taste. Flavor components are well known to those skilled in the art, and their properties are not warranted to be described in detail herein, nor are they exhaustive in any case. A flavorist of ordinary skill can select them based on their general knowledge according to the intended use or application and the sensory effects desired to be achieved. Many of these flavor components are listed in references such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent version, or other works of a similar nature such as Fenaroli’s Handbook of Flavor Ingredients, 1975, CRC Press or Synthetic Food Adjuncts, 1947 (M.B. Jacobs, van Nostrand Co., Inc.). Solvents and adjuvants currently used for the preparation of flavor formulations are also well known in the art.

[0106] In certain embodiments, the flavor is a mint flavor. In more specific embodiments, the mint is selected from the group consisting of peppermint and spearmint.

[0107] In further embodiments, the flavor is a cooling agent or a mixture thereof.

[0108] In another embodiment, the flavor is a menthol flavor.

[0109] Fruit-derived or fruit-based flavors in which citric acid is the dominant naturally occurring acid include, for example, citrus fruits (e.g., lemon, lime), limonene, strawberry, orange, and pineapple, but are not limited thereto. In one embodiment, the flavored food is lemon, lime or orange juice directly extracted from the fruit. Further embodiments of the flavor include juice or liquid extracted from orange, lemon, grapefruit, key lime, citron, clementine, mandarin, tangerine, and any other citrus fruit, or variants or hybrids thereof. In certain embodiments, the flavor includes liquids extracted or distilled from orange, lemon, grapefruit, key lime, citron, clementine, mandarin, tangerine, any other citrus fruit, or variants or hybrids thereof, pomegranate, kiwifruit, watermelon, apple, banana, blueberry, melon, ginger, bell pepper, cucumber, passion fruit, mango, pear, tomato, and strawberry.

[0110] In certain embodiments, the flavor includes a composition containing limonene, and in certain embodiments, the composition is a citrus fruit further containing limonene.

[0111] In another particular embodiment, the flavor includes a flavor selected from the group consisting of strawberry, orange, lime, tropical, berry mix, and pineapple.

[0112] The term "flavor" includes not only flavors that impart or modify the smell of food, but also materials that impart or modify taste. The latter does not necessarily have a taste or smell per se, but can modify the taste provided by other ingredients, such as saltiness enhancing ingredients, sweetness enhancing ingredients, umami enhancing ingredients, bitterness blocking ingredients, and the like.

[0113] In a further embodiment, a suitable sweetening component may be included in the particles described herein. In certain embodiments, the sweetening component is selected from the group consisting of sugars (e.g., but not limited to, sucrose), stevia components (e.g., but not limited to, stevioside or rebaudioside A), sodium cyclamate, aspartame, sucralose, sodium saccharin, and acesulfame K or mixtures thereof.

[0114] Specific embodiments of the aqueous phase According to certain embodiments, the method of the present invention includes the step of adding a reactant to the aqueous phase during the reaction. This optional reactant can participate in the shell formation of the microcapsules.

[0115] The reactant can be water-soluble or water-suspendable. Examples of suitable reactants include alcohols, amines, phenols, thiols, and mixtures thereof.

[0116] According to certain embodiments, the polyfunctional monomer is a polyfunctional isocyanate, and at any stage of the method, no substantial amount of an amine or other water-soluble reactants polymerizable with the polyfunctional isocyanate, such as alcohols, thiols, ureas, urethanes, and mixtures thereof, is added.

[0117] According to one embodiment, the weight ratio between the oil phase and the aqueous phase is included between 1:99 and 50:50, preferably between 10:90 and 40:60.

[0118] Coacervate particles Core-shell particles can be "simple" core-shell particles (i.e., produced by "simple" coacervation) or "complex" coacervates (i.e., produced by "complex" coacervation) or mixtures thereof. It is understood that by simple coacervation, only one polymer (or copolymer) is phase-separated and then precipitated from a homogeneous solution in the presence of a poor solvent to form core-shell particles. By complex coacervation, a method is understood in which at least two polymers (or polyelectrolytes) having opposite charges (under specific pH values) coacervate together to form core-shell particles. Complex coacervation also includes the formation of coacervates from charged polyions and polymers of opposite charge.

[0119] Complex coacervate particles According to certain embodiments, the coacervate is a complex coacervate particle. In other words, according to this embodiment, the coacervate particles comprise at least a first polymer and a second polymer. According to one embodiment, the first polymer and the second polymer are water-soluble.

[0120] The first polymer and the second polymer can also be named a first polyelectrolyte and a second polyelectrolyte, respectively.

[0121] According to one embodiment, the first and / or second polymer is a biopolymer.

[0122] According to one embodiment, the first polymer contains at least one cationic group such as an amino group, an azole group, an amide group, a quaternary ammonium cation or a guanidinium cation.

[0123] The first polymer is preferably selected from the group consisting of proteins (such as gelatin, whey protein, albumin, etc.), chitosan and derivatives, cationically modified polysaccharides, polyethyleneimine, poly(amidoamine), poly(amino-co-ester), cationic polyacrylate or mixtures thereof.

[0124] According to one embodiment, the protein is preferably a plant protein selected from the group consisting of potato protein, chickpea protein, pea protein, broad bean protein, barley protein, oatmeal protein, wheat gluten protein, lupin protein, canola protein, rice protein, sunflower seed protein, and mixtures thereof.

[0125] The second polymer is selected from the group of polymers consisting of modified starch, gum arabic, chitosan, alginate, cellulose derivatives, guar gum, pectate, pectin, carrageenan, sodium caseinate, hyaluronic acid, polyacrylic acid and methacrylic acid, xanthan gum, or preferably a polyanion selected from the group consisting of trisodium phosphate, trisodium trimetaphosphate, sodium pyrophosphate, sodium dextran sulfate salt, and mixtures thereof.

[0126] The weight ratio between the first polymer and the second polymer is preferably included between 1:9 and 9:1, more preferably between 3:7 and 7:3.

[0127] According to one embodiment, the coacervate particles contain chitosan (as the first polymer) and sodium caseinate (as the second polymer).

[0128] According to one embodiment, the coacervate particles contain whey protein (as the first polymer) and gum arabic (as the second polymer).

[0129] According to one embodiment, the coacervate particles contain whey protein (as the first polymer) and chitosan (as the second polymer).

[0130] According to one embodiment, the coacervate particles contain chitosan (as the first polymer) and sodium alginate (as the second polymer).

[0131] According to one embodiment, the coacervate particles include chitosan (as the first polymer) and pectin (as the second polymer).

[0132] According to one embodiment, the coacervate particles include a polymer and a polyion (such as anions and cations) that is oppositely charged to the polymer. Examples of anions are polyvalent anions such as sodium tripolyphosphate, trisodium trimeta phosphate, sodium pyrophosphate, sodium dextran sulfate salt, etc. Examples of cations are Sn 4+ , Al 3+ , Fe 3+ , Sb 3+ , Ga 3+ , Ca 2+ , Mg 2+ , Zn 2+ , Ba 2+ , Cd 2+ , Co 2+ , Cu 2+ and polyvalent metal cations such as mixtures thereof.

[0133] According to a particular embodiment, the coacervate particles are prepared by flash nanoprecipitation (FNP). The coacervate particles can typically be prepared using a multi-inlet vortex mixer (MIVM) device containing between 2 and 4 inlets.

[0134] The preparation of coacervate particles using the flash nanoprecipitation method (FNP) has been found to exhibit several advantages. In fact, by preparing through FNP, which is one of the important factors for the surface activity of these coacervate particles at the oil-in-water interface for preparing stable pickering emulsions, coacervate particles with a controlled size and a narrow size distribution can be obtained.

[0135] Furthermore, when the biopolymer is used as a polyelectrolyte, the FNP can provide a coacervate particle suspension having a higher biopolymer content, which means that more biopolymer can be embedded in the shell during the shell formation process.

[0136] Finally, it is possible to include the active ingredient in the coacervate particles during the FNP process, thus providing an additional advantage to the microcapsules.

[0137] According to one embodiment, when the coacervate particles are composite coacervate particles (i.e., containing at least two polymers), the coacervate particles are (i) injecting a first polymer solution into a first flow of a multi-inlet vortex mixer; (ii) injecting a second polymer solution into a second flow of the multi-inlet vortex mixer; (iii) optionally, injecting a third solution and / or a fourth solution into a third flow and / or a fourth flow of the multi-inlet vortex mixer; (iv) mixing the solutions injected from different flows to form a composite coacervate particle suspension; prepared by a flash nanoprecipitation (FNP) process comprising.

[0138] The first polymer and the second polymer are defined as described above.

[0139] The third solution and / or the fourth solution typically contains buffer water.

[0140] The buffer can be added in step (iii) to adjust the pH typically between 2.0 and 8.0.

[0141] The fourth solution and / or the third solution can contain the active ingredient. The third and / or fourth solutions are preferably water miscible.

[0142] A person skilled in the art could select appropriate process parameters. The injection is typically carried out at a rate within the range of 10 mL / min to 120 mL / min, preferably within the range of 20 mL / min to 80 mL / min, using a pump (e.g., Harvard's PHD ULTRA).

[0143] A typical process is shown in Figure 2.

[0144] Simple coacervate particles According to certain embodiments, the coacervate is simple coacervate particles. In other words, according to this embodiment, the coacervate particles are (a) water-soluble polymer (or copolymer): coacervate particles formed via precipitation from a water-soluble polymer solution in the presence of a poor solvent, or (b) water-insoluble polymer (or copolymer): coacervate particles formed via precipitation from a water-insoluble polymer solution in the presence of water or an aqueous solution (aqueous phase) and contain only.

[0145] Simple coacervation particles are (i) injecting a polymer solution into a first stream of a multi-inlet vortex mixer; (ii) injecting a poor solvent into a second stream of the multi-inlet vortex mixer; (iii) optionally, injecting a third solution and / or a fourth solution into a third stream and / or a fourth stream of the multi-inlet vortex mixer; (iv) mixing the solutions injected from different streams to form a simple coacervate particle suspension and can be obtained by a flash nanoprecipitation process.

[0146] Depending on the nature of the polymer (water-soluble or water-insoluble) used in step (i), a person skilled in the art could select an appropriate poor solvent in step (ii).

[0147] (a) Water-soluble polymer (or copolymer) For the purposes of the present invention, the "water-soluble polymer" is intended to encompass any polymer that forms a single-phase solution in water. Preferably, this forms a single-phase solution when dissolved in water at a high concentration of 20% by weight, more preferably at a high concentration of 50% by weight. Most preferably, this forms a single-phase solution when dissolved in water at any concentration.

[0148] Water-soluble polymers include proteins (such as gelatin, sodium caseinate, whey protein, albumin, etc.), chitosan and derivatives, cationically modified polysaccharides, polyethyleneimine, poly(amidoamine), poly(amino-co-ester), cationic polyacrylate, modified starch, gum arabic, chitosan, alginate, zein, cellulose derivatives, guar gum, pectate, pectin, carrageenan, hyaluronic acid, polyacrylic acid and methacrylic acid, xanthan gum, or polyanions consisting of sodium tripolyphosphate, trisodium trimetaphosphate, sodium pyrophosphate, sodium dextran sulfate salt, poly(ethylene glycol), polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, polyethylene oxide, polyhydroxyethyl methacrylate and other hydrophilic polyacrylates, poly(N-isopropylacrylamide), polyols, polyoxazolines, polyphosphates, polyphosphazenes, polyvinyl methyl ether, locust bean gum, xyloglucan, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methylcellulose, and may be selected from the group consisting of. According to one embodiment, a water-soluble copolymer containing a hydrophilic block in the copolymer, the hydrophilic block may be selected from polyvinyl alcohol, poly(ethylene glycol), polyethylene oxide, polyacrylate, polyacrylamide, polyol, polyvinyl pyrrolidone or other polyelectrolytes.

[0149] Examples of poor solvents include water-miscible organic solvents, acidic solutions, alkaline solutions, or salt solutions. Optionally, the process may further include a step for removing the organic solvent from the particle suspension.

[0150] (b) Water-insoluble polymer (or copolymer) The polymer (or copolymer) may include proteins, polycaprolactone polyols, polylactic acid-co-glycolic acid, polylactic acid, polyepoxides, polyanhydrides, poly(meth)acrylates, and copolymers containing blocks of polylactic acid-co-glycolic acid, polylactic acid, polyvinyl alcohol, poly(ethylene glycol), polyethylene oxide, polyacrylate, polyacrylamide, polyols, and polyvinyl pyrrolidone.

[0151] The water-insoluble polymer or copolymer should be dissolved in an organic solvent soluble in water in step i). Examples of water-soluble solvents include methanol, ethanol, ethylene glycol, propylene glycol, glycerin, acetone, ethyl acetate, tetrahydrofuran, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, acetonitrile, pyridine, acetic acid, 2-methoxyethanol, 2-ethoxyethanol, morpholine, N-methyl-2-pyrrolidone, formamide, and acetamide. The polymer or copolymer can be dissolved in these solvents and precipitated from the solution in the presence of water or an aqueous solution as a poor solvent in step ii).

[0152] Water or an aqueous solution acts as a poor solvent. For example, acidic solutions, alkaline solutions, or salt solutions can also be mentioned.

[0153] Optionally, the process may further include a step for removing the organic solvent from the particle suspension.

[0154] According to one embodiment, the coacervate particles have a particle size included between 100 nm and 10 μm, preferably between 200 nm and 5 μm.

[0155] "Particle size" means the average diameter of particles based on the size distribution measured by dynamic light scattering (DLS) using a Zetasizer Nano ZS device manufactured by Malvern Instruments Ltd. (UK) when the particles are dispersed in the aqueous phase.

[0156] Preferably, the total amount of coacervate particles present in the aqueous phase is included between 0.1 and 20% by weight, preferably between 0.2 and 10% by weight.

[0157] According to one embodiment, the coacervate particles preferably contain an active ingredient selected from the group consisting of cosmetic ingredients, skin care ingredients, fragrance ingredients, flavor ingredients, malodor preventing ingredients, antimicrobial ingredients, pharmaceutical or pesticide ingredients, disinfectant ingredients, insect repellents or attractants, and mixtures thereof.

[0158] According to one embodiment, the active ingredient is an antimicrobial ingredient. The antimicrobial ingredient can be an antibacterial ingredient, an antifungal ingredient, and / or an antiparasitic ingredient. Non-exhaustive examples of such ingredients include quaternary ammonium and polymers containing quaternary ammonium groups, cathelicidin antimicrobial peptides, chitosan and derivatives, polyphenols as well as silver particles, inorganic particles such as titanium dioxide particles and zinc oxide particles.

[0159] When prepared by FNP, the active ingredient can be added by mixing the active ingredient (or active ingredient solution) into the polymer solution during the process, or by injecting the active ingredient into one of the flows of a multi-inlet vortex mixer.

[0160] Optional step: outer coating According to a particular embodiment, the surface of the microcapsules obtained by the method of the invention can be modified in an additional step. Monomers or polymers suitable for surface modification are selected from compounds that can form a chemical bond between the monomer or polymer and the microcapsules and can improve the compatibility between the microcapsules and the target substrate.

[0161] Thus, according to certain embodiments of the present invention, at the end of step 3) of the method, in order to form an outer coating on the microcapsules, a polymer selected from the group consisting of non-ionic polysaccharides, cationic polymers, polysuccinimide derivatives (e.g., described in WO 2021 / 185724), and mixtures thereof can also be added to the slurry of the present invention.

[0162] Non-ionic polysaccharide polymers are well known to those skilled in the art. Preferred non-ionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose, and hydroxypropyl methylcellulose.

[0163] 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, and further preferably less than about 7 meq / g, more preferably less than about 6.2 meq / g. The cationic charge density of the cationic polymer may be determined under a chemical test for nitrogen determination by the Kjeldahl method described in the United States Pharmacopeia. Preferred cationic polymers are selected from those containing units comprising primary, secondary, tertiary, and / or quaternary amine groups that can form part of the main polymer chain or be carried by side substituents directly attached thereto. The weight average (Mw) molecular weight of the cationic polymer is preferably from 10,000 to 3.5 million daltons, more preferably from 50,000 to 2 million daltons.

[0164] According to certain embodiments, 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 galactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride are used. Preferably, the copolymer is selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium 10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or galactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.

[0165] Specific examples of commercial products may include Salcare® SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, manufacturer: BASF) or Luviquat®, for example PQ 11N, FC 550 or Style (copolymer of polyquaternium-11 to 68 or quaternized vinylpyrrolidone, manufacturer: BASF), or Jaguar® (C13S or C17, manufacturer Rhodia).

[0166] According to any one of the above embodiments of the present invention, an amount of the above polymer contained between about 0% to 5% w / w, or even between about 0.1% to 2% w / w is added, and the percentage is expressed on a w / w basis relative to the total weight of the slurry obtained after step 3). It is clearly understood by those skilled in the art that only a part of the added polymer is incorporated into the microcapsule shell / deposited on the microcapsule shell.

[0167] Another object of the present invention is a method for preparing microcapsule powder, comprising: 1) suspending coacervate particles in water to form an aqueous phase; 2) mixing at least one polyfunctional monomer with a hydrophobic material to form an oil phase; 3) adding the oil phase to the aqueous phase and mixing them to form a water-in-oil type Pickering emulsion under conditions enabling the formation of a microcapsule slurry by interfacial polymerization; 4) drying the microcapsule slurry to obtain microcapsule powder. The method includes the above steps.

[0168] Any drying method known to those skilled in the art can be used. In particular, the slurry can be spray-dried in the presence of a polymer carrier material such as preferably polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, plant gum, pectin, xanthan, alginate, carrageenan or cellulose derivative to obtain microcapsules in powder form.

[0169] The microcapsule powder may also contain a free fragrance.

[0170] Microcapsule An object of the present invention is a microcapsule slurry or microcapsule powder obtained by the method defined above.

[0171] Another object of the present invention is a microcapsule or a microcapsule slurry containing at least one microcapsule, wherein the microcapsule comprises a core containing a hydrophobic material, preferably a perfume oil, preferably an oil-based core, and a composite shell containing a first material and a second material, the first material and the second material are different, the first material is core sebacic acid particles, the second material is a polymer material, a composite shell, and a microcapsule or a microcapsule slurry comprising

[0172] Regarding hydrophobic materials in particular, the previous embodiments and definitions, and the above core sebacic acid particles in this specification are applied mutatis mutandis.

[0173] The polymer material is preferably selected from the group consisting of polyureas, polyesters, polyurethanes, polyamides, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal, and mixtures thereof.

[0174] Preferably, the weight ratio in the slurry between the first material and the second material is included between 1:99 and 99:1, preferably between 10:90 and 99:1.

[0175] Preferably, the second material is present in an amount of less than 5% by weight based on the total weight of the microcapsule slurry.

[0176] In a specific embodiment, the shell material is a biodegradable material.

[0177] In a specific embodiment, the shell has a biodegradability of at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.

[0178] In certain embodiments, the core-shell microcapsules have a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.

[0179] It is understood that the core-shell microcapsules, including all components such as the core, shell and optionally the coating, may have a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.

[0180] In certain embodiments, the oil-based core, preferably the perfume oil, has a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.

[0181] OECD301F is a standard test method for biodegradability by the Organization for Economic Cooperation and Development.

[0182] A typical method for extracting the shell to measure biodegradability is disclosed in Gasparini and all in Molecules 2020, 25, 718.

[0183] According to one embodiment, the core sebate particles have a particle size included between 100 nm and 10 μm, preferably between 200 nm and 5 μm.

[0184] Any component When the microcapsules are in the form of a slurry, the microcapsule slurry can contain auxiliary components selected from the group consisting of a thickener / rheology modifier, an antimicrobial agent, an opacifying agent, mica particles, a salt, and a pH stabilizer / buffer component, preferably in an amount between 0 and 15% by weight based on the total weight of the slurry.

[0185] According to another embodiment, the microcapsule slurry of the present invention contains an additional free (i.e., non-encapsulated) fragrance, preferably in an amount between 5 and 50% by weight based on the total weight of the slurry.

[0186] Multiple microcapsule systems According to one embodiment, the microcapsules (first type of microcapsules) of the present invention can be used in combination with a second type of microcapsules.

[0187] Another object of the present invention is a microcapsule delivery system, the microcapsules of the present invention as a first type of microcapsules, a second type of microcapsules, wherein the first type of microcapsules and the second type of microcapsules are different in their hydrophobic materials and / or their wall materials and / or their coacervate particles and / or their coating materials, and a microcapsule delivery system comprising the same.

[0188] According to a specific embodiment, the microcapsule delivery system is in the form of a slurry.

[0189] The wall of the second type of microcapsule can vary. By way of non-limiting example, the polymer shell of the second type of microcapsule comprises a material selected from the group consisting of polyureas, polyurethanes, polyamides, polyhydroxyalkanoates, polyacrylates, polyesters, polyaminoesters, polyepoxides, organosilicons, polycarbonates, polysulfonamides, urea formaldehyde, melamine formaldehyde resins crosslinked with aromatic polyols or polyisocyanates, melamine urea resins, melamine glyoxal resins, gelatin / arabic gum shell walls, and mixtures thereof.

[0190] The second type of microcapsules can include an oil-based core containing a hydrophobic active substance, preferably a fragrance, and a composite shell containing a first material and a second material, where the first material and the second material are different, the first material is a coacervate, and the second material is a polymer material. In certain embodiments, the weight ratio of the first material to the second material is included between 50:50 and 99.9:0.1. In certain embodiments, the coacervate preferably includes a first polyelectrolyte selected from proteins (such as gelatin), polypeptides, or polysaccharides (such as chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate, a cellulose derivative guar gum, pectate, carrageenan, polyacrylic acid and methacrylic acid or xanthan gum, or further plant gums such as gum arabic (acacia gum), most preferably gum arabic. The first material that is a coacervate can be chemically hardened using a suitable cross-linking agent such as glutaraldehyde, glyoxal, formaldehyde, tannic acid, or genipin, or can be enzymatically hardened using an enzyme such as transglutaminase. The second polymer material can be selected from the group consisting of polyureas, polyurethanes, polyamides, polyesters, polyacrylates, organosilicons, polycarbonates, polysulfonamides, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal, and mixtures thereof, preferably polyureas and / or polyurethanes. The second material is preferably present in an amount of less than 3% by weight, preferably less than 1% by weight, based on the total weight of the second type of microcapsule slurry.

[0191] As a non-limiting example, the shell of the second type of microcapsules can be aminoplast-based, polyurethane-based, or polyurethane-based. The shell of the second type of microcapsules can also be a hybrid, i.e., organic-inorganic, for example, a hybrid shell composed of at least two types of cross-linked inorganic particles, or further can be a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0192] According to one aspect, the shell of the second type of microcapsules comprises an aminoplast copolymer such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glyoxal.

[0193] According to another aspect, the shell of the second type of microcapsules is, for example, but not limited to, polyurethane-based made from isocyanate-based monomers and amine-containing crosslinking agents such as guanidine carbonate and / or guanazole. Certain polyurethane microcapsules comprise a polyurethane wall that is a reaction product of polymerization between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of amines (such as water-soluble guanidine salts and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of amines can be omitted. According to a particular aspect, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% of a cationic copolymer of vinyl pyrrolidone and quaternized vinyl imidazole (all percentages are defined by weight relative to the total weight of the colloidal stabilizer). According to another aspect, the emulsifier is an anionic or amphiphilic biopolymer and, in one aspect, may be selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0194] According to another embodiment, the microcapsule wall material of the second type of microcapsules may include any suitable resin, particularly including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include reaction products of aldehydes and amines. Suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include methylol melamine, methylated methylol melamine, imino melamine, and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol, and mixtures thereof. Materials suitable for production can be obtained from one or more of Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (Paterson, New Jersey, USA), and Sigma-Aldrich (St. Louis, Missouri, USA).

[0195] According to another embodiment, the second type of microcapsules 1) a step of mixing a flavor oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) a step of dispersing or dissolving an aminoplast resin and optionally a stabilizer in water to form a dispersion phase; 3) a step of preparing an oil-in-water type dispersion liquid having an average droplet size included between 1 and 100 microns by mixing the oil phase and the dispersion phase; 4) a step of performing a curing step to form the wall of the microcapsules; 5) optionally, a step of drying the final dispersion liquid to obtain dry core-shell microcapsules; are core-shell aminoplast core-shell microcapsules obtained by a method including

[0196] According to one embodiment, the second type of microcapsules is a formaldehyde-free capsule. A typical method for preparing an aminoplast formaldehyde-free microcapsule slurry is 1) preparing an oligomer composition comprising the following reaction products or obtained by reacting the following reaction products together: a. a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound containing two NH2 functional groups; b. an aldehyde component in the form of a mixture of glyoxal, C 4~6 2,2-dialkoxy-ethanal and optionally glyoxalate, wherein the mixture has a molar ratio of glyoxal / C 4~6 2,2-dialkoxy-ethanal of 1 / 1 to 10 / 1; and c. a protic acid catalyst; 2) preparing an oil-in-water dispersion having a droplet size between 1 and 600 microns and comprising: a. oil; b. an aqueous medium; c. at least one oligomer composition obtained in step 1; d. at least one crosslinking agent selected from the following: i. C4-C 12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimers, trimethylolpropane adducts and mixtures thereof; and / or ii. a di- or tri-oxirane compound of the following formula: A-(oxiran-2-ylmethyl) n (wherein, n represents 2 or 3, and 1 represents a C2-C6 group optionally containing 2 to 6 nitrogen atoms and / or oxygen atoms); e. optionally, a C1-C4 compound containing two NH2 functional groups; 3) heating the dispersion; and 4) cooling the dispersion.

[0197] In another specific embodiment, the second type of microcapsules comprises an oil-based core containing a hydrophobic active substance, preferably a fragrance; optionally, an inner shell made of a polymerized polyfunctional monomer; a biopolymer shell containing a protein, wherein at least one protein is crosslinked and.

[0198] According to a specific embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed protein, gelatin, gluten, pea protein, soy protein, silk protein, and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate.

[0199] According to a specific embodiment, the protein comprises sodium caseinate and a globular protein selected from the group consisting of preferably whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins, and mixtures thereof.

[0200] The protein is preferably a mixture of sodium caseinate and whey protein.

[0201] According to a specific embodiment, the biopolymer shell comprises a crosslinked protein selected from the group consisting of sodium caseinate and / or whey protein.

[0202] According to a specific embodiment, the second type of microcapsule slurry comprises an oil-based core containing a hydrophobic active substance, preferably a fragrance; an inner shell made of a polymerized polyfunctional monomer; preferably, a polyisocyanate having at least two isocyanate functional groups; A biopolymer shell containing a protein, wherein at least one protein is crosslinked, and the protein preferably contains a mixture of sodium caseinate and a globular protein, preferably whey protein, the biopolymer shell; Optionally, at least one outer mineral layer; Comprising at least one microcapsule made of.

[0203] According to one embodiment, sodium caseinate and / or whey protein is a crosslinked protein.

[0204] The weight ratio between sodium caseinate and whey protein is preferably between 0.01 and 100, preferably between 0.1 and 10, more preferably between 0.2 and 5.

[0205] According to another specific embodiment, the second type of microcapsule is An oil-based core containing a hydrophobic active substance, preferably a fragrance, and A polyamide shell, Acyl chloride, A first amino compound, A second amino compound Optionally, carbohydrates Containing or obtained from them, a polyamide shell, and A polyamide core-shell polyamide microcapsule containing.

[0206] According to a specific embodiment, the second type of microcapsule is An oil-based core containing a hydrophobic active substance, preferably a fragrance, and A polyamide shell, Preferably, an amount of acyl chloride contained between 5% and 98%, preferably between 20% and 98%, more preferably between 30% and 85% w / w, Preferably, an amount of the first amino compound contained between 1% and 50% w / w, preferably between 7% and 40% w / w, Preferably, it contains a second amino compound in an amount between 1% and 50% w / w, preferably between 2% and 25% w / w. Preferably, it contains a stabilizer, preferably a biopolymer, in an amount between 0% and 90%, preferably between 0.1% and 75%, more preferably between 1% and 70%. Optionally, a carbohydrate comprising or obtained from them, a polyamide shell, and contains

[0207] According to a particular embodiment, the second type of microcapsules comprise an oil-based core containing a hydrophobic active substance, preferably a fragrance, and a polyamide shell, an acyl chloride, a first amino compound, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof, a second amino compound, preferably selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, a biopolymer, preferably selected from the group consisting of potato protein, chickpea protein, pea protein, algal protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, soy protein, rice protein, whey protein, egg white albumin, casein, sodium caseinate, gelatin (preferably fish gelatin), bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo-collagen, silk protein, sericin powder, gelatin and mixtures thereof, Optionally, a carbohydrate, preferably an anionic salt of alginic acid, preferably sodium alginate, pectin, lignin, anionic modified starch, carboxymethyl cellulose, carrageenan and mixtures thereof, a polyamide shell, comprising or obtained from them, and comprises.

[0208] According to another aspect, the shell of the second type of microcapsules is polyurea-based or polyurethane-based. Examples of methods for preparing polyurea-based and polyurethane-based microcapsule slurries are described, for example, in International Patent Application Publication No. WO 2007 / 004166, European Patent Application Publication No. EP 2300146, and European Patent Application Publication No. 25799. Typically, the method for preparing a polyurea-based or polyurethane-based microcapsule slurry is a) dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or a colloid stabilizer to form a dispersion phase; c) adding the oil phase to the dispersion phase to form a water-in-oil type dispersion, wherein the average droplet size is between 1 and 500 μm, preferably between 5 and 50 μm; d) inducing interfacial polymerization and applying conditions sufficient to form microcapsules in the form of a slurry. comprises.

[0209] Flavor compositions and consumer products The microcapsules of the present invention can be used in combination with an active ingredient. Accordingly, an object of the present invention is a composition comprising (i) the microcapsules or microcapsule slurry as defined above, and (ii) an active ingredient, preferably selected from the group consisting of cosmetic ingredients, skin care ingredients, fragrance ingredients, flavor ingredients, malodor preventing ingredients, bactericidal ingredients, fungicidal ingredients, pharmaceutical or pesticidal ingredients, disinfecting ingredients, insect repellents or attractants, and mixtures thereof. a composition comprising.

[0210] The capsules of the present invention exhibit good performance with respect to stability in difficult media.

[0211] Another object of the present invention is a perfume composition comprising: (i) a microcapsule or microcapsule slurry as defined above, wherein the oil contains a perfume; (ii) at least one component selected from the group consisting of a perfume carrier, a perfume adjuvant component, and mixtures thereof; (iii) optionally, at least one perfume adjuvant; A liquid perfume carrier may include, as non-limiting examples, an emulsion system, i.e., a solvent and surfactant system, or a solvent commonly used in perfumes. A detailed description of the nature and types of solvents commonly used in perfumes cannot be exhaustive. However, non-limiting examples include solvents such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol, or ethyl citrate, which are most commonly used. In the case of a composition containing both a perfume carrier and a perfume adjuvant component, other suitable perfume carriers other than those specified above may also be ethanol, a water / ethanol mixture, limonene or other terpenes, isoparaffin, such as those known under the trademark Isopar® (manufacturer: Exxon Chemical), or glycol ethers and glycol ether esters, such as those known under the trademark Dowanol® (manufacturer: Dow Chemical Company). As used herein, "perfume adjuvant component" means a compound that is used in a perfume preparation or composition to impart a pleasant effect and is not a microcapsule as defined above. In other words, such an adjuvant component must be recognized by those skilled in the art as being able to not only have an odor but also positively or at least pleasantly impart or modify the odor of the composition in order to be considered odoriferous.

[0212]

[0213] ​The nature and types of auxiliary perfume components present in the perfume composition do not warrant a more detailed description herein, are not exhaustive in any case, and those skilled in the art can select them based on their general knowledge according to the intended use or application and the desired sensory stimulating effect. Generally speaking, these auxiliary perfume components belong to various chemical classifications such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds, and essential oils, and the said auxiliary perfume components can be of natural or synthetic origin. Many of these co-components are listed in references such as books, S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent version, or other works of similar nature, as well as numerous patent documents in the field of cosmetics. It is also understood that the said auxiliary components may also be compounds known to release various types of perfume compounds in a controlled manner. The auxiliary components are 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yl oxo(phenyl)acetate, (Z)-hex-3-en-1-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,(6-dien-1-yl) succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or a mixture thereof or a mixture thereof may be selected from the group consisting of.,

[0214] As used herein, "fragrance adjuvant" means a component that can impart additional benefits such as color, specific lightfastness, chemical stability, etc. Although a detailed description of the nature and types of adjuvants commonly used in fragrance bases is not exhaustive, it should be mentioned that the said components are well known to those skilled in the art.

[0215] Preferably, the fragrance composition according to the present invention contains microcapsules defined above in an amount of 0.01 to 30% by weight.

[0216] The microcapsules of the present invention can be advantageously used in many application fields and can be used in consumer products. The microcapsules can be used in a liquid form applicable to liquid consumer products and in a powder form applicable to powder consumer products.

[0217] According to a particular embodiment, the consumer product defined above is liquid and a) at least one surfactant in an amount of 2 to 65% by weight relative to the total weight of the consumer product, and b) water or a water-miscible hydrophilic organic solvent, and c) the microcapsule slurry or microcapsules defined above, and d) optionally, an unencapsulated fragrance. and comprises.

[0218] According to a particular embodiment, the consumer product defined above is in powder form and, hereinafter, a) at least one surfactant in an amount of 2 to 65% by weight relative to the total weight of the consumer product, and b) the microcapsule powder defined above, and c) optionally, a fragrance powder different from the microcapsules defined above. and comprises.

[0219] In the case of microcapsules containing a spice oil-based core, the products of the present invention can be used, in particular, in scented consumer products such as products belonging to fine fragrances or "functional" spices. Functional spices include, in particular, personal care products including hair care, body cleansing, skin care, and hygiene care, as well as home care products including laundry care, surface care, and air care. Accordingly, another object of the present invention consists of a scented consumer product containing the microcapsules defined above or the spice composition defined above as a spice component. The spice element of the consumer product can be a combination of the spice microcapsules defined above, free or non-encapsulated spices, and other types of spice microcapsules other than those disclosed herein.

[0220] In particular, a liquid consumer product a) at least one surfactant in an amount of 2 to 65% by weight based on the total weight of the consumer product, and b) water or a water-miscible hydrophilic organic solvent, and c) the spice composition defined above, A liquid consumer product containing the same is another object of the present invention.

[0221] Also, a powder consumer product (a) at least one surfactant in an amount of 2 to 65% by weight based on the total weight of the consumer product, and (b) the spice composition defined above, A powder consumer product containing the same is also part of the present invention.

[0222] Therefore, the microcapsules of the present invention can be added as such or as part of the spice composition of the present invention to scented consumer products.

[0223] For the sake of clarity, it should be mentioned that, among various benefits, a "scented consumer product" is expected to have a scenting effect on the surface to which it is applied (e.g., skin, hair, fabric, paper, or household surfaces) or in the air (such as air fresheners, deodorants). In other words, a scented consumer product according to the present invention is a manufactured product that contains a functional formulation, also referred to as a "base", together with a beneficial agent, in particular, an effective amount of the microcapsules according to the present invention.

[0224] The nature and type of other constituents present in the scented consumer product do not warrant a more detailed description herein, are not exhaustive in any case, and a person skilled in the art can select them according to the nature of the product and the desired effects based on their general knowledge. The base formulations of consumer products into which the microcapsules of the present invention can be incorporated can be found in the extensive literature on such products. These formulations do not warrant a detailed description herein and are not exhaustive in any case. A person skilled in the art of formulating such consumer products can fully select the appropriate ingredients based on their general knowledge and the available literature.

[0225] Non-limiting examples of suitable scented consumer products include fragrances, such as fine fragrances, colognes, aftershave lotions, body splashes; fabric care products, such as liquid or solid detergents, tablets and unit doses (single or multiple chambers), fabric softeners, dryer sheets, fabric fresheners, iron waters, or bleaches; personal care products, such as hair care products (e.g., shampoos, hair conditioners, coloring agents or hair sprays), cosmetics (e.g., vanishing creams, body lotions or deodorants or antiperspirants), or skin care products (e.g., scented soaps, shower or bath mousses, body washes, oils or gels, 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 cleaners, or products for cleaning various surfaces, such as sprays and wipes for treating / refreshing fabrics or hard surfaces (floors, tiles, stone floors, etc.); hygiene products, such as sanitary napkins, diapers, toilet paper.

[0226] Another object of the present invention is a consumer product, a personal care active base, and the microcapsules or microcapsule slurry as defined above or the fragrance composition as defined above, and wherein the consumer product is in the form of a personal care composition. A consumer product.

[0227] Personal care active bases into which the microcapsules of the present invention can be incorporated can be found in the extensive literature regarding such products. These formulations are not meant to warrant the detailed descriptions herein and are not exhaustive in any case. Those skilled in formulating such consumer products can fully select appropriate ingredients based on their general knowledge and the available literature.

[0228] The personal care composition is preferably selected from the group consisting of hair care products (e.g., shampoo, hair conditioner, coloring agent or hair spray), cosmetics (e.g., vanishing cream, body lotion or deodorant or antiperspirant), or skin care products (e.g., scented soap, shower or bath mousse, body wash, oil or gel, bath salt, or hygiene products).

[0229] Another object of the present invention is a consumer product, a home care or fabric care active base, and the microcapsules or microcapsule slurry as defined above or the fragrance composition as defined above, and wherein the consumer product is in the form of a home care or fabric care composition, a consumer product.

[0230] The home care or fabric care active bases into which the microcapsules of the present invention can be incorporated can be found in the extensive literature on such products. These formulations are not guaranteed by the detailed description herein and are not exhaustive in any case. Those skilled in formulating such consumer products can fully select the appropriate ingredients based on their general knowledge and the available literature.

[0231] Preferably, the consumer product contains 0.1 to 15% by weight, more preferably 0.2 to 5% by weight of the microcapsules of the present invention, and these percentages are defined by weight relative to the total weight of the consumer product. Of course, the above concentrations may be adapted according to the beneficial effects desired in each product.

[0232] An object of the present invention is a consumer product containing the microcapsules or microcapsule slurry as defined above, preferably a home care or fabric care consumer product, having a pH of less than 7.

[0233] The object of the present invention is a consumer product containing the microcapsules or microcapsule slurry defined above, preferably a home care or fabric care consumer product, which has a pH of 7 or higher.

[0234] In the case of the liquid consumer products mentioned below, with respect to the "active base", it should be understood that the active base includes an active material (typically including a surfactant) and water.

[0235] In the case of the solid consumer products mentioned below, with respect to the "active base", it should be understood that the active base includes an active material (typically including a surfactant) and auxiliaries (for example, bleaching agents, buffers; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, defoamers, foam suppressants; dyes, fillers, and mixtures thereof).

[0236] Fabric softener The object of the present invention is A fabric softener active base, preferably containing at least one active material selected from the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (ester quaternary ammonium salts), Hamburg ester quaternary ammonium salts (HEQ), TEAQ (triethanolamine quaternary ammonium salts), silicones, and mixtures thereof, wherein the active base is preferably used in an amount contained between 85% and 99.95% by weight based on the total weight of the composition, a fabric softener active base, The microcapsule slurry or microcapsules defined above, preferably in an amount contained between 0.05% and 15% by weight, more preferably between 0.1% and 5% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules, Optionally, a free perfume oil, A consumer product in the form of a fabric softener composition containing

[0237] Liquid detergent The object of the present invention is a liquid detergent active base, preferably at least one active material selected from the group consisting of anionic surfactants such as alkylbenzene sulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES), and nonionic surfactants such as alkylamine, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymer, amine oxide, alkyl polyglucoside, alkyl polyglucosamide, etc., and the active base is preferably used in an amount contained between 85 and 99.95% of the total weight of the composition, a liquid detergent active base, and a microcapsule slurry or microcapsule as defined above, preferably in an amount contained between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight of the total weight of the composition, a microcapsule slurry or microcapsule, and optionally, a free perfume oil, and a consumer product in the form of a liquid detergent composition containing

[0238] Solid detergent The object of the present invention is A solid detergent active base, preferably at least one active material selected from the group consisting of anionic surfactants such as alkylbenzene sulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES), and nonionic surfactants such as alkylamine, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymer, amine oxide, alkyl polyglucoside, alkyl polyglucosamide, and the active base is preferably used in an amount included between 85% and 99.95% with respect to the total weight of the composition, the solid detergent active base, The microcapsule powder or microcapsule slurry or microcapsule as defined above, preferably in an amount included between 0.05% and 15% by weight, more preferably between 0.1% and 5% by weight with respect to the total weight of the composition, the microcapsule powder or microcapsule slurry or microcapsule, Optionally, a free perfume oil, A consumer product in the form of a solid detergent composition containing

[0239] Shampoo / Shower Gel The object of the present invention is A shampoo or shower gel active base, preferably 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, and the active base is preferably used in an amount included between 85% and 99.95% with respect to the total weight of the composition, the shampoo or shower gel active base, A microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition, of the microcapsule slurry or microcapsules, and Optionally, free perfume oil, and A consumer product in the form of a shampoo or shower gel composition containing the same.

[0240] Rinse-off conditioner The object of the present invention is A rinse-off conditioner active base, preferably containing at least one active material selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride and mixtures thereof, and the active base is preferably used in an amount of 85 to 99.95% by weight based on the total weight of the composition. A rinse-off conditioner active base, A microcapsule slurry or microcapsules as defined above, preferably in an amount of 0.05 to 15% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition, of the microcapsule slurry or microcapsules, and Optionally, free perfume oil, and A consumer product in the form of a rinse-off conditioner composition containing the same.

[0241] Solid fragrance booster The object of the present invention is 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, saccharides such as sucrose, monosaccharides, disaccharides and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyol / sugar alcohol such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohol or fatty acid and mixtures thereof, a solid carrier, A microcapsule slurry or microcapsule as defined above, in powder form, preferably in an amount of between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, of the microcapsule slurry or microcapsule, Optionally, a free perfume oil, A consumer product in the form of a solid fragrance booster composition comprising.

[0242] Liquid fragrance booster The object of the present invention is An aqueous phase, A surfactant system consisting essentially of one or more nonionic surfactants, the surfactant system having 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 polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxyl esters, alkyl polyglucosides, amine oxides and combinations thereof, a surfactant system, 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 having an HLB of less than 10 and mixtures thereof, A microcapsule slurry or microcapsules as defined above, in the form of a slurry, preferably in an amount between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, of the microcapsule slurry or microcapsules, and Optionally, a free perfume oil, and A consumer product in the form of a liquid fragrance booster composition comprising.

[0243] Hair coloring ring The object of the present invention is An oxidation phase containing an oxidizing agent, and an alkaline phase containing an alkalizing 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 an oxidizing agent, preferably in an amount between 85 and 99.95% by weight, based on the total weight of the composition, of the oxidation phase and the alkaline phase, and A microcapsule slurry or microcapsules as defined above, preferably in an amount between 0.05 and 15%, more preferably between 0.1 and 5% by weight, based on the total weight of the composition, of the microcapsule slurry or microcapsules, and Optionally, a free perfume oil, and A consumer product in the form of an oxidative hair coloring composition comprising.

[0244] Perfume composition According to certain embodiments, the consumer product is 0.1 to 30%, preferably 0.1 to 20%, of the microcapsule slurry or microcapsules as defined above, and 0 to 40%, preferably 3 to 40%, of a perfume, and 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol, based on the total weight of the perfume composition, and In the form of a perfume composition comprising.

[0245] Next, the present invention will be further described by way of examples. It will be understood that the claimed invention is not intended to be limited in any way by these examples.

Example

[0246] [Example 1] [Preparation of Microcapsules According to the Present Invention]

Table 1

[0247] ·Microcapsule A (Preparation of Sodium Caseinate / Chitosan Composite Particle Suspension) A 2.0% sodium caseinate solution (sodium caseinate dissolved in deionized water) and a 0.4% chitosan solution (chitosan dissolved in 1% acetic acid solution) were injected into two different flows of a four-stream multi-inlet vortex. Water with a pH of 5.0 was injected into the other two flows. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA).

[0248] The resulting complex coacervation suspension contained 0.5% sodium caseinate and 0.1% chitosan (average particle size: 347 nm), and the pH was included between 4.8 and 5.0.

[0249] (Preparation of Microcapsules) An oil phase containing flavor oil (see Table 1) and Takenate (registered trademark) (xylene diisocyanate adduct polymer) was added to the complex coacervation suspension at an oil / water ratio of 3:7. Subsequently, a stable Pickering emulsion was formed using a homogenizer.

[0250] The Pickering emulsion was transferred to a reactor, and an interfacial reaction was carried out at 70 °C for 3 hours.

[0251]

Table 2

[0252] ·Microcapsule B (Preparation of Sodium Caseinate / Chitosan Composite Particle Suspension) A 2.0% sodium caseinate solution (sodium caseinate dissolved in deionized water) and a 0.4% chitosan solution (chitosan dissolved in 1% acetic acid solution) were injected into a two-inlet vortex. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA).

[0253] The resulting composite coacervation suspension contained 1.0% sodium caseinate and 0.2% chitosan (average particle size: 764 nm), and the pH of the suspension was adjusted to 4.8 - 5.0.

[0254] (Preparation of Microcapsules) An oil phase containing flavor oil (see Table 1) and Takenate (registered trademark) (xylene diisocyanate adduct polymer) was added to the composite coacervation suspension at an oil / water ratio of 3:7. Then, a stable Pickering emulsion was formed using a homogenizer.

[0255] The Pickering emulsion was transferred to a reactor, and an interfacial reaction was carried out at 70 °C for 3 hours.

[0256]

Table 3

[0257] Figure 2 represents a micrograph of microcapsule B.

[0258] · Microcapsule C (Preparation of Whey Protein / Arabic Gum Composite Particle Suspension) A 0.6% whey protein solution (whey protein dissolved in deionized water) and a 1.2% arabic gum solution (arabic gum dissolved in DI water) were injected into a two-inlet vortex. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA).

[0259] The obtained complex coacervation suspension contained 0.3% whey protein and 0.6% gum arabic (average particle size: 1.2 μm), and the pH was adjusted to between 4.3 and 4.6.

[0260] An oil phase containing flavor oil (see Table 1) and Takenate® (xylene diisocyanate adduct polymer) was added to the complex coacervation suspension at an oil / water ratio of 3:7. Subsequently, a stable Pickering emulsion was formed using a homogenizer.

[0261] The Pickering emulsion was transferred to a reactor, and the interfacial reaction was carried out at 70 °C for 3 hours.

[0262]

Table 4

[0263] ·Microcapsule D (Preparation of whey protein / chitosan composite particle suspension) A 4.0% whey protein solution (whey protein dissolved in deionized water) and a 0.8% chitosan solution (chitosan dissolved in 1% acetic acid solution) were injected into two streams of a four-stream multi-inlet vortex, and water with a pH of 5.5 was injected into the other two streams. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA).

[0264] The obtained complex coacervation suspension contained 1.0% whey protein and 0.2% chitosan (average particle size: 5.0 μm), and the pH was approximately 5.5.

[0265] An oil phase containing flavor oil (see Table 1) and Takenate® (xylene diisocyanate adduct polymer) was added to the complex coacervation suspension at an oil / water ratio of 3:7. Subsequently, a stable Pickering emulsion was formed using a homogenizer.

[0266] The pickering emulsion was transferred to a reactor, and the interfacial reaction was carried out at 70 °C for 3 hours.

[0267]

Table 5

[0268] ·Microcapsule E (Preparation of potato protein / arabic gum composite particle suspension) A 2.0% potato protein solution (pH adjusted to 2 using 5.0% hydrochloric acid solution and 5.0% sodium hydroxide solution) and a 2.0% arabic gum solution (pH adjusted to 2 using 5.0% hydrochloric acid solution and 5.0% sodium hydroxide solution) were injected into two different flows of a two-stream multi-inlet vortex. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA).

[0269] The obtained composite coacervation suspension contained 1.0% potato protein and 1.0% arabic gum (average particle size: 814.7 nm), and the pH was 2.

[0270] (Preparation of microcapsules) An oil phase containing flavor oil (see Table 1) and Takenate (registered trademark) (xylene diisocyanate adduct polymer) was added to an aqueous phase containing a composite coacervation suspension and melamine-formaldehyde resin (MF resin) at an oil / water ratio of 3:7. Then, a stable pickering emulsion was formed using a homogenizer. The pickering emulsion was transferred to a reactor, and the interfacial reaction was carried out at 80 °C for 2 hours. Then, ethylene urea was added, and the slurry was cooled to room temperature.

[0271]

Table 6

[0272] ·Microcapsule F (Preparation of zein simple particle suspension) For a solution having a solids content of 2.0%, zein was dissolved in an ethanol / water (70 / 30 v / v) mixture. The zein solution and water were injected into two different streams of a two-stream multi-inlet vortex. The injection was carried out at a rate of 40 mL / min using a pump (Harvard's PHD ULTRA). The resulting suspension was evaporated by removing ethanol with a rotary evaporator to obtain a final suspension having a solids content of about 6.8% (average particle size: 615.1 nm).

[0273] (Preparation of Microcapsules) An oil phase containing flavor oil (see Table 1) and ethylene glycol dimethacrylate (EGDMA) was added to a diluted zein simple coacervation suspension (2.0% zein particles in the suspension) at an oil / water ratio of 3:7. Then, a homogenizer was used to form a stable Pickering emulsion, and the Pickering emulsion was transferred to a reactor. An ammonium persulfate (APS) solution and a sodium bisulfite solution were added to the Pickering emulsion. Then, the reaction was carried out at 40 °C for 3 hours and 60 °C for 1 hour under a N2 atmosphere.

[0274] [Table 7]

[0275] [Example 2] [Characterization and Performance of Microcapsules According to the Present Invention] Size Measurement: The average size (D[4,3]) of the microcapsule slurry was measured using a Mastersizer 3000 apparatus manufactured by Malvern Instruments Ltd. (UK).

[0276] Zeta Potential Measurement: The zeta potential of the microcapsules was examined using a Zetasizer Nano ZS manufactured by Malvern Instruments Ltd. (UK).

[0277] Example Average Size Zeta Potential A 21.8μm -70.0mV B 25.8μm -37.5mV C 8.9μm -37.7mV D 39.7μm -4.5mV E 31.5μm -32.7mV F 48.9μm -12.5mV

[0278] ·Stability The storage stability of the capsules was evaluated with a fabric softener formulation (see the composition in Table 8). The capsule dispersion was diluted with a fabric softener (29.73 g) to obtain a final concentration of 0.20 wt% of the fragrance. The softener was stored at 37 °C for up to 3 days. Subsequently, the amount of the fragrance leaked from the capsules was measured by solvent extraction using isooctane (10 mL) under stirring.

[0279]

Table 8

[0280] (Protocol for Stability Evaluation) A fabric softener base containing microcapsules (2 g) was introduced into a 20 mL vial. The sample was diluted with water (2 mL) using a Socorex 10 mL bottle top dispenser to reduce the viscosity. The sample was shaken for 5 minutes using a Turbulat Shaker set at 40 rpm. Isooctane containing 1,4-dibromobenzene as an internal standard with an accurately known concentration of about 90 ng / μL was added to the vial (10 mL). The sample was shaken at 40 rpm for 45 minutes to extract the free fragrance and then centrifuged at 3.0 G for 10 minutes to separate the two phases. The solvent phase was recovered and dried over MgSO4 for GC analysis.

[0281]

Table 9

[0282] Therefore, the microcapsules according to the present invention exhibit good stability in fabric softeners.

[0283] · Performance strength Fragrance oil dosage in fabric softener: 0.1% Washing protocol: (1) The capsule slurry was added to 26 g of a fragrance-free fabric softener with a fragrance oil dosage of 0.1% while stirring at 200 rpm for 5 minutes, and a cotton towel was washed using the fabric softener.

[0284] (2) Cotton towels (1.4 kg for 36 towels of 30 cm × 30 cm) were washed in a washing machine (containing 65 g of a fragrance-free detergent and the fabric softener containing the capsules from step 1) at a normal washing cycle: water level - 43 L, washing cycle and time - 42 minutes in normal mode, water temperature - 25°C at room temperature.

[0285] (3) After drying the washed towels at room temperature for 24 hours, they were evaluated before and after rubbing.

[0286] A sensory evaluation panel was conducted, and 8 panelists were asked to evaluate the fragrance intensity of the dried towels before and after rubbing using a scale of 1 (imperceptible fragrance) to 7 (very strong fragrance intensity).

[0287] Performance strength (scale of 1 - 7): For microcapsule A, 2.8 ± 0.1 before rubbing; 4.5 ± 0.1 after rubbing.

[0288] Performance strength (scale of 1 - 7): For microcapsule B, 3.2 ± 0.1 before rubbing; 4.6 ± 0.1 after rubbing.

[0289] Performance strength (scale of 1 - 7): For microcapsule C, 3.0 ± 0.1 before rubbing; 4.3 ± 0.1 after rubbing.

[0290] Performance strength (scale of 1 - 7): For microcapsule D, 2.1 ± 0.1 before rubbing; 4.7 ± 0.1 after rubbing.

[0291] [Example 3] [Liquid detergent composition] The microcapsules of the present invention are dispersed in the liquid detergent base described below to obtain a concentration of encapsulated perfume oil of 0.22%.

[0292] [Table 10]

[0293] [Example 4] [Rinse-off conditioner] The microcapsules of the present invention are dispersed in the rinse-off conditioner base described below to obtain a concentration of encapsulated perfume oil of 0.5%.

[0294] [Table 11]

[0295] [Example 5] [Shampoo composition] The microcapsules of the present invention are weighed and mixed in the shampoo composition, and a perfume equivalent to 0.2% is added.

[0296] [Table 12]

[0297] [Example 6] [Antiperspirant roll-on emulsion composition] The microcapsules of the present invention are weighed and mixed in the antiperspirant roll-on emulsion composition, and a perfume equivalent to 0.2% is added.

[0298] [Table 13]

[0299] Heat Part A and Part B separately to 75°C; add Part A to Part B with stirring and homogenize the mixture for 10 minutes. Then, cool the mixture with stirring; when the mixture reaches 45°C, slowly add Part C while stirring, and when the mixture reaches 35°C, slowly add Part D while stirring. Then, cool the mixture to room temperature.

[0300] [Example 7] [Deodorant Spray Composition] Weigh the microcapsules of the present invention and mix them in an antiperspirant roll-on emulsion composition, and add 0.2% equivalent of fragrance.

[0301] [Table 14]

[0302] Mix and dissolve all the components in the order according to Table 11. Then, fill an aerosol can, compress it, and add a propellant (aerosol filling: 40% active solution, 60% propane / butane, 2.5 bar).

[0303] [Example 8] [Shower Gel Composition] Weigh the microcapsules of the present invention and mix them in the following composition, and add 0.2% equivalent of fragrance.

[0304] [Table 15]

[0305] [Example 9] [Unit Dose Formulation] Weigh a sufficient amount of the exemplified microcapsules and mix them in a unit dose formulation, and add 0.2% equivalent of fragrance.

[0306] The unit dose formulation can be included in a PVOH (polyvinyl alcohol) film.

[0307] [Table 16]

Claims

1. A method for preparing a microcapsule slurry, 1) A step of suspending coacervate particles in a solvent to form a dispersed phase; 2) A step of mixing at least one polyfunctional monomer with a hydrophobic material to form an oil phase; 3) Adding the oil phase to the dispersed phase and mixing them to form a two-phase Pickering emulsion under conditions that enable the formation of a microcapsule slurry by interfacial polymerization; A method that includes this.

2. The method according to claim 1, wherein the coacervate particles are prepared by a flash nanoprecipitation process.

3. The method according to claim 1 or 2, wherein the coacervate particles comprise at least one polymer.

4. The method according to claim 1 or 2, wherein the coacervate particles comprise a first polymer and a second polymer.

5. The method according to claim 4, wherein the first polymer contains at least one cationic group such as an amino group, an azole group, an amide group, a quaternary ammonium cation, or a guanidinium cation.

6. The method according to claim 4, wherein the first polymer is selected from the group consisting of proteins, chitosan and derivatives, cationically modified polysaccharides, polyethyleneimines, poly(amideamines), poly(amino-coesters), cationic polyacrylates, and mixtures thereof.

7. The method according to claim 4, wherein the second polymer is selected from the group consisting of modified starch, gum arabic, chitosan, sodium caseinate, alginate, cellulose derivatives, guar gum, pectinate, pectin, carrageenan, polyacrylic acid and methacrylic acid, xanthan gum, or polyanions consisting of sodium triphosphate, trisodium trimetaphosphate, sodium pyrophosphate, sodium dextran sulfate salt, and polymers consisting of mixtures thereof.

8. The method according to claim 1 or 2, wherein the coacervate particles comprise a polymer and polyions charged in the opposite direction to the polymer.

9. The method according to claim 1 or 2, wherein the coacervate particles preferably contain an active ingredient selected from the group consisting of cosmetic ingredients, skincare ingredients, fragrance ingredients, flavor ingredients, odor-preventing ingredients, antimicrobial ingredients, pharmaceutical or pesticide ingredients, disinfectant ingredients, insect repellents or attractants, and mixtures thereof.

10. The method according to claim 1 or 2, wherein the polyfunctional monomer is selected from the group consisting of at least one isocyanate, an anhydride or maleic anhydride, acyl chloride, epoxide, (meth)acrylate monomer, alkoxysilane, and mixtures thereof.

11. A microcapsule slurry obtained by the method of claim 1 or 2, wherein the microcapsules are A core containing a hydrophobic material, preferably a fragrance oil, preferably an oil-based core, A composite shell comprising a first material and a second material, The first material and the second material are different, The first material is a coacervate particle, The second material is a polymer material. Composite shell and A microcapsule slurry containing [the specified substance].

12. The microcapsule slurry according to claim 11, wherein the weight ratio of the first material and the second material in the slurry is between 10:90 and 99:1, preferably between 30:70 and 99:

1.

13. The microcapsule slurry according to claim 11, wherein the second material is present in an amount of less than 5% by weight relative to the total weight of the microcapsule slurry.

14. Personal care activation base, A microcapsule slurry or microcapsule as defined in claim 11 and A consumer product that includes and is in the form of a personal care composition.

15. Home care or fabric care active base, A microcapsule slurry or microcapsule as defined in claim 11 and A consumer product that includes, and is in the form of a home care or fabric care composition.

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