Polyamide Microcapsules

Abstract

The present invention relates to polyamide microcapsules. A method for producing polyamide microcapsules is also an object of the present invention. Perfume compositions and consumer products, especially perfumed consumer products in the form of home care or personal care products, comprising said microcapsules are also part of the present invention.

Description

[Technical Field]

[0001] The present invention relates to polyamide microcapsules. A method for producing polyamide microcapsules is also an object of the present invention. Perfume compositions and consumer products, especially perfumed consumer products in the form of home or personal care products, comprising said microcapsules are also part of the present invention.

[0002] Background of the Invention One of the challenges facing the fragrance industry is that the volatility of odor compounds, especially "top notes," means that the olfactory benefits they impart are lost relatively quickly. To control the release rate of volatiles, delivery systems such as fragrance-containing microcapsules must protect the core payload and release it in a delayed manner when triggered. A key requirement for these systems from the industry is that they remain in suspension in challenging media without physical separation or degradation. This is referred to as delivery system stability. For example, fragranced personal and household cleaning products, which contain high levels of harsh surfactant detergents, present significant challenges for stabilizing microcapsules.

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

[0004] There remains a need to provide new microcapsules that offer superior performance in terms of stability, particularly in difficult media such as consumer product bases, without compromising the performance of the microcapsules, as well as in terms of delivery of active ingredients, e.g., olfactory performance in the case of perfume ingredients.

[0005] The present invention proposes a solution to the above-mentioned problems by providing novel polyamide microcapsules and a method for producing said microcapsules.

[0006] Summary of the Invention It has now been found that by reacting the acyl chlorides defined in the present invention with at least one amino compound during the manufacturing process, core-shell microcapsules containing encapsulated hydrophobic materials can be obtained.

[0007] The first object of the present invention is to - an oily core containing a hydrophobic material, preferably a fragrance; a polyamide shell, The following formula (I): [ka] wherein n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is an (n+1)-valent C3 to C6 alkyl group, or (i) to (vi) [ka] (n+1)-valent C2 to C containing at least one group selected from 45 a hydrocarbon group, R is a hydrogen atom, a methyl group, or an ethyl group, preferably a hydrogen atom. but is not cyclohexane-1,3,5-tricarbonyl trichloride and 2,2'-oxydiacetyl chloride, and at least one amino compound, a polyamide shell comprising: The polyamide core-shell microcapsules are

[0008] In a second aspect, the present invention provides a method for producing a medicament for the treatment of a pulmonary arthritis, comprising: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to obtain an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry; 1. A method for producing a polyamide core-shell microcapsule slurry, comprising: A stabilizer is added to the oil and / or water phase; at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), The acyl chloride is represented by the following formula (I): [ka] wherein n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is an (n+1)-valent C3 to C6 alkyl group, or (i) to (vi) [ka] (n+1)-valent C2 to C containing at least one group selected from 45 a hydrocarbon group, R is a hydrogen atom, a methyl group, or an ethyl group, preferably a hydrogen atom. but not cyclohexane-1,3,5-tricarbonyl trichloride and 2,2'-oxydiacetyl chloride.

[0009] A third object of the present invention is a polyamide core-shell microcapsule slurry obtainable by the process defined above.

[0010] (i) microcapsules as defined above, wherein the hydrophobic material comprises a perfume; (ii) at least one component selected from the group consisting of a fragrance carrier and a fragrance base; (iii) optionally at least one flavoring adjuvant; A perfuming composition comprising:

[0011] Another object of the present invention is to provide - Effective bases for personal care and - microcapsules as defined above or a perfuming composition as defined above, and a consumer product in the form of a personal care composition comprising:

[0012] Another object of the present invention is to provide - a base effective for home or clothing care; - microcapsules as defined above or a perfuming composition as defined above, and a consumer product in the form of a home care or clothing care composition comprising:

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

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

[0015] "Fragrance or flavor oil" means a single fragrance or flavoring compound or a mixture of fragrance or flavoring compounds.

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

[0017] For the sake of clarity, the expression "dispersion" in the present invention refers to a system in which particles are dispersed in a continuous phase of different composition, including in particular suspensions or emulsions.

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

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

[0020] An "amino compound" is to be understood as a compound having at least two reactive amine groups.

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

[0022] In the present invention, the terms "2,2'-oxydiacetyl chloride" and "diglycolyl chloride" are used interchangeably.

[0023] By "polyamide microcapsules" is meant that the shell of the microcapsules comprises a polyamide-based material made from the reaction product between an acyl chloride and at least one amino compound, optionally containing a stabilizer. The term "polyamide microcapsules" can also encompass shells made from a composite material comprising a polyamide-based material and another material, such as a biopolymer.

[0024] Polyamide Microcapsules The object of the present invention is to - an oily core containing a hydrophobic material, preferably a fragrance; a polyamide shell, The following formula (I): [ka] wherein n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is an (n+1)-valent C3 to C6 alkyl group, or (i) to (vi) [ka] (n+1)-valent C2 to C containing at least one group selected from 45 a hydrocarbon group, R is a hydrogen atom, a methyl group, or an ethyl group, preferably a hydrogen atom. but is not cyclohexane-1,3,5-tricarbonyl trichloride and 2,2'-oxydiacetyl chloride, and at least one amino compound, a polyamide shell comprising: The polyamide core-shell microcapsules are

[0025] Another object of the present invention is a polyamide core-shell microcapsule slurry comprising at least one polyamide core-shell microcapsule as defined above.

[0026] According to one embodiment, when the hydrocarbon group X comprises several groups selected from (i) to (vi), they are each separated by at least one carbon atom of X.

[0027] By "...hydrocarbon group..." it is understood to mean that the group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e., a linear or branched saturated hydrocarbon (e.g., an alkyl group), a linear or branched unsaturated hydrocarbon (e.g., an alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g., a cycloalkyl), or an unsaturated cyclic hydrocarbon (e.g., a cycloalkenyl or cycloalkynyl), or in the form of an aromatic hydrocarbon, i.e., an aryl group, or in the form of a mixture of the above types of groups; for example, unless specifically limited to only one type, a particular group may contain linear alkyl, branched alkenyl (e.g., having one or more carbon-carbon double bonds), (poly)cycloalkyl, and aryl moieties. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of more than one type of topology (e.g., linear, cyclic, or branched) and / or saturated or unsaturated (e.g., alkyl, aromatic, or alkenyl), it also means that the group may have any one of the above-described topologies or contain moieties that are 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 (e.g., alkyl) form, it is intended that the group may be in any type of topology (e.g., linear, cyclic, or branched) form or have multiple moieties with different topologies.

[0028] The term "hydrocarbon group optionally comprising" is understood to mean that said hydrocarbon group may optionally contain heteroatoms to form ether, thioether, amine, nitrile, or carboxylic acid groups, and derivatives (e.g., esters, acids, amides, etc.).

[0029] These groups can be linked laterally to a hydrocarbon group by replacing a hydrogen atom of said hydrocarbon, or can be inserted into a hydrocarbon chain or ring by replacing a carbon atom of the hydrocarbon group (where chemically possible).

[0030] According to one embodiment, when group (vi) is present, it is only present in combination with any one of groups (i) to (v).

[0031] According to certain embodiments, the acyl chloride is selected from the group consisting of propane-1,2,3-tricarbonyl trichloride, cyclohexane-1,2,4,5-tetracarbonyl tetrachloride, 2,2′-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate, [2-[2,2-bis[(4-chloro-4-oxo [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonylbenzoate, and mixtures thereof.

[0032] By "a polyamide shell comprising at least one acyl chloride and at least one amino compound," it is to be understood that the polyamide shell is derived from at least one acyl chloride and at least one amino compound. In other words, it is to be understood that the polyamide shell comprises the reaction product of at least one acyl chloride and at least one amino compound.

[0033] According to one embodiment, when a stabilizer is present in the shell, it should be understood that the polyamide shell is derived from an acyl chloride, at least one amino compound, and the stabilizer. In other words, according to this embodiment, it should be understood that the polyamide shell comprises the reaction product of an acyl chloride, at least one amino compound, and the stabilizer.

[0034] The weight ratio between the acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.2, preferably between 0.01 and 0.09, more preferably between 0.03 and 0.07.

[0035] According to one embodiment, the molar ratio between the functional group NH2 of the amino compound and the functional group COCl of the acyl chloride is comprised between 0.01 and 50, preferably between 0.01 and 20, more preferably between 0.01 and 10.

[0036] According to a particular embodiment, the acyl chloride of the present invention is a mixture of at least two different acyl chlorides defined by formula (I).

[0037] According to a particular embodiment, the acyl chloride of the present invention as defined by formula (I) can be used in combination with another acyl chloride, in particular selected from the group consisting of benzene-1,3,5-tricarbonyl chloride, benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthalyol dichloride, 2,2'-oxydiacetyl chloride (diglycolyl dichloride), succinic acid dichloride, and mixtures thereof.

[0038] Hydrophobic materials According to one embodiment, the hydrophobic material is a hydrophobic active ingredient.

[0039] According to a preferred embodiment, the active ingredient comprises a perfume oil or a flavor oil. Alternative ingredients that may benefit from encapsulation can be used instead of or in combination with the fragrance or flavor. Non-limiting examples of such ingredients include cosmetics, skin care, malodor control, bactericides, fungicides, pharmaceutical or pesticide ingredients, disinfectants, insect repellents or attractants, and mixtures thereof.

[0040] The nature and type of insect repellent or attractant that may be present in the hydrophobic inner phase does not warrant a more detailed description herein, and in any case is not exhaustive, but can be selected by a person skilled in the art on the basis of his general knowledge and according to the intended use or application.

[0041] Examples of such insect repellents or attractants are birch, DEET (N,N-diethyl-m-toluamide), lemon eucalyptus (Corymbia citriodora) essential oil and its active compound p-menthane-3,8-diol (PMD), icaridin (hydroxyethyl isobutylpiperidine carboxylate), nepelactone, citronella oil, neem oil, Myrica Gale, dimethyl carbonate, tricyclodecenyl allyl ether, IR3535 (3-[N-butyl-N-acetyl]-aminopropionic acid, ethyl ester, ethyl hexanediol, dimethyl phthalate, metofluthrin, indalone, SS220, anthranilate-based insect repellents, and mixtures thereof.

[0042] "Perfume" (or "perfume oil"), as used herein, refers to an ingredient or composition that is liquid at about 20°C. According to any one of the above embodiments, the perfume oil may be a perfuming ingredient alone or a mixture of ingredients in the form of a perfume composition. "Perfuming ingredient" as used herein refers to a compound used for the primary purpose of imparting or modifying an odor. In other words, to be considered a perfuming ingredient, such an ingredient must not only have an odor but must also be recognized by those skilled in the art as being able to at least impart or modify the odor of the composition in a positive or pleasant way. For purposes of the present invention, perfume oil includes not only combinations of perfuming ingredients with substances that together improve, enhance, or modify the delivery of the perfuming ingredient, such as perfume precursors, emulsions, or dispersions, but also combinations that provide additional benefits beyond modifying or imparting an odor, such as longevity, blooming, malodor suppression, antimicrobial effect, microbial stability, and pest control.

[0043] The nature and type of perfume ingredients present in the oil phase do not warrant a more detailed description herein, and in any case are not exhaustive, and those skilled in the art can select them based on their general knowledge and according to the intended use or application and the desired sensory effect.Generally, these perfume ingredients belong to various chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpenoids, nitrogen or sulfur heterocyclic compounds, and essential oils, and said perfume co-ingredients can be of natural or synthetic origin.Many of these co-ingredients are listed in reference texts, such as the book "Perfume and Flavor Chemicals" by S. Arctander, 1969, Montclair, New Jersey, USA, or its more recent version, or other works of similar nature, as well as in the abundant patent literature in the perfumery field.

[0044] Mention may be made in particular of the perfuming ingredients commonly used in perfume formulations, such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal, and / or nonenal; - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol, and / or alpha-pinene; - Balsam ingredients: coumarin, ethyl vanillin, and / or vanillin; - Citrus ingredients: 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 ingredients: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, 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-cyclohexene) -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, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexene- 1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-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, high-cis-methyl dihydrojasmonate, 3-methyl ethyl-5-phenyl-1-pentanol, vergyl proprionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl, vergyl isobutyrate, and / or methyl ionone isomer mixture;, - Fruity ingredients: gamma undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate, and / or diethyl 1,4-cyclohexanedicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, 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 ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, 3-methyl-5-cyclopentadecanone decen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one, and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one, and / or isobornyl acetate; Other ingredients (e.g., amber, powdery, spicy, or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any stereoisomers thereof, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, and / or 3-(3-isopropyl-1-phenyl)butanal.

[0045] According to a particular embodiment, the perfuming ingredient is one with high steric hindrance and is in particular selected from the following group: - Group 1: Perfuming ingredients containing a cyclohexane ring, a cyclohexene ring, a cyclohexanone ring, or a cyclohexenone ring substituted with at least one linear or branched C1-C4 alkyl or alkenyl substituent; - Group 2: Perfuming ingredients containing a cyclopentane ring, a cyclopentene ring, a cyclopentanone ring, or a cyclopentenone ring substituted with at least one linear or branched C4-C8 alkyl or alkenyl substituent; - Group 3: Perfuming ingredients 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 with at least one phenyl substituent and optionally with one or more linear or branched C1-C3 alkyl or alkenyl substituents; - Group 4: Perfuming ingredients containing at least two fused or linked C5 and / or C6 rings; - Group 5: Fragrance compounds containing ring structures such as camphor; - Group 6: Perfuming ingredients containing at least one C7-C20 ring structure; - Group 7: Perfuming ingredients having a logP value greater than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent.

[0046] Examples of ingredients in each of these groups are: - Group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (Supplier: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (Supplier: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1,8-p-menthadien-7-ol (Supplier: Firmenich SA, Geneva, Switzerland). 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 (Supplier: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1,4-cyclohexanediethyl dicarboxylate (Supplier: Firmenich SA, Geneva, Switzerland), (3ARS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Supplier: Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Supplier: Firmenich SA, Geneva, Switzerland). Switzerland), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde; Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (supplied by Givaudan SA, Vernier, Switzerland), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol (supplied by Firmenich SA, Geneva, Switzerland), (1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol (supplied by Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone, methyl-cis-3-oxo-2-pentyl-1-cyclopentane acetate (supplied by Firmenich SA, Geneva, Switzerland). Switzerland), 2,2,5-trimethyl-5-pentyl-1-cyclopentanone (Supplier: Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (Supplier: Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (Supplier: Givaudan SA, Vernier, Switzerland); - Group 3: damascone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (supplied by Firmenich SA, Geneva, Switzerland), nectalactone ((1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'-yl)propyl]cyclopentanone), alpha-ionone, beta-ionone, damascenone, a mixture of 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (supplied by Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (supplied by Firmenich SA, Geneva, Switzerland). Switzerland), (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate (supplied by Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1-cyclohexyl acetate (supplied by International Flavors and Fragrances, USA), 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (supplied by Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (supplied by Firmenich SA, Geneva, Switzerland). 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 (Supplier: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate (Supplier: Firmenich SA, Geneva, Switzerland).Switzerland), para-tert-butylcyclohexanone, menthenethiol, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate; - Group 4: Methyl cedryl ketone (Supplier: International Flavors and Fragrances, USA), a mixture of (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0~2,6~]dec-3-en-8-yl 2-methylpropanoate and (1RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0~2,6~]dec-4-en-8-yl 2-methylpropanoate, vetiverol, vetiveron, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone (Supplier: International Flavors and Fragrances, (Supplier: 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) isomers, 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 (Supplier: International Flavors and Fragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal (Supplier: Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9-spiro-2'-oxirane (Supplier: Firmenich SA, Geneva, Switzerland), 9 / 10-ethyldiene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8a-trimethyl-2-naphthalenyl acetate (Supplier: Firmenich SA, Geneva, Switzerland), octalinol, (dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan, Supplier: Firmenich SA, Geneva, Switzerland Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl acetate, as well as tricyclo[5.2.1.0(2,6)]dec-3-en-8-ylpropanoate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-ylpropanoate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'-cyclohexen-4'-one;. - Group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane (Supplier: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, a mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one and 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one (Supplier: Firmenich SA, Geneva, Switzerland). Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (Supplier: Firmenich SA, Geneva, Switzerland); - Group 6: (Trimethyl-13-oxabicyclo-[10.1.0]-trideca-4,8-diene (Supplier: Firmenich SA, Geneva, Switzerland), Ambrettolide LG ((E)-9-hexadecen-16-olide, Supplier: Firmenich SA, Geneva, Switzerland), Pentadecenolide (Supplier: Firmenich SA, Geneva, Switzerland), Musenone (3-methyl-(4 / 5)-cyclopentadecenone, Supplier: Firmenich SA, Geneva, Switzerland), 3-methylcyclopentadecanone (Supplier: Firmenich SA, Geneva, Switzerland), Pentadecanolide (Supplier: Firmenich SA, Geneva, Switzerland), Cyclopentadecanone (Supplier: Firmenich SA, Geneva, Switzerland), 1-ethoxyethoxy)cyclododecane (Supplier: Firmenich SA, Geneva, Switzerland) Switzerland), 1,4-dioxacycloheptadecane-5,17-dione, 4,8-cyclododecadien-1-one; - Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal (Supplier: Givaudan SA, Vernier, Switzerland), 2,2,2-trichloro-1-phenylethyl acetate.

[0047] According to one embodiment, the perfume comprises at least 30%, in particular at least 50%, more particularly at least 60% of ingredients selected from groups 1 to 7 as defined above. According to one embodiment, the perfume comprises at least 30%, in particular at least 50%, of ingredients selected from groups 3 to 7 as defined above. According to one embodiment, the perfume comprises at least 30%, in particular at least 50%, of ingredients from groups 3, 4, 6 or 7 as defined above.

[0048] According to one embodiment, the perfume comprises at least 30%, in particular at least 50%, more in particular at least 60% of ingredients having a logP greater than 3, in particular greater than 3.5, more in particular greater than 3.75.

[0049] According to one embodiment, the fragrance used in the present invention contains less than 10% by weight of primary alcohols, less than 15% by weight of secondary alcohols, and less than 20% by weight of tertiary alcohols. According to one embodiment, the fragrance used in the present invention contains no primary alcohols and less than 15% of secondary and tertiary alcohols.

[0050] It is also understood that the perfuming ingredient may be a compound known to release various types of perfuming compounds, also known as perfume precursors or fragrance precursors, in a controlled manner. Non-limiting examples of suitable perfume precursors 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, 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-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(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-ene- 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, or mixtures thereof.

[0051] The perfume ingredients can be dissolved in solvents currently used in the perfume industry. According to one embodiment, the solvent is not alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, limonene or other terpenes, or isoparaffins. According to one embodiment, the solvent is very hydrophobic and highly sterically hindered, such as Abalyn® or benzyl benzoate. According to one embodiment, the perfume contains less than 30% solvent. According to one embodiment, the perfume contains less than 20%, particularly less than 10%, of solvent, all of which percentages are defined by weight relative to the total weight of the perfume. According to one embodiment, the perfume is essentially solvent-free.

[0052] According to one embodiment, the oily phase (or oily core) comprises: - 25-100% by weight of perfume oil containing at least 15% by weight of high impact perfume ingredients with LogT<-4, and - 1.07g / cm 3 0 to 75% by weight of a density-balanced material having a density greater than Includes.

[0053] High impact fragrance ingredients with LogT<-4 and 1.07g / cm 3 The properties of density-balanced materials having densities greater than 10 ...

[0054] According to a particular embodiment, the hydrophobic material does not include any active ingredients (such as fragrances), and according to this particular embodiment, it comprises, preferably consists of, a hydrophobic solvent, preferably selected from the group consisting of isopropyl myristate, triglycerides (e.g., Neobee® MCT oil, vegetable oils), D-limonene, silicone oil, mineral oil, and mixtures thereof, and optionally a hydrophilic solvent, preferably 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.

[0055] "Flavor" (or flavor oil) is used herein to mean a flavoring ingredient or a mixture of flavoring ingredients with solvents or adjuvants currently used in the preparation of flavoring formulations, i.e., a specific mixture of ingredients intended to be added to an edible composition or chewable product to impart, improve, or modify its organoleptic properties, in particular its flavor and / or taste. Taste modifiers are also encompassed by said definition. Flavoring ingredients are well known to those skilled in the art, and their nature does not warrant a more detailed description herein, which is in any case not exhaustive, and which the skilled flavorist can select on the basis of his general knowledge and according to the intended use or application and the sensory effect desired to be achieved. Many of these flavoring ingredients are listed in reference texts such as the book Perfume and Flavor Chemicals by S. Arctander, 1969, Montclair, New Jersey, USA, or its more recent versions, or other works of a similar nature, such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press, or Synthetic Food Adjuncts, 1947, by M.B. Jacobs, can Nostrand Co., Inc. The solvents and adjuvants, or their current uses for the preparation of flavoring formulations, are also well known in the art.

[0056] In certain embodiments, the flavor is selected from the group consisting of citrus oils, mint oils, and terpene-based flavors, including sulfur-based flavors.

[0057] The term "biocide" refers to a chemical substance that can kill living organisms (e.g., microorganisms) or reduce or prevent their growth and / or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and industry, where they prevent 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 antimicrobials, such as bactericides, antibiotics, antibacterial agents, antivirals, antifungals, antiprotozoals, and / or antiparasitics.

[0058] As used herein, "pest control agent" means a substance that functions to repel or attract pests, or to reduce, inhibit, or promote their growth, development, or activity. A pest is any organism, whether animal, plant, or fungus, that invades or causes problems for plants or animals, and includes insects, especially arthropods, mites, spiders, fungi, weeds, bacteria, and other microorganisms.

[0059] Amino compounds The amino compound is preferably selected from the group consisting of amino acids (such as L-lysine, L-lysine ethyl ester, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, and L-threonine), guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, polyetheramines (Jeffamine®), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, amines having a disulfide bond, such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.

[0060] According to a particular embodiment, the shell comprises two different amino compounds, namely a first amino compound and a second amino compound.

[0061] According to certain embodiments, the first amino compound is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, and mixtures thereof, preferably L-lysine, L-arginine, L-histidine, L-tryptophan, and mixtures thereof, more preferably L-lysine, L-arginine, L-histidine, and mixtures thereof.

[0062] The amino acid preferably has two nucleophilic groups.

[0063] The first amino compound can be selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof. According to a particular embodiment, the first amino compound is L-lysine.

[0064] By way of non-limiting example, the second amino compound may be selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine (Jeffamine®), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines having a disulfide bond, such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.

[0065] According to one embodiment, the second amino compound is an amine having a disulfide bond and is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.

[0066] According to another embodiment, the second amino compound is selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, Jeffamine®, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, and mixtures thereof.

[0067] According to a particular embodiment, the second amino compound is a mixture of two amino compounds, preferably a mixture of ethylenediamine and diethylenetriamine.

[0068] According to one embodiment, the weight ratio between the first amino compound and the second amino compound is 0.5-25, preferably 1.3-10, more preferably 1.3-7.

[0069] When the first and second amino compounds are present in the shell: the molar ratio between the functional group NH2 of the second amino compound and the functional group COCl of the acyl chloride is preferably comprised between 0.01 and 7.5, more preferably between 0.1 and 3.0, and / or The functional group NH2 of the first amino compound and the functional group COCl of the acyl chloride are preferably comprised between 0.2 and 3, more preferably between 0.5 and 2.

[0070] stabilizers According to one embodiment, the shell comprises a stabilizer.

[0071] For clarity, in the context of the present invention, the term "stabilizer" or similar expressions has the usual meaning understood by those skilled in the art, i.e., a compound capable of stabilizing or added to stabilize the oil-in-water interface, for example, to prevent phase separation or aggregation or agglomeration of microcapsules, for example, during application or their preparation. The use of such stabilizers is standard knowledge for those skilled in the art. For the purposes of the present invention, the stabilizer may be an ionic or nonionic surfactant, a solid particle (Pickering) or a colloidal stabilizer. The exact nature of such stabilizers is well known to those skilled in the art.

[0072] According to one embodiment, the stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo-collagen, silk protein, sericin powder, and mixtures thereof.

[0073] According to certain embodiments, the stabilizer is a biopolymer.

[0074] "Biopolymer" means a biological macromolecule produced by an organism. Biopolymers are characterized by a molecular weight distribution ranging from 1,000 (one thousand) to 1,000,000,000 (one billion) daltons. These macromolecules may be carbohydrates (sugar-based) or proteins (amino acid-based), or a combination of both (gums), and may be linear or branched.

[0075] According to certain embodiments, the stabilizer is a biopolymer selected from the group consisting of proteins such as whey protein, casein, sodium caseinate, bovine serum albumin, and mixtures thereof.

[0076] According to certain embodiments, the polyamide core-shell microcapsules comprise: - an oily core containing a hydrophobic material, preferably a fragrance; a polyamide shell, at least one acyl chloride as defined above, preferably in an amount comprised between 5 and 98% w / w; a first amino compound as defined above, preferably in an amount comprised between 1% and 80% w / w; optionally a second amino compound as defined above, preferably in an amount comprised between 1% and 80% w / w; optionally a stabilizer as defined above, preferably a biopolymer, preferably in an amount comprised between 0 and 90% w / w; a polyamide shell comprising: Includes.

[0077] It should be understood that the total of the shell components equals 100%.

[0078] According to certain embodiments, the polyamide core-shell microcapsules comprise: - an oily core containing a hydrophobic material, preferably a fragrance; a polyamide shell, at least one acyl chloride as defined above, a first amino compound, which is 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 selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine, and mixtures thereof, and a biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein, and mixtures thereof; a polyamide shell comprising: Includes.

[0079] According to certain embodiments, the polyamide core-shell microcapsules comprise an additional polyurea layer.

[0080] Optional outer coating According to certain embodiments of the present invention, the microcapsules of the present invention may comprise an outer coating comprising a polymer selected from the group consisting of nonionic polysaccharides, anionic coatings, cationic polymers, polysuccinimide derivatives, and mixtures thereof to form an outer coating on the microcapsules.

[0081] Nonionic polysaccharide polymers are well known to those skilled in the art and are described, for example, in WO 2012 / 007438, page 29, lines 1-25, and WO 2013 / 026657, page 2, lines 12-19, and page 4, lines 3-12. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose, and hydroxypropyl methylcellulose.

[0082] Cationic polymers are well known to those skilled in the art. Preferred cationic polymers have a cationic charge density of at least 0.5 meq / g, more preferably at least about 1.5 meq / g, but also preferably less than about 7 meq / g, more preferably less than about 6.2 meq / g. The cationic charge density of the cationic polymer can be determined by the Kjeldahl method described in the United States Pharmacopeia under Chemical Tests for Nitrogen Determination. Preferred cationic polymers are selected from those containing units containing primary, secondary, tertiary, and / or quaternary amine groups, which may form part of the polymer backbone or may have side-chain substituents directly attached thereto. The weight-average (Mw) molecular weight of the cationic polymer is preferably 10,000 to 3.5 M Daltons, more preferably 50,000 to 1.5 M Daltons. According to particular embodiments, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylamino methacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1-vinyl-1H-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride, and cellulose hydroxypropyltrimonium chloride are used. Preferably, the copolymer should be selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.Specific examples of commercially available products include Salcare® SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, supplier: BASF) or Luviquat®, such as PQ 11N, FC 550, or Style (quaternized copolymer of polyquaternium-11-68 or vinylpyrrolidone, supplier: BASF), or Jaguar® (C13S or C17, supplier: Rhodia).

[0083] Another object of the present invention is to provide - a polymeric carrier material, preferably selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginate, carrageenan, cellulose derivatives, and mixtures thereof; - microcapsules as defined above incorporated into said carrier material; - optionally a free flavoring incorporated in said carrier material; are solid particles containing

[0084] The solid particles and microcapsule powders defined above are used interchangeably in the present invention.

[0085] Method for producing polyamide microcapsules Another object of the present invention is to provide a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to obtain an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry; 1. A method for producing a polyamide core-shell microcapsule slurry, comprising: A stabilizer is added to the oil and / or water phase; at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), The acyl chloride is represented by the following formula (I): [ka] wherein n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is an (n+1)-valent C3 to C6 alkyl group, or (i) to (vi) [ka] (n+1)-valent C2 to C containing at least one group selected from 45 a hydrocarbon group, R is a hydrogen atom, a methyl group, or an ethyl group, preferably a hydrogen atom. but not cyclohexane-1,3,5-tricarbonyl trichloride and diglycocyl chloride.

[0086] In one step of this process, an oil phase is formed by mixing at least one hydrophobic material with at least one acyl chloride as defined above.

[0087] The hydrophobic material is as defined above.

[0088] According to any one of the embodiments of the present invention, the hydrophobic material is present in an amount of about 10% to 60% w / w, or even 15% to 45% w / w, by weight, relative to the total weight of the emulsion obtained after step b).

[0089] According to a particular embodiment, an additional acyl chloride, preferably selected from the group consisting of benzene-1,3,5-tricarbonyl chloride, benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthalyl dichloride, diglycolyl dichloride, succinic acid dichloride, and mixtures thereof, is added to the oil phase together with the acyl chloride of formula (I).

[0090] The weight ratio between the acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.2, preferably between 0.01 and 0.09, more preferably between 0.03 and 0.07.

[0091] The acyl chloride can be dissolved directly in the hydrophobic material, preferably perfume oil, or it can be pre-dispersed in an inert solvent such as benzyl benzoate before mixing with the hydrophobic material.

[0092] According to a particular embodiment, a polyisocyanate having at least two isocyanate functional groups is added to the oil phase.

[0093] Suitable polyisocyanates for use in accordance with the present invention include aromatic polyisocyanates, aliphatic polyisocyanates, and mixtures thereof. The polyisocyanates contain at least two, preferably at least three, isocyanate functional groups, but may contain up to six, or even only four, isocyanate functional groups. According to certain embodiments, triisocyanates (three isocyanate functional groups) are used.

[0094] According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.

[0095] The term "aromatic polyisocyanate" is intended herein to encompass any polyisocyanate containing an aromatic moiety. Preferably, it contains a phenyl, toluyl, xylyl, naphthyl, or diphenyl moiety, more preferably a toluyl or xylyl moiety. Preferred aromatic polyisocyanates are biurets, polyisocyanates, and trimethylolpropane adducts of diisocyanates, more preferably containing one of the specific aromatic moieties listed above. More preferably, the aromatic polyisocyanate 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 a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0096] According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain an aromatic moiety. Preferred aliphatic polyisocyanates are hexamethylene diisocyanate trimer, isophorone diisocyanate trimer, hexamethylene diisocyanate trimethylolpropane adduct (available from Mitsui Chemicals), or hexamethylene diisocyanate biuret (commercially available from Bayer under the trade name Desmodur® N100), of which hexamethylene diisocyanate biuret is more preferred.

[0097] According to another embodiment, the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and at least one aromatic polyisocyanate, both of which contain at least two or three isocyanate functional groups, such as a mixture of hexamethylene diisocyanate biuret and xylylene diisocyanate trimethylolpropane adduct, a mixture of hexamethylene diisocyanate biuret and toluene diisocyanate polyisocyanurate, and a mixture of hexamethylene diisocyanate biuret and toluene diisocyanate trimethylolpropane adduct. Most preferably, this is a mixture of hexamethylene diisocyanate biuret and xylylene diisocyanate trimethylolpropane adduct. Preferably, when used as a mixture, the molar ratio between the aliphatic polyisocyanate and the aromatic polyisocyanate ranges from 80:20 to 10:90.

[0098] According to one embodiment, the at least one polyisocyanate used in the process of the invention is present in an amount corresponding to 0.1 to 15% by weight, preferably 0.5 to 10% by weight, more preferably 0.8 to 6% by weight, even more preferably 1 to 3% by weight, based on the total amount of the oil phase.

[0099] According to the method of the present invention, a stabilizer is added to the oil phase and / or the aqueous phase, the stabilizer being as defined above.

[0100] If a colloidal stabilizer is added to the oil phase, it is preferably selected from the group consisting of proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo-collagen, silk protein, sericin powder, and mixtures thereof.

[0101] When added to the oil phase, the stabilizer can be pre-dispersed in an inert solvent such as benzyl benzoate or can be mixed with the active ingredient, preferably with the active ingredient including the perfume oil.

[0102] The stabilizer and acyl chloride may be premixed and heated, for example at a temperature of 10 to 80° C., before mixing with the hydrophobic material, preferably a hydrophobic material comprising a perfume oil.

[0103] If a colloidal stabilizer is added to the aqueous phase, it is preferably selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo-collagen, silk protein, sericin powder, and mixtures thereof.

[0104] According to any one of the above embodiments of the present invention, the emulsion comprises about 0.01% to 3.0% of at least one stabilizer, the percentage being expressed on a w / w basis relative to the total weight of the oil-in-water emulsion obtained after step b). In yet another aspect of the present invention, the emulsion comprises about 0.05% to 2.0%, preferably 0.05 to 1%, of at least one colloidal stabilizer. In yet another aspect of the present invention, the emulsion comprises about 0.1% to 1.6%, preferably 0.1% to 0.8% by weight of at least one colloidal stabilizer.

[0105] According to the process of the present invention, at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), the nature of which is as defined above.

[0106] According to a particular embodiment, the oil phase of step a) is dispersed in an aqueous phase comprising a first amino compound and, optionally, a stabilizer, to form an oil-in-water emulsion.

[0107] According to another embodiment, the oil phase of step a) is dispersed in an aqueous phase comprising two amino compounds and, optionally, a stabilizer, to form an oil-in-water emulsion.

[0108] The emulsion can be produced by high shear mixing and adjusted to the desired droplet size, preferably 1 to 1000 microns, more preferably 1 to 500 microns, and even more preferably 5 to 50 microns.

[0109] The first amino compound is as defined above.

[0110] According to one embodiment, in another step of the method according to one embodiment, a second amino compound is added to the oil-in-water emulsion obtained in step b), the second amino compound being as defined above.

[0111] According to certain embodiments, the method comprises: i) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; ii) dispersing the oil phase obtained in step a) in an aqueous phase containing a first amino compound to obtain an oil-in-water emulsion; iii) adding a second amino compound to the oil-in-water emulsion; iv) carrying out a curing step to form polyamide microcapsules in the form of a slurry; Including, The stabilizer is added to the oil phase and / or the water phase, The acyl chloride is as defined above.

[0112] Without being bound by any theory, the inventors believe that when two amino compounds are added during the process, the first amino compound reacts with the acyl chloride to form a polyamide, and the second amino compound reacts with the remaining acyl chloride group of the acyl chloride.

[0113] According to a particular embodiment, the first amino compound and the second amino compound are the same.

[0114] According to another particular embodiment, the first amino compound and the second amino compound are different.

[0115] According to one embodiment, the weight ratio between the first amino compound and the second amino compound is comprised between 0.5 and 25, preferably between 1.3 and 10, more preferably between 1.3 and 7.

[0116] According to a particular embodiment, two amino compounds are added during the process, preferably sequentially, with the first amino compound being added to the aqueous phase in step b) and preferably at least the second amino compound being added after the emulsion has been formed. Indeed, without being bound by any theory, the inventors have observed that the combination of both amino compounds results in stable microcapsules in consumer products.

[0117] The amount of the second amino compound used is typically adjusted so that the molar ratio between the functional group NH2 of the second amino compound and the functional group COCl of the acyl chloride is comprised between 0.01 and 7.5, preferably between 0.1 and 3.0.

[0118] The amount of the first amino compound used is typically adjusted so that the molar ratio between the functional group NH2 of the first amino compound and the functional group COCl of the acyl chloride is comprised between 0.2 and 3, preferably between 0.5 and 2.

[0119] According to one embodiment, a base is added at the end of step b) to adjust the pH, non-limiting examples of which include guanidine carbonate, sodium bicarbonate, or triethanolamine.

[0120] According to a particular embodiment, the base is not an amino compound.

[0121] The base is preferably added in an amount of 0.1% to 10% by weight, more preferably 0.5% to 5% by weight, based on the oil-in-water emulsion.

[0122] This is followed by a hardening step c), which finally gives rise to microcapsules in the form of a slurry. According to a preferred embodiment, in order to increase the reaction rate, said step is carried out at a temperature comprised between 5 and 90°C, optionally under pressure, for a period of 1 to 8 hours. More preferably, it is carried out at a temperature comprised between 10 and 80°C for a period of 30 minutes to 5 hours.

[0123] According to a particular embodiment of the present invention, at the end of or during step d), a polymer selected from the group consisting of non-ionic polysaccharides, anionic coatings, cationic polymers, polysuccinimide derivatives, and mixtures thereof may also be added to the slurry of the present invention to form the outer coating of the microcapsules, wherein the non-ionic polysaccharides or cationic polymers are as defined above.

[0124] According to any one of the above embodiments of the present invention, the above mentioned polymer is added in an amount comprised between about 0% and 5% w / w, or even between about 0.1% and 2% w / w, the percentage being expressed on a w / w basis relative to the total weight of the slurry obtained after step c) or d). It will be clearly understood by those skilled in the art that only a portion of said added polymer will be incorporated into / deposited on the microcapsule shell.

[0125] Another object of the present invention is a method for producing a microcapsule powder, comprising the steps defined above and an additional step d) or e) consisting in subjecting the slurry obtained in step c) or d) to drying, such as spray drying, to obtain the microcapsules as such, i.e. in powder form. It is understood that any standard method known to those skilled in the art for carrying out such drying is applicable. In particular, the slurry can be spray-dried, preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginate, carrageenan or a cellulose derivative, to obtain microcapsules in powder form.

[0126] According to a particular embodiment, the carrier material comprises free perfume oil, which may be the same as or different from the perfume from the core of the microcapsules.

[0127] Another object of the present invention is the polyamide microcapsule slurry obtained by the above process.

[0128] Multi-Capsule System According to one embodiment, the microcapsules of the present invention (microcapsules of a first type) can be used in combination with microcapsules of a second type.

[0129] Another object of the present invention is to provide - microcapsules of the invention as a first type of microcapsules, - a second type of microcapsules; wherein the first type of microcapsules and the second type of microcapsules differ in hydrophobic material and / or wall material and / or coating material.

[0130] Fragrance compositions / consumer products The microcapsules of the present invention can be used in combination with active ingredients. (i) a microcapsule as defined above; (ii) an active ingredient, preferably selected from the group consisting of a cosmetic ingredient, a skin care ingredient, a fragrance ingredient, a flavor ingredient, a malodor control ingredient, a bactericidal ingredient, a fungicidal ingredient, a pharmaceutical or pesticide ingredient, a disinfectant ingredient, an insect repellent or insect attractant ingredient, and mixtures thereof; A composition comprising:

[0131] The microcapsules of the invention can be used for the preparation of perfuming or flavoring compositions, which are also the object of the present invention.

[0132] The capsules of the present invention exhibit excellent performance in terms of stability in difficult media.

[0133] Another object of the present invention is to provide (i) microcapsules as defined above, wherein the oil contains a fragrance; (ii) at least one component selected from the group consisting of a fragrance carrier, a fragrance co-ingredient, and mixtures thereof; (iii) optionally at least one flavoring adjuvant; A fragrance composition comprising:

[0134] Liquid perfume carriers include, but are not limited to, emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in perfumery. A detailed description of the nature and types of solvents commonly used in perfumery is not exhaustive. However, non-limiting examples include the most commonly used solvents, such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol, or ethyl citrate. For compositions containing both a perfume carrier and a perfume co-ingredient, other suitable perfume carriers besides those specified above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (supplied by Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (supplied by Dow Chemical Company). The term "perfume co-ingredient" as used herein refers to a compound, other than a microcapsule as defined above, used in a perfume formulation or composition to impart a hedonic effect. In other words, such co-ingredients should be recognized by those skilled in the art not only to have an odor but also to be capable of at least imparting or modifying the odor of the composition in a positive or pleasant way.

[0135] The nature and type of perfume co-ingredients present in perfume compositions do not warrant a more detailed description herein, and in any case, are not exhaustive; those skilled in the art can select them based on their general knowledge and according to the intended use or application and the desired sensory effect. Generally, these perfume co-ingredients belong to chemical classes such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpenoids, nitrogen or sulfur heterocyclic compounds, and essential oils, and said perfume co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are listed in reference texts such as S. Arctander's book "Perfume and Flavor Chemicals" (1969, Montclair, New Jersey, USA) or its more recent versions, or other works of a similar nature, as well as in the abundant patent literature in the perfumery field. It is also understood that said co-ingredients can be compounds known to release various types of perfume compounds in a controlled manner.

[0136] The concomitant ingredients are 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, and 2-phenylethyloxo(phenyl)acetate. , 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-ylhexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethyl) (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, or mixtures thereof.

[0137] By "perfuming adjuvant" is meant herein an ingredient that may provide additional benefits such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfume bases cannot be exhaustive, but it should be mentioned that said ingredients are well known to those skilled in the art.

[0138] Preferably, the perfuming composition according to the invention comprises 0.01 to 30% by weight of microcapsules as defined above.

[0139] The microcapsules of the present invention can be advantageously used in many fields of application and can be used in consumer products: the microcapsules can be used in liquid form for liquid consumer products and in powder form for powder consumer products.

[0140] According to a particular embodiment, the consumer product as defined above is a liquid, a) 2 to 65% by weight of at least one surfactant, based on the total weight of the consumer product; b) water or a water-miscible hydrophilic organic solvent; c) a microcapsule slurry as defined above; d) optionally, a non-encapsulated fragrance; and Includes.

[0141] According to a particular embodiment, the consumer product as defined above is in powder form, a) 2 to 65% by weight of at least one surfactant, based on the total weight of the consumer product; b) a microcapsule powder as defined above; c) optionally a flavoring powder different from the microcapsules defined above; Includes.

[0142] In the case of microcapsules containing an oily perfume core, the products of the present invention can be used in perfumed consumer products, especially those belonging to the fine perfumery or "functional" perfumery category. Functional perfumery includes in particular personal care products such as hair care, body cleansing, skin care, and hygiene care, as well as home care products such as laundry care and air care. Consequently, another object of the present invention consists in perfumed consumer products containing the microcapsules defined above or the perfume composition defined above as perfuming ingredients. The perfume element of said consumer product may be a combination of perfume microcapsules defined above, free or non-encapsulated perfume, and other types of perfume microcapsules other than those disclosed herein.

[0143] especially, a) 2 to 65% by weight of at least one surfactant, based on the total weight of the consumer product; b) water or a water-miscible hydrophilic organic solvent; c) a perfuming composition as defined above; A liquid consumer product comprising:

[0144] Also, a) 2 to 65% by weight of at least one surfactant, based on the total weight of the consumer product; b) a perfuming composition as defined above; Powdered consumer products comprising:

[0145] Thus, the microcapsules of the present invention can be added by themselves or as part of the perfume composition of the present invention to perfumed consumer products.

[0146] For the sake of clarity, it should be stated that by "perfumed consumer product" is meant a consumer product that is expected to provide, among other benefits, a fragrance effect on the surface to which it is applied (e.g., skin, hair, fabric, paper, or residential surfaces) or in the air (fragrance, deodorizer, etc.) In other words, a perfumed consumer product according to the invention is a manufactured product that includes a functional formulation, also called a "base", together with a beneficial agent, among other things, an effective amount of the microcapsules according to the invention.

[0147] The nature and type of other ingredients of perfumed consumer products do not warrant a more detailed description herein, and in any case, this is not exhaustive, and those skilled in the art can select them based on common knowledge and according to the nature and desired effect of the product.Base formulations of consumer products that can incorporate the microcapsules of the present invention can be found in the abundant literature related to such products.These formulations do not warrant a more detailed description herein, and in any case, this is not exhaustive.Those skilled in the art of formulating such consumer products can completely select suitable ingredients based on common knowledge and available literature.

[0148] Non-limiting examples of suitable perfumed consumer products include perfumes such as fine fragrances, colognes, aftershaves, and body splashes; clothing care products such as liquid or solid detergents, tablets and pods, fabric softeners, dryer sheets, fabric fresheners, ironing water, or bleach; personal care products such as hair care products (e.g., shampoo, hair conditioner, dye, or hairspray), 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 deodorants or "ready-to-use" powdered deodorants; or home care products such as all-purpose detergents, liquid, powder, or tablet dishwashing products, toilet cleaners, or products for cleaning various surfaces, e.g., sprays and wipes intended to treat / restore clothing or hard surfaces (floors, tiles, stone paving, etc.); hygiene products such as sanitary napkins, diapers, toilet paper, etc.

[0149] Another object of the present invention is to provide - Effective bases for personal care and - microcapsules as defined above or a perfuming composition as defined above, and a consumer product in the form of a personal care composition comprising:

[0150] The personal care active bases that can be formulated with the microcapsules of the present invention can be found in the abundant literature related to such products. These formulations do not warrant a more detailed description herein, and are in any case not exhaustive. Those skilled in the art of formulating such consumer products can fully select the appropriate ingredients based on common knowledge and available literature.

[0151] The personal care composition is preferably selected from the group consisting of a hair care product (e.g., shampoo, hair conditioner, dye, or hair spray), a cosmetic product (e.g., vanishing cream, body lotion, or deodorant or antiperspirant), or a skin care product (e.g., perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or hygiene product);

[0152] Another object of the present invention is to provide - a base effective for home or clothing care; - microcapsules as defined above or a perfuming composition as defined above, and a consumer product in the form of a home care or clothing care composition comprising:

[0153] The useful bases for home or clothing care that can be formulated with the microcapsules of the present invention can be found in the abundant literature related to such products. These formulations do not warrant a more detailed description herein, and are in any case not exhaustive. Those skilled in the art of formulating such consumer products are fully capable of selecting the appropriate ingredients based on common knowledge and available literature.

[0154] Preferably, the consumer product comprises 0.1 to 15% by weight, more preferably 0.2 to 5% by weight, of the microcapsules of the invention, these percentages being defined by weight relative to the total weight of the consumer product. Naturally, these concentrations can be adjusted depending on the beneficial effect desired for each product.

[0155] According to certain embodiments, the consumer product in which the microcapsules are incorporated has a pH of less than 4.5.

[0156] By "effective base" in reference to liquid consumer products referred to below, it is to be understood that the effective base comprises an active agent (typically including a surfactant) and water.

[0157] "Active base" in reference to solid consumer products referred to below should be understood to include active materials (typically including surfactants) and adjuvants (such as bleaches, buffers, builders, soil release or soil suspension polymers, granular enzyme particles, corrosion inhibitors, defoamers, suds suppressors, dyes, fillers, and mixtures thereof).

[0158] Fabric softener The object of the present invention is to - a base useful in fabric softeners, preferably a base comprising at least one active material selected from the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquats (HEQs), TEAQs (triethanolamine quats), silicones, and mixtures thereof, preferably used in an amount of 85 to 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a consumer product in the form of a fabric softener composition comprising:

[0159] Liquid detergent The object of the present invention is to - a base useful in liquid detergents, preferably comprising at least one active substance selected from the group consisting of anionic surfactants such as alkyl benzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and nonionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), copolymers of ethylene oxide (EO) and propylene oxide (PO), amine oxides, alkyl polyglucosides, alkyl polyglucosamides, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a liquid detergent composition comprising:

[0160] Solid detergent The object of the present invention is to - a base useful for solid detergents, preferably containing at least one active substance selected from the group consisting of anionic surfactants such as alkyl benzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and nonionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), copolymers of ethylene oxide (EO) and propylene oxide (PO), amine oxides, alkyl polyglucosides, alkyl polyglucosamides, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule powder or a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a consumer product in the form of a solid detergent composition comprising:

[0161] Shampoo / Shower gel The object of the present invention is to - a base useful for shampoos or shower gels, preferably comprising at least one active substance selected from the group consisting of sodium alkyl ether sulfates, ammonium alkyl ether sulfates, alkyl amphoacetates, cocamidopropyl betaine, cocamide MEA, alkyl glucosides, and amino acid-based surfactants, and mixtures thereof, preferably used in an amount comprised between 85 and 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a consumer product in the form of a shampoo or shower gel composition comprising:

[0162] Rinse-off conditioner The object of the present invention is to a base useful in rinse-off conditioners, preferably comprising at least one active substance selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride, and mixtures thereof, preferably used in an amount of 85 to 99.95% by weight, based on the total weight of the composition; - a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, The present invention relates to a consumer product in the form of a rinse-off conditioner composition comprising:

[0163] Solid fragrance enhancer The object of the present invention is to a solid carrier, preferably selected from the group consisting of urea, sodium chloride, sodium sulfate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars such as sucrose, monosaccharides, disaccharides, and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PEG, PVP, citric acid, or any water-soluble solid acid, fatty alcohol, or fatty acid, and mixtures thereof, - a microcapsule slurry as defined above in powder form, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a consumer product in the form of a solid fragrance enhancer, comprising:

[0164] Liquid fragrance enhancer The object of the present invention is to an aqueous phase; - a surfactant system consisting essentially of one or more nonionic surfactants having an average HLB of 10 to 14, preferably selected from the group consisting of ethoxylated fatty 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 linker selected from the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxylcarboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactants with an HLB of less than 10, and mixtures thereof; - a microcapsule slurry as defined above in slurry form, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a liquid fragrance enhancer comprising:

[0165] hair dye The object of the present invention is to - an oxidation phase containing an oxidizing agent, an alkaline phase containing an alkali agent, a dye precursor, and a coupling compound, preferably in an amount of 85 to 99.95% by weight based on the total weight of the composition (the dye precursor and the coupling compound form an oxidation hair dye in the presence of the oxidizing agent); - a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; optionally free perfume oil, and a consumer product in the form of an oxidation hair dye composition comprising:

[0166] "Oxidation hair dye composition" refers to a composition containing two groups of colorless dye molecules: dye precursors and coupling agents. When reacted with each other through an oxidation process, they form a variety of colored molecules (dyes), which are then incorporated into hair due to their size. In other words, the dye precursors and coupling compounds form an oxidation hair dye in the presence of an oxidizing agent.

[0167] The terms "dye precursor" and "oxidation dye precursor" are used interchangeably in the present invention.

[0168] The dye precursor can be an aromatic compound derived from benzene substituted with at least two electron-donating groups such as NH2 or OH at the para or ortho positions to impart easy oxidation properties.

[0169] According to one embodiment, the dye precursor is selected from the group consisting of p-phenylenediamine, 2,5-diaminotoluene, N,N-bis(2-hydroxymethyl)-p-phenylenediamine, 4-aminophenol, 1,4-diaminobenzene, and mixtures thereof.

[0170] The primary dye precursors are used in combination with a coupling agent, preferably an aromatic compound derived from benzene and meta-substituted with groups such as NH or OH, which does not produce color by itself but modifies the color, hue, or intensity of the color produced by the dye precursor.

[0171] According to one embodiment, the coupling agent is selected from the group consisting of resorcinol, 2-methylresorcinol, 4-chlororesorchinol, 2,5-diaminotoluene, 1,3-diaminobenzene, 2,4-diaminophenoxyethanol HCl, 2-amino-hydroxyethylaminoanisole sulfate, 4-amino-2-hydroxytoluene, and mixtures thereof.

[0172] The oxidation dye precursor is preferably used in an amount comprised between 0.001% and 5% by weight, preferably between 0.1% and 4% by weight, based on the total weight of the composition.

[0173] The use of oxidative dye precursors and coupling agents in hair dye formulations has been widely disclosed in the prior art and is well known to those skilled in the art, for example, EP 0 946 133 A1, which is incorporated by reference in its entirety.

[0174] The alkaline phase preferably comprises an alkaline agent selected from the group consisting of ammonium hydroxide, ammonium carbonate, ethanolamine, potassium hydroxide, sodium borate, sodium carbonate, triethanolamine, and mixtures thereof.

[0175] The alkaline agent is preferably used in an amount comprised between 1% and 10% by weight, preferably between 3% and 9% by weight, based on the total weight of the composition.

[0176] According to the present invention, a coupling agent and a dye precursor in an alkaline medium form an oxidation hair dye in the presence of an oxidizing agent.

[0177] The oxidizing agent provides the oxygen gas necessary to develop the color molecules and change the color of the hair.

[0178] The oxidizing agent should be safe and effective for use in the compositions herein.

[0179] Preferably, the oxidizing agents suitable for use herein are soluble in the compositions according to the invention when in liquid form and / or in the form in which they are intended for use.

[0180] Preferably, the oxidizing agents suitable for use herein are water soluble. The oxidizing agents suitable for use herein are selected from inorganic peroxygen oxidizing agents, preformed organic peroxyacid oxidizing agents and organic peroxide oxidizing agents, or mixtures thereof.

[0181] The oxidizing agent is preferably used in an amount comprised between 5 and 30% by weight, preferably between 5 and 25% by weight, based on the total weight of the composition.

[0182] Ingredients commonly used in cosmetic compositions can be added to the hair dye composition defined in the present invention, such as surfactants, cationic polymers, oily substances, silicone derivatives, free fragrances, preservatives, UV absorbers, antioxidants, bactericides, propellants, and thickeners.

[0183] According to certain embodiments, the hair dye composition comprises one or more quaternary ammonium compounds, preferably selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride, and mixtures thereof, to impart hair conditioner benefits.

[0184] Perfuming composition According to certain embodiments, the consumer product comprises, based on the total weight of the fragrance composition, - 0.1 to 30%, preferably 0.1 to 20%, of microcapsules as defined above, - 0 to 40%, preferably 3 to 40% of fragrance, 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol; The fragrance composition is in the form of a fragrance composition comprising:

[0185] The present invention is further illustrated by the following examples, it being understood that the invention as claimed is not intended to be limited in any way by these examples.

[0186] Example Hereinafter, the present invention will be described in more detail by the following examples, in which abbreviations have their usual meaning in the art and temperatures are given in degrees Celsius (°C). NMR spectral data are given in the following order unless otherwise indicated. 1 For H, it is 500MHz, 13 C was recorded on a Bruker AMX 500 spectrometer at 125.8 MHz in deuterated tetrahydrofuran (THF)-d. Chemical shifts δ are given in ppm relative to Si(CH) as the standard. Coupling constants J are expressed in Hz (br. = broad peak). Reactions were carried out in standard glassware under N. Commercially available reagents and solvents were used without further purification unless otherwise stated.

[0187] Although specific conformations or configurations are shown for some compounds, this is not intended to limit the use of these compounds to the isomers depicted, and all possible conformational or configurational isomers are expected to have similar effects according to the present invention.

[0188] Example 1 Preparation of acyl chlorides of formula (I) (a) Synthesis of propane-1,2,3-tricarbonyl trichloride (acyl chloride 1) In a Schlenk tube previously dried in an oven at 150 °C, thionyl chloride (20.0 mL, 1.64 g mL -1 , 276 mmol) and 2-3 drops of N,N-dimethylformamide (DMF) were added to propane-1,2,3-tricarboxylic acid (2.00 g, 11 mmol, supplier: TCI). The reaction mixture was heated to reflux overnight under a stream of nitrogen and neutralized by passing a wash bottle containing aqueous NaOH (10%) through it. An aliquot (0.1 mL) of the reaction mixture was removed with a pipette and placed in a small vial. After evaporating the SOCl2 and flushing with argon, a sample (38 mg) was analyzed by NMR spectroscopy. The remaining SOCl2 from the sample was evaporated and the product was flushed with argon.

[0189] [ka]

[0190] (b) Synthesis of cyclohexane-1,2,4,5-tetracarbonyl tetrachloride (acyl chloride 2) In a Schlenk tube previously dried in an oven at 150 °C, SOCl2 (25.0 mL, 345 mmol) and three drops of DMF were added to cyclohexane-1,2,4,5-tetracarboxylic acid (6.64 g, 26 mmol, supplier: TCI). The reaction mixture was stirred under a stream of nitrogen at room temperature for 2 days and neutralized by passing a wash bottle containing aqueous NaOH (10%) through it. An aliquot (0.05 mL) of the reaction mixture was pipetted into a small vial. After evaporating the SOCl2 and flushing with argon, a sample (34 mg) was analyzed by NMR spectroscopy. The remaining SOCl2 from the sample was evaporated, and the product was flushed with argon. [ka]

[0191] (c) Synthesis of 2,2'-disulfanediyldisuccinyl dichloride (acyl chloride 3) Ferrous sulfate hydrate (FeSO4 x 7HO, 80 mg, 0.3 mmol) was added to a stirred solution of 2-mercaptosuccinic acid (thiomalic acid, 32, 29.6 g, 197.1 mmol, supplier: TCI) in water (250 mL). Hydrogen peroxide (35%, 14.59 g, 150.1 mmol) was then added dropwise over 5–10 min, maintaining the temperature below 35 °C with an ice bath. After stirring overnight at room temperature, the reaction mixture was extracted with ethyl acetate (250 mL, 3×). The aqueous layer was re-extracted with ethyl acetate (250 mL), and the combined organic layers were washed with a saturated aqueous solution of NaCl (100 mL, 2×), dried (Na2SO4), and concentrated (45 °C, 5 mbar) to give 23.40 g of a white crystalline solid. The solid (22.38 g) was crushed and dried in a desiccator (0.06 mbar) to give 22.10 g (79%) of 2,2'-disulfanediyldisuccinic acid as a diastereoisomeric mixture. [ka]

[0192] In a Schlenk tube, SOCl2 (11.6 mL, 160.0 mmol) was rapidly added to a suspension of 2,2'-disulfanediyldisuccinic acid (5.96 g, 20.0 mmol) in dichloromethane (40 mL). The reaction mixture was heated to reflux under a stream of nitrogen and neutralized by passing a wash bottle containing aqueous NaOH (10%). After 1 h, additional dichloromethane (15 mL) was added, and the reaction was continued to be heated at reflux overnight. The solvent and excess SOCl2 were then removed under nitrogen using a distillation bridge. The product was dried using a membrane pump to give the desired compound. [ka]

[0193] (d) Synthesis of 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride (acyl chloride 4) In a Schlenk tube previously dried in an oven at 150 °C, SOCl2 (10.0 mL, 138 mmol) and three drops of DMF were added to 2-(carboxymethylsulfanyl)butanedioic acid (4.30 g, 20 mmol, supplied by Alfa Aesar). The reaction mixture was heated to reflux overnight at room temperature under a stream of nitrogen and neutralized by passing a wash bottle containing aqueous NaOH (10%) through it. An aliquot (0.1 mL) of the reaction mixture was pipetted into a small vial. After evaporating the SOCl2 and flushing with argon, a sample (38 mg) was analyzed by NMR spectroscopy. The remaining SOCl2 was evaporated from the sample and flushed with argon to give the desired compound. [ka]

[0194] (e) Synthesis of (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride (acyl chloride 5) Sodium hydroxide (2.50 g) was rapidly added to a suspension of L-glutamic acid (8.83 g, 60 mmol) in water (100 mL), which was cooled in a water bath to maintain the temperature below 20 °C. The pH was adjusted to 8.25-9.50 by adding aqueous NaOH (10%, 8 mL). Succinic anhydride (6.00 g, 60 mmol) was added in 1 g increments every 15 min, while maintaining the reaction temperature at approximately 20 °C using a cold water bath. Each addition of aqueous NaOH (10%, 10 mL required for a total of 50 mL) maintained the pH between 9.0 and 9.5. A colorless solution (pH 9.40) was obtained. The reaction mixture was left stirring at room temperature over the weekend (pH 9.13). Dowex® Marathon resin (65 g) was washed in a Buchner filter with an aqueous solution of HCl (10%) and deionized water until neutral. The Dowex® resin was slowly added in small portions to the reaction (pH 2.76), left to stir for 1 h, then filtered and rinsed with water (50 mL). The filtrate was lyophilized (16 h) and dried under vacuum (0.05 mbar) for 3 h to give 15.76 g (quantitative) of (3-carboxypropanoyl)-L-glutamic acid. [ka]

[0195] In a Schlenk tube previously dried in an oven at 150 °C, SOCl2 (20.0 mL, 276 mmol) and three drops of DMF were added to (3-carboxypropanoyl)-L-glutamic acid (6.18 g, 25 mmol). The reaction mixture was slowly heated under a stream of nitrogen and neutralized by passing a wash bottle containing aqueous NaOH (10%) through it. After heating at 60 °C overnight, an aliquot (0.2 mL) of the reaction mixture was pipetted into a small vial. After evaporation of the SOCl2, a sample (63 mg) was analyzed by NMR spectroscopy (purity approximately 90%). The remaining SOCl2 from the sample was evaporated, and the residue was dried under vacuum (0.26 mbar) to yield 7.12 g (94%) of the desired compound. [ka]

[0196] (f) Synthesis of a mixture of (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride (acyl chloride 5) and (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid (acyl chloride 6) In a Schlenk tube previously dried in an oven at 150 °C, SOCl (10.0 mL, 138 mmol) was added to (3-carboxypropanoyl)-L-glutamic acid (1.24 g, 5 mmol). The reaction mixture was stirred under a stream of nitrogen and neutralized by passing a wash bottle containing aqueous NaOH (10%) through it. After heating at 70 °C overnight and stirring at room temperature for 9 days, an aliquot (0.15 mL) of the reaction mixture was pipetted into a small vial. The SOCl was evaporated, and a sample (48 mg) was analyzed by NMR spectroscopy. Analysis indicated the formation of a mixture of acyl chloride 6 and acyl chloride 5 in a ratio of approximately 1:1.7 (approximately 40:60%). [ka]

[0197] (g) Synthesis of 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate (acyl chloride 7) In a three-neck round-bottom flask, 1,1,1-tris-(hydroxymethyl)propane (5.01 g, 37.31 mmol) and triethylamine (30 mL, 215.24 mmol) were dissolved in THF (250 mL) to give a colorless solution. Succinic anhydride (23.49 g, 234.75 mmol) was added, and the reaction mixture was stirred at room temperature for 15 h. The solvent was evaporated, and ethyl acetate was added to the crude oil. The organic layer was washed with saturated aqueous NH4Cl (2x) and saturated aqueous NaCl, and dried (MgSO4). After filtration, the solvent was evaporated to give a brown solid (17.7 g). [ka]

[0198] (h) Synthesis of [2-[2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl]4-chloro-4-oxo-butanoate (acyl chloride 8) In a three-neck round-bottom flask, 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethyl-propane-1,3-diol (2.01 g, 8.04 mmol) and triethylamine (9 mL, 64.57 mmol) were dissolved in THF (100 mL) to give a colorless solution. Succinic anhydride (6.4 g, 64 mmol) was added, and the reaction mixture was stirred at room temperature for 6 h. The solvent was then evaporated, and the residue was diluted with ethyl acetate. The organic phase was washed with saturated aqueous NHCl (2×) and saturated aqueous NaCl, and dried (MgSO). After filtration, the ethyl acetate was evaporated to give 4-[2-[2,2-bis(3-carboxypropanoyloxymethyl)butoxymethyl]-2-(3-carboxypropanoyloxymethyl)butoxy]-4-oxobutanoic acid as a solid. [ka]

[0199] In a three-neck round-bottom flask, 4-[2-[2,2-bis(3-carboxypropanoyloxymethyl)butoxymethyl]-2-(3-carboxypropanoyloxymethyl)butoxy]-4-oxobutanoic acid (13.39 g, 20.58 mmol) was dissolved in THF (60 mL). SOCl2 (12.01 mL, 164.64 mmol) was then added dropwise over 10 min (yellow solution), and the reaction mixture was stirred at room temperature for 3 h. The solvent and excess SOCl2 were evaporated, and the product was dried using a membrane pump to obtain the target compound. [ka]

[0200] (i) Synthesis of 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate (acyl chloride 9) In a three-neck round-bottom flask, 1,1,1-tris-(hydroxymethyl)propane (5 g, 37.27 mmol) and triethylamine (20.78 mL, 149.06 mmol) were dissolved in THF (250 mL) to give a colorless solution. The reaction mixture was cooled to 5 °C in a cold water bath. Phthalic anhydride (17.11 g, 115.53 mmol) was added, and the reaction mixture was stirred for 15 minutes while warming to room temperature. The solvent was evaporated, and saturated aqueous NaHCO3 was added. Diethyl ether was added, and the organic layer was removed. Aqueous HCl (10%) was added to the aqueous phase to adjust the pH to 3. A white solid precipitated and was filtered off. This solid was dissolved in acetone, and the solution was dried over (MgSO4). The solvent was then evaporated to give 21.16 g of 2-[2,2-bis[(2-carboxybenzoyl)oxymethyl]butoxycarbonyl]benzoic acid as a white solid. [ka]

[0201] In a three-neck round-bottom flask, 2-[2,2-bis[(2-carboxybenzoyl)oxymethyl]butoxycarbonyl]benzoic acid (19.56 g, 33.82 mmol) and SOCl2 (100 mL, 1370.9 mmol) were combined to give a yellow solution. The reaction mixture was stirred for 4 h. Then, SOCl2 was evaporated and the crude product was dried under vacuum overnight to give an orange oil. [ka]

[0202] (j) Synthesis of [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzoate (acyl chloride 10) In a three-necked round-bottom flask, 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethyl-propane-1,3-diol (2.01 g, 8.02 mmol) and triethylamine (5.8 mL, 41.61 mmol) were dissolved in THF (75 mL). The solution was cooled to 5 °C in a cold water bath. Phthalic anhydride (5 g, 33.75 mmol) was added, and the reaction mixture was stirred for 15 h while warming to room temperature. The solvent was evaporated, and diethyl ether was added. Deionized water was added, and the organic layer was removed. An aqueous solution of HCl (10%) was added to the aqueous phase to bring the pH to 4. A white solid precipitated, which was filtered off, dissolved in acetone, and dried (MgSO4). Thereafter, the solvent was distilled off to obtain 6.3 g of 2-[2-[2,2-bis[(2-carboxybenzoyl)oxymethyl]butoxymethyl]-2-[(2-carboxybenzoyl)oxymethyl]butoxy]carbonylbenzoic acid as a white solid. [ka]

[0203] In a three-neck round-bottom flask, 2-[2-[2,2-bis[(2-carboxybenzoyl)oxymethyl]butoxymethyl]-2-[(2-carboxybenzoyl)oxymethyl]butoxy]carbonylbenzoic acid (20.2 g, 23.52 mmol) and SOCl2 (100 mL, 1370.9 mmol) were combined to give a yellow solution. DMF (50 mg) was added, and the reaction mixture was stirred for 15 h. The SOCl2 was then evaporated to give an orange oil, which was then dried overnight under vacuum. [ka]

[0204] (k) Synthesis of 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonylbenzoate (acyl chloride 11) In a three-neck round-bottom flask, 2,2,4,5-benzenetetracarboxylic anhydride (4.93 g, 22.6 mmol) and triethylamine (8 mL, 57.4 mmol) were dissolved in THF (150 mL) to give an orange solution. A solution of 1,4-butanediol (1 mL, 11.28 mmol) in THF (20 mL) was added dropwise. The reaction mixture was stirred at room temperature for 4 hours. The solvent was then evaporated to give a solid. Acetone (25 mL) was added, and the suspension was stirred for 15 hours. A saturated aqueous solution of NaHCO3 (100 mL) was added, and the reaction mixture was stirred until the solid was completely dissolved. The solution was washed with ethyl acetate (100 mL). The organic layer was removed, and the pH of the aqueous phase was adjusted to 3 with aqueous HCl (10%). A white, viscous oily phase separated. The water was removed, and the precipitate was washed with water, dissolved in acetone, dried (MgSO4), and filtered. The solvent was evaporated to give 6.2 g of 5-[4-(2,4,5-tricarboxybenzoyl)oxybutoxycarbonyl]benzene-1,2,4-tricarboxylic acid as a white solid. [ka]

[0205] In a three-necked round-bottom flask, 5-[4-(2,4,5-tricarboxybenzoyl)oxybutoxycarbonyl]benzene-1,2,4-tricarboxylic acid (5.52 g, 9.81 mmol), SOCl2 (50 mL, 236.4 mmol), and DMF (0.05 g, 0.68 mmol) were mixed to give an orange solution. The reaction mixture was stirred at 80 °C for 24 h. The SOCl2 was then evaporated to give an orange oil. [ka]

[0206] Example 2 Preparation of polyamide microcapsules A using colloidal stabilizers in the oil phase and acyl chlorides of formula (I) Perfume oils 1 and 2 were prepared by mixing the ingredients listed in Tables 1 and 2.

[0207] [Table 1]

[0208] [Table 2]

[0209] An acyl chloride of formula (I) according to the present invention (20 mmol, Table 3) was dissolved in benzyl benzoate (5 g). Sodium caseinate (2 g) was dispersed in benzyl benzoate (5 g) and, optionally, maintained at 60°C for 1 hour with stirring. Both solutions were mixed together and stirred for 10 minutes, then added to perfume oil (25 g, Table 1 or Table 2) at room temperature to form an oil phase. The oil phase was mixed with a solution of L-lysine (2.5 g) in water (95 g). The reaction mixture was stirred at 24,000 rpm for 5 minutes using an Ultra Turrax® to obtain an emulsion. Ethylenediamine (0.24 g) was dissolved in water (5 g), and this solution was added dropwise to the emulsion. The reaction mixture was stirred at 30°C for 4 hours to obtain a white dispersion.

[0210] [Table 3]

[0211] Example 3 Preparation of polyamide microcapsules B using a colloidal stabilizer in the oil phase and a mixture of 1,3,5-benzenetricarbonyl chloride and acyl chloride of formula (I) Polyamide microcapsules B were prepared according to the protocol used for polyamide microcapsules A (Example 2). An acyl chloride of formula (I) according to the present invention and 1,3,5-benzenetricarbonyl chloride (having a total of 20 mmol of acid chloride functional groups) were dissolved in benzyl benzoate (5 g). The composition of the acid chloride mixture is shown in Table 4.

[0212] [Table 4]

[0213] Example 4 Storage stability of microcapsules in fabric softener compositions The storage stability of the capsules was evaluated in a fabric softener formulation. A dispersion of polyamide microcapsules (0.27 g) according to the invention (encapsulated perfume oil 2, Table 2) was diluted with 29.73 g of the fabric softener composition described in Table 5. The fabric softener was stored at 37°C for up to one month. The amount of perfume leaked from the capsules was then determined by solvent extraction and GC-FID analysis (Table 6).

[0214] [Table 5]

[0215] [Table 6]

[0216] The data in Table 6 show that the microcapsules according to the present invention exhibit satisfactory stability in difficult application formulations such as fabric softeners.

[0217] Example 4 Liquid detergent composition Microcapsules A1-A7 and B1-B12 of the present invention are dispersed in the liquid detergent base described in Table 7 to give a concentration of 0.22% encapsulated perfume oil.

[0218] [Table 7]

[0219] Example 5 Rinse-off conditioner Microcapsules A1-A7 and B1-B12 of the present invention are dispersed in the rinse-off conditioner base described in Table 8 to give a concentration of 0.5% encapsulated perfume oil.

[0220] [Table 8]

[0221] Example 6 Shampoo composition Microcapsules A1 to A7 and B1 to B12 of the present invention are weighed and mixed into a shampoo composition, and a fragrance equivalent to 0.2% is added (Table 9).

[0222] [Table 9]

[0223] Example 7 Antiperspirant roll-on emulsion composition Microcapsules A1 to A7 and B1 to B12 of the present invention are weighed and mixed into an antiperspirant roll-on emulsion composition, and a fragrance equivalent to 0.2% is added (Table 10).

[0224] [Table 10]

[0225] Parts A and B are heated separately to 75°C. Part A is added to part B while stirring, and the mixture is homogenized for 10 minutes. The mixture is then cooled while stirring. When the mixture reaches 45°C, part C is slowly added, and when the mixture reaches 35°C, part D is added while stirring. The mixture is then cooled to room temperature.

[0226] Example 8 Deodorant spray composition Microcapsules A1 to A7 and B1 to B12 of the present invention are weighed and mixed into an antiperspirant roll-on emulsion composition, and a fragrance equivalent to 0.2% is added (Table 11).

[0227] [Table 11]

[0228] All ingredients are mixed and dissolved according to the order in Table 11. Aerosol cans are then filled, crimped and propellant is added (aerosol fill: 40% active solution, 60% propane / butane 2.5 bar).

[0229] Example 9 Shower gel composition Microcapsules A1 to A7 and B1 to B12 of the present invention are weighed and mixed in the following composition, and a fragrance equivalent to 0.2% is added (Table 12).

[0230] [Table 12]

Claims

1. an oily core comprising a hydrophobic material; a polyamide shell, Propane-1,2,3-tricarbonyl trichloride, cyclohexane-1,2,4,5-tetracarbonyl tetrachloride, 2,2'-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate, [2-[2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate acyl chloride selected from the group consisting of [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl] 4-chloro-4-oxo-butanoate, 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate, [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, and mixtures thereof; and at least one amino compound, a polyamide shell comprising:

1. A polyamide core-shell microcapsule comprising:

2. 2. The microcapsules of claim 1, wherein the amino compound is selected from the group consisting of guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines having a disulfide bond, and mixtures thereof.

3. 3. The microcapsule of claim 1, wherein the shell comprises a first amino compound and a second amino compound.

4. 4. The microcapsule of claim 3, wherein the first amino compound is selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof.

5. 4. The microcapsules of claim 3, wherein the second amino compound is selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine (Jeffamine®), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines having a disulfide bond, and mixtures thereof.

6. 6. Microcapsules according to any one of claims 1 to 5, wherein the weight ratio between the acyl chloride and the hydrophobic material is between 0.01 and 0.

2.

7. The functional group NH of the amino compound ２ Microcapsules according to any one of claims 1 to 6, wherein the molar ratio between α- and the functional group COCl of said acyl chloride is comprised between 0.01 and 50.

8. 8. The microcapsule of claim 1, wherein the microcapsule comprises an outer cationic coating.

9. a) dissolving at least one acyl chloride in a hydrophobic material to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase to obtain an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry; 1. A method for producing a core-shell polyamide microcapsule slurry, comprising: a stabilizer is added to the oil phase and / or the water phase; at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b), The acyl chloride may be selected from the group consisting of propane-1,2,3-tricarbonyl trichloride, cyclohexane-1,2,4,5-tetracarbonyl tetrachloride, 2,2′-disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glutamoyl dichloride, (S)-4-((1,5-dichloro-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid, 2,2-bis[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl 4-chloro-4-oxo-butanoate, [2-[2,2-bis[(4-chloro-4-oxo-butano 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(4-chloro-4-oxo-butanoyl)oxymethyl]butyl] 4-chloro-4-oxo-butanoate, 2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butyl 2-chlorocarbonyl-benzoate, [2-[2,2-bis[(2-chlorocarbonylbenzoyl)oxymethyl]butoxymethyl]-2-[(2-chlorocarbonylbenzoyl)oxymethyl]butyl] 2-chlorocarbonylbenzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, and mixtures thereof.

10. 10. The method of claim 9, wherein a first amino compound is added to the aqueous phase and a second amino compound is added to the oil-in-water emulsion.

11. 11. The method of claim 9 or 10, wherein the stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethyl cellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins, and mixtures thereof.

12. (i) perfume microcapsules as defined in claims 1 to 8, wherein the hydrophobic material comprises a perfume; (ii) at least one component selected from the group consisting of a fragrance carrier and a fragrance base; (iii) optionally at least one flavoring adjuvant; and A fragrance composition comprising:

13. - Effective bases for personal care, - microcapsules as defined in claims 1 to 8 or a perfuming composition as defined in claim 12, 1. A consumer product in the form of a personal care composition comprising:

14. - a base effective for home or clothing care; - microcapsules as defined in claims 1 to 8 or a perfuming composition as defined in claim 12, 1. A consumer product in the form of a home care or clothing care composition comprising:

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