Poly(amide-ester) microcapsules

Abstract

The present invention relates to a novel method for producing poly(amide-ester) microcapsules. The poly(amide-ester) microcapsules are 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, containing said capsules are also part of the present invention.

Description

[Technical field]

[0001] The present invention relates to a novel method for producing poly(amide-ester) microcapsules. The poly(amide-ester) microcapsules are also an object of the present invention. Perfumed compositions and consumer products, especially perfumed consumer products in the form of home or personal care products, containing said capsules are also part of the present invention.

[0002] 2. Background of the Invention One of the challenges facing the fragrance industry is that the olfactory benefits imparted by odoriferous compounds are lost relatively quickly, especially due to the volatility of the "top notes". To tune the release rate of volatile substances, delivery systems such as fragrance-containing microcapsules need to protect the core payload and release it after a delay when triggered. A key requirement from industry for these systems is to remain in suspension in a challenging base without physical separation or degradation. This is referred to as the stability of the delivery system. For example, fragranced personal and household cleaning products that contain high levels of harsh surfactant detergents are very difficult to stabilize in microcapsules.

[0003] Polyurea and polyurethane based microcapsule slurries are widely used, for example in the perfume industry, to impart a long-lasting and pleasant olfactory effect after deposition 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] Therefore, there remains a need to use alternative microcapsules without compromising the performance of the microcapsules, in particular in terms of stability in difficult media such as consumer product bases, as well as in terms of providing superior performance in terms of delivery of active ingredients, e.g. olfactory performance in the case of perfume ingredients.

[0005] The present invention offers a solution to the above problems by providing novel poly(amide-ester) microcapsules.

[0006] Summary of the Invention It has now surprisingly been found that the encapsulation of hydrophobic materials into core-shell microcapsules can be carried out by reacting an acyl chloride and a polyol with at least one amino compound during interfacial polymerization.The method of the present invention thus provides a solution to the above-mentioned problems, since it makes it possible to produce microcapsules with the desired stability in difficult substrates.

[0007] In a first aspect, the present invention provides a method for producing a composition comprising the steps of: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase which may optionally contain an amino compound A or a base to form an oil-in-water emulsion; c) adding an amino compound B to the oil-in-water emulsion obtained in step b); d) performing a curing step to form poly(amide-ester) microcapsules in the form of a slurry; 1. A method for producing a core-shell poly(amide-ester) microcapsule slurry comprising: A stabilizer is added in step a) and / or step b), The polyol is added in step a) and / or step b) and / or step c).

[0008] A second object of the present invention is a hydrophobic material, preferably an oily core containing a fragrance; a poly(amide-ester) shell; and wherein the poly(amide-ester) core-shell microcapsule comprises:

[0009] A third object of the present invention is to a hydrophobic material, preferably an oily core containing a fragrance; a poly(amide-ester) shell; and wherein the poly(amide-ester) core-shell microcapsule slurry has at least one poly(amide-ester) core-shell microcapsule comprising:

[0010] A fourth subject of the present invention is a poly(amide-ester) core-shell microcapsule slurry obtainable by the process defined above.

[0011] (i) a microcapsule slurry or microcapsules as defined above, wherein the hydrophobic material comprises a perfume; (ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; (iii) optionally at least one flavor adjuvant; and A perfuming composition comprising the compound is another object of the present invention.

[0012] Another subject of the present invention is - Effective bases for personal care, - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above, Consumer products, including The consumer product is in the form of a personal care composition.

[0013] Another subject of the present invention is - a base effective for home or clothing care; - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above, Consumer products, including The consumer product is in the form of a home care composition or a clothing care composition.

[0014] Detailed Description of the Invention Unless otherwise stated, percentages (%) are intended to represent weight percent of the composition.

[0015] By "hydrophobic material" is meant any hydrophobic material (single material or mixture of materials) that forms a two-phase dispersion when mixed with water.

[0016] "Component" means a single compound or a combination of components.

[0017] "Fragrance or flavor oil" means a single fragrance or flavoring compound or a mixture of fragrance or flavoring compounds.

[0018] "Consumer product" or "final product" means a manufactured product that is ready for distribution, sale, and use by a consumer.

[0019] By "polyamide (ester) based microcapsules" is meant that the polymer contains both amide and ester bonds, the amide and ester bonds being formed by the amino groups of the amino compound and the polyol, respectively, which can be further reacted with acyl chlorides.

[0020] "Polyol" means a compound having at least two hydroxyl functional groups.

[0021] 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.

[0022] By "microcapsule" or the like in the present invention is meant a core-shell microcapsule having a particle size distribution in the micron range (e.g. a mean diameter (d(v,0.5)) comprised between about 1 and 3000 microns, preferably between 1 and 1000 microns, more preferably between 1 and 500 microns, even more preferably between 5 and 50 microns) and comprising an outer solid polymer-based shell and an inner continuous oil phase encapsulated by the outer shell.

[0023] "Microcapsule slurry" means microcapsules dispersed in a liquid. According to one embodiment, the slurry is an aqueous slurry, i.e., the microcapsules are dispersed in an aqueous phase.

[0024] An "amino compound" should be understood as a compound having at least two reactive amine groups.

[0025] In the present invention, the terms "acyl chloride" and "acid chloride" are used interchangeably.

[0026] It has now been discovered that reaction of an acyl chloride and a polyol with at least one amino compound during interfacial polymerization can result in core-shell poly(amide-ester) microcapsules with excellent overall performance in difficult substrates. [Brief description of the drawings]

[0027] [Figure 1] 1 is a SEM image of a microcapsule according to the present invention. [Diagram 2] FIG. 2 is a TGA measurement of microcapsules according to the present invention. [Diagram 3] FIG. 2 is a TGA measurement of microcapsules according to the present invention.

[0028] Method for producing poly(amide-ester) microcapsule slurry The first object of the present invention is therefore 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 which may optionally contain an amino compound A or a base to form an oil-in-water emulsion; c) adding an amino compound B to the oil-in-water emulsion obtained in step b); d) performing a curing step to form poly(amide-ester) microcapsules in the form of a slurry; 1. A method for producing a core-shell poly(amide-ester) microcapsule slurry comprising: A stabilizer is added in step a) and / or step b), A process wherein a polyol is added in step a) and / or step b) and / or step c).

[0029] According to one embodiment, the polyol is added to the oil phase.

[0030] In one step of the process, an oil phase is formed by mixing at least one hydrophobic material with at least one acyl chloride.

[0031] According to one embodiment, the acyl chloride is selected from the group consisting of benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthalyl dichloride, diglycolyl dichloride, terephthaloyl chloride, succinic acid dichloride, and mixtures thereof.

[0032] According to a particular embodiment, the acyl chloride is 1,3,5-benzenetricarbonyl chloride.

[0033] According to a particular embodiment, the acyl chloride has the following formula (I): [ka] [In the formula, n is an integer varying from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4; X is a (n+1)-valent C3 to C6 alkyl group, or (i) to (vi). [ka] (n+1)-valent C2 to C 45 is any of the hydrocarbon groups, R is a hydrogen atom or a methyl group or an ethyl group, preferably a hydrogen atom.

[0034] 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.

[0035] By "...hydrocarbon group..." it is understood to mean that said group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e. linear or branched, saturated hydrocarbon (e.g. alkyl group), linear or branched, unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), saturated cyclic hydrocarbon (e.g. cycloalkyl), or unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or in the form of an aromatic hydrocarbon, i.e. aryl group, or in the form of a mixture of said types of groups, e.g. a particular group may contain linear alkyl, branched alkenyl (e.g. having one or more carbon-carbon double bonds), (poly)cycloalkyl, and aryl moieties, unless specifically limited to only one type is stated. 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 a group that 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 can be in the form of any type of topology (e.g., linear, cyclic, or branched) or have multiple moieties with different topologies.

[0036] 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, which may be linked laterally to said hydrocarbon group by replacing hydrogen atoms of said hydrocarbon group or may be inserted into a hydrocarbon chain or ring by replacing carbon atoms of the hydrocarbon group (where chemically possible).

[0037] According to one embodiment, when group (vi) is present, it is only present in combination with any one of groups (i) to (v).

[0038] 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-chlorocarbonyl-benzoate, 4-(2,4,5-trichlorocarbonylbenzoyl)oxybutyl 2,4,5-trichlorocarbonyl-benzoate, and mixtures thereof.

[0039] The weight ratio between the acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.09, more preferably between 0.03 and 0.07.

[0040] The acyl chloride can be dissolved directly in the hydrophobic material or can be pre-dispersed in an inert solvent such as benzyl benzoate prior to mixing with the hydrophobic material, preferably the perfume oil.

[0041] According to a particular embodiment, a polyisocyanate having at least two isocyanate functional groups is added to the oil phase.

[0042] Suitable polyisocyanates for use according to the present invention include aromatic polyisocyanates, aliphatic polyisocyanates, and mixtures thereof. The polyisocyanates contain at least two, preferably at least three, isocyanate functional groups, but may contain up to six, or even only four, isocyanate functional groups. According to a particular embodiment, triisocyanates (three isocyanate functional groups) are used.

[0043] According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.

[0044] The term "aromatic polyisocyanate" is intended herein to encompass any polyisocyanate that contains 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 polyisocyanate of toluene diisocyanate (commercially available from Bayer under the trade name Desmodur® RC), a trimethylolpropane adduct of toluene diisocyanate (commercially available from Bayer under the trade name Desmodur® L75), or a trimethylolpropane adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the trade name Takenate® D-110N). In the most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0045] According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain aromatic moieties. The preferred aliphatic polyisocyanate is the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, the trimethylolpropane adduct of hexamethylene diisocyanate (available from Mitsui Chemicals), or the biuret of hexamethylene diisocyanate (commercially available under the trade name Desmodur® N100 from Bayer), of which the biuret of hexamethylene diisocyanate is more preferred.

[0046] According to another embodiment, the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and at least one aromatic polyisocyanate, both containing at least two or three isocyanate functionalities, such as a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate, a mixture of biuret of hexamethylene diisocyanate and polyisocyanurate of toluene diisocyanate, and a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of toluene diisocyanate. Most preferably, this is a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate. Preferably, when used as a mixture, the molar ratio of aliphatic polyisocyanate to aromatic polyisocyanate ranges from 80:20 to 10:90.

[0047] 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.

[0048] Polyol Examples of polyols that can be used in the present invention are triethanolamine, di(trimethylolpropane), ethylene glycol, glycerol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, 2-ethyl-2-(hydroxymethyl)propane-1,3-diol (trimethylolpropane, TMP), 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol), 2-amino-2-ethylpropane-1,3-diol, 2-amino-2-(hydroxymethyl)propane-1,3-diol, 2,2'-azanediylbis(ethan-1-ol), 2-aminopropane-1,3-diol, 2-amino-2-methylpropane-1,3-diol, polyphenols, or mixtures thereof.

[0049] According to one embodiment, the polyol is a non-cleavable polyol.

[0050] According to one embodiment, the polyol is not polyvinyl alcohol.

[0051] According to one embodiment, the polyol is not glycerol.

[0052] Polyphenols can be simple monocyclic phenols (such as phloroglucinol) or polymers thereof (such as condensed tannins, hydrolyzable tannins).

[0053] The polyphenols may be monocyclic or polycyclic plant polyphenols, such as flavonoids, isoflavonoids, neoflavonoids, gallotannins and ellagotannins, catechols and derivatives thereof, such as DL-3,4-dihydroxyphenylalanine or DL-DOPA, catecholamines, such as 3-hydroxytyramine or dopamine, phloroglucinol, phenolic acids, such as caffeic acid, dihydrocaffeic acid, protocatechinic acid, chlorogenic acid, isochlorogenic acid, gentisic acid, homogentisic acid, gallic acid, hexahydroxydiphenic acid, ellagic acid, rosmarinic acid or lithospermic acid, phenolic acid derivatives, in particular their esters or heterosides thereof, curcumin, polyhydroxylated coumarins, polyhydroxylated lignans or neolignans, or mixtures comprising one or more plant polyphenols or derivatives thereof, such as silymarin.

[0054] If a polyphenol is used, it is preferably added in step b) (in the aqueous phase) and / or in step c) (after the oil-in-water emulsion has been formed). If added in step c), it is preferably added before the addition of the amino compound B.

[0055] According to any one of the embodiments of the invention, the polyol represents approximately 0.1% to 5% by weight, or even 0.2% to 3% by weight, relative to the total weight of the dispersion obtained after step b).

[0056] The polyol can be pre-dissolved in an inert solvent such as ethyl acetate.

[0057] According to a particular embodiment, the molar ratio between polyol and acyl chloride is between 0.01 and 2, preferably between 0.05 and 1.5.

[0058] Hydrophobic Materials A hydrophobic material according to the present invention can be an "inert" material such as a solvent or an active ingredient.

[0059] When the hydrophobic material is an active ingredient, it is preferably selected from the group consisting of flavors, flavor ingredients, fragrances, fragrance ingredients, dietary supplements, cosmetics, pest control agents, biocides, and mixtures thereof.

[0060] According to certain embodiments, the hydrophobic material comprises a mixture of a fragrance and another ingredient selected from the group consisting of a nutritional supplement, a cosmetic, a pest control agent, and a biocidal active.

[0061] According to certain embodiments, the hydrophobic material comprises a mixture of a biocidal active and another ingredient selected from the group consisting of fragrances, dietary supplements, cosmetics, and pest control agents.

[0062] According to certain embodiments, the hydrophobic material comprises a mixture of a pest control agent and another ingredient selected from the group consisting of fragrances, dietary supplements, cosmetics, and biocidal actives.

[0063] According to certain embodiments, the hydrophobic material comprises a fragrance.

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

[0065] According to a particular embodiment, the hydrophobic material comprises a biocidal active.

[0066] According to a particular embodiment, the hydrophobic material comprises a pest control agent.

[0067] By "perfume" (or "perfume oil") herein is meant an ingredient or composition that is liquid at about 20°C. According to any one of the above embodiments, said perfume oil may be only a perfume ingredient or a mixture of ingredients in the form of a perfume composition. By "perfume ingredient" herein is meant a compound that is used for the primary purpose of imparting or modulating an odor. In other words, such an ingredient, in order to be considered a perfume ingredient, must not only have an odor but must also be recognized by the skilled artisan as being able to at least impart or modify the odor of the composition in a positive or pleasant way. For the purposes of the present invention, perfume oil includes combinations of perfume ingredients and substances that together improve, enhance or modify the delivery of the perfume ingredient, such as perfume precursors, emulsions or dispersions, but also combinations that provide additional benefits beyond modifying or imparting an odor, such as persistence, blooming, malodor suppression, antibacterial effect, microbial stability, pest control.

[0068] The nature and type of perfume ingredients present in the oil phase do not warrant a more detailed description here, and in any case are not exhaustive, and can be selected by a person skilled in the art based on his 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, aldehydes, ketones, esters, ethers, acetates, nitriles, 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 in any case listed in reference texts, such as S. Arctander, 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 ingredient can be a compound known to release various types of perfume compounds in a controlled manner.

[0069] Mention may in particular be made of perfuming ingredients commonly used in perfume formulations such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal, and / or nonenal; - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undec-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 components: coumarin, ethyl vanillin, and / or vanillin; -Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-P-menthen-8-yl acetate, and / or 1,4(8)-P-menthadiene; -Floral ingredients: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta-ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexene 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, methyl cis-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 isomeric mixture;, -Fruity ingredients: gamma undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 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 components: 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-cyclopentene tadecen-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 components: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ]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.

[0070] It is also understood that the ingredient may be a compound known to release in a controlled manner various types of perfuming compounds, also known as perfume precursors or fragrance precursors. 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-phenylethyloxo(phenyl)-1-prop ... ) acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-ylhexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy 4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy 4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, or mixtures thereof.

[0071] The perfuming ingredients can be dissolved in solvents currently used in the perfume industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, limonene or other terpenes, or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, such as Abalyn® or benzyl benzoate. Preferably, the perfume contains less than 30% solvent. More preferably, the perfume contains less than 20% and even more preferably less than 10% solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially solvent-free.

[0072] Preferred perfuming ingredients are those with high steric hindrance, in particular those from one of the following groups: - Group 1: Perfuming ingredients containing a cyclohexane, cyclohexene, cyclohexanone, or cyclohexenone ring substituted with at least one linear or branched C1-C4 alkyl or alkenyl substituent; - Group 2: Perfuming ingredients containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4-C8 alkyl or alkenyl substituent; - Group 3: Perfuming ingredients 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 one or more linear or branched C1-C3 alkyl or alkenyl substituents; - Group 4: Perfuming ingredients containing at least two fused or linked C5 and / or C6 rings; - Group 5: Odour 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 of more than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent; Examples of components in each of these groups are: - Group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (Supplied by Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate (Supplied by Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylates, rose oxide, (S)-1,8-p-menthadien-7-ol (Supplied by 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 (Supplied by Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1,4-cyclohexanediethyl dicarboxylate (Supplied by Firmenich SA, Geneva, Switzerland), (3ARS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Supplied by Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (Supplied by Firmenich SA, Geneva, Switzerland). 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 (supplied by Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (supplied by Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (supplied by Givaudan SA, Vernier, Switzerland); - group 3: damascone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (supplied by Firmenich SA, Geneva, Switzerland), 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 (Supplied by Firmenich SA, Geneva, Switzerland), 8-Methoxy-1-p-menthene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate (Supplied by Firmenich SA, Geneva, Switzerland).Switzerland), para-tert-butylcyclohexanone, menthenthiol, 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), 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, 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 (supplied by International Flavors and Fragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal (supplied by Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9-spiro-2'-oxirane (Supplied by Firmenich SA, Geneva, Switzerland), 9 / 10-ethyldiene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate (Supplied by Firmenich SA, Geneva, Switzerland), octalinol, (dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan, Supplied by Firmenich SA, Geneva, Switzerland). 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-methoxycedrene, (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane (supplied by Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecane-4-one and 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecane-4-one (supplied by 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 (Supplied by Firmenich SA, Geneva, Switzerland), Ambrettolide LG ((E)-9-hexadecen-16-olide, Supplied by Firmenich SA, Geneva, Switzerland), Pentadecenolide (Supplied by Firmenich SA, Geneva, Switzerland), Musenone (3-Methyl-(4 / 5)-cyclopentadecenone, Supplied by Firmenich SA, Geneva, Switzerland), 3-Methylcyclopentadecanone (Supplied by Firmenich SA, Geneva, Switzerland), Pentadecanolide (Supplied by Firmenich SA, Geneva, Switzerland), Cyclopentadecanone (Supplied by Firmenich SA, Geneva, Switzerland), 1-Ethoxyethoxy)cyclododecane (Supplied by 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.

[0073] Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from groups 1 to 7 as defined above. More preferably, the perfume comprises at least 30%, preferably at least 50% of ingredients selected from groups 3 to 7 as defined above. Most preferably, the perfume comprises at least 30%, preferably at least 50% of ingredients from groups 3, 4, 6 or 7 as defined above.

[0074] According to another preferred embodiment, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP greater than 3, preferably greater than 3.5, even more preferably greater than 3.75.

[0075] Preferably, 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. Advantageously, the fragrance used in the present invention contains no primary alcohols and less than 15% of secondary and tertiary alcohols.

[0076] 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 raw materials with LogT < -4, and -1.07g / cm 3 0 to 75% by weight of a density-balanced material having a density greater than include.

[0077] High impact fragrance ingredients with LogT<-4 and 1.07g / cm 3 The properties of density-balanced materials having densities greater than 10 ...

[0078] The term "biocide" refers to a chemical 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 may be pesticides, including bactericides, herbicides, insecticides, algaecides, molluscicides, acaricides, and rodenticides, and / or antimicrobials, such as bactericides, antibiotics, antibacterial agents, antivirals, antifungals, antiprotozoals, and / or antiparasitics.

[0079] As used herein, "pest control agent" means a substance that functions to repel or attract pests, reduce, inhibit, or promote their growth, development, or their activity. A pest refers to any organism, whether animal, plant, or fungus, that invades or causes problems for plants or animals, and includes insects, particularly arthropods, mites, spiders, fungi, weeds, bacteria, and other microorganisms.

[0080] According to a particular embodiment, the hydrophobic material does not include any active ingredient (such as fragrances). According to this particular embodiment, it comprises, preferably consists of, a hydrophobic solvent, preferably selected in the group consisting of isopropyl myristate, triglycerides (such as Neobee® MCT oil, vegetable oils), D-limonene, silicone oils, mineral oils, and mixtures thereof, and optionally a hydrophilic solvent, preferably selected in the group consisting of 1,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1,2-propanediol), 1,3-propanediol, dipropylene glycol, glycerol, glycol ethers, and mixtures thereof.

[0081] According to any one of the embodiments of the present invention, the hydrophobic material represents between 10% and 60% w / w, or even between 15% and 45% w / w, relative to the total weight of the dispersion obtained after step b).

[0082] According to certain embodiments, the oil phase consists essentially of an acyl chloride, a polyol, and a perfume or flavor oil.

[0083] In another step of the process according to the invention, the oily phase of step a) is dispersed in an aqueous solution, optionally containing an amino compound A and / or a base, to form an oil-in-water emulsion.

[0084] The average droplet size of the emulsion is preferably comprised between 1 and 1000 microns, more preferably between 1 and 500 microns, and even more preferably between 5 and 50 microns.

[0085] By "amino compound A" it is to be understood that this is a compound capable of reacting with an acyl chloride to form an amide bond.

[0086] When present, the amino compound A can be selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof, and when present, the base is preferably NaOH. According to a particular embodiment, the amino compound A is L-lysine.

[0087] If present, the amino compound A or the base is preferably added in an amount comprised between 1% and 10% by weight, more preferably between 0.5% and 5% by weight, based on the dispersion obtained after step b).

[0088] According to the present invention, the emulsion is stabilized by adding a stabilizer to the water phase and / or the oil phase.

[0089] The stabilizer may be an ionic or non-ionic emulsifier or colloidal stabilizer.

[0090] The stabilizer may be a molecular emulsifier (standard emulsion) or a solid particle emulsifier (Pickering emulsion).

[0091] The terms "stabilizer" and "emulsifier" are used interchangeably in the present invention.

[0092] According to one embodiment, the stabilizer is selected in the group consisting of gum arabic, modified starch, polyvinyl alcohol, PVP (polyvinylpyrrolidone), CMC (carboxymethylcellulose), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins, and mixtures thereof.

[0093] According to one embodiment, the stabilizer is selected in the group consisting of gum arabic, modified starch, polyvinyl alcohol, PVP, 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.

[0094] If a stabilizer is added to the oil phase, it is preferably selected in 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.

[0095] If added to the oil phase, the stabilizer can be predispersed in an inert solvent such as benzyl benzoate.

[0096] If a stabilizer is added to the aqueous phase, it is preferably selected in the group consisting of gum arabic, modified starch, polyvinyl alcohol, PVP, 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.

[0097] According to any one of the above embodiments of the invention, the dispersion comprises about 0.01% to 3.0% of at least one stabilizer, the percentage being expressed on a w / w basis relative to the total weight of the dispersion obtained after step b). In yet another aspect of the invention, the dispersion comprises about 0.05% to 1.0% of at least one stabilizer. In yet another aspect of the invention, the dispersion comprises about 0.1% to 0.8% of at least one stabilizer.

[0098] In another step of the process according to the invention, an amino compound B is added to the oil-in-water emulsion obtained in step b).

[0099] By "amino compound B" it is to be understood that this is a compound capable of reacting with an acyl chloride to form an amide bond.

[0100] As non-limiting examples, the amino compound B is selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, Jeffamine® (O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines with disulfide bonds, such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.

[0101] According to one embodiment, the amino compound B 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.

[0102] According to another embodiment, the amino compound B is selected in the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, Jeffamine® (O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, or mixtures thereof.

[0103] According to a particular embodiment, amino compound A and amino compound B are the same.

[0104] According to another particular embodiment, the amino compound A and the amino compound B are different.

[0105] According to one embodiment, the weight ratio between amino compound A and amino compound B is comprised between 0.5 and 25, preferably between 1.3 and 7.

[0106] The method of the present invention is particularly characterized by the fact that a polyol and an acyl chloride react with at least one amino compound during the method. Indeed, without being bound by any theory, the inventors have observed that this combination stabilizes the microcapsules in consumer products.

[0107] The amount of amino compound B used is typically adjusted so that the molar ratio of the functional group NH2 of amino compound B to the acyl chloride COCl is comprised between 0.01 and 7.5, preferably between 0.1 and 3.0.

[0108] According to one embodiment, a base is added to adjust the pH, non-limiting examples of which include guanidine carbonate, sodium bicarbonate, or triethanolamine.

[0109] The base is preferably added in an amount comprised between 0.1% and 10% by weight, more preferably between 0.5% and 5% by weight, based on the weight of the dispersion.

[0110] This is followed by a hardening step d) which finally results in microcapsules in the form of a slurry or liquid dispersion, said step can be carried out at a temperature comprised between 50 and 130° C., possibly under pressure, for a period of 15 minutes to 8 hours, in order to increase the reaction rate.

[0111] No specific action is required to induce polymerization between the acyl chloride and the amino compound.

[0112] Optional outer coating: According to a particular embodiment of the present invention, at the end of step d) or during step d), a polymer selected from the group consisting of non-ionic polysaccharides, cationic polymers, and mixtures thereof may also be added to the slurry of the present invention to form an outer coating of the microcapsules.

[0113] Nonionic polysaccharide polymers are well known to those skilled in the art and are described, for example, in WO 2012 / 007438, page 29, lines 1-25, and in WO 2013 / 026657, page 2, lines 12-19, and page 4, lines 3-12. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose, and hydroxypropyl methylcellulose.

[0114] 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 that contain units that contain primary, secondary, tertiary, and / or quaternary amine groups, which may form part of the polymer backbone or may have side chain substituents directly connected thereto. The weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5 M Daltons, more preferably between 50,000 and 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 that may be mentioned are Salcare® SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, supplier: BASF) or Luviquat®, such as PQ 11N, FC 550 or Style (polyquaternium-11-68 or quaternized copolymer of vinylpyrrolidone, supplier: BASF) or Jaguar® (C13S or C17, supplier: Rhodia).

[0115] 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, even between about 0.1% and 2% w / w, the percentage being expressed on a w / w basis with respect to the total weight of the slurry obtained after step d), it will be clearly understood by those skilled in the art that only a part of said added polymer is incorporated into / deposited on the microcapsule shell.

[0116] Another subject of the invention is a method for producing a microcapsule powder, comprising the steps defined above and an additional step e) consisting of subjecting the slurry obtained in step d) to drying, such as spray drying, in order to obtain the microcapsules themselves, i.e. in powder form. It is understood that any standard method known to the skilled artisan to carry 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 cellulose derivatives, to obtain microcapsules in powder form.

[0117] However, other drying methods may also be mentioned, such as extrusion, plating, spray granulation, fluidized bed, or even drying at room temperature using materials (carriers, desiccants) that meet the specific criteria disclosed in WO 2017 / 134179.

[0118] According to a particular embodiment, the carrier material comprises free perfume oil, which may be the same or different from the perfume from the core of the microcapsule.

[0119] Multi-Capsule System According to one embodiment, the microcapsules of the present invention (first type of microcapsules) can be used in combination with a second type of microcapsules.

[0120] Another subject of the present invention is - microcapsules of the invention as a first type of microcapsule, - microcapsules of the invention as a second type of microcapsule, wherein the first type of microcapsules and the second type of microcapsules differ in hydrophobic material and / or wall material and / or coating material.

[0121] Poly(amide-ester) microcapsules Another subject of the present invention is a poly(amide-ester) microcapsule slurry obtainable by the process described above.

[0122] The specific composition of the poly(amide-ester) wall is important in obtaining microcapsules that exhibit desirable stability on a product basis (e.g., effectively counteracting fragrance leaching by surfactants in consumer products).

[0123] Another subject of the present invention is therefore a poly(amide-ester) core-shell microcapsule or a poly(amide-ester) core-shell microcapsule slurry having at least one poly(amide-ester) core-shell microcapsule, said poly(amide-ester) core-shell microcapsule comprising: an oily core containing a hydrophobic material, preferably a fragrance; a poly(amide-ester) shell; Includes.

[0124] According to one embodiment, the poly(amide-ester) shell comprises, based on the total weight of the shell: an optional stabilizer, preferably 0% to 75% w / w of a stabilizer, - acyl chloride, preferably 10% to 90% w / w, more preferably 23% to 90% acyl chloride, an optional amino compound A, preferably 0-50%, more preferably 5%-50% w / w of amino compound A, an amino compound B, preferably from 1% to 40% w / w of an amino compound B, a polyol, preferably 1 to 60% w / w of a polyol, Includes.

[0125] It should be understood that the sum of all components equals 100%.

[0126] By "a poly(amide-ester) shell comprising an acyl chloride, at least one amino compound, and a polyol," it is to be understood that the poly(amide-ester) shell is derived from the acyl chloride, at least one amino compound, and a polyol. In other words, it is to be understood that the poly(amide-ester) shell comprises the reaction product of the acyl chloride, at least one amino compound, and a polyol.

[0127] According to one embodiment, it should be understood that when a stabilizer is present in the shell, the poly(amide-ester) shell is derived from an acyl chloride, at least one amino compound, a polyol, and a stabilizer. In other words, according to this embodiment, it should be understood that the poly(amide-ester) shell comprises the reaction product of an acyl chloride, at least one amino compound, and a stabilizer and a polyol.

[0128] Another subject of the present invention is a carrier material, preferably a polymeric carrier material selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginates, 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 comprising:

[0129] The solid particles and microcapsule powders defined above can be used interchangeably in the present invention.

[0130] The embodiments described above regarding the nature of the hydrophobic material, the polyol, the stabilizer, the acyl chloride, the amino compound A, and the amino compound B also apply to the poly(amide-ester) microcapsules.

[0131] According to a particular embodiment, when amino compound A is present, the amino compounds A and B contained in the shell of the poly(amide-ester) microcapsules are different.

[0132] The composition of the shell can be quantified, for example, by elemental analysis and identified by solid-state NMR, two techniques well known to those skilled in the art.

[0133] Perfume compositions / consumer products The microcapsules of the invention can be used in combination with active ingredients. The subject of the invention is therefore (i) microcapsules or a microcapsule slurry 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:

[0134] The microcapsules of the invention can be used for the preparation of perfuming or flavoring compositions, which are also the subject of the present invention.

[0135] The capsules of the present invention exhibit very good performance with respect to stability in difficult media.

[0136] Another subject of the present invention is (i) a microcapsule or microcapsule slurry as defined above, wherein the oil contains a perfume; (ii) at least one component selected from the group consisting of a fragrance carrier, a fragrance co-ingredients, and mixtures thereof; (iii) optionally at least one flavor adjuvant; and A fragrance composition comprising:

[0137] As liquid perfume carriers, non-limiting examples may include emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, non-limiting examples may 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 that include both perfume carriers and perfume co-ingredients, other suitable perfume carriers other than 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). By "perfume co-ingredient" herein is meant a compound that is not a microcapsule as defined above, that is used in perfume formulations or compositions to provide a hedonic effect. In other words, it must be recognized by one of ordinary skill in the art that such co-ingredients not only have an odor, but are also capable of at least imparting or modifying the odor of the composition in a positive or pleasant way.

[0138] The nature and type of perfume co-ingredients present in perfume compositions do not warrant a more detailed description here, and in any case are not exhaustive, and can be selected by a person skilled in the art based on his general knowledge and according to the intended use or application and the desired sensory effect.Generally, these perfume co-ingredients belong to various chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, 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 any case in reference texts, such as S. Arctander, 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.

[0139] By "perfuming adjuvant" is meant herein an ingredient capable of imparting additional added benefits such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfume bases cannot be exhaustive, but it should be mentioned that said ingredients are well known to those skilled in the art.

[0140] Preferably, the perfuming composition according to the invention comprises 0.01 to 30% by weight of microcapsules as defined above.

[0141] The microcapsules of the present invention can be advantageously used in many fields of application and can be used in consumer products: they can be used in liquid form for liquid consumer products and in powder form for powder consumer products.

[0142] According to a particular embodiment, the consumer product 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 or microcapsules as defined above; d) optional non-encapsulated fragrance; and Includes.

[0143] According to a particular embodiment, the consumer product 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.

[0144] In the case of microcapsules containing an oily core of perfume, the products of the invention can be used in perfumed consumer products, such as those belonging in particular to fine perfumery or "functional" perfumery. Functional perfumery includes in particular personal care products such as hair care, body cleansing, skin care, hygiene care, and home care products such as laundry care and air care. As a result, another subject of the invention consists of perfumed consumer products comprising as perfuming ingredients the microcapsules defined above or the perfume composition defined above. The perfume elements of said consumer products may be combinations of perfume microcapsules defined above, free or non-encapsulated perfumes, and other types of perfume microcapsules other than those disclosed herein.

[0145] 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, Liquid consumer products comprising the compound are another subject of the present invention.

[0146] 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, A powdered consumer product comprising the compound is also part of the invention.

[0147] Thus, the microcapsules of the present invention can be added by themselves or as part of the perfume composition of the present invention in perfumed consumer products.

[0148] 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 perfuming effect on the surface to which it is applied (e.g. skin, hair, fabric, paper or residential surfaces) or in the air (fragrance, deodorant, etc.) In other words, a perfumed consumer product according to the invention is a manufactured product that comprises 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.

[0149] The nature and type of other ingredients of perfumed consumer products 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 common knowledge and according to the nature and desired effect of said 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 are not exhaustive.Those skilled in the art of formulating such consumer products can completely select suitable ingredients based on common knowledge and according to available literature.

[0150] Non-limiting examples of suitable perfumed consumer products include perfumes such as fine fragrances, colognes, aftershaves, body splashes, etc.; 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. shampoos, hair conditioners, dyes, or hairsprays), 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 or 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.

[0151] Another subject of the present invention is - Effective bases for personal care, - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above, The present invention relates to a consumer product in the form of a personal care composition comprising:

[0152] The personal care effective 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 suitable ingredients based on common knowledge and available literature.

[0153] The personal care composition is preferably selected in the group consisting of a hair care product (e.g. shampoo, hair conditioner, dye, or hairspray), a cosmetic product (e.g. vanishing cream, body lotion, or deodorant or antiperspirant), or a skin care product (e.g. perfumed soap, shower or bath smooth, body wash, oil or gel, bath salts, or hygiene product);

[0154] Another subject of the present invention is - a base effective for home or clothing care; - a microcapsule or a microcapsule slurry as defined above, or a perfuming composition as defined above, The present invention relates to a consumer product in the form of a home care composition or a clothing care composition comprising:

[0155] 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 entirely able to select the appropriate ingredients based on common knowledge and available literature.

[0156] Preferably, the consumer product comprises 0.1-15% by weight, more preferably 0.2-5% by weight, of the microcapsules of the invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, said concentrations can be adjusted depending on the beneficial effect desired for each product.

[0157] Fabric softener The subject of the present invention is a fabric softener useful base, preferably 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 in an amount of 85 to 99.95% by weight based on the total weight of the composition; - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; and a fabric softener composition comprising:

[0158] Liquid detergent The subject of the present invention is a base useful in liquid detergents, preferably selected from the group consisting of anionic surfactants such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic 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 in an amount of 85 to 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; and a consumer product in the form of a liquid detergent composition comprising:

[0159] Solid detergent The subject of the present invention is a base useful in solid detergents, preferably selected from the group consisting of anionic surfactants such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic 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 in an amount of 85 to 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; The present invention relates to a consumer product in the form of a solid detergent composition comprising:

[0160] Shampoo / Shower gel The subject of the present invention is a base useful in shampoos or shower gels, preferably 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 in an amount ranging from 85 to 99.95% by weight, based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; A consumer product in the form of a shampoo or shower gel composition comprising:

[0161] Rinse-off conditioner The subject of the present invention is a base useful in rinse-off conditioners, preferably selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride, and mixtures thereof, preferably in an amount of 85 to 99.95% by weight based on the total weight of the composition, - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; The present invention relates to a consumer product in the form of a rinse-off conditioner comprising:

[0162] Hair dye The subject of the present invention is - an oxidation phase containing an oxidizing agent, an alkaline phase containing an alkaline 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 an oxidizing agent); - a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 and 15% by weight, more preferably between 0.1 and 5% by weight, based on the total weight of the composition; A consumer product in the form of an oxidative hair dye composition comprising:

[0163] By "oxidative hair dye composition" is meant a composition that contains 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) that are incorporated into the hair due to their size. In other words, the dye precursors and coupling compounds form an oxidative hair dye in the presence of an oxidizing agent.

[0164] The terms "dye precursor" and "oxidation dye precursor" are used interchangeably in the present invention.

[0165] The dye precursors can be aromatic compounds derived from benzene substituted at the para or ortho positions with at least two electron donating groups such as NH2 and OH to impart easy oxidation properties.

[0166] According to one embodiment, the dye precursor is selected in the group consisting of p-phenylenediamine, 2,5-diaminotoluene, N,N-bis(2-hydroxymethyl)-p-phenylenediamine, 4-aminophenol, 1,4-diaminobenzene, and mixtures thereof.

[0167] The primary dye precursors are used in combination with coupling agents, preferably aromatic compounds derived from benzene and meta-substituted with groups such as NH2 or OH, which do not produce color by themselves but modify the color, shade, or intensity of color produced by the dye precursor.

[0168] 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.

[0169] 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.

[0170] 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 in EP 0 946 133 A1, which is incorporated by reference in its entirety.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] The oxidizing agent provides the oxygen gas needed to develop the color molecules and change the color of the hair.

[0175] The oxidizing agent must be safe and effective for use in the compositions herein.

[0176] Preferably, the oxidizing agents suitable for use herein are soluble in the composition according to the invention when in liquid form and / or in the form in which they are intended for use.

[0177] Preferably, the oxidizing agents suitable for use herein will be 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.

[0178] 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.

[0179] 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, germicides, propellants, and thickeners.

[0180] 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 conditioning benefits.

[0181] Perfuming composition According to certain embodiments, the consumer product comprises: - 0.1 to 30%, preferably 0.1 to 20%, of microcapsules or a microcapsule slurry as defined above, - 0 to 40%, preferably 3 to 40%, of a fragrance; 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol based on the total weight of the fragrance composition; The fragrance composition is in the form of a fragrance composition comprising:

[0182] The present invention is further illustrated by the following examples, it being understood that the invention as claimed is not intended to be in any way limited by these examples.

[0183] Working Example material [Table 1-1]

[0184] [Table 1-2]

[0185] Composition of the balm: [Table 2]

[0186] Example 1 Preparation of poly(amide-ester) microcapsules using colloidal stabilizers in the oil phase Capsule A: Preparation of capsule A by using trimethylolpropane as polyol.

[0187] 1,3,5-Benzenetricarbonyl chloride (BTC, 0.88 g, Table 1) was dissolved in benzyl benzoate (2 g). Bovine serum albumin (0.95 g) was dispersed in benzyl benzoate at 60°C, and the acyl chloride solution was added and stirred for 2 minutes. Trimethylolpropane (0.45 g) was dissolved in ethyl acetate (2 g) at room temperature, and this solution was added to a second solution of 1,3,5-benzenetricarbonyl chloride (0.88 g) in benzyl benzoate (2 g). The solution and dispersion were added to perfume oil (25 g, Table 2) at room temperature to form an oil phase. The oil phase was added to an aqueous solution of L-lysine (2.5 g) (amino compound A) in water (95 g). The reaction mixture was stirred with an Ultra Turrax at 24,000 rpm for 1 minute to obtain an emulsion. Polyamine (amino compound B, Table 3) was dissolved in water (5 g) and the solution was added dropwise to the emulsion. The reaction mixture was stirred at 30° C. for 4 hours to obtain a white dispersion.

[0188] [Table 3]

[0189] Example 2 Preparation of poly(amide-ester) microcapsules using colloidal stabilizers in the aqueous phase. Capsule B - Preparation of Capsule B using trimethylolpropane as polyol Trimethylolpropane (TMP) was dissolved in ethyl acetate (5 g) at 40° C. A solution of polyol was added to a solution of 1,3,5-benzenetricarbonyl chloride in benzyl benzoate (5 g) and the solution was left stirring at room temperature for 10 minutes. This solution was added to perfume oil (25 g, Table 2) to form the oil phase. L-lysine (3.5 g, 24 mmol) was dissolved in an aqueous solution of gum arabic (95 g, 1 wt%). The solution was stirred for 15 minutes to form the aqueous phase. The oil phase was added to the aqueous phase and the reaction mixture was stirred with an Ultra Turrax at 24,000 rpm for 30 seconds to obtain an emulsion. Polyamine (Table 7) was dissolved in water (1 g) and this solution was added dropwise to the emulsion. A solution of guanidine carbonate (10 wt%) was added to obtain a pH value of 7. The reaction mixture was stirred with an anchor at 200 rpm at 30° C. for 2 hours and then at 60° C. for 2 hours to obtain a white dispersion.

[0190] [Table 4-1]

[0191] [Table 4-2]

[0192] Capsule C - Preparation of Capsule C using triethanolamine as polyol Capsule C was prepared as described above for Capsule B using triethanolamine (0.50 g) in ethyl acetate (2.5 g), 1,3,5-benzenetricarbonyl chloride (1.76 g) in benzyl benzoate (5 g), m-xylylenediamine (5 g) in water, and L-lysine (2.5 g) in 1 wt % aqueous gum arabic solution (95 g) at 30° C. for 4 hours.

[0193] Capsule D - Preparation of Capsule D using Ethylene Glycol as Polyol Ethylene glycol (0.12 g) was dissolved in ethyl acetate (2.5 g) at 40 ° C. A solution of polyol (ethylene glycol) was added to a solution of 1,3,5-benzenetricarbonyl chloride (0.35 g) in benzyl benzoate (2.5 g) and the solution was left stirring at 60 ° C for 60 min. This solution was added to perfume oil (25 g, Table 2) dispersed with colloidal stabilizer (0.95 g sodium caseinate) and a solution of 1,3,5-benzenetricarbonyl chloride (1.4 g) in benzyl benzoate (2.5 g) to form the oil phase. L-lysine (2.5 g, 17 mmol) was dissolved in water. The solution was stirred for 15 min to form the aqueous phase. The oil phase was added to the aqueous phase and the reaction mixture was stirred with an Ultra Turrax at 24,000 rpm for 30 s to obtain an emulsion. Ethylenediamine (0.2 g) was dissolved in water (5 g) and the solution was added dropwise to the emulsion. The reaction mixture was stirred at 250 rpm in an incubator at 30° C. for 4 hours.

[0194] The average size of microcapsules D is about 30 μm.

[0195] The microcapsules exhibit 16% perfume leakage in a fabric softener base (see composition in Table 5) at 43° C. for 3 days.

[0196] Capsule E - Preparation of Capsule E using pentaerythritol as polyol Capsule E was prepared as described above for Capsule D using pentaerythritol (0.2 g) in ethanol (2.5 g), 1,3,5-benzenetricarbonyl chloride (1.76 g total) in benzyl benzoate (5 g total), ethylenediamine (0.18 g) in water (5 g), and L-lysine (2.5 g) in water at 30° C. for 4 hours.

[0197] TGA measurements from 30°C to 50°C (5°C / min) and held at 50°C for 250 minutes show that the microcapsules retain 100% of the perfume oil after 250 minutes.

[0198] Capsule F - Preparation of Capsule F using di(trimethylolpropane) as polyol Capsule F was prepared as described above for Capsule D using di(trimethylolpropane) (0.25 g) in acetone (2.5 g), 1,3,5-benzenetricarbonyl chloride (1.76 g total) in benzyl benzoate (5 g total), ethylenediamine (0.23 g) in water (5 g), and L-lysine (2.5 g) in water at 30° C. for 4 hours.

[0199] The average size of the microcapsules F is about 30 μm.

[0200] Example 3 Preparation of poly(amide-ester) microcapsules using polyphenols Capsule G: Preparation of Capsule G using phloroglucinol as the polyol 1,3,5-Benzenetricarbonyl chloride (BTC, 1.7799 g, Table 1) was dissolved in benzyl benzoate (5.02 g). Sodium caseinate (0.95 g) was dispersed in 5.10 g of benzyl benzoate. The solution and dispersion were added to perfume oil (25.30 g, Table 2) at room temperature to form an oil phase. The oil phase was then quickly added to an aqueous solution of L-lysine (2.5 g) in water (94 g) followed by emulsification for 30-45 seconds at 24,000 rpm using an Ultra Turrax. A previously prepared solution of phloroglucinol (0.13 g) in ethanol (1 g) was then added to the emulsion while stirring with a propeller at 400 rpm. After 3-5 minutes, a solution of ethylenediamine (EDA, 0.18 g, Table 1) dissolved in water (5 g) was slowly added to the reaction mixture while stirring. The reaction mixture was stirred at 30° C. for 4 hours to give a white dispersion.

[0201] The average size of the microcapsules G is 50 microns (see FIG. 1).

[0202] TGA measurements from 30°C to 50°C (10°C / min) with a hold at 50°C for 240 minutes show that the microcapsules retain 100% of the perfume oil after 240 minutes (see Figure 2).

[0203] Stability of Microcapsule G in Fabric Softener Base: An amount of Microcapsule Suspension G corresponding to 0.116% perfume was dispersed in fabric softener (see Table 5) and stored for 3 days at 38° C. The perfume leakage was then quantified and was determined to be 14% after 3 days.

[0204] Capsule H: Preparation of capsule H by using condensed tannin as polyphenol.

[0205] 1,3,5-Benzenetricarbonyl chloride (BTC, 1.7878 g, Table 1) was dissolved in benzyl benzoate (5.20 g). Sodium caseinate (0.96 g) was dispersed in 5.05 g of benzyl benzoate. The solution and dispersion were added to perfume oil (25.22 g, Table 2) at room temperature to form an oil phase. The oil phase was then quickly added to an aqueous solution of L-lysine (2.51 g) in water (95 g) followed by emulsification for 30-45 seconds at 24,000 rpm using an Ultra Turrax. A previously prepared solution of Tan' activ U condensed tannin (0.20 g) in water (5 g) was then added to the emulsion under stirring with a propeller at 400 rpm. After 3–5 min, a solution of ethylenediamine (EDA, 0.24 g, Table 1) dissolved in water (5 g) was slowly added to the reaction mixture with stirring. The reaction mixture was stirred at 30 °C for 4 h, resulting in a white dispersion.

[0206] The average size of the microcapsules H is 50 microns.

[0207] TGA measurements from 30°C to 50°C (10°C / min) with a hold at 50°C for 240 minutes show that the microcapsules retain 100% of the perfume oil after 240 minutes (see Figure 3).

[0208] Stability of Microcapsule H in Fabric Softener Bases: An amount of Microcapsule Suspension H corresponding to 0.116% perfume was dispersed in fabric softener (see composition in Table 5) and stored for 3 days at 38° C. The perfume leakage was then quantified and was determined to be 14% after 3 days.

[0209] Example 4 Fabric softener composition Capsules A, B, C, D, E, F, G, or H (A-H) were dispersed in the fabric softener base described in Table 5 to obtain a concentration of 0.22% encapsulated perfume oil.

[0210] [Table 5]

[0211] Example 5 Liquid detergent composition Capsules AH were dispersed in the liquid detergent base described in Table 6 to give a concentration of 0.22% encapsulated perfume oil.

[0212] [Table 6]

[0213] Example 6 Rinse-off conditioner Capsules AH were dispersed in the rinse-off conditioner bases described in Table 7 to give a concentration of 0.5% encapsulated perfume oil.

[0214] [Table 7]

[0215] Example 7 Shampoo Composition Capsules A to H of the present invention are weighed and mixed into a shampoo composition, and a fragrance equivalent to 0.2% is added.

[0216] [Table 8-1]

[0217] [Table 8-2]

[0218] Example 8 Antiperspirant roll-on emulsion composition Capsules A to H of the present invention are weighed and mixed into an antiperspirant roll-on emulsion composition, and a fragrance equivalent to 0.2% is added.

[0219] [Table 9]

[0220] 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 with 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.

[0221] Example 9 Shower gel composition Capsules A to H of the present invention are weighed and mixed in the following composition, and a flavor equivalent to 0.2% is added.

[0222] [Table 10]

Claims

1. 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 containing an amino compound A and optionally a base to form an oil-in-water emulsion; c) adding an amino compound B to the oil-in-water emulsion obtained in step b); d) performing a curing step to form poly(amide-ester) microcapsules in the form of a slurry; 1. A method for producing a core-shell poly(amide-ester) microcapsule slurry comprising: A stabilizer is added in step a) and / or step b), A polyol is added in step a) and / or step b) and / or step c), The method, wherein said amino compound A and said amino compound B are different.

2. 2. The method of claim 1, wherein the acyl chloride is selected from the group consisting of 1,3,5-benzenetricarbonyl chloride, benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthaloyl dichloride, diglycolyl dichloride, terephthaloyl chloride, succinic acid dichloride, and mixtures thereof.

3. 3. The method of claim 1, wherein the amino compound A is selected from the group consisting of L-lysine, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof.

4. 4. The method of any one of claims 1 to 3, wherein the amino compound B is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine ethyl ester, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), tris-(2-aminoethyl)amine, L-arginine, and mixtures thereof.

5. 5. The method of claim 1, wherein the stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone, carboxymethyl cellulose, anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins, and mixtures thereof.

6. The functional group NH of the amino compound B ２ 6. The process according to claim 1, wherein the molar ratio of aryloxycarbonyl to the functional group COCl of said acyl chloride is comprised between 0.01 and 7.

5.

7. The method according to any one of claims 1 to 6, wherein the weight ratio between acyl chloride and said hydrophobic material is comprised between 0.02 and 0.

09.

8. 8. The method of any one of claims 1 to 7, wherein the polyol is selected from the group consisting of triethanolamine, di(trimethylolpropane), ethylene glycol, glycerol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, 2-ethyl-2-(hydroxymethyl)propane-1,3-diol (trimethylolpropane, TMP), 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol), 2-amino-2-ethylpropane-1,3-diol, 2-amino-2-(hydroxymethyl)propane-1,3-diol, 2,2'-azanediylbis(ethan-1-ol), 2-aminopropane-1,3-diol, 2-amino-2-methylpropane-1,3-diol, polyphenols, and mixtures thereof.

9. an oily core comprising a hydrophobic material; - a poly(amide-ester) shell; A poly(amide-ester) core-shell microcapsule comprising: the poly(amide-ester) shell being - an optional stabilizer, - acyl chloride, an amino compound A, an amino compound B; - a polyol, Including, the amino compound A and the amino compound B are different, the stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone, carboxymethylcellulose, anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins, and mixtures thereof; 10. Poly(amide-ester) core-shell microcapsules, wherein the polyol is selected from the group consisting of triethanolamine, di(trimethylolpropane), ethylene glycol, glycerol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, 2-ethyl-2-(hydroxymethyl)propane-1,3-diol (trimethylolpropane, TMP), 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol), 2-amino-2-ethylpropane-1,3-diol, 2-amino-2-(hydroxymethyl)propane-1,3-diol, 2,2′-azanediylbis(ethan-1-ol), 2-aminopropane-1,3-diol, 2-amino-2-methylpropane-1,3-diol, polyphenols, and mixtures thereof.

10. The poly(amide-ester) core-shell microcapsule of claim 9, wherein the amino compound A is selected from the group consisting of L-lysine, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof.

11. The poly(amide-ester) core-shell microcapsule of claim 9 or 10, wherein the amino compound B is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine ethyl ester, O,O'-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), tris-(2-aminoethyl)amine, L-arginine, and mixtures thereof.

12. (i) the microcapsules of any one of claims 9 to 11, 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 flavor adjuvant; and A fragrance composition comprising:

13. - Effective bases for personal care; - a microcapsule according to any one of claims 9 to 11 or a fragrance composition according to claim 12, A consumer product in the form of a personal care composition comprising:

14. - a base useful for home or clothing care, - a microcapsule according to any one of claims 9 to 11 or a fragrance composition according to claim 12, 1. A consumer product in the form of a home care or clothing care composition comprising:

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