Polyamide microcapsules

Abstract

To provide microcapsules, and perfuming compositions and consumer products comprising the microcapsules.SOLUTION: There is provided a polyamide core-shell microcapsule comprising: an oil-based core comprising a hydrophobic material, and a polyamide shell comprising: an acyl chloride, in an amount comprised between 5 and 98% w / w; a first amino compound, in an amount comprised between 1% and 50% w / w; a second amino compound, in an amount comprised between 1% and 50% w / w; and a stabilizer, a biopolymer, in an amount comprised between 0.1 and 75% w / w, wherein the first amino-compound is an amino-acid, and the first amino compound and the second amino compound are different, and the biopolymer is protein.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel method for the preparation of polyamide microcapsules, which are also the subject of the present invention. Perfumed compositions and consumer products, especially in the form of home care products or personal care products, containing said microcapsules are also part of the present invention.

[0002] Background technology One of the problems faced by the perfume industry is the relatively fast loss of the olfactory benefits provided by the perfume compounds due to their volatility, especially the volatility of "top notes". To control the release rate of volatiles, delivery systems, such as perfume-containing microcapsules, require the core payload to be protected and later released when triggered. The key requirement from the perfume industry for these systems is to maintain suspension in interesting bases without physical separation or decomposition. This is referred to as stability for the delivery system. For example, perfumed personal and household cleansers that contain high levels of strong surfactant detergents are very challenging for the stability of microcapsules.

[0003] Polyurea and polyurethane-based microcapsule slurries are widely used, for example, in the perfume industry, for example, to provide long-lasting pleasant olfactory effects after application on different substrates. These microcapsules have been widely disclosed in the prior art (see, for example, the applicant's International Publication No. WO2007 / 004166 or European Patent No. EP 2300146).

[0004] There remains a need to provide new microcapsules without compromising their performance, particularly in terms of their stability in interesting media, such as consumer product bases, as well as in terms of providing good performance in terms of delivery of active ingredients, such as olfactory performance in the case of perfuming ingredients.

[0005] The present invention provides a solution to the above problems by providing new polyamide microcapsules and methods for making the microcapsules.

[0006] Summary of the Invention Surprisingly, it has been found that core-shell microcapsules encapsulating hydrophobic materials can be obtained by reacting acyl chloride with two amino compounds during the process, preferably adding the amino compounds successively during the process.The process of the present invention therefore provides a solution to the above problem, making it possible to produce microcapsules with the desired stability in interesting bases.

[0007] In a first aspect, the present invention provides a method for producing a method for manufacturing a semiconductor device comprising the steps of: a) dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; and c) carrying out a curing step to form polyamide microcapsules in the form of a slurry. wherein a stabilizer is added to the oil phase and / or to the aqueous phase, and at least a second amino compound is added to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0008] The second object of the present invention is to provide - a hydrophobic material, preferably an oil-based core, comprising a perfume, and - below: Acyl chlorides, a first amino compound, A second amino compound Polyamide shell comprising The polyamide core-shell microcapsules are

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

[0010] below, (i) a microcapsule 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 flavoring adjuvant; A perfuming composition comprising the compound is another object of the present invention.

[0011] Another object of the present invention is to - personal care active bases, and - a microcapsule as defined above or a perfuming composition as defined above wherein the consumer product is in the form of a personal care composition.

[0012] Another object of the present invention is to - a home care or fabric care active base, and - a microcapsule as defined above or a perfuming composition as defined above wherein the consumer product is in the form of a home care or fabric care composition.

[0013] Detailed Description of the Invention Unless otherwise specified, percentages (%) are meant to indicate weight percentages of a composition.

[0014] By "active ingredient" it is meant a single compound or a combination of ingredients.

[0015] By "perfume oil or flavor oil" is meant a single perfuming or flavoring compound or a mixture of several perfuming or flavoring compounds.

[0016] By "consumer product" or "final product" is meant a manufactured product that is prepared for distribution, sale and use by a consumer.

[0017] For reasons of clarity, with regard to the expression "dispersion" in the present invention it is meant systems in which particles are dispersed in a continuous phase of any composition, including in particular suspensions or emulsions.

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

[0019] By "amino compound" it is to be understood a compound having at least two reactive amine groups.

[0020] In the present invention, the terms "chloride" and "acid chloride" are used interchangeably. By "polyamide microcapsules" it is meant that the shell of the microcapsule comprises a polyamide material. The term "polyamide microcapsules" may also encompass shells that are constructed from composite materials that include polyamide materials and other materials, such as biopolymers.

[0021] It has been found that core-shell polyamide microcapsules with overall good performance in terms of stability in interesting bases are obtained when two amino compounds are added, preferably sequentially, during the process.

[0022] Process for producing polyamide microcapsule slurry In a first aspect, the present invention provides a method for producing a method for manufacturing a semiconductor device comprising the steps of: a) dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; and c) carrying out a curing step to form polyamide microcapsules in the form of a slurry. wherein a stabilizer is added to the oil phase and / or to the aqueous phase, and at least a second amino compound is added to the aqueous phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0023] According to certain embodiments, the method comprises the steps of: a) dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) adding a second amino compound to the oil-in-water emulsion obtained in step b); and d) carrying out a curing step to form polyamide microcapsules in the form of a slurry. wherein a stabilizer is added to the oil phase and / or the water phase.

[0024] In one step of the process, an oil phase is formed by mixing at least one hydrophobic material and at least one acyl chloride.

[0025] According to a particular embodiment, the acyl chloride is selected from the group consisting of benzene-1,3,5-tricarbonyl chloride, benzene-1,2,4-tricarbonyl trichloride, benzene-1,2,4,5-tetracarbonyl tetrachloride, cyclohexane-1,3,5-tricarbonyl trichloride, isophthaloyl dichloride, diglycolyl dichloride, succinyl dichloride, and mixtures thereof.

[0026] The mass ratio of the acyl chloride to the hydrophobic material is preferably 0.01 to 0.09, and more preferably 0.03 to 0.07.

[0027] The acyl chloride may be dissolved directly in the perfume oil or may be pre-dispersed in an inert solvent, such as benzyl benzoate, before mixing with the perfume oil.

[0028] According to a particular embodiment, a polyisocyanate having at least two isocyanate groups is added in the oil phase.

[0029] Suitable polyisocyanates used according to the present invention include aromatic polyisocyanates, aliphatic polyisocyanates, and mixtures thereof. The polyisocyanates contain at least two, preferably at least three, but up to six, or even only four, isocyanate functional groups. According to a particular embodiment, triisocyanates (three isocyanate functional groups) are used.

[0030] According to one embodiment, said polyisocyanate is an aromatic polyisocyanate.

[0031] The term "aromatic polyisocyanate" is meant here to include any polyisocyanate that contains an aromatic moiety. Preferably, the aromatic moiety is a phenyl, toluyl, xylyl, naphthyl or diphenyl moiety, more preferably a toluyl or xylyl moiety. Preferred aromatic polyisocyanates are biurets, polyisocyanurates and trimethylolpropane adducts of diisocyanurates, more preferably containing one of the above specific aromatic moieties. More preferably, the aromatic polyisocyanates are polyisocyanurates of toluene diisocyanate (commercially available under the trade name Desmodur® RC from Bayer), trimethylolpropane adducts of toluene diisocyanate (commercially available under the trade name Desmodur® L75 from Bayer), trimethylolpropane adducts of xylylene diisocyanate (commercially available under the trade name Takenate® D-110N from Mitsui Chemicals). In a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0032] According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain any aromatic moiety. Preferred aliphatic polyisocyanates are the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, the trimethylolpropane adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or the biuret of hexamethylene diisocyanate (available from Bayer under the trade name Desmodur® N 100), of which the biuret of hexamethylene diisocyanate is even more preferred.

[0033] 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 functional groups, such as a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate and a polyisocyanurate of toluene diisocyanate, and a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of toluene diisocyanate. Most preferred is a mixture of a biuret of hexamethylene diisocyanate and a trimethylolpropane adduct of xylylene diisocyanate. Preferably, when used as a mixture, the molar ratio of aliphatic polyisocyanate to aromatic polyisocyanate is in the range of 80:20 to 10:90.

[0034] 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, relative to the total amount of the oil phase.

[0035] Hydrophobic Materials According to one embodiment, the hydrophobic material is a hydrophobic active ingredient.

[0036] By "hydrophobic active ingredient" is meant any hydrophobic active ingredient (single ingredient or mixture of ingredients) that forms a two-phase dispersion when mixed with water. A hydrophobic active ingredient is a liquid at about 20° C.

[0037] The hydrophobic active ingredient is preferably selected from the group consisting of flavors, flavor ingredients, fragrances, fragrance ingredients, dietary supplements, cosmetics, pest control agents, biocides, and mixtures thereof.

[0038] According to a particular embodiment, the hydrophobic active ingredient is a mixture of fragrances and other ingredients selected from the group consisting of functional food, cosmetic, pest control and biocide actives.

[0039] According to a particular embodiment, the hydrophobic active ingredient is a mixture of a biocidal active agent and other ingredients selected from the group consisting of fragrances, functional foods, cosmetics, pest control agents.

[0040] According to a particular embodiment, the hydrophobic active ingredient is a mixture of a pesticide and other ingredients selected from the group consisting of fragrances, functional foods, cosmetics, biocide actives.

[0041] According to certain embodiments, the hydrophobic active ingredient comprises a fragrance.

[0042] According to a particular embodiment, the hydrophobic active ingredient consists of a fragrance.

[0043] According to a particular embodiment, the hydrophobic active ingredient consists of a biocidal active agent.

[0044] According to certain embodiments, the hydrophobic active ingredient consists of a pesticide.

[0045] By "perfume" (or "perfume oil"), we mean here 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 perfuming ingredient or a mixture of perfuming ingredients in the form of a perfuming composition. By "perfuming ingredient" we mean here a compound that is used for the main purpose of imparting or adjusting an odor. In other words, such an ingredient to be considered as a perfuming ingredient must be recognized by the skilled person as being at least capable of imparting or modifying the odor of the composition in a positive or favorable way, and not merely having one odor. For the purposes of the present invention, perfume oil also includes combinations of perfuming ingredients, such as perfume precursors, emulsions or dispersions, with substances that together improve, enhance or modify the delivery of the perfuming ingredient, and combinations that impart additional benefits beyond modifying or imparting an odor, such as longevity, blooming, malodor neutralization, antimicrobial effect, microbial stability, pest control.

[0046] The nature and type of perfuming ingredients present in the oil phase, which will in any case not be exhaustive, do not warrant a more detailed description here, and those skilled in the art can select said base on the basis of their general knowledge and according to any use or application and the organoleptic effect desired.In general terms, these perfuming ingredients belong to various chemical classes: alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.Many of these co-ingredients are in any case mentioned in references, for example in Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or its latest editions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.It is also understood that said ingredients may be compounds known to release various types of perfuming ingredients in a controlled manner.

[0047] Mention may in particular be made of perfuming ingredients customarily used in perfume formulations, such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecanal, octanal, nonanal and / or nonenal; - aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or alpha-pinene; - Balsam components: coumarin, ethyl vanillin and / or vanillin; - citrus constituents, dihydromyricenol, 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, Hexyl Cinnamaldehyde, Benzyl Acetate, Benzyl Salicylate, Tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, Beta-Ionone, Methyl 2-(Methylamino)benzoate, (E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2- cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexen 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-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis-methyl dihydroxide Rojasmonate, 3-methyl-5-phenyl-1-pentanol, virgyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-P-methanol, 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 acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; - 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, allylheptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxaethylpropionate, 3-methyl-5-cyclopentadecanone entadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody Ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.02,7]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-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 of its stereoisomers, 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.

[0048] It is also understood that said ingredients may be compounds known to release various types of perfuming compounds in a controlled manner, also known as properfumes or profragrances. Non-limiting examples of suitable pro-perfumes may include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-phenylethyloxo(phenyl)acetate or mixtures thereof.

[0049] The perfuming ingredients may be dissolved in a solvent currently used in the perfume industry. The said 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 said solvent is very hydrophobic and highly sterically hindered, such as Abalyn® or benzyl benzoate. Preferably, the perfume comprises less than 30% solvent. More preferably, the perfume comprises 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. More preferably, the perfume is substantially free of solvent.

[0050] Preferred perfuming ingredients are those with high steric hindrance and in particular those from one of the following groups: - Group 1: at least one linear or branched C 1 ~C 4 Perfuming ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with an alkyl or alkenyl substituent - Group 2: at least one linear or branched C 4 ~C 8 Perfuming ingredients containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with alkyl or alkenyl substituents. - Group 3: Perfuming ingredients containing a phenyl ring or at least one linear or branched C 5 ~C 8 at least one phenyl substituent and optionally one or more straight or branched chain C 1 ~C 3 Perfuming ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with an alkyl or alkenyl substituent; - Group 4: at least two fused or linked C 5 Ring and / or C 6Fragrance components containing rings - Group 5: Odorants containing ring structures such as camphor; - Group 6: at least one C 7 ~C 20 Perfuming ingredients containing ring structures; - Group 7: perfuming ingredients having a logP value of about 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substituent.

[0051] Examples of components from each of the above groups are: - group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (supplier: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, Romascone® (methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate, supplier: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylates, rose oxide, Perycorolle® ((S)-1,8-p-menthadien-7-ol, supplier: Firmenich SA, Geneva, Switzerland), 1-p-menthen-4-ol, (1RS,3RS,4SR)-3-p-menthanyl acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-2-ol, Doremox® (tetrahydro-4-methyl-2-phenyl-2H-pyran, supplier: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, Fructalate® (1,4-cyclohexanediethyl dicarboxylate, supplier: Firmenich SA, Geneva, Switzerland), Koumalactone® ((3ARS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one, supplier: Firmenich SA, Geneva, Switzerland), Natactone® ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one, Supplier: Firmenich SA, Geneva, 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 (supplier: Givaudan SA, Vernier, Switzerland), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol (supplier: Firmenich SA, Geneva, Switzerland), Polysantol® ((1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol, supplier: Firmenich SA, Geneva, Switzerland), fleuramone, Hedione® HC (methyl-cis-3-oxo-2-pentyl-1-cyclopentane acetate, supplied by Firmenich SA, Geneva, Switzerland), Veloutone® (2,2,5-trimethyl-5-pentyl-1-cyclopentanone, supplied by Firmenich SA, Geneva, Switzerland), Nirvanol® (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, Neobutenone® (1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, supplier: Firmenich SA, Geneva, Switzerland), nectalactone ((1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'-yl)propyl]cyclopentanone), alpha-ionone, beta-ionone, damascenone, Dynascone® (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, supplier: Firmenich SA, Geneva, Switzerland), Dorinone® beta (1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, supplied by Firmenich SA, Geneva, Switzerland), Romandolide® ((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), Limbanol® (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), (E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, terpenyl isobutyrate, Lorysia® (4-(1,1-dimethylethyl)-1-cyclohexyl acetate, Supplied by: Firmenich SA, Geneva, Switzerland), 8-Methoxy-1-p-menthene, Helvetolide® ((1S,1'R)-2-[1-(3',3'-Dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, Supplier: Firmenich SA, Geneva, Switzerland), para-tert-butylcyclohexanone, Menthenethiol, 1-Methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, Allyl cyclohexylpropionate, Cyclohexyl salicylate, 2-Methoxy-4-methylphenyl methyl carbonate, Ethyl 2-Methoxy-4-methylphenyl carbonate, 4-Ethyl-2-Methoxyphenyl methyl carbonate; - Group 4: Methyl cedryl ketone (Supplier: International Flavors and Fragrances, USA), Verdylate, vetiverol, vetiverone, 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 (Supplier: International Flavors and Fragrances, USA). Fragrances, USA), Hivernal® (mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal, supplier: Firmenich SA, Geneva, Switzerland), Rhubofix® (3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9-spiro-2'-oxirane, supplier: Firmenich SA, Geneva, Switzerland), 9 / 10-ethylidyne-3-oxatricyclo[6.2.1.0(2,7)]undecane, Polywood® (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate, supplier: Firmenich SA, Geneva, Switzerland), octalinol, Cetalox® (dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan, supplier: Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl acetate as well as tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl propanoate 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, camphopinene, cedrumber (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane, supplier: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, Florex® (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, supplier: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (Supplier: Firmenich SA, Geneva, Switzerland); - group 6: Cedroxyde® (trimethyl-13-oxabicyclo-[10.1.0]-trideca-4,8-diene, supplier: Firmenich SA, Geneva, Switzerland), Ambrettolide LG ((E)-9-hexadecen-16-olide, supplier: Firmenich SA, Geneva, Switzerland), Habanolide® (pentadecenolide, supplier: Firmenich SA, Geneva, Switzerland), Muscone (3-methyl-(4 / 5)-cyclopentadecenone, supplier: Firmenich SA, Geneva, Switzerland), Exaltolide® (pentadecanolide, supplier: Firmenich SA, Geneva, Switzerland), SA, Geneva, Switzerland), Exaltone® (cyclopentadecanone, supplier: Firmenich SA, Geneva, Switzerland), (1-ethoxyethoxy)cyclododecane (supplier: Firmenich SA, Geneva, Switzerland), Astrotone, 4,8-cyclododecadien-1-one; - Group 7: Lilial® (supplier: Givaudan SA, Vernier, Switzerland), Rodinol.

[0052] 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 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.

[0053] According to another preferred embodiment, said perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients with a logP above 3, preferably above 3.5, even more preferably above 3.75.

[0054] Preferably, the perfume used in the present invention contains less than 5% by weight of primary alcohols, less than 10% by weight of secondary alcohols, and less than 15% by weight of tertiary alcohols. Advantageously, the perfume used in the present invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.

[0055] According to one embodiment, the oil phase (or oil-based core) comprises: - 25-100% by weight of perfume oil containing at least 15% by weight of impact-resistant perfume raw materials having a Log T<-4, and - 1.07g / cm 3 Density balance material with density exceeding 0-75% by mass Includes.

[0056] A "high impact perfume raw material" is to be understood as a perfume raw material having a Log T<-4. The odor threshold concentration of a compound is determined in part by its shape, polarity, partial charge, and molecular weight. For convenience, the threshold concentration is expressed as the base 10 logarithm of the threshold concentration, i.e., Log[Threshold] ("LogT").

[0057] "Density balanced material" is 1.07g / cm 3 By this is meant a material which has a high density and preferably has a low or no odor.

[0058] The odor threshold concentration of the odorant compound is determined by using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact amount of the odorant oil component injected by syringe, the exact split ratio, and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate is accurately measured and the amount sampled is calculated, assuming a human inhalation lasts 12 seconds. Since the exact concentration at the detector at any time is known, the mass per inhaled volume is known, and therefore the concentration of the odorant compound. To determine the threshold concentration, the solution is sent to a receptacle for smelling at the back-calculated concentration. Panelists smell the GC effluent and identify the retention time when they notice an odor. The average of all panelists determines the odor threshold concentration of the odorant compound. The determination of odor thresholds is described in detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.

[0059] Impact resistant fragrance ingredients with Log T<-4 and 1.07g / cm 3 The properties of density-balanced materials having densities greater than 10 ...

[0060] According to one embodiment, the high impact perfume raw materials having a Log T<-4 are selected from the list in Table A below.

[0061] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5]

[0062] According to one embodiment, the perfume raw material having a Log T<-4 comprises at least one perfume raw material selected from the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.

[0063] According to one embodiment, the perfume raw material having a Log T<-4 comprises at least one compound selected in the group consisting of alcohols, phenols, ester lactones, ethers, epoxides, nitriles and mixtures thereof, preferably in an amount of 20-70% by weight based on the total amount of the perfume raw material having a Log T<-4.

[0064] According to one embodiment, the perfume raw materials having a Log T<-4 comprise aldehydes, ketones and mixtures thereof in an amount of 20-70% by weight based on the total amount of perfume raw materials having a Log T<-4.

[0065] Thus, the remaining perfume raw materials contained in the oil-based core may have a Log T > -4.

[0066] Non-limiting examples of perfume raw materials with a Log T>-4 are shown in Table B below.

[0067] [Table 2-1] [Table 2-2] [Table 2-3]

[0068] According to one embodiment, the oil phase (oil-based core) has a viscosity of 1.07 g / cm 3 % by weight of a density balanced material having a density greater than 25-98% by weight of perfume oil comprising at least 15% by weight of an impact resistant perfume raw material having a LogT>-4.

[0069] The density of a component is the ratio of its mass to its volume (g / cm 3 )

[0070] There are several methods for determining the density of a component.

[0071] For example, reference may be made to the ISO 298:1998 method for determining the d20 density of essential oils.

[0072] According to one embodiment, the density balancing material is selected in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenyl acetate, phenylethylphenoxyacetate, triacetin, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.

[0073] According to certain embodiments, the density-balancing material is selected in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, and mixtures thereof.

[0074] According to a particular embodiment, the hydrophobic material does not have any active ingredient (e.g., fragrance).In this particular embodiment, the hydrophobic material preferably comprises a hydrophobic solvent, preferably selected from the group consisting of isopropyl myristate, triglyceride (e.g., Neobee® MCT oil, vegetable oil), D-limonene, silicone oil, mineral oil, and mixtures thereof, optionally selected from the group consisting of 1,4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1,2-propanediol), 1,3-propanediol, dipropylene glycol, glycerol, glycol ether, and mixtures thereof.

[0075] 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 in industries to prevent fouling 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, antibacterials, antivirals, antifungals, antiprotozoals, and / or antiparasitics.

[0076] As used herein, "pesticide" refers to a substance that serves 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 is invasive or bothersome to plants or animals, and pests include insects, particularly arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.

[0077] With respect to "flavor ingredient or flavor composition" is meant in this specification a flavor ingredient or a mixture of flavor ingredients, solvents or current auxiliaries for the preparation of a flavor formulation, i.e. for the preparation of a specific mixture of ingredients intended to be added to an edible composition or a chewable product in order to impart, improve or modify its organoleptic properties, in particular its flavor and / or taste. Taste modulators are also included in said definition. Flavor ingredients are well known to the person skilled in the art and their nature does not warrant a detailed description herein, which is in all cases not exhaustive, whereby the person skilled in the art can select said base on the basis of general knowledge and according to any use or application and the organoleptic effect desired to be achieved. Many of these flavor ingredients are listed in the literature, for example in the book Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA, by S. Arctander, or in its latest editions, or in other similar works, for example Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press, or Synthetic Food Adjuncts, 1947, by MB Jacobs, can Nostrand Co., Inc. Solvents and adjuvants or those currently used for the preparation of flavor formulations are well known to those skilled in the art.

[0078] In certain embodiments, the flavors are selected from the group consisting of terpene flavors, including citrus and mint oils, and sulfuryl flavors.

[0079] According to any one of the embodiments of the invention, the hydrophobic active ingredient represents from about 10% to 60% by weight (w / w), or even from 15% to 45% by weight (w / w), relative to the total weight of the dispersion obtained after step b).

[0080] According to a particular embodiment, the oil phase consists essentially of the acyl chloride and the perfume or flavour oil, and optionally a stabiliser.

[0081] In another step of the process according to the invention, the oil phase is dispersed in an aqueous solution containing a first amino compound and optionally a stabilizer to form an oil-in-water emulsion.

[0082] The average droplet size of the emulsion is preferably from 1 to 1000 microns, more preferably from 1 to 500 microns, and even more preferably from 5 to 50 microns.

[0083] According to a particular embodiment, the first amino compound is preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine and mixtures thereof, preferably L-lysine, L-arginine, L-histidine, L-tryptophan and mixtures thereof, more preferably L-lysine, L-arginine, L-histidine and mixtures thereof.

[0084] The amino acid preferably has two nucleophilic groups. The first amino compound may be selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof. According to a particular embodiment, the first amino compound is L-lysine.

[0085] According to the invention, a stabilizer is added to the water phase and / or the oil phase to form the emulsion. According to one embodiment, the stabilizer is a colloidal stabilizer.

[0086] Colloidal stabilizers can be molecular emulsifiers (standard emulsions) or solid particles (Pickering emulsions).

[0087] By "stabilizer" is meant a compound capable of stabilizing an oil / water interface as an emulsion.

[0088] According to certain embodiments, the stabilizer is a biopolymer.

[0089] "Biopolymer" means a biological macromolecule produced by living organisms. Biopolymers are characterized by a molecular weight distribution ranging from 1000 (one thousand) to 1000 million (one billion) Daltons. These macromolecules can be carbohydrates (sugar based) or proteins (amino acid based) or a combination of both (rubbers), and can be linear or branched.

[0090] According to one embodiment, the colloidal stabilizer or emulsifier is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, and mixtures thereof.

[0091] When a colloidal stabilizer is added to the oil phase, the stabilizer is selected from the group consisting of proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, and mixtures thereof.

[0092] According to certain embodiments, the stabilizer is a biopolymer selected from the group consisting of proteins, such as whey proteins, casein, sodium caseinate, bovine serum albumin, and mixtures thereof.

[0093] When added to the oil phase, the stabilizer may be pre-dispersed in an inert solvent, such as benzyl benzoate, or may be mixed with the active ingredient, preferably the active ingredient including the perfume oil.

[0094] The stabilizer and acyl chloride may be pre-mixed and heated, for example at a temperature of from 10 to 80° C., before mixing with the hydrophobic material, for example the hydrophobic material containing the perfume oil.

[0095] In case a colloidal stabilizer is added to the aqueous phase, said stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), carboxymethylcellulose (CMC), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudo collagen, silk protein, sericin powder, and mixtures thereof.

[0096] According to any one of the above embodiments of the invention, the dispersion comprises about 0.01% to 3.0% (w / w) of at least one colloidal stabilizer, the percentage being expressed as w / w relative to the total weight of the oil-in-water emulsion obtained after step b). In yet another aspect of the invention, the dispersion comprises about 0.05% to 2.0%, preferably 0.05% to 1%, of at least one colloidal stabilizer. In yet another aspect of the invention, the dispersion comprises about 0.1% to 1.6%, preferably 0.1% to 0.8%, by weight of at least one colloidal stabilizer.

[0097] In another step of the process according to one embodiment, a second amino compound is added to the oil-in-water emulsion obtained in step b).

[0098] Without being bound by theory, the inventors believe that a first amino compound reacts with an acyl chloride to form a polyamide, and a second amino compound reacts with the remaining acyl chloride group of the acyl chloride.

[0099] By way of non-limiting example, the second amino compound may be selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramine (Jeffamine®), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines having disulfide bonds, such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochloride, and mixtures thereof.

[0100] According to one embodiment, the second amino compound is an amine having a disulfide bond and is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.

[0101] According to another embodiment, the second amino compound is selected from the group consisting of xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, Jeffamine®, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, and mixtures thereof.

[0102] According to a particular embodiment, the second amino compound is a mixture of two amino compounds, preferably a mixture of ethylenediamine and diethylenetriamine.

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

[0104] According to other particular embodiments, the first amino compound and the second amino compound are different.

[0105] According to one embodiment, the mass ratio of the first amino compound to the second amino compound is 0.5-25, preferably 1.3-10, more preferably 1.3-7.

[0106] The method of the present invention is particularly characterized by the fact that two amino compounds are added, preferably consecutively, during the process, the first amino compound being added in step b) and preferably at least the second amino compound being added once the emulsion has been formed. Indeed, without being bound by theory, the inventors have observed that the combination of both amino compounds results in stable microcapsules in consumer products.

[0107] The amount of the second amino compound used is typically determined by the amount of the functional group NH 2 The molar ratio of the functional group COCl of the acyl chloride to the carboxylic acid is adjusted to be 0.01 to 7.5, preferably 0.1 to 3.0.

[0108] The amount of the first amino compound used is typically determined by the amount of the functional group NH 2 The molar ratio of the functional group COCl of the acyl chloride to the carboxylic acid is adjusted to 0.2 to 3, preferably 0.5 to 2.

[0109] According to one embodiment, a base is added at the end of step c) to adjust the pH, non-limiting examples include guanidine carbonate, sodium bicarbonate or triethanolamine.

[0110] According to a particular embodiment, the base is not an amino compound.

[0111] The base is preferably added in an amount of 0.1% to 10%, more preferably 0.5% to 5%, relative to the oil-in-water emulsion.

[0112] This is followed by a hardening step c) resulting in microcapsules in the form of a slurry. According to a preferred embodiment, in order to increase the reaction rate, said step is carried out at a temperature of 5-80° C. or under pressure for 1-8 hours, more preferably at 10-80° C. for 30 minutes to 5 hours.

[0113] According to a particular embodiment, no polyol is added at any step of the process.

[0114] 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 be added to the slurry of the present invention to form an outer coating on the microcapsules.

[0115] 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.

[0116] 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 advantageously at least about 1.5 meq / g, but advantageously less than about 7 meq / g, advantageously less than about 6.2 meq / g. The cationic charge density of the cationic polymer may be measured by the Kjeldahl method described in the US Pharmacopeia under Chemical Tests for Nitrogen Determination. Preferred cationic polymers are selected from those that contain units containing primary, secondary, tertiary and / or quaternary amine groups, which may form part of the polymer backbone or be carried by secondary substituents directly attached thereto. The weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5 M Daltons, more advantageously between 50,000 and 1.5 M Daltons. According to a particular embodiment, 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.As specific examples of commercially available products, mention may be made of Salcare® SC60 (cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF) or Luviquat®, such as PQ 11N, FC 550 or Style (polyquaternium-11-68 or quaternized copolymer of vinylpyrrolidone, origin: BASF), or Jaguar® (C13S or C17, origin: Rhodia).

[0117] According to any of the above embodiments of the present invention, an amount of said polymer is added of about 0% to 5% (w / w), or even about 0.1% to 2% (w / w), the percentage being expressed w / w relative to the total mass of the slurry obtained after step c) or d), it is clearly understood by the skilled person that only a part of said added polymer is introduced into / deposited on the shell of the microcapsules.

[0118] Another object of the invention is a method for producing a microcapsule powder comprising the steps defined above and an additional step d) or e) consisting in subjecting the slurry obtained in step c) or d) to drying, such as spray drying, to provide the microcapsules themselves, i.e. in powder form. It is understood that any standard method known to the skilled artisan for carrying out such drying can be applied. In particular, the slurry may be spray-dried, preferably in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan, alginate, carrageenan or cellulose derivative, to provide the microcapsules in powder form.

[0119] According to a particular embodiment, the carrier material comprises free perfume oil, which may be the same or different from the perfume from the microcapsule core.

[0120] Another object of the present invention is the polyamide microcapsule slurry obtained by the above process.

[0121] Polyamide Microcapsules The composition of the polyamide shell makes it possible to provide microcapsules that exhibit the desired stability in the product base (e.g., effectively preventing extraction of the perfume by surfactants in consumer products).

[0122] Therefore, another object of the present invention is to provide a method for producing a method for the preparation of a - a hydrophobic material, preferably an oil-based core, comprising a perfume, and - below: Acyl chlorides, a first amino compound, and A second amino compound Polyamide shell comprising The polyamide core-shell microcapsules are

[0123] According to one embodiment, the shell comprises a stabilizing agent, preferably a biopolymer.

[0124] According to one embodiment, the shell does not include a polyol.

[0125] According to certain embodiments, the polyamide core-shell microcapsules are - a hydrophobic material, preferably an oil-based core, comprising a perfume, and a polyamide shell comprising: acyl chloride, preferably in an amount of 5-98%, preferably 20-98%, more preferably 30-85% (w / w); a first amino compound, preferably in an amount of 1 to 50% (w / w), preferably 7 to 40% (w / w), a second amino compound, preferably in an amount of 1 to 50% (w / w), preferably 2 to 25% (w / w), A stabilizer, preferably in an amount of 0-90% (w / w), preferably 0.1-75% (w / w), more preferably 1-70% (w / w) Polyamide shell comprising Includes.

[0126] It should be understood that the sum of the shell components equals 100%.

[0127] According to certain embodiments, the polyamide core-shell microcapsules are - a hydrophobic material, preferably an oil-based core, comprising a perfume, and a polyamide shell comprising: Acyl chlorides, a first amino compound which is an amino acid, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof, a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine, and mixtures thereof; A biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein, and mixtures thereof. Polyamide shell comprising Includes.

[0128] The embodiments previously described with respect to the nature of the hydrophobic material, the stabilizer, the acyl chloride, the first amino compound and the second amino compound also apply to the polyamide microcapsules defined above.

[0129] Without being bound by any theory, the inventors believe that the presence of the stabilizer, preferably a biopolymer, forms a complex structure with the polyamide, and more particularly with the acid chloride compound.

[0130] According to a particular embodiment, the first amino compound and the second amino compound contained in the shell of the polyamide microcapsule are different.

[0131] According to certain embodiments, the polyamide microcapsules include an inner shell of polyurea.

[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] Multiple Microcapsule System According to one embodiment, the microcapsules of the present invention (a first type of microcapsules) may be used in combination with a second type of microcapsules.

[0134] Other objects of the present invention are to provide - microcapsules of the invention as a first type of microcapsule, and - a second type of microcapsules, in which the first type of microcapsules and the second type of microcapsules differ in hydrophobic material and / or wall material and / or coating material. A microcapsule delivery system comprising:

[0135] By way of non-limiting example, the nature of the polymer shell of the second type of microcapsules can vary. By way of non-limiting example, the shell of the second type of microcapsules can be aminoplast-based, polyurea-based, or polyurethane-based. The shell of the second type of microcapsules can be hybrid, i.e. organic-inorganic, for example a hybrid shell composed of at least two types of inorganic particles crosslinked, or a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0136] According to one embodiment, the shell of the second type of microcapsule comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glioxal.

[0137] According to another embodiment, the shell of the second type of microcapsule is polyurea-based, composed of, for example, but not limited to, an isocyanate-based monomer and an amine-containing crosslinker, such as guanidine carbonate and / or guanazole. A preferred polyurea microcapsule comprises a polyurea wall that is the reaction product of polymerization between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from the group consisting of an amine (e.g., a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of an amine can be omitted.

[0138] According to a particular embodiment, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol and 0.6% to 1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages defined by weight relative to the total amount of colloidal stabilizer). According to another embodiment, the emulsifier is an anionic or amphiphilic biopolymer, preferably selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0139] According to a particular embodiment, the shell of the second type of microcapsule comprises an inner layer of polyurea and an outer layer of hydrogel, preferably composed of gelatin and gum arabic.

[0140] According to a particular embodiment, the shell of the second type of microcapsule comprises an inner layer of polyurea and an outer layer of a cross-linked protein, preferably a mixture of sodium caseinate and whey protein.

[0141] According to another embodiment, the shell of the second type of microcapsule is polyurethane-based, composed of, for example but not limited to, polyisocyanates and polyols, polyamides, polyesters, and the like.

[0142] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In one embodiment, the microcapsule wall material may comprise any suitable resin, in particular melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, and the like. Suitable resins include reaction products of aldehydes and amines, suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include methylol melamine, methylated methylol amine, imino melamine, and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea resorcinol, and mixtures thereof. Materials suitable for manufacturing are available from one or more of the following companies: Solutia Inc. (St Louis, Missouri USA), Cytec Industries (West Paterson, New Jersey USA), and Sigma-Aldrich (St. Louis, Missouri USA).

[0143] According to certain embodiments, the second type of core-shell microcapsules are formaldehyde-free capsules. A typical process for the production of aminoplast formaldehyde-free microcapsule slurry is: 1) The following: a) Melamine, or melamine and two NH 2 At least one C containing functional group 1 ~C 4 a polyamine component in the form of a mixture with a compound, b) Glyoxal, C 4-6 A mixture of 2,2-dialkoxy-ethanols and optionally glyoxalates, with a ratio of glyoxal / C of 1 / 1 to 10 / 1. 4-6 an aldehyde component in the form of a mixture having a molar ratio of 2,2-dialkoxy-ethanol; c) Protonic acid catalyst preparing an oligomeric composition comprising or obtained by reacting together the reaction products of 2) The droplet size is 1 to 600 μm, and i. Oily substances, ii. aqueous medium; iii. at least one oligomeric composition as obtained in step 1; iv. at least one cross-linking agent selected from: A) C 4 ~C 12 Aromatic or aliphatic diisocyanates or triisocyanates and their biurets, triuret, trimers, trimethylolpropane adducts and mixtures thereof, and / or B) Formula A-(Oxirane-2-ylmethyl) n [In the formula, n represents 2 or 3, and A represents a C group optionally containing 2 to 6 nitrogen atoms and / or oxygen atoms. 2 ~C 6 Dioxirane or trioxirane compounds of the formula v. Any two NH 2 C containing functional groups 1 ~C 4 compound preparing an oil-in-water dispersion comprising: 3) heating the dispersion. 4) Cooling the dispersion Includes.

[0144] Said method is described in detail in WO 2013 / 068255, the contents of which are incorporated by reference.

[0145] According to another embodiment, the shell of the second type of microcapsule slurry is polyurea-based or polyurethane-based. Examples of polyurea and methods for producing polyurea-based microcapsule slurries are described, for example, in WO2007 / 004166, EP2300146, and EP2579976, the contents of which are incorporated by reference. Typically, the preparation method for polyurea-based or polyurethane-based microcapsule slurries includes the following steps: a) dissolving at least one polyisocyanate having at least two isocyanates in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding the oil phase to the water phase to form an oil-in-water dispersion having an average droplet size of 1-500 μm, preferably 5-50 μm; d) applying conditions sufficient to induce interfacial polymerization and form microcapsules in the form of a slurry. Includes.

[0146] Flavoring compositions / consumer products The microcapsules of the present invention can be used in combination with active ingredients. (i) microcapsules 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 neutralizing ingredient, a bactericide ingredient, a fungicide ingredient, a pharmaceutical ingredient or a pesticide ingredient, a disinfectant ingredient, an insect repellent or attractant, and mixtures thereof; A composition comprising:

[0147] The microcapsules of the invention can be used for the preparation of perfuming or flavouring compositions, which are also the object of the present invention.

[0148] The capsules of the present invention show good performance in terms of stability in media of interest.

[0149] Another object of the present invention is to (i) Microcapsules as defined above, in which the oil contains a perfume. (ii) at least one component selected from the group consisting of perfume carriers, perfume co-ingredients, and mixtures thereof; (iii) optionally at least one flavoring adjuvant; A fragrance composition comprising:

[0150] As liquid perfume carriers, mention may be made, as non-limiting examples, of 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, mention may be made of the most commonly used solvents, such as, but not limited to, dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate. With regard to compositions that contain both perfume carriers and perfume co-ingredients, other perfume carriers that are more suitable than those mentioned above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, such as those known under the trade name Isopar® (source: Exxon Chemical) or glycol ethers and glycol ether esters, such as those known under the trade name Dowanol® (source: Dow Chemical Company). Furthermore, with regard to "perfume co-ingredients", here we mean compounds that are used in perfumed preparations or compositions to impart a pleasant effect and that are not microcapsules as defined above. In other words, such an auxiliary ingredient to be considered a perfuming auxiliary ingredient must be recognized by the skilled artisan as being at least capable of imparting or modifying the odor of the composition in a positive or desirable way, and not merely having one odor.

[0151] The nature and type of perfuming co-ingredients present in said perfuming composition, which will in any case not be exhaustive, do not warrant a more detailed description here, whereby a person skilled in the art can select said base on the basis of his general knowledge and according to any use or application and the organoleptic effect desired.In general terms, these perfuming co-ingredients belong to various chemical classes: alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds and essential oils, and said perfuming co-ingredients may be of natural or synthetic origin.Many of these co-ingredients are in any case mentioned in references, for example in Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or its latest editions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.It is also understood that said co-ingredients may be compounds known to release various types of perfuming compounds in a controlled manner.

[0152] By "perfuming adjuvants" is meant here ingredients capable of imparting additional added effects, such as color, particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants customarily used in perfuming bases cannot be exhaustive, but it should be mentioned that said ingredients are well known to the person skilled in the art.

[0153] Preferably, the perfuming composition according to the invention comprises between 0.01 and 30% by weight of microcapsules as defined above.

[0154] 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.

[0155] According to a particular embodiment, the consumer product as defined above is liquid and a) from 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent, and c) Microcapsules as defined above d) Optionally, unencapsulated flavorings. Contains:

[0156] According to a particular embodiment, the consumer product as defined above is in the form of a powder, and a) from 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) a microcapsule powder as defined above, c) optionally, a flavor powder different from the microcapsules defined above Contains:

[0157] In the case of microcapsules comprising a perfume oil-based core, the products of the invention can be used in particular in perfumed consumer products, such as those belonging to refined fragrances or "functional" perfumery. Functional perfumery includes in particular personal care products, including hair care, body cleansing, skin care, hygiene care, and home care products, including laundry care and air care. Another object of the invention therefore consists in perfumed consumer products comprising, as perfuming ingredient, a microcapsule as defined above or a perfuming composition as defined above. The perfume elements of said consumer products may be combinations of perfume microcapsules as defined above and free or non-encapsulated perfumes, as well as other types of perfume microcapsules other than those disclosed herein.

[0158] In particular, a) from 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent, and c) a perfuming composition as defined above A liquid consumer product containing the compound is another object of the present invention.

[0159] below, a) from 2 to 65% by weight, based on the total weight of the consumer product, of at least one surfactant, and b) a perfuming composition as defined above Powdered consumer products containing the compound are also part of the invention.

[0160] The microcapsules of the present invention may therefore be added as such or as part of the perfuming composition of the present invention in perfumed consumer products.

[0161] For reasons of clarity, it should be noted that by "perfumed consumer product" is meant a consumer product that is expected to provide, among other benefits, a perfuming effect to the surface to which it is applied (e.g. skin, hair, textiles, paper or household surfaces) or in the air (air fresheners, deodorizers, etc.) In other words, a perfumed consumer product according to the invention is a product that comprises a functional formulation, also referred to as a "base", together with an active substance, in an effective amount of the microcapsules according to the invention.

[0162] The nature and type of other constituents of the perfumed consumer product do not warrant a more detailed description here, which in any case will not be exhaustive, and the skilled person can select the nature and type of ingredients of the perfumed consumer product based on their general knowledge and according to the nature of the product and the desired effect. The base preparations of consumer products that can be introduced into the microcapsules of the present invention can be found in the abundant literature on such products. Their preparations do not warrant a detailed description here and are not in every case exhaustive. The skilled person who prepares such consumer products can completely select suitable ingredients based on their general knowledge and available literature.

[0163] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, colognes, aftershave lotions, body splashes; fabric care products, such as liquid or solid detergents, tablets and pods, fabric softeners, dryer sheets, fabric refreshers, ironing water, or bleach; personal care products, such as hair care products (e.g., shampoos, hair conditioners, hair dyes, or hairsprays), cosmetic formulations (e.g., vanishing creams, body lotions, or deodorants or antiperspirants), or skin care products (e.g., clothing products). It may be a perfumed soap, a shower or bath smooth, a body wash, an oil or gel, a bath salt, or a hygiene product; an air care product, such as an air freshener or a "ready to use" powder air freshener; or a home care product, such as an all purpose cleanser, a liquid or powder or tablet dish washing product, a toilet cleanser or a product for cleaning various surfaces, such as sprays and wipes for fabrics or for treating / refreshing hard surfaces (floors, tiles, stone floors, etc.); a hygiene product, such as a sanitary napkin, a diaper, a toilet paper.

[0164] Another object of the present invention is to - personal care active bases, and - a microcapsule as defined above or a perfuming composition as defined above wherein the consumer product is in the form of a personal care composition.

[0165] The personal care active bases that can be incorporated into the microcapsules of the present invention can be found in the abundant literature on such products. Their preparation does not warrant a detailed description herein and is not exhaustive in every case. The skilled person in the art of preparing such consumer products is entirely capable of selecting suitable ingredients based on his general knowledge and the available literature.

[0166] The personal care composition is preferably selected in the group consisting of a hair care product (e.g. shampoo, hair conditioner, hair dye or hairspray), a cosmetic formulation (e.g. vanishing cream, body lotion or deodorant or antiperspirant), or a skin care product (e.g. perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or hygiene product).

[0167] Another object of the present invention is to - a home care or fabric care active base, and - a microcapsule as defined above or a perfuming composition as defined above wherein the consumer product is in the form of a home care or fabric care composition.

[0168] Home care or fabric care active bases that can be incorporated into the microcapsules of the present invention can be found in the abundant literature on such products. Their preparation does not warrant a detailed description herein and is not exhaustive in every case. Those skilled in the art of preparing such consumer products are entirely capable of selecting suitable ingredients based on their general knowledge and the available literature.

[0169] Preferably, the consumer product comprises 0.1 to 15% by weight, more preferably 0.2 to 5% by weight, of the microcapsules of the invention, all these percentages being defined as weight relative to the total weight of the consumer product. Of course, said concentrations may be adapted according to the beneficial effects desired in the respective product.

[0170] According to certain embodiments, the consumer product in which the microcapsules are incorporated has a pH of less than 4.5.

[0171] Fabric softener The object of the present invention is to provide the following: - a fabric softener active base in an amount preferably ranging from 85 to 99.95% by weight, relative to the total weight of the composition; preferably a fabric softener active base selected from the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquats (HEQ), TEAQ (triethanolamine quats), cationic guar, silicones and mixtures thereof, a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; The present invention relates to a consumer product in the form of a fabric softener composition comprising:

[0172] Liquid detergent The object of the present invention is to provide the following: - a liquid detergent active base, preferably in an amount ranging from 85 to 99.95% by weight, relative to the total weight of the composition; preferably a liquid detergent active base selected in the group consisting of anionic surfactants, such as alkylbenzenesulfonates (ABS), secondary alkylsulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides. a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; The present invention relates to a consumer product in the form of a liquid detergent composition comprising:

[0173] Solid detergent The object of the present invention is to provide the following: - a solid detergent active base, preferably in an amount ranging from 85 to 99.95% by weight, relative to the total weight of the composition; preferably a liquid detergent active base selected in the group consisting of anionic surfactants, such as alkylbenzenesulfonates (ABS), secondary alkylsulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and non-ionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides, a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; The present invention relates to a consumer product in the form of a solid detergent composition comprising:

[0174] Solid scent booster The object of the present invention is to provide the following: - solid carriers, preferably selected from the group consisting of urea, sodium chloride, sodium sulfate, sodium acetate, zeolites, sodium carbonate, sodium bicarbonate, clays, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars such as sucrose, mono-, di- and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohol or fatty acid, and mixtures thereof, microcapsules as defined above, in powder form, preferably in an amount ranging from 0.05 to 15% by weight and more preferably from 0.1 to 5% by weight relative to the total weight of the composition; and a consumer product in the form of a solid flavoring agent comprising:

[0175] Liquid scent booster The object of the present invention is to - aqueous phase, - a surfactant system consisting essentially of one or more non-ionic surfactants, wherein the surfactant system has an average HLB of 10 to 14 and is preferably selected from the group consisting of ethoxylated fatty alcohols, POE / PPG (polyoxyethylene and polyoxypropylene) ethers, monoglyceryl esters, polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxyl esters, alkyl polyglucosides, amine oxides and combinations thereof, - a linker selected from the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxyl carboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactants with an HLB of less than 10, and mixtures thereof; and microcapsules as defined above, in the form of a slurry, in an amount preferably ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; and a consumer product in the form of a liquid flavoring comprising:

[0176] Shampoo / Shower gel The object of the present invention is to provide the following: a shampoo or shower gel active base, preferably in an amount ranging from 85 to 99.95% by weight relative to the total weight of the composition; preferably a shampoo or shower gel active base 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, a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; The present invention relates to a consumer product in the form of a shampoo or shower gel composition comprising:

[0177] Rinse-off conditioner The object of the present invention is to provide the following: a rinse-off conditioner active base, preferably in an amount ranging from 85 to 99.95% by weight relative to the total weight of the composition; preferably a rinse-off conditioner active base selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride and mixtures thereof, a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; The present invention relates to a consumer product in the form of a rinse-off conditioner composition comprising:

[0178] Hair dye The object of the present invention is to provide the following: an oxidation phase comprising an oxidizing agent, preferably in an amount ranging from 85 to 99.95% by weight relative to the total weight of the composition, and an alkaline phase comprising an alkynyl agent, a dye precursor and a coupling compound, said dye precursor and said coupling compound forming an oxidative hair dye in the presence of the oxidizing agent, a microcapsule slurry as defined above, preferably in an amount ranging from 0.05 to 15% by weight, more preferably from 0.1 to 5% by weight, relative to the total weight of the composition; and a consumer product in the form of a hair dye composition comprising:

[0179] By "oxidative hair dye composition" we mean a composition that contains two groups of colorless dye molecules: dye precursors and coupling agents. When they react with each other through an oxidation process, they form a wide range of colored molecules (dyes) that are trapped in 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.

[0180] "Dye precursor" and "oxidative dye precursor" are used interchangeably in the present invention.

[0181] The dye precursor has at least two electron donating groups, e.g., NH, at the para or ortho positions to impart the property of easy oxidation. 2 and aromatic compounds derived from benzene substituted with OH.

[0182] 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.

[0183] The primary dye precursor is used in combination with a coupling agent, which is preferably derived from benzene and has an NH 2 and OH, which do not produce color by themselves but modify the color, shade, or intensity produced by the dye precursor.

[0184] According to one embodiment, the coupling agent is selected in the group consisting of resorcinol, 2-methylresorcinol, 4-chlororesorquinol, 2,5-diaminotoluene, 1,3-diaminobenzene, 2,4-diaminophenoxyethanol HCl, 2-amino-hydroxyethylaminoanisole sulfate, 4-amino-2-hydroxytoluene, and mixtures thereof.

[0185] The oxidative dye precursor is preferably used in an amount ranging from 0.001% to 5% by weight, preferably from 0.1% to 4% by weight, relative to the total weight of the composition.

[0186] 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, see for example EP 0946133 A1, the contents of which are incorporated by reference.

[0187] 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.

[0188] The alkaline agent is preferably used in an amount ranging from 1% to 20% by weight, preferably from 3% to 9% by weight, relative to the total weight of the composition.

[0189] In accordance with the present invention, a coupling agent and a dye precursor in an alkaline medium form an oxidative hair dye in the presence of an oxidizing agent.

[0190] The oxidizing agent provides the oxygen gas necessary to develop the color molecules and produce the color change in the hair.

[0191] Oxidizing agents must be safe and effective for use in the compositions herein.

[0192] Preferably, 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 to be used.

[0193] Preferably, the oxidizing agents suitable for use herein are water soluble. The oxidizing agents suitable for use herein are selected from inorganic peroxygen oxidizing agents, preformed organic peracid oxidizing agents and organic peroxide oxidizing agents or mixtures thereof.

[0194] The oxidizing agent is preferably used in an amount ranging from 5% to 30% by weight, preferably from 5% to 25% by weight, relative to the total weight of the composition.

[0195] Ingredients commonly used in cosmetic compositions may 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.

[0196] According to a particular embodiment, 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.

[0197] Perfuming composition According to a particular embodiment, the consumer product comprises, based on the total weight of the perfuming composition: - 0.1 to 30% by weight, preferably 0.1 to 20% by weight, of microcapsules as defined above, 0 to 40% by weight, preferably 3 to 40% by weight, of a fragrance, and - 20 to 90% by weight of ethanol, preferably 40 to 90% by weight The composition is in the form of a fragrance composition comprising:

[0198] The invention will now be further illustrated by the following examples, with the understanding that the invention as claimed is in no way limited by these examples.

[0199] Working Example [Table 3-1] [Table 3-2] 1) Benzene-1,3,5-tricarbonyl chloride; Supplier: Aldrich, Switzerland 2) m-Xylylenediamine; Supplier: Aldrich, Switzerland 3) L-Lysine; Supplier: Aldrich, Switzerland 4) Ethylenediamine; Supplier: Aldrich, Switzerland 5) Diethylenetriamine; Supplier: Aldrich, Switzerland 6) Spermine dihydrate; Supplier: Aldrich, Switzerland 7) 3-Aminopropyltriethoxysilane; Supplier: Alfa Aesar Switzerland 8) Guanidine carbonate; Supplier: Aldrich, Switzerland 9) Cystamine hydrochloride; Supplier: Aldrich, Switzerland 10) Cystine diethyl butyl ester; Supplier: Aldrich, Switzerland 11) L-Arginine; Supplier: Aldrich, Switzerland 12) L-Glutamine; Supplier: Aldrich, Switzerland 13) L-Theorine;Supplier: Aldrich, Switzerland 14) Lactose; Supplier: Aldrich, Switzerland 15) Zain; Supplier: Aldrich, Switzerland 16) Acacia Gum Superstab AA, Supplier: Nexira, France 17) Bovine serum albumin; Supplier: Aldrich, Switzerland 18) New Rice; Supplier: TER Chemicals Ingredients GMBH&Co 19) White eggs 20) Bio Pro 2E063;Supplier:Agropur Inc.USA 21) Bio Pur β-lactoglobulin;Supplier:Danisco 22) Sodium caseinate; Supplier: Aldrich, Switzerland 23) Sodium bicarbonate; Supplier: Aldrich, Switzerland 24) Sodium carbonate; Supplier: Aldrich, Switzerland 25) Sodium hydroxide; Supplier: Aldrich, Switzerland 26) Triethanolamine; Supplier: Aldrich, Switzerland 27) Takenate D-110N.

[0200] Balm composition: [Table 4] 1) Methyl dihydrojasmonate, Firmenich SA, Geneva, Switzerland 2) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, International Flavors & Fragrances, USA 3) (-)-(8R)-8,12-epoxy-13,14,15,16-tetranorlabdane, Firmenich SA, Geneva, Switzerland.

[0201] [Table 5] 1) Supplier: Firmenich SA, Geneva, Switzerland 2) Trademark from IFF; 2-tert-butyl-1-cyclohexyl acetate.

[0202] Example 1 Preparation of polyamide microcapsules with colloidal stabilizers in oil phase. Benzene-1,3,5-tricarbonyl chloride (1.77 g, Table 1) was dissolved in benzyl benzoate (5 g). Bovine serum albumin (0.95 g) was dissolved in benzyl benzoate (5 g) and optionally kept under stirring at 60° C. for 1 hour. Both solutions were mixed together, stirred at room temperature for 10 minutes and added to perfume oil (25 g, Table 2a or Table 2b) at room temperature to form an oil phase. The oil phase was mixed with water (94.05 g) containing the first amino compound. The reaction mixture was stirred with an Ultra Turrax at 24000 rpm for 30 seconds or 1 minute to obtain an emulsion. The second amino compound (Table 3) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. A solution of guanidine carbonate (30% by weight in water, 5-10 g) was optionally added to adjust the pH value to about 8. The reaction mixture was stirred at 30° C. for 4 hours to obtain a white dispersion.

[0203] [Table 6-1] [Table 6-2]

[0204] Capsule C(a) Production - Different Stabilizers Capsule C was prepared in the presence of different proteins according to the protocol described above in the presence of L-lysine (2.5 g) as the first amino compound and ethylenediamine (0.48 g) as the second amino compound.

[0205] [Table 7]

[0206] Capsule C(b) Production – Different Stabilizers Capsules C(b) were prepared according to the protocol used for capsules A with L-lysine (2.5 g) as the first amino compound, cystamine dihydrochloride (1.8 g) as the second amino compound, and a different colloidal stabilizer.

[0207] [Table 8]

[0208] Capsule D – Preparation of Capsule D in Oil Phase with Different Amounts of Acyl BCT Chloride Capsules were prepared with BSA (0.95 g), L-lysine and different amounts of 1,3,5-benzenetricarbonyl chloride (BTC) in the oil phase according to the method for capsule A.

[0209] [Table 9]

[0210] Capsule E - Preparation of Capsule E with Two or More Amino Compounds Capsule E was prepared according to the protocol used for Capsule A with sodium caseinate (2 g) as colloidal stabilizer, L-lysine (2.5 g) as the first amino compound, and a mixture of secondary and tertiary amino compounds.

[0211] [Table 10]

[0212] Capsule F - Preparation of capsule F by adding two or more amino compounds before the addition of emulsion 1,3,5-Benzenetricarbonyl chloride (1.77g, Table 1) was dispersed in benzyl benzoate (5g). Sodium caseinate (0.95g-2g) was dissolved in benzyl benzoate (5g) and optionally maintained under stirring at 60°C for 30 minutes. Both solutions were mixed together and added to perfume oil (25g, Table 2) at room temperature to form an oil phase. The oil phase was mixed with water (94.05g) containing two amino compounds. The reaction mixture was stirred with Ultra Turrax at 24000 rpm for 30 seconds or 1 minute to obtain an emulsion. The reaction mixture was stirred at 30°C for 4 hours to obtain a white dispersion.

[0213] [Table 11]

[0214] Example 2 Preparation of polyamide microcapsules with colloidal stabilizers in aqueous phase. A solution of 1,3,5-benzenetricarbonyl chloride (1.77 g) in benzyl benzoate (5 g) was added to the perfume oil (25 g, Table 2) to form an oil phase. A first amino compound was dissolved in an aqueous solution of gum arabic (95 g, 2% by weight). The solution was stirred for 15 minutes to form an aqueous phase. The oil phase was added to the aqueous phase and the reaction mixture was stirred with an Ultra Turrax at 24000 rpm for 30 seconds to obtain an emulsion. A second amino compound (Table 7) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. The reaction mixture was stirred with an anchor at 200 rpm at 30° C. for 4 hours to obtain a white dispersion.

[0215] Capsule G - Preparation of Capsule G in the Presence of Gum Arabic Capsule G was prepared in the presence of 2% by weight (95 g) of an aqueous solution of gum arabic.

[0216] [Table 12]

[0217] Preparation of capsules H1 containing other colloidal stabilizers and their mixtures in water A solution of 1,3,5-benzenetricarbonyl chloride (1.77 g) in benzyl benzoate (5 g) was added to the perfume oil (25 g, Table 2) to form the oil phase. L-lysine (2.5 g) was dissolved in an aqueous solution of colloidal stabilizer (95 g, 2% by weight). 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 24000 rpm for 30 seconds to obtain an emulsion. Ethylenediamine (0.24-0.48 g) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. The reaction mixture was stirred with an anchor at 200 rpm at 30°C for 4 hours to obtain a white dispersion.

[0218] [Table 13]

[0219] Example 3 Storage stability of fabric softeners The storage stability of the capsules in the fabric softener was evaluated. 0.27 g of the capsule dispersion of the present invention (containing encapsulated perfume oil B) was diluted with 29.73 g of the fabric softener composition described in Table 11. The fabric softener was stored at 37° C. for up to one month, and the amount of perfume leaked from the capsules was measured by solvent extraction and GC-FID analysis (Table 12).

[0220] [Table 14]

[0221] [Table 15]

[0222] It can be concluded that the microcapsules of the present invention show satisfactory stability in the bases of interest.

[0223] Example 4 Preparation of polyamide microcapsules with colloidal stabilizers in oil phase. Benzene-1,3,5-tricarbonyl chloride (1.77 g, Table 1) and Takenate D110N (0.031 g, Table 1) were dispersed in benzyl benzoate (5 g). Sodium caseinate (2 g) was dissolved in benzyl benzoate (5 g) and optionally maintained under stirring at 60° C. for 1 hour. Both solutions were mixed together, stirred at room temperature for 1 minute and added to perfume oil (25 g, Table 2b) at room temperature to form an oil phase. The oil phase was mixed with water (94.05 g) containing the first amino compound. The reaction mixture was stirred with an Ultra Turrax at 24000 rpm for 30 seconds or 10 minutes to obtain an emulsion. The second amino compound (Table 13) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. A solution of guanidine carbonate (30% by weight in water, 5-10 g) was optionally added to adjust the pH value to about 8. The reaction mixture was stirred at 30° C. for 4 hours to obtain a white dispersion.

[0224] [Table 16]

[0225] Capsule J - Preparation of Capsule J with Different Amounts of Caseinate Dispersed in Oil Phase 1,3,5-Benzenetricarbonyl chloride (1.77 g, Table 1) was dispersed in benzyl benzoate (5 g). Sodium caseinate (0.95 g-2 g) was dissolved in benzyl benzoate (5 g) and optionally kept under stirring at 60° C. for 30 minutes. Both solutions were mixed together and added to perfume oil (25 g, Table 2b) at room temperature to form an oil phase. The oil phase was mixed with water (94.05 g) containing an amino compound. The reaction mixture was stirred in an Ultra Turrax at 24000 rpm for 30 seconds or 1 minute to obtain an emulsion. A second amino compound (Table 14) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. A solution of guanidine carbonate (30% by weight in water, 5-10 g) was optionally added to adjust the pH value to about 8. The reaction mixture was stirred at 30° C. for 4 h to give a white dispersion.

[0226] [Table 17]

[0227] Example 5 Polyamide capsules with cationic coating The manufacturing method of Microcapsule S corresponds to that of Microcapsule J5, except that an additional step of adding a cationic copolymer (0.8% by weight relative to the slurry), namely acrylamidopropyltrimonium chloride / acrylamide copolymer (Salcare® SC60, supplier BASF) (3% by weight in water) was carried out at the end of the process.

[0228] Example 6 Polyamide capsules with mixtures of acyl chlorides Capsule E: Preparation of capsule K with mixture of acyl chloride and caseinate in oil phase Capsule K was prepared in the presence of caseinate and diamine according to the protocol used to prepare capsule A in the presence of L-lysine (2.5 g) as the first amino compound and ethylenediamine (0.48 g or 0.24 g) as the second amino compound.

[0229] [Table 18]

[0230] Example 7 Olfactory performance of polyamide microcapsules The microcapsule slurry is diluted in fabric softener base with 0.11% free perfume (see composition in Table 11). The sample is agitated in an agitator for 5 minutes at 41 rpm. The sample is diluted to 2% with deionized water to approximate the dilution in the washing machine during the rinse cycle. 1 mL of this solution is withdrawn and placed on blotting paper. The sample is allowed to dry at room temperature for 24 hours before evaluation before and after abrasion.

[0231] Rating scale: (scent strength): 1 = no fragrance smell; 2 = barely detectable; 3 = weak; 4 = moderate; 5 = moderately strong; 6 = strong; 7 = very strong.

[0232] [Table 19]

[0233] The capsules exhibit good friction effects which ensure efficient encapsulation.

[0234] Example 8 Shell composition by elemental analysis Shell Extraction The slurry is washed three times with deionized water in a separatory funnel. The washed microcapsules are centrifuged at 5000 RPM for 20 minutes. The microcapsules are removed and dried at room temperature for 2 days. The dried shells are crushed and placed in an Erlenmeyer flask and the perfume is extracted with ethyl acetate (concentration 5% by weight) and magnetic stirring (1 hour, 500 rpm). The shells are filtered under vacuum in a sintered glass funnel. The extraction was carried out five times. The shells were collected in a crystallizer, dried at 50° C. under vacuum and crushed in an IKA Tube Mill (5 minutes; 20100 rpm) to obtain a white powder. The shells were stirred in water for 24 hours and collected by filtration. The shells were dried and crushed again in an IKA Tube Mill (5 minutes; 20100 rpm). The shells were extracted with ethyl acetate and magnetic stirring (1 hour; 600 rpm) and filtered under vacuum in a sintered glass funnel. This process was repeated five times. The shells were collected in a crystallizer and dried under vacuum at 50° C. The resulting product was milled (IKA Tube Mill, 5 min; 20100 rpm).

[0235] Determination of shell composition by elemental analysis Elemental analyses of the various shell components were calculated using ChemDraw Professional (Version: 17.1.0.105, Supplier: PerkinElmer Informatics, Inc., USA). Compositions were estimated by calculation based on the component compositions reported in Table 17.

[0236] [Table 20]

[0237] The results showed that the shells contained the reaction products of 1,3,5-benzenetricarbonyl chloride with both amino compounds. Analysis confirmed the presence of cystamine in the shells along with lysine.

[0238] The results showed that the shell contained more than 50 mol% of the reaction product of 1,3,5-benzenetricarbonyl chloride with amino compounds. Analysis confirmed the presence of ethylenediamine in the shell with lysine when lysine was used in the formulation. The presence of colloidal stabilizers was also observed in capsules E1 and E2 (gum arabic).

[0239] Example 9 Spray-dried microcapsule preparations Emulsions A to E are prepared having the following components:

[0240] [Table 21-1] [Table 21-2] 1) CapsulTM, Ingredion 2) Maltodextrin 10DE Supplier: Roquette 3) Maltose, Lehmann&Voss 4) Silica, Evonik 5) See Table 19.

[0241] [Table 22] 1) Firmenich SA, Switzerland 2) 3-(4-tert-butylphenyl)-2-methylpropanal, Givaudan SA, Vernier, Switzerland 3) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, International Flavors & Fragrances, USA 4) Firmenich SA, Switzerland 5) Methyl dihydrojasmonate, Firmenich SA, Switzerland 6) Firmenich SA, Switzerland.

[0242] The components of the polymer matrix (maltodextrin and capsule TM , or capsule TM and citric acid and tripotassium citrate) in water at 45-50°C until completely dissolved.

[0243] For Emulsion D, Free Fragrance C is added to the water phase.

[0244] The microcapsule slurry is added to obtain a mixture, and the resulting mixture is mixed gently at 25° C. (room temperature).

[0245] Granular powders A-E are produced by spray drying emulsions A-E using a Sodeva Spray Dryer (supplier France) with the air inlet temperature set at 215° C. and a throughput of 500 ml per hour. The air outlet temperature is 105° C. The emulsions are allowed to come to room temperature before spraying.

[0246] Example 10 Liquid fragrance composition A sufficient amount of microcapsule slurries A through J is weighed and mixed in the liquid flavoring (Table 20) to add an amount equivalent to 0.2% flavoring.

[0247] [Table 23] 1) Deces-8; Brand and Supplier: KLK Oleo 2) Laureth-9; Trademark and Source 3) Plantacare 2000UP; trademark and supplier: BASF.

[0248] Produce different ringing gel compositions (compositions 1-6) according to the following protocol.

[0249] In a first step, the aqueous phase (water), the solvent (propylene glycol), if present, and the surfactant are mixed at room temperature with stirring using a magnetic stirrer at 300 rpm for 5 minutes.

[0250] In the second step, the linker is dissolved in the hydrophobic active ingredient (fragrance) at room temperature with a magnetic stirrer at 300 rpm. The resulting mixture is mixed for 5 minutes.

[0251] The water and oil phases are then mixed together at room temperature for 5 minutes to form a clear or milky ringing gel.

[0252] Example 11 Liquid detergent composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into a liquid detergent (Table 21) and an amount equivalent to 0.2% fragrance is added.

[0253] [Table 24] 1) Hostapur SAS 60;Supplier: Clariant 2) Edenor K 12-18;Supplier:Cognis 3) Genapol LA 070;Supplier: Clariant 4) Supplier: Genencor International 5) Aculyn 88; Supplier: Dow Chemical.

[0254] Example 12 Powder detergent composition A sufficient amount of granules A-E is weighed and mixed into a powder detergent composition (Table 22) to add the equivalent of 0.2% perfume.

[0255] [Table 25]

[0256] Example 13 Concentrated All-Purpose Cleanser Formula A sufficient amount of Microcapsule Slurries A through J is weighed and mixed into a concentrated all-purpose cleanser composition (Table 23) to add the equivalent of 0.2% fragrance.

[0257] [Table 26] 1) Neodol 91-8 (registered trademark); Trademark and Supplier: Shell Chemical 2) Biosoft D-40 (registered trademark); trademark and supplier: Stepan Company 3) Stepanate SCS (registered trademark); Trademark and Supplier: Stepan Company 4) Kathon CG®; Trademark and Supplier: Dow Chemical Company.

[0258] All ingredients are mixed together and the mixture is diluted to 100% with water.

[0259] Example 14 Solid fragrance composition The following composition is prepared:

[0260] [Table 27]

[0261] [Table 28]

[0262] Example 15 Shampoo Composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into a shampoo composition (Table 26) to add an amount equivalent to 0.2% fragrance.

[0263] [Table 29] 1) Ucare Polymer JR-400, Noveon 2) Schweizerhall 3) Glydant, Lonza 4) Texapon NSO IS, Cognis 5) Tego Betain F 50, Evonik 6) Amphotensid GB 2009, Zschimmer&Schwarz 7) Monomuls 90 L-12, Gruenau 8) Nipagin Monosodium, NIPA.

[0264] Polyquaternium-10 is dispersed in water. The remaining ingredients of Phase A are mixed by adding them one after the other with good mixing after each addition. This premix is ​​then added to the Polyquaternium-10 dispersion and mixed for 5 minutes. Phase B and premixed Phase C (Heat Monomuls 90L-12 in Texapon NSO IS to melt) are then added. The mixture is mixed thoroughly. Phases D and E are then added with stirring. The pH is adjusted with citric acid solution until pH: 5.5-6.0.

[0265] Example 16 Shampoo Composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into a shampoo composition (Table 27) to add an amount equivalent to 0.2% fragrance.

[0266] [Table 30] 1) EDETA B Powder, BASF 2) Jaguar C14 S, Rhodia 3) Ucare Polymer JR-400, Noveon 4) Sulfetal LA BE, Zschimmer&Schwarz 5) Zetesol LA, Zschimmer&Schwarz 6) Tego Betain F 50, Evonik 7) Xiameter MEM-1691, Dow Corning 8) Lanette 16, BASF 9) Comperlan 100, Cognis 10) Cutina AGS, Cognis 11) KathonCG, Rohm&Haas 12) D-Panthenol, Roche.

[0267] A premix containing guar hydroxypropyltrimonium chloride and polyquaternium-10 is added to the water and tetrasodium EDTA and mixed. When the mixture is homogenous, NaOH is added. Phase C ingredients are then added and the mixture is heated to 75°C. Phase D ingredients are added and mixed until homogenous. Heat is removed and the mixture is cooled to room temperature. At 45°C, Phase E ingredients are added and the final viscosity is adjusted with 25% NaCl solution and pH is adjusted to 5.5-6 with 10% NaOH solution.

[0268] Example 17 Rinse-off hair composition Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed into a rinse-off composition (Table 28) to add the equivalent of 0.2% fragrance.

[0269] [Table 31] 1) Genamin KDMP, Clariant 2) Tylose H10 Y G4, Shin Etsu 3) Lanette O, BASF 4) Arlacel 165, Croda 5) Incroquat Behenyl TMS-50-PA-(MH), Croda 6) Brij S20, Croda 7) Xiameter MEM-949, Dow Corning 8) Alfa Aesar.

[0270] Mix Phase A ingredients until a homogenous mixture is obtained. Dissolve Tylose completely. Heat the mixture to 70-75°C. Combine Phase B ingredients and melt at 70-75°C. Add Phase B ingredients to Phase A with good mixing and continue mixing until cooled to 60°C. Add Phase C ingredients and maintain mixing with stirring until the mixture cools to 40°C. Adjust pH with citric acid solution to pH: 3.5-4.0.

[0271] Example 18 Antiperspirant spray anhydrous composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into an antiperspirant spray anhydrous composition (Table 29) to add an amount equivalent to 0.2% fragrance.

[0272] [Table 32] 1) Dow Corning® 345 Fluid; Brand and Supplier: Dow Corning 2) Aerosil® 200; Brand and Supplier: Evonik 3) Bentone® 38; Trademark and Supplier: Elementis Specialities 4) Micro Dry Ultrafine; Brand and Supplier: Reheis.

[0273] Using a high speed stirrer, add the silica and Quaternium-18-Hectorite to the mixture of isopropyl myristate and cyclomethicone. Once fully swollen, add the aluminum chlorohydrate in small portions while stirring until the mixture is homogenous and free of lumps. Fill an aerosol can with 25% of the suspension and 75% of propane / butane (2.5 bar).

[0274] Example 19 Antiperspirant spray emulsion composition Sufficient amounts of microcapsule slurries A through J are weighed and mixed into an antiperspirant spray emulsion composition (Table 30) to add an amount equivalent to 0.2% fragrance.

[0275] [Table 33] 1) Tween 65; Brand and Supplier: CRODA 2) Dehymuls PGPH; Trademark and Supplier: BASF 3) Abil EM-90; Brand and Supplier: BASF 4) Dow Corning 345 Fluid; Brand and Supplier: Dow Corning 5) Crodamol ipis; Brand and Supplier: CRODA 6) Phenoxyethanol; Brand and Supplier: LANXESS 7) Sensiva sc 50; Brand and Supplier: KRAFT 8) Tegosoft TN; Trademark and Supplier: Evonik 9) Aerosil R 812; Brand and Supplier: Evonik 10) Nipagin mna; Trademark and Supplier: CLARIANT 11) Locron L; Trademark and supplier: CLARIANT.

[0276] Weigh out the ingredients of Part A and Part B separately. Heat the ingredients of Part A to 60°C and the ingredients of Part B to 55°C. Pour the ingredients of Part B into A in small portions with continuous stirring. Stir the mixture well until it reaches room temperature. Then add the ingredients of Part C. Mix the emulsion and introduce it into an aerosol can. Crimp and add the propellant. Aerosol filling: Emulsion 30%: Propane / Butane 70%, 2.5bar.

[0277] Example 20 Deodorant spray composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into an antiperspirant deodorant spray composition (Table 31) to add an amount equivalent to 0.2% fragrance.

[0278] [Table 34] 1) Irgasan® DP 300; Trademark and Supplier: BASF.

[0279] Mix and dissolve all ingredients according to the order in Table 24. Then fill the aerosol can, crimp and add the propellant (aerosol fill: 40% active solution, 60% propane / butane, 2.5 bar).

[0280] Example 21 Antiperspirant roll-on emulsion composition A sufficient amount of microcapsule slurries A through J is weighed and mixed into an antiperspirant roll-on emulsion composition (Table 32) to add an amount equivalent to 0.2% fragrance.

[0281] [Table 35] 1) BRIJ 72;Supplier:ICI 2) BRIJ 721;Supplier:ICI 3) ARLAMOL E;Supplier:UNIQEMA-CRODA 4) LOCRON L;Supplier: CLARIAN.

[0282] Part A and Part B are heated separately to 75°C; Part A is added to Part B with stirring and the mixture is homogenized for 10 minutes. The mixture is then cooled with stirring; and when the mixture reaches 45°C, Part C is added slowly and when the mixture reaches 35°C, Part D is added with stirring. The mixture is then cooled to room temperature.

[0283] Example 22 Antiperspirant roll-on composition A sufficient amount of Microcapsule Slurries A through J is weighed and mixed into an antiperspirant roll-on composition (Table 33) to add an amount equivalent to 0.2% fragrance.

[0284] [Table 36] 1) LOCRON L;Supplier: CLARIANT 2) EUMULGIN B-1;Supplier: BASF 3) EUMULGIN B-3;Supplier: BASF.

[0285] The ingredients of Part B are mixed in a container and the ingredients of Part A are added. Then Part C is dissolved in Parts A and B. Along with the fragrance, add 1 part Cremophor RH40 to 1 part fragrance with good mixing.

[0286] Example 23 Antiperspirant roll-on composition Sufficient amounts of microcapsule slurries A through J are weighed and mixed into an antiperspirant roll-on emulsion composition (Table 34) to add an amount equivalent to 0.2% fragrance.

[0287] [Table 37] 1) Natrosol® 250 H; Brand and Supplier: Ashland 2) Irgasan® DP 300; Trademark and Supplier: BASF 3) CREMOPHOR® RH 40; trademark and supplier: BASF.

[0288] Part A is prepared by gradually sprinkling hydroxyethyl cellulose into water while stirring rapidly with a turbine. Stirring is continued until the hydroxyethyl cellulose is completely swollen and a clear gel is obtained. Then, gradually pour Part B into Part A while continuing to stir until the whole is homogenous. Add Part C.

[0289] Example 24 Alcohol-free deodorant pump Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 35) to add an amount equivalent to 0.2% fragrance.

[0290] [Table 38] 1) Ceraphyl 41; Brand and Supplier: ASHLAND 2) DOW CORNING 200 FLUID 0.65cs; Trademark and Supplier: DOW CORNING CORPORATION 3) Ceraphyl 28; Brand and Supplier: ASHLAND 4) Eutanol G; Trademark and Supplier: BASF 5) Irgasan® DP 300; Trademark and Supplier: BASF.

[0291] All ingredients in Table 28 are mixed in the order listed and the mixture is heated slightly to dissolve the cetyl lactate.

[0292] Example 25 Deodorant pump containing alcohol Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 36) to add an amount equivalent to 0.2% fragrance.

[0293] [Table 39] 1) Softigen 767; Brand and Supplier: CRODA 2) CREMOPHOR® RH 40; trademark and supplier: BASF.

[0294] Mix together the ingredients from Part B. Dissolve the ingredients of Part A in the order listed and pour into Part B.

[0295] Example 26 Talc Compound A sufficient amount of granules A to E is weighed out and introduced into a standard talc base (100% talc, very slight characteristic odor, white powder, supplier: LUZENAC), mixed and an amount equivalent to 0.2% of fragrance is added.

[0296] Example 27 Shower Gel Reference Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 37) to add an amount equivalent to 0.2% fragrance.

[0297] [Table 40] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) 2) CARBOPOL AQUA SF-1 POLYMER; Trademark and supplier: NOVEON 3) ZETESOL AO 328 U; Trademark and Supplier: ZSCHIMMER&SCHWARZ 4) TEGO-BETAIN F 50; Brand and Supplier: GOLDSCHMIDT 5) KATHON CG; Trademark and supplier: ROHM&HASS.

[0298] Mix ingredients and adjust pH to 6-6.3 (Viscosity: 4500 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0299] Example 28 Shower gel composition Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 38) to add an amount equivalent to 0.2% fragrance.

[0300] [Table 41] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) ZETESOL AO 328 U; Trademark and Supplier: ZSCHIMMER&SCHWARZ 3) TEGO-BETAIN F 50; Brand and Supplier: GOLDSCHMIDT 4) MERQUAT 550; Brand and Supplier: LUBRIZOL.

[0301] The ingredients are mixed and the pH is adjusted to 4.5 (Viscosity: 3000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0302] Example 29 Shower gel composition Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 39) to add an amount equivalent to 0.2% fragrance.

[0303] [Table 42] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) Texapon NSO IS; Trademark and Supplier: Cognis 3) MERQUAT 550; Brand and Supplier: LUBRIZOL 4) DEHYTON AB-30; Trademark and supplier: COGNIS 5) GLUCAMATE LT; Trademark and Supplier: LUBRIZOL 6) EUPERLAN PK 3000 AM; Trademark and supplier: COGNIS 7) CREMOPHOR RH 40; trademark and supplier: BASF.

[0304] The ingredients are mixed and the pH adjusted to 4.5 (Viscosity: 4000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0305] Example 30 Hand Dish Wash Sufficient amounts of Microcapsule Slurries A through J are weighed and mixed in the following composition (Table 40) to add an amount equivalent to 0.2% fragrance.

[0306] [Table 43] 1) Biosoft S-118 (registered trademark); trademark and supplier: Stepan Company 2) Ninol 40-CO (registered trademark); Trademark and Supplier: Stepan Company 3) Stepanate SXS (registered trademark); Trademark and Supplier: Stepan Company 4) Tergitol 15-S-9 (registered trademark); Trademark and Supplier: Dow Chemical Company.

[0307] Mix water with sodium hydroxide and diethanolamide. Add LAS. After neutralizing LAS, add remaining ingredients. Check pH (=7-8) and adjust if necessary.

[0308] Example 31 Toothpaste formulations A sufficient amount of Microcapsule Slurry M (corresponding to Microcapsule A except that menthol flavour is encapsulated) is weighed out and mixed in the following composition (Table 42) to add an amount equivalent to 0.2% of flavour.

[0309] [Table 44] 1) Tixosil 73; Trademark and Supplier: 2) Tixosil 43; Trademark and Supplier:.

[0310] Example 32 Dicalcium phosphate-based toothpaste formulations A sufficient amount of Microcapsule Slurry M (corresponding to Microcapsule A except that menthol flavour is encapsulated) is weighed out and mixed in the following composition (Table 43) to add an amount equivalent to 0.2% of flavour.

[0311] [Table 45] 1) Aerosil® 200; Trademark and Supplier:.

[0312] Example 33 Alcohol-free mouthwash formulation A sufficient amount of Microcapsule Slurry M (corresponding to Microcapsule A except that menthol flavour is encapsulated) is weighed out and mixed in the following composition (Table 44) to add an amount equivalent to 0.2% of flavour.

[0313] [Table 46]

[0314] Example 34 Mouthwash formulations A sufficient amount of Microcapsule Slurry M (corresponding to Microcapsule A except that menthol flavour is encapsulated) is weighed out and mixed in the following composition (Table 45) to add an amount equivalent to 0.2% of flavour.

[0315] [Table 47]

Claims

1. below, 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) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; and c) carrying out a curing step to form polyamide microcapsules in the form of a slurry. wherein a stabilizer is added to the oil phase and / or the water phase, and at least a second amino compound is added to the water phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

2. below: 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) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) adding a second amino compound to the oil-in-water emulsion obtained in step b); and d) carrying out a curing step to form polyamide microcapsules in the form of a slurry.

2. The method of claim 1, wherein the stabilizer is added to the oil phase and / or the water phase.

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

4. 4. The method according to any one of claims 1 to 3, wherein the first amino compound is an amino acid, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine and mixtures thereof.

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

6. 6. The method of any one of claims 1 to 5, wherein the second amino compound is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochloride, xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, polyetheramines, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, and mixtures thereof.

7. 7. The method of claim 1, wherein the first amino compound and the second amino compound are different.

8. 8. The method of claim 1, wherein the stabilizer comprises a biopolymer, preferably selected from the group consisting of whey protein, casein, sodium caseinate, bovine serum albumin, and mixtures thereof.

9. The functional group NH of the second amino compound 2 9. The process according to claim 1, wherein the molar ratio of aryloxycarbonyl to the functional group COCl of said acyl chloride is between 0.01 and 7.

5.

10. 10. The method of any one of claims 1 to 9, wherein the mass ratio of the acyl chloride to the hydrophobic material is from 0.01 to 0.

09.

11. 1. A polyamide core-shell microcapsule comprising: - an oil-based core comprising a hydrophobic material, preferably a perfume, and - a polyamide shell, hereinafter acyl chlorides, preferably in an amount of 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% (w / w); a first amino compound, preferably in an amount of 1 to 50% (w / w), preferably 7 to 40% (w / w), a second amino compound, preferably in an amount of 1 to 50% (w / w), preferably 2 to 25% (w / w), a stabilizer, preferably a biopolymer, preferably in an amount of 0-90% (w / w), preferably 0.1-75% (w / w), more preferably 1-70% (w / w); Polyamide shell comprising 2. A polyamide core-shell microcapsule comprising:

12. The polyamide core-shell microcapsule of claim 11 , wherein the first amino compound and the second amino compound are different.

13. below, - an oil-based core comprising a hydrophobic material, preferably a perfume, and - a polyamide shell, hereinafter acyl chloride, a first amino compound which is an amino acid, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and mixtures thereof; a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine, and mixtures thereof; a biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein, and mixtures thereof; Polyamide shell comprising The polyamide core-shell microcapsule according to claim 11 or 12, comprising:

14. below, (i) a perfume microcapsule as defined in any one of claims 11 to 13, wherein the hydrophobic material comprises a perfume; (ii) at least one component selected from the group consisting of a perfume carrier and a perfume base; (iii) optionally at least one flavor adjuvant; A fragrance composition comprising:

15. below, - personal care active bases, and - a microcapsule as defined in any one of claims 11 to 13 or a perfuming composition as defined in claim 14 1. A consumer product comprising:

16. below, - home care or fabric care active bases, and - a microcapsule as defined in any one of claims 11 to 13 or a perfuming composition as defined in claim 14 wherein the consumer product is in the form of a home care or fabric care composition.

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