Method for preparing polyamide microcapsules

Abstract

The invention relates to a novel method for preparing polyamide microcapsules. Polyamide microcapsules obtainable by said method are also an object of the invention. Perfuming compositions and consumer products comprising said capsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the invention.

Description

[0001] This invention is a divisional application of the patent application No. 201980084629.X, with the invention title of "Method for Preparing Polyamide Microcapsules", which was filed on December 19, 2019. Technical Field

[0002] The present invention relates to a new method for preparing polyamide microcapsules. The polyamide microcapsules obtainable by said method are also an object of the present invention. Perfumed compositions and consumer products containing said capsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the present invention. Background Art

[0003] One of the problems faced by the fragrance (cosmetic fragrance) industry is that odoriferous compounds, due to their volatility, especially the volatility of "top notes", lose their olfactory benefits relatively quickly. To adjust the release rate of volatiles, delivery systems (such as microcapsules containing fragrances) are needed to protect and release the core payload upon triggering. For these systems, a key requirement in the industry is to be able to remain suspended on a challenging basis without physical decomposition or degradation. This is called the stability of the delivery system. For example, aromatic personal and household cleaners containing high levels of aggressive surfactants are very challenging for the stability of microcapsules.

[0004] Microcapsule slurries based on polyureas and polyurethanes are widely used, for example, in the fragrance industry because they provide long-lasting and pleasant olfactory effects after being applied to different substrates. These microcapsules have been widely disclosed in the prior art (see, for example, WO2007 / 004166 or EP 2300146 from the applicant).

[0005] Therefore, there is still a need to use new microcapsules without compromising their performance, especially in terms of stability in challenging media such as consumer product bases and good delivery performance in the delivery of hydrophobic materials, such as olfactory performance in the case of perfuming ingredients.

[0006] The present invention provides a solution to the above problems by providing a new method for preparing polyamide microcapsules. Summary of the Invention

[0007] It has now been found that core-shell microcapsules encapsulating a hydrophobic material, preferably a hydrophobic active ingredient, can be obtained by reacting an acyl chloride with at least one amino compound during an interfacial polymerization process. Therefore, the method of the present invention provides a solution to the above problems because it allows the preparation of microcapsules having the required stability in challenging bases.

[0008] In a first aspect, the present invention relates to a method for preparing a polyamide core-shell microcapsule slurry, which comprises the following steps:

[0009] a) Dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a perfume, to form an oil phase;

[0010] b) Dispersing the oil phase obtained in step a) into an aqueous phase optionally containing an amino compound A or a base to form an oil-in-water emulsion; and

[0011] c) Performing a curing step to form polyamide microcapsules in the form of a slurry,

[0012] wherein at least one amino compound B is added to the aqueous phase before forming the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0013] A second object of the present invention is a polyamide core-shell microcapsule slurry obtainable by the above method.

[0014] Another object of the present invention is a flavoring composition comprising:

[0015] (i) A microcapsule slurry as defined above, wherein the hydrophobic material comprises a perfume,

[0016] (ii) At least one component selected from the group consisting of a perfume carrier and a perfume base,

[0017] (iii) Optionally, at least one perfume adjuvant.

[0018] Another object of the present invention is a consumer product comprising:

[0019] - A personal care active ingredient, and

[0020] - A microcapsule as defined above or a flavoring composition as defined above,

[0021] wherein the consumer product is in the form of a personal care composition.

[0022] Another object of the present invention is a consumer product comprising:

[0023] - A household care or fabric care active ingredient, and

[0024] - A microcapsule as defined above or a flavoring composition as defined above,

[0025] wherein the consumer product is in the form of a household care or fabric care composition. Detailed Description

[0026] Unless otherwise specified, percentages (%) refer to weight percentages of the composition.

[0027] By "active ingredient" is meant a single compound or a combination of multiple ingredients.

[0028] By "perfume oil or flavoring oil" is meant a single flavoring or flavoring compound, or a mixture of several flavoring or flavoring compounds.

[0029] By "consumer product" or "end product" is meant a finished product ready to be distributed, sold and used by the consumer.

[0030] For the sake of clarity, the expression "dispersion" in the present invention refers to a system in which particles are dispersed in a continuous phase of different composition, and specifically includes suspensions or emulsions.

[0031] "Microcapsule" or similar expressions in the present invention refer to core-shell microcapsules having a particle size distribution in the micron range (e.g., average diameter (d(v,0.5)), preferably about 1 to 3000 microns) and comprising an outer solid polymer-based shell and an internal continuous oil phase surrounded by the outer shell.

[0032] By "amino compound" is to be understood a compound having at least two reactive amine groups.

[0033] In the present invention, the terms "acyl chloride" or "acid chloride" are used interchangeably.

[0034] By "polyamide microcapsule" is meant that the outer shell of the microcapsule contains a polyamide material. The term "polyamide microcapsule" may also include a shell made of a composite material comprising a polyamide material and another material, such as a biopolymer.

[0035] It has been found that when a stabilizer is added to the oil phase in this method, polyamide core-shell microcapsules with generally good performance in terms of stability in challenging substrates can be obtained.

[0036] Method for preparing a polyamide microcapsule slurry

[0037] Thus, a first object of the present invention is a method for preparing a polyamide core-shell microcapsule slurry, the method comprising the following steps:

[0038] a) Dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a perfume, to form an oil phase;

[0039] b) Dispersing the oil phase obtained in step a) into an aqueous phase optionally containing an amino compound A or a base to form an oil-in-water emulsion; and

[0040] c) Performing a curing step to form polyamide microcapsules in the form of a slurry,

[0041] At least one amino compound B is added to the aqueous phase before forming the oil-in-water emulsion and / or added to the oil-in-water emulsion obtained after step b).

[0042] According to one embodiment, the method comprises the following steps:

[0043] a) Dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a perfume, to form an oil phase;

[0044] b) Dispersing the oil phase obtained in step a) into an aqueous phase optionally containing amino compound A or a base to form an oil-in-water emulsion;

[0045] c) Adding amino compound B to the oil-in-water emulsion obtained in step b); and

[0046] d) Performing a curing step to form polyamide microcapsules in the form of a slurry.

[0047] In one step of the method, the oil phase is formed by mixing at least one hydrophobic material with at least one acyl chloride and a stabilizer.

[0048] According to a specific 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, oxydiacetyl dichloride, succinyl dichloride, and mixtures thereof.

[0049] The weight ratio between the acyl chloride and the hydrophobic material is preferably from 0.01 to 0.09, more preferably from 0.03 to 0.07.

[0050] The acyl chloride can be directly dissolved in the perfume oil, or it can be pre-dispersed in an inert solvent such as benzyl benzoate before mixing with the hydrophobic material, preferably the perfume oil.

[0051] According to a specific embodiment, a polyisocyanate having at least two isocyanate functional groups is added to the oil phase.

[0052] Suitable polyisocyanates used according to the present invention include aromatic polyisocyanates, aliphatic polyisocyanates, and mixtures thereof. The polyisocyanate contains at least 2, preferably at least 3, but can contain up to 6, or even only 4 isocyanate functional groups. According to a specific embodiment, a triisocyanate (3 isocyanate functional groups) is used.

[0053] According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.

[0054] The term "aromatic polyisocyanate" as used herein means any polyisocyanate containing an aromatic moiety. Preferably, it contains a phenyl, toluoyl, xylyl, naphthyl or diphenyl moiety. More preferably a toluoyl or xylyl moiety. Preferred aromatic polyisocyanates are biurets, polyisocyanurates and trimethylolpropane adducts of diisocyanates, more preferably containing one of the above specific aromatic moieties. More preferably, the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (available from Bayer under the trade name RC), a trimethylolpropane adduct of toluene diisocyanate (available from Bayer under the trade name L75), a trimethylolpropane adduct of xylylene diisocyanate (available from Mitsui Chemicals under the trade name D-110N). In a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.

[0055] 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 trimers of hexamethylene diisocyanate, trimers of isophorone diisocyanate, trimethylolpropane adducts of hexamethylene diisocyanate (available from Mitsui Chemicals) or biurets of hexamethylene diisocyanate (commercially available from Bayer under the trade name N 100), with the biuret of hexamethylene diisocyanate being even more preferred.

[0056] 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 preferably, it 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 between the aliphatic polyisocyanate and the aromatic polyisocyanate is from 80:20 to 10:90.

[0057] According to one embodiment, based on the total amount of the oil phase, the amount of the at least one polyisocyanate used in the process according to the invention is from 0.1 to 15% by weight, preferably from 0.5 to 10% by weight, more preferably from 0.8 to 6% by weight, even more preferably from 1 to 3% by weight.

[0058] Hydrophobic material

[0059] According to one embodiment, the hydrophobic material is a hydrophobic active ingredient.

[0060] By "hydrophobic active ingredient" is meant any hydrophobic active ingredient that forms a two-phase dispersion when mixed with water, i.e., a single ingredient or a mixture of multiple ingredients. The hydrophobic active ingredient is a liquid at about 20 °C.

[0061] The hydrophobic active ingredient is preferably selected from the group consisting of flavorings, flavoring ingredients, fragrances, fragrance ingredients, nutritional products, cosmetics, pest control agents, biocide active substances, and mixtures thereof.

[0062] According to a particular embodiment, the hydrophobic active ingredient comprises a mixture of a fragrance and another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents, and biocide active ingredients.

[0063] According to a particular embodiment, the hydrophobic active ingredient comprises a mixture of a biocide active ingredient and another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, and pest control agents.

[0064] According to a particular embodiment, the hydrophobic active ingredient comprises a mixture of a pest control agent and another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, and biocide active ingredients.

[0065] According to a particular embodiment, the hydrophobic active ingredient comprises a fragrance.

[0066] According to a particular embodiment, the hydrophobic active ingredient consists of a fragrance.

[0067] According to a particular embodiment, the hydrophobic active ingredient consists of a biocide active ingredient.

[0068] According to a particular embodiment, the hydrophobic active ingredient consists of a pest control agent.

[0069] By "perfume" (or also referred to as "perfume oil"), here it means a component or composition that is liquid at about 20°C. According to any of the above embodiments, the perfume oil can be a single perfuming ingredient or a mixture of ingredients in the form of a perfuming composition. As a "perfuming ingredient", here it means a compound whose main purpose is to impart or modify an odor. In other words, such an ingredient to be considered a perfuming ingredient must be recognized by those skilled in the art as being capable of imparting or altering the odor of a composition at least in an active or pleasant manner, rather than merely having an odor. For the purposes of the present invention, the perfume oil also includes combinations of perfuming ingredients with substances that jointly improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, emulsions or dispersions, and combinations that confer other benefits in addition to altering or imparting an odor, said benefits such as persistence, burst, malodor counteraction, antibacterial effects, microbiological stability, pest control.

[0070] The nature and type of the perfuming ingredients present in the oil phase are not guaranteed to be described in more detail here, and in any case, they are not exhaustive. Those skilled in the art are able to select them based on their common general knowledge and according to the intended use or application and the desired sensory effects. Generally speaking, these perfuming ingredients belong to different chemical classes, such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and the perfuming co-ingredients can be of natural or synthetic origin. In any case, many of these co-ingredients are listed in reference works such as the book Perfume and Flavor Chemicals by S. Arctander, 1969, Montclair, New Jersey, USA or its updated versions or other works of a similar nature, as well as in the extensive patent literature in the field of the perfume industry. It should also be understood that the ingredients can also be compounds known to release various types of perfuming compounds in a controlled manner.

[0071] In particular, perfuming ingredients commonly used in perfume formulations can be cited, such as:

[0072] - Aldehyde perfuming ingredients: decanal, dodecanal, 2-methylundecanal, 10-undecenal, octanal, nonanal and / or nonenal;

[0073] - Aromatic herbaceous ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene;

[0074] - Balsam components: coumarin, ethyl vanillin, and / or vanillin;

[0075] - Citrus fragrance components: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellonitrile, orange terpenene, limonene, 1-p-menthene-8-yl acetate, and / or 1,4(8)-p-menthadiene;

[0076] - Floral fragrance components: methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-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-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, tricyclodecenyl acetate, geraniol, p-menth-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, pentyl salicylate, highly cis-methyl dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, (S)-2-(1,1-dimethylpropoxy)propyl propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, pentyl cinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or a mixture of methyl ionone isomers;

[0077] - Fruity aroma components: γ-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiacyclopentane, 4-decanoic acid ethyl ester, hexyl acetate, 2-methylbutyric acid ethyl ester, γ-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, [3-ethyl-2-oxiranyl]acetate 1-[3,3-dimethylcyclohexyl]ethyl ester and / or diethyl 1,4-cyclohexanedicarboxylate;

[0078] - Green fragrance ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, (2-methylbutoxy) allyl 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;

[0079] - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecen-1-one, 1-oxa-12-cyclohexadecene-2-one, 1-oxa-13-cyclohexadecene-2-one, (9Z)-9-cycloheptadecene-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclohexane Pentadecene-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, oxacyclohexadecane-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate;

[0080] - Woody components: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[2,9'-tricyclo[6.2.1.0 2,7 ] undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, (1'R,E)-2-Ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate;

[0081] - Other components (such as amber, powdery, spicy or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthol, 1-phenylethenyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0082] It should also be understood that the components may also be compounds known to release various types of flavoring compounds in a controlled manner, also known as properfumes or profragrances. Non-limiting examples of suitable properfumes 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-phenylethyl oxo(phenyl)acetate or mixtures thereof.

[0083] The flavoring components can be dissolved in solvents currently used in the fragrance industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, (rosin resin, available from Eastman), benzyl benzoate, ethyl citrate, limonene or other terpenes or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, such as or benzyl benzoate. Preferably, the fragrance contains less than 30% solvent. More preferably, the fragrance contains less than 20%, even more preferably less than 10% solvent, all these percentages being by weight relative to the total weight of the fragrance. Most preferably, the fragrance is substantially solvent-free.

[0084] Preferred perfuming ingredients are ingredients with high steric hindrance, in particular those from one of the following groups:

[0085] - Group 1: perfuming ingredients containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted by at least one linear or branched C 1 - C 4 alkyl or alkenyl substituent;

[0086] - Group 2: perfuming ingredients containing a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted by at least one linear or branched C 4 - C 8 alkyl or alkenyl substituent;

[0087] - Group 3: perfuming ingredients containing a benzene ring, or containing a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted by at least one linear or branched C 5 - C 8 alkyl or alkenyl substituent, or substituted by at least one phenyl substituent and optionally by one or more linear or branched C 1 - C 3 alkyl or alkenyl substituents;

[0088] - Group 4: perfuming ingredients containing at least two fused or linked C 5 and / or C 6 rings;

[0089] - Group 5: perfuming ingredients containing a camphor-like ring structure;

[0090] - Group 6: perfuming ingredients containing at least one C 7 - C 20 ring structure;

[0091] - Group 7: perfuming ingredients with a logP value higher than 3.5 and containing at least one tert-butyl or at least one trichloromethyl substituent;

[0092] Examples of ingredients from each of these groups are:

[0093] - Group 1: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (source: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, (methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate, source: Firmenich SA, Geneva, Switzerland), neralide, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, ((S)-1,8-p-Menthadiene-7-ol, source: Firmenich SA, Geneva, Switzerland), l-p-menthen-4-ol, (1RS,3RS,4SR)-3-p-menthyl acetate, (1R,2S,4R)-4,6,6-trimethyl-bicyclo[3,1,1]heptan-2-ol, (tetrahydro-4-methyl-2-phenyl-2H-pyran, source: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, trimethylcyclohexyl acetate (cyclanol), (1,4-cyclohexanedicarboxylic acid diethyl ester, source: Firmenich SA, Geneva, Switzerland), ((3ARS,6SR,7ASR)-perhydro-3,6-dimethyl-benzofuran-2-one, source: Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzofuran-2-one, source: Firmenich SA, Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 2,4,6-trimethyl-3-cyclohexene-1-carbaldehyde;

[0094] - Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (source: Givaudan SA, Vernier, Switzerland), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol (source: Firmenich SA, Geneva, Switzerland), ((1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol, source: Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone (fleuramone), HC (methyl-cis-3-oxo-2-pentyl-1-cyclopentaneacetate, source: Firmenich SA, Geneva, Switzerland), (2,2,5-trimethyl-5-pentyl-1-cyclopentanone, source: Firmenich SA, Geneva, Switzerland), (3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, source: Firmenich SA, Geneva, Switzerland), 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (source: Givaudan SA, Vernier, Switzerland);

[0095] - Group 3: damascenone, (1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, source: Firmenich SA, Geneva, Switzerland), nectalactone ((1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'-yl)propyl]cyclopentanone), α-ionone, β-ionone, damascenone, (mixture of 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, source: Firmenich SA, Geneva, Switzerland), β(1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, source: Firmenich SA, Geneva, Switzerland), ((1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate, source: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1-cyclohexyl acetate (source: International Flavors and Fragrances, USA), (1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol, source: Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (source: Firmenich SA, Geneva, Switzerland), (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, terpenyl isobutyrate, (4-(1,1-dimethylethyl)-1-cyclohexyl acetate, source: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, ((1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, source: Firmenich SA, Geneva, Switzerland), p-tert-butylcyclohexanone, menthenethiol, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexanecarboxylate, cyclohexyl salicylate, methyl 2-methoxy-4-methylphenyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, methyl 4-ethyl-2-methoxyphenyl carbonate;

[0096] - Group 4: methyl cedryl ketone (source: International Flavors and Fragrances, USA), Verdylate, vetyverol, vetyverone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone (source: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10-tetramethyl-1-oxaspiro[4.5]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-indanone (source: International Flavors and Fragrances, USA), (Mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1,1-dimethyl-5-indanyl)propanal, source: Firmenich SA, Geneva, Switzerland), (3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9-spiro-2'-oxirane, source: Firmenich SA, Geneva, Switzerland), 9 / 10-ethyldiene-3-oxatricyclo[6.2.1.0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthyl acetate, source: Firmenich SA, Geneva, Switzerland), 1-naphthol (octalynol), (dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan, source: Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl acetate and tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl propionate and tricyclo[5.2.1.0(2,6)]dec-4-en-8-yl propionate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'-cyclohexen-4'-one;

[0097] - Group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, camphorpinene, cedarwood methyl ether (8-methoxy-2,6,6,8-tetramethyl-tricyclo[5.3.1.0(1,5)]undecane, source: Firmenich SA, Geneva, Switzerland), cedrene, cedrene alcohol, cedrene alcohol, (a mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one and 10-ethylidene-3-oxatricyclo[6.2.1.0(2,7)]undecan-4-one, source: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (source: Firmenich SA, Geneva, Switzerland);

[0098] - Group 6: (trimethyl-13-oxabicyclo-[10.1.0]-tridec-4,8-diene, source: Firmenich SA, Geneva, Switzerland), galanthus pyrrolidone LG ((E)-9-cyclohexadecene-16-olide, source: Firmenich SA, Geneva, Switzerland), (cyclopentadecenolide, origin: Firmenich SA, Geneva, Switzerland), musk ketone (3-methyl (4 / 5)-cyclopentadecenone, source: Firmenich SA, Geneva, Switzerland), musk ketone (source: Firmenich SA, Geneva, Switzerland), (pentadecalactone, source: Firmenich SA, Geneva, Switzerland), (cyclopentadecanone, source: Firmenich SA, Geneva, Switzerland), (1-ethoxyethoxy)cyclododecane (source: Firmenich SA, Geneva, Switzerland), Musk T (Astrotone), 4,8-cyclododecadien-1-one;

[0099] - Group 7: (Source: Givaudan SA, Vergne, Switzerland), rosin oil.

[0100] Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7 as defined above. More preferably, the perfume comprises at least 30%, preferably at least 50% of ingredients selected from Groups 3 to 7 as defined above. Most preferably, the perfume comprises at least 30%, preferably at least 50% of ingredients selected from Groups 3, 4, 6 or 7 as defined above.

[0101] According to another preferred embodiment, the fragrance comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5, even more preferably above 3.75.

[0102] Preferably, the perfume used in the present invention contains less than 10% of its own weight of primary alcohol, less than 15% of its own weight of secondary alcohol and less than 20% of its own weight of tertiary alcohol. Advantageously, the perfume used in the present invention does not contain any primary alcohol, but contains less than 15% of secondary and tertiary alcohols.

[0103] According to one embodiment, the oil phase (or oil-based core) comprises:

[0104] - 25 to 100 wt% of a fragrance oil comprising at least 15 wt% of a high impact fragrance raw material having a Log T < -4, and

[0105] -0 to 75 wt% of density-balanced material, the density of which is greater than 1.07 g / cm 3 .

[0106] "High impact fragrance raw materials" are understood to be fragrance raw materials with Log T < -4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charge and molecular weight. For convenience, the threshold concentration is expressed as the common logarithm of the threshold concentration, i.e. Log[threshold] ("LogT").

[0107] "Density balanced material" should be understood as having a density greater than 1.07 g / cm 3 And materials with low odor or no odor are preferred.

[0108] The odor threshold concentration of the flavoring compounds is determined by using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact volume of the fragrance oil component injected by the syringe, the exact split ratio and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate is accurately measured and the sampling volume is calculated assuming that the duration of human inhalation lasts 12 seconds. Since the exact concentration at the detector at any point in time is known, the mass per volume inhaled is known, so the concentration of the flavoring compound is known. To determine the threshold concentration, the solution is delivered to the sniffing port with the back-calculated concentration. The panelist sniffs the GC effluent and determines the retention time when the odor is perceived. The average of all panelists determines the odor threshold concentration of the flavoring compound. The determination of odor thresholds is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.

[0109] WO2018115250 describes high impact fragrance raw materials with Log T < -4 and with a density greater than 1.07 g / cm 3 The density of the density balance material properties, the contents of which are incorporated by reference.

[0110] According to one embodiment, the high impact fragrance raw materials with Log T<-4 are selected from the list in Table A below.

[0111] Table A: High impact fragrance raw materials with Log T < -4

[0112]

[0113]

[0114]

[0115]

[0116] According to one embodiment, the fragrance raw material with Log T<-4 is selected from the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.

[0117] According to one embodiment, the fragrance raw material with Log T <-4 comprises at least one compound selected from the group consisting of alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof, preferably in an amount of 20 to 70% by weight, based on the total weight of the fragrance raw materials with Log T <-4.

[0118] According to one embodiment, the fragrance raw materials with Log T <-4 comprise 20 to 70 wt. % of aldehydes, ketones and mixtures thereof, based on the total weight of the fragrance raw materials with Log T <-4.

[0119] Therefore, the remaining perfume raw materials contained in the oil-based core may have a Log T>-4.

[0120] Non-limiting examples of fragrance raw materials having a Log T > -4 are listed in Table B below.

[0121] Table B: Fragrance Raw Materials with log T>-4

[0122]

[0123]

[0124] According to one embodiment, the oil phase (or oil-based core) comprises 2 to 75% by weight of a substance with a density greater than 1.07 g / cm 3 density balancing material, and 25-98 wt. % of a fragrance oil comprising at least 15 wt. % of a high impact fragrance raw material having a Log T<-4.

[0125] The density of a component is defined as the ratio of its mass to its volume (g / cm 3 ).

[0126] There are several methods that can be used to determine the density of a component.

[0127] The d20 density of essential oils may be measured with reference to, for example, the ISO 298:1998 method.

[0128] According to one embodiment, the density balancing material is selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, phenyl phenylacetate, phenethyl phenoxyacetate, triacetin, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.

[0129] According to a specific embodiment, the density balancing material is selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, and mixtures thereof.

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

[0131] The term "biocide" refers to a chemical substance that 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 such as preventing scaling of water, agricultural products (including seeds), and oil pipelines. Biocides can be pesticides, including fungicides, herbicides, insecticides, algaecides, molluscicides, miticides, and rodenticides; and / or antimicrobial agents, such as bactericides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal and / or antiparasitic agents.

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

[0133] By "flavoring ingredient or composition", it is meant here a flavoring ingredient, or a mixture of a plurality of flavoring ingredients, solvents or adjuvants currently used to prepare a flavoring formula, i.e. a specific mixture of ingredients intended to be added to an edible composition or chewing product to impart, improve or modify its organoleptic properties, in particular its flavor and / or taste. Taste modifiers are also included in the definition. Flavoring ingredients are well known to those skilled in the art, and their properties do not warrant a detailed description here, and in any case they are inexhaustible, and a skilled flavorist can select them according to his general knowledge and according to the intended use or application and the organoleptic effect desired to be achieved. Many of these flavoring ingredients are listed in references, such as S. Arctander's book Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA or its latest version, or other works of similar nature, such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press or MB Jacobs' Synthetic Food Adjuncts, 1947, van Nostrand Co., Inc. Solvents and adjuvants currently used in preparing flavoring formulations are also well known in the art.

[0134] In a particular embodiment, the flavoring is selected from the group consisting of terpene flavorings including citrus and mint oils, and sulfur-containing flavorings.

[0135] According to any embodiment of the invention, the hydrophobic material represents about 10% to 60% w / w, or even 15% to 45% w / w, relative to the total weight of the dispersion obtained after step b).

[0136] According to a particular embodiment, the oil phase consists essentially of the acid chloride, the fragrance oil or flavoring oil and the stabilizer.

[0137] According to the invention, a stabilizer is added to the oil phase to be subsequently formed on the emulsion. According to one embodiment, the stabilizer is a colloidal stabilizer.

[0138] Colloidal stabilizers can be molecular emulsifiers (standard emulsions) or solid particles (Pickering emulsions).

[0139] By "stabilizer" is meant a compound capable of stabilizing an oil / water interface as an emulsion. According to a particular embodiment, the stabilizer is a biopolymer.

[0140] By "biopolymer" is meant a biological macromolecule produced by a living organism. Biopolymers are characterized by a molecular weight distribution ranging from 1,000 (one thousand) Daltons to 1,000,000,000 (one billion) Daltons. These macromolecules can be carbohydrates (sugar based) or proteins (amino acid based) or a combination of both (gum), and can be straight or branched chain.

[0141] According to one embodiment, the stabilizer is selected from the group consisting of gum arabic, modified starch, polyvinyl alcohol, PVP (polyvinyl pyrrolidone), CMC (carboxymethyl cellulose), anionic polysaccharides, acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, ovalbumin (white egg albumin), sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, and mixtures thereof.

[0142] According to a particular embodiment, the stabilizer is a biopolymer selected from the group consisting of whey protein, sodium caseinate, bovine serum albumin, and mixtures thereof.

[0143] 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, which preferably comprises a fragrance oil.

[0144] The stabilizer and acid chloride may be premixed and may be heated at a temperature of, for example, 10 to 80°C before mixing with the hydrophobic material, which preferably comprises a fragrance oil.

[0145] According to any of the above embodiments of the invention, the dispersion comprises at least about 0.01% to 3.0% of a stabilizer, the percentage being expressed on a w / w basis relative to the total weight of the dispersion obtained after step b). In another aspect of the invention, the dispersion comprises about 0.05% to 2.0%, preferably about 0.05% to 1.0%, of at least one colloidal stabilizer. In another aspect of the invention, the dispersion comprises about 0.1% to 1.6%, preferably about 0.1% to 0.8%, of at least one colloidal stabilizer.

[0146] In a further step of the process according to the invention, the oil phase of step a) is dispersed in an aqueous solution, optionally comprising an amino compound A or a base, to form an oil-in-water emulsion.

[0147] The average droplet size of the emulsion is preferably from 1 to 1000 microns, more preferably from 1 to 500 microns, even more preferably from 5 to 50 microns.

[0148] When added, the amino compound A can be an amino acid, preferably selected from the group consisting of: L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine and mixtures thereof, preferably L-lysine, L-arginine, L-histidine, L-tryptophan and mixtures thereof, more preferably L-lysine, L-arginine, L-histidine and mixtures thereof. The amino acid preferably has two nucleophilic groups.

[0149] When added, the amino compound A 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 amino compound A is L-lysine.

[0150] According to a particular embodiment, the base, when added, is not an amino compound and is selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, and mixtures thereof.

[0151] The amount of base added is preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, of the dispersion.

[0152] In a further step of the method according to one embodiment, an amino compound B is added to the oil-in-water emulsion obtained in step b) to form a polyamide shell.

[0153] As a non-limiting example, the amino compound B is selected from the group consisting of xylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, (polyetheramine), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, amines with disulfide bonds such as cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochloride and mixtures thereof.

[0154] According to one embodiment, the amino compound B is an amine having a disulfide bond and is selected from the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride and mixtures thereof.

[0155] According to another embodiment, the amino compound B is selected from the group consisting of: xylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, L-lysine, L-lysine ethyl ester, (polyetheramine), ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine and mixtures thereof.

[0156] According to a particular embodiment, when amino compound A is present, the amino compound A and the amino compound B are identical.

[0157] According to another particular embodiment, when amide A is present, said amide A and said amide B are different.

[0158] According to one embodiment, when amino compound A is present, the weight ratio between amino compound A and amino compound B is from 0.5 to 25, preferably from 1.3 to 10, more preferably from 1.3 to 7.

[0159] The amount of amino compound B is usually adjusted so that the functional group NH 2 The molar ratio between COCl and the acid chloride is from 0.01 to 7.5, preferably from 0.1 to 3.0.

[0160] When added, the amount of amino compound A is usually adjusted so that the functional group NH 2 The molar ratio between the functional group COCl and the acyl chloride is 0.2 to 3, preferably 0.5 to 2.

[0161] According to one embodiment, a base is added at the end of step c) or d) to adjust the pH. As non-limiting examples, one may cite guanidine carbonate, sodium bicarbonate or triethanolamine.

[0162] The amount of base added is preferably from 0.1% to 10%, more preferably from 0.5% to 5%, of the dispersion.

[0163] This is followed by a curing step c) or d) which allows the microcapsules to end up in the form of a slurry. According to a preferred embodiment, said step is carried out at a temperature ranging from 5 to 90° C., possibly under pressure, for 1 to 8 hours, in order to enhance the kinetics. More preferably, it is carried out at a temperature ranging from 10 to 80° C. for 30 minutes to 5 hours.

[0164] According to a particular embodiment, no polyol is added during any step of the process.

[0165] Optional outer coating: According to a specific embodiment of the present invention, during or at the end of step c) or d), a polymer selected from the group consisting of nonionic polysaccharides, cationic polymers and mixtures thereof may also be added to the slurry of the present invention to form an outer coating of the microcapsules.

[0166] Nonionic polysaccharide polymers are well known to the person skilled in the art and are described, for example, in WO2012 / 007438, page 29, lines 1 to 25 and WO2013 / 026657, page 2, lines 12 to 19 and page 4, lines 3 to 12. Preferred nonionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar gum, hydroxypropyl cellulose and hydroxypropyl methylcellulose.

[0167] Cationic polymers are well known to those skilled in the art. The cationic charge density of the preferred cationic polymer is at least 0.5 meq / g, more preferably at least about 1.5 meq / g, but also preferably less than about 7 meq / g, more preferably less than about 6.2 meq / g. The cationic charge density of the cationic polymer can be determined by the Kjeldahl method, as described in the chemical test for nitrogen determination by the USP. Preferred cationic polymers are selected from those containing primary, secondary, tertiary and / or quaternary amine groups, which units can form part of the main polymer chain or can be carried by side substituents directly connected thereto. The weight average molecular weight (Mw) of the cationic polymer is preferably 10,000 to 3.5 M Daltons, more preferably 50,000 to 1.5 M Daltons. According to a particular embodiment, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N,N-dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1-vinyl-1H-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimethylammonium chloride, cassia hydroxypropyltrimethylammonium chloride, guar hydroxypropyltrimethylammonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimethylammonium chloride and cellulose hydroxypropyltrimethylammonium chloride will be 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-hydroxypropyltrimonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride. As specific examples of commercially available products, there can be cited: SC60 (cationic copolymer of acrylamidopropyltrimethylammonium chloride and acrylamide, source: BASF) or For example, PQ 11N, FC 550 or Style (polyquaternium-11-68 or vinyl pyrrolidone quaternized copolymer, source: BASF), or (C13S or C17, source: Rhodia).

[0168] According to any of the above embodiments of the present invention, an amount of the above polymer is added, and its content is about 0% to 5% w / w, or even about 0.1% to 2% w / w, the percentage being expressed on a w / w basis relative to the total weight of the slurry obtained after step c) or d). It is clearly understood by those skilled in the art that only a part of the added polymer will be incorporated into / deposited on the microcapsule shells.

[0169] Another object of the present invention is a method for preparing a microcapsule slurry, which comprises the steps as defined above and an additional step d) or e), the additional step comprising drying the slurry obtained in step c) or d), such as spray drying, to provide the microcapsules as is, i.e. in powder form. It should be understood that any standard method for such drying known to those skilled in the art is also applicable. In particular, the slurry may be spray dried, preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gum, pectin, xanthan gum, alginate, carrageenan or a cellulose derivative, to provide microcapsules in powder form.

[0170] According to a particular embodiment, the carrier material comprises free fragrance oil, which may be the same as or different from the fragrance from the microcapsule core.

[0171] Another object of the present invention is a polyamide microcapsule slurry obtainable by the process as described above. Another object of the present invention is a polyamide microcapsule powder obtainable by drying the microcapsule slurry defined above.

[0172] Perfuming compositions / consumer products

[0173] The microcapsules of the present invention can be used in combination with active ingredients. Therefore, the object of the present invention is a composition comprising:

[0174] (i) microcapsules as defined above;

[0175] (ii) an active ingredient, preferably selected from the group consisting of a cosmetic ingredient, a skin care ingredient, a fragrance ingredient, a flavoring ingredient, an odor counteracting ingredient, a bactericide ingredient, a fungicide ingredient, a pharmaceutical or agricultural chemical ingredient, a disinfectant ingredient, an insect repellent or attractant, and mixtures thereof.

[0176] The microcapsules according to the invention can be used for the preparation of perfuming or flavouring compositions, which are also an object of the present invention.

[0177] The capsules of the present invention show very good performance in terms of stability in challenging media.

[0178] Another object of the present invention is a perfuming composition comprising:

[0179] (i) Microcapsules as defined above, wherein the oil contains fragrance;

[0180] (ii) at least one ingredient selected from the group consisting of a perfume carrier, a perfume co-ingredient, and mixtures thereof;

[0181] (iii) optionally, at least one flavor adjuvant.

[0182] As liquid perfume carriers, there may be cited as non-limiting examples emulsifying systems, i.e. solvent and surfactant systems, or solvents commonly used in perfumes. A detailed description of the properties and types of solvents commonly used in perfumes is not exhaustive. However, there may be cited as non-limiting examples solvents such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used. For compositions comprising perfume carriers and perfume co-ingredients, in addition to those previously specified, other suitable perfume carriers may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, such as those sold under the trademark (Source: Exxon Chemical) Those known as glycol ethers and glycol ether esters, such as those sold under the trademark (Source: Dow Chemical Company) are known to those skilled in the art. By "fragrance co-ingredient" it is meant herein a compound which is used in a perfuming preparation or composition to impart a hedonic effect and which is not a microcapsule as defined above. In other words, to be considered a perfuming co-ingredient it must be recognized by a person skilled in the art as being capable of imparting or modifying the odor of a composition in an active or pleasant manner, rather than merely possessing an odor.

[0183] The nature and type of the perfuming auxiliary components present in the perfuming composition do not guarantee a more detailed description here, which is inexhaustible in any case, and the technician can select them according to their common sense and according to the intended use or application and the required sensory effect. Generally speaking, these perfuming auxiliary components belong to different chemical classifications, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen-containing or sulfur-containing heterocyclic compounds and essential oils, and the perfuming auxiliary components can be natural or synthetic in origin. In any case, many of these auxiliary components are listed in references such as S.Arctander's work Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated version or other works of similar nature, and in the patent literature rich in the field of spices. It is also understandable that the auxiliary component can also be a known compound that releases various types of perfuming compounds in a controlled manner.

[0184] By "perfume adjuvants" it is meant here ingredients capable of imparting additional added benefits such as colour, specific lightfastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming bases is not exhaustive, but it must be mentioned that said ingredients are well known to those skilled in the art.

[0185] Preferably, the perfuming composition according to the invention comprises from 0.1% to 30% by weight of microcapsules as defined above.

[0186] The microcapsules of the present invention can be advantageously used in many fields of application and in consumer products. The microcapsules can be used in liquid form for liquid consumer products or in powder form for powder consumer products.

[0187] According to a particular embodiment, the consumer product as defined above is a liquid and comprises:

[0188] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0189] b) water or a water-miscible hydrophilic organic solvent; and

[0190] c) a microcapsule slurry as defined above,

[0191] d) Alternatively, non-encapsulated flavorants.

[0192] According to a particular embodiment, the consumer product as defined above is in powder form and comprises:

[0193] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0194] b) Microcapsule powders as defined above.

[0195] c) Optionally, a flavor powder, which is different from the microcapsules as defined above.

[0196] In the case of microcapsules comprising a perfume oil-based core, the product of the invention is particularly useful for perfumed consumer products, such as products belonging to fine fragrances or "functional" fragrances. Functional fragrances include in particular personal care products, including hair care, body cleaning, skin care, hygiene care and home care products, including clothing care and air care. Therefore, another object of the present invention is a perfumed consumer product comprising as a perfume ingredient a microcapsule as defined above or a perfume composition as defined above. The perfume ingredient of the consumer product may be a combination of perfume microcapsules as defined above and free or non-encapsulated perfumes, as well as other types of perfume microcapsules than those disclosed herein.

[0197] In particular, the following liquid consumer product is another object of the present invention, comprising:

[0198] a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product;

[0199] b) water or a water-miscible hydrophilic organic solvent; and

[0200] c) A perfuming composition as defined above.

[0201] Likewise, the following powdered consumer product is also part of the present invention, comprising:

[0202] (a) 2 to 65% by weight of at least one surfactant relative to the total weight of the consumer product; and

[0203] (b) A perfuming composition as defined above.

[0204] The microcapsules of the invention can thus be added as such or as part of a perfuming composition of the invention to an already perfumed consumer product.

[0205] For the sake of clarity, it has to be mentioned that a "perfumed consumer product" refers to a consumer product intended to deliver a perfuming effect among different benefits to the surface to which it is applied (e.g. skin, hair, textiles, paper or household surfaces) or into the air (air fresheners, deodorants / deodorants, etc.). In other words, a perfumed consumer product according to the present invention is a processed product comprising a functional formulation (also called "base") and benefit agents, wherein an effective amount of microcapsules according to the present invention are present.

[0206] The nature and type of the other ingredients of the perfumed consumer product do not warrant a more detailed description here, which is in any case not exhaustive, and the skilled person is able to select them according to his general knowledge and according to the nature and the desired effect of the product in question. The formulations of the bases of the consumer product in which the microcapsules according to the invention can be incorporated can be found in the extensive literature relating to such products. These formulations do not warrant a detailed description here, which is in any case not exhaustive. The skilled person in the field of formulating such consumer products is fully able to select suitable components according to his general knowledge and the available literature.

[0207] Non-limiting examples of suitable perfumed consumer products may be perfumes, such as fine perfumes, colognes, aftershaves, body splashes; fabric care products, such as liquid or solid detergents, tablets and capsules, fabric softeners, dryer sheets, fabric refreshers, ironing water, or bleaching agents; personal care products, such as hair care products (e.g. shampoos, hair conditioners, coloring preparations or hair sprays), cosmetic preparations (e.g. vanishing creams, body lotions, or deodorants or antiperspirants), or skin care products (e.g. soaps, bath mousses, body washes, wash), bath oil or shower gel, bath salts, or hygiene products); air care products, such as air fresheners or "ready-to-use" powdered air fresheners; or home care products, such as all-purpose cleaners, liquid or powdered or tablet dishwashing products, toilet bowl cleaners or products for cleaning various surfaces, such as sprays and wipes for treating / renovating textiles or hard surfaces (floors, tiles, stone floors, etc.); hygiene products, such as sanitary napkins, diapers, toilet paper.

[0208] Another object of the present invention is a consumer product comprising:

[0209] - personal care active bases, and

[0210] - a microcapsule or a microcapsule powder as defined above or a perfuming composition as defined above,

[0211] Wherein the consumer product is in the form of a personal care composition.

[0212] Personal care active bases in which the microcapsules of the present invention can be incorporated can be found in the extensive literature relating to such products. These formulations do not warrant a detailed description here, which is in no way exhaustive. A person skilled in the art of formulating such consumer products is fully capable of selecting suitable components based on his general knowledge and the available literature.

[0213] The personal care composition is preferably selected from the group consisting of a hair care product (e.g. a shampoo, a hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, a body lotion, or a deodorant or an antiperspirant), or a skin care product (e.g. a soap, a bath mousse, a shower gel, a bath oil or shower gel, bath salts, or a hygiene product).

[0214] Another object of the present invention is a consumer product comprising:

[0215] - home care or fabric care active bases, and

[0216] - a microcapsule or a microcapsule powder as defined above or a perfuming composition as defined above,

[0217] Wherein the consumer product is in the form of a home care or fabric care composition.

[0218] Home care or fabric care bases in which the microcapsules of the invention can be incorporated can be found in the extensive literature relating to such products. These formulations do not warrant a detailed description here, which is in no way exhaustive. A person skilled in the art of formulating such consumer products is fully capable of selecting suitable components based on his general knowledge and the available literature.

[0219] Preferably, the consumer product comprises 0.1 to 15 wt%, more preferably 0.2 to 5 wt% of the microcapsules of the invention, these percentages being by weight relative to the total weight of the consumer product. Of course, the above concentrations can be adjusted according to the desired olfactory effect of each product.

[0220] According to a particular embodiment, the pH of the consumer product into which the microcapsules are incorporated is preferably below 4.5.

[0221] Fabric softener

[0222] An object of the present invention is a consumer product in the form of a fabric softener composition comprising:

[0223] - fabric softener active base; preferably selected from the group consisting of: dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg ester quaternary ammonium salts (HEQ), TEAQ (triethanolamine quaternary ammonium salts), silicones and mixtures thereof, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition

[0224] - Microcapsule slurry as defined above, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0225] Liquid detergent

[0226] An object of the present invention is a consumer product in the form of a liquid detergent composition comprising:

[0227] - liquid detergent active base; preferably selected from the group consisting of anionic surfactants, such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and nonionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucamides, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition.

[0228] - Microcapsule slurry as defined above, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0229] Solid detergent

[0230] An object of the present invention is a consumer product in the form of a solid detergent composition comprising:

[0231] - solid detergent active base; preferably selected from the group consisting of anionic surfactants, such as alkylbenzene sulfonates (ABS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), methyl ester sulfonates (MES), and nonionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucamides, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition.

[0232] - Microcapsule slurry or microcapsule powder as defined above, preferably in an amount of 0.05 to 15 wt %, more preferably 0.1 to 5 wt %, based on the total weight of the composition.

[0233] Solid odor enhancer

[0234] An object of the present invention is a consumer product in the form of a solid scent booster comprising:

[0235] - a solid carrier, preferably selected from the group consisting of urea, sodium chloride, sodium sulfate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars such as sucrose, mono-, disaccharides and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohol or fatty acid and mixtures thereof.

[0236] - Microcapsule powder as defined above, in powder form, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0237] Liquid scent enhancers

[0238] An object of the present invention is a consumer product in the form of a liquid odor enhancer comprising:

[0239] - aqueous phase,

[0240] - a surfactant system consisting essentially of one or more than one nonionic surfactant, wherein the surfactant system has an average HLB of 10 to 14, preferably selected from the group consisting of ethoxylated aliphatic alcohols, POE / PPG (polyoxyethylene and polyoxypropylene) ethers, mono- and polyglycerol esters, sucrose ester compounds, polyoxyethylene hydroxy esters, alkyl polyglucosides, amine oxides and combinations thereof;

[0241] - a linker selected from the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxycarboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactants with an HLB of less than 10, and mixtures thereof, and

[0242] - Microcapsule slurry as defined above, in the form of a slurry, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0243] Shampoo / shower gel

[0244] An object of the present invention is a consumer product in the form of a shampoo or shower gel composition comprising:

[0245] - shampoo or shower gel active base; preferably selected from the group consisting of sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoacetate, cocamidopropyl betaine, cocamide MEA, alkyl glucoside and amino acid surfactants, and mixtures thereof, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition;

[0246] - Microcapsule slurry as defined above, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0247] Rinse-off conditioner

[0248] An object of the present invention is a consumer product in the form of a rinse-off conditioner composition comprising:

[0249] - rinse-off conditioner active base; preferably selected from the group consisting of: cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, benzalkonium chloride, behenyl trimethyl ammonium chloride and mixtures thereof, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition;

[0250] - Microcapsule slurry as defined above, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0251] Hair dye

[0252] An object of the present invention is a consumer product in the form of an oxidative hair dyeing composition comprising:

[0253] - an oxidizing phase comprising an oxidizing agent and a basic phase comprising an alkaline agent, a dye precursor and a coupling compound; wherein the dye precursor and the coupling compound form an oxidative hair dye in the presence of the oxidizing agent, preferably in an amount of 85 to 99.95% by weight, based on the total weight of the composition,

[0254] - Microcapsule slurry as defined above, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.

[0255] "Oxidative hair dyeing composition" refers to a composition that contains two sets of colorless dye molecules: a dye precursor and a coupler. When they react with each other through an oxidation process, they form various colored molecules (dyes) that are then trapped in the hair due to their size. In other words, the dye precursor and the coupler compound form an oxidative hair dye in the presence of an oxidizing agent.

[0256] In the present invention, "dye precursor" and "oxidative dye precursor" are used without distinction.

[0257] The dye precursor may be an aromatic compound derived from benzene substituted with at least two electron donor groups in the para or ortho position, such as NH 2 and OH to impart oxidizable properties.

[0258] According to one embodiment, the dye precursor is selected from the group consisting of p-phenylenediamine, 2,5-diaminotoluene, N,N-bis(2-hydroxymethyl)-p-phenylenediamine, 4-aminophenol, 1,4-diaminobenzene, and mixtures thereof.

[0259] The primary dye precursor is used in combination with a coupling agent. The coupling agent is preferably derived from benzene and substituted at the meta position with a moiety such as NH 2 and OH groups, and do not produce color alone, but will change the color, shade or intensity formed by the dye precursor.

[0260] According to one embodiment, the coupling agent is selected from the group consisting of resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2,5-diaminotoluene, 1,3-diaminobenzene, 2,4-diaminophenoxyethanol HCl, 2-amino-hydroxyethylaminoanisole sulfate, 4-amino-2-hydroxytoluene, and mixtures thereof.

[0261] The oxidative dye precursor is preferably used in an amount of 0.001 to 5% by weight, preferably 0.1 to 4% by weight, based on the total weight of the composition.

[0262] The use of oxidative dye precursors and couplers in hair dyeing preparations has been widely disclosed in the prior art and is well known to those skilled in the art. For example, EP 0 946 133 A1 can be cited, the content of which is incorporated herein by reference.

[0263] The alkaline phase comprises an alkaline agent, preferably selected from the group consisting of ammonium hydroxide, ammonium carbonate, ethanolamine, potassium hydroxide, sodium borate, sodium carbonate, triethanolamine, and mixtures thereof.

[0264] The alkaline agent is preferably used in an amount of 1 to 10% by weight, preferably 3 to 9% by weight, based on the total weight of the composition.

[0265] According to the present invention, a coupler and a dye precursor are combined in an alkaline medium in the presence of an oxidizing agent to form an oxidative hair dye.

[0266] The oxidizing agent will provide the necessary oxygen to form color molecules and change the color of your hair.

[0267] Oxidizing agents should be safe and effective for use in the compositions herein.

[0268] Preferably, oxidising agents suitable for use herein will be soluble in the compositions according to the present invention when used in liquid form and / or in the form in which they are intended to be used.

[0269] Preferably, oxidizing agents suitable for use herein will be water soluble. Suitable oxidizing agents for use herein are selected from inorganic peroxygen oxidizing agents, preformed organic peroxyacid oxidizing agents and organic peroxide oxidizing agents or mixtures thereof.

[0270] The oxidizing agent is preferably used in an amount of 5 to 30% by weight, preferably 5 to 25% by weight, based on the total weight of the composition.

[0271] Components commonly used in cosmetic compositions can be added to the hair dye composition defined in the present invention, such as surfactants, cationic polymers, oily substances, silicone derivatives, free fragrances, preservatives, ultraviolet absorbers, antioxidants, bactericides, propellants, and thickeners.

[0272] According to a particular embodiment, the hair dyeing composition comprises one or more quaternary ammonium compounds, preferably selected from the group consisting of cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behenyltrimonium chloride and mixtures thereof, to impart conditioning benefits to the hair.

[0273] Perfuming composition

[0274] According to a particular embodiment, the consumer product is in the form of a perfuming composition comprising, based on the total weight of the perfuming composition:

[0275] - 0.1 to 30% by weight, preferably 0.1 to 20% by weight, of microcapsules as defined previously,

[0276] - 0 to 40% by weight, preferably 3 to 40% by weight, of fragrance, and

[0277] - 20 to 90% by weight, preferably 40 to 90% by weight, of ethanol.

[0278] The present invention will now be further described by way of examples. It should be understood that the invention as claimed is not intended to be limited in any way by these examples.

[0279] Example

[0280] General solution

[0281] 1,3,5-benzenetricarboxylic acid chloride (BTC, 1.77g, Table 1) is dissolved in benzyl benzoate (5g). Emulsifier (0.95g) is dispersed in benzyl benzoate (5g) and optionally kept under stirring at 60°C for 1 hour. The two solutions are mixed together, stirred at room temperature for 10 minutes, and then added to perfume oil (25g, Table 2a or Table 2b) at room temperature to form an oil phase. The oil phase is mixed with water (94.05g), which optionally contains amino compound A (the first amino compound) or a base. The reaction mixture is stirred at 24,000rpm for 30 seconds or 1 minute to provide an emulsion with Ultra Turrax. Amino compound B (the second amino compound) (Table 3) is dissolved in water (5g), and the solution is added dropwise to the emulsion. A solution of guanidine carbonate (30% by weight aqueous solution, 5 to 10g) is optionally added to control the pH value to about 8. The reaction mixture was stirred at 30 °C for 4 hours to afford a white dispersion.

[0282] Example 1

[0283] Preparation of microcapsules according to the method of the present invention

[0284] Microcapsules were prepared according to the general protocol described previously.

[0285] Material

[0286] Table 1: List of ingredients used in the examples

[0287] Composition Function <![CDATA[BTC 1) > Acyl chloride <![CDATA[Isophthaloyl dichloride 2) > Acyl chloride <![CDATA[mXDA 3) > Amino compound <![CDATA[L-Lysine 4) > Amino compound <![CDATA[EDA 5) > Amino compound <![CDATA[Cystamine dihydrochloride 6) > Amino compound <![CDATA[Diethylenetriamine 7) > Amino compound <![CDATA[Spermine dihydrate 8) > Amino compound <![CDATA[Guanidine carbonate 9) > Amino compound <![CDATA[Cystine di-tert-butyl ester 10) > Amino compound <![CDATA[zein 11) > Colloid stabilizer <![CDATA[Gum arabic 12) > Colloid stabilizer <![CDATA[Bovine serum albumin 13) > Colloid stabilizer <![CDATA[Albumin 14) > Colloid stabilizer <![CDATA[Bio Pro 2E063 15) > Colloid stabilizer <![CDATA[Bio Purβ-Lactoglobulin 16) > Colloid stabilizer <![CDATA[Sodium caseinate 17) > Colloid stabilizer <![CDATA[lactose 18) > Colloid stabilizer <![CDATA[Sodium bicarbonate 19) > Base <![CDATA[Sodium carbonate 20) > Base <![CDATA[Sodium hydroxide 21) > Base

[0288] 1) 1,3,5-Benzenetricarboxylic acid chloride; Source: Aldrich, Switzerland

[0289] 2) Isophthaloyl dichloride2) ; Source: Aldrich, Switzerland

[0290] 3) m-Xylenediamine; Source: Aldrich, Switzerland

[0291] 4) L-Lysine; Source: Aldrich, Switzerland

[0292] 5) Ethylenediamine; Source: Aldrich, Switzerland

[0293] 6) Cystamine dihydrochloride; Source: Aldrich, Switzerland

[0294] 7) Diethylenetriamine; Source: Aldrich, Switzerland

[0295] 8) Spermine dihydrate; Source: A Swiss Aldrich

[0296] 9) Guanidine carbonate; Source: Aldrich, Switzerland

[0297] 10) Cystine di-tert-butyl ester; Source: Aldrich, Switzerland

[0298] 11) Zein; Source: Aldrich, Switzerland

[0299] 12) Gum Arabic Superstab AA; Source: Nexira, France

[0300] 13) Bovine serum albumin; Source: Aldrich, Switzerland

[0301] 14) Albumin

[0302] 15) Bio Pro 2E063; Source: Agropur Inc., USA

[0303] 16) Bio Pur β-lactoglobulin; Source: Danisco

[0304] 17) Sodium caseinate; Source: Aldrich, Switzerland

[0305] 18) Lactose; Source: Aldrich, Switzerland

[0306] 19) Sodium bicarbonate; Source: Aldrich, Switzerland

[0307] 20) Sodium carbonate; Source: Aldrich, Switzerland

[0308] 21) Sodium hydroxide; Source: Aldrich, Switzerland

[0309] Fragrance oil composition:

[0310] Table 2a: Composition of Fragrance Oil A

[0311]

[0312]

[0313] 1) Methyl dihydrojasmonate, Firmenich SA, Geneva, Switzerland

[0314] 2) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, International Flavors & Fragrances, USA

[0315] 3)(-)-(8R)-8,12-Epoxy-13,14,15,16-detetramethyllysine, Firmenich SA, Geneva, Switzerland

[0316] Table 2b: Composition of Fragrance Oil B

[0317]

[0318] 1) Source: Firmenich SA, Geneva, Switzerland

[0319] 2) Trademark from IFF, 2-tert-butyl-1-cyclohexyl acetate

[0320] Capsule A: Preparation of capsule A with bovine serum albumin as stabilizer

[0321] Table 3: Composition of Capsule A

[0322]

[0323] Capsule B: Preparation of capsule B with bovine serum albumin

[0324] Table 4: Composition of Capsule B

[0325]

[0326] ** Protein and acyl chloride were mixed at 60°C for 1 hour

[0327] Capsule C: Preparation of capsule C with sodium caseinate

[0328] Table 5: Composition of Capsule C

[0329]

[0330] Capsule D: Preparation of capsule D with different stabilizers and combination in oil phase

[0331] Capsules D were prepared according to the protocol for preparing capsules B in the presence of L-lysine (2.5 g) as amino compound A and ethylenediamine (0.48 g or 0.24 g) as amino compound B in the presence of different proteins and diamines.

[0332] Table 6: Composition of Capsule D

[0333]

[0334] Capsule E: Preparation of capsule E with a mixture of acyl chloride and caseinate in oil phase

[0335] Capsules E were prepared according to the protocol for preparing capsules B in the presence of caseinate and diamine in the presence of L-lysine (2.5 g) as amino compound A and ethylenediamine (0.48 g or 0.24 g) as amino compound B.

[0336] Table 7: Composition of Capsule E

[0337]

[0338] Capsule F: Preparation of capsule F using only one amino compound and caseinate and protein mixture in oil phase Capsule F

[0339] Capsules F were prepared in the presence of proteins from the protein mixture with only L-lysine (2.5 g) present as amino compound A in the aqueous phase during emulsification according to the protocol used to prepare capsules B. No additional amino compound B was added after emulsification.

[0340] Table 8: Composition of Capsule F

[0341] Capsule Protein (g) F1 Caseinate 2 F2 75% caseinate / 25% whey protein 2

[0342] Example 2

[0343] Storage stability in fabric softener compositions

[0344] The storage stability of the capsules in a fabric softener was evaluated. A dispersion of the capsules of the present invention (0.27 g) (with encapsulated perfume oil B) was diluted in a fabric softener composition described in Table 9 (29.73 g). The softener was stored at 37°C for up to one month. The amount of perfume leaked from the capsules was then measured by solvent extraction and GC-FID analysis (Table 10).

[0345] Table 9: Composition of fabric softener

[0346] Product Wt% Stepantex VL 90A 8.88 10% calcium chloride solution 0.36 Proxel GXL 0.04 Fragrance 1 Water 89.72 Total 100

[0347] Table 10: Oil leakage of microcapsules in fabric softener compositions

[0348] Capsule Leakage amount in 3 days (%) Leakage amount in 30 days (%) A1 7 25 A3 14 25 A4 4 5 A5 8 8 A2 9.5 20.8 B8 10.8 16.6 B11 8.2 19.7 C1 22 32 C2 11 25 C3 13 23 C4 25 49 C5 24 33 D1 21 29 D4 22 37 D5 19 38 D6 9 22 D7 11 22 D8 16 27 E1 21 50 E2 20 48 F1 25 49 F2 20 56

[0349] It can be concluded that the microcapsules of the present invention show satisfactory stability in challenging media.

[0350] Example 3

[0351] Spray-dried microcapsule preparation

[0352] Emulsions A to E were prepared having the following compositions.

[0353] Table 11: Compositions of emulsions A to E and compositions of granular powders A to E after spray drying

[0354]

[0355] 1) CapsulTM, Ingredion

[0356] 2) Maltodextrin 10DE Source: Roquette

[0357] 3) Maltose, Lehmann & Voss

[0358] 4) Silica, Evonik

[0359] 5) See Table 12

[0360] Table 12: Composition of Fragrance C

[0361]

[0362] 1) Firmenich SA, Switzerland

[0363] 2) 3-(4-tert-Butylphenyl)-2-methylpropanal, Givaudan SA, Vergne, Switzerland

[0364] 3) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, International Flavors & Fragrances, USA

[0365] 4) Firmenich SA, Switzerland

[0366] 5) Methyl dihydrojasmonate, Firmenich SA, Switzerland

[0367] 6) Firmenich SA, Switzerland

[0368] The components of the polymer matrix (maltodextrin and capsul TM , or capsul TM, citric acid and tripotassium citrate) are added to water at 45-50°C until completely dissolved.

[0369] For Emulsion D, free perfume C was added to the water phase.

[0370] The microcapsule slurry was added to the resulting mixture.The resulting mixture was then gently mixed at 25°C (room temperature).

[0371] Granular powders A to E were prepared by spray drying emulsions A to E using a Sodeva spray dryer (origin: France) with an inlet air temperature set at 215° C. and a throughput set at 500 ml per hour. The outlet air temperature was 105° C. The emulsions before atomization were at ambient temperature.

[0372] Example 4

[0373] Liquid odor enhancer composition

[0374] Sufficient amount of microcapsule slurries A to F were weighed and mixed into the liquid aroma enhancer (Table 13) to add the equivalent of 0.2% fragrance.

[0375] Table 13: Liquid scent enhancer composition

[0376]

[0377] 1) Deceth-8; Trademark and source: KLK Oleo

[0378] 2) Laureth-9; Trademark and source:

[0379] 3) Plantacare 2000UP; Trademark and source: BASF

[0380] Different ringing gel compositions (Compositions 1 to 6) were prepared according to the following protocol.

[0381] In the first step, the aqueous phase (water), solvent (propylene glycol) (if present) and surfactant were mixed together at room temperature under stirring with a magnetic stirrer at 300 rpm for 5 minutes.

[0382] In a second step, the linker was dissolved in the hydrophobic active ingredient (fragrance) at room temperature with stirring on a magnetic stirrer at 300 rpm. The resulting mixture was mixed for 5 minutes.

[0383] The water phase and the oil phase were then mixed together at room temperature for 5 minutes, resulting in the formation of a clear or milky ringing gel.

[0384] Example 5

[0385] Liquid detergent composition

[0386] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into liquid detergent (Table 14) to add the equivalent of 0.2% fragrance.

[0387] Table 14: Liquid detergent composition

[0388]

[0389] 1) Hostapur SAS 60; Source: Clariant

[0390] 2) Edenor K 12-18; Source: Cognis

[0391] 3) Genapol LA 070; Source: Clariant

[0392] 4) Source: Genencor International

[0393] 5) Aculyn 88; Source: Dow Chemical

[0394] Example 6

[0395] Powder detergent composition

[0396] Sufficient amounts of microparticles A-E were weighed and mixed into a powder detergent composition (Table 15) to add the equivalent of 0.2% perfume.

[0397] Table 15: Powder detergent composition

[0398] Composition Parts Anionic surfactant (linear alkylbenzene sulfonate) 20％ Nonionic surfactant (alcohol ethoxylate (5 - 9 ethylene oxides)) 6％ Auxiliary agent (zeolite, sodium carbonate) 25％ Silicate 6％ Sodium sulfate 35％ Others (enzyme, polymer, bleach) 7.5％ Spray-dried particulate powders A - E 0.5％

[0399] Example 7

[0400] Concentrated general cleaner ingredients

[0401] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the concentrated all-purpose cleaner composition (Table 16) to add the equivalent of 0.2% fragrance.

[0402] Table 16: Concentrated All-Purpose Cleaner Composition

[0403]

[0404] 1) Neodol Trademark and source: Shell Chemical

[0405] 2) Biosoft Trademark and source: Stepan Company

[0406] 3) Stepanate Trademark and source: Stepan Company

[0407] 4) Kathon Trademark and source: Dow Chemical Company

[0408] Mix all ingredients together and then dilute the mixture to 100% with water.

[0409] Example 8

[0410] Solid odor enhancer composition

[0411] The following compositions were prepared.

[0412] Table 17: Salt-based solid odor enhancer composition

[0413] Composition Parts Sodium chloride 95 Spray-dried particulate powders A - E 5

[0414] Table 18: Urea-based solid odor enhancer composition

[0415] Composition Parts Urea (beads) 94 Spray-dried particulate powders A - E 8 Bentonite 3 Fragrance 3

[0416] Example 9

[0417] Shampoo composition

[0418] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the shampoo composition (Table 19) to add the equivalent of 0.2% fragrance.

[0419] Table 19: Shampoo composition

[0420]

[0421] 1)Ucare Polymer JR-400, Noveon

[0422] 2) Schweizerhall

[0423] 3) Glydant, Lonza

[0424] 4)Texapon NSO IS, Cognis

[0425] 5) Tego Betain F 50, Evonik

[0426] 6)Amphotensid GB 2009,Zschimmer&Schwarz

[0427] 7) Monomuls 90L-12, Gruenau

[0428] 8) Monosodium paraben, NIPA

[0429] Disperse Polyquaternium-10 in water. Add the remaining ingredients of Phase A one by one, mixing thoroughly after each additive is added. Then add this premix to the Polyquaternium-10 dispersion and mix for an additional 5 minutes. Then, add Phase B and premixed Phase C (heat Monomuls 90L-12 to melt in Texapon NSO IS) while stirring. Mix the mixture thoroughly. Then, add Phase D and Phase E while stirring. Adjust the pH with citric acid solution until pH: 5.5-6.0

[0430] Example 10

[0431] Shampoo composition

[0432] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the shampoo composition (Table 20) to add the equivalent of 0.2% fragrance.

[0433] Table 20: Shampoo composition

[0434]

[0435] 1) EDETA B powder, BASF

[0436] 2) Jaguar C14 S, Rhodia

[0437] 3) Ucare Polymer JR-400, Noveon

[0438] 4)Sulfetal LA BE,Zschimmer&Schwarz

[0439] 5)Zetesol LA,Zschimmer&Schwarz

[0440] 6) Tego Betain F 50, Evonik

[0441] 7)Xiameter MEM-1691,Dow Corning

[0442] 8) Lanette 16, BASF

[0443] 9) Comperlan 100, Cognis

[0444] 10) Cutina AGS, Cognis

[0445] 11) Kathon CG, Rohm & Haas

[0446] 12) D-Panthenol, Roche

[0447] Add the premix of guar hydroxypropyltrimonium chloride and polyquaternium-10 to water and tetrasodium EDTA while mixing. When the mixture is uniform, add NaOH. Then, add phase C ingredients. And heat the mixture to 75°C. Add phase D ingredients and mix until uniform. Stop heating and reduce the temperature of the mixture to room temperature. At 45°C, add phase E ingredients while mixing, adjust the final viscosity with 25% NaCl solution, and adjust the pH to 5.5-6 with 10% NaOH solution.

[0448] Embodiment 11

[0449] Wash-off hair composition

[0450] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the rinse-off composition (Table 21) to add the equivalent of 0.2% fragrance.

[0451] Table 21: Rinse-off Composition

[0452]

[0453] 1) Genamin KDMP, Clariant

[0454] 2) Tylose H10 Y G4, Shin Etsu

[0455] 3) Lanette O, BASF

[0456] 4) Arlacel 165, Croda

[0457] 5)Incroquat Behenyl TMS-50-PA-(MH),Croda

[0458] 6) Brij S20, Croda

[0459] 7)Xiameter MEM-949,Dow Corning

[0460] 8) Alfa Aesar

[0461] Mix the ingredients of phase A until a homogeneous mixture is obtained. Allow the Tylose to dissolve completely. Then heat the mixture to 70-75°C. Combine the ingredients of phase B and melt at 70-75°C. Then add the ingredients of phase B to phase A with good stirring and continue mixing until cooled to 60°C. Then add the ingredients of phase C while stirring and keep mixing until the mixture cools to 40°C. Adjust the pH with citric acid solution until pH: 3.5-4.0.

[0462] Example 12

[0463] Antiperspirant spray anhydrous composition

[0464] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the antiperspirant spray anhydrous composition (Table 22) to add the equivalent of 0.2% fragrance.

[0465] Table 22: Antiperspirant Spray Anhydrous Composition

[0466] Composition Amount (wt%) <![CDATA[Cyclic polydimethylsiloxane 1) > 53.51 Isopropyl myristate 9.04 <![CDATA[Silicon dioxide 2) > 1.03 <![CDATA[Quaternary ammonium salt-18 hectorite 3) > 3.36 <![CDATA[Aluminum Chlorohydrate 4) > 33.06

[0467] 1) Dow 345Fluid; Trademark and source: Dow Corning

[0468] 2) 200; Trademark and source: Evonik

[0469] 3) 38; Trademark and source: Elementis Specialities

[0470] 4) Micro Dry Ultrafine; Source: Reheis

[0471] Using a high speed stirrer, add silica and quaternium-18-hectorite to the mixture of isopropyl myristate and cyclomethicone. Once fully swollen, add aluminum chlorohydrate in portions under stirring until the mixture is homogeneous and free of lumps. Fill an aerosol can with 25% of the suspension and 75% of propane / butane (2.5 bar).

[0472] Embodiment 13

[0473] Antiperspirant spray emulsion composition

[0474] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the antiperspirant spray emulsion composition (Table 23) to add fragrance equivalent to 0.2%.

[0475] Table 23: Antiperspirant spray emulsion composition

[0476] Composition Amount (wt%) <![CDATA[Polysorbate 65 1) (Part A)]]> 0.95 <![CDATA[Diglycerin-2 Dimer Dihydroxystearate 2) (Part A)]]> 1.05 <![CDATA[Cetyl PEG / PPG-10 / 1 Polydimethylsiloxane 3) (Part A)]]> 2.75 <![CDATA[Cyclic polydimethylsiloxane 4) (Part A)]]> 16.4 <![CDATA[Isopropyl isostearate 5) (Part A)]]> 4.5 <![CDATA[Phenoxyethanol 6) (Part A)]]> 0.5 <![CDATA[Ethylhexylglycerin 7) (Part A)]]> 0.2 <![CDATA[C12-15 alkyl benzoate 8) (Part A)]]> 5.65 <![CDATA[Silanized silica 9) (Part A)]]> 0.1 <![CDATA[Sodium methylparaben 10) (Part B)]]> 0.1 <![CDATA[Aluminum Chlorohydrate 11) (Part B)]]> 20 Water (Part B) 44.47 Fragrance (Part C) 3.33

[0477] 1) Tween 65; Trademark and source: CRODA

[0478] 2) Dehymuls PGPH; Trademark and source: BASF

[0479] 3) Abil EM-90; Trademark and source: BASF

[0480] 4) Dow Corning 345fluid; Trademark and source: Dow Corning

[0481] 5) Crodamol ipis; Trademark and source: CRODA

[0482] 6) Phenoxyethanol; Trademark and source: LANXESS

[0483] 7) Sensiva sc 50; Trademark and source: KRAFT

[0484] 8) Tegosoft TN; Trademark and source: Evonik

[0485] 9) Aerosil R 812; Trademark and source: Evonik

[0486] 10) Nipagin mna; Trademark and source: CLARIANT

[0487] 11) Locron L; Trademark and source: CLARIANT

[0488] The ingredients of Part A and Part B are weighed 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 in a small portion while stirring continuously into Part A. 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. Compact the propellant and add it.

[0489] Aerosol filling: 30% emulsion: 70% propane / butane 2.5 bar

[0490] Embodiment 14

[0491] Body fragrance spray composition

[0492] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the antiperspirant deodorant spray composition (Table 24) to add the equivalent of 0.2% fragrance.

[0493] Table 24: Deodorant Spray Composition

[0494] Composition Amount (wt%) 95% ethanol 90.65 <![CDATA[Triclosan 1) > 0.26 Isopropyl myristate 9.09

[0495] 1) DP 300; Trademark and source: BASF

[0496] All ingredients were mixed and dissolved according to the order of Table 24. The aerosol can was then filled, compacted and the propellant added (aerosol fill: 40% active solution, 60% propane / butane 2.5 bar).

[0497] Embodiment 15

[0498] Antiperspirant roll-on emulsion composition

[0499] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the antiperspirant roll-on emulsion composition (Table 25) to add the equivalent of 0.2% fragrance.

[0500] Table 25: Antiperspirant Roll-On Lotion Composition

[0501] Composition Amount (wt%) <![CDATA[Stearyl alcohol polyether-2 1) (Part A)]]> 3.25 <![CDATA[Polyoxyethylene (21) Stearyl Ether 2) (Part A)]]> 0.75 <![CDATA[PPG-15 Stearyl Ether 3) (Part A)]]> 4 Deionized water (Part B) 51 <![CDATA[50% aqueous solution of aluminum chlorohydrate 4) (Part C)]]> 40 Fragrance (Part D) 1

[0502] 1) BRIJ 72; Source: ICI

[0503] 2) BRIJ 721; Source: ICI

[0504] 3) ARLAMOL E; Source: UNIQEMA-CRODA

[0505] 4) LOCRON L; Source: CLARIAN

[0506] Heat Part A and Part B separately to 75°C; add Part A to Part B while stirring, and homogenize the mixture for 10 minutes. Then, cool the mixture while stirring. When the mixture reaches 45°C, slowly add Part C, and when the mixture reaches 35°C, slowly add Part D while stirring. Then cool the mixture to room temperature.

[0507] Example 16

[0508] Antiperspirant roll-on composition

[0509] Sufficient amounts of microcapsule slurries A-F were weighed and mixed into the antiperspirant roll-on composition (Table 26) to add the equivalent of 0.2% fragrance.

[0510] Table 26: Antiperspirant Roll-On Composition

[0511] Composition Amount Water (Part A) 45 <![CDATA[50% aqueous solution of aluminum chlorohydrate 1) (Part B)]]> 20 Denatured alcohol (96% ethanol) (Part B) 30 <![CDATA[Ceteth-12 2) (Part C)]]> 2 <![CDATA[Ceteareth-30 3) (Part C)]]> 2 Fragrance (Part D) 1

[0512] 1) LOCRON L; Source: CLARIANT

[0513] 2)EUMULGIN B-1; Source: BASF

[0514] 3)EUMULGIN B-3; Source: BASF

[0515] Mix the ingredients of Part B in a container and then add the ingredients of Part A. Then dissolve Part C into Part A and Part B. For fragrance, add 1 part Cremophor RH40 to 1 part fragrance while mixing well.

[0516] Embodiment 17

[0517] Antiperspirant roll-on composition

[0518] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the antiperspirant roll-on emulsion composition (Table 27) to add the equivalent of 0.2% fragrance.

[0519] Table 27: Antiperspirant Roll-On Lotion Composition

[0520] Composition Amount (wt%) Water (Part A) 50.51 <![CDATA[Hydroxyethyl cellulose 1) (Part A)]]> 0.71 95% ethanol (Part B) 40.40 1,2 - propylene glycol (Part B) 5.05 <![CDATA[Triclosan 2) (Part B)]]> 0.30 <![CDATA[PEG - 40 Hydrogenated Castor Oil 3) (Part C)]]> 3.03

[0521] 1) 250H; Trademark and source: Ashland

[0522] 2) DP 300; Trademark and source: BASF

[0523] 3) RH 40; Trademark and source: BASF

[0524] Part A is prepared by sprinkling hydroxyethylcellulose little by little in water while stirring rapidly with a turbine. Continue stirring until the hydroxyethylcellulose is completely swollen and gives a transparent gel. Then, pour part B into part A little by little while continuing to stir until the whole is uniform. Add part C.

[0525] Embodiment 18

[0526] Alcohol-free body fragrance pump

[0527] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 28) to add the equivalent of 0.2% fragrance.

[0528] Table 28: Deodorant Composition

[0529] Composition Amount (wt%) <![CDATA[C12-15 alkyl lactate 1) > 5 <![CDATA[Polydimethylsiloxane 2) > 91.6 <![CDATA[Cetyl lactate 3) > 1 <![CDATA[Octyldodecanol 4) > 0.8 <![CDATA[Triclosan 5) > 0.1 Fragrance 1.5

[0530] 1) Ceraphyl 41; Trademark and source: ASHLAND

[0531] 2)DOW CORNING 200FLUID 0.65cs; Trademark and source: DOW CORNING CORPORATION

[0532] 3) Ceraphyl 28; Brand and source: ASHLAND

[0533] 4)Eutanol G; Trademark and source: BASF

[0534] 5) DP 300; Trademark and source: BASF

[0535] All ingredients of Table 28 were mixed according to the order of the table, and the mixture was slightly heated to dissolve the cetyl lactate.

[0536] Embodiment 19

[0537] Alcohol-containing body fragrance pump

[0538] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 29) to add the equivalent of 0.2% fragrance.

[0539] Table 29: Deodorant Composition

[0540] Composition Amount (wt%) Ethanol (Part A) 60 <![CDATA[PEG-6 Caprylic / Capric Glycerides 1) (Part A)]]> 2 Water (Part A) 35.6 <![CDATA[PEG-40 Hydrogenated Castor Oil 2) (Part B)]]> 0.4 Fragrance (Part B) 2

[0541] 1)Softigen 767; Trademark and source: CRODA

[0542] 2) RH 40; Trademark and source: BASF

[0543] Mix together the ingredients in Part B. Dissolve the ingredients in Part A in the order listed and pour into Part B.

[0544] Embodiment 20

[0545] Talc formula

[0546] Weigh out a sufficient amount of granules A to F and mix into a standard talc base: 100% talc, very slight characteristic odor, white powder, source: LUZENAC, to add the equivalent of 0.2% of fragrance.

[0547] Embodiment 21

[0548] Bath gel reference

[0549] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 30) to add the equivalent of 0.2% fragrance.

[0550] Table 30: Body wash composition

[0551] Composition Amount (% wt) Function Deionized water 49.350 Solvent <![CDATA[Sodium EDTA 1) > 0.050 Chelating agent <![CDATA[Acrylate copolymer 2) > 6.000 Thickening agent <![CDATA[Sodium C12-C15 pareth sulfate 3) > 35.000 Surfactant 20% aqueous sodium hydroxide solution 1.000 pH regulator <![CDATA[Cocamidopropyl betaine 4) > 8.000 Surfactant <![CDATA[Methylchloroisothiazolinone and Methylisothiazolinone 5) > 0.100 Preservative Citric acid (40%) 0.500 pH regulator

[0552] 1)EDETA B POWDER; Trademark and source: BASF

[0553] 2) CARBOPOL AQUA SF-1 POLYMER; Trademark and source: NOVEON

[0554] 3) ZETESOL AO 328U; Trademark and source: ZSCHIMMER&SCHWARZ

[0555] 4)TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0556] 5) KATHON CG; Trademark and source: ROHM & HASS

[0557] The ingredients were mixed and the pH was adjusted to 6-6.3 (viscosity: 4500 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0558] Embodiment 22

[0559] Bath gel composition

[0560] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 31) to add the equivalent of 0.2% fragrance.

[0561] Table 31: Body wash composition

[0562] Composition Amount (% wt) Function Deionized water 52.40 Solvent <![CDATA[Sodium EDTA 1) > 0.10 Chelating agent Sodium benzoate 0.50 Preservative Propylene glycol 2.00 Solvent <![CDATA[Sodium C12 - C15 alcohol polyether sulfate 2) > 35.00 Surfactant <![CDATA[Cocamidopropyl betaine 3) > 8.00 Surfactant <![CDATA[Polyquaternium-7 4) > 0.20 Conditioning agent Citric acid (40%) 1.00 pH regulator Sodium chloride 0.80 Viscosity regulator

[0563] 1) EDETA B powder; Trademark and source: BASF

[0564] 2) ZETESOL AO 328U; Trademark and source: ZSCHIMMER&SCHWARZ

[0565] 3)TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0566] 4) MERQUAT 550; Trademark and source: LUBRIZOL

[0567] The ingredients were mixed and the pH was adjusted to 4.5 (viscosity: 3000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0568] Embodiment 23

[0569] Bath gel composition

[0570] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 32) to add the equivalent of 0.2% fragrance.

[0571] Table 32: Body wash composition

[0572]

[0573] 1) EDETA B powder; Trademark and source: BASF

[0574] 2)Texapon NSO IS; Trademark and source: COGNIS

[0575] 3) MERQUAT 550; Trademark and source: LUBRIZOL

[0576] 4)DEHYTON AB-30; Trademark and source: COGNIS

[0577] 5) GLUCAMATE LT; Trademark and source: LUBRIZOL

[0578] 6)EUPERLAN PK 3000AM; Trademark and source: COGNIS

[0579] 7) CREMOPHOR RH 40; Trademark and source: BASF

[0580] The ingredients were mixed and the pH was adjusted to 4.5 (viscosity: 4000 cPo + / - 1500 cPo (Brookfield RV / Spindle #4 / 20 RPM)).

[0581] Embodiment 24

[0582] Hand sanitizer

[0583] Sufficient amounts of microcapsule slurries A to F were weighed and mixed into the following composition (Table 33) to add the equivalent of 0.2% fragrance.

[0584] Table 33: Hand sanitizer composition

[0585] Composition Amount (% wt) Function <![CDATA[Linear alkylbenzene sulfonic acid (1) > 20 Anionic surfactant <![CDATA[Diethanolamide (2) > 3.5 Foam enhancer <![CDATA[Sodium hydroxide (50%) (3) > 3.4 pH regulator / neutralizer <![CDATA[Secondary alcohol ethoxolate (4) > 2.5 Non-ionic surfactant Sodium xylene sulfonate 6.3 Hydrotrope Water 64.3 Solvent

[0586] 1) Biosoft Trademark and source: Stepan Company

[0587] 2) Ninol Trademark and source: Stepan Company

[0588] 3) Stepanate Trademark and source: Stepan Company

[0589] 4) Tergitol Trademark and source: Dow Chemical Company

[0590] Mix water with sodium hydroxide and diethanolamide. Add LAS. After neutralizing the LAS, add the remaining ingredients. Check the pH (=7-8) and adjust if necessary.

[0591] Embodiment 25

[0592] Toothpaste formulation

[0593] A sufficient amount of microcapsule slurry M (corresponding to microcapsule A except that menthol flavoring is encapsulated) is weighed and mixed into the following composition (Table 34) to add the flavoring equivalent to 0.2%.

[0594] Table 34: Toothpaste formula

[0595] Ingredient Amount (% by weight) Polyethylene glycol 400 2.0％ Xanthan gum 0.6％ Sorbitol 70% solution 50％ Sodium fluoride 0.220％ Sodium benzoate 0.2％ Water 15.230％ <![CDATA[Hydrated silica 1) > 22.0％ <![CDATA[Hydrated silicon dioxide 2) > 7.0％ Titanium dioxide CI77891 0.5％ Sodium lauryl sulfate 1.250％ Flavoring agent 1.2％ Total 100％

[0596] 1) Tixosil 73; Trademark and source:

[0597] 2) Tixosil 43; Trademark and source:

[0598] Embodiment 26

[0599] Calcium hydrogen phosphate-based toothpaste formulation

[0600] A sufficient amount of microcapsule slurry M (corresponding to microcapsule A except that menthol flavoring is encapsulated) is weighed and mixed into the following composition (Table 35) to add the flavoring equivalent to 0.2%.

[0601] Table 35: Toothpaste formula

[0602]

[0603]

[0604] 1) Trademarks and sources:

[0605] Embodiment 27

[0606] Alcohol-free mouthwash formulation

[0607] A sufficient amount of microcapsule slurry M (corresponding to microcapsule A except that menthol flavoring is encapsulated) is weighed and mixed into the following composition (Table 36) to add the flavoring equivalent to 0.2%.

[0608] Table 36: Mouthwash formulation

[0609] Ingredient Amount (% by weight) Propylene glycol 10％ Flavoring agent 0.240％ Deionized water / Pure water Balance to final weight Poloxamer 407NF 0.240％ Sodium lauryl sulfate 0.040％ Sorbitol 70% solution 10.0％ Sodium saccharin 0.030％ Glycerol 3.0％ Sodium benzoate 0.100％ Sucralose 0.020％ Benzoic acid 0.050％ Total 100％

[0610] Embodiment 28

[0611] Mouthwash formulation

[0612] A sufficient amount of microcapsule slurry M (corresponding to microcapsule A except that menthol flavoring is encapsulated) is weighed and mixed into the following composition (Table 37) to add the flavoring equivalent to 0.2%.

[0613] Table 37: Mouthwash formulation

[0614] Ingredient Amount (% by weight) Ethanol 190 Proof 15.0％ Flavoring agent 0.240％ Deionized water / Pure water Balance to final weight Poloxamer 407NF 0.240％ Sodium lauryl sulfate 0.040％ Sorbitol 70% solution 10.0％ Sodium saccharin 0.030％ Glycerol 3.0％ Sodium benzoate 0.100％ Sucralose 0.020％ Benzoic acid 0.050％ Total 100％ .

Claims

1. A method for preparing a polyamide core-shell microcapsule sizing agent, comprising the following steps: a) Dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a perfume, to form an oil phase; b) Dispersing the oil phase obtained in step a) into an aqueous phase containing an amino compound A or a base to form an oil-in-water emulsion; and c) Performing a curing step to form polyamide microcapsules in the form of a sizing agent, wherein at least one amino compound B is added to the aqueous phase before forming the oil-in-water emulsion and / or added to the oil-in-water emulsion obtained after step b), wherein the amino compound A is an amino acid and the stabilizer is a protein.

2. The method according to claim 1, wherein the method comprises the following steps: a) Dissolving at least one acyl chloride and at least one stabilizer in a hydrophobic material, preferably a perfume, to form an oil phase; b) Dispersing the oil phase obtained in step a) into an aqueous phase containing an amino compound A or a base to form an oil-in-water emulsion; c) Adding an amino compound B to the oil-in-water emulsion obtained in step b); and d) Performing a curing step to form polyamide microcapsules in the form of a sizing agent.

3. The method according to 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, oxydiacetyl dichloride, succinyl dichloride, and mixtures thereof.

4. The method according to any one of the preceding claims, wherein the aqueous phase contains a base selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, and mixtures thereof.

5. The method according to any one of the preceding claims, wherein the aqueous phase contains an amino compound A selected from the group consisting of L-lysine, L-lysine ethyl ester, guanidine carbonate, chitosan, 3-aminopropyltriethoxysilane, and mixtures thereof.

6. The method according to claim 1, wherein the amino acid is selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, and mixtures thereof.

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

8. The method according to any one of the preceding claims, wherein the amino compound A and the amino compound B are different.

9. The method according to claim 1, wherein the stabilizer is a protein selected from the group consisting of: soy protein, rice protein, whey protein, ovalbumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk fibroin, sericin protein powder, and mixtures thereof.

10. The method according to any one of the preceding claims, wherein the molar ratio between the functional group NH of the amino compound B 2 and the functional group COCl of the acyl chloride is from 0.01 to 7.

5.

11. The method according to any one of the preceding claims, wherein the weight ratio between the acyl chloride and the hydrophobic material is from 0.01 to 0.

09.

12. A polyamide core - shell microcapsule slurry obtainable by the method according to any one of claims 1 to 11.

13. A perfuming composition comprising: (i) the perfume microcapsules as defined in claim 12, 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 perfume adjuvant.

14. A consumer product comprising: - a personal care active base, and - the microcapsules as defined in claim 12 or the perfuming composition as defined in claim 13, wherein the consumer product is in the form of a personal care composition.

15. A consumer product comprising: - a household care or fabric care active ingredient, and - the microcapsules as defined in claim 12 or the perfuming composition as defined in claim 13, wherein the consumer product is in the form of a household care or fabric care composition.

Images